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_7119491
_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         'C20 H18 N2 O4 S'
_chemical_formula_sum            'C20 H18 N2 O4 S'
_chemical_formula_weight         382.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-08-08
_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                111.680(5)
_cell_angle_beta                 91.034(4)
_cell_angle_gamma                90.043(4)
_cell_formula_units_Z            4
_cell_length_a                   11.1094(5)
_cell_length_b                   13.0608(7)
_cell_length_c                   13.2880(7)
_cell_measurement_reflns_used    11430
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.9810
_cell_measurement_theta_min      2.4280
_cell_volume                     1791.32(17)
_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      293(2)
_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  70.00   0.50    8.00    --  -20.00   0.00  36.00  360
  2  \w    -67.50   5.00   0.50    8.00    --  -20.00 -72.00-180.00  145
  3  \w    -77.50   3.50   0.50    8.00    --  -20.00 -72.00  36.00  162
  4  \w    -56.50   1.00   0.50    8.00    --  -20.00  72.00 -36.00  115
  5  \w    -59.00 -27.50   0.50    8.00    --  -20.00  72.00-180.00   63
  6  \w   -110.00  70.00   0.50    8.00    --  -20.00   0.00 -36.00  360
  7  \w    -73.00  10.50   0.50    8.00    --  -20.00 -72.00 108.00  167
  8  \w    -70.00   5.00   0.50    8.00    --  -20.00 -72.00 -36.00  150
  9  \w    -52.50   1.00   0.50    8.00    --  -20.00  72.00-108.00  107
 10  \w    -59.00 -28.50   0.50    8.00    --  -20.00  72.00 108.00   61
 11  \w    -54.00  70.00   0.50    8.00    --  -20.00   0.00 108.00  248
 12  \w     -4.00  40.00   0.50    8.00    --  -20.00   0.00-180.00   88
;
_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      0.0421082000
_diffrn_orient_matrix_UB_12      0.0383978000
_diffrn_orient_matrix_UB_13      0.0345791000
_diffrn_orient_matrix_UB_21      0.0069571000
_diffrn_orient_matrix_UB_22      -0.0336109000
_diffrn_orient_matrix_UB_23      0.0311469000
_diffrn_orient_matrix_UB_31      0.0475030000
_diffrn_orient_matrix_UB_32      -0.0284881000
_diffrn_orient_matrix_UB_33      -0.0336911000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1189
_diffrn_reflns_av_unetI/netI     0.0722
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            34781
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         1.649
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61543
_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    1.418
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.035
_refine_diff_density_max         1.190
_refine_diff_density_min         -0.906
_refine_diff_density_rms         0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         6319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.1147
_refine_ls_R_factor_gt           0.0881
_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^)+(0.0870P)^2^+6.7068P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2157
_refine_ls_wR_factor_ref         0.2363
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4749
_reflns_number_total             6319
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc08622e2.cif
_cod_data_source_block           cmrv-nt-112_mo
_cod_depositor_comments
'Adding full bibliography for 7119490--7119492.cif.'
_cod_original_cell_volume        1791.31(16)
_cod_database_code               7119491
_chemical_oxdiff_formula         C20H18N2O4S1
_reflns_odcompleteness_completeness 90.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.09
_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:
 C00M(H00A,H00B), C00X(H00C,H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00I(H00I), C00J(H00J), C00O(H00O), C00P(H00P), C00Q(H00Q),
 C00T(H00T), C00U(H00U), C00W(H00W), C00Z(H00Z), C010(H010), C014(H014),
 C015(H015), C017(H017), C018(H018), C019(H019), C01A(H01G), C01C(H01H),
 C01D(H01I), C01E(H01J)
2.c Idealised Me refined as rotating group:
 C01F(H01K,H01L,H01M), C01G(H01A,H01B,H01C), C01H(H01N,H01O,H01P), C01I(H01D,
 H01E,H01F)
;
_shelx_res_checksum              54453
_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 1.966
_oxdiff_exptl_absorpt_empirical_full_min 0.574