#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/22/7122246.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_7122246
loop_
_publ_author_name
'Maguire, Casey J.'
'Chen, Zhi'
'Mocharla, Vani P.'
'Sriram, Madhavi'
'Strecker, Tracy E.'
'Hamel, Ernest'
'Zhou, Heling'
'Lopez, Ramona'
'Wang, Yifan'
'Mason, Ralph P.'
'Chaplin, David J.'
'Trawick, Mary Lynn'
'Pinney, Kevin G.'
_publ_section_title
;
 Synthesis of dihydronaphthalene analogues inspired by combretastatin A-4
 and their biological evaluation as anticancer agents.
;
_journal_issue                   10
_journal_name_full               MedChemComm
_journal_page_first              1649
_journal_page_last               1662
_journal_paper_doi               10.1039/c8md00322j
_journal_volume                  9
_journal_year                    2018
_chemical_formula_sum            'C20 H22 O5'
_chemical_formula_weight         342.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2018-05-10 deposited with the CCDC.
2018-08-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.1342(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1996(5)
_cell_length_b                   6.7253(2)
_cell_length_c                   20.3499(9)
_cell_measurement_reflns_used    9845
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      3.19
_cell_volume                     1665.28(11)
_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-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            29603
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.360
_diffrn_reflns_theta_min         3.191
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.187
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.671
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         4152
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.671
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0557P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1366
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3406
_reflns_number_total             4152
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8md00322j2.cif
_cod_data_source_block           KP90
_cod_depositor_comments
'Adding full bibliography for 7122245--7122246.cif.'
_cod_database_code               7122246
_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   0.960
_shelx_estimated_absorpt_t_max   0.982
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.03387(8) 1.14021(14) -0.17670(5) 0.0259(2) Uani 1 1 d . .
H1 H 0.0158(14) 1.092(2) -0.2170(10) 0.049(5) Uiso 1 1 d . .
O2 O 0.11915(8) 0.82738(14) -0.23449(4) 0.0280(2) Uani 1 1 d . .
O3 O 0.56131(7) 0.60228(12) 0.09235(5) 0.0231(2) Uani 1 1 d . .
O4 O 0.46634(7) 0.39069(12) 0.18516(4) 0.0209(2) Uani 1 1 d . .
O5 O 0.25621(7) 0.44354(14) 0.20816(4) 0.0260(2) Uani 1 1 d . .
C1 C 0.10043(9) 1.01370(17) -0.13910(6) 0.0187(3) Uani 1 1 d . .
C2 C 0.14635(10) 0.84649(18) -0.16833(6) 0.0218(3) Uani 1 1 d . .
C3 C 0.21304(11) 0.71906(19) -0.13054(7) 0.0259(3) Uani 1 1 d . .
H3 H 0.2441 0.6057 -0.1499 0.031 Uiso 1 1 calc R U
C4 C 0.23437(11) 0.75817(18) -0.06377(6) 0.0230(3) Uani 1 1 d . .
H4 H 0.2796 0.6692 -0.0377 0.028 Uiso 1 1 calc R U
C5 C 0.19111(9) 0.92427(16) -0.03419(6) 0.0172(3) Uani 1 1 d . .
C6 C 0.12253(9) 1.05450(17) -0.07276(6) 0.0177(3) Uani 1 1 d . .
C7 C 0.06944(11) 1.23243(19) -0.04287(7) 0.0275(3) Uani 1 1 d . .
H7A H -0.0110 1.2104 -0.0456 0.033 Uiso 1 1 calc R U
H7B H 0.0834 1.3501 -0.0703 0.033 Uiso 1 1 calc R U
C8 C 0.10613(12) 1.28144(19) 0.02788(7) 0.0280(3) Uani 1 1 d . .
H8A H 0.1492 1.4062 0.0283 0.034 Uiso 1 1 calc R U
H8B H 0.0399 1.3075 0.0519 0.034 Uiso 1 1 calc R U
C9 C 0.17335(10) 1.12740(18) 0.06492(6) 0.0218(3) Uani 1 1 d . .
H9 H 0.1882 1.1452 0.1110 0.026 Uiso 1 1 calc R U
C10 C 0.21394(9) 0.96555(17) 0.03703(6) 0.0181(3) Uani 1 1 d . .
C11 C 0.28183(10) 0.81749(17) 0.07755(6) 0.0179(3) Uani 1 1 d . .
C12 C 0.39149(10) 0.78640(17) 0.06513(6) 0.0191(3) Uani 1 1 d . .
H12 H 0.4239 0.8618 0.0322 0.023 Uiso 1 1 calc R U
C13 C 0.45323(10) 0.64472(17) 0.10116(6) 0.0182(3) Uani 1 1 d . .
C14 C 0.40559(9) 0.53213(17) 0.14917(6) 0.0177(3) Uani 1 1 d . .
C15 C 0.29602(10) 0.56355(17) 0.16137(6) 0.0188(3) Uani 1 1 d . .
C16 C 0.23467(10) 0.70893(18) 0.12613(6) 0.0194(3) Uani 1 1 d . .
H16 H 0.1607 0.7334 0.1355 0.023 Uiso 1 1 calc R U
C17 C 0.17371(13) 0.6739(2) -0.26762(7) 0.0340(4) Uani 1 1 d . .
H17A H 0.2534 0.6898 -0.2596 0.051 Uiso 1 1 calc R U
H17B H 0.1536 0.6820 -0.3150 0.051 Uiso 1 1 calc R U
H17C H 0.1517 0.5441 -0.2510 0.051 Uiso 1 1 calc R U
C18 C 0.61370(11) 0.7191(2) 0.04545(7) 0.0290(3) Uani 1 1 d . .
H18A H 0.5785 0.6947 0.0014 0.044 Uiso 1 1 calc R U
H18B H 0.6916 0.6827 0.0462 0.044 Uiso 1 1 calc R U
H18C H 0.6071 0.8602 0.0564 0.044 Uiso 1 1 calc R U
C19 C 0.47978(11) 0.21105(18) 0.14903(6) 0.0261(3) Uani 1 1 d . .
H19A H 0.4075 0.1601 0.1329 0.039 Uiso 1 1 calc R U
H19B H 0.5174 0.1119 0.1778 0.039 Uiso 1 1 calc R U
H19C H 0.5236 0.2380 0.1115 0.039 Uiso 1 1 calc R U
C20 C 0.14383(11) 0.4734(2) 0.22187(7) 0.0336(4) Uani 1 1 d . .
H20A H 0.1335 0.6112 0.2358 0.050 Uiso 1 1 calc R U
H20B H 0.1251 0.3830 0.2571 0.050 Uiso 1 1 calc R U
H20C H 0.0961 0.4463 0.1821 0.050 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 0.0033 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
C2 O2 C17 116.43(10)
C13 O3 C18 117.05(9)
C14 O4 C19 112.69(9)
C15 O5 C20 116.55(9)
O1 C1 C6 119.14(11)
O1 C1 C2 119.86(11)
C6 C1 C2 120.99(11)
O2 C2 C3 125.59(11)
O2 C2 C1 114.52(10)
C3 C2 C1 119.89(12)
C2 C3 C4 119.29(12)
C3 C4 C5 121.66(11)
C4 C5 C6 119.10(11)
C4 C5 C10 121.55(10)
C6 C5 C10 119.34(10)
C1 C6 C5 119.05(11)
C1 C6 C7 119.39(10)
C5 C6 C7 121.52(11)
C6 C7 C8 116.75(10)
C9 C8 C7 116.34(11)
C10 C9 C8 123.85(12)
C9 C10 C5 121.17(11)
C9 C10 C11 120.80(11)
C5 C10 C11 118.00(10)
C16 C11 C12 120.18(11)
C16 C11 C10 119.96(11)
C12 C11 C10 119.85(11)
C13 C12 C11 119.83(11)
O3 C13 C12 124.21(11)
O3 C13 C14 115.52(10)
C12 C13 C14 120.26(11)
O4 C14 C15 119.63(11)
O4 C14 C13 120.64(10)
C15 C14 C13 119.73(11)
O5 C15 C14 115.41(10)
O5 C15 C16 124.60(11)
C14 C15 C16 119.99(11)
C11 C16 C15 119.99(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3709(14)
O2 C2 1.3694(15)
O2 C17 1.4242(16)
O3 C13 1.3734(14)
O3 C18 1.4227(15)
O4 C14 1.3829(13)
O4 C19 1.4299(15)
O5 C15 1.3638(15)
O5 C20 1.4329(15)
C1 C6 1.3849(17)
C1 C2 1.4072(17)
C2 C3 1.3774(18)
C3 C4 1.3902(18)
C4 C5 1.3908(16)
C5 C6 1.4101(16)
C5 C10 1.4822(16)
C6 C7 1.5093(16)
C7 C8 1.5130(18)
C8 C9 1.4916(17)
C9 C10 1.3389(17)
C10 C11 1.5029(16)
C11 C16 1.3869(17)
C11 C12 1.3950(17)
C12 C13 1.3904(17)
C13 C14 1.3955(17)
C14 C15 1.3932(17)
C15 C16 1.3975(16)
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
O1 H1 O4 0.90(2) 2.04(2) 2.8794(13) 155.2(15) 4_575
O1 H1 O2 0.90(2) 2.222(17) 2.6587(13) 109.5(13) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 66556146
