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_7119490
_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         'C31 H26 N2 O3 P S, C H Cl3'
_chemical_formula_sum            'C32 H27 Cl3 N2 O3 P S'
_chemical_formula_weight         656.93
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'I -2ya'
_space_group_name_H-M_alt        'I 1 a 1'
_symmetry_space_group_name_Hall  'I -2ya'
_symmetry_space_group_name_H-M   'I 1 a 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-06-02
_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                 93.511(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6757(3)
_cell_length_b                   24.7111(7)
_cell_length_c                   12.3147(4)
_cell_measurement_reflns_used    20873
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.6570
_cell_measurement_theta_min      2.2460
_cell_volume                     2938.88(16)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -94.00  70.00   0.50   16.00    --  -20.00   0.00  36.00  328
  2  \w    -70.00  19.00   0.50   16.00    --  -20.00 -72.00-180.00  178
  3  \w    -73.00   5.00   0.50   16.00    --  -20.00 -72.00  36.00  156
  4  \w    -63.00 -13.00   0.50   16.00    --  -20.00 -72.00 -36.00  100
  5  \w    -59.00 -28.50   0.50   16.00    --  -20.00  72.00-180.00   61
  6  \w    -20.00  10.00   0.50   16.00    --  -20.00  72.00-108.00   60
  7  \w   -110.00  70.00   0.50   16.00    --  -20.00   0.00 108.00  360
  8  \w    -81.00  19.00   0.50   16.00    --  -20.00 -72.00-108.00  200
  9  \w    -84.50  19.00   0.50   16.00    --  -20.00 -72.00 108.00  207
 10  \w    -44.00   0.00   0.50   16.00    --  -20.00  72.00  36.00   88
 11  \w   -110.00  30.50   0.50   16.00    --  -20.00   0.00-180.00  281
 12  \w    -78.00  19.00   0.50   16.00    --  -20.00 -72.00 108.00  194
 13  \w    -78.00  19.00   0.50   16.00    --  -20.00 -72.00 -72.00  194
 14  \w    -57.50  24.00   0.50   16.00    --  -20.00   0.00-108.00  163
 15  \w    -30.00   0.00   0.50   16.00    --  -20.00  72.00  36.00   60
 16  \w    -36.00  40.50   0.50   16.00    --  -20.00  72.00 108.00  153
;
_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      0.0726690000
_diffrn_orient_matrix_UB_12      0.0040789000
_diffrn_orient_matrix_UB_13      0.0018195000
_diffrn_orient_matrix_UB_21      0.0102331000
_diffrn_orient_matrix_UB_22      -0.0282982000
_diffrn_orient_matrix_UB_23      -0.0049223000
_diffrn_orient_matrix_UB_31      -0.0030624000
_diffrn_orient_matrix_UB_32      0.0025435000
_diffrn_orient_matrix_UB_33      -0.0574628000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1030
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            37874
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.264
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.476
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78794
_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    1.485
_exptl_crystal_description       plate
_exptl_crystal_F_000             1356
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.637
_refine_diff_density_min         -0.705
_refine_diff_density_rms         0.133
_refine_ls_abs_structure_details
;
 Flack x determined using 2149 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         5180
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0660
_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^)+(0.1208P)^2^+4.9391P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1765
_refine_ls_wR_factor_ref         0.1851
_reflns_Friedel_coverage         0.993
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4846
_reflns_number_total             5180
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc08622e2.cif
_cod_data_source_block           cmrv-nt-3-99_mo
_cod_depositor_comments
'Adding full bibliography for 7119490--7119492.cif.'
_cod_original_cell_volume        2938.90(15)
_cod_database_code               7119490
_chemical_oxdiff_formula         'C31 H25 N2 O3 P1 S1'
_reflns_odcompleteness_completeness 95.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.13
_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. Uiso/Uaniso restraints and constraints
Uanis(C32) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.001
3.a Ternary CH refined with riding coordinates:
 C32(H32)
3.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C28(H28), C15(H15), C29(H29), C21(H21), C22(H22), C23(H23), C7(H7),
 C27(H27), C25(H25), C17(H17), C5(H5), C31(H31), C24(H24), C30(H30), C2(H2),
 C11(H11), C1(H1A), C3(H3), C12(H12), C6(H6)
3.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              51699
_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 3.833
_oxdiff_exptl_absorpt_empirical_full_min 0.723