# Electronic Supplementary Material (ESI) for CrystEngComm. # This journal is © The Royal Society of Chemistry 2016 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_no01pxg _database_code_depnum_ccdc_archive 'CCDC 1460868' _audit_update_record ; 2016-05-24 deposited with the CCDC. 2016-07-12 downloaded from the CCDC. ; _audit_creation_method SHELXL-2013 _chemical_name_systematic 'bis(4,5-dihydronaphto[1,2-d])tetrathiafulvalene ' _chemical_name_common BDHN-TTF _chemical_melting_point ? _chemical_formula_moiety 'C22 H16 S4' _chemical_formula_sum 'C22 H16 S4' _chemical_formula_weight 408.59 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.1748(18) _cell_length_b 7.7639(9) _cell_length_c 7.5390(8) _cell_angle_alpha 90 _cell_angle_beta 91.191(2) _cell_angle_gamma 90 _cell_volume 946.54(18) _cell_formula_units_Z 2 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 1850 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 28.28 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.434 _exptl_crystal_F_000 424 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_absorpt_coefficient_mu 0.505 _shelx_estimated_absorpt_T_min ? _shelx_estimated_absorpt_T_max ? _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6864 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details 'SADABS v2.10 BRUKER 2001' _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega sacans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 14203 _diffrn_reflns_av_unetI/netI 0.0287 _diffrn_reflns_av_R_equivalents 0.0468 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.519 _diffrn_reflns_theta_max 28.280 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.988 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.988 _diffrn_reflns_point_group_measured_fraction_full 0.998 _reflns_number_total 2318 _reflns_number_gt 1854 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT+' _computing_structure_solution SHELXTL _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0567P)^2^+0.1454P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 2318 _refine_ls_number_parameters 150 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.1062 _refine_ls_wR_factor_gt 0.0985 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.46964(3) 0.55969(7) 0.22131(5) 0.06121(17) Uani 1 1 d . . . . . C1 C 0.46682(10) 0.4981(2) 0.44595(19) 0.0510(4) Uani 1 1 d . . . . . S2 S 0.36914(3) 0.42942(6) 0.51678(5) 0.06036(17) Uani 1 1 d . . . . . C2 C 0.31757(10) 0.47896(18) 0.31561(19) 0.0460(3) Uani 1 1 d . . . . . C3 C 0.22797(10) 0.46362(18) 0.2991(2) 0.0484(3) Uani 1 1 d . . . . . C4 C 0.18004(13) 0.3804(2) 0.4249(3) 0.0648(5) Uani 1 1 d . . . . . H4A H 0.2082(12) 0.325(3) 0.524(3) 0.073(6) Uiso 1 1 d . . . . . C5 C 0.09517(15) 0.3787(4) 0.4082(3) 0.0852(7) Uani 1 1 d . . . . . H5A H 0.0646(15) 0.323(3) 0.485(3) 0.103(8) Uiso 1 1 d . . . . . C6 C 0.05649(16) 0.4601(4) 0.2674(4) 0.0898(7) Uani 1 1 d . . . . . H6A H -0.0007(19) 0.462(3) 0.264(4) 0.092(7) Uiso 1 1 d . . . . . C7 C 0.10316(14) 0.5419(3) 0.1417(3) 0.0761(6) Uani 1 1 d . . . . . H7A H 0.0787(15) 0.597(3) 0.046(4) 0.091(7) Uiso 1 1 d . . . . . C8 C 0.18839(11) 0.5444(2) 0.1542(2) 0.0554(4) Uani 1 1 d . . . . . C9 C 0.23952(13) 0.6440(3) 0.0245(3) 0.0681(5) Uani 1 1 d . . . . . H9A H 0.2106(13) 0.644(3) -0.095(3) 0.090(7) Uiso 1 1 d . . . . . H9B H 0.2454(14) 0.770(3) 0.067(3) 0.094(7) Uiso 1 1 d . . . . . C10 C 0.32605(13) 0.5753(3) 0.0028(2) 0.0583(4) Uani 1 1 d . . . . . H10A H 0.3576(11) 0.658(2) -0.055(3) 0.060(5) Uiso 1 1 d . . . . . H10B H 0.3201(13) 0.468(3) -0.069(3) 0.078(6) Uiso 1 1 d . . . . . C11 C 0.36403(10) 0.53643(18) 0.18242(19) 0.0475(3) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0576(3) 0.0900(3) 0.0364(2) 0.01374(19) 0.00717(17) 0.0095(2) C1 0.0576(9) 0.0618(9) 0.0339(7) 0.0054(6) 0.0064(6) 0.0136(7) S2 0.0601(3) 0.0840(3) 0.0371(2) 0.01864(18) 0.00431(17) 0.0090(2) C2 0.0612(9) 0.0433(7) 0.0335(7) 0.0030(5) -0.0001(6) 0.0049(6) C3 0.0625(9) 0.0413(7) 0.0414(8) -0.0029(6) 0.0027(7) -0.0014(6) C4 0.0721(12) 0.0665(10) 0.0561(10) 0.0085(9) 0.0047(9) -0.0076(9) C5 0.0766(14) 0.1040(17) 0.0755(14) 0.0069(13) 0.0127(11) -0.0237(13) C6 0.0606(13) 0.128(2) 0.0806(16) -0.0035(14) -0.0017(11) -0.0144(13) C7 0.0670(12) 0.0981(15) 0.0628(12) -0.0013(11) -0.0125(10) -0.0008(11) C8 0.0624(10) 0.0568(9) 0.0467(9) -0.0022(7) -0.0054(7) -0.0006(7) C9 0.0720(12) 0.0806(13) 0.0514(10) 0.0201(9) -0.0079(8) 0.0030(10) C10 0.0713(11) 0.0684(11) 0.0351(8) 0.0104(7) -0.0007(7) 0.0011(9) C11 0.0610(9) 0.0479(8) 0.0338(7) 0.0024(6) 0.0013(6) 0.0069(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C11 1.7366(18) . ? S1 C1 1.7613(15) . ? C1 C1 1.335(3) 3_666 ? C1 S2 1.7608(17) . ? S2 C2 1.7582(15) . ? C2 C11 1.343(2) . ? C2 C3 1.457(2) . ? C3 C4 1.396(2) . ? C3 C8 1.403(2) . ? C4 C5 1.376(3) . ? C5 C6 1.375(4) . ? C6 C7 1.378(4) . ? C7 C8 1.380(3) . ? C8 C9 1.507(3) . ? C9 C10 1.510(3) . ? C10 C11 1.506(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 S1 C1 95.10(7) . . ? C1 C1 S2 122.48(16) 3_666 . ? C1 C1 S1 122.98(17) 3_666 . ? S2 C1 S1 114.53(9) . . ? C2 S2 C1 94.86(7) . . ? C11 C2 C3 122.29(14) . . ? C11 C2 S2 117.05(13) . . ? C3 C2 S2 120.61(11) . . ? C4 C3 C8 119.03(17) . . ? C4 C3 C2 123.03(15) . . ? C8 C3 C2 117.85(14) . . ? C5 C4 C3 120.6(2) . . ? C6 C5 C4 120.2(2) . . ? C5 C6 C7 119.7(2) . . ? C6 C7 C8 121.4(2) . . ? C7 C8 C3 119.06(18) . . ? C7 C8 C9 121.61(17) . . ? C3 C8 C9 119.14(16) . . ? C8 C9 C10 114.33(15) . . ? C11 C10 C9 109.58(15) . . ? C2 C11 C10 120.99(16) . . ? C2 C11 S1 118.17(12) . . ? C10 C11 S1 120.82(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 S1 C1 C1 -175.5(2) . . . 3_666 ? C11 S1 C1 S2 4.84(10) . . . . ? C1 C1 S2 C2 175.1(2) 3_666 . . . ? S1 C1 S2 C2 -5.23(10) . . . . ? C1 S2 C2 C11 3.76(13) . . . . ? C1 S2 C2 C3 -174.00(12) . . . . ? C11 C2 C3 C4 169.99(16) . . . . ? S2 C2 C3 C4 -12.4(2) . . . . ? C11 C2 C3 C8 -13.4(2) . . . . ? S2 C2 C3 C8 164.24(12) . . . . ? C8 C3 C4 C5 -0.5(3) . . . . ? C2 C3 C4 C5 176.04(19) . . . . ? C3 C4 C5 C6 -0.4(4) . . . . ? C4 C5 C6 C7 0.8(4) . . . . ? C5 C6 C7 C8 -0.2(4) . . . . ? C6 C7 C8 C3 -0.7(3) . . . . ? C6 C7 C8 C9 -175.6(2) . . . . ? C4 C3 C8 C7 1.1(2) . . . . ? C2 C3 C8 C7 -175.67(16) . . . . ? C4 C3 C8 C9 176.13(17) . . . . ? C2 C3 C8 C9 -0.6(2) . . . . ? C7 C8 C9 C10 -154.22(19) . . . . ? C3 C8 C9 C10 30.9(2) . . . . ? C8 C9 C10 C11 -45.2(2) . . . . ? C3 C2 C11 C10 -4.8(2) . . . . ? S2 C2 C11 C10 177.47(12) . . . . ? C3 C2 C11 S1 176.75(11) . . . . ? S2 C2 C11 S1 -0.98(17) . . . . ? C9 C10 C11 C2 33.8(2) . . . . ? C9 C10 C11 S1 -147.75(14) . . . . ? C1 S1 C11 C2 -2.37(14) . . . . ? C1 S1 C11 C10 179.18(13) . . . . ? _refine_diff_density_max 0.277 _refine_diff_density_min -0.149 _refine_diff_density_rms 0.044 _shelxl_version_number 2013-3 _shelx_res_file ; TITL NO01pxg in P2(1)/c CELL 0.71073 16.1748 7.7639 7.5390 90.000 91.191 90.000 ZERR 2.00 0.0018 0.0009 0.0008 0.000 0.002 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H S UNIT 44 32 8 LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!! TEMP 300 L.S. 4 BOND conf acta FMAP 2 PLAN 5 WGHT 0.056700 0.145400 FVAR 0.54942 S1 3 0.469645 0.559693 0.221313 11.00000 0.05756 0.08995 = 0.03638 0.01374 0.00717 0.00948 C1 1 0.466816 0.498068 0.445946 11.00000 0.05762 0.06178 = 0.03391 0.00539 0.00644 0.01360 S2 3 0.369139 0.429416 0.516776 11.00000 0.06012 0.08400 = 0.03712 0.01864 0.00431 0.00900 C2 1 0.317568 0.478961 0.315608 11.00000 0.06124 0.04334 = 0.03351 0.00303 -0.00007 0.00494 C3 1 0.227971 0.463619 0.299058 11.00000 0.06251 0.04133 = 0.04144 -0.00287 0.00273 -0.00135 C4 1 0.180036 0.380385 0.424914 11.00000 0.07209 0.06646 = 0.05607 0.00848 0.00470 -0.00755 H4A 2 0.208216 0.325447 0.523743 11.00000 0.07266 C5 1 0.095169 0.378668 0.408177 11.00000 0.07662 0.10404 = 0.07551 0.00687 0.01269 -0.02367 H5A 2 0.064593 0.322992 0.485360 11.00000 0.10304 C6 1 0.056491 0.460134 0.267380 11.00000 0.06061 0.12819 = 0.08058 -0.00348 -0.00167 -0.01439 H6A 2 -0.000704 0.461984 0.264213 11.00000 0.09174 C7 1 0.103161 0.541867 0.141688 11.00000 0.06704 0.09808 = 0.06275 -0.00135 -0.01255 -0.00085 H7A 2 0.078697 0.597455 0.045982 11.00000 0.09056 C8 1 0.188391 0.544434 0.154159 11.00000 0.06241 0.05683 = 0.04669 -0.00223 -0.00540 -0.00057 C9 1 0.239515 0.643950 0.024466 11.00000 0.07196 0.08061 = 0.05141 0.02009 -0.00787 0.00299 H9A 2 0.210565 0.643869 -0.094848 11.00000 0.08970 H9B 2 0.245401 0.770444 0.067211 11.00000 0.09359 C10 1 0.326054 0.575341 0.002771 11.00000 0.07134 0.06844 = 0.03512 0.01043 -0.00075 0.00112 H10A 2 0.357637 0.658397 -0.054973 11.00000 0.06002 H10B 2 0.320071 0.468408 -0.068552 11.00000 0.07787 C11 1 0.364033 0.536431 0.182417 11.00000 0.06098 0.04792 = 0.03376 0.00235 0.00135 0.00689 HKLF 4 REM NO01pxg in P2(1)/c REM R1 = 0.0360 for 1854 Fo > 4sig(Fo) and 0.0463 for all 2318 data REM 150 parameters refined using 0 restraints END WGHT 0.0567 0.1454 REM Highest difference peak 0.277, deepest hole -0.149, 1-sigma level 0.044 Q1 1 0.4160 0.5715 0.2081 11.00000 0.05 0.28 Q2 1 0.2555 0.5439 -0.0302 11.00000 0.05 0.27 Q3 1 0.4259 0.4597 0.4848 11.00000 0.05 0.27 Q4 1 0.3875 0.3652 0.4493 11.00000 0.05 0.23 Q5 1 0.3459 0.4692 0.4045 11.00000 0.05 0.23 ; _shelx_res_checksum 49028 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent' _solvent_exptl_crystal_recrystallization_method p-xylene ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_no047g _database_code_depnum_ccdc_archive 'CCDC 1460869' _audit_update_record ; 2016-05-24 deposited with the CCDC. 2016-07-12 downloaded from the CCDC. ; _audit_creation_method SHELXL-2013 _chemical_name_systematic 'bis(naphtho[1,2-d])tetrathiafulvalene ' _chemical_name_common BN-TTF _chemical_melting_point ? _chemical_formula_moiety 'C22 H12 S4' _chemical_formula_sum 'C22 H12 S4' _chemical_formula_weight 404.56 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 3.9274(14) _cell_length_b 7.167(3) _cell_length_c 15.716(6) _cell_angle_alpha 83.267(6) _cell_angle_beta 89.379(6) _cell_angle_gamma 80.859(6) _cell_volume 433.7(3) _cell_formula_units_Z 1 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 1732 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 28.25 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.549 _exptl_crystal_F_000 208 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_absorpt_coefficient_mu 0.551 _shelx_estimated_absorpt_T_min ? _shelx_estimated_absorpt_T_max ? _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8965 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details 'SADABS v2.10 BRUKER 2001' _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6365 _diffrn_reflns_av_unetI/netI 0.0913 _diffrn_reflns_av_R_equivalents 0.0614 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.610 _diffrn_reflns_theta_max 28.254 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.946 _diffrn_measured_fraction_theta_full 0.990 _diffrn_reflns_Laue_measured_fraction_max 0.946 _diffrn_reflns_Laue_measured_fraction_full 0.990 _diffrn_reflns_point_group_measured_fraction_max 0.946 _diffrn_reflns_point_group_measured_fraction_full 0.990 _reflns_number_total 2036 _reflns_number_gt 1145 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT+' _computing_structure_solution SHELXTL _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0514P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 2036 _refine_ls_number_parameters 142 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1119 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1131 _refine_ls_wR_factor_gt 0.0980 _refine_ls_goodness_of_fit_ref 0.968 _refine_ls_restrained_S_all 0.968 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0865(7) 0.4473(4) 0.03398(17) 0.0309(7) Uani 1 1 d . . . . . C2 C 0.4088(7) 0.1770(4) 0.14109(18) 0.0324(7) Uani 1 1 d . . . . . C3 C 0.5762(8) 0.0003(5) 0.1808(2) 0.0436(9) Uani 1 1 d . . . . . H3A H 0.564(8) -0.106(5) 0.154(2) 0.064(11) Uiso 1 1 d . . . . . C4 C 0.7133(9) -0.0098(5) 0.2608(2) 0.0484(9) Uani 1 1 d . . . . . H4A H 0.824(8) -0.141(5) 0.285(2) 0.058(10) Uiso 1 1 d . . . . . C5 C 0.6954(8) 0.1532(5) 0.3041(2) 0.0416(8) Uani 1 1 d . . . . . C6 C 0.8412(10) 0.1450(7) 0.3870(2) 0.0557(10) Uani 1 1 d . . . . . H6A H 0.982(9) 0.032(5) 0.412(2) 0.063(11) Uiso 1 1 d . . . . . C7 C 0.8199(10) 0.3036(7) 0.4273(2) 0.0616(12) Uani 1 1 d . . . . . H7A H 0.918(9) 0.310(5) 0.481(2) 0.075(12) Uiso 1 1 d . . . . . C8 C 0.6549(10) 0.4787(7) 0.3879(2) 0.0586(11) Uani 1 1 d . . . . . H8A H 0.629(10) 0.594(6) 0.415(2) 0.090(14) Uiso 1 1 d . . . . . C9 C 0.5152(9) 0.4917(5) 0.3087(2) 0.0452(9) Uani 1 1 d . . . . . H9A H 0.417(7) 0.605(4) 0.2834(18) 0.033(9) Uiso 1 1 d . . . . . C10 C 0.5303(7) 0.3306(5) 0.26420(19) 0.0366(8) Uani 1 1 d . . . . . C11 C 0.3855(7) 0.3385(4) 0.18177(19) 0.0318(7) Uani 1 1 d . . . . . S1 S 0.2290(2) 0.20326(11) 0.03832(5) 0.0414(3) Uani 1 1 d . . . . . S2 S 0.1789(2) 0.55073(11) 0.12536(5) 0.0387(3) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0272(16) 0.0381(18) 0.0297(17) -0.0091(13) 0.0004(12) -0.0081(13) C2 0.0309(17) 0.0380(18) 0.0294(17) -0.0027(14) 0.0010(13) -0.0098(14) C3 0.043(2) 0.036(2) 0.052(2) -0.0035(18) 0.0010(17) -0.0082(17) C4 0.049(2) 0.045(2) 0.048(2) 0.0088(19) -0.0068(17) -0.0083(18) C5 0.0355(19) 0.055(2) 0.0342(19) 0.0033(17) -0.0024(14) -0.0122(17) C6 0.052(2) 0.071(3) 0.041(2) 0.008(2) -0.0133(18) -0.011(2) C7 0.063(3) 0.089(3) 0.037(2) -0.002(2) -0.0156(19) -0.027(2) C8 0.067(3) 0.075(3) 0.041(2) -0.010(2) -0.0064(19) -0.027(2) C9 0.046(2) 0.050(2) 0.041(2) -0.0078(19) -0.0039(16) -0.0120(18) C10 0.0320(18) 0.048(2) 0.0319(18) -0.0037(16) -0.0006(14) -0.0125(15) C11 0.0269(16) 0.0380(17) 0.0311(17) -0.0036(14) 0.0016(12) -0.0072(13) S1 0.0462(5) 0.0400(5) 0.0383(5) -0.0089(4) -0.0075(4) -0.0043(4) S2 0.0445(5) 0.0385(5) 0.0338(5) -0.0068(4) -0.0096(4) -0.0063(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C1 1.355(5) 2_565 ? C1 S1 1.743(3) . ? C1 S2 1.758(3) . ? C2 C11 1.376(4) . ? C2 C3 1.409(4) . ? C2 S1 1.748(3) . ? C3 C4 1.362(5) . ? C4 C5 1.411(5) . ? C5 C10 1.411(4) . ? C5 C6 1.420(4) . ? C6 C7 1.356(5) . ? C7 C8 1.396(6) . ? C8 C9 1.353(5) . ? C9 C10 1.412(4) . ? C10 C11 1.412(4) . ? C11 S2 1.751(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C1 S1 123.4(3) 2_565 . ? C1 C1 S2 121.3(3) 2_565 . ? S1 C1 S2 115.31(15) . . ? C11 C2 C3 120.8(3) . . ? C11 C2 S1 117.0(2) . . ? C3 C2 S1 122.2(2) . . ? C4 C3 C2 119.2(3) . . ? C3 C4 C5 121.4(3) . . ? C10 C5 C4 119.5(3) . . ? C10 C5 C6 118.5(3) . . ? C4 C5 C6 122.0(3) . . ? C7 C6 C5 120.9(4) . . ? C6 C7 C8 120.5(4) . . ? C9 C8 C7 120.1(4) . . ? C8 C9 C10 121.4(4) . . ? C5 C10 C11 118.4(3) . . ? C5 C10 C9 118.6(3) . . ? C11 C10 C9 123.0(3) . . ? C2 C11 C10 120.6(3) . . ? C2 C11 S2 116.8(2) . . ? C10 C11 S2 122.6(2) . . ? C1 S1 C2 95.63(13) . . ? C11 S2 C1 95.31(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 C2 C3 C4 0.5(5) . . . . ? S1 C2 C3 C4 179.4(2) . . . . ? C2 C3 C4 C5 -0.9(5) . . . . ? C3 C4 C5 C10 0.4(5) . . . . ? C3 C4 C5 C6 -179.2(3) . . . . ? C10 C5 C6 C7 0.6(5) . . . . ? C4 C5 C6 C7 -179.8(3) . . . . ? C5 C6 C7 C8 -0.3(6) . . . . ? C6 C7 C8 C9 -0.2(6) . . . . ? C7 C8 C9 C10 0.3(5) . . . . ? C4 C5 C10 C11 0.4(4) . . . . ? C6 C5 C10 C11 180.0(3) . . . . ? C4 C5 C10 C9 180.0(3) . . . . ? C6 C5 C10 C9 -0.4(5) . . . . ? C8 C9 C10 C5 0.0(5) . . . . ? C8 C9 C10 C11 179.6(3) . . . . ? C3 C2 C11 C10 0.3(4) . . . . ? S1 C2 C11 C10 -178.7(2) . . . . ? C3 C2 C11 S2 178.8(2) . . . . ? S1 C2 C11 S2 -0.2(3) . . . . ? C5 C10 C11 C2 -0.7(4) . . . . ? C9 C10 C11 C2 179.7(3) . . . . ? C5 C10 C11 S2 -179.2(2) . . . . ? C9 C10 C11 S2 1.3(4) . . . . ? C1 C1 S1 C2 -179.1(3) 2_565 . . . ? S2 C1 S1 C2 0.36(18) . . . . ? C11 C2 S1 C1 -0.1(2) . . . . ? C3 C2 S1 C1 -179.1(3) . . . . ? C2 C11 S2 C1 0.3(2) . . . . ? C10 C11 S2 C1 178.9(2) . . . . ? C1 C1 S2 C11 179.0(3) 2_565 . . . ? S1 C1 S2 C11 -0.43(18) . . . . ? _refine_diff_density_max 0.379 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.069 _shelxl_version_number 2013-3 _shelx_res_file ; TITL no047g in P-1 CELL 0.71073 3.9274 7.1673 15.7162 83.267 89.379 80.859 ZERR 1.00 0.0014 0.0026 0.0057 0.006 0.006 0.006 LATT 1 SFAC C H S UNIT 22 12 4 LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!! TEMP 100 L.S. 4 BOND conf acta FMAP 2 PLAN 15 WGHT 0.051400 FVAR 0.89147 C1 1 0.086518 0.447307 0.033978 11.00000 0.02717 0.03805 = 0.02969 -0.00914 0.00041 -0.00814 C2 1 0.408847 0.177034 0.141086 11.00000 0.03092 0.03804 = 0.02937 -0.00274 0.00097 -0.00982 C3 1 0.576167 0.000329 0.180845 11.00000 0.04254 0.03636 = 0.05221 -0.00347 0.00103 -0.00817 H3A 2 0.564018 -0.105881 0.154470 11.00000 0.06350 C4 1 0.713307 -0.009794 0.260772 11.00000 0.04932 0.04472 = 0.04811 0.00876 -0.00683 -0.00834 H4A 2 0.824228 -0.140820 0.285073 11.00000 0.05821 C5 1 0.695437 0.153153 0.304059 11.00000 0.03547 0.05481 = 0.03417 0.00328 -0.00237 -0.01218 C6 1 0.841238 0.144990 0.386969 11.00000 0.05181 0.07132 = 0.04126 0.00844 -0.01327 -0.01129 H6A 2 0.981716 0.031603 0.411803 11.00000 0.06315 C7 1 0.819945 0.303557 0.427318 11.00000 0.06311 0.08851 = 0.03684 -0.00162 -0.01561 -0.02651 H7A 2 0.918177 0.309556 0.481080 11.00000 0.07496 C8 1 0.654949 0.478720 0.387913 11.00000 0.06688 0.07467 = 0.04055 -0.01039 -0.00645 -0.02744 H8A 2 0.628889 0.593695 0.414896 11.00000 0.09011 C9 1 0.515238 0.491749 0.308711 11.00000 0.04606 0.05048 = 0.04110 -0.00782 -0.00388 -0.01198 H9A 2 0.416611 0.605208 0.283376 11.00000 0.03250 C10 1 0.530269 0.330556 0.264203 11.00000 0.03204 0.04755 = 0.03193 -0.00368 -0.00061 -0.01246 C11 1 0.385466 0.338459 0.181773 11.00000 0.02693 0.03795 = 0.03114 -0.00359 0.00163 -0.00719 S1 3 0.228966 0.203264 0.038324 11.00000 0.04618 0.03999 = 0.03831 -0.00890 -0.00751 -0.00425 S2 3 0.178938 0.550729 0.125361 11.00000 0.04451 0.03854 = 0.03380 -0.00679 -0.00963 -0.00630 HKLF 4 REM no047g in P-1 REM R1 = 0.0492 for 1145 Fo > 4sig(Fo) and 0.1119 for all 2036 data REM 142 parameters refined using 0 restraints END WGHT 0.0514 0.0000 REM Highest difference peak 0.379, deepest hole -0.285, 1-sigma level 0.069 Q1 1 0.0978 0.4792 -0.0092 11.00000 0.05 0.38 Q2 1 0.0347 0.7041 0.1364 11.00000 0.05 0.35 Q3 1 0.5036 0.2662 0.1467 11.00000 0.05 0.33 Q4 1 0.0397 0.5160 0.0618 11.00000 0.05 0.33 Q5 1 0.3308 0.2580 0.0868 11.00000 0.05 0.31 Q6 1 0.3391 0.4460 0.1770 11.00000 0.05 0.29 Q7 1 0.1046 0.3645 0.0531 11.00000 0.05 0.29 Q8 1 0.4513 0.3150 0.2226 11.00000 0.05 0.26 Q9 1 0.1678 0.3967 0.1877 11.00000 0.05 0.26 Q10 1 0.4255 0.2031 -0.0114 11.00000 0.05 0.24 Q11 1 0.9895 -0.0531 0.3881 11.00000 0.05 0.24 Q12 1 0.6076 0.4205 0.2821 11.00000 0.05 0.24 Q13 1 0.5973 0.0998 0.0027 11.00000 0.05 0.24 Q14 1 0.3745 0.4003 0.1271 11.00000 0.05 0.23 Q15 1 0.2965 0.2692 0.1885 11.00000 0.05 0.23 ; _shelx_res_checksum 4213 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent' _solvent_exptl_crystal_recrystallization_method 'diffusion of diethyl ether into a solution of chlorobenzene'

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