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_4034452
_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 N3 O2'
_chemical_formula_sum            'C12 H11 N3 O2'
_chemical_formula_weight         229.24
_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             2018-10-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.289(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9313(18)
_cell_length_b                   9.6546(17)
_cell_length_c                   13.094(2)
_cell_measurement_reflns_used    2215
_cell_measurement_temperature    197(130)
_cell_measurement_theta_max      23.3280
_cell_measurement_theta_min      2.5730
_cell_volume                     1122.3(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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_environment      N~2~
_diffrn_ambient_temperature      197(130)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega  -50.00   65.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0898  -57.0000 -120.0000 115

  2 omega  -17.00  114.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0898   77.0000   90.0000 131

  3 omega  -20.00   31.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.6054  -99.0000  150.0000 51

  4 omega  -20.00   31.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.6054  -99.0000  -60.0000 51

  5 omega -122.00  -55.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.6054  178.0000   30.0000 67

  6 omega  -11.00  104.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0898   57.0000    0.0000 115

  7 omega  -50.00   65.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0898  -57.0000    0.0000 115

  8 omega  -59.00  115.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0898   19.0000  -30.0000 174

  9 omega -102.00   13.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.6054  -57.0000  150.0000 115

 10 omega   35.00   61.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0898  178.0000 -150.0000 26

 11 omega  -20.00   83.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0898  -99.0000 -150.0000 103
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0544249000
_diffrn_orient_matrix_UB_12      0.0520226000
_diffrn_orient_matrix_UB_13      -0.0138245000
_diffrn_orient_matrix_UB_21      0.0552879000
_diffrn_orient_matrix_UB_22      0.0518263000
_diffrn_orient_matrix_UB_23      0.0121586000
_diffrn_orient_matrix_UB_31      0.0187798000
_diffrn_orient_matrix_UB_32      -0.0015815000
_diffrn_orient_matrix_UB_33      -0.0513398000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0907
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14374
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.023
_diffrn_reflns_theta_max         25.023
_diffrn_reflns_theta_min         2.627
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48966
_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            brown
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       block
_exptl_crystal_F_000             462
_exptl_crystal_size_max          0.2497
_exptl_crystal_size_mid          0.2479
_exptl_crystal_size_min          0.1254
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         1968
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.158
_refine_ls_R_factor_all          0.1169
_refine_ls_R_factor_gt           0.0833
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2027
_refine_ls_wR_factor_ref         0.2480
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1185
_reflns_number_total             1968
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01946_si_004.cif
_cod_data_source_block           phacacn3
_cod_original_cell_volume        1122.3(4)
_cod_database_code               4034452
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N O'
_reflns_odcompleteness_completeness 93.60
_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:
 C7(H7), C5(H5), C2(H2), C4(H4), C3(H3)
2.b Idealised Me refined as rotating group:
 C12(H12C,H12B,H12A), C10(H10C,H10B,H10A)
;
_olex2_date_sample_data_collection 2018-10-03
_olex2_submission_special_instructions 'No special instructions were received'