NCS-promoted thiocyanation and selenocyanation of pyrrolo[1,2-a]quinoxalines
Yang, Zhen; He, Jing; Wei, Yueting; Li, Weiwei; Liu, Ping; Zhao, Jixing; Wei, Yu; Organic & Biomolecular Chemistry 18 (2020) 9088–9094; doi:10.1039/D0OB01818J

data_7157780
_publ_section_title
;
 NCS-promoted thiocyanation and selenocyanation of
 pyrrolo[1,2-a]quinoxalines
;
_journal_issue                   44
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              9088
_journal_page_last               9094
_journal_paper_doi               10.1039/D0OB01818J
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C12 H7 N3 S'
_chemical_formula_sum            'C12 H7 N3 S'
_chemical_formula_weight         225.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-27 deposited with the CCDC.	2020-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.9340(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.2160(5)
_cell_length_b                   8.5645(2)
_cell_length_c                   16.5649(5)
_cell_measurement_reflns_used    5390
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.327
_cell_measurement_theta_min      2.410
_cell_volume                     2032.52(10)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      150.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0683
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18145
_diffrn_reflns_point_group_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.379
_diffrn_reflns_theta_min         2.378
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1050 before and 0.0558 after correction. The Ratio of minimum to maximum transmission is 0.9125. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 2226 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         7628
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0319P)^2^+0.6438P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0997
_reflns_Friedel_coverage         0.851
_reflns_Friedel_fraction_full    0.868
_reflns_Friedel_fraction_max     0.843
_reflns_number_gt                5963
_reflns_number_total             7628
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01818j2.cif
_cod_data_source_block           22019820shz_0m
_cod_database_code               7157780
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.955
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C19(H19), C31(H31), C22(H22), C9(H9), C14(H14), C21(H21), C2(H2),
 C16(H16), C40(H40), C15(H15), C37(H37), C13(H13), C34(H34), C10(H10), C1(H1),
 C26(H26), C28(H28), C33(H33), C3(H3), C45(H45), C27(H27), C39(H39), C7(H7),
 C46(H46), C38(H38), C43(H43), C25(H25)
;
_olex2_submission_special_instructions 'No special instructions were received'