#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/65/2016574.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_2016574
loop_
_publ_author_name
'Yamada, Shinji'
'Ohta, Emiko'
_publ_section_title
;
 (1-Pyridinio)perfluorophenacylide: a new stable pyridinium ylide in
 the enol form
;
_journal_coeditor_code           SQ3132
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o230
_journal_page_last               o232
_journal_paper_doi               10.1107/S0108270108006318
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C13 H6 F5 N O'
_chemical_formula_moiety         'C13 H6 F5 N O'
_chemical_formula_sum            'C13 H6 F5 N O'
_chemical_formula_weight         287.19
_chemical_name_systematic
;
(1-Pyridinio)perfluorophenacylide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 93.453(2)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   11.5658(4)
_cell_length_b                   8.0116(3)
_cell_length_c                   12.2308(4)
_cell_measurement_reflns_used    5146
_cell_measurement_temperature    296.1
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.6
_cell_volume                     1131.26(7)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction
'CrystalStructure (Rigaku/MSC & Rigaku, 2006) or SHELXTL?'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'CrystalStructure (Rigaku/MSC & Rigaku, 2006)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12696
_diffrn_reflns_theta_full        68.23
_diffrn_reflns_theta_max         68.23
_diffrn_reflns_theta_min         6.61
_exptl_absorpt_coefficient_mu    1.465
_exptl_absorpt_correction_T_max  0.8674
_exptl_absorpt_correction_T_min  0.5921
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             576.00
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.164
_refine_ls_extinction_coef       0.0037(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2056
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0339
_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/[σ²(Fo²)+(0.0616P)²+0.1477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1040
_reflns_number_gt                1825
_reflns_number_total             2056
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sq3132.cif
_cod_data_source_block           I
_cod_original_cell_volume        1131.24(7)
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               2016574
_cod_database_fobs_code          2016574
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +x,+y,+z
2 1/2-x,1/2+y,-z
3 -x,-y,-z
4 1/2+x,1/2-y,+z
loop_
_atom_site_type_symbol
_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_occupancy
F F1 0.24693(8) 1.06550(12) 0.85795(7) 0.0647(3) Uani d 1
F F2 0.28115(8) 1.03358(13) 1.07499(7) 0.0673(3) Uani d 1
F F3 0.44075(9) 0.81399(13) 1.16103(7) 0.0687(3) Uani d 1
F F4 0.57016(9) 0.63476(12) 1.02752(8) 0.0706(3) Uani d 1
F F5 0.53203(8) 0.65352(12) 0.81009(8) 0.0679(3) Uani d 1
O O1 0.46787(9) 0.90855(16) 0.65392(8) 0.0649(3) Uani d 1
N N1 0.23436(10) 0.86968(15) 0.54225(9) 0.0503(3) Uani d 1
C C1 0.30972(14) 0.9183(2) 0.46700(12) 0.0574(4) Uani d 1
C C2 0.27583(16) 0.9272(2) 0.35822(13) 0.0659(4) Uani d 1
C C3 0.16487(17) 0.8845(3) 0.32194(14) 0.0714(5) Uani d 1
C C4 0.08934(17) 0.8350(3) 0.39810(15) 0.0761(5) Uani d 1
C C5 0.12391(14) 0.8283(2) 0.50654(14) 0.0666(5) Uani d 1
C C6 0.26590(13) 0.8601(2) 0.65533(11) 0.0534(4) Uani d 1
C C7 0.37595(12) 0.87934(18) 0.70037(11) 0.0484(3) Uani d 1
C C8 0.38702(11) 0.85931(17) 0.82457(10) 0.0462(3) Uani d 1
C C9 0.32453(12) 0.95199(17) 0.89630(11) 0.0479(3) Uani d 1
C C10 0.34107(12) 0.93749(18) 1.00832(11) 0.0498(3) Uani d 1
C C11 0.42220(12) 0.82862(18) 1.05265(11) 0.0507(3) Uani d 1
C C12 0.48707(12) 0.73598(18) 0.98433(11) 0.0512(3) Uani d 1
C C13 0.46833(12) 0.75087(18) 0.87253(11) 0.0494(3) Uani d 1
H H1 0.3862(16) 0.946(2) 0.4967(14) 0.066(5) Uiso d 1
H H2 0.3308(17) 0.971(2) 0.3078(16) 0.074(5) Uiso d 1
H H3 0.1399(17) 0.894(2) 0.2488(16) 0.077(5) Uiso d 1
H H4 0.011(2) 0.811(3) 0.3766(17) 0.086(6) Uiso d 1
H H5 0.0733(18) 0.802(3) 0.5631(16) 0.081(6) Uiso d 1
H H6 0.2045(15) 0.834(2) 0.6978(14) 0.061(5) Uiso d 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
F F 0.073 0.053
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.049 0.032
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.031 0.018
;
International Tables for Crystallography
(1992, 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_publ_flag
C1 N1 C5 118.53(12) n
C1 N1 C6 122.66(12) n
C5 N1 C6 118.81(12) n
N1 C1 C2 121.02(14) n
C1 C2 C3 120.57(16) n
C2 C3 C4 118.18(15) n
C3 C4 C5 120.66(17) n
N1 C5 C4 121.04(15) n
N1 C6 C7 124.70(13) n
O1 C7 C6 129.20(12) n
O1 C7 C8 116.56(11) n
C6 C7 C8 114.23(12) n
C7 C8 C9 123.96(11) n
C7 C8 C13 120.14(11) n
C9 C8 C13 115.78(11) n
F1 C9 C8 120.34(11) n
F1 C9 C10 117.05(12) n
C8 C9 C10 122.57(12) n
F2 C10 C9 120.64(12) n
F2 C10 C11 119.40(11) n
C9 C10 C11 119.92(13) n
F3 C11 C10 120.96(12) n
F3 C11 C12 119.70(12) n
C10 C11 C12 119.32(12) n
F4 C12 C11 119.45(12) n
F4 C12 C13 120.65(12) n
C11 C12 C13 119.88(12) n
F5 C13 C8 120.37(11) n
F5 C13 C12 117.11(12) n
C8 C13 C12 122.51(12) n
N1 C1 H1 115.0(10) no
C2 C1 H1 124.0(10) no
C1 C2 H2 118.3(11) no
C3 C2 H2 121.0(11) no
C2 C3 H3 121.4(12) no
C4 C3 H3 120.4(12) no
C3 C4 H4 120.4(13) no
C5 C4 H4 118.8(13) no
N1 C5 H5 115.1(12) no
C4 C5 H5 123.8(12) no
N1 C6 H6 113.5(10) no
C7 C6 H6 121.7(10) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C9 1.3423(16) n
F2 C10 1.3438(17) n
F3 C11 1.3352(15) n
F4 C12 1.3413(16) n
F5 C13 1.3424(17) n
O1 C7 1.2572(17) n
N1 C1 1.3619(19) n
N1 C5 1.3657(19) n
N1 C6 1.4110(17) n
C1 C2 1.366(2) n
C2 C3 1.376(2) n
C3 C4 1.373(2) n
C4 C5 1.363(2) n
C6 C7 1.3648(19) n
C7 C8 1.5252(18) n
C8 C9 1.3856(19) n
C8 C13 1.3845(18) n
C9 C10 1.3768(18) n
C10 C11 1.3689(19) n
C11 C12 1.374(2) n
C12 C13 1.3767(18) n
C1 H1 0.962(18) no
C2 H2 0.98(2) no
C3 H3 0.926(19) no
C4 H4 0.94(2) no
C5 H5 0.96(2) no
C6 H6 0.928(18) no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
F1 F3 2.9442(14) 2_557
F1 F4 3.4420(13) 3_677
F1 F4 3.4009(13) 4_465
F1 F5 3.0698(13) 4_465
F1 C3 3.562(2) 2_556
F1 C10 3.5768(17) 2_557
F1 C11 3.1182(17) 2_557
F2 F4 3.4423(14) 3_677
F2 F4 2.8178(13) 4_465
F2 F5 3.5444(13) 3_677
F2 C2 3.5716(18) 1_556
F2 C3 3.584(2) 1_556
F2 C8 3.5200(16) 2_557
F2 C9 3.5924(17) 2_557
F2 C12 3.5367(16) 2_557
F2 C12 3.3698(17) 3_677
F2 C13 3.4628(17) 2_557
F2 C13 3.4008(16) 3_677
F3 F1 2.9442(14) 2_547
F3 O1 3.3004(14) 3_677
F3 C2 3.291(2) 1_556
F3 C3 3.537(2) 4_566
F3 C4 3.491(2) 4_566
F3 C8 3.2875(16) 3_677
F3 C9 3.4067(17) 3_677
F4 F1 3.4420(13) 3_677
F4 F1 3.4009(13) 4_565
F4 F2 3.4423(14) 3_677
F4 F2 2.8178(13) 4_565
F4 F4 2.7600(13) 3_667
F4 F5 3.3104(13) 3_667
F4 C9 3.5047(17) 4_565
F4 C10 3.2088(17) 4_565
F4 C12 3.0446(17) 3_667
F4 C13 3.3620(17) 3_667
F5 F1 3.0698(13) 4_565
F5 F2 3.5444(13) 3_677
F5 F4 3.3104(13) 3_667
F5 C3 3.463(2) 2_546
F5 C6 3.3953(17) 4_565
F5 C9 3.5835(16) 4_565
O1 F3 3.3004(14) 3_677
O1 C1 3.3448(19) 3_676
O1 C2 3.255(2) 3_676
O1 C4 3.531(2) 2_556
O1 C5 3.240(2) 4_565
C1 O1 3.3448(19) 3_676
C1 C5 3.385(2) 2_556
C2 F2 3.5716(18) 1_554
C2 F3 3.291(2) 1_554
C2 O1 3.255(2) 3_676
C2 C6 3.504(2) 2_556
C3 F1 3.562(2) 2_546
C3 F2 3.584(2) 1_554
C3 F3 3.537(2) 4_464
C3 F5 3.463(2) 2_556
C4 F3 3.491(2) 4_464
C4 O1 3.531(2) 2_546
C5 O1 3.240(2) 4_465
C5 C1 3.385(2) 2_546
C6 F5 3.3953(17) 4_465
C6 C2 3.504(2) 2_546
C8 F2 3.5200(16) 2_547
C8 F3 3.2875(16) 3_677
C9 F2 3.5924(17) 2_547
C9 F3 3.4067(17) 3_677
C9 F4 3.5047(17) 4_465
C9 F5 3.5835(16) 4_465
C9 C11 3.4408(19) 3_677
C9 C12 3.5701(19) 3_677
C10 F1 3.5768(17) 2_547
C10 F4 3.2088(17) 4_465
C10 C11 3.437(2) 3_677
C10 C12 3.283(2) 3_677
C10 C13 3.5819(19) 3_677
C11 F1 3.1182(17) 2_547
C11 C9 3.4408(19) 3_677
C11 C10 3.437(2) 3_677
C11 C11 3.566(2) 3_677
C12 F2 3.5367(16) 2_547
C12 F2 3.3698(17) 3_677
C12 F4 3.0446(17) 3_667
C12 C9 3.5701(19) 3_677
C12 C10 3.283(2) 3_677
C13 F2 3.4628(17) 2_547
C13 F2 3.4008(16) 3_677
C13 F4 3.3620(17) 3_667
C13 C10 3.5819(19) 3_677
F1 H3 3.250(19) 2_556
F2 H2 2.914(19) 1_556
F2 H3 2.98(2) 1_556
F3 H2 2.59(2) 1_556
F3 H3 2.991(19) 4_566
F3 H4 2.89(2) 4_566
F4 H3 2.787(19) 4_566
F5 H3 2.935(19) 2_546
F5 H4 3.58(2) 2_546
F5 H5 3.11(2) 4_565
F5 H6 2.492(18) 4_565
O1 H1 2.824(18) 3_676
O1 H2 2.539(19) 3_676
O1 H4 3.26(2) 2_556
O1 H5 2.39(2) 4_565
O1 H6 3.372(17) 4_565
C1 H4 3.22(2) 4_565
C1 H5 3.39(2) 2_556
C2 H4 3.32(2) 4_565
C2 H5 3.57(2) 2_556
C2 H6 3.339(16) 2_556
C4 H1 3.377(18) 2_546
C4 H1 3.519(18) 4_465
C4 H5 3.51(2) 3_576
C5 H1 3.066(18) 2_546
C5 H1 3.516(18) 4_465
C6 H2 3.353(19) 2_546
C7 H5 3.26(2) 4_565
C11 H2 3.54(2) 1_556
C13 H3 3.421(19) 2_546
H1 O1 2.824(18) 3_676
H1 C4 3.377(18) 2_556
H1 C4 3.519(18) 4_565
H1 C5 3.066(18) 2_556
H1 C5 3.516(18) 4_565
H1 H1 2.77(2) 3_676
H1 H4 3.48(2) 2_556
H1 H4 2.96(2) 4_565
H1 H5 2.99(2) 2_556
H1 H5 3.01(2) 4_565
H2 F2 2.914(19) 1_554
H2 F3 2.59(2) 1_554
H2 O1 2.539(19) 3_676
H2 C6 3.353(19) 2_556
H2 C11 3.54(2) 1_554
H2 H4 3.16(2) 4_565
H2 H5 3.25(2) 2_556
H2 H6 2.94(2) 2_556
H3 F1 3.250(19) 2_546
H3 F2 2.98(2) 1_554
H3 F3 2.991(19) 4_464
H3 F4 2.787(19) 4_464
H3 F5 2.935(19) 2_556
H3 C13 3.421(19) 2_556
H4 F3 2.89(2) 4_464
H4 F5 3.58(2) 2_556
H4 O1 3.26(2) 2_546
H4 C1 3.22(2) 4_465
H4 C2 3.32(2) 4_465
H4 H1 3.48(2) 2_546
H4 H1 2.96(2) 4_465
H4 H2 3.16(2) 4_465
H4 H5 3.35(3) 3_576
H5 F5 3.11(2) 4_465
H5 O1 2.39(2) 4_465
H5 C1 3.39(2) 2_546
H5 C2 3.57(2) 2_546
H5 C4 3.51(2) 3_576
H5 C7 3.26(2) 4_465
H5 H1 2.99(2) 2_546
H5 H1 3.01(2) 4_465
H5 H2 3.25(2) 2_546
H5 H4 3.35(3) 3_576
H6 F5 2.492(18) 4_465
H6 O1 3.372(17) 4_465
H6 C2 3.339(16) 2_546
H6 H2 2.94(2) 2_546
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C6 H6 F1 . 0.94(2) 2.72(2) 2.994(2) 97.7(11) y
C1 H1 O1 . 0.97(2) 2.10(2) 2.842(2) 131.7(15) y
C5 H5 O1 4_465 0.97(2) 2.39(2) 3.240(2) 147.3(17) y
C6 H6 F5 4_465 0.94(2) 2.48(2) 3.396(2) 164.9(14) y
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
C1 N1 C5 C4 0.1(2)
C5 N1 C1 C2 0.6(2)
C1 N1 C6 C7 -7.7(2)
C6 N1 C1 C2 -179.52(15)
C5 N1 C6 C7 172.20(15)
C6 N1 C5 C4 -179.78(17)
N1 C1 C2 C3 -1.1(2)
C1 C2 C3 C4 0.8(2)
C2 C3 C4 C5 -0.1(2)
C3 C4 C5 N1 -0.4(3)
N1 C6 C7 O1 0.2(2)
N1 C6 C7 C8 -178.72(13)
O1 C7 C8 C9 124.87(15)
O1 C7 C8 C13 -50.93(18)
C6 C7 C8 C9 -56.04(19)
C6 C7 C8 C13 128.16(14)
C7 C8 C9 F1 1.3(2)
C7 C8 C9 C10 -176.32(13)
C7 C8 C13 F5 -4.95(19)
C7 C8 C13 C12 175.72(13)
C9 C8 C13 F5 178.91(12)
C9 C8 C13 C12 -0.4(2)
C13 C8 C9 F1 177.32(12)
C13 C8 C9 C10 -0.4(2)
F1 C9 C10 F2 0.15(19)
F1 C9 C10 C11 -177.48(12)
C8 C9 C10 F2 177.89(12)
C8 C9 C10 C11 0.3(2)
F2 C10 C11 F3 1.5(2)
F2 C10 C11 C12 -177.06(12)
C9 C10 C11 F3 179.15(12)
C9 C10 C11 C12 0.6(2)
F3 C11 C12 F4 -1.5(2)
F3 C11 C12 C13 -179.91(12)
C10 C11 C12 F4 177.04(12)
C10 C11 C12 C13 -1.3(2)
F4 C12 C13 F5 3.6(2)
F4 C12 C13 C8 -177.09(12)
C11 C12 C13 F5 -178.08(12)
C11 C12 C13 C8 1.3(2)
