#------------------------------------------------------------------------------
#$Date: 2016-03-22 10:30:34 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178873 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/02/4110236.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_4110236
loop_
_publ_author_name
'Matthew J. Horner'
'K. Travis Holman'
'Michael D. Ward'
_publ_section_title
;
 Architectural Diversity and Elastic Networks in Hydrogen-Bonded Host
 Frameworks: From Molecular Jaws to Cylinders
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14640
_journal_page_last               14660
_journal_paper_doi               10.1021/ja0741574
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C22 H30 N8 O10 S2'
_chemical_formula_weight         630.68
_chemical_name_common            'guanidinium sulfonate clathrate'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 114.4260(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.9819(17)
_cell_length_b                   7.4270(6)
_cell_length_c                   19.0067(14)
_cell_measurement_reflns_used    4298
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.114
_cell_measurement_theta_min      2.351
_cell_volume                     2953.8(4)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'SMART, Bruker (or Siemens)'
_computing_data_reduction        'SAINT, Bruker'
_computing_molecular_graphics    'XSEED, L. Barbour; http://www.xseed.com'
_computing_publication_material  CIFTAB
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'SMART platform CCD, Bruker (or Siemens)'
_diffrn_measurement_method       'omega 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  0.0721
_diffrn_reflns_av_sigmaI/netI    0.0737
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17843
_diffrn_reflns_theta_full        27.12
_diffrn_reflns_theta_max         27.12
_diffrn_reflns_theta_min         0.97
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  0.9687
_exptl_absorpt_correction_T_min  0.9037
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, G. Sheldrick (1999)'
_exptl_crystal_colour            off-white
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       plate
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.752
_refine_diff_density_min         -0.657
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         6511
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.1245
_refine_ls_R_factor_gt           0.0728
_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)+(0.1407P)²+1.3703P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2191
_refine_ls_wR_factor_ref         0.2593
_reflns_number_gt                3508
_reflns_number_total             6511
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0741574si20070910_040750_35.cif
_cod_data_source_block           G4NBS_p-xylene
_cod_database_code               4110236
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-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
S1 S 0.35136(4) 0.75842(12) 0.17753(6) 0.0290(3) Uani 1 1 d .
O1 O 0.29910(14) 0.7682(3) 0.10101(17) 0.0361(7) Uani 1 1 d .
N1 N 0.26791(18) 0.5883(5) 0.3041(2) 0.0410(9) Uani 1 1 d .
H1A H 0.2971 0.5859 0.2854 0.049 Uiso 1 1 calc R
H1B H 0.2532 0.4868 0.3144 0.049 Uiso 1 1 calc R
C1 C 0.4227(2) 0.7363(5) 0.1633(2) 0.0309(9) Uani 1 1 d .
S2 S 0.14891(5) 0.24422(12) 0.32610(6) 0.0294(3) Uani 1 1 d .
O2 O 0.35763(13) 0.9212(3) 0.22337(16) 0.0346(7) Uani 1 1 d .
N2 N 0.20195(19) 0.7442(4) 0.3452(2) 0.0414(9) Uani 1 1 d .
H2B H 0.1869 0.8466 0.3541 0.050 Uiso 1 1 calc R
H2A H 0.1878 0.6414 0.3551 0.050 Uiso 1 1 calc R
C2 C 0.4775(2) 0.8221(6) 0.2123(2) 0.0344(9) Uani 1 1 d .
H2 H 0.4770 0.8975 0.2524 0.041 Uiso 1 1 calc R
O3 O 0.34788(14) 0.5972(3) 0.21992(16) 0.0345(7) Uani 1 1 d .
N3 N 0.26731(18) 0.8978(5) 0.3017(2) 0.0412(9) Uani 1 1 d .
H3B H 0.2965 0.8975 0.2830 0.049 Uiso 1 1 calc R
H3A H 0.2524 1.0006 0.3104 0.049 Uiso 1 1 calc R
C3 C 0.5339(2) 0.7976(6) 0.2026(2) 0.0343(9) Uani 1 1 d .
H3 H 0.5722 0.8566 0.2355 0.041 Uiso 1 1 calc R
O4 O 0.59160(15) 0.5516(4) 0.08459(19) 0.0468(8) Uani 1 1 d .
N4 N 0.23242(17) 0.1096(5) 0.0329(2) 0.0404(9) Uani 1 1 d .
H4A H 0.2036 0.1124 -0.0152 0.049 Uiso 1 1 calc R
H4B H 0.2467 0.0056 0.0558 0.049 Uiso 1 1 calc R
C4 C 0.5325(2) 0.6856(5) 0.1442(2) 0.0306(9) Uani 1 1 d .
O5 O 0.64019(14) 0.7432(4) 0.17698(17) 0.0382(7) Uani 1 1 d .
N5 N 0.29821(19) 0.2569(4) 0.1433(2) 0.0421(9) Uani 1 1 d .
H5B H 0.3132 0.3577 0.1686 0.051 Uiso 1 1 calc R
H5A H 0.3124 0.1526 0.1659 0.051 Uiso 1 1 calc R
C5 C 0.4781(2) 0.5996(5) 0.0942(2) 0.0355(9) Uani 1 1 d .
H5 H 0.4786 0.5259 0.0537 0.043 Uiso 1 1 calc R
O6 O 0.20117(14) 0.2478(3) 0.30178(18) 0.0381(7) Uani 1 1 d .
N6 N 0.23316(18) 0.4177(4) 0.0373(2) 0.0417(9) Uani 1 1 d .
H6A H 0.2044 0.4210 -0.0108 0.050 Uiso 1 1 calc R
H6B H 0.2478 0.5185 0.0627 0.050 Uiso 1 1 calc R
C6 C 0.42205(19) 0.6239(5) 0.1047(2) 0.0354(9) Uani 1 1 d .
H6 H 0.3838 0.5641 0.0721 0.043 Uiso 1 1 calc R
O7 O 0.15059(13) 0.0847(3) 0.37165(15) 0.0337(6) Uani 1 1 d .
N7 N -0.09358(17) 0.1537(5) 0.0416(2) 0.0372(8) Uani 1 1 d .
C7 C 0.24598(19) 0.7448(5) 0.3167(2) 0.0316(9) Uani 1 1 d .
O8 O 0.14339(13) 0.4082(3) 0.36481(15) 0.0344(7) Uani 1 1 d .
N8 N 0.59221(17) 0.6592(5) 0.1349(2) 0.0338(8) Uani 1 1 d .
C8 C 0.2543(2) 0.2620(5) 0.0711(2) 0.0344(9) Uani 1 1 d .
O9 O -0.09288(15) 0.0518(4) -0.00883(18) 0.0493(8) Uani 1 1 d .
C9 C 0.07729(19) 0.2255(5) 0.2410(2) 0.0305(9) Uani 1 1 d .
O10 O -0.14081(14) 0.2368(4) 0.03675(17) 0.0387(7) Uani 1 1 d .
C10 C 0.0766(2) 0.1153(6) 0.1814(2) 0.0369(10) Uani 1 1 d .
H10 H 0.1146 0.0556 0.1860 0.044 Uiso 1 1 calc R
C11 C 0.0209(2) 0.0924(6) 0.1153(2) 0.0388(10) Uani 1 1 d .
H11 H 0.0202 0.0197 0.0739 0.047 Uiso 1 1 calc R
C12 C -0.03383(19) 0.1783(5) 0.1114(2) 0.0324(9) Uani 1 1 d .
C13 C -0.0341(2) 0.2869(6) 0.1689(3) 0.0400(10) Uani 1 1 d .
H13 H -0.0723 0.3460 0.1640 0.048 Uiso 1 1 calc R
C14 C 0.0222(2) 0.3102(6) 0.2349(2) 0.0358(10) Uani 1 1 d .
H14 H 0.0226 0.3846 0.2758 0.043 Uiso 1 1 calc R
C15 C 0.0570(3) 0.5400(7) 0.0647(3) 0.0559(14) Uani 1 1 d .
C16 C -0.0020(3) 0.6078(7) 0.0567(3) 0.0589(14) Uani 1 1 d .
H16 H -0.0043 0.6809 0.0965 0.071 Uiso 1 1 calc R
C17 C -0.0565(3) 0.5710(7) -0.0072(4) 0.0620(15) Uani 1 1 d .
H17 H -0.0955 0.6245 -0.0119 0.074 Uiso 1 1 calc R
C18 C 0.4966(3) 0.8867(7) -0.0582(3) 0.0558(13) Uani 1 1 d .
H18 H 0.4939 0.8094 -0.0993 0.067 Uiso 1 1 calc R
C19 C 0.5550(2) 0.9554(7) -0.0089(3) 0.0535(13) Uani 1 1 d .
C20 C 0.5589(3) 1.0703(7) 0.0483(3) 0.0608(15) Uani 1 1 d .
H20 H 0.5988 1.1210 0.0813 0.073 Uiso 1 1 calc R
C21 C 0.1175(3) 0.5830(9) 0.1342(4) 0.091(2) Uani 1 1 d .
H21B H 0.1369 0.4712 0.1611 0.137 Uiso 1 1 calc R
H21A H 0.1076 0.6617 0.1692 0.137 Uiso 1 1 calc R
H21C H 0.1475 0.6442 0.1175 0.137 Uiso 1 1 calc R
C22 C 0.6158(3) 0.9054(9) -0.0189(5) 0.090(2) Uani 1 1 d .
H22A H 0.6418 1.0136 -0.0130 0.135 Uiso 1 1 calc R
H22B H 0.6042 0.8540 -0.0704 0.135 Uiso 1 1 calc R
H22C H 0.6402 0.8168 0.0205 0.135 Uiso 1 1 calc R
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'
S S 0.1246 0.1234 '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
O1 S1 O2 113.05(16) . .
O1 S1 O3 112.36(16) . .
O2 S1 O3 111.27(17) . .
O1 S1 C1 106.55(18) . .
O2 S1 C1 107.30(17) . .
O3 S1 C1 105.77(17) . .
C7 N1 H1A 120.0 . .
C7 N1 H1B 120.0 . .
H1A N1 H1B 120.0 . .
C2 C1 C6 121.7(4) . .
C2 C1 S1 119.9(3) . .
C6 C1 S1 118.3(3) . .
O6 S2 O8 113.67(16) . .
O6 S2 O7 112.38(17) . .
O8 S2 O7 111.47(17) . .
O6 S2 C9 106.77(19) . .
O8 S2 C9 106.55(17) . .
O7 S2 C9 105.34(17) . .
C7 N2 H2B 120.0 . .
C7 N2 H2A 120.0 . .
H2B N2 H2A 120.0 . .
C1 C2 C3 119.4(4) . .
C1 C2 H2 120.3 . .
C3 C2 H2 120.3 . .
C7 N3 H3B 120.0 . .
C7 N3 H3A 120.0 . .
H3B N3 H3A 120.0 . .
C4 C3 C2 118.2(4) . .
C4 C3 H3 120.9 . .
C2 C3 H3 120.9 . .
C8 N4 H4A 120.0 . .
C8 N4 H4B 120.0 . .
H4A N4 H4B 120.0 . .
C5 C4 C3 123.2(4) . .
C5 C4 N8 118.9(4) . .
C3 C4 N8 117.9(4) . .
C8 N5 H5B 120.0 . .
C8 N5 H5A 120.0 . .
H5B N5 H5A 120.0 . .
C4 C5 C6 118.1(4) . .
C4 C5 H5 121.0 . .
C6 C5 H5 121.0 . .
C8 N6 H6A 120.0 . .
C8 N6 H6B 120.0 . .
H6A N6 H6B 120.0 . .
C1 C6 C5 119.3(4) . .
C1 C6 H6 120.4 . .
C5 C6 H6 120.4 . .
O10 N7 O9 123.5(4) . .
O10 N7 C12 118.4(3) . .
O9 N7 C12 118.1(3) . .
N3 C7 N1 121.0(4) . .
N3 C7 N2 120.4(4) . .
N1 C7 N2 118.7(4) . .
O5 N8 O4 123.2(4) . .
O5 N8 C4 119.1(3) . .
O4 N8 C4 117.7(3) . .
N6 C8 N4 120.2(4) . .
N6 C8 N5 120.0(4) . .
N4 C8 N5 119.7(3) . .
C14 C9 C10 120.0(4) . .
C14 C9 S2 121.0(3) . .
C10 C9 S2 118.8(3) . .
C11 C10 C9 120.3(4) . .
C11 C10 H10 119.8 . .
C9 C10 H10 119.8 . .
C12 C11 C10 118.1(4) . .
C12 C11 H11 120.9 . .
C10 C11 H11 120.9 . .
C13 C12 C11 122.4(4) . .
C13 C12 N7 119.0(4) . .
C11 C12 N7 118.6(4) . .
C12 C13 C14 119.1(4) . .
C12 C13 H13 120.5 . .
C14 C13 H13 120.5 . .
C9 C14 C13 120.0(4) . .
C9 C14 H14 120.0 . .
C13 C14 H14 120.0 . .
C17 C15 C16 116.4(5) 3_565 .
C17 C15 C21 122.0(6) 3_565 .
C16 C15 C21 121.6(6) . .
C17 C16 C15 121.2(5) . .
C17 C16 H16 119.4 . .
C15 C16 H16 119.4 . .
C16 C17 C15 122.3(5) . 3_565
C16 C17 H17 118.8 . .
C15 C17 H17 118.8 3_565 .
C19 C18 C20 120.6(5) . 3_675
C19 C18 H18 119.7 . .
C20 C18 H18 119.7 3_675 .
C20 C19 C18 120.1(5) . .
C20 C19 C22 119.3(6) . .
C18 C19 C22 120.6(6) . .
C19 C20 C18 119.3(5) . 3_675
C19 C20 H20 120.4 . .
C18 C20 H20 120.4 3_675 .
C15 C21 H21B 109.5 . .
C15 C21 H21A 109.5 . .
H21B C21 H21A 109.5 . .
C15 C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
C19 C22 H22A 109.5 . .
C19 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C19 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.455(3) .
S1 O2 1.462(3) .
S1 O3 1.464(3) .
S1 C1 1.776(4) .
N1 C7 1.328(5) .
N1 H1A 0.8800 .
N1 H1B 0.8800 .
C1 C2 1.375(6) .
C1 C6 1.387(5) .
S2 O6 1.455(3) .
S2 O8 1.455(3) .
S2 O7 1.458(3) .
S2 C9 1.773(4) .
N2 C7 1.330(5) .
N2 H2B 0.8800 .
N2 H2A 0.8800 .
C2 C3 1.393(6) .
C2 H2 0.9500 .
N3 C7 1.315(5) .
N3 H3B 0.8800 .
N3 H3A 0.8800 .
C3 C4 1.378(6) .
C3 H3 0.9500 .
O4 N8 1.243(4) .
N4 C8 1.326(5) .
N4 H4A 0.8800 .
N4 H4B 0.8800 .
C4 C5 1.376(6) .
C4 N8 1.467(5) .
O5 N8 1.231(4) .
N5 C8 1.326(5) .
N5 H5B 0.8800 .
N5 H5A 0.8800 .
C5 C6 1.394(6) .
C5 H5 0.9500 .
N6 C8 1.314(5) .
N6 H6A 0.8800 .
N6 H6B 0.8800 .
C6 H6 0.9500 .
N7 O10 1.218(4) .
N7 O9 1.227(4) .
N7 C12 1.474(5) .
C9 C14 1.375(6) .
C9 C10 1.393(5) .
C10 C11 1.384(6) .
C10 H10 0.9500 .
C11 C12 1.384(6) .
C11 H11 0.9500 .
C12 C13 1.360(6) .
C13 C14 1.392(6) .
C13 H13 0.9500 .
C14 H14 0.9500 .
C15 C17 1.365(8) 3_565
C15 C16 1.395(8) .
C15 C21 1.503(8) .
C16 C17 1.365(8) .
C16 H16 0.9500 .
C17 C15 1.365(8) 3_565
C17 H17 0.9500 .
C18 C19 1.377(8) .
C18 C20 1.401(8) 3_675
C18 H18 0.9500 .
C19 C20 1.356(8) .
C19 C22 1.531(7) .
C20 C18 1.401(8) 3_675
C20 H20 0.9500 .
C21 H21B 0.9800 .
C21 H21A 0.9800 .
C21 H21C 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
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_4
O1 S1 C1 C2 142.4(3) . .
O2 S1 C1 C2 21.0(4) . .
O3 S1 C1 C2 -97.9(3) . .
O1 S1 C1 C6 -40.9(3) . .
O2 S1 C1 C6 -162.3(3) . .
O3 S1 C1 C6 78.8(3) . .
C6 C1 C2 C3 0.7(6) . .
S1 C1 C2 C3 177.3(3) . .
C1 C2 C3 C4 -0.7(6) . .
C2 C3 C4 C5 1.3(6) . .
C2 C3 C4 N8 -179.4(3) . .
C3 C4 C5 C6 -1.7(6) . .
N8 C4 C5 C6 179.0(4) . .
C2 C1 C6 C5 -1.2(6) . .
S1 C1 C6 C5 -177.8(3) . .
C4 C5 C6 C1 1.6(6) . .
C5 C4 N8 O5 176.3(4) . .
C3 C4 N8 O5 -3.1(5) . .
C5 C4 N8 O4 -4.0(5) . .
C3 C4 N8 O4 176.7(4) . .
O6 S2 C9 C14 -144.6(3) . .
O8 S2 C9 C14 -22.8(4) . .
O7 S2 C9 C14 95.7(4) . .
O6 S2 C9 C10 38.7(4) . .
O8 S2 C9 C10 160.5(3) . .
O7 S2 C9 C10 -80.9(4) . .
C14 C9 C10 C11 0.9(6) . .
S2 C9 C10 C11 177.6(3) . .
C9 C10 C11 C12 -1.4(6) . .
C10 C11 C12 C13 1.7(6) . .
C10 C11 C12 N7 -179.5(4) . .
O10 N7 C12 C13 2.5(6) . .
O9 N7 C12 C13 -178.2(4) . .
O10 N7 C12 C11 -176.3(4) . .
O9 N7 C12 C11 3.0(6) . .
C11 C12 C13 C14 -1.3(7) . .
N7 C12 C13 C14 179.9(4) . .
C10 C9 C14 C13 -0.5(6) . .
S2 C9 C14 C13 -177.1(3) . .
C12 C13 C14 C9 0.7(7) . .
C17 C15 C16 C17 -3.0(8) 3_565 .
C21 C15 C16 C17 178.7(5) . .
C15 C16 C17 C15 3.2(9) . 3_565
C20 C18 C19 C20 -2.1(8) 3_675 .
C20 C18 C19 C22 178.9(4) 3_675 .
C18 C19 C20 C18 2.1(8) . 3_675
C22 C19 C20 C18 -178.9(4) . 3_675
