#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:29:13 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180301 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/15/7151582.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_7151582
loop_
_publ_author_name
'DiMartino, Gianluca'
'Hursthouse, Michael B.'
'Light, Mark E.'
'Percy, Jonathan M.'
'Spencer, Neil S.'
'Tolley, Malcolm'
_publ_section_title
;
 Syntheses of selectively fluorinated cyclodecenones: the first
 deployment of the neutral oxy-Cope rearrangement in organofluorine
 chemistry
;
_journal_issue                   24
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              4423
_journal_paper_doi               10.1039/b311261f
_journal_volume                  1
_journal_year                    2003
_chemical_formula_sum            'C13 H17 F3 O2'
_chemical_formula_weight         262.27
_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                 96.703(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1391(5)
_cell_length_b                   8.2152(4)
_cell_length_c                   14.6853(5)
_cell_measurement_reflns_used    9829
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.02
_cell_measurement_theta_min      3.20
_cell_volume                     1214.85(9)
_computing_cell_refinement       'DENZO (Otwinowski and MInor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        'DENZO, COLLECT, MAXUS (Mackay et al., 1998)'
_computing_molecular_graphics    'CAMERON (Watkin, et al., 1993)'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Nonius Kappa CCD Area detector'
_diffrn_measurement_method       'φ and ω scans to fill the asymmetric unit'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR591 Rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9829
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.20
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing, 1997)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2130
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.111
_refine_ls_shift/su_mean         0.019
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0443P)²+0.1870P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0933
_reflns_number_gt                1701
_reflns_number_total             2130
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b311261f.txt
_cod_data_source_block           14b
_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.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' 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      P21/c
_cod_database_code               7151582
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
C1 C 0.87436(14) -0.0512(2) 0.70130(10) 0.0262(4) Uani 1 1 d . . .
C2 C 0.79193(14) 0.0619(2) 0.75493(10) 0.0254(4) Uani 1 1 d . . .
C3 C 0.61989(17) 0.0731(2) 0.84813(11) 0.0324(4) Uani 1 1 d . . .
C4 C 0.57531(16) 0.2401(2) 0.81435(11) 0.0325(4) Uani 1 1 d . . .
C5 C 0.68833(17) 0.3314(2) 0.77760(12) 0.0319(4) Uani 1 1 d . . .
C6 C 0.75902(15) 0.2285(2) 0.71058(10) 0.0267(4) Uani 1 1 d . . .
C7 C 0.68235(14) 0.22007(19) 0.61499(10) 0.0267(4) Uani 1 1 d . . .
C8 C 0.74741(14) 0.1215(2) 0.54768(10) 0.0266(4) Uani 1 1 d . . .
C9 C 0.71133(15) -0.0228(2) 0.51567(10) 0.0268(4) Uani 1 1 d . . .
C10 C 0.79037(18) -0.1341(2) 0.46259(11) 0.0329(4) Uani 1 1 d . . .
C11 C 0.80906(18) -0.3010(2) 0.50877(12) 0.0331(4) Uani 1 1 d . . .
C12 C 0.89152(17) -0.3052(2) 0.60284(11) 0.0310(4) Uani 1 1 d . . .
C13 C 0.82942(16) -0.2234(2) 0.68122(11) 0.0284(4) Uani 1 1 d . . .
O1 O 0.98116(10) -0.00087(15) 0.68330(7) 0.0344(3) Uani 1 1 d . . .
O2 O 0.67704(9) -0.01810(13) 0.77860(7) 0.0281(3) Uani 1 1 d . . .
F1 F 0.86234(9) 0.19248(12) 0.52942(6) 0.0375(3) Uani 1 1 d . . .
F2 F 0.66532(10) 0.37706(12) 0.58226(6) 0.0415(3) Uani 1 1 d . . .
F3 F 0.55670(8) 0.16122(11) 0.61718(6) 0.0326(3) Uani 1 1 d . . .
H2 H 0.8511(14) 0.0848(19) 0.8110(11) 0.026(4) Uiso 1 1 d . . .
H3A H 0.6897(16) 0.082(2) 0.9048(11) 0.034(4) Uiso 1 1 d . . .
H3B H 0.5470(17) 0.006(2) 0.8655(11) 0.034(4) Uiso 1 1 d . . .
H4A H 0.5445(15) 0.301(2) 0.8652(11) 0.031(4) Uiso 1 1 d . . .
H4B H 0.5002(16) 0.228(2) 0.7661(11) 0.033(4) Uiso 1 1 d . . .
H5A H 0.6573(16) 0.432(2) 0.7494(12) 0.037(5) Uiso 1 1 d . . .
H5B H 0.7534(17) 0.357(2) 0.8266(12) 0.037(5) Uiso 1 1 d . . .
H6 H 0.8417(17) 0.280(2) 0.7017(11) 0.035(4) Uiso 1 1 d . . .
H9 H 0.6288(16) -0.066(2) 0.5334(11) 0.034(4) Uiso 1 1 d . . .
H10A H 0.7437(17) -0.148(2) 0.4019(13) 0.042(5) Uiso 1 1 d . . .
H10B H 0.8744(17) -0.083(2) 0.4549(11) 0.030(4) Uiso 1 1 d . . .
H11A H 0.8498(17) -0.372(2) 0.4673(13) 0.042(5) Uiso 1 1 d . . .
H11B H 0.7213(17) -0.3505(19) 0.5135(11) 0.029(4) Uiso 1 1 d . . .
H12A H 0.9787(16) -0.256(2) 0.5973(11) 0.028(4) Uiso 1 1 d . . .
H12B H 0.9089(15) -0.418(2) 0.6174(11) 0.033(4) Uiso 1 1 d . . .
H13A H 0.8545(16) -0.284(2) 0.7375(12) 0.033(4) Uiso 1 1 d . . .
H13B H 0.7312(16) -0.228(2) 0.6729(10) 0.028(4) Uiso 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'
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
O1 C1 C13 122.25(14) . . ?
O1 C1 C2 117.36(14) . . ?
C13 C1 C2 120.08(13) . . ?
O2 C2 C1 111.08(13) . . ?
O2 C2 C6 111.94(12) . . ?
C1 C2 C6 115.35(12) . . ?
O2 C3 C4 111.66(13) . . ?
C3 C4 C5 110.85(14) . . ?
C4 C5 C6 112.51(14) . . ?
C7 C6 C2 114.33(13) . . ?
C7 C6 C5 112.88(13) . . ?
C2 C6 C5 108.26(13) . . ?
F3 C7 F2 105.05(11) . . ?
F3 C7 C8 108.03(12) . . ?
F2 C7 C8 108.90(12) . . ?
F3 C7 C6 111.77(12) . . ?
F2 C7 C6 107.92(12) . . ?
C8 C7 C6 114.70(13) . . ?
C9 C8 F1 121.84(14) . . ?
C9 C8 C7 127.04(14) . . ?
F1 C8 C7 110.75(13) . . ?
C8 C9 C10 126.60(15) . . ?
C9 C10 C11 111.30(14) . . ?
C12 C11 C10 116.54(15) . . ?
C11 C12 C13 116.09(14) . . ?
C1 C13 C12 114.75(14) . . ?
C2 O2 C3 110.07(12) . . ?
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
C1 O1 1.2166(18) . ?
C1 C13 1.505(2) . ?
C1 C2 1.528(2) . ?
C2 O2 1.4157(18) . ?
C2 C6 1.536(2) . ?
C3 O2 1.4414(19) . ?
C3 C4 1.510(3) . ?
C4 C5 1.521(2) . ?
C5 C6 1.537(2) . ?
C6 C7 1.525(2) . ?
C7 F3 1.3665(17) . ?
C7 F2 1.3801(18) . ?
C7 C8 1.490(2) . ?
C8 C9 1.311(2) . ?
C8 F1 1.3575(17) . ?
C9 C10 1.494(2) . ?
C10 C11 1.531(2) . ?
C11 C12 1.529(2) . ?
C12 C13 1.530(2) . ?
