#------------------------------------------------------------------------------
#$Date: 2016-03-24 17:12:39 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179681 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/03/7000399.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7000399
loop_
_publ_author_name
'Sazonov, Petr K.'
'Minacheva, Lidiya Kh.'
'Churakov, Andrei V.'
'Sergienko, Vladimir S.'
'Artamkina, Galina A.'
'Oprunenko, Yuri F.'
'Beletskaya, Irina P.'
_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
;
_journal_issue                   5
_journal_name_full               'Dalton Transactions'
_journal_page_first              843
_journal_page_last               850
_journal_paper_doi               10.1039/b807199c
_journal_year                    2009
_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
_chemical_name_common
;aqua(N,N'-bis(o-fluorophenyl)diaza-18-crown-
6)lead(ii)diperchlorate
;
_chemical_name_systematic
;
aqua{N,N'-bis(o-fluorophenyl)diaza-18-crown-6}lead(II)diperchlorate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.711(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.423(5)
_cell_length_b                   12.719(3)
_cell_length_c                   13.109(3)
_cell_measurement_reflns_used    1649
_cell_measurement_temperature    303(2)
_cell_measurement_theta_max      18.465
_cell_measurement_theta_min      3.118
_cell_volume                     3227.5(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      303(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_av_sigmaI/netI    0.0609
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12378
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.12
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.468
_exptl_absorpt_correction_T_max  0.8985
_exptl_absorpt_correction_T_min  0.2184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_crystal_colour            light-brown
_exptl_crystal_density_diffrn    1.800
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1720
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         2.977
_refine_diff_density_min         -1.006
_refine_diff_density_rms         0.193
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3154
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0679
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1326P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1773
_refine_ls_wR_factor_ref         0.1967
_reflns_number_gt                2435
_reflns_number_total             3154
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b807199c.txt
_cod_data_source_block           m
_cod_original_cell_volume        3227.4(14)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7000399
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'
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_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'
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_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_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
