Stereoselective copper-catalyzed heteroarene C-H functionalization/Michael-type annulation cascade with α-diazocarbonyls.
Bhat, Aabid; Tucker, Nathan; Lin, Jian-Bin; Grover, Huck; Chemical communications (Cambridge, England) 57 (2021) 10556–10559; doi:10.1039/d1cc04590c

data_7128976
_publ_section_title
;
 Stereoselective copper-catalyzed heteroarene C-H
 functionalization/Michael-type annulation cascade with \a-diazocarbonyls.
;
_journal_issue                   81
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              10556
_journal_page_last               10559
_journal_paper_doi               10.1039/d1cc04590c
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C25 H25 N O5'
_chemical_formula_sum            'C25 H25 N O5'
_chemical_formula_weight         419.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-10-07
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-08-04 deposited with the CCDC.	2021-09-20 downloaded from the CCDC.
;
_cell_angle_alpha                70.812(4)
_cell_angle_beta                 83.459(4)
_cell_angle_gamma                69.525(4)
_cell_formula_units_Z            2
_cell_length_a                   9.2549(5)
_cell_length_b                   10.9358(4)
_cell_length_c                   11.8353(5)
_cell_measurement_reflns_used    6326
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.8320
_cell_measurement_theta_min      3.9350
_cell_volume                     1059.83(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_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     29.00 120.00   0.50    0.08    --   47.95  67.00 -62.00  182
  2  \w     85.00 178.00   0.50    0.32    --  107.75  77.00  60.00  186
  3  \w     87.00 177.00   0.50    0.32    --  107.75  77.00  30.00  180
  4  \w     96.00 121.00   0.50    0.32    --  107.75  30.00  30.00   50
  5  \w    132.00 173.00   0.50    0.32    --  107.75  15.00 -30.00   82
  6  \w     89.00 178.00   0.50    0.32    --  107.75  67.00 -62.00  178
  7  \w     94.00 178.00   0.50    0.32    --  107.75  15.00-120.00  168
  8  \w     95.00 178.00   0.50    0.32    --  107.75  45.00-180.00  166
  9  \w     93.00 149.00   0.50    0.32    --  107.75  61.00-150.00  112
 10  \w     36.00  66.00   0.50    0.32    --  107.75 -94.00  90.00   60
 11  \w     35.00 112.00   0.50    0.32    --  107.75-125.00 150.00  154
 12  \w     39.00  77.00   0.50    0.32    --  107.75-125.00  60.00   76
 13  \w     78.00 106.00   0.50    0.32    --  107.75 -94.00   0.00   56
 14  \w     34.00  96.00   0.50    0.08    --   47.95-125.00   0.00  124
 15  \w     35.00  66.00   0.50    0.32    --  107.75 -94.00   0.00   62
 16  \w     36.00 106.00   0.50    0.32    --  107.75 -94.00 -60.00  140
 17  \w     82.00 107.00   0.50    0.32    --  107.75-104.00 -82.80   50
 18  \w     44.00  69.00   0.50    0.32    --  107.75-104.00 -82.80   50
 19  \w     66.00 105.00   0.50    0.32    --  107.75 -94.00-150.00   78
 20  \w     34.00  96.00   0.50    0.08    --   47.95-125.00-180.00  124
 21  \w     54.00 106.00   0.50    0.32    --  107.75 -94.00-180.00  104
 22  \w     58.00 104.00   0.50    0.32    --  107.75 -94.00 -30.00   92
 23  \w     80.00 105.00   0.50    0.32    --  107.75 -94.00  30.00   50
 24  \w     70.00 105.00   0.50    0.32    --  107.75 -94.00  90.00   70
 25  \w     35.00 106.00   0.50    0.32    --  107.75 -94.00  60.00  142
 26  \w     49.00  97.00   0.50    0.32    --  107.75 -94.00 120.00   96
 27  \w     44.00 105.00   0.50    0.32    --  107.75 -94.00 150.00  122
 28  \w    -24.00  67.00   0.50    0.08    --   47.95 -67.00 163.00  182
 29  \w     35.00  89.00   0.50    0.32    --  107.75 -67.00 163.00  108
 30  \w     35.00  60.00   0.50    0.32    --  107.75 -61.00  90.00   50
 31  \w    -26.00  30.00   0.50    0.08    --   47.95 -19.00-120.00  112
 32  \w     51.00  79.00   0.50    0.32    --  107.75 -61.00 -30.00   56
 33  \w     37.00  64.00   0.50    0.32    --  107.75 -61.00 -60.00   54
 34  \w     37.00  73.00   0.50    0.32    --  107.75 -61.00-150.00   72
 35  \w     95.00 138.00   0.50    0.32    --  107.75 125.00  30.00   86
 36  \w    146.00 175.00   0.50    0.32    --  107.75 125.00  30.00   58
 37  \w     96.00 147.00   0.50    0.32    --  107.75 125.00-120.00  102
 38  \w    -67.00  25.00   0.50    0.08    --  -47.95  67.00 -62.00  184
 39  \w    -75.00 -13.00   0.50    0.32    --  -86.25  67.00 -62.00  124
 40  \w    -43.00 -14.00   0.50    0.32    --  -86.25  45.00  60.00   58
 41  \w    -43.00 -14.00   0.50    0.32    --  -86.25  45.00  90.00   58
 42  \w    -43.00 -14.00   0.50    0.32    --  -86.25  45.00 120.00   58
 43  \w   -120.00 -29.00   0.50    0.08    --  -47.95 -67.00 163.00  182
 44  \w   -159.00 -67.00   0.50    0.32    --  -86.25 -67.00 163.00  184
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1523264000
_diffrn_orient_matrix_UB_12      0.0450444000
_diffrn_orient_matrix_UB_13      -0.0671253000
_diffrn_orient_matrix_UB_21      0.0321439000
_diffrn_orient_matrix_UB_22      0.1300647000
_diffrn_orient_matrix_UB_23      -0.0817275000
_diffrn_orient_matrix_UB_31      0.0856460000
_diffrn_orient_matrix_UB_32      -0.0779446000
_diffrn_orient_matrix_UB_33      -0.0883746000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17518
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.352
_diffrn_reflns_theta_min         3.955
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.314
_exptl_crystal_description       irregular
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.264
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0013(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4403
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0436
_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^)+(0.0510P)^2^+0.3185P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1217
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3765
_reflns_number_total             4403
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04590c2.cif
_cod_data_source_block           nt-c-118-b-2
_cod_depositor_comments
'Adding full bibliography for 7128973--7128976.cif.'
_cod_original_cell_volume        1059.84(9)
_cod_database_code               7128976
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.929
_shelx_estimated_absorpt_t_min   0.827
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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:
 C12(H12A,H12B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C9(H9), C10(H10), C19(H19), C20(H20), C21(H21), C22(H22),
 C23(H23)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C17(H17A,H17B,H17C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C)
;
_shelx_res_checksum              71172
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.646
_oxdiff_exptl_absorpt_empirical_full_min 0.736