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_7160197
_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         'C23 H18 Cl N3 O2'
_chemical_formula_sum            'C23 H18 Cl N3 O2'
_chemical_formula_weight         403.85
_chemical_name_systematic        'spiroindimicin F'
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2fpr74
_audit_creation_date             2023-04-07
_audit_creation_method
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_audit_update_record
;
2023-08-17 deposited with the CCDC.	2024-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.8740(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.26480(10)
_cell_length_b                   14.87010(10)
_cell_length_c                   12.73740(10)
_cell_measurement_reflns_used    22973
_cell_measurement_temperature    100.01(12)
_cell_measurement_theta_max      76.8160
_cell_measurement_theta_min      2.9590
_cell_volume                     1925.89(3)
_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)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(12)
_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 0.982
_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    -81.00   3.00   0.50    6.50    --  -47.20 105.00  29.00  168
  2  \w     18.00  83.00   0.50    6.50    --   47.20-105.00 -69.00  130
  3  \w     37.00 107.00   0.50   26.00    --  107.75-105.00 -69.00  140
  4  \w    105.00 178.00   0.50   26.00    --  107.75 105.00  29.00  146
  5  \w   -120.00 -32.00   0.50    6.50    --  -47.20 -57.00 -90.00  176
  6  \w    -86.00 -13.00   0.50    6.50    --  -47.20 125.00  60.00  146
  7  \w    -60.00  26.00   0.50    6.50    --  -47.20  38.00  30.00  172
  8  \w     35.00 123.00   0.50   26.00    --  107.75 -57.00 -60.00  176
  9  \w     95.00 178.00   0.50   26.00    --  107.75  38.00-180.00  166
 10  \w     95.00 178.00   0.50   26.00    --  107.75  19.00  30.00  166
 11  \w     38.00 112.00   0.50   26.00    --  107.75-125.00-120.00  148
 12  \w     37.00 106.00   0.50   26.00    --  107.75 -99.00  60.00  138
 13  \w     35.00 120.00   0.50   26.00    --  107.75 -38.00-120.00  170
 14  \w     95.00 178.00   0.50   26.00    --  107.75  38.00  90.00  166
 15  \w     38.00 112.00   0.50   26.00    --  107.75-125.00  90.00  148
 16  \w     35.00 123.00   0.50   26.00    --  107.75 -57.00  60.00  176
 17  \w   -120.00 -24.00   0.50    6.50    --  -47.20 -77.00  30.00  192
 18  \w   -120.00 -32.00   0.50    6.50    --  -47.20 -57.00  60.00  176
 19  \w   -120.00 -24.00   0.50    6.50    --  -47.20 -77.00 150.00  192
 20  \w   -120.00 -24.00   0.50    6.50    --  -47.20 -77.00 -30.00  192
 21  \w   -120.00 -24.00   0.50    6.50    --  -47.20 -77.00-120.00  192
 22  \w     95.00 178.00   0.50   26.00    --  107.75  19.00-120.00  166
 23  \w     95.00 178.00   0.50   26.00    --  107.75  19.00 -60.00  166
 24  \w     95.00 178.00   0.50   26.00    --  107.75  38.00 -30.00  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      -0.0638299000
_diffrn_orient_matrix_UB_12      0.0939262000
_diffrn_orient_matrix_UB_13      -0.0046709000
_diffrn_orient_matrix_UB_21      -0.1131250000
_diffrn_orient_matrix_UB_22      -0.0346492000
_diffrn_orient_matrix_UB_23      -0.0820224000
_diffrn_orient_matrix_UB_31      -0.0780436000
_diffrn_orient_matrix_UB_32      -0.0265727000
_diffrn_orient_matrix_UB_33      0.0903257000
_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  0.0151
_diffrn_reflns_av_unetI/netI     0.0067
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25979
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.999
_diffrn_reflns_theta_min         4.596
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.962
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023)
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    1.393
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane, methanol'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3983
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0343
_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^)+(0.0459P)^2^+1.0147P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0895
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3942
_reflns_number_total             3983
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01552e2.cif
_cod_data_source_block           1-ab-183a
_cod_depositor_comments
'Adding full bibliography for 7160196--7160199.cif.'
_cod_database_code               7160197
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O Cl'
_shelx_estimated_absorpt_t_max   0.813
_shelx_estimated_absorpt_t_min   0.672
_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 Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C9(H9), C17(H17), C18(H18), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              22855
_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 1.230
_oxdiff_exptl_absorpt_empirical_full_min 0.840