#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:19:20 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178894 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/23/4112348.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_4112348
loop_
_publ_author_name
'Jun Harada'
'Keiichiro Ogawa'
_publ_section_title
;
 X-ray Diffraction Analysis of Nonequilibrium States in Crystals:
 Observation of an Unstable Conformer in Flash-Cooled Crystals
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3539
_journal_page_last               3544
_journal_paper_doi               10.1021/ja038203l
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22
_chemical_melting_point          341
_chemical_name_common            azobenzene
_chemical_name_systematic
; 
(E)-1,2-diphenyldiazene 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   geom
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.4540(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0635(5)
_cell_length_b                   5.7161(3)
_cell_length_c                   15.0384(7)
_cell_measurement_reflns_used    8020
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.7
_cell_volume                     958.37(8)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD diffractometer'
_diffrn_measurement_method       ω_scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0112
_diffrn_reflns_av_sigmaI/netI    0.0075
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11870
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.988586
_exptl_absorpt_correction_T_min  0.875279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.054(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2206
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0386
_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)+(0.0519P)²+0.3360P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1056
_reflns_number_gt                2013
_reflns_number_total             2206
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja038203lsi20030829_041457.cif
_cod_data_source_block           azo150k
_cod_database_code               4112348
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.00477(8) 0.39524(16) 0.48986(6) 0.0218(2) Uani 1 1 d . . .
C11 C 0.07518(9) 0.36263(18) 0.43287(7) 0.0200(2) Uani 1 1 d . . .
C12 C 0.06144(9) 0.14850(19) 0.38570(8) 0.0241(2) Uani 1 1 d . . .
C13 C 0.12575(10) 0.1030(2) 0.32816(8) 0.0270(3) Uani 1 1 d . . .
C14 C 0.20699(10) 0.2665(2) 0.32082(8) 0.0267(3) Uani 1 1 d . . .
C15 C 0.22326(9) 0.4774(2) 0.37076(8) 0.0250(3) Uani 1 1 d . . .
C16 C 0.15708(9) 0.52743(19) 0.42634(7) 0.0215(2) Uani 1 1 d . . .
H12 H 0.0056(13) 0.032(3) 0.3935(10) 0.031(3) Uiso 1 1 d . . .
H13 H 0.1130(13) -0.046(3) 0.2938(10) 0.032(4) Uiso 1 1 d . . .
H14 H 0.2553(12) 0.235(3) 0.2821(10) 0.029(3) Uiso 1 1 d . . .
H15 H 0.2843(12) 0.594(3) 0.3673(10) 0.030(3) Uiso 1 1 d . . .
H16 H 0.1671(11) 0.672(2) 0.4606(9) 0.021(3) Uiso 1 1 d . . .
N21 N 0.52334(9) 0.57510(18) 0.03176(7) 0.0258(2) Uani 0.94 1 d PD . 1
C21 C 0.64902(5) 0.55128(16) 0.08041(6) 0.0228(3) Uani 0.94 1 d PGD A 1
C22 C 0.70610(7) 0.73565(13) 0.14221(7) 0.0270(3) Uani 0.94 1 d PGD A 1
H22 H 0.6606 0.8650 0.1491 0.032 Uiso 0.94 1 calc PR A 1
C23 C 0.83028(8) 0.72939(14) 0.19389(6) 0.0297(3) Uani 0.94 1 d PG A 1
H23 H 0.8690 0.8545 0.2358 0.036 Uiso 0.94 1 calc PR A 1
C24 C 0.89737(5) 0.53875(18) 0.18375(6) 0.0286(3) Uani 0.94 1 d PG A 1
H24 H 0.9816 0.5345 0.2188 0.034 Uiso 0.94 1 calc PR A 1
C25 C 0.84028(7) 0.35437(14) 0.12195(7) 0.0289(3) Uani 0.94 1 d PG A 1
H25 H 0.8858 0.2250 0.1151 0.035 Uiso 0.94 1 calc PR A 1
C26 C 0.71611(8) 0.36063(13) 0.07027(6) 0.0256(3) Uani 0.94 1 d PG A 1
H26 H 0.6774 0.2355 0.0283 0.031 Uiso 0.94 1 calc PR A 1
N21' N 0.5374(7) 0.418(2) 0.0066(14) 0.043(4) Uiso 0.06 1 d PD . 2
C21' C 0.6533(8) 0.476(3) 0.0707(16) 0.043(4) Uiso 0.06 1 d PGD B 2
C22' C 0.6735(14) 0.691(3) 0.1187(16) 0.043(4) Uiso 0.06 1 d PG B 2
H22' H 0.6082 0.7933 0.1105 0.052 Uiso 0.06 1 calc PR B 2
C23' C 0.7901(18) 0.757(3) 0.1786(16) 0.043(4) Uiso 0.06 1 d PG B 2
H23' H 0.8038 0.9026 0.2112 0.052 Uiso 0.06 1 calc PR B 2
C24' C 0.8864(11) 0.606(4) 0.1906(18) 0.043(4) Uiso 0.06 1 d PG B 2
H24' H 0.9655 0.6506 0.2313 0.052 Uiso 0.06 1 calc PR B 2
C25' C 0.8662(7) 0.391(4) 0.1426(19) 0.043(4) Uiso 0.06 1 d PG B 2
H25' H 0.9316 0.2893 0.1507 0.052 Uiso 0.06 1 calc PR B 2
C26' C 0.7497(10) 0.326(3) 0.0826(17) 0.043(4) Uiso 0.06 1 d PGD B 2
H26' H 0.7360 0.1800 0.0501 0.052 Uiso 0.06 1 calc PR B 2
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'
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
N11 N11 C11 113.67(11) 3_566
C12 C11 C16 120.48(9) .
C12 C11 N11 115.93(9) .
C16 C11 N11 123.54(9) .
C13 C12 C11 119.70(10) .
C13 C12 H12 121.2(8) .
C11 C12 H12 119.1(8) .
C14 C13 C12 120.16(10) .
C14 C13 H13 121.1(8) .
C12 C13 H13 118.7(8) .
C13 C14 C15 119.84(10) .
C13 C14 H14 121.4(8) .
C15 C14 H14 118.8(9) .
C16 C15 C14 120.48(10) .
C16 C15 H15 119.6(8) .
C14 C15 H15 119.9(8) .
C15 C16 C11 119.27(10) .
C15 C16 H16 121.3(8) .
C11 C16 H16 119.4(8) .
N21 N21 C21 114.24(12) 3_665
C22 C21 C26 120.0 .
C22 C21 N21 115.39(8) .
C26 C21 N21 124.61(8) .
C21 C22 C23 120.0 .
C21 C22 H22 120.0 .
C23 C22 H22 120.0 .
C22 C23 C24 120.0 .
C22 C23 H23 120.0 .
C24 C23 H23 120.0 .
C25 C24 C23 120.0 .
C25 C24 H24 120.0 .
C23 C24 H24 120.0 .
C24 C25 C26 120.0 .
C24 C25 H25 120.0 .
C26 C25 H25 120.0 .
C25 C26 C21 120.0 .
C25 C26 H26 120.0 .
C21 C26 H26 120.0 .
N21' N21' C21' 113.2(12) 3_665
C22' C21' C26' 120.0 .
C22' C21' N21' 119.7(9) .
C26' C21' N21' 120.2(9) .
C23' C22' C21' 120.0 .
C23' C22' H22' 120.0 .
C21' C22' H22' 120.0 .
C22' C23' C24' 120.0 .
C22' C23' H23' 120.0 .
C24' C23' H23' 120.0 .
C25' C24' C23' 120.0 .
C25' C24' H24' 120.0 .
C23' C24' H24' 120.0 .
C26' C25' C24' 120.0 .
C26' C25' H25' 120.0 .
C24' C25' H25' 120.0 .
C25' C26' C21' 120.0 .
C25' C26' H26' 120.0 .
C21' C26' H26' 120.0 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 N11 1.2521(18) 3_566
N11 C11 1.4305(13) .
C11 C12 1.3924(15) .
C11 C16 1.3955(14) .
C12 C13 1.3896(15) .
C12 H12 0.986(15) .
C13 C14 1.3888(17) .
C13 H13 0.977(15) .
C14 C15 1.3940(16) .
C14 H14 0.984(14) .
C15 C16 1.3884(14) .
C15 H15 1.010(14) .
C16 H16 0.955(14) .
N21 N21 1.2473(19) 3_665
N21 C21 1.4160(11) .
C21 C22 1.4000 .
C21 C26 1.4000 .
C22 C23 1.4000 .
C22 H22 0.9500 .
C23 C24 1.4000 .
C23 H23 0.9500 .
C24 C25 1.4000 .
C24 H24 0.9500 .
C25 C26 1.4000 .
C25 H25 0.9500 .
C26 H26 0.9500 .
N21' N21' 1.265(10) 3_665
N21' C21' 1.402(9) .
C21' C22' 1.4000 .
C21' C26' 1.4000 .
C22' C23' 1.4000 .
C22' H22' 0.9500 .
C23' C24' 1.4000 .
C23' H23' 0.9500 .
C24' C25' 1.4000 .
C24' H24' 0.9500 .
C25' C26' 1.4000 .
C25' H25' 0.9500 .
C26' H26' 0.9500 .
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
N11 N11 C11 C12 -162.44(11) 3_566
N11 N11 C11 C16 20.09(16) 3_566
C16 C11 C12 C13 -2.97(16) .
N11 C11 C12 C13 179.47(9) .
C11 C12 C13 C14 2.60(16) .
C12 C13 C14 C15 -0.49(17) .
C13 C14 C15 C16 -1.29(16) .
C14 C15 C16 C11 0.93(16) .
C12 C11 C16 C15 1.20(15) .
N11 C11 C16 C15 178.57(9) .
N21 N21 C21 C22 171.30(11) 3_665
N21 N21 C21 C26 -8.76(16) 3_665
C26 C21 C22 C23 0.0 .
N21 C21 C22 C23 179.94(9) .
C21 C22 C23 C24 0.0 .
C22 C23 C24 C25 0.0 .
C23 C24 C25 C26 0.0 .
C24 C25 C26 C21 0.0 .
C22 C21 C26 C25 0.0 .
N21 C21 C26 C25 -179.93(10) .
N21' N21' C21' C22' 6(4) 3_665
N21' N21' C21' C26' -171(2) 3_665
C26' C21' C22' C23' 0.0 .
N21' C21' C22' C23' -177(2) .
C21' C22' C23' C24' 0.0 .
C22' C23' C24' C25' 0.0 .
C23' C24' C25' C26' 0.0 .
C24' C25' C26' C21' 0.0 .
C22' C21' C26' C25' 0.0 .
N21' C21' C26' C25' 177(3) .
