#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202144.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_2202144
loop_
_publ_author_name
'Gunatilleke, Shamila S.'
'Norman, Richard E.'
_publ_section_title
;
N,N,N',N'-Tetrakis(2-pyridiniomethyl)ethylenediamine
tetraperchlorate
;
_journal_issue 3
_journal_name_full 'Acta Crystallographica Section E'
_journal_page_first o269
_journal_page_last o271
_journal_volume 59
_journal_year 2003
_chemical_formula_iupac 'C26 H32 N6 4+, 4Cl O4 1-'
_chemical_formula_moiety 'C26 H32 N6 4+, 4Cl O4 1-'
_chemical_formula_structural 'C26 H32 N6 4+, 4Cl O4 1-'
_chemical_formula_sum 'C26 H32 Cl4 N6 O16'
_chemical_formula_weight 826.38
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_cell_angle_alpha 100.2225(9)
_cell_angle_beta 105.5358(10)
_cell_angle_gamma 94.4063(13)
_cell_formula_units_Z 1
_cell_length_a 8.4278(2)
_cell_length_b 9.2848(2)
_cell_length_c 11.3490(3)
_cell_measurement_reflns_used 3927
_cell_measurement_temperature 100
_cell_measurement_theta_max 30.0
_cell_measurement_theta_min 2.5
_cell_volume 834.76(4)
_computing_cell_refinement 'DENZO and SCALEPACK'
_computing_data_collection 'COLLECT (Nonius 2000)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_publication_material TEXSAN
_computing_structure_refinement
'TEXSAN (Molecular Structure Corporation, 1997-1999)'
_computing_structure_solution 'SIR92 (Altomare et. al. 1993)'
_diffrn_ambient_temperature 100
_diffrn_measured_fraction_theta_full 0.97
_diffrn_measured_fraction_theta_max 0.97
_diffrn_measurement_device
'Nonius KappaCCD (with an Oxford Cryosystems Cryostream cooler)'
_diffrn_measurement_method ' \w scans with \k offsets'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.7107
_diffrn_reflns_av_R_equivalents 0.0298
_diffrn_reflns_av_sigmaI/netI 0.096
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -11
_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 16863
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full 29.5
_diffrn_reflns_theta_max 29.5
_diffrn_reflns_theta_min 2.69
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 0.439
_exptl_absorpt_correction_T_max 0.957
_exptl_absorpt_correction_T_min 0.891
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(HKL SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour gold
_exptl_crystal_density_diffrn 1.64
_exptl_crystal_density_meas 'not measured'
_exptl_crystal_description fragment
_exptl_crystal_F_000 426.00
_exptl_crystal_size_max 0.25
_exptl_crystal_size_mid 0.25
_exptl_crystal_size_min 0.10
_refine_diff_density_max 0.47
_refine_diff_density_min -0.40
_refine_ls_extinction_coef 0.204493
_refine_ls_extinction_method Zachariasen
_refine_ls_goodness_of_fit_all 0.969
_refine_ls_goodness_of_fit_ref 1.046
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_constraints 0
_refine_ls_number_parameters 236
_refine_ls_number_reflns 2656
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0742
_refine_ls_R_factor_gt 0.0612
_refine_ls_shift/su_max 0.0004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.0014|Fo|^2^]'
_refine_ls_weighting_scheme sigma
_refine_ls_wR_factor_all 0.1354
_refine_ls_wR_factor_ref 0.1110
_reflns_number_gt 2656
_reflns_number_total 4500
_reflns_threshold_expression I>3\s(I)
_[local]_cod_data_source_file om6127.cif
_[local]_cod_data_source_block I
_cod_database_code 2202144
loop_
_symmetry_equiv_pos_as_xyz
' +x, +y, +z'
' -x, -y, -z'
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_calc_attached_atom
_atom_site_occupancy
Cl1 0.84351(7) 0.63815(7) 0.17548(6) 0.0230(2) Uani d . 1.000
Cl2 0.73827(7) 0.74387(6) 0.67727(6) 0.0216(2) Uani d . 1.000
O1 0.9857(3) 0.7327(2) 0.1791(2) 0.0387(7) Uani d . 1.000
O2 0.7002(3) 0.6622(2) 0.0834(2) 0.0367(6) Uani d . 1.000
O3 0.8708(3) 0.4842(2) 0.1450(2) 0.0366(6) Uani d . 1.000
O4 0.8162(3) 0.6646(2) 0.2977(2) 0.0358(6) Uani d . 1.000
O5 0.7968(2) 0.8769(2) 0.6446(2) 0.0332(6) Uani d . 1.000
O6 0.7417(3) 0.6186(2) 0.5859(2) 0.0485(7) Uani d . 1.000
O7 0.5726(2) 0.7496(2) 0.6860(2) 0.0394(7) Uani d . 1.000
O8 0.8436(3) 0.7323(2) 0.7976(2) 0.0449(7) Uani d . 1.000
N1 0.7134(3) 0.1240(2) 0.0577(2) 0.0187(6) Uani d . 1.000
N2 0.8153(3) 0.2779(2) 0.3004(2) 0.0210(6) Uani d . 1.000
N3 0.7004(3) 0.3405(2) -0.1057(2) 0.0225(6) Uani d . 1.000
C1 0.5326(3) 0.0808(3) 0.0335(2) 0.0172(6) Uani d . 1.000
C2 0.8222(3) 0.3616(3) 0.4112(3) 0.0230(7) Uani d . 1.000
C3 0.8304(3) 0.2993(3) 0.5117(3) 0.0247(7) Uani d . 1.000
C4 0.8311(3) 0.1470(3) 0.4975(3) 0.0271(8) Uani d . 1.000
C5 0.8220(3) 0.0629(3) 0.3812(3) 0.0257(7) Uani d . 1.000
C6 0.8137(3) 0.1298(3) 0.2816(3) 0.0218(7) Uani d . 1.000
C7 0.8130(3) 0.0538(3) 0.1530(3) 0.0241(7) Uani d . 1.000
C8 0.6368(3) 0.4327(3) -0.1791(3) 0.0254(7) Uani d . 1.000
C9 0.5456(3) 0.3778(3) -0.3002(3) 0.0258(8) Uani d . 1.000
C10 0.5186(3) 0.2266(3) -0.3449(3) 0.0261(7) Uani d . 1.000
C11 0.5874(3) 0.1338(3) -0.2670(3) 0.0245(7) Uani d . 1.000
C12 0.6812(3) 0.1923(3) -0.1460(3) 0.0198(7) Uani d . 1.000
C13 0.7681(3) 0.1034(3) -0.0556(3) 0.0211(7) Uani d . 1.000
H1 0.5056 0.1070 0.1235 0.022 Uiso d . 1.000
H2 0.4668 0.1445 -0.0211 0.022 Uiso d . 1.000
H3 0.8115 0.3247 0.2320 0.025 Uiso calc N2 1.000
H4 0.8213 0.4651 0.4193 0.028 Uiso calc C2 1.000
H5 0.8356 0.3583 0.5904 0.030 Uiso calc C3 1.000
H6 0.8377 0.1012 0.5669 0.032 Uiso calc C4 1.000
H7 0.8216 -0.0409 0.3707 0.031 Uiso calc C5 1.000
H8 0.7674 -0.0467 0.1384 0.029 Uiso calc C7 1.000
H9 0.9238 0.0593 0.1477 0.029 Uiso calc C7 1.000
H10 0.7618 0.3812 -0.0214 0.027 Uiso calc N3 1.000
H11 0.6552 0.5362 -0.1469 0.030 Uiso calc C8 1.000
H12 0.5013 0.4424 -0.3531 0.031 Uiso calc C9 1.000
H13 0.4535 0.1865 -0.4284 0.031 Uiso calc C10 1.000
H14 0.5696 0.0300 -0.2973 0.029 Uiso calc C11 1.000
H15 0.7447 0.0018 -0.0950 0.025 Uiso calc C13 1.000
H16 0.8844 0.1334 -0.0330 0.025 Uiso calc C13 1.000
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0222(3) 0.0168(3) 0.0292(4) 0.0026(2) 0.0051(3) 0.0056(3)
Cl2 0.0230(3) 0.0178(3) 0.0247(4) 0.0022(2) 0.0082(3) 0.0044(3)
O1 0.0336(12) 0.0335(11) 0.054(2) -0.0031(9) 0.0195(11) 0.0157(11)
O2 0.0349(12) 0.0331(11) 0.0366(13) 0.0120(9) -0.0021(10) 0.0090(10)
O3 0.0499(13) 0.0191(10) 0.0370(13) 0.0105(9) 0.0045(10) 0.0058(9)
O4 0.0365(12) 0.0426(12) 0.0323(13) 0.0062(9) 0.0154(10) 0.0093(10)
O5 0.0323(11) 0.0254(10) 0.0470(10) 0.0015(8) 0.0132(10) 0.0182(10)
O6 0.078(2) 0.0253(11) 0.048(2) 0.0047(11) 0.0370(10) -0.0051(10)
O7 0.0249(11) 0.0324(11) 0.064(2) 0.0026(9) 0.0199(11) 0.0077(11)
O8 0.0406(13) 0.0465(13) 0.041(2) -0.0084(10) -0.0041(11) 0.0230(11)
N1 0.0168(10) 0.0191(11) 0.0199(12) 0.0017(8) 0.0054(9) 0.0033(9)
N2 0.0227(11) 0.0209(11) 0.0199(12) 0.0036(9) 0.0051(10) 0.0064(9)
N3 0.0255(11) 0.0209(11) 0.0214(13) 0.0000(9) 0.0090(10) 0.0028(9)
C1 0.0163(11) 0.0162(12) 0.0190(10) 0.0021(9) 0.0051(10) 0.0031(10)
C2 0.0216(13) 0.0205(13) 0.026(2) 0.0011(10) 0.0067(12) 0.0032(11)
C3 0.0207(13) 0.031(2) 0.023(2) 0.0022(11) 0.0071(12) 0.0065(12)
C4 0.0230(10) 0.031(2) 0.031(2) 0.0025(11) 0.0094(12) 0.0138(13)
C5 0.0199(13) 0.0182(13) 0.038(2) 0.0010(10) 0.0067(12) 0.0073(12)
C6 0.0137(12) 0.0222(13) 0.025(2) -0.0010(10) 0.0014(11) 0.0016(11)
C7 0.0200(13) 0.0189(13) 0.030(2) 0.0031(10) 0.0023(12) 0.0022(11)
C8 0.030(2) 0.0181(13) 0.032(2) 0.0022(11) 0.0139(13) 0.0086(12)
C9 0.0280(10) 0.0250(10) 0.030(2) 0.0038(11) 0.0143(13) 0.0130(12)
C10 0.0260(10) 0.030(2) 0.023(2) -0.0006(11) 0.0088(12) 0.0068(12)
C11 0.0250(10) 0.0199(13) 0.029(2) -0.0005(11) 0.0119(13) 0.0020(11)
C12 0.0201(12) 0.0182(12) 0.025(2) -0.0003(10) 0.0140(12) 0.0045(11)
C13 0.0176(12) 0.0200(12) 0.026(2) 0.0014(10) 0.0086(11) 0.0035(11)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.002 0.002
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
Cl 0.132 0.159
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N 0.004 0.003
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O 0.008 0.006
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
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
O1 Cl1 O2 . . 110.90(10) no
O1 Cl1 O3 . . 109.90(10) no
O1 Cl1 O4 . . 109.10(10) no
O2 Cl1 O3 . . 108.70(10) no
O2 Cl1 O4 . . 110.20(10) no
O3 Cl1 O4 . . 108.00(10) no
O5 Cl2 O6 . . 110.10(10) no
O5 Cl2 O7 . . 109.90(10) no
O5 Cl2 O8 . . 109.10(10) no
O6 Cl2 O7 . . 109.80(10) no
O6 Cl2 O8 . . 109.60(10) no
O7 Cl2 O8 . . 108.30(10) no
C1 N1 C7 . . 112.1(2) yes
C1 N1 C13 . . 113.7(2) yes
C7 N1 C13 . . 111.8(2) yes
C2 N2 C6 . . 123.0(2) yes
C8 N3 C12 . . 123.1(2) yes
N1 C1 C1 . 2_655 115.3(2) yes
N2 C2 C3 . . 120.3(2) yes
C2 C3 C4 . . 118.9(3) yes
C3 C4 C5 . . 119.4(3) yes
C4 C5 C6 . . 120.0(2) yes
N2 C6 C5 . . 118.2(3) yes
N2 C6 C7 . . 116.1(2) yes
C5 C6 C7 . . 125.6(2) yes
N1 C7 C6 . . 110.8(2) yes
N3 C8 C9 . . 119.9(2) yes
C8 C9 C10 . . 119.1(2) yes
C9 C10 C11 . . 119.7(3) yes
C10 C11 C12 . . 120.0(2) yes
N3 C12 C11 . . 118.1(2) yes
N3 C12 C13 . . 117.3(2) yes
C11 C12 C13 . . 124.6(2) yes
N1 C13 C12 . . 111.6(2) yes
C2 N2 H3 . . 118.48 no
C6 N2 H3 . . 118.48 no
C8 N3 H10 . . 118.43 no
C12 N3 H10 . . 118.43 no
N1 C1 H1 . . 107.03 no
N1 C1 H2 . . 110.19 no
C1 C1 H1 2_655 . 111.66 no
C1 C1 H2 2_655 . 106.23 no
H1 C1 H2 . . 106.03 no
N2 C2 H4 . . 119.83 no
C3 C2 H4 . . 119.83 no
C2 C3 H5 . . 120.55 no
C4 C3 H5 . . 120.55 no
C3 C4 H6 . . 120.28 no
C5 C4 H6 . . 120.28 no
C4 C5 H7 . . 119.98 no
C6 C5 H7 . . 119.98 no
N1 C7 H8 . . 109.14 no
N1 C7 H9 . . 109.14 no
C6 C7 H8 . . 109.14 no
C6 C7 H9 . . 109.14 no
H8 C7 H9 . . 109.46 no
N3 C8 H11 . . 120.03 no
C9 C8 H11 . . 120.03 no
C8 C9 H12 . . 120.44 no
C10 C9 H12 . . 120.44 no
C9 C10 H13 . . 120.17 no
C11 C10 H13 . . 120.18 no
C10 C11 H14 . . 119.98 no
C12 C11 H14 . . 119.98 no
N1 C13 H15 . . 108.94 no
N1 C13 H16 . . 108.94 no
C12 C13 H15 . . 108.95 no
C12 C13 H16 . . 108.94 no
H15 C13 H16 . . 109.46 no
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
Cl1 O1 . 1.417(2) no
Cl1 O2 . 1.432(2) no
Cl1 O3 . 1.460(2) no
Cl1 O4 . 1.447(2) no
Cl2 O5 . 1.440(2) no
Cl2 O6 . 1.422(2) no
Cl2 O7 . 1.431(2) no
Cl2 O8 . 1.443(2) no
N1 C1 . 1.483(3) yes
N1 C7 . 1.465(3) yes
N1 C13 . 1.466(3) yes
N2 C2 . 1.340(3) yes
N2 C6 . 1.352(3) yes
N3 C8 . 1.341(3) yes
N3 C12 . 1.354(3) yes
C1 C1 2_655 1.542(5) yes
C2 C3 . 1.356(4) yes
C3 C4 . 1.395(4) yes
C4 C5 . 1.389(4) yes
C5 C6 . 1.372(4) yes
C6 C7 . 1.502(4) yes
C8 C9 . 1.366(4) yes
C9 C10 . 1.384(4) yes
C10 C11 . 1.390(4) yes
C11 C12 . 1.376(4) yes
C12 C13 . 1.504(4) yes
N2 H3 . 0.950 no
N3 H10 . 0.950 no
C1 H1 . 1.096 no
C1 H2 . 1.019 no
C2 H4 . 0.950 no
C3 H5 . 0.950 no
C4 H6 . 0.950 no
C5 H7 . 0.950 no
C7 H8 . 0.950 no
C7 H9 . 0.950 no
C8 H11 . 0.950 no
C9 H12 . 0.950 no
C10 H13 . 0.950 no
C11 H14 . 0.950 no
C13 H15 . 0.950 no
C13 H16 . 0.950 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 C12 2.977(3) 2_765 no
O1 N3 3.068(3) 2_765 no
O1 C13 3.227(3) 2_765 no
O1 C7 3.442(3) 1_565 no
O1 C3 3.511(4) 2_766 no
O1 C4 3.513(4) 2_766 no
O1 C11 3.526(3) 2_765 no
O2 C8 3.228(4) . no
O2 N3 3.355(3) . no
O2 C8 3.411(3) 2_665 no
O2 C1 3.428(3) 2_665 no
O2 N3 3.451(3) 2_665 no
O2 C7 3.577(3) 1_565 no
O3 N3 2.847(3) . no
O3 N2 2.917(3) . no
O3 O8 3.261(3) 2_766 no
O3 N1 3.371(3) . no
O3 C2 3.522(3) . no
O4 C9 3.053(3) 2_665 no
O4 C3 3.131(3) 2_766 no
O4 C10 3.214(3) 2_665 no
O4 C2 3.294(3) . no
O4 C4 3.369(4) 2_766 no
O4 O6 3.582(3) . no
O4 N2 3.596(3) . no
O5 C6 3.172(3) 2_766 no
O5 C11 3.250(3) 1_566 no
O5 C4 3.285(3) 1_565 no
O5 C5 3.317(3) 2_766 no
O5 C7 3.407(3) 2_766 no
O6 C2 3.062(3) . no
O6 C3 3.139(3) . no
O6 C9 3.318(3) 1_556 no
O6 C9 3.496(4) 2_665 no
O6 N2 3.599(3) 2_766 no
O7 C2 3.233(3) 2_666 no
O7 N2 3.306(3) 2_666 no
O7 C9 3.477(3) 1_556 no
O7 C3 3.478(3) 2_666 no
O7 C11 3.500(3) 1_566 no
O7 C8 3.562(3) 1_556 no
O8 C7 3.238(4) 2_766 no
O8 C8 3.257(3) 1_556 no
O8 N2 3.351(3) 2_766 no
O8 C6 3.467(3) 2_766 no
C3 C10 3.524(4) 1_556 no
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_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C1 N1 . 2_655 2_655 180 no
N1 C7 C6 N2 . . . -36.3(3) no
N1 C7 C6 C5 . . . 147.6(3) no
N1 C13 C12 N3 . . . 59.6(3) no
N1 C13 C12 C11 . . . -122.0(3) no
N2 C2 C3 C4 . . . -0.2(4) no
N2 C6 C5 C4 . . . 0.3(4) no
N3 C8 C9 C10 . . . 0.7(4) no
N3 C12 C11 C10 . . . 1.5(4) no
C1 N1 C7 C6 . . . -77.4(3) no
C1 N1 C13 C12 . . . 59.5(3) no
C1 C1 N1 C7 2_655 . . -69.7(3) no
C1 C1 N1 C13 2_655 . . 58.3(3) no
C2 N2 C6 C5 . . . -1.1(4) no
C2 N2 C6 C7 . . . -177.5(2) no
C2 C3 C4 C5 . . . -0.5(4) no
C3 C2 N2 C6 . . . 1.0(4) no
C3 C4 C5 C6 . . . 0.5(4) no
C4 C5 C6 C7 . . . 176.4(2) no
C6 C7 N1 C13 . . . 153.6(2) no
C7 N1 C13 C12 . . . -172.3(2) no
C8 N3 C12 C11 . . . -2.2(4) no
C8 N3 C12 C13 . . . 176.4(2) no
C8 C9 C10 C11 . . . -1.3(4) no
C9 C8 N3 C12 . . . 1.1(4) no
C9 C10 C11 C12 . . . 0.2(4) no
C10 C11 C12 C13 . . . -176.9(2) no