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

data_global
_journal_name_full               'Dalton Trans.'

_journal_coden_Cambridge         0222

loop_
_publ_author_name
_publ_author_address
'Irina Beletskaya'
; Moscow State University, Department of Chemistry,
Vorob'evy Gory,
Moscow, 119899, Russia
;
'Galina A Artamkina'
; N.S.Kurnakov Institute of General and Inorganic Chemistry
of Russian Academy of Science, 31 Leninskii prospect,
Moscow, 119991, Russia
;
'Andrei Churakov'
; N.S.Kurnakov Institute of General and Inorganic Chemistry
of Russian Academy of Science, 31 Leninskii prospect,
Moscow, 119991, Russia
;
'Lidiya Kh Minacheva'
; N.S.Kurnakov Institute of General and Inorganic Chemistry
of Russian Academy of Science, 31 Leninskii prospect,
Moscow, 119991, Russia

;
;
Y.F.Oprunenko
;
; Moscow State University, Department of Chemistry,
Vorobevy Gory,
Moscow, 119899, Russia
;
'Petr Sazonov'
; Moscow State University, Department of Chemistry,
Vorobevy Gory,
Moscow, 119899, Russia

;
'Vladimir S Sergienko'
; Moscow State University, Department of Chemistry,
Vorobevy Gory,
Moscow, 119899, Russia
;

_publ_contact_author_name        'Irina Beletskaya'
_publ_contact_author_email       BELETSKA@ORG.CHEM.MSU.RU

_publ_section_title              
;
Lariat ethers with fluoroaryl side-arms: a study of
CF...metal cation interaction in the complexes of
N-(o-fluoroaryl)azacrown ethers
;

# Attachment 'M.CIF'

_publ_contact_author             
; Minacheva Lidiya Kh.
N.S.Kurnakov Institute of General and Inorganic Chemistry
of Russian Academy of Science, 31 Leninskii prospect,
Moscow, 119991, Russia
;

_publ_contact_letter             
; Please consider this CIF submission for deposition in CCDC
;

# Attachment 'BA5.CIF'

data_ba5
_database_code_depnum_ccdc_archive 'CCDC 681113'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
{N,N'-bis(o-fluorophenyl)diaza-18-crown-6}diperchlorato barium(II)
;
_chemical_name_common            
;(N,N'-bis(o-fluorophenyl)diaza-18-crown-6)diperchlorato
barium(ii)
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H32 Ba Cl2 F2 N2 O12'
_chemical_formula_sum            'C24 H32 Ba Cl2 F2 N2 O12'
_chemical_formula_weight         786.76

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ba Ba -0.3244 2.2819 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   8.178(3)
_cell_length_b                   12.054(3)
_cell_length_c                   15.072(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.02(3)
_cell_angle_gamma                90.00
_cell_volume                     1467.4(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    24
_cell_measurement_theta_min      12
_cell_measurement_theta_max      18

_exptl_crystal_description       block
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             788
_exptl_absorpt_coefficient_mu    1.613
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.7655
_exptl_absorpt_correction_T_max  0.8955
_exptl_absorpt_process_details   'SHELXTL (Bruker, 2001)'

_exptl_special_details           
;
The low ratio of observed/unique reflections is caused by
poor crystal quality.
;

_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  'Enraf-Nonius Cad-4'
_diffrn_measurement_method       w/
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count 98
_diffrn_standards_interval_time  7200
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6568
_diffrn_reflns_av_R_equivalents  0.0824
_diffrn_reflns_av_sigmaI/netI    0.2190
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         29.97
_reflns_number_total             4269
_reflns_number_gt                1642
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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^)+(0.0332P)^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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4269
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2164
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.0992
_refine_ls_wR_factor_gt          0.0694
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_restrained_S_all      0.949
_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
Ba1 Ba 0.0000 0.5000 0.5000 0.03215(13) Uani 1 2 d S . .
Cl1 Cl 0.15047(18) 0.73442(13) 0.37830(9) 0.0442(4) Uani 1 1 d . . .
F1 F -0.1000(4) 0.5242(2) 0.67980(19) 0.0488(9) Uani 1 1 d . . .
N1 N 0.2120(5) 0.5957(3) 0.6616(2) 0.0316(10) Uani 1 1 d . . .
O1 O -0.0785(4) 0.7097(3) 0.5652(2) 0.0367(9) Uani 1 1 d . . .
O2 O -0.3147(4) 0.5895(3) 0.4493(2) 0.0375(9) Uani 1 1 d . . .
O3 O 0.2343(5) 0.6578(3) 0.4442(2) 0.0518(11) Uani 1 1 d . . .
O4 O -0.0180(5) 0.6975(4) 0.3573(3) 0.0596(13) Uani 1 1 d . . .
O5 O 0.1574(6) 0.8427(4) 0.4149(3) 0.0767(14) Uani 1 1 d . . .
O6 O 0.2279(6) 0.7318(4) 0.3008(3) 0.0753(14) Uani 1 1 d . . .
C1 C 0.1876(6) 0.7172(4) 0.6554(3) 0.0364(13) Uani 1 1 d . . .
H1A H 0.2325 0.7444 0.6036 0.044 Uiso 1 1 calc R . .
H1B H 0.2496 0.7515 0.7084 0.044 Uiso 1 1 calc R . .
C2 C 0.0086(7) 0.7528(5) 0.6471(3) 0.0398(15) Uani 1 1 d . . .
H2A H -0.0395 0.7247 0.6975 0.048 Uiso 1 1 calc R . .
H2B H 0.0013 0.8332 0.6471 0.048 Uiso 1 1 calc R . .
C3 C -0.2508(6) 0.7379(5) 0.5540(4) 0.0441(15) Uani 1 1 d . . .
H3A H -0.2629 0.8170 0.5628 0.053 Uiso 1 1 calc R . .
H3B H -0.3031 0.6992 0.5986 0.053 Uiso 1 1 calc R . .
C4 C -0.3327(7) 0.7063(5) 0.4622(4) 0.0448(15) Uani 1 1 d . . .
H4A H -0.4492 0.7255 0.4547 0.054 Uiso 1 1 calc R . .
H4B H -0.2827 0.7468 0.4176 0.054 Uiso 1 1 calc R . .
C5 C -0.4097(8) 0.5521(5) 0.3668(4) 0.0403(16) Uani 1 1 d . . .
H5B H -0.3780 0.5933 0.3169 0.048 Uiso 1 1 calc R . .
H5C H -0.5265 0.5652 0.3678 0.048 Uiso 1 1 calc R . .
C6 C -0.3801(7) 0.4309(5) 0.3550(4) 0.0392(16) Uani 1 1 d . . .
H6B H -0.4003 0.3920 0.4085 0.047 Uiso 1 1 calc R . .
H6C H -0.4592 0.4038 0.3050 0.047 Uiso 1 1 calc R . .
C7 C 0.1770(7) 0.5527(4) 0.7458(3) 0.0351(13) Uani 1 1 d . . .
C8 C 0.2940(7) 0.5449(4) 0.8233(4) 0.0447(15) Uani 1 1 d . . .
H8A H 0.4011 0.5703 0.8222 0.054 Uiso 1 1 calc R . .
C9 C 0.2549(8) 0.5004(6) 0.9018(3) 0.0543(14) Uani 1 1 d . . .
H9A H 0.3359 0.4949 0.9523 0.065 Uiso 1 1 calc R . .
C10 C 0.0983(10) 0.4644(5) 0.9054(4) 0.0574(19) Uani 1 1 d . . .
H10A H 0.0728 0.4330 0.9579 0.069 Uiso 1 1 calc R . .
C11 C -0.0231(8) 0.4748(5) 0.8305(4) 0.055(2) Uani 1 1 d . . .
H11A H -0.1315 0.4531 0.8327 0.066 Uiso 1 1 calc R . .
C12 C 0.0198(7) 0.5172(5) 0.7539(3) 0.0409(15) Uani 1 1 d . . .

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
Ba1 0.0285(2) 0.0348(2) 0.0332(2) -0.0020(3) 0.00487(16) 0.0021(4)
Cl1 0.0389(8) 0.0500(10) 0.0426(8) 0.0013(7) 0.0030(7) 0.0015(7)
F1 0.0421(17) 0.054(3) 0.0505(17) 0.0033(15) 0.0090(15) -0.0094(17)
N1 0.027(2) 0.036(3) 0.032(2) 0.0017(19) 0.004(2) 0.001(2)
O1 0.034(2) 0.038(2) 0.040(2) -0.0076(17) 0.0099(19) 0.0055(18)
O2 0.031(2) 0.036(2) 0.044(2) 0.0004(17) 0.0008(18) 0.0039(18)
O3 0.047(3) 0.061(3) 0.047(2) 0.011(2) 0.004(2) 0.005(2)
O4 0.032(2) 0.073(3) 0.069(3) -0.021(2) -0.006(2) 0.001(2)
O5 0.078(3) 0.051(3) 0.093(3) -0.013(3) -0.011(3) -0.001(3)
O6 0.082(3) 0.095(4) 0.056(3) 0.024(2) 0.033(3) 0.000(3)
C1 0.047(4) 0.028(3) 0.033(3) 0.001(2) 0.001(3) -0.009(3)
C2 0.044(4) 0.026(3) 0.048(4) -0.006(3) 0.005(3) 0.003(3)
C3 0.031(3) 0.044(4) 0.059(4) -0.010(3) 0.014(3) 0.009(3)
C4 0.029(3) 0.043(4) 0.062(4) -0.003(3) 0.007(3) 0.006(3)
C5 0.028(3) 0.057(4) 0.036(3) 0.002(3) 0.003(3) 0.009(3)
C6 0.029(3) 0.053(4) 0.035(3) 0.000(3) 0.001(3) -0.003(3)
C7 0.048(3) 0.028(3) 0.029(3) -0.004(2) 0.004(3) 0.000(3)
C8 0.049(4) 0.041(3) 0.043(3) -0.006(3) 0.003(3) 0.002(3)
C9 0.085(4) 0.040(3) 0.035(3) -0.005(4) 0.002(3) 0.006(6)
C10 0.096(6) 0.042(4) 0.039(3) 0.004(3) 0.028(4) 0.009(4)
C11 0.067(4) 0.051(6) 0.054(3) 0.007(3) 0.030(3) 0.000(3)
C12 0.046(3) 0.036(4) 0.041(3) -0.001(3) 0.008(3) 0.001(3)

_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
Ba1 O2 2.785(3) . ?
Ba1 O2 2.785(3) 3_566 ?
Ba1 O1 2.822(3) . ?
Ba1 O1 2.822(3) 3_566 ?
Ba1 O3 2.916(4) . ?
Ba1 O3 2.916(4) 3_566 ?
Ba1 F1 2.965(3) 3_566 ?
Ba1 F1 2.965(3) . ?
Ba1 N1 2.991(4) 3_566 ?
Ba1 N1 2.991(4) . ?
Ba1 O4 3.196(5) . ?
Ba1 O4 3.196(5) 3_566 ?
Cl1 O6 1.413(4) . ?
Cl1 O5 1.414(4) . ?
Cl1 O4 1.435(4) . ?
Cl1 O3 1.448(4) . ?
F1 C12 1.368(6) . ?
N1 C7 1.440(6) . ?
N1 C6 1.471(7) 3_566 ?
N1 C1 1.479(6) . ?
O1 C2 1.424(6) . ?
O1 C3 1.433(6) . ?
O2 C4 1.433(6) . ?
O2 C5 1.431(6) . ?
C1 C2 1.511(7) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.490(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.497(7) . ?
C5 H5B 0.9700 . ?
C5 H5C 0.9700 . ?
C6 N1 1.471(7) 3_566 ?
C6 H6B 0.9700 . ?
C6 H6C 0.9700 . ?
C7 C12 1.378(7) . ?
C7 C8 1.392(7) . ?
C8 C9 1.381(7) . ?
C8 H8A 0.9300 . ?
C9 C10 1.361(8) . ?
C9 H9A 0.9300 . ?
C10 C11 1.387(8) . ?
C10 H10A 0.9300 . ?
C11 C12 1.358(7) . ?
C11 H11A 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
O2 Ba1 O2 180.000(1) . 3_566 ?
O2 Ba1 O1 59.85(10) . . ?
O2 Ba1 O1 120.15(10) 3_566 . ?
O2 Ba1 O1 120.15(10) . 3_566 ?
O2 Ba1 O1 59.85(10) 3_566 3_566 ?
O1 Ba1 O1 180.0 . 3_566 ?
O2 Ba1 O3 106.80(11) . . ?
O2 Ba1 O3 73.20(11) 3_566 . ?
O1 Ba1 O3 73.26(11) . . ?
O1 Ba1 O3 106.74(11) 3_566 . ?
O2 Ba1 O3 73.20(11) . 3_566 ?
O2 Ba1 O3 106.80(11) 3_566 3_566 ?
O1 Ba1 O3 106.74(11) . 3_566 ?
O1 Ba1 O3 73.26(11) 3_566 3_566 ?
O3 Ba1 O3 180.0 . 3_566 ?
O2 Ba1 F1 99.36(9) . 3_566 ?
O2 Ba1 F1 80.64(9) 3_566 3_566 ?
O1 Ba1 F1 121.11(9) . 3_566 ?
O1 Ba1 F1 58.89(9) 3_566 3_566 ?
O3 Ba1 F1 60.83(9) . 3_566 ?
O3 Ba1 F1 119.17(9) 3_566 3_566 ?
O2 Ba1 F1 80.64(9) . . ?
O2 Ba1 F1 99.36(9) 3_566 . ?
O1 Ba1 F1 58.89(9) . . ?
O1 Ba1 F1 121.11(9) 3_566 . ?
O3 Ba1 F1 119.17(9) . . ?
O3 Ba1 F1 60.83(9) 3_566 . ?
F1 Ba1 F1 180.000(1) 3_566 . ?
O2 Ba1 N1 62.17(11) . 3_566 ?
O2 Ba1 N1 117.83(11) 3_566 3_566 ?
O1 Ba1 N1 119.65(10) . 3_566 ?
O1 Ba1 N1 60.35(10) 3_566 3_566 ?
O3 Ba1 N1 109.86(11) . 3_566 ?
O3 Ba1 N1 70.14(11) 3_566 3_566 ?
F1 Ba1 N1 54.93(9) 3_566 3_566 ?
F1 Ba1 N1 125.07(10) . 3_566 ?
O2 Ba1 N1 117.83(11) . . ?
O2 Ba1 N1 62.17(11) 3_566 . ?
O1 Ba1 N1 60.35(10) . . ?
O1 Ba1 N1 119.65(10) 3_566 . ?
O3 Ba1 N1 70.14(11) . . ?
O3 Ba1 N1 109.86(11) 3_566 . ?
F1 Ba1 N1 125.07(10) 3_566 . ?
F1 Ba1 N1 54.93(10) . . ?
N1 Ba1 N1 180.000(1) 3_566 . ?
O2 Ba1 O4 65.40(10) . . ?
O2 Ba1 O4 114.60(10) 3_566 . ?
O1 Ba1 O4 65.06(10) . . ?
O1 Ba1 O4 114.94(10) 3_566 . ?
O3 Ba1 O4 44.20(10) . . ?
O3 Ba1 O4 135.80(11) 3_566 . ?
F1 Ba1 O4 56.52(9) 3_566 . ?
F1 Ba1 O4 123.48(9) . . ?
N1 Ba1 O4 77.27(10) 3_566 . ?
N1 Ba1 O4 102.73(10) . . ?
O2 Ba1 O4 114.60(10) . 3_566 ?
O2 Ba1 O4 65.40(10) 3_566 3_566 ?
O1 Ba1 O4 114.94(10) . 3_566 ?
O1 Ba1 O4 65.06(10) 3_566 3_566 ?
O3 Ba1 O4 135.80(11) . 3_566 ?
O3 Ba1 O4 44.20(10) 3_566 3_566 ?
F1 Ba1 O4 123.48(9) 3_566 3_566 ?
F1 Ba1 O4 56.52(9) . 3_566 ?
N1 Ba1 O4 102.73(10) 3_566 3_566 ?
N1 Ba1 O4 77.27(10) . 3_566 ?
O4 Ba1 O4 180.000(1) . 3_566 ?
O6 Cl1 O5 110.3(3) . . ?
O6 Cl1 O4 110.5(3) . . ?
O5 Cl1 O4 110.5(3) . . ?
O6 Cl1 O3 109.1(2) . . ?
O5 Cl1 O3 109.6(3) . . ?
O4 Cl1 O3 106.8(3) . . ?
C12 F1 Ba1 118.4(3) . . ?
C7 N1 C6 113.0(4) . 3_566 ?
C7 N1 C1 111.7(4) . . ?
C6 N1 C1 109.0(4) 3_566 . ?
C7 N1 Ba1 114.1(3) . . ?
C6 N1 Ba1 102.4(3) 3_566 . ?
C1 N1 Ba1 106.0(3) . . ?
C2 O1 C3 111.4(4) . . ?
C2 O1 Ba1 121.3(3) . . ?
C3 O1 Ba1 116.4(3) . . ?
C4 O2 C5 111.9(4) . . ?
C4 O2 Ba1 117.0(3) . . ?
C5 O2 Ba1 118.0(3) . . ?
Cl1 O3 Ba1 110.6(2) . . ?
Cl1 O4 Ba1 98.1(2) . . ?
N1 C1 C2 113.9(4) . . ?
N1 C1 H1A 108.8 . . ?
C2 C1 H1A 108.8 . . ?
N1 C1 H1B 108.8 . . ?
C2 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
O1 C2 C1 108.3(4) . . ?
O1 C2 H2A 110.0 . . ?
C1 C2 H2A 110.0 . . ?
O1 C2 H2B 110.0 . . ?
C1 C2 H2B 110.0 . . ?
H2A C2 H2B 108.4 . . ?
O1 C3 C4 109.8(4) . . ?
O1 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
O1 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
O2 C4 C3 109.7(4) . . ?
O2 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
O2 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
O2 C5 C6 109.5(5) . . ?
O2 C5 H5B 109.8 . . ?
C6 C5 H5B 109.8 . . ?
O2 C5 H5C 109.8 . . ?
C6 C5 H5C 109.8 . . ?
H5B C5 H5C 108.2 . . ?
N1 C6 C5 114.0(5) 3_566 . ?
N1 C6 H6B 108.7 3_566 . ?
C5 C6 H6B 108.7 . . ?
N1 C6 H6C 108.7 3_566 . ?
C5 C6 H6C 108.7 . . ?
H6B C6 H6C 107.6 . . ?
C12 C7 C8 115.6(5) . . ?
C12 C7 N1 120.5(5) . . ?
C8 C7 N1 123.9(5) . . ?
C9 C8 C7 121.6(5) . . ?
C9 C8 H8A 119.2 . . ?
C7 C8 H8A 119.2 . . ?
C10 C9 C8 120.2(5) . . ?
C10 C9 H9A 119.9 . . ?
C8 C9 H9A 119.9 . . ?
C9 C10 C11 119.8(5) . . ?
C9 C10 H10A 120.1 . . ?
C11 C10 H10A 120.1 . . ?
C12 C11 C10 118.6(6) . . ?
C12 C11 H11A 120.7 . . ?
C10 C11 H11A 120.7 . . ?
C11 C12 F1 118.0(5) . . ?
C11 C12 C7 124.2(5) . . ?
F1 C12 C7 117.8(5) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        29.97
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.786
_refine_diff_density_min         -1.585
_refine_diff_density_rms         0.143

data_m
_database_code_depnum_ccdc_archive 'CCDC 681114'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
aqua{N,N'-bis(o-fluorophenyl)diaza-18-crown-6}lead(II)diperchlorate
;
_chemical_name_common            
;aqua(N,N'-bis(o-fluorophenyl)diaza-18-crown-
6)lead(ii)diperchlorate
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H34 F2 N2 O5 Pb, 2(Cl O4)'
_chemical_formula_sum            'C24 H34 Cl2 F2 N2 O13 Pb'
_chemical_formula_weight         874.62

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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                   19.423(5)
_cell_length_b                   12.719(3)
_cell_length_c                   13.109(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.711(3)
_cell_angle_gamma                90.00
_cell_volume                     3227.4(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    303(2)
_cell_measurement_reflns_used    1649
_cell_measurement_theta_min      3.118
_cell_measurement_theta_max      18.465

_exptl_crystal_description       needle
_exptl_crystal_colour            light-brown
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.800
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1720
_exptl_absorpt_coefficient_mu    5.468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2184
_exptl_absorpt_correction_T_max  0.8985
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      303(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 SMART APEX II'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12378
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_av_sigmaI/netI    0.0609
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3154
_reflns_number_gt                2435
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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^)+(0.1326P)^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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3154
_refine_ls_number_parameters     181
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0679
_refine_ls_wR_factor_ref         0.1967
_refine_ls_wR_factor_gt          0.1773
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.015
_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
Pb1 Pb 0.5000 0.23665(4) 0.2500 0.0545(3) Uani 1 2 d S . .
Cl1 Cl 0.34062(17) 0.1350(3) -0.2676(3) 0.0818(9) Uani 1 1 d D . .
O11 O 0.3139(9) 0.1374(17) -0.3625(12) 0.209(8) Uiso 1 1 d D . .
O12 O 0.4006(8) 0.0972(18) -0.2462(19) 0.35(2) Uani 1 1 d D . .
O13 O 0.3437(15) 0.2422(13) -0.238(2) 0.228(15) Uiso 1 1 d D . .
O14 O 0.2927(7) 0.0943(12) -0.2048(9) 0.156(6) Uani 1 1 d D . .
N1 N 0.4317(6) 0.2863(9) 0.0559(8) 0.071(3) Uani 1 1 d . . .
O1 O 0.3710(4) 0.1748(7) 0.2183(7) 0.072(2) Uani 1 1 d . . .
O2 O 0.4279(5) 0.2102(8) 0.4101(7) 0.081(3) Uani 1 1 d . . .
O3 O 0.5015(10) 0.0476(11) 0.2762(10) 0.061(4) Uiso 0.50 1 d P . .
H1 H 0.4715 -0.0010 0.2769 0.06(6) Uiso 0.50 1 d PR . .
H2 H 0.5297 0.0004 0.2602 0.05(6) Uiso 0.50 1 d PR . .
C1 C 0.3800(8) 0.1970(12) 0.0387(11) 0.083(4) Uani 1 1 d . . .
H1A H 0.3528 0.2074 -0.0259 0.100 Uiso 1 1 calc R . .
H1B H 0.4046 0.1309 0.0351 0.100 Uiso 1 1 calc R . .
C2 C 0.3324(6) 0.1920(12) 0.1246(12) 0.083(4) Uani 1 1 d . . .
H2A H 0.3069 0.2574 0.1275 0.100 Uiso 1 1 calc R . .
H2B H 0.2993 0.1354 0.1116 0.100 Uiso 1 1 calc R . .
C3 C 0.3289(6) 0.1765(13) 0.3029(12) 0.088(4) Uani 1 1 d . . .
H3B H 0.2901 0.1289 0.2897 0.106 Uiso 1 1 calc R . .
H3C H 0.3108 0.2468 0.3114 0.106 Uiso 1 1 calc R . .
C4 C 0.3702(7) 0.1444(14) 0.3966(11) 0.091(4) Uani 1 1 d . . .
H4A H 0.3428 0.1500 0.4550 0.109 Uiso 1 1 calc R . .
H4B H 0.3848 0.0719 0.3908 0.109 Uiso 1 1 calc R . .
C5 C 0.4693(12) 0.2045(16) 0.5064(12) 0.105(6) Uani 1 1 d . . .
H5A H 0.4391 0.2100 0.5616 0.126 Uiso 1 1 calc R . .
H5B H 0.4915 0.1362 0.5118 0.126 Uiso 1 1 calc R . .
C6 C 0.5146(10) 0.2742(18) 0.5181(15) 0.106(7) Uani 1 1 d . . .
H6A H 0.5387 0.2634 0.5851 0.127 Uiso 1 1 calc R . .
H6B H 0.4908 0.3410 0.5206 0.127 Uiso 1 1 calc R . .
C7 C 0.3934(4) 0.3843(6) 0.0440(6) 0.066(3) Uani 1 1 d G . .
C8 C 0.3607(5) 0.4156(8) -0.0493(6) 0.094(4) Uani 1 1 d G . .
H8 H 0.3611 0.3718 -0.1061 0.113 Uiso 1 1 calc R . .
C9 C 0.3274(5) 0.5123(9) -0.0578(8) 0.122(6) Uani 1 1 d G . .
H9 H 0.3056 0.5333 -0.1203 0.147 Uiso 1 1 calc R . .
C10 C 0.3268(6) 0.5778(7) 0.0270(10) 0.114(6) Uani 1 1 d G . .
H10 H 0.3046 0.6425 0.0213 0.137 Uiso 1 1 calc R . .
C11 C 0.3595(6) 0.5464(7) 0.1204(8) 0.130(7) Uani 1 1 d G . .
H11 H 0.3591 0.5902 0.1772 0.156 Uiso 1 1 calc R . .
C12 C 0.3928(5) 0.4497(7) 0.1289(6) 0.087(4) Uani 1 1 d G . .
F1 F 0.4206(6) 0.4200(8) 0.2208(5) 0.124(4) Uani 1 1 d . . .

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
Pb1 0.0465(4) 0.0538(4) 0.0630(4) 0.000 0.0034(3) 0.000
Cl1 0.0706(19) 0.070(2) 0.104(2) -0.0079(17) 0.0044(17) 0.0016(14)
O12 0.168(16) 0.22(2) 0.70(6) 0.19(3) 0.23(3) 0.120(17)
O14 0.149(11) 0.179(15) 0.150(11) 0.057(10) 0.083(9) 0.020(10)
N1 0.079(7) 0.076(7) 0.058(6) -0.005(5) 0.009(5) 0.012(6)
O1 0.042(4) 0.064(5) 0.110(7) -0.004(4) 0.006(4) -0.006(3)
O2 0.075(6) 0.089(6) 0.083(6) -0.007(5) 0.026(5) -0.017(5)
C1 0.102(11) 0.067(8) 0.078(9) -0.006(7) -0.005(8) -0.007(8)
C2 0.060(7) 0.071(8) 0.113(11) -0.009(8) -0.021(7) -0.008(6)
C3 0.049(7) 0.089(10) 0.127(12) -0.018(9) 0.018(8) -0.008(6)
C4 0.071(8) 0.116(12) 0.088(9) -0.009(8) 0.026(7) -0.028(8)
C5 0.138(17) 0.108(13) 0.064(9) -0.006(9) -0.015(10) 0.037(13)
C6 0.077(11) 0.165(19) 0.079(11) 0.052(11) 0.026(9) -0.001(10)
C7 0.056(7) 0.069(7) 0.072(7) 0.000(6) -0.005(6) 0.005(5)
C8 0.092(10) 0.109(12) 0.079(9) 0.007(8) -0.014(8) 0.017(9)
C9 0.095(11) 0.113(15) 0.153(16) 0.050(13) -0.026(11) 0.020(10)
C10 0.087(10) 0.081(11) 0.169(17) 0.043(12) -0.027(11) 0.014(8)
C11 0.178(19) 0.064(10) 0.153(16) 0.002(10) 0.046(14) 0.043(11)
C12 0.085(9) 0.065(8) 0.111(11) 0.003(7) 0.009(8) 0.026(7)
F1 0.199(10) 0.106(7) 0.063(5) -0.017(4) -0.015(5) 0.080(7)

_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
Pb1 O3 2.429(14) . ?
Pb1 O3 2.429(14) 2_655 ?
Pb1 O1 2.626(7) . ?
Pb1 O1 2.626(7) 2_655 ?
Pb1 O2 2.639(9) . ?
Pb1 O2 2.639(9) 2_655 ?
Cl1 O12 1.270(14) . ?
Cl1 O11 1.307(14) . ?
Cl1 O14 1.392(10) . ?
Cl1 O13 1.417(15) . ?
N1 C7 1.453(13) . ?
N1 C6 1.49(2) 2_655 ?
N1 C1 1.519(19) . ?
O1 C2 1.404(15) . ?
O1 C3 1.432(15) . ?
O2 C4 1.398(15) . ?
O2 C5 1.442(18) . ?
O3 O3 0.68(2) 2_655 ?
O3 H1 0.8501 . ?
O3 H2 0.8499 . ?
C1 C2 1.52(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.47(2) . ?
C3 H3B 0.9700 . ?
C3 H3C 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.25(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 N1 1.49(2) 2_655 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.3900 . ?
C7 C12 1.3900 . ?
C8 C9 1.3900 . ?
C8 H8 0.9300 . ?
C9 C10 1.3900 . ?
C9 H9 0.9300 . ?
C10 C11 1.3900 . ?
C10 H10 0.9300 . ?
C11 C12 1.3900 . ?
C11 H11 0.9300 . ?
C12 F1 1.334(9) . ?

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
O3 Pb1 O3 16.2(6) . 2_655 ?
O3 Pb1 O1 74.1(5) . . ?
O3 Pb1 O1 71.4(5) 2_655 . ?
O3 Pb1 O1 71.4(5) . 2_655 ?
O3 Pb1 O1 74.1(5) 2_655 2_655 ?
O1 Pb1 O1 145.2(4) . 2_655 ?
O3 Pb1 O2 76.2(4) . . ?
O3 Pb1 O2 89.1(4) 2_655 . ?
O1 Pb1 O2 61.7(3) . . ?
O1 Pb1 O2 113.4(3) 2_655 . ?
O3 Pb1 O2 89.1(4) . 2_655 ?
O3 Pb1 O2 76.2(4) 2_655 2_655 ?
O1 Pb1 O2 113.4(3) . 2_655 ?
O1 Pb1 O2 61.7(3) 2_655 2_655 ?
O2 Pb1 O2 165.3(5) . 2_655 ?
O12 Cl1 O11 120.3(12) . . ?
O12 Cl1 O14 111.9(10) . . ?
O11 Cl1 O14 109.8(10) . . ?
O12 Cl1 O13 106.7(13) . . ?
O11 Cl1 O13 103.9(11) . . ?
O14 Cl1 O13 102.3(11) . . ?
C7 N1 C6 113.5(12) . 2_655 ?
C7 N1 C1 107.4(11) . . ?
C6 N1 C1 108.4(12) 2_655 . ?
C2 O1 C3 112.1(10) . . ?
C2 O1 Pb1 121.8(7) . . ?
C3 O1 Pb1 118.2(7) . . ?
C4 O2 C5 117.7(13) . . ?
C4 O2 Pb1 116.6(8) . . ?
C5 O2 Pb1 114.1(10) . . ?
O3 O3 Pb1 81.9(3) 2_655 . ?
O3 O3 H1 90.5 2_655 . ?
Pb1 O3 H1 136.2 . . ?
O3 O3 H2 76.0 2_655 . ?
Pb1 O3 H2 131.7 . . ?
H1 O3 H2 86.9 . . ?
C2 C1 N1 111.0(11) . . ?
C2 C1 H1A 109.4 . . ?
N1 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
N1 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
O1 C2 C1 110.0(10) . . ?
O1 C2 H2A 109.7 . . ?
C1 C2 H2A 109.7 . . ?
O1 C2 H2B 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
O1 C3 C4 109.6(10) . . ?
O1 C3 H3B 109.8 . . ?
C4 C3 H3B 109.8 . . ?
O1 C3 H3C 109.8 . . ?
C4 C3 H3C 109.8 . . ?
H3B C3 H3C 108.2 . . ?
O2 C4 C3 108.5(12) . . ?
O2 C4 H4A 110.0 . . ?
C3 C4 H4A 110.0 . . ?
O2 C4 H4B 110.0 . . ?
C3 C4 H4B 110.0 . . ?
H4A C4 H4B 108.4 . . ?
C6 C5 O2 114.1(18) . . ?
C6 C5 H5A 108.7 . . ?
O2 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
O2 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C5 C6 N1 121(2) . 2_655 ?
C5 C6 H6A 107.0 . . ?
N1 C6 H6A 107.0 2_655 . ?
C5 C6 H6B 107.0 . . ?
N1 C6 H6B 107.0 2_655 . ?
H6A C6 H6B 106.8 . . ?
C8 C7 C12 120.0 . . ?
C8 C7 N1 122.2(7) . . ?
C12 C7 N1 117.8(7) . . ?
C9 C8 C7 120.0 . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C11 120.0 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
F1 C12 C11 118.3(7) . . ?
F1 C12 C7 121.6(7) . . ?
C11 C12 C7 120.0 . . ?

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 H2 O12 0.85 1.86 2.70(2) 170.4 5_655
O3 H1 O12 0.85 1.85 2.69(2) 169.0 6_556

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         2.977
_refine_diff_density_min         -1.006
_refine_diff_density_rms         0.193