#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/47/2214716.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2214716
loop_
_publ_author_name
'González Martínez, Sandra Patricia'
'Bernès, Sylvain'
_publ_section_title
;
 trans-Diphenyldiazene oxide
;
_journal_coeditor_code           HG2265
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3639
_journal_page_last               o3639
_journal_paper_doi               10.1107/S1600536807035787
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C12 H10 N2 O'
_chemical_formula_moiety         'C12 H10 N2 O'
_chemical_formula_sum            'C12 H10 N2 O'
_chemical_formula_weight         198.22
_chemical_melting_point          .305E-305
_chemical_name_common            trans-Azoxybenzene
_chemical_name_systematic
;
trans-Diphenyldiazene oxide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL-Plus
_cell_angle_alpha                90.00
_cell_angle_beta                 103.30(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.844(3)
_cell_length_b                   15.864(7)
_cell_length_c                   11.073(5)
_cell_measurement_reflns_used    68
_cell_measurement_temperature    299.0(10)
_cell_measurement_theta_max      12.03
_cell_measurement_theta_min      4.54
_cell_volume                     999.0(8)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1999)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'Mercury (Macrae et al.,  2006)'
_computing_publication_material  SHELXTL-Plus
_computing_structure_refinement  SHELXTL-Plus
_computing_structure_solution    'SHELXTL-Plus (Sheldrick, 1998)'
_diffrn_ambient_temperature      299.0(10)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1149
_diffrn_reflns_av_sigmaI/netI    0.0801
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4750
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         2.28
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 48
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.149
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1746
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0551
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.043P)²+0.2419P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1254
_refine_ls_wR_factor_ref         0.1564
_reflns_number_gt                1034
_reflns_number_total             1746
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2265.cif
_cod_data_source_block           I
_cod_original_cell_volume        998.9(8)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2214716
_cod_database_fobs_code          2214716
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1A -0.0378(16) 0.4162(9) 0.5903(12) 0.080(3) Uani d P 0.60 A 1
O O1B -0.015(3) 0.3914(15) 0.6080(18) 0.109(7) Uani d P 0.40 A 2
N N1 0.1816(4) 0.42455(16) 0.6174(2) 0.0637(7) Uani d . 1 . .
N N2 0.3345(4) 0.39334(15) 0.5698(2) 0.0634(7) Uani d . 1 A .
C C1 0.2717(5) 0.48817(17) 0.7134(3) 0.0566(7) Uani d . 1 A .
C C2 0.1399(6) 0.50318(19) 0.7979(3) 0.0713(9) Uani d . 1 . .
H H2 -0.0068 0.4734 0.7936 0.086 Uiso calc R 1 A .
C C3 0.2203(6) 0.5616(2) 0.8893(3) 0.0805(10) Uani d . 1 A .
H H3 0.1325 0.5713 0.9525 0.097 Uiso calc R 1 . .
C C4 0.4186(6) 0.6056(2) 0.8930(3) 0.0819(10) Uani d . 1 . .
H H4 0.4712 0.6475 0.9573 0.098 Uiso calc R 1 A .
C C5 0.5464(6) 0.5911(2) 0.8052(3) 0.0792(9) Uani d . 1 A .
H H5 0.6882 0.6232 0.8067 0.095 Uiso calc R 1 . .
C C6 0.4729(5) 0.53096(18) 0.7152(3) 0.0663(8) Uani d . 1 . .
H H6 0.5638 0.5194 0.6539 0.080 Uiso calc R 1 A .
C C7 0.2709(5) 0.32809(17) 0.4804(2) 0.0551(7) Uani d . 1 . .
C C8 0.4621(5) 0.28069(19) 0.4705(3) 0.0621(8) Uani d . 1 A .
H H8 0.6153 0.2926 0.5236 0.075 Uiso calc R 1 . .
C C9 0.4369(5) 0.2169(2) 0.3863(3) 0.0658(8) Uani d . 1 . .
H H9 0.5719 0.1826 0.3815 0.079 Uiso calc R 1 A .
C C10 0.2243(5) 0.20073(18) 0.3086(3) 0.0627(8) Uani d . 1 A .
H H10 0.2077 0.1550 0.2490 0.075 Uiso calc R 1 . .
C C11 0.0350(5) 0.24936(18) 0.3153(3) 0.0645(8) Uani d . 1 . .
H H11 -0.1155 0.2389 0.2586 0.077 Uiso calc R 1 A .
C C12 0.0550(5) 0.31344(18) 0.4019(3) 0.0615(7) Uani d . 1 A .
H H12 -0.0804 0.3474 0.4071 0.074 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 2 1
-1 -1 1
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 N1 O1B 122.4(10)
N2 N1 O1A 130.7(6)
N2 N1 C1 114.0(2)
O1B N1 C1 121.3(9)
O1A N1 C1 114.9(6)
N1 N2 C7 119.2(2)
C6 C1 C2 121.9(3)
C6 C1 N1 121.3(3)
C2 C1 N1 116.8(3)
C1 C2 C3 118.2(3)
C1 C2 H2 120.9
C3 C2 H2 120.9
C4 C3 C2 121.3(3)
C4 C3 H3 119.4
C2 C3 H3 119.4
C3 C4 C5 119.7(3)
C3 C4 H4 120.2
C5 C4 H4 120.2
C6 C5 C4 120.0(3)
C6 C5 H5 120.0
C4 C5 H5 120.0
C1 C6 C5 118.9(3)
C1 C6 H6 120.5
C5 C6 H6 120.5
C8 C7 C12 120.1(3)
C8 C7 N2 111.6(3)
C12 C7 N2 128.1(3)
C9 C8 C7 120.0(3)
C9 C8 H8 120.0
C7 C8 H8 120.0
C8 C9 C10 120.8(3)
C8 C9 H9 119.6
C10 C9 H9 119.6
C9 C10 C11 119.5(3)
C9 C10 H10 120.3
C11 C10 H10 120.3
C10 C11 C12 120.8(3)
C10 C11 H11 119.6
C12 C11 H11 119.6
C7 C12 C11 118.7(3)
C7 C12 H12 120.6
C11 C12 H12 120.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1A N1 1.255(10)
O1B N1 1.243(18)
N1 N2 1.240(3)
N1 C1 1.473(4)
N2 C7 1.421(3)
C1 C6 1.354(4)
C1 C2 1.363(4)
C2 C3 1.373(5)
C2 H2 0.9700
C3 C4 1.346(5)
C3 H3 0.9700
C4 C5 1.375(5)
C4 H4 0.9700
C5 C6 1.374(4)
C5 H5 0.9700
C6 H6 0.9700
C7 C8 1.372(4)
C7 C12 1.378(4)
C8 C9 1.361(4)
C8 H8 0.9700
C9 C10 1.363(4)
C9 H9 0.9700
C10 C11 1.364(4)
C10 H10 0.9700
C11 C12 1.384(4)
C11 H11 0.9700
C12 H12 0.9700
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
O1B N1 N2 C7 13.5(13)
O1A N1 N2 C7 -10.0(10)
C1 N1 N2 C7 176.8(2)
N2 N1 C1 C6 23.9(4)
O1B N1 C1 C6 -172.6(13)
O1A N1 C1 C6 -150.4(8)
N2 N1 C1 C2 -157.7(3)
O1B N1 C1 C2 5.8(13)
O1A N1 C1 C2 28.0(8)
C6 C1 C2 C3 -2.2(5)
N1 C1 C2 C3 179.4(3)
C1 C2 C3 C4 2.7(5)
C2 C3 C4 C5 -1.2(5)
C3 C4 C5 C6 -0.9(5)
C2 C1 C6 C5 0.2(5)
N1 C1 C6 C5 178.5(3)
C4 C5 C6 C1 1.4(5)
N1 N2 C7 C8 -158.1(3)
N1 N2 C7 C12 27.2(4)
C12 C7 C8 C9 -2.5(4)
N2 C7 C8 C9 -177.7(2)
C7 C8 C9 C10 1.8(4)
C8 C9 C10 C11 0.3(4)
C9 C10 C11 C12 -1.6(4)
C8 C7 C12 C11 1.2(4)
N2 C7 C12 C11 175.5(2)
C10 C11 C12 C7 0.9(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 10316
