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_7062661
_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         'C35 H59 N O'
_chemical_formula_sum            'C35 H59 N O'
_chemical_formula_weight         509.83
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-07-25 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                   37.2840(16)
_cell_length_b                   12.3609(5)
_cell_length_c                   6.9822(3)
_cell_measurement_reflns_used    3172
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.9490
_cell_measurement_theta_min      1.8430
_cell_volume                     3217.8(2)
_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 1.3 (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 1.000
_diffrn_measured_fraction_theta_max 0.878
_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    -87.00 -33.75   0.75   20.00    --  -20.27 138.00 -41.00   71
  2  \w    -35.00  85.00   0.75   20.00    --   22.46   3.00 -39.00  160
  3  \w    -94.00 -61.75   0.75   20.00    --  -20.27-178.00-180.00   43
;
_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      -0.0181390000
_diffrn_orient_matrix_UB_12      -0.0171960000
_diffrn_orient_matrix_UB_13      -0.0025359000
_diffrn_orient_matrix_UB_21      -0.0056874000
_diffrn_orient_matrix_UB_22      0.0547537000
_diffrn_orient_matrix_UB_23      -0.0013270000
_diffrn_orient_matrix_UB_31      0.0005351000
_diffrn_orient_matrix_UB_32      -0.0002725000
_diffrn_orient_matrix_UB_33      -0.1015678000
_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  0.0239
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            12440
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.740
_diffrn_reflns_theta_min         1.736
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78916
_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 light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.052
_exptl_crystal_description       prism
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1105 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   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         7245
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.1346
_refine_ls_R_factor_gt           0.0822
_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^)+(0.1134P)^2^+0.4341P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1964
_refine_ls_wR_factor_ref         0.2361
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.851
_reflns_number_gt                4205
_reflns_number_total             7245
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj02738d2.cif
_cod_data_source_block           shi_6129_miha_auto
_cod_depositor_comments
'Adding full bibliography for 7062660--7062662.cif.'
_cod_database_code               7062661
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C20H10N2O2
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.985
_reflns_odcompleteness_completeness 99.95
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C29-C30X \\sim C29-C30
 with sigma of 0.0001
 C32-C31X \\sim C32X-C31
 with sigma of 0.0001
 C31X-C30X \\sim C31-C30
 with sigma of 0.0001
3. Others
 Fixed Sof: C30X(0.5) H30A(0.5) H30B(0.5) C32(0.5) H32A(0.5) H32B(0.5)
 H32C(0.5) C30(0.5) H30C(0.5) H30D(0.5) C32X(0.5) H32D(0.5) H32E(0.5) H32F(0.5)
 H29A(0.5) H29B(0.5) H29C(0.5) H29D(0.5) C31X(0.5) H31A(0.5) H31B(0.5) C31(0.5)
 H31C(0.5) H31D(0.5)
4.a Riding coordinates:
 O1(H1), C35(H35A,H35B,H35C), C30X(H30A,H30B), C32(H32A,H32B,H32C), C8(H8A,H8B,
 H8C), C30(H30C,H30D), C32X(H32D,H32E,H32F), C19(H19A,H19B,H19C), C34(H34A,
 H34B), C29(H29A,H29B), C29(H29C,H29D), C31X(H31A,H31B), C31(H31C,H31D),
 C14(H14A,H14B,H14C), C7(H7A,H7B,H7C)
4.b Ternary CH refined with riding coordinates:
 C26(H26), C5(H5), C13(H13), C3(H3), C16(H16), C23(H23)
4.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C28(H28A,H28B), C10(H10A,H10B), C20(H20A,H20B), C1(H1A,H1B),
 C11(H11A,H11B), C25(H25A,H25B), C24(H24A,H24B), C17(H17A,H17B), C18(H18A,H18B),
  C21(H21A,H21B)
4.d Aromatic/amide H refined with riding coordinates:
 C27(H27)
4.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              87801
_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 1.165
_oxdiff_exptl_absorpt_empirical_full_min 0.757