#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:32:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180304 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/18/7151848.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_7151848
loop_
_publ_author_name
'Moody, Justin D.'
'VanDerveer, Don'
'Smith Jr., Dennis W.'
'Iacono, Scott T.'
_publ_section_title
;
 Synthesis of internal fluorinated alkenes via facile aryloxylation of
 substituted phenols with aryl trifluorovinyl ethers
;
_journal_issue                   13
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              4842
_journal_paper_doi               10.1039/c1ob05041a
_journal_volume                  9
_journal_year                    2011
_chemical_formula_sum            'C16 H14 F2 O4'
_chemical_formula_weight         308.27
_chemical_name_systematic
;
?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.434(2)
_cell_length_b                   7.7903(16)
_cell_length_c                   17.852(4)
_cell_measurement_reflns_used    2772
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      26.3607
_cell_measurement_theta_min      3.0034
_cell_volume                     1451.1(5)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_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      153(2)
_diffrn_detector_area_resol_mean 14.6306
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
scan:
Number of images: 260
Slice: -40.0000 - 90.0000
Image width: 0.5000
Exp time: 80.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 45.0000
Phi: 0.0000
XTD: 27.7129
2theta: -0.1763
scan:
Number of images: 220
Slice: -30.0000 - 80.0000
Image width: 0.5000
Exp time: 80.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 45.0000
Phi: 90.0000
XTD: 27.7129
2theta: -0.1763

;
_diffrn_measurement_device
;
Mercury CCD
;
_diffrn_measurement_device_details
;
AFC8: Eulerian 3 circle
;
_diffrn_measurement_method       omega
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8770
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         3.00
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.9861
_exptl_absorpt_correction_T_min  0.9458
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R., (1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.697
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.066
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1270
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0875
_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)+(0.1431P)²+1.4540P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2396
_refine_ls_wR_factor_ref         0.2567
_reflns_number_gt                1032
_reflns_number_total             1270
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob05041a.txt
_cod_data_source_block           jm3
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        1451.0(5)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7151848
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'
'-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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4066(3) 0.1559(3) 0.54999(14) 0.0571(9) Uani 1 1 d . . .
O2 O 0.3397(3) 0.1629(3) 0.85712(14) 0.0561(9) Uani 1 1 d . . .
C1 C 0.3657(3) 0.1538(3) 0.78168(18) 0.0421(9) Uani 1 1 d . . .
C2 C 0.2801(3) 0.2409(4) 0.73563(19) 0.0454(9) Uani 1 1 d . . .
H2 H 0.2091 0.3017 0.7573 0.054 Uiso 1 1 calc R . .
C3 C 0.2966(3) 0.2402(4) 0.6593(2) 0.0478(10) Uani 1 1 d . . .
H3 H 0.2382 0.3013 0.6275 0.057 Uiso 1 1 calc R . .
C4 C 0.3982(3) 0.1505(4) 0.62889(18) 0.0421(9) Uani 1 1 d . . .
C5 C 0.4840(3) 0.0643(4) 0.67354(18) 0.0432(9) Uani 1 1 d . . .
H5 H 0.5545 0.0034 0.6515 0.052 Uiso 1 1 calc R . .
C6 C 0.4681(3) 0.0659(4) 0.75047(18) 0.0419(9) Uani 1 1 d . . .
H6 H 0.5277 0.0063 0.7821 0.050 Uiso 1 1 calc R . .
C7 C 0.4974(5) 0.0663(7) 0.5164(2) 0.0837(17) Uani 1 1 d . . .
C8 C 0.4112(4) 0.0544(5) 0.9051(2) 0.0632(11) Uani 1 1 d . . .
H8A H 0.4036 -0.0623 0.8884 0.095 Uiso 1 1 calc R . .
H8B H 0.3788 0.0638 0.9553 0.095 Uiso 1 1 calc R . .
H8C H 0.4997 0.0880 0.9042 0.095 Uiso 1 1 calc R . .
F1 F 0.6186(3) 0.1557(4) 0.50969(19) 0.0984(12) Uani 1 1 d . . .
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
O1 0.0651(16) 0.0559(15) 0.0502(15) 0.0029(11) 0.0030(11) 0.0190(12)
O2 0.0671(17) 0.0471(14) 0.0542(16) -0.0053(10) 0.0135(12) 0.0074(11)
C1 0.0449(17) 0.0305(15) 0.0509(19) -0.0055(12) 0.0096(13) -0.0046(12)
C2 0.0414(16) 0.0333(15) 0.062(2) -0.0048(14) 0.0073(13) 0.0021(12)
C3 0.0422(17) 0.0337(16) 0.068(2) -0.0002(14) 0.0002(14) 0.0045(13)
C4 0.0442(17) 0.0355(16) 0.0466(18) 0.0005(12) 0.0039(13) 0.0022(12)
C5 0.0407(16) 0.0392(16) 0.0496(18) -0.0009(13) 0.0054(13) 0.0039(12)
C6 0.0423(16) 0.0344(15) 0.0492(18) -0.0008(12) 0.0031(13) -0.0003(12)
C7 0.107(4) 0.090(3) 0.053(2) 0.005(2) 0.001(2) 0.049(3)
C8 0.078(3) 0.065(2) 0.046(2) -0.0056(17) 0.0008(17) 0.006(2)
F1 0.0727(18) 0.092(2) 0.130(3) 0.0228(17) -0.0160(15) -0.0363(15)
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'
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
C7 O1 C4 118.7(3) . . ?
C1 O2 C8 117.3(3) . . ?
O2 C1 C6 124.8(3) . . ?
O2 C1 C2 115.3(3) . . ?
C6 C1 C2 119.9(3) . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 O1 123.6(3) . . ?
C3 C4 O1 115.1(3) . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 119.7(3) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C7 C7 O1 135.7(8) 5_656 . ?
C7 C7 F1 109.7(6) 5_656 . ?
O1 C7 F1 114.2(4) . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
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
O1 C7 1.321(5) . ?
O1 C4 1.412(4) . ?
O2 C1 1.375(4) . ?
O2 C8 1.416(5) . ?
C1 C6 1.387(4) . ?
C1 C2 1.391(5) . ?
C2 C3 1.373(5) . ?
C2 H2 0.9600 . ?
C3 C4 1.381(4) . ?
C3 H3 0.9600 . ?
C4 C5 1.373(5) . ?
C5 C6 1.383(5) . ?
C5 H5 0.9600 . ?
C6 H6 0.9600 . ?
C7 C7 1.189(10) 5_656 ?
C7 F1 1.449(7) . ?
C8 H8A 0.9599 . ?
C8 H8B 0.9599 . ?
C8 H8C 0.9599 . ?
