#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/63/2206381.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_2206381
loop_
_publ_author_name
'Wang, Shi-Fan'
'Li, Huan-Qiu'
'Ruan, Ban-Feng'
'Zhu, Hai-Liang'
'Ng, Seik Weng'
_publ_section_title
;1,4,8,11-Tetrakis(carboxymethyl)-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazoniacyclotetradecane
 tetrachloride octahydrate
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2413
_journal_page_last               o2414
_journal_paper_doi               10.1107/S1600536805020817
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C24 H48 N4 O8 4+, 4Cl -, 8H2 O'
_chemical_formula_moiety         'C24 H48 N4 O8 4+, 4Cl -, 8H2 O'
_chemical_formula_sum            'C24 H64 Cl4 N4 O16'
_chemical_formula_weight         806.59
_chemical_name_systematic
;
1,4,8,11-Tetrakis(carboxymethyl)-5,5,7,12,12,14-hexamethyl-1,4,8,11-
tetraazoniacyclotetradecane tetrachloride octahydrate
;
_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                100.1610(10)
_cell_angle_beta                 94.4820(10)
_cell_angle_gamma                103.1680(10)
_cell_formula_units_Z            1
_cell_length_a                   8.6283(3)
_cell_length_b                   10.6995(4)
_cell_length_c                   11.0065(4)
_cell_measurement_reflns_used    8332
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.4
_cell_volume                     966.42(6)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device_type  'Bruker APEX 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  0.017
_diffrn_reflns_av_sigmaI/netI    0.020
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11066
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         1.9
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.375
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.34
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4351
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.045
_refine_ls_R_factor_gt           0.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0657P)²+0.404P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.120
_refine_ls_wR_factor_ref         0.121
_reflns_number_gt                4153
_reflns_number_total             4351
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6606.cif
_cod_data_source_block           I
_cod_database_code               2206381
_cod_database_fobs_code          2206381
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_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Cl1 0.11305(7) 0.11797(7) 0.82315(7) 0.0675(2) Uani d . 1 Cl
Cl2 0.33315(5) 0.50102(5) 0.64405(4) 0.04240(10) Uani d . 1 Cl
O1 0.5550(2) 0.36970(10) 0.9693(2) 0.0536(4) Uani d D 1 O
O2 0.7493(2) 0.30500(10) 0.87210(10) 0.0421(3) Uani d . 1 O
O3 0.4001(2) 0.02550(10) 0.33130(10) 0.0443(3) Uani d D 1 O
O4 0.5725(2) 0.15780(10) 0.24030(10) 0.0439(3) Uani d . 1 O
O1w 0.4483(2) 0.1343(2) 0.9836(2) 0.0635(4) Uani d D 1 O
O2w 0.2368(2) -0.05110(10) 1.11780(10) 0.0438(3) Uani d D 1 O
O3w 0.3759(2) 0.2107(2) 0.6470(2) 0.0764(5) Uani d D 1 O
O4w 1.0933(2) 0.4259(2) 0.83880(10) 0.0462(3) Uani d D 1 O
N1 0.81870(10) 0.51710(10) 0.76650(10) 0.0231(2) Uani d D 1 N
N2 0.77040(10) 0.26830(10) 0.46070(10) 0.0229(2) Uani d D 1 N
C1 0.6725(2) 0.3838(2) 0.90250(10) 0.0321(3) Uani d . 1 C
C2 0.7058(2) 0.5156(2) 0.86430(10) 0.0300(3) Uani d . 1 C
C3 0.8961(2) 0.66030(10) 0.75030(10) 0.0266(3) Uani d . 1 C
C4 0.7630(2) 0.7287(2) 0.7296(2) 0.0479(5) Uani d . 1 C
C5 1.0092(3) 0.7278(2) 0.8689(2) 0.0506(5) Uani d . 1 C
C6 0.7308(2) 0.42390(10) 0.64770(10) 0.0252(3) Uani d . 1 C
C7 0.8344(2) 0.33470(10) 0.59370(10) 0.0247(3) Uani d . 1 C
C8 0.6282(2) 0.1562(2) 0.45660(10) 0.0313(3) Uani d . 1 C
C9 0.5319(2) 0.1135(2) 0.3288(2) 0.0303(3) Uani d . 1 C
C10 0.9026(2) 0.22770(10) 0.38790(10) 0.0247(3) Uani d . 1 C
C11 0.9892(2) 0.1493(2) 0.4596(2) 0.0414(4) Uani d . 1 C
C12 1.0085(2) 0.35450(10) 0.36190(10) 0.0244(3) Uani d . 1 C
H1w1 0.438(6) 0.127(5) 1.058(2) 0.15(2) Uiso d D 1 H
H1w2 0.351(2) 0.120(3) 0.952(3) 0.080(10) Uiso d D 1 H
H2w1 0.254(3) -0.126(2) 1.098(3) 0.070(10) Uiso d D 1 H
H2w2 0.141(2) -0.070(3) 1.134(2) 0.060(10) Uiso d D 1 H
H3w1 0.318(4) 0.165(3) 0.690(3) 0.090(10) Uiso d D 1 H
H3w2 0.344(4) 0.278(2) 0.638(3) 0.100(10) Uiso d D 1 H
H4w1 1.085(4) 0.3450(10) 0.833(3) 0.070(10) Uiso d D 1 H
H4w2 1.177(3) 0.447(3) 0.805(3) 0.090(10) Uiso d D 1 H
H1o 0.528(4) 0.2910(10) 0.979(3) 0.080(10) Uiso d D 1 H
H3o 0.351(3) 0.005(3) 0.2580(10) 0.070(10) Uiso d D 1 H
H1n 0.897(2) 0.488(2) 0.792(2) 0.030(10) Uiso d D 1 H
H2n 0.738(2) 0.3240(10) 0.424(2) 0.020(10) Uiso d D 1 H
H2a 0.6061 0.5317 0.8315 0.036 Uiso calc R 1 H
H2b 0.7532 0.5843 0.9361 0.036 Uiso calc R 1 H
H4a 0.6950 0.6837 0.6540 0.072 Uiso calc R 1 H
H4b 0.8091 0.8176 0.7233 0.072 Uiso calc R 1 H
H4c 0.7009 0.7281 0.7982 0.072 Uiso calc R 1 H
H5a 1.0915 0.6819 0.8785 0.076 Uiso calc R 1 H
H5b 0.9500 0.7275 0.9391 0.076 Uiso calc R 1 H
H5c 1.0575 0.8166 0.8636 0.076 Uiso calc R 1 H
H6a 0.7046 0.4739 0.5871 0.030 Uiso calc R 1 H
H6b 0.6313 0.3709 0.6656 0.030 Uiso calc R 1 H
H7a 0.9434 0.3861 0.5970 0.030 Uiso calc R 1 H
H7b 0.8365 0.2687 0.6436 0.030 Uiso calc R 1 H
H8a 0.5601 0.1822 0.5173 0.038 Uiso calc R 1 H
H8b 0.6647 0.0829 0.4787 0.038 Uiso calc R 1 H
H10 0.8516 0.1715 0.3080 0.030 Uiso calc R 1 H
H11a 0.9138 0.0725 0.4711 0.062 Uiso calc R 1 H
H11b 1.0374 0.2021 0.5393 0.062 Uiso calc R 1 H
H11c 1.0710 0.1239 0.4138 0.062 Uiso calc R 1 H
H12a 1.0841 0.3965 0.4356 0.029 Uiso calc R 1 H
H12b 0.9405 0.4130 0.3494 0.029 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'
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
_geom_angle_publ_flag
C2 N1 C6 . . 108.40(10) no
C2 N1 C3 . . 112.00(10) no
C6 N1 C3 . . 114.80(10) no
C8 N2 C7 . . 110.40(10) no
C8 N2 C10 . . 112.90(10) no
C7 N2 C10 . . 111.80(10) no
O2 C1 O1 . . 126.4(2) no
O2 C1 C2 . . 122.00(10) no
O1 C1 C2 . . 111.60(10) no
N1 C2 C1 . . 109.70(10) no
C4 C3 C5 . . 112.0(2) no
C4 C3 C12 . 2_766 112.60(10) no
C5 C3 C12 . 2_766 110.40(10) no
C4 C3 N1 . . 108.70(10) no
C5 C3 N1 . . 106.80(10) no
C12 C3 N1 2_766 . 106.00(10) no
N1 C6 C7 . . 110.70(10) no
N2 C7 C6 . . 111.20(10) no
N2 C8 C9 . . 111.70(10) no
O4 C9 O3 . . 126.2(2) no
O4 C9 C8 . . 123.50(10) no
O3 C9 C8 . . 110.30(10) no
C11 C10 C12 . . 115.50(10) no
C11 C10 N2 . . 109.80(10) no
C12 C10 N2 . . 106.50(10) no
C10 C12 C3 . 2_766 116.60(10) no
C1 O1 H1o . . 109(2) no
C9 O3 H3o . . 106(2) no
H1w1 O1w H1w2 . . 102(4) no
H2w1 O2w H2w2 . . 101(3) no
H3w1 O3w H3w2 . . 112(3) no
H4w1 O4w H4w2 . . 101(3) no
C2 N1 H1n . . 108.0(10) no
C6 N1 H1n . . 108.0(10) no
C3 N1 H1n . . 105.0(10) no
C8 N2 H2n . . 107.0(10) no
C7 N2 H2n . . 108.0(10) no
C10 N2 H2n . . 106.0(10) no
N1 C2 H2a . . 109.7 no
C1 C2 H2a . . 109.7 no
N1 C2 H2b . . 109.7 no
C1 C2 H2b . . 109.7 no
H2a C2 H2b . . 108.2 no
C3 C4 H4a . . 109.5 no
C3 C4 H4b . . 109.5 no
H4a C4 H4b . . 109.5 no
C3 C4 H4c . . 109.5 no
H4a C4 H4c . . 109.5 no
H4b C4 H4c . . 109.5 no
C3 C5 H5a . . 109.5 no
C3 C5 H5b . . 109.5 no
H5a C5 H5b . . 109.5 no
C3 C5 H5c . . 109.5 no
H5a C5 H5c . . 109.5 no
H5b C5 H5c . . 109.5 no
N1 C6 H6a . . 109.5 no
C7 C6 H6a . . 109.5 no
N1 C6 H6b . . 109.5 no
C7 C6 H6b . . 109.5 no
H6a C6 H6b . . 108.1 no
N2 C7 H7a . . 109.4 no
C6 C7 H7a . . 109.4 no
N2 C7 H7b . . 109.4 no
C6 C7 H7b . . 109.4 no
H7a C7 H7b . . 108.0 no
N2 C8 H8a . . 109.3 no
C9 C8 H8a . . 109.3 no
N2 C8 H8b . . 109.3 no
C9 C8 H8b . . 109.3 no
H8a C8 H8b . . 107.9 no
C11 C10 H10 . . 108.3 no
C12 C10 H10 . . 108.3 no
N2 C10 H10 . . 108.3 no
C10 C11 H11a . . 109.5 no
C10 C11 H11b . . 109.5 no
H11a C11 H11b . . 109.5 no
C10 C11 H11c . . 109.5 no
H11a C11 H11c . . 109.5 no
H11b C11 H11c . . 109.5 no
C10 C12 H12a . . 108.1 no
C3 C12 H12a 2_766 . 108.1 no
C10 C12 H12b . . 108.1 no
C3 C12 H12b 2_766 . 108.1 no
H12a C12 H12b . . 107.3 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
O1 C1 . 1.295(2) no
O2 C1 . 1.205(2) no
O3 C9 . 1.306(2) no
O4 C9 . 1.200(2) no
N1 C2 . 1.506(2) no
N1 C6 . 1.523(2) no
N1 C3 . 1.573(2) no
N2 C8 . 1.499(2) no
N2 C7 . 1.510(2) no
N2 C10 . 1.543(2) no
C1 C2 . 1.513(2) no
C3 C4 . 1.519(2) no
C3 C5 . 1.525(2) no
C3 C12 2_766 1.542(2) no
C6 C7 . 1.528(2) no
C8 C9 . 1.515(2) no
C10 C11 . 1.520(2) no
C10 C12 . 1.539(2) no
C12 C3 2_766 1.542(2) no
O1 H1o . 0.850(10) no
O3 H3o . 0.850(10) no
O1w H1w1 . 0.850(10) no
O1w H1w2 . 0.850(10) no
O2w H2w1 . 0.840(10) no
O2w H2w2 . 0.840(10) no
O3w H3w1 . 0.850(10) no
O3w H3w2 . 0.850(10) no
O4w H4w1 . 0.850(10) no
O4w H4w2 . 0.850(10) no
N1 H1n . 0.860(10) no
N2 H2n . 0.860(10) no
C2 H2a . 0.97 no
C2 H2b . 0.97 no
C4 H4a . 0.96 no
C4 H4b . 0.96 no
C4 H4c . 0.96 no
C5 H5a . 0.96 no
C5 H5b . 0.96 no
C5 H5c . 0.96 no
C6 H6a . 0.97 no
C6 H6b . 0.97 no
C7 H7a . 0.97 no
C7 H7b . 0.97 no
C8 H8a . 0.97 no
C8 H8b . 0.97 no
C10 H10 . 0.98 no
C11 H11a . 0.96 no
C11 H11b . 0.96 no
C11 H11c . 0.96 no
C12 H12a . 0.97 no
C12 H12b . 0.97 no
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
O1 H1o O1w . 0.850(10) 1.670(10) 2.514(2) 171(3) yes
O3 H3o O2w 1_554 0.850(10) 1.690(10) 2.541(2) 173(3) yes
O1w H1w1 O4 1_556 0.850(10) 2.17(3) 2.889(2) 143(4) yes
O1w H1w2 Cl1 . 0.850(10) 2.400(10) 3.221(2) 163(3) yes
O2w H2w1 O2 2_657 0.840(10) 2.00(2) 2.767(2) 152(3) yes
O2w H2w2 Cl1 2_557 0.840(10) 2.250(10) 3.087(2) 179(2) yes
O3w H3w1 Cl1 . 0.850(10) 2.41(2) 3.198(2) 156(3) yes
O3w H3w2 Cl2 . 0.850(10) 2.400(10) 3.216(2) 163(3) yes
O4w H4w1 Cl1 1_655 0.850(10) 2.470(10) 3.313(2) 170(3) yes
O4w H4w2 Cl2 1_655 0.850(10) 2.38(2) 3.172(2) 157(3) yes
N1 H1n O4w . 0.860(10) 2.020(10) 2.869(2) 174(2) yes
N2 H2n Cl2 2_666 0.860(10) 2.320(10) 3.173(2) 170(2) 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
_geom_torsion_publ_flag
C6 N1 C2 C1 . 68.5(2) no
C3 N1 C2 C1 . -163.80(10) no
O2 C1 C2 N1 . 11.4(2) no
O1 C1 C2 N1 . -168.50(10) no
C2 N1 C3 C4 . -52.2(2) no
C6 N1 C3 C4 . 72.0(2) no
C2 N1 C3 C5 . 68.8(2) no
C6 N1 C3 C5 . -166.90(10) no
C2 N1 C3 C12 2_766 -173.50(10) no
C6 N1 C3 C12 2_766 -49.3(2) no
C2 N1 C6 C7 . -132.80(10) no
C3 N1 C6 C7 . 101.20(10) no
C8 N2 C7 C6 . -77.80(10) no
C10 N2 C7 C6 . 155.70(10) no
N1 C6 C7 N2 . -164.70(10) no
C7 N2 C8 C9 . 163.00(10) no
C10 N2 C8 C9 . -71.1(2) no
N2 C8 C9 O4 . 5.4(2) no
N2 C8 C9 O3 . -173.30(10) no
C8 N2 C10 C11 . -73.5(2) no
C7 N2 C10 C11 . 51.7(2) no
C8 N2 C10 C12 . 160.80(10) no
C7 N2 C10 C12 . -74.00(10) no
C11 C10 C12 C3 2_766 81.8(2) no
N2 C10 C12 C3 2_766 -156.00(10) no
