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_1574321
_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   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-03-17
_audit_creation_method           'CIF-fill 1.3s (K.Radacki, 2005-23)'
_audit_update_record
;
2024-02-29 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.64(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.592(9)
_cell_length_b                   5.4837(2)
_cell_length_c                   10.385(4)
_cell_measurement_pressure       24110000
_cell_measurement_reflns_used    473
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.5660
_cell_measurement_theta_min      2.4870
_cell_volume                     590.1(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_collection       'ESRF ID15B beamline software'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      He
_diffrn_ambient_pressure         24110000
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 HPA
_diffrn_detector_area_resol_mean 13.3333
_diffrn_detector_type            'EIGER2 X 9M CdTe'
_diffrn_measured_fraction_theta_full 0.345
_diffrn_measured_fraction_theta_max 0.223
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w    -33.00  32.00   0.50    1.00    --    0.00   0.00   0.00  130
;
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       '\w scan'
_diffrn_orient_matrix_type
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0395082264
_diffrn_orient_matrix_UB_12      0.0056405142
_diffrn_orient_matrix_UB_13      -0.0217005204
_diffrn_orient_matrix_UB_21      0.0027608210
_diffrn_orient_matrix_UB_22      0.0231711567
_diffrn_orient_matrix_UB_23      -0.0360027609
_diffrn_orient_matrix_UB_31      -0.0021233225
_diffrn_orient_matrix_UB_32      -0.0707772409
_diffrn_orient_matrix_UB_33      -0.0134492612
_diffrn_radiation_monochromator  'Si(111) Bragg monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.410
_diffrn_reflns_av_R_equivalents  0.0115
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.345
_diffrn_reflns_Laue_measured_fraction_max 0.223
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2705
_diffrn_reflns_point_group_measured_fraction_full 0.345
_diffrn_reflns_point_group_measured_fraction_max 0.223
_diffrn_reflns_theta_full        14.241
_diffrn_reflns_theta_max         21.707
_diffrn_reflns_theta_min         2.263
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_exptl_absorpt_coefficient_mu    0.056
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.051
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_preparation
;
 For data collection the crystal was mounted in a diamond-anvil cell.
;
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2705
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0675
_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^)+(0.1589P)^2^+0.0086P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2059
_refine_ls_wR_factor_ref         0.2147
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2201
_reflns_number_total             2705
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc00432b4.cif
_cod_data_source_block           AZO_24p1GPa
_cod_depositor_comments
'Adding full bibliography for 1574311--1574352.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1574321
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              83257