#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:45:29 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178962 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/91/4119187.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_4119187
loop_
_publ_author_name
'De-Xian Wang'
'Mei-Xiang Wang'
_publ_section_title
;
 Anion-π Interactions: Generality, Binding Strength, and Structure
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              892
_journal_page_last               897
_journal_paper_doi               10.1021/ja310834w
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C18 H8 Cl2 N6 O4, C8 H20 N, F6 P'
_chemical_formula_sum            'C26 H28 Cl2 F6 N7 O4 P'
_chemical_formula_weight         718.42
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           67
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-C 2a 2'
_symmetry_space_group_name_H-M   'C m m a'
_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            4
_cell_length_a                   15.947(2)
_cell_length_b                   16.119(2)
_cell_length_c                   12.028(2)
_cell_measurement_reflns_used    4165
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      1.80
_cell_volume                     3091.8(7)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5765
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_T_max  0.9697
_exptl_absorpt_correction_T_min  0.9344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.563
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1526
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.195
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0674
_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)+(0.0371P)²+10.5300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1394
_refine_ls_wR_factor_ref         0.1424
_reflns_number_gt                1431
_reflns_number_total             1526
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja310834w_si_003.cif
_cod_data_source_block           a
_cod_original_cell_volume        3091.7(8)
_cod_database_code               4119187
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z'
'-x, y+1/2, -z'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z'
'-x+1/2, y+1, -z'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z'
'x, -y-1/2, z'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z'
'x+1/2, -y, z'
'-x+1/2, y+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
Cl1 Cl 0.0000 0.59117(8) 0.18027(11) 0.0432(4) Uani 1 2 d S
P1 P 0.0000 0.7500 -0.08595(17) 0.0436(5) Uani 1 4 d S
F1 F -0.0699(4) 0.7500 -0.1730(5) 0.157(3) Uani 1 2 d S
F2 F 0.0000 0.6536(3) -0.0790(6) 0.127(2) Uani 1 2 d S
F3 F -0.0704(3) 0.7500 0.0043(5) 0.1239(19) Uani 1 2 d S
O1 O 0.14380(13) 0.39822(13) 0.42153(18) 0.0328(6) Uani 1 1 d .
N1 N 0.07479(16) 0.48742(16) 0.3106(2) 0.0307(6) Uani 1 1 d .
N2 N 0.0000 0.3939(2) 0.4275(3) 0.0277(8) Uani 1 2 d S
N3 N 0.2500 0.5000 0.0000 0.0270(11) Uani 1 4 d S
C1 C 0.0000 0.5129(3) 0.2781(4) 0.0318(10) Uani 1 2 d S
C2 C 0.06939(18) 0.42632(19) 0.3860(2) 0.0279(7) Uani 1 1 d .
C3 C 0.14157(18) 0.32279(18) 0.4827(3) 0.0275(7) Uani 1 1 d .
C4 C 0.14533(19) 0.3251(2) 0.5967(3) 0.0315(7) Uani 1 1 d .
H4A H 0.1475 0.3764 0.6354 0.038 Uiso 1 1 calc R
C5 C 0.1459(3) 0.2500 0.6539(4) 0.0338(11) Uani 1 2 d S
H5A H 0.1468 0.2500 0.7329 0.041 Uiso 1 2 calc SR
C6 C 0.1404(3) 0.2500 0.4235(4) 0.0282(10) Uani 1 2 d S
H6A H 0.1389 0.2500 0.3446 0.034 Uiso 1 2 calc SR
C7 C 0.2383(3) 0.3874(3) 0.1478(3) 0.0632(12) Uani 1 1 d .
H7A H 0.1971 0.3551 0.1898 0.095 Uiso 1 1 calc R
H7B H 0.2737 0.4188 0.1996 0.095 Uiso 1 1 calc R
H7C H 0.2734 0.3499 0.1037 0.095 Uiso 1 1 calc R
C8 C 0.1934(2) 0.4468(2) 0.0714(3) 0.0385(8) Uani 1 1 d .
H8A H 0.1577 0.4837 0.1170 0.046 Uiso 1 1 calc R
H8B H 0.1560 0.4145 0.0221 0.046 Uiso 1 1 calc R
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'
P P 0.1023 0.0942 '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'
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
F1 P1 F1 93.6(5) 2_565 .
F1 P1 F2 92.11(18) 2_565 2_565
F1 P1 F2 92.11(18) . 2_565
F1 P1 F2 92.11(18) 2_565 .
F1 P1 F2 92.11(18) . .
F2 P1 F2 173.8(5) 2_565 .
F1 P1 F3 87.2(4) 2_565 2_565
F1 P1 F3 179.2(4) . 2_565
F2 P1 F3 87.86(19) 2_565 2_565
F2 P1 F3 87.86(19) . 2_565
F1 P1 F3 179.2(4) 2_565 .
F1 P1 F3 87.2(4) . .
F2 P1 F3 87.86(19) 2_565 .
F2 P1 F3 87.86(19) . .
F3 P1 F3 91.9(5) 2_565 .
C2 O1 C3 115.6(2) . .
C1 N1 C2 111.8(3) . .
C2 N2 C2 113.7(4) . 12
C8 N3 C8 106.8(3) 6 7_545
C8 N3 C8 110.9(3) 6 4_565
C8 N3 C8 110.8(3) 7_545 4_565
C8 N3 C8 110.8(3) 6 .
C8 N3 C8 110.9(3) 7_545 .
C8 N3 C8 106.8(3) 4_565 .
N1 C1 N1 129.1(4) . 12
N1 C1 Cl1 115.4(2) . .
N1 C1 Cl1 115.4(2) 12 .
N2 C2 O1 119.2(3) . .
N2 C2 N1 126.8(3) . .
O1 C2 N1 114.0(3) . .
C6 C3 C4 122.8(3) . .
C6 C3 O1 117.6(3) . .
C4 C3 O1 119.5(3) . .
C3 C4 C5 118.1(3) . .
C3 C4 H4A 121.0 . .
C5 C4 H4A 121.0 . .
C4 C5 C4 120.7(4) 11_565 .
C4 C5 H5A 119.6 11_565 .
C4 C5 H5A 119.6 . .
C3 C6 C3 117.5(4) . 11_565
C3 C6 H6A 121.3 . .
C3 C6 H6A 121.2 11_565 .
C8 C7 H7A 109.5 . .
C8 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C8 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C7 C8 N3 115.0(3) . .
C7 C8 H8A 108.5 . .
N3 C8 H8A 108.5 . .
C7 C8 H8B 108.5 . .
N3 C8 H8B 108.5 . .
H8A C8 H8B 107.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C1 1.725(5) .
P1 F1 1.530(5) 2_565
P1 F1 1.530(5) .
P1 F2 1.556(4) 2_565
P1 F2 1.556(5) .
P1 F3 1.561(5) 2_565
P1 F3 1.561(5) .
O1 C2 1.340(4) .
O1 C3 1.422(4) .
N1 C1 1.321(3) .
N1 C2 1.341(4) .
N2 C2 1.322(4) .
N2 C2 1.322(4) 12
N3 C8 1.512(3) 6
N3 C8 1.512(3) 7_545
N3 C8 1.512(3) 4_565
N3 C8 1.512(3) .
C1 N1 1.321(3) 12
C3 C6 1.372(4) .
C3 C4 1.373(4) .
C4 C5 1.392(4) .
C4 H4A 0.9500 .
C5 C4 1.392(4) 11_565
C5 H5A 0.9500 .
C6 C3 1.372(4) 11_565
C6 H6A 0.9500 .
C7 C8 1.507(5) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
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_4
C2 N1 C1 N1 1.0(7) . 12
C2 N1 C1 Cl1 -179.6(3) . .
C2 N2 C2 O1 -179.80(19) 12 .
C2 N2 C2 N1 1.4(6) 12 .
C3 O1 C2 N2 13.8(4) . .
C3 O1 C2 N1 -167.3(2) . .
C1 N1 C2 N2 -1.2(5) . .
C1 N1 C2 O1 179.9(3) . .
C2 O1 C3 C6 83.6(4) . .
C2 O1 C3 C4 -99.9(3) . .
C6 C3 C4 C5 -1.6(5) . .
O1 C3 C4 C5 -177.8(3) . .
C3 C4 C5 C4 1.9(6) . 11_565
C4 C3 C6 C3 1.2(6) . 11_565
O1 C3 C6 C3 177.5(2) . 11_565
C8 N3 C8 C7 -60.3(3) 6 .
C8 N3 C8 C7 58.1(3) 7_545 .
C8 N3 C8 C7 178.8(4) 4_565 .
