Rhodium(iii)-catalyzed asymmetric [4+1] spiroannulations of O-pivaloyl oximes with α-diazo compounds.
Sun, Lincong; Liu, Bingxian; Zhao, Yanlian; Chang, Junbiao; Kong, Lingheng; Wang, Fen; Deng, Wei-Qiao; Li, Xingwei; Chemical communications (Cambridge, England) 57 (2021) 8268–8271; doi:10.1039/d1cc02888j

data_7128674
_publ_section_title
;
 Rhodium(iii)-catalyzed asymmetric [4+1] spiroannulations of O-pivaloyl
 oximes with \a-diazo compounds.
;
_journal_issue                   67
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              8268
_journal_page_last               8271
_journal_paper_doi               10.1039/d1cc02888j
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C23 H15 Br N2 O2'
_chemical_formula_sum            'C23 H15 Br N2 O2'
_chemical_formula_weight         431.28
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc27gs2l
_audit_creation_date             2021-03-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-03-11 deposited with the CCDC.	2021-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.46680(10)
_cell_length_b                   12.02910(10)
_cell_length_c                   18.2481(2)
_cell_measurement_reflns_used    16164
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.3120
_cell_measurement_theta_min      4.3800
_cell_volume                     1858.53(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -57.00  31.00   1.00    1.00    --  -35.62  68.00 -47.00   88
  2  \w   -102.00 -14.00   1.00    1.00    --  -35.62 -68.00 179.00   88
  3  \w    -32.00  62.00   1.00    1.00    --   35.62 -76.00  59.00   94
  4  \w     40.00 133.00   1.00    1.24    --  107.12 -76.00  59.00   93
  5  \w     40.00 134.00   1.00    1.24    --  107.12 -77.00 -55.00   94
  6  \w     41.00 129.00   1.00    1.24    --  107.12 -68.00 179.00   88
  7  \w    -32.00  52.00   1.00    1.00    --   35.62 -57.00  90.00   84
  8  \w      1.00  75.00   1.00    1.00    --   35.62 -99.00 -60.00   74
  9  \w     55.00 108.00   1.00    1.00    --   35.62-178.00  90.00   53
 10  \w     39.00 125.00   1.00    1.24    --  107.12 -45.00  60.00   86
 11  \w     38.00 110.00   1.00    1.24    --  107.12 -95.00 -90.00   72
 12  \w     57.00 150.00   1.00    1.24    --  107.12 178.00 -30.00   93
 13  \w     86.00 177.00   1.00    1.24    --  107.12  30.00 -90.00   91
 14  \w     38.00 110.00   1.00    1.24    --  107.12 -95.00   0.00   72
 15  \w   -103.00 -19.00   1.00    1.00    --  -35.62 -57.00 -90.00   84
 16  \w   -103.00 -19.00   1.00    1.00    --  -35.62 -57.00  90.00   84
 17  \w   -103.00  -9.00   1.00    1.00    --  -35.62 -77.00  30.00   94
 18  \w     57.00 108.00   1.00    1.00    --   35.62 178.00 -60.00   51
 19  \w      6.00 107.00   1.00    1.00    --   35.62  19.00  60.00  101
 20  \w     69.00 178.00   1.00    1.24    --  107.12  15.00  60.00  109
 21  \w     80.00 175.00   1.00    1.24    --  107.12  77.00  60.00   95
 22  \w     69.00 178.00   1.00    1.24    --  107.12  15.00-180.00  109
 23  \w     80.00 175.00   1.00    1.24    --  107.12  77.00 150.00   95
 24  \w     89.00 174.00   1.00    1.24    --  107.12  61.00-150.00   85
 25  \w     80.00 175.00   1.00    1.24    --  107.12  77.00  90.00   95
 26  \w     80.00 175.00   1.00    1.24    --  107.12  77.00 -30.00   95
 27  \w     80.00 175.00   1.00    1.24    --  107.12  77.00-180.00   95
 28  \w     80.00 175.00   1.00    1.24    --  107.12  77.00 -90.00   95
 29  \w     86.00 177.00   1.00    1.24    --  107.12  30.00 -30.00   91
 30  \w    -32.00  52.00   1.00    1.00    --   35.62 -57.00-120.00   84
 31  \w      9.00  86.00   1.00    1.00    --   35.62  77.00 -30.00   77
 32  \w      9.00 103.00   1.00    1.00    --   35.62  77.00-120.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0580518000
_diffrn_orient_matrix_UB_12      -0.0579384000
_diffrn_orient_matrix_UB_13      0.0703373000
_diffrn_orient_matrix_UB_21      -0.1293956000
_diffrn_orient_matrix_UB_22      0.0890430000
_diffrn_orient_matrix_UB_23      0.0089376000
_diffrn_orient_matrix_UB_31      -0.1138594000
_diffrn_orient_matrix_UB_32      -0.0716425000
_diffrn_orient_matrix_UB_33      -0.0458194000
_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  0.0347
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_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       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            24553
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.427
_diffrn_reflns_theta_min         4.402
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.192
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78324
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 1470 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.026(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3613
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0271
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0410P)^2^+0.4514P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0736
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3529
_reflns_number_total             3613
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc02888j2.cif
_cod_data_source_block           slc-5-33-20210310
_cod_depositor_comments
'Adding full bibliography for 7128674--7128676.cif.'
_cod_database_code               7128674
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'N1 Br1 C1 H1 O1'
_shelx_estimated_absorpt_t_max   0.741
_shelx_estimated_absorpt_t_min   0.741
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C23(H23), C20(H20), C12(H12), C15(H15), C22(H22), C21(H21),
 C16(H16), C7(H7), C4(H4), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_shelx_res_checksum              56634
_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 1.361
_oxdiff_exptl_absorpt_empirical_full_min 0.821