#------------------------------------------------------------------------------ #$Date: 2014-12-24 13:15:43 +0200 (Wed, 24 Dec 2014) $ #$Revision: 129038 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/60/7116091.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7116091 loop_ _publ_author_name 'Huanhuan Li' 'Yang Wang' 'Kai Yuan' 'Ye Tao' 'Runfeng Chen' 'Chao Zheng' 'Xinhui Zhou' 'Junfeng Li' 'Wei Huang' _publ_section_title ; Efficient synthesis of pi-extended phenazasilines for optical and electronic applications ; _journal_name_full Chem.Commun. _journal_page_first 15760 _journal_paper_doi 10.1039/C4cc06636G _journal_volume 50 _journal_year 2014 _chemical_formula_sum 'C20 H17 N Si' _chemical_formula_weight 299.44 _chemical_name_systematic PhCzSi _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 115.360(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.4672(19) _cell_length_b 17.673(4) _cell_length_c 10.494(2) _cell_measurement_temperature 296(2) _cell_volume 1586.6(6) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1042 _diffrn_reflns_av_sigmaI/netI 0.0694 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 7781 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.30 _exptl_absorpt_coefficient_mu 0.144 _exptl_absorpt_correction_T_max 0.9830 _exptl_absorpt_correction_T_min 0.9802 _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 632 _exptl_crystal_preparation Luminescent _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: dichloromethane and ethanol solution' _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.203 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.054 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 201 _refine_ls_number_reflns 2795 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.102 _refine_ls_R_factor_all 0.0523 _refine_ls_R_factor_gt 0.0438 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0531P)^2^+0.1838P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1138 _refine_ls_wR_factor_ref 0.1235 _reflns_number_gt 2305 _reflns_number_total 2795 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file c4cc06636g2.cif _[local]_cod_data_source_block PhCzSi _[local]_cod_cif_authors_sg_H-M P2(1)/n _cod_original_cell_volume 1586.5(6) _cod_database_code 7116091 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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 C1 C 0.2446(2) 0.24146(11) 0.98863(18) 0.0397(4) Uani 1 1 d . C2 C 0.2519(2) 0.31380(12) 1.04392(19) 0.0486(5) Uani 1 1 d . H2 H 0.3466 0.3396 1.0773 0.058 Uiso 1 1 calc R C3 C 0.1259(3) 0.34906(12) 1.0516(2) 0.0543(5) Uani 1 1 d . H3 H 0.1367 0.3966 1.0928 0.065 Uiso 1 1 calc R C4 C -0.0173(3) 0.31225(12) 0.9969(2) 0.0522(5) Uani 1 1 d . H4 H -0.1045 0.3360 0.9981 0.063 Uiso 1 1 calc R C5 C -0.0309(2) 0.24045(11) 0.94076(19) 0.0439(4) Uani 1 1 d . H5 H -0.1276 0.2164 0.9033 0.053 Uiso 1 1 calc R C6 C 0.0991(2) 0.20378(10) 0.93981(17) 0.0357(4) Uani 1 1 d . C7 C -0.0402(2) 0.07794(10) 0.85620(17) 0.0363(4) Uani 1 1 d . C8 C -0.1460(2) 0.07280(11) 0.91629(19) 0.0431(4) Uani 1 1 d . H8 H -0.1472 0.1089 0.9804 0.052 Uiso 1 1 calc R C9 C -0.2488(2) 0.01260(12) 0.8778(2) 0.0500(5) Uani 1 1 d . H9 H -0.3199 0.0084 0.9170 0.060 Uiso 1 1 calc R C10 C -0.2491(2) -0.04179(12) 0.7822(2) 0.0547(5) Uani 1 1 d . H10 H -0.3218 -0.0809 0.7563 0.066 Uiso 1 1 calc R C11 C -0.1418(2) -0.03795(11) 0.7257(2) 0.0493(5) Uani 1 1 d . H11 H -0.1408 -0.0747 0.6627 0.059 Uiso 1 1 calc R C12 C -0.0351(2) 0.02156(10) 0.76399(17) 0.0387(4) Uani 1 1 d . C13 C 0.0988(2) 0.03712(10) 0.73636(17) 0.0380(4) Uani 1 1 d . C14 C 0.1676(2) 0.00042(12) 0.65924(19) 0.0482(5) Uani 1 1 d . H14 H 0.1218 -0.0425 0.6064 0.058 Uiso 1 1 calc R C15 C 0.3051(2) 0.02916(13) 0.6630(2) 0.0540(5) Uani 1 1 d . H15 H 0.3502 0.0061 0.6097 0.065 Uiso 1 1 calc R C16 C 0.3770(2) 0.09179(12) 0.7449(2) 0.0478(5) Uani 1 1 d . H16 H 0.4708 0.1088 0.7465 0.057 Uiso 1 1 calc R C17 C 0.3143(2) 0.13039(11) 0.82502(17) 0.0389(4) Uani 1 1 d . C18 C 0.1712(2) 0.10228(10) 0.81365(17) 0.0356(4) Uani 1 1 d . C19 C 0.5638(3) 0.15715(15) 1.1234(2) 0.0654(6) Uani 1 1 d . H19A H 0.5194 0.1135 1.1469 0.098 Uiso 1 1 calc R H19B H 0.5979 0.1925 1.2003 0.098 Uiso 1 1 calc R H19C H 0.6514 0.1420 1.1061 0.098 Uiso 1 1 calc R C20 C 0.5097(3) 0.27795(14) 0.9030(3) 0.0709(7) Uani 1 1 d . H20A H 0.5768 0.2551 0.8667 0.106 Uiso 1 1 calc R H20B H 0.5704 0.3099 0.9815 0.106 Uiso 1 1 calc R H20C H 0.4313 0.3077 0.8305 0.106 Uiso 1 1 calc R N1 N 0.08200(16) 0.12988(8) 0.88196(14) 0.0359(3) Uani 1 1 d . Si1 Si 0.41355(6) 0.20274(3) 0.96215(5) 0.0419(2) 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 0.0376(9) 0.0451(10) 0.0342(8) -0.0007(8) 0.0134(7) -0.0023(8) C2 0.0474(12) 0.0510(11) 0.0453(11) -0.0100(8) 0.0180(9) -0.0105(9) C3 0.0623(14) 0.0462(11) 0.0545(12) -0.0129(9) 0.0251(10) -0.0007(10) C4 0.0534(13) 0.0523(12) 0.0556(11) -0.0062(9) 0.0279(10) 0.0082(10) C5 0.0407(10) 0.0460(11) 0.0464(10) -0.0038(8) 0.0198(8) -0.0005(9) C6 0.0365(9) 0.0386(10) 0.0323(8) 0.0001(7) 0.0150(7) 0.0003(8) C7 0.0327(9) 0.0364(9) 0.0374(9) 0.0047(7) 0.0127(7) 0.0023(8) C8 0.0389(10) 0.0469(11) 0.0448(10) 0.0051(8) 0.0193(8) 0.0019(9) C9 0.0377(10) 0.0569(12) 0.0546(11) 0.0125(10) 0.0189(9) -0.0014(9) C10 0.0452(12) 0.0503(12) 0.0617(12) 0.0037(10) 0.0162(10) -0.0109(10) C11 0.0462(11) 0.0445(11) 0.0486(11) -0.0030(9) 0.0122(9) -0.0047(9) C12 0.0369(10) 0.0378(9) 0.0366(9) 0.0034(7) 0.0111(7) 0.0020(8) C13 0.0370(9) 0.0393(9) 0.0342(8) 0.0018(7) 0.0119(7) 0.0060(8) C14 0.0519(12) 0.0488(11) 0.0417(10) -0.0061(9) 0.0178(9) 0.0075(10) C15 0.0541(12) 0.0687(14) 0.0446(10) -0.0029(10) 0.0264(9) 0.0141(11) C16 0.0405(10) 0.0618(12) 0.0459(10) 0.0054(9) 0.0230(8) 0.0068(10) C17 0.0350(9) 0.0464(10) 0.0374(9) 0.0061(8) 0.0174(7) 0.0051(8) C18 0.0337(9) 0.0409(9) 0.0317(8) 0.0031(7) 0.0136(7) 0.0056(8) C19 0.0476(12) 0.0832(17) 0.0522(12) 0.0027(11) 0.0086(9) 0.0084(12) C20 0.0614(15) 0.0650(15) 0.0975(18) 0.0039(13) 0.0446(14) -0.0101(13) N1 0.0331(8) 0.0373(8) 0.0405(8) -0.0019(6) 0.0190(6) 0.0002(6) Si1 0.0323(3) 0.0471(3) 0.0455(3) 0.0017(2) 0.0158(2) -0.0033(2) 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' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 C1 C6 116.76(17) C2 C1 Si1 120.34(15) C6 C1 Si1 122.50(13) C3 C2 C1 123.30(19) C3 C2 H2 118.4 C1 C2 H2 118.4 C2 C3 C4 118.73(19) C2 C3 H3 120.6 C4 C3 H3 120.6 C5 C4 C3 120.22(19) C5 C4 H4 119.9 C3 C4 H4 119.9 C4 C5 C6 120.55(18) C4 C5 H5 119.7 C6 C5 H5 119.7 C5 C6 C1 120.29(17) C5 C6 N1 119.40(15) C1 C6 N1 120.21(15) C8 C7 C12 120.55(17) C8 C7 N1 130.12(16) C12 C7 N1 109.05(15) C9 C8 C7 118.03(18) C9 C8 H8 121.0 C7 C8 H8 121.0 C8 C9 C10 121.91(19) C8 C9 H9 119.0 C10 C9 H9 119.0 C11 C10 C9 120.14(19) C11 C10 H10 119.9 C9 C10 H10 119.9 C10 C11 C12 119.32(19) C10 C11 H11 120.3 C12 C11 H11 120.3 C11 C12 C7 119.96(17) C11 C12 C13 132.63(17) C7 C12 C13 107.21(15) C14 C13 C18 118.75(17) C14 C13 C12 134.10(18) C18 C13 C12 107.07(15) C15 C14 C13 118.71(18) C15 C14 H14 120.6 C13 C14 H14 120.6 C14 C15 C16 121.13(18) C14 C15 H15 119.4 C16 C15 H15 119.4 C15 C16 C17 122.65(18) C15 C16 H16 118.7 C17 C16 H16 118.7 C16 C17 C18 114.90(17) C16 C17 Si1 126.82(15) C18 C17 Si1 117.51(13) C17 C18 C13 123.71(16) C17 C18 N1 127.11(16) C13 C18 N1 109.07(15) Si1 C19 H19A 109.5 Si1 C19 H19B 109.5 H19A C19 H19B 109.5 Si1 C19 H19C 109.5 H19A C19 H19C 109.5 H19B C19 H19C 109.5 Si1 C20 H20A 109.5 Si1 C20 H20B 109.5 H20A C20 H20B 109.5 Si1 C20 H20C 109.5 H20A C20 H20C 109.5 H20B C20 H20C 109.5 C18 N1 C7 107.39(14) C18 N1 C6 123.55(14) C7 N1 C6 127.95(14) C17 Si1 C20 113.08(10) C17 Si1 C19 110.06(10) C20 Si1 C19 108.63(12) C17 Si1 C1 100.75(8) C20 Si1 C1 111.12(10) C19 Si1 C1 113.12(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.393(3) C1 C6 1.414(2) C1 Si1 1.8670(19) C2 C3 1.379(3) C2 H2 0.9300 C3 C4 1.387(3) C3 H3 0.9300 C4 C5 1.382(3) C4 H4 0.9300 C5 C6 1.395(2) C5 H5 0.9300 C6 N1 1.420(2) C7 C8 1.396(3) C7 C12 1.404(2) C7 N1 1.410(2) C8 C9 1.380(3) C8 H8 0.9300 C9 C10 1.388(3) C9 H9 0.9300 C10 C11 1.380(3) C10 H10 0.9300 C11 C12 1.393(3) C11 H11 0.9300 C12 C13 1.443(3) C13 C14 1.397(3) C13 C18 1.406(2) C14 C15 1.382(3) C14 H14 0.9300 C15 C16 1.388(3) C15 H15 0.9300 C16 C17 1.398(3) C16 H16 0.9300 C17 C18 1.399(2) C17 Si1 1.8521(19) C18 N1 1.408(2) C19 Si1 1.864(2) C19 H19A 0.9600 C19 H19B 0.9600 C19 H19C 0.9600 C20 Si1 1.861(2) C20 H20A 0.9600 C20 H20B 0.9600 C20 H20C 0.9600