S8-Catalyzed Triple Cleavage of Bromodifluoro Compounds for the Assembly of N-containing Heterocycles
Deng, Shuilin; Chen, Haohua; Ma, Xingxing; Zhou, Yao; Yang, Kai; Lan, Yu; Song, Qiuling; Chemical Science  (2019) –; doi:10.1039/C9SC01333D

data_1551249
_publ_section_title
;
 S8-Catalyzed Triple Cleavage of Bromodifluoro Compounds for the Assembly
 of N-containing Heterocycles
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC01333D
_journal_year                    2019
_chemical_formula_moiety         'C8 H5 F2 N O S'
_chemical_formula_sum            'C8 H5 F2 N O S'
_chemical_formula_weight         201.19
_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     dual
_audit_block_doi                 10.5517/ccdc.csd.cc20ynf2
_audit_creation_date             2018-10-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2018-10-26 deposited with the CCDC.    2019-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.787(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9739(6)
_cell_length_b                   16.0078(17)
_cell_length_c                   7.5851(8)
_cell_measurement_reflns_used    1331
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.8950
_cell_measurement_theta_min      3.9140
_cell_volume                     836.84(15)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -45.00  73.00   1.00    1.00    --   15.65   0.00  60.00  118
  2  \w     10.00  53.00   1.00    1.00    --   15.65 -99.00 -90.00   43
  3  \w     -6.00  21.00   1.00    1.00    --  -16.59 -99.00 -30.00   27
  4  \w    -21.00   8.00   1.00    1.00    --  -16.59 -99.00 -60.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0193384000
_diffrn_orient_matrix_UB_12      -0.0101978000
_diffrn_orient_matrix_UB_13      -0.0919699000
_diffrn_orient_matrix_UB_21      -0.0056812000
_diffrn_orient_matrix_UB_22      0.0431357000
_diffrn_orient_matrix_UB_23      -0.0217373000
_diffrn_orient_matrix_UB_31      0.1009078000
_diffrn_orient_matrix_UB_32      0.0005033000
_diffrn_orient_matrix_UB_33      -0.0041401000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0527
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            3212
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         3.724
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.374
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.946
_refine_diff_density_rms         0.248
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.396
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.396
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0894
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2058
_refine_ls_wR_factor_ref         0.2188
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1154
_reflns_number_total             1461
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc01333d2.cif
_cod_data_source_block           exp_6002
_cod_database_code               1551249
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N003(H003), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C)
;
_shelx_res_checksum              81194
_olex2_date_sample_data_collection 2018-10-24
_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 1.453
_oxdiff_exptl_absorpt_empirical_full_min 0.792