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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/1/57/43/1574342.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_1574342
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             2023-03-15
_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                 112.41(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.455(9)
_cell_length_b                   5.4916(2)
_cell_length_c                   11.591(3)
_cell_measurement_pressure       1909000
_cell_measurement_reflns_used    497
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.6330
_cell_measurement_theta_min      2.1900
_cell_volume                     850.6(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         1909000
_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 0.350
_diffrn_measured_fraction_theta_max 0.211
_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      0.0304349931
_diffrn_orient_matrix_UB_12      0.0062909746
_diffrn_orient_matrix_UB_13      0.0178745702
_diffrn_orient_matrix_UB_21      -0.0035451251
_diffrn_orient_matrix_UB_22      0.0199373149
_diffrn_orient_matrix_UB_23      0.0321485951
_diffrn_orient_matrix_UB_31      0.0016774555
_diffrn_orient_matrix_UB_32      -0.0716744013
_diffrn_orient_matrix_UB_33      0.0105118571
_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  0.0239
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.350
_diffrn_reflns_Laue_measured_fraction_max 0.211
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3995
_diffrn_reflns_point_group_measured_fraction_full 0.350
_diffrn_reflns_point_group_measured_fraction_max 0.211
_diffrn_reflns_theta_full        14.241
_diffrn_reflns_theta_max         21.167
_diffrn_reflns_theta_min         2.313
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_exptl_absorpt_coefficient_mu    0.039
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66623
_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    1.423
_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         0.384
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         3995
_refine_ls_number_restraints     96
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0559
_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)+(0.1065P)²+0.0453P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1582
_refine_ls_wR_factor_ref         0.1660
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3372
_reflns_number_total             3995
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5sc00432b3.cif
_cod_data_source_block           AZO_1p9GPa
_cod_depositor_comments
'Adding full bibliography for 1574311--1574352.cif.'
_cod_original_cell_volume        850.6(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1574342
_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 0.4893(3) 0.1087(3) 0.5055(2) 0.0247(10) Uani 1 1 d . U . . .
C1 C 0.4315(3) 0.1405(3) 0.5795(2) 0.0211(10) Uani 1 1 d . U . . .
C2 C 0.3811(3) 0.3610(3) 0.5664(2) 0.0251(11) Uani 1 1 d . U . . .
H2 H 0.386163 0.477853 0.511062 0.030 Uiso 1 1 calc R U . . .
C3 C 0.3234(3) 0.4063(3) 0.6356(3) 0.0266(11) Uani 1 1 d . U . . .
H3 H 0.287915 0.551488 0.624787 0.032 Uiso 1 1 calc R U . . .
C4 C 0.3183(3) 0.2347(3) 0.7214(3) 0.0275(12) Uani 1 1 d . U . . .
H4 H 0.279873 0.265471 0.768484 0.033 Uiso 1 1 calc R U . . .
C5 C 0.3708(3) 0.0174(3) 0.7365(2) 0.0262(12) Uani 1 1 d . U . . .
H5 H 0.368700 -0.095164 0.795380 0.031 Uiso 1 1 calc R U . . .
C6 C 0.4263(3) -0.0336(3) 0.6648(2) 0.0219(10) Uani 1 1 d . U . . .
H6 H 0.459681 -0.181436 0.673384 0.026 Uiso 1 1 calc R U . . .
N2A N 0.9673(4) 0.0771(3) 0.9761(4) 0.0307(13) Uani 0.946(10) 1 d . U P A 1
N2B N 0.995(7) -0.097(7) 0.958(7) 0.033(4) Uani 0.054(10) 1 d . U P A 2
C7 C 0.9183(3) 0.0543(4) 0.8446(3) 0.0279(13) Uani 1 1 d . U . . .
C8 C 0.9280(4) -0.1439(4) 0.7740(3) 0.0315(13) Uani 1 1 d . U . . .
H8 H 0.968706 -0.275204 0.812547 0.038 Uiso 1 1 calc R U . . .
C9 C 0.8763(4) -0.1415(4) 0.6463(3) 0.0354(15) Uani 1 1 d . U . . .
H9 H 0.882397 -0.272493 0.598790 0.043 Uiso 1 1 calc R U . . .
C10 C 0.8156(4) 0.0532(4) 0.5879(3) 0.0326(15) Uani 1 1 d . U . . .
H10 H 0.780770 0.052464 0.501853 0.039 Uiso 1 1 calc R U . . .
C11 C 0.8071(4) 0.2497(4) 0.6589(3) 0.0361(15) Uani 1 1 d . U . . .
H11 H 0.767756 0.382716 0.620012 0.043 Uiso 1 1 calc R U . . .
C12 C 0.8565(4) 0.2481(4) 0.7855(3) 0.0322(14) Uani 1 1 d . U . . .
H12 H 0.848651 0.377689 0.832646 0.039 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 113.8(2) 3_656 . ?
C2 C1 C6 120.4(2) . . ?
C2 C1 N1 116.49(15) . . ?
C6 C1 N1 123.1(2) . . ?
C3 C2 C1 120.02(16) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.0(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C6 C5 C4 120.79(17) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 119.0(2) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N2A N2A C7 113.9(3) 3_757 . ?
N2B N2B C7 91(6) 3_757 . ?
C12 C7 C8 119.7(3) . . ?
C12 C7 N2A 115.2(2) . . ?
C8 C7 N2A 125.1(3) . . ?
C12 C7 N2B 157.0(19) . . ?
C8 C7 N2B 83.3(18) . . ?
C9 C8 C7 119.0(3) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 121.0(2) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C11 119.5(3) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C7 120.6(2) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
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 1.252(3) 3_656 ?
N1 C1 1.418(3) . ?
C1 C2 1.391(3) . ?
C1 C6 1.398(2) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2A N2A 1.232(8) 3_757 ?
N2A C7 1.420(5) . ?
N2B N2B 1.41(11) 3_757 ?
N2B C7 1.60(8) . ?
C7 C12 1.390(5) . ?
C7 C8 1.401(3) . ?
C8 C9 1.381(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.385(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.391(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.366(5) . ?
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 -161.9(4) 3_656 . . . ?
N1 N1 C1 C6 20.0(6) 3_656 . . . ?
C6 C1 C2 C3 -1.7(5) . . . . ?
N1 C1 C2 C3 -179.8(3) . . . . ?
C1 C2 C3 C4 2.1(6) . . . . ?
C2 C3 C4 C5 -0.5(6) . . . . ?
C3 C4 C5 C6 -1.6(6) . . . . ?
C4 C5 C6 C1 2.0(6) . . . . ?
C2 C1 C6 C5 -0.4(6) . . . . ?
N1 C1 C6 C5 177.6(3) . . . . ?
N2A N2A C7 C12 -169.6(4) 3_757 . . . ?
N2A N2A C7 C8 10.5(7) 3_757 . . . ?
N2B N2B C7 C12 -5(12) 3_757 . . . ?
N2B N2B C7 C8 174(6) 3_757 . . . ?
C12 C7 C8 C9 0.5(5) . . . . ?
N2A C7 C8 C9 -179.6(4) . . . . ?
N2B C7 C8 C9 -179(3) . . . . ?
C7 C8 C9 C10 0.1(6) . . . . ?
C8 C9 C10 C11 0.4(6) . . . . ?
C9 C10 C11 C12 -1.5(6) . . . . ?
C10 C11 C12 C7 2.2(6) . . . . ?
C8 C7 C12 C11 -1.6(5) . . . . ?
N2A C7 C12 C11 178.4(3) . . . . ?
N2B C7 C12 C11 177(6) . . . . ?
