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#$Date: 2023-10-06 02:52:28 +0300 (Fri, 06 Oct 2023) $
#$Revision: 286716 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/97/1569704.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_1569704
loop_
_publ_author_name
'Bolotova, Iumzhana A.'
'Ustyuzhanin, Alexander O.'
'Sergeeva, Ekaterina S.'
'Faizdrakhmanova, Anna A.'
'Hai, Yu'
'Stepanov, Andrey V.'
'Ushakov, Igor A.'
'Lyssenko, Konstantin A.'
'You, Lei'
'Lvov, Andrey G.'
_publ_section_title
;
 2,3-Diarylmaleate salts as a versatile class of diarylethenes with a full
 spectrum of photoactivity in water.
;
_journal_issue                   35
_journal_name_full               'Chemical science'
_journal_page_first              9553
_journal_page_last               9559
_journal_paper_doi               10.1039/d3sc02165c
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C19 H18 O5'
_chemical_formula_sum            'C19 H18 O5'
_chemical_formula_weight         326.33
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-04-11 deposited with the CCDC.	2023-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.677(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.538(2)
_cell_length_b                   10.289(2)
_cell_length_c                   16.613(4)
_cell_measurement_reflns_used    1661
_cell_measurement_temperature    139(2)
_cell_measurement_theta_max      28.12
_cell_measurement_theta_min      2.32
_cell_volume                     1624.9(6)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      139(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Quest with Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_av_unetI/netI     0.0808
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12180
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.330
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9622
_exptl_absorpt_correction_T_min  0.8238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3739
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0604
_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)+(0.0352P)²+0.8335P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1416
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2695
_reflns_number_total             3739
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc02165c2.cif
_cod_data_source_block           a_a_CCDC2
_cod_depositor_comments
'Adding full bibliography for 1569699--1569704.cif.'
_cod_original_cell_volume        1625.0(7)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1569704
_shelx_shelxl_version_number     2018/3
_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   0.987
_shelx_estimated_absorpt_t_max   0.992
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.99988(16) 0.73189(16) 0.70052(10) 0.0285(4) Uani 1 1 d . . . . .
O2 O 0.34641(17) 0.66336(18) 0.65676(10) 0.0329(4) Uani 1 1 d . . . . .
O3 O 0.27623(16) 0.55464(15) 0.54372(9) 0.0257(4) Uani 1 1 d . . . . .
O4 O 0.62731(17) 0.73695(17) 0.39185(10) 0.0342(4) Uani 1 1 d . . . . .
O5 O 0.51701(16) 0.92833(15) 0.39386(10) 0.0293(4) Uani 1 1 d . . . . .
C1 C 0.4601(2) 0.7037(2) 0.53697(13) 0.0221(5) Uani 1 1 d . . . . .
C2 C 0.4214(2) 0.7566(2) 0.46445(13) 0.0217(5) Uani 1 1 d . . . . .
C3 C 0.6048(2) 0.7120(2) 0.57656(12) 0.0204(4) Uani 1 1 d . . . . .
C4 C 0.6706(2) 0.6029(2) 0.61334(13) 0.0233(5) Uani 1 1 d . . . . .
H4A H 0.623172 0.521618 0.611352 0.028 Uiso 1 1 calc R U . . .
C5 C 0.8031(2) 0.6122(2) 0.65227(13) 0.0238(5) Uani 1 1 d . . . . .
H5A H 0.847947 0.537010 0.675465 0.029 Uiso 1 1 calc R U . . .
C6 C 0.8718(2) 0.7322(2) 0.65770(13) 0.0214(5) Uani 1 1 d . . . . .
C7 C 0.8078(2) 0.8414(2) 0.62251(13) 0.0229(5) Uani 1 1 d . . . . .
H7A H 0.853777 0.923310 0.626180 0.028 Uiso 1 1 calc R U . . .
C8 C 0.6759(2) 0.8294(2) 0.58198(13) 0.0237(5) Uani 1 1 d . . . . .
H8A H 0.632791 0.904022 0.557066 0.028 Uiso 1 1 calc R U . . .
C9 C 1.0729(2) 0.8530(2) 0.70937(15) 0.0315(6) Uani 1 1 d . . . . .
H9A H 1.163020 0.839850 0.741089 0.047 Uiso 1 1 calc R U . . .
H9B H 1.015880 0.915257 0.737165 0.047 Uiso 1 1 calc R U . . .
H9C H 1.090003 0.887005 0.655934 0.047 Uiso 1 1 calc R U . . .
C10 C 0.2749(2) 0.7730(2) 0.42821(13) 0.0214(4) Uani 1 1 d . . . . .
C11 C 0.1652(2) 0.8105(2) 0.47392(14) 0.0262(5) Uani 1 1 d . . . . .
H11A H 0.184009 0.828026 0.529904 0.031 Uiso 1 1 calc R U . . .
C12 C 0.0298(2) 0.8223(2) 0.43876(15) 0.0296(5) Uani 1 1 d . . . . .
H12A H -0.043836 0.846825 0.470854 0.036 Uiso 1 1 calc R U . . .
C13 C 0.0004(2) 0.7989(2) 0.35724(15) 0.0287(5) Uani 1 1 d . . . . .
H13A H -0.093205 0.806370 0.333301 0.034 Uiso 1 1 calc R U . . .
C14 C 0.1082(2) 0.7646(2) 0.31100(14) 0.0281(5) Uani 1 1 d . . . . .
H14A H 0.088999 0.749689 0.254747 0.034 Uiso 1 1 calc R U . . .
C15 C 0.2444(2) 0.7518(2) 0.34605(13) 0.0246(5) Uani 1 1 d . . . . .
H15A H 0.317755 0.728229 0.313508 0.029 Uiso 1 1 calc R U . . .
C16 C 0.3551(2) 0.6404(2) 0.58656(13) 0.0227(5) Uani 1 1 d . . . . .
C17 C 0.1643(2) 0.4948(2) 0.58352(16) 0.0315(5) Uani 1 1 d . . . . .
H17A H 0.113523 0.433667 0.546489 0.047 Uiso 1 1 calc R U . . .
H17B H 0.099307 0.562012 0.599623 0.047 Uiso 1 1 calc R U . . .
H17C H 0.203768 0.448121 0.631538 0.047 Uiso 1 1 calc R U . . .
C18 C 0.5350(2) 0.8036(2) 0.41369(13) 0.0212(5) Uani 1 1 d . . . . .
C19 C 0.6203(2) 0.9818(2) 0.34444(15) 0.0321(6) Uani 1 1 d . . . . .
H19A H 0.598721 1.073442 0.333182 0.048 Uiso 1 1 calc R U . . .
H19B H 0.618356 0.933587 0.293478 0.048 Uiso 1 1 calc R U . . .
H19C H 0.713946 0.974660 0.373056 0.048 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 C9 117.43(18) . . ?
C16 O3 C17 116.55(18) . . ?
C18 O5 C19 115.35(17) . . ?
C2 C1 C3 123.5(2) . . ?
C2 C1 C16 121.4(2) . . ?
C3 C1 C16 114.93(18) . . ?
C1 C2 C10 126.1(2) . . ?
C1 C2 C18 118.25(19) . . ?
C10 C2 C18 115.64(18) . . ?
C8 C3 C4 118.1(2) . . ?
C8 C3 C1 120.80(19) . . ?
C4 C3 C1 121.0(2) . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C4 C5 C6 120.0(2) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
O1 C6 C7 124.6(2) . . ?
O1 C6 C5 115.32(19) . . ?
C7 C6 C5 120.1(2) . . ?
C6 C7 C8 119.0(2) . . ?
C6 C7 H7A 120.5 . . ?
C8 C7 H7A 120.5 . . ?
C3 C8 C7 122.0(2) . . ?
C3 C8 H8A 119.0 . . ?
C7 C8 H8A 119.0 . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 118.1(2) . . ?
C15 C10 C2 119.71(19) . . ?
C11 C10 C2 122.2(2) . . ?
C12 C11 C10 120.8(2) . . ?
C12 C11 H11A 119.6 . . ?
C10 C11 H11A 119.6 . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
C14 C13 C12 119.3(2) . . ?
C14 C13 H13A 120.4 . . ?
C12 C13 H13A 120.4 . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14A 119.8 . . ?
C13 C14 H14A 119.8 . . ?
C14 C15 C10 120.8(2) . . ?
C14 C15 H15A 119.6 . . ?
C10 C15 H15A 119.6 . . ?
O2 C16 O3 124.8(2) . . ?
O2 C16 C1 123.5(2) . . ?
O3 C16 C1 111.68(18) . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 O5 124.1(2) . . ?
O4 C18 C2 124.6(2) . . ?
O5 C18 C2 111.31(17) . . ?
O5 C19 H19A 109.5 . . ?
O5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
O1 C6 1.362(3) . ?
O1 C9 1.430(3) . ?
O2 C16 1.199(3) . ?
O3 C16 1.328(3) . ?
O3 C17 1.439(3) . ?
O4 C18 1.196(3) . ?
O5 C18 1.333(3) . ?
O5 C19 1.442(3) . ?
C1 C2 1.346(3) . ?
C1 C3 1.482(3) . ?
C1 C16 1.497(3) . ?
C2 C10 1.485(3) . ?
C2 C18 1.506(3) . ?
C3 C8 1.385(3) . ?
C3 C4 1.402(3) . ?
C4 C5 1.375(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.397(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.386(3) . ?
C7 C8 1.383(3) . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.389(3) . ?
C10 C11 1.397(3) . ?
C11 C12 1.378(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.382(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.379(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.386(3) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
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
C3 C1 C2 C10 -168.2(2) . . . . ?
C16 C1 C2 C10 6.9(3) . . . . ?
C3 C1 C2 C18 12.3(3) . . . . ?
C16 C1 C2 C18 -172.55(19) . . . . ?
C2 C1 C3 C8 47.9(3) . . . . ?
C16 C1 C3 C8 -127.5(2) . . . . ?
C2 C1 C3 C4 -135.6(2) . . . . ?
C16 C1 C3 C4 49.0(3) . . . . ?
C8 C3 C4 C5 -1.2(3) . . . . ?
C1 C3 C4 C5 -177.9(2) . . . . ?
C3 C4 C5 C6 2.0(3) . . . . ?
C9 O1 C6 C7 -0.2(3) . . . . ?
C9 O1 C6 C5 -178.60(19) . . . . ?
C4 C5 C6 O1 177.22(19) . . . . ?
C4 C5 C6 C7 -1.3(3) . . . . ?
O1 C6 C7 C8 -178.62(19) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C4 C3 C8 C7 -0.3(3) . . . . ?
C1 C3 C8 C7 176.3(2) . . . . ?
C6 C7 C8 C3 1.1(3) . . . . ?
C1 C2 C10 C15 -140.8(2) . . . . ?
C18 C2 C10 C15 38.7(3) . . . . ?
C1 C2 C10 C11 39.8(3) . . . . ?
C18 C2 C10 C11 -140.7(2) . . . . ?
C15 C10 C11 C12 1.9(3) . . . . ?
C2 C10 C11 C12 -178.7(2) . . . . ?
C10 C11 C12 C13 -0.8(4) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C12 C13 C14 C15 1.0(4) . . . . ?
C13 C14 C15 C10 0.1(3) . . . . ?
C11 C10 C15 C14 -1.5(3) . . . . ?
C2 C10 C15 C14 179.1(2) . . . . ?
C17 O3 C16 O2 6.1(3) . . . . ?
C17 O3 C16 C1 -175.42(18) . . . . ?
C2 C1 C16 O2 -131.1(2) . . . . ?
C3 C1 C16 O2 44.4(3) . . . . ?
C2 C1 C16 O3 50.4(3) . . . . ?
C3 C1 C16 O3 -134.07(19) . . . . ?
C19 O5 C18 O4 -1.4(3) . . . . ?
C19 O5 C18 C2 -179.42(18) . . . . ?
C1 C2 C18 O4 58.0(3) . . . . ?
C10 C2 C18 O4 -121.5(2) . . . . ?
C1 C2 C18 O5 -124.0(2) . . . . ?
C10 C2 C18 O5 56.4(2) . . . . ?
