#------------------------------------------------------------------------------
#$Date: 2024-02-04 13:40:59 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289455 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/79/7247908.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_7247908
loop_
_publ_author_name
'Bandaru, Ravi Kumar'
'Giri, Lopamudra'
'Krishna, Gamidi Rama'
'Dandela, Rambabu'
_publ_section_title
;
 Novel molecular adducts of an anti-cancer drug vandetanib with enhanced
 solubility
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              248
_journal_page_last               260
_journal_paper_doi               10.1039/D3CE01130E
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C22 H25 Br F N4 O2, C6 H9 O4, 3(H2 O)'
_chemical_formula_sum            'C28 H40 Br F N4 O9'
_chemical_formula_weight         675.54
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-09-07 deposited with the CCDC.	2023-12-14 downloaded from the CCDC.
;
_cell_angle_alpha                100.34(1)
_cell_angle_beta                 96.88(1)
_cell_angle_gamma                91.489(1)
_cell_formula_units_Z            2
_cell_length_a                   8.913(1)
_cell_length_b                   12.550(1)
_cell_length_c                   14.540(1)
_cell_measurement_reflns_used    5044
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      0.850
_cell_measurement_theta_min      0.762
_cell_volume                     1586.6(3)
_computing_cell_refinement       'Bruker SHELXL'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture photon 100 CMOS detector'
_diffrn_measurement_method       'Omega and Phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1192
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            69030
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.579
_diffrn_reflns_theta_min         2.304
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    1.357
_exptl_absorpt_correction_T_max  0.850
_exptl_absorpt_correction_T_min  0.762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         7318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0421P)²+0.4671P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0981
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5044
_reflns_number_total             7318
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce01130e2.cif
_cod_data_source_block           VANADP_XPREP_1_a
_cod_depositor_comments
'Adding full bibliography for 7247904--7247909.cif.'
_cod_original_cell_volume        1586.8(1)
_cod_database_code               7247908
_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.
;
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
Br1 Br 0.04156(3) 0.88136(2) 1.25019(2) 0.05656(11) Uani 1 1 d . . . . .
C1 C 0.5252(3) 0.6830(3) 0.01020(16) 0.0665(8) Uani 1 1 d . . . . .
H1A H 0.474256 0.613495 -0.013867 0.100 Uiso 1 1 calc R U . . .
H1B H 0.626003 0.682161 -0.006866 0.100 Uiso 1 1 calc R U . . .
H1C H 0.470886 0.737845 -0.016068 0.100 Uiso 1 1 calc R U . . .
O1 O 0.34464(17) 0.85363(15) 0.43306(10) 0.0491(4) Uani 1 1 d . . . . .
N1 N 0.5323(2) 0.70703(16) 0.11460(11) 0.0403(4) Uani 1 1 d . . . . .
H1 H 0.588992 0.650254 0.139379 0.048 Uiso 1 1 calc R U . . .
F1 F 0.24486(15) 1.02697(11) 0.97683(9) 0.0495(3) Uani 1 1 d . . . . .
N3 N 0.38408(18) 0.85582(16) 0.87090(11) 0.0393(4) Uani 1 1 d . . . . .
C3 C 0.6274(2) 0.8323(2) 0.26237(15) 0.0420(5) Uani 1 1 d . . . . .
H3A H 0.677601 0.902829 0.287407 0.050 Uiso 1 1 calc R U . . .
H3AB H 0.689176 0.777965 0.285638 0.050 Uiso 1 1 calc R U . . .
O3 O 0.7718(4) 0.6114(2) 0.57815(18) 0.1265(12) Uani 1 1 d . . . . .
N2 N 0.55131(18) 0.86006(16) 0.75488(12) 0.0410(4) Uani 1 1 d . . . . .
O2 O 0.07419(16) 0.85845(16) 0.47513(10) 0.0519(4) Uani 1 1 d . . . . .
C2 C 0.6137(3) 0.8122(2) 0.15566(15) 0.0461(6) Uani 1 1 d . . . . .
H2A H 0.559726 0.870132 0.132488 0.055 Uiso 1 1 calc R U . . .
H2AB H 0.713878 0.812358 0.135987 0.055 Uiso 1 1 calc R U . . .
N4 N 0.12559(17) 0.85563(15) 0.83793(11) 0.0353(4) Uani 1 1 d . . . . .
H4A H 0.046125 0.851753 0.797371 0.042 Uiso 1 1 calc R U . . .
C4 C 0.4732(2) 0.82830(19) 0.29718(14) 0.0387(5) Uani 1 1 d . . . . .
H4 H 0.415410 0.888043 0.278565 0.046 Uiso 1 1 calc R U . . .
O4 O 0.6411(4) 0.4770(2) 0.61182(17) 0.1055(9) Uani 1 1 d . . . . .
H4B H 0.647467 0.516086 0.663921 0.158 Uiso 1 1 calc R U . . .
O5 O 0.8608(2) 0.55757(18) 0.11111(14) 0.0746(6) Uani 1 1 d . . . . .
C5 C 0.3887(3) 0.7221(2) 0.25101(16) 0.0455(5) Uani 1 1 d . . . . .
H5A H 0.439904 0.662712 0.273612 0.055 Uiso 1 1 calc R U . . .
H5AB H 0.287325 0.722226 0.268925 0.055 Uiso 1 1 calc R U . . .
O6 O 0.6545(2) 0.53739(16) 0.17748(13) 0.0657(5) Uani 1 1 d . . . . .
C6 C 0.3790(3) 0.7041(2) 0.14477(16) 0.0489(6) Uani 1 1 d . . . . .
H6A H 0.327684 0.634429 0.117873 0.059 Uiso 1 1 calc R U . . .
H6AB H 0.320292 0.759944 0.121494 0.059 Uiso 1 1 calc R U . . .
O9 O 0.8426(3) 0.5263(2) 0.91574(18) 0.0728(6) Uani 1 1 d . . . . .
H5 H 0.851(4) 0.531(3) 0.970(3) 0.077(12) Uiso 1 1 d . . . . .
H3 H 0.931(5) 0.498(3) 0.904(3) 0.119(16) Uiso 1 1 d . . . . .
C9 C 0.4528(2) 0.85914(19) 0.59427(14) 0.0386(5) Uani 1 1 d . . . . .
H9 H 0.551049 0.859529 0.578865 0.046 Uiso 1 1 calc R U . . .
O8 O 0.8435(2) 0.7923(2) 0.72328(15) 0.0628(6) Uani 1 1 d . . . . .
H2 H 0.834(4) 0.743(3) 0.692(2) 0.069(12) Uiso 1 1 d . . . . .
H8 H 0.764(4) 0.817(3) 0.732(2) 0.070(10) Uiso 1 1 d . . . . .
C8 C 0.3338(2) 0.85726(18) 0.52570(14) 0.0370(5) Uani 1 1 d . . . . .
O7 O 0.6068(4) 0.5756(2) 0.78297(17) 0.0808(7) Uani 1 1 d . . . . .
H10 H 0.531(5) 0.546(4) 0.795(3) 0.130(19) Uiso 1 1 d . . . . .
H7 H 0.713(6) 0.589(4) 0.816(4) 0.17(2) Uiso 1 1 d . . . . .
C7 C 0.4925(2) 0.8426(2) 0.40326(14) 0.0437(5) Uani 1 1 d . . . . .
H7A H 0.539145 0.780117 0.423230 0.052 Uiso 1 1 calc R U . . .
H7AB H 0.556673 0.906660 0.430866 0.052 Uiso 1 1 calc R U . . .
C11 C 0.2797(2) 0.86074(16) 0.71155(13) 0.0297(4) Uani 1 1 d . . . . .
C10 C 0.4280(2) 0.86049(17) 0.68833(13) 0.0330(4) Uani 1 1 d . . . . .
C12 C 0.1575(2) 0.86148(17) 0.64012(13) 0.0331(4) Uani 1 1 d . . . . .
H12 H 0.058991 0.863304 0.655243 0.040 Uiso 1 1 calc R U . . .
C14 C 0.5196(2) 0.8572(2) 0.83973(15) 0.0444(5) Uani 1 1 d . . . . .
H14 H 0.602542 0.855979 0.884851 0.053 Uiso 1 1 calc R U . . .
C13 C 0.1829(2) 0.85954(18) 0.54920(13) 0.0357(5) Uani 1 1 d . . . . .
C15 C 0.2639(2) 0.85795(16) 0.80765(13) 0.0311(4) Uani 1 1 d . . . . .
C16 C 0.1078(2) 0.85935(17) 0.93363(13) 0.0320(4) Uani 1 1 d . . . . .
C17 C 0.1688(2) 0.94528(17) 1.00293(14) 0.0341(5) Uani 1 1 d . . . . .
C18 C 0.1502(2) 0.95342(18) 1.09612(13) 0.0361(5) Uani 1 1 d . . . . .
H18 H 0.193550 1.011805 1.140981 0.043 Uiso 1 1 calc R U . . .
C19 C 0.0654(2) 0.87254(18) 1.12126(13) 0.0361(5) Uani 1 1 d . . . . .
C20 C 0.0014(2) 0.78595(19) 1.05539(15) 0.0404(5) Uani 1 1 d . . . . .
H20 H -0.055587 0.731849 1.073375 0.048 Uiso 1 1 calc R U . . .
C21 C 0.0228(2) 0.78021(18) 0.96161(14) 0.0383(5) Uani 1 1 d . . . . .
H21 H -0.021048 0.721948 0.916788 0.046 Uiso 1 1 calc R U . . .
C22 C -0.0791(3) 0.8540(3) 0.49443(17) 0.0688(9) Uani 1 1 d . . . . .
H22A H -0.145970 0.854602 0.437624 0.103 Uiso 1 1 calc R U . . .
H22B H -0.095517 0.915690 0.541049 0.103 Uiso 1 1 calc R U . . .
H22C H -0.098919 0.788690 0.517565 0.103 Uiso 1 1 calc R U . . .
C23 C 0.7927(3) 0.5242(2) 0.17028(16) 0.0527(6) Uani 1 1 d . . . . .
C24 C 0.8861(5) 0.4645(3) 0.2359(2) 0.0996(13) Uani 1 1 d . . . . .
H24A H 0.927895 0.403969 0.197516 0.119 Uiso 1 1 calc R U . . .
H24B H 0.970666 0.512920 0.267514 0.119 Uiso 1 1 calc R U . . .
C25 C 0.8152(5) 0.4220(3) 0.3087(2) 0.0878(11) Uani 1 1 d . . . . .
H25A H 0.876817 0.365701 0.328654 0.105 Uiso 1 1 calc R U . . .
H25B H 0.717239 0.388387 0.280643 0.105 Uiso 1 1 calc R U . . .
C26 C 0.7936(4) 0.5031(3) 0.3935(2) 0.0770(9) Uani 1 1 d . . . . .
H26A H 0.723661 0.555939 0.375649 0.092 Uiso 1 1 calc R U . . .
H26B H 0.889577 0.541153 0.419904 0.092 Uiso 1 1 calc R U . . .
C27 C 0.7325(5) 0.4487(3) 0.4672(2) 0.0835(10) Uani 1 1 d . . . . .
H27A H 0.633363 0.415347 0.441452 0.100 Uiso 1 1 calc R U . . .
H27B H 0.798178 0.391207 0.479836 0.100 Uiso 1 1 calc R U . . .
C28 C 0.7190(4) 0.5219(3) 0.5577(2) 0.0718(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 0.0033 0.0016 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C8 O1 C7 117.49(16) . . ?
C2 N1 C6 110.52(17) . . ?
C2 N1 C1 111.71(19) . . ?
C6 N1 C1 111.55(19) . . ?
C15 N3 C14 116.55(17) . . ?
C2 C3 C4 111.69(18) . . ?
C14 N2 C10 115.15(17) . . ?
C13 O2 C22 116.54(16) . . ?
N1 C2 C3 110.92(18) . . ?
C15 N4 C16 122.31(15) . . ?
C7 C4 C5 111.81(19) . . ?
C7 C4 C3 109.94(17) . . ?
C5 C4 C3 109.31(18) . . ?
C6 C5 C4 111.80(19) . . ?
N1 C6 C5 110.87(18) . . ?
C8 C9 C10 120.50(18) . . ?
O1 C8 C9 125.34(18) . . ?
O1 C8 C13 114.59(17) . . ?
C9 C8 C13 120.08(18) . . ?
O1 C7 C4 107.55(17) . . ?
C10 C11 C12 119.27(17) . . ?
C10 C11 C15 116.23(16) . . ?
C12 C11 C15 124.49(17) . . ?
N2 C10 C11 121.83(17) . . ?
N2 C10 C9 118.50(17) . . ?
C11 C10 C9 119.66(17) . . ?
C13 C12 C11 120.49(17) . . ?
N2 C14 N3 128.98(18) . . ?
O2 C13 C12 125.38(17) . . ?
O2 C13 C8 114.64(17) . . ?
C12 C13 C8 119.98(17) . . ?
N3 C15 N4 117.29(17) . . ?
N3 C15 C11 121.24(17) . . ?
N4 C15 C11 121.46(16) . . ?
C21 C16 C17 117.12(18) . . ?
C21 C16 N4 121.39(18) . . ?
C17 C16 N4 121.42(18) . . ?
F1 C17 C18 118.39(18) . . ?
F1 C17 C16 118.40(17) . . ?
C18 C17 C16 123.15(19) . . ?
C17 C18 C19 117.96(19) . . ?
C20 C19 C18 121.32(18) . . ?
C20 C19 Br1 120.20(16) . . ?
C18 C19 Br1 118.46(15) . . ?
C19 C20 C21 119.2(2) . . ?
C16 C21 C20 121.26(19) . . ?
O5 C23 O6 124.2(2) . . ?
O5 C23 C24 115.4(3) . . ?
O6 C23 C24 120.4(3) . . ?
C25 C24 C23 119.4(3) . . ?
C24 C25 C26 115.6(3) . . ?
C25 C26 C27 110.9(3) . . ?
C28 C27 C26 114.9(3) . . ?
O3 C28 O4 123.5(3) . . ?
O3 C28 C27 123.9(3) . . ?
O4 C28 C27 112.6(3) . . ?
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
Br1 C19 1.8958(19) . ?
C1 N1 1.487(3) . ?
O1 C8 1.355(2) . ?
O1 C7 1.438(3) . ?
N1 C2 1.479(3) . ?
N1 C6 1.486(3) . ?
F1 C17 1.349(2) . ?
N3 C15 1.330(2) . ?
N3 C14 1.341(3) . ?
C3 C2 1.516(3) . ?
C3 C4 1.523(3) . ?
O3 C28 1.180(4) . ?
N2 C14 1.305(3) . ?
N2 C10 1.375(2) . ?
O2 C13 1.357(2) . ?
O2 C22 1.430(3) . ?
N4 C15 1.359(2) . ?
N4 C16 1.412(2) . ?
C4 C7 1.509(3) . ?
C4 C5 1.517(3) . ?
O4 C28 1.300(4) . ?
O5 C23 1.235(3) . ?
C5 C6 1.512(3) . ?
O6 C23 1.261(3) . ?
C9 C8 1.362(3) . ?
C9 C10 1.408(3) . ?
C8 C13 1.427(3) . ?
C11 C10 1.403(3) . ?
C11 C12 1.414(3) . ?
C11 C15 1.428(3) . ?
C12 C13 1.364(3) . ?
C16 C21 1.381(3) . ?
C16 C17 1.386(3) . ?
C17 C18 1.371(3) . ?
C18 C19 1.377(3) . ?
C19 C20 1.374(3) . ?
C20 C21 1.389(3) . ?
C23 C24 1.505(4) . ?
C24 C25 1.465(5) . ?
C25 C26 1.488(4) . ?
C26 C27 1.515(4) . ?
C27 C28 1.482(4) . ?
