#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/46/2234660.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_2234660
loop_
_publ_author_name
'Ismail, Wafiuddin'
'Yamin, Bohari M.'
'Daran, Jean-Claude'
_publ_section_title
;
 5,5,7,12,14,14-Hexamethyl-1,8-diaza-4,11-diazoniacyclotetradeca-4,11-diene
 dichloride trihydrate
;
_journal_coeditor_code           HG5196
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1476
_journal_page_last               o1477
_journal_paper_doi               10.1107/S1600536812016649
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C16 H34 N4 2+, 2Cl -, 3H2 O'
_chemical_formula_moiety         'C16 H34 N4 2+, 2(Cl -), 3(H2 O)'
_chemical_formula_sum            'C16 H40 Cl2 N4 O3'
_chemical_formula_weight         407.42
_chemical_melting_point_gt       372.1
_chemical_melting_point_lt       372.8
_chemical_name_systematic
;
5,5,7,12,14,14-Hexamethyl-1,8-diaza-4,11-diazoniacyclotetradeca-4,11-diene
dichloride trihydrate
;
_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                73.752(9)
_cell_angle_beta                 86.085(9)
_cell_angle_gamma                71.886(8)
_cell_formula_units_Z            2
_cell_length_a                   8.576(4)
_cell_length_b                   10.735(4)
_cell_length_c                   13.438(6)
_cell_measurement_reflns_used    2072
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1.58
_cell_volume                     1128.6(8)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON
(Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 83.66
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type
;
Bruker SMART APEX CCD area-detector
;
_diffrn_measurement_method       'ω scan'
_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  0.0506
_diffrn_reflns_av_sigmaI/netI    0.0580
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11977
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.58
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_T_max  0.9610
_exptl_absorpt_correction_T_min  0.8971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3987
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0546
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0559P)²+0.1922P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1358
_reflns_number_gt                2878
_reflns_number_total             3987
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            hg5196.cif
_cod_data_source_block           I
_cod_original_cell_volume        1128.7(8)
_cod_database_code               2234660
_cod_database_fobs_code          2234660
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_symmetry_multiplicity
Cl Cl1 0.54889(10) 0.63892(9) 0.26242(6) 0.0731(3) Uani d . 1 1
Cl Cl2 0.91229(9) 0.98055(8) 0.24245(6) 0.0552(2) Uani d . 1 1
O O1W 0.2897(3) 0.9092(3) 0.3252(2) 0.1010(9) Uani d . 1 1
H H1W1 0.2055 0.9197 0.2942 0.151 Uiso d R 1 1
H H2W1 0.3523 0.8513 0.2998 0.151 Uiso d R 1 1
O O2W 0.2391(3) 0.5665(3) 0.18015(19) 0.0887(8) Uani d . 1 1
H H1W2 0.1576 0.6126 0.2037 0.133 Uiso d R 1 1
H H2W2 0.3136 0.5769 0.2095 0.133 Uiso d R 1 1
O O3W 0.9133(3) 0.6822(2) 0.26157(19) 0.0869(8) Uani d . 1 1
H H1W3 0.8192 0.6909 0.2442 0.130 Uiso d R 1 1
H H2W3 0.9170 0.7602 0.2532 0.130 Uiso d R 1 1
N N1 1.1625(2) 0.3762(2) 0.45434(15) 0.0365(5) Uani d . 1 1
N N2 0.8331(3) 0.4327(2) 0.42420(16) 0.0336(5) Uani d . 1 1
H H1N2 0.754(3) 0.494(3) 0.377(2) 0.049(8) Uiso d . 1 1
H H2N2 0.920(3) 0.463(2) 0.4218(17) 0.032(7) Uiso d . 1 1
N N3 0.3084(2) 1.0996(2) 0.03415(16) 0.0394(5) Uani d . 1 1
N N4 0.6102(3) 1.1063(2) 0.08282(16) 0.0335(5) Uani d . 1 1
H H1N4 0.688(3) 1.061(3) 0.136(2) 0.054(8) Uiso d . 1 1
H H2N4 0.542(3) 1.063(2) 0.0808(17) 0.026(6) Uiso d . 1 1
C C1 1.2999(3) 0.4269(3) 0.4597(2) 0.0409(6) Uani d . 1 1
H H1A 1.3631 0.4267 0.3971 0.049 Uiso calc R 1 1
H H1B 1.3712 0.3675 0.5182 0.049 Uiso calc R 1 1
C C2 1.1821(3) 0.2496(3) 0.47770(18) 0.0365(6) Uani d . 1 1
C C3 1.0377(3) 0.2016(3) 0.4681(2) 0.0421(6) Uani d . 1 1
H H3A 0.9935 0.1775 0.5367 0.051 Uiso calc R 1 1
H H3B 1.0785 0.1188 0.4460 0.051 Uiso calc R 1 1
C C4 0.8963(3) 0.2984(2) 0.39511(19) 0.0365(6) Uani d . 1 1
C C5 0.7616(3) 0.4304(3) 0.52835(19) 0.0392(6) Uani d . 1 1
H H5A 0.8443 0.3738 0.5815 0.047 Uiso calc R 1 1
H H5B 0.6717 0.3918 0.5368 0.047 Uiso calc R 1 1
C C6 1.3381(3) 0.1384(3) 0.5155(3) 0.0673(9) Uani d . 1 1
H H6A 1.4014 0.1686 0.5548 0.101 Uiso calc R 1 1
H H6B 1.4000 0.1158 0.4573 0.101 Uiso calc R 1 1
H H6C 1.3131 0.0595 0.5587 0.101 Uiso calc R 1 1
C C7 0.9524(3) 0.3337(3) 0.2835(2) 0.0477(7) Uani d . 1 1
H H7A 1.0376 0.3754 0.2794 0.072 Uiso calc R 1 1
H H7B 0.8613 0.3959 0.2397 0.072 Uiso calc R 1 1
H H7C 0.9936 0.2522 0.2612 0.072 Uiso calc R 1 1
C C8 0.7565(3) 0.2372(3) 0.4025(2) 0.0503(7) Uani d . 1 1
H H8A 0.7280 0.2089 0.4738 0.076 Uiso calc R 1 1
H H8B 0.7904 0.1600 0.3746 0.076 Uiso calc R 1 1
H H8C 0.6629 0.3043 0.3637 0.076 Uiso calc R 1 1
C C9 0.2026(3) 1.0191(3) 0.0267(2) 0.0434(7) Uani d . 1 1
H H9A 0.1299 1.0660 -0.0334 0.052 Uiso calc R 1 1
H H9B 0.1355 1.0093 0.0878 0.052 Uiso calc R 1 1
C C10 0.2476(3) 1.2250(3) 0.02649(19) 0.0392(6) Uani d . 1 1
C C11 0.3598(3) 1.3067(3) 0.0326(2) 0.0446(7) Uani d . 1 1
H H11A 0.2945 1.3883 0.0511 0.054 Uiso calc R 1 1
H H11B 0.4019 1.3353 -0.0360 0.054 Uiso calc R 1 1
C C12 0.5058(3) 1.2355(2) 0.10895(19) 0.0385(6) Uani d . 1 1
C C13 0.6969(3) 1.1195(3) -0.01763(19) 0.0418(6) Uani d . 1 1
H H13A 0.7678 1.1756 -0.0216 0.050 Uiso calc R 1 1
H H13B 0.6174 1.1634 -0.0745 0.050 Uiso calc R 1 1
C C14 0.0690(4) 1.3023(3) 0.0107(3) 0.0748(10) Uani d . 1 1
H H14A 0.0055 1.2405 0.0349 0.112 Uiso calc R 1 1
H H14B 0.0458 1.3466 -0.0617 0.112 Uiso calc R 1 1
H H14C 0.0409 1.3694 0.0489 0.112 Uiso calc R 1 1
C C15 0.6104(3) 1.3283(3) 0.1027(2) 0.0520(7) Uani d . 1 1
H H15A 0.7093 1.2782 0.1434 0.078 Uiso calc R 1 1
H H15B 0.5504 1.4037 0.1290 0.078 Uiso calc R 1 1
H H15C 0.6378 1.3616 0.0318 0.078 Uiso calc R 1 1
C C16 0.4492(3) 1.1912(3) 0.2195(2) 0.0495(7) Uani d . 1 1
H H16A 0.5431 1.1463 0.2654 0.074 Uiso calc R 1 1
H H16B 0.3871 1.1296 0.2231 0.074 Uiso calc R 1 1
H H16C 0.3818 1.2697 0.2396 0.074 Uiso calc R 1 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'
Cl Cl 0.1484 0.1585 '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
H1W1 O1W H2W1 . . 98.0
H1W2 O2W H2W2 . . 101.4
H1W3 O3W H2W3 . . 105.5
C2 N1 C1 . . 120.7(2)
C5 N2 C4 . . 118.08(19)
C5 N2 H1N2 . . 106.4(16)
C4 N2 H1N2 . . 109.7(16)
C5 N2 H2N2 . . 106.5(15)
C4 N2 H2N2 . . 105.8(15)
H1N2 N2 H2N2 . . 110(2)
C10 N3 C9 . . 120.1(2)
C13 N4 C12 . . 118.30(19)
C13 N4 H1N4 . . 108.3(17)
C12 N4 H1N4 . . 106.2(16)
C13 N4 H2N4 . . 106.8(15)
C12 N4 H2N4 . . 104.3(15)
H1N4 N4 H2N4 . . 113(2)
N1 C1 C5 . 2_766 110.30(19)
N1 C1 H1A . . 109.6
C5 C1 H1A 2_766 . 109.6
N1 C1 H1B . . 109.6
C5 C1 H1B 2_766 . 109.6
H1A C1 H1B . . 108.1
N1 C2 C6 . . 126.2(2)
N1 C2 C3 . . 119.0(2)
C6 C2 C3 . . 114.9(2)
C2 C3 C4 . . 118.2(2)
C2 C3 H3A . . 107.8
C4 C3 H3A . . 107.8
C2 C3 H3B . . 107.8
C4 C3 H3B . . 107.8
H3A C3 H3B . . 107.1
C8 C4 C3 . . 110.6(2)
C8 C4 C7 . . 110.3(2)
C3 C4 C7 . . 111.4(2)
C8 C4 N2 . . 108.9(2)
C3 C4 N2 . . 109.49(19)
C7 C4 N2 . . 106.1(2)
N2 C5 C1 . 2_766 109.9(2)
N2 C5 H5A . . 109.7
C1 C5 H5A 2_766 . 109.7
N2 C5 H5B . . 109.7
C1 C5 H5B 2_766 . 109.7
H5A C5 H5B . . 108.2
C2 C6 H6A . . 109.5
C2 C6 H6B . . 109.5
H6A C6 H6B . . 109.5
C2 C6 H6C . . 109.5
H6A C6 H6C . . 109.5
H6B C6 H6C . . 109.5
C4 C7 H7A . . 109.5
C4 C7 H7B . . 109.5
H7A C7 H7B . . 109.5
C4 C7 H7C . . 109.5
H7A C7 H7C . . 109.5
H7B C7 H7C . . 109.5
C4 C8 H8A . . 109.5
C4 C8 H8B . . 109.5
H8A C8 H8B . . 109.5
C4 C8 H8C . . 109.5
H8A C8 H8C . . 109.5
H8B C8 H8C . . 109.5
N3 C9 C13 . 2_675 110.7(2)
N3 C9 H9A . . 109.5
C13 C9 H9A 2_675 . 109.5
N3 C9 H9B . . 109.5
C13 C9 H9B 2_675 . 109.5
H9A C9 H9B . . 108.1
N3 C10 C14 . . 124.9(2)
N3 C10 C11 . . 119.1(2)
C14 C10 C11 . . 116.0(2)
C10 C11 C12 . . 116.8(2)
C10 C11 H11A . . 108.1
C12 C11 H11A . . 108.1
C10 C11 H11B . . 108.1
C12 C11 H11B . . 108.1
H11A C11 H11B . . 107.3
C15 C12 N4 . . 109.0(2)
C15 C12 C16 . . 110.2(2)
N4 C12 C16 . . 106.2(2)
C15 C12 C11 . . 110.4(2)
N4 C12 C11 . . 109.54(19)
C16 C12 C11 . . 111.3(2)
N4 C13 C9 . 2_675 109.9(2)
N4 C13 H13A . . 109.7
C9 C13 H13A 2_675 . 109.7
N4 C13 H13B . . 109.7
C9 C13 H13B 2_675 . 109.7
H13A C13 H13B . . 108.2
C10 C14 H14A . . 109.5
C10 C14 H14B . . 109.5
H14A C14 H14B . . 109.5
C10 C14 H14C . . 109.5
H14A C14 H14C . . 109.5
H14B C14 H14C . . 109.5
C12 C15 H15A . . 109.5
C12 C15 H15B . . 109.5
H15A C15 H15B . . 109.5
C12 C15 H15C . . 109.5
H15A C15 H15C . . 109.5
H15B C15 H15C . . 109.5
C12 C16 H16A . . 109.5
C12 C16 H16B . . 109.5
H16A C16 H16B . . 109.5
C12 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_site_symmetry_2
_geom_bond_distance
O1W H1W1 . 0.8197
O1W H2W1 . 0.8227
O2W H1W2 . 0.8219
O2W H2W2 . 0.8240
O3W H1W3 . 0.8259
O3W H2W3 . 0.8234
N1 C2 . 1.265(3)
N1 C1 . 1.457(3)
N2 C5 . 1.486(3)
N2 C4 . 1.525(3)
N2 H1N2 . 0.92(3)
N2 H2N2 . 0.90(2)
N3 C10 . 1.260(3)
N3 C9 . 1.459(3)
N4 C13 . 1.489(3)
N4 C12 . 1.518(3)
N4 H1N4 . 0.93(3)
N4 H2N4 . 0.86(2)
C1 C5 2_766 1.508(3)
C1 H1A . 0.9700
C1 H1B . 0.9700
C2 C6 . 1.494(3)
C2 C3 . 1.507(3)
C3 C4 . 1.523(3)
C3 H3A . 0.9700
C3 H3B . 0.9700
C4 C8 . 1.522(3)
C4 C7 . 1.523(4)
C5 C1 2_766 1.508(3)
C5 H5A . 0.9700
C5 H5B . 0.9700
C6 H6A . 0.9600
C6 H6B . 0.9600
C6 H6C . 0.9600
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 C13 2_675 1.504(4)
C9 H9A . 0.9700
C9 H9B . 0.9700
C10 C14 . 1.495(4)
C10 C11 . 1.509(3)
C11 C12 . 1.532(3)
C11 H11A . 0.9700
C11 H11B . 0.9700
C12 C15 . 1.517(3)
C12 C16 . 1.522(4)
C13 C9 2_675 1.504(4)
C13 H13A . 0.9700
C13 H13B . 0.9700
C14 H14A . 0.9600
C14 H14B . 0.9600
C14 H14C . 0.9600
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
_geom_hbond_publ_flag
N2 H2N2 N1 1_555 0.90(3) 2.02(3) 2.732(3) 135.6(18) yes
N4 H2N4 N3 1_555 0.86(3) 2.03(3) 2.740(3) 140(2) yes
O1W H2W1 Cl1 1_555 0.82 2.54 3.343(4) 167 yes
O2W H2W2 Cl1 1_555 0.82 2.51 3.324(3) 168 yes
O3W H1W3 Cl1 1_555 0.83 2.53 3.298(3) 156 yes
O3W H2W3 Cl2 1_555 0.82 2.32 3.138(3) 175 yes
N2 H1N2 Cl1 1_555 0.92(3) 2.28(3) 3.201(3) 177(3) yes
N4 H1N4 Cl2 1_555 0.93(3) 2.27(3) 3.178(3) 167(2) yes
O1W H1W1 Cl2 1_455 0.82 2.49 3.282(3) 163 yes
O2W H1W2 O3W 1_455 0.82 2.16 2.955(4) 161 yes
C9 H9B Cl2 1_455 0.97 2.75 3.709(3) 172 yes
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_4
_geom_torsion
C2 N1 C1 C5 2_766 -157.0(2)
C1 N1 C2 C6 . 2.0(4)
C1 N1 C2 C3 . -178.3(2)
N1 C2 C3 C4 . 22.6(3)
C6 C2 C3 C4 . -157.6(2)
C2 C3 C4 C8 . -175.2(2)
C2 C3 C4 C7 . 61.8(3)
C2 C3 C4 N2 . -55.2(3)
C5 N2 C4 C8 . 58.2(3)
C5 N2 C4 C3 . -62.8(3)
C5 N2 C4 C7 . 176.9(2)
C4 N2 C5 C1 2_766 -177.59(19)
C10 N3 C9 C13 2_675 169.2(2)
C9 N3 C10 C14 . 0.6(4)
C9 N3 C10 C11 . -179.0(2)
N3 C10 C11 C12 . -37.1(4)
C14 C10 C11 C12 . 143.3(3)
C13 N4 C12 C15 . -55.2(3)
C13 N4 C12 C16 . -174.0(2)
C13 N4 C12 C11 . 65.7(3)
C10 C11 C12 C15 . 177.6(2)
C10 C11 C12 N4 . 57.5(3)
C10 C11 C12 C16 . -59.7(3)
C12 N4 C13 C9 2_675 178.0(2)
