#------------------------------------------------------------------------------ #$Date: 2020-05-12 06:54:16 +0300 (Tue, 12 May 2020) $ #$Revision: 251979 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157497.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_7157497 loop_ _publ_author_name 'Mondal, Santa' 'Mahato, Karuna' 'Arora, Neha' 'Kankane, Dheerendra' 'Singh, Umed Pratap' 'Ali, Saghir' 'Khan, Aftab Hossain' 'Ghosh, Siddhartha Sankar' 'Khan, Abu Taleb' _publ_section_title ; Newly Synthesized 3-Sulfenylindole Derivatives from 4-Hydroxydithiocoumarin using Oxidative Cross Dehydrogenative Coupling Reaction (OCDCR): Potential Lead Molecules for Antiproliferative Activity† ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D0OB00054J _journal_year 2020 _chemical_formula_sum 'C17 H11 N O3 S2' _chemical_formula_weight 341.39 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2018-12-27 deposited with the CCDC. 2020-05-11 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.4978(4) _cell_length_b 14.5164(14) _cell_length_c 16.2262(14) _cell_measurement_reflns_used 1024 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 23.2280 _cell_measurement_theta_min 3.3590 _cell_volume 1530.5(2) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0405 _diffrn_reflns_av_unetI/netI 0.0858 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 4734 _diffrn_reflns_point_group_measured_fraction_full 0.977 _diffrn_reflns_point_group_measured_fraction_max 0.977 _diffrn_reflns_theta_full 25.040 _diffrn_reflns_theta_max 25.040 _diffrn_reflns_theta_min 2.876 _exptl_absorpt_coefficient_mu 0.362 _exptl_crystal_colour brown _exptl_crystal_density_diffrn 1.482 _exptl_crystal_description block _exptl_crystal_F_000 704 _refine_diff_density_max 0.285 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.049 _refine_ls_abs_structure_details ; Flack x determined using 463 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.15(9) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 208 _refine_ls_number_reflns 2644 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.011 _refine_ls_R_factor_all 0.0933 _refine_ls_R_factor_gt 0.0576 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0232P)^2^+0.3631P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0900 _refine_ls_wR_factor_ref 0.1094 _reflns_Friedel_coverage 0.673 _reflns_Friedel_fraction_full 0.948 _reflns_Friedel_fraction_max 0.948 _reflns_number_gt 1798 _reflns_number_total 2644 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00054j2.cif _cod_data_source_block exp_5482 _cod_database_code 7157497 _shelx_shelxl_version_number 2014/7 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_res_file ; exp_5482.res created by SHELXL-2014/7 TITL exp_5482_a.res in P2(1)2(1)2(1) CELL 0.71073 6.4978 14.5164 16.2262 90 90 90 ZERR 4 0.0004 0.0014 0.0014 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H O S N UNIT 68 44 12 8 4 OMIT -3 50.1 L.S. 20 ACTA BOND $H FMAP 2 PLAN 5 WGHT 0.023200 0.363100 FVAR 0.62414 S1 4 -0.006733 0.437060 0.535973 11.00000 0.03996 0.05763 = 0.06689 -0.00839 0.00553 -0.00774 S2 4 0.188305 0.584725 0.630605 11.00000 0.04931 0.04854 = 0.07811 -0.01263 0.00402 0.00165 O14 3 0.577023 0.440544 0.394989 11.00000 0.04743 0.09513 = 0.06718 0.00408 0.01857 0.00089 O13 3 -0.024909 0.584192 0.654126 11.00000 0.04203 0.07568 = 0.09953 -0.02020 0.00456 0.01355 O12 3 0.283294 0.668479 0.603887 11.00000 0.09555 0.04599 = 0.10494 -0.00861 0.01132 -0.01265 C5 1 0.257113 0.367066 0.416074 11.00000 0.04631 0.04826 = 0.04359 0.00842 -0.00788 0.00373 C2 1 0.210151 0.504730 0.546975 11.00000 0.03807 0.03880 = 0.05855 0.00494 0.00107 0.00464 C10 1 0.069085 0.362649 0.457785 11.00000 0.04448 0.04083 = 0.04160 0.00001 -0.00231 0.00030 C4 1 0.414902 0.436959 0.433878 11.00000 0.03898 0.06001 = 0.04392 0.00718 -0.00206 0.00679 C3 1 0.379016 0.500160 0.500577 11.00000 0.03492 0.05015 = 0.06405 0.00479 0.00039 -0.00019 AFIX 43 H3 2 0.483631 0.541814 0.512462 11.00000 -1.20000 AFIX 0 C9 1 -0.072915 0.295125 0.437460 11.00000 0.06273 0.04295 = 0.05531 0.00358 -0.00529 -0.00677 AFIX 43 H9 2 -0.198327 0.292711 0.464994 11.00000 -1.20000 AFIX 0 N1 5 0.602162 0.512209 0.788552 11.00000 0.03939 0.10967 = 0.08168 -0.03373 -0.00232 0.00676 AFIX 43 H22 2 0.720582 0.518650 0.811510 11.00000 -1.20000 AFIX 0 C15 1 0.333666 0.536276 0.706735 11.00000 0.03644 0.05032 = 0.06429 -0.01866 0.00047 -0.00261 C16 1 0.285127 0.458583 0.758175 11.00000 0.04339 0.05966 = 0.05882 -0.02752 0.00154 0.00334 C17 1 0.115051 0.400571 0.766958 11.00000 0.06695 0.05512 = 0.07650 -0.01773 0.00920 -0.00405 AFIX 43 H17 2 -0.002066 0.408327 0.734752 11.00000 -1.20000 AFIX 0 C6 1 0.298516 0.302067 0.353957 11.00000 0.06715 0.06962 = 0.04820 0.00488 -0.00099 0.01347 AFIX 43 H6 2 0.422279 0.304497 0.325252 11.00000 -1.20000 AFIX 0 C8 1 -0.030323 0.232187 0.377431 11.00000 0.07979 0.04951 = 0.07259 -0.00023 -0.01550 -0.01267 AFIX 43 H8 2 -0.126445 0.187059 0.364266 11.00000 -1.20000 AFIX 0 C21 1 0.458656 0.445239 0.808696 11.00000 0.05912 0.07622 = 0.06481 -0.03074 -0.00593 0.02104 C7 1 0.157534 0.235460 0.335716 11.00000 0.09061 0.05955 = 0.06049 -0.01214 -0.00399 0.00440 AFIX 43 H7 2 0.186706 0.191988 0.295270 11.00000 -1.20000 AFIX 0 C23 1 0.528147 0.565517 0.727720 11.00000 0.05022 0.08286 = 0.07540 -0.02830 0.00652 -0.01215 AFIX 43 H23 2 0.597594 0.614583 0.703537 11.00000 -1.20000 AFIX 0 C18 1 0.126734 0.331432 0.824992 11.00000 0.09965 0.06473 = 0.08558 -0.01376 0.01879 -0.00646 AFIX 43 H18 2 0.014574 0.292434 0.832095 11.00000 -1.20000 AFIX 0 C19 1 0.302422 0.318111 0.873610 11.00000 0.15490 0.07132 = 0.07372 -0.00575 0.00437 0.03438 AFIX 43 H19 2 0.306253 0.269468 0.910876 11.00000 -1.20000 AFIX 0 C20 1 0.469973 0.376156 0.867000 11.00000 0.09653 0.10364 = 0.07218 -0.03319 -0.01494 0.04383 AFIX 43 H20 2 0.585303 0.369031 0.900337 11.00000 -1.20000 AFIX 0 HKLF 4 REM exp_5482_a.res in P2(1)2(1)2(1) REM R1 = 0.0576 for 1798 Fo > 4sig(Fo) and 0.0933 for all 2644 data REM 208 parameters refined using 0 restraints END WGHT 0.0192 0.0633 REM Highest difference peak 0.285, deepest hole -0.187, 1-sigma level 0.049 Q1 1 -0.0142 0.4328 0.4597 11.00000 0.05 0.23 Q2 1 0.4772 0.6783 0.5027 11.00000 0.05 0.18 Q3 1 0.2088 0.5036 0.6024 11.00000 0.05 0.16 Q4 1 0.5168 0.5505 0.7982 11.00000 0.05 0.16 Q5 1 0.3632 0.3869 0.8811 11.00000 0.05 0.16 ; _shelx_res_checksum 47760 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S -0.0067(2) 0.43706(12) 0.53597(11) 0.0548(5) Uani 1 1 d . . . . . S2 S 0.1883(3) 0.58472(13) 0.63061(12) 0.0587(5) Uani 1 1 d . . . . . O14 O 0.5770(6) 0.4405(4) 0.3950(3) 0.0699(15) Uani 1 1 d . . . . . O13 O -0.0249(6) 0.5842(3) 0.6541(3) 0.0724(15) Uani 1 1 d . . . . . O12 O 0.2833(8) 0.6685(3) 0.6039(3) 0.0822(17) Uani 1 1 d . . . . . C5 C 0.2571(9) 0.3671(5) 0.4161(4) 0.0461(17) Uani 1 1 d . . . . . C2 C 0.2102(9) 0.5047(4) 0.5470(4) 0.0451(16) Uani 1 1 d . . . . . C10 C 0.0691(9) 0.3626(4) 0.4578(4) 0.0423(16) Uani 1 1 d . . . . . C4 C 0.4149(9) 0.4370(5) 0.4339(4) 0.0476(17) Uani 1 1 d . . . . . C3 C 0.3790(9) 0.5002(5) 0.5006(4) 0.0497(18) Uani 1 1 d . . . . . H3 H 0.4836 0.5418 0.5125 0.060 Uiso 1 1 calc R U . . . C9 C -0.0729(10) 0.2951(5) 0.4375(4) 0.0537(18) Uani 1 1 d . . . . . H9 H -0.1983 0.2927 0.4650 0.064 Uiso 1 1 calc R U . . . N1 N 0.6022(9) 0.5122(5) 0.7886(4) 0.077(2) Uani 1 1 d . . . . . H22 H 0.7206 0.5187 0.8115 0.092 Uiso 1 1 calc R U . . . C15 C 0.3337(9) 0.5363(5) 0.7067(4) 0.0504(18) Uani 1 1 d . . . . . C16 C 0.2851(10) 0.4586(5) 0.7582(4) 0.0540(19) Uani 1 1 d . . . . . C17 C 0.1151(11) 0.4006(5) 0.7670(5) 0.066(2) Uani 1 1 d . . . . . H17 H -0.0021 0.4083 0.7348 0.079 Uiso 1 1 calc R U . . . C6 C 0.2985(11) 0.3021(5) 0.3540(4) 0.062(2) Uani 1 1 d . . . . . H6 H 0.4223 0.3045 0.3253 0.074 Uiso 1 1 calc R U . . . C8 C -0.0303(12) 0.2322(5) 0.3774(5) 0.067(2) Uani 1 1 d . . . . . H8 H -0.1264 0.1871 0.3643 0.081 Uiso 1 1 calc R U . . . C21 C 0.4587(12) 0.4452(6) 0.8087(5) 0.067(2) Uani 1 1 d . . . . . C7 C 0.1575(12) 0.2355(5) 0.3357(5) 0.070(2) Uani 1 1 d . . . . . H7 H 0.1867 0.1920 0.2953 0.084 Uiso 1 1 calc R U . . . C23 C 0.5281(10) 0.5655(6) 0.7277(5) 0.069(2) Uani 1 1 d . . . . . H23 H 0.5976 0.6146 0.7035 0.083 Uiso 1 1 calc R U . . . C18 C 0.1267(14) 0.3314(6) 0.8250(6) 0.083(3) Uani 1 1 d . . . . . H18 H 0.0146 0.2924 0.8321 0.100 Uiso 1 1 calc R U . . . C19 C 0.3024(18) 0.3181(6) 0.8736(6) 0.100(3) Uani 1 1 d . . . . . H19 H 0.3063 0.2695 0.9109 0.120 Uiso 1 1 calc R U . . . C20 C 0.4700(15) 0.3762(7) 0.8670(6) 0.091(3) Uani 1 1 d . . . . . H20 H 0.5853 0.3690 0.9003 0.109 Uiso 1 1 calc R U . . . 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 S1 0.0400(8) 0.0576(12) 0.0669(11) -0.0084(10) 0.0055(9) -0.0077(10) S2 0.0493(10) 0.0485(12) 0.0781(13) -0.0126(11) 0.0040(10) 0.0016(9) O14 0.047(2) 0.095(4) 0.067(3) 0.004(3) 0.019(2) 0.001(3) O13 0.042(2) 0.076(4) 0.100(4) -0.020(3) 0.005(3) 0.014(3) O12 0.096(4) 0.046(3) 0.105(4) -0.009(3) 0.011(4) -0.013(3) C5 0.046(4) 0.048(4) 0.044(4) 0.008(3) -0.008(3) 0.004(3) C2 0.038(3) 0.039(4) 0.059(4) 0.005(3) 0.001(3) 0.005(3) C10 0.044(4) 0.041(4) 0.042(4) 0.000(3) -0.002(3) 0.000(3) C4 0.039(3) 0.060(5) 0.044(4) 0.007(4) -0.002(3) 0.007(4) C3 0.035(3) 0.050(4) 0.064(5) 0.005(4) 0.000(3) 0.000(3) C9 0.063(4) 0.043(4) 0.055(5) 0.004(4) -0.005(4) -0.007(4) N1 0.039(3) 0.110(6) 0.082(5) -0.034(5) -0.002(3) 0.007(4) C15 0.036(3) 0.050(5) 0.064(5) -0.019(4) 0.000(3) -0.003(3) C16 0.043(4) 0.060(5) 0.059(5) -0.028(4) 0.002(4) 0.003(4) C17 0.067(5) 0.055(5) 0.076(6) -0.018(4) 0.009(4) -0.004(4) C6 0.067(5) 0.070(5) 0.048(4) 0.005(4) -0.001(4) 0.013(5) C8 0.080(6) 0.050(5) 0.073(6) 0.000(4) -0.016(5) -0.013(4) C21 0.059(5) 0.076(6) 0.065(5) -0.031(5) -0.006(4) 0.021(5) C7 0.091(6) 0.060(6) 0.060(5) -0.012(4) -0.004(5) 0.004(5) C23 0.050(4) 0.083(6) 0.075(6) -0.028(5) 0.007(4) -0.012(5) C18 0.100(7) 0.065(6) 0.086(7) -0.014(5) 0.019(6) -0.006(5) C19 0.155(9) 0.071(7) 0.074(7) -0.006(6) 0.004(8) 0.034(7) C20 0.097(7) 0.104(8) 0.072(6) -0.033(6) -0.015(6) 0.044(7) 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' 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' N N 0.0061 0.0033 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 S1 C10 101.4(3) . . ? O12 S2 O13 120.1(3) . . ? O12 S2 C15 109.3(3) . . ? O13 S2 C15 109.8(3) . . ? O12 S2 C2 106.7(3) . . ? O13 S2 C2 105.9(3) . . ? C15 S2 C2 103.7(3) . . ? C10 C5 C6 118.9(6) . . ? C10 C5 C4 123.1(6) . . ? C6 C5 C4 118.0(6) . . ? C3 C2 S1 125.8(5) . . ? C3 C2 S2 121.7(5) . . ? S1 C2 S2 112.5(3) . . ? C9 C10 C5 119.9(6) . . ? C9 C10 S1 115.1(5) . . ? C5 C10 S1 124.9(5) . . ? O14 C4 C3 119.9(6) . . ? O14 C4 C5 121.7(7) . . ? C3 C4 C5 118.4(5) . . ? C2 C3 C4 126.2(6) . . ? C2 C3 H3 116.9 . . ? C4 C3 H3 116.9 . . ? C8 C9 C10 120.6(7) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C23 N1 C21 109.7(6) . . ? C23 N1 H22 125.2 . . ? C21 N1 H22 125.2 . . ? C23 C15 C16 107.4(7) . . ? C23 C15 S2 124.1(6) . . ? C16 C15 S2 128.5(5) . . ? C17 C16 C21 119.4(8) . . ? C17 C16 C15 134.9(7) . . ? C21 C16 C15 105.7(7) . . ? C18 C17 C16 117.7(8) . . ? C18 C17 H17 121.1 . . ? C16 C17 H17 121.1 . . ? C7 C6 C5 120.2(7) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C9 C8 C7 120.0(7) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C20 C21 N1 129.4(8) . . ? C20 C21 C16 122.8(9) . . ? N1 C21 C16 107.8(8) . . ? C6 C7 C8 120.4(7) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? N1 C23 C15 109.4(7) . . ? N1 C23 H23 125.3 . . ? C15 C23 H23 125.3 . . ? C17 C18 C19 122.0(9) . . ? C17 C18 H18 119.0 . . ? C19 C18 H18 119.0 . . ? C20 C19 C18 121.0(9) . . ? C20 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C21 C20 C19 117.0(9) . . ? C21 C20 H20 121.5 . . ? C19 C20 H20 121.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C2 1.727(6) . ? S1 C10 1.738(6) . ? S2 O12 1.431(5) . ? S2 O13 1.437(4) . ? S2 C15 1.707(7) . ? S2 C2 1.792(6) . ? O14 C4 1.229(6) . ? C5 C10 1.398(8) . ? C5 C6 1.407(9) . ? C5 C4 1.471(8) . ? C2 C3 1.332(8) . ? C10 C9 1.386(8) . ? C4 C3 1.438(8) . ? C3 H3 0.9300 . ? C9 C8 1.364(9) . ? C9 H9 0.9300 . ? N1 C23 1.343(9) . ? N1 C21 1.386(10) . ? N1 H22 0.8600 . ? C15 C23 1.376(8) . ? C15 C16 1.438(9) . ? C16 C17 1.397(9) . ? C16 C21 1.407(9) . ? C17 C18 1.378(10) . ? C17 H17 0.9300 . ? C6 C7 1.364(9) . ? C6 H6 0.9300 . ? C8 C7 1.397(9) . ? C8 H8 0.9300 . ? C21 C20 1.381(11) . ? C7 H7 0.9300 . ? C23 H23 0.9300 . ? C18 C19 1.401(11) . ? C18 H18 0.9300 . ? C19 C20 1.381(11) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ?