#------------------------------------------------------------------------------
#$Date: 2023-09-17 02:35:31 +0300 (Sun, 17 Sep 2023) $
#$Revision: 286368 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/74/7247414.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_7247414
loop_
_publ_author_name
'Huo, Zhipeng'
'Min, Delin'
'Zhang, Shijie'
'Tang, Mei-Lin'
'Sun, Xun'
_publ_section_title
;
 Discovery of Novel Tubulin CBSI (R)-9k from Indanone Scaffold for the
 Treatment of Colorectal Cancer
;
_journal_name_full               'RSC Medicinal Chemistry'
_journal_paper_doi               10.1039/D3MD00337J
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H21 F O5'
_chemical_formula_weight         360.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2022-06-21 deposited with the CCDC.	2023-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.9050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.3474(5)
_cell_length_b                   4.42800(10)
_cell_length_c                   14.8423(5)
_cell_measurement_reflns_used    9729
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      140.244
_cell_measurement_theta_min      16.429
_cell_volume                     886.60(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.927
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10827
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.387
_diffrn_reflns_theta_min         8.214
_exptl_absorpt_coefficient_mu    0.864
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.4831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.101
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details
; 
 Flack x determined using 1168 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.08(5)
_refine_ls_extinction_coef       0.037(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         2940
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0320
_refine_ls_shift/su_max          0.033
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0467P)²+0.0761P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0872
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    0.903
_reflns_Friedel_fraction_max     0.924
_reflns_number_gt                2817
_reflns_number_total             2940
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3md00337j2.cif
_cod_data_source_block           cu_ddz21062_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7247414
_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   0.853
_shelx_estimated_absorpt_t_max   0.942
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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 0.12787(10) 0.8586(4) 0.40193(10) 0.0709(5) Uani 1 1 d . . . . .
O1 O 0.56789(12) 0.7843(5) 0.81058(13) 0.0757(6) Uani 1 1 d . . . . .
O2 O 0.25842(13) 0.7024(5) 0.94241(11) 0.0679(5) Uani 1 1 d . . . . .
O3 O 0.13837(12) 0.3368(4) 0.80950(12) 0.0588(4) Uani 1 1 d . . . . .
O4 O 0.19478(10) 0.1106(4) 0.65954(11) 0.0554(4) Uani 1 1 d . . . . .
O5 O 0.16936(13) 0.6107(4) 0.25756(11) 0.0658(5) Uani 1 1 d . . . . .
C1 C 0.49268(16) 0.4326(7) 0.68067(18) 0.0620(6) Uani 1 1 d . . . . .
H1A H 0.5430 0.2761 0.6979 0.074 Uiso 1 1 calc R U . . .
H1B H 0.5028 0.5580 0.6312 0.074 Uiso 1 1 calc R U . . .
C2 C 0.49896(15) 0.6204(6) 0.76701(16) 0.0567(6) Uani 1 1 d . . . . .
C3 C 0.40719(15) 0.5740(5) 0.78795(15) 0.0517(5) Uani 1 1 d . . . . .
C4 C 0.38229(16) 0.6918(6) 0.86413(15) 0.0558(6) Uani 1 1 d . . . . .
H4 H 0.4256 0.8179 0.9094 0.067 Uiso 1 1 calc R U . . .
C5 C 0.29179(17) 0.6156(5) 0.87003(15) 0.0531(5) Uani 1 1 d . . . . .
C6 C 0.22552(16) 0.4270(5) 0.80011(15) 0.0495(5) Uani 1 1 d . . . . .
C7 C 0.25194(15) 0.3111(5) 0.72508(14) 0.0460(5) Uani 1 1 d . . . . .
C8 C 0.34397(15) 0.3872(5) 0.71898(14) 0.0465(5) Uani 1 1 d . . . . .
C9 C 0.38781(15) 0.2897(5) 0.64422(15) 0.0496(5) Uani 1 1 d . . . . .
H9 H 0.3948 0.0695 0.6468 0.060 Uiso 1 1 calc R U . . .
C10 C 0.32978(15) 0.3807(5) 0.54175(15) 0.0467(5) Uani 1 1 d . . . . .
C11 C 0.25285(15) 0.5885(5) 0.51822(15) 0.0487(5) Uani 1 1 d . . . . .
H11 H 0.2349 0.6811 0.5661 0.058 Uiso 1 1 calc R U . . .
C12 C 0.20328(15) 0.6566(5) 0.42345(15) 0.0500(5) Uani 1 1 d . . . . .
C13 C 0.22660(16) 0.5277(5) 0.34893(15) 0.0521(5) Uani 1 1 d . . . . .
C14 C 0.30492(19) 0.3282(6) 0.37276(17) 0.0604(6) Uani 1 1 d . . . . .
H14 H 0.3244 0.2424 0.3248 0.072 Uiso 1 1 calc R U . . .
C15 C 0.35495(18) 0.2543(6) 0.46771(17) 0.0586(6) Uani 1 1 d . . . . .
H15 H 0.4068 0.1162 0.4822 0.070 Uiso 1 1 calc R U . . .
C16 C 0.1864(2) 0.4518(8) 0.18109(17) 0.0741(8) Uani 1 1 d . . . . .
H16A H 0.1822 0.2358 0.1897 0.089 Uiso 1 1 calc R U . . .
H16B H 0.2519 0.4982 0.1795 0.089 Uiso 1 1 calc R U . . .
C17 C 0.1083(2) 0.5505(10) 0.08925(19) 0.0854(9) Uani 1 1 d . . . . .
H17A H 0.1160 0.4401 0.0366 0.128 Uiso 1 1 calc R U . . .
H17B H 0.1153 0.7627 0.0799 0.128 Uiso 1 1 calc R U . . .
H17C H 0.0438 0.5117 0.0928 0.128 Uiso 1 1 calc R U . . .
C18 C 0.09387(17) 0.1894(8) 0.60863(19) 0.0689(7) Uani 1 1 d . . . . .
H18A H 0.0739 0.1048 0.5453 0.103 Uiso 1 1 calc R U . . .
H18B H 0.0876 0.4052 0.6043 0.103 Uiso 1 1 calc R U . . .
H18C H 0.0524 0.1110 0.6420 0.103 Uiso 1 1 calc R U . . .
C19 C 0.06682(19) 0.5676(7) 0.8045(2) 0.0695(7) Uani 1 1 d . . . . .
H19A H 0.0593 0.6940 0.7499 0.104 Uiso 1 1 calc R U . . .
H19B H 0.0889 0.6874 0.8618 0.104 Uiso 1 1 calc R U . . .
H19C H 0.0043 0.4760 0.7984 0.104 Uiso 1 1 calc R U . . .
C20 C 0.3223(2) 0.8861(8) 1.01628(18) 0.0758(8) Uani 1 1 d . . . . .
H20A H 0.3410 1.0617 0.9885 0.114 Uiso 1 1 calc R U . . .
H20B H 0.3805 0.7735 1.0512 0.114 Uiso 1 1 calc R U . . .
H20C H 0.2884 0.9474 1.0590 0.114 Uiso 1 1 calc R U . . .
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'
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
C5 O2 C20 117.4(2) . . ?
C6 O3 C19 116.8(2) . . ?
C7 O4 C18 118.21(19) . . ?
C13 O5 C16 116.52(19) . . ?
C2 C1 C9 107.00(18) . . ?
C2 C1 H1A 110.3 . . ?
C9 C1 H1A 110.3 . . ?
C2 C1 H1B 110.3 . . ?
C9 C1 H1B 110.3 . . ?
H1A C1 H1B 108.6 . . ?
O1 C2 C3 126.5(2) . . ?
O1 C2 C1 125.7(2) . . ?
C3 C2 C1 107.78(19) . . ?
C8 C3 C4 122.5(2) . . ?
C8 C3 C2 109.6(2) . . ?
C4 C3 C2 127.9(2) . . ?
C5 C4 C3 117.9(2) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
O2 C5 C4 124.8(2) . . ?
O2 C5 C6 114.37(19) . . ?
C4 C5 C6 120.8(2) . . ?
O3 C6 C7 118.86(19) . . ?
O3 C6 C5 120.52(19) . . ?
C7 C6 C5 120.41(19) . . ?
O4 C7 C6 123.32(18) . . ?
O4 C7 C8 117.58(18) . . ?
C6 C7 C8 118.99(19) . . ?
C3 C8 C7 119.46(19) . . ?
C3 C8 C9 112.38(19) . . ?
C7 C8 C9 128.15(19) . . ?
C8 C9 C10 115.84(17) . . ?
C8 C9 C1 102.96(18) . . ?
C10 C9 C1 112.17(18) . . ?
C8 C9 H9 108.5 . . ?
C10 C9 H9 108.5 . . ?
C1 C9 H9 108.5 . . ?
C15 C10 C11 117.90(19) . . ?
C15 C10 C9 119.00(18) . . ?
C11 C10 C9 123.09(19) . . ?
C12 C11 C10 119.5(2) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
F1 C12 C11 118.61(19) . . ?
F1 C12 C13 118.36(18) . . ?
C11 C12 C13 123.03(19) . . ?
O5 C13 C14 125.9(2) . . ?
O5 C13 C12 116.90(19) . . ?
C14 C13 C12 117.2(2) . . ?
C13 C14 C15 120.5(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 121.8(2) . . ?
C14 C15 H15 119.1 . . ?
C10 C15 H15 119.1 . . ?
O5 C16 C17 107.5(2) . . ?
O5 C16 H16A 110.2 . . ?
C17 C16 H16A 110.2 . . ?
O5 C16 H16B 110.2 . . ?
C17 C16 H16B 110.2 . . ?
H16A C16 H16B 108.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
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 C12 1.355(2) . ?
O1 C2 1.220(3) . ?
O2 C5 1.372(3) . ?
O2 C20 1.421(3) . ?
O3 C6 1.364(3) . ?
O3 C19 1.432(3) . ?
O4 C7 1.365(2) . ?
O4 C18 1.430(3) . ?
O5 C13 1.375(3) . ?
O5 C16 1.426(3) . ?
C1 C2 1.504(4) . ?
C1 C9 1.550(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.467(3) . ?
C3 C8 1.387(3) . ?
C3 C4 1.398(3) . ?
C4 C5 1.373(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.416(3) . ?
C6 C7 1.391(3) . ?
C7 C8 1.395(3) . ?
C8 C9 1.513(3) . ?
C9 C10 1.519(3) . ?
C9 H9 0.9800 . ?
C10 C15 1.386(3) . ?
C10 C11 1.387(3) . ?
C11 C12 1.376(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.383(3) . ?
C13 C14 1.378(3) . ?
C14 C15 1.385(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.505(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C19 H19B O2 0.96 2.32 2.876(3) 116.5 .
C11 H11 O4 0.93 2.53 3.410(3) 157.4 1_565
C19 H19B O2 0.96 2.32 2.876(3) 116.5 .
C11 H11 O4 0.93 2.53 3.410(3) 157.4 1_565
C11 H11 O4 0.93 2.53 3.410(3) 157.4 1_565
C19 H19B O2 0.96 2.32 2.876(3) 116.5 .
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
C9 C1 C2 O1 -174.3(2) . . . . ?
C9 C1 C2 C3 4.9(2) . . . . ?
O1 C2 C3 C8 176.1(2) . . . . ?
C1 C2 C3 C8 -3.1(3) . . . . ?
O1 C2 C3 C4 -4.0(4) . . . . ?
C1 C2 C3 C4 176.8(2) . . . . ?
C8 C3 C4 C5 0.4(3) . . . . ?
C2 C3 C4 C5 -179.5(2) . . . . ?
C20 O2 C5 C4 0.4(4) . . . . ?
C20 O2 C5 C6 178.6(2) . . . . ?
C3 C4 C5 O2 177.2(2) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C19 O3 C6 C7 -119.9(2) . . . . ?
C19 O3 C6 C5 65.3(3) . . . . ?
O2 C5 C6 O3 -2.3(3) . . . . ?
C4 C5 C6 O3 175.9(2) . . . . ?
O2 C5 C6 C7 -177.0(2) . . . . ?
C4 C5 C6 C7 1.2(3) . . . . ?
C18 O4 C7 C6 54.3(3) . . . . ?
C18 O4 C7 C8 -129.7(2) . . . . ?
O3 C6 C7 O4 0.2(3) . . . . ?
C5 C6 C7 O4 175.0(2) . . . . ?
O3 C6 C7 C8 -175.78(19) . . . . ?
C5 C6 C7 C8 -1.0(3) . . . . ?
C4 C3 C8 C7 -0.2(3) . . . . ?
C2 C3 C8 C7 179.68(19) . . . . ?
C4 C3 C8 C9 180.0(2) . . . . ?
C2 C3 C8 C9 -0.1(2) . . . . ?
O4 C7 C8 C3 -175.69(18) . . . . ?
C6 C7 C8 C3 0.5(3) . . . . ?
O4 C7 C8 C9 4.0(3) . . . . ?
C6 C7 C8 C9 -179.75(19) . . . . ?
C3 C8 C9 C10 -119.7(2) . . . . ?
C7 C8 C9 C10 60.5(3) . . . . ?
C3 C8 C9 C1 3.1(2) . . . . ?
C7 C8 C9 C1 -176.7(2) . . . . ?
C2 C1 C9 C8 -4.7(2) . . . . ?
C2 C1 C9 C10 120.5(2) . . . . ?
C8 C9 C10 C15 -168.4(2) . . . . ?
C1 C9 C10 C15 73.8(3) . . . . ?
C8 C9 C10 C11 12.4(3) . . . . ?
C1 C9 C10 C11 -105.4(2) . . . . ?
C15 C10 C11 C12 1.4(3) . . . . ?
C9 C10 C11 C12 -179.4(2) . . . . ?
C10 C11 C12 F1 179.5(2) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C16 O5 C13 C14 6.9(4) . . . . ?
C16 O5 C13 C12 -173.1(2) . . . . ?
F1 C12 C13 O5 -1.4(3) . . . . ?
C11 C12 C13 O5 178.4(2) . . . . ?
F1 C12 C13 C14 178.6(2) . . . . ?
C11 C12 C13 C14 -1.6(4) . . . . ?
O5 C13 C14 C15 -177.7(3) . . . . ?
C12 C13 C14 C15 2.3(4) . . . . ?
C13 C14 C15 C10 -1.2(4) . . . . ?
C11 C10 C15 C14 -0.7(4) . . . . ?
C9 C10 C15 C14 -179.9(2) . . . . ?
C13 O5 C16 C17 173.2(2) . . . . ?
