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_7128973
_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      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             2020-02-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-04 deposited with the CCDC.	2021-09-20 downloaded from the CCDC.
;
_cell_angle_alpha                111.4045(10)
_cell_angle_beta                 93.4027(8)
_cell_angle_gamma                104.9018(9)
_cell_formula_units_Z            2
_cell_length_a                   8.24253(9)
_cell_length_b                   10.98466(11)
_cell_length_c                   12.92511(13)
_cell_measurement_reflns_used    36431
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.0590
_cell_measurement_theta_min      3.7160
_cell_volume                     1037.52(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (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 0.999
_diffrn_measured_fraction_theta_max 0.986
_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     -3.00  41.00   0.50    0.05    --   26.00  90.00 171.99   88
  2  \w     36.00 121.00   0.50    0.05    --   47.82  37.00 -30.00  170
  3  \w     35.00 122.00   0.50    0.05    --   47.82  19.00 -90.00  174
  4  \w     25.00 120.00   0.50    0.05    --   47.82  77.00-120.00  190
  5  \w      8.00  39.00   0.50    0.05    --   38.00  92.00 -52.39   62
  6  \w     10.00  43.00   0.50    0.05    --   38.00  89.00  23.75   66
  7  \w    -21.00  43.00   0.50    0.05    --    6.00  86.00  84.54  128
  8  \w     31.00 126.00   0.50    0.05    --   54.00  77.00 178.41  190
  9  \w     43.00 139.00   0.50    0.05    --   66.00  77.00 154.84  192
 10  \w     90.00 149.00   0.50    0.20    --  107.75  77.00  60.00  118
 11  \w     86.00 133.00   0.50    0.20    --  107.75  77.00  90.00   94
 12  \w     85.00 150.00   0.50    0.20    --  107.75  77.00   0.00  130
 13  \w     85.00 154.00   0.50    0.20    --  107.75  77.00  30.00  138
 14  \w     95.00 121.00   0.50    0.20    --  107.75  77.00 -30.00   52
 15  \w    141.00 167.00   0.50    0.20    --  107.75  77.00 -60.00   52
 16  \w     85.00 121.00   0.50    0.20    --  107.75  77.00 -60.00   72
 17  \w     87.00 128.00   0.50    0.20    --  107.75  77.00-120.00   82
 18  \w     70.00 113.00   0.50    0.20    --   90.00  77.00-118.63   86
 19  \w     87.00 125.00   0.50    0.20    --  107.75  77.00-180.00   76
 20  \w    136.00 175.00   0.50    0.20    --  107.75  77.00-180.00   78
 21  \w    144.00 176.00   0.50    0.20    --  107.75  77.00-150.00   64
 22  \w    123.00 176.00   0.50    0.20    --  107.75  77.00 -90.00  106
 23  \w     85.00 117.00   0.50    0.20    --  107.75  77.00 -90.00   64
 24  \w    137.00 168.00   0.50    0.20    --  107.75  77.00 -30.00   62
 25  \w    143.00 177.00   0.50    0.20    --  107.75  77.00 150.00   68
 26  \w     85.00 129.00   0.50    0.20    --  107.75  77.00 150.00   88
 27  \w     93.00 155.00   0.50    0.20    --  107.75  77.00 120.00  124
 28  \w     32.00 126.00   0.50    0.05    --   54.00  76.00 147.57  188
 29  \w     36.00 131.00   0.50    0.05    --   58.00  75.00  -8.85  190
 30  \w     37.00 131.00   0.50    0.05    --   58.00  73.00 -78.67  188
 31  \w     85.00 134.00   0.50    0.20    --  107.75  77.00-150.00   98
 32  \w    134.00 178.00   0.50    0.20    --  107.75  77.00-120.00   88
 33  \w     98.00 124.00   0.50    0.20    --  107.75  61.00 -60.00   52
 34  \w     87.00 171.00   0.50    0.20    --  107.75  73.00 -44.08  168
 35  \w     91.00 160.00   0.50    0.20    --  107.75  61.00-150.00  138
 36  \w    136.00 161.00   0.50    0.20    --  107.75  61.00 -60.00   50
 37  \w     94.00 140.00   0.50    0.20    --  107.75  61.00  60.00   92
 38  \w     91.00 178.00   0.50    0.20    --  107.75  61.00  90.00  174
 39  \w    141.00 175.00   0.50    0.20    --  102.00  71.00 116.87   68
 40  \w     93.00 150.00   0.50    0.20    --  107.75  61.00 150.00  114
 41  \w     82.00 112.00   0.50    0.20    --  102.00  71.00 116.87   60
 42  \w    153.00 178.00   0.50    0.20    --  107.75  61.00  60.00   50
 43  \w     95.00 148.00   0.50    0.20    --  107.75  45.00   0.00  106
 44  \w     98.00 155.00   0.50    0.20    --  107.75  15.00 -60.00  114
 45  \w     95.00 143.00   0.50    0.20    --  107.75  61.00-180.00   96
 46  \w     89.00 178.00   0.50    0.20    --  107.75 135.00-104.00  178
 47  \w     90.00 178.00   0.50    0.20    --  107.75 133.00  76.00  176
 48  \w    140.00 166.00   0.50    0.20    --  107.75 125.00   0.00   52
 49  \w    100.00 137.00   0.50    0.20    --  107.75 125.00   0.00   74
 50  \w     39.00  84.00   0.50    0.20    --  107.75 -77.00-180.00   90
 51  \w     40.00 101.00   0.50    0.05    --   47.82-135.00-170.00  122
 52  \w     39.00 100.00   0.50    0.05    --   47.82-133.00   8.00  122
 53  \w     41.00 120.00   0.50    0.20    --  107.75-136.00  62.76  158
 54  \w     39.00 118.00   0.50    0.20    --  107.75-133.00   8.00  158
 55  \w     36.00  71.00   0.50    0.20    --  107.75-125.00 -30.00   70
 56  \w     77.00 108.00   0.50    0.20    --  107.75-125.00 -30.00   62
 57  \w     40.00 119.00   0.50    0.20    --  107.75-135.00-170.00  158
 58  \w     81.00 112.00   0.50    0.20    --  107.75-125.00 -90.00   62
 59  \w     35.00  76.00   0.50    0.20    --  107.75-125.00 -90.00   82
 60  \w     35.00  97.00   0.50    0.20    --  107.75 -94.00 -30.00  124
 61  \w     36.00 107.00   0.50    0.20    --  107.75-125.00  90.00  142
 62  \w     46.00  96.00   0.50    0.20    --  107.75-125.00 150.00  100
 63  \w     35.00  66.00   0.50    0.20    --  107.75 -94.00  90.00   62
 64  \w     41.00  66.00   0.50    0.20    --  107.75 -94.00 120.00   50
 65  \w     37.00  95.00   0.50    0.20    --  107.75 -94.00 150.00  116
 66  \w     77.00 103.00   0.50    0.20    --  107.75 -94.00 120.00   52
 67  \w     67.00 102.00   0.50    0.20    --  107.75 -94.00  30.00   70
 68  \w     73.00 106.00   0.50    0.20    --  107.75 -94.00  90.00   66
 69  \w     35.00  66.00   0.50    0.20    --  107.75 -94.00   0.00   62
 70  \w     36.00  80.00   0.50    0.20    --  107.75 -94.00 -90.00   88
 71  \w     35.00 105.00   0.50    0.20    --  107.75 -94.00-180.00  140
 72  \w    -93.00 -18.00   0.50    0.05    --  -47.82 135.00-104.00  150
 73  \w    -92.00 -17.00   0.50    0.20    --  -86.25 133.00  76.00  150
 74  \w    -92.00 -17.00   0.50    0.05    --  -47.82 133.00  76.00  150
 75  \w   -119.00 -25.00   0.50    0.05    --  -47.82 -77.00  90.00  188
 76  \w   -119.00 -25.00   0.50    0.05    --  -47.82 -77.00 120.00  188
 77  \w   -119.00 -25.00   0.50    0.05    --  -47.82 -77.00 -90.00  188
 78  \w   -135.00 -44.00   0.50    0.05    --  -62.00 -65.00 -81.11  182
 79  \w   -159.00 -63.00   0.50    0.20    --  -86.25 -77.00-180.00  192
 80  \w   -135.00 -38.00   0.50    0.05    --  -62.00 -80.00-146.14  194
 81  \w   -139.00 -43.00   0.50    0.05    --  -66.00 -78.00 -83.88  192
 82  \w   -139.00-112.00   0.50    0.20    --  -86.25 -77.00 -90.00   54
 83  \w    -89.00 -63.00   0.50    0.20    --  -86.25 -77.00 -90.00   52
 84  \w    -90.00 -64.00   0.50    0.20    --  -86.25 -77.00 -30.00   52
 85  \w   -158.00-131.00   0.50    0.20    --  -86.25 -77.00 -30.00   54
 86  \w   -139.00 -42.00   0.50    0.05    --  -66.00 -80.00 100.18  194
 87  \w    -88.00 -63.00   0.50    0.20    --  -86.25 -77.00 120.00   50
 88  \w    -94.00 -63.00   0.50    0.20    --  -86.25 -77.00 112.08   62
 89  \w   -158.00 -63.00   0.50    0.20    --  -86.25 -78.00 141.89  190
 90  \w    -94.00 -63.00   0.50    0.20    --  -86.25 -77.00  60.00   62
 91  \w   -151.00 -55.00   0.50    0.20    --  -78.00 -76.00  54.43  192
 92  \w   -131.00 -35.00   0.50    0.05    --  -58.00 -76.00  44.13  192
 93  \w    -93.00 -63.00   0.50    0.20    --  -86.25 -77.00   0.00   60
 94  \w   -154.00 -60.00   0.50    0.20    --  -82.00 -75.00   9.20  188
 95  \w   -126.00 -31.00   0.50    0.05    --  -54.00 -77.00 -33.41  190
 96  \w   -151.00 -55.00   0.50    0.20    --  -78.00 -76.00-116.62  192
 97  \w   -154.00 -60.00   0.50    0.20    --  -82.00 -75.00-172.21  188
 98  \w    -98.00 -64.00   0.50    0.20    --  -86.25 -75.00-113.68   68
 99  \w    -92.00 -66.00   0.50    0.20    --  -86.25 -74.00-140.52   52
100  \w   -154.00 -61.00   0.50    0.20    --  -82.00 -73.00-142.00  186
101  \w   -154.00 -61.00   0.50    0.20    --  -82.00 -73.00 -77.21  186
102  \w    -98.00 -65.00   0.50    0.20    --  -86.25 -73.00 -22.11   66
103  \w   -139.00 -45.00   0.50    0.05    --  -66.00 -72.00   5.87  188
104  \w   -119.00 -65.00   0.50    0.20    --  -86.25 -72.00  33.47  108
105  \w    -93.00 -65.00   0.50    0.20    --  -86.25 -72.00 148.04   56
106  \w    -91.00 -65.00   0.50    0.20    --  -86.25 -72.00  85.71   52
107  \w    -92.00 -66.00   0.50    0.20    --  -86.25 -71.00  73.41   52
108  \w   -151.00 -58.00   0.50    0.20    --  -78.00 -69.00 -66.76  186
109  \w   -146.00 -56.00   0.50    0.20    --  -74.00 -66.00-178.00  180
110  \w   -119.00 -67.00   0.50    0.05    --  -47.82-135.00-170.00  104
111  \w   -159.00 -67.00   0.50    0.20    --  -86.25-135.00-170.00  184
112  \w   -159.00 -68.00   0.50    0.20    --  -86.25-133.00   8.00  182
113  \w   -119.00 -68.00   0.50    0.05    --  -47.82-133.00   8.00  102
;
_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      0.1249135000
_diffrn_orient_matrix_UB_12      0.1257644000
_diffrn_orient_matrix_UB_13      0.0959731000
_diffrn_orient_matrix_UB_21      -0.0855333000
_diffrn_orient_matrix_UB_22      -0.0466970000
_diffrn_orient_matrix_UB_23      0.0875584000
_diffrn_orient_matrix_UB_31      0.1249187000
_diffrn_orient_matrix_UB_32      -0.0832970000
_diffrn_orient_matrix_UB_33      -0.0012570000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            50608
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.224
_diffrn_reflns_theta_min         3.728
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.846
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
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    1.375
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4341
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0324
_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^)+(0.0398P)^2^+0.4393P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0825
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4185
_reflns_number_total             4341
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04590c2.cif
_cod_data_source_block           ahb-5-84
_cod_depositor_comments
'Adding full bibliography for 7128973--7128976.cif.'
_cod_database_code               7128973
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C23H27NO7
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.829
_diffrn_oxdiff_digest_frames
;
012572d4ae9beed76ff333c02c615ee36b13182ea1a
;
_diffrn_oxdiff_digest_hkl
;
01277a49e9a46b99574af27218b0f9eaba3cc8
;
_reflns_odcompleteness_completeness 99.69
_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:
 C11(H11A,H11B), C12(H12A,H12B), 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              61670
_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 1.663
_oxdiff_exptl_absorpt_empirical_full_min 0.676