New betulin imine derivatives with antioxidant and selective antitumor activity
Iftime, Manuela-Maria; Ailiesei, Gabriela Liliana; Shova, Sergiu; Miron, Camelia; Tanaka, Hiromasa; Hori, Masaru; Marin, Luminita; New Journal of Chemistry 47 (2023) 16551–16563; doi:10.1039/D3NJ02738D

data_7062662
_publ_section_title
;
 New betulin imine derivatives with antioxidant and selective antitumor
 activity
;
_journal_issue                   35
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16551
_journal_page_last               16563
_journal_paper_doi               10.1039/D3NJ02738D
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C33 H55 N O'
_chemical_formula_sum            'C33 H55 N O'
_chemical_formula_weight         481.78
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-04-20 deposited with the CCDC.	2023-08-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9924(8)
_cell_length_b                   12.499(2)
_cell_length_c                   34.223(4)
_cell_measurement_reflns_used    1498
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.0070
_cell_measurement_theta_min      2.4050
_cell_volume                     2991.0(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1593
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -39.00 -11.00   1.00  150.00    --  -15.29  72.00 -40.00   28
  2  \w    -83.00 -17.00   1.00  150.00    --  -15.29 -52.00  26.00   66
  3  \w     -4.00  39.00   1.00  150.00    --   17.71  77.00   0.00   43
  4  \w    -19.00   6.00   1.00  150.00    --   17.71 -99.00-180.00   25
  5  \w      9.00  42.00   1.00  150.00    --   17.71 -99.00-180.00   33
  6  \w     -9.00  39.00   1.00  150.00    --   17.71  77.00-150.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0097437000
_diffrn_orient_matrix_UB_12      0.0552524000
_diffrn_orient_matrix_UB_13      0.0042575000
_diffrn_orient_matrix_UB_21      -0.0638281000
_diffrn_orient_matrix_UB_22      -0.0056967000
_diffrn_orient_matrix_UB_23      0.0160032000
_diffrn_orient_matrix_UB_31      0.0781109000
_diffrn_orient_matrix_UB_32      -0.0115014000
_diffrn_orient_matrix_UB_33      0.0125110000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0845
_diffrn_reflns_av_unetI/netI     0.1716
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            13161
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         1.735
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.070
_exptl_crystal_description       prism
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 506 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         5286
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.2194
_refine_ls_R_factor_gt           0.0843
_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^)+(0.0349P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1557
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2177
_reflns_number_total             5286
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj02738d2.cif
_cod_data_source_block           shi_6089_luma_auto
_cod_depositor_comments
'Adding full bibliography for 7062660--7062662.cif.'
_cod_database_code               7062662
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C35H35N1O1
_chemical_oxdiff_usercomment     P3BA
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.991
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C5(H5), C13(H13), C16(H16), C23(H23), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C10(H10A,H10B), C11(H11A,H11B), C17(H17A,H17B),
 C18(H18A,H18B), C20(H20A,H20B), C21(H21A,H21B), C24(H24A,H24B), C25(H25A,H25B),
  C28(H28A,H28B), C29(H29A,H29B)
2.c Aromatic/amide H refined with riding coordinates:
 C27(H27)
2.d X=CH2 refined with riding coordinates:
 C33(H33A,H33B)
2.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C14(H14A,H14B,H14C),
 C19(H19A,H19B,H19C), C30(H30A,H30B,H30C), C32(H32A,H32B,H32C)
2.f Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              22978
_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 1.334
_oxdiff_exptl_absorpt_empirical_full_min 0.693