# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Marina Fonari'
_publ_contact_author_email       FONARI.XRAY@PHYS.ASM.MD

_publ_section_title              
;
Inclusion of triphenylmethane derivatives by crown and
linear O-containing molecules: selective interactions and crystal
structures
;
loop_
_publ_author_name
'Marina Fonari'
'Eduard V. Ganin'
'Yurii A Simonov'
'Shang-Wei Tang.'
'Wen-Jwu Wang.'

# Attachment '6m.cif'

data_6m
_database_code_depnum_ccdc_archive 'CCDC 690773'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
bis(triphenylmethanol) 1,4,7,10-tetraoxacyclooctadecane
clathrate
;
_chemical_name_common            
;bis(triphenylmethanol) 1,4,7,10-tetraoxacyclooctadecane
clathrate
;
_chemical_melting_point          188-190/oC
_chemical_formula_moiety         '2(C19 H16 O), C8 H16 O4'
_chemical_formula_sum            'C46 H48 O6'
_chemical_formula_weight         696.84

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3614(7)
_cell_length_b                   10.4963(9)
_cell_length_c                   11.7100(10)
_cell_angle_alpha                82.114(2)
_cell_angle_beta                 86.716(2)
_cell_angle_gamma                66.740(2)
_cell_volume                     935.25(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    3159
_cell_measurement_theta_min      2.586
_cell_measurement_theta_max      25.973

_exptl_crystal_description       parallelpiped
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.34
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5310
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         26.02
_reflns_number_total             3605
_reflns_number_gt                2978
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0927P)²+0.0926P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.103(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3605
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1466
_refine_ls_wR_factor_gt          0.1382
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.23143(14) 0.83849(11) 0.00181(9) 0.0495(3) Uani 1 1 d . . .
O2 O 0.09743(15) 1.07960(12) 0.12683(10) 0.0570(3) Uani 1 1 d . . .
O3 O 0.25045(13) 0.59090(11) 0.13900(8) 0.0424(3) Uani 1 1 d . . .
H3A H 0.247(2) 0.672(2) 0.1044(18) 0.064 Uiso 1 1 d . . .
C1 C 0.2142(2) 0.82607(19) -0.11612(14) 0.0583(5) Uani 1 1 d . . .
H1A H 0.3165 0.7504 -0.1404 0.070 Uiso 1 1 calc R . .
H1B H 0.2055 0.9118 -0.1637 0.070 Uiso 1 1 calc R . .
C2 C 0.3184(2) 0.92720(18) 0.01844(17) 0.0564(4) Uani 1 1 d . . .
H2A H 0.4009 0.9243 -0.0438 0.068 Uiso 1 1 calc R . .
H2B H 0.3827 0.8935 0.0902 0.068 Uiso 1 1 calc R . .
C3 C 0.1912(2) 1.07501(18) 0.02178(16) 0.0568(4) Uani 1 1 d . . .
H3B H 0.2523 1.1371 0.0176 0.068 Uiso 1 1 calc R . .
H3C H 0.1121 1.1044 -0.0431 0.068 Uiso 1 1 calc R . .
C4 C -0.0568(2) 1.20187(18) 0.13180(16) 0.0604(5) Uani 1 1 d . . .
H4A H -0.0528 1.2744 0.0721 0.073 Uiso 1 1 calc R . .
H4B H -0.0633 1.2355 0.2058 0.073 Uiso 1 1 calc R . .
C5 C 0.33748(17) 0.56115(14) 0.24767(11) 0.0345(3) Uani 1 1 d . . .
C6 C 0.39359(17) 0.40389(14) 0.28445(11) 0.0358(3) Uani 1 1 d . . .
C7 C 0.3090(2) 0.32935(16) 0.24278(13) 0.0451(4) Uani 1 1 d . . .
H7A H 0.2182 0.3752 0.1906 0.054 Uiso 1 1 calc R . .
C8 C 0.3583(2) 0.18765(18) 0.27798(15) 0.0550(4) Uani 1 1 d . . .
H8A H 0.3014 0.1389 0.2487 0.066 Uiso 1 1 calc R . .
C9 C 0.4915(2) 0.11846(17) 0.35634(15) 0.0555(4) Uani 1 1 d . . .
H9A H 0.5241 0.0234 0.3801 0.067 Uiso 1 1 calc R . .
C10 C 0.5757(2) 0.19112(17) 0.39912(14) 0.0508(4) Uani 1 1 d . . .
H10A H 0.6651 0.1451 0.4523 0.061 Uiso 1 1 calc R . .
C11 C 0.52772(19) 0.33235(15) 0.36328(12) 0.0431(4) Uani 1 1 d . . .
H11A H 0.5860 0.3802 0.3923 0.052 Uiso 1 1 calc R . .
C12 C 0.49924(17) 0.59716(14) 0.23146(11) 0.0359(3) Uani 1 1 d . . .
C13 C 0.60223(19) 0.56268(16) 0.13387(13) 0.0455(4) Uani 1 1 d . . .
H13A H 0.5693 0.5224 0.0783 0.055 Uiso 1 1 calc R . .
C14 C 0.7528(2) 0.58748(18) 0.11845(17) 0.0582(5) Uani 1 1 d . . .
H14A H 0.8199 0.5641 0.0525 0.070 Uiso 1 1 calc R . .
C15 C 0.8046(2) 0.6463(2) 0.19933(18) 0.0620(5) Uani 1 1 d . . .
H15A H 0.9069 0.6618 0.1890 0.074 Uiso 1 1 calc R . .
C16 C 0.7033(2) 0.6820(2) 0.29592(17) 0.0620(5) Uani 1 1 d . . .
H16A H 0.7371 0.7223 0.3509 0.074 Uiso 1 1 calc R . .
C17 C 0.5513(2) 0.65831(17) 0.31199(14) 0.0488(4) Uani 1 1 d . . .
H17A H 0.4836 0.6837 0.3774 0.059 Uiso 1 1 calc R . .
C18 C 0.20871(17) 0.64685(14) 0.33509(11) 0.0361(3) Uani 1 1 d . . .
C19 C 0.1272(2) 0.79080(16) 0.30728(14) 0.0496(4) Uani 1 1 d . . .
H19A H 0.1510 0.8329 0.2369 0.059 Uiso 1 1 calc R . .
C20 C 0.0113(2) 0.87216(18) 0.38296(16) 0.0583(4) Uani 1 1 d . . .
H20A H -0.0412 0.9685 0.3634 0.070 Uiso 1 1 calc R . .
C21 C -0.0272(2) 0.81195(18) 0.48696(15) 0.0554(4) Uani 1 1 d . . .
H21A H -0.1058 0.8671 0.5374 0.067 Uiso 1 1 calc R . .
C22 C 0.0514(2) 0.66972(18) 0.51573(14) 0.0517(4) Uani 1 1 d . . .
H22A H 0.0261 0.6283 0.5860 0.062 Uiso 1 1 calc R . .
C23 C 0.16885(19) 0.58748(16) 0.43992(13) 0.0429(3) Uani 1 1 d . . .
H23A H 0.2213 0.4912 0.4601 0.051 Uiso 1 1 calc R . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.425(2) . ?
O1 C2 1.426(2) . ?
O2 C3 1.416(2) . ?
O2 C4 1.421(2) . ?
O3 C5 1.4367(15) . ?
O3 H3A 0.89(2) . ?
C1 C4 1.483(3) 2_575 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.500(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3B 0.9700 . ?
C3 H3C 0.9700 . ?
C4 C1 1.483(3) 2_575 ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.5318(19) . ?
C5 C12 1.5372(18) . ?
C5 C18 1.5421(18) . ?
C6 C7 1.390(2) . ?
C6 C11 1.392(2) . ?
C7 C8 1.385(2) . ?
C7 H7A 0.9300 . ?
C8 C9 1.380(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.378(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.383(2) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C17 1.387(2) . ?
C12 C13 1.390(2) . ?
C13 C14 1.380(2) . ?
C13 H13A 0.9300 . ?
C14 C15 1.372(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.376(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.386(2) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 C23 1.383(2) . ?
C18 C19 1.389(2) . ?
C19 C20 1.382(2) . ?
C19 H19A 0.9300 . ?
C20 C21 1.375(3) . ?
C20 H20A 0.9300 . ?
C21 C22 1.373(2) . ?
C21 H21A 0.9300 . ?
C22 C23 1.392(2) . ?
C22 H22A 0.9300 . ?
C23 H23A 0.9300 . ?

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
_geom_angle_publ_flag
C1 O1 C2 113.92(13) . . ?
C3 O2 C4 114.86(13) . . ?
C5 O3 H3A 108.6(13) . . ?
O1 C1 C4 110.21(14) . 2_575 ?
O1 C1 H1A 109.6 . . ?
C4 C1 H1A 109.6 2_575 . ?
O1 C1 H1B 109.6 . . ?
C4 C1 H1B 109.6 2_575 . ?
H1A C1 H1B 108.1 . . ?
O1 C2 C3 111.08(13) . . ?
O1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
O1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
O2 C3 C2 107.58(13) . . ?
O2 C3 H3B 110.2 . . ?
C2 C3 H3B 110.2 . . ?
O2 C3 H3C 110.2 . . ?
C2 C3 H3C 110.2 . . ?
H3B C3 H3C 108.5 . . ?
O2 C4 C1 111.35(14) . 2_575 ?
O2 C4 H4A 109.4 . . ?
C1 C4 H4A 109.4 2_575 . ?
O2 C4 H4B 109.4 . . ?
C1 C4 H4B 109.4 2_575 . ?
H4A C4 H4B 108.0 . . ?
O3 C5 C6 106.32(10) . . ?
O3 C5 C12 109.34(10) . . ?
C6 C5 C12 109.58(10) . . ?
O3 C5 C18 108.61(10) . . ?
C6 C5 C18 111.31(11) . . ?
C12 C5 C18 111.54(10) . . ?
C7 C6 C11 118.08(13) . . ?
C7 C6 C5 121.08(12) . . ?
C11 C6 C5 120.81(12) . . ?
C8 C7 C6 120.81(15) . . ?
C8 C7 H7A 119.6 . . ?
C6 C7 H7A 119.6 . . ?
C9 C8 C7 120.31(15) . . ?
C9 C8 H8A 119.8 . . ?
C7 C8 H8A 119.8 . . ?
C10 C9 C8 119.58(15) . . ?
C10 C9 H9A 120.2 . . ?
C8 C9 H9A 120.2 . . ?
C9 C10 C11 120.21(15) . . ?
C9 C10 H10A 119.9 . . ?
C11 C10 H10A 119.9 . . ?
C10 C11 C6 121.01(14) . . ?
C10 C11 H11A 119.5 . . ?
C6 C11 H11A 119.5 . . ?
C17 C12 C13 118.10(14) . . ?
C17 C12 C5 122.97(13) . . ?
C13 C12 C5 118.89(12) . . ?
C14 C13 C12 120.77(15) . . ?
C14 C13 H13A 119.6 . . ?
C12 C13 H13A 119.6 . . ?
C15 C14 C13 120.75(17) . . ?
C15 C14 H14A 119.6 . . ?
C13 C14 H14A 119.6 . . ?
C14 C15 C16 119.16(15) . . ?
C14 C15 H15A 120.4 . . ?
C16 C15 H15A 120.4 . . ?
C15 C16 C17 120.60(16) . . ?
C15 C16 H16A 119.7 . . ?
C17 C16 H16A 119.7 . . ?
C16 C17 C12 120.62(16) . . ?
C16 C17 H17A 119.7 . . ?
C12 C17 H17A 119.7 . . ?
C23 C18 C19 118.08(13) . . ?
C23 C18 C5 123.27(13) . . ?
C19 C18 C5 118.64(12) . . ?
C20 C19 C18 120.79(15) . . ?
C20 C19 H19A 119.6 . . ?
C18 C19 H19A 119.6 . . ?
C21 C20 C19 120.58(15) . . ?
C21 C20 H20A 119.7 . . ?
C19 C20 H20A 119.7 . . ?
C22 C21 C20 119.47(15) . . ?
C22 C21 H21A 120.3 . . ?
C20 C21 H21A 120.3 . . ?
C21 C22 C23 120.11(15) . . ?
C21 C22 H22A 119.9 . . ?
C23 C22 H22A 119.9 . . ?
C18 C23 C22 120.96(14) . . ?
C18 C23 H23A 119.5 . . ?
C22 C23 H23A 119.5 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O1 C2 C3 91.11(17) . . . . ?
O1 C2 C3 O2 71.22(18) . . . . ?
C2 C3 O2 C4 -164.82(14) . . . . ?
C3 O2 C4 C1 103.04(17) . . . 2_575 ?
O2 C4 C1 O1 -74.74(18) . . 2_575 2_575 ?
C4 C1 O1 C2 151.28(14) . 2_575 2_575 2_575 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3A O1 0.89(2) 1.94(2) 2.8136(15) 168.8(19) .

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        26.02
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.046

# Attachment 'a12m_revised.cif'

data_a12m
_database_code_depnum_ccdc_archive 'CCDC 690774'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
triphenylmethanaminium trifluoroacetate
2-methoxyethanol clathrate
;
_chemical_name_common            
;triphenylmethanaminium trifluoroacetate 2-methoxyethanol
clathrate
;
_chemical_melting_point          155-156/oC
_chemical_formula_moiety         'C19 H18 N, C3 H8 O2, C2 F3 O2'
_chemical_formula_sum            'C24 H26 F3 N O4'
_chemical_formula_weight         449.46

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.069(4)
_cell_length_b                   10.694(3)
_cell_length_c                   26.520(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.367(5)
_cell_angle_gamma                90.00
_cell_volume                     4620(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1888
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12877
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         26.10
_reflns_number_total             4554
_reflns_number_gt                3066
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0818P)²+0.0315P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4554
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1344
_refine_ls_wR_factor_gt          0.1215
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.1287(3) 1.2885(5) 0.3299(3) 0.119(2) Uani 0.578(11) 1 d P A 1
F2 F -0.1057(8) 1.3076(8) 0.2589(3) 0.181(4) Uani 0.578(11) 1 d P A 1
F3 F -0.0089(5) 1.2989(7) 0.3283(4) 0.131(2) Uani 0.578(11) 1 d P A 1
O3 O -0.0417(8) 1.0572(11) 0.3406(4) 0.096(3) Uani 0.578(11) 1 d P A 1
O4 O -0.1053(7) 1.0702(9) 0.2552(3) 0.147(3) Uani 0.578(11) 1 d P A 1
O1 O -0.0915(3) 0.6384(7) 0.3252(2) 0.0900(16) Uani 0.578(11) 1 d P A 1
F1' F -0.0954(14) 1.2895(8) 0.3459(5) 0.205(6) Uani 0.422(11) 1 d P A 2
F2' F -0.1309(5) 1.3041(9) 0.2654(5) 0.143(5) Uani 0.422(11) 1 d P A 2
F3' F -0.0112(9) 1.2915(14) 0.3026(9) 0.191(6) Uani 0.422(11) 1 d P A 2
O3' O -0.0529(10) 1.0486(15) 0.3405(4) 0.076(3) Uani 0.422(11) 1 d P A 2
O4' O -0.1301(6) 1.0600(10) 0.2585(4) 0.094(2) Uani 0.422(11) 1 d P A 2
O1' O -0.1161(4) 0.6878(6) 0.3306(2) 0.0647(14) Uani 0.422(11) 1 d P A 2
O2 O -0.09805(7) 0.82429(13) 0.24256(4) 0.0698(3) Uani 1 1 d . . .
H2B H -0.1051(13) 0.911(2) 0.2472(9) 0.105 Uiso 1 1 d . . .
N1 N 0.03360(7) 0.82801(13) 0.34542(5) 0.0474(3) Uani 1 1 d . . .
H1N H 0.0557(11) 0.8239(15) 0.3173(7) 0.071 Uiso 1 1 d . . .
H2N H -0.0076(10) 0.7677(17) 0.3412(7) 0.071 Uiso 1 1 d . . .
H3N H 0.0071(10) 0.9071(18) 0.3436(7) 0.071 Uiso 1 1 d . . .
C1 C 0.10045(8) 0.80963(12) 0.39756(5) 0.0437(3) Uani 1 1 d . . .
C2 C 0.15418(8) 0.70097(12) 0.38907(5) 0.0470(3) Uani 1 1 d . . .
C3 C 0.23876(9) 0.70816(14) 0.40220(6) 0.0526(4) Uani 1 1 d . . .
H3A H 0.2651 0.7817 0.4167 0.063 Uiso 1 1 calc R . .
C4 C 0.28505(10) 0.60809(17) 0.39424(6) 0.0651(4) Uani 1 1 d . . .
H4A H 0.3419 0.6147 0.4037 0.078 Uiso 1 1 calc R . .
C5 C 0.24745(12) 0.49959(17) 0.37257(7) 0.0748(5) Uani 1 1 d . . .
H5A H 0.2785 0.4324 0.3670 0.090 Uiso 1 1 calc R . .
C6 C 0.16326(12) 0.49061(16) 0.35909(8) 0.0795(5) Uani 1 1 d . . .
H6A H 0.1374 0.4170 0.3443 0.095 Uiso 1 1 calc R . .
C7 C 0.11727(10) 0.58918(15) 0.36734(7) 0.0665(4) Uani 1 1 d . . .
H7A H 0.0605 0.5813 0.3583 0.080 Uiso 1 1 calc R . .
C8 C 0.05789(8) 0.78130(13) 0.43976(5) 0.0480(3) Uani 1 1 d . . .
C9 C 0.08162(10) 0.68338(16) 0.47482(6) 0.0649(4) Uani 1 1 d . . .
H9A H 0.1226 0.6290 0.4721 0.078 Uiso 1 1 calc R . .
C10 C 0.04435(14) 0.6658(2) 0.51433(7) 0.0844(6) Uani 1 1 d . . .
H10A H 0.0615 0.6003 0.5382 0.101 Uiso 1 1 calc R . .
C11 C -0.01697(13) 0.7431(2) 0.51865(8) 0.0846(6) Uani 1 1 d . . .
H11A H -0.0422 0.7297 0.5448 0.102 Uiso 1 1 calc R . .
C12 C -0.04089(12) 0.84070(19) 0.48404(8) 0.0770(5) Uani 1 1 d . . .
H12A H -0.0824 0.8941 0.4869 0.092 Uiso 1 1 calc R . .
C13 C -0.00409(10) 0.86054(15) 0.44499(6) 0.0608(4) Uani 1 1 d . . .
H13A H -0.0208 0.9275 0.4219 0.073 Uiso 1 1 calc R . .
C14 C 0.14946(8) 0.93140(12) 0.41141(5) 0.0444(3) Uani 1 1 d . . .
C15 C 0.15123(10) 1.01966(14) 0.37383(6) 0.0581(4) Uani 1 1 d . . .
H15A H 0.1215 1.0062 0.3387 0.070 Uiso 1 1 calc R . .
C16 C 0.19649(11) 1.12737(16) 0.38783(7) 0.0731(5) Uani 1 1 d . . .
H16A H 0.1962 1.1870 0.3622 0.088 Uiso 1 1 calc R . .
C17 C 0.24255(11) 1.14765(17) 0.43975(8) 0.0748(5) Uani 1 1 d . . .
H17A H 0.2737 1.2201 0.4490 0.090 Uiso 1 1 calc R . .
C18 C 0.24198(10) 1.06045(16) 0.47734(7) 0.0675(5) Uani 1 1 d . . .
H18A H 0.2731 1.0733 0.5123 0.081 Uiso 1 1 calc R . .
C19 C 0.19541(8) 0.95365(14) 0.46362(6) 0.0558(4) Uani 1 1 d . . .
H19A H 0.1946 0.8956 0.4896 0.067 Uiso 1 1 calc R . .
C20 C -0.08073(12) 1.10826(19) 0.29958(8) 0.0731(5) Uani 1 1 d . . .
C21 C -0.08054(13) 1.2502(2) 0.30375(9) 0.0811(5) Uani 1 1 d . A .
C22 C -0.1246(6) 0.5980(10) 0.3620(3) 0.143(4) Uani 0.578(11) 1 d P A 1
H22D H -0.0830 0.5584 0.3900 0.215 Uiso 0.578(11) 1 calc PR A 1
H22F H -0.1674 0.5390 0.3465 0.215 Uiso 0.578(11) 1 calc PR A 1
H22G H -0.1470 0.6676 0.3758 0.215 Uiso 0.578(11) 1 calc PR A 1
C23 C -0.1432(7) 0.6360(7) 0.2750(3) 0.121(3) Uani 0.578(11) 1 d P A 1
H23C H -0.1928 0.5926 0.2756 0.146 Uiso 0.578(11) 1 calc PR A 1
H23D H -0.1176 0.5867 0.2536 0.146 Uiso 0.578(11) 1 calc PR A 1
C24 C -0.1686(4) 0.7647(7) 0.2469(3) 0.116(5) Uani 0.578(11) 1 d P A 1
H24B H -0.2071 0.7518 0.2121 0.139 Uiso 0.578(11) 1 calc PR A 1
H24C H -0.1950 0.8161 0.2673 0.139 Uiso 0.578(11) 1 calc PR A 1
C22' C -0.1049(4) 0.5812(7) 0.3666(3) 0.105(3) Uani 0.422(11) 1 d PR A 2
H22A H -0.0910 0.6107 0.4024 0.157 Uiso 0.422(11) 1 calc PR A 2
H22B H -0.0615 0.5290 0.3625 0.157 Uiso 0.422(11) 1 calc PR A 2
H22C H -0.1549 0.5338 0.3586 0.157 Uiso 0.422(11) 1 calc PR A 2
C23' C -0.1583(11) 0.678(2) 0.2817(8) 0.252(13) Uani 0.422(11) 1 d P A 2
H23A H -0.1398 0.6001 0.2707 0.303 Uiso 0.422(11) 1 calc PR A 2
H23B H -0.2136 0.6623 0.2830 0.303 Uiso 0.422(11) 1 calc PR A 2
C24' C -0.1684(7) 0.7460(12) 0.2433(4) 0.083(4) Uani 0.422(11) 1 d P A 2
H24A H -0.2148 0.8003 0.2411 0.099 Uiso 0.422(11) 1 calc PR A 2
H24D H -0.1828 0.6940 0.2119 0.099 Uiso 0.422(11) 1 calc PR A 2


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C21 1.290(5) . ?
F2 C21 1.293(6) . ?
F3 C21 1.310(8) . ?
O3 C20 1.222(10) . ?
O4 C20 1.197(8) . ?
O1 C22 1.336(10) . ?
O1 C23 1.359(9) . ?
F1' C21 1.288(8) . ?
F2' C21 1.259(7) . ?
F3' C21 1.271(14) . ?
O3' C20 1.226(12) . ?
O4' C20 1.271(11) . ?
O1' C23' 1.286(19) . ?
O1' C22' 1.463(10) . ?
O2 C24 1.398(7) . ?
O2 C24' 1.469(9) . ?
O2 H2B 0.95(2) . ?
N1 C1 1.5200(16) . ?
N1 H1N 0.932(19) . ?
N1 H2N 0.936(18) . ?
N1 H3N 0.953(18) . ?
C1 C14 1.5321(19) . ?
C1 C8 1.535(2) . ?
C1 C2 1.5380(19) . ?
C2 C3 1.382(2) . ?
C2 C7 1.393(2) . ?
C3 C4 1.383(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.367(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.377(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.370(2) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 C9 1.379(2) . ?
C8 C13 1.394(2) . ?
C9 C10 1.391(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.365(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.369(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.378(2) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 C15 1.379(2) . ?
C14 C19 1.3932(19) . ?
C15 C16 1.375(2) . ?
C15 H15A 0.9300 . ?
C16 C17 1.384(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.367(3) . ?
C17 H17A 0.9300 . ?
C18 C19 1.377(2) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?
C20 C21 1.522(3) . ?
C22 H22D 0.9600 . ?
C22 H22F 0.9600 . ?
C22 H22G 0.9600 . ?
C23 C24 1.563(11) . ?
C23 H23C 0.9700 . ?
C23 H23D 0.9700 . ?
C24 H24B 0.9700 . ?
C24 H24C 0.9700 . ?
C22' H22A 0.9600 . ?
C22' H22B 0.9600 . ?
C22' H22C 0.9600 . ?
C23' C24' 1.220(19) . ?
C23' H23A 0.9700 . ?
C23' H23B 0.9700 . ?
C24' H24A 0.9700 . ?
C24' H24D 0.9700 . ?

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
_geom_angle_publ_flag
C22 O1 C23 114.6(7) . . ?
C23' O1' C22' 121.4(9) . . ?
C24 O2 C24' 8.4(8) . . ?
C24 O2 H2B 106.9(13) . . ?
C24' O2 H2B 114.9(14) . . ?
C1 N1 H1N 110.4(11) . . ?
C1 N1 H2N 110.6(10) . . ?
H1N N1 H2N 109.9(15) . . ?
C1 N1 H3N 112.1(10) . . ?
H1N N1 H3N 107.5(14) . . ?
H2N N1 H3N 106.1(14) . . ?
N1 C1 C14 108.42(10) . . ?
N1 C1 C8 107.37(11) . . ?
C14 C1 C8 109.65(10) . . ?
N1 C1 C2 106.45(10) . . ?
C14 C1 C2 111.75(11) . . ?
C8 C1 C2 112.96(11) . . ?
C3 C2 C7 117.46(13) . . ?
C3 C2 C1 123.00(12) . . ?
C7 C2 C1 119.54(12) . . ?
C2 C3 C4 121.31(15) . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
C5 C4 C3 120.19(16) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C5 C6 119.42(15) . . ?
C4 C5 H5A 120.3 . . ?
C6 C5 H5A 120.3 . . ?
C7 C6 C5 120.54(17) . . ?
C7 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
C6 C7 C2 121.08(15) . . ?
C6 C7 H7A 119.5 . . ?
C2 C7 H7A 119.5 . . ?
C9 C8 C13 118.26(14) . . ?
C9 C8 C1 122.27(13) . . ?
C13 C8 C1 119.39(12) . . ?
C8 C9 C10 120.15(17) . . ?
C8 C9 H9A 119.9 . . ?
C10 C9 H9A 119.9 . . ?
C11 C10 C9 121.03(18) . . ?
C11 C10 H10A 119.5 . . ?
C9 C10 H10A 119.5 . . ?
C10 C11 C12 119.22(18) . . ?
C10 C11 H11A 120.4 . . ?
C12 C11 H11A 120.4 . . ?
C11 C12 C13 120.63(18) . . ?
C11 C12 H12A 119.7 . . ?
C13 C12 H12A 119.7 . . ?
C12 C13 C8 120.70(16) . . ?
C12 C13 H13A 119.6 . . ?
C8 C13 H13A 119.6 . . ?
C15 C14 C19 118.29(13) . . ?
C15 C14 C1 122.45(12) . . ?
C19 C14 C1 119.25(12) . . ?
C16 C15 C14 120.66(15) . . ?
C16 C15 H15A 119.7 . . ?
C14 C15 H15A 119.7 . . ?
C15 C16 C17 120.44(16) . . ?
C15 C16 H16A 119.8 . . ?
C17 C16 H16A 119.8 . . ?
C18 C17 C16 119.54(15) . . ?
C18 C17 H17A 120.2 . . ?
C16 C17 H17A 120.2 . . ?
C17 C18 C19 120.15(15) . . ?
C17 C18 H18A 119.9 . . ?
C19 C18 H18A 119.9 . . ?
C18 C19 C14 120.90(15) . . ?
C18 C19 H19A 119.6 . . ?
C14 C19 H19A 119.5 . . ?
O4 C20 O3 131.4(7) . . ?
O4 C20 O3' 128.6(9) . . ?
O3 C20 O3' 9.9(14) . . ?
O4 C20 O4' 21.7(10) . . ?
O3 C20 O4' 128.9(8) . . ?
O3' C20 O4' 122.1(10) . . ?
O4 C20 C21 113.8(5) . . ?
O3 C20 C21 113.1(6) . . ?
O3' C20 C21 117.5(8) . . ?
O4' C20 C21 117.0(4) . . ?
F2' C21 F3' 103.8(9) . . ?
F2' C21 F1' 106.7(8) . . ?
F3' C21 F1' 109.4(8) . . ?
F2' C21 F1 84.1(6) . . ?
F3' C21 F1 130.4(8) . . ?
F1' C21 F1 26.9(9) . . ?
F2' C21 F2 23.1(7) . . ?
F3' C21 F2 82.5(8) . . ?
F1' C21 F2 123.1(7) . . ?
F1 C21 F2 104.7(5) . . ?
F2' C21 F3 122.1(6) . . ?
F3' C21 F3 30.2(10) . . ?
F1' C21 F3 80.5(9) . . ?
F1 C21 F3 104.9(5) . . ?
F2 C21 F3 105.8(6) . . ?
F2' C21 C20 114.3(5) . . ?
F3' C21 C20 109.1(7) . . ?
F1' C21 C20 113.1(4) . . ?
F1 C21 C20 111.6(3) . . ?
F2 C21 C20 114.4(5) . . ?
F3 C21 C20 114.5(4) . . ?
O1 C22 H22D 109.5 . . ?
O1 C22 H22F 109.5 . . ?
H22D C22 H22F 109.5 . . ?
O1 C22 H22G 109.5 . . ?
H22D C22 H22G 109.5 . . ?
H22F C22 H22G 109.5 . . ?
O1 C23 C24 117.2(6) . . ?
O1 C23 H23C 108.0 . . ?
C24 C23 H23C 108.0 . . ?
O1 C23 H23D 108.0 . . ?
C24 C23 H23D 108.0 . . ?
H23C C23 H23D 107.2 . . ?
O2 C24 C23 108.5(6) . . ?
O2 C24 H24B 110.0 . . ?
C23 C24 H24B 110.0 . . ?
O2 C24 H24C 110.0 . . ?
C23 C24 H24C 110.0 . . ?
H24B C24 H24C 108.4 . . ?
O1' C22' H22A 109.5 . . ?
O1' C22' H22B 109.5 . . ?
H22A C22' H22B 109.5 . . ?
O1' C22' H22C 109.5 . . ?
H22A C22' H22C 109.5 . . ?
H22B C22' H22C 109.5 . . ?
C24' C23' O1' 133.9(16) . . ?
C24' C23' H23A 103.7 . . ?
O1' C23' H23A 103.7 . . ?
C24' C23' H23B 103.7 . . ?
O1' C23' H23B 103.7 . . ?
H23A C23' H23B 105.4 . . ?
C23' C24' O2 115.8(10) . . ?
C23' C24' H24A 108.3 . . ?
O2 C24' H24A 108.3 . . ?
C23' C24' H24D 108.3 . . ?
O2 C24' H24D 108.3 . . ?
H24A C24' H24D 107.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H2N O1 0.936(18) 1.945(19) 2.877(5) 173.9(16) .
N1 H2N O1' 0.936(18) 1.982(19) 2.886(6) 161.9(15) .
N1 H1N O2 0.932(19) 1.93(2) 2.8615(19) 176.7(16) 2
N1 H3N O3 0.953(18) 1.80(2) 2.752(11) 179.3(19) .
N1 H3N O3' 0.953(18) 1.82(2) 2.766(14) 173.9(16) .
O2 H2B O4 0.95(2) 1.71(3) 2.658(10) 173(2) .
O2 H2B O4' 0.95(2) 1.69(3) 2.640(10) 171(2) .

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        26.10
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.034

# Attachment 'h188m.cif'

data_h188m
_database_code_depnum_ccdc_archive 'CCDC 690775'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
bis{3-[hydroxy(diphenyl)methyl]benzenesulfonamide}
1,4,7,10,13,16-hexaoxacyclooctadecane clathrate
;
_chemical_name_common            
;
bis(3-(hydroxy(diphenyl)methyl)benzenesulfonamide)
1,4,7,10,13,16-hexaoxacyclooctadecane clathrate
;
_chemical_melting_point          '174-176 /oC'
_chemical_formula_moiety         '2(C19 H17 N O3 S), C12 H24 O6'
_chemical_formula_sum            'C50 H58 N2 O12 S2'
_chemical_formula_weight         943.10

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4707(6)
_cell_length_b                   12.4699(9)
_cell_length_c                   12.8600(9)
_cell_angle_alpha                115.3720(10)
_cell_angle_beta                 97.9290(10)
_cell_angle_gamma                99.5400(10)
_cell_volume                     1176.63(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       cubic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             500
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_type   'empirical using SADABS'
_exptl_absorpt_correction_T_min  0.8850
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6829
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_sigmaI/netI    0.0410
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4541
_reflns_number_gt                3154
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0564P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4541
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1025
_refine_ls_wR_factor_gt          0.0963
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_restrained_S_all      0.925
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.12262(5) -0.25176(4) 0.01185(4) 0.04052(14) Uani 1 1 d . . .
O1 O -0.21202(16) -0.20386(12) 0.10080(12) 0.0591(4) Uani 1 1 d . . .
H1O H 0.220(3) 0.262(2) 0.257(2) 0.089 Uiso 1 1 d . . .
O2 O -0.20402(16) -0.30135(11) -0.11019(10) 0.0530(3) Uani 1 1 d . . .
O3 O 0.21251(17) 0.25370(11) 0.31352(11) 0.0452(3) Uani 1 1 d . . .
O4 O -0.23802(16) 0.38825(12) 0.07840(11) 0.0555(3) Uani 1 1 d . . .
O5 O 0.05607(18) 0.57383(13) 0.21857(11) 0.0618(4) Uani 1 1 d . A .
O6 O 0.29281(19) 0.72374(19) 0.18037(14) 0.0527(7) Uani 0.899(7) 1 d P A 1
N1 N -0.0597(2) -0.36008(15) 0.02529(15) 0.0470(4) Uani 1 1 d . . .
H1N H -0.011(3) -0.3371(19) 0.094(2) 0.071 Uiso 1 1 d . . .
H2N H -0.007(3) -0.396(2) -0.0284(19) 0.071 Uiso 1 1 d . . .
C1 C 0.2685(2) 0.13121(15) 0.40761(14) 0.0358(4) Uani 1 1 d . . .
C2 C 0.3066(2) 0.02913(17) 0.41096(16) 0.0480(5) Uani 1 1 d . . .
H2 H 0.3502 -0.0218 0.3514 0.058 Uiso 1 1 calc R . .
C3 C 0.2811(3) 0.00119(19) 0.50154(17) 0.0553(5) Uani 1 1 d . . .
H3A H 0.3087 -0.0675 0.5027 0.066 Uiso 1 1 calc R . .
C4 C 0.2152(3) 0.07433(19) 0.58957(17) 0.0569(5) Uani 1 1 d . . .
H4 H 0.1979 0.0556 0.6504 0.068 Uiso 1 1 calc R . .
C5 C 0.1755(3) 0.17494(19) 0.58667(17) 0.0612(6) Uani 1 1 d . . .
H5 H 0.1300 0.2246 0.6457 0.073 Uiso 1 1 calc R . .
C6 C 0.2019(2) 0.20401(17) 0.49687(16) 0.0497(5) Uani 1 1 d . . .
H6 H 0.1747 0.2731 0.4966 0.060 Uiso 1 1 calc R . .
C7 C 0.4903(2) 0.22412(15) 0.34139(14) 0.0369(4) Uani 1 1 d . . .
C8 C 0.6040(2) 0.15347(17) 0.31807(15) 0.0448(4) Uani 1 1 d . . .
H8 H 0.5675 0.0684 0.2815 0.054 Uiso 1 1 calc R . .
C9 C 0.7713(2) 0.20804(19) 0.34859(16) 0.0524(5) Uani 1 1 d . . .
H9 H 0.8459 0.1595 0.3316 0.063 Uiso 1 1 calc R . .
C10 C 0.8272(3) 0.3336(2) 0.40382(17) 0.0580(5) Uani 1 1 d . . .
H10 H 0.9393 0.3702 0.4240 0.070 Uiso 1 1 calc R . .
C11 C 0.7173(3) 0.40405(19) 0.42880(18) 0.0623(6) Uani 1 1 d . . .
H11 H 0.7550 0.4890 0.4673 0.075 Uiso 1 1 calc R . .
C12 C 0.5491(3) 0.35018(16) 0.39737(16) 0.0505(5) Uani 1 1 d . . .
H12 H 0.4755 0.3995 0.4142 0.061 Uiso 1 1 calc R . .
C13 C 0.2460(2) 0.05653(14) 0.18556(14) 0.0335(4) Uani 1 1 d . . .
C14 C 0.3168(2) 0.05628(15) 0.09402(14) 0.0389(4) Uani 1 1 d . . .
H14 H 0.4073 0.1194 0.1105 0.047 Uiso 1 1 calc R . .
C15 C 0.2556(2) -0.03541(16) -0.02034(15) 0.0427(4) Uani 1 1 d . . .
H15 H 0.3046 -0.0331 -0.0800 0.051 Uiso 1 1 calc R . .
C16 C 0.1222(2) -0.13090(15) -0.04754(14) 0.0401(4) Uani 1 1 d . . .
H16 H 0.0823 -0.1938 -0.1246 0.048 Uiso 1 1 calc R . .
C17 C 0.0490(2) -0.13118(14) 0.04230(14) 0.0348(4) Uani 1 1 d . . .
C18 C 0.1092(2) -0.03854(14) 0.15722(14) 0.0356(4) Uani 1 1 d . . .
H18 H 0.0577 -0.0398 0.2162 0.043 Uiso 1 1 calc R . .
C19 C 0.3043(2) 0.16544(14) 0.31019(14) 0.0356(4) Uani 1 1 d . . .
C20 C -0.3965(3) 0.3481(2) 0.0024(2) 0.0706(6) Uani 1 1 d . . .
H20A H -0.4250 0.4165 -0.0064 0.085 Uiso 1 1 calc R . .
H20B H -0.4771 0.3190 0.0373 0.085 Uiso 1 1 calc R . .
C21 C -0.2270(3) 0.4868(2) 0.19020(18) 0.0619(6) Uani 1 1 d . . .
H21A H -0.3073 0.4624 0.2280 0.074 Uiso 1 1 calc R . .
H21B H -0.2503 0.5560 0.1806 0.074 Uiso 1 1 calc R . .
C22 C -0.0576(3) 0.5226(2) 0.26541(18) 0.0604(6) Uani 1 1 d . . .
H22A H -0.0533 0.5819 0.3457 0.073 Uiso 1 1 calc R . .
H22B H -0.0296 0.4511 0.2675 0.073 Uiso 1 1 calc R . .
C23 C 0.2186(3) 0.6202(2) 0.29040(19) 0.0713(7) Uani 1 1 d . . .
H23A H 0.2455 0.5623 0.3174 0.086 Uiso 0.899(7) 1 calc PR A 1
H23B H 0.2266 0.6969 0.3593 0.086 Uiso 0.899(7) 1 calc PR A 1
H23C H 0.2141 0.6577 0.3731 0.086 Uiso 0.101(7) 1 calc PR A 2
H23D H 0.2700 0.5528 0.2761 0.086 Uiso 0.101(7) 1 calc PR A 2
C24 C 0.3367(3) 0.6404(3) 0.2210(3) 0.0652(8) Uani 0.899(7) 1 d P A 1
H24A H 0.4479 0.6740 0.2702 0.078 Uiso 0.899(7) 1 calc PR A 1
H24B H 0.3329 0.5632 0.1540 0.078 Uiso 0.899(7) 1 calc PR A 1
C25 C 0.4020(3) 0.7519(2) 0.1159(2) 0.0658(6) Uani 1 1 d . . .
H25A H 0.5135 0.7784 0.1638 0.079 Uiso 0.899(7) 1 calc PR A 1
H25B H 0.3789 0.8208 0.1057 0.079 Uiso 0.899(7) 1 calc PR A 1
H25C H 0.3334 0.8063 0.1139 0.079 Uiso 0.101(7) 1 calc PR A 2
H25D H 0.5125 0.7977 0.1634 0.079 Uiso 0.101(7) 1 calc PR A 2
O6' O 0.323(3) 0.653(2) 0.146(2) 0.086(8) Uiso 0.101(7) 1 d P A 2
C24' C 0.315(4) 0.706(3) 0.268(3) 0.075(9) Uiso 0.101(7) 1 d P A 2
H24C H 0.4246 0.7355 0.3185 0.090 Uiso 0.101(7) 1 calc PR A 2
H24D H 0.2669 0.7762 0.2859 0.090 Uiso 0.101(7) 1 calc PR A 2


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4291(13) . ?
S1 O2 1.4316(12) . ?
S1 N1 1.5972(16) . ?
S1 C17 1.7722(17) . ?
O3 C19 1.4387(19) . ?
O3 H1O 0.78(2) . ?
O4 C21 1.413(2) . ?
O4 C20 1.416(2) . ?
O5 C22 1.409(2) . ?
O5 C23 1.418(2) . ?
O6 C25 1.421(2) . ?
O6 C24 1.424(4) . ?
N1 H1N 0.82(2) . ?
N1 H2N 0.87(2) . ?
C1 C2 1.380(2) . ?
C1 C6 1.384(2) . ?
C1 C19 1.537(2) . ?
C2 C3 1.385(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.366(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.382(2) . ?
C7 C8 1.389(2) . ?
C7 C19 1.540(2) . ?
C8 C9 1.387(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.374(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.361(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.391(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.392(2) . ?
C13 C18 1.392(2) . ?
C13 C19 1.533(2) . ?
C14 C15 1.375(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.386(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.383(2) . ?
C18 H18 0.9300 . ?
C20 C25 1.486(3) 2_565 ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.492(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24' 1.39(3) . ?
C23 C24 1.490(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?
C23 H23D 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C20 1.486(3) 2_565 ?
C25 O6' 1.52(2) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 H25C 0.9700 . ?
C25 H25D 0.9700 . ?
O6' C24' 1.44(5) . ?
C24' H24C 0.9700 . ?
C24' H24D 0.9700 . ?

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
_geom_angle_publ_flag
O1 S1 O2 119.33(8) . . ?
O1 S1 N1 107.41(9) . . ?
O2 S1 N1 106.10(8) . . ?
O1 S1 C17 106.88(8) . . ?
O2 S1 C17 107.40(7) . . ?
N1 S1 C17 109.49(8) . . ?
C19 O3 H1O 105.3(18) . . ?
C21 O4 C20 112.43(16) . . ?
C22 O5 C23 113.26(15) . . ?
C25 O6 C24 112.9(2) . . ?
S1 N1 H1N 110.8(14) . . ?
S1 N1 H2N 113.0(14) . . ?
H1N N1 H2N 115(2) . . ?
C2 C1 C6 117.91(16) . . ?
C2 C1 C19 121.09(14) . . ?
C6 C1 C19 120.97(15) . . ?
C1 C2 C3 121.13(17) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 120.33(18) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C5 C4 C3 119.14(17) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 120.85(18) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 120.65(18) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C12 C7 C8 117.99(17) . . ?
C12 C7 C19 120.28(16) . . ?
C8 C7 C19 121.70(15) . . ?
C9 C8 C7 120.87(17) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C10 C9 C8 120.21(19) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 119.57(19) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 120.66(19) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C7 C12 C11 120.69(19) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C18 117.72(15) . . ?
C14 C13 C19 120.86(14) . . ?
C18 C13 C19 121.05(13) . . ?
C15 C14 C13 121.35(16) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 120.71(15) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C17 118.65(16) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
C18 C17 C16 120.81(15) . . ?
C18 C17 S1 118.83(12) . . ?
C16 C17 S1 120.35(13) . . ?
C17 C18 C13 120.73(14) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
O3 C19 C13 107.21(13) . . ?
O3 C19 C1 106.49(12) . . ?
C13 C19 C1 113.17(13) . . ?
O3 C19 C7 110.19(13) . . ?
C13 C19 C7 112.11(13) . . ?
C1 C19 C7 107.54(13) . . ?
O4 C20 C25 111.06(17) . 2_565 ?
O4 C20 H20A 109.4 . . ?
C25 C20 H20A 109.4 2_565 . ?
O4 C20 H20B 109.4 . . ?
C25 C20 H20B 109.4 2_565 . ?
H20A C20 H20B 108.0 . . ?
O4 C21 C22 109.20(17) . . ?
O4 C21 H21A 109.8 . . ?
C22 C21 H21A 109.8 . . ?
O4 C21 H21B 109.8 . . ?
C22 C21 H21B 109.8 . . ?
H21A C21 H21B 108.3 . . ?
O5 C22 C21 109.51(16) . . ?
O5 C22 H22A 109.8 . . ?
C21 C22 H22A 109.8 . . ?
O5 C22 H22B 109.8 . . ?
C21 C22 H22B 109.8 . . ?
H22A C22 H22B 108.2 . . ?
C24' C23 O5 112.3(13) . . ?
C24' C23 C24 34.4(14) . . ?
O5 C23 C24 109.61(18) . . ?
C24' C23 H23A 132.5 . . ?
O5 C23 H23A 109.7 . . ?
C24 C23 H23A 109.7 . . ?
C24' C23 H23B 77.2 . . ?
O5 C23 H23B 109.7 . . ?
C24 C23 H23B 109.7 . . ?
H23A C23 H23B 108.2 . . ?
C24' C23 H23C 109.2 . . ?
O5 C23 H23C 109.2 . . ?
C24 C23 H23C 135.6 . . ?
H23A C23 H23C 75.9 . . ?
H23B C23 H23C 35.2 . . ?
C24' C23 H23D 109.2 . . ?
O5 C23 H23D 109.2 . . ?
C24 C23 H23D 78.6 . . ?
H23A C23 H23D 34.1 . . ?
H23B C23 H23D 134.0 . . ?
H23C C23 H23D 107.9 . . ?
O6 C24 C23 108.7(3) . . ?
O6 C24 H24A 110.0 . . ?
C23 C24 H24A 110.0 . . ?
O6 C24 H24B 110.0 . . ?
C23 C24 H24B 110.0 . . ?
H24A C24 H24B 108.3 . . ?
O6 C25 C20 116.69(19) . 2_565 ?
O6 C25 O6' 35.6(10) . . ?
C20 C25 O6' 87.3(10) 2_565 . ?
O6 C25 H25A 108.1 . . ?
C20 C25 H25A 108.1 2_565 . ?
O6' C25 H25A 101.5 . . ?
O6 C25 H25B 108.1 . . ?
C20 C25 H25B 108.1 2_565 . ?
O6' C25 H25B 140.5 . . ?
H25A C25 H25B 107.3 . . ?
O6 C25 H25C 83.1 . . ?
C20 C25 H25C 114.1 2_565 . ?
O6' C25 H25C 114.1 . . ?
H25A C25 H25C 124.8 . . ?
H25B C25 H25C 26.4 . . ?
O6 C25 H25D 113.9 . . ?
C20 C25 H25D 114.1 2_565 . ?
O6' C25 H25D 114.1 . . ?
H25A C25 H25D 14.4 . . ?
H25B C25 H25D 92.9 . . ?
H25C C25 H25D 111.3 . . ?
C24' O6' C25 110(2) . . ?
C23 C24' O6' 110(3) . . ?
C23 C24' H24C 109.6 . . ?
O6' C24' H24C 109.6 . . ?
C23 C24' H24D 109.6 . . ?
O6' C24' H24D 109.6 . . ?
H24C C24' H24D 108.1 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C20 O4 C21 C22 179.29(17) . . . . ?
O4 C21 C22 O5 67.6(2) . . . . ?
C21 C22 O5 C23 174.87(18) . . . . ?
C22 O5 C23 C24 164.5(2) . . . . ?
O5 C23 C24 O6 58.3(3) . . . . ?
C23 C24 O6 C25 178.16(19) . . . . ?
C24 O6 C25 C20 69.6(3) . . . 2_565 ?
O6 C25 C20 O4 60.1(3) . . 2_565 2_565 ?
C25 C20 O4 C21 -177.64(17) . 2_565 2_565 2_565 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H1O O2 0.78(2) 2.14(2) 2.9136(17) 169(2) 2
N1 H1N O5 0.82(2) 2.37(2) 3.028(2) 137.9(18) 1_545
N1 H1N O6 0.82(2) 2.51(2) 3.086(2) 128.4(18) 1_545
N1 H2N O4 0.87(2) 2.26(2) 3.014(2) 145(2) 2
N1 H2N O5 0.87(2) 2.41(2) 3.135(2) 140(2) 2

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.041

# Attachment 'h271n_revised.cif'

data_h271n
_database_code_depnum_ccdc_archive 'CCDC 690776'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
bis (triphenylmethanaminium thiocyanate)
1,4,7,10-tetraoxacyclododecane clathrate
;
_chemical_name_common            
;
bis (triphenylmethanaminium thiocyanate) 1,4,7,10-
tetraoxacyclododecane clathrate
;
_chemical_melting_point          174-176/oC
_chemical_formula_moiety         '2(C19 H18 N, N C S), C8 H16 O4'
_chemical_formula_sum            'C48 H52 N4 O4 S2'
_chemical_formula_weight         813.06

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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'

_cell_length_a                   14.7301(15)
_cell_length_b                   16.1984(16)
_cell_length_c                   9.7290(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.973(2)
_cell_angle_gamma                90.00
_cell_volume                     2252.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       'hexagonal plate'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_type   'empirical using SADABS'
_exptl_absorpt_correction_T_min  0.8206
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12820
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_sigmaI/netI    0.1217
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4413
_reflns_number_gt                1462
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0445P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4413
_refine_ls_number_parameters     271
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1620
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1326
_refine_ls_wR_factor_gt          0.1173
_refine_ls_goodness_of_fit_ref   0.831
_refine_ls_restrained_S_all      0.831
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.41686(8) 0.83419(7) 0.58668(14) 0.1053(5) Uani 1 1 d . . .
N1 N 0.6760(2) 0.98563(16) 0.3955(3) 0.0480(7) Uani 1 1 d D . .
H1N H 0.650(2) 1.0340(13) 0.411(3) 0.072 Uiso 1 1 d D . .
H2N H 0.651(2) 0.9728(18) 0.305(2) 0.072 Uiso 1 1 d D . .
H3N H 0.659(2) 0.9500(15) 0.455(3) 0.072 Uiso 1 1 d D . .
N2 N 0.5988(2) 0.8610(2) 0.5472(3) 0.0954(12) Uani 1 1 d . . .
O1 O 0.59473(16) 0.91825(13) 0.1305(2) 0.0663(7) Uani 1 1 d . . .
O2 O 0.39380(16) 0.95714(17) 0.0725(2) 0.0738(7) Uani 1 1 d . . .
C1 C 0.5218(3) 0.8611(2) 0.1317(4) 0.0814(12) Uani 1 1 d . . .
H1B H 0.5459 0.8161 0.1960 0.098 Uiso 1 1 calc R . .
H1C H 0.4988 0.8381 0.0376 0.098 Uiso 1 1 calc R . .
C2 C 0.4440(3) 0.9025(3) 0.1771(4) 0.0844(12) Uani 1 1 d . . .
H2A H 0.4016 0.8609 0.1973 0.101 Uiso 1 1 calc R . .
H2B H 0.4692 0.9330 0.2637 0.101 Uiso 1 1 calc R . .
C3 C 0.4083(3) 1.0410(3) 0.1088(4) 0.0826(12) Uani 1 1 d . . .
H3A H 0.4748 1.0530 0.1351 0.099 Uiso 1 1 calc R . .
H3B H 0.3823 1.0539 0.1888 0.099 Uiso 1 1 calc R . .
C4 C 0.3618(3) 1.0916(2) -0.0158(4) 0.0792(12) Uani 1 1 d . . .
H4A H 0.2966 1.0755 -0.0464 0.095 Uiso 1 1 calc R . .
H4B H 0.3641 1.1493 0.0114 0.095 Uiso 1 1 calc R . .
C5 C 0.7814(2) 0.99306(17) 0.4302(3) 0.0415(8) Uani 1 1 d . . .
C6 C 0.8154(2) 0.99111(18) 0.5921(3) 0.0450(8) Uani 1 1 d . . .
C7 C 0.7734(2) 1.0410(2) 0.6740(4) 0.0640(10) Uani 1 1 d . . .
H7A H 0.7237 1.0748 0.6308 0.077 Uiso 1 1 calc R . .
C8 C 0.8051(3) 1.0410(3) 0.8199(4) 0.0788(12) Uani 1 1 d . . .
H8A H 0.7768 1.0749 0.8745 0.095 Uiso 1 1 calc R . .
C9 C 0.8784(3) 0.9907(3) 0.8841(4) 0.0780(12) Uani 1 1 d . . .
H9A H 0.8990 0.9899 0.9823 0.094 Uiso 1 1 calc R . .
C10 C 0.9211(3) 0.9417(2) 0.8034(4) 0.0745(11) Uani 1 1 d . . .
H10A H 0.9710 0.9081 0.8466 0.089 Uiso 1 1 calc R . .
C11 C 0.8901(2) 0.94249(19) 0.6585(4) 0.0576(9) Uani 1 1 d . . .
H11A H 0.9199 0.9097 0.6042 0.069 Uiso 1 1 calc R . .
C12 C 0.8178(2) 0.91954(18) 0.3598(3) 0.0451(8) Uani 1 1 d . . .
C13 C 0.7816(2) 0.8412(2) 0.3676(4) 0.0632(10) Uani 1 1 d . . .
H13A H 0.7350 0.8330 0.4158 0.076 Uiso 1 1 calc R . .
C14 C 0.8150(3) 0.7746(2) 0.3032(4) 0.0823(13) Uani 1 1 d . . .
H14A H 0.7899 0.7222 0.3072 0.099 Uiso 1 1 calc R . .
C15 C 0.8849(3) 0.7861(2) 0.2339(4) 0.0792(12) Uani 1 1 d . . .
H15A H 0.9072 0.7416 0.1913 0.095 Uiso 1 1 calc R . .
C16 C 0.9215(3) 0.8627(2) 0.2275(4) 0.0666(10) Uani 1 1 d . . .
H16A H 0.9690 0.8703 0.1809 0.080 Uiso 1 1 calc R . .
C17 C 0.8884(2) 0.92900(19) 0.2897(3) 0.0529(9) Uani 1 1 d . . .
H17A H 0.9141 0.9810 0.2844 0.063 Uiso 1 1 calc R . .
C18 C 0.8040(2) 1.07587(17) 0.3682(3) 0.0432(8) Uani 1 1 d . . .
C19 C 0.7549(2) 1.1021(2) 0.2351(4) 0.0609(9) Uani 1 1 d . . .
H19A H 0.7069 1.0694 0.1828 0.073 Uiso 1 1 calc R . .
C20 C 0.7759(3) 1.1756(2) 0.1792(4) 0.0756(11) Uani 1 1 d . . .
H20A H 0.7420 1.1925 0.0902 0.091 Uiso 1 1 calc R . .
C21 C 0.8468(3) 1.2238(2) 0.2547(5) 0.0808(13) Uani 1 1 d . . .
H21A H 0.8608 1.2738 0.2174 0.097 Uiso 1 1 calc R . .
C22 C 0.8972(3) 1.1985(2) 0.3853(4) 0.0724(11) Uani 1 1 d . . .
H22A H 0.9459 1.2311 0.4356 0.087 Uiso 1 1 calc R . .
C23 C 0.8764(2) 1.12513(19) 0.4429(3) 0.0536(9) Uani 1 1 d . . .
H23A H 0.9108 1.1087 0.5319 0.064 Uiso 1 1 calc R . .
C24 C 0.5196(3) 0.85726(19) 0.5568(3) 0.0606(10) Uani 1 1 d . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C24 1.652(4) . ?
N1 C5 1.511(4) . ?
N1 H1N 0.904(16) . ?
N1 H2N 0.891(17) . ?
N1 H3N 0.899(17) . ?
N2 C24 1.193(4) . ?
O1 C1 1.421(3) . ?
O1 C4 1.423(4) 3_675 ?
O2 C3 1.407(4) . ?
O2 C2 1.416(4) . ?
C1 C2 1.484(4) . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.486(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O1 1.423(4) 3_675 ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C12 1.534(4) . ?
C5 C6 1.534(4) . ?
C5 C18 1.540(4) . ?
C6 C11 1.380(4) . ?
C6 C7 1.381(4) . ?
C7 C8 1.383(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.377(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.371(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.373(4) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C13 1.386(4) . ?
C12 C17 1.383(4) . ?
C13 C14 1.396(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.373(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.359(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.379(4) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 C23 1.388(4) . ?
C18 C19 1.389(4) . ?
C19 C20 1.375(4) . ?
C19 H19A 0.9300 . ?
C20 C21 1.368(5) . ?
C20 H20A 0.9300 . ?
C21 C22 1.371(5) . ?
C21 H21A 0.9300 . ?
C22 C23 1.380(4) . ?
C22 H22A 0.9300 . ?
C23 H23A 0.9300 . ?

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
_geom_angle_publ_flag
C5 N1 H1N 111(2) . . ?
C5 N1 H2N 113(2) . . ?
H1N N1 H2N 106(3) . . ?
C5 N1 H3N 110(2) . . ?
H1N N1 H3N 104(3) . . ?
H2N N1 H3N 112(3) . . ?
C1 O1 C4 114.7(3) . 3_675 ?
C3 O2 C2 113.7(3) . . ?
O1 C1 C2 110.3(3) . . ?
O1 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
O1 C1 H1C 109.6 . . ?
C2 C1 H1C 109.6 . . ?
H1B C1 H1C 108.1 . . ?
O2 C2 C1 112.1(3) . . ?
O2 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
O2 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
O2 C3 C4 108.4(3) . . ?
O2 C3 H3A 110.0 . . ?
C4 C3 H3A 110.0 . . ?
O2 C3 H3B 110.0 . . ?
C4 C3 H3B 110.0 . . ?
H3A C3 H3B 108.4 . . ?
O1 C4 C3 111.8(3) 3_675 . ?
O1 C4 H4A 109.3 3_675 . ?
C3 C4 H4A 109.3 . . ?
O1 C4 H4B 109.3 3_675 . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
N1 C5 C12 106.9(2) . . ?
N1 C5 C6 106.9(2) . . ?
C12 C5 C6 112.3(2) . . ?
N1 C5 C18 106.9(2) . . ?
C12 C5 C18 111.7(2) . . ?
C6 C5 C18 111.8(2) . . ?
C11 C6 C7 118.8(3) . . ?
C11 C6 C5 121.2(3) . . ?
C7 C6 C5 120.0(3) . . ?
C8 C7 C6 120.3(3) . . ?
C8 C7 H7A 119.9 . . ?
C6 C7 H7A 119.9 . . ?
C9 C8 C7 120.0(4) . . ?
C9 C8 H8A 120.0 . . ?
C7 C8 H8A 120.0 . . ?
C10 C9 C8 120.0(4) . . ?
C10 C9 H9A 120.0 . . ?
C8 C9 H9A 120.0 . . ?
C11 C10 C9 119.9(4) . . ?
C11 C10 H10A 120.1 . . ?
C9 C10 H10A 120.1 . . ?
C10 C11 C6 121.0(3) . . ?
C10 C11 H11A 119.5 . . ?
C6 C11 H11A 119.5 . . ?
C13 C12 C17 118.3(3) . . ?
C13 C12 C5 120.4(3) . . ?
C17 C12 C5 121.3(3) . . ?
C12 C13 C14 120.1(3) . . ?
C12 C13 H13A 120.0 . . ?
C14 C13 H13A 120.0 . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 H14A 119.9 . . ?
C13 C14 H14A 119.9 . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15A 120.0 . . ?
C14 C15 H15A 120.0 . . ?
C15 C16 C17 120.4(3) . . ?
C15 C16 H16A 119.8 . . ?
C17 C16 H16A 119.8 . . ?
C16 C17 C12 121.1(3) . . ?
C16 C17 H17A 119.4 . . ?
C12 C17 H17A 119.4 . . ?
C23 C18 C19 118.3(3) . . ?
C23 C18 C5 120.5(3) . . ?
C19 C18 C5 121.2(3) . . ?
C20 C19 C18 121.2(3) . . ?
C20 C19 H19A 119.4 . . ?
C18 C19 H19A 119.4 . . ?
C21 C20 C19 119.9(4) . . ?
C21 C20 H20A 120.1 . . ?
C19 C20 H20A 120.1 . . ?
C20 C21 C22 119.9(4) . . ?
C20 C21 H21A 120.0 . . ?
C22 C21 H21A 120.0 . . ?
C21 C22 C23 120.7(4) . . ?
C21 C22 H22A 119.6 . . ?
C23 C22 H22A 119.6 . . ?
C22 C23 C18 120.0(3) . . ?
C22 C23 H23A 120.0 . . ?
C18 C23 H23A 120.0 . . ?
N2 C24 S1 168.3(3) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 O2 71.2(4) . . . . ?
C1 C2 O2 C3 -109.1(4) . . . . ?
C2 O2 C3 C4 173.0(3) . . . . ?
O2 C3 C4 O1 -66.5(4) . . . 3_675 ?
C3 C4 O1 C1 -90.7(4) . . 3_675 3_675 ?
C4 O1 C1 C2 141.3(3) . 3_675 3_675 3_675 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H2N O1 0.891(17) 1.918(19) 2.790(3) 166(3) .
N1 H3N N2 0.899(17) 2.010(19) 2.892(4) 166(3) .
N1 H1N S1 0.904(16) 2.351(18) 3.246(3) 170(3) 3_676

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.042

# Attachment 'tku1030_revised.cif'

data_tku1030
_database_code_depnum_ccdc_archive 'CCDC 690777'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
bis(1,1,1-triphenylmethanamine) 1,4,7,10-teraoxacyclododecane
clathrate
;
_chemical_name_common            
;bis(1,1,1-triphenylmethanamine) 1,4,7,10-teraoxacyclododecane
clathrate
;
_chemical_melting_point          147-148/oC
_chemical_formula_moiety         '2(C19 H17 N), C8 H16 O4'
_chemical_formula_sum            'C46 H50 N2 O4'
_chemical_formula_weight         694.88

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4675(8)
_cell_length_b                   10.2973(13)
_cell_length_c                   11.943(2)
_cell_angle_alpha                84.058(9)
_cell_angle_beta                 88.008(12)
_cell_angle_gamma                67.966(8)
_cell_volume                     960.1(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3625
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3373
_reflns_number_gt                2622
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0560P)²+0.1147P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.029(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3373
_refine_ls_number_parameters     242
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1184
_refine_ls_wR_factor_gt          0.1110
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.22731(16) 0.84728(13) -0.00454(10) 0.0663(3) Uani 1 1 d . . .
O2 O 0.09174(17) 1.07933(14) 0.13390(11) 0.0730(4) Uani 1 1 d . . .
N1 N 0.24745(18) 0.57642(16) 0.14221(11) 0.0517(3) Uani 1 1 d D . .
H1N H 0.233(3) 0.6609(17) 0.1086(16) 0.078 Uiso 1 1 d D . .
H2N H 0.295(3) 0.522(2) 0.1010(16) 0.078 Uiso 1 1 d D . .
C1 C 0.2126(3) 0.8401(2) -0.12124(16) 0.0768(6) Uani 1 1 d . . .
H1A H 0.3154 0.7693 -0.1477 0.092 Uiso 1 1 calc R . .
H1B H 0.1993 0.9301 -0.1620 0.092 Uiso 1 1 calc R . .
C2 C 0.3083(2) 0.9388(2) 0.02084(19) 0.0746(5) Uani 1 1 d . . .
H2A H 0.3876 0.9429 -0.0388 0.090 Uiso 1 1 calc R . .
H2B H 0.3727 0.9017 0.0903 0.090 Uiso 1 1 calc R . .
C3 C 0.1827(3) 1.0830(2) 0.03300(17) 0.0736(5) Uani 1 1 d . . .
H3B H 0.2410 1.1477 0.0353 0.088 Uiso 1 1 calc R . .
H3C H 0.1048 1.1149 -0.0306 0.088 Uiso 1 1 calc R . .
C4 C -0.0632(3) 1.1962(2) 0.14303(18) 0.0791(6) Uani 1 1 d . . .
H4A H -0.0632 1.2737 0.0894 0.095 Uiso 1 1 calc R . .
H4B H -0.0717 1.2266 0.2180 0.095 Uiso 1 1 calc R . .
C5 C 0.33629(17) 0.55094(15) 0.25111(11) 0.0399(3) Uani 1 1 d . . .
C6 C 0.39712(18) 0.39287(15) 0.29022(11) 0.0411(3) Uani 1 1 d . . .
C7 C 0.3155(2) 0.30982(18) 0.25505(14) 0.0575(4) Uani 1 1 d . . .
H7A H 0.2231 0.3500 0.2061 0.069 Uiso 1 1 calc R . .
C8 C 0.3698(3) 0.1677(2) 0.29185(17) 0.0697(5) Uani 1 1 d . . .
H8A H 0.3141 0.1135 0.2668 0.084 Uiso 1 1 calc R . .
C9 C 0.5049(3) 0.10648(18) 0.36482(16) 0.0689(5) Uani 1 1 d . . .
H9A H 0.5412 0.0111 0.3892 0.083 Uiso 1 1 calc R . .
C10 C 0.5859(2) 0.18721(17) 0.40154(14) 0.0608(5) Uani 1 1 d . . .
H10A H 0.6768 0.1466 0.4517 0.073 Uiso 1 1 calc R . .
C11 C 0.5330(2) 0.32882(16) 0.36435(12) 0.0491(4) Uani 1 1 d . . .
H11A H 0.5897 0.3821 0.3896 0.059 Uiso 1 1 calc R . .
C12 C 0.49191(17) 0.59458(14) 0.23685(12) 0.0411(3) Uani 1 1 d . . .
C13 C 0.5929(2) 0.56322(18) 0.14200(14) 0.0578(4) Uani 1 1 d . . .
H13A H 0.5639 0.5190 0.0865 0.069 Uiso 1 1 calc R . .
C14 C 0.7363(2) 0.5969(2) 0.12904(18) 0.0741(6) Uani 1 1 d . . .
H14A H 0.8032 0.5745 0.0651 0.089 Uiso 1 1 calc R . .
C15 C 0.7809(2) 0.6626(2) 0.20873(19) 0.0749(6) Uani 1 1 d . . .
H15A H 0.8763 0.6866 0.1988 0.090 Uiso 1 1 calc R . .
C16 C 0.6837(2) 0.6928(2) 0.30372(18) 0.0688(5) Uani 1 1 d . . .
H16A H 0.7149 0.7356 0.3594 0.083 Uiso 1 1 calc R . .
C17 C 0.5391(2) 0.66001(18) 0.31742(14) 0.0539(4) Uani 1 1 d . . .
H17A H 0.4732 0.6824 0.3817 0.065 Uiso 1 1 calc R . .
C18 C 0.20979(17) 0.63870(15) 0.33587(12) 0.0409(3) Uani 1 1 d . . .
C19 C 0.1282(2) 0.78388(17) 0.30878(14) 0.0548(4) Uani 1 1 d . . .
H19A H 0.1516 0.8251 0.2405 0.066 Uiso 1 1 calc R . .
C20 C 0.0139(2) 0.86676(18) 0.38131(16) 0.0628(5) Uani 1 1 d . . .
H20A H -0.0389 0.9631 0.3616 0.075 Uiso 1 1 calc R . .
C21 C -0.0230(2) 0.80844(19) 0.48273(16) 0.0625(5) Uani 1 1 d . . .
H21A H -0.1005 0.8647 0.5316 0.075 Uiso 1 1 calc R . .
C22 C 0.0559(2) 0.66614(19) 0.51115(14) 0.0572(4) Uani 1 1 d . . .
H22A H 0.0318 0.6259 0.5797 0.069 Uiso 1 1 calc R . .
C23 C 0.17155(19) 0.58192(16) 0.43828(12) 0.0474(4) Uani 1 1 d . . .
H23A H 0.2241 0.4858 0.4587 0.057 Uiso 1 1 calc R . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.415(2) . ?
O1 C2 1.417(2) . ?
O2 C3 1.412(2) . ?
O2 C4 1.419(2) . ?
N1 C5 1.4749(18) . ?
N1 H1N 0.886(15) . ?
N1 H2N 0.769(15) . ?
C1 C4 1.486(3) 2_575 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.485(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3B 0.9700 . ?
C3 H3C 0.9700 . ?
C4 C1 1.486(3) 2_575 ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.537(2) . ?
C5 C18 1.5417(19) . ?
C5 C12 1.5428(19) . ?
C6 C11 1.387(2) . ?
C6 C7 1.387(2) . ?
C7 C8 1.386(2) . ?
C7 H7A 0.9300 . ?
C8 C9 1.371(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.370(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.383(2) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C17 1.379(2) . ?
C12 C13 1.386(2) . ?
C13 C14 1.382(2) . ?
C13 H13A 0.9300 . ?
C14 C15 1.362(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.370(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.388(2) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 C23 1.382(2) . ?
C18 C19 1.399(2) . ?
C19 C20 1.375(2) . ?
C19 H19A 0.9300 . ?
C20 C21 1.374(3) . ?
C20 H20A 0.9300 . ?
C21 C22 1.374(2) . ?
C21 H21A 0.9300 . ?
C22 C23 1.388(2) . ?
C22 H22A 0.9300 . ?
C23 H23A 0.9300 . ?

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
_geom_angle_publ_flag
C1 O1 C2 113.91(15) . . ?
C3 O2 C4 115.39(15) . . ?
C5 N1 H1N 111.1(13) . . ?
C5 N1 H2N 113.0(16) . . ?
H1N N1 H2N 107(2) . . ?
O1 C1 C4 109.98(16) . 2_575 ?
O1 C1 H1A 109.7 . . ?
C4 C1 H1A 109.7 2_575 . ?
O1 C1 H1B 109.7 . . ?
C4 C1 H1B 109.7 2_575 . ?
H1A C1 H1B 108.2 . . ?
O1 C2 C3 111.52(16) . . ?
O1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
O1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
O2 C3 C2 108.36(15) . . ?
O2 C3 H3B 110.0 . . ?
C2 C3 H3B 110.0 . . ?
O2 C3 H3C 110.0 . . ?
C2 C3 H3C 110.0 . . ?
H3B C3 H3C 108.4 . . ?
O2 C4 C1 111.28(17) . 2_575 ?
O2 C4 H4A 109.4 . . ?
C1 C4 H4A 109.4 2_575 . ?
O2 C4 H4B 109.4 . . ?
C1 C4 H4B 109.4 2_575 . ?
H4A C4 H4B 108.0 . . ?
N1 C5 C6 108.40(11) . . ?
N1 C5 C18 108.10(11) . . ?
C6 C5 C18 110.95(11) . . ?
N1 C5 C12 109.76(11) . . ?
C6 C5 C12 109.23(11) . . ?
C18 C5 C12 110.37(11) . . ?
C11 C6 C7 117.52(14) . . ?
C11 C6 C5 121.17(12) . . ?
C7 C6 C5 121.29(13) . . ?
C8 C7 C6 120.95(16) . . ?
C8 C7 H7A 119.5 . . ?
C6 C7 H7A 119.5 . . ?
C9 C8 C7 120.51(17) . . ?
C9 C8 H8A 119.7 . . ?
C7 C8 H8A 119.7 . . ?
C10 C9 C8 119.37(16) . . ?
C10 C9 H9A 120.3 . . ?
C8 C9 H9A 120.3 . . ?
C9 C10 C11 120.28(17) . . ?
C9 C10 H10A 119.9 . . ?
C11 C10 H10A 119.9 . . ?
C10 C11 C6 121.35(15) . . ?
C10 C11 H11A 119.3 . . ?
C6 C11 H11A 119.3 . . ?
C17 C12 C13 117.97(14) . . ?
C17 C12 C5 122.40(13) . . ?
C13 C12 C5 119.59(13) . . ?
C14 C13 C12 120.71(17) . . ?
C14 C13 H13A 119.6 . . ?
C12 C13 H13A 119.6 . . ?
C15 C14 C13 120.83(18) . . ?
C15 C14 H14A 119.6 . . ?
C13 C14 H14A 119.6 . . ?
C14 C15 C16 119.26(16) . . ?
C14 C15 H15A 120.4 . . ?
C16 C15 H15A 120.4 . . ?
C15 C16 C17 120.40(18) . . ?
C15 C16 H16A 119.8 . . ?
C17 C16 H16A 119.8 . . ?
C12 C17 C16 120.82(17) . . ?
C12 C17 H17A 119.6 . . ?
C16 C17 H17A 119.6 . . ?
C23 C18 C19 117.51(14) . . ?
C23 C18 C5 123.58(13) . . ?
C19 C18 C5 118.92(13) . . ?
C20 C19 C18 121.18(16) . . ?
C20 C19 H19A 119.4 . . ?
C18 C19 H19A 119.4 . . ?
C21 C20 C19 120.53(16) . . ?
C21 C20 H20A 119.7 . . ?
C19 C20 H20A 119.7 . . ?
C22 C21 C20 119.27(15) . . ?
C22 C21 H21A 120.4 . . ?
C20 C21 H21A 120.4 . . ?
C21 C22 C23 120.46(16) . . ?
C21 C22 H22A 119.8 . . ?
C23 C22 H22A 119.8 . . ?
C18 C23 C22 121.05(15) . . ?
C18 C23 H23A 119.5 . . ?
C22 C23 H23A 119.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.886(15) 2.216(16) 3.0874(19) 168.0(18) .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.029


