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_7128974
_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         'C22 H25 N O7'
_chemical_formula_sum            'C22 H25 N O7'
_chemical_formula_weight         415.43
_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             2020-01-28
_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                70.006(2)
_cell_angle_beta                 77.003(2)
_cell_angle_gamma                88.377(3)
_cell_formula_units_Z            2
_cell_length_a                   8.1806(3)
_cell_length_b                   11.5207(3)
_cell_length_c                   12.2742(2)
_cell_measurement_reflns_used    15941
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      76.5000
_cell_measurement_theta_min      4.0820
_cell_volume                     1057.73(5)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173(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 0.987
_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     95.00 178.00   0.50    0.50    --  107.75  45.00  30.00  166
  2  \w     95.00 178.00   0.50    0.50    --  107.75  45.00 -30.00  166
  3  \w     95.00 178.00   0.50    0.50    --  107.75  30.00   0.00  166
  4  \w     95.00 178.00   0.50    0.50    --  107.75  45.00 -60.00  166
  5  \w     33.00 122.00   0.50    0.05    --   47.95  13.00  92.00  178
  6  \w     93.00 178.00   0.50    0.50    --  107.75  13.00  92.00  170
  7  \w     95.00 178.00   0.50    0.50    --  107.75  45.00-120.00  166
  8  \w     95.00 178.00   0.50    0.50    --  107.75  45.00-180.00  166
  9  \w     94.00 178.00   0.50    0.50    --  107.75  15.00-180.00  168
 10  \w    -59.00  25.00   0.50    0.05    --  -47.95  57.00 -30.00  168
 11  \w    -16.00  28.00   0.50    0.05    --  -47.95  19.00-150.00   88
 12  \w    -16.00  28.00   0.50    0.05    --  -47.95  19.00-120.00   88
 13  \w    -43.00 -14.00   0.50    0.50    --  -86.25  45.00  60.00   58
 14  \w    -11.00  27.00   0.50    0.05    --  -47.95  13.00  92.00   76
 15  \w     35.00 112.00   0.50    0.50    --  107.75-125.00 120.00  154
 16  \w     35.00 112.00   0.50    0.50    --  107.75-125.00 150.00  154
 17  \w     35.00 107.00   0.50    0.50    --  107.75-102.00  14.36  144
 18  \w     35.00 112.00   0.50    0.50    --  107.75-125.00 -30.00  154
 19  \w     35.00 106.00   0.50    0.50    --  107.75 -94.00 -30.00  142
 20  \w     35.00 112.00   0.50    0.50    --  107.75-125.00-120.00  154
 21  \w     35.00 112.00   0.50    0.50    --  107.75-125.00-180.00  154
 22  \w     35.00 106.00   0.50    0.50    --  107.75 -94.00-129.37  142
 23  \w     35.00 106.00   0.50    0.50    --  107.75 -94.00-120.00  142
 24  \w     35.00 106.00   0.50    0.50    --  107.75 -94.00 -90.00  142
 25  \w     35.00 106.00   0.50    0.50    --  107.75 -94.00 -60.00  142
 26  \w     35.00 106.00   0.50    0.50    --  107.75 -94.00  30.00  142
 27  \w     35.00 106.00   0.50    0.50    --  107.75 -94.00  90.00  142
 28  \w     35.00 106.00   0.50    0.50    --  107.75 -94.00 120.00  142
 29  \w     35.00 131.00   0.50    0.50    --  107.75 -77.00 120.00  192
 30  \w     35.00  79.00   0.50    0.50    --  107.75 -61.00 150.00   88
 31  \w     35.00  79.00   0.50    0.50    --  107.75 -61.00 120.00   88
 32  \w     35.00  79.00   0.50    0.50    --  107.75 -61.00  30.00   88
 33  \w     35.00  79.00   0.50    0.50    --  107.75 -61.00   0.00   88
 34  \w     35.00  79.00   0.50    0.50    --  107.75 -61.00 -60.00   88
 35  \w     35.00  79.00   0.50    0.50    --  107.75 -61.00-120.00   88
 36  \w    -26.00  25.00   0.50    0.05    --   47.95 -13.00 -79.00  102
 37  \w    -26.00  30.00   0.50    0.05    --   47.95 -19.00 150.00  112
 38  \w     95.00 178.00   0.50    0.50    --  107.75 125.00  60.00  166
 39  \w   -122.00 -33.00   0.50    0.05    --  -47.95 -13.00 -79.00  178
 40  \w   -120.00 -25.00   0.50    0.05    --  -47.95 -77.00 -30.00  190
 41  \w   -120.00 -25.00   0.50    0.05    --  -47.95 -77.00 150.00  190
 42  \w   -120.00 -25.00   0.50    0.05    --  -47.95 -77.00  60.00  190
 43  \w   -120.00 -25.00   0.50    0.05    --  -47.95 -77.00 -90.00  190
 44  \w   -120.00 -25.00   0.50    0.05    --  -47.95 -77.00-120.00  190
 45  \w   -120.00 -25.00   0.50    0.05    --  -47.95 -77.00-180.00  190
 46  \w   -120.00 -51.00   0.50    0.05    --  -47.95 -77.00  90.00  138
 47  \w    -86.00 -13.00   0.50    0.05    --  -47.95 125.00-180.00  146
 48  \w    -86.00 -13.00   0.50    0.50    --  -86.25 125.00  90.00  146
 49  \w   -161.00 -71.00   0.50    0.50    --  -86.25 -13.00 -79.00  180
;
_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      -0.1022263000
_diffrn_orient_matrix_UB_12      0.1168168000
_diffrn_orient_matrix_UB_13      -0.0240958000
_diffrn_orient_matrix_UB_21      -0.1503993000
_diffrn_orient_matrix_UB_22      -0.0756821000
_diffrn_orient_matrix_UB_23      -0.0026572000
_diffrn_orient_matrix_UB_31      -0.0662513000
_diffrn_orient_matrix_UB_32      -0.0305242000
_diffrn_orient_matrix_UB_33      0.1350541000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            26839
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.442
_diffrn_reflns_theta_min         3.937
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57610
_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    1.304
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         4446
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0434
_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^)+(0.0574P)^2^+0.1941P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1122
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4027
_reflns_number_total             4446
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04590c2.cif
_cod_data_source_block           nt186_173k
_cod_depositor_comments
'Adding full bibliography for 7128973--7128976.cif.'
_cod_database_code               7128974
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C22H25NO7
_shelx_estimated_absorpt_t_max   0.923
_shelx_estimated_absorpt_t_min   0.868
_diffrn_oxdiff_digest_frames
;
0121c51874c7844028688461a791bd7cd70003248d0
;
_diffrn_oxdiff_digest_hkl
;
01631328b65304280523791576368939b8e94d
;
_reflns_odcompleteness_completeness 99.82
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C18-C19 \\sim C18-C19A
 with sigma of 0.02
3. Others
 Sof(H18C)=Sof(H18D)=Sof(C19A)=Sof(H19D)=Sof(H19E)=Sof(H19F)=1-FVAR(1)
 Sof(H18A)=Sof(H18B)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H19C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C15(H15A,H15B), C18(H18A,H18B), C18(H18C,H18D)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C20(H20)
4.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C16(H16A,H16B,H16C), C19(H19A,H19B,
 H19C), C19A(H19D,H19E,H19F), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              73305
_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 1.728
_oxdiff_exptl_absorpt_empirical_full_min 0.647