Copper catalysed amidation of aryl halides through chelation assistance
Subban Kathiravan; Shishir Ghosh; Graeme Hogarth; Ian A. Nicholls; Chem.Commun. 51 (2015) 4834–; doi:10.1039/C4cc09940K

data_7116707
_publ_section_title
;
 Copper catalysed amidation of aryl halides through chelation assistance
;
_journal_name_full               Chem.Commun.
_journal_page_first              4834
_journal_paper_doi               10.1039/C4cc09940K
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C19 H20 N2 O S'
_chemical_formula_sum            'C19 H20 N2 O S'
_chemical_formula_weight         324.45
_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_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-07-18
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4709)
;
_audit_update_record
;
2014-12-08 deposited with the CCDC.
2015-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.9165(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.8737(3)
_cell_length_b                   9.68667(17)
_cell_length_c                   10.28958(19)
_cell_measurement_reflns_used    4151
_cell_measurement_temperature    150.02(10)
_cell_measurement_theta_max      73.9460
_cell_measurement_theta_min      6.6130
_cell_volume                     1669.59(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      150.02(10)
_diffrn_detector_area_resol_mean 5.2031
_diffrn_measured_fraction_theta_full 0.9491
_diffrn_measured_fraction_theta_max 0.9485
_diffrn_measurement_details
;
  1 omega  -47.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   30.0000  -90.0000 82

  2 omega -105.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -57.0000  120.0000 90

  3 omega    8.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.2890  -99.0000    0.0000 27

  4 omega   84.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.2890   19.0000 -180.0000 26

  5 omega   33.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  -30.0000    0.0000 35

  6 omega   88.00  119.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441   30.0000 -180.0000 31

  7 omega   49.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  -94.0000  150.0000 59

  8 omega   43.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  -45.0000  150.0000 45

  9 omega   38.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  -45.0000  -60.0000 60

 10 omega   89.00  172.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441   45.0000 -120.0000 83

 11 omega   38.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  -30.0000   60.0000 36

 12 omega   35.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  -30.0000  120.0000 27
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0473475000
_diffrn_orient_matrix_UB_12      -0.0479526000
_diffrn_orient_matrix_UB_13      0.1108611000
_diffrn_orient_matrix_UB_21      0.0774630000
_diffrn_orient_matrix_UB_22      -0.0561622000
_diffrn_orient_matrix_UB_23      0.0763335000
_diffrn_orient_matrix_UB_31      0.0146249000
_diffrn_orient_matrix_UB_32      0.1408172000
_diffrn_orient_matrix_UB_33      0.0681188000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6145
_diffrn_reflns_theta_full        74.1793
_diffrn_reflns_theta_max         74.18
_diffrn_reflns_theta_min         5.27
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.759
_exptl_absorpt_correction_T_max  0.632
_exptl_absorpt_correction_T_min  0.573
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2907
_exptl_crystal_description       block
_exptl_crystal_F_000             691.1676
_exptl_crystal_size_max          0.3156
_exptl_crystal_size_mid          0.2639
_exptl_crystal_size_min          0.2395
_refine_diff_density_max         0.3723
_refine_diff_density_min         -0.2990
_refine_diff_density_rms         0.0546
_refine_ls_d_res_high            0.8013
_refine_ls_d_res_low             8.3855
_refine_ls_goodness_of_fit_ref   1.0519
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3226
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0519
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0754P)^2^+0.3280P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1232
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              20
_reflns_limit_h_min              -20
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                2886
_reflns_number_total             3226
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c4cc09940k2.cif
_cod_data_source_block           xstr0259
_cod_database_code               7116707
_chemical_oxdiff_formula         'S1 N2 O1 C19 H20'
_chemical_oxdiff_usercomment     SK415
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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:
 C2(H2a,H2b), C3(H3a,H3b), C4(H4a,H4b), C5(H5a,H5b)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17),
 C18(H18)
2.c Idealised Me refined as rotating group:
 C6(H6a,H6b,H6c)
;