#------------------------------------------------------------------------------
#$Date: 2020-11-07 01:55:54 +0200 (Sat, 07 Nov 2020) $
#$Revision: 259025 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/22/2022250.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2022250
loop_
_publ_author_name
'Grześkiewicz, Anita M.'
'Stefański, Tomasz'
'Dutkiewicz, Zbigniew'
'Buśko, Daria'
'Kubicki, Maciej'
_publ_section_title
;
 Two new polymorphic forms of combretastatin A-4, an antitumour agent
;
_journal_coeditor_code           VP3009
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              958
_journal_page_last               964
_journal_paper_doi               10.1107/S205322962001236X
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C18 H20 O5'
_chemical_formula_sum            'C18 H20 O5'
_chemical_formula_weight         316.34
_chemical_name_common
;
Combretastatin A-4
;
_chemical_name_systematic
;
2-Methoxy-5-[(E)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_cell_angle_alpha                90
_cell_angle_beta                 96.988(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9167(5)
_cell_length_b                   6.9587(5)
_cell_length_c                   23.2803(15)
_cell_measurement_reflns_used    1286
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.1760
_cell_measurement_theta_min      3.8560
_cell_volume                     1594.58(17)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0338
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Xcalibur EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            5526
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.722
_diffrn_reflns_theta_min         3.418
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.166
_refine_ls_extinction_coef       0.0030(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3277
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0355P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.1075
_reflns_number_gt                1952
_reflns_number_total             3277
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vp3009sup1.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 2022250--2022251.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2022250
_cod_database_fobs_code          2022250
_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.64520(19) 0.5250(3) 0.66822(8) 0.0417(5) Uani d 1 . .
C C2 0.6923(2) 0.3847(3) 0.63298(8) 0.0447(5) Uani d 1 . .
H H2 0.6367(19) 0.280(3) 0.6220(7) 0.046(6) Uiso d 1 . .
C C3 0.8193(2) 0.4025(3) 0.61426(8) 0.0444(5) Uani d 1 . .
O O3 0.87314(15) 0.2769(2) 0.57784(6) 0.0630(4) Uani d 1 . .
C C31 0.7950(3) 0.1154(4) 0.55791(13) 0.0676(7) Uani d 1 . .
H H31A 0.851(3) 0.051(4) 0.5314(10) 0.089(8) Uiso d 1 . .
H H31B 0.708(3) 0.155(3) 0.5380(10) 0.084(9) Uiso d 1 . .
H H31C 0.779(2) 0.034(4) 0.5893(10) 0.084(9) Uiso d 1 . .
C C4 0.90185(19) 0.5578(3) 0.63217(8) 0.0417(5) Uani d 1 . .
O O4 1.03300(13) 0.5646(2) 0.61755(6) 0.0521(4) Uani d 1 . .
C C41 1.0506(3) 0.6887(4) 0.57004(12) 0.0637(7) Uani d 1 . .
H H41A 0.994(3) 0.652(4) 0.5350(11) 0.104(10) Uiso d 1 . .
H H41B 1.144(3) 0.681(4) 0.5616(11) 0.109(10) Uiso d 1 . .
H H41C 1.032(2) 0.829(4) 0.5808(10) 0.092(9) Uiso d 1 . .
C C5 0.85588(19) 0.6977(3) 0.66787(8) 0.0408(5) Uani d 1 . .
O O5 0.94493(13) 0.8433(2) 0.68289(6) 0.0518(4) Uani d 1 . .
C C51 0.9053(3) 0.9916(4) 0.71985(11) 0.0559(6) Uani d 1 . .
H H51A 0.818(3) 1.057(3) 0.7021(10) 0.089(8) Uiso d 1 . .
H H51B 0.983(2) 1.080(3) 0.7234(9) 0.075(7) Uiso d 1 . .
H H51C 0.890(2) 0.939(3) 0.7587(9) 0.073(7) Uiso d 1 . .
C C6 0.7269(2) 0.6821(3) 0.68547(8) 0.0429(5) Uani d 1 . .
H H6 0.6927(19) 0.786(3) 0.7105(8) 0.059(6) Uiso d 1 . .
C C7 0.5106(2) 0.5001(3) 0.68909(9) 0.0492(5) Uani d 1 . .
H H7 0.500(2) 0.373(3) 0.7085(8) 0.060(6) Uiso d 1 . .
C C8 0.4057(2) 0.6211(3) 0.68502(9) 0.0487(5) Uani d 1 . .
H H8 0.326(2) 0.585(3) 0.7048(8) 0.057(6) Uiso d 1 . .
C C9 0.38408(18) 0.8059(3) 0.65414(8) 0.0409(5) Uani d 1 . .
C C10 0.2861(2) 0.9306(3) 0.67065(8) 0.0446(5) Uani d 1 . .
H H10 0.2391(18) 0.902(3) 0.7030(7) 0.046(5) Uiso d 1 . .
C C11 0.25260(19) 1.1000(3) 0.64108(8) 0.0439(5) Uani d 1 . .
O O11 0.15689(16) 1.2179(2) 0.65950(7) 0.0642(5) Uani d 1 . .
H H11 0.140(3) 1.323(4) 0.6358(10) 0.101(10) Uiso d 1 . .
C C12 0.31594(19) 1.1449(3) 0.59253(8) 0.0424(5) Uani d 1 . .
O O12 0.27104(14) 1.3122(2) 0.56505(6) 0.0598(4) Uani d 1 . .
C C121 0.3414(3) 1.3783(5) 0.51988(12) 0.0691(8) Uani d 1 . .
H H12A 0.331(3) 1.278(4) 0.4871(11) 0.101(10) Uiso d 1 . .
H H12B 0.440(3) 1.401(4) 0.5346(11) 0.109(10) Uiso d 1 . .
H H12C 0.301(2) 1.501(4) 0.5090(9) 0.083(8) Uiso d 1 . .
C C13 0.4142(2) 1.0231(3) 0.57612(8) 0.0464(5) Uani d 1 . .
H H13 0.4551(18) 1.055(3) 0.5417(7) 0.053(6) Uiso d 1 . .
C C14 0.4478(2) 0.8562(3) 0.60633(8) 0.0459(5) Uani d 1 . .
H H14 0.513(2) 0.774(3) 0.5935(8) 0.052(6) Uiso d 1 . .
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 119.73(19) ?
C6 C1 C7 . . 120.83(18) ?
C2 C1 C7 . . 119.38(19) ?
C3 C2 C1 . . 120.3(2) ?
C3 C2 H2 . . 120.9(12) ?
C1 C2 H2 . . 118.8(12) ?
O3 C3 C2 . . 125.01(19) ?
O3 C3 C4 . . 115.01(18) ?
C2 C3 C4 . . 119.98(19) ?
C3 O3 C31 . . 118.2(2) ?
O3 C31 H31A . . 104.0(15) ?
O3 C31 H31B . . 110.6(15) ?
H31A C31 H31B . . 111(2) ?
O3 C31 H31C . . 111.0(15) ?
H31A C31 H31C . . 111(2) ?
H31B C31 H31C . . 108(2) ?
O4 C4 C3 . . 119.29(17) ?
O4 C4 C5 . . 120.57(18) ?
C3 C4 C5 . . 119.98(18) ?
C4 O4 C41 . . 114.67(17) ?
O4 C41 H41A . . 112.3(16) ?
O4 C41 H41B . . 109.5(16) ?
H41A C41 H41B . . 107(2) ?
O4 C41 H41C . . 110.1(13) ?
H41A C41 H41C . . 111(2) ?
H41B C41 H41C . . 107(2) ?
O5 C5 C4 . . 115.11(17) ?
O5 C5 C6 . . 124.91(18) ?
C4 C5 C6 . . 119.98(19) ?
C5 O5 C51 . . 118.36(17) ?
O5 C51 H51A . . 111.1(13) ?
O5 C51 H51B . . 103.6(13) ?
H51A C51 H51B . . 111.9(19) ?
O5 C51 H51C . . 111.0(13) ?
H51A C51 H51C . . 108.5(19) ?
H51B C51 H51C . . 110.7(17) ?
C1 C6 C5 . . 119.97(19) ?
C1 C6 H6 . . 120.2(11) ?
C5 C6 H6 . . 119.8(11) ?
C8 C7 C1 . . 128.9(2) ?
C8 C7 H7 . . 117.6(12) ?
C1 C7 H7 . . 113.5(12) ?
C7 C8 C9 . . 130.6(2) ?
C7 C8 H8 . . 117.8(12) ?
C9 C8 H8 . . 111.6(11) ?
C14 C9 C10 . . 117.71(19) ?
C14 C9 C8 . . 123.79(19) ?
C10 C9 C8 . . 118.28(18) ?
C11 C10 C9 . . 121.79(19) ?
C11 C10 H10 . . 117.2(11) ?
C9 C10 H10 . . 121.0(11) ?
O11 C11 C10 . . 119.34(18) ?
O11 C11 C12 . . 121.36(19) ?
C10 C11 C12 . . 119.29(19) ?
C11 O11 H11 . . 112.0(17) ?
O12 C12 C13 . . 126.18(18) ?
O12 C12 C11 . . 114.47(17) ?
C13 C12 C11 . . 119.35(19) ?
C12 O12 C121 . . 117.51(18) ?
O12 C121 H12A . . 108.4(15) ?
O12 C121 H12B . . 110.2(15) ?
H12A C121 H12B . . 111(2) ?
O12 C121 H12C . . 104.8(14) ?
H12A C121 H12C . . 113.9(19) ?
H12B C121 H12C . . 108(2) ?
C14 C13 C12 . . 120.7(2) ?
C14 C13 H13 . . 121.0(11) ?
C12 C13 H13 . . 118.2(11) ?
C13 C14 C9 . . 121.1(2) ?
C13 C14 H14 . . 119.1(12) ?
C9 C14 H14 . . 119.8(12) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.391(3) ?
C1 C2 . 1.392(3) ?
C1 C7 . 1.485(3) ?
C2 C3 . 1.388(3) ?
C2 H2 . 0.933(19) ?
C3 O3 . 1.370(2) ?
C3 C4 . 1.388(3) ?
O3 C31 . 1.411(3) ?
C31 H31A . 0.99(3) ?
C31 H31B . 0.96(2) ?
C31 H31C . 0.95(2) ?
C4 O4 . 1.385(2) ?
C4 C5 . 1.392(3) ?
O4 C41 . 1.431(3) ?
C41 H41A . 0.97(3) ?
C41 H41B . 0.97(3) ?
C41 H41C . 1.03(3) ?
C5 O5 . 1.361(2) ?
C5 C6 . 1.394(3) ?
O5 C51 . 1.429(2) ?
C51 H51A . 1.02(2) ?
C51 H51B . 0.98(2) ?
C51 H51C . 1.00(2) ?
C6 H6 . 1.01(2) ?
C7 C8 . 1.332(3) ?
C7 H7 . 1.01(2) ?
C8 C9 . 1.477(3) ?
C8 H8 . 0.99(2) ?
C9 C14 . 1.390(3) ?
C9 C10 . 1.391(3) ?
C10 C11 . 1.385(3) ?
C10 H10 . 0.954(18) ?
C11 O11 . 1.363(2) ?
C11 C12 . 1.394(3) ?
O11 H11 . 0.92(3) ?
C12 O12 . 1.376(2) ?
C12 C13 . 1.380(3) ?
O12 C121 . 1.408(3) ?
C121 H12A . 1.03(3) ?
C121 H12B . 1.01(3) ?
C121 H12C . 0.97(3) ?
C13 C14 . 1.377(3) ?
C13 H13 . 0.966(18) ?
C14 H14 . 0.94(2) ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -1.0(3) ?
C7 C1 C2 C3 . . . . -178.28(18) ?
C1 C2 C3 O3 . . . . -177.42(17) ?
C1 C2 C3 C4 . . . . 2.0(3) ?
C2 C3 O3 C31 . . . . -0.6(3) ?
C4 C3 O3 C31 . . . . 179.9(2) ?
O3 C3 C4 O4 . . . . -6.4(2) ?
C2 C3 C4 O4 . . . . 174.08(16) ?
O3 C3 C4 C5 . . . . 178.08(16) ?
C2 C3 C4 C5 . . . . -1.4(3) ?
C3 C4 O4 C41 . . . . 101.4(2) ?
C5 C4 O4 C41 . . . . -83.1(2) ?
O4 C4 C5 O5 . . . . 4.4(2) ?
C3 C4 C5 O5 . . . . 179.88(16) ?
O4 C4 C5 C6 . . . . -175.62(16) ?
C3 C4 C5 C6 . . . . -0.2(3) ?
C4 C5 O5 C51 . . . . -179.52(18) ?
C6 C5 O5 C51 . . . . 0.5(3) ?
C2 C1 C6 C5 . . . . -0.6(3) ?
C7 C1 C6 C5 . . . . 176.64(18) ?
O5 C5 C6 C1 . . . . -178.89(16) ?
C4 C5 C6 C1 . . . . 1.2(3) ?
C6 C1 C7 C8 . . . . 55.8(3) ?
C2 C1 C7 C8 . . . . -127.0(2) ?
C1 C7 C8 C9 . . . . 6.9(4) ?
C7 C8 C9 C14 . . . . 24.8(3) ?
C7 C8 C9 C10 . . . . -160.8(2) ?
C14 C9 C10 C11 . . . . -0.3(3) ?
C8 C9 C10 C11 . . . . -175.11(18) ?
C9 C10 C11 O11 . . . . -179.29(18) ?
C9 C10 C11 C12 . . . . 1.7(3) ?
O11 C11 C12 O12 . . . . -1.6(3) ?
C10 C11 C12 O12 . . . . 177.38(17) ?
O11 C11 C12 C13 . . . . 178.74(18) ?
C10 C11 C12 C13 . . . . -2.3(3) ?
C13 C12 O12 C121 . . . . -7.7(3) ?
C11 C12 O12 C121 . . . . 172.7(2) ?
O12 C12 C13 C14 . . . . -178.10(18) ?
C11 C12 C13 C14 . . . . 1.6(3) ?
C12 C13 C14 C9 . . . . -0.2(3) ?
C10 C9 C14 C13 . . . . -0.5(3) ?
C8 C9 C14 C13 . . . . 174.00(18) ?
