#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202143.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2202143
loop_
_publ_author_name
'Sluka, Radek'
'Ne\<cas, Marek'
'\<Cern\'ik, Milo\<s'
_publ_section_title
;
 Bis(4-dimethylaminopyridinium) 1,2-difluorodiphosphate
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o190
_journal_page_last               o192
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          '2C7 H11 N2 1+, F2 O5 P2 2-'
_chemical_formula_moiety         '2C7 H11 N2 1+, F2 O5 P2 2-'
_chemical_formula_sum            'C14 H22 F2 N4 O5 P2'
_chemical_formula_weight         426.30
_chemical_name_common
'bis(4-dimethylaminopyridinium) 1,2-difluorodiphosphate'
_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                 92.13(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.386(2)
_cell_length_b                   31.076(6)
_cell_length_c                   7.0720(10)
_cell_measurement_reflns_used    100
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.41
_cell_measurement_theta_min      5.23
_cell_volume                     1841.7(6)
_computing_cell_refinement       Xcalibur
_computing_data_collection       'Xcalibur (Oxford Diffraction Ltd, 2001)'
_computing_data_reduction        Xcalibur
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean '0.06 mm'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Kuma KM-4 CCDr'
_diffrn_measurement_method       \w
_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  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0482
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9769
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.76
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.580
_refine_ls_extinction_coef       0.024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.282
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3200
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.282
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0728P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1421
_reflns_number_gt                2625
_reflns_number_total             3200
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    om6125.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2202143
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_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
P1 0.50995(9) 0.39336(3) 0.38213(11) 0.0174(3) Uani d . 1 P
P2 0.29290(9) 0.36514(3) 0.07473(12) 0.0190(3) Uani d . 1 P
F1 0.4704(2) 0.36060(6) 0.5421(3) 0.0330(5) Uani d . 1 F
F2 0.3839(2) 0.39260(7) -0.0731(3) 0.0362(5) Uani d . 1 F
O1 0.5207(2) 0.43656(7) 0.4706(3) 0.0210(5) Uani d . 1 O
O2 0.6431(2) 0.37618(7) 0.2761(3) 0.0260(6) Uani d . 1 O
O3 0.3633(3) 0.32172(7) 0.0799(4) 0.0300(6) Uani d . 1 O
O4 0.1210(3) 0.37169(7) 0.0402(3) 0.0264(6) Uani d . 1 O
O5 0.3443(2) 0.39163(7) 0.2633(3) 0.0260(6) Uani d . 1 O
N3 0.7739(3) 0.48075(8) 0.3380(4) 0.0196(6) Uani d . 1 N
H3 0.6853 0.4693 0.3778 0.024 Uiso calc R 1 H
N4 1.1937(3) 0.53510(8) 0.1725(4) 0.0173(6) Uani d . 1 N
C10 1.0560(3) 0.51725(10) 0.2224(4) 0.0158(7) Uani d . 1 C
C11 0.9173(3) 0.54253(10) 0.2518(4) 0.0180(7) Uani d . 1 C
H11 0.9193 0.5727 0.2301 0.022 Uiso calc R 1 H
C8 0.8998(4) 0.45539(11) 0.3049(4) 0.0207(7) Uani d . 1 C
H8 0.8905 0.4251 0.3207 0.025 Uiso calc R 1 H
C12 0.7821(4) 0.52348(10) 0.3109(4) 0.0188(7) Uani d . 1 C
H12 0.6914 0.5408 0.3335 0.023 Uiso calc R 1 H
C9 1.0396(4) 0.47221(10) 0.2494(4) 0.0186(7) Uani d . 1 C
H9 1.1274 0.4537 0.2284 0.022 Uiso calc R 1 H
C14 1.2105(4) 0.58139(10) 0.1459(5) 0.0240(7) Uani d . 1 C
H14A 1.1132 0.5928 0.0834 0.036 Uiso calc R 1 H
H14B 1.3019 0.5871 0.0671 0.036 Uiso calc R 1 H
H14C 1.2278 0.5953 0.2692 0.036 Uiso calc R 1 H
C13 1.3379(4) 0.50879(11) 0.1593(5) 0.0233(7) Uani d . 1 C
H13A 1.3621 0.4949 0.2815 0.035 Uiso calc R 1 H
H13B 1.4276 0.5271 0.1258 0.035 Uiso calc R 1 H
H13C 1.3204 0.4867 0.0618 0.035 Uiso calc R 1 H
N1 0.6680(3) 0.29100(10) 0.0629(4) 0.0279(7) Uani d . 1 N
H1 0.5869 0.3088 0.0712 0.033 Uiso calc R 1 H
N2 1.0459(3) 0.20659(8) 0.0372(4) 0.0221(6) Uani d . 1 N
C2 0.7634(4) 0.21968(11) 0.0417(5) 0.0247(8) Uani d . 1 C
H2 0.7410 0.1897 0.0345 0.030 Uiso calc R 1 H
C4 0.9458(4) 0.27985(10) 0.0512(4) 0.0206(7) Uani d . 1 C
H4 1.0503 0.2916 0.0492 0.025 Uiso calc R 1 H
C5 0.8176(4) 0.30645(11) 0.0620(4) 0.0244(8) Uani d . 1 C
H5 0.8342 0.3367 0.0691 0.029 Uiso calc R 1 H
C3 0.9236(4) 0.23451(10) 0.0429(4) 0.0190(7) Uani d . 1 C
C1 0.6425(4) 0.24865(12) 0.0510(5) 0.0285(8) Uani d . 1 C
H1A 0.5357 0.2384 0.0490 0.034 Uiso calc R 1 H
C6 1.2130(4) 0.21998(12) 0.0482(6) 0.0309(9) Uani d . 1 C
H6A 1.2189 0.2514 0.0573 0.046 Uiso calc R 1 H
H6B 1.2660 0.2104 -0.0656 0.046 Uiso calc R 1 H
H6C 1.2662 0.2071 0.1602 0.046 Uiso calc R 1 H
C7 1.0196(4) 0.16017(10) 0.0342(6) 0.0312(9) Uani d . 1 C
H7A 0.9854 0.1507 0.1585 0.047 Uiso calc R 1 H
H7B 1.1190 0.1455 0.0044 0.047 Uiso calc R 1 H
H7C 0.9368 0.1531 -0.0623 0.047 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
P1 0.0133(4) 0.0160(4) 0.0230(5) -0.0004(3) 0.0009(3) -0.0009(3)
P2 0.0151(4) 0.0159(4) 0.0256(5) -0.0001(3) -0.0019(3) -0.0003(3)
F1 0.0377(12) 0.0268(11) 0.0347(12) -0.0080(9) 0.0026(9) 0.0079(9)
F2 0.0300(11) 0.0439(13) 0.0351(12) -0.0035(9) 0.0051(9) 0.0121(10)
O1 0.0179(11) 0.0181(11) 0.0271(13) -0.0020(9) 0.0041(9) -0.0035(9)
O2 0.0142(11) 0.0270(13) 0.0369(14) 0.0002(9) 0.0024(10) -0.0076(11)
O3 0.0190(12) 0.0190(12) 0.0514(16) 0.0034(9) -0.0057(11) -0.0072(11)
O4 0.0170(12) 0.0215(12) 0.0400(14) 0.0000(9) -0.0058(10) -0.0008(10)
O5 0.0144(11) 0.0299(13) 0.0336(13) 0.0029(9) -0.0023(10) -0.0119(11)
N3 0.0146(13) 0.0257(15) 0.0187(14) -0.0049(11) 0.0014(10) 0.0005(12)
N4 0.0141(13) 0.0167(13) 0.0212(14) 0.0014(10) 0.0004(10) 0.0009(11)
C10 0.0128(15) 0.0253(17) 0.0092(14) 0.0007(12) -0.0002(12) -0.0007(13)
C11 0.0177(16) 0.0171(16) 0.0192(16) 0.0014(13) -0.0003(13) -0.0010(13)
C8 0.0256(17) 0.0183(16) 0.0178(16) -0.0014(13) -0.0019(13) 0.0028(13)
C12 0.0140(15) 0.0236(17) 0.0187(16) 0.0000(13) -0.0008(12) -0.0029(13)
C9 0.0176(16) 0.0189(16) 0.0190(16) 0.0053(13) -0.0014(13) -0.0016(13)
C14 0.0192(17) 0.0199(17) 0.0328(19) -0.0015(13) 0.0010(14) 0.0035(15)
C13 0.0137(16) 0.0307(19) 0.0255(17) 0.0045(13) 0.0014(13) -0.0034(15)
N1 0.0218(15) 0.0319(17) 0.0302(16) 0.0112(12) 0.0043(12) 0.0015(13)
N2 0.0151(13) 0.0180(14) 0.0333(16) 0.0019(11) 0.0024(12) -0.0009(12)
C2 0.0224(17) 0.0185(17) 0.0334(19) -0.0032(13) 0.0010(15) -0.0007(15)
C4 0.0214(17) 0.0178(16) 0.0226(17) -0.0017(13) 0.0025(13) -0.0020(13)
C5 0.0313(19) 0.0195(17) 0.0227(18) 0.0044(14) 0.0052(15) -0.0007(14)
C3 0.0201(17) 0.0199(17) 0.0170(15) 0.0016(13) 0.0005(13) -0.0016(13)
C1 0.0164(17) 0.035(2) 0.034(2) -0.0007(14) -0.0009(14) -0.0011(16)
C6 0.0175(17) 0.0285(19) 0.047(2) 0.0014(14) 0.0021(16) -0.0038(17)
C7 0.0281(19) 0.0201(18) 0.046(2) 0.0061(15) 0.0053(16) -0.0001(16)
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
O2 P1 O1 120.62(13)
O2 P1 F1 108.54(13)
O1 P1 F1 107.16(12)
O2 P1 O5 112.46(13)
O1 P1 O5 106.87(12)
F1 P1 O5 98.90(12)
O4 P2 O3 121.44(13)
O4 P2 F2 108.23(13)
O3 P2 F2 108.09(13)
O4 P2 O5 107.30(13)
O3 P2 O5 110.66(14)
F2 P2 O5 98.72(12)
P1 O5 P2 130.74(14)
C12 N3 C8 120.6(3)
C12 N3 H3 119.7
C8 N3 H3 119.7
C10 N4 C14 122.1(3)
C10 N4 C13 120.5(3)
C14 N4 C13 117.3(3)
N4 C10 C9 122.2(3)
N4 C10 C11 121.7(3)
C9 C10 C11 116.1(3)
C12 C11 C10 120.0(3)
C12 C11 H11 120.0
C10 C11 H11 120.0
N3 C8 C9 121.2(3)
N3 C8 H8 119.4
C9 C8 H8 119.4
N3 C12 C11 121.5(3)
N3 C12 H12 119.2
C11 C12 H12 119.2
C8 C9 C10 120.6(3)
C8 C9 H9 119.7
C10 C9 H9 119.7
N4 C14 H14A 109.5
N4 C14 H14B 109.5
H14A C14 H14B 109.5
N4 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
N4 C13 H13A 109.5
N4 C13 H13B 109.5
H13A C13 H13B 109.5
N4 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C1 N1 C5 120.0(3)
C1 N1 H1 120.0
C5 N1 H1 120.0
C3 N2 C7 121.5(3)
C3 N2 C6 123.1(3)
C7 N2 C6 115.2(3)
C1 C2 C3 119.5(3)
C1 C2 H2 120.3
C3 C2 H2 120.3
C5 C4 C3 120.1(3)
C5 C4 H4 119.9
C3 C4 H4 119.9
N1 C5 C4 121.5(3)
N1 C5 H5 119.2
C4 C5 H5 119.2
N2 C3 C2 120.8(3)
N2 C3 C4 122.8(3)
C2 C3 C4 116.4(3)
N1 C1 C2 122.5(3)
N1 C1 H1A 118.7
C2 C1 H1A 118.7
N2 C6 H6A 109.5
N2 C6 H6B 109.5
H6A C6 H6B 109.5
N2 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
N2 C7 H7A 109.5
N2 C7 H7B 109.5
H7A C7 H7B 109.5
N2 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O2 1.468(2)
P1 O1 1.483(2)
P1 F1 1.567(2)
P1 O5 1.598(2)
P2 O4 1.468(2)
P2 O3 1.473(2)
P2 F2 1.569(2)
P2 O5 1.612(2)
N3 C12 1.344(4)
N3 C8 1.345(4)
N3 H3 0.8800
N4 C10 1.340(4)
N4 C14 1.458(4)
N4 C13 1.465(4)
C10 C9 1.420(4)
C10 C11 1.426(4)
C11 C12 1.358(4)
C11 H11 0.9500
C8 C9 1.355(4)
C8 H8 0.9500
C12 H12 0.9500
C9 H9 0.9500
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
N1 C1 1.336(4)
N1 C5 1.343(4)
N1 H1 0.8800
N2 C3 1.345(4)
N2 C7 1.459(4)
N2 C6 1.461(4)
C2 C1 1.360(5)
C2 C3 1.419(4)
C2 H2 0.9500
C4 C5 1.360(4)
C4 C3 1.422(4)
C4 H4 0.9500
C5 H5 0.9500
C1 H1A 0.9500
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
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
N3 H3 O1 0.88 1.85 2.724(3) 170
N1 H1 O3 0.88 1.92 2.735(3) 153
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
O2 P1 O5 P2 16.2(3)
O1 P1 O5 P2 150.69(19)
F1 P1 O5 P2 -98.2(2)
O4 P2 O5 P1 173.33(19)
O3 P2 O5 P1 38.8(2)
F2 P2 O5 P1 -74.4(2)
C14 N4 C10 C9 -179.6(3)
C13 N4 C10 C9 -5.2(4)
C14 N4 C10 C11 0.3(4)
C13 N4 C10 C11 174.7(3)
N4 C10 C11 C12 -176.9(3)
C9 C10 C11 C12 3.0(4)
C12 N3 C8 C9 2.1(5)
C8 N3 C12 C11 -0.8(4)
C10 C11 C12 N3 -1.8(5)
N3 C8 C9 C10 -0.8(5)
N4 C10 C9 C8 178.2(3)
C11 C10 C9 C8 -1.7(4)
C1 N1 C5 C4 -0.7(5)
C3 C4 C5 N1 -0.8(5)
C7 N2 C3 C2 -1.5(5)
C6 N2 C3 C2 -176.7(3)
C7 N2 C3 C4 178.2(3)
C6 N2 C3 C4 3.1(5)
C1 C2 C3 N2 178.8(3)
C1 C2 C3 C4 -0.9(5)
C5 C4 C3 N2 -178.2(3)
C5 C4 C3 C2 1.6(5)
C5 N1 C1 C2 1.4(5)
C3 C2 C1 N1 -0.6(5)