#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:19:20 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178894 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/23/4112347.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_4112347
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                 112.4560(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0949(6)
_cell_length_b                   5.7366(3)
_cell_length_c                   15.0923(8)
_cell_measurement_reflns_used    7333
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.7
_cell_volume                     967.76(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      200
_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  0.0113
_diffrn_reflns_av_sigmaI/netI    0.0078
_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            11994
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.988587
_exptl_absorpt_correction_T_min  0.860013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.251
_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         0.288
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.071(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2224
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0389
_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)+(0.0546P)²+0.2485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1105
_reflns_number_gt                1988
_reflns_number_total             2224
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja038203lsi20030829_041438.cif
_cod_data_source_block           azo200k
_cod_database_code               4112347
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 0.00436(8) 0.39600(16) 0.48949(7) 0.0280(2) Uani 1 1 d . . .
C11 C 0.07457(9) 0.36354(18) 0.43273(7) 0.0255(2) Uani 1 1 d . . .
C12 C 0.06080(10) 0.15062(19) 0.38566(8) 0.0314(3) Uani 1 1 d . . .
C13 C 0.12486(11) 0.1055(2) 0.32845(8) 0.0351(3) Uani 1 1 d . . .
C14 C 0.20570(11) 0.2680(2) 0.32109(8) 0.0348(3) Uani 1 1 d . . .
C15 C 0.22199(10) 0.4777(2) 0.37085(8) 0.0327(3) Uani 1 1 d . . .
C16 C 0.15622(9) 0.52746(19) 0.42628(7) 0.0276(2) Uani 1 1 d . . .
H12 H 0.0037(13) 0.035(3) 0.3925(10) 0.042(4) Uiso 1 1 d . . .
H13 H 0.1121(13) -0.044(3) 0.2957(11) 0.044(4) Uiso 1 1 d . . .
H14 H 0.2536(13) 0.239(3) 0.2824(10) 0.039(4) Uiso 1 1 d . . .
H15 H 0.2833(13) 0.594(3) 0.3680(10) 0.039(4) Uiso 1 1 d . . .
H16 H 0.1661(11) 0.671(2) 0.4603(9) 0.029(3) Uiso 1 1 d . . .
N21 N 0.52310(9) 0.5755(2) 0.03122(7) 0.0343(3) Uani 0.91 1 d PD . 1
C21 C 0.64833(5) 0.55224(18) 0.08005(6) 0.0298(3) Uani 0.91 1 d PGD A 1
C22 C 0.70480(8) 0.73623(14) 0.14166(8) 0.0358(3) Uani 0.91 1 d PGD A 1
H22 H 0.6591 0.8649 0.1483 0.043 Uiso 0.91 1 calc PR A 1
C23 C 0.82860(8) 0.73061(16) 0.19348(7) 0.0394(4) Uani 0.91 1 d PG A 1
H23 H 0.8669 0.8555 0.2353 0.047 Uiso 0.91 1 calc PR A 1
C24 C 0.89592(5) 0.5410(2) 0.18368(8) 0.0375(4) Uani 0.91 1 d PG A 1
H24 H 0.9799 0.5372 0.2188 0.045 Uiso 0.91 1 calc PR A 1
C25 C 0.83945(8) 0.35703(16) 0.12206(8) 0.0385(3) Uani 0.91 1 d PG A 1
H25 H 0.8851 0.2284 0.1154 0.046 Uiso 0.91 1 calc PR A 1
C26 C 0.71566(8) 0.36264(15) 0.07025(7) 0.0340(3) Uani 0.91 1 d PG A 1
H26 H 0.6773 0.2378 0.0284 0.041 Uiso 0.91 1 calc PR A 1
N21' N 0.5371(6) 0.4179(14) 0.0074(9) 0.042(2) Uiso 0.09 1 d PD . 2
C21' C 0.6539(5) 0.477(2) 0.0688(9) 0.042(2) Uiso 0.09 1 d PGD B 2
C22' C 0.6745(9) 0.6913(19) 0.1168(10) 0.042(2) Uiso 0.09 1 d PG B 2
H22' H 0.6095 0.7937 0.1084 0.051 Uiso 0.09 1 calc PR B 2
C23' C 0.7907(12) 0.755(2) 0.1771(10) 0.042(2) Uiso 0.09 1 d PG B 2
H23' H 0.8047 0.9001 0.2096 0.051 Uiso 0.09 1 calc PR B 2
C24' C 0.8864(8) 0.604(3) 0.1894(11) 0.042(2) Uiso 0.09 1 d PG B 2
H24' H 0.9653 0.6467 0.2303 0.051 Uiso 0.09 1 calc PR B 2
C25' C 0.8659(6) 0.389(2) 0.1414(11) 0.042(2) Uiso 0.09 1 d PG B 2
H25' H 0.9308 0.2869 0.1498 0.051 Uiso 0.09 1 calc PR B 2
C26' C 0.7496(7) 0.3260(19) 0.0811(10) 0.042(2) Uiso 0.09 1 d PGD B 2
H26' H 0.7356 0.1806 0.0486 0.051 Uiso 0.09 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 113.79(11) 3_566
C12 C11 C16 120.45(10) .
C12 C11 N11 115.95(9) .
C16 C11 N11 123.55(9) .
C13 C12 C11 119.70(10) .
C13 C12 H12 121.1(9) .
C11 C12 H12 119.2(8) .
C14 C13 C12 120.22(11) .
C14 C13 H13 122.1(9) .
C12 C13 H13 117.6(9) .
C13 C14 C15 119.81(10) .
C13 C14 H14 121.9(9) .
C15 C14 H14 118.3(9) .
C16 C15 C14 120.51(11) .
C16 C15 H15 119.2(8) .
C14 C15 H15 120.2(8) .
C15 C16 C11 119.24(10) .
C15 C16 H16 121.3(8) .
C11 C16 H16 119.4(8) .
N21 N21 C21 114.25(13) 3_665
C22 C21 C26 120.0 .
C22 C21 N21 115.37(8) .
C26 C21 N21 124.63(8) .
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 .
N21' N21' C21' 113.9(10) 3_665
C22' C21' C26' 120.0 .
C22' C21' N21' 119.3(7) .
C26' C21' N21' 120.7(7) .
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 .
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 1.2495(18) 3_566
N11 C11 1.4302(13) .
C11 C12 1.3907(15) .
C11 C16 1.3937(14) .
C12 C13 1.3871(16) .
C12 H12 0.992(15) .
C13 C14 1.3857(18) .
C13 H13 0.970(16) .
C14 C15 1.3920(17) .
C14 H14 0.981(15) .
C15 C16 1.3865(15) .
C15 H15 1.011(15) .
C16 H16 0.952(14) .
N21 N21 1.244(2) 3_665
N21 C21 1.4150(12) .
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' 1.261(9) 3_665
N21' C21' 1.403(8) .
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 -162.98(12) 3_566
N11 N11 C11 C16 19.50(17) 3_566
C16 C11 C12 C13 -2.91(16) .
N11 C11 C12 C13 179.48(10) .
C11 C12 C13 C14 2.49(17) .
C12 C13 C14 C15 -0.41(18) .
C13 C14 C15 C16 -1.27(17) .
C14 C15 C16 C11 0.86(16) .
C12 C11 C16 C15 1.24(16) .
N11 C11 C16 C15 178.66(9) .
N21 N21 C21 C22 172.03(12) 3_665
N21 N21 C21 C26 -7.98(18) 3_665
C26 C21 C22 C23 0.0 .
N21 C21 C22 C23 179.99(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 -179.99(11) .
N21' N21' C21' C22' 8(2) 3_665
N21' N21' C21' C26' -170.5(14) 3_665
C26' C21' C22' C23' 0.0 .
N21' C21' C22' C23' -178.9(14) .
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' 178.9(14) .
