#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/72/2007262.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_2007262 loop_ _publ_author_name 'Govindasamy, L.' 'Velmurugan, D.' 'Ravikumar, K.' 'Mohanakrishnan, A.K.' _publ_section_title ; (3-Bromo-1-phenylsulfonyl-2-indolyl)methyl Benzoate ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 635 _journal_page_last 637 _journal_paper_doi 10.1107/S0108270197016995 _journal_volume 54 _journal_year 1998 _chemical_formula_sum 'C22 H16 Br N O4 S' _chemical_formula_weight 470.33 _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' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 95.9910(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.012(2) _cell_length_b 13.492(2) _cell_length_c 16.808(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 22 _cell_measurement_theta_min 5 _cell_volume 2032.5(6) _computing_cell_refinement P3 _computing_data_collection 'P3 (Siemens, 1994)' _computing_data_reduction 'SHELXTl-Plus (Sheldrick, 1991)' _computing_molecular_graphics 'ZORTEP (Zolani, 1995)' _computing_publication_material 'PARST (Nardelli, 1983)' _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 273(2) _diffrn_measurement_device 'Siemens R3m/V diffractometer' _diffrn_measurement_method \w/2\q _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 0.041 _diffrn_reflns_av_sigmaI/netI 0.055 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 2836 _diffrn_reflns_theta_max 22.55 _diffrn_reflns_theta_min 1.94 _diffrn_standards_decay_% >1 _diffrn_standards_interval_count 200 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 2.154 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.537 _exptl_crystal_density_meas ? _exptl_crystal_description prism _exptl_crystal_F_000 952 _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.37 _refine_diff_density_max 0.531 _refine_diff_density_min -0.521 _refine_ls_extinction_coef 0.0017(5) _refine_ls_extinction_method SHELXL93_(Sheldrick,_1993) _refine_ls_goodness_of_fit_all 1.069 _refine_ls_goodness_of_fit_obs 1.125 _refine_ls_hydrogen_treatment H_atoms_riding _refine_ls_matrix_type fullcycle _refine_ls_number_parameters 263 _refine_ls_number_reflns 2638 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.069 _refine_ls_restrained_S_obs 1.125 _refine_ls_R_factor_all 0.0909 _refine_ls_R_factor_obs .0509 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0419P)^2^+5.3546P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1311 _refine_ls_wR_factor_obs .1101 _reflns_number_observed 1767 _reflns_number_total 2638 _reflns_observed_criterion >2sigma(I) _cod_data_source_file pt1045.cif _cod_data_source_block dv06 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0419P)^2^+5.3546P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0419P)^2^+5.3546P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2007262 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_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 N1 .036(3) .042(3) .039(3) .006(3) .007(3) .003(3) C2 .033(4) .041(4) .051(5) .001(3) .003(3) -.002(3) C3 .033(4) .036(4) .068(5) .001(3) .006(3) .008(4) C4 .035(4) .046(4) .081(6) -.003(3) -.005(4) -.001(4) C5 .047(5) .061(5) .074(6) -.015(4) -.005(4) -.003(5) C6 .065(5) .047(4) .072(6) -.008(4) .003(4) -.015(4) C7 .046(4) .044(4) .066(5) .002(3) .002(4) -.003(4) C8 .031(4) .039(4) .067(5) .000(3) .002(3) .007(4) C9 .030(4) .042(4) .049(4) -.006(3) .000(3) .002(4) S10 .0307(9) .0522(11) .0545(12) .0083(8) .0002(8) .0069(9) O11 .051(3) .044(3) .075(4) .016(2) .002(3) .008(2) O12 .036(3) .083(4) .048(3) .006(2) -.008(2) -.003(3) C13 .024(3) .052(4) .055(5) .003(3) .000(3) -.001(4) C14 .074(5) .052(5) .066(6) -.005(4) .014(4) -.004(4) C15 .087(6) .053(5) .089(7) -.002(4) .016(5) .008(5) C16 .058(5) .077(6) .063(6) -.004(4) .002(4) .015(5) C17 .046(4) .071(6) .062(5) -.010(4) -.004(4) -.001(5) C18 .037(4) .044(4) .063(5) -.005(3) -.001(4) -.001(4) C19 .044(4) .047(4) .063(5) -.003(3) .016(4) .003(4) O20 .047(3) .045(3) .056(3) -.005(2) -.002(2) -.001(2) C21 .057(5) .037(4) .060(5) -.001(4) -.002(4) -.013(4) O22 .103(4) .061(3) .046(3) -.020(3) -.013(3) .004(3) C23 .038(4) .040(4) .057(5) .004(3) -.001(3) -.007(4) C24 .047(4) .056(5) .071(5) .006(4) -.002(4) -.014(4) C25 .041(5) .071(6) .090(7) -.007(4) .001(5) -.027(5) C26 .062(6) .059(5) .095(7) -.012(4) .025(5) -.015(5) C27 .075(6) .055(5) .080(6) -.004(4) .013(5) .010(5) C28 .045(4) .052(4) .069(5) .000(4) -.001(4) -.002(4) Br .0459(5) .0538(5) .1147(8) .0117(4) .0174(4) -.0058(5) loop_ _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_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol N1 .0828(5) .2683(4) .3652(3) .0388(13) Uani d . 1 . N C2 .1505(7) .1881(5) .3277(4) .042(2) Uani d . 1 . C C3 .2922(7) .1808(5) .3612(4) .046(2) Uani d . 1 . C C4 .4496(7) .2813(5) .4742(5) .055(2) Uani d . 1 . C H4 .5382(7) .2460(5) .4736(5) .066 Uiso calc R 1 . H C5 .4413(8) .3604(6) .5247(5) .062(2) Uani d . 1 . C H5 .5262(8) .3804(6) .5568(5) .074 Uiso calc R 1 . H C6 .3085(8) .4112(5) .5286(5) .061(2) Uani d . 1 . C H6 .3050(8) .4629(5) .5650(5) .074 Uiso calc R 1 . H C7 .1806(8) .3866(5) .4793(4) .052(2) Uani d . 1 . C H7 .0923(8) .4219(5) .4809(4) .063 Uiso calc R 1 . H C8 .3223(7) .2540(5) .4232(4) .046(2) Uani d . 1 . C C9 .1896(6) .3075(5) .4278(4) .040(2) Uani d . 1 . C S10 -.1017(2) .28458(13) .36894(11) .0461(5) Uani d . 1 . S O11 -.1213(5) .3878(3) .3831(3) .0573(13) Uani d . 1 . O O12 -.1740(5) .2390(4) .2975(3) .0568(13) Uani d . 1 . O C13 -.1443(6) .2178(5) .4541(4) .044(2) Uani d . 1 . C C14 -.1685(8) .1165(5) .4479(5) .064(2) Uani d . 1 . C H14 -.1603(8) .0839(5) .3998(5) .076 Uiso calc R 1 . H C15 -.2048(9) .0646(6) .5135(6) .076(2) Uani d . 1 . C H15 -.2213(9) -.0033(6) .5096(6) .091 Uiso calc R 1 . H C16 -.2172(8) .1130(6) .5861(5) .066(2) Uani d . 1 . C H16 -.2419(8) .0775(6) .6302(5) .080 Uiso calc R 1 . H C17 -.1927(7) .2131(6) .5916(5) .060(2) Uani d . 1 . C H17 -.2007(7) .2454(6) .6399(5) .072 Uiso calc R 1 . H C18 -.1562(7) .2666(5) .5262(4) .049(2) Uani d . 1 . C H18 -.1397(7) .3346(5) .5303(4) .058 Uiso calc R 1 . H C19 .0824(7) .1346(5) .2545(4) .051(2) Uani d . 1 . C H19A .0243(7) .1806(5) .2195(4) .061 Uiso calc R 1 . H H19B .1606(7) .1074(5) .2255(4) .061 Uiso calc R 1 . H O20 -.0130(5) .0551(3) .2779(3) .0499(12) Uani d . 1 . O C21 -.1266(8) .0296(5) .2211(5) .052(2) Uani d . 1 . C O22 -.1474(6) .0664(4) .1566(3) .071(2) Uani d . 1 . O C23 -.2261(7) -.0464(5) .2544(4) .045(2) Uani d . 1 . C C24 -.3655(8) -.0627(5) .2109(5) .058(2) Uani d . 1 . C H24 -.3924(8) -.0287(5) .1634(5) .070 Uiso calc R 1 . H C25 -.4626(8) -.1303(6) .2398(6) .068(2) Uani d . 1 . C H25 -.5563(8) -.1400(6) .2122(6) .081 Uiso calc R 1 . H C26 -.4224(9) -.1835(6) .3092(6) .071(2) Uani d . 1 . C H26 -.4887(9) -.2283(6) .3281(6) .085 Uiso calc R 1 . H C27 -.2839(9) -.1692(6) .3496(5) .070(2) Uani d . 1 . C H27 -.2557(9) -.2059(6) .3956(5) .084 Uiso calc R 1 . H C28 -.1859(8) -.1016(5) .3232(5) .056(2) Uani d . 1 . C H28 -.0925(8) -.0926(5) .3515(5) .067 Uiso calc R 1 . H Br .43854(8) .09596(6) .32873(6) .0708(4) Uani d . 1 . Br 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 _geom_angle_publ_flag C2 N1 C9 108.4(5) yes C2 N1 S10 125.9(4) yes C9 N1 S10 120.6(4) yes C3 C2 N1 107.6(6) yes C3 C2 C19 126.7(6) yes N1 C2 C19 124.8(5) yes C2 C3 C8 110.6(6) yes C2 C3 Br 126.1(6) yes C8 C3 Br 123.1(5) yes C5 C4 C8 119.1(7) ? C5 C4 H4 120.4(4) ? C8 C4 H4 120.4(4) ? C4 C5 C6 121.2(7) ? C4 C5 H5 119.4(4) ? C6 C5 H5 119.4(4) ? C7 C6 C5 121.3(7) ? C7 C6 H6 119.3(4) ? C5 C6 H6 119.3(4) ? C9 C7 C6 117.4(6) ? C9 C7 H7 121.3(4) ? C6 C7 H7 121.3(4) ? C4 C8 C9 118.4(6) ? C4 C8 C3 134.4(6) ? C9 C8 C3 107.2(5) ? C7 C9 C8 122.5(6) ? C7 C9 N1 131.2(6) yes C8 C9 N1 106.1(5) yes O11 S10 O12 120.1(3) yes O11 S10 N1 105.8(3) yes O12 S10 N1 106.0(3) yes O11 S10 C13 108.8(3) yes O12 S10 C13 109.9(3) yes N1 S10 C13 105.2(3) yes C14 C13 C18 120.4(7) ? C14 C13 S10 119.2(6) yes C18 C13 S10 120.4(5) yes C15 C14 C13 119.4(7) ? C15 C14 H14 120.3(5) ? C13 C14 H14 120.3(5) ? C14 C15 C16 120.7(8) ? C14 C15 H15 119.7(5) ? C16 C15 H15 119.7(5) ? C17 C16 C15 119.5(8) ? C17 C16 H16 120.2(5) ? C15 C16 H16 120.2(5) ? C16 C17 C18 120.7(8) ? C16 C17 H17 119.7(5) ? C18 C17 H17 119.7(4) ? C17 C18 C13 119.4(7) ? C17 C18 H18 120.3(5) ? C13 C18 H18 120.3(4) ? O20 C19 C2 109.6(5) no O20 C19 H19A 109.8(3) ? C2 C19 H19A 109.8(4) ? O20 C19 H19B 109.8(3) ? C2 C19 H19B 109.8(3) ? H19A C19 H19B 108.2 ? C21 O20 C19 114.7(5) no O22 C21 O20 124.5(7) no O22 C21 C23 125.3(7) no O20 C21 C23 110.1(7) no C28 C23 C24 119.3(7) ? C28 C23 C21 124.0(6) ? C24 C23 C21 116.7(7) ? C25 C24 C23 119.0(7) ? C25 C24 H24 120.5(5) ? C23 C24 H24 120.5(5) ? C24 C25 C26 121.2(7) ? C24 C25 H25 119.4(5) ? C26 C25 H25 119.4(5) ? C27 C26 C25 119.3(8) ? C27 C26 H26 120.4(5) ? C25 C26 H26 120.4(5) ? C26 C27 C28 121.0(8) ? C26 C27 H27 119.5(5) ? C28 C27 H27 119.5(5) ? C27 C28 C23 120.2(7) ? C27 C28 H28 119.9(5) ? C23 C28 H28 119.9(4) ? 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 N1 C2 . 1.422(8) yes N1 C9 . 1.450(8) yes N1 S10 . 1.685(5) yes C2 C3 . 1.344(8) yes C2 C19 . 1.501(9) yes C3 C8 . 1.441(9) yes C3 Br . 1.871(6) yes C4 C5 . 1.371(10) no C4 C8 . 1.407(9) no C4 H4 . .93 ? C5 C6 . 1.387(10) no C5 H5 . .93 ? C6 C7 . 1.388(10) no C6 H6 . .93 ? C7 C9 . 1.381(9) no C7 H7 . .93 ? C8 C9 . 1.406(8) no S10 O11 . 1.427(5) yes S10 O12 . 1.443(5) yes S10 C13 . 1.767(7) yes C13 C14 . 1.386(9) no C13 C18 . 1.392(9) no C14 C15 . 1.374(10) no C14 H14 . .93 ? C15 C16 . 1.398(11) no C15 H15 . .93 ? C16 C17 . 1.370(10) no C16 H16 . .93 ? C17 C18 . 1.384(9) no C17 H17 . .93 ? C18 H18 . .93 ? C19 O20 . 1.454(7) no C19 H19A . .97 ? C19 H19B . .97 ? O20 C21 . 1.369(8) no C21 O22 . 1.190(8) no C21 C23 . 1.507(10) no C23 C28 . 1.392(9) no C23 C24 . 1.404(9) no C24 C25 . 1.386(10) no C24 H24 . .93 ? C25 C26 . 1.384(11) no C25 H25 . .93 ? C26 C27 . 1.372(11) no C26 H26 . .93 ? C27 C28 . 1.376(10) no C27 H27 . .93 ? C28 H28 . .93 ? 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 C14 H14 O20 1_555 0.930 2.584 3.413(9) 148.7 yes C18 H18 O22 4_566 0.930 2.515 3.138(8) 124.6 yes C17 H17 O12 4_566 0.930 2.643 3.507(8) 154.7 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 C9 N1 C2 C3 -3.1(7) no S10 N1 C2 C3 -157.7(5) no C9 N1 C2 C19 -173.3(6) no S10 N1 C2 C19 32.1(9) no N1 C2 C3 C8 1.4(7) no C19 C2 C3 C8 171.3(6) no N1 C2 C3 Br -173.9(4) no C19 C2 C3 Br -4.0(10) no C8 C4 C5 C6 2.6(11) ? C4 C5 C6 C7 -2.7(12) ? C5 C6 C7 C9 1.9(11) ? C5 C4 C8 C9 -1.8(10) ? C5 C4 C8 C3 176.2(7) ? C2 C3 C8 C4 -177.3(7) ? Br C3 C8 C4 -1.8(11) no C2 C3 C8 C9 0.9(8) ? Br C3 C8 C9 176.3(4) no C6 C7 C9 C8 -1.1(10) ? C6 C7 C9 N1 -174.3(6) no C4 C8 C9 C7 1.1(10) ? C3 C8 C9 C7 -177.4(6) ? C4 C8 C9 N1 175.8(6) no C3 C8 C9 N1 -2.7(7) no C2 N1 C9 C7 177.6(7) no S10 N1 C9 C7 -26.2(9) no C2 N1 C9 C8 3.6(7) no S10 N1 C9 C8 159.8(4) no C2 N1 S10 O11 -158.1(5) no C9 N1 S10 O11 50.1(5) no C2 N1 S10 O12 -29.6(6) no C9 N1 S10 O12 178.7(4) no C2 N1 S10 C13 86.8(6) no C9 N1 S10 C13 -65.0(5) no O11 S10 C13 C14 164.5(5) no O12 S10 C13 C14 31.2(6) no N1 S10 C13 C14 -82.4(6) no O11 S10 C13 C18 -14.3(6) no O12 S10 C13 C18 -147.5(5) no N1 S10 C13 C18 98.8(5) no C18 C13 C14 C15 0.2(11) ? S10 C13 C14 C15 -178.6(6) no C13 C14 C15 C16 -0.1(12) ? C14 C15 C16 C17 -0.1(12) ? C15 C16 C17 C18 0.1(11) ? C16 C17 C18 C13 0.0(10) ? C14 C13 C18 C17 -0.1(10) ? S10 C13 C18 C17 178.6(5) no C3 C2 C19 O20 105.0(7) ? N1 C2 C19 O20 -86.8(7) no C2 C19 O20 C21 153.3(5) ? C19 O20 C21 O22 1.4(10) ? C19 O20 C21 C23 -174.8(5) ? O22 C21 C23 C28 167.6(7) ? O20 C21 C23 C28 -16.3(9) ? O22 C21 C23 C24 -10.8(10) ? O20 C21 C23 C24 165.4(6) ? C28 C23 C24 C25 2.9(10) ? C21 C23 C24 C25 -178.6(6) ? C23 C24 C25 C26 -1.8(11) ? C24 C25 C26 C27 -0.3(12) ? C25 C26 C27 C28 1.4(12) ? C26 C27 C28 C23 -0.3(12) ? C24 C23 C28 C27 -1.9(10) ? C21 C23 C28 C27 179.8(6) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21137089 2 PubChem 102120483