#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:57:57 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178926 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/55/4115500.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_4115500
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            'C13 H17 N3 O3 S'
_chemical_formula_weight         295.36
_chemical_name_common
'bis(guanidinium)-1,4-benzenedisulfonate, benzene clathrate '
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 96.2110(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6465(6)
_cell_length_b                   11.6218(9)
_cell_length_c                   17.6250(13)
_cell_measurement_reflns_used    4458
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.1
_cell_measurement_theta_min      5.4
_cell_volume                     1557.1(2)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9065
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  0.9807
_exptl_absorpt_correction_T_min  0.9083
_exptl_absorpt_correction_type   'simulated psi-scans '
_exptl_absorpt_process_details   'SADABS, G. Sheldrick (1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.190
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2725
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.190
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0418
_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)+(0.0334P)²+1.4573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1158
_reflns_number_gt                2288
_reflns_number_total             2725
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0030257_02.cif
_cod_data_source_block           g:\travis\00068\00068
_cod_database_code               4115500
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.48951(8) 0.46260(5) 0.17627(4) 0.02957(18) Uani 1 1 d .
O1 O 0.3336(2) 0.52141(15) 0.19771(10) 0.0335(4) Uani 1 1 d .
N1 N 1.1486(3) 0.2477(2) 0.23221(13) 0.0384(6) Uani 1 1 d .
H1A H 1.2460 0.2816 0.2216 0.046 Uiso 1 1 calc R
H1B H 1.1505 0.1750 0.2461 0.046 Uiso 1 1 calc R
C1 C 0.4899(3) 0.4823(2) 0.07671(14) 0.0277(5) Uani 1 1 d .
O2 O 0.6515(2) 0.51619(16) 0.21125(10) 0.0371(4) Uani 1 1 d .
N2 N 0.9950(3) 0.41585(19) 0.20635(13) 0.0385(5) Uani 1 1 d .
H2A H 1.0921 0.4500 0.1957 0.046 Uiso 1 1 calc R
H2B H 0.8955 0.4545 0.2031 0.046 Uiso 1 1 calc R
C2 C 0.5751(3) 0.4018(2) 0.03512(15) 0.0336(6) Uani 1 1 d .
H2 H 0.6260 0.3350 0.0595 0.040 Uiso 1 1 calc R
O3 O 0.4867(2) 0.33929(15) 0.18970(10) 0.0353(4) Uani 1 1 d .
N3 N 0.8511(3) 0.2543(2) 0.24232(14) 0.0446(6) Uani 1 1 d .
H3A H 0.7513 0.2926 0.2384 0.054 Uiso 1 1 calc R
H3B H 0.8536 0.1815 0.2562 0.054 Uiso 1 1 calc R
C3 C 0.4146(3) 0.5804(2) 0.04185(15) 0.0333(6) Uani 1 1 d .
H3 H 0.3565 0.6347 0.0707 0.040 Uiso 1 1 calc R
C4 C 0.9985(3) 0.3065(2) 0.22723(14) 0.0333(6) Uani 1 1 d .
C5 C 0.9664(4) 0.2191(3) 0.02620(17) 0.0504(8) Uani 1 1 d .
H5 H 0.9487 0.1989 0.0770 0.061 Uiso 1 1 calc R
C6 C 0.9073(4) 0.1468(3) -0.03319(18) 0.0497(8) Uani 1 1 d .
H6 H 0.8497 0.0768 -0.0235 0.060 Uiso 1 1 calc R
C7 C 0.9328(4) 0.1773(3) -0.10685(17) 0.0492(8) Uani 1 1 d .
H7 H 0.8924 0.1282 -0.1482 0.059 Uiso 1 1 calc R
C8 C 1.0170(4) 0.2789(3) -0.12041(17) 0.0469(7) Uani 1 1 d .
H8 H 1.0345 0.2998 -0.1712 0.056 Uiso 1 1 calc R
C9 C 1.0752(4) 0.3498(3) -0.06117(18) 0.0474(7) Uani 1 1 d .
H9 H 1.1331 0.4198 -0.0707 0.057 Uiso 1 1 calc R
C10 C 1.0500(4) 0.3195(3) 0.01234(18) 0.0508(8) Uani 1 1 d .
H10 H 1.0908 0.3686 0.0536 0.061 Uiso 1 1 calc R
C11 C 0.4072(5) 0.0966(3) -0.0199(3) 0.0711(11) Uani 1 1 d .
H11 H 0.3424 0.1644 -0.0340 0.085 Uiso 1 1 calc R
C12 C 0.4721(6) 0.0806(4) 0.0536(3) 0.0787(13) Uani 1 1 d .
H12 H 0.4525 0.1363 0.0912 0.094 Uiso 1 1 calc R
C13 C 0.5671(5) -0.0178(4) 0.0735(2) 0.0787(12) Uani 1 1 d .
H13 H 0.6143 -0.0299 0.1250 0.094 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
O3 S1 O1 113.14(10) .
O3 S1 O2 112.22(11) .
O1 S1 O2 111.71(10) .
O3 S1 C1 106.89(11) .
O1 S1 C1 106.58(11) .
O2 S1 C1 105.73(11) .
C3 C1 C2 120.9(2) .
C3 C1 S1 119.94(18) .
C2 C1 S1 119.09(19) .
C3 C2 C1 119.7(2) 3_665
C2 C3 C1 119.4(2) 3_665
N2 C4 N1 120.2(2) .
N2 C4 N3 120.1(2) .
N1 C4 N3 119.7(2) .
C10 C5 C6 120.4(3) .
C5 C6 C7 119.3(3) .
C8 C7 C6 119.9(3) .
C9 C8 C7 120.3(3) .
C8 C9 C10 119.9(3) .
C5 C10 C9 120.2(3) .
C13 C11 C12 120.9(4) 3_655
C11 C12 C13 119.2(4) .
C11 C13 C12 119.9(4) 3_655
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O3 1.4531(18) .
S1 O1 1.4589(17) .
S1 O2 1.4621(18) .
S1 C1 1.770(2) .
N1 C4 1.330(3) .
C1 C3 1.390(3) .
C1 C2 1.393(3) .
N2 C4 1.323(3) .
C2 C3 1.383(4) 3_665
N3 C4 1.332(3) .
C3 C2 1.383(4) 3_665
C5 C10 1.365(4) .
C5 C6 1.379(4) .
C6 C7 1.380(4) .
C7 C8 1.378(4) .
C8 C9 1.366(4) .
C9 C10 1.376(4) .
C11 C13 1.346(6) 3_655
C11 C12 1.349(6) .
C12 C13 1.379(6) .
C13 C11 1.346(6) 3_655
