#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:59:37 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180326 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/40/7154074.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_7154074
loop_
_publ_author_name
'Zhang, Li'
'Zeng, Qin'
'Mao, Ao'
'Wu, Ziang'
'Luo, Tian'
'Xiao, Yuanjing'
'Zhang, Junliang'
_publ_section_title
;
 NIS-mediated oxidative cyclization of N-(2-trifluoromethyl-3-alkynyl)
 hydroxylamines: a facile access to 4-trifluoromethyl-5-acylisoxazoles.
;
_journal_issue                   44
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8942
_journal_page_last               8946
_journal_paper_doi               10.1039/c4ob01790k
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C11 H5 F3 N2 O4'
_chemical_formula_weight         286.17
_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                 107.601(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.2169(9)
_cell_length_b                   15.8678(13)
_cell_length_c                   6.8648(6)
_cell_measurement_temperature    296(2)
_cell_volume                     1164.65(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0548
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            13493
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  0.9740
_exptl_absorpt_correction_T_min  0.9533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2054
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0519
_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)+(0.0502P)²+0.8402P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1429
_reflns_number_gt                1273
_reflns_number_total             2054
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob01790k2.cif
_cod_data_source_block           z
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 7154074.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7154074
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 0.6519(2) 0.1304(2) 0.5404(6) 0.1789(18) Uani 1 1 d .
F2 F 0.5204(3) 0.13147(18) 0.7080(4) 0.1221(10) Uani 1 1 d .
F3 F 0.5428(2) 0.23807(15) 0.5422(4) 0.0986(8) Uani 1 1 d .
O1 O 0.1904(3) 0.02018(17) 0.4746(5) 0.0885(9) Uani 1 1 d .
O2 O 0.0333(3) -0.05139(18) 0.2923(6) 0.1257(13) Uani 1 1 d .
O3 O 0.2761(2) 0.21913(17) 0.5270(4) 0.0792(8) Uani 1 1 d .
O4 O 0.26993(19) 0.08618(13) 0.1181(3) 0.0605(6) Uani 1 1 d .
N1 N 0.0879(3) 0.01441(19) 0.3456(6) 0.0753(9) Uani 1 1 d .
N2 N 0.3672(3) 0.0493(2) 0.0583(5) 0.0772(9) Uani 1 1 d .
C1 C 0.0264(3) 0.0931(2) 0.2550(5) 0.0558(8) Uani 1 1 d .
C2 C -0.1011(4) 0.0923(3) 0.1574(6) 0.0781(12) Uani 1 1 d .
H2A H -0.1461 0.0422 0.1390 0.094 Uiso 1 1 calc R
C3 C -0.1597(4) 0.1676(4) 0.0879(6) 0.0870(13) Uani 1 1 d .
H3A H -0.2453 0.1684 0.0211 0.104 Uiso 1 1 calc R
C4 C -0.0939(4) 0.2407(3) 0.1162(6) 0.0792(12) Uani 1 1 d .
H4A H -0.1351 0.2911 0.0699 0.095 Uiso 1 1 calc R
C5 C 0.0325(3) 0.2413(2) 0.2118(5) 0.0589(9) Uani 1 1 d .
H5A H 0.0762 0.2919 0.2296 0.071 Uiso 1 1 calc R
C6 C 0.0958(3) 0.16670(18) 0.2826(4) 0.0463(7) Uani 1 1 d .
C7 C 0.2333(3) 0.17336(19) 0.3830(5) 0.0509(8) Uani 1 1 d .
C8 C 0.3198(3) 0.12817(17) 0.2941(5) 0.0465(7) Uani 1 1 d .
C9 C 0.4455(3) 0.12134(18) 0.3510(5) 0.0526(8) Uani 1 1 d .
C10 C 0.4682(3) 0.0713(2) 0.1972(6) 0.0735(11) Uani 1 1 d .
H10A H 0.5478 0.0557 0.1957 0.088 Uiso 1 1 calc R
C11 C 0.5401(3) 0.1550(3) 0.5334(7) 0.0772(11) 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
C8 O4 N2 108.7(2)
O2 N1 O1 124.2(4)
O2 N1 C1 118.4(4)
O1 N1 C1 117.4(3)
C10 N2 O4 104.9(3)
C2 C1 C6 122.0(3)
C2 C1 N1 118.8(3)
C6 C1 N1 119.1(3)
C3 C2 C1 118.4(4)
C3 C2 H2A 120.8
C1 C2 H2A 120.8
C4 C3 C2 120.6(4)
C4 C3 H3A 119.7
C2 C3 H3A 119.7
C3 C4 C5 120.9(4)
C3 C4 H4A 119.5
C5 C4 H4A 119.5
C4 C5 C6 120.4(4)
C4 C5 H5A 119.8
C6 C5 H5A 119.8
C1 C6 C5 117.7(3)
C1 C6 C7 125.7(3)
C5 C6 C7 116.7(3)
O3 C7 C8 118.9(3)
O3 C7 C6 121.5(3)
C8 C7 C6 119.4(3)
O4 C8 C9 109.6(3)
O4 C8 C7 117.7(2)
C9 C8 C7 132.7(3)
C8 C9 C10 103.8(3)
C8 C9 C11 129.7(3)
C10 C9 C11 126.5(3)
N2 C10 C9 113.0(3)
N2 C10 H10A 123.5
C9 C10 H10A 123.5
F1 C11 F3 106.8(3)
F1 C11 F2 107.6(4)
F3 C11 F2 104.2(3)
F1 C11 C9 111.2(3)
F3 C11 C9 113.6(3)
F2 C11 C9 112.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C11 1.300(4)
F2 C11 1.336(5)
F3 C11 1.320(4)
O1 N1 1.224(4)
O2 N1 1.210(4)
O3 C7 1.204(3)
O4 C8 1.345(3)
O4 N2 1.405(3)
N1 C1 1.470(4)
N2 C10 1.289(4)
C1 C2 1.384(5)
C1 C6 1.385(4)
C2 C3 1.378(6)
C2 H2A 0.9300
C3 C4 1.358(6)
C3 H3A 0.9300
C4 C5 1.370(5)
C4 H4A 0.9300
C5 C6 1.390(4)
C5 H5A 0.9300
C6 C7 1.491(4)
C7 C8 1.479(4)
C8 C9 1.348(4)
C9 C10 1.405(4)
C9 C11 1.475(5)
C10 H10A 0.9300
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
C8 O4 N2 C10 -0.6(4)
O2 N1 C1 C2 17.0(5)
O1 N1 C1 C2 -161.1(3)
O2 N1 C1 C6 -167.5(3)
O1 N1 C1 C6 14.3(4)
C6 C1 C2 C3 -0.6(5)
N1 C1 C2 C3 174.7(3)
C1 C2 C3 C4 -0.4(6)
C2 C3 C4 C5 0.8(6)
C3 C4 C5 C6 -0.2(5)
C2 C1 C6 C5 1.2(4)
N1 C1 C6 C5 -174.1(3)
C2 C1 C6 C7 -179.1(3)
N1 C1 C6 C7 5.6(5)
C4 C5 C6 C1 -0.8(4)
C4 C5 C6 C7 179.5(3)
C1 C6 C7 O3 -123.7(4)
C5 C6 C7 O3 55.9(4)
C1 C6 C7 C8 61.3(4)
C5 C6 C7 C8 -119.0(3)
N2 O4 C8 C9 0.7(3)
N2 O4 C8 C7 178.9(3)
O3 C7 C8 O4 -171.6(3)
C6 C7 C8 O4 3.5(4)
O3 C7 C8 C9 6.1(5)
C6 C7 C8 C9 -178.8(3)
O4 C8 C9 C10 -0.5(4)
C7 C8 C9 C10 -178.4(3)
O4 C8 C9 C11 -178.8(3)
C7 C8 C9 C11 3.4(6)
O4 N2 C10 C9 0.3(4)
C8 C9 C10 N2 0.1(4)
C11 C9 C10 N2 178.4(4)
C8 C9 C11 F1 176.0(4)
C10 C9 C11 F1 -1.9(6)
C8 C9 C11 F3 -63.4(5)
C10 C9 C11 F3 118.7(4)
C8 C9 C11 F2 55.0(5)
C10 C9 C11 F2 -122.9(4)
