Combined Experimental/theoretical Study on D-Glucosamine Promoted Regioselective Sulfenylation of Indoles Catalyzed by Copper
Ge, Xin; Sun, Fengli; Liu, Xuemin; Chen, Xinzhi; Qian, Chao; Zhou, Shaodong; New J. Chem. 41 (2017) 13175–13180; doi:10.1039/C7NJ02784B

data_7056614
_publ_section_title
;
 Combined Experimental/theoretical Study on D-Glucosamine Promoted
 Regioselective Sulfenylation of Indoles Catalyzed by Copper
;
_journal_issue                   21
_journal_name_full               'New J. Chem.'
_journal_page_first              13175
_journal_page_last               13180
_journal_paper_doi               10.1039/C7NJ02784B
_journal_volume                  41
_journal_year                    2017
_chemical_formula_sum            'C14 H10 Cl N S'
_chemical_formula_weight         259.74
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-06-09 deposited with the CCDC.
2017-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 113.8380(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.4123(5)
_cell_length_b                   5.7309(2)
_cell_length_c                   16.0699(5)
_cell_measurement_reflns_used    9885
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.41
_cell_measurement_theta_min      3.09
_cell_volume                     1214.07(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0124
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8076
_diffrn_reflns_theta_full        25.60
_diffrn_reflns_theta_max         25.60
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.460
_exptl_absorpt_correction_T_max  0.9818
_exptl_absorpt_correction_T_min  0.9342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4530
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0231
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0638P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0745
_reflns_number_gt                4401
_reflns_number_total             4530
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7nj02784b2.cif
_cod_data_source_block           mo_za2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7056614