#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:08:31 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180289 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/03/7150340.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_7150340
loop_
_publ_author_name
'Arany, Andrea'
'Crowley, Patrick J.'
'Fawcett, John'
'Hursthouse, Michael B.'
'Kariuki, Benson M.'
'Light, Mark E.'
'Moralee, Andrew C.'
'Percy, Jonathan M.'
'Salafia, Vittoria'
_publ_section_title
;
 Highly-functionalised difluorinated (hydroxymethyl)conduritol
 analogues via the Diels-Alder reactions of a difluorinated dienophile.
;
_journal_issue                   4
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              455
_journal_page_last               465
_journal_paper_doi               10.1039/b314314g
_journal_volume                  2
_journal_year                    2004
_chemical_formula_moiety         'C11 H16 F2 O3'
_chemical_formula_sum            'C11 H16 F2 O3'
_chemical_formula_weight         234.24
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 98.998(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8294(12)
_cell_length_b                   8.3435(13)
_cell_length_c                   13.9113(16)
_cell_measurement_reflns_used    1818
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.7
_cell_measurement_theta_min      2.75
_cell_volume                     1126.8(3)
_computing_cell_refinement       'MSC Software'
_computing_data_collection       'MSC Software'
_computing_data_reduction        'MSC Software'
_computing_structure_refinement  SHELXL97
_computing_structure_solution    SHELXS86
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.900
_diffrn_measured_fraction_theta_max 0.900
_diffrn_measurement_device_type  'Rigaku R-axis IIc Image plate'
_diffrn_measurement_method       'Image plate slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0792
_diffrn_reflns_av_sigmaI/netI    0.0798
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8756
_diffrn_reflns_theta_full        28.70
_diffrn_reflns_theta_max         28.70
_diffrn_reflns_theta_min         2.75
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.9650
_exptl_absorpt_correction_T_min  0.9537
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2615
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0646
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1341P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1743
_refine_ls_wR_factor_ref         0.2216
_reflns_number_gt                1818
_reflns_number_total             2615
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b314314g.txt
_cod_data_source_block           31
_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.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7150340
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O1 O 0.68104(16) 0.34485(18) 0.50665(11) 0.0299(4) Uani 1 1 d . . .
O2 O 0.88700(17) 0.43949(19) 0.58690(11) 0.0352(4) Uani 1 1 d . . .
O3 O 0.8272(2) 0.4511(2) 0.36262(12) 0.0369(4) Uani 1 1 d . . .
F1 F 0.70824(17) 0.04677(18) 0.57809(10) 0.0436(4) Uani 1 1 d . . .
F2 F 0.85039(16) -0.02924(16) 0.48284(11) 0.0438(4) Uani 1 1 d . . .
C1 C 0.7858(2) 0.2454(2) 0.47679(14) 0.0282(5) Uani 1 1 d . . .
C2 C 0.7390(3) 0.0718(3) 0.48627(16) 0.0328(5) Uani 1 1 d . . .
C3 C 0.6205(2) 0.0231(3) 0.41178(17) 0.0350(5) Uani 1 1 d . . .
H3 H 0.5720 -0.0727 0.4210 0.042 Uiso 1 1 calc R . .
C4 C 0.5812(2) 0.1109(3) 0.33270(16) 0.0361(5) Uani 1 1 d . . .
H4 H 0.5043 0.0748 0.2879 0.043 Uiso 1 1 calc R . .
C5 C 0.6500(2) 0.2632(3) 0.30942(16) 0.0354(5) Uani 1 1 d . . .
H5A H 0.5916 0.3551 0.3220 0.043 Uiso 1 1 calc R . .
H5B H 0.6575 0.2639 0.2393 0.043 Uiso 1 1 calc R . .
C6 C 0.7951(2) 0.2854(3) 0.36915(15) 0.0304(5) Uani 1 1 d . . .
C7 C 0.9012(3) 0.1839(3) 0.32598(17) 0.0410(6) Uani 1 1 d . . .
H7A H 0.8696 0.0724 0.3196 0.062 Uiso 1 1 calc R . .
H7B H 0.9901 0.1887 0.3690 0.062 Uiso 1 1 calc R . .
H7C H 0.9115 0.2258 0.2617 0.062 Uiso 1 1 calc R . .
C8 C 0.9159(2) 0.2858(3) 0.55032(15) 0.0316(5) Uani 1 1 d . . .
H8A H 0.9310 0.2056 0.6033 0.038 Uiso 1 1 calc R . .
H8B H 0.9985 0.2897 0.5178 0.038 Uiso 1 1 calc R . .
C9 C 0.7394(2) 0.4530(3) 0.58263(15) 0.0318(5) Uani 1 1 d . . .
C10 C 0.6972(3) 0.6220(3) 0.5531(2) 0.0437(6) Uani 1 1 d . . .
H10A H 0.5970 0.6322 0.5474 0.066 Uiso 1 1 calc R . .
H10B H 0.7257 0.6465 0.4902 0.066 Uiso 1 1 calc R . .
H10C H 0.7417 0.6971 0.6024 0.066 Uiso 1 1 calc R . .
C11 C 0.6956(3) 0.4018(4) 0.67754(18) 0.0480(7) Uani 1 1 d . . .
H11A H 0.5949 0.3945 0.6691 0.072 Uiso 1 1 calc R . .
H11B H 0.7278 0.4808 0.7281 0.072 Uiso 1 1 calc R . .
H11C H 0.7358 0.2969 0.6968 0.072 Uiso 1 1 calc R . .
H12 H 0.909(3) 0.464(4) 0.373(2) 0.042(8) 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
C1 O1 C9 110.72(16) . . ?
C8 O2 C9 108.07(16) . . ?
O1 C1 C2 106.48(18) . . ?
O1 C1 C8 103.88(16) . . ?
C2 C1 C8 112.19(17) . . ?
O1 C1 C6 108.01(16) . . ?
C2 C1 C6 110.50(17) . . ?
C8 C1 C6 115.12(18) . . ?
F1 C2 F2 103.25(17) . . ?
F1 C2 C3 110.1(2) . . ?
F2 C2 C3 110.22(18) . . ?
F1 C2 C1 109.66(17) . . ?
F2 C2 C1 108.80(19) . . ?
C3 C2 C1 114.23(18) . . ?
C4 C3 C2 121.4(2) . . ?
C3 C4 C5 124.3(2) . . ?
C4 C5 C6 113.27(19) . . ?
O3 C6 C7 109.84(19) . . ?
O3 C6 C5 106.08(18) . . ?
C7 C6 C5 110.46(18) . . ?
O3 C6 C1 108.49(17) . . ?
C7 C6 C1 113.92(18) . . ?
C5 C6 C1 107.73(18) . . ?
O2 C8 C1 103.99(17) . . ?
O1 C9 O2 105.28(17) . . ?
O1 C9 C10 108.95(18) . . ?
O2 C9 C10 108.35(19) . . ?
O1 C9 C11 109.21(19) . . ?
O2 C9 C11 111.3(2) . . ?
C10 C9 C11 113.5(2) . . ?
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 C1 1.433(3) . ?
O1 C9 1.439(2) . ?
O2 C8 1.425(3) . ?
O2 C9 1.447(3) . ?
O3 C6 1.424(3) . ?
F1 C2 1.374(3) . ?
F2 C2 1.389(3) . ?
C1 C2 1.532(3) . ?
C1 C8 1.545(3) . ?
C1 C6 1.551(3) . ?
C2 C3 1.489(3) . ?
C3 C4 1.328(3) . ?
C4 C5 1.498(3) . ?
C5 C6 1.545(3) . ?
C6 C7 1.536(3) . ?
C9 C10 1.509(3) . ?
C9 C11 1.513(3) . ?
