#------------------------------------------------------------------------------ #$Date: 2025-08-19 12:52:15 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301804 $ #$URL: svn://www.crystallography.net/cod/cif/2/21/45/2214557.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_2214557 loop_ _publ_author_name 'G. Chakkaravarthi' 'N. Ramesh' 'A. K. Mohanakrishnan' 'V. Manivannan' _publ_section_title ; Ethyl 2-bromomethyl-1-phenylsulfonyl-1H-indole-3-carboxylate ; _journal_coeditor_code BT2442 _journal_issue 8 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3564 _journal_page_last o3564 _journal_paper_doi 10.1107/S1600536807034800 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C18 H16 Br N O4 S' _chemical_formula_moiety 'C18 H16 Br N O4 S' _chemical_formula_sum 'C18 H16 Br N O4 S' _chemical_formula_weight 422.29 _chemical_name_systematic ; Ethyl 2-bromomethyl-1-phenylsulfonyl-1H-indole-3-carboxylate ; _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 SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 94.1470(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.1684(3) _cell_length_b 9.4962(4) _cell_length_c 23.0376(9) _cell_measurement_reflns_used 6136 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 24.9 _cell_measurement_theta_min 2.3 _cell_volume 1782.32(12) _computing_cell_refinement APEX2 _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_data_reduction APEX2 _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 295(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker Kappa APEX II' _diffrn_measurement_method '\w and \f' _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 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0387 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_number 23119 _diffrn_reflns_theta_full 30.15 _diffrn_reflns_theta_max 30.15 _diffrn_reflns_theta_min 2.32 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.446 _exptl_absorpt_correction_T_max 0.6404 _exptl_absorpt_correction_T_min 0.5274 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.574 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 856 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.430 _refine_diff_density_min -0.507 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 226 _refine_ls_number_reflns 5283 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.004 _refine_ls_R_factor_all 0.0884 _refine_ls_R_factor_gt 0.0397 _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^)+(0.0502P)^2^+0.431P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0973 _refine_ls_wR_factor_ref 0.1147 _reflns_number_gt 3029 _reflns_number_total 5283 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bt2442.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_geom_hbond_publ_flag' value 'Y' changed to 'y' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (7 times). Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_geom_hbond_publ_flag' value 'Y' changed to 'y' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (7 times). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2214557 _cod_database_fobs_code 2214557 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_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_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy C C1 0.2387(3) 0.2446(3) 0.68219(9) 0.0461(5) Uani d . 1 C C2 0.2765(3) 0.3652(3) 0.71316(11) 0.0589(6) Uani d . 1 H H2 0.3853 0.3907 0.7222 0.071 Uiso calc R 1 C C3 0.1510(4) 0.4474(3) 0.73057(13) 0.0747(8) Uani d . 1 H H3 0.1748 0.5289 0.7519 0.090 Uiso calc R 1 C C4 -0.0089(4) 0.4103(3) 0.71671(13) 0.0739(8) Uani d . 1 H H4 -0.0932 0.4660 0.7292 0.089 Uiso calc R 1 C C5 -0.0456(3) 0.2918(3) 0.68459(13) 0.0699(8) Uani d . 1 H H5 -0.1546 0.2690 0.6743 0.084 Uiso calc R 1 C C6 0.0785(3) 0.2060(3) 0.66739(12) 0.0590(6) Uani d . 1 H H6 0.0545 0.1241 0.6463 0.071 Uiso calc R 1 C C7 0.2583(3) -0.0606(3) 0.59266(11) 0.0548(6) Uani d . 1 C C8 0.2107(4) -0.1621(3) 0.63136(14) 0.0756(8) Uani d . 1 H H8 0.2394 -0.1554 0.6711 0.091 Uiso calc R 1 C C9 0.1188(4) -0.2737(4) 0.60822(19) 0.0861(10) Uani d . 1 H H9 0.0865 -0.3439 0.6331 0.103 Uiso calc R 1 C C10 0.0738(4) -0.2844(3) 0.55022(18) 0.0802(9) Uani d . 1 H H10 0.0090 -0.3598 0.5367 0.096 Uiso calc R 1 C C11 0.1223(3) -0.1862(3) 0.51146(14) 0.0658(7) Uani d . 1 H H11 0.0935 -0.1955 0.4718 0.079 Uiso calc R 1 C C12 0.2166(3) -0.0711(2) 0.53288(11) 0.0518(6) Uani d . 1 C C13 0.2853(3) 0.0485(2) 0.50541(10) 0.0472(5) Uani d . 1 C C14 0.3655(3) 0.1301(3) 0.54708(10) 0.0467(5) Uani d . 1 C C15 0.4574(3) 0.2627(3) 0.53971(12) 0.0589(6) Uani d . 1 H H15A 0.5022 0.2631 0.5019 0.071 Uiso calc R 1 H H15B 0.5481 0.2683 0.5692 0.071 Uiso calc R 1 C C16 0.2679(3) 0.0703(3) 0.44194(11) 0.0565(6) Uani d . 1 C C17 0.3131(4) 0.2231(4) 0.36344(11) 0.0755(9) Uani d . 1 H H17A 0.2003 0.2113 0.3479 0.091 Uiso calc R 1 H H17B 0.3820 0.1598 0.3429 0.091 Uiso calc R 1 C C18 0.3658(5) 0.3693(5) 0.35624(15) 0.1081(13) Uani d . 1 H H18A 0.3578 0.3931 0.3156 0.162 Uiso calc R 1 H H18B 0.4774 0.3796 0.3717 0.162 Uiso calc R 1 H H18C 0.2966 0.4309 0.3767 0.162 Uiso calc R 1 N N1 0.3515(2) 0.0648(2) 0.60141(8) 0.0529(5) Uani d . 1 O O1 0.5447(2) 0.2186(3) 0.66281(9) 0.0900(8) Uani d . 1 O O2 0.4074(3) 0.0190(3) 0.70652(8) 0.0897(7) Uani d . 1 O O3 0.2063(3) -0.0149(2) 0.40830(9) 0.0834(6) Uani d . 1 O O4 0.3275(2) 0.1922(2) 0.42551(7) 0.0658(5) Uani d . 1 S S1 0.40267(8) 0.13478(9) 0.66717(3) 0.0608(2) Uani d . 1 Br Br1 0.31355(4) 0.42658(3) 0.546316(14) 0.07439(13) Uani d . 1 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 C1 0.0396(11) 0.0612(14) 0.0374(11) 0.0051(10) 0.0012(9) -0.0013(10) C2 0.0543(14) 0.0657(15) 0.0552(14) -0.0019(13) -0.0056(12) -0.0089(13) C3 0.094(2) 0.0675(18) 0.0618(17) 0.0152(16) -0.0029(16) -0.0147(14) C4 0.073(2) 0.081(2) 0.0690(18) 0.0306(16) 0.0164(15) 0.0056(16) C5 0.0412(13) 0.084(2) 0.085(2) 0.0091(13) 0.0078(13) 0.0100(17) C6 0.0432(13) 0.0621(15) 0.0710(16) -0.0007(11) -0.0006(12) -0.0062(13) C7 0.0471(13) 0.0575(14) 0.0597(15) 0.0160(11) 0.0036(11) -0.0021(12) C8 0.0763(19) 0.076(2) 0.0755(19) 0.0153(16) 0.0082(15) 0.0103(16) C9 0.077(2) 0.0643(19) 0.119(3) 0.0090(16) 0.020(2) 0.023(2) C10 0.0606(17) 0.0526(16) 0.127(3) 0.0066(13) 0.0039(18) -0.0018(18) C11 0.0529(15) 0.0556(15) 0.087(2) 0.0102(12) -0.0040(14) -0.0149(14) C12 0.0408(12) 0.0511(13) 0.0630(15) 0.0150(10) 0.0009(11) -0.0110(11) C13 0.0395(11) 0.0520(13) 0.0498(13) 0.0120(9) 0.0006(10) -0.0119(10) C14 0.0369(11) 0.0558(13) 0.0474(13) 0.0120(10) 0.0032(9) -0.0105(10) C15 0.0478(13) 0.0648(15) 0.0641(15) 0.0025(12) 0.0034(11) -0.0143(13) C16 0.0504(14) 0.0670(16) 0.0521(14) 0.0143(12) 0.0035(11) -0.0147(13) C17 0.0757(19) 0.106(2) 0.0452(15) 0.0131(17) 0.0034(13) -0.0012(15) C18 0.134(4) 0.125(3) 0.064(2) -0.018(3) -0.002(2) 0.023(2) N1 0.0481(11) 0.0638(12) 0.0461(11) 0.0088(9) -0.0015(9) -0.0099(9) O1 0.0357(9) 0.160(2) 0.0733(12) -0.0026(12) -0.0043(8) -0.0447(14) O2 0.1038(16) 0.1094(17) 0.0528(11) 0.0539(14) -0.0144(11) -0.0001(11) O3 0.1037(16) 0.0862(14) 0.0584(12) -0.0081(13) -0.0063(11) -0.0274(11) O4 0.0751(12) 0.0783(13) 0.0436(9) -0.0006(10) 0.0008(8) -0.0060(9) S1 0.0430(3) 0.0916(5) 0.0460(3) 0.0190(3) -0.0092(3) -0.0135(3) Br1 0.0816(2) 0.05670(18) 0.0855(2) 0.00656(14) 0.01067(16) -0.00998(14) 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' S S 0.1246 0.1234 '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 C2 C1 C6 121.6(2) C2 C1 S1 116.92(18) C6 C1 S1 121.26(19) C3 C2 C1 118.8(2) C3 C2 H2 120.6 C1 C2 H2 120.6 C4 C3 C2 120.4(3) C4 C3 H3 119.8 C2 C3 H3 119.8 C3 C4 C5 120.4(3) C3 C4 H4 119.8 C5 C4 H4 119.8 C4 C5 C6 120.3(3) C4 C5 H5 119.9 C6 C5 H5 119.9 C1 C6 C5 118.4(3) C1 C6 H6 120.8 C5 C6 H6 120.8 C8 C7 C12 121.6(3) C8 C7 N1 131.6(3) C12 C7 N1 106.8(2) C9 C8 C7 117.0(3) C9 C8 H8 121.5 C7 C8 H8 121.5 C10 C9 C8 122.4(3) C10 C9 H9 118.8 C8 C9 H9 118.8 C9 C10 C11 121.2(3) C9 C10 H10 119.4 C11 C10 H10 119.4 C10 C11 C12 118.6(3) C10 C11 H11 120.7 C12 C11 H11 120.7 C7 C12 C11 119.3(3) C7 C12 C13 107.6(2) C11 C12 C13 133.1(2) C14 C13 C12 108.8(2) C14 C13 C16 128.8(2) C12 C13 C16 122.4(2) C13 C14 N1 108.1(2) C13 C14 C15 128.6(2) N1 C14 C15 123.4(2) C14 C15 Br1 110.73(16) C14 C15 H15A 109.5 Br1 C15 H15A 109.5 C14 C15 H15B 109.5 Br1 C15 H15B 109.5 H15A C15 H15B 108.1 O3 C16 O4 123.3(3) O3 C16 C13 123.4(3) O4 C16 C13 113.3(2) O4 C17 C18 107.4(3) O4 C17 H17A 110.2 C18 C17 H17A 110.2 O4 C17 H17B 110.2 C18 C17 H17B 110.2 H17A C17 H17B 108.5 C17 C18 H18A 109.5 C17 C18 H18B 109.5 H18A C18 H18B 109.5 C17 C18 H18C 109.5 H18A C18 H18C 109.5 H18B C18 H18C 109.5 C14 N1 C7 108.65(19) C14 N1 S1 126.64(17) C7 N1 S1 123.76(18) C16 O4 C17 116.9(2) O1 S1 O2 119.62(14) O1 S1 N1 108.05(12) O2 S1 N1 105.23(13) O1 S1 C1 108.76(13) O2 S1 C1 108.65(12) N1 S1 C1 105.66(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.373(3) C1 C6 1.378(3) C1 S1 1.752(2) C2 C3 1.371(4) C2 H2 0.9300 C3 C4 1.368(5) C3 H3 0.9300 C4 C5 1.368(4) C4 H4 0.9300 C5 C6 1.381(4) C5 H5 0.9300 C6 H6 0.9300 C7 C8 1.388(4) C7 C12 1.398(4) C7 N1 1.420(3) C8 C9 1.383(5) C8 H8 0.9300 C9 C10 1.364(5) C9 H9 0.9300 C10 C11 1.370(4) C10 H10 0.9300 C11 C12 1.406(4) C11 H11 0.9300 C12 C13 1.434(3) C13 C14 1.364(3) C13 C16 1.473(3) C14 N1 1.409(3) C14 C15 1.482(4) C15 Br1 1.962(2) C15 H15A 0.9700 C15 H15B 0.9700 C16 O3 1.205(3) C16 O4 1.322(3) C17 O4 1.456(3) C17 C18 1.467(5) C17 H17A 0.9700 C17 H17B 0.9700 C18 H18A 0.9600 C18 H18B 0.9600 C18 H18C 0.9600 N1 S1 1.679(2) O1 S1 1.416(2) O2 S1 1.424(3) 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 C2 H2 O2 2_656 0.93 2.58 3.396(3) 146.9 y C5 H5 O1 1_455 0.93 2.50 3.419(3) 170.9 y C2 H2 O1 . 0.93 2.55 2.907(3) 103 y C8 H8 O2 . 0.93 2.27 2.852(4) 121 y C11 H11 O3 . 0.93 2.48 3.000(4) 116 y C15 H15A O4 . 0.97 2.28 2.845(3) 116 y C15 H15B O1 . 0.97 2.21 2.904(3) 128 y 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 C6 C1 C2 C3 1.2(4) S1 C1 C2 C3 -174.0(2) C1 C2 C3 C4 -0.7(4) C2 C3 C4 C5 -0.9(5) C3 C4 C5 C6 2.0(5) C2 C1 C6 C5 -0.1(4) S1 C1 C6 C5 174.9(2) C4 C5 C6 C1 -1.5(4) C12 C7 C8 C9 -0.6(4) N1 C7 C8 C9 -179.9(3) C7 C8 C9 C10 -0.8(5) C8 C9 C10 C11 2.0(5) C9 C10 C11 C12 -1.7(4) C8 C7 C12 C11 0.9(3) N1 C7 C12 C11 -179.7(2) C8 C7 C12 C13 -179.4(2) N1 C7 C12 C13 0.1(2) C10 C11 C12 C7 0.3(3) C10 C11 C12 C13 -179.5(2) C7 C12 C13 C14 -0.4(2) C11 C12 C13 C14 179.3(2) C7 C12 C13 C16 178.8(2) C11 C12 C13 C16 -1.4(4) C12 C13 C14 N1 0.5(2) C16 C13 C14 N1 -178.7(2) C12 C13 C14 C15 179.0(2) C16 C13 C14 C15 -0.2(4) C13 C14 C15 Br1 91.9(3) N1 C14 C15 Br1 -89.9(2) C14 C13 C16 O3 173.3(2) C12 C13 C16 O3 -5.8(4) C14 C13 C16 O4 -6.3(3) C12 C13 C16 O4 174.6(2) C13 C14 N1 C7 -0.5(2) C15 C14 N1 C7 -179.0(2) C13 C14 N1 S1 -169.61(16) C15 C14 N1 S1 11.9(3) C8 C7 N1 C14 179.6(3) C12 C7 N1 C14 0.2(2) C8 C7 N1 S1 -10.9(4) C12 C7 N1 S1 169.74(16) O3 C16 O4 C17 1.3(4) C13 C16 O4 C17 -179.1(2) C18 C17 O4 C16 172.4(3) C14 N1 S1 O1 -36.3(2) C7 N1 S1 O1 156.06(19) C14 N1 S1 O2 -165.21(19) C7 N1 S1 O2 27.2(2) C14 N1 S1 C1 79.9(2) C7 N1 S1 C1 -87.67(19) C2 C1 S1 O1 -29.9(2) C6 C1 S1 O1 154.9(2) C2 C1 S1 O2 101.9(2) C6 C1 S1 O2 -73.4(2) C2 C1 S1 N1 -145.64(19) C6 C1 S1 N1 39.1(2) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21123956 2 PubChem 91089451