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_7116706
_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         'C25 H24 N2 O'
_chemical_formula_sum            'C25 H24 N2 O'
_chemical_formula_weight         368.48
_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_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_primary     direct
_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                91.766(3)
_cell_angle_beta                 93.926(3)
_cell_angle_gamma                97.631(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4910(4)
_cell_length_b                   9.5574(3)
_cell_length_c                   10.9648(4)
_cell_measurement_reflns_used    5260
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.7450
_cell_measurement_theta_min      5.9900
_cell_volume                     982.69(6)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 5.2031
_diffrn_measured_fraction_theta_full 0.9323
_diffrn_measured_fraction_theta_max 0.9323
_diffrn_measurement_details
;
  1 omega  -48.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000    0.0000 80

  2 omega -116.00   -6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -19.0000 -180.0000 110

  3 omega   27.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.2890 -130.0000 -130.0000 33

  4 omega    9.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.2890  -99.0000   90.0000 74

  5 omega   72.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.2890 -130.0000 -130.0000 26

  6 omega   30.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  -94.0000 -180.0000 72

  7 omega   33.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  -30.0000   30.0000 57

  8 omega   35.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  -30.0000 -120.0000 54

  9 omega  129.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441   30.0000  -60.0000 49

 10 omega   86.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441   30.0000  -60.0000 29

 11 omega   95.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  125.0000  120.0000 25

 12 omega  138.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  125.0000  120.0000 38

 13 omega   34.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  -30.0000  -60.0000 54

 14 omega   37.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  -94.0000   60.0000 45

 15 omega   63.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  -94.0000  -90.0000 45

 16 omega   33.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  -30.0000  120.0000 47

 17 omega  110.00  169.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441   45.0000 -150.0000 59

 18 omega   40.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  -45.0000 -180.0000 53

 19 omega  138.00  173.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441  125.0000 -120.0000 35

 20 omega   83.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9441 -125.0000  120.0000 34
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1540797000
_diffrn_orient_matrix_UB_12      0.0308117000
_diffrn_orient_matrix_UB_13      0.0103842000
_diffrn_orient_matrix_UB_21      0.0217225000
_diffrn_orient_matrix_UB_22      -0.0009658000
_diffrn_orient_matrix_UB_23      0.1404861000
_diffrn_orient_matrix_UB_31      0.0524609000
_diffrn_orient_matrix_UB_32      0.1598171000
_diffrn_orient_matrix_UB_33      0.0046404000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6341
_diffrn_reflns_theta_full        74.0294
_diffrn_reflns_theta_max         74.03
_diffrn_reflns_theta_min         5.99
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.593
_exptl_absorpt_correction_T_max  0.516
_exptl_absorpt_correction_T_min  0.362
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.2452
_exptl_crystal_description       block
_exptl_crystal_F_000             393.1307
_exptl_crystal_size_max          0.5911
_exptl_crystal_size_mid          0.4497
_exptl_crystal_size_min          0.3462
_refine_diff_density_max         0.2037
_refine_diff_density_min         -0.1514
_refine_diff_density_rms         0.0311
_refine_ls_d_res_high            0.8019
_refine_ls_d_res_low             7.3915
_refine_ls_goodness_of_fit_ref   1.0610
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    42
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3716
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0610
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0553P)^2^+0.1700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1069
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                3441
_reflns_number_total             3716
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c4cc09940k2.cif
_cod_data_source_block           xstr0256
_cod_database_code               7116706
_chemical_oxdiff_formula         'C25 H26 N2 O1'
_chemical_oxdiff_usercomment     SK413
_reflns_odcompleteness_completeness 96.81
_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), C17(H17), C18(H18),
 C20(H20), C21(H21), C22(H22), C23(H23), C25(H25)
2.c Idealised Me refined as rotating group:
 C6(H6a,H6b,H6c)
;