#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/02/4110223.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_4110223
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            'C17 H25 N3 O3 S'
_chemical_formula_weight         351.46
_chemical_name_common            'guanidinium sulfonate clathrate'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 92.765(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5080(14)
_cell_length_b                   20.473(4)
_cell_length_c                   12.377(2)
_cell_measurement_reflns_used    825
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.891
_cell_measurement_theta_min      2.584
_cell_volume                     1900.3(6)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5910
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, G. Sheldrick (1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.15(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3691
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0362
_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)+(0.0566P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0867
_reflns_number_gt                3203
_reflns_number_total             3691
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0741574si20070910_040750_22.cif
_cod_data_source_block           G4EBS_o-xylene
_cod_database_code               4110223
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, 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 0.29725(5) 0.19508(3) 0.75539(4) 0.03377(13) Uani 1 1 d .
O1 O 0.29768(19) 0.21105(8) 0.87082(12) 0.0403(4) Uani 1 1 d .
N1 N 0.8002(2) 0.22398(9) 0.81573(15) 0.0363(4) Uani 1 1 d .
H1A H 0.6971 0.2184 0.7801 0.044 Uiso 1 1 calc R
H1B H 0.9001 0.2207 0.7817 0.044 Uiso 1 1 calc R
C1 C 0.3214(3) 0.10902(10) 0.74609(17) 0.0343(4) Uani 1 1 d .
O2 O 0.45171(18) 0.22392(7) 0.70337(11) 0.0391(3) Uani 1 1 d .
N2 N 0.9627(2) 0.24522(9) 0.97504(15) 0.0386(4) Uani 1 1 d .
H2A H 1.0623 0.2416 0.9409 0.046 Uiso 1 1 calc R
H2B H 0.9666 0.2540 1.0447 0.046 Uiso 1 1 calc R
C2 C 0.2527(3) 0.07484(11) 0.65630(18) 0.0405(5) Uani 1 1 d .
H2 H 0.1877 0.0974 0.6001 0.049 Uiso 1 1 calc R
O3 O 0.12855(18) 0.21197(8) 0.69651(11) 0.0385(4) Uani 1 1 d .
N3 N 0.6544(2) 0.24229(9) 0.97301(14) 0.0372(4) Uani 1 1 d .
H3A H 0.5510 0.2367 0.9377 0.045 Uiso 1 1 calc R
H3B H 0.6583 0.2511 1.0427 0.045 Uiso 1 1 calc R
C3 C 0.2786(3) 0.00801(12) 0.64841(19) 0.0465(6) Uani 1 1 d .
H3 H 0.2324 -0.0146 0.5861 0.056 Uiso 1 1 calc R
C4 C 0.3719(3) -0.02707(13) 0.7308(2) 0.0490(6) Uani 1 1 d .
C5 C 0.4410(3) 0.00792(13) 0.8195(2) 0.0503(6) Uani 1 1 d .
H5 H 0.5064 -0.0147 0.8755 0.060 Uiso 1 1 calc R
C6 C 0.4173(3) 0.07501(13) 0.82887(18) 0.0449(6) Uani 1 1 d .
H6 H 0.4653 0.0977 0.8906 0.054 Uiso 1 1 calc R
C7 C 0.4024(4) -0.10098(15) 0.7268(3) 0.0686(8) Uani 1 1 d .
H7A H 0.5326 -0.1088 0.7285 0.082 Uiso 1 1 calc R
H7B H 0.3573 -0.1202 0.7937 0.082 Uiso 1 1 calc R
C8 C 0.3198(6) -0.13742(15) 0.6327(2) 0.0838(11) Uani 1 1 d .
H8A H 0.1899 -0.1324 0.6317 0.126 Uiso 1 1 calc R
H8B H 0.3506 -0.1838 0.6391 0.126 Uiso 1 1 calc R
H8C H 0.3647 -0.1200 0.5655 0.126 Uiso 1 1 calc R
C9 C 0.8051(3) 0.23732(9) 0.92101(16) 0.0298(4) Uani 1 1 d .
C10 C 0.8092(3) -0.04937(12) 1.0251(2) 0.0470(6) Uani 1 1 d .
C11 C 0.8910(3) -0.05001(12) 0.9242(2) 0.0463(6) Uani 1 1 d .
C12 C 0.9484(3) 0.00897(14) 0.8831(2) 0.0531(6) Uani 1 1 d .
H12 H 1.0053 0.0089 0.8162 0.064 Uiso 1 1 calc R
C13 C 0.9267(4) 0.06739(13) 0.9349(2) 0.0566(7) Uani 1 1 d .
H13 H 0.9689 0.1067 0.9045 0.068 Uiso 1 1 calc R
C14 C 0.8424(4) 0.06844(14) 1.0322(3) 0.0594(7) Uani 1 1 d .
H14 H 0.8235 0.1086 1.0685 0.071 Uiso 1 1 calc R
C15 C 0.7869(3) 0.01077(16) 1.0751(2) 0.0546(7) Uani 1 1 d .
H15 H 0.7306 0.0118 1.1422 0.066 Uiso 1 1 calc R
C16 C 0.7447(4) -0.11182(17) 1.0746(3) 0.0783(10) Uani 1 1 d .
H16A H 0.6994 -0.1025 1.1459 0.117 Uiso 1 1 calc R
H16B H 0.8438 -0.1429 1.0823 0.117 Uiso 1 1 calc R
H16C H 0.6491 -0.1306 1.0277 0.117 Uiso 1 1 calc R
C17 C 0.9199(5) -0.11248(15) 0.8641(3) 0.0782(9) Uani 1 1 d .
H17A H 0.9548 -0.1025 0.7906 0.117 Uiso 1 1 calc R
H17B H 0.8093 -0.1380 0.8605 0.117 Uiso 1 1 calc R
H17C H 1.0145 -0.1378 0.9018 0.117 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
O1 S1 O3 113.06(9)
O1 S1 O2 111.79(9)
O3 S1 O2 111.43(9)
O1 S1 C1 106.80(9)
O3 S1 C1 106.81(9)
O2 S1 C1 106.48(9)
C2 C1 C6 119.3(2)
C2 C1 S1 121.05(16)
C6 C1 S1 119.59(17)
C3 C2 C1 120.32(19)
C2 C3 C4 121.3(2)
C5 C4 C3 117.6(2)
C5 C4 C7 118.9(2)
C3 C4 C7 123.4(2)
C4 C5 C6 122.0(2)
C5 C6 C1 119.4(2)
C8 C7 C4 117.5(2)
N1 C9 N3 120.32(17)
N1 C9 N2 119.71(18)
N3 C9 N2 119.97(18)
C15 C10 C11 117.8(2)
C15 C10 C16 121.5(3)
C11 C10 C16 120.7(3)
C12 C11 C10 118.0(2)
C12 C11 C17 120.4(3)
C10 C11 C17 121.6(3)
C13 C12 C11 122.9(3)
C12 C13 C14 119.3(3)
C15 C14 C13 118.9(3)
C14 C15 C10 123.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4655(16)
S1 O3 1.4716(14)
S1 O2 1.4765(15)
S1 C1 1.776(2)
N1 C9 1.330(3)
C1 C2 1.391(3)
C1 C6 1.408(3)
N2 C9 1.341(3)
C2 C3 1.386(3)
N3 C9 1.332(3)
C3 C4 1.406(3)
C4 C5 1.390(4)
C4 C7 1.532(4)
C5 C6 1.391(4)
C7 C8 1.493(5)
C10 C15 1.392(4)
C10 C11 1.418(4)
C10 C16 1.507(4)
C11 C12 1.387(4)
C11 C17 1.501(4)
C12 C13 1.370(4)
C13 C14 1.388(4)
C14 C15 1.368(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660386
