# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_0524

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C14 H17 F O4'
_chemical_formula_moiety         'C14 H17 F O4'
_chemical_formula_weight         268.28
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.0995(8)
_cell_length_b                   8.0775(9)
_cell_length_c                   11.9904(15)
_cell_angle_alpha                89.359(4)
_cell_angle_beta                 77.992(4)
_cell_angle_gamma                74.584(4)
_cell_volume                     647.65(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5348
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      27.51
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284.00
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.661
_exptl_absorpt_correction_T_max  0.995

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            6366
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2933
_reflns_number_gt                2421
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1215
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         2933
_refine_ls_number_parameters     182
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0607P)²+0.1190P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.220
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
F1 F 0.47044(15) -0.02346(11) 0.76654(9) 0.0610(3) Uani 1.0 2 d . . .
O1 O 0.28357(14) 0.97809(12) 0.48309(8) 0.0413(3) Uani 1.0 2 d . . .
O2 O 0.51799(15) 0.77440(14) 0.54091(9) 0.0455(3) Uani 1.0 2 d . . .
O3 O -0.03550(14) 0.91974(12) 0.67674(9) 0.0403(3) Uani 1.0 2 d . . .
O4 O 0.00203(17) 0.45495(13) 0.67291(11) 0.0528(3) Uani 1.0 2 d . . .
C1 C 0.07225(18) 0.74321(15) 0.65922(10) 0.0316(3) Uani 1.0 2 d . . .
C2 C 0.19261(18) 0.69728(15) 0.75385(10) 0.0312(3) Uani 1.0 2 d . . .
C3 C 0.27062(18) 0.50380(15) 0.75316(10) 0.0310(3) Uani 1.0 2 d . . .
C4 C 0.4517(2) 0.42514(17) 0.78412(12) 0.0403(3) Uani 1.0 2 d . . .
C5 C 0.5224(3) 0.24838(18) 0.78871(13) 0.0451(4) Uani 1.0 2 d . . .
C6 C 0.4057(3) 0.15053(17) 0.76130(12) 0.0404(3) Uani 1.0 2 d . . .
C7 C 0.2304(2) 0.21805(17) 0.72618(11) 0.0392(3) Uani 1.0 2 d . . .
C8 C 0.16698(19) 0.39620(16) 0.71959(10) 0.0340(3) Uani 1.0 2 d . . .
C9 C -0.0777(2) 0.63516(18) 0.66512(13) 0.0422(4) Uani 1.0 2 d . . .
C10 C 0.0805(3) 0.78190(19) 0.87425(12) 0.0478(4) Uani 1.0 2 d . . .
C11 C 0.2214(3) 0.7520(3) 0.95717(13) 0.0632(5) Uani 1.0 2 d . . .
C12 C -0.1076(3) 0.7300(4) 0.92812(15) 0.0771(6) Uani 1.0 2 d . . .
C13 C 0.2120(2) 0.71140(16) 0.53823(10) 0.0349(3) Uani 1.0 2 d . . .
C14 C 0.34011(19) 0.83355(16) 0.51739(10) 0.0336(3) Uani 1.0 2 d . . .
H2 H 0.3100 0.7418 0.7314 0.0375 Uiso 1.0 2 calc R . .
H4 H 0.5279 0.4942 0.8024 0.0483 Uiso 1.0 2 calc R . .
H5 H 0.6434 0.1983 0.8094 0.0542 Uiso 1.0 2 calc R . .
H7 H 0.1561 0.1476 0.7074 0.0470 Uiso 1.0 2 calc R . .
H9A H -0.1860 0.6767 0.7308 0.0506 Uiso 1.0 2 calc R . .
H9B H -0.1345 0.6540 0.5976 0.0506 Uiso 1.0 2 calc R . .
H10 H 0.0395 0.9062 0.8651 0.0574 Uiso 1.0 2 calc R . .
H11A H 0.2536 0.6331 0.9753 0.0758 Uiso 1.0 2 calc R . .
H11B H 0.1575 0.8221 1.0258 0.0758 Uiso 1.0 2 calc R . .
H11C H 0.3418 0.7820 0.9226 0.0758 Uiso 1.0 2 calc R . .
H12A H -0.0811 0.6072 0.9218 0.0925 Uiso 1.0 2 calc R . .
H12B H -0.2126 0.7822 0.8894 0.0925 Uiso 1.0 2 calc R . .
H12C H -0.1479 0.7678 1.0072 0.0925 Uiso 1.0 2 calc R . .
H13A H 0.2969 0.5944 0.5306 0.0419 Uiso 1.0 2 calc R . .
H13B H 0.1312 0.7245 0.4810 0.0419 Uiso 1.0 2 calc R . .
H2A H 0.576(4) 0.859(3) 0.5305(18) 0.071(6) Uiso 1.0 2 d . . .
H3 H -0.107(3) 0.952(3) 0.6250(17) 0.064(6) Uiso 1.0 2 d . . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
F1 C6 1.3627(16) yes . .
O1 C14 1.2256(16) yes . .
O2 C14 1.3142(18) yes . .
O3 C1 1.4221(14) yes . .
O4 C8 1.3716(19) yes . .
O4 C9 1.4244(17) yes . .
C1 C2 1.5430(19) yes . .
C1 C9 1.537(3) yes . .
C1 C13 1.5584(16) yes . .
C2 C3 1.5124(17) yes . .
C2 C10 1.5619(18) yes . .
C3 C4 1.397(2) yes . .
C3 C8 1.389(2) yes . .
C4 C5 1.3865(19) yes . .
C5 C6 1.373(3) yes . .
C6 C7 1.370(3) yes . .
C7 C8 1.3955(18) yes . .
C10 C11 1.526(3) yes . .
C10 C12 1.520(3) yes . .
C13 C14 1.497(2) yes . .
O2 H2A 0.88(3) no . .
O3 H3 0.88(3) no . .
C2 H2 0.980 no . .
C4 H4 0.930 no . .
C5 H5 0.930 no . .
C7 H7 0.930 no . .
C9 H9A 0.970 no . .
C9 H9B 0.970 no . .
C10 H10 0.980 no . .
C11 H11A 0.960 no . .
C11 H11B 0.960 no . .
C11 H11C 0.960 no . .
C12 H12A 0.960 no . .
C12 H12B 0.960 no . .
C12 H12C 0.960 no . .
C13 H13A 0.970 no . .
C13 H13B 0.970 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C8 O4 C9 119.46(13) yes . . .
O3 C1 C2 107.81(11) yes . . .
O3 C1 C9 108.68(10) yes . . .
O3 C1 C13 109.81(10) yes . . .
C2 C1 C9 110.99(11) yes . . .
C2 C1 C13 111.48(10) yes . . .
C9 C1 C13 108.05(11) yes . . .
C1 C2 C3 108.58(11) yes . . .
C1 C2 C10 114.76(10) yes . . .
C3 C2 C10 113.64(11) yes . . .
C2 C3 C4 121.63(13) yes . . .
C2 C3 C8 121.37(12) yes . . .
C4 C3 C8 116.98(12) yes . . .
C3 C4 C5 122.73(15) yes . . .
C4 C5 C6 116.99(14) yes . . .
F1 C6 C5 118.21(14) yes . . .
F1 C6 C7 118.23(15) yes . . .
C5 C6 C7 123.54(13) yes . . .
C6 C7 C8 117.73(15) yes . . .
O4 C8 C3 123.06(12) yes . . .
O4 C8 C7 115.08(14) yes . . .
C3 C8 C7 121.79(13) yes . . .
O4 C9 C1 115.43(12) yes . . .
C2 C10 C11 110.80(12) yes . . .
C2 C10 C12 116.12(15) yes . . .
C11 C10 C12 109.31(14) yes . . .
C1 C13 C14 111.84(11) yes . . .
O1 C14 O2 122.42(14) yes . . .
O1 C14 C13 123.10(13) yes . . .
O2 C14 C13 114.47(11) yes . . .
C14 O2 H2A 106.5(14) no . . .
C1 O3 H3 111.3(13) no . . .
C1 C2 H2 106.416 no . . .
C3 C2 H2 106.417 no . . .
C10 C2 H2 106.422 no . . .
C3 C4 H4 118.636 no . . .
C5 C4 H4 118.631 no . . .
C4 C5 H5 121.509 no . . .
C6 C5 H5 121.498 no . . .
C6 C7 H7 121.132 no . . .
C8 C7 H7 121.142 no . . .
O4 C9 H9A 108.421 no . . .
O4 C9 H9B 108.414 no . . .
C1 C9 H9A 108.422 no . . .
C1 C9 H9B 108.417 no . . .
H9A C9 H9B 107.463 no . . .
C2 C10 H10 106.698 no . . .
C11 C10 H10 106.695 no . . .
C12 C10 H10 106.699 no . . .
C10 C11 H11A 109.471 no . . .
C10 C11 H11B 109.470 no . . .
C10 C11 H11C 109.475 no . . .
H11A C11 H11B 109.469 no . . .
H11A C11 H11C 109.474 no . . .
H11B C11 H11C 109.469 no . . .
C10 C12 H12A 109.475 no . . .
C10 C12 H12B 109.470 no . . .
C10 C12 H12C 109.469 no . . .
H12A C12 H12B 109.474 no . . .
H12A C12 H12C 109.471 no . . .
H12B C12 H12C 109.468 no . . .
C1 C13 H13A 109.247 no . . .
C1 C13 H13B 109.248 no . . .
C14 C13 H13A 109.249 no . . .
C14 C13 H13B 109.248 no . . .
H13A C13 H13B 107.924 no . . .

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
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C8 O4 C9 C1 26.11(17) no . . . .
C9 O4 C8 C3 -4.62(18) no . . . .
C9 O4 C8 C7 178.35(10) no . . . .
O3 C1 C2 C3 167.47(9) no . . . .
O3 C1 C2 C10 39.08(14) no . . . .
O3 C1 C9 O4 -167.50(10) no . . . .
O3 C1 C13 C14 51.83(14) no . . . .
C2 C1 C9 O4 -49.12(14) no . . . .
C9 C1 C2 C3 48.56(11) no . . . .
C9 C1 C2 C10 -79.83(12) no . . . .
C2 C1 C13 C14 -67.58(12) no . . . .
C13 C1 C2 C3 -71.94(12) no . . . .
C13 C1 C2 C10 159.67(10) no . . . .
C9 C1 C13 C14 170.21(9) no . . . .
C13 C1 C9 O4 73.39(14) no . . . .
C1 C2 C3 C4 148.50(10) no . . . .
C1 C2 C3 C8 -30.28(14) no . . . .
C1 C2 C10 C11 -171.17(11) no . . . .
C1 C2 C10 C12 63.36(15) no . . . .
C3 C2 C10 C11 63.03(16) no . . . .
C3 C2 C10 C12 -62.44(16) no . . . .
C10 C2 C3 C4 -82.48(15) no . . . .
C10 C2 C3 C8 98.74(14) no . . . .
C2 C3 C4 C5 177.27(10) no . . . .
C2 C3 C8 O4 7.70(17) no . . . .
C2 C3 C8 C7 -175.46(9) no . . . .
C4 C3 C8 O4 -171.13(10) no . . . .
C4 C3 C8 C7 5.70(16) no . . . .
C8 C3 C4 C5 -3.89(18) no . . . .
C3 C4 C5 C6 -0.1(2) no . . . .
C4 C5 C6 F1 -179.17(12) no . . . .
C4 C5 C6 C7 2.6(2) no . . . .
F1 C6 C7 C8 -179.11(10) no . . . .
C5 C6 C7 C8 -0.8(2) no . . . .
C6 C7 C8 O4 173.58(10) no . . . .
C6 C7 C8 C3 -3.48(17) no . . . .
C1 C13 C14 O1 -84.76(14) no . . . .
C1 C13 C14 O2 94.05(11) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
F1 C4 3.5973(18) no . .
O1 O3 3.0165(14) no . .
O1 C1 3.2273(16) no . .
O2 C1 3.2616(17) no . .
O2 C2 3.2432(16) no . .
O3 C10 2.7913(19) no . .
O3 C12 3.372(3) no . .
O3 C14 2.8581(15) no . .
O4 C2 2.933(2) no . .
O4 C6 3.5835(19) no . .
O4 C13 3.1121(19) no . .
C1 C8 2.8263(18) no . .
C1 C12 3.223(2) no . .
C2 C14 3.1072(17) no . .
C3 C6 2.7658(18) no . .
C3 C9 2.832(2) no . .
C3 C11 3.083(3) no . .
C3 C12 3.175(2) no . .
C3 C13 3.0993(18) no . .
C4 C7 2.762(3) no . .
C4 C10 3.3561(19) no . .
C4 C11 3.219(2) no . .
C5 C8 2.779(2) no . .
C8 C10 3.487(2) no . .
C8 C12 3.557(3) no . .
C8 C13 3.3664(19) no . .
C9 C10 3.302(3) no . .
C9 C12 3.204(3) no . .
F1 O1 3.2069(14) no . 2_666
F1 O2 3.0863(16) no . 1_545
F1 O3 3.3551(15) no . 1_645
F1 C2 3.3912(19) no . 1_545
F1 C10 3.548(2) no . 1_545
F1 C11 3.401(3) no . 1_545
F1 C14 3.5931(19) no . 1_545
O1 F1 3.2069(14) no . 2_666
O1 O1 3.2914(16) no . 2_676
O1 O2 2.7167(17) no . 2_676
O1 O3 2.8376(16) no . 2_576
O1 C5 3.5764(18) no . 2_666
O1 C6 3.2700(16) no . 2_666
O1 C7 3.4168(18) no . 1_565
O1 C14 3.4069(19) no . 2_676
O2 F1 3.0863(16) no . 1_565
O2 O1 2.7167(17) no . 2_676
O2 C7 3.3354(17) no . 2_666
O2 C8 3.4940(15) no . 2_666
O2 C9 3.427(2) no . 1_655
O2 C14 3.5896(19) no . 2_676
O3 F1 3.3551(15) no . 1_465
O3 O1 2.8376(16) no . 2_576
O3 C5 3.5494(16) no . 1_465
O3 C7 3.555(2) no . 1_565
C2 F1 3.3912(19) no . 1_565
C5 O1 3.5764(18) no . 2_666
C5 O3 3.5494(16) no . 1_645
C6 O1 3.2700(16) no . 2_666
C6 C14 3.4705(18) no . 2_666
C7 O1 3.4168(18) no . 1_545
C7 O2 3.3354(17) no . 2_666
C7 O3 3.555(2) no . 1_545
C8 O2 3.4940(15) no . 2_666
C9 O2 3.427(2) no . 1_455
C10 F1 3.548(2) no . 1_565
C11 F1 3.401(3) no . 1_565
C14 F1 3.5931(19) no . 1_565
C14 O1 3.4069(19) no . 2_676
C14 O2 3.5896(19) no . 2_676
C14 C6 3.4705(18) no . 2_666
F1 H5 2.5365 no . .
F1 H7 2.5279 no . .
O1 H2 3.5295 no . .
O1 H13A 3.1250 no . .
O1 H13B 2.5608 no . .
O1 H2A 2.23(3) no . .
O1 H3 2.99(2) no . .
O2 H2 2.5011 no . .
O2 H13A 2.4274 no . .
O2 H13B 3.1041 no . .
O3 H2 2.6994 no . .
O3 H9A 2.4928 no . .
O3 H9B 2.6696 no . .
O3 H10 2.4202 no . .
O3 H12B 2.9433 no . .
O3 H13A 3.2605 no . .
O3 H13B 2.7076 no . .
O4 H7 2.5006 no . .
O4 H12A 3.1188 no . .
O4 H12B 3.5236 no . .
O4 H13A 2.8787 no . .
O4 H13B 3.3087 no . .
C1 H10 2.7476 no . .
C1 H12A 3.3815 no . .
C1 H12B 3.0276 no . .
C2 H4 2.6785 no . .
C2 H9A 2.8061 no . .
C2 H9B 3.3588 no . .
C2 H11A 2.7994 no . .
C2 H11B 3.3632 no . .
C2 H11C 2.6444 no . .
C2 H12A 2.7296 no . .
C2 H12B 2.9017 no . .
C2 H12C 3.4131 no . .
C2 H13A 2.7026 no . .
C2 H13B 3.3865 no . .
C2 H3 3.18(2) no . .
C3 H5 3.2835 no . .
C3 H7 3.2722 no . .
C3 H9A 3.2365 no . .
C3 H10 3.3769 no . .
C3 H11A 2.8393 no . .
C3 H11C 3.2507 no . .
C3 H12A 2.8015 no . .
C3 H13A 2.7414 no . .
C4 H2 2.6102 no . .
C4 H11A 2.7463 no . .
C4 H11C 3.1699 no . .
C4 H13A 3.5802 no . .
C5 H7 3.2520 no . .
C6 H4 3.1924 no . .
C7 H5 3.2536 no . .
C8 H2 3.2278 no . .
C8 H4 3.2144 no . .
C8 H9A 2.8771 no . .
C8 H9B 3.1499 no . .
C8 H12A 2.9331 no . .
C8 H13A 2.8955 no . .
C9 H2 3.3373 no . .
C9 H12A 3.0786 no . .
C9 H12B 2.8207 no . .
C9 H13A 2.7468 no . .
C9 H13B 2.6010 no . .
C9 H3 2.56(2) no . .
C10 H4 3.3485 no . .
C10 H9A 3.0819 no . .
C11 H2 2.6459 no . .
C11 H4 2.9172 no . .
C11 H12A 2.8086 no . .
C11 H12B 3.2944 no . .
C11 H12C 2.5342 no . .
C12 H2 3.4059 no . .
C12 H9A 2.6053 no . .
C12 H11A 2.6528 no . .
C12 H11B 2.6737 no . .
C12 H11C 3.3145 no . .
C13 H2 2.5852 no . .
C13 H9A 3.3294 no . .
C13 H9B 2.5774 no . .
C13 H2A 3.11(3) no . .
C13 H3 2.591(17) no . .
C14 H2 2.6443 no . .
C14 H3 3.059(19) no . .
H2 H4 2.4457 no . .
H2 H10 2.3309 no . .
H2 H11A 3.0213 no . .
H2 H11B 3.4844 no . .
H2 H11C 2.3842 no . .
H2 H13A 2.7277 no . .
H2 H13B 3.5121 no . .
H2 H2A 3.0443 no . .
H2 H3 3.4818 no . .
H4 H5 2.3183 no . .
H4 H11A 2.5608 no . .
H4 H11C 2.6223 no . .
H9A H10 3.3620 no . .
H9A H12A 2.5628 no . .
H9A H12B 2.0442 no . .
H9A H12C 3.4826 no . .
H9A H13B 3.4384 no . .
H9A H3 2.6797 no . .
H9B H12B 3.5482 no . .
H9B H13A 2.9083 no . .
H9B H13B 2.3008 no . .
H9B H3 2.4981 no . .
H10 H11A 2.8133 no . .
H10 H11B 2.2843 no . .
H10 H11C 2.3549 no . .
H10 H12A 2.8015 no . .
H10 H12B 2.2405 no . .
H10 H12C 2.3938 no . .
H10 H3 3.2432 no . .
H11A H12A 2.6470 no . .
H11A H12B 3.5694 no . .
H11A H12C 2.7137 no . .
H11B H12A 3.1511 no . .
H11B H12B 3.4543 no . .
H11B H12C 2.3776 no . .
H11C H12C 3.4458 no . .
H12B H3 3.4584 no . .
H13A H2A 3.2775 no . .
H13A H3 3.4879 no . .
H13B H3 2.5341 no . .
F1 H2 2.5370 no . 1_545
F1 H9A 2.9065 no . 1_645
F1 H9B 3.5531 no . 1_645
F1 H10 3.2382 no . 1_545
F1 H11C 2.6058 no . 1_545
F1 H12B 3.0245 no . 1_645
F1 H12C 3.4488 no . 2_567
F1 H2A 2.88(2) no . 1_545
F1 H3 3.08(2) no . 1_645
O1 H7 2.8872 no . 1_565
O1 H9B 3.0948 no . 2_576
O1 H13B 3.2189 no . 2_576
O1 H2A 1.84(3) no . 2_676
O1 H3 1.96(3) no . 2_576
O2 H7 3.5328 no . 2_666
O2 H9A 3.3610 no . 1_655
O2 H9B 2.6271 no . 1_655
O2 H13A 2.9738 no . 2_666
O2 H2A 3.01(2) no . 2_676
O3 H5 2.9386 no . 1_465
O3 H7 2.6316 no . 1_565
O3 H13B 3.4164 no . 2_576
O4 H4 3.3335 no . 1_455
O4 H9B 3.2460 no . 2_566
O4 H13B 2.8135 no . 2_566
C1 H7 3.5461 no . 1_565
C4 H12C 3.5764 no . 2_567
C5 H11B 3.4385 no . 2_667
C5 H12C 3.2468 no . 2_567
C5 H3 3.334(17) no . 1_645
C6 H2 3.5793 no . 1_545
C6 H12C 2.9620 no . 2_567
C6 H2A 3.45(2) no . 1_545
C6 H2A 3.48(2) no . 2_666
C6 H3 3.460(18) no . 1_645
C7 H10 3.4260 no . 1_545
C7 H12C 3.1254 no . 2_567
C7 H2A 3.09(2) no . 2_666
C8 H12C 3.5094 no . 2_567
C8 H2A 3.526(19) no . 2_666
C9 H4 3.4030 no . 1_455
C9 H13B 3.5539 no . 2_566
C9 H2A 3.34(3) no . 1_455
C10 H11B 3.3007 no . 2_577
C11 H5 3.2035 no . 2_667
C11 H10 3.3716 no . 2_577
C11 H12A 3.5154 no . 2_567
C12 H11A 3.4722 no . 2_567
C12 H11B 3.5784 no . 2_577
C12 H12A 3.3774 no . 2_567
C13 H3 3.34(2) no . 2_576
C14 H7 3.2340 no . 1_565
C14 H2A 2.73(3) no . 2_676
C14 H3 2.87(2) no . 2_576
H2 F1 2.5370 no . 1_565
H2 C6 3.5793 no . 1_565
H2 H7 3.1980 no . 1_565
H2 H9A 3.4742 no . 1_655
H4 O4 3.3335 no . 1_655
H4 C9 3.4030 no . 1_655
H4 H9A 2.8062 no . 1_655
H4 H9B 3.5446 no . 1_655
H4 H11A 3.3731 no . 2_667
H5 O3 2.9386 no . 1_645
H5 C11 3.2035 no . 2_667
H5 H7 3.5042 no . 1_655
H5 H10 3.3374 no . 1_645
H5 H11A 3.2319 no . 2_667
H5 H11B 2.6384 no . 2_667
H5 H11C 3.2437 no . 2_667
H5 H12B 3.4309 no . 1_645
H5 H3 2.9295 no . 1_645
H7 O1 2.8872 no . 1_545
H7 O2 3.5328 no . 2_666
H7 O3 2.6316 no . 1_545
H7 C1 3.5461 no . 1_545
H7 C14 3.2340 no . 1_545
H7 H2 3.1980 no . 1_545
H7 H5 3.5042 no . 1_455
H7 H10 2.8612 no . 1_545
H7 H11B 3.4667 no . 2_567
H7 H12C 3.4830 no . 2_567
H7 H13B 3.3276 no . 2_566
H7 H2A 3.5505 no . 1_545
H7 H2A 3.0739 no . 2_666
H7 H3 3.0532 no . 1_545
H9A F1 2.9065 no . 1_465
H9A O2 3.3610 no . 1_455
H9A H2 3.4742 no . 1_455
H9A H4 2.8062 no . 1_455
H9A H11C 3.5454 no . 1_455
H9A H2A 3.3287 no . 1_455
H9B F1 3.5531 no . 1_465
H9B O1 3.0948 no . 2_576
H9B O2 2.6271 no . 1_455
H9B O4 3.2460 no . 2_566
H9B H4 3.5446 no . 1_455
H9B H9B 3.3262 no . 2_566
H9B H13A 3.1229 no . 2_566
H9B H13B 3.2021 no . 2_566
H9B H2A 2.5418 no . 1_455
H10 F1 3.2382 no . 1_565
H10 C7 3.4260 no . 1_565
H10 C11 3.3716 no . 2_577
H10 H5 3.3374 no . 1_465
H10 H7 2.8612 no . 1_565
H10 H10 3.4621 no . 2_577
H10 H11B 2.4814 no . 2_577
H10 H12C 3.3962 no . 2_577
H11A C12 3.4722 no . 2_567
H11A H4 3.3731 no . 2_667
H11A H5 3.2319 no . 2_667
H11A H12A 2.7149 no . 2_567
H11A H12C 3.5073 no . 2_567
H11B C5 3.4385 no . 2_667
H11B C10 3.3007 no . 2_577
H11B C12 3.5784 no . 2_577
H11B H5 2.6384 no . 2_667
H11B H7 3.4667 no . 2_567
H11B H10 2.4814 no . 2_577
H11B H11B 3.2810 no . 2_577
H11B H12B 3.5081 no . 2_577
H11B H12C 3.3167 no . 2_577
H11C F1 2.6058 no . 1_565
H11C H5 3.2437 no . 2_667
H11C H9A 3.5454 no . 1_655
H11C H12B 3.1054 no . 1_655
H11C H12C 3.5712 no . 2_577
H12A C11 3.5154 no . 2_567
H12A C12 3.3774 no . 2_567
H12A H11A 2.7149 no . 2_567
H12A H12A 2.7590 no . 2_567
H12A H12C 3.2314 no . 2_567
H12B F1 3.0245 no . 1_465
H12B H5 3.4309 no . 1_465
H12B H11B 3.5081 no . 2_577
H12B H11C 3.1054 no . 1_455
H12C F1 3.4488 no . 2_567
H12C C4 3.5764 no . 2_567
H12C C5 3.2468 no . 2_567
H12C C6 2.9620 no . 2_567
H12C C7 3.1254 no . 2_567
H12C C8 3.5094 no . 2_567
H12C H7 3.4830 no . 2_567
H12C H10 3.3962 no . 2_577
H12C H11A 3.5073 no . 2_567
H12C H11B 3.3167 no . 2_577
H12C H11C 3.5712 no . 2_577
H12C H12A 3.2314 no . 2_567
H13A O2 2.9738 no . 2_666
H13A H9B 3.1229 no . 2_566
H13A H13A 2.8265 no . 2_666
H13A H2A 3.5757 no . 2_666
H13B O1 3.2189 no . 2_576
H13B O3 3.4164 no . 2_576
H13B O4 2.8135 no . 2_566
H13B C9 3.5539 no . 2_566
H13B H7 3.3276 no . 2_566
H13B H9B 3.2021 no . 2_566
H13B H3 2.8714 no . 2_576
H2A F1 2.88(2) no . 1_565
H2A O1 1.84(3) no . 2_676
H2A O2 3.01(2) no . 2_676
H2A C6 3.45(2) no . 1_565
H2A C6 3.48(2) no . 2_666
H2A C7 3.09(2) no . 2_666
H2A C8 3.526(19) no . 2_666
H2A C9 3.34(3) no . 1_655
H2A C14 2.73(3) no . 2_676
H2A H7 3.5505 no . 1_565
H2A H7 3.0739 no . 2_666
H2A H9A 3.3287 no . 1_655
H2A H9B 2.5418 no . 1_655
H2A H13A 3.5757 no . 2_666
H2A H2A 2.42(3) no . 2_676
H2A H3 2.98(4) no . 1_655
H3 F1 3.08(2) no . 1_465
H3 O1 1.96(3) no . 2_576
H3 C5 3.334(17) no . 1_465
H3 C6 3.460(18) no . 1_465
H3 C13 3.34(2) no . 2_576
H3 C14 2.87(2) no . 2_576
H3 H5 2.9295 no . 1_465
H3 H7 3.0532 no . 1_565
H3 H13B 2.8714 no . 2_576
H3 H2A 2.98(4) no . 1_455
H3 H3 3.25(3) no . 2_576

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2A O1 . . 2_676 2.7167(17) 0.882 1.84(3) 174(2) no
O3 H3 O1 . . 2_576 2.8376(16) 0.876 1.96(3) 175.8(19) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_database_code_depnum_ccdc_archive 'CCDC 980275'
