#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/48/2104834.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_2104834
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_coeditor_code           OG5042
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.693(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6182(2)
_cell_length_b                   26.8034(6)
_cell_length_c                   6.9510(2)
_cell_measurement_temperature    83(2)
_cell_volume                     979.20(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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15452
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.52
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9951
_exptl_absorpt_correction_T_min  0.9677
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Program SADABS was used. '
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.203
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2851
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0364
_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)+(0.0600P)²+0.1765P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1047
_reflns_number_gt                2498
_reflns_number_total             2851
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            og5042.cif
_cod_data_source_block           2-before
_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               2104834
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 -0.01736(14) 0.08054(3) 0.37278(11) 0.01601(16) Uani d . 1 . .
N N2 0.10351(15) 0.04458(3) 0.33983(12) 0.01774(17) Uani d . 1 . .
N N3 0.23354(18) 0.01306(4) 0.32928(14) 0.0280(2) Uani d . 1 . .
C C1 -0.26601(15) 0.08879(3) 0.22189(12) 0.01314(17) Uani d . 1 . .
C C2 -0.36019(17) 0.06088(3) 0.04041(13) 0.01591(17) Uani d . 1 . .
H H2 -0.256(3) 0.0353(5) 0.009(2) 0.025(3) Uiso d . 1 . .
C C3 -0.60738(18) 0.06922(3) -0.09572(13) 0.01726(18) Uani d . 1 . .
H H3 -0.673(3) 0.0496(5) -0.222(2) 0.027(3) Uiso d . 1 . .
C C4 -0.76077(17) 0.10526(3) -0.05261(13) 0.01707(18) Uani d . 1 . .
H H4 -0.930(3) 0.1108(5) -0.144(2) 0.029(3) Uiso d . 1 . .
C C5 -0.66326(16) 0.13344(3) 0.12766(13) 0.01499(17) Uani d . 1 . .
H H5 -0.773(3) 0.1602(5) 0.157(2) 0.023(3) Uiso d . 1 . .
C C6 -0.41493(15) 0.12608(3) 0.26737(12) 0.01263(16) Uani d . 1 . .
C C7 -0.31489(15) 0.15764(3) 0.45579(12) 0.01207(16) Uani d . 1 . .
C C8 -0.43761(16) 0.15812(3) 0.60016(13) 0.01402(17) Uani d . 1 . .
H H8 -0.585(3) 0.1368(5) 0.579(2) 0.024(3) Uiso d . 1 . .
C C9 -0.34892(17) 0.18897(3) 0.77357(13) 0.01571(17) Uani d . 1 . .
H H9 -0.435(3) 0.1882(5) 0.875(2) 0.023(3) Uiso d . 1 . .
C C10 -0.14016(16) 0.22026(3) 0.80274(13) 0.01570(17) Uani d . 1 . .
H H10 -0.079(3) 0.2430(5) 0.920(2) 0.023(3) Uiso d . 1 . .
C C11 -0.01779(16) 0.22010(3) 0.65872(13) 0.01553(17) Uani d . 1 . .
H H11 0.133(3) 0.2413(5) 0.676(2) 0.025(3) Uiso d . 1 . .
C C12 -0.10290(16) 0.18877(3) 0.48788(13) 0.01417(17) Uani d . 1 . .
H H12 -0.012(2) 0.1890(5) 0.3843(19) 0.018(3) Uiso d . 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'
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 . . 115.93(7) ?
N2 N1 C12 . . 156.65(6) ?
C1 N1 C12 . . 81.06(5) ?
N2 N1 N1 . 3_556 53.02(5) ?
C1 N1 N1 . 3_556 108.68(5) ?
C12 N1 N1 . 3_556 139.76(3) ?
N3 N2 N1 . . 172.64(9) ?
C2 C1 C6 . . 121.06(7) ?
C2 C1 N1 . . 122.41(7) ?
C6 C1 N1 . . 116.52(7) ?
C3 C2 C1 . . 119.64(8) ?
C3 C2 H2 . . 119.4(8) ?
C1 C2 H2 . . 120.9(8) ?
C2 C3 C4 . . 120.50(8) ?
C2 C3 H3 . . 119.5(8) ?
C4 C3 H3 . . 120.0(8) ?
C3 C4 C5 . . 119.35(8) ?
C3 C4 H4 . . 120.6(9) ?
C5 C4 H4 . . 120.0(9) ?
C4 C5 C6 . . 121.52(8) ?
C4 C5 H5 . . 119.5(7) ?
C6 C5 H5 . . 119.0(7) ?
C5 C6 C1 . . 117.91(7) ?
C5 C6 C7 . . 120.10(7) ?
C1 C6 C7 . . 121.98(7) ?
C8 C7 C12 . . 118.92(7) ?
C8 C7 C6 . . 120.31(7) ?
C12 C7 C6 . . 120.73(7) ?
C9 C8 C7 . . 120.36(8) ?
C9 C8 H8 . . 120.2(8) ?
C7 C8 H8 . . 119.5(8) ?
C10 C9 C8 . . 120.30(8) ?
C10 C9 H9 . . 120.5(8) ?
C8 C9 H9 . . 119.2(8) ?
C9 C10 C11 . . 119.56(8) ?
C9 C10 H10 . . 121.4(8) ?
C11 C10 H10 . . 119.0(8) ?
C12 C11 C10 . . 120.24(8) ?
C12 C11 H11 . . 118.1(8) ?
C10 C11 H11 . . 121.7(8) ?
C11 C12 C7 . . 120.60(8) ?
C11 C12 N1 . . 138.41(6) ?
C7 C12 N1 . . 66.58(5) ?
C11 C12 H12 . . 119.4(7) ?
C7 C12 H12 . . 120.0(7) ?
N1 C12 H12 . . 70.2(7) ?
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 . 1.2461(11) ?
N1 C1 . 1.4370(11) ?
N1 C12 . 3.0916(11) ?
N1 N1 3_556 4.6436(16) ?
N2 N3 . 1.1360(12) ?
C1 C2 . 1.3997(11) ?
C1 C6 . 1.4093(11) ?
C2 C3 . 1.3947(12) ?
C2 H2 . 0.976(14) ?
C3 C4 . 1.3958(13) ?
C3 H3 . 0.978(14) ?
C4 C5 . 1.3985(12) ?
C4 H4 . 0.951(15) ?
C5 C6 . 1.4039(11) ?
C5 H5 . 1.012(13) ?
C6 C7 . 1.4922(11) ?
C7 C8 . 1.4042(11) ?
C7 C12 . 1.4059(11) ?
C8 C9 . 1.4001(12) ?
C8 H8 . 0.972(14) ?
C9 C10 . 1.3972(12) ?
C9 H9 . 0.982(14) ?
C10 C11 . 1.4005(12) ?
C10 H10 . 0.980(13) ?
C11 C12 . 1.3938(12) ?
C11 H11 . 0.990(14) ?
C12 H12 . 1.020(12) ?
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(4) ?
C12 N1 N2 N3 . . . . 48.4(9) ?
N1 N1 N2 N3 3_556 . . . -83.4(8) ?
N2 N1 C1 C2 . . . . -4.94(12) ?
C12 N1 C1 C2 . . . . 158.17(8) ?
N1 N1 C1 C2 3_556 . . . -62.14(9) ?
N2 N1 C1 C6 . . . . 173.79(8) ?
C12 N1 C1 C6 . . . . -23.10(7) ?
N1 N1 C1 C6 3_556 . . . 116.59(7) ?
C6 C1 C2 C3 . . . . -1.48(13) ?
N1 C1 C2 C3 . . . . 177.19(8) ?
C1 C2 C3 C4 . . . . 0.24(13) ?
C2 C3 C4 C5 . . . . 0.73(13) ?
C3 C4 C5 C6 . . . . -0.49(13) ?
C4 C5 C6 C1 . . . . -0.71(12) ?
C4 C5 C6 C7 . . . . 178.55(8) ?
C2 C1 C6 C5 . . . . 1.70(12) ?
N1 C1 C6 C5 . . . . -177.05(7) ?
C2 C1 C6 C7 . . . . -177.55(8) ?
N1 C1 C6 C7 . . . . 3.70(11) ?
C5 C6 C7 C8 . . . . 59.51(11) ?
C1 C6 C7 C8 . . . . -121.25(9) ?
C5 C6 C7 C12 . . . . -118.00(9) ?
C1 C6 C7 C12 . . . . 61.23(11) ?
C12 C7 C8 C9 . . . . -0.31(12) ?
C6 C7 C8 C9 . . . . -177.88(8) ?
C7 C8 C9 C10 . . . . 1.17(12) ?
C8 C9 C10 C11 . . . . -0.86(13) ?
C9 C10 C11 C12 . . . . -0.29(13) ?
C10 C11 C12 C7 . . . . 1.15(13) ?
C10 C11 C12 N1 . . . . -87.17(11) ?
C8 C7 C12 C11 . . . . -0.84(12) ?
C6 C7 C12 C11 . . . . 176.71(7) ?
C8 C7 C12 N1 . . . . 132.85(8) ?
C6 C7 C12 N1 . . . . -49.60(6) ?
N2 N1 C12 C11 . . . . -65.50(19) ?
C1 N1 C12 C11 . . . . 155.72(10) ?
N1 N1 C12 C11 3_556 . . . 47.30(11) ?
N2 N1 C12 C7 . . . . -175.85(16) ?
C1 N1 C12 C7 . . . . 45.37(6) ?
N1 N1 C12 C7 3_556 . . . -63.05(7) ?
