#------------------------------------------------------------------------------ #$Date: 2025-08-19 12:52:15 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301804 $ #$URL: svn://www.crystallography.net/cod/cif/2/21/44/2214499.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2214499 loop_ _publ_author_name 'Boulcina, Raouf' 'Bouacida, Sofiane' 'Roisnel, Thierry' 'Debache, Abdelmadjid' _publ_section_title ; Diethyl 4-(4-bromophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate ; _journal_coeditor_code AT2352 _journal_issue 8 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3635 _journal_page_last o3636 _journal_paper_doi 10.1107/S160053680703646X _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C19 H22 Br N O4' _chemical_formula_moiety 'C19 H22 Br N O4' _chemical_formula_structural 'C19 H22 Br N O4' _chemical_formula_sum 'C19 H22 Br N O4' _chemical_formula_weight 408.28 _chemical_name_systematic ; Diethyl 4-(4-bromophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate ; _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 _cell_angle_alpha 90.00 _cell_angle_beta 98.126(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.0597(5) _cell_length_b 7.4244(4) _cell_length_c 24.3726(13) _cell_measurement_reflns_used 8206 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 27.49 _cell_measurement_theta_min 2.32 _cell_volume 1802.05(16) _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_collection 'APEX2 (Bruker, 2003)' _computing_data_reduction SAINT _computing_molecular_graphics ; ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001) ; _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR2002 (Burla et al., 2003)' _diffrn_ambient_temperature 295(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker APEXII' _diffrn_measurement_method 'CCD rotation images, thin slices, \f scans, and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0438 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 19743 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 1.69 _exptl_absorpt_coefficient_mu 2.304 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.505 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 840 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.550 _refine_diff_density_min -0.332 _refine_ls_extinction_coef none _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.132 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 230 _refine_ls_number_reflns 4132 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.132 _refine_ls_R_factor_all 0.0370 _refine_ls_R_factor_gt 0.0270 _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^)+(0.0459P)^2^+0.9623P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0749 _refine_ls_wR_factor_ref 0.0933 _reflns_number_gt 3460 _reflns_number_total 4132 _reflns_threshold_expression I>2\s(I) _cod_data_source_file at2352.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2214499 _cod_database_fobs_code 2214499 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_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br 0.02430(10) 0.0300(2) 0.01610(10) 0.00650(10) 0.00680(10) -0.00150(10) O1 0.0172(7) 0.0324(9) 0.0236(8) 0.0037(6) -0.0011(6) 0.0056(6) O2 0.0174(7) 0.0263(8) 0.0184(8) -0.0045(6) -0.0032(6) -0.0026(6) O3 0.0208(7) 0.0123(7) 0.0201(7) 0.0007(5) 0.0004(5) -0.0008(5) O4 0.0179(7) 0.0148(7) 0.0195(8) -0.0010(5) -0.0044(6) 0.0042(5) N1 0.0183(8) 0.0097(7) 0.0187(8) -0.0010(6) 0.0002(6) -0.0012(6) C1 0.0202(10) 0.0182(10) 0.0234(11) 0.0044(8) 0.0055(8) 0.0035(8) C2 0.0147(9) 0.0167(10) 0.0144(9) 0.0010(7) 0.0041(7) 0.0033(7) C3 0.0138(8) 0.0164(9) 0.0117(9) 0.0003(7) 0.0032(7) 0.0016(7) C4 0.0149(8) 0.0124(9) 0.0122(9) -0.0023(7) 0.0011(7) -0.0003(7) C5 0.0132(8) 0.0133(9) 0.0118(9) -0.0005(7) 0.0027(7) 0.0008(7) C6 0.0151(9) 0.0149(10) 0.0110(9) -0.0006(7) 0.0027(7) 0.0013(7) C7 0.0215(10) 0.0153(10) 0.0163(10) -0.0016(8) -0.0011(8) -0.0030(7) C8 0.0137(9) 0.0157(10) 0.0103(9) -0.0004(7) 0.0044(7) -0.0002(7) C9 0.0176(9) 0.0165(10) 0.0218(10) 0.0019(8) -0.0043(8) 0.0053(8) C10 0.0378(13) 0.0325(13) 0.0202(11) 0.0103(10) 0.0023(9) 0.0078(9) C11 0.0144(9) 0.0242(11) 0.0127(9) -0.0024(7) 0.0038(7) 0.0024(7) C12 0.0195(10) 0.0386(14) 0.0198(11) -0.0103(9) -0.0013(9) -0.0050(9) C13 0.0273(12) 0.0371(14) 0.0226(12) -0.0052(9) 0.0020(9) -0.0058(9) C14 0.0135(9) 0.0157(9) 0.0111(8) 0.0013(7) -0.0007(7) 0.0003(7) C15 0.0242(10) 0.0152(10) 0.0162(9) -0.0022(8) 0.0048(8) -0.0034(7) C16 0.0222(10) 0.0206(10) 0.0180(10) -0.0028(8) 0.0047(8) 0.0007(8) C17 0.0163(9) 0.0242(11) 0.0106(9) 0.0064(7) 0.0027(7) 0.0003(7) C18 0.0226(10) 0.0185(10) 0.0210(10) -0.0001(8) 0.0022(8) -0.0070(8) C19 0.0202(10) 0.0173(10) 0.0205(10) -0.0025(8) 0.0028(8) -0.0032(8) loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy Br Br 0.53359(2) 0.25548(3) 0.271070(10) 0.02310(10) Uani 1.000 O O1 1.15604(14) -0.0716(2) 0.14212(6) 0.0248(5) Uani 1.000 O O2 1.07916(15) 0.2138(2) 0.13729(6) 0.0213(4) Uani 1.000 O O3 0.72372(13) 0.42820(18) 0.00338(6) 0.0180(4) Uani 1.000 O O4 0.57284(14) 0.24035(17) -0.04326(6) 0.0181(4) Uani 1.000 N N1 0.81110(17) -0.1926(2) 0.02334(7) 0.0158(4) Uani 1.000 C C1 1.0102(2) -0.3304(3) 0.07312(9) 0.0204(6) Uani 1.000 C C2 0.92482(18) -0.1649(3) 0.06168(8) 0.0151(5) Uani 1.000 C C3 0.95008(18) 0.0016(3) 0.08344(8) 0.0138(5) Uani 1.000 C C4 0.84771(18) 0.1524(3) 0.07128(7) 0.0133(5) Uani 1.000 C C5 0.75149(18) 0.1147(3) 0.01826(7) 0.0127(5) Uani 1.000 C C6 0.73320(18) -0.0549(3) -0.00198(7) 0.0136(5) Uani 1.000 C C7 0.63769(19) -0.1155(3) -0.05182(8) 0.0181(6) Uani 1.000 C C8 0.68440(19) 0.2753(2) -0.00735(8) 0.0130(5) Uani 1.000 C C9 0.51398(19) 0.3921(3) -0.07597(8) 0.0193(6) Uani 1.000 C C10 0.5891(2) 0.4244(3) -0.12397(9) 0.0303(7) Uani 1.000 C C11 1.07165(18) 0.0371(3) 0.12318(8) 0.0169(6) Uani 1.000 C C12 1.1835(2) 0.2660(3) 0.18190(10) 0.0264(7) Uani 1.000 C C13 1.1395(3) 0.2357(3) 0.23741(10) 0.0292(7) Uani 1.000 C C14 0.76975(18) 0.1802(3) 0.12001(7) 0.0137(5) Uani 1.000 C C15 0.6847(2) 0.0454(3) 0.13475(8) 0.0184(6) Uani 1.000 C C16 0.6134(2) 0.0666(3) 0.17933(8) 0.0201(6) Uani 1.000 C C17 0.6288(2) 0.2243(3) 0.20965(8) 0.0170(6) Uani 1.000 C C18 0.7117(2) 0.3610(3) 0.19590(8) 0.0208(6) Uani 1.000 C C19 0.7813(2) 0.3375(3) 0.15105(8) 0.0193(6) Uani 1.000 H H1 0.78782 -0.30168 0.01486 0.0190 Uiso 1.000 H H1A 1.09448 -0.31251 0.05973 0.0305 Uiso 1.000 H H1B 0.96477 -0.43187 0.05462 0.0305 Uiso 1.000 H H1C 1.02581 -0.35245 0.11231 0.0305 Uiso 1.000 H H4 0.89637 0.26388 0.06592 0.0159 Uiso 1.000 H H7A 0.54706 -0.10591 -0.04401 0.0271 Uiso 1.000 H H7B 0.65646 -0.23841 -0.06021 0.0271 Uiso 1.000 H H7C 0.64872 -0.04066 -0.08299 0.0271 Uiso 1.000 H H9A 0.51786 0.49911 -0.05295 0.0232 Uiso 1.000 H H9B 0.42047 0.36700 -0.08950 0.0232 Uiso 1.000 H H10A 0.68067 0.45441 -0.11041 0.0455 Uiso 1.000 H H10B 0.54807 0.52207 -0.14601 0.0455 Uiso 1.000 H H10C 0.58662 0.31751 -0.14624 0.0455 Uiso 1.000 H H12A 1.20504 0.39234 0.17800 0.0317 Uiso 1.000 H H12B 1.26403 0.19640 0.17941 0.0317 Uiso 1.000 H H13A 1.05396 0.29215 0.23823 0.0437 Uiso 1.000 H H13B 1.20446 0.28677 0.26579 0.0437 Uiso 1.000 H H13C 1.13192 0.10873 0.24375 0.0437 Uiso 1.000 H H15 0.67545 -0.06086 0.11435 0.0220 Uiso 1.000 H H16 0.55656 -0.02388 0.18853 0.0241 Uiso 1.000 H H18 0.72077 0.46701 0.21640 0.0249 Uiso 1.000 H H19 0.83673 0.42932 0.14163 0.0232 Uiso 1.000 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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 _geom_angle_publ_flag C11 O2 C12 117.15(16) no C8 O4 C9 116.32(14) no C2 N1 C6 123.64(17) no C6 N1 H1 118.00 no C2 N1 H1 118.00 no N1 C2 C3 119.37(18) no N1 C2 C1 113.54(18) no C1 C2 C3 127.07(18) no C4 C3 C11 118.21(18) no C2 C3 C4 120.71(17) no C2 C3 C11 120.87(19) no C3 C4 C14 110.84(16) no C3 C4 C5 111.13(17) no C5 C4 C14 110.44(15) no C4 C5 C8 114.20(18) no C4 C5 C6 121.03(18) no C6 C5 C8 124.76(16) no N1 C6 C7 113.35(18) no C5 C6 C7 127.52(18) no N1 C6 C5 119.10(16) no O4 C8 C5 114.28(14) no O3 C8 O4 122.29(16) no O3 C8 C5 123.41(18) no O4 C9 C10 109.88(16) no O2 C11 C3 110.57(17) no O1 C11 C3 127.0(2) no O1 C11 O2 122.40(18) no O2 C12 C13 111.17(18) no C15 C14 C19 118.05(17) no C4 C14 C15 120.27(18) no C4 C14 C19 121.69(18) no C14 C15 C16 121.44(19) no C15 C16 C17 118.8(2) no Br C17 C18 119.27(16) no Br C17 C16 119.56(16) no C16 C17 C18 121.17(19) no C17 C18 C19 119.1(2) no C14 C19 C18 121.46(19) no C2 C1 H1A 109.00 no C2 C1 H1B 109.00 no C2 C1 H1C 109.00 no H1A C1 H1B 109.00 no H1A C1 H1C 110.00 no H1B C1 H1C 109.00 no C3 C4 H4 108.00 no C5 C4 H4 108.00 no C14 C4 H4 108.00 no C6 C7 H7A 109.00 no C6 C7 H7B 109.00 no C6 C7 H7C 109.00 no H7A C7 H7B 109.00 no H7A C7 H7C 109.00 no H7B C7 H7C 109.00 no O4 C9 H9A 110.00 no O4 C9 H9B 110.00 no C10 C9 H9A 110.00 no C10 C9 H9B 110.00 no H9A C9 H9B 108.00 no C9 C10 H10A 109.00 no C9 C10 H10B 109.00 no C9 C10 H10C 109.00 no H10A C10 H10B 109.00 no H10A C10 H10C 109.00 no H10B C10 H10C 109.00 no O2 C12 H12A 109.00 no O2 C12 H12B 109.00 no C13 C12 H12A 109.00 no C13 C12 H12B 109.00 no H12A C12 H12B 108.00 no C12 C13 H13A 109.00 no C12 C13 H13B 109.00 no C12 C13 H13C 109.00 no H13A C13 H13B 109.00 no H13A C13 H13C 109.00 no H13B C13 H13C 109.00 no C14 C15 H15 119.00 no C16 C15 H15 119.00 no C15 C16 H16 121.00 no C17 C16 H16 121.00 no C17 C18 H18 120.00 no C19 C18 H18 120.00 no C14 C19 H19 119.00 no C18 C19 H19 119.00 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Br C17 1.902(2) no O1 C11 1.214(2) no O2 C11 1.356(3) no O2 C12 1.453(3) no O3 C8 1.218(2) no O4 C8 1.347(2) no O4 C9 1.457(3) no N1 C2 1.386(3) no N1 C6 1.380(3) no N1 H1 0.8600 no C1 C2 1.503(3) no C2 C3 1.355(3) no C3 C11 1.473(3) no C3 C4 1.522(3) no C4 C14 1.527(2) no C4 C5 1.527(2) no C5 C6 1.355(3) no C5 C8 1.466(3) no C6 C7 1.507(3) no C9 C10 1.499(3) no C12 C13 1.499(3) no C14 C19 1.387(3) no C14 C15 1.396(3) no C15 C16 1.393(3) no C16 C17 1.382(3) no C17 C18 1.385(3) no C18 C19 1.390(3) no C1 H1A 0.9600 no C1 H1B 0.9600 no C1 H1C 0.9600 no C4 H4 0.9800 no C7 H7A 0.9600 no C7 H7B 0.9600 no C7 H7C 0.9600 no C9 H9A 0.9700 no C9 H9B 0.9700 no C10 H10A 0.9600 no C10 H10B 0.9600 no C10 H10C 0.9600 no C12 H12A 0.9700 no C12 H12B 0.9700 no C13 H13A 0.9600 no C13 H13B 0.9600 no C13 H13C 0.9600 no C15 H15 0.9300 no C16 H16 0.9300 no C18 H18 0.9300 no C19 H19 0.9300 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1 O3 1_545 0.86 2.11 2.969(2) 173 yes C4 H4 O3 . 0.98 2.47 2.811(2) 100 yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag C11 O2 C12 C13 -83.5(2) no C12 O2 C11 O1 -7.9(3) no C12 O2 C11 C3 171.77(16) no C8 O4 C9 C10 80.4(2) no C9 O4 C8 O3 10.3(3) no C9 O4 C8 C5 -171.06(15) no C6 N1 C2 C1 -166.26(17) no C6 N1 C2 C3 12.1(3) no C2 N1 C6 C5 -12.9(3) no C2 N1 C6 C7 165.30(17) no C1 C2 C3 C11 -0.3(3) no N1 C2 C3 C4 6.9(3) no N1 C2 C3 C11 -178.42(17) no C1 C2 C3 C4 -174.97(18) no C2 C3 C4 C14 101.3(2) no C11 C3 C4 C5 163.28(17) no C11 C3 C4 C14 -73.5(2) no C2 C3 C11 O1 -3.2(3) no C2 C3 C11 O2 177.10(17) no C4 C3 C11 O1 171.59(19) no C4 C3 C11 O2 -8.1(2) no C2 C3 C4 C5 -21.9(2) no C3 C4 C5 C6 21.2(2) no C3 C4 C5 C8 -158.58(16) no C14 C4 C5 C6 -102.3(2) no C14 C4 C5 C8 78.0(2) no C3 C4 C14 C15 -65.5(2) no C3 C4 C14 C19 114.0(2) no C5 C4 C14 C15 58.1(2) no C5 C4 C14 C19 -122.3(2) no C4 C5 C6 C7 176.77(17) no C8 C5 C6 N1 174.40(17) no C8 C5 C6 C7 -3.5(3) no C4 C5 C8 O3 17.5(3) no C4 C5 C8 O4 -161.12(16) no C6 C5 C8 O3 -162.23(19) no C6 C5 C8 O4 19.1(3) no C4 C5 C6 N1 -5.4(3) no C4 C14 C15 C16 179.40(18) no C19 C14 C15 C16 -0.2(3) no C4 C14 C19 C18 -178.99(18) no C15 C14 C19 C18 0.6(3) no C14 C15 C16 C17 -0.6(3) no C15 C16 C17 Br -179.49(15) no C15 C16 C17 C18 1.0(3) no Br C17 C18 C19 179.87(15) no C16 C17 C18 C19 -0.6(3) no C17 C18 C19 C14 -0.2(3) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 856318 2 PubChem 988635