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#$Date: 2025-04-05 01:15:10 +0300 (Sat, 05 Apr 2025) $
#$Revision: 298722 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/43/1574351.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_1574351
loop_
_publ_author_name
'Agati, Milo'
'Romi, Sebastiano'
'Fanetti, Samuele'
'Radacki, Krzysztof'
'Michael, Hanfland'
'Braunschweig, Holger'
'Marder, Todd B.'
'Clark, Stewart'
'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_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC00432B
_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                 112.40(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.547(13)
_cell_length_b                   5.5258(3)
_cell_length_c                   11.659(4)
_cell_measurement_pressure       1513000
_cell_measurement_reflns_used    426
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.5960
_cell_measurement_theta_min      2.2110
_cell_volume                     866.5(9)
_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         1513000
_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 0.349
_diffrn_measured_fraction_theta_max 0.214
_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      0.0302311043
_diffrn_orient_matrix_UB_12      0.0062797562
_diffrn_orient_matrix_UB_13      0.0177904356
_diffrn_orient_matrix_UB_21      -0.0035535390
_diffrn_orient_matrix_UB_22      0.0197920863
_diffrn_orient_matrix_UB_23      0.0319471627
_diffrn_orient_matrix_UB_31      0.0016687863
_diffrn_orient_matrix_UB_32      -0.0712413295
_diffrn_orient_matrix_UB_33      0.0104479785
_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  0.0209
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.349
_diffrn_reflns_Laue_measured_fraction_max 0.214
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_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            4050
_diffrn_reflns_point_group_measured_fraction_full 0.349
_diffrn_reflns_point_group_measured_fraction_max 0.214
_diffrn_reflns_theta_full        14.241
_diffrn_reflns_theta_max         21.065
_diffrn_reflns_theta_min         2.016
_diffrn_source                   synchrotron
_diffrn_source_type              'ESRF EBS (Extremely Brilliant Source)'
_exptl_absorpt_coefficient_mu    0.038
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23878
_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    1.397
_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         0.257
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         4050
_refine_ls_number_restraints     96
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0586
_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)+(0.1072P)²+0.0353P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1621
_refine_ls_wR_factor_ref         0.1708
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3314
_reflns_number_total             4050
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5sc00432b3.cif
_cod_data_source_block           AZO_1p5GPa
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1574351
_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) 0.1080(3) 0.5054(2) 0.0267(10) Uani 1 1 d . U . . .
C1 C 0.4316(3) 0.1399(3) 0.5787(2) 0.0229(10) Uani 1 1 d . U . . .
C2 C 0.3820(3) 0.3591(3) 0.5658(2) 0.0282(11) Uani 1 1 d . U . . .
H2 H 0.387635 0.475473 0.511261 0.034 Uiso 1 1 calc R U . . .
C3 C 0.3241(3) 0.4044(3) 0.6339(3) 0.0306(11) Uani 1 1 d . U . . .
H3 H 0.288839 0.548671 0.622840 0.037 Uiso 1 1 calc R U . . .
C4 C 0.3188(3) 0.2342(4) 0.7191(3) 0.0306(12) Uani 1 1 d . U . . .
H4 H 0.280335 0.264812 0.765568 0.037 Uiso 1 1 calc R U . . .
C5 C 0.3711(3) 0.0183(3) 0.7344(3) 0.0280(12) Uani 1 1 d . U . . .
H5 H 0.368968 -0.093235 0.793123 0.034 Uiso 1 1 calc R U . . .
C6 C 0.4263(3) -0.0330(3) 0.6636(2) 0.0240(10) Uani 1 1 d . U . . .
H6 H 0.459332 -0.180021 0.672279 0.029 Uiso 1 1 calc R U . . .
N2A N 0.9671(5) 0.0768(4) 0.9758(5) 0.0347(15) Uani 0.934(12) 1 d . U P A 1
N2B N 0.991(7) -0.094(6) 0.960(7) 0.035(4) Uani 0.066(12) 1 d . U P A 2
C7 C 0.9187(3) 0.0539(4) 0.8455(3) 0.0312(13) Uani 1 1 d . U . . .
C8 C 0.9281(4) -0.1427(4) 0.7747(3) 0.0352(14) Uani 1 1 d . U . . .
H8 H 0.968791 -0.273049 0.812722 0.042 Uiso 1 1 calc R U . . .
C9 C 0.8764(4) -0.1402(4) 0.6481(3) 0.0392(15) Uani 1 1 d . U . . .
H9 H 0.882352 -0.270022 0.600601 0.047 Uiso 1 1 calc R U . . .
C10 C 0.8156(4) 0.0537(5) 0.5905(3) 0.0383(16) Uani 1 1 d . U . . .
H10 H 0.780752 0.053303 0.504995 0.046 Uiso 1 1 calc R U . . .
C11 C 0.8072(4) 0.2482(4) 0.6613(3) 0.0399(16) Uani 1 1 d . U . . .
H11 H 0.767580 0.379986 0.623039 0.048 Uiso 1 1 calc R U . . .
C12 C 0.8570(4) 0.2461(4) 0.7871(3) 0.0358(14) Uani 1 1 d . U . . .
H12 H 0.849571 0.374820 0.834238 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 114.0(2) 3_656 . ?
C2 C1 C6 120.4(2) . . ?
C2 C1 N1 116.47(16) . . ?
C6 C1 N1 123.1(2) . . ?
C3 C2 C1 120.07(17) . . ?
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 120.2 . . ?
C3 C4 H4 120.2 . . ?
C6 C5 C4 120.88(18) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 118.9(2) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N2A N2A C7 114.1(4) 3_757 . ?
N2B N2B C7 94(5) 3_757 . ?
C12 C7 C8 119.6(3) . . ?
C12 C7 N2A 115.0(2) . . ?
C8 C7 N2A 125.5(3) . . ?
C12 C7 N2B 155.4(17) . . ?
C8 C7 N2B 85.0(18) . . ?
C9 C8 C7 119.1(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 120.9(2) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 119.6(3) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C7 120.8(2) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
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 1.252(3) 3_656 ?
N1 C1 1.419(3) . ?
C1 C2 1.388(3) . ?
C1 C6 1.399(2) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2A N2A 1.242(10) 3_757 ?
N2A C7 1.416(6) . ?
N2B N2B 1.35(11) 3_757 ?
N2B C7 1.58(7) . ?
C7 C12 1.389(5) . ?
C7 C8 1.403(3) . ?
C8 C9 1.378(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.389(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.389(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(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 -162.1(4) 3_656 . . . ?
N1 N1 C1 C6 20.1(6) 3_656 . . . ?
C6 C1 C2 C3 -2.2(6) . . . . ?
N1 C1 C2 C3 180.0(3) . . . . ?
C1 C2 C3 C4 2.5(6) . . . . ?
C2 C3 C4 C5 -0.5(6) . . . . ?
C3 C4 C5 C6 -1.9(6) . . . . ?
C4 C5 C6 C1 2.2(6) . . . . ?
C2 C1 C6 C5 -0.1(5) . . . . ?
N1 C1 C6 C5 177.5(3) . . . . ?
N2A N2A C7 C12 -169.7(5) 3_757 . . . ?
N2A N2A C7 C8 10.6(7) 3_757 . . . ?
N2B N2B C7 C12 -16(11) 3_757 . . . ?
N2B N2B C7 C8 168(6) 3_757 . . . ?
C12 C7 C8 C9 0.5(5) . . . . ?
N2A C7 C8 C9 -179.9(4) . . . . ?
N2B C7 C8 C9 179(2) . . . . ?
C7 C8 C9 C10 0.1(6) . . . . ?
C8 C9 C10 C11 0.3(6) . . . . ?
C9 C10 C11 C12 -1.3(6) . . . . ?
C10 C11 C12 C7 1.8(6) . . . . ?
C8 C7 C12 C11 -1.4(6) . . . . ?
N2A C7 C12 C11 178.9(4) . . . . ?
N2B C7 C12 C11 -177(6) . . . . ?
