Experimental and theoretical study of bidirectional photoswitching behavior of 5,5′-diphenylhydantoin Schiff bases: synthesis, crystal structure and kinetic approaches
Todorov, Petar; Georgieva, Stela; Peneva, Petia; Rusew, Rusi; Shivachev, Boris; Georgiev, Anton; New Journal of Chemistry 44 (2020) 15081–15099; doi:10.1039/D0NJ03301D

data_7059932
_publ_section_title
;
 Experimental and theoretical study of bidirectional photoswitching
 behavior of 5,5&#x2032;-diphenylhydantoin Schiff bases: synthesis,
 crystal structure and kinetic approaches
;
_journal_issue                   35
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              15081
_journal_page_last               15099
_journal_paper_doi               10.1039/D0NJ03301D
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C22 H17 N3 O3'
_chemical_formula_sum            'C22 H17 N3 O3'
_chemical_formula_weight         371.38
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-06-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-06-23 deposited with the CCDC.	2020-08-03 downloaded from the CCDC.
;
_cell_angle_alpha                107.718(14)
_cell_angle_beta                 96.228(10)
_cell_angle_gamma                106.521(11)
_cell_formula_units_Z            2
_cell_length_a                   8.5374(8)
_cell_length_b                   10.4625(17)
_cell_length_c                   11.6521(17)
_cell_measurement_reflns_used    1733
_cell_measurement_temperature    290
_cell_measurement_theta_max      26.7520
_cell_measurement_theta_min      3.4490
_cell_volume                     928.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      290
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3974
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.803
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -14.00  82.00   1.00   90.00    --    7.68  38.00 -90.00   96
  2  \w    -17.00  78.00   1.00   90.00    --    7.68  77.00   0.00   95
  3  \w    -67.00  39.00   1.00   90.00    --    7.68 -77.00 120.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0755735000
_diffrn_orient_matrix_UB_12      -0.0015586000
_diffrn_orient_matrix_UB_13      0.0204553000
_diffrn_orient_matrix_UB_21      -0.0180163000
_diffrn_orient_matrix_UB_22      0.0375648000
_diffrn_orient_matrix_UB_23      -0.0382671000
_diffrn_orient_matrix_UB_31      -0.0428101000
_diffrn_orient_matrix_UB_32      -0.0655187000
_diffrn_orient_matrix_UB_33      -0.0489501000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0886
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.803
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5865
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.803
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.560
_diffrn_reflns_theta_min         2.737
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         5865
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1352
_refine_ls_R_factor_gt           0.0618
_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/[\s^2^(Fo^2^)+(0.0896P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1746
_refine_ls_wR_factor_ref         0.1927
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2745
_reflns_number_total             5865
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 179.9778\% 
 around [-0.00 -0.71 0.71] (reciprocal) or [-0.21 -0.82 0.53] (direct)
;
_cod_data_source_file            d0nj03301d2.cif
_cod_data_source_block           exp_531_2_twin1_hklf4
_cod_depositor_comments
'Adding full bibliography for 7059930--7059932.cif.'
_cod_original_cell_volume        928.6(2)
_cod_database_code               7059932
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 N3 O2 H20'
_chemical_oxdiff_usercomment     'Petyia SB2 Ph'
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.982
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7129(16)
 0.2871(16)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 O16-H16
 1.01 with sigma of 0.002
4.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C5(H5), C9(H9), C8(H8), C7(H7), C9A(H9A), C5A(H5A), C12(H12),
 C13(H13), C6(H6), C8A(H8A), C15(H15), C14(H14), C6A(H6A), C7A(H7A)
;
_shelx_res_checksum              33089
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.418
_oxdiff_exptl_absorpt_empirical_full_min 0.750
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2