[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_7156934
_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         'C23 H22 Br N O9'
_chemical_formula_sum            'C23 H22 Br N O9'
_chemical_formula_weight         536.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 91.1330(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.66080(10)
_cell_length_b                   15.21840(10)
_cell_length_c                   13.20380(10)
_cell_measurement_reflns_used    18645
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.7170
_cell_measurement_theta_min      2.8660
_cell_volume                     2342.67(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_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    -96.00 -16.00   0.50    0.20    --  -38.70 -68.00 -25.00  160
  2  \w     19.00  52.00   0.50    0.20    --   38.70 -68.00 -25.00   66
  3  \w     16.00  42.00   0.50    0.20    --   38.70  68.00 107.00   52
  4  \w     61.00  96.00   0.50    0.20    --   38.70  68.00 107.00   70
  5  \w     73.00 128.00   0.50    0.20    --  104.92 -68.00 -25.00  110
  6  \w     81.00 157.00   0.50    0.20    --  104.92  68.00 107.00  152
  7  \w    -62.00 -21.00   0.50    0.20    --  -38.70  68.00 107.00   82
  8  \w    -26.00  32.00   0.50    0.20    --  -38.70  21.00  60.00  116
  9  \w    -26.00   5.00   0.50    0.20    --  -38.70  32.00 -30.00   62
 10  \w   -110.00 -19.00   0.50    0.20    --  -38.70 -21.00 150.00  182
 11  \w     20.00  65.00   0.50    0.20    --   38.70  54.00-150.00   90
 12  \w     73.00 101.00   0.50    0.20    --   38.70  54.00-150.00   56
 13  \w     20.00  55.00   0.50    0.20    --   38.70  54.00-120.00   70
 14  \w     31.00 106.00   0.50    0.20    --   38.70  32.00 150.00  150
 15  \w     22.00  50.00   0.50    0.20    --   38.70  21.00  90.00   56
 16  \w     64.00 111.00   0.50    0.20    --   38.70  21.00  90.00   94
 17  \w     -7.00  58.00   0.50    0.20    --   38.70 -21.00   0.00  130
 18  \w     46.00  71.00   0.50    0.20    --   38.70  32.00   0.00   50
 19  \w     60.00  92.00   0.50    0.20    --   38.70  54.00-120.00   64
 20  \w     42.00 121.00   0.50    0.20    --  104.92 -53.00 -60.00  158
 21  \w    132.00 157.00   0.50    0.20    --  104.92  22.00-120.00   50
 22  \w     41.00 111.00   0.50    0.20    --  104.92 -45.00-180.00  140
 23  \w    114.00 155.00   0.50    0.20    --  104.92  30.00-150.00   82
 24  \w     41.00 118.00   0.50    0.20    --  104.92-133.00   0.00  154
 25  \w     39.00 114.00   0.50    0.20    --  104.92-111.00   0.00  150
 26  \w     42.00 123.00   0.50    0.20    --  104.92-133.00-150.00  162
 27  \w     92.00 151.00   0.50    0.20    --  104.92  30.00  90.00  118
 28  \w     87.00 152.00   0.50    0.20    --  104.92  61.00  90.00  130
 29  \w     84.00 121.00   0.50    0.20    --  104.92 -53.00  90.00   74
 30  \w     84.00 130.00   0.50    0.20    --  104.92  77.00  60.00   92
 31  \w     38.00 123.00   0.50    0.20    --  104.92 -22.00 120.00  170
 32  \w     60.00  85.00   0.50    0.20    --  104.92 -68.00 -25.00   50
 33  \w   -107.00 -81.00   0.50    0.20    --  -38.70 -32.00   0.00   52
 34  \w    -89.00 -63.00   0.50    0.20    --  -38.70 -43.00 150.00   52
 35  \w    -66.00 -40.00   0.50    0.20    --  -38.70 -32.00   0.00   52
 36  \w    -25.00  12.00   0.50    0.20    --  -38.70 104.00-120.00   74
 37  \w    -77.00 -41.00   0.50    0.20    --  -38.70 104.00-120.00   72
 38  \w     37.00  63.00   0.50    0.20    --   38.70 -77.00-120.00   52
 39  \w     80.00 106.00   0.50    0.20    --   38.70  32.00-120.00   52
 40  \w     15.00  46.00   0.50    0.20    --   38.70  11.00  60.00   62
 41  \w     -3.00  41.00   0.50    0.20    --   38.70 -32.00-180.00   88
 42  \w      7.00  36.00   0.50    0.20    --   38.70 -77.00-120.00   58
 43  \w     25.00  51.00   0.50    0.20    --   38.70  54.00 -90.00   52
 44  \w     76.00 101.00   0.50    0.20    --   38.70  11.00  60.00   50
 45  \w    129.00 156.00   0.50    0.20    --  104.92  77.00-120.00   54
 46  \w     80.00 106.00   0.50    0.20    --  104.92  77.00-120.00   52
 47  \w     40.00 119.00   0.50    0.20    --  104.92 -30.00 -30.00  158
 48  \w    132.00 157.00   0.50    0.20    --  104.92  22.00  30.00   50
 49  \w     49.00 104.00   0.50    0.20    --  104.92 -86.00   0.00  110
 50  \w     85.00 152.00   0.50    0.20    --  104.92  53.00 -90.00  134
 51  \w     81.00 114.00   0.50    0.20    --  104.92  69.00-150.00   66
 52  \w     78.00 112.00   0.50    0.20    --  104.92  77.00-180.00   68
 53  \w     92.00 122.00   0.50    0.20    --  104.92 -45.00 -30.00   60
 54  \w     79.00 152.00   0.50    0.20    --  104.92  77.00 150.00  146
 55  \w     87.00 113.00   0.50    0.20    --  104.92  53.00-180.00   52
 56  \w    125.00 150.00   0.50    0.20    --  104.92  53.00-180.00   50
 57  \w     41.00  66.00   0.50    0.20    --  104.92 -45.00 -30.00   50
 58  \w     78.00 104.00   0.50    0.20    --  104.92  77.00-150.00   52
 59  \w    115.00 145.00   0.50    0.20    --  104.92 111.00 120.00   60
 60  \w     85.00 150.00   0.50    0.20    --  104.92  53.00-120.00  130
 61  \w     83.00 125.00   0.50    0.20    --  104.92 111.00 -30.00   84
 62  \w     88.00 124.00   0.50    0.20    --  104.92 111.00   0.00   72
 63  \w     86.00 112.00   0.50    0.20    --  104.92  61.00-180.00   52
 64  \w    116.00 142.00   0.50    0.20    --  104.92  75.00-163.69   52
 65  \w     85.00 111.00   0.50    0.20    --  104.92  53.00-150.00   52
 66  \w     81.00 106.00   0.50    0.20    --  104.92  69.00-120.00   50
 67  \w     79.00 104.00   0.50    0.20    --  104.92  75.00-163.69   50
 68  \w     89.00 144.00   0.50    0.20    --  104.92  93.00 120.00  110
 69  \w    127.00 152.00   0.50    0.20    --  104.92  69.00-150.00   50
 70  \w     82.00 117.00   0.50    0.20    --  104.92  69.00-180.00   70
 71  \w     83.00 108.00   0.50    0.20    --  104.92  61.00-120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0698815000
_diffrn_orient_matrix_UB_12      0.0596089000
_diffrn_orient_matrix_UB_13      0.0700695000
_diffrn_orient_matrix_UB_21      -0.0456241000
_diffrn_orient_matrix_UB_22      0.0514839000
_diffrn_orient_matrix_UB_23      -0.0928312000
_diffrn_orient_matrix_UB_31      -0.1024297000
_diffrn_orient_matrix_UB_32      -0.0636225000
_diffrn_orient_matrix_UB_33      -0.0094274000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23811
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.901
_diffrn_reflns_theta_min         4.434
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.867
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_description       prizm
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.545
_refine_diff_density_min         -1.189
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       0.00271(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4641
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0661P)^2^+3.5162P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1147
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4579
_reflns_number_total             4641
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01301f2.cif
_cod_data_source_block           10681-11733_agf1
_cod_depositor_comments
'Adding full bibliography for 7156931--7156934.cif.'
_cod_database_code               7156934
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C23 H22 Br N O9'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_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 Ternary CH refined with riding coordinates:
 C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C9(H9), C10(H10), C8(H8)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C17(H17A,H17B,H17C), C13(H13A,H13B,
 H13C)
;
_shelx_res_checksum              34046
_shelx_hkl_checksum              2320
_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 1.683
_oxdiff_exptl_absorpt_empirical_full_min 0.697