# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is (c) The Royal Society of Chemistry and 
# The Centre National de la Recherche Scientifique, 2009


data_global
_journal_name_full               'New J.Chem.'

_journal_coden_Cambridge         0440

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

_publ_section_title              
;
Conformational Mobility of 7,16-Bis(4-methoxybenzyl)
-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane in Molecular and Proton
Transfer Complexes: X-ray and DFT Study
;
loop_
_publ_author_name
'Marina Fonari'
'Stepan S. Basok'
'Mark Botoshansky'
'Yurii M Chumakov'
'Eduard V. Ganin'
;
Y.A.Simonov
;
'Kinga Suwinska'

# Attachment 'ych1.cif'

data_ych1
_database_code_depnum_ccdc_archive 'CCDC 717106'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
7,16-bis(4-methoxybenzyl)-1,4,10,13-tetraoxa-7,16-
diazoniacyclooctadecane dihexafluorotantalate dihydrate
;
_chemical_name_common            
;
7,16-bis(4-methoxybenzyl)-1,4,10,13-tetraoxa-7,16-
diazoniacyclooctadecane dihexafluorotantalate dihydrate
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H44 N2 O6, 2(Ta F6), 2(H2 O)'
_chemical_formula_sum            'C28 H48 F12 N2 O8 Ta2'
_chemical_formula_weight         1130.58

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'
Ta Ta -0.7052 6.5227 '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                   6.8062(11)
_cell_length_b                   11.3381(18)
_cell_length_c                   14.098(2)
_cell_angle_alpha                105.873(9)
_cell_angle_beta                 101.336(9)
_cell_angle_gamma                106.175(6)
_cell_volume                     960.2(3)
_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       block
_exptl_crystal_colour            light-brown
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.955
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             548
_exptl_absorpt_coefficient_mu    5.797
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.290
_exptl_absorpt_correction_T_max  0.531
_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  'Bruker CCD diffractometer'
_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            5444
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0601
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3640
_reflns_number_gt                2021
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1169P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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         3640
_refine_ls_number_parameters     238
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1874
_refine_ls_wR_factor_gt          0.1575
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_restrained_S_all      0.926
_refine_ls_shift/su_max          0.001
_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
Ta1 Ta 0.0000 0.0000 0.5000 0.0885(3) Uani 1 2 d S . .
Ta2 Ta 0.0000 0.0000 0.0000 0.0870(3) Uani 1 2 d S . .
F1 F -0.0128(18) 0.1673(9) 0.5253(7) 0.147(4) Uani 1 1 d . . .
F2 F -0.1518(18) -0.0507(10) 0.3609(7) 0.165(4) Uani 1 1 d . . .
F3 F 0.2584(15) 0.0583(9) 0.4727(9) 0.167(4) Uani 1 1 d . . .
F4 F 0.0768(17) -0.0901(10) -0.1091(7) 0.163(3) Uani 1 1 d . . .
F5 F 0.2820(12) 0.0527(7) 0.0858(7) 0.120(2) Uani 1 1 d . . .
F6 F 0.0765(15) 0.1525(9) -0.0300(9) 0.156(4) Uani 1 1 d . . .
O1 O 0.6328(14) 0.2845(8) 0.8962(6) 0.091(2) Uani 1 1 d . . .
O2 O 1.2286(16) 0.5316(9) 0.9010(6) 0.107(3) Uani 1 1 d . . .
O3 O 0.2431(14) 0.6530(8) 0.6180(7) 0.102(2) Uani 1 1 d . . .
N1 N 0.8471(16) 0.3453(9) 0.7544(7) 0.085(2) Uani 1 1 d D . .
H1N1 H 0.85(2) 0.422(6) 0.792(8) 0.127 Uiso 1 1 d D . .
C1 C 1.045(2) 0.3124(13) 0.7845(10) 0.110(4) Uani 1 1 d . . .
H1A H 1.0496 0.2460 0.7255 0.132 Uiso 1 1 calc R . .
H1B H 1.0358 0.2758 0.8389 0.132 Uiso 1 1 calc R . .
C2 C 1.250(2) 0.4307(15) 0.8217(10) 0.100(4) Uani 1 1 d . . .
H2A H 1.3712 0.4080 0.8483 0.120 Uiso 1 1 calc R . .
H2B H 1.2723 0.4603 0.7650 0.120 Uiso 1 1 calc R . .
C3 C 1.410(3) 0.6512(15) 0.9374(12) 0.133(6) Uani 1 1 d . . .
H3A H 1.4315 0.6794 0.8800 0.160 Uiso 1 1 calc R . .
H3B H 1.5376 0.6372 0.9685 0.160 Uiso 1 1 calc R . .
C4 C 0.649(2) 0.2300(11) 0.7276(8) 0.098(3) Uani 1 1 d . . .
H4A H 0.6488 0.1605 0.6691 0.118 Uiso 1 1 calc R . .
H4B H 0.5266 0.2542 0.7058 0.118 Uiso 1 1 calc R . .
C5 C 0.621(3) 0.1765(12) 0.8123(10) 0.102(4) Uani 1 1 d . . .
H5A H 0.4842 0.1063 0.7908 0.122 Uiso 1 1 calc R . .
H5B H 0.7342 0.1431 0.8315 0.122 Uiso 1 1 calc R . .
C6 C 0.630(3) 0.2492(13) 0.9871(10) 0.126(5) Uani 1 1 d . . .
H6A H 0.7656 0.2421 1.0159 0.152 Uiso 1 1 calc R . .
H6B H 0.5178 0.1650 0.9689 0.152 Uiso 1 1 calc R . .
C7 C 0.842(2) 0.4039(12) 0.6668(9) 0.094(3) Uani 1 1 d . . .
H7A H 0.9826 0.4673 0.6801 0.113 Uiso 1 1 calc R . .
H7B H 0.8114 0.3343 0.6020 0.113 Uiso 1 1 calc R . .
C8 C 0.6795(19) 0.4694(12) 0.6558(8) 0.076(3) Uani 1 1 d . . .
C9 C 0.4770(19) 0.4044(10) 0.5880(8) 0.077(3) Uani 1 1 d . . .
H9A H 0.4343 0.3159 0.5495 0.092 Uiso 1 1 calc R . .
C10 C 0.3390(18) 0.4702(10) 0.5774(8) 0.077(3) Uani 1 1 d . . .
H10A H 0.2031 0.4263 0.5304 0.092 Uiso 1 1 calc R . .
C11 C 0.3967(18) 0.5984(10) 0.6343(8) 0.077(3) Uani 1 1 d . . .
C12 C 0.6009(19) 0.6643(10) 0.7021(8) 0.083(3) Uani 1 1 d . . .
H12A H 0.6439 0.7526 0.7414 0.100 Uiso 1 1 calc R . .
C13 C 0.738(2) 0.5974(12) 0.7105(9) 0.084(3) Uani 1 1 d . . .
H13A H 0.8766 0.6416 0.7554 0.101 Uiso 1 1 calc R . .
C14 C 0.300(3) 0.7884(14) 0.6775(13) 0.134(6) Uani 1 1 d . . .
H14A H 0.1892 0.8193 0.6534 0.202 Uiso 1 1 calc R . .
H14B H 0.4321 0.8382 0.6702 0.202 Uiso 1 1 calc R . .
H14C H 0.3177 0.7984 0.7489 0.202 Uiso 1 1 calc R . .
O1W O 0.836(5) 0.549(3) 0.924(2) 0.047(10) Uiso 0.167(16) 1 d P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ta1 0.1015(5) 0.0673(4) 0.0803(5) 0.0117(3) 0.0053(4) 0.0341(4)
Ta2 0.0954(5) 0.0671(4) 0.0884(5) 0.0277(3) 0.0058(4) 0.0278(4)
F1 0.205(10) 0.107(6) 0.113(6) 0.021(5) 0.011(6) 0.076(7)
F2 0.200(10) 0.156(8) 0.107(6) 0.011(5) -0.009(6) 0.088(8)
F3 0.147(8) 0.155(8) 0.190(10) 0.036(7) 0.079(8) 0.045(7)
F4 0.188(10) 0.170(8) 0.117(7) 0.018(6) 0.028(7) 0.084(8)
F5 0.113(6) 0.104(5) 0.128(6) 0.043(5) -0.002(5) 0.038(4)
F6 0.132(7) 0.128(7) 0.219(11) 0.105(8) 0.022(7) 0.040(6)
O1 0.126(7) 0.084(5) 0.080(5) 0.040(4) 0.036(5) 0.045(5)
O2 0.138(8) 0.132(7) 0.076(5) 0.045(5) 0.048(5) 0.067(7)
O3 0.123(7) 0.096(6) 0.098(6) 0.039(5) 0.028(5) 0.054(5)
N1 0.097(6) 0.092(7) 0.074(6) 0.028(5) 0.029(5) 0.043(6)
C1 0.143(12) 0.122(10) 0.090(8) 0.036(8) 0.026(9) 0.089(10)
C2 0.104(9) 0.127(12) 0.085(8) 0.044(8) 0.027(8) 0.058(9)
C3 0.156(15) 0.122(12) 0.120(12) 0.051(10) 0.066(12) 0.021(11)
C4 0.123(10) 0.092(8) 0.069(6) 0.016(6) 0.006(7) 0.049(8)
C5 0.144(12) 0.073(7) 0.081(7) 0.030(6) 0.015(8) 0.037(8)
C6 0.200(16) 0.120(10) 0.107(9) 0.066(8) 0.087(11) 0.073(11)
C7 0.128(10) 0.105(8) 0.081(7) 0.048(7) 0.054(8) 0.057(8)
C8 0.086(7) 0.093(8) 0.064(6) 0.038(6) 0.027(6) 0.041(7)
C9 0.111(8) 0.071(6) 0.059(5) 0.029(5) 0.031(6) 0.037(6)
C10 0.089(7) 0.078(6) 0.076(6) 0.037(5) 0.029(6) 0.036(6)
C11 0.092(7) 0.076(6) 0.069(6) 0.032(5) 0.020(6) 0.034(6)
C12 0.106(8) 0.065(6) 0.073(6) 0.021(5) 0.022(6) 0.028(6)
C13 0.083(7) 0.080(7) 0.074(7) 0.028(6) 0.013(6) 0.012(6)
C14 0.198(18) 0.113(12) 0.124(12) 0.047(10) 0.040(13) 0.102(13)

_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
Ta1 F3 1.854(8) 2_556 ?
Ta1 F3 1.854(8) . ?
Ta1 F1 1.862(8) . ?
Ta1 F1 1.862(8) 2_556 ?
Ta1 F2 1.871(9) 2_556 ?
Ta1 F2 1.871(9) . ?
Ta2 F6 1.850(8) 2 ?
Ta2 F6 1.850(8) . ?
Ta2 F4 1.854(8) 2 ?
Ta2 F4 1.854(8) . ?
Ta2 F5 1.886(7) . ?
Ta2 F5 1.886(7) 2 ?
O1 C5 1.423(14) . ?
O1 C6 1.446(13) . ?
O2 C2 1.426(15) . ?
O2 C3 1.435(16) . ?
O3 C11 1.369(12) . ?
O3 C14 1.430(16) . ?
N1 C4 1.488(15) . ?
N1 C1 1.507(13) . ?
N1 C7 1.553(12) . ?
N1 H1N1 0.88(2) . ?
C1 C2 1.519(19) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C6 1.450(18) 2_767 ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.500(16) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C3 1.450(18) 2_767 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.500(14) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C13 1.343(16) . ?
C8 C9 1.374(15) . ?
C9 C10 1.362(13) . ?
C9 H9A 0.9300 . ?
C10 C11 1.353(13) . ?
C10 H10A 0.9300 . ?
C11 C12 1.383(14) . ?
C12 C13 1.367(15) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
F3 Ta1 F3 180.000(1) 2_556 . ?
F3 Ta1 F1 90.9(4) 2_556 . ?
F3 Ta1 F1 89.1(4) . . ?
F3 Ta1 F1 89.1(4) 2_556 2_556 ?
F3 Ta1 F1 90.9(4) . 2_556 ?
F1 Ta1 F1 180.000(2) . 2_556 ?
F3 Ta1 F2 91.3(5) 2_556 2_556 ?
F3 Ta1 F2 88.7(5) . 2_556 ?
F1 Ta1 F2 89.1(4) . 2_556 ?
F1 Ta1 F2 90.9(4) 2_556 2_556 ?
F3 Ta1 F2 88.7(5) 2_556 . ?
F3 Ta1 F2 91.3(5) . . ?
F1 Ta1 F2 90.9(4) . . ?
F1 Ta1 F2 89.1(4) 2_556 . ?
F2 Ta1 F2 180.000(2) 2_556 . ?
F6 Ta2 F6 180.0(9) 2 . ?
F6 Ta2 F4 92.3(5) 2 2 ?
F6 Ta2 F4 87.7(5) . 2 ?
F6 Ta2 F4 87.7(5) 2 . ?
F6 Ta2 F4 92.3(5) . . ?
F4 Ta2 F4 180.0(6) 2 . ?
F6 Ta2 F5 90.7(4) 2 . ?
F6 Ta2 F5 89.3(4) . . ?
F4 Ta2 F5 90.6(4) 2 . ?
F4 Ta2 F5 89.4(4) . . ?
F6 Ta2 F5 89.3(4) 2 2 ?
F6 Ta2 F5 90.7(4) . 2 ?
F4 Ta2 F5 89.4(4) 2 2 ?
F4 Ta2 F5 90.6(4) . 2 ?
F5 Ta2 F5 180.0(6) . 2 ?
C5 O1 C6 110.7(9) . . ?
C2 O2 C3 112.3(11) . . ?
C11 O3 C14 116.5(11) . . ?
C4 N1 C1 111.1(9) . . ?
C4 N1 C7 110.8(9) . . ?
C1 N1 C7 113.9(9) . . ?
C4 N1 H1N1 117(8) . . ?
C1 N1 H1N1 117(9) . . ?
C7 N1 H1N1 84(8) . . ?
N1 C1 C2 112.7(10) . . ?
N1 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
N1 C1 H1B 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
O2 C2 C1 107.8(11) . . ?
O2 C2 H2A 110.1 . . ?
C1 C2 H2A 110.1 . . ?
O2 C2 H2B 110.1 . . ?
C1 C2 H2B 110.1 . . ?
H2A C2 H2B 108.5 . . ?
O2 C3 C6 109.0(12) . 2_767 ?
O2 C3 H3A 109.9 . . ?
C6 C3 H3A 109.9 2_767 . ?
O2 C3 H3B 109.9 . . ?
C6 C3 H3B 109.9 2_767 . ?
H3A C3 H3B 108.3 . . ?
N1 C4 C5 115.7(11) . . ?
N1 C4 H4A 108.4 . . ?
C5 C4 H4A 108.4 . . ?
N1 C4 H4B 108.4 . . ?
C5 C4 H4B 108.4 . . ?
H4A C4 H4B 107.4 . . ?
O1 C5 C4 105.1(9) . . ?
O1 C5 H5A 110.7 . . ?
C4 C5 H5A 110.7 . . ?
O1 C5 H5B 110.7 . . ?
C4 C5 H5B 110.7 . . ?
H5A C5 H5B 108.8 . . ?
O1 C6 C3 109.1(11) . 2_767 ?
O1 C6 H6A 109.9 . . ?
C3 C6 H6A 109.9 2_767 . ?
O1 C6 H6B 109.9 . . ?
C3 C6 H6B 109.9 2_767 . ?
H6A C6 H6B 108.3 . . ?
C8 C7 N1 114.0(8) . . ?
C8 C7 H7A 108.8 . . ?
N1 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
N1 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C13 C8 C9 119.2(11) . . ?
C13 C8 C7 118.6(12) . . ?
C9 C8 C7 122.1(11) . . ?
C10 C9 C8 119.8(10) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C11 C10 C9 121.0(11) . . ?
C11 C10 H10A 119.5 . . ?
C9 C10 H10A 119.5 . . ?
C10 C11 O3 115.6(10) . . ?
C10 C11 C12 119.3(10) . . ?
O3 C11 C12 125.1(10) . . ?
C13 C12 C11 118.9(10) . . ?
C13 C12 H12A 120.6 . . ?
C11 C12 H12A 120.6 . . ?
C8 C13 C12 121.7(12) . . ?
C8 C13 H13A 119.1 . . ?
C12 C13 H13A 119.1 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.962
_refine_diff_density_max         0.751
_refine_diff_density_min         -1.973
_refine_diff_density_rms         0.198