Insights into topochemical versus stress-induced high-pressure reactivity of azobenzene by single crystal X-ray diffraction
Agati, Milo; Romi, Sebastiano; Fanetti, Samuele; Radacki, Krzysztof; Hanfland, Michael; Braunschweig, Holger; Marder, Todd B.; Clark, Stewart J.; Friedrich, Alexandra; Bini, Roberto; Chemical Science 16 (2025) 9240–9254; doi:10.1039/D5SC00432B

data_1574325
_publ_section_title
;
 Insights into topochemical versus stress-induced high-pressure reactivity
 of azobenzene by single crystal X-ray diffraction
;
_journal_issue                   21
_journal_name_full               'Chemical Science'
_journal_page_first              9240
_journal_page_last               9254
_journal_paper_doi               10.1039/D5SC00432B
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
_chemical_name_systematic        trans-azobenzene
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   iterative
_audit_creation_date             2021-08-06
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.452(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9840(4)
_cell_length_b                   5.69830(10)
_cell_length_c                   12.0341(3)
_cell_measurement_reflns_used    6726
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.5080
_cell_measurement_theta_min      3.1830
_cell_volume                     949.63(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_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     75.00 131.00   0.50    0.05    --   85.25  22.00-144.75  112
  2  \w     87.00 132.00   0.50    0.05    --   82.37  15.00 -90.00   90
  3  \w     60.00 132.00   0.50    0.05    --   82.37  15.00 120.00  144
  4  \w     98.00 134.00   0.50    0.05    --   85.25 122.00  94.09   72
  5  \w     48.00  73.00   0.50    0.05    --   85.25 -84.00-114.47   50
  6  \w     73.00  99.00   0.50    0.05    --   85.25-138.00-132.97   52
  7  \w     34.00 100.00   0.50    0.05    --   82.37-114.00 -52.00  132
  8  \w     12.00  81.00   0.50    0.05    --   58.71-114.00 -52.00  138
  9  \w     23.00  93.00   0.50    0.05    --   71.33-114.00 -52.00  140
 10  \w     53.00 100.00   0.50    0.05    --   85.25-112.00   7.03   94
 11  \w     39.00 100.00   0.50    0.05    --   82.37-112.00  30.00  122
 12  \w     55.00  99.00   0.50    0.05    --   82.37-112.00  60.00   88
 13  \w     47.00  97.00   0.50    0.05    --   85.25-129.00 170.19  100
 14  \w     40.00  65.00   0.50    0.05    --   82.37 -95.00 150.00   50
 15  \w     43.00  81.00   0.50    0.05    --   82.37-112.00 120.00   76
 16  \w     39.00  65.00   0.50    0.05    --   85.25-109.00-172.69   52
 17  \w     44.00  85.00   0.50    0.05    --   85.25-101.00-115.07   82
 18  \w     41.00  89.00   0.50    0.05    --   85.25-108.00 -39.72   96
 19  \w    -33.00  -7.00   0.50    0.05    --  -10.00 115.00 107.70   52
 20  \w    -82.00 -12.00   0.50    0.05    --  -60.25 114.00  38.00  140
 21  \w    -92.00 -21.00   0.50    0.05    --  -69.78 114.00  38.00  142
 22  \w    -98.00 -28.00   0.50    0.05    --  -76.33 114.00  38.00  140
 23  \w   -124.00 -95.00   0.50    0.05    --  -79.50 -65.00  16.03   58
 24  \w   -106.00 -71.00   0.50    0.05    --  -58.00 -51.00 -39.80   70
 25  \w   -123.00 -88.00   0.50    0.05    --  -74.00 -47.00 -57.92   70
 26  \w   -129.00 -92.00   0.50    0.05    --  -79.50 -45.00 -86.23   74
 27  \w   -116.00 -79.00   0.50    0.05    --  -66.00 -45.00   0.45   74
 28  \w   -126.00 -92.00   0.50    0.05    --  -79.50 -57.00 178.65   68
 29  \w   -128.00 -93.00   0.50    0.05    --  -79.50 -50.00 125.24   70
 30  \w   -127.00 -99.00   0.50    0.05    --  -79.50-110.00 -84.21   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0166850000
_diffrn_orient_matrix_UB_12      0.2641430000
_diffrn_orient_matrix_UB_13      0.0116398000
_diffrn_orient_matrix_UB_21      -0.1079206000
_diffrn_orient_matrix_UB_22      -0.0310851000
_diffrn_orient_matrix_UB_23      -0.0789037000
_diffrn_orient_matrix_UB_31      -0.0213918000
_diffrn_orient_matrix_UB_32      -0.0489608000
_diffrn_orient_matrix_UB_33      0.1132176000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10160
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.476
_diffrn_reflns_theta_min         3.191
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.603
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.827
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Numerical
absorption correction based on gaussian integration over a 
multifaceted crystal model Empirical absorption correction using 
spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.208
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0045(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         1920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0335
_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^)+(0.0375P)^2^+0.3792P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0856
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1759
_reflns_number_total             1920
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc00432b3.cif
_cod_data_source_block           AZO_100K
_cod_depositor_comments
'Adding full bibliography for 1574311--1574352.cif.'
_cod_database_code               1574325
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.885
_diffrn_oxdiff_digest_frames
;
01824503bce61dfe1cb41afd55941c155e0270408fd
;
_diffrn_oxdiff_digest_hkl
;
0139d209c9f97b4e294c0951eb1ea7403065e0
;
_reflns_odcompleteness_completeness 98.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
;
_shelx_res_checksum              14444
_olex2_date_sample_data_collection 2021-08-03
_olex2_date_sample_submission    2021-07-29
_olex2_exptl_crystal_mounting_method
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
 polyimide microloop and transferred to stream of cold 
 nitrogen (Oxford Cryostream 800).
;
_olex2_submission_original_sample_id AZOBEN
_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 1.203
_oxdiff_exptl_absorpt_empirical_full_min 0.881