#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/48/2104845.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_2104845
loop_
_publ_author_name
'Mitsumori, Takahiro'
'Sekine, Akiko'
'Uekusa, Hidehiro'
'Ohashi, Yuji'
_publ_section_title
;
 Direct observation of various reaction pathways of arylnitrenes in
 different crystal environments caused by acid--base complex formation
;
_journal_coeditor_code           OG5043
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              647
_journal_page_last               661
_journal_paper_doi               10.1107/S010876811003661X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_moiety         'C19 H28 N4 O2'
_chemical_formula_sum            'C19 H28 N4 O2'
_chemical_formula_weight         344.45
_chemical_melting_point          ?
_chemical_name_common            'Dicyclohexylammonium 3-azidebenzoate'
_chemical_name_systematic
;
Dicyclohexylammonium 3-azidebenzoate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                110.8160(10)
_cell_angle_beta                 103.168(2)
_cell_angle_gamma                103.3700(10)
_cell_formula_units_Z            2
_cell_length_a                   9.1925(5)
_cell_length_b                   10.1813(5)
_cell_length_c                   11.3543(6)
_cell_measurement_reflns_used    6022
_cell_measurement_temperature    82(2)
_cell_volume                     908.51(8)
_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      82(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14513
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9786
_exptl_absorpt_correction_T_min  0.9642
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Program SADABS was used. '
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.241
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         5259
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0343
_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)+(0.0603P)²+0.1086P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.0999
_reflns_number_gt                4561
_reflns_number_total             5259
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            og5043.cif
_cod_data_source_block           3a-dc-i
_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      P-1
_cod_database_code               2104845
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C C7 0.70855(8) 0.21243(8) 0.35622(7) 0.01268(14) Uani d . 1 . .
C C1 0.32743(9) -0.12205(8) 0.23699(8) 0.01447(15) Uani d . 1 . .
C C2 0.45174(9) 0.01540(8) 0.31880(7) 0.01310(14) Uani d . 1 . .
H H2 0.4580(13) 0.0764(12) 0.4099(11) 0.016 Uiso d . 1 . .
C C3 0.57277(8) 0.06267(8) 0.27095(7) 0.01286(14) Uani d . 1 . .
C C4 0.56854(9) -0.02721(9) 0.14289(8) 0.01656(15) Uani d . 1 . .
H H4 0.6537(14) 0.0086(13) 0.1104(11) 0.020 Uiso d . 1 . .
C C5 0.44280(10) -0.16295(9) 0.06162(8) 0.01891(16) Uani d . 1 . .
H H5 0.4334(14) -0.2283(13) -0.0342(12) 0.023 Uiso d . 1 . .
C C6 0.32247(10) -0.21067(9) 0.10857(8) 0.01750(15) Uani d . 1 . .
H H6 0.2340(14) -0.3066(13) 0.0532(11) 0.021 Uiso d . 1 . .
O O1 0.70011(7) 0.29827(6) 0.46504(6) 0.01637(12) Uani d . 1 . .
O O2 0.81882(7) 0.23951(7) 0.30949(6) 0.01751(13) Uani d . 1 . .
N N1 0.19848(8) -0.18239(8) 0.27522(7) 0.01976(15) Uani d . 1 . .
N N2 0.19097(8) -0.10182(8) 0.38449(7) 0.01736(14) Uani d . 1 . .
N N3 0.16737(9) -0.04166(8) 0.48004(8) 0.02245(16) Uani d . 1 . .
C C8 0.19607(8) 0.33539(8) 0.51332(7) 0.01066(13) Uani d . 1 . .
H H8 0.1478(13) 0.2249(12) 0.4671(10) 0.013 Uiso d . 1 . .
C C9 0.37823(8) 0.38432(8) 0.56345(7) 0.01276(14) Uani d . 1 . .
H H91 0.4184(13) 0.4932(12) 0.5983(10) 0.015 Uiso d . 1 . .
H H92 0.4197(13) 0.3430(12) 0.4900(11) 0.015 Uiso d . 1 . .
C C10 0.43700(9) 0.33466(9) 0.67339(8) 0.01423(14) Uani d . 1 . .
H H101 0.3959(13) 0.2232(13) 0.6352(11) 0.017 Uiso d . 1 . .
H H102 0.5546(13) 0.3669(12) 0.7044(11) 0.017 Uiso d . 1 . .
C C11 0.37735(10) 0.39622(9) 0.79020(8) 0.01746(15) Uani d . 1 . .
H H111 0.4231(14) 0.5096(13) 0.8321(12) 0.021 Uiso d . 1 . .
H H112 0.4142(14) 0.3637(13) 0.8620(11) 0.021 Uiso d . 1 . .
C C12 0.19439(10) 0.34459(10) 0.73900(8) 0.01672(15) Uani d . 1 . .
H H121 0.1516(14) 0.2336(13) 0.7038(11) 0.020 Uiso d . 1 . .
H H122 0.1563(14) 0.3861(13) 0.8138(11) 0.020 Uiso d . 1 . .
C C13 0.13321(9) 0.39282(8) 0.62883(7) 0.01319(14) Uani d . 1 . .
H H131 0.0127(13) 0.3532(12) 0.5901(11) 0.016 Uiso d . 1 . .
H H132 0.1684(13) 0.5036(12) 0.6655(11) 0.016 Uiso d . 1 . .
C C14 0.18670(8) 0.35429(8) 0.29082(7) 0.01063(13) Uani d . 1 . .
H H14 0.3007(13) 0.4071(12) 0.3229(10) 0.013 Uiso d . 1 . .
C C15 0.09930(9) 0.41119(8) 0.19752(7) 0.01276(14) Uani d . 1 . .
H H151 0.1219(13) 0.5200(12) 0.2462(11) 0.015 Uiso d . 1 . .
H H152 -0.0179(13) 0.3587(12) 0.1705(11) 0.015 Uiso d . 1 . .
C C16 0.14699(9) 0.37695(9) 0.07112(7) 0.01443(14) Uani d . 1 . .
H H161 0.0811(13) 0.4088(13) 0.0098(11) 0.017 Uiso d . 1 . .
H H162 0.2609(14) 0.4398(13) 0.0977(11) 0.017 Uiso d . 1 . .
C C17 0.12389(10) 0.21029(9) -0.00144(8) 0.01670(15) Uani d . 1 . .
H H171 0.1639(14) 0.1907(13) -0.0790(11) 0.020 Uiso d . 1 . .
H H172 0.0067(14) 0.1506(13) -0.0381(12) 0.020 Uiso d . 1 . .
C C18 0.20933(10) 0.15616(9) 0.09535(8) 0.01642(15) Uani d . 1 . .
H H181 0.3260(14) 0.2096(13) 0.1283(11) 0.020 Uiso d . 1 . .
H H182 0.1905(14) 0.0468(13) 0.0484(11) 0.020 Uiso d . 1 . .
C C19 0.15390(9) 0.18612(8) 0.21759(7) 0.01370(14) Uani d . 1 . .
H H191 0.0384(13) 0.1314(12) 0.1899(11) 0.016 Uiso d . 1 . .
H H192 0.2127(13) 0.1476(12) 0.2772(11) 0.016 Uiso d . 1 . .
N N4 0.13682(7) 0.39406(7) 0.41333(6) 0.01020(12) Uani d . 1 . .
H H1N 0.0246(14) 0.3568(13) 0.3842(11) 0.021(3) Uiso d . 1 . .
H H2N 0.1767(15) 0.4977(14) 0.4572(12) 0.024(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'
O O 0.0106 0.0060 '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
O1 C7 O2 . . 126.05(7) ?
O1 C7 C3 . . 117.77(6) ?
O2 C7 C3 . . 116.18(7) ?
C6 C1 C2 . . 120.65(7) ?
C6 C1 N1 . . 114.95(7) ?
C2 C1 N1 . . 124.40(7) ?
C3 C2 C1 . . 119.36(7) ?
C3 C2 H2 . . 119.4(6) ?
C1 C2 H2 . . 121.1(6) ?
C4 C3 C2 . . 119.87(7) ?
C4 C3 C7 . . 119.28(7) ?
C2 C3 C7 . . 120.84(7) ?
C3 C4 C5 . . 120.20(7) ?
C3 C4 H4 . . 118.7(7) ?
C5 C4 H4 . . 121.0(7) ?
C6 C5 C4 . . 120.22(7) ?
C6 C5 H5 . . 117.8(7) ?
C4 C5 H5 . . 121.9(7) ?
C5 C6 C1 . . 119.68(7) ?
C5 C6 H6 . . 121.2(7) ?
C1 C6 H6 . . 119.1(7) ?
N2 N1 C1 . . 117.16(7) ?
N3 N2 N1 . . 171.75(8) ?
N4 C8 C13 . . 107.56(5) ?
N4 C8 C9 . . 111.33(6) ?
C13 C8 C9 . . 111.57(6) ?
N4 C8 H8 . . 107.0(6) ?
C13 C8 H8 . . 108.5(6) ?
C9 C8 H8 . . 110.7(6) ?
C6 C9 C10 . . 110.60(6) ?
C6 C9 H91 . . 106.7(6) ?
C10 C9 H91 . . 110.9(6) ?
C6 C9 H92 . . 112.1(6) ?
C10 C9 H92 . . 108.8(6) ?
H91 C9 H92 . . 107.7(9) ?
C11 C10 C9 . . 111.16(6) ?
C11 C10 H101 . . 108.2(6) ?
C9 C10 H101 . . 109.4(6) ?
C11 C10 H102 . . 111.3(6) ?
C9 C10 H102 . . 109.5(7) ?
H101 C10 H102 . . 107.2(9) ?
C10 C11 C12 . . 110.10(6) ?
C10 C11 H111 . . 108.5(7) ?
C12 C11 H111 . . 109.6(7) ?
C10 C11 H112 . . 111.8(6) ?
C12 C11 H112 . . 109.5(7) ?
H111 C11 H112 . . 107.3(9) ?
C13 C12 C11 . . 111.07(6) ?
C13 C12 H121 . . 110.3(7) ?
C11 C12 H121 . . 108.5(7) ?
C13 C12 H122 . . 109.8(7) ?
C11 C12 H122 . . 110.0(7) ?
H121 C12 H122 . . 107.0(9) ?
C6 C13 C12 . . 111.18(6) ?
C6 C13 H131 . . 107.8(6) ?
C12 C13 H131 . . 111.6(6) ?
C6 C13 H132 . . 108.1(6) ?
C12 C13 H132 . . 110.5(6) ?
H131 C13 H132 . . 107.6(9) ?
N4 C14 C19 . . 112.60(6) ?
N4 C14 C15 . . 108.14(5) ?
C19 C14 C15 . . 111.00(6) ?
N4 C14 H14 . . 106.2(6) ?
C19 C14 H14 . . 108.9(6) ?
C15 C14 H14 . . 109.9(6) ?
C14 C15 C16 . . 111.01(6) ?
C14 C15 H151 . . 110.0(6) ?
C16 C15 H151 . . 110.6(6) ?
C14 C15 H152 . . 107.8(6) ?
C16 C15 H152 . . 109.3(6) ?
H151 C15 H152 . . 108.1(9) ?
C17 C16 C15 . . 111.83(6) ?
C17 C16 H161 . . 110.5(6) ?
C15 C16 H161 . . 108.4(6) ?
C17 C16 H162 . . 110.2(6) ?
C15 C16 H162 . . 108.8(6) ?
H161 C16 H162 . . 106.9(9) ?
C16 C17 C18 . . 110.97(6) ?
C16 C17 H171 . . 111.2(7) ?
C18 C17 H171 . . 109.5(7) ?
C16 C17 H172 . . 108.8(7) ?
C18 C17 H172 . . 108.7(7) ?
H171 C17 H172 . . 107.7(9) ?
C17 C18 C19 . . 111.51(6) ?
C17 C18 H181 . . 109.7(7) ?
C19 C18 H181 . . 108.2(6) ?
C17 C18 H182 . . 110.6(7) ?
C19 C18 H182 . . 109.4(7) ?
H181 C18 H182 . . 107.4(9) ?
C14 C19 C18 . . 109.03(6) ?
C14 C19 H191 . . 109.1(6) ?
C18 C19 H191 . . 111.1(6) ?
C14 C19 H192 . . 111.9(6) ?
C18 C19 H192 . . 108.2(6) ?
H191 C19 H192 . . 107.5(9) ?
C14 N4 C6 . . 117.34(5) ?
C14 N4 H1N . . 108.1(7) ?
C6 N4 H1N . . 106.9(7) ?
C14 N4 H2N . . 105.4(7) ?
C6 N4 H2N . . 107.6(7) ?
H1N N4 H2N . . 111.7(10) ?
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
C7 O1 . 1.2665(9) ?
C7 O2 . 1.2668(9) ?
C7 C3 . 1.5298(10) ?
C1 C6 . 1.3993(11) ?
C1 C2 . 1.4071(10) ?
C1 N1 . 1.4346(10) ?
C2 C3 . 1.4065(10) ?
C2 H2 . 0.979(11) ?
C3 C4 . 1.4019(10) ?
C4 C5 . 1.4023(11) ?
C4 H4 . 0.989(12) ?
C5 C6 . 1.3957(12) ?
C5 H5 . 1.025(11) ?
C6 H6 . 0.987(12) ?
N1 N2 . 1.2486(10) ?
N2 N3 . 1.1382(11) ?
C8 N4 . 1.5143(9) ?
C8 C13 . 1.5337(10) ?
C8 C9 . 1.5344(10) ?
C8 H8 . 0.991(11) ?
C9 C10 . 1.5406(10) ?
C9 H91 . 0.976(11) ?
C9 H92 . 0.994(11) ?
C10 C11 . 1.5337(11) ?
C10 H101 . 0.998(11) ?
C10 H102 . 0.990(11) ?
C11 C12 . 1.5399(11) ?
C11 H111 . 1.015(12) ?
C11 H112 . 1.003(12) ?
C12 C13 . 1.5382(10) ?
C12 H121 . 0.997(12) ?
C12 H122 . 0.986(11) ?
C13 H131 . 1.014(11) ?
C13 H132 . 0.993(11) ?
C14 N4 . 1.5116(9) ?
C14 C19 . 1.5327(10) ?
C14 C15 . 1.5386(10) ?
C14 H14 . 0.973(11) ?
C15 C16 . 1.5412(10) ?
C15 H151 . 0.991(11) ?
C15 H152 . 1.004(11) ?
C16 C17 . 1.5372(11) ?
C16 H161 . 1.008(11) ?
C16 H162 . 1.003(12) ?
C17 C18 . 1.5381(11) ?
C17 H171 . 1.003(11) ?
C17 H172 . 1.008(12) ?
C18 C19 . 1.5402(10) ?
C18 H181 . 0.994(12) ?
C18 H182 . 1.000(11) ?
C19 H191 . 0.994(11) ?
C19 H192 . 1.012(11) ?
N4 H1N . 0.944(12) ?
N4 H2N . 0.928(13) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N4 H1N O2 1_455 0.944(12) 1.797(12) 2.7194(8) 164.9(11)
N4 H2N O1 2_666 0.928(13) 1.879(13) 2.7888(8) 166.3(11)
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
C6 C1 C2 C3 . . . . -0.73(11) ?
N1 C1 C2 C3 . . . . 179.46(7) ?
C1 C2 C3 C4 . . . . -0.06(11) ?
C1 C2 C3 C7 . . . . 179.13(6) ?
O1 C7 C3 C4 . . . . 172.53(7) ?
O2 C7 C3 C4 . . . . -6.57(10) ?
O1 C7 C3 C2 . . . . -6.66(10) ?
O2 C7 C3 C2 . . . . 174.24(7) ?
C2 C3 C4 C5 . . . . 0.96(12) ?
C7 C3 C4 C5 . . . . -178.24(7) ?
C3 C4 C5 C6 . . . . -1.09(12) ?
C4 C5 C6 C1 . . . . 0.30(12) ?
C2 C1 C6 C5 . . . . 0.61(12) ?
N1 C1 C6 C5 . . . . -179.57(7) ?
C6 C1 N1 N2 . . . . -174.40(7) ?
C2 C1 N1 N2 . . . . 5.42(11) ?
C1 N1 N2 N3 . . . . 175.5(5) ?
N4 C8 C9 C10 . . . . 175.39(6) ?
C13 C8 C9 C10 . . . . 55.21(8) ?
C8 C9 C10 C11 . . . . -56.76(8) ?
C9 C10 C11 C12 . . . . 57.53(8) ?
C10 C11 C12 C13 . . . . -56.87(8) ?
N4 C8 C13 C12 . . . . -177.31(6) ?
C9 C8 C13 C12 . . . . -54.94(8) ?
C11 C12 C13 C6 . . . . 55.71(8) ?
N4 C14 C15 C16 . . . . 178.95(6) ?
C19 C14 C15 C16 . . . . -57.08(8) ?
C14 C15 C16 C17 . . . . 53.71(8) ?
C15 C16 C17 C18 . . . . -53.06(8) ?
C16 C17 C18 C19 . . . . 55.98(9) ?
N4 C14 C19 C18 . . . . -179.58(6) ?
C15 C14 C19 C18 . . . . 59.03(8) ?
C17 C18 C19 C14 . . . . -58.68(8) ?
C19 C14 N4 C8 . . . . 51.17(8) ?
C15 C14 N4 C8 . . . . 174.17(6) ?
C13 C6 N4 C14 . . . . 178.82(6) ?
O2 C6 N4 C14 . . . . 56.30(8) ?
