#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:29:24 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180476 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/45/7214539.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_7214539
loop_
_publ_author_name
'Banerjee, Subhabrata'
'Dastidar, Parthasarathi'
_publ_section_title
;
 Studying fluorous interactions in a series of coordination compounds
 derived from mono-pyridyl ligands equipped with hydrogen bonding
 functionality: exploiting anion⋯\pF interaction in separating
 ClO4− anion from a competing mixture of anions
;
_journal_issue                   45
_journal_name_full               CrystEngComm
_journal_page_first              9415
_journal_paper_doi               10.1039/c3ce40359a
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C96 H48 Cl4 Cu2 F40 N16 O12'
_chemical_formula_weight         2646.32
_chemical_name_systematic
;
?
;
_space_group_IT_number           85
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-P 4a'
_symmetry_space_group_name_H-M   'P 4/n :2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   22.2079(12)
_cell_length_b                   22.2079(12)
_cell_length_c                   11.9119(13)
_cell_measurement_temperature    100(2)
_cell_volume                     5874.8(8)
_computing_cell_refinement       'Bruker Apex II'
_computing_data_collection       'Bruker Apex II'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Mercury 2.3'
_computing_publication_material  Shelxl-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Apex II'
_diffrn_measurement_method       'Omega scan'
_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  0.0814
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            55537
_diffrn_reflns_theta_full        25.80
_diffrn_reflns_theta_max         25.80
_diffrn_reflns_theta_min         1.30
_exptl_absorpt_coefficient_mu    0.578
_exptl_absorpt_correction_T_max  0.9032
_exptl_absorpt_correction_T_min  0.8278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2620
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.18
_platon_squeeze_details
;
;
_refine_diff_density_max         2.118
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         5650
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1122
_refine_ls_R_factor_gt           0.0982
_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)+(0.1501P)²+44.7474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2629
_refine_ls_wR_factor_ref         0.2771
_reflns_number_gt                4823
_reflns_number_total             5650
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce40359a.txt
_cod_data_source_block           sb56_0m
_cod_original_sg_symbol_H-M      P4/n
_cod_database_code               7214539
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y+1/2, x, z'
'y, -x+1/2, z'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y-1/2, -x, -z'
'-y, x-1/2, -z'
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
Cu1 Cu 0.2500 0.2500 0.87212(13) 0.0211(4) Uani 1 4 d S
Cu2 Cu 0.2500 0.2500 0.41649(12) 0.0201(4) Uani 1 4 d S
Cl1 Cl 0.2500 0.2500 0.6542(2) 0.0201(6) Uani 1 4 d S
Cl2 Cl 0.2500 0.2500 0.1978(2) 0.0243(6) Uani 1 4 d S
Cl3 Cl 0.59752(15) 0.32454(16) 0.5367(3) 0.0348(7) Uani 0.50 1 d P
F1 F -0.07009(19) -0.00984(18) 1.0716(4) 0.0443(11) Uani 1 1 d .
F2 F -0.1835(2) -0.0468(2) 1.0300(5) 0.0583(14) Uani 1 1 d .
F3 F -0.2629(2) 0.0290(2) 0.9297(5) 0.0563(13) Uani 1 1 d .
F4 F -0.23003(19) 0.1432(2) 0.8808(5) 0.0580(14) Uani 1 1 d .
F5 F -0.11670(18) 0.17987(18) 0.9194(4) 0.0450(11) Uani 1 1 d .
F6 F 0.59475(19) 0.34805(19) 0.2638(4) 0.0418(10) Uani 1 1 d .
F7 F 0.7086(2) 0.3730(3) 0.2145(5) 0.0646(15) Uani 1 1 d .
F8 F 0.7540(2) 0.4847(3) 0.2588(5) 0.0783(19) Uani 1 1 d .
F9 F 0.6839(2) 0.5694(2) 0.3538(5) 0.0698(17) Uani 1 1 d .
F10 F 0.5688(2) 0.5457(2) 0.4027(4) 0.0510(12) Uani 1 1 d .
N1 N 0.1723(2) 0.2045(2) 0.8906(4) 0.0221(10) Uani 1 1 d .
C2 C 0.1481(3) 0.1975(3) 0.9921(6) 0.0286(14) Uani 1 1 d .
H2 H 0.1696 0.2115 1.0537 0.034 Uiso 1 1 calc R
C3 C 0.0922(3) 0.1703(3) 1.0118(5) 0.0265(13) Uani 1 1 d .
H3 H 0.0772 0.1667 1.0843 0.032 Uiso 1 1 calc R
C4 C 0.0597(3) 0.1489(3) 0.9202(5) 0.0243(13) Uani 1 1 d .
C5 C 0.0865(3) 0.1547(3) 0.8140(6) 0.0288(14) Uani 1 1 d .
H5 H 0.0668 0.1403 0.7506 0.035 Uiso 1 1 calc R
C6 C 0.1414(3) 0.1816(3) 0.8041(5) 0.0255(13) Uani 1 1 d .
H6 H 0.1584 0.1841 0.7329 0.031 Uiso 1 1 calc R
N7 N 0.0027(2) 0.1247(2) 0.9266(5) 0.0254(11) Uani 1 1 d .
H7 H -0.0167 0.1213 0.8644 0.030 Uiso 1 1 calc R
C8 C -0.0260(3) 0.1056(3) 1.0198(5) 0.0270(13) Uani 1 1 d .
O9 O -0.0045(2) 0.1029(2) 1.1130(4) 0.0356(11) Uani 1 1 d .
C10 C -0.0898(3) 0.0857(3) 0.9978(6) 0.0303(14) Uani 1 1 d .
C11 C -0.1085(3) 0.0290(3) 1.0246(6) 0.0326(15) Uani 1 1 d .
C12 C -0.1665(3) 0.0090(3) 1.0027(7) 0.0392(17) Uani 1 1 d .
C13 C -0.2077(3) 0.0471(3) 0.9544(7) 0.0393(17) Uani 1 1 d .
C14 C -0.1903(3) 0.1053(3) 0.9275(7) 0.0386(16) Uani 1 1 d .
C15 C -0.1323(3) 0.1237(3) 0.9485(6) 0.0334(15) Uani 1 1 d .
N16 N 0.3281(2) 0.2986(2) 0.4190(4) 0.0211(10) Uani 1 1 d .
C17 C 0.3730(3) 0.2851(3) 0.4903(5) 0.0260(13) Uani 1 1 d .
H17 H 0.3663 0.2558 0.5445 0.031 Uiso 1 1 calc R
C18 C 0.4289(3) 0.3128(3) 0.4869(5) 0.0274(13) Uani 1 1 d .
H18 H 0.4587 0.3020 0.5379 0.033 Uiso 1 1 calc R
C19 C 0.4399(3) 0.3570(3) 0.4060(5) 0.0256(13) Uani 1 1 d .
C20 C 0.3925(3) 0.3724(3) 0.3338(5) 0.0281(13) Uani 1 1 d .
H20 H 0.3972 0.4029 0.2810 0.034 Uiso 1 1 calc R
C21 C 0.3389(3) 0.3414(3) 0.3426(5) 0.0252(13) Uani 1 1 d .
H21 H 0.3083 0.3509 0.2922 0.030 Uiso 1 1 calc R
N22 N 0.4968(2) 0.3817(2) 0.3993(5) 0.0301(12) Uani 1 1 d .
H22 H 0.5258 0.3612 0.4277 0.036 Uiso 1 1 calc R
C23 C 0.5111(3) 0.4354(3) 0.3522(6) 0.0312(15) Uani 1 1 d .
O24 O 0.4737(2) 0.4737(2) 0.3249(5) 0.0382(12) Uani 1 1 d .
C25 C 0.5768(3) 0.4461(3) 0.3352(6) 0.0312(15) Uani 1 1 d .
C26 C 0.6149(3) 0.4040(3) 0.2884(6) 0.0323(15) Uani 1 1 d .
C27 C 0.6742(3) 0.4159(4) 0.2627(7) 0.0430(18) Uani 1 1 d .
C28 C 0.6966(3) 0.4722(5) 0.2842(8) 0.053(2) Uani 1 1 d .
C29 C 0.6612(4) 0.5155(4) 0.3314(7) 0.047(2) Uani 1 1 d .
C30 C 0.6016(3) 0.5022(3) 0.3554(7) 0.0400(17) Uani 1 1 d .
O31 O -0.0482(3) 0.0976(3) 0.7227(5) 0.0520(15) 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'
Cu Cu 0.3201 1.2651 '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
N1 Cu1 N1 89.32(3) 2 4
N1 Cu1 N1 89.32(3) 2 3
N1 Cu1 N1 167.5(3) 4 3
N1 Cu1 N1 167.5(3) 2 .
N1 Cu1 N1 89.32(3) 4 .
N1 Cu1 N1 89.32(3) 3 .
N1 Cu1 Cl1 96.27(15) 2 .
N1 Cu1 Cl1 96.27(15) 4 .
N1 Cu1 Cl1 96.27(15) 3 .
N1 Cu1 Cl1 96.27(15) . .
N16 Cu2 N16 89.987(5) . 3
N16 Cu2 N16 89.989(5) . 4
N16 Cu2 N16 178.3(3) 3 4
N16 Cu2 N16 178.3(3) . 2
N16 Cu2 N16 89.988(5) 3 2
N16 Cu2 N16 89.987(5) 4 2
N16 Cu2 Cl2 90.83(14) . .
N16 Cu2 Cl2 90.83(14) 3 .
N16 Cu2 Cl2 90.83(14) 4 .
N16 Cu2 Cl2 90.83(14) 2 .
C2 N1 C6 116.5(5) . .
C2 N1 Cu1 120.3(4) . .
C6 N1 Cu1 123.2(4) . .
N1 C2 C3 124.1(6) . .
N1 C2 H2 117.9 . .
C3 C2 H2 117.9 . .
C4 C3 C2 118.4(6) . .
C4 C3 H3 120.8 . .
C2 C3 H3 120.8 . .
N7 C4 C3 124.6(6) . .
N7 C4 C5 118.3(6) . .
C3 C4 C5 117.1(6) . .
C6 C5 C4 119.8(6) . .
C6 C5 H5 120.1 . .
C4 C5 H5 120.1 . .
N1 C6 C5 124.0(6) . .
N1 C6 H6 118.0 . .
C5 C6 H6 118.0 . .
C8 N7 C4 127.0(6) . .
C8 N7 H7 116.5 . .
C4 N7 H7 116.5 . .
O9 C8 N7 125.8(6) . .
O9 C8 C10 121.1(6) . .
N7 C8 C10 113.1(6) . .
C11 C10 C15 116.8(6) . .
C11 C10 C8 121.1(6) . .
C15 C10 C8 122.2(6) . .
F1 C11 C10 119.9(6) . .
F1 C11 C12 117.7(6) . .
C10 C11 C12 122.3(6) . .
F2 C12 C13 119.0(6) . .
F2 C12 C11 120.9(7) . .
C13 C12 C11 120.1(6) . .
F3 C13 C12 121.6(6) . .
F3 C13 C14 119.3(7) . .
C12 C13 C14 119.1(6) . .
F4 C14 C15 120.3(6) . .
F4 C14 C13 119.9(6) . .
C15 C14 C13 119.8(7) . .
F5 C15 C14 118.2(6) . .
F5 C15 C10 119.8(6) . .
C14 C15 C10 122.0(6) . .
C21 N16 C17 117.1(5) . .
C21 N16 Cu2 121.1(4) . .
C17 N16 Cu2 121.4(4) . .
N16 C17 C18 123.2(6) . .
N16 C17 H17 118.4 . .
C18 C17 H17 118.4 . .
C17 C18 C19 119.2(6) . .
C17 C18 H18 120.4 . .
C19 C18 H18 120.4 . .
N22 C19 C18 118.7(6) . .
N22 C19 C20 123.6(6) . .
C18 C19 C20 117.6(6) . .
C21 C20 C19 118.7(6) . .
C21 C20 H20 120.7 . .
C19 C20 H20 120.7 . .
N16 C21 C20 124.1(6) . .
N16 C21 H21 118.0 . .
C20 C21 H21 118.0 . .
C23 N22 C19 126.1(6) . .
C23 N22 H22 116.9 . .
C19 N22 H22 116.9 . .
O24 C23 N22 123.9(6) . .
O24 C23 C25 120.9(6) . .
N22 C23 C25 115.2(6) . .
C26 C25 C30 116.0(6) . .
C26 C25 C23 123.1(6) . .
C30 C25 C23 120.6(7) . .
F6 C26 C25 120.6(6) . .
F6 C26 C27 116.3(7) . .
C25 C26 C27 123.0(7) . .
F7 C27 C28 121.2(7) . .
F7 C27 C26 120.1(7) . .
C28 C27 C26 118.7(8) . .
F8 C28 C29 119.7(8) . .
F8 C28 C27 119.5(9) . .
C29 C28 C27 120.7(7) . .
F9 C29 C28 120.0(8) . .
F9 C29 C30 121.0(9) . .
C28 C29 C30 119.0(7) . .
F10 C30 C25 120.5(7) . .
F10 C30 C29 117.0(7) . .
C25 C30 C29 122.5(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 2.012(5) 2
Cu1 N1 2.012(5) 4
Cu1 N1 2.012(5) 3
Cu1 N1 2.012(5) .
Cu1 Cl1 2.596(3) .
Cu2 N16 2.043(5) .
Cu2 N16 2.043(5) 3
Cu2 N16 2.043(5) 4
Cu2 N16 2.043(5) 2
Cu2 Cl2 2.605(3) .
Cl3 Cl3 0.000(9) 1
F1 C11 1.336(8) .
F2 C12 1.336(8) .
F3 C13 1.324(8) .
F4 C14 1.341(8) .
F5 C15 1.339(8) .
F6 C26 1.351(8) .
F7 C27 1.348(10) .
F8 C28 1.340(9) .
F9 C29 1.327(9) .
F10 C30 1.336(9) .
N1 C2 1.332(8) .
N1 C6 1.339(8) .
C2 C3 1.399(9) .
C2 H2 0.9300 .
C3 C4 1.391(9) .
C3 H3 0.9300 .
C4 N7 1.378(8) .
C4 C5 1.404(9) .
C5 C6 1.362(9) .
C5 H5 0.9300 .
C6 H6 0.9300 .
N7 C8 1.348(8) .
N7 H7 0.8600 .
C8 O9 1.210(8) .
C8 C10 1.507(9) .
C10 C11 1.365(9) .
C10 C15 1.395(10) .
C11 C12 1.387(10) .
C12 C13 1.371(11) .
C13 C14 1.386(10) .
C14 C15 1.376(10) .
N16 C21 1.337(8) .
N16 C17 1.344(8) .
C17 C18 1.384(9) .
C17 H17 0.9300 .
C18 C19 1.398(9) .
C18 H18 0.9300 .
C19 N22 1.380(8) .
C19 C20 1.401(9) .
C20 C21 1.381(9) .
C20 H20 0.9300 .
C21 H21 0.9300 .
N22 C23 1.355(9) .
N22 H22 0.8600 .
C23 O24 1.233(9) .
C23 C25 1.493(9) .
C25 C26 1.378(10) .
C25 C30 1.382(9) .
C26 C27 1.379(10) .
C27 C28 1.370(13) .
C28 C29 1.365(13) .
C29 C30 1.385(11) .
O31 O31 0.000(18) 1
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
N7 H7 O31 0.86 1.90 2.745(8) 166.5 1
N22 H22 Cl3 0.86 2.21 3.050(7) 165.3 1
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.250 0.750 0.000 11.1 1.8
2 0.750 0.250 0.000 11.1 1.8
3 0.072 0.258 0.207 12.3 1.1
4 0.242 0.072 0.207 12.3 0.7
5 0.258 0.428 0.207 12.3 0.9
6 0.428 0.242 0.207 12.3 1.1
7 0.572 0.758 0.793 12.3 0.9
8 0.742 0.572 0.793 12.3 1.0
9 0.758 0.928 0.793 12.3 1.3
10 0.928 0.742 0.793 12.3 0.9
