#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:57:57 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178926 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/55/4115503.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_4115503
loop_
_publ_author_name
'K. Travis Holman'
'Stephen M. Martin'
'Daniel P. Parker'
'Michael D. Ward'
_publ_section_title
;
 The Generality of Architectural Isomerism in Designer Inclusion
 Frameworks
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4421
_journal_page_last               4431
_journal_paper_doi               10.1021/ja0030257
_journal_volume                  123
_journal_year                    2001
_chemical_formula_sum            'C14 H16 N3 O3 S'
_chemical_formula_weight         306.36
_chemical_name_common
'bis(guanidinium)-1,4-benzenedisulfonate, naphthalene clathrate '
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   13.3600(10)
_cell_length_b                   12.6471(10)
_cell_length_c                   18.1682(14)
_cell_measurement_reflns_used    5990
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      53.4
_cell_measurement_theta_min      5.0
_cell_volume                     3069.8(4)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'SMART, Bruker (or Siemens)'
_computing_data_reduction        'SAINT, Bruker'
_computing_molecular_graphics
'XSEED, L. Barbour (1999); http://www.lbarbour.com/xseed'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0501
_diffrn_reflns_av_sigmaI/netI    0.0276
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21693
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_correction_T_min  0.9040
_exptl_absorpt_correction_type   'simulated psi-scans '
_exptl_absorpt_process_details   'SADABS, G. Sheldrick (1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       plate
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.041
_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     190
_refine_ls_number_reflns         2696
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0427P)²+0.6435P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0851
_reflns_number_gt                1969
_reflns_number_total             2696
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0030257_05.cif
_cod_data_source_block           g:\travis\00080\00080
_cod_database_code               4115503
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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 0.08193(3) 0.02748(3) 0.16148(2) 0.02802(14) Uani 1 1 d .
O1 O 0.18038(9) -0.02213(9) 0.16446(7) 0.0320(3) Uani 1 1 d .
N1 N 0.22121(12) -0.24420(12) 0.18904(9) 0.0394(4) Uani 1 1 d .
H1A H 0.2146 -0.1762 0.1799 0.047 Uiso 1 1 calc R
H1B H 0.2764 -0.2774 0.1762 0.047 Uiso 1 1 calc R
C1 C 0.03677(14) 0.01124(12) 0.07042(10) 0.0264(4) Uani 1 1 d .
O2 O 0.00906(9) -0.02422(9) 0.20908(7) 0.0337(3) Uani 1 1 d .
N2 N 0.06470(11) -0.24702(12) 0.24161(8) 0.0356(4) Uani 1 1 d .
H2A H 0.0578 -0.1790 0.2326 0.043 Uiso 1 1 calc R
H2B H 0.0163 -0.2821 0.2636 0.043 Uiso 1 1 calc R
C2 C 0.09761(14) -0.02994(15) 0.01609(10) 0.0328(4) Uani 1 1 d .
H2 H 0.1643 -0.0504 0.0273 0.039 Uiso 1 1 calc R
O3 O 0.08721(9) 0.14137(9) 0.17471(7) 0.0320(3) Uani 1 1 d .
N3 N 0.15825(12) -0.39902(11) 0.23595(9) 0.0366(4) Uani 1 1 d .
H3A H 0.2135 -0.4321 0.2231 0.044 Uiso 1 1 calc R
H3B H 0.1097 -0.4339 0.2579 0.044 Uiso 1 1 calc R
C3 C -0.06100(14) 0.04131(15) 0.05472(11) 0.0345(5) Uani 1 1 d .
H3 H -0.1025 0.0695 0.0924 0.041 Uiso 1 1 calc R
C4 C 0.14805(14) -0.29656(14) 0.22213(10) 0.0306(4) Uani 1 1 d .
C1A C 0.33779(16) 0.09008(18) 0.02562(13) 0.0484(6) Uani 1 1 d .
H1A1 H 0.3414 0.1049 0.0768 0.058 Uiso 1 1 calc R
C2A C 0.30464(18) 0.16608(18) -0.02103(14) 0.0560(6) Uani 1 1 d .
H2A1 H 0.2851 0.2331 -0.0023 0.067 Uiso 1 1 calc R
C3A C 0.29904(18) 0.14618(19) -0.09684(14) 0.0579(6) Uani 1 1 d .
H3A1 H 0.2753 0.1996 -0.1292 0.070 Uiso 1 1 calc R
C4A C 0.32732(17) 0.05116(19) -0.12418(12) 0.0506(6) Uani 1 1 d .
H4A H 0.3240 0.0391 -0.1757 0.061 Uiso 1 1 calc R
C5A C 0.39267(17) -0.13024(18) -0.10399(15) 0.0558(6) Uani 1 1 d .
H5A H 0.3905 -0.1443 -0.1553 0.067 Uiso 1 1 calc R
C6A C 0.42527(19) -0.2059(2) -0.05717(18) 0.0680(8) Uani 1 1 d .
H6A H 0.4462 -0.2724 -0.0760 0.082 Uiso 1 1 calc R
C7A C 0.42862(18) -0.1873(2) 0.01908(18) 0.0680(8) Uani 1 1 d .
H7A H 0.4505 -0.2416 0.0514 0.082 Uiso 1 1 calc R
C8A C 0.40067(16) -0.0922(2) 0.04666(14) 0.0539(6) Uani 1 1 d .
H8A H 0.4038 -0.0803 0.0982 0.065 Uiso 1 1 calc R
C9A C 0.36177(15) -0.03053(16) -0.07730(11) 0.0416(5) Uani 1 1 d .
C10A C 0.36694(15) -0.01033(17) -0.00022(12) 0.0405(5) Uani 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'
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
O2 S1 O1 112.80(7) . .
O2 S1 O3 112.13(7) . .
O1 S1 O3 111.98(7) . .
O2 S1 C1 105.93(8) . .
O1 S1 C1 106.96(8) . .
O3 S1 C1 106.50(7) . .
C2 C1 C3 120.65(17) . .
C2 C1 S1 120.69(14) . .
C3 C1 S1 118.66(14) . .
C1 C2 C3 119.72(17) . 5
C2 C3 C1 119.63(17) 5 .
N1 C4 N2 120.30(17) . .
N1 C4 N3 119.88(17) . .
N2 C4 N3 119.82(17) . .
C2A C1A C10A 121.4(2) . .
C1A C2A C3A 120.3(2) . .
C4A C3A C2A 120.3(2) . .
C3A C4A C9A 121.2(2) . .
C6A C5A C9A 120.6(2) . .
C5A C6A C7A 120.8(2) . .
C8A C7A C6A 120.2(2) . .
C7A C8A C10A 121.0(2) . .
C5A C9A C4A 122.7(2) . .
C5A C9A C10A 118.9(2) . .
C4A C9A C10A 118.43(19) . .
C1A C10A C8A 123.2(2) . .
C1A C10A C9A 118.4(2) . .
C8A C10A C9A 118.4(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O2 1.4572(13) .
S1 O1 1.4583(13) .
S1 O3 1.4620(12) .
S1 C1 1.7730(18) .
N1 C4 1.325(2) .
C1 C2 1.381(2) .
C1 C3 1.390(3) .
N2 C4 1.326(2) .
C2 C3 1.384(3) 5
N3 C4 1.327(2) .
C3 C2 1.384(3) 5
C1A C2A 1.356(3) .
C1A C10A 1.409(3) .
C2A C3A 1.402(4) .
C3A C4A 1.354(3) .
C4A C9A 1.416(3) .
C5A C6A 1.352(4) .
C5A C9A 1.413(3) .
C6A C7A 1.406(4) .
C7A C8A 1.356(4) .
C8A C10A 1.414(3) .
C9A C10A 1.425(3) .
