#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/40/4024063.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_4024063
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            'C12 H10 F4 N2 O'
_chemical_formula_weight         274.22
_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                 100.790(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.1074(14)
_cell_length_b                   17.390(5)
_cell_length_c                   12.980(3)
_cell_measurement_reflns_used    2185
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.34
_cell_volume                     1132.5(5)
_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 0.924
_diffrn_measured_fraction_theta_max 0.924
_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  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0521
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6710
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.989
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2600
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0580
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0865P)²+0.3845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1520
_refine_ls_wR_factor_ref         0.1625
_reflns_number_gt                2136
_reflns_number_total             2600
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070564msi20070514_030908.cif
_cod_data_source_block           r20i
_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/c'
_cod_database_code               4024063
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
F4 F 0.3601(3) 0.60317(8) 0.40334(10) 0.0247(3) Uani 1 1 d . . .
F1 F 0.9657(3) 0.50017(8) 0.29503(10) 0.0239(3) Uani 1 1 d . . .
O1 O 0.4391(3) 0.73023(10) -0.05506(11) 0.0228(4) Uani 1 1 d . . .
F2 F 0.5637(3) 0.49746(8) 0.39100(11) 0.0271(4) Uani 1 1 d . . .
F3 F 0.7823(3) 0.59544(11) 0.46102(10) 0.0376(4) Uani 1 1 d . . .
N2 N 0.3377(3) 0.70520(10) 0.24685(13) 0.0153(4) Uani 1 1 d . . .
N1 N 0.8927(3) 0.56338(11) 0.14288(14) 0.0175(4) Uani 1 1 d . . .
C4 C 0.7583(4) 0.61530(13) 0.07758(15) 0.0149(4) Uani 1 1 d . . .
C7 C 0.5625(4) 0.66361(12) 0.10802(15) 0.0143(4) Uani 1 1 d . . .
C8 C 0.5101(4) 0.65550(12) 0.21167(15) 0.0139(4) Uani 1 1 d . . .
C11 C 0.2353(4) 0.76957(13) 0.08310(16) 0.0182(5) Uani 1 1 d . . .
H11 H 0.1385 0.8074 0.0418 0.022 Uiso 1 1 calc R . .
C2 C 0.6414(4) 0.59636(12) 0.27676(15) 0.0153(4) Uani 1 1 d . . .
C12 C 0.4141(4) 0.72243(13) 0.03818(15) 0.0158(4) Uani 1 1 d . . .
C3 C 0.8282(4) 0.55543(13) 0.23562(16) 0.0172(4) Uani 1 1 d . . .
C5 C 0.8297(4) 0.61562(13) -0.02988(16) 0.0174(5) Uani 1 1 d . . .
H5A H 1.0077 0.5949 -0.0257 0.021 Uiso 1 1 calc R . .
H5B H 0.8291 0.6680 -0.0554 0.021 Uiso 1 1 calc R . .
C9 C 0.2018(4) 0.76113(13) 0.18361(16) 0.0166(4) Uani 1 1 d . . .
C6 C 0.6305(4) 0.56735(14) -0.10640(16) 0.0198(5) Uani 1 1 d . . .
H6A H 0.6466 0.5143 -0.0857 0.030 Uiso 1 1 calc R . .
H6B H 0.6673 0.5727 -0.1759 0.030 Uiso 1 1 calc R . .
H6C H 0.4526 0.5849 -0.1055 0.030 Uiso 1 1 calc R . .
C1 C 0.5866(4) 0.57332(13) 0.38311(16) 0.0187(5) Uani 1 1 d . . .
C10 C 0.0179(4) 0.81001(13) 0.23280(17) 0.0198(5) Uani 1 1 d . . .
H10A H -0.0796 0.8438 0.1809 0.030 Uiso 1 1 calc R . .
H10B H 0.1198 0.8399 0.2884 0.030 Uiso 1 1 calc R . .
H10C H -0.1045 0.7777 0.2606 0.030 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'
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
C8 N2 C9 122.09(17) . . ?
C3 N1 C4 117.71(18) . . ?
N1 C4 C7 121.93(18) . . ?
N1 C4 C5 113.89(18) . . ?
C7 C4 C5 124.16(19) . . ?
C4 C7 C8 118.08(18) . . ?
C4 C7 C12 123.13(18) . . ?
C8 C7 C12 118.78(18) . . ?
N2 C8 C2 121.36(18) . . ?
N2 C8 C7 119.79(18) . . ?
C2 C8 C7 118.84(18) . . ?
C9 C11 C12 122.4(2) . . ?
C3 C2 C8 115.41(18) . . ?
C3 C2 C1 118.53(19) . . ?
C8 C2 C1 126.02(19) . . ?
O1 C12 C11 121.5(2) . . ?
O1 C12 C7 122.42(19) . . ?
C11 C12 C7 116.10(18) . . ?
N1 C3 F1 114.03(18) . . ?
N1 C3 C2 127.8(2) . . ?
F1 C3 C2 118.21(18) . . ?
C4 C5 C6 110.59(16) . . ?
C11 C9 N2 120.72(19) . . ?
C11 C9 C10 123.5(2) . . ?
N2 C9 C10 115.77(18) . . ?
F2 C1 F4 106.15(17) . . ?
F2 C1 F3 106.90(18) . . ?
F4 C1 F3 106.93(18) . . ?
F2 C1 C2 111.52(17) . . ?
F4 C1 C2 113.01(17) . . ?
F3 C1 C2 111.93(17) . . ?
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
F4 C1 1.338(3) . ?
F1 C3 1.345(2) . ?
O1 C12 1.248(2) . ?
F2 C1 1.330(3) . ?
F3 C1 1.338(2) . ?
N2 C8 1.372(3) . ?
N2 C9 1.374(3) . ?
N1 C3 1.313(3) . ?
N1 C4 1.337(3) . ?
C4 C7 1.418(3) . ?
C4 C5 1.506(3) . ?
C7 C8 1.427(3) . ?
C7 C12 1.478(3) . ?
C8 C2 1.417(3) . ?
C11 C9 1.355(3) . ?
C11 C12 1.430(3) . ?
C2 C3 1.376(3) . ?
C2 C1 1.513(3) . ?
C5 C6 1.532(3) . ?
C9 C10 1.495(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 20575328
