Formation or Cleavage of Rings via Sulfide-Mediated Reduction Offers Background-Free Detection of Sulfide.
Ghosh, Sanjib; Roy, Biswajit; Bandyopadhyay, Subhajit; The Journal of organic chemistry 84 (2019) 12031–12039; doi:10.1021/acs.joc.9b01946

data_4034453
_publ_section_title
;
 Formation or Cleavage of Rings via Sulfide-Mediated Reduction Offers
 Background-Free Detection of Sulfide.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12031
_journal_page_last               12039
_journal_paper_doi               10.1021/acs.joc.9b01946
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C12 H11 N O'
_chemical_formula_sum            'C12 H11 N O'
_chemical_formula_weight         185.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-08
_audit_creation_method
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Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
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_cell_angle_alpha                90
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_cell_formula_units_Z            4
_cell_length_a                   7.0898(4)
_cell_length_b                   9.8867(4)
_cell_length_c                   14.0714(7)
_cell_measurement_reflns_used    2132
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.7880
_cell_measurement_theta_min      2.5070
_cell_volume                     974.03(8)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measurement_details
;
  1 omega   35.00  121.00   1.0000   75.0000
omega____ theta____ kappa____ phi______ frames
    -       26.5621  178.0000    0.0000 86

  2 omega  -55.00   82.00   1.0000   75.0000
omega____ theta____ kappa____ phi______ frames
    -       26.5621  -38.0000  -30.0000 137

  3 omega   35.00  121.00   1.0000   75.0000
omega____ theta____ kappa____ phi______ frames
    -       26.5621  178.0000  150.0000 86

  4 omega  -11.00   50.00   1.0000   75.0000
omega____ theta____ kappa____ phi______ frames
    -       26.5621   57.0000  120.0000 61

  5 omega  -11.00  103.00   1.0000   75.0000
omega____ theta____ kappa____ phi______ frames
    -       26.5621   57.0000    0.0000 114
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_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_11      0.0364577000
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_diffrn_orient_matrix_UB_21      -0.0123390000
_diffrn_orient_matrix_UB_22      -0.0256302000
_diffrn_orient_matrix_UB_23      -0.0477037000
_diffrn_orient_matrix_UB_31      -0.0936822000
_diffrn_orient_matrix_UB_32      0.0270841000
_diffrn_orient_matrix_UB_33      -0.0086666000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6802
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.653
_diffrn_reflns_theta_min         2.528
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.2589
_exptl_crystal_size_mid          0.2487
_exptl_crystal_size_min          0.1211
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2071
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0784
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_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^)+(0.0455P)^2^+0.4183P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1500
_refine_ls_wR_factor_ref         0.1597
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1535
_reflns_number_total             2071
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01946_si_005.cif
_cod_data_source_block           sb-br-aun
_cod_database_code               4034453
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O N'
_shelx_estimated_absorpt_t_max   0.990
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_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C2(H2), C1(H1), C7(H7)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C)
;
_olex2_date_sample_data_collection 2018-10-05
_olex2_submission_special_instructions 'No special instructions were received'