#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/76/7117629.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_7117629
loop_
_publ_author_name
'Duan, Yaya'
'Zhou, Bin'
'Lin, Jin-Hong'
'Xiao, Ji-Chang'
_publ_section_title
;
 Diastereoselective Johnson-Corey-Chaykovsky trifluoroethylidenation.
;
_journal_issue                   66
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              13127
_journal_page_last               13130
_journal_paper_doi               10.1039/c5cc04991a
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C9 H6 F3 N O3'
_chemical_formula_weight         233.15
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-02-09 deposited with the CCDC.
2015-07-06 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.8359(6)
_cell_length_b                   6.4223(8)
_cell_length_c                   30.645(4)
_cell_measurement_reflns_used    1964
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.971
_cell_measurement_theta_min      5.319
_cell_volume                     951.8(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            5407
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14145
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.311
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1850
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0483
_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)+(0.0858P)²+0.0954P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1383
_reflns_number_gt                1583
_reflns_number_total             1850
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc04991a2.cif
_cod_data_source_block           cd212733
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/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 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7117629
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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 -0.0856(6) 0.6497(4) 0.78352(8) 0.1142(9) Uani 1 1 d .
F2 F -0.4729(5) 0.6251(4) 0.81285(7) 0.1109(9) Uani 1 1 d .
F3 F -0.3973(6) 0.4718(4) 0.75356(6) 0.1222(10) Uani 1 1 d .
N1 N 0.5758(4) -0.1646(3) 0.95744(7) 0.0508(5) Uani 1 1 d .
O1 O -0.3934(5) 0.2057(4) 0.83343(8) 0.0897(8) Uani 1 1 d U
O2 O 0.6855(4) -0.0857(3) 0.98906(7) 0.0680(6) Uani 1 1 d .
O3 O 0.6322(5) -0.3388(3) 0.94406(7) 0.0718(6) Uani 1 1 d .
C1 C -0.2110(5) 0.3131(5) 0.86231(8) 0.0555(6) Uani 1 1 d .
H1 H -0.2886 0.4342 0.8774 0.067 Uiso 1 1 calc R
C2 C -0.1864(6) 0.3306(5) 0.81528(8) 0.0587(7) Uani 1 1 d .
H2 H -0.0304 0.2567 0.8020 0.070 Uiso 1 1 calc R
C3 C -0.2885(7) 0.5154(5) 0.79126(9) 0.0647(7) Uani 1 1 d .
C4 C -0.0139(5) 0.1842(4) 0.88777(7) 0.0485(6) Uani 1 1 d .
C5 C 0.1052(6) 0.2642(4) 0.92509(7) 0.0498(6) Uani 1 1 d .
H5 H 0.0560 0.3967 0.9346 0.060 Uiso 1 1 calc R
C6 C 0.2957(5) 0.1510(4) 0.94840(7) 0.0489(6) Uani 1 1 d .
H6 H 0.3760 0.2055 0.9735 0.059 Uiso 1 1 calc R
C7 C 0.3651(5) -0.0447(4) 0.93384(7) 0.0429(5) Uani 1 1 d .
C8 C 0.2442(6) -0.1306(4) 0.89754(8) 0.0559(6) Uani 1 1 d .
H8 H 0.2902 -0.2647 0.8887 0.067 Uiso 1 1 calc R
C9 C 0.0554(6) -0.0165(4) 0.87457(9) 0.0588(7) Uani 1 1 d .
H9 H -0.0276 -0.0734 0.8499 0.071 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.1157(16) 0.1059(17) 0.1208(18) 0.0470(15) -0.0073(15) -0.0224(16)
F2 0.1234(17) 0.1244(19) 0.0850(13) 0.0159(12) 0.0043(13) 0.0634(16)
F3 0.198(3) 0.0997(16) 0.0688(11) -0.0036(10) -0.0590(16) 0.004(2)
N1 0.0507(11) 0.0464(11) 0.0551(11) 0.0021(9) 0.0092(10) 0.0063(10)
O1 0.0787(14) 0.1016(18) 0.0889(14) 0.0301(13) -0.0270(13) -0.0361(14)
O2 0.0716(13) 0.0629(11) 0.0694(12) 0.0020(9) -0.0132(10) 0.0055(10)
O3 0.0812(13) 0.0542(10) 0.0801(13) -0.0046(10) 0.0091(11) 0.0238(11)
C1 0.0534(14) 0.0654(16) 0.0478(12) 0.0019(11) 0.0012(10) 0.0053(13)
C2 0.0630(15) 0.0658(15) 0.0474(12) -0.0006(12) 0.0000(12) 0.0021(14)
C3 0.0787(18) 0.0672(18) 0.0482(13) 0.0005(12) -0.0020(13) -0.0004(17)
C4 0.0464(12) 0.0562(14) 0.0427(11) 0.0005(10) 0.0072(9) -0.0016(11)
C5 0.0608(14) 0.0441(12) 0.0444(11) -0.0033(10) 0.0058(11) 0.0079(12)
C6 0.0575(14) 0.0470(12) 0.0422(11) -0.0064(10) 0.0008(10) 0.0019(12)
C7 0.0462(12) 0.0378(11) 0.0446(11) 0.0018(9) 0.0086(10) -0.0004(10)
C8 0.0722(16) 0.0384(11) 0.0570(13) -0.0073(11) 0.0013(13) -0.0021(13)
C9 0.0677(16) 0.0551(15) 0.0538(13) -0.0092(12) -0.0058(13) -0.0073(14)
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
O2 N1 O3 123.5(2)
O2 N1 C7 118.5(2)
O3 N1 C7 118.0(2)
C2 O1 C1 61.77(17)
O1 C1 C2 58.13(18)
O1 C1 C4 117.0(3)
C2 C1 C4 120.9(2)
O1 C1 H1 116.1
C2 C1 H1 116.1
C4 C1 H1 116.1
O1 C2 C1 60.10(18)
O1 C2 C3 114.8(3)
C1 C2 C3 121.9(3)
O1 C2 H2 116.0
C1 C2 H2 116.0
C3 C2 H2 116.0
F3 C3 F2 106.7(3)
F3 C3 F1 106.3(3)
F2 C3 F1 104.0(3)
F3 C3 C2 113.8(3)
F2 C3 C2 113.9(2)
F1 C3 C2 111.3(3)
C5 C4 C9 119.0(2)
C5 C4 C1 119.7(2)
C9 C4 C1 121.2(2)
C6 C5 C4 120.9(2)
C6 C5 H5 119.6
C4 C5 H5 119.6
C5 C6 C7 118.6(2)
C5 C6 H6 120.7
C7 C6 H6 120.7
C8 C7 C6 121.7(2)
C8 C7 N1 119.0(2)
C6 C7 N1 119.3(2)
C9 C8 C7 119.1(2)
C9 C8 H8 120.4
C7 C8 H8 120.4
C8 C9 C4 120.5(2)
C8 C9 H9 119.7
C4 C9 H9 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C3 1.328(4)
F2 C3 1.315(3)
F3 C3 1.300(3)
N1 O2 1.215(3)
N1 O3 1.222(3)
N1 C7 1.468(3)
O1 C2 1.398(4)
O1 C1 1.427(3)
C1 C2 1.451(3)
C1 C4 1.484(4)
C1 H1 0.9800
C2 C3 1.481(4)
C2 H2 0.9800
C4 C5 1.380(3)
C4 C9 1.392(4)
C5 C6 1.374(4)
C5 H5 0.9300
C6 C7 1.375(3)
C6 H6 0.9300
C7 C8 1.372(3)
C8 C9 1.366(4)
C8 H8 0.9300
C9 H9 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
C2 O1 C1 C4 -111.2(3)
C1 O1 C2 C3 -114.0(3)
C4 C1 C2 O1 104.5(3)
O1 C1 C2 C3 102.2(3)
C4 C1 C2 C3 -153.3(3)
O1 C2 C3 F3 -74.0(3)
C1 C2 C3 F3 -142.9(3)
O1 C2 C3 F2 48.7(4)
C1 C2 C3 F2 -20.2(4)
O1 C2 C3 F1 165.9(3)
C1 C2 C3 F1 97.0(4)
O1 C1 C4 C5 -160.0(2)
C2 C1 C4 C5 132.8(3)
O1 C1 C4 C9 20.5(4)
C2 C1 C4 C9 -46.8(4)
C9 C4 C5 C6 1.9(4)
C1 C4 C5 C6 -177.7(2)
C4 C5 C6 C7 -0.2(4)
C5 C6 C7 C8 -1.7(4)
C5 C6 C7 N1 177.7(2)
O2 N1 C7 C8 178.6(2)
O3 N1 C7 C8 -1.1(3)
O2 N1 C7 C6 -0.8(3)
O3 N1 C7 C6 179.4(2)
C6 C7 C8 C9 1.8(4)
N1 C7 C8 C9 -177.6(2)
C7 C8 C9 C4 0.0(4)
C5 C4 C9 C8 -1.8(4)
C1 C4 C9 C8 177.8(3)
