# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_yg004_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 5,5Bis(5nheptylpyridin-2-yl)2,2-bithiophene _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H40 N2 S2' _chemical_formula_weight 516.78 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' N N 0.0061 0.0033 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.911(3) _cell_length_b 11.088(6) _cell_length_c 11.978(7) _cell_angle_alpha 64.751(9) _cell_angle_beta 85.929(10) _cell_angle_gamma 83.362(10) _cell_volume 705.1(7) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1489 _cell_measurement_theta_min 3.31 _cell_measurement_theta_max 29.03 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.217 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 278 _exptl_absorpt_coefficient_mu 0.212 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9068 _exptl_absorpt_correction_T_max 0.9812 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5498 _diffrn_reflns_av_R_equivalents 0.0454 _diffrn_reflns_av_sigmaI/netI 0.0640 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2482 _reflns_number_gt 1800 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.6213P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2482 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0870 _refine_ls_R_factor_gt 0.0565 _refine_ls_wR_factor_ref 0.1626 _refine_ls_wR_factor_gt 0.1379 _refine_ls_goodness_of_fit_ref 0.904 _refine_ls_restrained_S_all 0.904 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.01333(13) 0.34014(8) 0.18960(7) 0.0251(3) Uani 1 1 d . . . N1 N 0.1484(4) 0.1645(3) 0.4413(2) 0.0278(6) Uani 1 1 d . . . C1 C 0.0712(5) 0.4775(3) 0.0539(3) 0.0229(7) Uani 1 1 d . . . C2 C 0.2616(5) 0.5319(3) 0.0657(3) 0.0260(7) Uani 1 1 d . . . H2 H 0.3184 0.6070 0.0031 0.031 Uiso 1 1 calc R . . C3 C 0.3609(5) 0.4621(3) 0.1818(3) 0.0280(7) Uani 1 1 d . . . H3 H 0.4904 0.4867 0.2035 0.034 Uiso 1 1 calc R . . C4 C 0.2493(5) 0.3543(3) 0.2605(3) 0.0242(7) Uani 1 1 d . . . C5 C 0.3006(5) 0.2561(3) 0.3865(3) 0.0249(7) Uani 1 1 d . . . C6 C 0.4951(5) 0.2538(3) 0.4470(3) 0.0287(7) Uani 1 1 d . . . H6 H 0.5991 0.3169 0.4079 0.034 Uiso 1 1 calc R . . C7 C 0.5318(5) 0.1566(3) 0.5663(3) 0.0291(7) Uani 1 1 d . . . H7 H 0.6614 0.1544 0.6071 0.035 Uiso 1 1 calc R . . C8 C 0.3763(5) 0.0627(3) 0.6249(3) 0.0243(7) Uani 1 1 d . . . C9 C 0.1890(5) 0.0721(3) 0.5555(3) 0.0276(7) Uani 1 1 d . . . H9 H 0.0846 0.0088 0.5920 0.033 Uiso 1 1 calc R . . C10 C 0.4003(5) -0.0466(3) 0.7544(3) 0.0275(7) Uani 1 1 d . . . H10A H 0.4102 -0.1323 0.7499 0.033 Uiso 1 1 calc R . . H10B H 0.2624 -0.0402 0.8014 0.033 Uiso 1 1 calc R . . C11 C 0.6042(5) -0.0462(3) 0.8262(3) 0.0262(7) Uani 1 1 d . . . H11A H 0.7435 -0.0566 0.7819 0.031 Uiso 1 1 calc R . . H11B H 0.5980 0.0399 0.8298 0.031 Uiso 1 1 calc R . . C12 C 0.6126(5) -0.1561(3) 0.9569(3) 0.0264(7) Uani 1 1 d . . . H12A H 0.6220 -0.2423 0.9533 0.032 Uiso 1 1 calc R . . H12B H 0.4721 -0.1468 1.0007 0.032 Uiso 1 1 calc R . . C13 C 0.8127(5) -0.1540(3) 1.0291(3) 0.0281(7) Uani 1 1 d . . . H13A H 0.9528 -0.1653 0.9858 0.034 Uiso 1 1 calc R . . H13B H 0.8052 -0.0667 1.0302 0.034 Uiso 1 1 calc R . . C14 C 0.8234(5) -0.2604(3) 1.1614(3) 0.0278(7) Uani 1 1 d . . . H14A H 0.6839 -0.2491 1.2051 0.033 Uiso 1 1 calc R . . H14B H 0.8309 -0.3479 1.1606 0.033 Uiso 1 1 calc R . . C15 C 1.0247(5) -0.2569(3) 1.2317(3) 0.0311(8) Uani 1 1 d . . . H15A H 1.1644 -0.2673 1.1877 0.037 Uiso 1 1 calc R . . H15B H 1.0163 -0.1700 1.2337 0.037 Uiso 1 1 calc R . . C16 C 1.0343(7) -0.3648(4) 1.3629(3) 0.0418(9) Uani 1 1 d . . . H16A H 0.9018 -0.3512 1.4089 0.063 Uiso 1 1 calc R . . H16B H 1.1687 -0.3604 1.4010 0.063 Uiso 1 1 calc R . . H16C H 1.0384 -0.4511 1.3619 0.063 Uiso 1 1 calc R . . 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 0.0158(4) 0.0323(5) 0.0265(4) -0.0123(3) 0.0016(3) -0.0016(3) N1 0.0177(14) 0.0364(15) 0.0280(14) -0.0127(12) 0.0010(11) -0.0027(12) C1 0.0157(15) 0.0297(16) 0.0257(16) -0.0163(14) 0.0061(12) 0.0026(12) C2 0.0182(16) 0.0267(16) 0.0313(17) -0.0115(14) 0.0047(13) -0.0012(13) C3 0.0154(16) 0.0374(18) 0.0311(17) -0.0151(15) 0.0022(13) -0.0014(13) C4 0.0143(15) 0.0319(17) 0.0305(17) -0.0190(15) 0.0033(13) 0.0031(13) C5 0.0164(15) 0.0333(18) 0.0283(17) -0.0177(14) 0.0049(13) 0.0009(13) C6 0.0155(16) 0.0374(18) 0.0320(17) -0.0138(15) 0.0033(13) -0.0036(13) C7 0.0129(15) 0.0432(19) 0.0325(17) -0.0174(16) -0.0012(13) -0.0018(14) C8 0.0164(15) 0.0319(17) 0.0281(17) -0.0175(14) 0.0031(13) 0.0016(13) C9 0.0163(16) 0.0377(18) 0.0294(17) -0.0143(15) 0.0028(13) -0.0064(13) C10 0.0190(16) 0.0367(18) 0.0270(17) -0.0147(15) 0.0041(13) -0.0015(13) C11 0.0179(16) 0.0311(17) 0.0296(17) -0.0141(14) 0.0008(13) 0.0015(13) C12 0.0164(15) 0.0329(17) 0.0303(17) -0.0150(15) 0.0049(13) -0.0007(13) C13 0.0203(16) 0.0333(18) 0.0316(17) -0.0154(15) 0.0040(13) -0.0021(13) C14 0.0205(16) 0.0325(17) 0.0311(17) -0.0159(15) 0.0051(13) 0.0003(13) C15 0.0278(18) 0.0339(19) 0.0313(17) -0.0144(15) -0.0015(14) 0.0013(15) C16 0.043(2) 0.047(2) 0.036(2) -0.0195(18) -0.0066(17) 0.0038(18) _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 C1 1.734(3) . ? S1 C4 1.739(3) . ? N1 C9 1.332(4) . ? N1 C5 1.353(4) . ? C1 C2 1.379(4) . ? C1 C1 1.460(6) 2_565 ? C2 C3 1.404(4) . ? C3 C4 1.373(4) . ? C4 C5 1.464(4) . ? C5 C6 1.395(4) . ? C6 C7 1.387(4) . ? C7 C8 1.389(4) . ? C8 C9 1.399(4) . ? C8 C10 1.511(4) . ? C10 C11 1.531(4) . ? C11 C12 1.519(4) . ? C12 C13 1.521(4) . ? C13 C14 1.519(4) . ? C14 C15 1.519(4) . ? C15 C16 1.516(5) . ? 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 S1 C4 92.08(15) . . ? C9 N1 C5 118.0(3) . . ? C2 C1 C1 127.9(4) . 2_565 ? C2 C1 S1 110.6(2) . . ? C1 C1 S1 121.5(3) 2_565 . ? C1 C2 C3 113.1(3) . . ? C4 C3 C2 113.8(3) . . ? C3 C4 C5 130.6(3) . . ? C3 C4 S1 110.3(2) . . ? C5 C4 S1 119.1(2) . . ? N1 C5 C6 121.3(3) . . ? N1 C5 C4 115.7(3) . . ? C6 C5 C4 123.0(3) . . ? C7 C6 C5 119.3(3) . . ? C6 C7 C8 120.4(3) . . ? C7 C8 C9 115.8(3) . . ? C7 C8 C10 124.5(3) . . ? C9 C8 C10 119.7(3) . . ? N1 C9 C8 125.2(3) . . ? C8 C10 C11 116.4(3) . . ? C12 C11 C10 113.4(3) . . ? C11 C12 C13 113.4(3) . . ? C14 C13 C12 114.9(3) . . ? C15 C14 C13 114.1(3) . . ? C16 C15 C14 113.4(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.655 _refine_diff_density_min -0.538 _refine_diff_density_rms 0.086 _database_code_depnum_ccdc_archive 'CCDC 808341' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_yg006 #TrackingRef 'Total_CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 5,5Bis(5nonylpyridin-2-yl)2,2-bithiophene _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H44 N2 S2' _chemical_formula_weight 544.83 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' N N 0.0061 0.0033 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.6000(11) _cell_length_b 11.400(2) _cell_length_c 11.920(2) _cell_angle_alpha 75.60(3) _cell_angle_beta 87.40(3) _cell_angle_gamma 76.20(3) _cell_volume 715.7(2) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 294 _exptl_absorpt_coefficient_mu 0.213 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8866 _exptl_absorpt_correction_T_max 0.9832 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5255 _diffrn_reflns_av_R_equivalents 0.0515 _diffrn_reflns_av_sigmaI/netI 0.0772 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2529 _reflns_number_gt 1773 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.8524P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2529 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0897 _refine_ls_R_factor_gt 0.0592 _refine_ls_wR_factor_ref 0.1644 _refine_ls_wR_factor_gt 0.1417 _refine_ls_goodness_of_fit_ref 0.863 _refine_ls_restrained_S_all 0.863 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.98775(16) 0.47052(8) -0.30960(7) 0.0255(3) Uani 1 1 d . . . N1 N 0.8522(5) 0.4063(3) -0.0697(2) 0.0289(7) Uani 1 1 d . . . C1 C 0.9361(6) 0.4693(3) -0.4526(3) 0.0239(7) Uani 1 1 d . . . C2 C 0.7608(6) 0.4056(3) -0.4580(3) 0.0249(8) Uani 1 1 d . . . H2 H 0.7070 0.3933 -0.5277 0.030 Uiso 1 1 calc R . . C3 C 0.6696(6) 0.3605(3) -0.3478(3) 0.0257(8) Uani 1 1 d . . . H3 H 0.5466 0.3140 -0.3362 0.031 Uiso 1 1 calc R . . C4 C 0.7712(6) 0.3885(3) -0.2593(3) 0.0245(8) Uani 1 1 d . . . C5 C 0.7203(6) 0.3626(3) -0.1338(3) 0.0244(7) Uani 1 1 d . . . C6 C 0.5456(6) 0.3013(3) -0.0852(3) 0.0304(8) Uani 1 1 d . . . H6 H 0.4507 0.2723 -0.1318 0.036 Uiso 1 1 calc R . . C7 C 0.5073(6) 0.2816(3) 0.0340(3) 0.0291(8) Uani 1 1 d . . . H7 H 0.3871 0.2380 0.0686 0.035 Uiso 1 1 calc R . . C8 C 0.6429(6) 0.3250(3) 0.1026(3) 0.0256(8) Uani 1 1 d . . . C9 C 0.8122(6) 0.3863(3) 0.0451(3) 0.0285(8) Uani 1 1 d . . . H9 H 0.9087 0.4171 0.0895 0.034 Uiso 1 1 calc R . . C10 C 0.6161(6) 0.3075(3) 0.2333(3) 0.0278(8) Uani 1 1 d . . . H10A H 0.7794 0.2658 0.2701 0.033 Uiso 1 1 calc R . . H10B H 0.5679 0.3909 0.2496 0.033 Uiso 1 1 calc R . . C11 C 0.4355(6) 0.2344(3) 0.2901(3) 0.0261(8) Uani 1 1 d . . . H11A H 0.4794 0.1512 0.2733 0.031 Uiso 1 1 calc R . . H11B H 0.2696 0.2773 0.2568 0.031 Uiso 1 1 calc R . . C12 C 0.4284(6) 0.2183(3) 0.4223(3) 0.0273(8) Uani 1 1 d . . . H12A H 0.5941 0.1745 0.4554 0.033 Uiso 1 1 calc R . . H12B H 0.3879 0.3018 0.4387 0.033 Uiso 1 1 calc R . . C13 C 0.2454(6) 0.1470(3) 0.4817(3) 0.0277(8) Uani 1 1 d . . . H13A H 0.2834 0.0643 0.4638 0.033 Uiso 1 1 calc R . . H13B H 0.0791 0.1919 0.4501 0.033 Uiso 1 1 calc R . . C14 C 0.2435(6) 0.1284(3) 0.6145(3) 0.0270(8) Uani 1 1 d . . . H14A H 0.4096 0.0832 0.6461 0.032 Uiso 1 1 calc R . . H14B H 0.2060 0.2111 0.6324 0.032 Uiso 1 1 calc R . . C15 C 0.0604(6) 0.0577(3) 0.6733(3) 0.0278(8) Uani 1 1 d . . . H15A H 0.0977 -0.0248 0.6549 0.033 Uiso 1 1 calc R . . H15B H -0.1056 0.1031 0.6416 0.033 Uiso 1 1 calc R . . C16 C 0.0574(6) 0.0383(3) 0.8056(3) 0.0304(8) Uani 1 1 d . . . H16A H 0.2218 -0.0093 0.8379 0.036 Uiso 1 1 calc R . . H16B H 0.0238 0.1205 0.8244 0.036 Uiso 1 1 calc R . . C17 C -0.1317(7) -0.0299(4) 0.8621(3) 0.0388(10) Uani 1 1 d . . . H17A H -0.2962 0.0203 0.8357 0.058 Uiso 1 1 calc R . . H17B H -0.1185 -0.0447 0.9464 0.058 Uiso 1 1 calc R . . H17C H -0.1039 -0.1098 0.8410 0.058 Uiso 1 1 calc R . . 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 0.0287(5) 0.0331(5) 0.0170(4) 0.0011(3) 0.0031(3) -0.0200(4) N1 0.0322(16) 0.0383(19) 0.0201(14) -0.0026(13) 0.0031(12) -0.0213(14) C1 0.0233(17) 0.0267(19) 0.0202(16) 0.0010(14) 0.0026(13) -0.0104(15) C2 0.0288(18) 0.028(2) 0.0184(15) 0.0010(14) 0.0006(13) -0.0154(16) C3 0.0255(17) 0.029(2) 0.0232(17) 0.0012(15) 0.0004(13) -0.0160(16) C4 0.0213(16) 0.0272(19) 0.0230(17) 0.0042(14) 0.0014(13) -0.0128(15) C5 0.0267(17) 0.028(2) 0.0167(16) 0.0017(14) 0.0017(13) -0.0107(15) C6 0.0324(19) 0.041(2) 0.0221(17) -0.0012(16) 0.0008(14) -0.0233(18) C7 0.0333(19) 0.036(2) 0.0195(16) 0.0027(15) 0.0041(14) -0.0206(17) C8 0.0278(18) 0.030(2) 0.0182(16) 0.0010(14) 0.0007(13) -0.0122(16) C9 0.0299(18) 0.038(2) 0.0209(16) -0.0020(15) 0.0029(14) -0.0213(17) C10 0.0300(18) 0.034(2) 0.0194(16) 0.0027(15) 0.0008(13) -0.0166(16) C11 0.0269(17) 0.031(2) 0.0194(16) 0.0003(14) 0.0027(13) -0.0123(16) C12 0.0299(18) 0.033(2) 0.0195(16) 0.0005(15) 0.0020(14) -0.0161(16) C13 0.0299(18) 0.033(2) 0.0196(16) 0.0017(15) 0.0001(13) -0.0153(17) C14 0.0278(18) 0.032(2) 0.0200(16) 0.0028(15) -0.0004(13) -0.0150(16) C15 0.0294(18) 0.034(2) 0.0205(17) 0.0014(15) 0.0007(14) -0.0160(16) C16 0.033(2) 0.036(2) 0.0224(17) 0.0027(16) -0.0003(15) -0.0189(17) C17 0.041(2) 0.053(3) 0.0251(18) 0.0005(18) 0.0046(16) -0.028(2) _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 C4 1.703(3) . ? S1 C1 1.746(3) . ? N1 C5 1.340(4) . ? N1 C9 1.347(4) . ? C1 C2 1.365(4) . ? C1 C1 1.432(6) 2_764 ? C2 C3 1.406(4) . ? C2 H2 0.9500 . ? C3 C4 1.360(4) . ? C3 H3 0.9500 . ? C4 C5 1.479(4) . ? C5 C6 1.361(4) . ? C6 C7 1.398(4) . ? C6 H6 0.9500 . ? C7 C8 1.387(4) . ? C7 H7 0.9500 . ? C8 C9 1.370(4) . ? C8 C10 1.526(4) . ? C9 H9 0.9500 . ? C10 C11 1.495(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.540(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.503(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.544(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.497(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.538(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.499(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? 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 C4 S1 C1 92.14(15) . . ? C5 N1 C9 118.6(3) . . ? C2 C1 C1 127.3(4) . 2_764 ? C2 C1 S1 110.6(2) . . ? C1 C1 S1 122.0(3) 2_764 . ? C1 C2 C3 111.9(3) . . ? C1 C2 H2 124.1 . . ? C3 C2 H2 124.1 . . ? C4 C3 C2 114.7(3) . . ? C4 C3 H3 122.6 . . ? C2 C3 H3 122.6 . . ? C3 C4 C5 131.2(3) . . ? C3 C4 S1 110.6(2) . . ? C5 C4 S1 118.1(2) . . ? N1 C5 C6 121.1(3) . . ? N1 C5 C4 116.0(3) . . ? C6 C5 C4 122.9(3) . . ? C5 C6 C7 119.3(3) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? C8 C7 C6 120.8(3) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C9 C8 C7 115.4(3) . . ? C9 C8 C10 119.9(3) . . ? C7 C8 C10 124.7(3) . . ? N1 C9 C8 124.9(3) . . ? N1 C9 H9 117.6 . . ? C8 C9 H9 117.6 . . ? C11 C10 C8 116.5(3) . . ? C11 C10 H10A 108.2 . . ? C8 C10 H10A 108.2 . . ? C11 C10 H10B 108.2 . . ? C8 C10 H10B 108.2 . . ? H10A C10 H10B 107.3 . . ? C10 C11 C12 112.5(3) . . ? C10 C11 H11A 109.1 . . ? C12 C11 H11A 109.1 . . ? C10 C11 H11B 109.1 . . ? C12 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? C13 C12 C11 113.8(3) . . ? C13 C12 H12A 108.8 . . ? C11 C12 H12A 108.8 . . ? C13 C12 H12B 108.8 . . ? C11 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? C12 C13 C14 113.5(3) . . ? C12 C13 H13A 108.9 . . ? C14 C13 H13A 108.9 . . ? C12 C13 H13B 108.9 . . ? C14 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C15 C14 C13 113.4(3) . . ? C15 C14 H14A 108.9 . . ? C13 C14 H14A 108.9 . . ? C15 C14 H14B 108.9 . . ? C13 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? C14 C15 C16 113.8(3) . . ? C14 C15 H15A 108.8 . . ? C16 C15 H15A 108.8 . . ? C14 C15 H15B 108.8 . . ? C16 C15 H15B 108.8 . . ? H15A C15 H15B 107.7 . . ? C17 C16 C15 112.8(3) . . ? C17 C16 H16A 109.0 . . ? C15 C16 H16A 109.0 . . ? C17 C16 H16B 109.0 . . ? C15 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.508 _refine_diff_density_min -0.513 _refine_diff_density_rms 0.082 _database_code_depnum_ccdc_archive 'CCDC 808342' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_yg001_chi #TrackingRef 'Total_CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 5,5Bis(5ndecylpyridin-2-yl)2,2-bithiophene _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H52 N2 S2' _chemical_formula_weight 600.94 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' N N 0.0061 0.0033 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.073(4) _cell_length_b 11.566(7) _cell_length_c 12.264(7) _cell_angle_alpha 95.841(11) _cell_angle_beta 91.877(10) _cell_angle_gamma 100.404(11) _cell_volume 841.7(9) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2166 _cell_measurement_theta_min 3.42 _cell_measurement_theta_max 30.51 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.186 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 326 _exptl_absorpt_coefficient_mu 0.187 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9206 _exptl_absorpt_correction_T_max 0.9601 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5841 _diffrn_reflns_av_R_equivalents 0.1428 _diffrn_reflns_av_sigmaI/netI 0.1310 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2950 _reflns_number_gt 2089 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.7581P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2950 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1105 _refine_ls_R_factor_gt 0.0624 _refine_ls_wR_factor_ref 0.1810 _refine_ls_wR_factor_gt 0.1540 _refine_ls_goodness_of_fit_ref 0.906 _refine_ls_restrained_S_all 0.906 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.4145(5) 0.5259(2) 0.0430(3) 0.0163(7) Uani 1 1 d . . . S1 S -0.47097(13) 0.52668(7) 0.18102(7) 0.0171(3) Uani 1 1 d . . . C6 C 0.0831(5) 0.6685(3) 0.3793(3) 0.0211(7) Uani 1 1 d . . . H6 H 0.1986 0.6876 0.3302 0.025 Uiso 1 1 calc R . . C2 C -0.1958(5) 0.5790(3) 0.0304(3) 0.0175(7) Uani 1 1 d . . . H2 H -0.1339 0.5886 -0.0390 0.021 Uiso 1 1 calc R . . C3 C -0.0737(5) 0.6177(3) 0.1318(3) 0.0182(7) Uani 1 1 d . . . H3 H 0.0795 0.6552 0.1375 0.022 Uiso 1 1 calc R . . C4 C -0.1988(5) 0.5955(2) 0.2213(3) 0.0165(7) Uani 1 1 d . . . C5 C -0.1339(5) 0.6205(2) 0.3391(3) 0.0171(7) Uani 1 1 d . . . N1 N -0.3002(4) 0.5910(2) 0.4070(2) 0.0217(7) Uani 1 1 d . . . C7 C -0.2504(5) 0.6098(3) 0.5154(3) 0.0209(7) Uani 1 1 d . . . H7 H -0.3682 0.5881 0.5626 0.025 Uiso 1 1 calc R . . C8 C -0.0391(5) 0.6588(2) 0.5643(3) 0.0170(7) Uani 1 1 d . . . C9 C 0.1298(5) 0.6882(3) 0.4917(3) 0.0197(7) Uani 1 1 d . . . H9 H 0.2777 0.7219 0.5197 0.024 Uiso 1 1 calc R . . C10 C -0.0040(5) 0.6760(3) 0.6876(3) 0.0199(7) Uani 1 1 d . . . H10A H -0.0433 0.5977 0.7150 0.024 Uiso 1 1 calc R . . H10B H -0.1109 0.7248 0.7174 0.024 Uiso 1 1 calc R . . C11 C 0.2284(5) 0.7330(3) 0.7341(3) 0.0185(7) Uani 1 1 d . . . H11A H 0.2704 0.8109 0.7061 0.022 Uiso 1 1 calc R . . H11B H 0.3359 0.6832 0.7069 0.022 Uiso 1 1 calc R . . C12 C 0.2513(5) 0.7507(3) 0.8586(3) 0.0184(7) Uani 1 1 d . . . H12A H 0.2137 0.6727 0.8868 0.022 Uiso 1 1 calc R . . H12B H 0.1414 0.7989 0.8861 0.022 Uiso 1 1 calc R . . C13 C 0.4849(5) 0.8112(3) 0.9043(3) 0.0193(7) Uani 1 1 d . . . H13A H 0.5937 0.7616 0.8783 0.023 Uiso 1 1 calc R . . H13B H 0.5241 0.8878 0.8738 0.023 Uiso 1 1 calc R . . C14 C 0.5114(5) 0.8336(3) 1.0289(3) 0.0188(7) Uani 1 1 d . . . H14A H 0.4036 0.8836 1.0554 0.023 Uiso 1 1 calc R . . H14B H 0.4729 0.7572 1.0599 0.023 Uiso 1 1 calc R . . C15 C 0.7464(5) 0.8938(3) 1.0717(3) 0.0189(7) Uani 1 1 d . . . H15A H 0.8537 0.8441 1.0440 0.023 Uiso 1 1 calc R . . H15B H 0.7837 0.9704 1.0409 0.023 Uiso 1 1 calc R . . C16 C 0.7791(5) 0.9162(3) 1.1960(3) 0.0202(7) Uani 1 1 d . . . H16A H 0.6779 0.9695 1.2237 0.024 Uiso 1 1 calc R . . H16B H 0.7356 0.8403 1.2274 0.024 Uiso 1 1 calc R . . C17 C 1.0182(5) 0.9710(3) 1.2359(3) 0.0221(8) Uani 1 1 d . . . H17A H 1.0635 1.0449 1.2014 0.027 Uiso 1 1 calc R . . H17B H 1.1180 0.9160 1.2104 0.027 Uiso 1 1 calc R . . C18 C 1.0545(5) 0.9995(3) 1.3599(3) 0.0219(8) Uani 1 1 d . . . H18A H 0.9545 1.0541 1.3858 0.026 Uiso 1 1 calc R . . H18B H 1.0116 0.9256 1.3946 0.026 Uiso 1 1 calc R . . C19 C 1.2944(6) 1.0551(3) 1.3970(3) 0.0340(9) Uani 1 1 d . . . H19A H 1.3408 1.1264 1.3604 0.051 Uiso 1 1 calc R . . H19B H 1.3931 0.9986 1.3779 0.051 Uiso 1 1 calc R . . H19C H 1.3043 1.0763 1.4766 0.051 Uiso 1 1 calc R . . 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 0.0206(16) 0.0129(15) 0.0164(18) 0.0001(12) 0.0002(13) 0.0064(12) S1 0.0166(4) 0.0176(4) 0.0168(5) -0.0005(3) 0.0006(3) 0.0038(3) C6 0.0184(16) 0.0223(16) 0.022(2) 0.0002(14) 0.0036(14) 0.0043(13) C2 0.0226(16) 0.0158(15) 0.0153(18) 0.0003(13) 0.0028(13) 0.0067(13) C3 0.0185(16) 0.0170(15) 0.0196(19) 0.0003(13) -0.0007(13) 0.0062(12) C4 0.0169(15) 0.0117(14) 0.0205(19) -0.0028(13) -0.0013(13) 0.0049(12) C5 0.0176(16) 0.0097(14) 0.024(2) -0.0009(13) 0.0035(14) 0.0027(12) N1 0.0193(14) 0.0230(14) 0.0212(17) -0.0029(12) 0.0002(12) 0.0031(11) C7 0.0187(16) 0.0250(17) 0.0174(19) 0.0015(14) 0.0034(13) 0.0000(13) C8 0.0192(16) 0.0108(14) 0.0208(19) -0.0019(13) -0.0009(14) 0.0045(12) C9 0.0157(16) 0.0216(16) 0.0196(19) -0.0040(13) -0.0033(13) 0.0018(13) C10 0.0182(16) 0.0184(16) 0.0218(19) -0.0022(13) 0.0007(13) 0.0025(12) C11 0.0183(16) 0.0157(15) 0.0212(19) 0.0004(13) 0.0011(13) 0.0034(12) C12 0.0190(16) 0.0178(15) 0.0185(19) -0.0012(13) 0.0030(13) 0.0050(13) C13 0.0190(16) 0.0148(15) 0.023(2) 0.0001(13) -0.0002(14) 0.0026(12) C14 0.0197(17) 0.0160(15) 0.0203(19) -0.0008(13) -0.0008(13) 0.0041(13) C15 0.0202(16) 0.0164(15) 0.0193(19) -0.0004(13) 0.0003(13) 0.0032(13) C16 0.0232(17) 0.0178(16) 0.0203(19) 0.0004(13) 0.0010(14) 0.0068(13) C17 0.0221(17) 0.0253(17) 0.0198(19) 0.0016(14) 0.0008(14) 0.0072(14) C18 0.0195(16) 0.0241(17) 0.022(2) -0.0004(14) 0.0006(14) 0.0053(13) C19 0.0279(19) 0.052(2) 0.021(2) -0.0015(17) -0.0035(15) 0.0077(17) _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 C2 1.379(4) . ? C1 C1 1.458(6) 2_465 ? C1 S1 1.737(3) . ? S1 C4 1.732(3) . ? C6 C9 1.386(5) . ? C6 C5 1.387(4) . ? C6 H6 0.9500 . ? C2 C3 1.416(4) . ? C2 H2 0.9500 . ? C3 C4 1.374(5) . ? C3 H3 0.9500 . ? C4 C5 1.471(5) . ? C5 N1 1.348(4) . ? N1 C7 1.340(4) . ? C7 C8 1.394(4) . ? C7 H7 0.9500 . ? C8 C9 1.398(5) . ? C8 C10 1.508(5) . ? C9 H9 0.9500 . ? C10 C11 1.512(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.518(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.525(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.522(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.521(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.521(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.519(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.523(5) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.517(5) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? 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 C2 C1 C1 127.6(4) . 2_465 ? C2 C1 S1 111.0(2) . . ? C1 C1 S1 121.4(3) 2_465 . ? C4 S1 C1 91.87(15) . . ? C9 C6 C5 119.4(3) . . ? C9 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C1 C2 C3 112.8(3) . . ? C1 C2 H2 123.6 . . ? C3 C2 H2 123.6 . . ? C4 C3 C2 113.3(3) . . ? C4 C3 H3 123.4 . . ? C2 C3 H3 123.4 . . ? C3 C4 C5 129.9(3) . . ? C3 C4 S1 111.1(2) . . ? C5 C4 S1 119.0(2) . . ? N1 C5 C6 121.5(3) . . ? N1 C5 C4 115.3(3) . . ? C6 C5 C4 123.2(3) . . ? C7 N1 C5 118.0(3) . . ? N1 C7 C8 125.1(3) . . ? N1 C7 H7 117.4 . . ? C8 C7 H7 117.4 . . ? C7 C8 C9 115.5(3) . . ? C7 C8 C10 120.2(3) . . ? C9 C8 C10 124.3(3) . . ? C6 C9 C8 120.5(3) . . ? C6 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C8 C10 C11 116.9(3) . . ? C8 C10 H10A 108.1 . . ? C11 C10 H10A 108.1 . . ? C8 C10 H10B 108.1 . . ? C11 C10 H10B 108.1 . . ? H10A C10 H10B 107.3 . . ? C10 C11 C12 114.3(3) . . ? C10 C11 H11A 108.7 . . ? C12 C11 H11A 108.7 . . ? C10 C11 H11B 108.7 . . ? C12 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C11 C12 C13 113.7(3) . . ? C11 C12 H12A 108.8 . . ? C13 C12 H12A 108.8 . . ? C11 C12 H12B 108.8 . . ? C13 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? C14 C13 C12 115.0(3) . . ? C14 C13 H13A 108.5 . . ? C12 C13 H13A 108.5 . . ? C14 C13 H13B 108.5 . . ? C12 C13 H13B 108.5 . . ? H13A C13 H13B 107.5 . . ? C15 C14 C13 113.6(3) . . ? C15 C14 H14A 108.8 . . ? C13 C14 H14A 108.8 . . ? C15 C14 H14B 108.8 . . ? C13 C14 H14B 108.8 . . ? H14A C14 H14B 107.7 . . ? C16 C15 C14 114.9(3) . . ? C16 C15 H15A 108.5 . . ? C14 C15 H15A 108.5 . . ? C16 C15 H15B 108.5 . . ? C14 C15 H15B 108.5 . . ? H15A C15 H15B 107.5 . . ? C17 C16 C15 113.5(3) . . ? C17 C16 H16A 108.9 . . ? C15 C16 H16A 108.9 . . ? C17 C16 H16B 108.9 . . ? C15 C16 H16B 108.9 . . ? H16A C16 H16B 107.7 . . ? C16 C17 C18 114.8(3) . . ? C16 C17 H17A 108.6 . . ? C18 C17 H17A 108.6 . . ? C16 C17 H17B 108.6 . . ? C18 C17 H17B 108.6 . . ? H17A C17 H17B 107.5 . . ? C19 C18 C17 113.5(3) . . ? C19 C18 H18A 108.9 . . ? C17 C18 H18A 108.9 . . ? C19 C18 H18B 108.9 . . ? C17 C18 H18B 108.9 . . ? H18A C18 H18B 107.7 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.617 _refine_diff_density_min -0.571 _refine_diff_density_rms 0.081 _database_code_depnum_ccdc_archive 'CCDC 808343' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_yg009 #TrackingRef 'Total_CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 5,5Bis(5ndodecylpyridin-2-yl)2,2-bithiophene _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H60 N2 S2' _chemical_formula_weight 657.04 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' N N 0.0061 0.0033 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.661(6) _cell_length_b 11.898(12) _cell_length_c 28.47(3) _cell_angle_alpha 98.440(15) _cell_angle_beta 91.421(16) _cell_angle_gamma 103.379(15) _cell_volume 1842(3) _cell_formula_units_Z 2 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 781 _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 20.08 _exptl_crystal_description Yellow _exptl_crystal_colour Block _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.185 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 716 _exptl_absorpt_coefficient_mu 0.176 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9826 _exptl_absorpt_correction_T_max 0.9912 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14498 _diffrn_reflns_av_R_equivalents 0.1615 _diffrn_reflns_av_sigmaI/netI 0.2483 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 0.72 _diffrn_reflns_theta_max 25.05 _reflns_number_total 6494 _reflns_number_gt 2523 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.4833P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment CONSTR _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6494 _refine_ls_number_parameters 417 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2106 _refine_ls_R_factor_gt 0.0737 _refine_ls_wR_factor_ref 0.2262 _refine_ls_wR_factor_gt 0.1556 _refine_ls_goodness_of_fit_ref 0.848 _refine_ls_restrained_S_all 0.848 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 1.5178(3) 0.03786(14) 0.07769(6) 0.0295(4) Uani 1 1 d . . . S2 S -0.5182(3) 0.93873(13) 0.42330(6) 0.0269(4) Uani 1 1 d . . . N1 N 1.4061(9) 0.0368(4) 0.17599(18) 0.0351(13) Uani 1 1 d . . . N2 N -0.4318(8) 0.8213(4) 0.33013(17) 0.0290(12) Uani 1 1 d . . . C1 C 1.4232(10) -0.0127(5) 0.0187(2) 0.0263(15) Uani 1 1 d . . . C2 C 1.1858(10) -0.0761(5) 0.0154(2) 0.0268(14) Uani 1 1 d . . . H2 H 1.1000 -0.1118 -0.0142 0.032 Uiso 1 1 calc R . . C3 C 1.0814(11) -0.0837(5) 0.0591(2) 0.0300(15) Uani 1 1 d . . . H3 H 0.9191 -0.1249 0.0625 0.036 Uiso 1 1 calc R . . C4 C 1.2405(10) -0.0247(5) 0.0967(2) 0.0267(15) Uani 1 1 d . . . C5 C 1.2046(10) -0.0103(5) 0.1478(2) 0.0272(15) Uani 1 1 d . . . C6 C 0.9785(11) -0.0426(5) 0.1661(2) 0.0309(15) Uani 1 1 d . . . H6 H 0.8370 -0.0733 0.1454 0.037 Uiso 1 1 calc R . . C7 C 0.9610(11) -0.0299(5) 0.2146(2) 0.0300(15) Uani 1 1 d . . . H7 H 0.8073 -0.0525 0.2276 0.036 Uiso 1 1 calc R . . C8 C 1.1705(11) 0.0165(5) 0.2447(2) 0.0295(15) Uani 1 1 d . . . C9 C 1.3825(11) 0.0492(6) 0.2226(2) 0.0385(17) Uani 1 1 d . . . H9 H 1.5256 0.0841 0.2425 0.046 Uiso 1 1 calc R . . C10 C 1.1611(12) 0.0328(5) 0.2977(2) 0.0340(16) Uani 1 1 d . . . H10A H 1.3282 0.0663 0.3121 0.041 Uiso 1 1 calc R . . H10B H 1.1030 -0.0448 0.3076 0.041 Uiso 1 1 calc R . . C11 C 0.9995(11) 0.1110(5) 0.3175(2) 0.0342(16) Uani 1 1 d . . . H11A H 1.0416 0.1848 0.3041 0.041 Uiso 1 1 calc R . . H11B H 0.8282 0.0720 0.3072 0.041 Uiso 1 1 calc R . . C12 C 1.0214(11) 0.1397(5) 0.3711(2) 0.0297(15) Uani 1 1 d . . . H12A H 1.1938 0.1765 0.3813 0.036 Uiso 1 1 calc R . . H12B H 0.9763 0.0657 0.3843 0.036 Uiso 1 1 calc R . . C13 C 0.8654(11) 0.2208(5) 0.3926(2) 0.0317(15) Uani 1 1 d . . . H13A H 0.9086 0.2948 0.3793 0.038 Uiso 1 1 calc R . . H13B H 0.6922 0.1837 0.3831 0.038 Uiso 1 1 calc R . . C14 C 0.8963(11) 0.2484(5) 0.4462(2) 0.0294(15) Uani 1 1 d . . . H14A H 1.0704 0.2835 0.4554 0.035 Uiso 1 1 calc R . . H14B H 0.8505 0.1742 0.4592 0.035 Uiso 1 1 calc R . . C15 C 0.7476(11) 0.3309(5) 0.4689(2) 0.0299(15) Uani 1 1 d . . . H15A H 0.5729 0.2964 0.4600 0.036 Uiso 1 1 calc R . . H15B H 0.7937 0.4059 0.4564 0.036 Uiso 1 1 calc R . . C16 C 0.7874(11) 0.3545(5) 0.5230(2) 0.0291(15) Uani 1 1 d . . . H16A H 0.7405 0.2790 0.5351 0.035 Uiso 1 1 calc R . . H16B H 0.9631 0.3872 0.5314 0.035 Uiso 1 1 calc R . . C17 C 0.6480(10) 0.4373(5) 0.5482(2) 0.0292(15) Uani 1 1 d . . . H17A H 0.4716 0.4045 0.5408 0.035 Uiso 1 1 calc R . . H17B H 0.6931 0.5131 0.5364 0.035 Uiso 1 1 calc R . . C18 C 0.7002(11) 0.4577(5) 0.6021(2) 0.0314(16) Uani 1 1 d . . . H18A H 0.6635 0.3812 0.6136 0.038 Uiso 1 1 calc R . . H18B H 0.8756 0.4937 0.6095 0.038 Uiso 1 1 calc R . . C19 C 0.5531(11) 0.5361(5) 0.6291(2) 0.0311(15) Uani 1 1 d . . . H19A H 0.5872 0.6119 0.6171 0.037 Uiso 1 1 calc R . . H19B H 0.3778 0.4992 0.6222 0.037 Uiso 1 1 calc R . . C20 C 0.6063(12) 0.5590(6) 0.6821(2) 0.0401(17) Uani 1 1 d . . . H20A H 0.7794 0.6002 0.6893 0.048 Uiso 1 1 calc R . . H20B H 0.5803 0.4833 0.6941 0.048 Uiso 1 1 calc R . . C21 C 0.4495(13) 0.6314(6) 0.7079(2) 0.049(2) Uani 1 1 d . . . H21A H 0.4692 0.7051 0.6953 0.074 Uiso 1 1 calc R . . H21B H 0.4985 0.6479 0.7419 0.074 Uiso 1 1 calc R . . H21C H 0.2787 0.5881 0.7032 0.074 Uiso 1 1 calc R . . C22 C -0.4428(9) 0.9645(5) 0.4838(2) 0.0217(14) Uani 1 1 d . . . C23 C -0.2642(10) 0.9089(5) 0.4939(2) 0.0273(15) Uani 1 1 d . . . H23 H -0.1976 0.9125 0.5252 0.033 Uiso 1 1 calc R . . C24 C -0.1901(10) 0.8467(5) 0.4536(2) 0.0280(15) Uani 1 1 d . . . H24 H -0.0686 0.8037 0.4549 0.034 Uiso 1 1 calc R . . C25 C -0.3106(10) 0.8538(5) 0.4119(2) 0.0228(14) Uani 1 1 d . . . C26 C -0.2810(10) 0.8028(5) 0.3638(2) 0.0245(14) Uani 1 1 d . . . C27 C -0.1058(10) 0.7388(5) 0.3522(2) 0.0310(16) Uani 1 1 d . . . H27 H 0.0043 0.7297 0.3762 0.037 Uiso 1 1 calc R . . C28 C -0.0940(11) 0.6897(5) 0.3061(2) 0.0352(16) Uani 1 1 d . . . H28 H 0.0234 0.6455 0.2983 0.042 Uiso 1 1 calc R . . C29 C -0.2531(10) 0.7041(5) 0.2707(2) 0.0310(15) Uani 1 1 d . . . C30 C -0.4141(10) 0.7712(5) 0.2859(2) 0.0323(16) Uani 1 1 d . . . H30 H -0.5235 0.7828 0.2622 0.039 Uiso 1 1 calc R . . C31 C -0.2521(11) 0.6503(6) 0.2201(2) 0.0375(17) Uani 1 1 d . . . H31A H -0.3584 0.6834 0.2007 0.045 Uiso 1 1 calc R . . H31B H -0.3253 0.5654 0.2174 0.045 Uiso 1 1 calc R . . C32 C -0.0075(11) 0.6661(5) 0.1990(2) 0.0324(16) Uani 1 1 d . . . H32A H 0.0881 0.6183 0.2132 0.039 Uiso 1 1 calc R . . H32B H 0.0817 0.7491 0.2070 0.039 Uiso 1 1 calc R . . C33 C -0.0299(11) 0.6309(6) 0.1453(2) 0.0337(16) Uani 1 1 d . . . H33A H -0.1031 0.5458 0.1377 0.040 Uiso 1 1 calc R . . H33B H -0.1419 0.6719 0.1316 0.040 Uiso 1 1 calc R . . C34 C 0.2102(10) 0.6580(5) 0.1220(2) 0.0297(15) Uani 1 1 d . . . H34A H 0.2868 0.7425 0.1308 0.036 Uiso 1 1 calc R . . H34B H 0.3198 0.6142 0.1347 0.036 Uiso 1 1 calc R . . C35 C 0.1864(11) 0.6276(5) 0.0685(2) 0.0336(16) Uani 1 1 d . . . H35A H 0.0566 0.6609 0.0563 0.040 Uiso 1 1 calc R . . H35B H 0.1345 0.5415 0.0598 0.040 Uiso 1 1 calc R . . C36 C 0.4185(10) 0.6714(5) 0.0441(2) 0.0303(15) Uani 1 1 d . . . H36A H 0.4696 0.7576 0.0526 0.036 Uiso 1 1 calc R . . H36B H 0.5485 0.6386 0.0565 0.036 Uiso 1 1 calc R . . C37 C 0.3958(10) 0.6404(5) -0.0096(2) 0.0301(15) Uani 1 1 d . . . H37A H 0.3470 0.5542 -0.0182 0.036 Uiso 1 1 calc R . . H37B H 0.2642 0.6723 -0.0220 0.036 Uiso 1 1 calc R . . C38 C 0.6256(10) 0.6854(5) -0.0338(2) 0.0320(16) Uani 1 1 d . . . H38A H 0.7565 0.6528 -0.0216 0.038 Uiso 1 1 calc R . . H38B H 0.6753 0.7715 -0.0248 0.038 Uiso 1 1 calc R . . C39 C 0.6044(11) 0.6561(6) -0.0876(2) 0.0367(16) Uani 1 1 d . . . H39A H 0.4784 0.6914 -0.1000 0.044 Uiso 1 1 calc R . . H39B H 0.5490 0.5702 -0.0967 0.044 Uiso 1 1 calc R . . C40 C 0.8391(11) 0.6981(6) -0.1110(2) 0.0350(16) Uani 1 1 d . . . H40A H 0.8990 0.7836 -0.1011 0.042 Uiso 1 1 calc R . . H40B H 0.9636 0.6599 -0.1001 0.042 Uiso 1 1 calc R . . C41 C 0.8064(12) 0.6719(6) -0.1642(2) 0.0432(18) Uani 1 1 d . . . H41A H 0.6895 0.7144 -0.1751 0.052 Uiso 1 1 calc R . . H41B H 0.7355 0.5871 -0.1739 0.052 Uiso 1 1 calc R . . C42 C 1.0448(13) 0.7063(7) -0.1889(3) 0.054(2) Uani 1 1 d . . . H42A H 1.1216 0.7890 -0.1780 0.081 Uiso 1 1 calc R . . H42B H 1.0100 0.6935 -0.2234 0.081 Uiso 1 1 calc R . . H42C H 1.1550 0.6583 -0.1811 0.081 Uiso 1 1 calc R . . 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 0.0243(9) 0.0377(10) 0.0255(10) 0.0023(7) 0.0041(7) 0.0067(7) S2 0.0256(9) 0.0315(10) 0.0258(9) 0.0040(7) 0.0021(7) 0.0116(7) N1 0.032(3) 0.047(4) 0.025(3) 0.005(3) -0.003(3) 0.008(3) N2 0.028(3) 0.035(3) 0.024(3) 0.006(2) -0.004(2) 0.008(2) C1 0.027(4) 0.032(4) 0.024(4) 0.008(3) -0.001(3) 0.014(3) C2 0.024(3) 0.040(4) 0.016(3) -0.004(3) 0.002(3) 0.011(3) C3 0.036(4) 0.028(4) 0.026(4) 0.001(3) -0.003(3) 0.010(3) C4 0.025(3) 0.026(4) 0.034(4) 0.008(3) 0.009(3) 0.012(3) C5 0.023(3) 0.026(4) 0.034(4) 0.006(3) 0.007(3) 0.008(3) C6 0.024(3) 0.040(4) 0.031(4) 0.008(3) 0.006(3) 0.010(3) C7 0.020(3) 0.037(4) 0.033(4) 0.007(3) 0.008(3) 0.006(3) C8 0.037(4) 0.029(4) 0.026(4) 0.003(3) 0.006(3) 0.015(3) C9 0.029(4) 0.049(5) 0.035(5) 0.005(3) -0.002(3) 0.007(3) C10 0.042(4) 0.039(4) 0.024(4) 0.001(3) 0.003(3) 0.018(3) C11 0.036(4) 0.037(4) 0.032(4) 0.007(3) 0.004(3) 0.013(3) C12 0.026(3) 0.033(4) 0.029(4) 0.002(3) 0.004(3) 0.007(3) C13 0.034(4) 0.029(4) 0.030(4) 0.002(3) 0.002(3) 0.006(3) C14 0.025(3) 0.032(4) 0.031(4) 0.002(3) -0.001(3) 0.011(3) C15 0.029(4) 0.029(4) 0.034(4) 0.007(3) 0.004(3) 0.010(3) C16 0.028(3) 0.027(4) 0.034(4) 0.004(3) 0.000(3) 0.011(3) C17 0.025(3) 0.028(4) 0.037(4) 0.008(3) 0.008(3) 0.007(3) C18 0.032(4) 0.032(4) 0.030(4) 0.005(3) 0.001(3) 0.009(3) C19 0.031(4) 0.034(4) 0.030(4) 0.002(3) 0.006(3) 0.012(3) C20 0.037(4) 0.042(4) 0.038(4) 0.001(3) -0.002(3) 0.006(3) C21 0.057(5) 0.058(5) 0.034(4) -0.007(4) 0.003(4) 0.025(4) C22 0.012(3) 0.027(3) 0.026(4) 0.002(3) 0.003(3) 0.005(2) C23 0.025(3) 0.028(4) 0.029(4) 0.004(3) -0.006(3) 0.008(3) C24 0.026(3) 0.027(4) 0.033(4) 0.003(3) -0.005(3) 0.011(3) C25 0.015(3) 0.018(3) 0.036(4) 0.003(3) 0.005(3) 0.005(2) C26 0.021(3) 0.027(3) 0.024(4) 0.005(3) 0.002(3) 0.002(3) C27 0.023(3) 0.031(4) 0.042(4) 0.010(3) 0.002(3) 0.013(3) C28 0.033(4) 0.037(4) 0.036(4) 0.001(3) 0.001(3) 0.013(3) C29 0.016(3) 0.043(4) 0.032(4) 0.001(3) 0.008(3) 0.006(3) C30 0.023(3) 0.045(4) 0.029(4) 0.009(3) 0.000(3) 0.005(3) C31 0.035(4) 0.050(4) 0.026(4) -0.001(3) 0.004(3) 0.010(3) C32 0.029(4) 0.038(4) 0.029(4) 0.002(3) 0.000(3) 0.009(3) C33 0.026(3) 0.042(4) 0.034(4) -0.004(3) 0.008(3) 0.015(3) C34 0.027(3) 0.034(4) 0.026(4) -0.003(3) -0.002(3) 0.010(3) C35 0.030(4) 0.038(4) 0.034(4) 0.004(3) 0.003(3) 0.010(3) C36 0.018(3) 0.037(4) 0.035(4) 0.002(3) -0.003(3) 0.009(3) C37 0.026(3) 0.033(4) 0.032(4) 0.004(3) -0.003(3) 0.008(3) C38 0.029(4) 0.035(4) 0.034(4) 0.005(3) 0.003(3) 0.012(3) C39 0.032(4) 0.047(4) 0.032(4) 0.007(3) 0.001(3) 0.012(3) C40 0.029(4) 0.042(4) 0.034(4) 0.011(3) 0.004(3) 0.004(3) C41 0.041(4) 0.049(5) 0.037(5) 0.005(3) -0.001(4) 0.007(3) C42 0.052(5) 0.073(6) 0.038(5) 0.017(4) 0.008(4) 0.012(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 S1 C4 1.712(6) . ? S1 C1 1.727(6) . ? S2 C25 1.727(6) . ? S2 C22 1.728(6) . ? N1 C9 1.326(8) . ? N1 C5 1.337(7) . ? N2 C30 1.329(8) . ? N2 C26 1.344(7) . ? C1 C2 1.374(8) . ? C1 C1 1.413(11) 2_855 ? C2 C3 1.398(8) . ? C2 H2 0.9500 . ? C3 C4 1.375(8) . ? C3 H3 0.9500 . ? C4 C5 1.463(8) . ? C5 C6 1.386(8) . ? C6 C7 1.376(8) . ? C6 H6 0.9500 . ? C7 C8 1.397(8) . ? C7 H7 0.9500 . ? C8 C9 1.372(8) . ? C8 C10 1.499(8) . ? C9 H9 0.9500 . ? C10 C11 1.512(8) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.508(8) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.527(8) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.510(8) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.521(8) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.527(8) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.513(8) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.528(8) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.528(8) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.505(8) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.506(9) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.376(7) . ? C22 C22 1.430(11) 2_476 ? C23 C24 1.400(8) . ? C23 H23 0.9500 . ? C24 C25 1.378(8) . ? C24 H24 0.9500 . ? C25 C26 1.442(8) . ? C26 C27 1.402(8) . ? C27 C28 1.364(8) . ? C27 H27 0.9500 . ? C28 C29 1.391(8) . ? C28 H28 0.9500 . ? C29 C30 1.383(8) . ? C29 C31 1.487(8) . ? C30 H30 0.9500 . ? C31 C32 1.506(8) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 C33 1.518(8) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.515(8) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.508(8) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.522(8) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 C37 1.513(8) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 C38 1.512(8) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 C39 1.514(8) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 C40 1.515(8) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 C41 1.499(9) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C41 C42 1.536(9) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? 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 C4 S1 C1 92.5(3) . . ? C25 S2 C22 92.5(3) . . ? C9 N1 C5 117.2(6) . . ? C30 N2 C26 116.7(5) . . ? C2 C1 C1 128.1(7) . 2_855 ? C2 C1 S1 109.7(4) . . ? C1 C1 S1 122.2(6) 2_855 . ? C1 C2 C3 114.3(5) . . ? C1 C2 H2 122.8 . . ? C3 C2 H2 122.8 . . ? C4 C3 C2 112.2(6) . . ? C4 C3 H3 123.9 . . ? C2 C3 H3 123.9 . . ? C3 C4 C5 129.8(6) . . ? C3 C4 S1 111.3(5) . . ? C5 C4 S1 118.9(4) . . ? N1 C5 C6 121.8(6) . . ? N1 C5 C4 115.3(5) . . ? C6 C5 C4 122.9(6) . . ? C7 C6 C5 119.4(6) . . ? C7 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C6 C7 C8 119.6(6) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C9 C8 C7 115.8(6) . . ? C9 C8 C10 122.4(6) . . ? C7 C8 C10 121.7(6) . . ? N1 C9 C8 126.1(6) . . ? N1 C9 H9 117.0 . . ? C8 C9 H9 117.0 . . ? C8 C10 C11 114.7(5) . . ? C8 C10 H10A 108.6 . . ? C11 C10 H10A 108.6 . . ? C8 C10 H10B 108.6 . . ? C11 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? C12 C11 C10 113.4(5) . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11B 108.9 . . ? C10 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C11 C12 C13 115.1(5) . . ? C11 C12 H12A 108.5 . . ? C13 C12 H12A 108.5 . . ? C11 C12 H12B 108.5 . . ? C13 C12 H12B 108.5 . . ? H12A C12 H12B 107.5 . . ? C14 C13 C12 113.2(5) . . ? C14 C13 H13A 108.9 . . ? C12 C13 H13A 108.9 . . ? C14 C13 H13B 108.9 . . ? C12 C13 H13B 108.9 . . ? H13A C13 H13B 107.8 . . ? C13 C14 C15 114.8(5) . . ? C13 C14 H14A 108.6 . . ? C15 C14 H14A 108.6 . . ? C13 C14 H14B 108.6 . . ? C15 C14 H14B 108.6 . . ? H14A C14 H14B 107.5 . . ? C14 C15 C16 111.9(5) . . ? C14 C15 H15A 109.2 . . ? C16 C15 H15A 109.2 . . ? C14 C15 H15B 109.2 . . ? C16 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C17 C16 C15 115.1(5) . . ? C17 C16 H16A 108.5 . . ? C15 C16 H16A 108.5 . . ? C17 C16 H16B 108.5 . . ? C15 C16 H16B 108.5 . . ? H16A C16 H16B 107.5 . . ? C16 C17 C18 111.9(5) . . ? C16 C17 H17A 109.2 . . ? C18 C17 H17A 109.2 . . ? C16 C17 H17B 109.2 . . ? C18 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C19 C18 C17 113.4(5) . . ? C19 C18 H18A 108.9 . . ? C17 C18 H18A 108.9 . . ? C19 C18 H18B 108.9 . . ? C17 C18 H18B 108.9 . . ? H18A C18 H18B 107.7 . . ? C20 C19 C18 114.1(5) . . ? C20 C19 H19A 108.7 . . ? C18 C19 H19A 108.7 . . ? C20 C19 H19B 108.7 . . ? C18 C19 H19B 108.7 . . ? H19A C19 H19B 107.6 . . ? C19 C20 C21 112.8(5) . . ? C19 C20 H20A 109.0 . . ? C21 C20 H20A 109.0 . . ? C19 C20 H20B 109.0 . . ? C21 C20 H20B 109.0 . . ? H20A C20 H20B 107.8 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 C22 127.9(7) . 2_476 ? C23 C22 S2 110.4(4) . . ? C22 C22 S2 121.7(6) 2_476 . ? C22 C23 C24 113.4(5) . . ? C22 C23 H23 123.3 . . ? C24 C23 H23 123.3 . . ? C25 C24 C23 113.4(5) . . ? C25 C24 H24 123.3 . . ? C23 C24 H24 123.3 . . ? C24 C25 C26 129.1(5) . . ? C24 C25 S2 110.3(5) . . ? C26 C25 S2 120.6(4) . . ? N2 C26 C27 121.2(6) . . ? N2 C26 C25 115.7(5) . . ? C27 C26 C25 123.1(5) . . ? C28 C27 C26 119.8(6) . . ? C28 C27 H27 120.1 . . ? C26 C27 H27 120.1 . . ? C27 C28 C29 120.3(6) . . ? C27 C28 H28 119.9 . . ? C29 C28 H28 119.9 . . ? C30 C29 C28 115.2(6) . . ? C30 C29 C31 122.2(6) . . ? C28 C29 C31 122.6(6) . . ? N2 C30 C29 126.8(6) . . ? N2 C30 H30 116.6 . . ? C29 C30 H30 116.6 . . ? C29 C31 C32 116.3(5) . . ? C29 C31 H31A 108.2 . . ? C32 C31 H31A 108.2 . . ? C29 C31 H31B 108.2 . . ? C32 C31 H31B 108.2 . . ? H31A C31 H31B 107.4 . . ? C31 C32 C33 112.1(5) . . ? C31 C32 H32A 109.2 . . ? C33 C32 H32A 109.2 . . ? C31 C32 H32B 109.2 . . ? C33 C32 H32B 109.2 . . ? H32A C32 H32B 107.9 . . ? C34 C33 C32 113.8(5) . . ? C34 C33 H33A 108.8 . . ? C32 C33 H33A 108.8 . . ? C34 C33 H33B 108.8 . . ? C32 C33 H33B 108.8 . . ? H33A C33 H33B 107.7 . . ? C35 C34 C33 113.8(5) . . ? C35 C34 H34A 108.8 . . ? C33 C34 H34A 108.8 . . ? C35 C34 H34B 108.8 . . ? C33 C34 H34B 108.8 . . ? H34A C34 H34B 107.7 . . ? C34 C35 C36 114.4(5) . . ? C34 C35 H35A 108.7 . . ? C36 C35 H35A 108.7 . . ? C34 C35 H35B 108.7 . . ? C36 C35 H35B 108.7 . . ? H35A C35 H35B 107.6 . . ? C37 C36 C35 114.5(5) . . ? C37 C36 H36A 108.6 . . ? C35 C36 H36A 108.6 . . ? C37 C36 H36B 108.6 . . ? C35 C36 H36B 108.6 . . ? H36A C36 H36B 107.6 . . ? C38 C37 C36 114.4(5) . . ? C38 C37 H37A 108.7 . . ? C36 C37 H37A 108.7 . . ? C38 C37 H37B 108.7 . . ? C36 C37 H37B 108.7 . . ? H37A C37 H37B 107.6 . . ? C37 C38 C39 114.9(5) . . ? C37 C38 H38A 108.5 . . ? C39 C38 H38A 108.5 . . ? C37 C38 H38B 108.5 . . ? C39 C38 H38B 108.5 . . ? H38A C38 H38B 107.5 . . ? C38 C39 C40 114.1(5) . . ? C38 C39 H39A 108.7 . . ? C40 C39 H39A 108.7 . . ? C38 C39 H39B 108.7 . . ? C40 C39 H39B 108.7 . . ? H39A C39 H39B 107.6 . . ? C41 C40 C39 112.1(5) . . ? C41 C40 H40A 109.2 . . ? C39 C40 H40A 109.2 . . ? C41 C40 H40B 109.2 . . ? C39 C40 H40B 109.2 . . ? H40A C40 H40B 107.9 . . ? C40 C41 C42 113.2(6) . . ? C40 C41 H41A 108.9 . . ? C42 C41 H41A 108.9 . . ? C40 C41 H41B 108.9 . . ? C42 C41 H41B 108.9 . . ? H41A C41 H41B 107.7 . . ? C41 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C41 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.330 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.077 #===END _database_code_depnum_ccdc_archive 'CCDC 808344'