Enhanced antitumour effect for hepatocellular carcinoma in the advanced stage using a cyclodextrin-sorafenib-chaperoned inclusion complex.
Phan, Chiuyen; Zheng, Ziyang; Wang, Jianwei; Wang, Qiwen; Hu, Xiurong; Tang, Guping; Bai, Hongzhen; Biomaterials science 7 (2019) 4758–4768; doi:10.1039/c9bm01190k

data_1554619
_publ_section_title
;
 Enhanced antitumour effect for hepatocellular carcinoma in the advanced
 stage using a cyclodextrin-sorafenib-chaperoned inclusion complex.
;
_journal_issue                   11
_journal_name_full               'Biomaterials science'
_journal_page_first              4758
_journal_page_last               4768
_journal_paper_doi               10.1039/c9bm01190k
_journal_volume                  7
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C42 H68 O35, 8.5(O), 2(C6)'
_chemical_formula_sum            'C54 H48 Cl0 F0 N0 O43.5'
_chemical_formula_weight         1392.93
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-26 deposited with the CCDC.	2019-08-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.513(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.1281(12)
_cell_length_b                   24.4901(12)
_cell_length_c                   15.6182(10)
_cell_measurement_reflns_used    9793
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.222
_cell_measurement_theta_min      3.002
_cell_volume                     6896.1(7)
_computing_cell_refinement       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_collection       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_reduction        'CrystalStructure (Rigaku,2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            37689
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.222
_diffrn_reflns_theta_max         67.222
_diffrn_reflns_theta_min         3.002
_exptl_absorpt_coefficient_mu    1.050
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_correction_T_min  0.690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Higashi, T. (1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             2880
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.10
_platon_squeeze_details
;
TITL 2s_a      C 2          R = 0.12
CELL   19.1281   24.4901   15.6182     90.00    109.51     90.00
SPGR C2
C101 1.001 0.500-0.003 !       2.90 eA-3
Q102 0.976 0.272 0.159 !       2.74 eA-3
Q103 0.414 0.060 0.972 !       2.54 eA-3
C104 0.500 0.023 0.497 !       2.33 eA-3
C105 0.499 0.351 0.499 !       1.98 eA-3
C106 0.940 0.006 0.532 !       1.93 eA-3
Q107 0.364 0.288 0.457 !       1.55 eA-3
Q108 0.444 0.467 0.499 !       1.21 eA-3
Q109 0.836 0.447 0.543 !       1.19 eA-3
Q110 1.000 0.031-0.005 !       1.03 eA-3
Q111 0.482 0.336 0.078 !       0.97 eA-3
Q112 0.995 0.351 0.020 !       0.93 eA-3
Q113 0.657 0.401 0.032 !       0.84 eA-3
Q114 0.438 0.405 0.455 !       0.82 eA-3
Q115 0.371 0.348 0.420 !       0.76 eA-3
Q116 0.898 0.351 0.670 !       0.75 eA-3
Q117 0.439 0.305 0.004 !       0.74 eA-3
Q118 0.486 0.404 0.438 !       0.71 eA-3
Q119 0.414 0.193 0.515 !       0.68 eA-3
Q120 0.461 0.338 0.906 !       0.68 eA-3
Q121 0.992 0.411 0.812 !       0.68 eA-3
Q122 0.939 0.043 0.484 !       0.63 eA-3
Q123 0.951 0.058 0.957 !       0.62 eA-3
Q124 0.493 0.424 0.388 !       0.62 eA-3
Q125 0.382 0.382 0.373 !       0.61 eA-3
Q126 0.640 0.460 0.031 !       0.55 eA-3
Q127 0.899 0.437 0.326 !       0.54 eA-3
Q128 0.865 0.026 0.449 !       0.53 eA-3
Q129 0.492 0.157 0.228 !       0.52 eA-3
Q130 0.773 0.281 0.810 !       0.52 eA-3
Q131 0.278 0.241 0.564 !       0.52 eA-3
Q132 0.332 0.280 0.115 !       0.51 eA-3
Q133 0.539 0.461 0.303 !       0.50 eA-3
;
_refine_diff_density_max         1.374
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.110
_refine_ls_abs_structure_details
;
 Flack x determined using 4393 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.290
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     875
_refine_ls_number_reflns         11994
_refine_ls_number_restraints     277
_refine_ls_restrained_S_all      1.276
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0944
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2731
_refine_ls_wR_factor_ref         0.2855
_reflns_Friedel_coverage         0.911
_reflns_Friedel_fraction_full    0.947
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                10710
_reflns_number_total             11994
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9bm01190k2.cif
_cod_data_source_block           2s_a_sq
_cod_original_formula_sum        'C54 H48 Cl0 F0 N0 O43.50'
_cod_database_code               1554619
_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
 At 1.5 times of:
  All O(H) groups
2. Rigid bond restraints
 C1_1, C2_1, C3_1, C4_1, C5_1, C6_1, C7_1, C8_1, C9_1, C10_1, C11_1, C12_1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C1_1 \\sim C2_1 \\sim C3_1 \\sim C4_1 \\sim C5_1 \\sim C6_1 \\sim C7_1 \\sim
C8_1 \\sim C9_1 \\sim C10_1 \\sim C11_1 \\sim C12_1: within 3A with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C1_1) \\sim Ueq, Uanis(C2_1) \\sim Ueq, Uanis(C3_1) \\sim Ueq,
Uanis(C4_1) \\sim Ueq, Uanis(C5_1) \\sim Ueq, Uanis(C6_1) \\sim Ueq,
Uanis(C7_1) \\sim Ueq, Uanis(C8_1) \\sim Ueq, Uanis(C9_1) \\sim Ueq,
Uanis(C10_1) \\sim Ueq, Uanis(C11_1) \\sim Ueq, Uanis(C12_1) \\sim Ueq: with
sigma of 0.02 and sigma for terminal atoms of 0.04
4.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10),
 C11(H11), C0AA(H0AA), C14(H14), C15(H15), C16(H16), C17(H17), C19(H19),
 C20(H20), C21(H21), C22(H22), C23(H23), C25(H25), C26(H26), C27(H27), C28(H28),
  C29(H29), C31(H31), C32(H32), C33(H33), C34(H34), C35(H35), C37(H37),
 C38(H38), C39(H39), C40(H40), C41(H41)
4.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C13(H13A,H13B), C24(H24A,H24B), C42(H42A,H42B), C12(H12A,H12B),
 C18(H18A,H18B)
4.c Aromatic/amide H refined with riding coordinates:
 C30(H30)
4.d Fitted hexagon refined as free rotating group:
 C1(C2,C3,C4,C5,C6), C7(C8,C9,C10,C11,C12)
4.e Idealised tetrahedral OH refined as rotating group:
 O9(H9A), O14(H14A), O13(H13), O29(H29A), O2(H2A), O3(H3A), O4(H4A), O7(H7A),
 O8(H8A), O12(H12), O17(H17A), O18(H18), O19(H19A), O22(H22A), O23(H23A),
 O27(H27A), O28(H28A), O32(H32A), O33(H33A), O34(H34A)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'