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_1575831
_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         'C10 H12 N4 O2'
_chemical_formula_sum            'C10 H12 N4 O2'
_chemical_formula_weight         220.24
_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
_atom_sites_solution_primary     'Intrinsic Phasing'
_audit_creation_method
;
FinalCif 2024.9-0 by Daniel Kratzert, Freiburg 2024, 
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                 101.967(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.1319(2)
_cell_length_b                   15.3888(7)
_cell_length_c                   8.5819(4)
_cell_measurement_reflns_used    9656
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.3688
_cell_measurement_theta_min      5.7503
_cell_measurement_wavelength     1.54178
_cell_volume                     533.82(4)
_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 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;<Phi   scan: start=   0.0; len= 180.0; end= 180.0 at [Counterclockwise Eulerian 
angles: dx= 42.20 mm theta=  27.500 deg omega= 360.000 deg chi=  54.740 deg] 
measure for 3.0 seconds; frame angle 1.00 degrees, wavelength=1.54184>
<Phi   scan: start= 180.0; len= 180.0; end= 360.0 at [Counterclockwise Eulerian 
angles: dx= 42.20 mm theta=  27.500 deg omega= 360.000 deg chi=  54.740 deg] 
measure for 3.0 seconds; frame angle 1.00 degrees, wavelength=1.54184>
<Omega scan: start= 354.1; len= 112.5; end= 466.6 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  54.313 deg phi= 256.000 deg chi=  57.500 deg] 
measure for 40.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Phi   scan: start=   0.0; len= 360.0; end= 360.0 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  54.312 deg omega= 113.272 deg chi= -38.000 deg] 
measure for 40.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Phi   scan: start=  44.0; len= 183.0; end= 227.0 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  54.312 deg omega=   3.914 deg chi=  38.000 deg] 
measure for 40.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Phi   scan: start= 360.0; len=   1.5; end= 361.5 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta= -24.312 deg omega=  60.605 deg chi= -46.500 deg] 
measure for 15.3 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Omega scan: start=  95.4; len=  79.5; end= 174.9 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  46.812 deg phi=  90.000 deg chi= -46.500 deg] 
measure for 30.2 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Omega scan: start= 314.4; len= 103.5; end= 417.9 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta= -23.464 deg phi=  40.000 deg chi= -57.500 deg] 
measure for 15.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Omega scan: start= 354.1; len= 112.5; end= 466.6 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  54.312 deg phi= 160.000 deg chi=  57.500 deg] 
measure for 40.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Phi   scan: start= 360.0; len=   1.5; end= 361.5 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  46.812 deg omega=  95.354 deg chi= -46.500 deg] 
measure for 30.2 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Omega scan: start= 354.1; len= 112.5; end= 466.6 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  54.312 deg phi=  64.000 deg chi=  57.500 deg] 
measure for 40.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Omega scan: start= 354.1; len= 112.5; end= 466.6 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  54.312 deg phi= 320.000 deg chi=  57.500 deg] 
measure for 40.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Phi   scan: start=   3.6; len= 160.5; end= 164.1 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta= -23.464 deg omega= 308.424 deg chi=  38.000 deg] 
measure for 15.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Omega scan: start=  95.4; len=  79.5; end= 174.9 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  46.812 deg phi=   0.000 deg chi= -46.500 deg] 
measure for 30.2 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Phi   scan: start= 360.0; len=   1.5; end= 361.5 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  39.312 deg omega=  80.354 deg chi= -46.500 deg] 
measure for 23.1 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Omega scan: start= 314.4; len= 103.5; end= 417.9 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta= -23.464 deg phi=   0.000 deg chi= -57.500 deg] 
measure for 15.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Omega scan: start= 354.1; len= 112.5; end= 466.6 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  54.312 deg phi= 128.000 deg chi=  57.500 deg] 
measure for 40.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Omega scan: start= 354.1; len= 112.5; end= 466.6 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  54.312 deg phi=  32.000 deg chi=  57.500 deg] 
measure for 40.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Omega scan: start=  95.4; len=  79.5; end= 174.9 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  46.812 deg phi= 270.000 deg chi= -46.500 deg] 
measure for 30.2 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Phi   scan: start= 360.0; len=   1.5; end= 361.5 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  54.312 deg omega= 110.354 deg chi= -46.500 deg] 
measure for 40.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Phi   scan: start=   3.6; len= 160.5; end= 164.1 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta= -23.464 deg omega= 308.424 deg chi=  38.000 deg] 
measure for 15.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Omega scan: start= 354.1; len= 112.5; end= 466.6 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  54.312 deg phi=  96.000 deg chi=  57.500 deg] 
measure for 40.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Phi   scan: start= 360.0; len=   1.5; end= 361.5 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta= -31.812 deg omega=  45.605 deg chi= -46.500 deg] 
measure for 18.3 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Omega scan: start=  80.4; len=  94.5; end= 174.9 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  39.312 deg phi=   0.000 deg chi= -46.500 deg] 
measure for 23.1 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Omega scan: start= 354.1; len= 112.5; end= 466.6 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  54.312 deg phi= 360.000 deg chi=  57.500 deg] 
measure for 40.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
;
_diffrn_measurement_device       'KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support loop
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14141
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_reduction_process narrow-frame
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.505
_diffrn_reflns_theta_min         5.75
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           1.0
_diffrn_source_target            Cu
_diffrn_source_type              'INCOATEC I\mS Diamant II'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.901
_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    1.37
_exptl_crystal_description       needle
_exptl_crystal_F_000             232
_exptl_crystal_recrystallization_method 'cyclohexane / DCM'
_exptl_crystal_size_max          0.129
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     75
_refine_ls_number_reflns         973
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0442P)^2^+0.1787P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0887
_reflns_Friedel_coverage         0.000
_reflns_number_gt                889
_reflns_number_total             973
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc04412j2.cif
_cod_data_source_block           rav10738_E-4iz-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_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1575831
_shelx_shelxl_version_number     2019/3
_exptl_bruker_absorpt_correction_t_ratio 0.874
_shelx_estimated_absorpt_t_min   0.901
_shelx_estimated_absorpt_t_max   0.965
_bruker_diffrn_measurement_temperature_device 'Oxford Cryostream 1000'
_diffrn_measurement_bruker_total_exposure_time 81553.09999999999
_diffrn_reflns_bruker_av_norm_i  22086.176
_diffrn_reflns_bruker_number_gt  12764
_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              16900