#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/48/2104850.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_2104850
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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                111.073(2)
_cell_angle_beta                 103.254(2)
_cell_angle_gamma                103.553(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2356(4)
_cell_length_b                   10.2844(5)
_cell_length_c                   11.3770(6)
_cell_measurement_temperature    82(2)
_cell_volume                     919.86(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  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0277
_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       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14760
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9789
_exptl_absorpt_correction_T_min  0.9646
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Program SADABS was used. '
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.244
_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         0.400
_refine_diff_density_min         -0.461
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.902
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         5328
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.906
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0486
_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)+(0.0866P)²+0.4358P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1410
_reflns_number_gt                4342
_reflns_number_total             5328
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            og5043.cif
_cod_data_source_block           3a-dc-f
_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               2104850
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 C8 0.19633(4) 0.33724(4) 0.51373(3) 0.01734(19) Uani d G 1 . .
H H8 0.1506 0.2261 0.4688 0.021 Uiso calc R 1 . .
C C9 0.37804(4) 0.38581(6) 0.56381(3) 0.0201(2) Uani d G 1 . .
H H91 0.4247 0.4953 0.6004 0.024 Uiso calc R 1 . .
H H92 0.4134 0.3410 0.4878 0.024 Uiso calc R 1 . .
C C10 0.43674(6) 0.33697(7) 0.67355(4) 0.0220(2) Uani d G 1 . .
H H101 0.3977 0.2270 0.6346 0.026 Uiso calc R 1 . .
H H102 0.5542 0.3728 0.7072 0.026 Uiso calc R 1 . .
C C11 0.37833(6) 0.39870(7) 0.79071(4) 0.0269(2) Uani d G 1 . .
H H111 0.4236 0.5087 0.8341 0.032 Uiso calc R 1 . .
H H112 0.4147 0.3633 0.8585 0.032 Uiso calc R 1 . .
C C12 0.19581(6) 0.34746(7) 0.73954(4) 0.0267(2) Uani d G 1 . .
H H121 0.1510 0.2379 0.7031 0.032 Uiso calc R 1 . .
H H122 0.1596 0.3911 0.8153 0.032 Uiso calc R 1 . .
C C13 0.13471(6) 0.39488(7) 0.62957(4) 0.0214(2) Uani d G 1 . .
H H131 0.0172 0.3555 0.5947 0.026 Uiso calc R 1 . .
H H132 0.1699 0.5047 0.6686 0.026 Uiso calc R 1 . .
C C14 0.18605(4) 0.35496(4) 0.29121(3) 0.01696(19) Uani d G 1 . .
H H14 0.3027 0.4082 0.3205 0.020 Uiso calc R 1 . .
C C15 0.09899(6) 0.41111(5) 0.19818(4) 0.0194(2) Uani d G 1 . .
H H151 0.1259 0.5198 0.2471 0.023 Uiso calc R 1 . .
H H152 -0.0171 0.3630 0.1716 0.023 Uiso calc R 1 . .
C C16 0.14561(7) 0.37646(6) 0.07154(4) 0.0214(2) Uani d G 1 . .
H H161 0.0807 0.4052 0.0098 0.026 Uiso calc R 1 . .
H H162 0.2584 0.4364 0.0973 0.026 Uiso calc R 1 . .
C C17 0.12131(7) 0.21073(6) -0.00159(3) 0.0242(2) Uani d G 1 . .
H H171 0.1632 0.1947 -0.0764 0.029 Uiso calc R 1 . .
H H172 0.0064 0.1517 -0.0401 0.029 Uiso calc R 1 . .
C C18 0.20644(8) 0.15734(6) 0.09495(4) 0.0241(2) Uani d G 1 . .
H H181 0.3225 0.2090 0.1259 0.029 Uiso calc R 1 . .
H H182 0.1842 0.0493 0.0467 0.029 Uiso calc R 1 . .
C C19 0.15208(6) 0.18773(4) 0.21741(3) 0.0205(2) Uani d G 1 . .
H H191 0.0371 0.1324 0.1877 0.025 Uiso calc R 1 . .
H H192 0.2097 0.1538 0.2785 0.025 Uiso calc R 1 . .
N N4 0.13726(5) 0.39508(5) 0.41397(3) 0.01682(17) Uani d G 1 . .
H H01 0.0281 0.3610 0.3854 0.020 Uiso calc R 1 . .
H H02 0.1716 0.4971 0.4586 0.020 Uiso calc R 1 . .
C C7 0.70870(5) 0.21398(4) 0.35477(4) 0.0208(2) Uani d G 1 A 1
C C1 0.33130(5) -0.12219(4) 0.23526(5) 0.0268(2) Uani d G 1 A 1
C C2 0.45416(4) 0.01587(4) 0.31703(4) 0.0226(2) Uani d G 1 A 1
H H2 0.4558 0.0763 0.4035 0.027 Uiso calc R 1 A 1
C C3 0.57452(4) 0.06359(4) 0.26956(4) 0.0214(2) Uani d G 1 A 1
C C4 0.57107(6) -0.02645(5) 0.14191(4) 0.0283(2) Uani d G 1 A 1
H H4 0.6532 0.0050 0.1104 0.034 Uiso calc R 1 A 1
C C5 0.44676(7) -0.16284(6) 0.06067(5) 0.0332(3) Uani d G 1 A 1
H H5 0.4440 -0.2227 -0.0264 0.040 Uiso calc R 1 A 1
C C6 0.32710(6) -0.21101(5) 0.10724(5) 0.0321(3) Uani d G 1 A 1
H H6 0.2432 -0.3036 0.0523 0.038 Uiso calc R 1 A 1
O O1 0.69944(6) 0.29962(5) 0.46306(5) 0.02617(19) Uani d G 1 A 1
O O2 0.81857(5) 0.24170(6) 0.30853(5) 0.02648(19) Uani d G 1 A 1
N N1 0.20316(6) -0.18301(6) 0.27312(6) 0.0354(3) Uani d G 1 . 1
N N2 0.19491(6) -0.10253(7) 0.38192(7) 0.0244(3) Uani d PG 0.817(4) B 1
N N3 0.17079(8) -0.04254(9) 0.47701(8) 0.0328(4) Uani d PG 0.817(4) B 1
N N2P 0.159(2) -0.0365(19) 0.4832(17) 0.092(4) Uiso d PD 0.183(4) B 2
N N3P 0.1175(18) -0.0435(17) 0.5514(15) 0.092(4) Uiso d PD 0.183(4) 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'
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
N4 C8 C13 . . 107.6 ?
N4 C8 C9 . . 111.3 ?
C13 C8 C9 . . 111.6 ?
N4 C8 H8 . . 108.8 ?
C13 C8 H8 . . 108.8 ?
C9 C8 H8 . . 108.8 ?
C8 C9 C10 . . 110.6 ?
C8 C9 H91 . . 109.5 ?
C10 C9 H91 . . 109.5 ?
C8 C9 H92 . . 109.5 ?
C10 C9 H92 . . 109.5 ?
H91 C9 H92 . . 108.1 ?
C11 C10 C9 . . 111.2 ?
C11 C10 H101 . . 109.4 ?
C9 C10 H101 . . 109.4 ?
C11 C10 H102 . . 109.4 ?
C9 C10 H102 . . 109.4 ?
H101 C10 H102 . . 108.0 ?
C10 C11 C12 . . 110.1 ?
C10 C11 H111 . . 109.6 ?
C12 C11 H111 . . 109.6 ?
C10 C11 H112 . . 109.6 ?
C12 C11 H112 . . 109.6 ?
H111 C11 H112 . . 108.2 ?
C13 C12 C11 . . 111.1 ?
C13 C12 H121 . . 109.4 ?
C11 C12 H121 . . 109.4 ?
C13 C12 H122 . . 109.4 ?
C11 C12 H122 . . 109.4 ?
H121 C12 H122 . . 108.0 ?
C8 C13 C12 . . 111.2 ?
C8 C13 H131 . . 109.4 ?
C12 C13 H131 . . 109.4 ?
C8 C13 H132 . . 109.4 ?
C12 C13 H132 . . 109.4 ?
H131 C13 H132 . . 108.0 ?
N4 C14 C19 . . 112.6 ?
N4 C14 C15 . . 108.1 ?
C19 C14 C15 . . 111.0 ?
N4 C14 H14 . . 108.3 ?
C19 C14 H14 . . 108.3 ?
C15 C14 H14 . . 108.3 ?
C14 C15 C16 . . 111.0 ?
C14 C15 H151 . . 109.4 ?
C16 C15 H151 . . 109.4 ?
C14 C15 H152 . . 109.4 ?
C16 C15 H152 . . 109.4 ?
H151 C15 H152 . . 108.0 ?
C17 C16 C15 . . 111.8 ?
C17 C16 H161 . . 109.2 ?
C15 C16 H161 . . 109.2 ?
C17 C16 H162 . . 109.2 ?
C15 C16 H162 . . 109.2 ?
H161 C16 H162 . . 107.9 ?
C16 C17 C18 . . 111.0 ?
C16 C17 H171 . . 109.4 ?
C18 C17 H171 . . 109.4 ?
C16 C17 H172 . . 109.4 ?
C18 C17 H172 . . 109.4 ?
H171 C17 H172 . . 108.0 ?
C17 C18 C19 . . 111.5 ?
C17 C18 H181 . . 109.3 ?
C19 C18 H181 . . 109.3 ?
C17 C18 H182 . . 109.3 ?
C19 C18 H182 . . 109.3 ?
H181 C18 H182 . . 108.0 ?
C14 C19 C18 . . 109.0 ?
C14 C19 H191 . . 109.9 ?
C18 C19 H191 . . 109.9 ?
C14 C19 H192 . . 109.9 ?
C18 C19 H192 . . 109.9 ?
H191 C19 H192 . . 108.3 ?
C14 N4 C8 . . 117.3 ?
C14 N4 H01 . . 108.0 ?
C8 N4 H01 . . 108.0 ?
C14 N4 H02 . . 108.0 ?
C8 N4 H02 . . 108.0 ?
H01 N4 H02 . . 107.2 ?
O1 C7 O2 . . 126.0 ?
O1 C7 C3 . . 117.8 ?
O2 C7 C3 . . 116.2 ?
C6 C1 C2 . . 120.7 ?
C6 C1 N1 . . 114.9 ?
C2 C1 N1 . . 124.4 ?
C3 C2 C1 . . 119.4 ?
C3 C2 H2 . . 120.3 ?
C1 C2 H2 . . 120.3 ?
C4 C3 C2 . . 119.9 ?
C4 C3 C7 . . 119.3 ?
C2 C3 C7 . . 120.8 ?
C3 C4 C5 . . 120.2 ?
C3 C4 H4 . . 119.9 ?
C5 C4 H4 . . 119.9 ?
C6 C5 C4 . . 120.2 ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C5 C6 C1 . . 119.7 ?
C5 C6 H6 . . 120.2 ?
C1 C6 H6 . . 120.2 ?
N2 N1 C1 . . 117.2 ?
N2 N1 N1 . 2_656 62.2 ?
C1 N1 N1 . 2_656 66.6 ?
N3 N2 N1 . . 171.7 ?
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
C8 N4 . 1.5143 ?
C8 C13 . 1.5337 ?
C8 C9 . 1.5344 ?
C8 H8 . 1.0000 ?
C9 C10 . 1.5406 ?
C9 H91 . 0.9900 ?
C9 H92 . 0.9900 ?
C10 C11 . 1.5337 ?
C10 H101 . 0.9900 ?
C10 H102 . 0.9900 ?
C11 C12 . 1.5399 ?
C11 H111 . 0.9900 ?
C11 H112 . 0.9900 ?
C12 C13 . 1.5382 ?
C12 H121 . 0.9900 ?
C12 H122 . 0.9900 ?
C13 H131 . 0.9900 ?
C13 H132 . 0.9900 ?
C14 N4 . 1.5116 ?
C14 C19 . 1.5327 ?
C14 C15 . 1.5386 ?
C14 H14 . 1.0000 ?
C15 C16 . 1.5412 ?
C15 H151 . 0.9900 ?
C15 H152 . 0.9900 ?
C16 C17 . 1.5371 ?
C16 H161 . 0.9900 ?
C16 H162 . 0.9900 ?
C17 C18 . 1.5382 ?
C17 H171 . 0.9900 ?
C17 H172 . 0.9900 ?
C18 C19 . 1.5401 ?
C18 H181 . 0.9900 ?
C18 H182 . 0.9900 ?
C19 H191 . 0.9900 ?
C19 H192 . 0.9900 ?
N4 H01 . 0.9200 ?
N4 H02 . 0.9200 ?
C7 O1 . 1.2665 ?
C7 O2 . 1.2668 ?
C7 C3 . 1.5298 ?
C1 C6 . 1.3993 ?
C1 C2 . 1.4071 ?
C1 N1 . 1.4346 ?
C2 C3 . 1.4065 ?
C2 H2 . 0.9500 ?
C3 C4 . 1.4019 ?
C4 C5 . 1.4023 ?
C4 H4 . 0.9500 ?
C5 C6 . 1.3957 ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
N1 N2 . 1.2486 ?
N1 N1 2_656 5.8529(11) ?
N2 N3 . 1.1382 ?
N2P N3P . 0.959(14) ?
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 O2 1_455 0.92 1.83 2.7266(11) 163.5
N4 H02 O1 2_666 0.92 1.89 2.7829(10) 161.6
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
N4 C8 C9 C10 . . . . 175.4 ?
C13 C8 C9 C10 . . . . 55.2 ?
C8 C9 C10 C11 . . . . -56.8 ?
C9 C10 C11 C12 . . . . 57.5 ?
C10 C11 C12 C13 . . . . -56.9 ?
N4 C8 C13 C12 . . . . -177.3 ?
C9 C8 C13 C12 . . . . -54.9 ?
C11 C12 C13 C8 . . . . 55.7 ?
N4 C14 C15 C16 . . . . 179.0 ?
C19 C14 C15 C16 . . . . -57.1 ?
C14 C15 C16 C17 . . . . 53.7 ?
C15 C16 C17 C18 . . . . -53.1 ?
C16 C17 C18 C19 . . . . 56.0 ?
N4 C14 C19 C18 . . . . -179.6 ?
C15 C14 C19 C18 . . . . 59.0 ?
C17 C18 C19 C14 . . . . -58.7 ?
C19 C14 N4 C8 . . . . 51.2 ?
C15 C14 N4 C8 . . . . 174.2 ?
C13 C8 N4 C14 . . . . 178.8 ?
C9 C8 N4 C14 . . . . 56.3 ?
C6 C1 C2 C3 . . . . -0.7 ?
N1 C1 C2 C3 . . . . 179.5 ?
C1 C2 C3 C4 . . . . -0.1 ?
C1 C2 C3 C7 . . . . 179.1 ?
O1 C7 C3 C4 . . . . 172.5 ?
O2 C7 C3 C4 . . . . -6.6 ?
O1 C7 C3 C2 . . . . -6.7 ?
O2 C7 C3 C2 . . . . 174.2 ?
C2 C3 C4 C5 . . . . 1.0 ?
C7 C3 C4 C5 . . . . -178.2 ?
C3 C4 C5 C6 . . . . -1.1 ?
C4 C5 C6 C1 . . . . 0.3 ?
C2 C1 C6 C5 . . . . 0.6 ?
N1 C1 C6 C5 . . . . -179.6 ?
C6 C1 N1 N2 . . . . -174.4 ?
C2 C1 N1 N2 . . . . 5.4 ?
C6 C1 N1 N1 . . . 2_656 148.2 ?
C2 C1 N1 N1 . . . 2_656 -32.0 ?
C1 N1 N2 N3 . . . . 175.5 ?
N1 N1 N2 N3 2_656 . . . -145.4 ?
