Design, synthesis and evaluation of multi-pharmacophore-containing spiropolycyclic harmaline-based hybrids as anticancer agents
Chen, Shuang; Yu, Ze-Hua; Wang, Wei-Na; Chen, Zi-Yue; Pan, Bo-Wen; Chen, Lin; Zhou, Ying; Liu, Xiong-Wei; Liu, Xiong-Li; New Journal of Chemistry 47 (2023) 6073–6085; doi:10.1039/D2NJ05987H

data_7062295
_publ_section_title
;
 Design, synthesis and evaluation of multi-pharmacophore-containing
 spiropolycyclic harmaline-based hybrids as anticancer agents
;
_journal_issue                   13
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6073
_journal_page_last               6085
_journal_paper_doi               10.1039/D2NJ05987H
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C22 H20 N4 O S, C H4 O'
_chemical_formula_sum            'C23 H24 N4 O2 S'
_chemical_formula_weight         420.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-01
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-08-02 deposited with the CCDC.	2023-02-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.201(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.1900(3)
_cell_length_b                   9.48160(10)
_cell_length_c                   14.9584(3)
_cell_measurement_reflns_used    7795
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      71.2560
_cell_measurement_theta_min      2.9760
_cell_volume                     2110.52(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_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     80.00 131.00   0.50    0.50    --   42.30  77.00-150.00  102
  2  \w    -30.00  -4.00   0.50    0.50    --   42.30 -57.00 150.00   52
  3  \w    -37.00  14.00   0.50    0.50    --   42.30 -77.00 -60.00  102
  4  \w      5.00  75.00   0.50    0.50    --   42.30 -82.00  60.00  140
  5  \w    -33.00  39.00   0.50    0.50    --   42.30 -82.00-180.00  144
  6  \w     18.00  61.00   0.50    0.50    --   42.30 -57.00 150.00   86
  7  \w     32.00  57.00   0.50    0.50    --   42.30 -77.00 -60.00   50
  8  \w     70.00 128.00   0.50    0.50    --  101.60  50.00-120.00  116
  9  \w    118.00 145.00   0.50    0.50    --  101.60 -82.00  60.00   54
 10  \w     12.00 134.00   0.50    0.50    --  101.60 -63.00  60.00  244
 11  \w     94.00 135.00   0.50    0.50    --  101.60 -82.00  90.00   82
 12  \w     40.00 114.00   0.50    0.50    --  101.60 -82.00  60.00  148
 13  \w     92.00 169.00   0.50    0.50    --  101.60  50.00-150.00  154
 14  \w     18.00 127.00   0.50    0.50    --  101.60 -50.00-120.00  218
 15  \w     16.00 128.00   0.50    0.50    --  101.60 -38.00-120.00  224
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0737084000
_diffrn_orient_matrix_UB_12      0.1061494000
_diffrn_orient_matrix_UB_13      -0.0578315000
_diffrn_orient_matrix_UB_21      -0.0703080000
_diffrn_orient_matrix_UB_22      -0.1192230000
_diffrn_orient_matrix_UB_23      -0.0283220000
_diffrn_orient_matrix_UB_31      -0.0184451000
_diffrn_orient_matrix_UB_32      0.0302126000
_diffrn_orient_matrix_UB_33      0.0916870000
_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  0.0165
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10488
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.383
_diffrn_reflns_theta_min         2.970
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.583
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4017
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0561P)^2^+1.0682P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1073
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3803
_reflns_number_total             4017
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj05987h2.cif
_cod_data_source_block           nme-7
_cod_depositor_comments
'Adding full bibliography for 7062295--7062296.cif.'
_cod_database_code               7062295
_shelx_shelxl_version_number     2017/1
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4), C11(H11), C12(H12), C13(H13), C14(H14), C21(H21), C22(H22), C23(H23),
 C24(H24)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C28(H28A,H28B,H28C), C30(H30A,H30B,H30C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2A)
;
_shelx_res_checksum              78392
_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 1.877
_oxdiff_exptl_absorpt_empirical_full_min 0.596