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#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/36/1503667.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_1503667
loop_
_publ_author_name
'Messaoudi, Samir'
'Tréguier, Bret'
'Hamze, Abdallah'
'Provot, Olivier'
'Peyrat, Jean-François'
'De Losada, Jordi Rodrigo'
'Liu, Jian-Miao'
'Bignon, Jérôme'
'Wdzieczak-Bakala, Joanna'
'Thoret, Sylviane'
'Dubois, Joëlle'
'Brion, Jean-Daniel'
'Alami, Mouâd'
_publ_section_title
;
 Isocombretastatins a versus combretastatins a: the forgotten isoCA-4
 isomer as a highly promising cytotoxic and antitubulin agent.
;
_journal_issue                   14
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              4538
_journal_page_last               4542
_journal_paper_doi               10.1021/jm900321u
_journal_volume                  52
_journal_year                    2009
_chemical_formula_sum            'C18 H20 O5'
_chemical_formula_weight         316.34
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00(5)
_cell_angle_beta                 104.00(5)
_cell_angle_gamma                90.00(5)
_cell_formula_units_Z            4
_cell_length_a                   10.8340(10)
_cell_length_b                   11.6230(10)
_cell_length_c                   13.5110(10)
_cell_measurement_temperature    293(2)
_cell_volume                     1650.8(4)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) COLLECT (Hooft, 1998)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997) COLLECT (Hooft, 1998)'
_computing_data_reduction        'HKL package (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 1980-2004)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .998
_diffrn_measured_fraction_theta_max .998
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6487
_diffrn_reflns_theta_full        26.34
_diffrn_reflns_theta_max         26.34
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.28
_refine_diff_density_max         .142
_refine_diff_density_min         -.154
_refine_diff_density_rms         .034
_refine_ls_extinction_coef       0.025(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3364
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0645P)²+0.2773P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1267
_reflns_number_gt                2371
_reflns_number_total             3364
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jm900321u_si_002.cif
_cod_data_source_block           shelxs97
_cod_original_cell_volume        1650.8(2)
_cod_original_sg_symbol_H-M      P21/C
_cod_database_code               1503667
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C3 C 1.23679(14) 0.22106(13) -0.03604(11) 0.0391(4) Uani 1 1 d .
O3 O 1.60339(11) 0.05685(12) 0.25946(9) 0.0611(4) Uani 1 1 d .
O4 O 1.80074(11) 0.20466(11) 0.27124(11) 0.0661(4) Uani 1 1 d .
C14 C 1.58059(14) 0.31040(15) 0.04035(14) 0.0475(4) Uani 1 1 d .
H14 H 1.5769 0.3691 -0.0071 0.057 Uiso 1 1 calc R
C6 C 0.99361(14) 0.17960(14) -0.00651(12) 0.0418(4) Uani 1 1 d .
C4 C 1.20206(14) 0.26262(14) 0.05014(12) 0.0426(4) Uani 1 1 d .
H4 H 1.2610 0.3037 0.0988 0.051 Uiso 1 1 calc R
C1 C 1.36340(14) 0.24662(14) -0.05478(12) 0.0421(4) Uani 1 1 d .
C10 C 1.48384(14) 0.15007(14) 0.10442(12) 0.0433(4) Uani 1 1 d .
H10 H 1.4150 0.1008 0.0998 0.052 Uiso 1 1 calc R
O2 O 1.05248(11) 0.28912(13) 0.14907(10) 0.0689(4) Uani 1 1 d .
H2 H 0.9790 0.2722 0.1491 0.103 Uiso 1 1 calc R
C8 C 1.14716(15) 0.15890(14) -0.10653(12) 0.0457(4) Uani 1 1 d .
H8 H 1.1681 0.1307 -0.1648 0.055 Uiso 1 1 calc R
C11 C 1.59157(14) 0.13704(15) 0.18387(12) 0.0451(4) Uani 1 1 d .
C9 C 1.47785(13) 0.23587(14) 0.03185(12) 0.0408(4) Uani 1 1 d .
C7 C 1.02673(15) 0.13795(14) -0.09165(12) 0.0466(4) Uani 1 1 d .
H7 H 0.9683 0.0955 -0.1396 0.056 Uiso 1 1 calc R
C5 C 1.08208(14) 0.24399(15) 0.06450(12) 0.0444(4) Uani 1 1 d .
C12 C 1.69504(14) 0.21029(15) 0.19132(13) 0.0468(4) Uani 1 1 d .
C2 C 1.3737(2) 0.27676(18) -0.14733(15) 0.0603(5) Uani 1 1 d .
H2A H 1.2990(19) 0.2866(17) -0.2029(16) 0.065(6) Uiso 1 1 d .
H2B H 1.4568(18) 0.2871(16) -0.1616(15) 0.066(6) Uiso 1 1 d .
C13 C 1.68798(14) 0.29732(14) 0.11910(14) 0.0484(4) Uani 1 1 d .
O1 O 0.87890(10) 0.16491(11) 0.01735(9) 0.0574(4) Uani 1 1 d .
C15 C 0.78355(15) 0.10007(16) -0.05059(14) 0.0555(5) Uani 1 1 d .
H15A H 0.7610 0.1378 -0.1157 0.083 Uiso 1 1 calc R
H15B H 0.7098 0.0941 -0.0233 0.083 Uiso 1 1 calc R
H15C H 0.8155 0.0245 -0.0587 0.083 Uiso 1 1 calc R
C16 C 1.50603(19) -0.02784(17) 0.24916(16) 0.0677(6) Uani 1 1 d .
H16A H 1.4269 0.0089 0.2498 0.102 Uiso 1 1 calc R
H16B H 1.5280 -0.0813 0.3048 0.102 Uiso 1 1 calc R
H16C H 1.4976 -0.0682 0.1859 0.102 Uiso 1 1 calc R
C17 C 1.87823(17) 0.10512(17) 0.27794(17) 0.0655(5) Uani 1 1 d .
H17A H 1.8359 0.0410 0.3000 0.098 Uiso 1 1 calc R
H17B H 1.9580 0.1184 0.3261 0.098 Uiso 1 1 calc R
H17C H 1.8932 0.0887 0.2122 0.098 Uiso 1 1 calc R
O5 O 1.79322(11) 0.36701(11) 0.13347(12) 0.0665(4) Uani 1 1 d .
C18 C 1.7932(2) 0.4521(2) 0.0568(2) 0.0973(9) Uani 1 1 d .
H18A H 1.7824 0.4152 -0.0083 0.146 Uiso 1 1 calc R
H18B H 1.8726 0.4929 0.0730 0.146 Uiso 1 1 calc R
H18C H 1.7246 0.5052 0.0544 0.146 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
C8 C3 C4 117.94(14)
C8 C3 C1 120.63(14)
C4 C3 C1 121.37(14)
C11 O3 C16 117.73(14)
C12 O4 C17 117.20(14)
C13 C14 C9 120.14(16)
C13 C14 H14 119.9
C9 C14 H14 119.9
O1 C6 C7 126.14(14)
O1 C6 C5 114.59(14)
C7 C6 C5 119.27(15)
C5 C4 C3 121.20(15)
C5 C4 H4 119.4
C3 C4 H4 119.4
C2 C1 C3 120.32(16)
C2 C1 C9 121.18(16)
C3 C1 C9 118.49(13)
C9 C10 C11 120.71(15)
C9 C10 H10 119.6
C11 C10 H10 119.6
C5 O2 H2 109.5
C3 C8 C7 121.20(15)
C3 C8 H8 119.4
C7 C8 H8 119.4
O3 C11 C10 124.15(15)
O3 C11 C12 115.80(15)
C10 C11 C12 120.03(16)
C10 C9 C14 119.23(15)
C10 C9 C1 120.17(14)
C14 C9 C1 120.60(15)
C6 C7 C8 120.29(15)
C6 C7 H7 119.9
C8 C7 H7 119.9
O2 C5 C4 118.61(14)
O2 C5 C6 121.31(14)
C4 C5 C6 120.08(15)
O4 C12 C11 122.13(17)
O4 C12 C13 118.63(15)
C11 C12 C13 119.09(15)
C1 C2 H2A 121.1(12)
C1 C2 H2B 120.7(12)
H2A C2 H2B 118.2(16)
O5 C13 C14 124.02(17)
O5 C13 C12 115.19(16)
C14 C13 C12 120.79(15)
C6 O1 C15 118.28(14)
O1 C15 H15A 109.5
O1 C15 H15B 109.5
H15A C15 H15B 109.5
O1 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
O3 C16 H16A 109.5
O3 C16 H16B 109.5
H16A C16 H16B 109.5
O3 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
O4 C17 H17A 109.5
O4 C17 H17B 109.5
H17A C17 H17B 109.5
O4 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C13 O5 C18 116.76(16)
O5 C18 H18A 109.5
O5 C18 H18B 109.5
H18A C18 H18B 109.5
O5 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C3 C8 1.387(2)
C3 C4 1.394(2)
C3 C1 1.484(2)
O3 C11 1.366(2)
O3 C16 1.425(2)
O4 C12 1.372(2)
O4 C17 1.419(2)
C14 C13 1.382(2)
C14 C9 1.393(2)
C14 H14 0.9300
C6 O1 1.3680(19)
C6 C7 1.373(2)
C6 C5 1.398(2)
C4 C5 1.377(2)
C4 H4 0.9300
C1 C2 1.329(3)
C1 C9 1.490(2)
C10 C9 1.389(2)
C10 C11 1.390(2)
C10 H10 0.9300
O2 C5 1.364(2)
O2 H2 0.8200
C8 C7 1.389(2)
C8 H8 0.9300
C11 C12 1.392(2)
C7 H7 0.9300
C12 C13 1.395(3)
C2 H2A 0.97(2)
C2 H2B 0.973(19)
C13 O5 1.373(2)
O1 C15 1.421(2)
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
O5 C18 1.432(3)
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
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
C8 C3 C4 C5 -0.8(2)
C1 C3 C4 C5 176.44(15)
C8 C3 C1 C2 40.9(2)
C4 C3 C1 C2 -136.31(18)
C8 C3 C1 C9 -138.19(16)
C4 C3 C1 C9 44.6(2)
C4 C3 C8 C7 -0.4(2)
C1 C3 C8 C7 -177.66(15)
C16 O3 C11 C10 8.3(2)
C16 O3 C11 C12 -173.33(15)
C9 C10 C11 O3 178.26(15)
C9 C10 C11 C12 -0.1(2)
C11 C10 C9 C14 -1.0(2)
C11 C10 C9 C1 178.09(14)
C13 C14 C9 C10 1.3(2)
C13 C14 C9 C1 -177.86(14)
C2 C1 C9 C10 -143.30(18)
C3 C1 C9 C10 35.8(2)
C2 C1 C9 C14 35.8(2)
C3 C1 C9 C14 -145.14(15)
O1 C6 C7 C8 -179.79(15)
C5 C6 C7 C8 0.5(2)
C3 C8 C7 C6 0.5(3)
C3 C4 C5 O2 -178.42(15)
C3 C4 C5 C6 1.9(3)
O1 C6 C5 O2 -1.1(2)
C7 C6 C5 O2 178.60(15)
O1 C6 C5 C4 178.58(15)
C7 C6 C5 C4 -1.7(2)
C17 O4 C12 C11 67.9(2)
C17 O4 C12 C13 -116.48(18)
O3 C11 C12 O4 -1.9(2)
C10 C11 C12 O4 176.54(14)
O3 C11 C12 C13 -177.53(15)
C10 C11 C12 C13 0.9(2)
C9 C14 C13 O5 -179.74(14)
C9 C14 C13 C12 -0.4(2)
O4 C12 C13 O5 2.9(2)
C11 C12 C13 O5 178.70(14)
O4 C12 C13 C14 -176.47(14)
C11 C12 C13 C14 -0.7(2)
C7 C6 O1 C15 0.5(2)
C5 C6 O1 C15 -179.76(15)
C14 C13 O5 C18 -5.0(3)
C12 C13 O5 C18 175.66(18)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 24709355 ChemSpider
2 24996163 PubChem
