#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/55/4115521.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_4115521
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            'C9.5 H19 N3 O4.5 S'
_chemical_formula_weight         279.34
_chemical_name_common
;
bis(guanidinium) 2-methoxy-4,6-dimethyl-1,5-benzenedisulfonate, 
tetrahydrofuran clathrate 
;
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m 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                   21.1037(8)
_cell_length_b                   7.5867(4)
_cell_length_c                   19.3182(8)
_cell_measurement_reflns_used    2362
_cell_measurement_temperature    173(2)
_cell_volume                     3093.0(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 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  0.1445
_diffrn_reflns_av_sigmaI/netI    0.0912
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16034
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.43
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.9760
_exptl_absorpt_correction_T_min  0.9611
_exptl_absorpt_correction_type   'simulated psi-scans '
_exptl_absorpt_process_details   'SADABS, G. Sheldrick (1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_description       prism
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.670
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1901
_refine_ls_R_factor_gt           0.0967
_refine_ls_shift/su_max          3.553
_refine_ls_shift/su_mean         0.030
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1641P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2432
_refine_ls_wR_factor_ref         0.2827
_reflns_number_gt                1469
_reflns_number_total             2943
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0030257_23.cif
_cod_data_source_block           g:\users\travis\99232\99232
_cod_original_formula_sum        'C9.50 H19 N3 O4.50 S'
_cod_database_code               4115521
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
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 0.38864(10) 0.2500 0.67916(12) 0.0500(7) Uani 1 2 d S
O1 O 0.42637(17) 0.0913(5) 0.6679(2) 0.0544(11) Uani 1 1 d .
N1 N 0.0964(4) 0.2500 0.2318(4) 0.068(2) Uani 1 2 d S
H1A H 0.0822 0.3505 0.2151 0.082 Uiso 0.50 1 calc PR
H1B H 0.0819 0.1495 0.2154 0.082 Uiso 0.50 1 calc PR
C1 C 0.3276(4) 0.2500 0.6153(4) 0.044(2) Uani 1 2 d S
S2 S 0.31379(10) 0.2500 0.40079(12) 0.0476(7) Uani 1 2 d S
O2 O 0.3588(2) 0.2500 0.7471(3) 0.0500(14) Uani 1 2 d S
N2 N 0.1619(2) 0.0996(6) 0.3069(3) 0.0603(14) Uani 1 1 d .
H2A H 0.1909 0.1004 0.3397 0.072 Uiso 1 1 calc R
H2B H 0.1476 -0.0012 0.2907 0.072 Uiso 1 1 calc R
C2 C 0.3467(4) 0.2500 0.5450(5) 0.048(2) Uani 1 2 d S
O3 O 0.28335(18) 0.0898(5) 0.3750(2) 0.0551(11) Uani 1 1 d .
N3 N 0.5630(2) 0.4024(6) 0.6457(3) 0.0580(14) Uani 1 1 d .
H3A H 0.5215 0.4043 0.6503 0.070 Uiso 1 1 calc R
H3B H 0.5843 0.5019 0.6434 0.070 Uiso 1 1 calc R
C3 C 0.2999(4) 0.2500 0.4921(4) 0.047(2) Uani 1 2 d S
O4 O 0.3814(2) 0.2500 0.3874(3) 0.0520(15) Uani 1 2 d S
N4 N 0.6549(3) 0.2500 0.6301(4) 0.060(2) Uani 1 2 d S
H4A H 0.6752 0.3504 0.6243 0.072 Uiso 0.50 1 calc PR
H4B H 0.6757 0.1496 0.6278 0.072 Uiso 0.50 1 calc PR
C4 C 0.2352(4) 0.2500 0.5145(5) 0.047(2) Uani 1 2 d S
O5 O 0.1919(3) 0.2500 0.4604(3) 0.0569(16) Uani 1 2 d S
C5 C 0.2198(4) 0.2500 0.5817(5) 0.048(2) Uani 1 2 d S
H5 H 0.1762 0.2500 0.5939 0.058 Uiso 1 2 calc SR
C6 C 0.2638(4) 0.2500 0.6336(4) 0.046(2) Uani 1 2 d S
C7 C 0.4167(4) 0.2500 0.5238(5) 0.063(3) Uani 1 2 d S
H7A H 0.4227 0.1706 0.4843 0.094 Uiso 0.50 1 calc PR
H7B H 0.4426 0.2097 0.5628 0.094 Uiso 0.50 1 calc PR
H7C H 0.4294 0.3697 0.5107 0.094 Uiso 0.50 1 calc PR
C8 C 0.2361(4) 0.2500 0.7039(5) 0.075(3) Uani 1 2 d S
H8A H 0.2522 0.3515 0.7299 0.112 Uiso 0.50 1 calc PR
H8B H 0.2479 0.1409 0.7279 0.112 Uiso 0.50 1 calc PR
H8C H 0.1898 0.2576 0.7006 0.112 Uiso 0.50 1 calc PR
C9 C 0.1251(4) 0.2500 0.4777(5) 0.070(3) Uani 1 2 d S
H9A H 0.1126 0.1322 0.4935 0.105 Uiso 0.50 1 calc PR
H9B H 0.1003 0.2820 0.4367 0.105 Uiso 0.50 1 calc PR
H9C H 0.1172 0.3357 0.5147 0.105 Uiso 0.50 1 calc PR
C10 C 0.1399(4) 0.2500 0.2820(5) 0.049(2) Uani 1 2 d S
C11 C 0.5932(4) 0.2500 0.6424(4) 0.048(2) Uani 1 2 d S
O1S O 0.2716(10) -0.2500 0.5504(19) 0.265(9) Uani 1 2 d S
C1S C 0.251(2) -0.2500 0.6283(13) 0.218(16) Uani 1 2 d S
H1S1 H 0.2664 -0.3564 0.6527 0.262 Uiso 0.50 1 calc PR
H1S2 H 0.2664 -0.1436 0.6527 0.262 Uiso 0.50 1 calc PR
O2S O 0.0519(12) 0.2500 0.6532(13) 0.327(11) Uiso 1 2 d S
C2S C 0.1825(19) -0.2500 0.622(2) 0.27(2) Uani 1 2 d S
H2S1 H 0.1655 -0.3554 0.6460 0.323 Uiso 0.50 1 calc PR
H2S2 H 0.1655 -0.1446 0.6460 0.323 Uiso 0.50 1 calc PR
C3S C 0.1627(13) -0.2500 0.5596(15) 0.223(16) Uani 1 2 d S
H3S1 H 0.1359 -0.3553 0.5523 0.268 Uiso 0.50 1 calc PR
H3S2 H 0.1359 -0.1447 0.5523 0.268 Uiso 0.50 1 calc PR
C4S C 0.2064(15) -0.2500 0.5151(14) 0.184(10) Uani 1 2 d S
H4S1 H 0.2024 -0.1444 0.4853 0.220 Uiso 0.50 1 calc PR
H4S2 H 0.2024 -0.3556 0.4853 0.220 Uiso 0.50 1 calc PR
C5S C 0.0271(14) 0.061(5) 0.6432(14) 0.329(15) Uiso 0.80 1 d P
H5S1 H 0.0590 -0.0197 0.6230 0.395 Uiso 0.80 1 calc PR
H5S2 H 0.0090 0.0096 0.6860 0.395 Uiso 0.80 1 calc PR
C6S C -0.0154(11) 0.109(4) 0.5995(13) 0.244(10) Uiso 0.80 1 d P
H6S1 H -0.0026 0.0518 0.5557 0.293 Uiso 0.80 1 calc PR
H6S2 H -0.0542 0.0472 0.6147 0.293 Uiso 0.80 1 calc PR
C7S C -0.0336(18) 0.2500 0.582(2) 0.255(16) Uiso 0.80 2 d SP
H7S1 H -0.0304 0.2500 0.5311 0.306 Uiso 0.80 2 calc SPR
H7S2 H -0.0795 0.2500 0.5929 0.306 Uiso 0.80 2 calc SPR
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 111.7(2) . 8_565
O2 S1 O1 111.7(2) . .
O1 S1 O1 111.1(3) 8_565 .
O2 S1 C1 108.1(3) . .
O1 S1 C1 106.9(2) 8_565 .
O1 S1 C1 106.9(2) . .
C6 C1 C2 121.2(8) . .
C6 C1 S1 121.6(6) . .
C2 C1 S1 117.1(6) . .
O4 S2 O3 111.8(2) . .
O4 S2 O3 111.8(2) . 8_565
O3 S2 O3 112.4(3) . 8_565
O4 S2 C3 109.7(4) . .
O3 S2 C3 105.3(2) . .
O3 S2 C3 105.3(2) 8_565 .
C1 C2 C3 119.4(7) . .
C1 C2 C7 122.1(8) . .
C3 C2 C7 118.5(8) . .
C2 C3 C4 116.4(8) . .
C2 C3 S2 126.5(6) . .
C4 C3 S2 117.0(7) . .
C5 C4 O5 124.7(7) . .
C5 C4 C3 121.7(8) . .
O5 C4 C3 113.6(8) . .
C4 O5 C9 117.9(6) . .
C4 C5 C6 123.1(8) . .
C5 C6 C1 118.1(8) . .
C5 C6 C8 114.0(7) . .
C1 C6 C8 127.9(8) . .
N2 C10 N2 119.3(8) 8_565 .
N2 C10 N1 120.4(4) 8_565 .
N2 C10 N1 120.4(4) . .
N3 C11 N3 121.9(7) . 8_565
N3 C11 N4 118.9(4) . .
N3 C11 N4 119.0(4) 8_565 .
C4S O1S C1S 100(2) . .
C2S C1S O1S 101(3) . .
C5S O2S C5S 137(3) 8_565 .
C3S C2S C1S 114(4) . .
C4S C3S C2S 114(3) . .
C3S C4S O1S 111(3) . .
C6S C5S O2S 93(3) . .
C7S C6S C5S 132(4) . .
C6S C7S C6S 129(5) 8_565 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O2 1.456(6) .
S1 O1 1.460(4) 8_565
S1 O1 1.460(4) .
S1 C1 1.784(8) .
N1 C10 1.337(10) .
C1 C6 1.392(10) .
C1 C2 1.418(11) .
S2 O4 1.450(6) .
S2 O3 1.462(4) .
S2 O3 1.462(4) 8_565
S2 C3 1.788(9) .
N2 C10 1.322(6) .
C2 C3 1.422(11) .
C2 C7 1.531(11) .
N3 C11 1.323(6) .
C3 C4 1.433(11) .
N4 C11 1.324(10) .
C4 C5 1.338(11) .
C4 O5 1.389(9) .
O5 C9 1.448(9) .
C5 C6 1.366(11) .
C6 C8 1.480(12) .
C10 N2 1.322(6) 8_565
C11 N3 1.323(6) 8_565
O1S C4S 1.54(2) .
O1S C1S 1.56(3) .
C1S C2S 1.45(4) .
O2S C5S 1.54(3) 8_565
O2S C5S 1.54(3) .
C2S C3S 1.28(4) .
C3S C4S 1.26(3) .
C5S C6S 1.29(3) .
C6S C7S 1.18(3) .
C7S C6S 1.18(3) 8_565
