#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/36/2013662.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_2013662
loop_
_publ_author_name
'Pospieszna-Markiewicz, Izabela'
'Kubicki, Maciej'
_publ_section_title
;
 Redetermination of sperminium tetrachloride
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o664
_journal_page_last               o665
_journal_paper_doi               10.1107/S0108270103023655
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C10 H30 N4 4+, 4Cl 1-'
_chemical_formula_moiety         'C10 H30 N4 4+, 4Cl 1-'
_chemical_formula_sum            'C10 H30 Cl4 N4'
_chemical_formula_weight         348.18
_chemical_name_common            'sperminium tetrachloride'
_chemical_name_systematic
;
1,5,10,14-tetraazoniatetradecane tetrachloride
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.210(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.5690(10)
_cell_length_b                   7.9130(10)
_cell_length_c                   13.0020(10)
_cell_measurement_reflns_used    2927
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      4
_cell_volume                     880.24(17)
_computing_cell_refinement       'CrysAlis CCD'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis Red (Oxford Diffraction, 2002)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'KUMA KM-4 CCD four-circle diffractometer'
_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  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8391
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  0.943
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1989)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1902
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0300
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.02P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0476
_refine_ls_wR_factor_ref         0.0532
_reflns_number_gt                1382
_reflns_number_total             1902
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na1618.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2013662
_cod_database_fobs_code          2013662
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_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
_atom_site_type_symbol
Cl1 0.86523(5) -0.03768(5) 0.38096(3) 0.03227(13) Uani d . 1 . . Cl
Cl2 0.59188(6) 0.25832(6) 0.67679(3) 0.05061(16) Uani d . 1 . . Cl
N1 0.2349(2) 0.0764(2) 0.37997(14) 0.0339(4) Uani d . 1 . . N
H11 0.279(2) -0.018(2) 0.3649(13) 0.042(6) Uiso d . 1 . . H
H12 0.167(2) 0.053(2) 0.4211(15) 0.055(7) Uiso d . 1 . . H
H13 0.188(2) 0.109(2) 0.3230(14) 0.036(5) Uiso d . 1 . . H
C2 0.3506(2) 0.2027(3) 0.41895(15) 0.0391(5) Uani d . 1 . . C
H21 0.386(2) 0.174(2) 0.4842(14) 0.051(6) Uiso d . 1 . . H
H22 0.295(2) 0.308(3) 0.4200(14) 0.064(7) Uiso d . 1 . . H
C3 0.4889(2) 0.2134(2) 0.35276(14) 0.0322(4) Uani d . 1 . . C
H31 0.456(2) 0.2426(19) 0.2823(15) 0.050(5) Uiso d . 1 . . H
H32 0.5349(19) 0.111(2) 0.3504(12) 0.035(5) Uiso d . 1 . . H
C4 0.6060(2) 0.3402(2) 0.39674(14) 0.0324(4) Uani d . 1 . . C
H41 0.6331(18) 0.3166(19) 0.4635(13) 0.034(5) Uiso d . 1 . . H
H42 0.5674(19) 0.451(2) 0.3940(12) 0.038(5) Uiso d . 1 . . H
N5 0.75101(17) 0.3410(2) 0.34029(11) 0.0276(3) Uani d . 1 . . N
H51 0.793(2) 0.243(2) 0.3436(12) 0.037(5) Uiso d . 1 . . H
H52 0.7269(19) 0.362(2) 0.2776(13) 0.034(5) Uiso d . 1 . . H
C6 0.8691(2) 0.4694(3) 0.37704(13) 0.0314(4) Uani d . 1 . . C
H61 0.9456(19) 0.4662(19) 0.3319(12) 0.028(5) Uiso d . 1 . . H
H62 0.8122(19) 0.574(2) 0.3728(12) 0.035(5) Uiso d . 1 . . H
C7 0.9378(2) 0.4350(2) 0.48443(13) 0.0295(4) Uani d . 1 . . C
H71 0.9823(18) 0.326(2) 0.4879(11) 0.031(4) Uiso d . 1 . . H
H72 0.8595(18) 0.4308(18) 0.5309(12) 0.028(4) Uiso d . 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'
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
C2 N1 H11 . . 111.9(12)
C2 N1 H12 . . 114.3(13)
H11 N1 H12 . . 106.3(18)
C2 N1 H13 . . 111.3(11)
H11 N1 H13 . . 104.7(16)
H12 N1 H13 . . 107.7(17)
N1 C2 C3 . . 112.13(15)
N1 C2 H21 . . 109.4(11)
C3 C2 H21 . . 108.3(12)
N1 C2 H22 . . 105.7(12)
C3 C2 H22 . . 111.3(12)
H21 C2 H22 . . 109.9(16)
C2 C3 C4 . . 110.42(15)
C2 C3 H31 . . 110.7(11)
C4 C3 H31 . . 110.7(10)
C2 C3 H32 . . 109.1(10)
C4 C3 H32 . . 109.2(10)
H31 C3 H32 . . 106.7(14)
N5 C4 C3 . . 111.98(14)
N5 C4 H41 . . 107.4(10)
C3 C4 H41 . . 110.8(10)
N5 C4 H42 . . 106.3(10)
C3 C4 H42 . . 112.5(10)
H41 C4 H42 . . 107.4(14)
C4 N5 C6 . . 114.67(14)
C4 N5 H51 . . 109.7(12)
C6 N5 H51 . . 108.8(12)
C4 N5 H52 . . 108.2(11)
C6 N5 H52 . . 107.5(11)
H51 N5 H52 . . 107.8(16)
N5 C6 C7 . . 113.28(15)
N5 C6 H61 . . 106.0(10)
C7 C6 H61 . . 109.6(9)
N5 C6 H62 . . 103.6(10)
C7 C6 H62 . . 112.3(10)
H61 C6 H62 . . 111.8(14)
C6 C7 C7 . 3_766 110.82(18)
C6 C7 H71 . . 110.2(9)
C7 C7 H71 3_766 . 109.2(10)
C6 C7 H72 . . 110.5(9)
C7 C7 H72 3_766 . 111.8(9)
H71 C7 H72 . . 104.1(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
N1 C2 . 1.477(2) ?
N1 H11 . 0.864(19) ?
N1 H12 . 0.83(2) ?
N1 H13 . 0.864(18) ?
C2 C3 . 1.505(3) ?
C2 H21 . 0.913(18) ?
C2 H22 . 0.96(2) ?
C3 C4 . 1.509(2) ?
C3 H31 . 0.972(19) ?
C3 H32 . 0.905(16) ?
C4 N5 . 1.478(2) ?
C4 H41 . 0.905(16) ?
C4 H42 . 0.940(17) ?
N5 C6 . 1.493(2) ?
N5 H51 . 0.855(17) ?
N5 H52 . 0.845(17) ?
C6 C7 . 1.509(2) ?
C6 H61 . 0.905(16) ?
C6 H62 . 0.959(17) ?
C7 C7 3_766 1.521(3) ?
C7 H71 . 0.940(17) ?
C7 H72 . 0.928(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
N1 H11 Cl2 3_656 0.864(19) 2.28(2) 3.144(2) 176.3(16)
N1 H12 Cl1 3_656 0.83(2) 2.61(2) 3.2848(19) 139.3(16)
N1 H12 Cl1 1_455 0.83(2) 2.70(2) 3.2945(18) 129.1(16)
N1 H13 Cl2 4_565 0.864(18) 2.283(18) 3.1351(18) 168.9(15)
C4 H41 Cl2 . 0.905(16) 2.853(17) 3.707(2) 157.9(13)
C4 H42 Cl2 3_666 0.940(17) 2.801(17) 3.701(2) 160.7(12)
N5 H51 Cl1 . 0.855(17) 2.350(18) 3.1873(17) 166.6(16)
N5 H52 Cl1 2_655 0.845(17) 2.308(18) 3.1414(15) 168.8(15)
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
N1 C2 C3 C4 . -178.51(17)
C2 C3 C4 N5 . 173.82(16)
C3 C4 N5 C6 . 177.39(15)
C4 N5 C6 C7 . 66.7(2)
N5 C6 C7 C7 3_766 177.4(2)
