[2 + 1 + 1] Assembly of spiro β-lactams by Rh(ii)-catalyzed reaction of diazocarbonyl compounds with azirines/isoxazoles.
Golubev, Artem A.; Smetanin, Ilia A.; Agafonova, Anastasiya V.; Rostovskii, Nikolai V.; Khlebnikov, Alexander F.; Starova, Galina L.; Novikov, Mikhail S.; Organic & biomolecular chemistry 17 (2019) 6821–6830; doi:10.1039/c9ob01301f

data_7156933
_publ_section_title
;
 [2 + 1 + 1] Assembly of spiro \b-lactams by Rh(ii)-catalyzed reaction of
 diazocarbonyl compounds with azirines/isoxazoles.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6821
_journal_page_last               6830
_journal_paper_doi               10.1039/c9ob01301f
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C26 H21 Br N2 O11'
_chemical_formula_sum            'C26 H21 Br N2 O11'
_chemical_formula_weight         617.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-24 deposited with the CCDC.    2019-06-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.5433(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.9781(2)
_cell_length_b                   10.33117(14)
_cell_length_c                   27.7978(4)
_cell_measurement_reflns_used    21217
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.7510
_cell_measurement_theta_min      4.7380
_cell_volume                     5153.15(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_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    -61.00  27.00   1.00    1.00    --  -40.38  38.00-150.00   88
  2  \w     72.00 113.00   1.00    1.00    --   40.38 178.00 -60.00   41
  3  \w    118.00 167.00   1.00    2.29    --  113.00 112.00  60.00   49
  4  \w    131.00 177.00   1.00    2.29    --  113.00 112.00  90.00   46
  5  \w     82.00 176.00   1.00    2.29    --  113.00  30.00 120.00   94
  6  \w     57.00 104.00   1.00    2.29    --  113.00 -95.00  90.00   47
  7  \w     36.00 122.00   1.00    2.29    --  113.00 -30.00 -60.00   86
  8  \w     69.00 143.00   1.00    2.29    --  113.00  15.00-120.00   74
  9  \w     51.00 107.00   1.00    2.29    --  113.00 -95.00 -90.00   56
 10  \w     38.00  76.00   1.00    2.29    --  113.00 -45.00-180.00   38
 11  \w    -94.00   4.00   1.00    1.00    --  -40.38 -19.00   0.00   98
 12  \w   -113.00 -88.00   1.00    1.00    --  -40.38-139.00 119.00   25
 13  \w   -111.00 -12.00   1.00    1.00    --  -40.38 -57.00-150.00   99
 14  \w    -92.00 -27.00   1.00    1.00    --  -40.38 -38.00 120.00   65
 15  \w    -76.00 -34.00   1.00    1.00    --  -40.38 -38.00-120.00   42
 16  \w     81.00 107.00   1.00    2.29    --  113.00  68.00-102.54   26
 17  \w     86.00 111.00   1.00    2.29    --  113.00  45.00-104.11   25
 18  \w     84.00 110.00   1.00    2.29    --  113.00  52.00-130.94   26
 19  \w    129.00 155.00   1.00    2.29    --  113.00  39.00-104.26   26
 20  \w     86.00 164.00   1.00    2.29    --  113.00  46.00 -95.39   78
 21  \w     83.00 108.00   1.00    2.29    --  113.00  66.00 -89.01   25
 22  \w     81.00 108.00   1.00    2.29    --  113.00  73.00-105.70   27
 23  \w     84.00 110.00   1.00    2.29    --  113.00  55.00-103.89   26
 24  \w     32.00  79.00   1.00    2.29    --  113.00 -15.00 150.00   47
 25  \w     84.00 109.00   1.00    2.29    --  113.00  61.00-120.00   25
 26  \w     83.00 116.00   1.00    2.29    --  113.00  61.00 -60.00   33
 27  \w    135.00 161.00   1.00    2.29    --  113.00  30.00 -30.00   26
 28  \w     86.00 111.00   1.00    2.29    --  113.00  61.00 -90.00   25
 29  \w     84.00 110.00   1.00    2.29    --  113.00  61.00-150.00   26
 30  \w     79.00 106.00   1.00    2.29    --  113.00  77.00 -90.00   27
 31  \w     83.00 110.00   1.00    2.29    --  113.00  61.00-180.00   27
 32  \w     79.00 105.00   1.00    2.29    --  113.00  77.00-150.00   26
 33  \w    141.00 168.00   1.00    2.29    --  113.00  77.00-150.00   27
 34  \w     79.00 105.00   1.00    2.29    --  113.00  77.00-180.00   26
 35  \w     79.00 106.00   1.00    2.29    --  113.00  77.00-120.00   27
 36  \w     86.00 111.00   1.00    2.29    --  113.00  45.00-150.00   25
 37  \w     42.00  67.00   1.00    2.29    --  113.00 -95.00  60.00   25
 38  \w     87.00 150.00   1.00    2.29    --  113.00  45.00 -60.00   63
 39  \w     84.00 111.00   1.00    2.29    --  113.00  55.00 -79.51   27
 40  \w     80.00 107.00   1.00    2.29    --  113.00  77.00 -60.00   27
 41  \w     87.00 114.00   1.00    2.29    --  113.00  45.00-180.00   27
 42  \w     90.00 115.00   1.00    2.29    --  113.00  45.00-120.00   25
 43  \w     89.00 116.00   1.00    2.29    --  113.00  39.00-104.26   27
 44  \w     83.00 110.00   1.00    2.29    --  113.00  30.00-120.00   27
 45  \w     86.00 124.00   1.00    2.29    --  113.00  30.00 -90.00   38
 46  \w    146.00 172.00   1.00    2.29    --  113.00  48.00-174.02   26
 47  \w     85.00 112.00   1.00    2.29    --  113.00  48.00-174.02   27
 48  \w   -119.00 -93.00   1.00    1.00    --  -40.38 -77.00 150.00   26
 49  \w      2.00  56.00   1.00    1.00    --   40.38 -99.00   0.00   54
 50  \w     60.00 106.00   1.00    1.00    --   40.38-141.00 121.00   46
 51  \w     57.00 114.00   1.00    2.29    --  113.00-112.00  30.00   57
 52  \w    117.00 177.00   1.00    2.29    --  113.00 112.00 -90.00   60
 53  \w    134.00 178.00   1.00    2.29    --  113.00 112.00 -30.00   44
 54  \w     90.00 115.00   1.00    2.29    --  113.00-112.00 120.00   25
 55  \w    153.00 178.00   1.00    2.29    --  113.00  61.00 120.00   25
 56  \w     73.00 106.00   1.00    2.29    --  113.00 -77.00 -90.00   33
 57  \w    122.00 147.00   1.00    2.29    --  113.00 -77.00 -90.00   25
 58  \w     55.00  80.00   1.00    2.29    --  113.00-112.00 120.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0442568000
_diffrn_orient_matrix_UB_12      -0.0261664000
_diffrn_orient_matrix_UB_13      -0.0482667000
_diffrn_orient_matrix_UB_21      -0.0647636000
_diffrn_orient_matrix_UB_22      -0.0553174000
_diffrn_orient_matrix_UB_23      0.0274189000
_diffrn_orient_matrix_UB_31      -0.0348525000
_diffrn_orient_matrix_UB_32      0.1359683000
_diffrn_orient_matrix_UB_33      0.0018794000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            34103
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.151
_diffrn_reflns_theta_min         3.186
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.770
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_description       prizm
_exptl_crystal_F_000             2512
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.932
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5332
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0346
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0598P)^2^+9.8360P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.0988
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5150
_reflns_number_total             5332
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01301f2.cif
_cod_data_source_block           10681-11733_agf2
_cod_depositor_comments
'Adding full bibliography for 7156931--7156934.cif.'
_cod_database_code               7156933
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'c26 h21 b'
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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:
 C23(H23), C6(H6), C22(H22), C26(H26), C25(H25), C10(H10), C7(H7), C9(H9),
 C8(H8)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C16(H16A,H16B,H16C), C13(H13A,H13B,H13C), C19(H19A,H19B,
 H19C)
;
_shelx_res_checksum              77805
_shelx_hkl_checksum              62426
_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 0.742