#------------------------------------------------------------------------------ #$Date: 2025-08-18 14:30:32 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301775 $ #$URL: svn://www.crystallography.net/cod/cif/1/50/16/1501611.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_1501611 loop_ _publ_author_name 'Dominic Lalibert\'e' 'Thierry Maris' 'James D. Wuest' _publ_section_title ; Molecular tectonics - Use of urethanes and ureas derived from tetraphenylmethane and tetraphenylsilane to build porous chiral hydrogenbonded networks ; _journal_name_full 'Can. J. Chem.' _journal_page_first 386 _journal_page_last 398 _journal_paper_doi 10.1139/v03-208 _journal_volume 82 _journal_year 2004 _chemical_compound_source 'Synthesized by the authors. See text' _chemical_formula_sum 'C44 H56 N4 O12 Si' _chemical_formula_weight 861.02 _space_group_IT_number 86 _symmetry_cell_setting tetragonal _symmetry_space_group_name_Hall '-P 4bc' _symmetry_space_group_name_H-M 'P 42/n :2' _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 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 17.7781(2) _cell_length_b 17.7781(2) _cell_length_c 7.19040(10) _cell_measurement_reflns_used 9912 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 72.26 _cell_measurement_theta_min 2.49 _cell_volume 2272.60(5) _computing_cell_refinement 'SMART (Bruker, 1999)' _computing_data_collection 'SAINT (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_molecular_graphics 'XP (Bruker, 1999)' _computing_publication_material 'UdMX (local program)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 5.5 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_device_type 'Bruker AXS Smart 2K/Platform' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.025 _diffrn_reflns_av_sigmaI/netI 0.0194 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 15976 _diffrn_reflns_theta_full 72.89 _diffrn_reflns_theta_max 72.89 _diffrn_reflns_theta_min 3.52 _diffrn_standards_decay_% 0.00 _diffrn_standards_number 5 _exptl_absorpt_coefficient_mu 0.995 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.7800 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Sadabs (Sheldrick,1996)' _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 916 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.364 _refine_diff_density_min -0.162 _refine_diff_density_rms 0.067 _refine_ls_extinction_coef 0.0000(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 139 _refine_ls_number_reflns 2240 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.023 _refine_ls_R_factor_all 0.0879 _refine_ls_R_factor_gt 0.0724 _refine_ls_shift/su_max 3.990 _refine_ls_shift/su_mean 0.029 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1542P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2024 _refine_ls_wR_factor_ref 0.2160 _reflns_number_gt 1627 _reflns_number_total 2240 _reflns_threshold_expression >2sigma(I) _cod_data_source_file deposit.cif _cod_data_source_block jiw371 _cod_original_sg_symbol_H-M P42/n _cod_database_code 1501611 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-y, x+1/2, z+1/2' 'y+1/2, -x, z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'y, -x-1/2, -z-1/2' '-y-1/2, x, -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 Si1 Si 0.2500 0.2500 1.2500 0.0522(4) Uani 1 4 d S C2 C 0.25498(11) 0.33434(12) 1.0953(3) 0.0534(6) Uani 1 1 d . C3 C 0.31634(12) 0.38327(13) 1.0861(3) 0.0612(6) Uani 1 1 d . H3 H 0.3557 0.3773 1.1699 0.073 Uiso 1 1 calc . C4 C 0.32006(13) 0.44029(13) 0.9561(4) 0.0638(6) Uani 1 1 d . H4 H 0.3615 0.4722 0.9546 0.077 Uiso 1 1 calc . C5 C 0.26310(12) 0.45061(12) 0.8282(3) 0.0559(6) Uani 1 1 d . C6 C 0.20068(13) 0.40420(14) 0.8362(4) 0.0659(7) Uani 1 1 d . H6 H 0.1611 0.4111 0.7535 0.079 Uiso 1 1 calc . C7 C 0.19745(13) 0.34796(13) 0.9666(4) 0.0643(6) Uani 1 1 d . H7 H 0.1550 0.3174 0.9697 0.077 Uiso 1 1 calc . N8 N 0.27326(11) 0.50568(12) 0.6895(3) 0.0695(6) Uani 1 1 d . H8 H 0.3166 0.5271 0.6854 0.083 Uiso 1 1 calc . C9 C 0.22219(16) 0.52855(16) 0.5621(4) 0.0768(8) Uani 1 1 d . O10 O 0.15698(12) 0.51303(14) 0.5551(4) 0.1106(8) Uani 1 1 d . O11 O 0.25706(11) 0.57425(13) 0.4380(3) 0.0995(8) Uani 1 1 d . C12 C 0.2115(2) 0.5999(3) 0.2835(6) 0.149(2) Uani 1 1 d . H12A H 0.1870 0.5572 0.2257 0.179 Uiso 1 1 calc R H12B H 0.1728 0.6337 0.3290 0.179 Uiso 1 1 calc R C13 C 0.2559(3) 0.6375(3) 0.1507(7) 0.158(2) Uani 1 1 d . H13A H 0.2249 0.6526 0.0479 0.236 Uiso 1 1 calc R H13B H 0.2948 0.6044 0.1071 0.236 Uiso 1 1 calc R H13C H 0.2784 0.6812 0.2064 0.236 Uiso 1 1 calc R O20 O 0.47941(12) 0.93381(10) 0.0936(3) 0.0874(7) Uani 1 1 d . C21 C 0.4846(3) 1.00338(19) 0.1854(5) 0.1116(12) Uani 1 1 d . H21A H 0.5012 0.9949 0.3122 0.134 Uiso 1 1 calc R H21B H 0.4351 1.0261 0.1906 0.134 Uiso 1 1 calc R C22 C 0.4641(3) 0.9449(2) -0.0962(5) 0.1150(13) Uani 1 1 d . H22A H 0.4132 0.9638 -0.1093 0.138 Uiso 1 1 calc R H22B H 0.4666 0.8967 -0.1596 0.138 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 Si1 0.0547(5) 0.0547(5) 0.0473(7) 0.000 0.000 0.000 C2 0.0557(11) 0.0582(12) 0.0464(13) -0.0051(10) 0.0002(10) -0.0014(8) C3 0.0595(12) 0.0670(13) 0.0571(15) 0.0042(11) -0.0107(11) -0.0051(9) C4 0.0622(13) 0.0674(14) 0.0617(15) 0.0038(12) -0.0058(11) -0.0114(10) C5 0.0634(13) 0.0600(12) 0.0443(13) 0.0011(10) 0.0021(10) 0.0041(9) C6 0.0627(14) 0.0800(16) 0.0550(15) 0.0062(12) -0.0114(11) -0.0037(11) C7 0.0624(13) 0.0724(14) 0.0582(15) 0.0062(12) -0.0087(11) -0.0144(10) N8 0.0699(12) 0.0766(13) 0.0621(13) 0.0189(10) -0.0033(10) -0.0040(9) C9 0.0702(16) 0.0968(19) 0.0635(17) 0.0212(14) 0.0028(13) 0.0072(13) O10 0.0724(13) 0.157(2) 0.1025(17) 0.0559(16) -0.0051(12) 0.0045(12) O11 0.0916(14) 0.1238(17) 0.0832(15) 0.0495(13) -0.0045(11) 0.0004(11) C12 0.105(3) 0.229(5) 0.113(3) 0.104(4) -0.016(2) 0.005(3) C13 0.194(5) 0.167(4) 0.112(3) 0.063(3) -0.010(3) 0.012(4) O20 0.1205(15) 0.0671(11) 0.0747(14) 0.0017(10) -0.0070(12) 0.0057(10) C21 0.184(4) 0.0764(19) 0.074(2) -0.0109(17) 0.020(2) -0.006(2) C22 0.168(4) 0.081(2) 0.096(3) -0.0011(19) -0.042(2) -0.016(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.2541 0.3302 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 SI1 C2 7_568 2 110.75(7) y C2 SI1 C2 7_568 . 110.75(7) y C2 SI1 C2 2 . 106.94(13) y C2 SI1 C2 7_568 8_658 106.94(13) y C2 SI1 C2 2 8_658 110.75(7) y C2 SI1 C2 . 8_658 110.75(7) y C3 C2 C7 . . 115.6(2) y C3 C2 SI1 . . 124.37(16) y C7 C2 SI1 . . 119.83(16) y C4 C3 C2 . . 121.8(2) y C4 C3 H3 . . 119.1 ? C2 C3 H3 . . 119.1 ? C5 C4 C3 . . 120.9(2) y C5 C4 H4 . . 119.5 ? C3 C4 H4 . . 119.5 ? C4 C5 C6 . . 118.8(2) y C4 C5 N8 . . 118.0(2) y C6 C5 N8 . . 123.1(2) y C7 C6 C5 . . 119.8(2) y C7 C6 H6 . . 120.1 ? C5 C6 H6 . . 120.1 ? C6 C7 C2 . . 123.2(2) y C6 C7 H7 . . 118.4 ? C2 C7 H7 . . 118.4 ? C9 N8 C5 . . 127.0(2) y C9 N8 H8 . . 116.5 ? C5 N8 H8 . . 116.5 ? O10 C9 N8 . . 127.7(3) y O10 C9 O11 . . 123.7(2) y N8 C9 O11 . . 108.6(2) y C9 O11 C12 . . 116.0(3) y C13 C12 O11 . . 110.9(3) y C13 C12 H12A . . 109.5 ? O11 C12 H12A . . 109.5 ? C13 C12 H12B . . 109.5 ? O11 C12 H12B . . 109.5 ? H12A C12 H12B . . 108 ? C12 C13 H13A . . 109.5 ? C12 C13 H13B . . 109.5 ? H13A C13 H13B . . 109.5 ? C12 C13 H13C . . 109.5 ? H13A C13 H13C . . 109.5 ? H13B C13 H13C . . 109.5 ? C21 O20 C22 . . 110.3(2) y O20 C21 C22 . 5_675 113.2(3) y O20 C21 H21A . . 108.9 ? C22 C21 H21A 5_675 . 108.9 ? O20 C21 H21B . . 108.9 ? C22 C21 H21B 5_675 . 108.9 ? H21A C21 H21B . . 107.8 ? O20 C22 C21 . 5_675 113.4(3) y O20 C22 H22A . . 108.9 ? C21 C22 H22A 5_675 . 108.9 ? O20 C22 H22B . . 108.9 ? C21 C22 H22B 5_675 . 108.9 ? H22A C22 H22B . . 107.7 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Si1 C2 7_568 1.869(2) y Si1 C2 2 1.869(2) y Si1 C2 . 1.869(2) y Si1 C2 8_658 1.869(2) y C2 C3 . 1.397(3) y C2 C7 . 1.400(3) y C3 C4 . 1.381(3) y C3 H3 . 0.93 ? C4 C5 . 1.380(3) y C4 H4 . 0.93 ? C5 C6 . 1.384(3) y C5 N8 . 1.409(3) y C6 C7 . 1.372(3) y C6 H6 . 0.93 ? C7 H7 . 0.93 ? N8 C9 . 1.352(3) y N8 H8 . 0.86 ? C9 O10 . 1.193(3) y C9 O11 . 1.357(3) y O11 C12 . 1.448(4) y C12 C13 . 1.408(6) y C12 H12a . 0.97 ? C12 H12b . 0.97 ? C13 H13a . 0.96 ? C13 H13b . 0.96 ? C13 H13c . 0.96 ? O20 C21 . 1.405(4) y O20 C22 . 1.406(4) y C21 C22 5_675 1.446(5) y C21 H21a . 0.97 ? C21 H21b . 0.97 ? C22 C21 5_675 1.446(5) y C22 H22a . 0.97 ? C22 H22b . 0.97 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N8 H8 O20 0.86 2.19 2.948(3) 147.2 4_465 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_site_symmetry_1 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C2 SI1 C2 C3 7_568 . 4.93(19) y C2 SI1 C2 C3 2 . -115.8(2) y C2 SI1 C2 C3 8_658 . 123.4(2) y C2 SI1 C2 C7 7_568 . 179.2(2) y C2 SI1 C2 C7 2 . 58.46(17) y C2 SI1 C2 C7 8_658 . -62.30(15) y C7 C2 C3 C4 . . -1.1(3) y SI1 C2 C3 C4 . . 173.40(19) y C2 C3 C4 C5 . . -0.6(4) y C3 C4 C5 C6 . . 2.1(4) y C3 C4 C5 N8 . . -174.7(2) y C4 C5 C6 C7 . . -1.8(4) y N8 C5 C6 C7 . . 174.9(2) y C5 C6 C7 C2 . . 0.0(4) y C3 C2 C7 C6 . . 1.4(4) y SI1 C2 C7 C6 . . -173.3(2) y C4 C5 N8 C9 . . -174.1(3) y C6 C5 N8 C9 . . 9.2(4) y C5 N8 C9 O10 . . 9.0(5) y C5 N8 C9 O11 . . -171.4(2) y O10 C9 O11 C12 . . -4.5(5) y N8 C9 O11 C12 . . 175.9(3) y C9 O11 C12 C13 . . -171.4(4) y C22 O20 C21 C22 . 5_675 -51.8(5) y C21 O20 C22 C21 . 5_675 51.9(5) y loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139036982