# Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Alamgir Hossain'
_publ_contact_author_email       ALAMGIR@CHEM.JSUMS.EDU

_publ_section_title              
;
Ditopic binding of perchlorate
anion to hexaazamacrocyclic hosts
;
loop_
_publ_author_name
'Alamgir Hossain'
'Frank R Fronczek'
'Musabbir. A. Saeed'
'Jameskia J. Thompson'

# Attachment 'Ligand_L2_ThEAClO4.cif'

data_THEMOCTCLO4
_database_code_depnum_ccdc_archive 'CCDC 739057'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H40 N6 S2, 6(Cl O4), 4(H2 O)'
_chemical_formula_sum            'C20 H48 Cl6 N6 O28 S2'
_chemical_formula_weight         1097.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1 '

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

_cell_length_a                   8.3060(6)
_cell_length_b                   10.5205(9)
_cell_length_c                   12.4149(10)
_cell_angle_alpha                103.619(5)
_cell_angle_beta                 90.201(5)
_cell_angle_gamma                94.123(5)
_cell_volume                     1051.39(15)
_cell_formula_units_Z            1
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    7445
_cell_measurement_theta_min      3.6
_cell_measurement_theta_max      68.3

_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    5.589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.314
_exptl_absorpt_correction_T_max  0.605
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa Apex-II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10176
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.6
_diffrn_reflns_theta_max         68.7
_reflns_number_total             3690
_reflns_number_gt                3561
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker Apex2'
_computing_cell_refinement       'Bruker Apex2'
_computing_data_reduction        'Bruker Apex2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_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.

The disordered perchlorate was modeled with SADI restraints in order to
yield similar Cl-O and O...O distances for all such occurrences in both
of the orientations. O-H and H...H distances were also restrained in
the water molecules. This led to 103 total restraints.

;

_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)+(0.0406P)²+1.0629P] 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       0.0022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3690
_refine_ls_number_parameters     345
_refine_ls_number_restraints     103
_refine_ls_R_factor_all          0.033
_refine_ls_R_factor_gt           0.032
_refine_ls_wR_factor_ref         0.087
_refine_ls_wR_factor_gt          0.086
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.002
_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 0.89877(6) 0.35253(5) 0.61960(4) 0.01703(14) Uani 1 1 d . . .
N1 N 0.6642(2) 0.36054(16) 0.84590(14) 0.0166(4) Uani 1 1 d . . .
H1A H 0.7501 0.3174 0.8571 0.020 Uiso 1 1 calc R . .
H1B H 0.6176 0.3876 0.9119 0.020 Uiso 1 1 calc R . .
N2 N 0.3952(2) 0.05329(16) 0.74913(14) 0.0163(4) Uani 1 1 d . . .
H2A H 0.4535 0.0322 0.6873 0.020 Uiso 1 1 calc R . .
H2B H 0.3007 0.0799 0.7303 0.020 Uiso 1 1 calc R . .
N3 N 0.13291(19) -0.18683(16) 0.66896(14) 0.0158(3) Uani 1 1 d . . .
H3A H 0.1268 -0.1326 0.6230 0.019 Uiso 1 1 calc R . .
H3B H 0.0738 -0.1558 0.7287 0.019 Uiso 1 1 calc R . .
C1 C 0.8500(2) 0.38043(19) 0.49209(16) 0.0162(4) Uani 1 1 d . . .
C2 C 0.7313(2) 0.4646(2) 0.50078(17) 0.0193(4) Uani 1 1 d . . .
H2 H 0.6915 0.4933 0.4412 0.023 Uiso 1 1 calc R . .
C3 C 0.6748(2) 0.5041(2) 0.61037(18) 0.0194(4) Uani 1 1 d . . .
H3 H 0.5925 0.5600 0.6299 0.023 Uiso 1 1 calc R . .
C4 C 0.7533(2) 0.45160(19) 0.68385(17) 0.0173(4) Uani 1 1 d . . .
C5 C 0.7238(3) 0.47987(19) 0.80581(17) 0.0193(4) Uani 1 1 d . . .
H5A H 0.6449 0.5449 0.8236 0.023 Uiso 1 1 calc R . .
H5B H 0.8235 0.5173 0.8454 0.023 Uiso 1 1 calc R . .
C6 C 0.5469(2) 0.26663(19) 0.77047(17) 0.0163(4) Uani 1 1 d . . .
H6A H 0.5995 0.2255 0.7029 0.020 Uiso 1 1 calc R . .
H6B H 0.4582 0.3126 0.7510 0.020 Uiso 1 1 calc R . .
C7 C 0.4839(2) 0.16329(19) 0.83021(16) 0.0175(4) Uani 1 1 d . . .
H7A H 0.5733 0.1309 0.8637 0.021 Uiso 1 1 calc R . .
H7B H 0.4123 0.2014 0.8886 0.021 Uiso 1 1 calc R . .
C8 C 0.3630(2) -0.0658(2) 0.79423(17) 0.0192(4) Uani 1 1 d . . .
H8A H 0.2817 -0.0487 0.8507 0.023 Uiso 1 1 calc R . .
H8B H 0.4610 -0.0833 0.8291 0.023 Uiso 1 1 calc R . .
C9 C 0.3055(2) -0.1860(2) 0.70522(18) 0.0182(4) Uani 1 1 d . . .
H9A H 0.3736 -0.1910 0.6413 0.022 Uiso 1 1 calc R . .
H9B H 0.3183 -0.2636 0.7330 0.022 Uiso 1 1 calc R . .
C10 C 0.9381(2) 0.32170(19) 0.38928(16) 0.0163(4) Uani 1 1 d . . .
H10A H 1.0502 0.3162 0.4088 0.020 Uiso 1 1 calc R . .
H10B H 0.9357 0.3791 0.3387 0.020 Uiso 1 1 calc R . .
Cl1 Cl -0.18286(6) -0.14686(5) 0.89583(4) 0.02019(15) Uani 1 1 d . . .
O1 O -0.26909(19) -0.03002(16) 0.93014(14) 0.0285(4) Uani 1 1 d . . .
O2 O -0.01534(19) -0.10825(17) 0.87822(14) 0.0294(4) Uani 1 1 d . . .
O3 O -0.1896(2) -0.21854(17) 0.98103(14) 0.0310(4) Uani 1 1 d . . .
O4 O -0.2516(2) -0.22729(16) 0.79432(14) 0.0355(4) Uani 1 1 d . . .
Cl2 Cl 0.27560(5) 0.07197(5) 0.46682(4) 0.01900(15) Uani 1 1 d . . .
O5 O 0.3174(2) 0.03091(18) 0.35281(14) 0.0329(4) Uani 1 1 d . . .
O6 O 0.11739(18) 0.12008(16) 0.47567(13) 0.0265(4) Uani 1 1 d . . .
O7 O 0.2767(2) -0.03843(17) 0.51668(14) 0.0331(4) Uani 1 1 d . . .
O8 O 0.3905(2) 0.1727(2) 0.52497(19) 0.0483(5) Uani 1 1 d . . .
Cl3A Cl 0.2636(5) 0.5500(4) 0.8741(4) 0.0216(8) Uani 0.351(6) 1 d PD A 1
O9A O 0.3017(15) 0.5087(12) 0.7590(6) 0.039(6) Uani 0.351(6) 1 d PD A 1
O10A O 0.3273(13) 0.4606(9) 0.9319(10) 0.074(5) Uani 0.351(6) 1 d PD A 1
O11A O 0.3409(9) 0.6761(5) 0.9189(4) 0.053(2) Uani 0.351(6) 1 d PD A 1
O12A O 0.0953(6) 0.5501(10) 0.8861(7) 0.114(5) Uani 0.351(6) 1 d PD A 1
Cl3B Cl 0.2353(3) 0.5114(2) 0.8614(2) 0.0175(4) Uani 0.649(6) 1 d PD A 2
O9B O 0.2952(8) 0.4982(7) 0.7518(4) 0.028(3) Uani 0.649(6) 1 d PD A 2
O10B O 0.3621(4) 0.4886(5) 0.9329(4) 0.0241(10) Uani 0.649(6) 1 d PD A 2
O11B O 0.1839(5) 0.6393(3) 0.9018(3) 0.0595(15) Uani 0.649(6) 1 d PD A 2
O12B O 0.1040(4) 0.4160(4) 0.8602(3) 0.0572(13) Uani 0.649(6) 1 d PD A 2
O1W O 0.08962(19) 0.09734(16) 0.70745(14) 0.0269(4) Uani 1 1 d D . .
H11W H 0.023(3) 0.124(3) 0.7586(18) 0.040 Uiso 1 1 d D . .
H12W H 0.055(3) 0.114(3) 0.6485(16) 0.040 Uiso 1 1 d D . .
O2W O 0.9011(2) 0.19797(18) 0.88324(14) 0.0306(4) Uani 1 1 d D . .
H21W H 0.968(5) 0.253(4) 0.921(4) 0.046 Uiso 0.649(6) 1 d PD . .
H22W H 0.868(6) 0.135(3) 0.911(4) 0.046 Uiso 0.649(6) 1 d PD . .
H23W H 0.968(9) 0.197(9) 0.937(6) 0.046 Uiso 0.351(6) 1 d PD . .
H24W H 0.937(10) 0.272(5) 0.867(8) 0.046 Uiso 0.351(6) 1 d PD . .


_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 C4 1.726(2) . ?
S1 C1 1.728(2) . ?
N1 C6 1.491(3) . ?
N1 C5 1.509(2) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
N2 C7 1.490(3) . ?
N2 C8 1.496(3) . ?
N2 H2A 0.9000 . ?
N2 H2B 0.9000 . ?
N3 C9 1.500(3) . ?
N3 C10 1.509(2) 2_656 ?
N3 H3A 0.9000 . ?
N3 H3B 0.9000 . ?
C1 C2 1.360(3) . ?
C1 C10 1.499(3) . ?
C2 C3 1.418(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.359(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.497(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.519(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.516(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N3 1.509(2) 2_656 ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
Cl1 O4 1.4331(17) . ?
Cl1 O3 1.4356(17) . ?
Cl1 O1 1.4448(16) . ?
Cl1 O2 1.4531(16) . ?
Cl2 O8 1.4300(19) . ?
Cl2 O5 1.4311(17) . ?
Cl2 O6 1.4372(15) . ?
Cl2 O7 1.4395(17) . ?
Cl3A O12A 1.406(5) . ?
Cl3A O11A 1.418(5) . ?
Cl3A O9A 1.435(5) . ?
Cl3A O10A 1.439(6) . ?
Cl3B O11B 1.418(3) . ?
Cl3B O12B 1.427(3) . ?
Cl3B O9B 1.429(4) . ?
Cl3B O10B 1.444(3) . ?
O1W H11W 0.854(17) . ?
O1W H12W 0.846(17) . ?
O2W H21W 0.831(19) . ?
O2W H22W 0.848(19) . ?
O2W H23W 0.87(2) . ?
O2W H24W 0.89(2) . ?

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
C4 S1 C1 91.61(10) . . ?
C6 N1 C5 115.63(16) . . ?
C6 N1 H1A 108.4 . . ?
C5 N1 H1A 108.4 . . ?
C6 N1 H1B 108.4 . . ?
C5 N1 H1B 108.4 . . ?
H1A N1 H1B 107.4 . . ?
C7 N2 C8 112.45(15) . . ?
C7 N2 H2A 109.1 . . ?
C8 N2 H2A 109.1 . . ?
C7 N2 H2B 109.1 . . ?
C8 N2 H2B 109.1 . . ?
H2A N2 H2B 107.8 . . ?
C9 N3 C10 112.89(15) . 2_656 ?
C9 N3 H3A 109.0 . . ?
C10 N3 H3A 109.0 2_656 . ?
C9 N3 H3B 109.0 . . ?
C10 N3 H3B 109.0 2_656 . ?
H3A N3 H3B 107.8 . . ?
C2 C1 C10 126.74(19) . . ?
C2 C1 S1 111.26(15) . . ?
C10 C1 S1 121.92(15) . . ?
C1 C2 C3 112.79(19) . . ?
C1 C2 H2 123.6 . . ?
C3 C2 H2 123.6 . . ?
C4 C3 C2 113.04(18) . . ?
C4 C3 H3 123.5 . . ?
C2 C3 H3 123.5 . . ?
C3 C4 C5 124.90(19) . . ?
C3 C4 S1 111.26(15) . . ?
C5 C4 S1 123.79(16) . . ?
C4 C5 N1 113.64(16) . . ?
C4 C5 H5A 108.8 . . ?
N1 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
N1 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
N1 C6 C7 108.26(16) . . ?
N1 C6 H6A 110.0 . . ?
C7 C6 H6A 110.0 . . ?
N1 C6 H6B 110.0 . . ?
C7 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
N2 C7 C6 109.10(16) . . ?
N2 C7 H7A 109.9 . . ?
C6 C7 H7A 109.9 . . ?
N2 C7 H7B 109.9 . . ?
C6 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
N2 C8 C9 112.46(17) . . ?
N2 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
N2 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
N3 C9 C8 113.85(17) . . ?
N3 C9 H9A 108.8 . . ?
C8 C9 H9A 108.8 . . ?
N3 C9 H9B 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C1 C10 N3 113.01(15) . 2_656 ?
C1 C10 H10A 109.0 . . ?
N3 C10 H10A 109.0 2_656 . ?
C1 C10 H10B 109.0 . . ?
N3 C10 H10B 109.0 2_656 . ?
H10A C10 H10B 107.8 . . ?
O4 Cl1 O3 110.15(11) . . ?
O4 Cl1 O1 110.16(10) . . ?
O3 Cl1 O1 109.67(10) . . ?
O4 Cl1 O2 109.03(11) . . ?
O3 Cl1 O2 109.11(10) . . ?
O1 Cl1 O2 108.68(10) . . ?
O8 Cl2 O5 110.43(12) . . ?
O8 Cl2 O6 109.42(11) . . ?
O5 Cl2 O6 110.23(10) . . ?
O8 Cl2 O7 108.58(13) . . ?
O5 Cl2 O7 108.89(10) . . ?
O6 Cl2 O7 109.26(10) . . ?
O12A Cl3A O11A 111.3(5) . . ?
O12A Cl3A O9A 110.0(5) . . ?
O11A Cl3A O9A 109.3(5) . . ?
O12A Cl3A O10A 110.0(5) . . ?
O11A Cl3A O10A 107.7(5) . . ?
O9A Cl3A O10A 108.4(5) . . ?
O11B Cl3B O12B 110.0(3) . . ?
O11B Cl3B O9B 109.9(3) . . ?
O12B Cl3B O9B 109.7(3) . . ?
O11B Cl3B O10B 109.7(3) . . ?
O12B Cl3B O10B 108.4(2) . . ?
O9B Cl3B O10B 109.1(3) . . ?
H11W O1W H12W 108(2) . . ?
H21W O2W H22W 116(3) . . ?
H21W O2W H23W 46(5) . . ?
H22W O2W H23W 73(5) . . ?
H21W O2W H24W 55(5) . . ?
H22W O2W H24W 169(6) . . ?
H23W O2W H24W 100(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
C4 S1 C1 C2 1.70(16) . . . . ?
C4 S1 C1 C10 178.79(16) . . . . ?
C10 C1 C2 C3 -178.89(18) . . . . ?
S1 C1 C2 C3 -2.0(2) . . . . ?
C1 C2 C3 C4 1.3(3) . . . . ?
C2 C3 C4 C5 177.51(18) . . . . ?
C2 C3 C4 S1 0.1(2) . . . . ?
C1 S1 C4 C3 -0.98(16) . . . . ?
C1 S1 C4 C5 -178.47(17) . . . . ?
C3 C4 C5 N1 118.2(2) . . . . ?
S1 C4 C5 N1 -64.7(2) . . . . ?
C6 N1 C5 C4 -38.9(2) . . . . ?
C5 N1 C6 C7 -172.67(16) . . . . ?
C8 N2 C7 C6 166.52(16) . . . . ?
N1 C6 C7 N2 -167.80(15) . . . . ?
C7 N2 C8 C9 -167.81(16) . . . . ?
C10 N3 C9 C8 -161.13(16) 2_656 . . . ?
N2 C8 C9 N3 -75.9(2) . . . . ?
C2 C1 C10 N3 -95.8(2) . . . 2_656 ?
S1 C1 C10 N3 87.63(19) . . . 2_656 ?

_diffrn_measured_fraction_theta_max 0.952
_diffrn_reflns_theta_full        66.6
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.45
_refine_diff_density_min         -0.37
_refine_diff_density_rms         0.063
# END OF CIF


