#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/48/2104846.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_2104846
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         'C22 H22 N4 O2'
_chemical_formula_sum            'C22 H22 N4 O2'
_chemical_formula_weight         374.44
_chemical_melting_point          ?
_chemical_name_common
;
 N-benzyl-2-phenylethylammonium 4-azidebenzoate
;
_chemical_name_systematic
;
 N-benzyl-2-phenylethylammonium 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                72.5030(10)
_cell_angle_beta                 72.9330(10)
_cell_angle_gamma                70.5060(10)
_cell_formula_units_Z            2
_cell_length_a                   8.0615(2)
_cell_length_b                   10.3615(2)
_cell_length_c                   13.5356(4)
_cell_measurement_reflns_used    6018
_cell_measurement_temperature    92(2)
_cell_volume                     992.76(4)
_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      92(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  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0528
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15962
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9934
_exptl_absorpt_correction_T_min  0.9748
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Program SADABS was used. '
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.259
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0495
_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)+(0.0855P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1365
_refine_ls_wR_factor_ref         0.1482
_reflns_number_gt                4057
_reflns_number_total             5766
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            og5043.cif
_cod_data_source_block           4a-bp-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               2104846
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 C1 0.74869(15) -0.00293(12) 0.52514(9) 0.0230(2) Uani d . 1 . .
C C2 0.66148(16) 0.10149(12) 0.58242(9) 0.0245(2) Uani d . 1 . .
H H2 0.567(2) 0.1882(15) 0.5564(11) 0.029 Uiso d . 1 . .
C C3 0.70655(16) 0.08587(12) 0.67811(9) 0.0243(2) Uani d . 1 . .
H H3 0.650(2) 0.1543(16) 0.7150(12) 0.029 Uiso d . 1 . .
C C4 0.83763(15) -0.03191(12) 0.71663(9) 0.0230(2) Uani d . 1 . .
C C5 0.92501(16) -0.13450(12) 0.65719(9) 0.0241(2) Uani d . 1 . .
H H5 1.020(2) -0.2167(15) 0.6795(12) 0.029 Uiso d . 1 . .
C C6 0.87929(16) -0.12180(12) 0.56236(9) 0.0241(2) Uani d . 1 . .
H H6 0.939(2) -0.1914(16) 0.5195(12) 0.029 Uiso d . 1 . .
C C7 0.88465(18) -0.04706(13) 0.82082(9) 0.0282(3) Uani d . 1 . .
N N1 0.71091(15) 0.00314(11) 0.42634(8) 0.0287(2) Uani d . 1 . .
N N2 0.61219(15) 0.11711(11) 0.38672(8) 0.0293(2) Uani d . 1 . .
N N3 0.52390(18) 0.21433(12) 0.34259(10) 0.0391(3) Uani d . 1 . .
O O2 0.77098(14) 0.02808(10) 0.88220(7) 0.0383(2) Uani d . 1 . .
O O1 1.03312(14) -0.13148(10) 0.83829(8) 0.0389(3) Uani d . 1 . .
N N4 0.75323(14) 0.07712(10) 0.06816(8) 0.0262(2) Uani d . 1 . .
H H01 0.792(2) 0.0517(15) -0.0021(12) 0.031 Uiso d . 1 . .
H H02 0.844(2) 0.0990(16) 0.0848(12) 0.031 Uiso d . 1 . .
C C9 0.66866(16) 0.33067(13) -0.01742(10) 0.0288(3) Uani d . 1 . .
C C10 0.64991(18) 0.35859(14) -0.12205(10) 0.0343(3) Uani d . 1 . .
H H10 0.592(2) 0.2991(17) -0.1427(13) 0.041 Uiso d . 1 . .
C C11 0.7074(2) 0.46757(16) -0.19835(12) 0.0468(4) Uani d . 1 . .
H H11 0.696(3) 0.489(2) -0.2740(16) 0.056 Uiso d . 1 . .
C C12 0.7841(2) 0.54888(17) -0.17177(16) 0.0564(5) Uani d . 1 . .
H H12 0.825(3) 0.621(2) -0.2236(17) 0.068 Uiso d . 1 . .
C C13 0.8065(2) 0.52141(16) -0.06864(18) 0.0535(5) Uani d . 1 . .
H H13 0.862(3) 0.570(2) -0.0520(17) 0.064 Uiso d . 1 . .
C C14 0.74753(19) 0.41174(15) 0.00941(13) 0.0399(3) Uani d . 1 . .
H H14 0.766(2) 0.3941(19) 0.0821(15) 0.048 Uiso d . 1 . .
C C8 0.60335(18) 0.21146(13) 0.06385(10) 0.0316(3) Uani d . 1 . .
H H81 0.567(2) 0.2277(17) 0.1372(13) 0.038 Uiso d . 1 . .
H H82 0.495(2) 0.1929(17) 0.0431(12) 0.038 Uiso d . 1 . .
C C17 0.81127(16) -0.29394(12) 0.24357(10) 0.0281(3) Uani d . 1 . .
C C18 0.8430(2) -0.30448(14) 0.34206(11) 0.0358(3) Uani d . 1 . .
H H18 0.895(2) -0.2346(18) 0.3501(13) 0.043 Uiso d . 1 . .
C C19 0.8016(2) -0.41065(17) 0.42900(13) 0.0523(5) Uani d . 1 . .
H H19 0.822(3) -0.417(2) 0.4979(17) 0.063 Uiso d . 1 . .
C C20 0.7294(2) -0.50740(18) 0.41942(19) 0.0646(6) Uani d . 1 . .
H H20 0.700(3) -0.582(2) 0.4825(18) 0.078 Uiso d . 1 . .
C C21 0.6957(2) -0.49794(18) 0.3224(2) 0.0662(6) Uani d . 1 . .
H H21 0.649(3) -0.554(2) 0.3083(18) 0.079 Uiso d . 1 . .
C C22 0.7375(2) -0.39237(16) 0.23419(16) 0.0444(4) Uani d . 1 . .
H H22 0.717(3) -0.385(2) 0.1652(16) 0.053 Uiso d . 1 . .
C C15 0.69815(18) -0.04372(13) 0.15029(10) 0.0293(3) Uani d . 1 . .
H H151 0.585(2) -0.0544(16) 0.1329(12) 0.035 Uiso d . 1 . .
H H152 0.669(2) -0.0169(16) 0.2163(13) 0.035 Uiso d . 1 . .
C C16 0.85513(18) -0.17717(13) 0.15046(10) 0.0303(3) Uani d . 1 . .
H H161 0.883(2) -0.2081(16) 0.0809(13) 0.036 Uiso d . 1 . .
H H162 0.963(2) -0.1550(16) 0.1562(12) 0.036 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
C2 C1 C6 . . 120.93(10) ?
C2 C1 N1 . . 123.11(10) ?
C6 C1 N1 . . 115.96(10) ?
C1 C2 C3 . . 118.96(10) ?
C1 C2 H2 . . 121.8(8) ?
C3 C2 H2 . . 119.2(8) ?
C2 C3 C4 . . 121.10(11) ?
C2 C3 H3 . . 118.8(9) ?
C4 C3 H3 . . 120.1(9) ?
C5 C4 C3 . . 118.95(11) ?
C5 C4 C7 . . 120.72(10) ?
C3 C4 C7 . . 120.33(10) ?
C6 C5 C4 . . 120.68(10) ?
C6 C5 H5 . . 117.4(8) ?
C4 C5 H5 . . 121.9(8) ?
C5 C6 C1 . . 119.35(11) ?
C5 C6 H6 . . 122.1(9) ?
C1 C6 H6 . . 118.5(9) ?
O1 C7 O2 . . 125.90(11) ?
O1 C7 C4 . . 117.71(11) ?
O2 C7 C4 . . 116.38(11) ?
N2 N1 C1 . . 115.54(10) ?
N3 N2 N1 . . 172.92(13) ?
C15 N4 C8 . . 112.72(9) ?
C15 N4 H01 . . 108.1(9) ?
C8 N4 H01 . . 109.5(9) ?
C15 N4 H02 . . 110.7(9) ?
C8 N4 H02 . . 103.8(9) ?
H01 N4 H02 . . 112.0(13) ?
C14 C9 C10 . . 119.50(13) ?
C14 C9 C8 . . 121.36(12) ?
C10 C9 C8 . . 119.15(13) ?
C11 C10 C9 . . 120.61(15) ?
C11 C10 H10 . . 119.3(9) ?
C9 C10 H10 . . 120.1(9) ?
C12 C11 C10 . . 120.03(15) ?
C12 C11 H11 . . 118.0(11) ?
C10 C11 H11 . . 122.0(11) ?
C11 C12 C13 . . 120.22(15) ?
C11 C12 H12 . . 119.7(13) ?
C13 C12 H12 . . 120.0(13) ?
C12 C13 C14 . . 120.17(17) ?
C12 C13 H13 . . 120.7(14) ?
C14 C13 H13 . . 119.1(14) ?
C9 C14 C13 . . 119.47(15) ?
C9 C14 H14 . . 122.2(10) ?
C13 C14 H14 . . 118.4(11) ?
N4 C8 C9 . . 110.35(10) ?
N4 C8 H81 . . 105.1(9) ?
C9 C8 H81 . . 112.2(9) ?
N4 C8 H82 . . 107.0(9) ?
C9 C8 H82 . . 110.9(8) ?
H81 C8 H82 . . 111.0(13) ?
C22 C17 C18 . . 118.34(13) ?
C22 C17 C16 . . 121.45(13) ?
C18 C17 C16 . . 120.20(12) ?
C19 C18 C17 . . 120.93(16) ?
C19 C18 H18 . . 119.8(10) ?
C17 C18 H18 . . 119.3(10) ?
C20 C19 C18 . . 120.56(18) ?
C20 C19 H19 . . 118.9(12) ?
C18 C19 H19 . . 120.5(12) ?
C19 C20 C21 . . 119.30(16) ?
C19 C20 H20 . . 119.2(13) ?
C21 C20 H20 . . 121.5(13) ?
C20 C21 C22 . . 120.81(18) ?
C20 C21 H21 . . 126.2(16) ?
C22 C21 H21 . . 113.0(16) ?
C17 C22 C21 . . 120.06(18) ?
C17 C22 H22 . . 117.8(11) ?
C21 C22 H22 . . 122.2(11) ?
N4 C15 C16 . . 110.34(10) ?
N4 C15 H151 . . 107.1(8) ?
C16 C15 H151 . . 112.5(9) ?
N4 C15 H152 . . 104.9(9) ?
C16 C15 H152 . . 109.7(9) ?
H151 C15 H152 . . 112.0(13) ?
C17 C16 C15 . . 110.85(10) ?
C17 C16 H161 . . 110.0(9) ?
C15 C16 H161 . . 109.6(9) ?
C17 C16 H162 . . 109.1(9) ?
C15 C16 H162 . . 108.1(9) ?
H161 C16 H162 . . 109.2(13) ?
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
C1 C2 . 1.3938(17) ?
C1 C6 . 1.3971(16) ?
C1 N1 . 1.4356(15) ?
C2 C3 . 1.3952(17) ?
C2 H2 . 1.010(14) ?
C3 C4 . 1.3992(16) ?
C3 H3 . 0.907(15) ?
C4 C5 . 1.3983(17) ?
C4 C7 . 1.5159(16) ?
C5 C6 . 1.3945(17) ?
C5 H5 . 0.976(15) ?
C6 H6 . 0.972(15) ?
C7 O1 . 1.2636(15) ?
C7 O2 . 1.2657(15) ?
N1 N2 . 1.2482(14) ?
N2 N3 . 1.1346(15) ?
N4 C15 . 1.4983(16) ?
N4 C8 . 1.5069(15) ?
N4 H01 . 0.996(15) ?
N4 H02 . 0.938(16) ?
C9 C14 . 1.385(2) ?
C9 C10 . 1.4009(18) ?
C9 C8 . 1.5133(18) ?
C10 C11 . 1.387(2) ?
C10 H10 . 1.022(17) ?
C11 C12 . 1.372(3) ?
C11 H11 . 1.005(19) ?
C12 C13 . 1.392(3) ?
C12 H12 . 0.93(2) ?
C13 C14 . 1.406(2) ?
C13 H13 . 0.88(2) ?
C14 H14 . 0.993(18) ?
C8 H81 . 0.998(16) ?
C8 H82 . 1.079(16) ?
C17 C22 . 1.392(2) ?
C17 C18 . 1.396(2) ?
C17 C16 . 1.5114(17) ?
C18 C19 . 1.394(2) ?
C18 H18 . 0.993(17) ?
C19 C20 . 1.369(3) ?
C19 H19 . 0.98(2) ?
C20 C21 . 1.386(3) ?
C20 H20 . 0.99(2) ?
C21 C22 . 1.400(3) ?
C21 H21 . 0.88(2) ?
C22 H22 . 0.971(19) ?
C15 C16 . 1.5315(17) ?
C15 H151 . 1.054(16) ?
C15 H152 . 0.955(16) ?
C16 H161 . 1.025(16) ?
C16 H162 . 0.996(16) ?
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_554 0.996(15) 1.720(15) 2.6689(14) 157.8(13)
N4 H02 O1 2_756 0.938(16) 1.792(16) 2.6914(16) 159.8(14)
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 . . . . 0.04(17) ?
N1 C1 C2 C3 . . . . 179.60(10) ?
C1 C2 C3 C4 . . . . 0.32(18) ?
C2 C3 C4 C5 . . . . 0.48(17) ?
C2 C3 C4 C7 . . . . -179.95(11) ?
C3 C4 C5 C6 . . . . -1.65(17) ?
C7 C4 C5 C6 . . . . 178.78(11) ?
C4 C5 C6 C1 . . . . 2.01(18) ?
C2 C1 C6 C5 . . . . -1.19(17) ?
N1 C1 C6 C5 . . . . 179.22(10) ?
C5 C4 C7 O1 . . . . 18.61(17) ?
C3 C4 C7 O1 . . . . -160.95(12) ?
C5 C4 C7 O2 . . . . -162.15(12) ?
C3 C4 C7 O2 . . . . 18.29(17) ?
C2 C1 N1 N2 . . . . 9.41(17) ?
C6 C1 N1 N2 . . . . -171.01(11) ?
C1 N1 N2 N3 . . . . -178.3(10) ?
C14 C9 C10 C11 . . . . -0.83(18) ?
C8 C9 C10 C11 . . . . 179.64(11) ?
C9 C10 C11 C12 . . . . 0.2(2) ?
C10 C11 C12 C13 . . . . 0.8(2) ?
C11 C12 C13 C14 . . . . -1.2(2) ?
C10 C9 C14 C13 . . . . 0.42(18) ?
C8 C9 C14 C13 . . . . 179.94(12) ?
C12 C13 C14 C9 . . . . 0.6(2) ?
C15 N4 C8 C9 . . . . 177.89(11) ?
C14 C9 C8 N4 . . . . -88.51(14) ?
C10 C9 C8 N4 . . . . 91.01(14) ?
C22 C17 C18 C19 . . . . -0.1(2) ?
C16 C17 C18 C19 . . . . 179.34(12) ?
C17 C18 C19 C20 . . . . 0.2(2) ?
C18 C19 C20 C21 . . . . -0.7(2) ?
C19 C20 C21 C22 . . . . 1.1(3) ?
C18 C17 C22 C21 . . . . 0.5(2) ?
C16 C17 C22 C21 . . . . -178.98(13) ?
C20 C21 C22 C17 . . . . -0.9(2) ?
C8 N4 C15 C16 . . . . 179.62(11) ?
C22 C17 C16 C15 . . . . 93.70(15) ?
C18 C17 C16 C15 . . . . -85.74(15) ?
N4 C15 C16 C17 . . . . 171.28(11) ?
