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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/1/57/43/1574333.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_1574333
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 1.3r (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                 113.15(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.162(11)
_cell_length_b                   5.1734(3)
_cell_length_c                   10.885(3)
_cell_measurement_pressure       11540000
_cell_measurement_reflns_used    528
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      19.9530
_cell_measurement_theta_min      2.1570
_cell_volume                     681.5(7)
_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         11540000
_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 0.341
_diffrn_measured_fraction_theta_max 0.197
_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      -0.0337245889
_diffrn_orient_matrix_UB_12      0.0071544001
_diffrn_orient_matrix_UB_13      -0.0185291991
_diffrn_orient_matrix_UB_21      0.0029949439
_diffrn_orient_matrix_UB_22      0.0218950646
_diffrn_orient_matrix_UB_23      -0.0346116966
_diffrn_orient_matrix_UB_31      -0.0022451494
_diffrn_orient_matrix_UB_32      -0.0757464859
_diffrn_orient_matrix_UB_33      -0.0116697558
_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  0.0170
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.341
_diffrn_reflns_Laue_measured_fraction_max 0.197
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2908
_diffrn_reflns_point_group_measured_fraction_full 0.341
_diffrn_reflns_point_group_measured_fraction_max 0.197
_diffrn_reflns_theta_full        14.241
_diffrn_reflns_theta_max         21.675
_diffrn_reflns_theta_min         2.159
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_exptl_absorpt_coefficient_mu    0.048
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57221
_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    1.776
_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         0.420
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2908
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0731
_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)+(0.1343P)²+0.0992P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2059
_refine_ls_wR_factor_ref         0.2192
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2206
_reflns_number_total             2908
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5sc00432b3.cif
_cod_data_source_block           AZO_11p5GPa
_cod_depositor_comments
'Adding full bibliography for 1574311--1574352.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1574333
_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 0.4898(5) 0.1165(5) 0.5068(3) 0.0214(18) Uani 1 1 d . . . . .
C1 C 0.4275(6) 0.1474(5) 0.5848(4) 0.021(2) Uani 1 1 d . . . . .
C2 C 0.3775(6) 0.3836(5) 0.5782(4) 0.021(2) Uani 1 1 d . . . . .
H2 H 0.382785 0.511238 0.520836 0.025 Uiso 1 1 calc R U . . .
C3 C 0.3195(6) 0.4289(6) 0.6573(4) 0.023(2) Uani 1 1 d . . . . .
H3 H 0.281448 0.583673 0.649029 0.028 Uiso 1 1 calc R U . . .
C4 C 0.3175(6) 0.2458(6) 0.7493(4) 0.022(2) Uani 1 1 d . . . . .
H4 H 0.279963 0.279173 0.804294 0.026 Uiso 1 1 calc R U . . .
C5 C 0.3717(6) 0.0138(5) 0.7587(4) 0.023(2) Uani 1 1 d . . . . .
H5 H 0.372877 -0.107096 0.822466 0.027 Uiso 1 1 calc R U . . .
C6 C 0.4238(6) -0.0399(5) 0.6743(4) 0.021(2) Uani 1 1 d . . . . .
H6 H 0.456392 -0.200546 0.677196 0.025 Uiso 1 1 calc R U . . .
N2A N 0.9637(14) 0.0804(9) 0.9741(12) 0.029(4) Uani 0.70(2) 1 d . U P A 1
N2B N 0.988(3) -0.096(2) 0.959(3) 0.029(4) Uani 0.30(2) 1 d . U P A 2
C7 C 0.9141(8) 0.0407(8) 0.8317(5) 0.033(3) Uani 1 1 d . . . . .
C8 C 0.9235(8) -0.1634(8) 0.7574(7) 0.040(3) Uani 1 1 d . . . . .
H8 H 0.962839 -0.310390 0.798582 0.048 Uiso 1 1 calc R U . . .
C9 C 0.8735(8) -0.1477(8) 0.6201(6) 0.038(3) Uani 1 1 d . . . . .
H9 H 0.879164 -0.284141 0.567498 0.046 Uiso 1 1 calc R U . . .
C10 C 0.8158(8) 0.0693(9) 0.5618(5) 0.037(3) Uani 1 1 d . . . . .
H10 H 0.781463 0.080105 0.469209 0.044 Uiso 1 1 calc R U . . .
C11 C 0.8083(8) 0.2722(7) 0.6395(6) 0.038(3) Uani 1 1 d . . . . .
H11 H 0.769692 0.420626 0.599309 0.045 Uiso 1 1 calc R U . . .
C12 C 0.8566(8) 0.2563(7) 0.7731(5) 0.036(3) Uani 1 1 d . . . . .
H12 H 0.850597 0.392637 0.825555 0.043 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 112.6(3) 3_656 . ?
C2 C1 C6 120.5(3) . . ?
C2 C1 N1 116.8(2) . . ?
C6 C1 N1 122.4(4) . . ?
C1 C2 C3 119.3(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C4 120.5(4) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N2A N2A C7 109.8(8) 3_757 . ?
N2B N2B C7 100(2) 3_757 . ?
C12 C7 C8 121.3(5) . . ?
C12 C7 N2A 108.7(4) . . ?
C8 C7 N2A 129.8(7) . . ?
C12 C7 N2B 148.2(7) . . ?
C8 C7 N2B 90.4(8) . . ?
C7 C8 C9 118.8(6) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C10 C9 C8 119.6(4) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 120.2(5) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.1(5) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C7 119.9(3) . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
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 1.256(5) 3_656 ?
N1 C1 1.401(5) . ?
C1 C2 1.376(5) . ?
C1 C6 1.389(4) . ?
C2 C3 1.377(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2A N2A 1.22(2) 3_757 ?
N2A C7 1.440(14) . ?
N2B N2B 1.29(4) 3_757 ?
N2B C7 1.52(3) . ?
C7 C12 1.358(9) . ?
C7 C8 1.366(6) . ?
C8 C9 1.378(10) . ?
C8 H8 0.9300 . ?
C9 C10 1.364(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.376(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.341(9) . ?
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 -164.1(7) 3_656 . . . ?
N1 N1 C1 C6 21.7(10) 3_656 . . . ?
C6 C1 C2 C3 -2.7(9) . . . . ?
N1 C1 C2 C3 -177.0(6) . . . . ?
C1 C2 C3 C4 4.3(10) . . . . ?
C2 C3 C4 C5 -1.8(10) . . . . ?
C3 C4 C5 C6 -2.4(10) . . . . ?
C4 C5 C6 C1 3.9(10) . . . . ?
C2 C1 C6 C5 -1.3(9) . . . . ?
N1 C1 C6 C5 172.6(6) . . . . ?
N2A N2A C7 C12 -163.8(11) 3_757 . . . ?
N2A N2A C7 C8 12.3(18) 3_757 . . . ?
N2B N2B C7 C12 -11(4) 3_757 . . . ?
N2B N2B C7 C8 165(2) 3_757 . . . ?
C12 C7 C8 C9 0.3(12) . . . . ?
N2A C7 C8 C9 -175.4(9) . . . . ?
N2B C7 C8 C9 -177.0(12) . . . . ?
C7 C8 C9 C10 -0.3(12) . . . . ?
C8 C9 C10 C11 0.6(11) . . . . ?
C9 C10 C11 C12 -0.8(11) . . . . ?
C10 C11 C12 C7 0.8(12) . . . . ?
C8 C7 C12 C11 -0.6(11) . . . . ?
N2A C7 C12 C11 175.9(8) . . . . ?
N2B C7 C12 C11 174(2) . . . . ?
