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_7160198
_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      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc2g0whw
_audit_creation_date             2023-05-16
_audit_creation_method
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_audit_update_record
;
2023-05-23 deposited with the CCDC.	2024-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                73.634(4)
_cell_angle_beta                 81.798(3)
_cell_angle_gamma                72.598(3)
_cell_formula_units_Z            2
_cell_length_a                   9.1305(3)
_cell_length_b                   9.5099(3)
_cell_length_c                   9.6003(4)
_cell_measurement_reflns_used    12449
_cell_measurement_temperature    100.02(14)
_cell_measurement_theta_max      76.6350
_cell_measurement_theta_min      4.8100
_cell_volume                     761.66(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(14)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.962
_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   -119.00 -61.00   0.50    4.50    --  -47.07-143.00 -25.00  116
  2  \w    -99.00 -22.00   0.50    4.50    --  -47.07 143.00  28.00  154
  3  \w    -88.00 -14.00   0.50    4.50    --  -47.07 127.00-140.00  148
  4  \w   -119.00 -72.00   0.50    4.50    --  -47.07-127.00 143.00   94
  5  \w     36.00  96.00   0.50    4.50    --   47.07-127.00 143.00  120
  6  \w     44.00 105.00   0.50    4.50    --   47.07-143.00 -25.00  122
  7  \w     83.00 171.00   0.50   18.00    --  107.75 143.00  28.00  176
  8  \w     36.00 113.00   0.50   18.00    --  107.75-127.00 143.00  154
  9  \w     44.00 125.00   0.50   18.00    --  107.75-143.00 -25.00  162
 10  \w     94.00 178.00   0.50   18.00    --  107.75 127.00-140.00  168
 11  \w   -119.00 -24.00   0.50    4.50    --  -47.07 -77.00 -30.00  190
 12  \w   -121.00 -34.00   0.50    4.50    --  -47.07 -19.00   0.00  174
 13  \w   -119.00 -73.00   0.50    4.50    --  -47.07-125.00   0.00   92
 14  \w     35.00 120.00   0.50   18.00    --  107.75 -38.00 120.00  170
 15  \w     85.00 178.00   0.50   18.00    --  107.75  77.00  30.00  186
 16  \w     35.00 120.00   0.50   18.00    --  107.75 -38.00 -90.00  170
 17  \w     35.00 106.00   0.50   18.00    --  107.75 -99.00 120.00  142
 18  \w     35.00 106.00   0.50   18.00    --  107.75 -99.00-150.00  142
 19  \w     35.00 106.00   0.50   18.00    --  107.75 -99.00 150.00  142
 20  \w     35.00 106.00   0.50   18.00    --  107.75 -99.00 -60.00  142
 21  \w     93.00 178.00   0.50   18.00    --  107.75  57.00-150.00  170
 22  \w     95.00 178.00   0.50   18.00    --  107.75  38.00 -60.00  166
 23  \w     35.00 106.00   0.50   18.00    --  107.75 -99.00  30.00  142
 24  \w     35.00 123.00   0.50   18.00    --  107.75 -57.00 -60.00  176
 25  \w     95.00 178.00   0.50   18.00    --  107.75  38.00 -30.00  166
 26  \w   -119.00 -24.00   0.50    4.50    --  -47.07 -77.00-150.00  190
 27  \w   -119.00 -24.00   0.50    4.50    --  -47.07 -77.00 120.00  190
 28  \w   -118.00 -32.00   0.50    4.50    --  -47.07 -57.00-120.00  172
 29  \w   -118.00 -32.00   0.50    4.50    --  -47.07 -57.00 150.00  172
 30  \w   -119.00 -73.00   0.50    4.50    --  -47.07-125.00-180.00   92
 31  \w   -119.00 -24.00   0.50    4.50    --  -47.07 -77.00  90.00  190
 32  \w   -119.00 -24.00   0.50    4.50    --  -47.07 -77.00 -60.00  190
 33  \w   -119.00 -24.00   0.50    4.50    --  -47.07 -77.00  30.00  190
 34  \w     95.00 178.00   0.50   18.00    --  107.75  38.00  90.00  166
 35  \w     95.00 178.00   0.50   18.00    --  107.75  19.00 150.00  166
;
_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      -0.0107940000
_diffrn_orient_matrix_UB_12      -0.0341925000
_diffrn_orient_matrix_UB_13      0.1672482000
_diffrn_orient_matrix_UB_21      -0.1755099000
_diffrn_orient_matrix_UB_22      0.0699013000
_diffrn_orient_matrix_UB_23      -0.0008109000
_diffrn_orient_matrix_UB_31      -0.0217618000
_diffrn_orient_matrix_UB_32      -0.1572873000
_diffrn_orient_matrix_UB_33      0.0106159000
_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  0.0193
_diffrn_reflns_av_unetI/netI     0.0096
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12747
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.971
_diffrn_reflns_theta_min         4.811
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.503
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56807
_exptl_absorpt_correction_type   'gaussian and multi-scan'
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023)
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    1.742
_exptl_crystal_description       prism
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.242
_exptl_crystal_size_min          0.143
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0237
_refine_ls_R_factor_gt           0.0237
_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^)+(0.0323P)^2^+0.8078P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0620
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3096
_reflns_number_total             3097
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01552e2.cif
_cod_data_source_block           1-ab-158a
_cod_depositor_comments
'Adding full bibliography for 7160196--7160199.cif.'
_cod_database_code               7160198
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C15H12N2O4ClBr
_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), C11(H11)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              55807
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
;
_oxdiff_exptl_absorpt_empirical_full_max 1.322
_oxdiff_exptl_absorpt_empirical_full_min 0.833