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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/1/56/97/1569703.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_1569703
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 O4'
_chemical_formula_sum            'C19 H18 O4'
_chemical_formula_weight         310.33
_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                 104.03(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.583(8)
_cell_length_b                   7.649(6)
_cell_length_c                   20.107(14)
_cell_measurement_reflns_used    542
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      18.22
_cell_measurement_theta_min      2.22
_cell_volume                     1579(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.1686
_diffrn_reflns_av_unetI/netI     0.1840
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11685
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.005
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.6238
_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    1.305
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       0.019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3098
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1618
_refine_ls_R_factor_gt           0.0893
_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)+(0.0785P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2088
_refine_ls_wR_factor_ref         0.2582
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1559
_reflns_number_total             3098
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc02165c2.cif
_cod_data_source_block           a_a_CCDC1
_cod_depositor_comments
'Adding full bibliography for 1569699--1569704.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1569703
_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   0.981
_shelx_estimated_absorpt_t_max   0.990
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 0.6525(3) 0.1411(4) 0.44814(15) 0.0342(8) Uani 1 1 d . . . . .
C1 C 0.6772(4) 0.4520(6) 0.4415(2) 0.0296(11) Uani 1 1 d . . . . .
O2 O 0.6156(3) 0.3103(4) 0.53218(15) 0.0345(8) Uani 1 1 d . . . . .
C2 C 0.6180(4) 0.4858(6) 0.3756(2) 0.0307(11) Uani 1 1 d . . . . .
O3 O 0.7727(3) 0.6415(4) 0.32646(17) 0.0395(9) Uani 1 1 d . . . . .
C3 C 0.7769(4) 0.5614(6) 0.4875(2) 0.0292(11) Uani 1 1 d . . . . .
O4 O 0.5714(3) 0.7499(4) 0.31693(16) 0.0346(8) Uani 1 1 d . . . . .
C4 C 0.8746(4) 0.4851(6) 0.5384(2) 0.0330(11) Uani 1 1 d . . . . .
H4A H 0.876770 0.361618 0.543614 0.040 Uiso 1 1 calc R U . . .
C5 C 0.9679(4) 0.5851(6) 0.5813(2) 0.0338(11) Uani 1 1 d . . . . .
H5A H 1.032946 0.529462 0.615639 0.041 Uiso 1 1 calc R U . . .
C6 C 0.9689(4) 0.7656(7) 0.5753(2) 0.0333(11) Uani 1 1 d . . . . .
C7 C 0.8706(4) 0.8425(6) 0.5254(2) 0.0302(10) Uani 1 1 d . . . . .
H7A H 0.868991 0.966104 0.520575 0.036 Uiso 1 1 calc R U . . .
C8 C 0.7760(4) 0.7449(6) 0.4830(2) 0.0293(11) Uani 1 1 d . . . . .
H8A H 0.708912 0.801713 0.450092 0.035 Uiso 1 1 calc R U . . .
C9 C 1.0716(5) 0.8745(7) 0.6219(2) 0.0407(13) Uani 1 1 d . . . . .
H9A H 1.132480 0.797915 0.653321 0.061 Uiso 1 1 calc R U . . .
H9B H 1.030222 0.954374 0.648376 0.061 Uiso 1 1 calc R U . . .
H9C H 1.118973 0.942359 0.594431 0.061 Uiso 1 1 calc R U . . .
C10 C 0.5050(4) 0.3879(5) 0.3341(2) 0.0277(10) Uani 1 1 d . . . . .
C11 C 0.4983(5) 0.3450(6) 0.2657(2) 0.0324(11) Uani 1 1 d . . . . .
H11A H 0.568128 0.375511 0.245910 0.039 Uiso 1 1 calc R U . . .
C12 C 0.3913(5) 0.2587(6) 0.2269(3) 0.0369(12) Uani 1 1 d . . . . .
H12A H 0.388355 0.229088 0.180629 0.044 Uiso 1 1 calc R U . . .
C13 C 0.2885(5) 0.2152(6) 0.2547(3) 0.0362(12) Uani 1 1 d . . . . .
H13A H 0.214623 0.156845 0.227521 0.043 Uiso 1 1 calc R U . . .
C14 C 0.2931(5) 0.2566(6) 0.3222(3) 0.0363(12) Uani 1 1 d . . . . .
H14A H 0.222967 0.225081 0.341657 0.044 Uiso 1 1 calc R U . . .
C15 C 0.4002(4) 0.3444(6) 0.3614(2) 0.0318(11) Uani 1 1 d . . . . .
H15A H 0.402133 0.375105 0.407460 0.038 Uiso 1 1 calc R U . . .
C16 C 0.6456(4) 0.2819(6) 0.4727(2) 0.0292(11) Uani 1 1 d . . . . .
C17 C 0.5997(5) 0.1546(6) 0.5714(2) 0.0392(12) Uani 1 1 d . . . . .
H17A H 0.577448 0.189685 0.614075 0.059 Uiso 1 1 calc R U . . .
H17B H 0.681173 0.087988 0.582224 0.059 Uiso 1 1 calc R U . . .
H17C H 0.529690 0.081809 0.544293 0.059 Uiso 1 1 calc R U . . .
C18 C 0.6662(4) 0.6325(6) 0.3379(2) 0.0305(11) Uani 1 1 d . . . . .
C19 C 0.6051(5) 0.9040(6) 0.2827(3) 0.0423(13) Uani 1 1 d . . . . .
H19A H 0.528771 0.980428 0.269341 0.063 Uiso 1 1 calc R U . . .
H19B H 0.633145 0.868501 0.241656 0.063 Uiso 1 1 calc R U . . .
H19C H 0.675944 0.967061 0.313837 0.063 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
C2 C1 C3 126.7(4) . . ?
C2 C1 C16 118.4(4) . . ?
C3 C1 C16 114.9(4) . . ?
C16 O2 C17 115.9(4) . . ?
C1 C2 C10 125.1(4) . . ?
C1 C2 C18 120.2(4) . . ?
C10 C2 C18 114.6(4) . . ?
C4 C3 C8 117.2(4) . . ?
C4 C3 C1 120.7(4) . . ?
C8 C3 C1 122.0(4) . . ?
C18 O4 C19 116.3(4) . . ?
C5 C4 C3 121.3(5) . . ?
C5 C4 H4A 119.4 . . ?
C3 C4 H4A 119.4 . . ?
C4 C5 C6 121.3(4) . . ?
C4 C5 H5A 119.3 . . ?
C6 C5 H5A 119.3 . . ?
C5 C6 C7 117.7(4) . . ?
C5 C6 C9 121.2(4) . . ?
C7 C6 C9 121.2(5) . . ?
C8 C7 C6 121.7(4) . . ?
C8 C7 H7A 119.1 . . ?
C6 C7 H7A 119.1 . . ?
C7 C8 C3 120.8(4) . . ?
C7 C8 H8A 119.6 . . ?
C3 C8 H8A 119.6 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 118.4(4) . . ?
C15 C10 C2 120.6(4) . . ?
C11 C10 C2 120.9(4) . . ?
C12 C11 C10 120.6(4) . . ?
C12 C11 H11A 119.7 . . ?
C10 C11 H11A 119.7 . . ?
C11 C12 C13 120.4(5) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C12 C13 C14 120.0(5) . . ?
C12 C13 H13A 120.0 . . ?
C14 C13 H13A 120.0 . . ?
C13 C14 C15 119.9(5) . . ?
C13 C14 H14A 120.1 . . ?
C15 C14 H14A 120.1 . . ?
C14 C15 C10 120.7(4) . . ?
C14 C15 H15A 119.6 . . ?
C10 C15 H15A 119.6 . . ?
O1 C16 O2 124.9(4) . . ?
O1 C16 C1 124.0(4) . . ?
O2 C16 C1 111.0(4) . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C18 O4 124.5(4) . . ?
O3 C18 C2 125.6(4) . . ?
O4 C18 C2 109.8(4) . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O4 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 C16 1.195(5) . ?
C1 C2 1.346(6) . ?
C1 C3 1.482(6) . ?
C1 C16 1.517(6) . ?
O2 C16 1.327(5) . ?
O2 C17 1.460(6) . ?
C2 C10 1.484(6) . ?
C2 C18 1.511(6) . ?
O3 C18 1.206(5) . ?
C3 C4 1.395(6) . ?
C3 C8 1.406(6) . ?
O4 C18 1.335(5) . ?
O4 C19 1.453(5) . ?
C4 C5 1.374(6) . ?
C4 H4A 0.9500 . ?
C5 C6 1.386(7) . ?
C5 H5A 0.9500 . ?
C6 C7 1.389(6) . ?
C6 C9 1.503(6) . ?
C7 C8 1.369(6) . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.392(6) . ?
C10 C11 1.399(6) . ?
C11 C12 1.378(6) . ?
C11 H11A 0.9500 . ?
C12 C13 1.380(7) . ?
C12 H12A 0.9500 . ?
C13 C14 1.383(7) . ?
C13 H13A 0.9500 . ?
C14 C15 1.388(6) . ?
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 -170.4(4) . . . . ?
C16 C1 C2 C10 12.5(7) . . . . ?
C3 C1 C2 C18 10.0(7) . . . . ?
C16 C1 C2 C18 -167.1(4) . . . . ?
C2 C1 C3 C4 -147.8(5) . . . . ?
C16 C1 C3 C4 29.4(6) . . . . ?
C2 C1 C3 C8 33.6(7) . . . . ?
C16 C1 C3 C8 -149.2(4) . . . . ?
C8 C3 C4 C5 -1.6(6) . . . . ?
C1 C3 C4 C5 179.8(4) . . . . ?
C3 C4 C5 C6 -0.3(7) . . . . ?
C4 C5 C6 C7 1.3(6) . . . . ?
C4 C5 C6 C9 -179.6(4) . . . . ?
C5 C6 C7 C8 -0.4(6) . . . . ?
C9 C6 C7 C8 -179.5(4) . . . . ?
C6 C7 C8 C3 -1.5(7) . . . . ?
C4 C3 C8 C7 2.5(6) . . . . ?
C1 C3 C8 C7 -178.9(4) . . . . ?
C1 C2 C10 C15 44.5(7) . . . . ?
C18 C2 C10 C15 -135.9(4) . . . . ?
C1 C2 C10 C11 -138.7(5) . . . . ?
C18 C2 C10 C11 40.9(6) . . . . ?
C15 C10 C11 C12 -1.2(7) . . . . ?
C2 C10 C11 C12 -178.0(4) . . . . ?
C10 C11 C12 C13 0.7(7) . . . . ?
C11 C12 C13 C14 -0.6(7) . . . . ?
C12 C13 C14 C15 1.0(7) . . . . ?
C13 C14 C15 C10 -1.5(7) . . . . ?
C11 C10 C15 C14 1.5(7) . . . . ?
C2 C10 C15 C14 178.4(4) . . . . ?
C17 O2 C16 O1 4.7(7) . . . . ?
C17 O2 C16 C1 -172.4(4) . . . . ?
C2 C1 C16 O1 52.9(6) . . . . ?
C3 C1 C16 O1 -124.6(5) . . . . ?
C2 C1 C16 O2 -130.0(4) . . . . ?
C3 C1 C16 O2 52.5(5) . . . . ?
C19 O4 C18 O3 -4.8(7) . . . . ?
C19 O4 C18 C2 177.0(4) . . . . ?
C1 C2 C18 O3 62.1(7) . . . . ?
C10 C2 C18 O3 -117.6(5) . . . . ?
C1 C2 C18 O4 -119.8(5) . . . . ?
C10 C2 C18 O4 60.6(5) . . . . ?
