#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/68/4026810.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_4026810
loop_
_publ_author_name
'Feifei Zhao'
'Xin Liu'
'Rui Qi'
'Daisy Zhang-Negrerie'
'Jianhui Huang'
'Yunfei Du'
'Kang Zhao'
_publ_section_title
;
 Synthesis of 2-(Trifluoromethyl)oxazoles from β-Monosubstituted Enamines
 via PhI(OCOCF3)2-Mediated Trifluoroacetoxylation and Cyclization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10338
_journal_page_last               10344
_journal_paper_doi               10.1021/jo202070h
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C12 H8 F3 N O3'
_chemical_formula_sum            'C12 H8 F3 N O3'
_chemical_formula_weight         271.19
_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                 126.37(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.925(2)
_cell_length_b                   8.6147(17)
_cell_length_c                   15.619(5)
_cell_measurement_reflns_used    2895
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      2.35
_cell_volume                     1183.6(6)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       ω
_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  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9723
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.02
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.9712
_exptl_absorpt_correction_T_min  0.9592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.782
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2319
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.545
_refine_ls_R_factor_all          0.1304
_refine_ls_R_factor_gt           0.0756
_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)+(0.0798P)²+0.8788P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1941
_refine_ls_wR_factor_ref         0.2353
_reflns_number_gt                1182
_reflns_number_total             2319
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202070h_si_002.cif
_cod_data_source_block           1
_cod_original_cell_volume        1183.6(5)
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               4026810
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
F1 F 0.1986(6) 0.1986(8) 1.0970(5) 0.163(2) Uani 1 1 d U
F2 F 0.1189(5) 0.0192(6) 0.9899(4) 0.1284(17) Uani 1 1 d U
F3 F 0.0408(6) 0.2376(7) 0.9370(5) 0.161(2) Uani 1 1 d U
O1 O 0.3126(4) 0.0120(5) 0.7801(3) 0.0757(12) Uani 1 1 d .
O2 O 0.5415(5) 0.1162(5) 0.8550(4) 0.0903(14) Uani 1 1 d .
O3 O 0.2784(4) 0.1178(4) 0.9166(3) 0.0646(10) Uani 1 1 d .
N1 N 0.4069(5) 0.2712(5) 1.0585(4) 0.0643(12) Uani 1 1 d .
C1 C 0.6409(6) 0.3341(6) 1.0753(4) 0.0583(13) Uani 1 1 d .
C2 C 0.7462(6) 0.3049(7) 1.0555(5) 0.0748(17) Uani 1 1 d .
H2 H 0.7239 0.2338 1.0032 0.090 Uiso 1 1 calc R
C3 C 0.8850(7) 0.3810(8) 1.1130(6) 0.0857(19) Uani 1 1 d .
H3 H 0.9558 0.3587 1.0998 0.103 Uiso 1 1 calc R
C4 C 0.9191(6) 0.4875(8) 1.1881(5) 0.0816(18) Uani 1 1 d .
H4 H 1.0113 0.5403 1.2248 0.098 Uiso 1 1 calc R
C5 C 0.8169(7) 0.5166(8) 1.2095(5) 0.0863(19) Uani 1 1 d .
H5 H 0.8408 0.5878 1.2621 0.104 Uiso 1 1 calc R
C6 C 0.6780(6) 0.4413(7) 1.1537(5) 0.0732(16) Uani 1 1 d .
H6 H 0.6092 0.4626 1.1688 0.088 Uiso 1 1 calc R
C7 C 0.4930(6) 0.2550(6) 1.0186(4) 0.0588(13) Uani 1 1 d .
C8 C 0.4123(6) 0.1607(6) 0.9312(4) 0.0578(13) Uani 1 1 d .
C10 C 0.2868(6) 0.1902(6) 0.9956(5) 0.0650(15) Uani 1 1 d .
C12 C 0.4303(6) 0.0967(6) 0.8521(5) 0.0620(14) Uani 1 1 d .
C13 C 0.3227(8) -0.0645(8) 0.7016(5) 0.0883(19) Uani 1 1 d .
H13A H 0.4070 -0.1353 0.7368 0.132 Uiso 1 1 calc R
H13B H 0.3374 0.0119 0.6637 0.132 Uiso 1 1 calc R
H13C H 0.2305 -0.1207 0.6526 0.132 Uiso 1 1 calc R
C14 C 0.1628(8) 0.1619(8) 1.0058(7) 0.085(2) 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'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C12 O1 C13 116.6(4)
C10 O3 C8 103.6(4)
C10 N1 C7 104.8(5)
C6 C1 C2 118.2(5)
C6 C1 C7 118.7(5)
C2 C1 C7 123.0(5)
C3 C2 C1 120.4(6)
C3 C2 H2 119.8
C1 C2 H2 119.8
C4 C3 C2 120.9(6)
C4 C3 H3 119.5
C2 C3 H3 119.5
C3 C4 C5 119.4(6)
C3 C4 H4 120.3
C5 C4 H4 120.3
C4 C5 C6 120.7(6)
C4 C5 H5 119.6
C6 C5 H5 119.6
C1 C6 C5 120.3(6)
C1 C6 H6 119.8
C5 C6 H6 119.8
C8 C7 N1 107.2(4)
C8 C7 C1 134.7(5)
N1 C7 C1 118.1(5)
C7 C8 O3 108.3(4)
C7 C8 C12 137.2(5)
O3 C8 C12 114.5(5)
N1 C10 O3 116.1(4)
N1 C10 C14 126.6(5)
O3 C10 C14 117.3(5)
O2 C12 O1 124.3(5)
O2 C12 C8 123.6(5)
O1 C12 C8 112.1(4)
O1 C13 H13A 109.5
O1 C13 H13B 109.5
H13A C13 H13B 109.5
O1 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
F2 C14 F3 103.9(7)
F2 C14 F1 106.6(7)
F3 C14 F1 106.7(6)
F2 C14 C10 113.4(5)
F3 C14 C10 112.8(6)
F1 C14 C10 112.8(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C14 1.273(8)
F2 C14 1.289(7)
F3 C14 1.287(8)
O1 C12 1.318(7)
O1 C13 1.452(7)
O2 C12 1.200(6)
O3 C10 1.336(6)
O3 C8 1.391(5)
N1 C10 1.283(7)
N1 C7 1.409(6)
C1 C6 1.389(8)
C1 C2 1.380(7)
C1 C7 1.471(7)
C2 C3 1.386(8)
C2 H2 0.9300
C3 C4 1.357(9)
C3 H3 0.9300
C4 C5 1.365(8)
C4 H4 0.9300
C5 C6 1.383(8)
C5 H5 0.9300
C6 H6 0.9300
C7 C8 1.369(7)
C8 C12 1.469(7)
C10 C14 1.475(7)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
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
C6 C1 C2 C3 0.1(9)
C7 C1 C2 C3 -178.7(6)
C1 C2 C3 C4 -1.3(10)
C2 C3 C4 C5 2.0(11)
C3 C4 C5 C6 -1.5(10)
C2 C1 C6 C5 0.3(9)
C7 C1 C6 C5 179.3(5)
C4 C5 C6 C1 0.3(10)
C10 N1 C7 C8 -0.1(6)
C10 N1 C7 C1 -179.3(5)
C6 C1 C7 C8 170.5(6)
C2 C1 C7 C8 -10.7(9)
C6 C1 C7 N1 -10.7(7)
C2 C1 C7 N1 168.1(5)
N1 C7 C8 O3 -0.2(6)
C1 C7 C8 O3 178.7(5)
N1 C7 C8 C12 179.4(6)
C1 C7 C8 C12 -1.7(11)
C10 O3 C8 C7 0.5(5)
C10 O3 C8 C12 -179.2(4)
C7 N1 C10 O3 0.5(6)
C7 N1 C10 C14 176.5(6)
C8 O3 C10 N1 -0.6(6)
C8 O3 C10 C14 -177.0(5)
C13 O1 C12 O2 1.6(8)
C13 O1 C12 C8 -176.5(5)
C7 C8 C12 O2 3.6(10)
O3 C8 C12 O2 -176.8(5)
C7 C8 C12 O1 -178.4(6)
O3 C8 C12 O1 1.3(6)
N1 C10 C14 F2 -135.4(7)
O3 C10 C14 F2 40.6(9)
N1 C10 C14 F3 106.9(8)
O3 C10 C14 F3 -77.1(8)
N1 C10 C14 F1 -14.1(10)
O3 C10 C14 F1 161.9(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 29357550
