Total synthesis of bicyclomahanimbine by Cu(ii)-promoted photoredox process.
Dangar, Shilpa; Roy, Tiyasa; Noskar, Suman; Bisai, Alakesh; RSC advances 14 (2024) 30110–30115; doi:10.1039/d4ra05863a

data_7249369
_publ_section_title
;
 Total synthesis of bicyclomahanimbine by Cu(ii)-promoted photoredox
 process.
;
_journal_issue                   41
_journal_name_full               'RSC advances'
_journal_page_first              30110
_journal_page_last               30115
_journal_paper_doi               10.1039/d4ra05863a
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         '2(C23 H25 N O)'
_chemical_formula_sum            'C46 H50 N2 O2'
_chemical_formula_weight         662.88
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-14
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-05-14 deposited with the CCDC.	2024-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                85.4510(10)
_cell_angle_beta                 82.6730(10)
_cell_angle_gamma                69.423(2)
_cell_formula_units_Z            2
_cell_length_a                   9.8359(2)
_cell_length_b                   13.2198(3)
_cell_length_c                   15.2566(2)
_cell_measurement_reflns_used    22830
_cell_measurement_temperature    100.00(13)
_cell_measurement_theta_max      67.9200
_cell_measurement_theta_min      2.8890
_cell_volume                     1840.79(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 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      100.00(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_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    -52.00  26.00   0.50    0.70    --  -40.58  46.00   3.00  156
  2  \w   -107.00 -23.00   0.50    0.70    --  -40.58 -46.00-145.00  168
  3  \w    -26.00  52.00   0.50    0.70    --   40.58 -46.00-145.00  156
  4  \w   -149.00 -64.00   0.50    2.78    --  -82.50 -46.00-145.00  170
  5  \w    -52.00 -16.00   0.50    2.78    --  -82.50  46.00   3.00   72
  6  \w     79.00 163.00   0.50    2.78    --   96.35  46.00   3.00  168
  7  \w    -43.00  26.00   0.50    0.70    --  -40.58  38.00-180.00  138
  8  \w    -24.00  35.00   0.50    0.70    --  -40.58  12.00 120.00  118
  9  \w     23.00 107.00   0.50    0.70    --   40.58  46.00   3.00  168
 10  \w    -35.00  24.00   0.50    0.70    --   40.58 -12.00  60.00  118
 11  \w     18.00  78.00   0.50    0.70    --   40.58-104.00 -30.00  120
 12  \w    -35.00  24.00   0.50    0.70    --   40.58 -12.00  90.00  118
 13  \w     41.00 100.00   0.50    0.70    --   40.58-138.00   0.00  118
 14  \w      9.00  42.00   0.50    0.70    --   40.58  91.00  22.99   66
 15  \w    -29.00  31.00   0.50    0.70    --   40.58 -25.00 -30.00  120
 16  \w     41.00 100.00   0.50    0.70    --   40.58-138.00 -30.00  118
 17  \w     13.00  43.00   0.50    0.70    --   40.58  81.00-138.17   60
 18  \w    -35.00  24.00   0.50    0.70    --   40.58 -12.00  30.00  118
 19  \w     12.00  43.00   0.50    0.70    --   40.58  83.00 176.46   62
 20  \w     18.00  78.00   0.50    0.70    --   40.58-104.00 120.00  120
 21  \w    -47.00 -15.00   0.50    2.78    --  -82.50  42.00 -90.00   64
 22  \w    -47.00 -15.00   0.50    2.78    --  -82.50  42.00-150.00   64
 23  \w    -47.00 -15.00   0.50    2.78    --  -82.50  42.00  30.00   64
 24  \w    -47.00 -15.00   0.50    2.78    --  -82.50  42.00 120.00   64
 25  \w    -47.00 -15.00   0.50    2.78    --  -82.50  42.00-120.00   64
 26  \w    -47.00 -15.00   0.50    2.78    --  -82.50  42.00-180.00   64
 27  \w    -57.00 -16.00   0.50    2.78    --  -82.50  50.00  90.00   82
 28  \w    -47.00 -15.00   0.50    2.78    --  -82.50  42.00 -30.00   64
 29  \w   -101.00 -23.00   0.50    2.78    --  -82.50 145.00  30.00  156
 30  \w     23.00 106.00   0.50    2.78    --   96.35 -96.00 -30.00  166
 31  \w     29.00  83.00   0.50    2.78    --   96.35 -68.00-120.00  108
 32  \w     30.00  57.00   0.50    2.78    --   96.35 -50.00   0.00   54
 33  \w     83.00 164.00   0.50    2.78    --   96.35  33.00  60.00  162
 34  \w     28.00 105.00   0.50    2.78    --   96.35 -77.00 -60.00  154
 35  \w     28.00  68.00   0.50    2.78    --   96.35 -59.00  60.00   80
 36  \w     30.00  57.00   0.50    2.78    --   96.35 -50.00 120.00   54
 37  \w     28.00  68.00   0.50    2.78    --   96.35 -59.00-150.00   80
 38  \w     33.00 110.00   0.50    2.78    --   96.35-117.00   0.00  154
 39  \w     23.00 106.00   0.50    2.78    --   96.35 -96.00-120.00  166
 40  \w     29.00  83.00   0.50    2.78    --   96.35 -68.00 120.00  108
 41  \w     99.00 160.00   0.50    2.78    --   96.35 117.00-120.00  122
 42  \w     33.00 110.00   0.50    2.78    --   96.35-117.00-120.00  154
 43  \w     33.00 110.00   0.50    2.78    --   96.35-117.00  90.00  154
 44  \w     83.00 164.00   0.50    2.78    --   96.35  33.00  90.00  162
 45  \w     28.00 105.00   0.50    2.78    --   96.35 -77.00   0.00  154
 46  \w     44.00 127.00   0.50    2.78    --   96.35-145.00-120.00  166
 47  \w     30.00  57.00   0.50    2.78    --   96.35 -50.00-150.00   54
 48  \w     28.00  68.00   0.50    2.78    --   96.35 -59.00-120.00   80
 49  \w     75.00 165.00   0.50    2.78    --   96.35  59.00 150.00  180
 50  \w     28.00  68.00   0.50    2.78    --   96.35 -59.00  30.00   80
 51  \w     80.00 164.00   0.50    2.78    --   96.35  42.00 -60.00  168
 52  \w     81.00 167.00   0.50    2.78    --   96.35  25.00-150.00  172
 53  \w     33.00 110.00   0.50    2.78    --   96.35-117.00 -30.00  154
 54  \w     72.00 165.00   0.50    2.78    --   96.35  69.00 -37.67  186
 55  \w     30.00  57.00   0.50    2.78    --   96.35 -50.00 -30.00   54
 56  \w     81.00 167.00   0.50    2.78    --   96.35  25.00 -90.00  172
 57  \w     77.00 163.00   0.50    2.78    --   96.35  50.00 120.00  172
 58  \w     26.00 127.00   0.50    2.78    --   96.35 -87.00  90.00  202
 59  \w     29.00  83.00   0.50    2.78    --   96.35 -68.00 -30.00  108
 60  \w   -108.00 -17.00   0.50    0.70    --  -40.58 -64.00  90.00  182
 61  \w   -107.00 -21.00   0.50    0.70    --  -40.58 -50.00 150.00  172
 62  \w   -108.00 -17.00   0.50    0.70    --  -40.58 -64.00-150.00  182
 63  \w   -109.00 -14.00   0.50    0.70    --  -40.58 -77.00 120.00  190
 64  \w   -107.00 -21.00   0.50    0.70    --  -40.58 -50.00  30.00  172
 65  \w    -78.00   4.00   0.50    0.70    --  -40.58 104.00-150.00  164
 66  \w   -107.00 -21.00   0.50    0.70    --  -40.58 -50.00 120.00  172
 67  \w     18.00 108.00   0.50    0.70    --   40.58  64.00 -60.00  180
 68  \w     14.00 109.00   0.50    0.70    --   40.58  77.00-120.00  190
 69  \w     22.00 107.00   0.50    0.70    --   40.58  50.00  90.00  170
 70  \w     14.00 109.00   0.50    0.70    --   40.58  77.00   0.00  190
 71  \w     14.00 109.00   0.50    0.70    --   40.58  77.00 -30.00  190
 72  \w     14.00 109.00   0.50    0.70    --   40.58  77.00  30.00  190
 73  \w     18.00 108.00   0.50    0.70    --   40.58  64.00-180.00  180
 74  \w      7.00  35.00   0.50    0.70    --   40.58  94.00-106.13   56
 75  \w      9.00  43.00   0.50    0.70    --   40.58  90.00  49.37   68
 76  \w      8.00  42.00   0.50    0.70    --   40.58  92.00  96.68   68
 77  \w   -151.00 -63.00   0.50    2.78    --  -82.50 -77.00  90.00  176
 78  \w   -151.00 -55.00   0.50    2.78    --  -82.50 -77.00 -79.74  192
 79  \w   -151.00 -55.00   0.50    2.78    --  -82.50 -77.00-150.00  192
 80  \w   -151.00 -55.00   0.50    2.78    --  -82.50 -77.00  30.00  192
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0124885000
_diffrn_orient_matrix_UB_12      0.1158749000
_diffrn_orient_matrix_UB_13      0.0188822000
_diffrn_orient_matrix_UB_21      0.1485949000
_diffrn_orient_matrix_UB_22      -0.0166290000
_diffrn_orient_matrix_UB_23      -0.0547130000
_diffrn_orient_matrix_UB_31      -0.0779480000
_diffrn_orient_matrix_UB_32      0.0425694000
_diffrn_orient_matrix_UB_33      -0.0838403000
_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  0.0463
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            35510
_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         68.205
_diffrn_reflns_theta_min         2.922
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     459
_refine_ls_number_reflns         6683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0587P)^2^+0.4151P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1164
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5712
_reflns_number_total             6683
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra05863a3.cif
_cod_data_source_block           ab_dgj_08scm_auto
_cod_database_code               7249369
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     RT
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C37(H37), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C38(H38A,H38B), C15(H15A,H15B), C42(H42A,H42B), C41(H41A,H41B), C19(H19A,
 H19B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 N003(H003), N004(H004), C4(H4), C5(H5), C8(H8), C6(H6), C7(H7), C27(H27),
 C31(H31), C28(H28), C29(H29), C30(H30)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C23(H23A,H23B,H23C), C45(H45A,H45B,H45C), C46(H46A,H46B,
 H46C), C17(H17A,H17B,H17C), C22(H22A,H22B,H22C), C36(H36A,H36B,H36C), C40(H40A,
 H40B,H40C)
;
_shelx_res_checksum              64107
_shelx_hkl_checksum              5695
_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 1.439
_oxdiff_exptl_absorpt_empirical_full_min 0.746