Synthesis of the 5/5-spiroindimicin alkaloids: development of a general synthetic approach and biological investigations.
Banerjee, Ankush; Brisco, Tiffany A.; Ray, Sneha; Datta, Arani; Zhang, Xiaoyu; Zhang, Zhen; Busse, Alexander A.; Niederstrasser, Hanspeter; Sumida, Krissty; Posner, Bruce A.; Wetzel, Dawn M.; Phillips, Margaret A.; Smith, Myles W.; Organic & biomolecular chemistry 22 (2024) 9413–9425; doi:10.1039/d4ob01552e

data_7160199
_publ_section_title
;
 Synthesis of the 5/5-spiroindimicin alkaloids: development of a general
 synthetic approach and biological investigations.
;
_journal_issue                   48
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9413
_journal_page_last               9425
_journal_paper_doi               10.1039/d4ob01552e
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C15 H12 Br Cl N2 O4'
_chemical_formula_sum            'C15 H12 Br Cl N2 O4'
_chemical_formula_weight         399.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2fhxd8
_audit_creation_date             2022-11-15
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-03-17 deposited with the CCDC.	2024-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.1410(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.45120(10)
_cell_length_b                   8.02230(10)
_cell_length_c                   14.9534(2)
_cell_measurement_reflns_used    20055
_cell_measurement_temperature    100.1(4)
_cell_measurement_theta_max      76.8570
_cell_measurement_theta_min      3.0670
_cell_volume                     1564.72(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Shelxtl-Plus/XP, Bruker AXS, Inc. 2009'
_computing_publication_material  'Shelxtl-Plus, Bruker AXS, Inc. 2009'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.1(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_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   -121.00 -37.00   0.50    6.00    --  -48.82 -41.00  20.00  168
  2  \w     37.00 121.00   0.50    6.00    --   48.82  41.00 173.00  168
  3  \w    -23.00  61.00   0.50    6.00    --   48.82 -41.00  20.00  168
  4  \w     35.00 120.00   0.50   24.00    --  107.75 -41.00  20.00  170
  5  \w     96.00 178.00   0.50   24.00    --  107.75  41.00 173.00  164
  6  \w    -61.00  24.00   0.50    6.00    --  -48.82  41.00 173.00  170
  7  \w     34.00  97.00   0.50    6.00    --   48.82-125.00-120.00  126
  8  \w     34.00  97.00   0.50    6.00    --   48.82-125.00  60.00  126
  9  \w     35.00 123.00   0.50   24.00    --  107.75 -57.00 150.00  176
 10  \w     32.00 121.00   0.50   24.00    --  107.75 -19.00   0.00  178
 11  \w     35.00 106.00   0.50   24.00    --  107.75 -99.00-120.00  142
 12  \w     35.00 112.00   0.50   24.00    --  107.75-125.00-180.00  154
 13  \w     35.00 106.00   0.50   24.00    --  107.75 -99.00  30.00  142
 14  \w     95.00 178.00   0.50   24.00    --  107.75  19.00-150.00  166
 15  \w     32.00 121.00   0.50   24.00    --  107.75 -19.00-150.00  178
 16  \w     35.00 112.00   0.50   24.00    --  107.75-125.00  30.00  154
 17  \w     35.00 112.00   0.50   24.00    --  107.75-125.00-120.00  154
 18  \w     35.00 120.00   0.50   24.00    --  107.75 -38.00-150.00  170
 19  \w   -121.00 -34.00   0.50    6.00    --  -48.82 -57.00 -60.00  174
 20  \w   -121.00 -34.00   0.50    6.00    --  -48.82 -57.00   0.00  174
 21  \w   -121.00 -26.00   0.50    6.00    --  -48.82 -77.00 120.00  190
 22  \w   -121.00 -26.00   0.50    6.00    --  -48.82 -77.00-180.00  190
 23  \w   -121.00 -26.00   0.50    6.00    --  -48.82 -77.00 -60.00  190
 24  \w   -121.00 -26.00   0.50    6.00    --  -48.82 -77.00-120.00  190
 25  \w     95.00 178.00   0.50   24.00    --  107.75  19.00  30.00  166
 26  \w     95.00 170.00   0.50   24.00    --  107.75  38.00 -60.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0493815000
_diffrn_orient_matrix_UB_12      0.1723442000
_diffrn_orient_matrix_UB_13      -0.0040476000
_diffrn_orient_matrix_UB_21      0.1040185000
_diffrn_orient_matrix_UB_22      -0.0690987000
_diffrn_orient_matrix_UB_23      0.0545201000
_diffrn_orient_matrix_UB_31      0.0261264000
_diffrn_orient_matrix_UB_32      -0.0489447000
_diffrn_orient_matrix_UB_33      -0.0911992000
_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  0.0336
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21679
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.235
_diffrn_reflns_theta_min         3.388
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.358
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.299
_exptl_absorpt_correction_type   'gaussian and multi-scan'
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.322
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.143
_refine_diff_density_max         0.728
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3240
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0276
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0426P)^2^+1.4442P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0758
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3238
_reflns_number_total             3240
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01552e2.cif
_cod_data_source_block           1-ab-101b-1vl
_cod_depositor_comments
'Adding full bibliography for 7160196--7160199.cif.'
_cod_database_code               7160199
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H12 N2 O4 Cl Br'
_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:
 C4(H4), C6(H6), C7(H7), C12(H12)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              71055
_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 2.079
_oxdiff_exptl_absorpt_empirical_full_min 0.513