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_1551250
_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 O3'
_chemical_formula_sum            'C16 H14 N2 O3'
_chemical_formula_weight         282.30
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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                97.492(10)
_cell_angle_beta                 98.979(10)
_cell_angle_gamma                100.301(11)
_cell_formula_units_Z            2
_cell_length_a                   6.3315(8)
_cell_length_b                   6.8983(9)
_cell_length_c                   16.780(2)
_cell_measurement_reflns_used    1203
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.7340
_cell_measurement_theta_min      4.2400
_cell_volume                     702.73(16)
_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 0.9972
_diffrn_measured_fraction_theta_max 0.9972
_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      -0.0744485000
_diffrn_orient_matrix_UB_12      -0.0387982000
_diffrn_orient_matrix_UB_13      -0.0372105000
_diffrn_orient_matrix_UB_21      -0.0806046000
_diffrn_orient_matrix_UB_22      -0.0371771000
_diffrn_orient_matrix_UB_23      0.0222420000
_diffrn_orient_matrix_UB_31      -0.0371343000
_diffrn_orient_matrix_UB_32      0.0912803000
_diffrn_orient_matrix_UB_33      0.0014408000
_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  0.0196
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5605
_diffrn_reflns_theta_full        24.9949
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.61
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52446
_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    1.3341
_exptl_crystal_description       block
_exptl_crystal_F_000             296.1544
_refine_diff_density_max         0.2093
_refine_diff_density_min         -0.2883
_refine_diff_density_rms         0.0669
_refine_ls_d_res_high            0.8410
_refine_ls_d_res_low             5.6516
_refine_ls_goodness_of_fit_ref   0.9286
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2474
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.9284
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.0000
_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          0.1319
_refine_ls_wR_factor_ref         0.1539
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                1783
_reflns_number_total             2474
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9sc01333d2.cif
_cod_data_source_block           exp_6200
_cod_original_cell_volume        702.72(16)
_cod_database_code               1551250
_reflns_odcompleteness_completeness 99.65
_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. Rigid bond restraints
 N002, C009
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Secondary CH2 refined with riding coordinates:
 C00G(H00a,H00c)
3.b Aromatic/amide H refined with riding coordinates:
 N005(H005), C00B(H00B), C00D(H00D), C00E(H00E), C00F(H00F), C00H(H00H),
 C00I(H00I), C00J(H00J), C00K(H00K)
3.c Idealised Me refined as rotating group:
 C00L(H00g,H00l,H00m)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.147
_oxdiff_exptl_absorpt_empirical_full_min 0.640