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_4034455
_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 O3'
_chemical_formula_sum            'C12 H11 N O3'
_chemical_formula_weight         217.22
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2018-05-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.579(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8591(4)
_cell_length_b                   12.2957(4)
_cell_length_c                   9.3813(4)
_cell_measurement_reflns_used    3668
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      25.0020
_cell_measurement_theta_min      2.7820
_cell_volume                     988.99(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -112.00  63.00   1.00    5.00    --  -25.76  19.00  90.00  175
  2  \w    -11.00 104.00   1.00    5.00    --   27.17  57.00-120.00  115
  3  \w    -20.00  30.00   1.00    5.00    --  -25.76 -99.00  90.00   50
  4  \w     35.00 124.00   1.00    5.00    --   27.17 178.00 -90.00   89
  5  \w    -20.00  32.00   1.00    5.00    --   27.17 -99.00 -90.00   52
  6  \w    -16.00 106.00   1.00    5.00    --   27.17  51.00  45.00  122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0104369000
_diffrn_orient_matrix_UB_12      -0.0318345000
_diffrn_orient_matrix_UB_13      -0.0597600000
_diffrn_orient_matrix_UB_21      -0.0744976000
_diffrn_orient_matrix_UB_22      0.0163770000
_diffrn_orient_matrix_UB_23      -0.0426526000
_diffrn_orient_matrix_UB_31      0.0344621000
_diffrn_orient_matrix_UB_32      0.0452056000
_diffrn_orient_matrix_UB_33      -0.0267752000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7426
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         2.375
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.2598
_exptl_crystal_size_mid          0.2589
_exptl_crystal_size_min          0.1258
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1752
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0520P)^2^+0.6798P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1246
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1538
_reflns_number_total             1752
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01946_si_003.cif
_cod_data_source_block           cun
_cod_original_cell_volume        989.00(8)
_cod_database_code               4034455
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N O'
_reflns_odcompleteness_completeness 93.20
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11B,H11A)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H13), C7(H7), C1(H1), C4(H4), C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C12(H12B,H12A,H12C)
;
_olex2_date_sample_data_collection 2018-03-27
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.341
_oxdiff_exptl_absorpt_empirical_full_min 0.781