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_1551251
_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         'C16 H14 N2 O S'
_chemical_formula_sum            'C16 H14 N2 O S'
_chemical_formula_weight         282.37
_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_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_primary     direct
_audit_creation_date             2018-12-04
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2018-12-05 deposited with the CCDC.    2019-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.111(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4561(8)
_cell_length_b                   18.2584(11)
_cell_length_c                   9.6555(7)
_cell_measurement_reflns_used    1732
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.4740
_cell_measurement_theta_min      4.1340
_cell_volume                     1472.0(2)
_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  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9973
_diffrn_measured_fraction_theta_max 0.9973
_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      0.0245961000
_diffrn_orient_matrix_UB_12      0.0371907000
_diffrn_orient_matrix_UB_13      0.0025772000
_diffrn_orient_matrix_UB_21      -0.0806026000
_diffrn_orient_matrix_UB_22      0.0112570000
_diffrn_orient_matrix_UB_23      -0.0027100000
_diffrn_orient_matrix_UB_31      0.0096383000
_diffrn_orient_matrix_UB_32      -0.0009441000
_diffrn_orient_matrix_UB_33      0.0743781000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7286
_diffrn_reflns_theta_full        24.9999
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.66
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76624
_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    1.2741
_exptl_crystal_description       block
_exptl_crystal_F_000             592.7175
_refine_diff_density_max         0.2599
_refine_diff_density_min         -0.4364
_refine_diff_density_rms         0.0591
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             5.5620
_refine_ls_goodness_of_fit_ref   0.9981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2586
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9981
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1362
_refine_ls_wR_factor_ref         0.1584
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -10
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                1874
_reflns_number_total             2586
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9sc01333d2.cif
_cod_data_source_block           exp_6199
_cod_database_code               1551251
_reflns_odcompleteness_completeness 99.62
_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 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:
 C009(H00a,H00b)
2.b Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00F(H00F), C00E(H00E), C00C(H00d), C00G(H00G), C00J(H00J),
 C00I(H00I), C00A(H00c), N003(H003)
2.c Idealised Me refined as rotating group:
 C00K(H00k,H00l,H00m)
;
_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 1.528
_oxdiff_exptl_absorpt_empirical_full_min 0.731