Design, synthesis and evaluation of structurally diverse polycyclic harmaline scaffolds as anticancer agents
Chen, Shuang; Wang, Xi-Rui; Wang, Wei-Na; Xu, Ke-Lan; Hu, Pan; Zhou, Ying; Pan, Bo-Wen; Wang, Qi-Lin; Liu, Xiong-Li; New Journal of Chemistry 48 (2024) 6322–6334; doi:10.1039/D4NJ00306C

data_7063079
_publ_section_title
;
 Design, synthesis and evaluation of structurally diverse polycyclic
 harmaline scaffolds as anticancer agents
;
_journal_issue                   14
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6322
_journal_page_last               6334
_journal_paper_doi               10.1039/D4NJ00306C
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C27 H21 Br N2 O2'
_chemical_formula_sum            'C27 H21 Br N2 O2'
_chemical_formula_weight         485.37
_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             2022-12-23
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-01-07 deposited with the CCDC.	2024-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                80.159(5)
_cell_angle_beta                 84.229(5)
_cell_angle_gamma                72.876(5)
_cell_formula_units_Z            4
_cell_length_a                   8.6905(5)
_cell_length_b                   13.8209(8)
_cell_length_c                   19.6302(11)
_cell_measurement_reflns_used    7299
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.7140
_cell_measurement_theta_min      2.2290
_cell_volume                     2217.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.965
_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    -65.00  29.00   1.00    2.93    --  -40.92  37.00 150.00   94
  2  \w     51.00  79.00   1.00    2.93    --   40.92-125.00  60.00   28
  3  \w     38.00  65.00   1.00    8.00    --  107.58 -45.00   0.00   27
  4  \w     83.00 114.00   1.00    8.00    --  107.58 -45.00   0.00   31
  5  \w     84.00 122.00   1.00    8.00    --  107.58-125.00 -30.00   38
  6  \w     53.00 109.00   1.00    8.00    --  107.58 -94.00  60.00   56
  7  \w     53.00 116.00   1.00    8.00    --  107.58-125.00  30.00   63
  8  \w     52.00 105.00   1.00    8.00    --  107.58 -30.00-120.00   53
  9  \w    108.00 171.00   1.00    8.00    --  107.58  45.00 -90.00   63
 10  \w     52.00 136.00   1.00    8.00    --  107.58 -61.00-180.00   84
 11  \w     35.00  97.00   1.00    2.93    --   40.92-125.00-150.00   62
 12  \w     28.00  59.00   1.00    8.00    --  107.58 -94.00-150.00   31
 13  \w     26.00 158.00   1.00    8.00    --  107.58 -15.00  90.00  132
 14  \w    129.00 178.00   1.00    8.00    --  107.58  77.00 150.00   49
 15  \w     90.00 116.00   1.00    8.00    --  107.58  77.00 150.00   26
 16  \w     35.00 109.00   1.00    8.00    --  107.58 -94.00 150.00   74
 17  \w     36.00  61.00   1.00    8.00    --  107.58-125.00 120.00   25
 18  \w   -107.00 -76.00   1.00    2.93    --  -40.92-142.00  80.00   31
 19  \w   -109.00 -17.00   1.00    2.93    --  -40.92 -37.00 -30.00   92
 20  \w   -114.00 -25.00   1.00    2.93    --  -40.92 -37.00-120.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0478117000
_diffrn_orient_matrix_UB_12      0.1161333000
_diffrn_orient_matrix_UB_13      -0.0254448000
_diffrn_orient_matrix_UB_21      -0.0362426000
_diffrn_orient_matrix_UB_22      0.0205927000
_diffrn_orient_matrix_UB_23      0.0754839000
_diffrn_orient_matrix_UB_31      0.1758013000
_diffrn_orient_matrix_UB_32      0.0005827000
_diffrn_orient_matrix_UB_33      0.0041450000
_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  0.0648
_diffrn_reflns_av_unetI/netI     0.0794
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14977
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.899
_diffrn_reflns_theta_min         2.288
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.742
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.060
_refine_diff_density_min         -1.080
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     579
_refine_ls_number_reflns         8678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0619
_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^)+(0.0257P)^2^+8.5217P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1480
_refine_ls_wR_factor_ref         0.1557
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7082
_reflns_number_total             8678
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj00306c2.cif
_cod_data_source_block           t-11
_cod_depositor_comments          'Adding full bibliography for 7063079.cif.'
_cod_database_code               7063079
_shelx_shelxl_version_number     2018/3
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C14(H14), C40(H40), C41(H41)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C36(H36A,H36B), C37(H37A,H37B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2A), C3(H3), C4(H4), C5(H5), C12(H12), C17(H17), C18(H18),
 C19(H19), C20(H20), C23(H23), C24(H24), C25(H25), C26(H26), N3(H3A), C29(H29),
 C30(H30), C31(H31), C32(H32), C39(H39), C44(H44), C45(H45), C46(H46), C47(H47),
  C51(H51), C52(H52), C53(H53), C54(H54)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4A)
;
_shelx_res_checksum              8655
_shelx_hkl_checksum              61401
_olex2_date_sample_data_collection 2022-12-22
_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 1.656
_oxdiff_exptl_absorpt_empirical_full_min 0.349