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_7128675
_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 H20 N2 O2'
_chemical_formula_sum            'C23 H20 N2 O2'
_chemical_formula_weight         356.41
_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     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc27m1nl
_audit_creation_date             2021-03-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-29 deposited with the CCDC.	2021-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.516(4)
_cell_angle_beta                 103.384(4)
_cell_angle_gamma                98.725(4)
_cell_formula_units_Z            2
_cell_length_a                   8.5174(4)
_cell_length_b                   10.7513(5)
_cell_length_c                   10.7978(6)
_cell_measurement_reflns_used    3357
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.1870
_cell_measurement_theta_min      5.7780
_cell_volume                     949.80(8)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.978
_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   -103.00 -78.00   1.00    1.00    --  -35.62-150.00-134.00   25
  2  \w    -68.00 -43.00   1.00    1.00    --  -35.62 123.00 108.00   25
  3  \w    -83.00 -56.00   1.00    1.00    --  -35.62 150.00 -89.00   27
  4  \w     36.00  88.00   1.00    1.00    --   35.62-123.00  27.00   52
  5  \w     74.00 101.00   1.00    1.00    --   35.62-150.00-134.00   27
  6  \w    114.00 140.00   1.00    1.47    --  107.12 123.00 108.00   26
  7  \w    101.00 126.00   1.00    1.47    --  107.12 150.00 -89.00   25
  8  \w     78.00 135.00   1.00    1.47    --  107.12-150.00-134.00   57
  9  \w     56.00 113.00   1.00    1.47    --  107.12-123.00  27.00   57
 10  \w    -64.00  33.00   1.00    1.00    --  -35.62  19.00  60.00   97
 11  \w    -63.00 -36.00   1.00    1.00    --  -35.62-178.00   0.00   27
 12  \w    -99.00 -19.00   1.00    1.00    --  -35.62 -57.00-120.00   80
 13  \w    -34.00  -6.00   1.00    1.00    --   35.62 -38.00 120.00   28
 14  \w     -5.00  54.00   1.00    1.00    --   35.62 -38.00 120.00   59
 15  \w     77.00 108.00   1.00    1.00    --   35.62 178.00 -60.00   31
 16  \w     60.00 107.00   1.00    1.00    --   35.62 178.00-180.00   47
 17  \w     90.00 174.00   1.00    1.47    --  107.12  61.00 150.00   84
 18  \w     44.00 101.00   1.00    1.47    --  107.12-111.00 -90.00   57
 19  \w     99.00 124.00   1.00    1.47    --  107.12 -45.00   0.00   25
 20  \w     57.00  83.00   1.00    1.47    --  107.12 -95.00-180.00   26
 21  \w     73.00 109.00   1.00    1.47    --  107.12 -95.00  30.00   36
 22  \w     95.00 120.00   1.00    1.47    --  107.12  45.00 -90.00   25
 23  \w    151.00 176.00   1.00    1.47    --  107.12  45.00 -90.00   25
 24  \w    124.00 177.00   1.00    1.47    --  107.12 111.00  60.00   53
 25  \w     73.00 124.00   1.00    1.47    --  107.12 -30.00  90.00   51
 26  \w     88.00 118.00   1.00    1.47    --  107.12 -61.00   0.00   30
 27  \w     40.00  70.00   1.00    1.47    --  107.12 -61.00   0.00   30
 28  \w     64.00  90.00   1.00    1.47    --  107.12 -45.00-150.00   26
 29  \w     93.00 124.00   1.00    1.47    --  107.12 -45.00-150.00   31
 30  \w     94.00 175.00   1.00    1.47    --  107.12  45.00  90.00   81
 31  \w    101.00 170.00   1.00    1.47    --  107.12 111.00 -30.00   69
 32  \w     42.00  82.00   1.00    1.47    --  107.12 -45.00   0.00   40
 33  \w    103.00 142.00   1.00    1.47    --  107.12 111.00 -90.00   39
 34  \w     95.00 172.00   1.00    1.47    --  107.12  61.00  30.00   77
;
_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      0.0653914000
_diffrn_orient_matrix_UB_12      -0.0541582000
_diffrn_orient_matrix_UB_13      -0.1071825000
_diffrn_orient_matrix_UB_21      -0.0757688000
_diffrn_orient_matrix_UB_22      -0.1338735000
_diffrn_orient_matrix_UB_23      0.0256909000
_diffrn_orient_matrix_UB_31      -0.1594866000
_diffrn_orient_matrix_UB_32      0.0143130000
_diffrn_orient_matrix_UB_33      -0.0969815000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.978
_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       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6678
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.488
_diffrn_reflns_theta_min         4.165
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93469
_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    1.246
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.723
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3614
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0561
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0783P)^2^+0.4151P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1589
_refine_ls_wR_factor_ref         0.1664
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3095
_reflns_number_total             3614
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc02888j2.cif
_cod_data_source_block           slc-20210326
_cod_depositor_comments
'Adding full bibliography for 7128674--7128676.cif.'
_cod_database_code               7128675
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C1 H1 O1 N1'
_shelx_estimated_absorpt_t_max   0.939
_shelx_estimated_absorpt_t_min   0.883
_diffrn_oxdiff_digest_frames
;
01ce9bc04c9b19a2704d46364866ea1d8c000279978
;
_diffrn_oxdiff_digest_hkl
;
01276f7eea2229018960702f9e1cd0dffbe6c8
;
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 N10(H10), N19(H19), C16(H16), C15(H15), C7(H7), C13(H13), C14(H14), C4(H4),
 C6(H6), C23(H23), C5(H5), C27(H27), C26(H26), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_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 1.245
_oxdiff_exptl_absorpt_empirical_full_min 0.679