#------------------------------------------------------------------------------
#$Date: 2023-06-06 05:21:56 +0300 (Tue, 06 Jun 2023) $
#$Revision: 284361 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/92/1569285.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_1569285
loop_
_publ_author_name
'Yu, Xiang'
'Xi, Yinkai'
'Sui, Yi'
'Liu, Yang'
'Chen, Guifen'
'Zhang, Minjie'
'Zhang, Yan'
'Luo, Guoyong'
'Long, Yi'
'Yang, Wude'
_publ_section_title
;
 Hydroxide-Mediated SNAr Rearrangement for Synthesis of Novel Depside
 Derivatives Containing Diaryl Ether Skeleton as Antitumor Agents
;
_journal_issue                   11
_journal_name_full               Molecules
_journal_page_first              4303
_journal_paper_doi               10.3390/molecules28114303
_journal_volume                  28
_journal_year                    2023
_chemical_formula_moiety         'C22 H26 O7'
_chemical_formula_sum            'C22 H26 O7'
_chemical_formula_weight         402.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-03-13
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                107.789(6)
_cell_angle_beta                 103.545(6)
_cell_angle_gamma                102.577(6)
_cell_formula_units_Z            2
_cell_length_a                   7.6363(16)
_cell_length_b                   11.878(3)
_cell_length_c                   13.501(3)
_cell_measurement_reflns_used    4720
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.19
_cell_measurement_theta_min      2.89
_cell_volume                     1076.8(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0662
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22524
_diffrn_reflns_theta_full        28.37
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         2.89
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         5337
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1641
_refine_ls_R_factor_gt           0.0789
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1348P)²+0.2573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2165
_refine_ls_wR_factor_ref         0.2722
_reflns_number_gt                2491
_reflns_number_total             5337
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            3d.cif
_cod_data_source_block           a
_cod_original_cell_volume        1076.9(4)
_cod_database_code               1569285
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C20 C 1.1872(7) 0.5377(5) 0.8990(5) 0.1155(18) Uani 1 1 d DU . .
H20A H 1.1756 0.5387 0.9693 0.139 Uiso 0.744(10) 1 calc PR A 1
H20B H 1.2929 0.6086 0.9118 0.139 Uiso 0.744(10) 1 calc PR A 1
H20C H 1.2510 0.6210 0.9542 0.139 Uiso 0.256(10) 1 calc PR A 2
H20D H 1.1517 0.4842 0.9376 0.139 Uiso 0.256(10) 1 calc PR A 2
O3 O 0.5059(3) 0.69603(19) 0.75629(16) 0.0528(6) Uani 1 1 d . . .
O6 O 1.0164(4) 0.5403(3) 0.8308(2) 0.0856(9) Uani 1 1 d . A .
O7 O 0.1333(3) 0.7360(3) 0.45064(19) 0.0738(7) Uani 1 1 d . . .
H7 H 0.1389 0.7600 0.4003 0.111 Uiso 1 1 calc R . .
O1 O 0.5966(4) 0.9000(3) 0.37922(18) 0.0735(7) Uani 1 1 d . . .
O4 O 0.5989(5) 0.9447(3) 0.8997(2) 0.0897(10) Uani 1 1 d . . .
H4 H 0.5359 0.9880 0.9226 0.135 Uiso 1 1 calc R . .
O2 O 0.2850(4) 0.8249(3) 0.3324(2) 0.0859(8) Uani 1 1 d . . .
O5 O 0.5841(5) 0.8962(3) 1.0419(2) 0.0946(10) Uani 1 1 d . . .
C5 C 0.5017(4) 0.7374(3) 0.6708(2) 0.0454(7) Uani 1 1 d . . .
C13 C 0.6807(4) 0.7063(3) 0.8257(2) 0.0472(7) Uani 1 1 d . . .
C7 C 0.6558(4) 0.8331(3) 0.5669(2) 0.0492(7) Uani 1 1 d . . .
C11 C 0.6372(5) 0.8851(3) 0.9610(2) 0.0504(8) Uani 1 1 d . . .
C12 C 0.7463(4) 0.7984(3) 0.9315(2) 0.0461(7) Uani 1 1 d . . .
C6 C 0.6645(4) 0.7935(3) 0.6535(2) 0.0503(7) Uani 1 1 d . . .
H6 H 0.7823 0.8047 0.7012 0.060 Uiso 1 1 calc R . .
C4 C 0.3215(4) 0.7191(3) 0.6046(2) 0.0510(7) Uani 1 1 d . . .
C3 C 0.3114(4) 0.7574(3) 0.5159(2) 0.0518(8) Uani 1 1 d . . .
C2 C 0.4741(4) 0.8137(3) 0.4943(2) 0.0493(7) Uani 1 1 d . . .
C17 C 0.9117(5) 0.8055(3) 1.0065(2) 0.0558(8) Uani 1 1 d . . .
C1 C 0.4412(5) 0.8457(3) 0.3958(2) 0.0549(8) Uani 1 1 d . . .
C14 C 0.7679(5) 0.6190(3) 0.7918(3) 0.0555(8) Uani 1 1 d . A .
C16 C 1.0071(5) 0.7205(4) 0.9720(3) 0.0647(9) Uani 1 1 d . A .
H16 H 1.1208 0.7258 1.0200 0.078 Uiso 1 1 calc R . .
C15 C 0.9348(5) 0.6286(3) 0.8676(3) 0.0613(9) Uani 1 1 d . . .
C8 C 0.8415(5) 0.8947(4) 0.5564(3) 0.0718(10) Uani 1 1 d . . .
H8A H 0.9444 0.8988 0.6154 0.108 Uiso 1 1 calc R . .
H8B H 0.8472 0.9774 0.5598 0.108 Uiso 1 1 calc R . .
H8C H 0.8511 0.8473 0.4873 0.108 Uiso 1 1 calc R . .
C18 C 0.6883(6) 0.5156(3) 0.6794(3) 0.0752(11) Uani 1 1 d . . .
H18A H 0.5561 0.5045 0.6485 0.113 Uiso 1 1 calc R A .
H18B H 0.7031 0.4397 0.6859 0.113 Uiso 1 1 calc R . .
H18C H 0.7551 0.5368 0.6323 0.113 Uiso 1 1 calc R . .
C9 C 0.1467(5) 0.6629(4) 0.6275(3) 0.0758(11) Uani 1 1 d . . .
H9A H 0.1364 0.5783 0.6192 0.114 Uiso 1 1 calc R . .
H9B H 0.0369 0.6648 0.5767 0.114 Uiso 1 1 calc R . .
H9C H 0.1550 0.7097 0.7013 0.114 Uiso 1 1 calc R . .
C19 C 0.9917(5) 0.9031(4) 1.1222(3) 0.0754(11) Uani 1 1 d . . .
H19A H 0.9956 0.9834 1.1195 0.113 Uiso 1 1 calc R . .
H19B H 1.1176 0.9038 1.1561 0.113 Uiso 1 1 calc R . .
H19C H 0.9125 0.8838 1.1643 0.113 Uiso 1 1 calc R . .
C10 C 0.5683(7) 0.9325(4) 0.2831(3) 0.0877(13) Uani 1 1 d . . .
H10A H 0.5080 0.8582 0.2182 0.132 Uiso 1 1 calc R . .
H10B H 0.6887 0.9755 0.2812 0.132 Uiso 1 1 calc R . .
H10C H 0.4894 0.9855 0.2863 0.132 Uiso 1 1 calc R . .
C21 C 1.2152(10) 0.4150(7) 0.8345(9) 0.142(4) Uani 0.744(10) 1 d PDU A 1
H21A H 1.1269 0.3473 0.8408 0.171 Uiso 0.744(10) 1 calc PR A 1
H21B H 1.1799 0.4040 0.7575 0.171 Uiso 0.744(10) 1 calc PR A 1
C22 C 1.3887(15) 0.4035(11) 0.8638(11) 0.206(6) Uani 0.744(10) 1 d PDU A 1
H22A H 1.3888 0.3248 0.8160 0.308 Uiso 0.744(10) 1 calc PR A 1
H22B H 1.4227 0.4077 0.9383 0.308 Uiso 0.744(10) 1 calc PR A 1
H22C H 1.4788 0.4696 0.8582 0.308 Uiso 0.744(10) 1 calc PR A 1
C1A C 1.278(2) 0.4042(17) 0.7654(15) 0.082(5) Uani 0.256(10) 1 d PDU A 2
H1AA H 1.1875 0.3352 0.7674 0.123 Uiso 0.256(10) 1 calc PR A 2
H1AB H 1.3901 0.3831 0.7596 0.123 Uiso 0.256(10) 1 calc PR A 2
H1AC H 1.2234 0.4231 0.7031 0.123 Uiso 0.256(10) 1 calc PR A 2
C1B C 1.320(3) 0.4996(19) 0.8540(18) 0.116(6) Uani 0.256(10) 1 d PDU A 2
H1BA H 1.3901 0.5701 0.8422 0.139 Uiso 0.256(10) 1 calc PR A 2
H1BB H 1.4083 0.4869 0.9108 0.139 Uiso 0.256(10) 1 calc PR A 2
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H20A C20 H20B 108.9 . . ?
H20A C20 H20C 70.8 . . ?
H20A C20 H20D 36.9 . . ?
H20B C20 H20C 43.0 . . ?
H20B C20 H20D 137.2 . . ?
H20C C20 H20D 106.8 . . ?
O6 C20 H20A 110.8 . . ?
O6 C20 H20B 110.8 . . ?
O6 C20 H20C 107.2 . . ?
O6 C20 H20D 107.2 . . ?
O6 C20 C21 104.8(5) . . ?
C21 C20 H20A 110.8 . . ?
C21 C20 H20B 110.8 . . ?
C21 C20 H20C 144.8 . . ?
C21 C20 H20D 76.9 . . ?
C1B C20 H20A 125.8 . . ?
C1B C20 H20B 69.1 . . ?
C1B C20 H20C 107.2 . . ?
C1B C20 H20D 107.2 . . ?
C1B C20 O6 120.4(10) . . ?
C1B C20 C21 41.7(9) . . ?
C5 O3 C13 119.0(2) . . ?
C15 O6 C20 121.1(3) . . ?
C3 O7 H7 109.5 . . ?
C1 O1 C10 116.2(3) . . ?
C11 O4 H4 109.5 . . ?
O3 C5 C6 122.7(3) . . ?
O3 C5 C4 114.5(3) . . ?
C4 C5 C6 122.8(3) . . ?
O3 C13 C12 117.0(2) . . ?
C14 C13 O3 119.0(3) . . ?
C14 C13 C12 123.7(3) . . ?
C6 C7 C2 118.3(3) . . ?
C6 C7 C8 117.1(3) . . ?
C2 C7 C8 124.6(3) . . ?
O4 C11 C12 117.8(2) . . ?
O5 C11 O4 122.0(3) . . ?
O5 C11 C12 120.1(3) . . ?
C13 C12 C11 119.3(3) . . ?
C17 C12 C13 119.1(3) . . ?
C17 C12 C11 121.6(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.4(3) . . ?
C7 C6 H6 119.3 . . ?
C5 C4 C3 116.2(3) . . ?
C5 C4 C9 122.0(3) . . ?
C3 C4 C9 121.8(3) . . ?
O7 C3 C4 115.1(3) . . ?
O7 C3 C2 122.0(3) . . ?
C4 C3 C2 122.9(3) . . ?
C7 C2 C1 124.8(3) . . ?
C3 C2 C7 118.5(3) . . ?
C3 C2 C1 116.7(3) . . ?
C12 C17 C16 118.1(3) . . ?
C12 C17 C19 122.0(3) . . ?
C16 C17 C19 119.9(3) . . ?
O1 C1 C2 115.1(3) . . ?
O2 C1 O1 120.8(3) . . ?
O2 C1 C2 124.1(3) . . ?
C13 C14 C15 116.4(3) . . ?
C13 C14 C18 122.8(3) . . ?
C15 C14 C18 120.8(3) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 C17 121.0(3) . . ?
C15 C16 H16 119.5 . . ?
O6 C15 C14 114.5(3) . . ?
O6 C15 C16 123.8(3) . . ?
C16 C15 C14 121.6(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C20 C21 H21A 107.9 . . ?
C20 C21 H21B 107.9 . . ?
H21A C21 H21B 107.2 . . ?
C22 C21 C20 117.5(8) . . ?
C22 C21 H21A 107.9 . . ?
C22 C21 H21B 107.9 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
C1B C1A H1AA 109.5 . . ?
C1B C1A H1AB 109.5 . . ?
C1B C1A H1AC 109.5 . . ?
C20 C1B H1BA 106.3 . . ?
C20 C1B H1BB 106.3 . . ?
C1A C1B C20 123.9(19) . . ?
C1A C1B H1BA 106.3 . . ?
C1A C1B H1BB 106.3 . . ?
H1BA C1B H1BB 106.4 . . ?
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
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C20 H20D 0.9700 . ?
C20 O6 1.422(5) . ?
C20 C21 1.541(8) . ?
C20 C1B 1.385(13) . ?
O3 C5 1.382(3) . ?
O3 C13 1.396(3) . ?
O6 C15 1.359(4) . ?
O7 H7 0.8200 . ?
O7 C3 1.357(3) . ?
O1 C1 1.324(4) . ?
O1 C10 1.446(4) . ?
O4 H4 0.8200 . ?
O4 C11 1.267(3) . ?
O2 C1 1.217(4) . ?
O5 C11 1.232(3) . ?
C5 C6 1.384(4) . ?
C5 C4 1.384(4) . ?
C13 C12 1.399(4) . ?
C13 C14 1.372(4) . ?
C7 C6 1.381(4) . ?
C7 C2 1.423(4) . ?
C7 C8 1.507(5) . ?
C11 C12 1.481(4) . ?
C12 C17 1.390(4) . ?
C6 H6 0.9300 . ?
C4 C3 1.397(4) . ?
C4 C9 1.502(5) . ?
C3 C2 1.414(4) . ?
C2 C1 1.474(4) . ?
C17 C16 1.399(4) . ?
C17 C19 1.515(5) . ?
C14 C15 1.393(5) . ?
C14 C18 1.512(5) . ?
C16 H16 0.9300 . ?
C16 C15 1.384(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.341(10) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C1A H1AA 0.9600 . ?
C1A H1AB 0.9600 . ?
C1A H1AC 0.9600 . ?
C1A C1B 1.284(15) . ?
C1B H1BA 0.9700 . ?
C1B H1BB 0.9700 . ?
