Design, synthesis and anticancer evaluation of imamine-1,3,5-triazine derivatives
Xue, Xuan-Yi; He, Jing-Liang; Li, Rui; Ding, Bo; Wu, Wen-Long; Cao, Yao-Yao; He, Ran; Hu, Peng-Hong; Ji, Jing; Shi, Da-Hua; New Journal of Chemistry 48 (2024) 12188–12198; doi:10.1039/D4NJ00819G

data_7063264
_publ_section_title
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 Design, synthesis and anticancer evaluation of imamine-1,3,5-triazine
 derivatives
;
_journal_issue                   27
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12188
_journal_page_last               12198
_journal_paper_doi               10.1039/D4NJ00819G
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C23 H24 Cl N9, C H Cl3'
_chemical_formula_sum            'C24 H25 Cl4 N9'
_chemical_formula_weight         581.33
_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             2023-06-17
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-02-02 deposited with the CCDC.	2024-06-03 downloaded from the CCDC.
;
_cell_angle_alpha                105.816(5)
_cell_angle_beta                 107.239(6)
_cell_angle_gamma                101.579(6)
_cell_formula_units_Z            2
_cell_length_a                   9.478(4)
_cell_length_b                   12.216(5)
_cell_length_c                   13.705(6)
_cell_measurement_reflns_used    3076
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      2.33
_cell_volume                     1388.1(10)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8622
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.554
_diffrn_reflns_theta_min         1.664
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.458
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5521
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1038 before and 0.0362 after correction.
The Ratio of minimum to maximum transmission is 0.7405.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.738
_refine_diff_density_min         -0.708
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         6174
_refine_ls_number_restraints     103
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.1091
_refine_ls_R_factor_gt           0.0806
_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^)+(0.1341P)^2^+1.0534P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2349
_refine_ls_wR_factor_ref         0.2625
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4128
_reflns_number_total             6174
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj00819g2.cif
_cod_data_source_block           20230616_0m
_cod_depositor_comments          'Adding full bibliography for 7063264.cif.'
_cod_database_code               7063264
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.910
_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. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C23) \\sim Ueq, Uanis(C24) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C25(H25)
4.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C23(H23A,H23B)
4.c Aromatic/amide H refined with riding coordinates:
 N5(H5), N4(H4), C15(H15), C7(H7), C13(H13), C5(H5A), C3(H3), C8(H8), C12(H12),
  C1(H1), C2(H2)
4.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              16107
_olex2_submission_special_instructions 'No special instructions were received'