#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/48/2104835.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_2104835
loop_
_publ_author_name
'Takayama, Terufumi'
'Mitsumori, Takahiro'
'Kawano, Masaki'
'Sekine, Akiko'
'Uekusa, Hidehiro'
'Ohashi, Yuji'
'Sugawara, Tadashi'
_publ_section_title
;
 Direct observation of arylnitrene formation in the photoreaction of
 arylazide crystals
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              639
_journal_page_last               646
_journal_paper_doi               10.1107/S0108768110036608
_journal_volume                  66
_journal_year                    2010
_chemical_formula_moiety         'C12 H9 N3'
_chemical_formula_sum            'C12 H9 N3'
_chemical_formula_weight         195.22
_chemical_melting_point          ?
_chemical_name_common
;
 2-azidobiphenyl
;
_chemical_name_systematic
;
 2-azidobiphenyl
;
_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     'rigid group'
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.830(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6598(2)
_cell_length_b                   27.1299(5)
_cell_length_c                   6.9417(2)
_cell_measurement_temperature    83(2)
_cell_volume                     996.23(5)
_computing_cell_refinement       'Siemens SMART'
_computing_data_collection       'Siemens SMART'
_computing_data_reduction        'Siemens SAINT & SADABS'
_computing_molecular_graphics    'ORTEP3 for Window (Farrugia,1998)'
_computing_publication_material  SHELXTL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      83(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area detector system'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_sigmaI/netI    0.0427
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15755
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         1.50
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9935
_exptl_absorpt_correction_T_min  0.9760
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Program SADABS was used. '
_exptl_crystal_colour            pale-brown
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.206
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         2890
_refine_ls_number_restraints     158
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0761P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1302
_reflns_number_gt                2048
_reflns_number_total             2890
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            og5042.cif
_cod_data_source_block           2-after
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               2104835
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
N N1 -0.03702(17) 0.08230(3) 0.36606(14) 0.0261(4) Uani d PG 0.801(5) A 1
N N2 0.08305(19) 0.04654(3) 0.33351(15) 0.0287(4) Uani d PG 0.801(5) A 1
N N3 0.2124(2) 0.01523(4) 0.3232(2) 0.0440(6) Uani d PG 0.801(5) A 1
C C1 -0.28567(17) 0.09026(3) 0.21509(16) 0.0225(5) Uani d PG 0.801(5) A 1
C C2 -0.3811(2) 0.06226(4) 0.03365(17) 0.0276(7) Uani d PG 0.801(5) A 1
H H2 -0.2779 0.0367 0.0017 0.029(5) Uiso d PG 0.801(5) A 1
C C3 -0.6282(3) 0.07034(6) -0.1026(2) 0.0294(7) Uani d PG 0.801(5) A 1
H H3 -0.6953 0.0506 -0.2296 0.041(6) Uiso d PG 0.801(5) A 1
C C4 -0.7805(2) 0.10620(7) -0.0595(3) 0.0281(6) Uani d PG 0.801(5) A 1
H H4 -0.9500 0.1115 -0.1511 0.026(5) Uiso d PG 0.801(5) A 1
C C5 -0.6819(2) 0.13448(5) 0.1207(3) 0.0259(7) Uani d PG 0.801(5) A 1
H H5 -0.7907 0.1612 0.1500 0.023(4) Uiso d PG 0.801(5) A 1
C C6 -0.43347(18) 0.12737(4) 0.2604(2) 0.0218(6) Uani d PG 0.801(5) A 1
C C7 -0.3324(2) 0.15901(5) 0.4485(2) 0.0203(7) Uani d PGD 0.801(5) A 1
C C8 -0.4528(3) 0.15978(7) 0.5944(3) 0.0244(8) Uani d PGD 0.801(5) A 1
H H8 -0.5989 0.1386 0.5744 0.028(5) Uiso d PG 0.801(5) A 1
C C9 -0.3630(4) 0.19067(8) 0.7677(3) 0.0271(8) Uani d PGD 0.801(5) A 1
H H9 -0.4467 0.1902 0.8703 0.035(5) Uiso d PG 0.801(5) A 1
C C10 -0.1554(4) 0.22169(8) 0.7952(3) 0.0244(7) Uani d PGD 0.801(5) A 1
H H10 -0.0942 0.2445 0.9123 0.027(4) Uiso d PG 0.801(5) A 1
C C11 -0.0353(4) 0.22124(6) 0.6496(3) 0.0235(7) Uani d PGD 0.801(5) A 1
H H11 0.1150 0.2422 0.6662 0.032(5) Uiso d PG 0.801(5) A 1
C C12 -0.1215(3) 0.18985(4) 0.4790(3) 0.0237(7) Uani d PGD 0.801(5) A 1
H H12 -0.0315 0.1898 0.3743 0.043(6) Uiso d PG 0.801(5) A 1
N N1P -0.034(3) 0.0857(6) 0.341(2) 0.112(6) Uani d PU 0.199(5) A 2
N N2P 0.313(3) 0.0194(9) 0.340(3) 0.259(16) Uani d PDU 0.199(5) A 2
N N3P 0.198(5) -0.0051(11) 0.397(4) 0.185(10) Uani d PDU 0.199(5) A 2
C C1P -0.282(3) 0.0916(7) 0.203(2) 0.092(6) Uani d PU 0.199(5) A 2
C C2P -0.363(4) 0.0635(6) 0.035(2) 0.086(6) Uani d PU 0.199(5) A 2
H H2P -0.2553 0.0395 0.0093 0.103 Uiso calc PR 0.199(5) A 2
C C3P -0.578(5) 0.0692(6) -0.084(3) 0.071(5) Uani d PU 0.199(5) A 2
H H3P -0.6306 0.0498 -0.2060 0.086 Uiso calc PR 0.199(5) A 2
C C4P -0.745(3) 0.1001(7) -0.059(3) 0.062(4) Uani d PU 0.199(5) A 2
H H4P -0.9129 0.1016 -0.1548 0.074 Uiso calc PR 0.199(5) A 2
C C5P -0.666(3) 0.1301(5) 0.112(3) 0.055(4) Uani d PU 0.199(5) A 2
H H5P -0.7761 0.1540 0.1351 0.067 Uiso calc PR 0.199(5) A 2
C C6P -0.426(3) 0.1246(5) 0.247(2) 0.059(5) Uani d PU 0.199(5) A 2
C C7P -0.345(2) 0.1540(5) 0.427(2) 0.046(4) Uani d PDU 0.199(5) A 2
C C8P -0.462(3) 0.1571(5) 0.572(2) 0.044(4) Uani d PDU 0.199(5) A 2
H H8P -0.6117 0.1383 0.5460 0.052 Uiso calc PR 0.199(5) A 2
C C9P -0.384(2) 0.1841(5) 0.743(2) 0.032(3) Uani d PDU 0.199(5) A 2
H H9P -0.4744 0.1837 0.8353 0.038 Uiso calc PR 0.199(5) A 2
C C10P -0.175(3) 0.2119(6) 0.7847(18) 0.031(3) Uani d PDU 0.199(5) A 2
H H10P -0.1154 0.2313 0.9064 0.037 Uiso calc PR 0.199(5) A 2
C C11P -0.050(2) 0.2116(5) 0.646(2) 0.035(3) Uani d PDU 0.199(5) A 2
H H11P 0.0967 0.2313 0.6703 0.042 Uiso calc PR 0.199(5) A 2
C C12P -0.138(2) 0.1832(4) 0.4789(16) 0.040(3) Uani d PDU 0.199(5) A 2
H H12P -0.0469 0.1835 0.3875 0.048 Uiso calc PR 0.199(5) A 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C1 . . 116.0 ?
N3 N2 N1 . . 172.7 ?
C2 C1 C6 . . 121.0 ?
C2 C1 N1 . . 122.4 ?
C6 C1 N1 . . 116.5 ?
C3 C2 C1 . . 119.6 ?
C2 C3 C4 . . 120.5 ?
C3 C4 C5 . . 119.3 ?
C4 C5 C6 . . 121.5 ?
C5 C6 C1 . . 118.0 ?
C5 C6 C7 . . 120.0 ?
C1 C6 C7 . . 122.0 ?
C8 C7 C12 . . 118.9 ?
C8 C7 C6 . . 120.3 ?
C12 C7 C6 . . 120.8 ?
C9 C8 C7 . . 120.3 ?
C10 C9 C8 . . 120.3 ?
C9 C10 C11 . . 119.6 ?
C12 C11 C10 . . 120.2 ?
C11 C12 C7 . . 120.7 ?
C6P C1P C2P . . 122.9(14) ?
C6P C1P N1P . . 118.3(13) ?
C2P C1P N1P . . 118.8(14) ?
C3P C2P C1P . . 118.3(14) ?
C3P C2P H2 . . 113.9 ?
C1P C2P H2 . . 127.5 ?
C3P C2P H2P . . 120.9 ?
C1P C2P H2P . . 120.9 ?
H2 C2P H2P . . 8.6 ?
C2P C3P C4P . . 125.4(13) ?
C2P C3P H3 . . 133.8 ?
C4P C3P H3 . . 100.7 ?
C2P C3P H3P . . 117.3 ?
C4P C3P H3P . . 117.3 ?
H3 C3P H3P . . 17.0 ?
C3P C4P C5P . . 117.6(14) ?
C3P C4P H4 . . 136.2 ?
C5P C4P H4 . . 106.0 ?
C3P C4P H4P . . 121.2 ?
C5P C4P H4P . . 121.2 ?
H4 C4P H4P . . 15.5 ?
C6P C5P C4P . . 117.9(14) ?
C6P C5P H5 . . 117.0 ?
C4P C5P H5 . . 125.1 ?
C6P C5P H5P . . 121.1 ?
C4P C5P H5P . . 121.1 ?
H5 C5P H5P . . 4.1 ?
C1P C6P C5P . . 117.8(13) ?
C1P C6P C7P . . 123.6(12) ?
C5P C6P C7P . . 118.5(13) ?
C12P C7P C8P . . 111.4(11) ?
C12P C7P C6P . . 122.6(9) ?
C8P C7P C6P . . 126.0(11) ?
C9P C8P C7P . . 126.0(11) ?
C9P C8P H8 . . 107.0 ?
C7P C8P H8 . . 126.7 ?
C9P C8P H8P . . 117.0 ?
C7P C8P H8P . . 117.0 ?
H8 C8P H8P . . 11.2 ?
C8P C9P C10P . . 119.1(9) ?
C8P C9P H9 . . 135.7 ?
C10P C9P H9 . . 105.2 ?
C8P C9P H9P . . 120.4 ?
C10P C9P H9P . . 120.4 ?
H9 C9P H9P . . 15.3 ?
C9P C10P C11P . . 118.6(9) ?
C9P C10P H10 . . 129.6 ?
C11P C10P H10 . . 110.7 ?
C9P C10P H10P . . 120.7 ?
C11P C10P H10P . . 120.7 ?
H10 C10P H10P . . 13.9 ?
C12P C11P C10P . . 118.8(9) ?
C12P C11P H11 . . 121.7 ?
C10P C11P H11 . . 118.7 ?
C12P C11P H11P . . 120.6 ?
C10P C11P H11P . . 120.6 ?
H11 C11P H11P . . 9.0 ?
C11P C12P C7P . . 126.1(9) ?
C11P C12P H12 . . 110.7 ?
C7P C12P H12 . . 122.9 ?
C11P C12P H12P . . 117.0 ?
C7P C12P H12P . . 117.0 ?
H12 C12P H12P . . 8.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 N2 . 1.2502 ?
N1 C1 . 1.4410 ?
N2 N3 . 1.1403 ?
C1 C2 . 1.4041 ?
C1 C6 . 1.4140 ?
C2 C3 . 1.3994 ?
C2 H2 . 0.9808 ?
C3 C4 . 1.4007 ?
C3 H3 . 0.9851 ?
C4 C5 . 1.4031 ?
C4 H4 . 0.9545 ?
C5 C6 . 1.4089 ?
C5 H5 . 1.0175 ?
C6 C7 . 1.4960 ?
C7 C8 . 1.4074 ?
C7 C12 . 1.4108 ?
C8 C9 . 1.4047 ?
C8 H8 . 0.9757 ?
C9 C10 . 1.4019 ?
C9 H9 . 0.9859 ?
C10 C11 . 1.4041 ?
C10 H10 . 0.9807 ?
C11 C12 . 1.3984 ?
C11 H11 . 0.9952 ?
C12 H12 . 1.0248 ?
N1P C1P . 1.396(19) ?
N2P N3P . 1.0977(11) ?
C1P C6P . 1.317(19) ?
C1P C2P . 1.33(2) ?
C2P C3P . 1.21(2) ?
C2P H2 . 0.9439 ?
C2P H2P . 0.9500 ?
C3P C4P . 1.32(2) ?
C3P H3 . 1.1126 ?
C3P H3P . 0.9500 ?
C4P C5P . 1.375(19) ?
C4P H4 . 1.1523 ?
C4P H4P . 0.9500 ?
C5P C6P . 1.355(17) ?
C5P H5 . 1.1877 ?
C5P H5P . 0.9500 ?
C6P C7P . 1.416(17) ?
C7P C12P . 1.354(12) ?
C7P C8P . 1.385(11) ?
C8P C9P . 1.334(12) ?
C8P H8 . 0.9286 ?
C8P H8P . 0.9500 ?
C9P C10P . 1.341(11) ?
C9P H9 . 1.0737 ?
C9P H9P . 0.9500 ?
C10P C11P . 1.383(10) ?
C10P H10 . 1.2197 ?
C10P H10P . 0.9500 ?
C11P C12P . 1.336(11) ?
C11P H11 . 1.2194 ?
C11P H11P . 0.9500 ?
C12P H12 . 1.1113 ?
C12P H12P . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N1 N2 N3 . . . . -18E1(5) ?
N2 N1 C1 C2 . . . . -4.9 ?
N2 N1 C1 C6 . . . . 173.8 ?
C6 C1 C2 C3 . . . . -1.5 ?
N1 C1 C2 C3 . . . . 177.2 ?
C1 C2 C3 C4 . . . . 0.2 ?
C2 C3 C4 C5 . . . . 0.8 ?
C3 C4 C5 C6 . . . . -0.5 ?
C4 C5 C6 C1 . . . . -0.7 ?
C4 C5 C6 C7 . . . . 178.5 ?
C2 C1 C6 C5 . . . . 1.7 ?
N1 C1 C6 C5 . . . . -177.0 ?
C2 C1 C6 C7 . . . . -177.5 ?
N1 C1 C6 C7 . . . . 3.7 ?
C5 C6 C7 C8 . . . . 59.6 ?
C1 C6 C7 C8 . . . . -121.2 ?
C5 C6 C7 C12 . . . . -118.1 ?
C1 C6 C7 C12 . . . . 61.2 ?
C12 C7 C8 C9 . . . . -0.3 ?
C6 C7 C8 C9 . . . . -177.9 ?
C7 C8 C9 C10 . . . . 1.1 ?
C8 C9 C10 C11 . . . . -0.8 ?
C9 C10 C11 C12 . . . . -0.3 ?
C10 C11 C12 C7 . . . . 1.2 ?
C8 C7 C12 C11 . . . . -0.9 ?
C6 C7 C12 C11 . . . . 176.7 ?
C6P C1P C2P C3P . . . . 1(3) ?
N1P C1P C2P C3P . . . . -179.4(15) ?
C1P C2P C3P C4P . . . . -2(3) ?
C2P C3P C4P C5P . . . . 3(2) ?
C3P C4P C5P C6P . . . . -2.5(17) ?
C2P C1P C6P C5P . . . . -1(2) ?
N1P C1P C6P C5P . . . . 179.8(13) ?
C2P C1P C6P C7P . . . . 178.3(13) ?
N1P C1P C6P C7P . . . . -1(2) ?
C4P C5P C6P C1P . . . . 1.4(17) ?
C4P C5P C6P C7P . . . . -177.6(10) ?
C1P C6P C7P C12P . . . . 56.3(16) ?
C5P C6P C7P C12P . . . . -124.7(11) ?
C1P C6P C7P C8P . . . . -123.9(14) ?
C5P C6P C7P C8P . . . . 55.1(15) ?
C12P C7P C8P C9P . . . . -1.3(14) ?
C6P C7P C8P C9P . . . . 178.9(10) ?
C7P C8P C9P C10P . . . . 1.0(15) ?
C8P C9P C10P C11P . . . . 0.3(14) ?
C9P C10P C11P C12P . . . . -1.1(14) ?
C10P C11P C12P C7P . . . . 0.6(16) ?
C8P C7P C12P C11P . . . . 0.5(14) ?
C6P C7P C12P C11P . . . . -179.7(10) ?
