Rhodium(III)-catalyzed cyanation of vinylic C–H bonds: N-cyano-N-phenyl-p-toluenesulfonamide as a cyanation reagent
Su, Wei; Gong, Tian-Jun; Xiao, Bin; Fu, Yao; Chemical Communications (Cambridge, United Kingdom) 51 (2015) 11848–11851; doi:10.1039/c4cc09790d

data_7117463
_publ_section_title
;
 Rhodium(III)-catalyzed cyanation of vinylic C--H bonds:
 N-cyano-N-phenyl-p-toluenesulfonamide as a cyanation reagent
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   59
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              11848
_journal_page_last               11851
_journal_paper_doi               10.1039/c4cc09790d
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_sum            'C11 H18 N2 O'
_chemical_formula_weight         194.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-08-08 deposited with the CCDC.
2015-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3992(4)
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_cell_length_c                   18.3176(11)
_cell_measurement_reflns_used    1102
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      69.2246
_cell_measurement_theta_min      4.7771
_cell_volume                     1253.60(14)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            2813
_diffrn_reflns_point_group_measured_fraction_full 0.875
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.350
_diffrn_reflns_theta_min         5.358
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.527
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.029
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 431 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   1.6(5)
_refine_ls_extinction_coef       0.026(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         2016
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0457
_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^)+(0.0923P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1672
_reflns_Friedel_coverage         0.511
_reflns_Friedel_fraction_full    0.726
_reflns_Friedel_fraction_max     0.703
_reflns_number_gt                1483
_reflns_number_total             2016
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc09790d2.cif
_cod_data_source_block           shelxl
_cod_database_code               7117463
_shelx_estimated_absorpt_t_min   0.833
_shelx_estimated_absorpt_t_max   0.897
_shelxl_version_number           2013-4
_shelx_res_checksum              93957