#------------------------------------------------------------------------------
#$Date: 2025-07-06 16:48:17 +0200 (Sun 06 de Jul de 2025) $
#$Revision: 300674 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/43/1574316.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_1574316
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             2023-03-17
_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                 116.8(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.44(3)
_cell_length_b                   5.4806(6)
_cell_length_c                   10.344(11)
_cell_measurement_pressure       26190000
_cell_measurement_reflns_used    372
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.0790
_cell_measurement_theta_min      2.4910
_cell_volume                     578.9(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         26190000
_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 0.338
_diffrn_measured_fraction_theta_max 0.221
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -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       'ω scan'
_diffrn_orient_matrix_type
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0400728483
_diffrn_orient_matrix_UB_12      0.0053320177
_diffrn_orient_matrix_UB_13      -0.0219314012
_diffrn_orient_matrix_UB_21      0.0027235804
_diffrn_orient_matrix_UB_22      0.0235621540
_diffrn_orient_matrix_UB_23      -0.0361397381
_diffrn_orient_matrix_UB_31      -0.0018887615
_diffrn_orient_matrix_UB_32      -0.0707108828
_diffrn_orient_matrix_UB_33      -0.0135202720
_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  0.0122
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.338
_diffrn_reflns_Laue_measured_fraction_max 0.221
_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            2459
_diffrn_reflns_point_group_measured_fraction_full 0.338
_diffrn_reflns_point_group_measured_fraction_max 0.221
_diffrn_reflns_theta_full        14.241
_diffrn_reflns_theta_max         21.758
_diffrn_reflns_theta_min         2.272
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_exptl_absorpt_coefficient_mu    0.057
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39410
_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    2.089
_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         0.809
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2459
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0871
_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)+(0.1771P)²+0.0831P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2703
_refine_ls_wR_factor_ref         0.2850
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1822
_reflns_number_total             2459
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5sc00432b4.cif
_cod_data_source_block           AZO_26p2GPa
_cod_depositor_comments
'Adding full bibliography for 1574311--1574352.cif.'
_cod_original_cell_volume        579.3(18)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1574316
_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(9) 0.1114(5) 0.5085(6) 0.025(2) Uani 1 1 d . U . . .
C1 C 0.4208(11) 0.1433(6) 0.5864(7) 0.025(3) Uani 1 1 d . U . . .
C2 C 0.3791(11) 0.3751(6) 0.5939(7) 0.024(3) Uani 1 1 d . U . . .
H2 H 0.386921 0.500863 0.537941 0.029 Uiso 1 1 calc R U . . .
C3 C 0.3254(11) 0.4151(6) 0.6872(7) 0.026(3) Uani 1 1 d . U . . .
H3 H 0.295536 0.569942 0.694149 0.031 Uiso 1 1 calc R U . . .
C4 C 0.3156(11) 0.2291(7) 0.7696(7) 0.026(3) Uani 1 1 d . U . . .
H4 H 0.279233 0.260315 0.832174 0.031 Uiso 1 1 calc R U . . .
C5 C 0.3578(10) -0.0019(6) 0.7626(7) 0.026(3) Uani 1 1 d . U . . .
H5 H 0.353016 -0.125248 0.821789 0.031 Uiso 1 1 calc R U . . .
C6 C 0.4070(10) -0.0473(7) 0.6672(7) 0.025(3) Uani 1 1 d . U . . .
H6 H 0.431193 -0.204962 0.656034 0.030 Uiso 1 1 calc R U . . .
N2 N 0.9908(9) 0.1115(5) 0.9822(6) 0.026(2) Uani 1 1 d . U . . .
C7 C 0.9211(11) 0.1434(7) 0.8348(7) 0.026(3) Uani 1 1 d . U . . .
C8 C 0.9048(11) -0.0453(7) 0.7397(7) 0.028(3) Uani 1 1 d . U . . .
H8 H 0.929256 -0.203052 0.774475 0.034 Uiso 1 1 calc R U . . .
C9 C 0.8528(11) -0.0001(7) 0.5941(7) 0.027(3) Uani 1 1 d . U . . .
H9 H 0.841459 -0.124868 0.528541 0.032 Uiso 1 1 calc R U . . .
C10 C 0.8182(11) 0.2341(6) 0.5486(7) 0.029(3) Uani 1 1 d . U . . .
H10 H 0.780497 0.267864 0.449992 0.035 Uiso 1 1 calc R U . . .
C11 C 0.8373(11) 0.4211(7) 0.6439(7) 0.030(3) Uani 1 1 d . U . . .
H11 H 0.816700 0.579810 0.609171 0.036 Uiso 1 1 calc R U . . .
C12 C 0.8859(11) 0.3788(7) 0.7890(7) 0.026(3) Uani 1 1 d . U . . .
H12 H 0.894654 0.503677 0.853663 0.032 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 112.4(5) 3_656 . ?
C2 C1 N1 117.3(4) . . ?
C2 C1 C6 121.7(5) . . ?
N1 C1 C6 120.6(5) . . ?
C1 C2 C3 117.7(4) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C4 C3 C2 120.5(4) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 121.8(5) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 118.6(4) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C1 119.6(4) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N2 N2 C7 112.5(6) 3_757 . ?
C12 C7 N2 115.8(5) . . ?
C12 C7 C8 122.3(6) . . ?
N2 C7 C8 121.2(5) . . ?
C9 C8 C7 120.0(5) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 117.7(4) . . ?
C10 C9 H9 121.2 . . ?
C8 C9 H9 121.2 . . ?
C9 C10 C11 121.9(6) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C12 C11 C10 121.2(4) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C7 116.8(4) . . ?
C11 C12 H12 121.6 . . ?
C7 C12 H12 121.6 . . ?
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 1.264(6) 3_656 ?
N1 C1 1.379(8) . ?
C1 C2 1.372(7) . ?
C1 C6 1.390(5) . ?
C2 C3 1.374(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.365(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.362(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 N2 1.267(6) 3_757 ?
N2 C7 1.377(10) . ?
C7 C12 1.371(6) . ?
C7 C8 1.381(6) . ?
C8 C9 1.370(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.363(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.365(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 -171.0(11) 3_656 . . . ?
N1 N1 C1 C6 16.2(15) 3_656 . . . ?
N1 C1 C2 C3 -171.2(9) . . . . ?
C6 C1 C2 C3 1.5(17) . . . . ?
C1 C2 C3 C4 0.5(16) . . . . ?
C2 C3 C4 C5 -0.2(16) . . . . ?
C3 C4 C5 C6 -2.1(16) . . . . ?
C4 C5 C6 C1 4.0(15) . . . . ?
C2 C1 C6 C5 -3.8(16) . . . . ?
N1 C1 C6 C5 168.6(9) . . . . ?
N2 N2 C7 C12 173.6(9) 3_757 . . . ?
N2 N2 C7 C8 -15.3(14) 3_757 . . . ?
C12 C7 C8 C9 0.5(16) . . . . ?
N2 C7 C8 C9 -170.0(9) . . . . ?
C7 C8 C9 C10 -0.2(15) . . . . ?
C8 C9 C10 C11 1.7(15) . . . . ?
C9 C10 C11 C12 -3.4(17) . . . . ?
C10 C11 C12 C7 3.5(16) . . . . ?
N2 C7 C12 C11 168.9(9) . . . . ?
C8 C7 C12 C11 -2.1(15) . . . . ?
