#------------------------------------------------------------------------------
#$Date: 2023-12-08 16:16:31 +0200 (Fri, 08 Dec 2023) $
#$Revision: 288183 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/00/97/7009739.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7009739
loop_
_publ_author_name
'Hynes, Michael J.'
'Maubert, Beatrice'
'McKee, Vickie'
'Town, Raewyn M.'
'Nelson, Jane'
_publ_section_title
;
 Protonated azacryptate hosts for nitrate and perchlorate
;
_journal_issue                   16
_journal_name_full
'Journal of the Chemical Society, Dalton Transactions'
_journal_page_first              2853
_journal_paper_doi               10.1039/b003249m
_journal_year                    2000
_chemical_formula_sum            'C36 H66 Cl6 N8 O27'
_chemical_formula_weight         1255.67
_space_group_IT_number           198
_symmetry_cell_setting           cubic
_symmetry_space_group_name_Hall  'P 2ac 2ab 3'
_symmetry_space_group_name_H-M   'P 21 3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.443(2)
_cell_length_b                   17.443(2)
_cell_length_c                   17.443(2)
_cell_measurement_reflns_used    27
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      11.51
_cell_measurement_theta_min      4.81
_cell_volume                     5307.2(11)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_method       'ω scans'
_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  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0631
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6903
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.02
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.419
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'trigonal prism'
_exptl_crystal_F_000             2624
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3141
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0554
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0603P)²+4.7820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1307
_reflns_number_gt                2464
_reflns_number_total             3141
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b003249m.txt
_cod_data_source_block           complex1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Cubic' changed to 'cubic' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

data name '_atom_site_symmetry_multiplicit' was replaced with
'_atom_site_symmetry_multiplicity' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_cell_volume        5307.5(12)
_cod_original_sg_symbol_H-M      P2(1)3
_cod_database_code               7009739
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'z, x, y'
'z+1/2, -x+1/2, -y'
'-z+1/2, -x, y+1/2'
'-z, x+1/2, -y+1/2'
'y, z, x'
'-y, z+1/2, -x+1/2'
'y+1/2, -z+1/2, -x'
'-y+1/2, -z, x+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6320(2) 0.8680(2) 0.1320(2) 0.0177(13) Uani 1 3 d S . .
C1 C 0.6090(3) 0.7868(3) 0.1246(3) 0.0250(11) Uani 1 1 d . . .
H1A H 0.6380 0.7565 0.1629 0.030 Uiso 1 1 calc R . .
H1B H 0.6244 0.7685 0.0732 0.030 Uiso 1 1 calc R . .
C2 C 0.5247(3) 0.7702(3) 0.1352(3) 0.0252(11) Uani 1 1 d . . .
H2A H 0.5169 0.7140 0.1363 0.030 Uiso 1 1 calc R . .
H2B H 0.5079 0.7910 0.1852 0.030 Uiso 1 1 calc R . .
N3 N 0.4764(2) 0.8037(2) 0.0735(2) 0.0239(9) Uani 1 1 d . . .
H3A H 0.4986 0.7938 0.0267 0.029 Uiso 1 1 calc R . .
H3B H 0.4742 0.8561 0.0796 0.029 Uiso 1 1 calc R . .
C3 C 0.3961(3) 0.7716(3) 0.0743(3) 0.0298(12) Uani 1 1 d . . .
H3C H 0.3984 0.7150 0.0716 0.036 Uiso 1 1 calc R . .
H3D H 0.3706 0.7858 0.1230 0.036 Uiso 1 1 calc R . .
C4 C 0.3494(3) 0.8015(3) 0.0079(3) 0.0284(11) Uani 1 1 d . . .
C5 C 0.3650(3) 0.7769(3) -0.0650(3) 0.0334(12) Uani 1 1 d . . .
H5 H 0.4053 0.7413 -0.0737 0.040 Uiso 1 1 calc R . .
C6 C 0.3226(3) 0.8035(3) -0.1253(3) 0.0343(12) Uani 1 1 d . . .
H6 H 0.3341 0.7868 -0.1758 0.041 Uiso 1 1 calc R . .
C7 C 0.2633(3) 0.8543(3) -0.1137(3) 0.0349(13) Uani 1 1 d . . .
H7 H 0.2343 0.8723 -0.1562 0.042 Uiso 1 1 calc R . .
C8 C 0.2454(3) 0.8795(3) -0.0403(3) 0.0290(11) Uani 1 1 d . . .
C9 C 0.2892(3) 0.8527(3) 0.0212(3) 0.0296(11) Uani 1 1 d . . .
H9 H 0.2780 0.8692 0.0719 0.036 Uiso 1 1 calc R . .
C10 C 0.1840(3) 0.9387(3) -0.0290(4) 0.0380(14) Uani 1 1 d . . .
H10A H 0.1558 0.9280 0.0190 0.046 Uiso 1 1 calc R . .
H10B H 0.1471 0.9362 -0.0721 0.046 Uiso 1 1 calc R . .
N4 N 0.2189(2) 1.0185(2) -0.0251(2) 0.0298(10) Uani 1 1 d . . .
H4A H 0.1802 1.0543 -0.0281 0.036 Uiso 1 1 calc R . .
H4B H 0.2428 1.0245 0.0215 0.036 Uiso 1 1 calc R . .
C11 C 0.2747(3) 1.0332(3) -0.0868(3) 0.0290(11) Uani 1 1 d . . .
H11A H 0.2524 1.0172 -0.1365 0.035 Uiso 1 1 calc R . .
H11B H 0.3213 1.0022 -0.0777 0.035 Uiso 1 1 calc R . .
C12 C 0.2965(3) 1.1177(3) -0.0909(3) 0.0285(11) Uani 1 1 d . . .
H12A H 0.2601 1.1456 -0.1243 0.034 Uiso 1 1 calc R . .
H12B H 0.2947 1.1409 -0.0391 0.034 Uiso 1 1 calc R . .
N2 N 0.3768(2) 1.1232(2) -0.1232(2) 0.0235(14) Uani 1 3 d S . .
Cl1 Cl 0.50929(6) 0.99071(6) 0.00929(6) 0.0259(5) Uani 1 3 d S . .
O11 O 0.4615(2) 1.0385(2) -0.0385(2) 0.0504(19) Uani 1 3 d S . .
O12 O 0.46436(19) 0.96324(19) 0.07552(19) 0.0283(8) Uani 1 1 d . . .
Cl2 Cl 0.45951(7) 0.54049(7) 0.04049(7) 0.0325(5) Uani 1 3 d S . .
O21 O 0.5061(3) 0.5827(3) 0.0936(3) 0.0590(12) Uani 1 1 d . . .
O22 O 0.5070(2) 0.4930(2) -0.0070(2) 0.0474(18) Uani 1 3 d S . .
Cl3 Cl 0.12948(8) 1.12948(8) 0.12948(8) 0.0376(5) Uani 1 3 d S . .
O31 O 0.1756(3) 1.1756(3) 0.1756(3) 0.067(2) Uani 1 3 d S . .
O32 O 0.1395(2) 1.1491(2) 0.0506(2) 0..0477(11) Uani 1 1 d . . .
Cl4 Cl 0.08676(8) 0.77652(8) 0.12597(8) 0.0404(3) Uani 1 1 d . . .
O41 O 0.0981(3) 0.8563(2) 0.1238(2) 0.0612(13) Uani 1 1 d . . .
O42 O 0.0755(4) 0.7484(4) 0.0535(3) 0.127(3) Uani 1 1 d . . .
O43 O 0.0214(3) 0.7593(3) 0.1729(3) 0.0788(17) Uani 1 1 d . . .
O44 O 0.1516(5) 0.7459(4) 0.1600(6) 0.158(4) Uani 1 1 d . . .
O1W O 0.3203(2) 1.0296(2) 0.0922(2) 0.0445(10) Uani 1 1 d . . .
H1WA H 0.3773 1.0070 0.0988 0.050 Uiso 1 1 d . . .
H1WB H 0.3057 1.0322 0.1431 0.050 Uiso 1 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C1 108.6(3) 6_566 . ?
C1 N1 C1 108.6(3) 6_566 12_664 ?
C1 N1 C1 108.6(3) . 12_664 ?
N1 C1 C2 115.9(4) . . ?
N3 C2 C1 112.8(4) . . ?
C2 N3 C3 111.9(4) . . ?
C4 C3 N3 111.5(4) . . ?
C5 C4 C9 120.2(5) . . ?
C5 C4 C3 119.8(5) . . ?
C9 C4 C3 119.9(5) . . ?
C6 C5 C4 120.0(5) . . ?
C5 C6 C7 120.8(5) . . ?
C6 C7 C8 120.5(5) . . ?
C7 C8 C9 118.7(5) . . ?
C7 C8 C10 119.8(5) . . ?
C9 C8 C10 121.3(5) . . ?
C8 C9 C4 119.8(5) . . ?
C8 C10 N4 110.5(4) . . ?
C11 N4 C10 113.0(4) . . ?
N4 C11 C12 111.6(4) . . ?
N2 C12 C11 108.1(4) . . ?
C12 N2 C12 112.3(3) 12_664 6_566 ?
C12 N2 C12 112.3(3) 12_664 . ?
C12 N2 C12 112.3(3) 6_566 . ?
O11 Cl1 O12 109.44(15) . 12_664 ?
O11 Cl1 O12 109.44(15) . . ?
O12 Cl1 O12 109.51(15) 12_664 . ?
O11 Cl1 O12 109.44(15) . 6_566 ?
O12 Cl1 O12 109.51(15) 12_664 6_566 ?
O12 Cl1 O12 109.51(15) . 6_566 ?
O22 Cl2 O21 110.02(19) . . ?
O22 Cl2 O21 110.02(19) . 7_564 ?
O21 Cl2 O21 108.92(19) . 7_564 ?
O22 Cl2 O21 110.02(19) . 10_655 ?
O21 Cl2 O21 108.92(19) . 10_655 ?
O21 Cl2 O21 108.92(19) 7_564 10_655 ?
O31 Cl3 O32 110.3(2) . 9_465 ?
O31 Cl3 O32 110.3(2) . 5_564 ?
O32 Cl3 O32 108.6(2) 9_465 5_564 ?
O31 Cl3 O32 110.3(2) . . ?
O32 Cl3 O32 108.6(2) 9_465 . ?
O32 Cl3 O32 108.6(2) 5_564 . ?
O42 Cl4 O44 112.0(5) . . ?
O42 Cl4 O41 110.5(4) . . ?
O44 Cl4 O41 106.2(4) . . ?
O42 Cl4 O43 109.7(3) . . ?
O44 Cl4 O43 108.9(5) . . ?
O41 Cl4 O43 109.5(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.479(5) 6_566 ?
N1 C1 1.479(5) . ?
N1 C1 1.479(5) 12_664 ?
C1 C2 1.510(6) . ?
C2 N3 1.487(6) . ?
N3 C3 1.509(6) . ?
C3 C4 1.508(7) . ?
C4 C5 1.370(7) . ?
C4 C9 1.398(7) . ?
C5 C6 1.367(8) . ?
C6 C7 1.377(8) . ?
C7 C8 1.389(7) . ?
C8 C9 1.397(7) . ?
C8 C10 1.501(7) . ?
C10 N4 1.521(6) . ?
N4 C11 1.473(6) . ?
C11 C12 1.524(7) . ?
C12 N2 1.513(5) . ?
N2 C12 1.513(5) 12_664 ?
N2 C12 1.513(5) 6_566 ?
Cl1 O11 1.444(7) . ?
Cl1 O12 1.476(3) 12_664 ?
Cl1 O12 1.476(3) . ?
Cl1 O12 1.476(3) 6_566 ?
Cl2 O22 1.434(7) . ?
Cl2 O21 1.436(4) . ?
Cl2 O21 1.436(4) 7_564 ?
Cl2 O21 1.436(4) 10_655 ?
Cl3 O31 1.392(8) . ?
Cl3 O32 1.429(4) 9_465 ?
Cl3 O32 1.429(4) 5_564 ?
Cl3 O32 1.429(4) . ?
Cl4 O42 1.370(5) . ?
Cl4 O44 1.385(7) . ?
Cl4 O41 1.406(4) . ?
Cl4 O43 1.436(5) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A O42 0.92 2.07 2.953(6) 159.7 4_565
N3 H3B O12 0.92 1.88 2.790(5) 170.7 .
N3 H3B O12 0.92 2.58 3.028(5) 110.5 12_664
N4 H4A O32 0.92 2.26 2.975(6) 133.8 .
N4 H4A O41 0.92 2.37 2.992(6) 124.8 5_564
N4 H4B O1W 0.92 1.83 2.712(6) 159.3 .
O1W H1WA O12 1.08 1.75 2.782(5) 159.8 .
O1W H1WB O43 0.92 2.26 3.049(6) 142.6 7_564
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C1 C2 70.2(7) 6_566 . . . ?
C1 N1 C1 C2 -171.8(4) 12_664 . . . ?
N1 C1 C2 N3 66.5(5) . . . . ?
C1 C2 N3 C3 166.6(4) . . . . ?
C2 N3 C3 C4 -175.7(4) . . . . ?
N3 C3 C4 C5 71.3(5) . . . . ?
N3 C3 C4 C9 -110.3(5) . . . . ?
C9 C4 C5 C6 1.2(7) . . . . ?
C3 C4 C5 C6 179.7(4) . . . . ?
C4 C5 C6 C7 -0.9(7) . . . . ?
C5 C6 C7 C8 0.0(8) . . . . ?
C6 C7 C8 C9 0.4(8) . . . . ?
C6 C7 C8 C10 176.1(5) . . . . ?
C7 C8 C9 C4 -0.1(7) . . . . ?
C10 C8 C9 C4 -175.6(4) . . . . ?
C5 C4 C9 C8 -0.8(7) . . . . ?
C3 C4 C9 C8 -179.2(4) . . . . ?
C7 C8 C10 N4 -94.7(6) . . . . ?
C9 C8 C10 N4 80.8(6) . . . . ?
C8 C10 N4 C11 47.4(6) . . . . ?
C10 N4 C11 C12 168.7(4) . . . . ?
N4 C11 C12 N2 152.0(4) . . . . ?
C11 C12 N2 C12 61.6(7) . . . 12_664 ?
C11 C12 N2 C12 -170.6(4) . . . 6_566 ?
