#------------------------------------------------------------------------------ #$Date: 2020-06-22 00:21:34 +0300 (Mon, 22 Jun 2020) $ #$Revision: 253300 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/03/85/4038504.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_4038504 loop_ _publ_author_name 'Qi, Peng' 'Sun, Fang' 'Chen, Ning' 'Du, Hongguang' _publ_section_title ; Cross-Dehydrogenative Coupling of Azoarenes with Dialkyl Disulfides. ; _journal_name_full 'The Journal of organic chemistry' _journal_paper_doi 10.1021/acs.joc.0c00953 _journal_year 2020 _chemical_formula_moiety 'C17 H18 N2 S2' _chemical_formula_sum 'C17 H18 N2 S2' _chemical_formula_weight 314.45 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2019-04-02 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _cell_angle_alpha 85.666(5) _cell_angle_beta 76.940(5) _cell_angle_gamma 82.440(5) _cell_formula_units_Z 2 _cell_length_a 8.2539(5) _cell_length_b 9.8450(6) _cell_length_c 10.1665(6) _cell_measurement_reflns_used 2941 _cell_measurement_temperature 108.45(10) _cell_measurement_theta_max 28.8230 _cell_measurement_theta_min 4.1090 _cell_volume 796.86(9) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)/Bruker' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 108.45(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.0971 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.9979 _diffrn_measured_fraction_theta_max 0.8385 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -13.00 24.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -13.5772 -99.0000 30.0000 37 #__ type_ start__ end____ width___ exp.time_ 2 omega -15.00 11.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -13.5772 -99.0000 150.0000 26 #__ type_ start__ end____ width___ exp.time_ 3 omega -42.00 0.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -13.5772 -19.0000 60.0000 42 #__ type_ start__ end____ width___ exp.time_ 4 omega 0.00 67.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 18.8116 37.0000 60.0000 67 #__ type_ start__ end____ width___ exp.time_ 5 omega 36.00 68.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 18.8116 178.0000 -150.0000 32 #__ type_ start__ end____ width___ exp.time_ 6 omega -44.00 -3.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -13.5772 83.0000 92.0000 41 #__ type_ start__ end____ width___ exp.time_ 7 omega -38.00 36.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 18.8116 -57.0000 -90.0000 74 #__ type_ start__ end____ width___ exp.time_ 8 omega -48.00 36.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 18.8116 -57.0000 -150.0000 84 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0721053000 _diffrn_orient_matrix_UB_12 0.0017355000 _diffrn_orient_matrix_UB_13 -0.0532342000 _diffrn_orient_matrix_UB_21 -0.0424755000 _diffrn_orient_matrix_UB_22 0.0546063000 _diffrn_orient_matrix_UB_23 -0.0333039000 _diffrn_orient_matrix_UB_31 0.0298090000 _diffrn_orient_matrix_UB_32 0.0480546000 _diffrn_orient_matrix_UB_33 0.0346136000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_unetI/netI 0.0369 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 6307 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_min 3.34 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.329 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.85899 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_description ; ; _exptl_crystal_F_000 332 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.23 _refine_diff_density_max 0.242 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.057 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 192 _refine_ls_number_reflns 3122 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.034 _refine_ls_R_factor_all 0.0379 _refine_ls_R_factor_gt 0.0333 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0362P)^2^+0.3020P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0792 _refine_ls_wR_factor_ref 0.0824 _reflns_number_gt 2802 _reflns_number_total 3122 _reflns_threshold_expression >2sigma(I) _cod_data_source_file jo0c00953_si_002.cif _cod_data_source_block exp_5909 _cod_original_cell_volume 796.86(8) _cod_database_code 4038504 _reflns_odcompleteness_completeness 99.79 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.92918(5) 0.17095(4) 0.17245(4) 0.01663(12) Uani 1 1 d . . . S2 S 0.92627(5) 0.34743(4) 0.05381(4) 0.01799(12) Uani 1 1 d . . . N1 N 0.62639(17) 0.14047(13) 0.11704(13) 0.0145(3) Uani 1 1 d . . . N2 N 0.41109(17) 0.27600(13) 0.05457(13) 0.0164(3) Uani 1 1 d . . . C3 C 0.3809(2) 0.26251(16) 0.19535(16) 0.0159(3) Uani 1 1 d . . . C7 C 0.5206(2) 0.15724(16) 0.37246(16) 0.0186(4) Uani 1 1 d . . . H7 H 0.6103 0.1039 0.3992 0.022 Uiso 1 1 calc R . . C1 C 0.5577(2) 0.20439(15) 0.01249(16) 0.0150(3) Uani 1 1 d . . . C8 C 0.6424(2) 0.19678(16) -0.13168(16) 0.0156(3) Uani 1 1 d . . . C2 C 0.5146(2) 0.18006(16) 0.23635(16) 0.0158(3) Uani 1 1 d . . . C14 C 0.7955(2) 0.07034(16) 0.10474(16) 0.0154(3) Uani 1 1 d . . . H14 H 0.8446 0.0601 0.0083 0.019 Uiso 1 1 calc R . . C13 C 0.7047(2) 0.07196(16) -0.19139(16) 0.0176(3) Uani 1 1 d . . . H13 H 0.6938 -0.0098 -0.1399 0.021 Uiso 1 1 calc R . . C6 C 0.3869(2) 0.21780(17) 0.46547(17) 0.0224(4) Uani 1 1 d . . . H6 H 0.3876 0.2060 0.5570 0.027 Uiso 1 1 calc R . . C12 C 0.7827(2) 0.06962(17) -0.32735(17) 0.0203(4) Uani 1 1 d . . . H12 H 0.8239 -0.0138 -0.3666 0.024 Uiso 1 1 calc R . . C15 C 0.7999(2) -0.07275(16) 0.17419(17) 0.0208(4) Uani 1 1 d . . . H15A H 0.9135 -0.1156 0.1594 0.031 Uiso 1 1 calc R . . H15B H 0.7339 -0.1270 0.1374 0.031 Uiso 1 1 calc R . . H15C H 0.7551 -0.0655 0.2695 0.031 Uiso 1 1 calc R . . C4 C 0.2448(2) 0.31997(16) 0.29100(17) 0.0204(4) Uani 1 1 d . . . H4 H 0.1540 0.3721 0.2648 0.024 Uiso 1 1 calc R . . C11 C 0.7996(2) 0.19119(18) -0.40507(17) 0.0225(4) Uani 1 1 d . . . H11 H 0.8529 0.1894 -0.4960 0.027 Uiso 1 1 calc R . . C10 C 0.7364(2) 0.31546(18) -0.34638(17) 0.0250(4) Uani 1 1 d . . . H10 H 0.7466 0.3970 -0.3985 0.030 Uiso 1 1 calc R . . C9 C 0.6582(2) 0.31886(17) -0.21077(17) 0.0208(4) Uani 1 1 d . . . H9 H 0.6160 0.4025 -0.1722 0.025 Uiso 1 1 calc R . . C16 C 0.7476(2) 0.45920(16) 0.14226(18) 0.0207(4) Uani 1 1 d . . . H16A H 0.7289 0.5402 0.0847 0.025 Uiso 1 1 calc R . . H16B H 0.6486 0.4117 0.1583 0.025 Uiso 1 1 calc R . . C5 C 0.2498(2) 0.29666(17) 0.42585(17) 0.0229(4) Uani 1 1 d . . . H5 H 0.1607 0.3338 0.4916 0.028 Uiso 1 1 calc R . . C17 C 0.7696(3) 0.5034(2) 0.2759(2) 0.0366(5) Uani 1 1 d . . . H17A H 0.8656 0.5527 0.2607 0.055 Uiso 1 1 calc R . . H17B H 0.7856 0.4239 0.3344 0.055 Uiso 1 1 calc R . . H17C H 0.6716 0.5617 0.3173 0.055 Uiso 1 1 calc R . . 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 0.0158(2) 0.0159(2) 0.0191(2) 0.00040(15) -0.00672(16) -0.00102(16) S2 0.0181(2) 0.0163(2) 0.0190(2) 0.00127(15) -0.00262(17) -0.00385(16) N1 0.0139(7) 0.0151(6) 0.0141(7) 0.0007(5) -0.0024(5) -0.0021(5) N2 0.0162(7) 0.0156(7) 0.0179(7) 0.0000(5) -0.0047(6) -0.0027(5) C3 0.0158(8) 0.0148(8) 0.0181(8) -0.0014(6) -0.0042(7) -0.0044(6) C7 0.0209(9) 0.0178(8) 0.0178(8) 0.0013(6) -0.0049(7) -0.0050(7) C1 0.0165(8) 0.0128(7) 0.0174(8) 0.0005(6) -0.0057(7) -0.0046(6) C8 0.0129(8) 0.0188(8) 0.0169(8) -0.0004(6) -0.0061(6) -0.0036(6) C2 0.0146(8) 0.0154(8) 0.0173(8) -0.0017(6) -0.0010(6) -0.0055(6) C14 0.0136(8) 0.0159(8) 0.0162(8) -0.0003(6) -0.0025(6) -0.0011(6) C13 0.0198(9) 0.0158(8) 0.0192(8) 0.0002(6) -0.0076(7) -0.0043(7) C6 0.0279(10) 0.0232(9) 0.0158(8) -0.0012(7) -0.0001(7) -0.0093(7) C12 0.0212(9) 0.0207(8) 0.0201(9) -0.0065(7) -0.0055(7) -0.0015(7) C15 0.0204(9) 0.0157(8) 0.0250(9) 0.0019(7) -0.0033(7) -0.0015(7) C4 0.0166(9) 0.0172(8) 0.0265(9) -0.0039(7) -0.0017(7) -0.0027(7) C11 0.0239(9) 0.0291(9) 0.0147(8) -0.0013(7) -0.0035(7) -0.0054(8) C10 0.0336(11) 0.0224(9) 0.0186(9) 0.0042(7) -0.0047(8) -0.0061(8) C9 0.0236(9) 0.0169(8) 0.0211(9) -0.0011(7) -0.0044(7) -0.0006(7) C16 0.0175(9) 0.0131(8) 0.0307(10) 0.0008(7) -0.0048(7) -0.0008(7) C5 0.0212(9) 0.0231(9) 0.0225(9) -0.0076(7) 0.0039(7) -0.0067(7) C17 0.0416(13) 0.0332(11) 0.0328(11) -0.0127(9) -0.0081(9) 0.0101(9) 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' 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 C14 S1 S2 102.41(5) . . ? C16 S2 S1 104.61(6) . . ? C1 N1 C2 106.01(13) . . ? C1 N1 C14 126.27(13) . . ? C2 N1 C14 126.63(13) . . ? C1 N2 C3 104.97(13) . . ? N2 C3 C2 110.27(14) . . ? N2 C3 C4 129.18(15) . . ? C4 C3 C2 120.54(15) . . ? C2 C7 H7 121.6 . . ? C6 C7 H7 121.6 . . ? C6 C7 C2 116.74(16) . . ? N1 C1 C8 123.60(14) . . ? N2 C1 N1 113.29(14) . . ? N2 C1 C8 123.08(14) . . ? C13 C8 C1 122.12(14) . . ? C13 C8 C9 119.24(15) . . ? C9 C8 C1 118.63(14) . . ? N1 C2 C3 105.41(14) . . ? N1 C2 C7 132.67(15) . . ? C7 C2 C3 121.84(15) . . ? S1 C14 H14 107.7 . . ? N1 C14 S1 111.67(10) . . ? N1 C14 H14 107.7 . . ? N1 C14 C15 113.06(13) . . ? C15 C14 S1 108.79(11) . . ? C15 C14 H14 107.7 . . ? C8 C13 H13 119.9 . . ? C12 C13 C8 120.17(15) . . ? C12 C13 H13 119.9 . . ? C7 C6 H6 119.0 . . ? C7 C6 C5 121.91(16) . . ? C5 C6 H6 119.0 . . ? C13 C12 H12 119.8 . . ? C13 C12 C11 120.35(15) . . ? C11 C12 H12 119.8 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C3 C4 H4 121.1 . . ? C5 C4 C3 117.71(16) . . ? C5 C4 H4 121.1 . . ? C12 C11 H11 120.2 . . ? C10 C11 C12 119.64(15) . . ? C10 C11 H11 120.2 . . ? C11 C10 H10 119.8 . . ? C9 C10 C11 120.44(16) . . ? C9 C10 H10 119.8 . . ? C8 C9 H9 119.9 . . ? C10 C9 C8 120.15(15) . . ? C10 C9 H9 119.9 . . ? S2 C16 H16A 108.9 . . ? S2 C16 H16B 108.9 . . ? H16A C16 H16B 107.7 . . ? C17 C16 S2 113.53(13) . . ? C17 C16 H16A 108.9 . . ? C17 C16 H16B 108.9 . . ? C6 C5 H5 119.4 . . ? C4 C5 C6 121.19(16) . . ? C4 C5 H5 119.4 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 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 S1 S2 2.0395(6) . ? S1 C14 1.8456(16) . ? S2 C16 1.8215(17) . ? N1 C1 1.387(2) . ? N1 C2 1.395(2) . ? N1 C14 1.456(2) . ? N2 C3 1.395(2) . ? N2 C1 1.316(2) . ? C3 C2 1.404(2) . ? C3 C4 1.396(2) . ? C7 H7 0.9300 . ? C7 C2 1.396(2) . ? C7 C6 1.381(2) . ? C1 C8 1.477(2) . ? C8 C13 1.396(2) . ? C8 C9 1.399(2) . ? C14 H14 0.9800 . ? C14 C15 1.527(2) . ? C13 H13 0.9300 . ? C13 C12 1.387(2) . ? C6 H6 0.9300 . ? C6 C5 1.405(3) . ? C12 H12 0.9300 . ? C12 C11 1.388(2) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C4 H4 0.9300 . ? C4 C5 1.382(2) . ? C11 H11 0.9300 . ? C11 C10 1.388(2) . ? C10 H10 0.9300 . ? C10 C9 1.385(2) . ? C9 H9 0.9300 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C16 C17 1.513(3) . ? C5 H5 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S1 S2 C16 C17 66.87(14) . . . . ? S2 S1 C14 N1 -60.44(11) . . . . ? S2 S1 C14 C15 174.08(10) . . . . ? N1 C1 C8 C13 52.5(2) . . . . ? N1 C1 C8 C9 -128.42(17) . . . . ? N2 C3 C2 N1 -1.29(17) . . . . ? N2 C3 C2 C7 175.95(14) . . . . ? N2 C3 C4 C5 -176.33(15) . . . . ? N2 C1 C8 C13 -129.41(17) . . . . ? N2 C1 C8 C9 49.6(2) . . . . ? C3 N2 C1 N1 1.51(17) . . . . ? C3 N2 C1 C8 -176.72(14) . . . . ? C3 C4 C5 C6 0.0(2) . . . . ? C7 C6 C5 C4 -1.6(3) . . . . ? C1 N1 C2 C3 2.08(16) . . . . ? C1 N1 C2 C7 -174.72(17) . . . . ? C1 N1 C14 S1 106.87(15) . . . . ? C1 N1 C14 C15 -130.05(15) . . . . ? C1 N2 C3 C2 -0.09(17) . . . . ? C1 N2 C3 C4 178.57(16) . . . . ? C1 C8 C13 C12 179.70(15) . . . . ? C1 C8 C9 C10 -179.78(16) . . . . ? C8 C13 C12 C11 0.0(3) . . . . ? C2 N1 C1 N2 -2.34(18) . . . . ? C2 N1 C1 C8 175.88(14) . . . . ? C2 N1 C14 S1 -59.46(18) . . . . ? C2 N1 C14 C15 63.62(19) . . . . ? C2 C3 C4 C5 2.2(2) . . . . ? C2 C7 C6 C5 1.1(2) . . . . ? C14 S1 S2 C16 89.75(8) . . . . ? C14 N1 C1 N2 -170.96(13) . . . . ? C14 N1 C1 C8 7.3(2) . . . . ? C14 N1 C2 C3 170.65(14) . . . . ? C14 N1 C2 C7 -6.2(3) . . . . ? C13 C8 C9 C10 -0.7(3) . . . . ? C13 C12 C11 C10 -0.7(3) . . . . ? C6 C7 C2 N1 177.52(16) . . . . ? C6 C7 C2 C3 1.1(2) . . . . ? C12 C11 C10 C9 0.6(3) . . . . ? C4 C3 C2 N1 179.92(14) . . . . ? C4 C3 C2 C7 -2.8(2) . . . . ? C11 C10 C9 C8 0.1(3) . . . . ? C9 C8 C13 C12 0.7(2) . . . . ?