#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/44/2224473.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_2224473
loop_
_publ_author_name
'Garza Rodríguez, Luis Angel'
'Bernès, Sylvain'
'Nájera Martínez, Blanca'
'Elizondo Martínez, Perla'
'Pérez Rodríguez, Nancy'
_publ_section_title
;N,N'-Bis(2-ammoniobenzyl)ethane-1,2-diammonium--nitrate--perchlorate
 (1/1.5/2.5)
;
_journal_coeditor_code           VM2008
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2995
_journal_paper_doi               10.1107/S160053680904519X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H26 N4 4+, 2.5Cl O4 -, 1.5N O3 -'
_chemical_formula_moiety         'C16 H26 N4 4+, 2.5(Cl O4 -), 1.5(N O3 -)'
_chemical_formula_sum            'C16 H26 Cl2.5 N5.5 O14.5'
_chemical_formula_weight         616.05
_chemical_name_systematic
;
N,N'-Bis(2-ammoniobenzyl)ethane-1,2-diammonium--nitrate--
perchlorate (1/1.5/2.5)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL-Plus
_cell_angle_alpha                90.00
_cell_angle_beta                 106.97(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.427(3)
_cell_length_b                   12.637(3)
_cell_length_c                   11.834(3)
_cell_measurement_pressure       101(2)
_cell_measurement_reflns_used    73
_cell_measurement_temperature    298.0(10)
_cell_measurement_theta_max      12.43
_cell_measurement_theta_min      4.95
_cell_volume                     1205.4(6)
_computing_cell_refinement       'XSCANS (Siemens, 1996)'
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        'XSCANS (Siemens, 1996)'
_computing_molecular_graphics
;
SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material  'SHELXTL-Plus (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL-Plus (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL-Plus (Sheldrick, 2008)'
_diffrn_ambient_temperature      298.0(10)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       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  0.0573
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6392
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.42
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.411
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             638
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.272
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2125
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0504
_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)+(0.0221P)²+1.6735P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1192
_reflns_number_gt                1757
_reflns_number_total             2125
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            vm2008.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C16 H26 Cl2.50 N5.50 O14.50'
_cod_database_code               2224473
_cod_database_fobs_code          2224473
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
N N1 -0.1084(4) 0.6532(2) 0.2742(2) 0.0430(7) Uani d . 1 . .
H H1A -0.2090 0.6242 0.2538 0.065 Uiso calc R 1 . .
H H1B -0.1163 0.7215 0.2897 0.065 Uiso calc R 1 . .
H H1C -0.0445 0.6208 0.3381 0.065 Uiso calc R 1 . .
C C2 -0.0347(4) 0.6416(2) 0.1763(3) 0.0326(7) Uani d . 1 . .
C C3 -0.1440(4) 0.6359(2) 0.0652(3) 0.0399(8) Uani d . 1 . .
H H3A -0.2578 0.6371 0.0546 0.048 Uiso calc R 1 . .
C C4 -0.0826(5) 0.6283(2) -0.0310(3) 0.0434(8) Uani d . 1 . .
H H4A -0.1553 0.6235 -0.1070 0.052 Uiso calc R 1 . .
C C5 0.0852(5) 0.6280(3) -0.0143(3) 0.0430(8) Uani d . 1 . .
H H5A 0.1263 0.6245 -0.0791 0.052 Uiso calc R 1 . .
C C6 0.1929(4) 0.6327(2) 0.0979(3) 0.0394(8) Uani d . 1 . .
H H6A 0.3066 0.6313 0.1082 0.047 Uiso calc R 1 . .
C C7 0.1348(4) 0.6396(2) 0.1969(3) 0.0311(7) Uani d . 1 . .
C C8 0.2604(4) 0.6487(2) 0.3159(3) 0.0371(7) Uani d . 1 . .
H H8A 0.2095 0.6834 0.3696 0.044 Uiso calc R 1 . .
H H8B 0.3513 0.6928 0.3091 0.044 Uiso calc R 1 . .
N N9 0.3283(3) 0.5437(2) 0.3671(2) 0.0350(6) Uani d . 1 . .
H H9A 0.2457 0.5053 0.3806 0.042 Uiso calc R 1 . .
H H9B 0.3660 0.5085 0.3140 0.042 Uiso calc R 1 . .
C C10 0.4644(4) 0.5534(3) 0.4787(3) 0.0380(8) Uani d . 1 . .
H H10A 0.4225 0.5862 0.5384 0.046 Uiso calc R 1 . .
H H10B 0.5509 0.5985 0.4662 0.046 Uiso calc R 1 . .
Cl Cl1 -0.00237(10) 0.35712(6) 0.40133(7) 0.0396(2) Uani d . 1 . .
O O1 -0.1221(4) 0.3829(3) 0.4604(3) 0.0752(9) Uani d . 1 . .
O O2 0.0116(4) 0.4419(2) 0.3253(2) 0.0643(8) Uani d . 1 . .
O O3 0.1540(4) 0.3438(2) 0.4887(2) 0.0648(8) Uani d . 1 . .
O O4 -0.0495(4) 0.2635(2) 0.3332(3) 0.0647(8) Uani d . 1 . .
Cl Cl2 0.5512(9) 0.4371(6) 0.1804(8) 0.0358(15) Uani d PD 0.25 A 1
O O5 0.587(4) 0.5336(15) 0.244(2) 0.039(7) Uani d PD 0.25 A 1
O O6 0.5011(19) 0.4701(12) 0.0603(8) 0.083(4) Uani d PD 0.25 . 1
O O7 0.415(4) 0.394(4) 0.211(4) 0.083(14) Uani d PD 0.25 A 1
O O8 0.675(2) 0.3628(14) 0.186(2) 0.052(5) Uani d PD 0.25 A 1
N N11 0.5525(14) 0.4327(9) 0.2076(9) 0.068(4) Uani d PD 0.75 B 2
O O12 0.5925(19) 0.5250(7) 0.2380(11) 0.071(4) Uani d PD 0.75 B 2
O O13 0.4469(14) 0.3860(9) 0.2416(13) 0.056(2) Uani d PD 0.75 B 2
O O14 0.6277(12) 0.3811(8) 0.1526(9) 0.099(3) Uani d PD 0.75 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 1 -2
-1 0 3
-2 0 2
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 N1 H1A . . 109.5 ?
C2 N1 H1B . . 109.5 ?
H1A N1 H1B . . 109.5 ?
C2 N1 H1C . . 109.5 ?
H1A N1 H1C . . 109.5 ?
H1B N1 H1C . . 109.5 ?
C3 C2 C7 . . 122.8(3) ?
C3 C2 N1 . . 116.1(3) ?
C7 C2 N1 . . 121.0(3) ?
C2 C3 C4 . . 119.0(3) ?
C2 C3 H3A . . 120.5 ?
C4 C3 H3A . . 120.5 ?
C5 C4 C3 . . 120.0(3) ?
C5 C4 H4A . . 120.0 ?
C3 C4 H4A . . 120.0 ?
C4 C5 C6 . . 120.2(3) ?
C4 C5 H5A . . 119.9 ?
C6 C5 H5A . . 119.9 ?
C5 C6 C7 . . 121.2(3) ?
C5 C6 H6A . . 119.4 ?
C7 C6 H6A . . 119.4 ?
C2 C7 C6 . . 116.8(3) ?
C2 C7 C8 . . 125.2(3) ?
C6 C7 C8 . . 117.9(3) ?
C7 C8 N9 . . 113.2(2) ?
C7 C8 H8A . . 108.9 ?
N9 C8 H8A . . 108.9 ?
C7 C8 H8B . . 108.9 ?
N9 C8 H8B . . 108.9 ?
H8A C8 H8B . . 107.8 ?
C10 N9 C8 . . 113.1(2) ?
C10 N9 H9A . . 109.0 ?
C8 N9 H9A . . 109.0 ?
C10 N9 H9B . . 109.0 ?
C8 N9 H9B . . 109.0 ?
H9A N9 H9B . . 107.8 ?
N9 C10 C10 . 3_666 110.7(3) ?
N9 C10 H10A . . 109.5 ?
C10 C10 H10A 3_666 . 109.5 ?
N9 C10 H10B . . 109.5 ?
C10 C10 H10B 3_666 . 109.5 ?
H10A C10 H10B . . 108.1 ?
O4 Cl1 O1 . . 110.36(19) ?
O4 Cl1 O2 . . 109.21(17) ?
O1 Cl1 O2 . . 109.82(19) ?
O4 Cl1 O3 . . 111.00(17) ?
O1 Cl1 O3 . . 107.96(19) ?
O2 Cl1 O3 . . 108.46(19) ?
O8 Cl2 O7 . . 112(2) ?
O8 Cl2 O5 . . 121.0(17) ?
O7 Cl2 O5 . . 105(3) ?
O8 Cl2 O6 . . 104.3(13) ?
O7 Cl2 O6 . . 110(2) ?
O5 Cl2 O6 . . 103.4(13) ?
O14 N11 O13 . . 117.1(12) ?
O14 N11 O12 . . 121.2(12) ?
O13 N11 O12 . . 121.3(12) ?
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
N1 C2 . 1.473(4) ?
N1 H1A . 0.8900 ?
N1 H1B . 0.8900 ?
N1 H1C . 0.8900 ?
C2 C3 . 1.369(4) ?
C2 C7 . 1.378(4) ?
C3 C4 . 1.385(5) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.369(5) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.374(5) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.398(4) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.498(4) ?
C8 N9 . 1.501(4) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
N9 C10 . 1.480(4) ?
N9 H9A . 0.9000 ?
N9 H9B . 0.9000 ?
C10 C10 3_666 1.503(6) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
Cl1 O4 . 1.421(3) ?
Cl1 O1 . 1.423(3) ?
Cl1 O2 . 1.426(3) ?
Cl1 O3 . 1.428(3) ?
Cl2 O8 . 1.389(9) ?
Cl2 O7 . 1.409(10) ?
Cl2 O5 . 1.417(10) ?
Cl2 O6 . 1.422(9) ?
N11 O14 . 1.222(8) ?
N11 O13 . 1.229(8) ?
N11 O12 . 1.238(8) ?
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
N1 H1C O2 . 0.89 2.32 2.856(4) 118.4 no
N1 H1B O13 2 0.89 2.61 3.270(13) 131.9 no
N9 H9B O5 . 0.90 2.27 2.96(3) 132.9 no
N9 H9B O12 . 0.90 2.35 3.055(15) 135.8 no
N9 H9A O2 . 0.90 2.05 2.872(4) 151.1 yes
N9 H9A O3 . 0.90 2.64 3.441(4) 148.6 no
N9 H9B O7 . 0.90 2.02 2.89(5) 162.8 yes
N9 H9B O13 . 0.90 1.98 2.836(13) 157.3 yes
N1 H1A O5 1_455 0.89 2.04 2.91(3) 165.2 yes
N1 H1A O12 1_455 0.89 2.05 2.920(13) 164.1 yes
N1 H1B O8 2 0.89 1.90 2.78(2) 169.7 yes
N1 H1B O14 2 0.89 2.14 3.026(11) 173.6 yes
N1 H1C O1 3_566 0.89 2.39 3.207(4) 153.0 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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 C2 C3 C4 . . . . -0.3(5) ?
N1 C2 C3 C4 . . . . 178.0(3) ?
C2 C3 C4 C5 . . . . -0.8(5) ?
C3 C4 C5 C6 . . . . 1.5(5) ?
C4 C5 C6 C7 . . . . -1.0(5) ?
C3 C2 C7 C6 . . . . 0.7(4) ?
N1 C2 C7 C6 . . . . -177.5(3) ?
C3 C2 C7 C8 . . . . 178.2(3) ?
N1 C2 C7 C8 . . . . -0.1(4) ?
C5 C6 C7 C2 . . . . -0.1(4) ?
C5 C6 C7 C8 . . . . -177.7(3) ?
C2 C7 C8 N9 . . . . 98.7(3) ?
C6 C7 C8 N9 . . . . -83.9(3) ?
C7 C8 N9 C10 . . . . 174.1(3) ?
C8 N9 C10 C10 . . . 3_666 -175.9(3) ?
O8 Cl2 O6 O6 . . . 3_665 -79(5) ?
O7 Cl2 O6 O6 . . . 3_665 160(6) ?
O5 Cl2 O6 O6 . . . 3_665 48(6) ?
