Non-directed copper-catalyzed regioselective C-H sulfonylation of phenothiazines.
Liu, Caiyan; Shen, Yongli; Yuan, Kedong; Organic & biomolecular chemistry 17 (2019) 5009–5013; doi:10.1039/c9ob00705a

data_7156802
_publ_section_title
;
 Non-directed copper-catalyzed regioselective C-H sulfonylation of
 phenothiazines.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5009
_journal_page_last               5013
_journal_paper_doi               10.1039/c9ob00705a
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         '0.4(C25 H22 N2 O2 S2)'
_chemical_formula_sum            'C11 H10 Cl0 N O S0.1'
_chemical_formula_weight         175.41
_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_creation_date             2017-06-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-07-16 deposited with the CCDC.    2019-04-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.832(2)
_cell_angle_gamma                90
_cell_formula_units_Z            10
_cell_length_a                   12.5619(2)
_cell_length_b                   19.6420(4)
_cell_length_c                   9.1574(2)
_cell_measurement_reflns_used    6065
_cell_measurement_temperature    299.83(10)
_cell_measurement_theta_max      78.5110
_cell_measurement_theta_min      3.5500
_cell_volume                     2219.25(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.23a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.23a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.23a (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_environment      air
_diffrn_ambient_temperature      299.83(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.948
_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     37.00  75.00   0.50    0.50    --    0.00  19.00-150.00   76
  2  \w    -87.00  17.00   0.50    0.50    --    0.00 -38.00  90.00  208
  3  \w    -36.00 -10.00   0.50    0.50    --    0.00 -38.00 -60.00   52
  4  \w    -80.00 -40.00   0.50    0.50    --    0.00 -38.00 -60.00   80
  5  \w     90.00 185.00   0.50    3.00    --  106.20  30.00 -60.00  190
  6  \w     83.00 109.00   0.50    3.00    --  106.20 -61.00   0.00   52
  7  \w     92.00 180.00   0.50    3.00    --  106.20  30.00-120.00  176
  8  \w    161.00 194.00   0.50    3.00    --  106.20  30.00 -30.00   66
  9  \w     90.00 141.00   0.50    3.00    --  106.20  30.00 -30.00  102
 10  \w     36.00 107.00   0.50    3.00    --  106.20 -45.00  30.00  142
 11  \w    109.00 158.00   0.50    3.00    --  106.20  45.00  30.00   98
 12  \w     17.00 123.00   0.50    3.00    --  106.20 -61.00  30.00  212
 13  \w     90.00 188.00   0.50    3.00    --  106.20  30.00 -90.00  196
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0991706000
_diffrn_orient_matrix_UB_12      0.0061399000
_diffrn_orient_matrix_UB_13      -0.1268491000
_diffrn_orient_matrix_UB_21      0.0475282000
_diffrn_orient_matrix_UB_22      0.0656806000
_diffrn_orient_matrix_UB_23      -0.0539243000
_diffrn_orient_matrix_UB_31      0.0590801000
_diffrn_orient_matrix_UB_32      -0.0424519000
_diffrn_orient_matrix_UB_33      -0.1016695000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13319
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.371
_diffrn_reflns_theta_min         3.582
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.887
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.23a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             926
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4561
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0536
_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^)+(0.0806P)^2^+0.7492P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1551
_refine_ls_wR_factor_ref         0.1608
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3863
_reflns_number_total             4561
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00705a2.cif
_cod_data_source_block           15501
_cod_depositor_comments
'Adding full bibliography for 7156801--7156802.cif.'
_cod_original_formula_sum        'C11 H10 Cl0 N O S0.10'
_cod_database_code               7156802
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 96.12
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C24(H24A,H24B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C2(H2), C19(H19), C15(H15), C8(H8), C14(H14), C20(H20),
 C18(H18), C11(H11), C16(H16), C9(H9), C3(H3)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_shelx_res_checksum              42188
_shelx_hkl_checksum              30048
_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 2.873
_oxdiff_exptl_absorpt_empirical_full_min 0.595