#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/40/4024062.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_4024062
loop_
_publ_author_name
'Hiroyuki Suzuki'
'Norio Sakai'
'Ryohei Iwahara'
'Takayuki Fujiwaka'
'Mitsunobu Satoh'
'Akikazu Kakehi'
'Takeo Konakahara'
_publ_section_title
;
 Novel Synthesis of 7-Fluoro-8-(trifluoromethyl)-1H-1,6-naphthyridin-4-one
 Derivatives: Intermolecular Cyclization of an N-Silyl-1-azaallyl
 Anion with Perfluoroalkene and Subsequent Intramolecular Skeletal
 Transformation of the Resulting Pentasubstituted Pyridines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5878
_journal_page_last               5881
_journal_paper_doi               10.1021/jo070564m
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C14 H9 F9 N2 O'
_chemical_formula_weight         392.23
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 106.986(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.563(4)
_cell_length_b                   9.543(4)
_cell_length_c                   15.602(6)
_cell_measurement_reflns_used    1702
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      22.98
_cell_measurement_theta_min      2.53
_cell_volume                     1504.2(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.918
_diffrn_measured_fraction_theta_max 0.918
_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  0.0631
_diffrn_reflns_av_sigmaI/netI    0.0818
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8879
_diffrn_reflns_theta_full        28.23
_diffrn_reflns_theta_max         28.23
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  -183
_exptl_absorpt_correction_T_min  -183
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.338
_exptl_crystal_size_mid          0.298
_exptl_crystal_size_min          0.221
_refine_diff_density_max         1.108
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.932
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3401
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.932
_refine_ls_R_factor_all          0.1315
_refine_ls_R_factor_gt           0.1017
_refine_ls_shift/su_max          0.175
_refine_ls_shift/su_mean         0.033
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1848P)²+4.7989P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2729
_refine_ls_wR_factor_ref         0.3046
_reflns_number_gt                2448
_reflns_number_total             3401
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070564msi20070514_030735.cif
_cod_data_source_block           r10i
_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 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4024062
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
F1 F 0.4208(3) 0.7611(3) 1.15951(19) 0.0430(8) Uani 1 1 d . . .
F5 F 0.1559(3) 0.7043(3) 0.84018(19) 0.0413(7) Uani 1 1 d . . .
F6 F 0.0595(3) 0.5076(3) 0.84143(19) 0.0406(7) Uani 1 1 d . . .
O1 O -0.0019(3) 0.3371(3) 0.9675(2) 0.0312(7) Uani 1 1 d . . .
N1 N 0.3239(4) 0.5551(4) 1.1548(2) 0.0301(8) Uani 1 1 d . . .
C4 C 0.2112(4) 0.4471(5) 1.0150(3) 0.0244(9) Uani 1 1 d . . .
N2 N -0.0641(4) 0.2123(4) 0.9293(3) 0.0309(9) Uani 1 1 d . . .
C12 C 0.1533(4) 0.2034(4) 0.9395(3) 0.0241(8) Uani 1 1 d . . .
H12 H 0.2339 0.1699 0.9353 0.029 Uiso 1 1 calc R . .
C5 C 0.2553(4) 0.4484(5) 1.1093(3) 0.0252(9) Uani 1 1 d . . .
F4 F 0.5120(3) 0.8065(4) 1.0278(3) 0.0654(11) Uani 1 1 d . . .
C11 C 0.1281(4) 0.3282(5) 0.9721(3) 0.0266(9) Uani 1 1 d . . .
C6 C 0.2290(4) 0.3301(5) 1.1653(3) 0.0308(10) Uani 1 1 d . . .
H6A H 0.1464 0.2849 1.1336 0.037 Uiso 1 1 calc R . .
H6B H 0.2198 0.3673 1.2210 0.037 Uiso 1 1 calc R . .
F7 F 0.2208(5) 0.5520(5) 0.7266(2) 0.0764(13) Uani 1 1 d . . .
C2 C 0.3559(4) 0.6566(5) 1.1099(3) 0.0286(9) Uani 1 1 d . . .
C7 C 0.2455(4) 0.5592(5) 0.9678(3) 0.0278(9) Uani 1 1 d . . .
C8 C 0.3401(5) 0.2223(5) 1.1860(3) 0.0330(10) Uani 1 1 d . . .
H8A H 0.3479 0.1835 1.1310 0.050 Uiso 1 1 calc R . .
H8B H 0.3205 0.1488 1.2221 0.050 Uiso 1 1 calc R . .
H8C H 0.4219 0.2666 1.2179 0.050 Uiso 1 1 calc R . .
F2 F 0.3237(4) 0.9057(4) 0.9832(3) 0.0696(12) Uani 1 1 d . . .
C13 C 0.0278(4) 0.1351(5) 0.9131(3) 0.0257(9) Uani 1 1 d . . .
C3 C 0.3278(4) 0.6655(5) 1.0170(3) 0.0269(9) Uani 1 1 d . . .
F8 F 0.2406(6) 0.3681(4) 0.8028(3) 0.0980(19) Uani 1 1 d . . .
C14 C -0.0035(5) -0.0061(5) 0.8741(3) 0.0326(10) Uani 1 1 d . . .
H14A H -0.0956 -0.0257 0.8650 0.049 Uiso 1 1 calc R . .
H14B H 0.0491 -0.0744 0.9142 0.049 Uiso 1 1 calc R . .
H14C H 0.0156 -0.0102 0.8176 0.049 Uiso 1 1 calc R . .
F3 F 0.3915(4) 0.7732(5) 0.8972(2) 0.0734(13) Uani 1 1 d . . .
C10 C 0.1804(5) 0.5705(5) 0.8665(3) 0.0321(10) Uani 1 1 d . . .
F9 F 0.3875(4) 0.5239(7) 0.8413(3) 0.108(2) Uani 1 1 d . . .
C1 C 0.3868(5) 0.7902(6) 0.9817(3) 0.0350(11) Uani 1 1 d . . .
C9 C 0.2594(6) 0.5010(6) 0.8076(3) 0.0440(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'
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
C11 O1 N2 108.0(3) . . ?
C2 N1 C5 118.1(4) . . ?
C5 C4 C7 118.9(4) . . ?
C5 C4 C11 117.1(4) . . ?
C7 C4 C11 124.0(4) . . ?
C13 N2 O1 106.2(3) . . ?
C11 C12 C13 104.1(4) . . ?
N1 C5 C4 121.9(4) . . ?
N1 C5 C6 115.5(4) . . ?
C4 C5 C6 122.7(4) . . ?
C12 C11 O1 110.1(4) . . ?
C12 C11 C4 134.0(4) . . ?
O1 C11 C4 115.8(4) . . ?
C5 C6 C8 111.7(4) . . ?
N1 C2 F1 114.7(4) . . ?
N1 C2 C3 126.7(4) . . ?
F1 C2 C3 118.6(4) . . ?
C4 C7 C3 118.4(4) . . ?
C4 C7 C10 119.2(4) . . ?
C3 C7 C10 122.1(4) . . ?
N2 C13 C12 111.6(4) . . ?
N2 C13 C14 120.5(4) . . ?
C12 C13 C14 127.9(4) . . ?
C2 C3 C7 115.6(4) . . ?
C2 C3 C1 116.0(4) . . ?
C7 C3 C1 128.4(4) . . ?
F5 C10 F6 104.5(4) . . ?
F5 C10 C7 111.8(4) . . ?
F6 C10 C7 111.5(4) . . ?
F5 C10 C9 108.2(4) . . ?
F6 C10 C9 105.2(4) . . ?
C7 C10 C9 115.0(4) . . ?
F4 C1 F2 109.3(5) . . ?
F4 C1 F3 103.3(4) . . ?
F2 C1 F3 106.7(5) . . ?
F4 C1 C3 110.4(4) . . ?
F2 C1 C3 113.2(4) . . ?
F3 C1 C3 113.4(4) . . ?
F8 C9 F7 108.3(5) . . ?
F8 C9 F9 108.1(6) . . ?
F7 C9 F9 108.6(5) . . ?
F8 C9 C10 110.8(4) . . ?
F7 C9 C10 110.0(4) . . ?
F9 C9 C10 111.0(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
F1 C2 1.324(5) . ?
F5 C10 1.343(5) . ?
F6 C10 1.361(6) . ?
O1 C11 1.358(5) . ?
O1 N2 1.406(5) . ?
N1 C2 1.297(6) . ?
N1 C5 1.328(6) . ?
C4 C5 1.408(6) . ?
C4 C7 1.406(6) . ?
C4 C11 1.471(6) . ?
N2 C13 1.301(6) . ?
C12 C11 1.351(6) . ?
C12 C13 1.426(6) . ?
C5 C6 1.502(6) . ?
F4 C1 1.317(6) . ?
C6 C8 1.522(7) . ?
F7 C9 1.304(6) . ?
C2 C3 1.395(6) . ?
C7 C3 1.408(7) . ?
C7 C10 1.532(6) . ?
F2 C1 1.292(6) . ?
C13 C14 1.476(6) . ?
C3 C1 1.519(6) . ?
F8 C9 1.282(7) . ?
F3 C1 1.344(6) . ?
C10 C9 1.559(7) . ?
F9 C9 1.319(7) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 20574992
