Azobisheteroarene photoswitches based on isoxazoles and pyrazoles: tunable photostationary states, thermal relaxation and sensitization under confinement.
Seyfried, Maximilian D.; Gemen, Julius; Wyszynski, Leonard; Giard, Carl L.; Daniliuc, Constantin G.; Schönhoff, Monika; Doltsinis, Nikos L.; Glorius, Frank; Ravoo, Bart Jan; Chemical science 16 (2025) 19448–19455; doi:10.1039/d5sc04412j

data_1575832
_publ_section_title
;
 Azobisheteroarene photoswitches based on isoxazoles and pyrazoles:
 tunable photostationary states, thermal relaxation and sensitization
 under confinement.
;
_journal_issue                   41
_journal_name_full               'Chemical science'
_journal_page_first              19448
_journal_page_last               19455
_journal_paper_doi               10.1039/d5sc04412j
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C9 H10 N4 O2'
_chemical_formula_sum            'C9 H10 N4 O2'
_chemical_formula_weight         206.21
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'Intrinsic Phasing'
_audit_creation_method
;
FinalCif 2024.9-0 by Daniel Kratzert, Freiburg 2025, 
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2025-06-11 deposited with the CCDC.	2025-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.9217(13)
_cell_length_b                   4.4554(2)
_cell_length_c                   10.4846(6)
_cell_measurement_reflns_used    5772
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.4755
_cell_measurement_theta_min      2.7505
_cell_measurement_wavelength     0.71073
_cell_volume                     977.32(9)
_computing_cell_refinement       'SAINT V8.41 (Bruker AXS LLC)'
_computing_data_collection       'Bruker Instrument Service v8.5.5.6'
_computing_data_reduction        'SAINT V8.41 (Bruker AXS LLC)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1503)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N2
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.391
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;<Phi   scan: start=   0.0; len= 180.0; end= 180.0 at [Counterclockwise Eulerian 
angles: dx= 42.20 mm theta=   0.000 deg omega= 359.849 deg chi=  54.740 deg] 
measure for 2.0 seconds; frame angle 1.00 degrees, wavelength=0.71073>
<Phi   scan: start= 180.0; len= 180.0; end= 360.0 at [Counterclockwise Eulerian 
angles: dx= 42.20 mm theta=   0.000 deg omega= 359.849 deg chi=  54.740 deg] 
measure for 2.0 seconds; frame angle 1.00 degrees, wavelength=0.71073>
<Phi   scan: start= 312.5; len= 142.8; end= 455.3 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=   3.062 deg omega=   7.853 deg chi= -46.500 deg] 
measure for 25.0 seconds; frame angle 0.60 degrees, wavelength=0.71073>
<Omega scan: start=   8.9; len= 105.0; end= 113.9 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=   3.062 deg phi= 360.000 deg chi= -46.500 deg] 
measure for 25.0 seconds; frame angle 0.60 degrees, wavelength=0.71073>
<Phi   scan: start=  40.5; len= 142.8; end= 183.3 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=   3.062 deg omega=  10.771 deg chi= -38.000 deg] 
measure for 25.0 seconds; frame angle 0.60 degrees, wavelength=0.71073>
;
_diffrn_measurement_device       'KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13266
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_reduction_process narrow-frame
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_min         1.947
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           1.6
_diffrn_source_target            Mo
_diffrn_source_type              'INCOATEC I\mS Diamant II'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for single-crystal
 structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       needle
_exptl_crystal_F_000             432
_exptl_crystal_recrystallization_method
'The crystals were crystallised from acetonitrile.'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 950 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2232
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0306
_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^)+(0.0491P)^2^+0.1637P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0801
_reflns_Friedel_coverage         0.893
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2112
_reflns_number_total             2232
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc04412j2.cif
_cod_data_source_block           rav10796_E-3iz-4iz
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1575831--1575832.cif.
;
_cod_database_code               1575832
_shelx_shelxl_version_number     2019/3
_exptl_bruker_absorpt_correction_t_ratio 0.9443
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.996
_bruker_diffrn_measurement_temperature_device 'Oxford Cryostream 1000'
_diffrn_measurement_bruker_total_exposure_time 16995.0
_diffrn_reflns_bruker_av_norm_i  442.943
_diffrn_reflns_bruker_number_gt  14566
_computing_bruker_data_scaling
'SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction'
_geom_details
; All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
_shelx_res_checksum              58666