#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:23:48 +0300 (Tue, 06 Oct 2020) $
#$Revision: 258019 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/08/7240834.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7240834
loop_
_publ_author_name
'Junaid, Ahmad'
'Lim, Felicia Phei Lin'
'Tiekink, Edward R. T.'
'Dolzhenko, Anton V.'
_publ_section_title
;
 Design, synthesis, and biological evaluation of new
 6,N2-diaryl-1,3,5-triazine-2,4-diamines as anticancer agents selectively
 targeting triple negative breast cancer cells
;
_journal_issue                   43
_journal_name_full               'RSC Advances'
_journal_page_first              25517
_journal_page_last               25528
_journal_paper_doi               10.1039/D0RA04970K
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C19 H18 F3 N5 O4'
_chemical_formula_sum            'C19 H18 F3 N5 O4'
_chemical_formula_weight         437.38
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-06-18 deposited with the CCDC.	2020-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                104.412(2)
_cell_angle_beta                 99.253(2)
_cell_angle_gamma                108.517(2)
_cell_formula_units_Z            2
_cell_length_a                   7.2212(2)
_cell_length_b                   10.9597(3)
_cell_length_c                   13.4202(3)
_cell_measurement_reflns_used    13071
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.2730
_cell_measurement_theta_min      3.4960
_cell_volume                     941.58(5)
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2017)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.2558
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22208
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.073
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         3.523
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.125
_exptl_absorpt_correction_T_max  0.669
_exptl_absorpt_correction_T_min  0.232
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'CrysAlisPro (Rigaku OD, 2017)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_description       prism
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.125
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.054
_refine_diff_density_max         1.731
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.080
_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     292
_refine_ls_number_reflns         3357
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0591
_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/[σ²(Fo²)+(0.1035P)²+1.1788P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1719
_refine_ls_wR_factor_ref         0.1764
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3044
_reflns_number_total             3357
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra04970k3.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7240834.cif.'
_cod_original_cell_volume        941.57(4)
_cod_database_code               7240834
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.872
_shelx_estimated_absorpt_t_max   0.942
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.3103(4) 0.1435(2) -0.17278(16) 0.0598(6) Uani 1 1 d . . . . .
F2 F 0.1779(4) -0.05955(19) -0.17066(15) 0.0638(6) Uani 1 1 d . . . . .
F3 F 0.4675(3) 0.0820(2) -0.06268(16) 0.0595(6) Uani 1 1 d . . . . .
O1 O 0.7523(2) 0.13811(15) 0.52670(12) 0.0195(4) Uani 1 1 d . . . . .
O2 O 0.9557(2) 0.23143(16) 0.73220(13) 0.0210(4) Uani 1 1 d . . . . .
O3 O 1.0869(2) 0.49518(16) 0.84574(13) 0.0219(4) Uani 1 1 d . . . . .
O4 O 0.1716(3) 0.10077(19) -0.04204(14) 0.0379(5) Uani 1 1 d . . . . .
N1 N 0.6838(3) 0.54545(18) 0.43247(15) 0.0166(4) Uani 1 1 d . . . . .
N2 N 0.7191(3) 0.77271(18) 0.44012(15) 0.0184(4) Uani 1 1 d . . . . .
N3 N 0.8713(3) 0.72872(18) 0.59236(15) 0.0175(4) Uani 1 1 d . . . . .
N4 N 0.8957(3) 0.94369(19) 0.59860(16) 0.0218(4) Uani 1 1 d D . . . .
H1N H 0.976(4) 0.970(3) 0.6628(12) 0.026 Uiso 1 1 d D U . . .
H2N H 0.873(4) 1.005(2) 0.572(2) 0.026 Uiso 1 1 d D U . . .
N5 N 0.5481(3) 0.59827(19) 0.28611(15) 0.0199(4) Uani 1 1 d D . . . .
H3N H 0.546(4) 0.667(2) 0.264(2) 0.024 Uiso 1 1 d D U . . .
C1 C 0.7955(3) 0.5981(2) 0.53370(17) 0.0156(5) Uani 1 1 d . . . . .
C2 C 0.6536(3) 0.6383(2) 0.39033(18) 0.0168(5) Uani 1 1 d . . . . .
C3 C 0.8263(3) 0.8117(2) 0.54106(18) 0.0177(5) Uani 1 1 d . . . . .
C4 C 0.8392(3) 0.5014(2) 0.58558(18) 0.0158(5) Uani 1 1 d . . . . .
C5 C 0.7707(3) 0.3641(2) 0.52748(17) 0.0161(5) Uani 1 1 d . . . . .
H5 H 0.697643 0.332025 0.454655 0.019 Uiso 1 1 calc R U . . .
C6 C 0.8102(3) 0.2747(2) 0.57676(18) 0.0165(5) Uani 1 1 d . . . . .
C7 C 0.9156(3) 0.3215(2) 0.68420(18) 0.0174(5) Uani 1 1 d . . . . .
C8 C 0.9857(3) 0.4599(2) 0.74164(18) 0.0179(5) Uani 1 1 d . . . . .
C9 C 0.9484(3) 0.5501(2) 0.69220(18) 0.0168(5) Uani 1 1 d . . . . .
H9 H 0.997027 0.644324 0.730740 0.020 Uiso 1 1 calc R U . . .
C10 C 0.6426(3) 0.0851(2) 0.41675(19) 0.0215(5) Uani 1 1 d . . . . .
H10A H 0.515128 0.100189 0.409311 0.032 Uiso 1 1 calc R U . . .
H10B H 0.613800 -0.012567 0.390091 0.032 Uiso 1 1 calc R U . . .
H10C H 0.723735 0.131253 0.375543 0.032 Uiso 1 1 calc R U . . .
C11 C 0.8178(4) 0.1916(2) 0.79419(19) 0.0245(5) Uani 1 1 d . . . . .
H11A H 0.826513 0.272171 0.849630 0.037 Uiso 1 1 calc R U . . .
H11B H 0.852814 0.129025 0.827547 0.037 Uiso 1 1 calc R U . . .
H11C H 0.679669 0.146188 0.747891 0.037 Uiso 1 1 calc R U . . .
C12 C 1.1669(4) 0.6367(2) 0.90513(19) 0.0243(5) Uani 1 1 d . . . . .
H12A H 1.259839 0.686901 0.870588 0.036 Uiso 1 1 calc R U . . .
H12B H 1.239902 0.650709 0.977762 0.036 Uiso 1 1 calc R U . . .
H12C H 1.055843 0.669568 0.907778 0.036 Uiso 1 1 calc R U . . .
C13 C 0.4559(3) 0.4705(2) 0.20805(18) 0.0189(5) Uani 1 1 d . . . . .
C14 C 0.3857(3) 0.4683(3) 0.1041(2) 0.0239(5) Uani 1 1 d . . . . .
H14 H 0.402939 0.551658 0.090515 0.029 Uiso 1 1 calc R U . . .
C15 C 0.2917(3) 0.3477(3) 0.02050(19) 0.0249(5) Uani 1 1 d . . . . .
H15 H 0.243682 0.347485 -0.049751 0.030 Uiso 1 1 calc R U . . .
C16 C 0.2693(4) 0.2277(3) 0.04178(19) 0.0261(5) Uani 1 1 d . . . . .
C17 C 0.3311(4) 0.2257(2) 0.1438(2) 0.0270(5) Uani 1 1 d . . . . .
H17 H 0.310097 0.141504 0.156661 0.032 Uiso 1 1 calc R U . . .
C18 C 0.4239(4) 0.3467(2) 0.22772(19) 0.0234(5) Uani 1 1 d . . . . .
H18 H 0.465631 0.345649 0.298230 0.028 Uiso 1 1 calc R U . . .
C19 C 0.2855(5) 0.0671(3) -0.1078(2) 0.0439(8) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 C10 117.56(16) . . ?
C7 O2 C11 112.18(16) . . ?
C8 O3 C12 116.35(17) . . ?
C19 O4 C16 115.8(2) . . ?
C1 N1 C2 113.68(19) . . ?
C3 N2 C2 113.67(18) . . ?
C1 N3 C3 114.26(19) . . ?
C3 N4 H1N 118.1(19) . . ?
C3 N4 H2N 122.3(19) . . ?
H1N N4 H2N 119(3) . . ?
C2 N5 C13 131.85(18) . . ?
C2 N5 H3N 113.0(19) . . ?
C13 N5 H3N 115.0(18) . . ?
N3 C1 N1 126.18(19) . . ?
N3 C1 C4 116.93(19) . . ?
N1 C1 C4 116.89(19) . . ?
N2 C2 N1 126.6(2) . . ?
N2 C2 N5 113.89(19) . . ?
N1 C2 N5 119.5(2) . . ?
N2 C3 N4 118.48(19) . . ?
N2 C3 N3 125.6(2) . . ?
N4 C3 N3 115.9(2) . . ?
C5 C4 C9 120.9(2) . . ?
C5 C4 C1 119.8(2) . . ?
C9 C4 C1 119.3(2) . . ?
C6 C5 C4 119.4(2) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
O1 C6 C5 124.2(2) . . ?
O1 C6 C7 115.47(18) . . ?
C5 C6 C7 120.3(2) . . ?
O2 C7 C8 120.4(2) . . ?
O2 C7 C6 119.79(19) . . ?
C8 C7 C6 119.82(19) . . ?
O3 C8 C9 124.8(2) . . ?
O3 C8 C7 115.24(19) . . ?
C9 C8 C7 120.0(2) . . ?
C8 C9 C4 119.5(2) . . ?
C8 C9 H9 120.2 . . ?
C4 C9 H9 120.2 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N5 C13 C18 124.7(2) . . ?
N5 C13 C14 116.7(2) . . ?
C18 C13 C14 118.6(2) . . ?
C15 C14 C13 121.7(2) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C14 C15 C16 118.3(2) . . ?
C14 C15 H15 120.9 . . ?
C16 C15 H15 120.9 . . ?
C17 C16 C15 121.6(2) . . ?
C17 C16 O4 118.2(2) . . ?
C15 C16 O4 120.1(2) . . ?
C16 C17 C18 119.9(2) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C13 119.7(2) . . ?
C17 C18 H18 120.1 . . ?
C13 C18 H18 120.1 . . ?
F3 C19 F2 111.9(3) . . ?
F3 C19 F1 104.6(3) . . ?
F2 C19 F1 105.9(2) . . ?
F3 C19 O4 116.8(2) . . ?
F2 C19 O4 106.3(3) . . ?
F1 C19 O4 110.9(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C19 1.346(4) . ?
F2 C19 1.328(3) . ?
F3 C19 1.296(4) . ?
O1 C6 1.370(3) . ?
O1 C10 1.431(3) . ?
O2 C7 1.383(3) . ?
O2 C11 1.430(3) . ?
O3 C8 1.363(3) . ?
O3 C12 1.429(3) . ?
O4 C19 1.363(4) . ?
O4 C16 1.428(3) . ?
N1 C1 1.338(3) . ?
N1 C2 1.338(3) . ?
N2 C3 1.335(3) . ?
N2 C2 1.344(3) . ?
N3 C1 1.331(3) . ?
N3 C3 1.354(3) . ?
N4 C3 1.341(3) . ?
N4 H1N 0.879(10) . ?
N4 H2N 0.876(10) . ?
N5 C2 1.367(3) . ?
N5 C13 1.398(3) . ?
N5 H3N 0.884(10) . ?
C1 C4 1.489(3) . ?
C4 C5 1.391(3) . ?
C4 C9 1.394(3) . ?
C5 C6 1.386(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.397(3) . ?
C7 C8 1.399(3) . ?
C8 C9 1.388(3) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.401(3) . ?
C13 C14 1.396(3) . ?
C14 C15 1.383(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.378(4) . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N3 C1 N1 0.1(3) . . . . ?
C3 N3 C1 C4 -179.86(17) . . . . ?
C2 N1 C1 N3 1.2(3) . . . . ?
C2 N1 C1 C4 -178.87(17) . . . . ?
C3 N2 C2 N1 0.9(3) . . . . ?
C3 N2 C2 N5 -178.43(17) . . . . ?
C1 N1 C2 N2 -1.7(3) . . . . ?
C1 N1 C2 N5 177.59(18) . . . . ?
C13 N5 C2 N2 -179.9(2) . . . . ?
C13 N5 C2 N1 0.7(3) . . . . ?
C2 N2 C3 N4 -178.81(18) . . . . ?
C2 N2 C3 N3 0.6(3) . . . . ?
C1 N3 C3 N2 -1.1(3) . . . . ?
C1 N3 C3 N4 178.35(18) . . . . ?
N3 C1 C4 C5 -177.65(18) . . . . ?
N1 C1 C4 C5 2.4(3) . . . . ?
N3 C1 C4 C9 2.4(3) . . . . ?
N1 C1 C4 C9 -177.60(18) . . . . ?
C9 C4 C5 C6 0.7(3) . . . . ?
C1 C4 C5 C6 -179.30(18) . . . . ?
C10 O1 C6 C5 -0.6(3) . . . . ?
C10 O1 C6 C7 179.57(18) . . . . ?
C4 C5 C6 O1 -179.06(18) . . . . ?
C4 C5 C6 C7 0.7(3) . . . . ?
C11 O2 C7 C8 81.7(2) . . . . ?
C11 O2 C7 C6 -100.4(2) . . . . ?
O1 C6 C7 O2 0.4(3) . . . . ?
C5 C6 C7 O2 -179.40(18) . . . . ?
O1 C6 C7 C8 178.38(18) . . . . ?
C5 C6 C7 C8 -1.4(3) . . . . ?
C12 O3 C8 C9 -3.0(3) . . . . ?
C12 O3 C8 C7 177.66(18) . . . . ?
O2 C7 C8 O3 -2.0(3) . . . . ?
C6 C7 C8 O3 -179.93(18) . . . . ?
O2 C7 C8 C9 178.67(18) . . . . ?
C6 C7 C8 C9 0.7(3) . . . . ?
O3 C8 C9 C4 -178.61(19) . . . . ?
C7 C8 C9 C4 0.7(3) . . . . ?
C5 C4 C9 C8 -1.4(3) . . . . ?
C1 C4 C9 C8 178.59(18) . . . . ?
C2 N5 C13 C18 11.5(4) . . . . ?
C2 N5 C13 C14 -170.7(2) . . . . ?
N5 C13 C14 C15 -179.9(2) . . . . ?
C18 C13 C14 C15 -2.0(3) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C17 2.5(4) . . . . ?
C14 C15 C16 O4 179.5(2) . . . . ?
C19 O4 C16 C17 -105.1(3) . . . . ?
C19 O4 C16 C15 77.9(3) . . . . ?
C15 C16 C17 C18 -2.0(4) . . . . ?
O4 C16 C17 C18 -179.0(2) . . . . ?
C16 C17 C18 C13 -0.5(4) . . . . ?
N5 C13 C18 C17 -179.8(2) . . . . ?
C14 C13 C18 C17 2.5(3) . . . . ?
C16 O4 C19 F3 46.7(4) . . . . ?
C16 O4 C19 F2 172.4(2) . . . . ?
C16 O4 C19 F1 -72.9(3) . . . . ?
