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#$Date: 2025-07-06 17:48:17 +0300 (Sun, 06 Jul 2025) $
#$Revision: 300674 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/43/1574339.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1574339
loop_
_publ_author_name
'Agati, Milo'
'Romi, Sebastiano'
'Fanetti, Samuele'
'Radacki, Krzysztof'
'Hanfland, Michael'
'Braunschweig, Holger'
'Marder, Todd B.'
'Clark, Stewart J.'
'Friedrich, Alexandra'
'Bini, Roberto'
_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             2023-03-16
_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                 112.98(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.08(3)
_cell_length_b                   5.1368(12)
_cell_length_c                   10.777(9)
_cell_measurement_pressure       13040000
_cell_measurement_reflns_used    335
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.0320
_cell_measurement_theta_min      2.1750
_cell_volume                     666.6(19)
_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         13040000
_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 0.339
_diffrn_measured_fraction_theta_max 0.228
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -33.00  32.00   0.50    0.50    --    0.00   0.00   0.00  130
;
_diffrn_measurement_device       'single-axis goniometer'
_diffrn_measurement_device_type  'in-house developed goniometer'
_diffrn_measurement_method       'ω scan'
_diffrn_orient_matrix_type
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0338818166
_diffrn_orient_matrix_UB_12      0.0092082210
_diffrn_orient_matrix_UB_13      -0.0185264091
_diffrn_orient_matrix_UB_21      0.0031797762
_diffrn_orient_matrix_UB_22      0.0226098340
_diffrn_orient_matrix_UB_23      -0.0348004424
_diffrn_orient_matrix_UB_31      -0.0030587996
_diffrn_orient_matrix_UB_32      -0.0757930484
_diffrn_orient_matrix_UB_33      -0.0124267416
_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  0.0543
_diffrn_reflns_av_unetI/netI     0.0843
_diffrn_reflns_Laue_measured_fraction_full 0.339
_diffrn_reflns_Laue_measured_fraction_max 0.228
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            1326
_diffrn_reflns_point_group_measured_fraction_full 0.339
_diffrn_reflns_point_group_measured_fraction_max 0.228
_diffrn_reflns_theta_full        14.241
_diffrn_reflns_theta_max         20.401
_diffrn_reflns_theta_min         2.181
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_exptl_absorpt_coefficient_mu    0.049
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21686
_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    1.816
_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         0.282
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         783
_refine_ls_number_restraints     102
_refine_ls_restrained_S_all      1.203
_refine_ls_R_factor_all          0.1379
_refine_ls_R_factor_gt           0.1062
_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/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2887
_refine_ls_wR_factor_ref         0.3108
_reflns_Friedel_coverage         0.000
_reflns_number_gt                513
_reflns_number_total             783
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5sc00432b3.cif
_cod_data_source_block           AZO_13GPa
_cod_depositor_comments
'Adding full bibliography for 1574311--1574352.cif.'
_cod_original_cell_volume        666.4(19)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1574339
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
 The symmetry employed for this shelxl refinement is uniquely defined by the 
 following loop, which should always be used as a source of symmetry 
 information in preference to the above space-group names. They are only 
 intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4908(10) 0.1172(8) 0.5069(6) 0.027(2) Uani 1 1 d . U . . .
C1 C 0.4273(11) 0.1488(8) 0.5855(7) 0.026(2) Uani 1 1 d . U . . .
C2 C 0.3781(11) 0.3861(8) 0.5805(7) 0.026(2) Uani 1 1 d . U . . .
H2 H 0.383770 0.515884 0.523315 0.031 Uiso 1 1 calc R U . . .
C3 C 0.3206(12) 0.4296(9) 0.6608(8) 0.029(2) Uani 1 1 d . U . . .
H3 H 0.282075 0.585095 0.652703 0.035 Uiso 1 1 calc R U . . .
C4 C 0.3188(11) 0.2460(10) 0.7537(7) 0.030(2) Uani 1 1 d . U . . .
H4 H 0.282641 0.281027 0.810901 0.036 Uiso 1 1 calc R U . . .
C5 C 0.3707(11) 0.0131(9) 0.7605(7) 0.027(2) Uani 1 1 d . U . . .
H5 H 0.369278 -0.110887 0.822702 0.032 Uiso 1 1 calc R U . . .
C6 C 0.4253(12) -0.0423(9) 0.6768(7) 0.025(2) Uani 1 1 d . U . . .
H6 H 0.459790 -0.202365 0.681093 0.030 Uiso 1 1 calc R U . . .
N2A N 0.9641(18) 0.0793(12) 0.9745(13) 0.030(2) Uani 0.67(2) 1 d . U P A 1
N2B N 0.984(4) -0.092(3) 0.954(3) 0.031(3) Uani 0.33(2) 1 d . U P A 2
C7 C 0.9129(15) 0.0395(14) 0.8289(9) 0.048(3) Uani 1 1 d . U . . .
C8 C 0.9231(18) -0.1637(14) 0.7533(12) 0.054(3) Uani 1 1 d . U . . .
H8 H 0.964456 -0.310582 0.793092 0.065 Uiso 1 1 calc R U . . .
C9 C 0.8687(18) -0.1419(12) 0.6133(11) 0.050(3) Uani 1 1 d . U . . .
H9 H 0.869266 -0.280050 0.557769 0.059 Uiso 1 1 calc R U . . .
C10 C 0.8159(15) 0.0792(14) 0.5600(9) 0.045(3) Uani 1 1 d . U . . .
H10 H 0.783284 0.096290 0.466725 0.054 Uiso 1 1 calc R U . . .
C11 C 0.8086(16) 0.2805(12) 0.6387(11) 0.045(2) Uani 1 1 d . U . . .
H11 H 0.770181 0.431435 0.599659 0.054 Uiso 1 1 calc R U . . .
C12 C 0.8581(14) 0.2574(11) 0.7745(9) 0.037(2) Uani 1 1 d . U . . .
H12 H 0.853969 0.392848 0.829650 0.045 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0006 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N1 C1 111.7(6) 3_656 . ?
C2 C1 C6 121.0(6) . . ?
C2 C1 N1 117.2(4) . . ?
C6 C1 N1 121.3(7) . . ?
C1 C2 C3 119.1(4) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 121.0(7) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.3(6) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.2(4) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 118.2(6) . . ?
C5 C6 H6 120.9 . . ?
C1 C6 H6 120.9 . . ?
N2A N2A C7 110.2(11) 3_757 . ?
N2B N2B C7 105(2) 3_757 . ?
C12 C7 C8 122.8(9) . . ?
C12 C7 N2A 107.3(7) . . ?
C8 C7 N2A 129.7(12) . . ?
C12 C7 N2B 145.7(9) . . ?
C8 C7 N2B 91.3(11) . . ?
C7 C8 C9 117.2(11) . . ?
C7 C8 H8 121.4 . . ?
C9 C8 H8 121.4 . . ?
C10 C9 C8 119.4(6) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 121.8(9) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C12 C11 C10 119.0(10) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C7 C12 C11 119.7(6) . . ?
C7 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N1 1.248(8) 3_656 ?
N1 C1 1.408(9) . ?
C1 C2 1.369(9) . ?
C1 C6 1.398(6) . ?
C2 C3 1.369(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.363(11) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(9) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2A N2A 1.20(3) 3_757 ?
N2A C7 1.461(17) . ?
N2B N2B 1.31(5) 3_757 ?
N2B C7 1.47(4) . ?
C7 C12 1.335(15) . ?
C7 C8 1.362(10) . ?
C8 C9 1.399(19) . ?
C8 H8 0.9300 . ?
C9 C10 1.337(15) . ?
C9 H9 0.9300 . ?
C10 C11 1.364(10) . ?
C10 H10 0.9300 . ?
C11 C12 1.355(15) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N1 C1 C2 -164.0(13) 3_656 . . . ?
N1 N1 C1 C6 23.4(18) 3_656 . . . ?
C6 C1 C2 C3 -4.0(18) . . . . ?
N1 C1 C2 C3 -176.5(11) . . . . ?
C1 C2 C3 C4 5.1(18) . . . . ?
C2 C3 C4 C5 -3.3(19) . . . . ?
C3 C4 C5 C6 0(2) . . . . ?
C4 C5 C6 C1 0.8(19) . . . . ?
C2 C1 C6 C5 1.1(18) . . . . ?
N1 C1 C6 C5 173.3(10) . . . . ?
N2A N2A C7 C12 -162.8(17) 3_757 . . . ?
N2A N2A C7 C8 11(3) 3_757 . . . ?
N2B N2B C7 C12 -13(6) 3_757 . . . ?
N2B N2B C7 C8 162(4) 3_757 . . . ?
C12 C7 C8 C9 -3(2) . . . . ?
N2A C7 C8 C9 -176.3(16) . . . . ?
N2B C7 C8 C9 -179.3(19) . . . . ?
C7 C8 C9 C10 4(2) . . . . ?
C8 C9 C10 C11 -3(2) . . . . ?
C9 C10 C11 C12 1(2) . . . . ?
C8 C7 C12 C11 1(2) . . . . ?
N2A C7 C12 C11 175.6(14) . . . . ?
N2B C7 C12 C11 174(3) . . . . ?
C10 C11 C12 C7 0(2) . . . . ?
