Cobalt-catalyzed aryl C-H activation and highly regioselective intermolecular annulation of sulfonamides with allenes.
Thrimurtulu, Neetipalli; Nallagonda, Rajender; Volla, Chandra M. R.; Chemical communications (Cambridge, England) 53 (2017) 1872–1875; doi:10.1039/c6cc08622e

data_7119492
_publ_section_title
;
 Cobalt-catalyzed aryl C-H activation and highly regioselective
 intermolecular annulation of sulfonamides with allenes.
;
_journal_issue                   11
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1872
_journal_page_last               1875
_journal_paper_doi               10.1039/c6cc08622e
_journal_volume                  53
_journal_year                    2017
_chemical_formula_moiety         'C30 H23 Br N2 O3 P S'
_chemical_formula_sum            'C30 H23 Br N2 O3 P S'
_chemical_formula_weight         602.44
_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
_audit_creation_date             2016-08-24
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.10.28 svn.r3245 for OlexSys, GUI svn.r5128)
;
_audit_update_record
;
2016-09-15 deposited with the CCDC.
2017-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.156(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8352(5)
_cell_length_b                   12.6037(6)
_cell_length_c                   20.8785(12)
_cell_measurement_reflns_used    7974
_cell_measurement_temperature    150
_cell_measurement_theta_max      31.1330
_cell_measurement_theta_min      2.0080
_cell_volume                     2573.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -110.00  30.00   0.50    8.00    --  -20.00   0.00  36.00  280
  2  \w    -63.00  19.00   0.50    8.00    --  -20.00 -72.00 -36.00  164
  3  \w    -22.00   8.00   0.50    8.00    --  -20.00  72.00  36.00   60
  4  \w    -49.00 -19.00   0.50    8.00    --  -20.00  72.00 -36.00   60
  5  \w    -85.00  70.00   0.50    8.00    --  -20.00   0.00 108.00  310
  6  \w    -35.00  19.00   0.50    8.00    --  -20.00 -72.00-108.00  108
  7  \w    -28.50  16.50   0.50    8.00    --  -20.00 -72.00  36.00   90
  8  \w    -59.00 -29.00   0.50    8.00    --  -20.00  72.00 108.00   60
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0188789000
_diffrn_orient_matrix_UB_12      0.0541996000
_diffrn_orient_matrix_UB_13      -0.0030181000
_diffrn_orient_matrix_UB_21      -0.0103941000
_diffrn_orient_matrix_UB_22      -0.0057421000
_diffrn_orient_matrix_UB_23      -0.0339550000
_diffrn_orient_matrix_UB_31      -0.0693051000
_diffrn_orient_matrix_UB_32      -0.0139829000
_diffrn_orient_matrix_UB_33      0.0021014000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0844
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25606
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.083
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.778
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.13632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_description       plate
_exptl_crystal_F_000             1228
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.229
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4522
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0434
_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^)+(0.0524P)^2^+2.6878P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1053
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3752
_reflns_number_total             4522
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc08622e2.cif
_cod_data_source_block           cmrv-nt-so2-br_mo
_cod_depositor_comments
'Adding full bibliography for 7119490--7119492.cif.'
_cod_database_code               7119492
_chemical_oxdiff_formula         C34H31N2O3P1S1
_reflns_odcompleteness_completeness 91.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.22
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C26(H26), C24(H24), C11(H11), C15(H15), C17(H17), C3(H3), C14(H14),
 C29(H29), C4(H4), C7(H7), C9(H9), C8(H8), C12(H12), C13(H13), C21(H21), C5(H5),
  C18(H18), C28(H28), C19(H19), C20(H20)
;
_shelx_res_checksum              26807
_shelx_shelxl_version_number     2014/7
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.683
_oxdiff_exptl_absorpt_empirical_full_min 0.596