#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:19:20 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178894 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/23/4112346.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_4112346
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                 112.4580(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1387(6)
_cell_length_b                   5.7622(3)
_cell_length_c                   15.1592(8)
_cell_measurement_reflns_used    6604
_cell_measurement_temperature    250
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      2.7
_cell_volume                     979.90(9)
_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      250
_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  0.0121
_diffrn_reflns_av_sigmaI/netI    0.0085
_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            12167
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.987943
_exptl_absorpt_correction_T_min  0.863761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.235
_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         0.250
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.125(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2251
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0398
_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)+(0.0540P)²+0.2034P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1145
_reflns_number_gt                1945
_reflns_number_total             2251
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja038203lsi20030829_041420.cif
_cod_data_source_block           azo250k
_cod_database_code               4112346
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 0.00383(8) 0.39689(16) 0.48905(7) 0.0354(2) Uani 1 1 d . . .
C11 C 0.07391(9) 0.36457(18) 0.43258(7) 0.0321(3) Uani 1 1 d . . .
C12 C 0.05995(10) 0.1530(2) 0.38563(9) 0.0397(3) Uani 1 1 d . . .
C13 C 0.12385(12) 0.1078(2) 0.32876(9) 0.0448(3) Uani 1 1 d . . .
C14 C 0.20424(11) 0.2693(2) 0.32152(9) 0.0442(3) Uani 1 1 d . . .
C15 C 0.22066(10) 0.4777(2) 0.37092(8) 0.0415(3) Uani 1 1 d . . .
C16 C 0.15524(9) 0.5273(2) 0.42614(8) 0.0350(3) Uani 1 1 d . . .
H12 H 0.0031(13) 0.038(3) 0.3930(10) 0.050(4) Uiso 1 1 d . . .
H13 H 0.1114(14) -0.040(3) 0.2954(11) 0.056(4) Uiso 1 1 d . . .
H14 H 0.2499(13) 0.240(3) 0.2836(11) 0.050(4) Uiso 1 1 d . . .
H15 H 0.2803(13) 0.593(3) 0.3678(10) 0.047(4) Uiso 1 1 d . . .
H16 H 0.1642(11) 0.670(2) 0.4597(9) 0.039(3) Uiso 1 1 d . . .
N21 N 0.52284(11) 0.5755(2) 0.03070(8) 0.0437(3) Uani 0.87 1 d PD . 1
C21 C 0.64763(6) 0.5529(2) 0.07965(7) 0.0380(3) Uani 0.87 1 d PGD A 1
C22 C 0.70348(9) 0.73638(16) 0.14099(9) 0.0460(4) Uani 0.87 1 d PGD A 1
H22 H 0.6582 0.8630 0.1473 0.055 Uiso 0.87 1 calc PR A 1
C23 C 0.82675(9) 0.73124(19) 0.19295(9) 0.0501(4) Uani 0.87 1 d PG A 1
H23 H 0.8642 0.8544 0.2341 0.060 Uiso 0.87 1 calc PR A 1
C24 C 0.89418(6) 0.5427(2) 0.18357(9) 0.0477(4) Uani 0.87 1 d PG A 1
H24 H 0.9770 0.5392 0.2185 0.057 Uiso 0.87 1 calc PR A 1
C25 C 0.83834(9) 0.35921(19) 0.12223(9) 0.0493(4) Uani 0.87 1 d PG A 1
H25 H 0.8836 0.2326 0.1159 0.059 Uiso 0.87 1 calc PR A 1
C26 C 0.71507(9) 0.36435(17) 0.07027(8) 0.0439(4) Uani 0.87 1 d PG A 1
H26 H 0.6776 0.2412 0.0291 0.053 Uiso 0.87 1 calc PR A 1
N21' N 0.5376(5) 0.4204(12) 0.0066(6) 0.0490(14) Uiso 0.13 1 d PD . 2
C21' C 0.6538(4) 0.4784(15) 0.0691(6) 0.0490(14) Uiso 0.13 1 d PGD B 2
C22' C 0.6740(7) 0.6911(15) 0.1173(7) 0.0490(14) Uiso 0.13 1 d PG B 2
H22' H 0.6099 0.7914 0.1094 0.059 Uiso 0.13 1 calc PR B 2
C23' C 0.7899(9) 0.7545(14) 0.1772(7) 0.0490(14) Uiso 0.13 1 d PG B 2
H23' H 0.8035 0.8974 0.2096 0.059 Uiso 0.13 1 calc PR B 2
C24' C 0.8854(6) 0.6052(18) 0.1889(8) 0.0490(14) Uiso 0.13 1 d PG B 2
H24' H 0.9632 0.6478 0.2291 0.059 Uiso 0.13 1 calc PR B 2
C25' C 0.8652(5) 0.3925(17) 0.1407(8) 0.0490(14) Uiso 0.13 1 d PG B 2
H25' H 0.9293 0.2922 0.1485 0.059 Uiso 0.13 1 calc PR B 2
C26' C 0.7493(6) 0.3291(13) 0.0808(7) 0.0490(14) Uiso 0.13 1 d PGD B 2
H26' H 0.7357 0.1862 0.0484 0.059 Uiso 0.13 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 113.91(11) 3_566
C12 C11 C16 120.43(10) .
C12 C11 N11 115.89(9) .
C16 C11 N11 123.64(10) .
C13 C12 C11 119.69(11) .
C13 C12 H12 121.5(9) .
C11 C12 H12 118.8(9) .
C14 C13 C12 120.16(11) .
C14 C13 H13 121.5(9) .
C12 C13 H13 118.4(9) .
C13 C14 C15 119.96(11) .
C13 C14 H14 121.2(9) .
C15 C14 H14 118.8(9) .
C16 C15 C14 120.43(11) .
C16 C15 H15 119.0(8) .
C14 C15 H15 120.5(8) .
C15 C16 C11 119.28(11) .
C15 C16 H16 121.8(8) .
C11 C16 H16 118.9(8) .
N21 N21 C21 114.30(16) 3_665
C22 C21 C26 120.0 .
C22 C21 N21 115.38(10) .
C26 C21 N21 124.62(10) .
C21 C22 C23 120.0 .
C21 C22 H22 120.0 .
C23 C22 H22 120.0 .
C24 C23 C22 120.0 .
C24 C23 H23 120.0 .
C22 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' 114.5(9) 3_665
C22' C21' C26' 120.0 .
C22' C21' N21' 119.4(6) .
C26' C21' N21' 120.6(6) .
C21' C22' C23' 120.0 .
C21' C22' H22' 120.0 .
C23' C22' H22' 120.0 .
C24' C23' C22' 120.0 .
C24' C23' H23' 120.0 .
C22' C23' H23' 120.0 .
C23' C24' C25' 120.0 .
C23' C24' H24' 120.0 .
C25' 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 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 N11 1.2468(19) 3_566
N11 C11 1.4310(13) .
C11 C12 1.3891(16) .
C11 C16 1.3917(15) .
C12 C13 1.3869(16) .
C12 H12 0.992(16) .
C13 C14 1.3827(19) .
C13 H13 0.974(17) .
C14 C15 1.3889(18) .
C14 H14 0.955(15) .
C15 C16 1.3860(15) .
C15 H15 0.997(15) .
C16 H16 0.951(14) .
N21 N21 1.239(2) 3_665
N21 C21 1.4155(13) .
C21 C22 1.4000 .
C21 C26 1.4000 .
C22 C23 1.4000 .
C22 H22 0.9400 .
C23 C24 1.4000 .
C23 H23 0.9400 .
C24 C25 1.4000 .
C24 H24 0.9400 .
C25 C26 1.4000 .
C25 H25 0.9400 .
C26 H26 0.9400 .
N21' N21' 1.256(9) 3_665
N21' C21' 1.405(7) .
C21' C22' 1.4000 .
C21' C26' 1.4000 .
C22' C23' 1.4000 .
C22' H22' 0.9400 .
C23' C24' 1.4000 .
C23' H23' 0.9400 .
C24' C25' 1.4000 .
C24' H24' 0.9400 .
C25' C26' 1.4000 .
C25' H25' 0.9400 .
C26' H26' 0.9400 .
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 -163.63(12) 3_566
N11 N11 C11 C16 18.71(18) 3_566
C16 C11 C12 C13 -2.73(17) .
N11 C11 C12 C13 179.52(10) .
C11 C12 C13 C14 2.30(19) .
C12 C13 C14 C15 -0.32(19) .
C13 C14 C15 C16 -1.24(19) .
C14 C15 C16 C11 0.81(17) .
C12 C11 C16 C15 1.18(16) .
N11 C11 C16 C15 178.74(10) .
N21 N21 C21 C22 172.57(14) 3_665
N21 N21 C21 C26 -7.5(2) 3_665
C26 C21 C22 C23 0.0 .
N21 C21 C22 C23 179.93(11) .
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 -179.92(12) .
N21' N21' C21' C22' 6.1(15) 3_665
N21' N21' C21' C26' -171.7(10) 3_665
C26' C21' C22' C23' 0.0 .
N21' C21' C22' C23' -177.8(10) .
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' 177.8(10) .
