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_7128975
_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         'C23 H27 N O7'
_chemical_formula_sum            'C23 H27 N O7'
_chemical_formula_weight         429.45
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-02
_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                90
_cell_angle_beta                 104.3152(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.27378(13)
_cell_length_b                   17.12971(15)
_cell_length_c                   9.94500(9)
_cell_measurement_reflns_used    10349
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.1660
_cell_measurement_theta_min      3.4260
_cell_volume                     2191.04(4)
_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 0.982
_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    -12.00  26.00   0.50    0.08    --  -47.95  19.00 -60.00   76
  2  \w    -16.00  21.00   0.50    0.08    --  -47.95  19.00 -90.00   74
  3  \w    -43.00 -14.00   0.50    0.33    --  -86.25  45.00-150.00   58
  4  \w    -80.00   2.00   0.50    0.08    --  -47.95 100.00  35.00  164
  5  \w     31.00  58.00   0.50    0.08    --   47.95-100.00 -69.00   54
  6  \w     64.00 106.00   0.50    0.33    --  107.75-100.00 -69.00   84
  7  \w     81.00 106.00   0.50    0.33    --  107.75 -94.00 -30.00   50
  8  \w     50.00  78.00   0.50    0.33    --  107.75 -61.00 -60.00   56
  9  \w     35.00  60.00   0.50    0.33    --  107.75 -94.00 -30.00   50
 10  \w     46.00  79.00   0.50    0.33    --  107.75 -61.00 -30.00   66
 11  \w     37.00  71.00   0.50    0.33    --  107.75 -61.00  30.00   68
 12  \w     53.00  79.00   0.50    0.33    --  107.75 -61.00  60.00   52
 13  \w     39.00  79.00   0.50    0.33    --  107.75 -61.00  90.00   80
 14  \w     36.00  78.00   0.50    0.33    --  107.75 -61.00 150.00   84
 15  \w     36.00  76.00   0.50    0.33    --  107.75-125.00  90.00   80
 16  \w     83.00 110.00   0.50    0.33    --  107.75-125.00  90.00   54
 17  \w     39.00  65.00   0.50    0.33    --  107.75 -94.00  30.00   52
 18  \w     97.00 167.00   0.50    0.33    --  107.75  30.00  90.00  140
 19  \w    140.00 173.00   0.50    0.33    --  107.75  77.00 150.00   66
 20  \w    152.00 178.00   0.50    0.33    --  107.75 125.00  90.00   52
 21  \w    122.00 147.00   0.50    0.33    --  107.75 125.00  90.00   50
 22  \w    112.00 165.00   0.50    0.33    --  107.75 100.00  35.00  106
 23  \w    153.00 178.00   0.50    0.33    --  107.75  61.00 -30.00   50
 24  \w    149.00 174.00   0.50    0.33    --  107.75  61.00 -90.00   50
 25  \w    109.00 135.00   0.50    0.33    --  107.75  61.00 -90.00   52
 26  \w     97.00 143.00   0.50    0.33    --  107.75  61.00 -30.00   92
 27  \w     96.00 165.00   0.50    0.33    --  107.75 125.00  60.00  138
 28  \w     86.00 123.00   0.50    0.33    --  107.75  77.00 150.00   74
 29  \w    -13.00  27.00   0.50    0.08    --  -47.95  19.00 150.00   80
 30  \w    -71.00 -46.00   0.50    0.33    --  -86.25 100.00  35.00   50
 31  \w   -130.00-105.00   0.50    0.33    --  -86.25-100.00 -69.00   50
 32  \w   -120.00 -95.00   0.50    0.08    --  -47.95-125.00  60.00   50
 33  \w   -118.00 -73.00   0.50    0.08    --  -47.95-125.00  90.00   90
 34  \w     38.00  63.00   0.50    0.33    --  107.75 -61.00-180.00   50
;
_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      -0.0310449000
_diffrn_orient_matrix_UB_12      0.0817866000
_diffrn_orient_matrix_UB_13      0.0400679000
_diffrn_orient_matrix_UB_21      -0.1148065000
_diffrn_orient_matrix_UB_22      -0.0254190000
_diffrn_orient_matrix_UB_23      -0.0336460000
_diffrn_orient_matrix_UB_31      0.0140567000
_diffrn_orient_matrix_UB_32      -0.0274268000
_diffrn_orient_matrix_UB_33      0.1511267000
_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  0.0550
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            19064
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.343
_diffrn_reflns_theta_min         3.436
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.801
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60225
_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    1.302
_exptl_crystal_description       irregular
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.199
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.00083(18)
_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   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4580
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0458P)^2^+0.6602P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1069
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3981
_reflns_number_total             4580
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04590c2.cif
_cod_data_source_block           ahb-a-106
_cod_depositor_comments
'Adding full bibliography for 7128973--7128976.cif.'
_cod_database_code               7128975
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C23H27NO7
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.857
_reflns_odcompleteness_completeness 99.98
_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:
 C10(H10A,H10B), C11(H11A,H11B), C16(H16A,H16B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C21(H21)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C17(H17A,H17B,H17C), C20(H20A,H20B,
 H20C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              37919
_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 1.601
_oxdiff_exptl_absorpt_empirical_full_min 0.395