#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/48/2104868.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_2104868
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_name_common
;
 Dicyclohexylammonium 4-azidebenzoate
;
_chemical_name_systematic
;
 Dicyclohexylammonium 4-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                107.9090(10)
_cell_angle_beta                 100.4540(10)
_cell_angle_gamma                91.6130(10)
_cell_formula_units_Z            2
_cell_length_a                   9.0015(2)
_cell_length_b                   9.3009(2)
_cell_length_c                   11.88190(10)
_cell_measurement_reflns_used    8192
_cell_measurement_temperature    80(2)
_cell_volume                     927.11(3)
_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      80(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  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14876
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9870
_exptl_absorpt_correction_T_min  0.9814
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Program SADABS was used. '
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.202
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         5369
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0427
_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)+(0.0705P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1085
_reflns_number_gt                4476
_reflns_number_total             5369
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            og5043.cif
_cod_data_source_block           4a-dc-i
_cod_depositor_comments
;
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               2104868
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 0.34728(9) 0.23018(9) -0.21129(7) 0.01336(15) Uani d . 1 . .
C C4 0.27903(9) 0.09543(8) -0.32075(7) 0.01275(15) Uani d . 1 . .
C C3 0.32593(10) 0.07436(10) -0.43020(7) 0.01852(17) Uani d . 1 . .
H H3 0.4041(13) 0.1445(13) -0.4340(11) 0.022 Uiso d . 1 . .
C C2 0.26616(11) -0.04998(10) -0.53101(8) 0.02156(18) Uani d . 1 . .
H H2 0.3003(13) -0.0659(14) -0.6067(11) 0.026 Uiso d . 1 . .
C C1 0.15619(10) -0.15322(9) -0.52292(7) 0.01729(16) Uani d . 1 . .
C C6 0.10717(9) -0.13356(9) -0.41448(7) 0.01653(16) Uani d . 1 . .
H H6 0.0270(13) -0.2037(13) -0.4082(10) 0.020 Uiso d . 1 . .
C C5 0.16986(9) -0.00971(9) -0.31390(7) 0.01507(16) Uani d . 1 . .
H H5 0.1354(12) 0.0026(12) -0.2382(10) 0.018 Uiso d . 1 . .
N N1 0.10055(10) -0.27766(9) -0.63098(7) 0.02580(18) Uani d . 1 . .
N N2 0.00167(9) -0.36899(9) -0.62448(7) 0.02437(18) Uani d . 1 . .
N N3 -0.08790(10) -0.46096(10) -0.63058(9) 0.0354(2) Uani d . 1 . .
O O1 0.32736(7) 0.22575(7) -0.10966(5) 0.01705(13) Uani d . 1 . .
O O2 0.42010(7) 0.33600(7) -0.22984(6) 0.01876(14) Uani d . 1 . .
C C8 0.44971(8) 0.29984(8) 0.18519(7) 0.01120(14) Uani d . 1 . .
H H8 0.4349(12) 0.1877(12) 0.1484(10) 0.013 Uiso d . 1 . .
C C9 0.29221(9) 0.35908(9) 0.18393(7) 0.01391(15) Uani d . 1 . .
H H91 0.2323(12) 0.3301(12) 0.0999(10) 0.017 Uiso d . 1 . .
H H92 0.3026(12) 0.4755(12) 0.2132(10) 0.017 Uiso d . 1 . .
C C10 0.20808(9) 0.29855(9) 0.26378(7) 0.01592(16) Uani d . 1 . .
H H101 0.1039(13) 0.3382(13) 0.2618(10) 0.019 Uiso d . 1 . .
H H102 0.1903(13) 0.1838(13) 0.2295(10) 0.019 Uiso d . 1 . .
C C11 0.30000(10) 0.34268(10) 0.39316(7) 0.01749(16) Uani d . 1 . .
H H111 0.2448(13) 0.3015(13) 0.4441(11) 0.021 Uiso d . 1 . .
H H112 0.3116(13) 0.4565(13) 0.4299(11) 0.021 Uiso d . 1 . .
C C12 0.45846(9) 0.28592(10) 0.39391(7) 0.01726(16) Uani d . 1 . .
H H121 0.4480(12) 0.1717(13) 0.3650(10) 0.021 Uiso d . 1 . .
H H122 0.5167(13) 0.3181(13) 0.4755(11) 0.021 Uiso d . 1 . .
C C13 0.54395(9) 0.34401(9) 0.31363(7) 0.01437(15) Uani d . 1 . .
H H131 0.5652(12) 0.4570(13) 0.3473(10) 0.017 Uiso d . 1 . .
H H132 0.6433(12) 0.3005(12) 0.3144(10) 0.017 Uiso d . 1 . .
C C14 0.67994(8) 0.30815(8) 0.08581(7) 0.01092(14) Uani d . 1 . .
H H14 0.7508(12) 0.3448(12) 0.1652(10) 0.013 Uiso d . 1 . .
C C15 0.67317(8) 0.13498(8) 0.03705(7) 0.01300(15) Uani d . 1 . .
H H151 0.5903(12) 0.0958(12) -0.0378(10) 0.016 Uiso d . 1 . .
H H152 0.6472(12) 0.0881(12) 0.0954(10) 0.016 Uiso d . 1 . .
C C16 0.82612(9) 0.08478(9) 0.00644(7) 0.01521(16) Uani d . 1 . .
H H161 0.9051 0.1157 0.0812 0.018 Uiso calc . 1 . .
H H162 0.8188 -0.0272 -0.0277 0.018 Uiso calc . 1 . .
C C17 0.87218(10) 0.15505(10) -0.08433(8) 0.01899(17) Uani d . 1 . .
H H171 0.9702(13) 0.1202(13) -0.1059(11) 0.023 Uiso d . 1 . .
H H172 0.7954(14) 0.1184(13) -0.1600(11) 0.023 Uiso d . 1 . .
C C18 0.88202(9) 0.32790(10) -0.03397(8) 0.01720(16) Uani d . 1 . .
H H181 0.9058(13) 0.3722(13) -0.0929(11) 0.021 Uiso d . 1 . .
H H182 0.9633(13) 0.3644(13) 0.0399(11) 0.021 Uiso d . 1 . .
C C19 0.73172(9) 0.38297(9) -0.00087(7) 0.01373(15) Uani d . 1 . .
H H191 0.6521(12) 0.3556(12) -0.0753(10) 0.016 Uiso d . 1 . .
H H192 0.7395(12) 0.4920(13) 0.0339(10) 0.016 Uiso d . 1 . .
N N4 0.52640(7) 0.36044(7) 0.10448(6) 0.01064(13) Uani d . 1 . .
H H01 0.4593(14) 0.3316(14) 0.0283(12) 0.025(3) Uiso d . 1 . .
H H02 0.5355(14) 0.4614(14) 0.1341(11) 0.026(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
O2 C7 O1 . . 125.91(7) ?
O2 C7 C4 . . 117.00(7) ?
O1 C7 C4 . . 117.09(7) ?
C5 C4 C3 . . 119.00(7) ?
C5 C4 C7 . . 120.91(7) ?
C3 C4 C7 . . 120.09(7) ?
C2 C3 C4 . . 120.82(8) ?
C2 C3 H3 . . 120.2(7) ?
C4 C3 H3 . . 118.9(7) ?
C3 C2 C1 . . 119.44(8) ?
C3 C2 H2 . . 120.9(7) ?
C1 C2 H2 . . 119.7(7) ?
C2 C1 C6 . . 120.56(7) ?
C2 C1 N1 . . 115.78(8) ?
C6 C1 N1 . . 123.66(8) ?
C5 C6 C1 . . 119.26(7) ?
C5 C6 H6 . . 119.3(7) ?
C1 C6 H6 . . 121.5(7) ?
C6 C5 C4 . . 120.91(7) ?
C6 C5 H5 . . 118.7(6) ?
C4 C5 H5 . . 120.4(6) ?
N2 N1 C1 . . 115.97(8) ?
N3 N2 N1 . . 172.81(9) ?
N4 C8 C13 . . 111.79(6) ?
N4 C8 C9 . . 108.21(6) ?
C13 C8 C9 . . 111.42(6) ?
N4 C8 H8 . . 107.0(6) ?
C13 C8 H8 . . 110.6(6) ?
C9 C8 H8 . . 107.6(6) ?
C8 C9 C10 . . 110.30(6) ?
C8 C9 H91 . . 110.6(6) ?
C10 C9 H91 . . 110.7(6) ?
C8 C9 H92 . . 109.9(6) ?
C10 C9 H92 . . 110.5(6) ?
H91 C9 H92 . . 104.7(8) ?
C11 C10 C9 . . 110.87(6) ?
C11 C10 H101 . . 111.3(7) ?
C9 C10 H101 . . 109.5(6) ?
C11 C10 H102 . . 109.1(6) ?
C9 C10 H102 . . 109.6(6) ?
H101 C10 H102 . . 106.4(9) ?
C10 C11 C12 . . 110.47(7) ?
C10 C11 H111 . . 110.2(7) ?
C12 C11 H111 . . 111.0(7) ?
C10 C11 H112 . . 109.5(7) ?
C12 C11 H112 . . 108.6(6) ?
H111 C11 H112 . . 107.0(9) ?
C11 C12 C13 . . 112.03(7) ?
C11 C12 H121 . . 108.9(6) ?
C13 C12 H121 . . 109.6(7) ?
C11 C12 H122 . . 109.7(7) ?
C13 C12 H122 . . 109.4(7) ?
H121 C12 H122 . . 107.1(9) ?
C8 C13 C12 . . 109.97(6) ?
C8 C13 H131 . . 109.8(6) ?
C12 C13 H131 . . 110.1(6) ?
C8 C13 H132 . . 111.1(6) ?
C12 C13 H132 . . 108.8(6) ?
H131 C13 H132 . . 107.1(9) ?
N4 C14 C15 . . 111.21(6) ?
N4 C14 C19 . . 107.16(6) ?
C15 C14 C19 . . 111.95(6) ?
N4 C14 H14 . . 107.7(6) ?
C15 C14 H14 . . 109.2(6) ?
C19 C14 H14 . . 109.5(6) ?
C14 C15 C16 . . 110.36(6) ?
C14 C15 H151 . . 109.6(6) ?
C16 C15 H151 . . 109.7(6) ?
C14 C15 H152 . . 111.5(6) ?
C16 C15 H152 . . 109.1(6) ?
H151 C15 H152 . . 106.4(9) ?
C17 C16 C15 . . 111.27(6) ?
C17 C16 H161 . . 109.4 ?
C15 C16 H161 . . 109.4 ?
C17 C16 H162 . . 109.4 ?
C15 C16 H162 . . 109.4 ?
H161 C16 H162 . . 108.0 ?
C18 C17 C16 . . 110.20(7) ?
C18 C17 H171 . . 110.8(7) ?
C16 C17 H171 . . 111.3(7) ?
C18 C17 H172 . . 110.1(7) ?
C16 C17 H172 . . 108.4(7) ?
H171 C17 H172 . . 106.0(9) ?
C17 C18 C19 . . 111.29(6) ?
C17 C18 H181 . . 110.2(7) ?
C19 C18 H181 . . 108.4(7) ?
C17 C18 H182 . . 109.7(7) ?
C19 C18 H182 . . 108.5(7) ?
H181 C18 H182 . . 108.7(9) ?
C18 C19 C14 . . 111.59(6) ?
C18 C19 H191 . . 109.0(6) ?
C14 C19 H191 . . 107.8(6) ?
C18 C19 H192 . . 111.1(7) ?
C14 C19 H192 . . 110.1(7) ?
H191 C19 H192 . . 107.0(9) ?
C8 N4 C14 . . 117.35(6) ?
C8 N4 H01 . . 106.3(7) ?
C14 N4 H01 . . 108.4(7) ?
C8 N4 H02 . . 108.0(8) ?
C14 N4 H02 . . 108.4(8) ?
H01 N4 H02 . . 108.0(11) ?
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 O2 . 1.2635(9) ?
C7 O1 . 1.2652(10) ?
C7 C4 . 1.5179(11) ?
C4 C5 . 1.3973(11) ?
C4 C3 . 1.3983(11) ?
C3 C2 . 1.3931(12) ?
C3 H3 . 0.962(11) ?
C2 C1 . 1.3961(12) ?
C2 H2 . 0.973(12) ?
C1 C6 . 1.3979(12) ?
C1 N1 . 1.4349(11) ?
C6 C5 . 1.3948(11) ?
C6 H6 . 0.987(11) ?
C5 H5 . 0.979(11) ?
N1 N2 . 1.2420(11) ?
N2 N3 . 1.1352(12) ?
C8 N4 . 1.5048(9) ?
C8 C13 . 1.5305(11) ?
C8 C9 . 1.5347(10) ?
C8 H8 . 0.993(11) ?
C9 C10 . 1.5349(11) ?
C9 H91 . 0.996(11) ?
C9 H92 . 1.026(11) ?
C10 C11 . 1.5322(11) ?
C10 H101 . 1.016(11) ?
C10 H102 . 1.015(11) ?
C11 C12 . 1.5343(12) ?
C11 H111 . 1.000(12) ?
C11 H112 . 1.008(12) ?
C12 C13 . 1.5341(11) ?
C12 H121 . 1.007(11) ?
C12 H122 . 0.966(12) ?
C13 H131 . 1.002(11) ?
C13 H132 . 0.992(11) ?
C14 N4 . 1.5095(9) ?
C14 C15 . 1.5301(10) ?
C14 C19 . 1.5358(10) ?
C14 H14 . 0.992(11) ?
C15 C16 . 1.5360(10) ?
C15 H151 . 1.012(11) ?
C15 H152 . 0.982(11) ?
C16 C17 . 1.5307(11) ?
C16 H161 . 0.9900 ?
C16 H162 . 0.9900 ?
C17 C18 . 1.5270(12) ?
C17 H171 . 0.998(12) ?
C17 H172 . 0.987(12) ?
C18 C19 . 1.5348(11) ?
C18 H181 . 0.966(12) ?
C18 H182 . 0.995(12) ?
C19 H191 . 0.991(11) ?
C19 H192 . 0.966(11) ?
N4 H01 . 0.949(13) ?
N4 H02 . 0.892(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 H01 O1 . 0.949(13) 1.817(13) 2.7409(9) 163.9(11)
N4 H02 O2 2_665 0.892(13) 1.865(13) 2.7384(9) 166.0(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
O2 C7 C4 C5 . . . . -165.63(7) ?
O1 C7 C4 C5 . . . . 15.02(11) ?
O2 C7 C4 C3 . . . . 14.85(11) ?
O1 C7 C4 C3 . . . . -164.50(7) ?
C5 C4 C3 C2 . . . . -0.53(13) ?
C7 C4 C3 C2 . . . . 179.00(8) ?
C4 C3 C2 C1 . . . . 1.11(14) ?
C3 C2 C1 C6 . . . . -0.70(14) ?
C3 C2 C1 N1 . . . . 179.85(8) ?
C2 C1 C6 C5 . . . . -0.27(13) ?
N1 C1 C6 C5 . . . . 179.13(8) ?
C1 C6 C5 C4 . . . . 0.86(13) ?
C3 C4 C5 C6 . . . . -0.46(12) ?
C7 C4 C5 C6 . . . . -179.99(7) ?
C2 C1 N1 N2 . . . . -179.36(9) ?
C6 C1 N1 N2 . . . . 1.21(14) ?
C1 N1 N2 N3 . . . . -176.4(8) ?
N4 C8 C9 C10 . . . . 179.22(6) ?
C13 C8 C9 C10 . . . . -57.50(8) ?
C8 C9 C10 C11 . . . . 57.14(9) ?
C9 C10 C11 C12 . . . . -56.24(9) ?
C10 C11 C12 C13 . . . . 55.91(9) ?
N4 C8 C13 C12 . . . . 177.54(6) ?
C9 C8 C13 C12 . . . . 56.33(8) ?
C11 C12 C13 C8 . . . . -55.67(9) ?
N4 C14 C15 C16 . . . . 174.20(6) ?
C19 C14 C15 C16 . . . . 54.36(8) ?
C14 C15 C16 C17 . . . . -56.99(8) ?
C15 C16 C17 C18 . . . . 58.26(9) ?
C16 C17 C18 C19 . . . . -56.65(9) ?
C17 C18 C19 C14 . . . . 54.45(9) ?
N4 C14 C19 C18 . . . . -175.65(6) ?
C15 C14 C19 C18 . . . . -53.46(8) ?
C13 C8 N4 C14 . . . . 60.74(8) ?
C9 C8 N4 C14 . . . . -176.20(6) ?
C15 C14 N4 C8 . . . . 56.33(8) ?
C19 C14 N4 C8 . . . . 178.98(6) ?
