Copper- or Nickel-Enabled Oxidative Cross-Coupling of Unreactive C(sp(3))-H Bonds with Azole C(sp(2))-H Bonds: Rapid Access to β-Azolyl Propanoic Acid Derivatives.
Tan, Guangying; Zhang, Luoqiang; Liao, Xingrong; Shi, Yang; Wu, Yimin; Yang, Yudong; You, Jingsong; Organic letters 19 (2017) 4830–4833; doi:10.1021/acs.orglett.7b02265

data_1547571
_publ_section_title
;
 Copper- or Nickel-Enabled Oxidative Cross-Coupling of Unreactive
 C(sp(3))-H Bonds with Azole C(sp(2))-H Bonds: Rapid Access to \b-Azolyl
 Propanoic Acid Derivatives.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4830
_journal_page_last               4833
_journal_paper_doi               10.1021/acs.orglett.7b02265
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C20 H26 Cu N4 O4, 3(C4 H8 O2)'
_chemical_formula_sum            'C32 H50 Cu N4 O10'
_chemical_formula_weight         714.30
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2017-08-16
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                88.759(6)
_cell_angle_beta                 86.694(5)
_cell_angle_gamma                66.762(7)
_cell_formula_units_Z            2
_cell_length_a                   10.8093(7)
_cell_length_b                   12.3197(11)
_cell_length_c                   14.2754(8)
_cell_measurement_reflns_used    5916
_cell_measurement_temperature    119.97(18)
_cell_measurement_theta_max      28.5250
_cell_measurement_theta_min      4.0810
_cell_volume                     1743.9(2)
_computing_cell_refinement
'CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48)'
_computing_data_collection
'CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48)'
_computing_data_reduction
'CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      119.97(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   -1.00   83.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       15.5694   57.0000  -90.0000 84

  2 omega   -1.00   83.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       15.5694   57.0000 -120.0000 84

  3 omega   34.00   88.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       15.5694 -178.0000 -120.0000 54

  4 omega  -14.00   87.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       15.5694   19.0000 -180.0000 101

  5 omega  -11.00   83.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       15.5694   77.0000    0.0000 94

  6 omega  -63.00  -13.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.5069  112.0000   61.0000 50

  7 omega  -43.00   51.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.5069   77.0000   30.0000 94

  8 omega   34.00   88.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       15.5694 -178.0000    0.0000 54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0165978000
_diffrn_orient_matrix_UB_12      -0.0196606000
_diffrn_orient_matrix_UB_13      -0.0471691000
_diffrn_orient_matrix_UB_21      0.0056414000
_diffrn_orient_matrix_UB_22      0.0539167000
_diffrn_orient_matrix_UB_23      -0.0126645000
_diffrn_orient_matrix_UB_31      0.0693335000
_diffrn_orient_matrix_UB_32      -0.0251479000
_diffrn_orient_matrix_UB_33      0.0095773000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_unetI/netI     0.0739
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_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       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20829
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.376
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'metallic greenish green'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       block
_exptl_crystal_F_000             758
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         3.280
_refine_diff_density_min         -0.906
_refine_diff_density_rms         0.148
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     430
_refine_ls_number_reflns         7129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.1242
_refine_ls_R_factor_gt           0.1055
_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^)+(0.1107P)^2^+13.4471P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2801
_refine_ls_wR_factor_ref         0.2911
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5636
_reflns_number_total             7129
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02265_si_002.cif
_cod_data_source_block           tgy007-120k
_cod_database_code               1547571
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C010(H01A,H01B), C011(H01I,H01J), C012(H01C,H01D), C013(H01E,H01F), C014(H01K,
 H01L), C015(H01M,H01N), C016(H01G,H01H), C017(H01Q,H01R), C018(H01S,H01T),
 C019(H01O,H01P), C01A(H01U,H01V), C01B(H01W,H01X)
2.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00I(H00I), C00J(H00J), C00N(H00N), C00Q(H00Q),
 C00R(H00R), C00S(H00S)
2.c Idealised Me refined as rotating group:
 C00U(H00A,H00B,H00C), C00V(H00D,H00G,H00H), C00W(H00K,H00L,H00M), C00X(H00O,
 H00P,H00T), C00Y(H00U,H00V,H00W), C00Z(H00X,H00Y,H)
;
_shelx_res_checksum              63546
_shelx_hkl_checksum              59313
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-03-27
_olex2_submission_special_instructions 'No special instructions were received'