#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:19:08 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180387 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/56/7205668.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_7205668
loop_
_publ_author_name
'Lee, Chia-Hao'
'Su, Fang-Yi'
'Lin, Yi-Hsiu'
'Chou, Chih-Ho'
'Lee, Kwang-Ming'
_publ_section_title
;
 Anion-controlled assemblies of C--H⋯O hydrogen bonded grid,
 stair or bilayer structures by L-shaped pyridinium salts
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              2318
_journal_paper_doi               10.1039/c0ce00610f
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C10 H13 F6 N2 O3 P'
_chemical_formula_weight         354.19
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 93.039(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2214(5)
_cell_length_b                   8.6255(6)
_cell_length_c                   26.3909(18)
_cell_measurement_reflns_used    5289
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.5
_cell_volume                     1414.21(18)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_computing_molecular_graphics    'Bruker APEX2'
_computing_publication_material  'Bruker APEX2'
_computing_structure_refinement  'Shelxtl-97 (Sheldrick, 2008)'
_computing_structure_solution    'Shelxtl-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            12089
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7040
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Columnar
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2879
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0297
_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)+(0.0554P)²+0.4436P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.1008
_reflns_number_gt                2562
_reflns_number_total             2879
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00610f.txt
_cod_data_source_block           PF6_1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7205668
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.8344(2) 0.75136(16) 0.12101(6) 0.0172(3) Uani 1 1 d . . .
H1 H 0.9551 0.6870 0.1157 0.021 Uiso 1 1 calc R . .
C2 C 0.7448(3) 0.83948(17) 0.08159(6) 0.0199(3) Uani 1 1 d . . .
C3 C 0.5684(3) 0.93328(17) 0.09010(6) 0.0213(3) Uani 1 1 d . . .
H3 H 0.5055 0.9951 0.0634 0.026 Uiso 1 1 calc R . .
C4 C 0.4851(3) 0.93582(17) 0.13784(6) 0.0218(3) Uani 1 1 d . . .
H4 H 0.3641 0.9988 0.1441 0.026 Uiso 1 1 calc R . .
C5 C 0.5790(2) 0.84655(17) 0.17588(6) 0.0189(3) Uani 1 1 d . . .
H5 H 0.5230 0.8480 0.2087 0.023 Uiso 1 1 calc R . .
C6 C 0.8330(3) 0.83487(19) 0.02983(6) 0.0249(4) Uani 1 1 d . . .
C7 C 1.0872(3) 0.7160(2) -0.02198(6) 0.0357(4) Uani 1 1 d . . .
H7A H 0.9849 0.6603 -0.0455 0.043 Uiso 1 1 calc R . .
H7B H 1.1185 0.8184 -0.0369 0.043 Uiso 1 1 calc R . .
C8 C 1.2866(3) 0.6263(3) -0.01385(7) 0.0372(4) Uani 1 1 d . . .
H8A H 1.3905 0.6860 0.0074 0.056 Uiso 1 1 calc R . .
H8B H 1.3472 0.6046 -0.0466 0.056 Uiso 1 1 calc R . .
H8C H 1.2551 0.5283 0.0031 0.056 Uiso 1 1 calc R . .
C9 C 0.8538(2) 0.66677(16) 0.20909(5) 0.0163(3) Uani 1 1 d . . .
H9A H 0.9141 0.5697 0.1957 0.020 Uiso 1 1 calc R . .
H9B H 0.7453 0.6388 0.2336 0.020 Uiso 1 1 calc R . .
C10 C 1.0328(2) 0.76130(16) 0.23576(5) 0.0156(3) Uani 1 1 d . . .
F1 F 0.62559(14) 0.40808(10) 0.15078(3) 0.0229(2) Uani 1 1 d . . .
F2 F 0.10913(15) 0.40837(11) 0.14802(4) 0.0284(3) Uani 1 1 d . . .
F3 F 0.37377(16) 0.26798(11) 0.18961(4) 0.0276(2) Uani 1 1 d . . .
F4 F 0.36287(16) 0.54943(11) 0.11030(4) 0.0301(3) Uani 1 1 d . . .
F5 F 0.36103(15) 0.28703(11) 0.10393(3) 0.0251(2) Uani 1 1 d . . .
F6 F 0.37343(16) 0.52859(12) 0.19580(4) 0.0301(3) Uani 1 1 d . . .
N1 N 0.7505(2) 0.75670(13) 0.16702(5) 0.0153(3) Uani 1 1 d . . .
N2 N 1.1190(2) 0.69403(14) 0.27707(5) 0.0186(3) Uani 1 1 d . . .
H2A H 1.2252 0.7395 0.2947 0.022 Uiso 1 1 calc R . .
H2B H 1.0700 0.6038 0.2869 0.022 Uiso 1 1 calc R . .
O1 O 0.7613(2) 0.91309(15) -0.00482(4) 0.0366(3) Uani 1 1 d . . .
O2 O 0.9944(2) 0.73577(14) 0.02776(4) 0.0293(3) Uani 1 1 d . . .
O3 O 1.08915(18) 0.88704(12) 0.21873(4) 0.0218(3) Uani 1 1 d . . .
P1 P 0.36636(6) 0.40833(4) 0.149328(14) 0.01490(13) 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'
P P 0.1023 0.0942 '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
N1 C1 C2 119.97(13) . . ?
N1 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C1 C2 C3 119.26(14) . . ?
C1 C2 C6 121.25(14) . . ?
C3 C2 C6 119.49(14) . . ?
C4 C3 C2 119.43(14) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C5 C4 C3 119.40(14) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N1 C5 C4 120.39(14) . . ?
N1 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
O1 C6 O2 125.65(15) . . ?
O1 C6 C2 122.61(15) . . ?
O2 C6 C2 111.74(13) . . ?
C8 C7 O2 107.39(14) . . ?
C8 C7 H7A 110.2 . . ?
O2 C7 H7A 110.2 . . ?
C8 C7 H7B 110.2 . . ?
O2 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 110.22(12) . . ?
N1 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
N1 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
O3 C10 N2 125.18(14) . . ?
O3 C10 C9 121.21(13) . . ?
N2 C10 C9 113.61(12) . . ?
C1 N1 C5 121.56(13) . . ?
C1 N1 C9 119.11(12) . . ?
C5 N1 C9 119.29(12) . . ?
C10 N2 H2A 120.0 . . ?
C10 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C6 O2 C7 116.52(13) . . ?
F5 P1 F4 90.94(5) . . ?
F5 P1 F2 90.17(5) . . ?
F4 P1 F2 90.38(5) . . ?
F5 P1 F6 179.03(6) . . ?
F4 P1 F6 89.96(6) . . ?
F2 P1 F6 90.18(5) . . ?
F5 P1 F3 90.08(5) . . ?
F4 P1 F3 178.68(6) . . ?
F2 P1 F3 90.46(5) . . ?
F6 P1 F3 89.01(6) . . ?
F5 P1 F1 89.88(5) . . ?
F4 P1 F1 89.75(5) . . ?
F2 P1 F1 179.86(6) . . ?
F6 P1 F1 89.76(5) . . ?
F3 P1 F1 89.41(5) . . ?
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
C1 N1 1.348(2) . ?
C1 C2 1.382(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.391(2) . ?
C2 C6 1.499(2) . ?
C3 C4 1.388(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.371(2) . ?
C4 H4 0.9500 . ?
C5 N1 1.3492(19) . ?
C5 H5 0.9500 . ?
C6 O1 1.2028(19) . ?
C6 O2 1.322(2) . ?
C7 C8 1.468(3) . ?
C7 O2 1.4718(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 N1 1.4735(17) . ?
C9 C10 1.522(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 O3 1.2319(18) . ?
C10 N2 1.3231(19) . ?
F1 P1 1.6112(10) . ?
F2 P1 1.5989(10) . ?
F3 P1 1.6102(9) . ?
F4 P1 1.5939(9) . ?
F5 P1 1.5897(9) . ?
F6 P1 1.6050(9) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
