#------------------------------------------------------------------------------ #$Date: 2016-03-26 14:43:29 +0200 (Sat, 26 Mar 2016) $ #$Revision: 180274 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/60/7116090.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_7116090 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 H19 N Si' _chemical_formula_weight 301.45 _chemical_name_systematic TPASi _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 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 93.953(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.649(4) _cell_length_b 8.213(3) _cell_length_c 17.429(6) _cell_measurement_temperature 296(2) _cell_volume 1663.5(10) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _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 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 5602 _diffrn_reflns_theta_full 21.57 _diffrn_reflns_theta_max 21.57 _diffrn_reflns_theta_min 1.75 _exptl_absorpt_coefficient_mu 0.137 _exptl_absorpt_correction_T_max 0.9837 _exptl_absorpt_correction_T_min 0.9810 _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.204 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 640 _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 0.120 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.032 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 201 _refine_ls_number_reflns 1917 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.048 _refine_ls_R_factor_all 0.0434 _refine_ls_R_factor_gt 0.0344 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0501P)^2^+0.4542P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0892 _refine_ls_wR_factor_ref 0.0968 _reflns_number_gt 1613 _reflns_number_total 1917 _reflns_threshold_expression >2sigma(I) _cod_data_source_file c4cc06636g2.cif _cod_data_source_block TPASi _cod_original_cell_volume 1663.6(9) _cod_original_sg_symbol_H-M P2(1)/c _cod_database_code 7116090 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 0.16413(18) 0.4022(3) 0.67901(12) 0.0440(6) Uani 1 1 d . C2 C 0.0772(2) 0.4261(3) 0.62056(13) 0.0555(7) Uani 1 1 d . H2 H 0.0718 0.3533 0.5796 0.067 Uiso 1 1 calc R C3 C -0.0007(2) 0.5522(3) 0.62063(14) 0.0602(7) Uani 1 1 d . H3 H -0.0573 0.5642 0.5807 0.072 Uiso 1 1 calc R C4 C 0.00720(19) 0.6597(3) 0.68093(14) 0.0562(7) Uani 1 1 d . H4 H -0.0442 0.7463 0.6816 0.067 Uiso 1 1 calc R C5 C 0.08971(18) 0.6412(3) 0.74009(13) 0.0486(6) Uani 1 1 d . H5 H 0.0931 0.7149 0.7807 0.058 Uiso 1 1 calc R C6 C 0.16928(17) 0.5129(3) 0.74062(11) 0.0405(5) Uani 1 1 d . C7 C 0.34192(17) 0.3844(3) 0.81420(12) 0.0423(6) Uani 1 1 d . C8 C 0.41532(19) 0.3925(3) 0.88118(12) 0.0513(6) Uani 1 1 d . H8 H 0.4009 0.4687 0.9188 0.062 Uiso 1 1 calc R C9 C 0.5083(2) 0.2899(3) 0.89244(15) 0.0611(7) Uani 1 1 d . H9 H 0.5561 0.2982 0.9372 0.073 Uiso 1 1 calc R C10 C 0.5312(2) 0.1753(3) 0.83824(16) 0.0699(8) Uani 1 1 d . H10 H 0.5952 0.1079 0.8452 0.084 Uiso 1 1 calc R C11 C 0.4579(2) 0.1626(3) 0.77379(15) 0.0620(7) Uani 1 1 d . H11 H 0.4726 0.0830 0.7378 0.074 Uiso 1 1 calc R C12 C 0.36177(19) 0.2637(3) 0.75918(13) 0.0471(6) Uani 1 1 d . C13 C 0.3446(2) 0.2417(3) 0.58272(14) 0.0718(8) Uani 1 1 d . H13A H 0.3874 0.3414 0.5822 0.108 Uiso 1 1 calc R H13B H 0.2903 0.2380 0.5387 0.108 Uiso 1 1 calc R H13C H 0.3964 0.1510 0.5812 0.108 Uiso 1 1 calc R C14 C 0.1932(3) 0.0299(3) 0.67479(17) 0.0790(8) Uani 1 1 d . H14A H 0.2481 -0.0550 0.6675 0.118 Uiso 1 1 calc R H14B H 0.1328 0.0248 0.6345 0.118 Uiso 1 1 calc R H14C H 0.1611 0.0159 0.7236 0.118 Uiso 1 1 calc R C15 C 0.24427(18) 0.6185(3) 0.86475(12) 0.0473(6) Uani 1 1 d . C16 C 0.1768(2) 0.5883(3) 0.92504(14) 0.0624(7) Uani 1 1 d . H16 H 0.1341 0.4928 0.9265 0.075 Uiso 1 1 calc R C17 C 0.1735(3) 0.7031(4) 0.98394(14) 0.0760(9) Uani 1 1 d . H17 H 0.1285 0.6843 1.0251 0.091 Uiso 1 1 calc R C18 C 0.2364(3) 0.8432(4) 0.98093(17) 0.0802(9) Uani 1 1 d . H18 H 0.2345 0.9187 1.0206 0.096 Uiso 1 1 calc R C19 C 0.3016(2) 0.8735(4) 0.92096(18) 0.0763(8) Uani 1 1 d . H19 H 0.3433 0.9699 0.9194 0.092 Uiso 1 1 calc R C20 C 0.3059(2) 0.7612(3) 0.86234(14) 0.0599(7) Uani 1 1 d . H20 H 0.3505 0.7819 0.8212 0.072 Uiso 1 1 calc R N1 N 0.25071(15) 0.4991(2) 0.80416(10) 0.0461(5) Uani 1 1 d . Si1 Si 0.26599(6) 0.23126(8) 0.67226(4) 0.0510(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 0.0502(13) 0.0401(14) 0.0424(13) -0.0002(11) 0.0077(11) -0.0086(11) C2 0.0630(16) 0.0544(16) 0.0490(14) -0.0064(12) 0.0038(12) -0.0127(14) C3 0.0555(15) 0.0690(18) 0.0549(15) 0.0063(14) -0.0055(12) -0.0047(14) C4 0.0522(14) 0.0562(16) 0.0600(15) 0.0055(14) 0.0029(12) 0.0038(12) C5 0.0524(14) 0.0438(14) 0.0497(14) -0.0021(11) 0.0041(12) 0.0035(12) C6 0.0441(12) 0.0391(13) 0.0391(13) 0.0013(11) 0.0085(10) -0.0064(11) C7 0.0473(13) 0.0375(13) 0.0433(13) 0.0044(11) 0.0121(10) 0.0010(11) C8 0.0579(14) 0.0513(15) 0.0449(14) 0.0008(11) 0.0045(11) 0.0082(13) C9 0.0597(16) 0.0630(18) 0.0597(16) 0.0084(14) -0.0022(12) 0.0122(14) C10 0.0665(17) 0.0650(18) 0.079(2) 0.0085(16) 0.0097(16) 0.0240(14) C11 0.0729(17) 0.0525(16) 0.0622(17) -0.0027(13) 0.0160(14) 0.0148(14) C12 0.0539(14) 0.0382(13) 0.0512(14) 0.0048(11) 0.0180(11) 0.0026(11) C13 0.0867(19) 0.0736(19) 0.0568(16) -0.0054(14) 0.0182(14) 0.0083(15) C14 0.093(2) 0.0501(17) 0.095(2) -0.0171(15) 0.0179(16) -0.0099(15) C15 0.0507(14) 0.0474(15) 0.0432(14) -0.0069(12) -0.0013(11) 0.0114(12) C16 0.0682(16) 0.0681(18) 0.0518(15) 0.0023(14) 0.0100(13) 0.0153(14) C17 0.085(2) 0.100(2) 0.0430(16) -0.0025(16) 0.0094(13) 0.040(2) C18 0.086(2) 0.086(2) 0.065(2) -0.0302(18) -0.0212(17) 0.0347(19) C19 0.0730(18) 0.0653(19) 0.088(2) -0.0296(17) -0.0127(17) 0.0112(15) C20 0.0592(16) 0.0566(18) 0.0635(16) -0.0134(14) 0.0014(12) 0.0063(13) N1 0.0531(11) 0.0431(11) 0.0419(10) -0.0067(9) 0.0024(9) 0.0082(9) Si1 0.0641(5) 0.0416(4) 0.0485(4) -0.0066(3) 0.0141(3) -0.0021(3) 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 117.1(2) C2 C1 Si1 119.75(17) C6 C1 Si1 123.14(16) C3 C2 C1 123.3(2) C3 C2 H2 118.4 C1 C2 H2 118.4 C4 C3 C2 118.4(2) C4 C3 H3 120.8 C2 C3 H3 120.8 C5 C4 C3 120.8(2) C5 C4 H4 119.6 C3 C4 H4 119.6 C4 C5 C6 121.2(2) C4 C5 H5 119.4 C6 C5 H5 119.4 C5 C6 C1 119.18(19) C5 C6 N1 118.22(18) C1 C6 N1 122.59(19) C8 C7 C12 118.8(2) C8 C7 N1 118.64(19) C12 C7 N1 122.60(19) C9 C8 C7 121.3(2) C9 C8 H8 119.4 C7 C8 H8 119.4 C10 C9 C8 120.7(2) C10 C9 H9 119.6 C8 C9 H9 119.6 C11 C10 C9 118.5(2) C11 C10 H10 120.7 C9 C10 H10 120.7 C10 C11 C12 123.3(2) C10 C11 H11 118.3 C12 C11 H11 118.3 C11 C12 C7 117.3(2) C11 C12 Si1 119.72(18) C7 C12 Si1 122.95(17) Si1 C13 H13A 109.5 Si1 C13 H13B 109.5 H13A C13 H13B 109.5 Si1 C13 H13C 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 Si1 C14 H14A 109.5 Si1 C14 H14B 109.5 H14A C14 H14B 109.5 Si1 C14 H14C 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 C20 C15 C16 120.2(2) C20 C15 N1 120.1(2) C16 C15 N1 119.7(2) C15 C16 C17 119.0(3) C15 C16 H16 120.5 C17 C16 H16 120.5 C18 C17 C16 119.9(3) C18 C17 H17 120.1 C16 C17 H17 120.1 C19 C18 C17 121.0(3) C19 C18 H18 119.5 C17 C18 H18 119.5 C18 C19 C20 119.9(3) C18 C19 H19 120.0 C20 C19 H19 120.0 C15 C20 C19 120.0(3) C15 C20 H20 120.0 C19 C20 H20 120.0 C6 N1 C7 127.24(17) C6 N1 C15 116.91(17) C7 N1 C15 115.80(16) C12 Si1 C1 101.16(10) C12 Si1 C14 111.16(12) C1 Si1 C14 112.23(12) C12 Si1 C13 112.21(11) C1 Si1 C13 111.90(11) C14 Si1 C13 108.14(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.400(3) C1 C6 1.405(3) C1 Si1 1.847(2) C2 C3 1.377(3) C2 H2 0.9300 C3 C4 1.371(3) C3 H3 0.9300 C4 C5 1.369(3) C4 H4 0.9300 C5 C6 1.403(3) C5 H5 0.9300 C6 N1 1.412(3) C7 C8 1.400(3) C7 C12 1.410(3) C7 N1 1.422(3) C8 C9 1.376(3) C8 H8 0.9300 C9 C10 1.372(4) C9 H9 0.9300 C10 C11 1.367(3) C10 H10 0.9300 C11 C12 1.403(3) C11 H11 0.9300 C12 Si1 1.838(2) C13 Si1 1.865(2) C13 H13A 0.9600 C13 H13B 0.9600 C13 H13C 0.9600 C14 Si1 1.860(3) C14 H14A 0.9600 C14 H14B 0.9600 C14 H14C 0.9600 C15 C20 1.377(3) C15 C16 1.377(3) C15 N1 1.447(3) C16 C17 1.396(4) C16 H16 0.9300 C17 C18 1.367(4) C17 H17 0.9300 C18 C19 1.357(4) C18 H18 0.9300 C19 C20 1.380(3) C19 H19 0.9300 C20 H20 0.9300