#------------------------------------------------------------------------------ #$Date: 2023-10-26 02:45:04 +0300 (Thu, 26 Oct 2023) $ #$Revision: 287121 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/75/7247578.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_7247578 loop_ _publ_author_name 'Majee, Adinath' 'Pal, Satyajit' 'Sarkar, Subhankar' 'Mukherjee, Anindita' 'Kundu, Anupam' 'Sen, Animesh' 'Rath, Jnanendra' 'Santra, Sougata' 'Zyryanov, Grigory V.' _publ_section_title ; Metal-free, tert-butyl nitrite promoted C(sp2)-S coupling reaction: Synthesis of aryl dithiocarbamates and analysis of antimicrobial activity by ‘in silico’ and ‘in vitro’ methods for drug modification ; _journal_name_full 'Green Chemistry' _journal_paper_doi 10.1039/D3GC03153E _journal_year 2023 _chemical_formula_moiety 'C9 H10 N2 O2 S2' _chemical_formula_sum 'C9 H10 N2 O2 S2' _chemical_formula_weight 242.31 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2022-10-16 deposited with the CCDC. 2023-10-25 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 96.9390(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.5418(3) _cell_length_b 11.3152(4) _cell_length_c 12.9845(5) _cell_measurement_reflns_used 4381 _cell_measurement_temperature 142(2) _cell_measurement_theta_max 34.610 _cell_measurement_theta_min 2.395 _cell_volume 1099.94(7) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 142(2) _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.868 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0515 _diffrn_reflns_av_unetI/netI 0.0433 _diffrn_reflns_Laue_measured_fraction_full 0.983 _diffrn_reflns_Laue_measured_fraction_max 0.868 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 16894 _diffrn_reflns_point_group_measured_fraction_full 0.983 _diffrn_reflns_point_group_measured_fraction_max 0.868 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 34.610 _diffrn_reflns_theta_min 2.395 _exptl_absorpt_coefficient_mu 0.456 _exptl_crystal_colour YELLOW _exptl_crystal_density_diffrn 1.463 _exptl_crystal_description BLOCK _exptl_crystal_F_000 456 _refine_diff_density_max 0.366 _refine_diff_density_min -0.684 _refine_diff_density_rms 0.070 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 138 _refine_ls_number_reflns 4079 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.023 _refine_ls_R_factor_all 0.0669 _refine_ls_R_factor_gt 0.0475 _refine_ls_shift/su_max 0.0 _refine_ls_shift/su_mean 0.0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.3923P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1383 _refine_ls_wR_factor_ref 0.1668 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3169 _reflns_number_total 4079 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3gc03153e2.cif _cod_data_source_block mo_BIJON6060521_0m_a _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7247578 _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 ; mo_BIJON6060521_0m_a.res created by SHELXL-2014/7 TITL mo_BIJON6060521_0m_a.res in P2(1)/c CELL 0.71073 7.5418 11.3152 12.9845 90.000 96.939 90.000 ZERR 4.000 0.0003 0.0004 0.0005 0.000 0.001 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H N O S UNIT 28 40 8 8 8 REM Old TITL mo_BIJON6060521_0m in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.134, Rweak 0.003, Alpha 0.019, Orientation as input REM Formula found by SHELXT: C10 N O2 S2 L.S. 10 ACTA BOND $H FMAP 2 PLAN 20 TEMP -130.740 WGHT 0.100000 0.392300 FVAR 1.23744 S001 5 0.392547 0.776918 0.394166 11.00000 0.03411 0.03895 = 0.02504 -0.00295 -0.00292 0.00799 S002 5 0.674351 0.764322 0.580767 11.00000 0.03137 0.04339 = 0.03020 -0.00879 -0.00543 0.01136 O003 4 0.913074 0.299606 0.317680 11.00000 0.04810 0.03101 = 0.03787 -0.00499 0.00104 0.00616 O004 4 1.022487 0.437142 0.229292 11.00000 0.04900 0.05148 = 0.04091 -0.00728 0.02036 -0.00205 N005 3 0.377682 0.885468 0.574140 11.00000 0.02964 0.02993 = 0.02623 0.00003 0.00367 0.00579 N1 3 0.938020 0.403915 0.298654 11.00000 0.02586 0.03555 = 0.02818 -0.00405 -0.00084 0.00255 C007 1 0.465600 0.815363 0.515469 11.00000 0.02422 0.02482 = 0.02455 0.00211 0.00220 0.00134 C008 1 0.865729 0.494353 0.363954 11.00000 0.01948 0.02914 = 0.02592 -0.00051 0.00003 0.00124 C009 1 0.718164 0.540681 0.510707 11.00000 0.02155 0.03453 = 0.02730 0.00164 0.00259 -0.00073 AFIX 43 H009 2 0.659764 0.517013 0.568203 11.00000 -1.20000 AFIX 0 C00A 1 0.779632 0.455973 0.446104 11.00000 0.02174 0.02817 = 0.03059 0.00185 0.00087 -0.00181 AFIX 43 H00A 2 0.763034 0.374094 0.457986 11.00000 -1.20000 AFIX 0 C00B 1 0.893442 0.612384 0.343321 11.00000 0.02763 0.03210 = 0.02872 0.00484 0.00375 0.00021 AFIX 43 H00B 2 0.953829 0.635442 0.286428 11.00000 -1.20000 AFIX 0 C00C 1 0.742225 0.660470 0.491119 11.00000 0.02257 0.03296 = 0.02756 -0.00187 -0.00162 0.00548 C00D 1 0.830530 0.696330 0.408095 11.00000 0.03103 0.02605 = 0.03408 0.00260 0.00379 0.00165 AFIX 43 H00D 2 0.847675 0.778067 0.395817 11.00000 -1.20000 AFIX 0 C00E 1 0.443232 0.917519 0.681464 11.00000 0.04832 0.04280 = 0.02753 -0.00652 0.00256 0.00897 AFIX 137 H00C 2 0.509076 0.850765 0.715599 11.00000 -1.50000 H00E 2 0.341791 0.937108 0.718889 11.00000 -1.50000 H00F 2 0.522624 0.986098 0.681610 11.00000 -1.50000 AFIX 0 C00F 1 0.203463 0.933119 0.533625 11.00000 0.03529 0.03962 = 0.03968 0.00055 0.00504 0.01494 AFIX 137 H00G 2 0.209205 0.965821 0.464218 11.00000 -1.50000 H00H 2 0.170041 0.995655 0.579811 11.00000 -1.50000 H00I 2 0.114070 0.869904 0.529620 11.00000 -1.50000 AFIX 0 HKLF 4 REM mo_BIJON6060521_0m_a.res in P2(1)/c REM R1 = 0.0475 for 3169 Fo > 4sig(Fo) and 0.0669 for all 4079 data REM 138 parameters refined using 0 restraints END WGHT 0.0637 0.6054 REM Highest difference peak 0.366, deepest hole -0.684, 1-sigma level 0.070 Q1 1 0.8922 0.4593 0.3375 11.00000 0.05 0.37 Q2 1 0.3986 1.0030 0.6943 11.00000 0.05 0.36 Q3 1 0.8620 0.6567 0.3753 11.00000 0.05 0.35 Q4 1 0.7282 0.8582 0.5539 11.00000 0.05 0.32 Q5 1 0.7189 0.7110 0.5243 11.00000 0.05 0.31 Q6 1 0.7331 0.5120 0.4691 11.00000 0.05 0.31 Q7 1 0.7912 0.8172 0.5845 11.00000 0.05 0.29 Q8 1 0.7804 0.6673 0.4431 11.00000 0.05 0.29 Q9 1 0.7875 0.4806 0.3842 11.00000 0.05 0.29 Q10 1 0.6677 0.6741 0.5741 11.00000 0.05 0.29 Q11 1 0.1183 0.9094 0.5802 11.00000 0.05 0.29 Q12 1 0.2721 0.7752 0.4425 11.00000 0.05 0.28 Q13 1 0.7480 0.6035 0.4975 11.00000 0.05 0.28 Q14 1 0.5416 0.9203 0.6864 11.00000 0.05 0.28 Q15 1 0.3879 0.6812 0.4026 11.00000 0.05 0.27 Q16 1 0.4996 0.7231 0.3821 11.00000 0.05 0.27 Q17 1 0.5461 0.7613 0.5671 11.00000 0.05 0.27 Q18 1 0.1699 0.8926 0.4717 11.00000 0.05 0.27 Q19 1 0.4763 0.7887 0.4691 11.00000 0.05 0.26 Q20 1 0.9106 0.5406 0.3667 11.00000 0.05 0.26 ; _shelx_res_checksum 23540 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, 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_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 S001 S 0.39255(6) 0.77692(4) 0.39417(3) 0.03323(13) Uani 1 1 d . . . . . S002 S 0.67435(6) 0.76432(4) 0.58077(3) 0.03574(14) Uani 1 1 d . . . . . O003 O 0.91307(19) 0.29961(11) 0.31768(10) 0.0393(3) Uani 1 1 d . . . . . O004 O 1.0225(2) 0.43714(14) 0.22929(11) 0.0459(3) Uani 1 1 d . . . . . N005 N 0.37768(17) 0.88547(12) 0.57414(10) 0.0286(3) Uani 1 1 d . . . . . N1 N 0.93802(18) 0.40391(12) 0.29865(10) 0.0302(3) Uani 1 1 d . . . . . C007 C 0.46560(18) 0.81536(13) 0.51547(10) 0.0246(3) Uani 1 1 d . . . . . C008 C 0.86573(17) 0.49435(13) 0.36395(11) 0.0251(3) Uani 1 1 d . . . . . C009 C 0.71816(19) 0.54068(14) 0.51071(11) 0.0278(3) Uani 1 1 d . . . . . H009 H 0.6598 0.5170 0.5682 0.033 Uiso 1 1 calc R U . . . C00A C 0.77963(19) 0.45597(13) 0.44610(12) 0.0270(3) Uani 1 1 d . . . . . H00A H 0.7630 0.3741 0.4580 0.032 Uiso 1 1 calc R U . . . C00B C 0.8934(2) 0.61238(14) 0.34332(12) 0.0295(3) Uani 1 1 d . . . . . H00B H 0.9538 0.6354 0.2864 0.035 Uiso 1 1 calc R U . . . C00C C 0.74223(19) 0.66047(13) 0.49112(12) 0.0281(3) Uani 1 1 d . . . . . C00D C 0.8305(2) 0.69633(14) 0.40810(12) 0.0304(3) Uani 1 1 d . . . . . H00D H 0.8477 0.7781 0.3958 0.036 Uiso 1 1 calc R U . . . C00E C 0.4432(3) 0.91752(17) 0.68146(13) 0.0397(4) Uani 1 1 d . . . . . H00C H 0.5091 0.8508 0.7156 0.060 Uiso 1 1 calc R U . . . H00E H 0.3418 0.9371 0.7189 0.060 Uiso 1 1 calc R U . . . H00F H 0.5226 0.9861 0.6816 0.060 Uiso 1 1 calc R U . . . C00F C 0.2035(2) 0.93312(17) 0.53362(15) 0.0382(4) Uani 1 1 d . . . . . H00G H 0.2092 0.9658 0.4642 0.057 Uiso 1 1 calc R U . . . H00H H 0.1700 0.9957 0.5798 0.057 Uiso 1 1 calc R U . . . H00I H 0.1141 0.8699 0.5296 0.057 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 S001 0.0341(2) 0.0390(2) 0.0250(2) -0.00295(14) -0.00292(15) 0.00799(15) S002 0.0314(2) 0.0434(2) 0.0302(2) -0.00879(15) -0.00543(15) 0.01136(15) O003 0.0481(7) 0.0310(5) 0.0379(6) -0.0050(5) 0.0010(5) 0.0062(5) O004 0.0490(8) 0.0515(8) 0.0409(7) -0.0073(6) 0.0204(6) -0.0021(6) N005 0.0296(6) 0.0299(6) 0.0262(6) 0.0000(5) 0.0037(5) 0.0058(5) N1 0.0259(6) 0.0355(6) 0.0282(6) -0.0041(5) -0.0008(5) 0.0026(5) C007 0.0242(6) 0.0248(6) 0.0245(6) 0.0021(5) 0.0022(5) 0.0013(4) C008 0.0195(6) 0.0291(6) 0.0259(6) -0.0005(5) 0.0000(5) 0.0012(5) C009 0.0216(6) 0.0345(7) 0.0273(6) 0.0016(5) 0.0026(5) -0.0007(5) C00A 0.0217(6) 0.0282(6) 0.0306(7) 0.0018(5) 0.0009(5) -0.0018(5) C00B 0.0276(7) 0.0321(7) 0.0287(7) 0.0048(5) 0.0038(5) 0.0002(5) C00C 0.0226(6) 0.0330(7) 0.0276(6) -0.0019(5) -0.0016(5) 0.0055(5) C00D 0.0310(7) 0.0261(6) 0.0341(7) 0.0026(5) 0.0038(6) 0.0016(5) C00E 0.0483(10) 0.0428(9) 0.0275(7) -0.0065(6) 0.0026(7) 0.0090(7) C00F 0.0353(8) 0.0396(8) 0.0397(8) 0.0006(7) 0.0050(6) 0.0149(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' 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' 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 C00C S002 C007 102.12(7) . . ? C007 N005 C00F 120.22(13) . . ? C007 N005 C00E 123.86(13) . . ? C00F N005 C00E 115.90(13) . . ? O003 N1 O004 123.42(14) . . ? O003 N1 C008 118.43(13) . . ? O004 N1 C008 118.13(13) . . ? N005 C007 S001 124.56(11) . . ? N005 C007 S002 113.04(10) . . ? S001 C007 S002 122.40(8) . . ? C00B C008 C00A 123.25(14) . . ? C00B C008 N1 118.93(13) . . ? C00A C008 N1 117.76(13) . . ? C00A C009 C00C 119.99(13) . . ? C00A C009 H009 120.0 . . ? C00C C009 H009 120.0 . . ? C008 C00A C009 118.07(13) . . ? C008 C00A H00A 121.0 . . ? C009 C00A H00A 121.0 . . ? C008 C00B C00D 118.18(14) . . ? C008 C00B H00B 120.9 . . ? C00D C00B H00B 120.9 . . ? C009 C00C C00D 120.57(14) . . ? C009 C00C S002 118.05(11) . . ? C00D C00C S002 121.18(12) . . ? C00B C00D C00C 119.93(14) . . ? C00B C00D H00D 120.0 . . ? C00C C00D H00D 120.0 . . ? N005 C00E H00C 109.5 . . ? N005 C00E H00E 109.5 . . ? H00C C00E H00E 109.5 . . ? N005 C00E H00F 109.5 . . ? H00C C00E H00F 109.5 . . ? H00E C00E H00F 109.5 . . ? N005 C00F H00G 109.5 . . ? N005 C00F H00H 109.5 . . ? H00G C00F H00H 109.5 . . ? N005 C00F H00I 109.5 . . ? H00G C00F H00I 109.5 . . ? H00H C00F H00I 109.5 . . ? 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 S001 C007 1.6625(14) . ? S002 C00C 1.7725(15) . ? S002 C007 1.7912(14) . ? O003 N1 1.2250(19) . ? O004 N1 1.2235(19) . ? N005 C007 1.3309(18) . ? N005 C00F 1.458(2) . ? N005 C00E 1.467(2) . ? N1 C008 1.4748(19) . ? C008 C00B 1.383(2) . ? C008 C00A 1.3840(19) . ? C009 C00A 1.390(2) . ? C009 C00C 1.395(2) . ? C009 H009 0.9500 . ? C00A H00A 0.9500 . ? C00B C00D 1.390(2) . ? C00B H00B 0.9500 . ? C00C C00D 1.394(2) . ? C00D H00D 0.9500 . ? C00E H00C 0.9800 . ? C00E H00E 0.9800 . ? C00E H00F 0.9800 . ? C00F H00G 0.9800 . ? C00F H00H 0.9800 . ? C00F H00I 0.9800 . ?