#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/61/2206199.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2206199
loop_
_publ_author_name
'Sun, Xian-Ming'
'Qu, Yang'
_publ_section_title
;
 1,4-Dimethyl-1,4-diazoniabicyclo[2.2.2]octane tetrachlorocuprate(II)
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1360
_journal_page_last               m1362
_journal_paper_doi               10.1107/S160053680501860X
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          '(C8 H18 N2) [Cu Cl4]'
_chemical_formula_moiety         ' C8 H18 N2 2+ , Cl Cu 2-'
_chemical_formula_sum            'C8 H18 Cl4 Cu N2'
_chemical_formula_weight         347.58
_chemical_name_systematic
;
1,4-Dimethyl-1,4-diazoniabicyclo[2.2.2]octane tetrachlorocuprate(II)
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.6572(16)
_cell_length_b                   8.0741(7)
_cell_length_c                   17.6413(15)
_cell_measurement_reflns_used    3800
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.02
_cell_volume                     2799.9(4)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13376
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.07
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.296
_exptl_absorpt_correction_T_max  0.560
_exptl_absorpt_correction_T_min  0.412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1416
_exptl_crystal_size_max          0.442
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.264
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.344
_refine_ls_abs_structure_details 'Flack (1983), how many Friedel pairs'
_refine_ls_abs_structure_Flack   0.422(13)
_refine_ls_extinction_coef       0.0088(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997a)'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4444
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0305
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0434P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0754
_reflns_number_gt                4074
_reflns_number_total             4444
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg6186.cif
_cod_data_source_block           I
_cod_database_code               2206199
_cod_database_fobs_code          2206199
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
loop_
_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_type_symbol
Cu1 0.98750(2) 0.17093(4) 0.51273(3) 0.03287(13) Uani d . 1 Cu
Cu2 0.75845(2) 0.67886(4) 0.26378(3) 0.03302(13) Uani d . 1 Cu
Cl1 0.76059(7) 0.49620(13) 0.16849(8) 0.0539(4) Uani d . 1 Cl
Cl2 0.84625(5) 0.84057(12) 0.23143(8) 0.0559(3) Uani d . 1 Cl
Cl3 0.74523(8) 0.49756(14) 0.35848(8) 0.0529(4) Uani d . 1 Cl
Cl4 0.68310(5) 0.87701(12) 0.29374(7) 0.0457(3) Uani d . 1 Cl
Cl5 0.89349(5) 0.32206(10) 0.53355(7) 0.0496(3) Uani d . 1 Cl
Cl6 0.98513(6) -0.01845(14) 0.60637(7) 0.0492(3) Uani d . 1 Cl
Cl7 1.00403(7) -0.00179(13) 0.41576(8) 0.0529(4) Uani d . 1 Cl
Cl8 1.06010(5) 0.37969(12) 0.49128(7) 0.0502(3) Uani d . 1 Cl
N1 0.70350(14) 1.0942(3) 0.5176(2) 0.0362(7) Uani d . 1 N
N2 0.78896(14) 0.8582(3) 0.5161(2) 0.0359(7) Uani d . 1 N
N3 1.04192(15) 0.6038(4) 0.2619(2) 0.0370(7) Uani d . 1 N
N4 0.95721(15) 0.3659(4) 0.2633(2) 0.0351(7) Uani d . 1 N
C1 0.9521(2) 0.4566(5) 0.1901(3) 0.0467(10) Uani d . 1 C
H1A 0.9054 0.4914 0.1818 0.056 Uiso calc R 1 H
H1B 0.9652 0.3840 0.1488 0.056 Uiso calc R 1 H
C2 0.9985(2) 0.6074(6) 0.1917(3) 0.0509(11) Uani d . 1 C
H2A 1.0273 0.6077 0.1470 0.061 Uiso calc R 1 H
H2B 0.9713 0.7076 0.1912 0.061 Uiso calc R 1 H
C3 1.02823(17) 0.2993(4) 0.2711(3) 0.0436(10) Uani d . 1 C
H3A 1.0371 0.2187 0.2315 0.052 Uiso calc R 1 H
H3B 1.0334 0.2448 0.3198 0.052 Uiso calc R 1 H
C4 1.07815(19) 0.4423(4) 0.2648(3) 0.0519(11) Uani d . 1 C
H4A 1.1086 0.4410 0.3081 0.062 Uiso calc R 1 H
H4B 1.1054 0.4290 0.2194 0.062 Uiso calc R 1 H
C5 0.9430(2) 0.4810(5) 0.3265(3) 0.0453(11) Uani d . 1 C
H5A 0.9437 0.4208 0.3741 0.054 Uiso calc R 1 H
H5B 0.8982 0.5290 0.3201 0.054 Uiso calc R 1 H
C6 0.9956(2) 0.6168(5) 0.3285(3) 0.0580(13) Uani d . 1 C
H6A 0.9731 0.7238 0.3280 0.070 Uiso calc R 1 H
H6B 1.0218 0.6086 0.3749 0.070 Uiso calc R 1 H
C7 1.0927(2) 0.7427(5) 0.2602(4) 0.0657(14) Uani d . 1 C
H7A 1.1202 0.7386 0.3051 0.098 Uiso calc R 1 H
H7B 1.0691 0.8467 0.2582 0.098 Uiso calc R 1 H
H7C 1.1212 0.7315 0.2163 0.098 Uiso calc R 1 H
C8 0.9076(2) 0.2236(5) 0.2634(3) 0.0583(12) Uani d . 1 C
H8A 0.8622 0.2653 0.2571 0.087 Uiso calc R 1 H
H8B 0.9109 0.1650 0.3106 0.087 Uiso calc R 1 H
H8C 0.9182 0.1497 0.2224 0.087 Uiso calc R 1 H
C9 0.7509(2) 1.1126(5) 0.4509(3) 0.0444(10) Uani d . 1 C
H9A 0.7751 1.2169 0.4546 0.053 Uiso calc R 1 H
H9B 0.7249 1.1128 0.4042 0.053 Uiso calc R 1 H
C10 0.8009(2) 0.9707(5) 0.4504(3) 0.0444(10) Uani d . 1 C
H10A 0.7961 0.9089 0.4035 0.053 Uiso calc R 1 H
H10B 0.8469 1.0139 0.4527 0.053 Uiso calc R 1 H
C11 0.66734(17) 0.9317(4) 0.5113(3) 0.0418(9) Uani d . 1 C
H11A 0.6408 0.9294 0.4649 0.050 Uiso calc R 1 H
H11B 0.6364 0.9188 0.5537 0.050 Uiso calc R 1 H
C12 0.71757(17) 0.7913(4) 0.5108(3) 0.0458(10) Uani d . 1 C
H12A 0.7125 0.7276 0.4645 0.055 Uiso calc R 1 H
H12B 0.7087 0.7183 0.5534 0.055 Uiso calc R 1 H
C13 0.7444(2) 1.0952(5) 0.5884(3) 0.0446(10) Uani d . 1 C
H13A 0.7145 1.0827 0.6318 0.054 Uiso calc R 1 H
H13B 0.7680 1.2001 0.5932 0.054 Uiso calc R 1 H
C14 0.7959(2) 0.9537(5) 0.5869(2) 0.0425(10) Uani d . 1 C
H14A 0.8416 0.9983 0.5905 0.051 Uiso calc R 1 H
H14B 0.7884 0.8814 0.6300 0.051 Uiso calc R 1 H
C15 0.8395(2) 0.7190(5) 0.5138(4) 0.0645(13) Uani d . 1 C
H15A 0.8847 0.7632 0.5168 0.097 Uiso calc R 1 H
H15B 0.8344 0.6589 0.4672 0.097 Uiso calc R 1 H
H15C 0.8316 0.6459 0.5558 0.097 Uiso calc R 1 H
C16 0.6536(2) 1.2351(5) 0.5183(4) 0.0661(13) Uani d . 1 C
H16A 0.6234 1.2230 0.5607 0.099 Uiso calc R 1 H
H16B 0.6278 1.2345 0.4721 0.099 Uiso calc R 1 H
H16C 0.6778 1.3380 0.5226 0.099 Uiso calc R 1 H
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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
_geom_angle_publ_flag
Cl7 Cu1 Cl8 104.36(5) y
Cl7 Cu1 Cl5 125.81(5) y
Cl8 Cu1 Cl5 98.22(4) y
Cl7 Cu1 Cl6 98.11(4) y
Cl8 Cu1 Cl6 130.39(5) y
Cl5 Cu1 Cl6 103.42(5) y
Cl3 Cu2 Cl1 97.59(4) y
Cl3 Cu2 Cl2 131.45(5) y
Cl1 Cu2 Cl2 100.28(5) y
Cl3 Cu2 Cl4 102.36(5) y
Cl1 Cu2 Cl4 131.28(5) y
Cl2 Cu2 Cl4 98.81(4) y
C13 N1 C11 108.9(3) ?
C13 N1 C16 110.0(4) ?
C11 N1 C16 110.8(3) ?
C13 N1 C9 108.8(3) ?
C11 N1 C9 108.8(3) ?
C16 N1 C9 109.6(3) ?
C14 N2 C10 109.0(3) ?
C14 N2 C15 110.7(4) ?
C10 N2 C15 109.3(4) ?
C14 N2 C12 109.0(3) ?
C10 N2 C12 108.5(3) ?
C15 N2 C12 110.3(3) ?
C4 N3 C6 109.1(3) ?
C4 N3 C7 109.7(3) ?
C6 N3 C7 111.6(4) ?
C4 N3 C2 108.5(3) ?
C6 N3 C2 107.5(3) ?
C7 N3 C2 110.3(3) ?
C5 N4 C1 109.4(3) ?
C5 N4 C3 109.4(3) ?
C1 N4 C3 108.6(3) ?
C5 N4 C8 111.0(3) ?
C1 N4 C8 109.4(3) ?
C3 N4 C8 109.1(3) ?
N4 C1 C2 109.7(3) ?
N4 C1 H1A 109.7 ?
C2 C1 H1A 109.7 ?
N4 C1 H1B 109.7 ?
C2 C1 H1B 109.7 ?
H1A C1 H1B 108.2 ?
N3 C2 C1 109.9(3) ?
N3 C2 H2A 109.7 ?
C1 C2 H2A 109.7 ?
N3 C2 H2B 109.7 ?
C1 C2 H2B 109.7 ?
H2A C2 H2B 108.2 ?
N4 C3 C4 108.7(3) ?
N4 C3 H3A 109.9 ?
C4 C3 H3A 109.9 ?
N4 C3 H3B 109.9 ?
C4 C3 H3B 109.9 ?
H3A C3 H3B 108.3 ?
N3 C4 C3 111.1(3) ?
N3 C4 H4A 109.4 ?
C3 C4 H4A 109.4 ?
N3 C4 H4B 109.4 ?
C3 C4 H4B 109.4 ?
H4A C4 H4B 108.0 ?
N4 C5 C6 110.3(3) ?
N4 C5 H5A 109.6 ?
C6 C5 H5A 109.6 ?
N4 C5 H5B 109.6 ?
C6 C5 H5B 109.6 ?
H5A C5 H5B 108.1 ?
N3 C6 C5 110.4(3) ?
N3 C6 H6A 109.6 ?
C5 C6 H6A 109.6 ?
N3 C6 H6B 109.6 ?
C5 C6 H6B 109.6 ?
H6A C6 H6B 108.1 ?
N3 C7 H7A 109.5 ?
N3 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
N3 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
N4 C8 H8A 109.5 ?
N4 C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
N4 C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
N1 C9 C10 109.4(3) ?
N1 C9 H9A 109.8 ?
C10 C9 H9A 109.8 ?
N1 C9 H9B 109.8 ?
C10 C9 H9B 109.8 ?
H9A C9 H9B 108.2 ?
N2 C10 C9 110.8(3) ?
N2 C10 H10A 109.5 ?
C9 C10 H10A 109.5 ?
N2 C10 H10B 109.5 ?
C9 C10 H10B 109.5 ?
H10A C10 H10B 108.1 ?
N1 C11 C12 110.5(3) ?
N1 C11 H11A 109.6 ?
C12 C11 H11A 109.6 ?
N1 C11 H11B 109.6 ?
C12 C11 H11B 109.6 ?
H11A C11 H11B 108.1 ?
C11 C12 N2 109.9(3) ?
C11 C12 H12A 109.7 ?
N2 C12 H12A 109.7 ?
C11 C12 H12B 109.7 ?
N2 C12 H12B 109.7 ?
H12A C12 H12B 108.2 ?
N1 C13 C14 109.8(3) ?
N1 C13 H13A 109.7 ?
C14 C13 H13A 109.7 ?
N1 C13 H13B 109.7 ?
C14 C13 H13B 109.7 ?
H13A C13 H13B 108.2 ?
N2 C14 C13 110.2(3) ?
N2 C14 H14A 109.6 ?
C13 C14 H14A 109.6 ?
N2 C14 H14B 109.6 ?
C13 C14 H14B 109.6 ?
H14A C14 H14B 108.1 ?
N2 C15 H15A 109.5 ?
N2 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
N2 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
N1 C16 H16A 109.5 ?
N1 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
N1 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 Cl7 2.2309(14) y
Cu1 Cl8 2.2407(10) y
Cu1 Cl5 2.2448(9) y
Cu1 Cl6 2.2515(14) y
Cu2 Cl3 2.2364(14) y
Cu2 Cl1 2.2367(13) y
Cu2 Cl2 2.2382(10) y
Cu2 Cl4 2.2434(10) y
N1 C13 1.486(5) ?
N1 C11 1.496(4) ?
N1 C16 1.502(4) ?
N1 C9 1.506(5) ?
N2 C14 1.474(5) ?
N2 C10 1.491(5) ?
N2 C15 1.500(4) ?
N2 C12 1.506(4) ?
N3 C4 1.486(5) ?
N3 C6 1.491(5) ?
N3 C7 1.501(5) ?
N3 C2 1.505(5) ?
N4 C5 1.477(5) ?
N4 C1 1.488(5) ?
N4 C3 1.503(4) ?
N4 C8 1.507(5) ?
C1 C2 1.522(6) ?
C1 H1A 0.9700 ?
C1 H1B 0.9700 ?
C2 H2A 0.9700 ?
C2 H2B 0.9700 ?
C3 C4 1.519(5) ?
C3 H3A 0.9700 ?
C3 H3B 0.9700 ?
C4 H4A 0.9700 ?
C4 H4B 0.9700 ?
C5 C6 1.507(6) ?
C5 H5A 0.9700 ?
C5 H5B 0.9700 ?
C6 H6A 0.9700 ?
C6 H6B 0.9700 ?
C7 H7A 0.9600 ?
C7 H7B 0.9600 ?
C7 H7C 0.9600 ?
C8 H8A 0.9600 ?
C8 H8B 0.9600 ?
C8 H8C 0.9600 ?
C9 C10 1.510(6) ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C10 H10A 0.9700 ?
C10 H10B 0.9700 ?
C11 C12 1.503(5) ?
C11 H11A 0.9700 ?
C11 H11B 0.9700 ?
C12 H12A 0.9700 ?
C12 H12B 0.9700 ?
C13 C14 1.527(5) ?
C13 H13A 0.9700 ?
C13 H13B 0.9700 ?
C14 H14A 0.9700 ?
C14 H14B 0.9700 ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
C16 H16A 0.9600 ?
C16 H16B 0.9600 ?
C16 H16C 0.9600 ?
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
C2 H2B Cl2 . 0.97 2.77 3.604(5) 144
C3 H3B Cl7 . 0.97 2.68 3.556(5) 151
C12 H12A Cl3 . 0.97 2.71 3.626(5) 157
C6 H6A Cl7 1_565 0.97 2.77 3.446(4) 127
C2 H2A Cl5 2_764 0.97 2.60 3.552(5) 167
C3 H3A Cl6 2_754 0.97 2.77 3.695(5) 160
C12 H12B Cl1 4_655 0.97 2.78 3.688(5) 157
C13 H13B Cl1 4_665 0.97 2.79 3.534(4) 134
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
_geom_torsion_publ_flag
C5 N4 C1 C2 54.4(4) ?
C3 N4 C1 C2 -64.8(4) ?
C8 N4 C1 C2 176.2(3) ?
C4 N3 C2 C1 54.2(4) ?
C6 N3 C2 C1 -63.7(4) ?
C7 N3 C2 C1 174.4(4) ?
N4 C1 C2 N3 7.9(5) y
C5 N4 C3 C4 -62.8(5) ?
C1 N4 C3 C4 56.5(4) ?
C8 N4 C3 C4 175.6(4) ?
C6 N3 C4 C3 54.2(5) ?
C7 N3 C4 C3 176.8(4) ?
C2 N3 C4 C3 -62.7(5) ?
N4 C3 C4 N3 6.5(5) y
C1 N4 C5 C6 -62.7(4) ?
C3 N4 C5 C6 56.1(4) ?
C8 N4 C5 C6 176.6(4) ?
C4 N3 C6 C5 -61.4(5) ?
C7 N3 C6 C5 177.1(4) ?
C2 N3 C6 C5 56.1(4) ?
N4 C5 C6 N3 5.5(5) y
C13 N1 C9 C10 59.8(4) ?
C11 N1 C9 C10 -58.7(4) ?
C16 N1 C9 C10 -180.0(3) ?
C14 N2 C10 C9 -58.8(4) ?
C15 N2 C10 C9 -180.0(3) ?
C12 N2 C10 C9 59.7(4) ?
N1 C9 C10 N2 -0.9(5) y
C13 N1 C11 C12 -58.7(5) ?
C16 N1 C11 C12 -179.8(5) ?
C9 N1 C11 C12 59.7(5) ?
N1 C11 C12 N2 -0.6(6) y
C14 N2 C12 C11 59.6(5) ?
C10 N2 C12 C11 -58.9(5) ?
C15 N2 C12 C11 -178.6(5) ?
C11 N1 C13 C14 59.5(4) ?
C16 N1 C13 C14 -179.0(3) ?
C9 N1 C13 C14 -59.0(4) ?
C10 N2 C14 C13 59.5(4) ?
C15 N2 C14 C13 179.8(3) ?
C12 N2 C14 C13 -58.7(4) ?
N1 C13 C14 N2 -0.6(5) y
