Convenient one-pot access to 2H-3-nitrothiochromenes from 2-bromobenzaldehydes, sodium sulfide and β-nitrostyrenes.
Le, Thi Thu Huong; Youhei, Chitose; Le, Quy Hien; Nguyen, Thanh Binh; Mac, Dinh Hung; Organic & biomolecular chemistry 17 (2019) 6355–6358; doi:10.1039/c9ob01060b

data_7156905
_publ_section_title
;
 Convenient one-pot access to 2H-3-nitrothiochromenes from
 2-bromobenzaldehydes, sodium sulfide and \b-nitrostyrenes.
;
_journal_issue                   26
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6355
_journal_page_last               6358
_journal_paper_doi               10.1039/c9ob01060b
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C15 H11 N O2 S'
_chemical_formula_sum            'C15 H11 N O2 S'
_chemical_formula_weight         269.31
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-09-26
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2016-09-26 deposited with the CCDC.    2019-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.8620(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9636(3)
_cell_length_b                   10.3969(4)
_cell_length_c                   13.4271(5)
_cell_measurement_reflns_used    9096
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.257
_cell_measurement_theta_min      3.007
_cell_volume                     1246.82(8)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            31745
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.332
_diffrn_reflns_theta_min         3.007
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/2 (Bruker,2014/2) was used for absorption correction. wR2(int) was 0.0541 before and 0.0452 after correction. The Ratio of minimum to maximum transmission is 0.9662. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3105
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0310P)^2^+0.7448P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0747
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2788
_reflns_number_total             3105
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01060b2.cif
_cod_data_source_block           MDH_thiochrom
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7156905.cif.
;
_cod_database_code               7156905
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
;
_shelx_res_checksum              4454
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'