Amine organocatalysts for highly ortho-Selective chlorination of anilines with sulfuryl chloride
Wang, Xinzhe; Chen, Zhihuang; Liu, Qingqing; Lin, Wenqing; Xiong, Xiaodong; Chemical Communications  (2022) –; doi:10.1039/D2CC05320A

data_7130887
_publ_section_title
;
 Amine organocatalysts for highly ortho-Selective chlorination of anilines
 with sulfuryl chloride
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC05320A
_journal_year                    2022
_chemical_formula_sum            'C14 H11 Cl F N O2'
_chemical_formula_weight         279.69
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-03-12 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.234(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.7305(2)
_cell_length_b                   11.4393(4)
_cell_length_c                   12.2488(4)
_cell_measurement_temperature    293(2)
_cell_volume                     661.02(4)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4639
_diffrn_reflns_point_group_measured_fraction_full 0.921
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.061
_diffrn_reflns_theta_min         3.864
_exptl_absorpt_coefficient_mu    2.658
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 903 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2209
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0891P)^2^+0.0039P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1291
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_full    0.845
_reflns_Friedel_fraction_max     0.838
_reflns_number_gt                2114
_reflns_number_total             2209
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc05320a2.cif
_cod_data_source_block           exp_1569_auto
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               7130887
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.857
_shelx_estimated_absorpt_t_max   0.901
_shelx_res_checksum              25822
_shelx_hkl_checksum              79174