# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_8
_database_code_depnum_ccdc_archive 'CCDC 1817386'
_audit_update_record             
;
2018-01-16 deposited with the CCDC.
2018-02-19 downloaded from the CCDC.
;
_audit_creation_date             2018-01-08
_audit_creation_method           'by CrystalStructure 4.2'


_chemical_formula_sum            'C12 H12 F4 O'
_chemical_formula_moiety         'C12 H12 F4 O'
_chemical_formula_weight         248.22
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   6.0422(12)
_cell_length_b                   11.778(3)
_cell_length_c                   15.448(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1099.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1219
_cell_measurement_theta_min      40.50
_cell_measurement_theta_max      68.00
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512.00
_exptl_absorpt_coefficient_mu    1.232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.740
_exptl_absorpt_correction_T_max  0.976

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

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            11746
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_theta_max         68.225
_diffrn_reflns_theta_min         4.721
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1998
_reflns_number_gt                1911
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.680
_reflns_Friedel_fraction_max     0.987
_reflns_Friedel_fraction_full    0.991

#==============================================================================
# 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).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0841
_refine_ls_wR_factor_gt          0.0833
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         1998
_refine_ls_number_parameters     158
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0548P)²+0.0186P] 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         0.14
_refine_diff_density_min         -0.13
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 746 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(6)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 0.1835(2) 0.35526(9) 0.70271(7) 0.0435(3) Uani 1 1 d . . . . .
F3 F 0.4378(3) 0.39588(12) 0.84392(8) 0.0603(4) Uani 1 1 d . . . . .
F5 F -0.1757(3) 0.16099(13) 0.91137(9) 0.0629(4) Uani 1 1 d . . . . .
F6 F -0.1692(2) 0.22179(12) 0.74306(8) 0.0496(3) Uani 1 1 d . . . . .
O1 O 0.3458(3) 0.07006(12) 0.75558(9) 0.0444(4) Uani 1 1 d D . . . .
C1 C 0.1983(3) 0.15263(15) 0.71971(11) 0.0308(4) Uani 1 1 d . . . . .
C2 C 0.3121(3) 0.26799(16) 0.73672(12) 0.0337(4) Uani 1 1 d . . . . .
H2 H 0.460046 0.268441 0.707739 0.040 Uiso 1 1 calc R U . . .
C3 C 0.3434(4) 0.28774(18) 0.83282(12) 0.0400(5) Uani 1 1 d . . . . .
H3 H 0.446149 0.228930 0.856567 0.048 Uiso 1 1 calc R U . . .
C4 C 0.1270(4) 0.28358(19) 0.88183(12) 0.0411(5) Uani 1 1 d . . . . .
H4A H 0.024930 0.342781 0.860046 0.049 Uiso 1 1 calc R U . . .
H4B H 0.153002 0.296994 0.944271 0.049 Uiso 1 1 calc R U . . .
C5 C 0.0284(4) 0.16693(18) 0.86791(13) 0.0425(5) Uani 1 1 d . . . . .
H5 H 0.130933 0.108123 0.891826 0.051 Uiso 1 1 calc R U . . .
C6 C -0.0145(3) 0.14263(17) 0.77308(12) 0.0393(4) Uani 1 1 d . . . . .
H6 H -0.076463 0.064322 0.766775 0.047 Uiso 1 1 calc R U . . .
C7 C 0.1634(4) 0.13085(15) 0.62307(11) 0.0328(4) Uani 1 1 d . . . . .
C8 C -0.0332(4) 0.08568(18) 0.59158(15) 0.0466(5) Uani 1 1 d . . . . .
H8 H -0.153694 0.072525 0.629813 0.056 Uiso 1 1 calc R U . . .
C9 C -0.0538(5) 0.0597(2) 0.50409(16) 0.0598(7) Uani 1 1 d . . . . .
H9 H -0.188347 0.028513 0.482951 0.072 Uiso 1 1 calc R U . . .
C10 C 0.1180(5) 0.0787(2) 0.44824(14) 0.0601(8) Uani 1 1 d . . . . .
H10 H 0.102255 0.060849 0.388578 0.072 Uiso 1 1 calc R U . . .
C11 C 0.3133(6) 0.1236(2) 0.47844(14) 0.0578(7) Uani 1 1 d . . . . .
H11 H 0.432011 0.137025 0.439447 0.069 Uiso 1 1 calc R U . . .
C12 C 0.3382(4) 0.14958(18) 0.56634(13) 0.0431(5) Uani 1 1 d . . . . .
H12 H 0.473921 0.179884 0.587102 0.052 Uiso 1 1 calc R U . . .
H1 H 0.377(6) 0.009(2) 0.7146(16) 0.086(11) Uiso 1 1 d D . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2017/1 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
F2 C2 1.392(2) . ?
F3 C3 1.406(2) . ?
F5 C5 1.406(3) . ?
F6 C6 1.399(2) . ?
O1 C1 1.431(2) . ?
O1 H1 0.975(7) . ?
C1 C7 1.529(2) . ?
C1 C6 1.532(3) . ?
C1 C2 1.545(2) . ?
C2 C3 1.514(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.511(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.513(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.515(3) . ?
C5 H5 1.0000 . ?
C6 H6 1.0000 . ?
C7 C8 1.390(3) . ?
C7 C12 1.390(3) . ?
C8 C9 1.391(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.368(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.375(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.400(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

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 H1 112(2) . . ?
O1 C1 C7 110.48(14) . . ?
O1 C1 C6 105.20(14) . . ?
C7 C1 C6 113.37(16) . . ?
O1 C1 C2 104.75(15) . . ?
C7 C1 C2 112.01(14) . . ?
C6 C1 C2 110.46(14) . . ?
F2 C2 C3 109.05(15) . . ?
F2 C2 C1 109.69(15) . . ?
C3 C2 C1 110.94(15) . . ?
F2 C2 H2 109.0 . . ?
C3 C2 H2 109.0 . . ?
C1 C2 H2 109.0 . . ?
F3 C3 C4 108.61(17) . . ?
F3 C3 C2 108.02(16) . . ?
C4 C3 C2 112.21(17) . . ?
F3 C3 H3 109.3 . . ?
C4 C3 H3 109.3 . . ?
C2 C3 H3 109.3 . . ?
C3 C4 C5 107.39(16) . . ?
C3 C4 H4A 110.2 . . ?
C5 C4 H4A 110.2 . . ?
C3 C4 H4B 110.2 . . ?
C5 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
F5 C5 C4 108.83(17) . . ?
F5 C5 C6 107.58(19) . . ?
C4 C5 C6 112.12(16) . . ?
F5 C5 H5 109.4 . . ?
C4 C5 H5 109.4 . . ?
C6 C5 H5 109.4 . . ?
F6 C6 C5 108.00(16) . . ?
F6 C6 C1 109.33(14) . . ?
C5 C6 C1 111.22(17) . . ?
F6 C6 H6 109.4 . . ?
C5 C6 H6 109.4 . . ?
C1 C6 H6 109.4 . . ?
C8 C7 C12 119.32(18) . . ?
C8 C7 C1 121.58(19) . . ?
C12 C7 C1 118.96(19) . . ?
C7 C8 C9 120.0(2) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 120.0(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 120.4(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C7 C12 C11 119.7(2) . . ?
C7 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 F2 178.92(14) . . . . ?
C7 C1 C2 F2 59.13(19) . . . . ?
C6 C1 C2 F2 -68.27(18) . . . . ?
O1 C1 C2 C3 -60.55(19) . . . . ?
C7 C1 C2 C3 179.66(17) . . . . ?
C6 C1 C2 C3 52.3(2) . . . . ?
F2 C2 C3 F3 -56.4(2) . . . . ?
C1 C2 C3 F3 -177.30(16) . . . . ?
F2 C2 C3 C4 63.3(2) . . . . ?
C1 C2 C3 C4 -57.6(2) . . . . ?
F3 C3 C4 C5 179.40(16) . . . . ?
C2 C3 C4 C5 60.1(2) . . . . ?
C3 C4 C5 F5 -178.84(16) . . . . ?
C3 C4 C5 C6 -60.0(2) . . . . ?
F5 C5 C6 F6 57.5(2) . . . . ?
C4 C5 C6 F6 -62.2(2) . . . . ?
F5 C5 C6 C1 177.42(15) . . . . ?
C4 C5 C6 C1 57.8(2) . . . . ?
O1 C1 C6 F6 179.33(14) . . . . ?
C7 C1 C6 F6 -59.8(2) . . . . ?
C2 C1 C6 F6 66.80(19) . . . . ?
O1 C1 C6 C5 60.15(19) . . . . ?
C7 C1 C6 C5 -179.02(16) . . . . ?
C2 C1 C6 C5 -52.4(2) . . . . ?
O1 C1 C7 C8 106.4(2) . . . . ?
C6 C1 C7 C8 -11.4(2) . . . . ?
C2 C1 C7 C8 -137.27(18) . . . . ?
O1 C1 C7 C12 -69.2(2) . . . . ?
C6 C1 C7 C12 172.97(17) . . . . ?
C2 C1 C7 C12 47.1(2) . . . . ?
C12 C7 C8 C9 0.0(3) . . . . ?
C1 C7 C8 C9 -175.6(2) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C8 C7 C12 C11 0.5(3) . . . . ?
C1 C7 C12 C11 176.17(18) . . . . ?
C10 C11 C12 C7 -0.6(3) . . . . ?

#==============================================================================
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
O1 H1 F3 . . 4_646 2.878(2) 0.98(2) 1.96(3) 155(3) no

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


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_12a
_database_code_depnum_ccdc_archive 'CCDC 1817387'
_audit_update_record             
;
2018-01-16 deposited with the CCDC.
2018-02-19 downloaded from the CCDC.
;
_audit_creation_date             2016-10-06
_audit_creation_method           'by CrystalStructure 4.2'

_chemical_formula_sum            'C12 H14 F2 O'
_chemical_formula_moiety         'C12 H14 F2 O'
_chemical_formula_weight         212.24
_chemical_melting_point          ?
_chemical_absolute_configuration 'ad '
#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   5.25889(6)
_cell_length_b                   9.75241(11)
_cell_length_c                   20.4698(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1049.83(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10468
_cell_measurement_theta_min      4.25
_cell_measurement_theta_max      75.22
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448.00
_exptl_absorpt_coefficient_mu    0.911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.568
_exptl_absorpt_correction_T_max  0.991

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

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            12388
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_theta_max         75.399
_diffrn_reflns_theta_min         4.320
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2150
_reflns_number_gt                2109
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.663
_reflns_Friedel_fraction_max     0.973
_reflns_Friedel_fraction_full    1.000

#==============================================================================
# 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).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0260
_refine_ls_wR_factor_ref         0.0709
_refine_ls_wR_factor_gt          0.0705
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         2150
_refine_ls_number_parameters     140
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0403P)²+0.1640P] 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          0.001
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.15
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 842 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 0.19895(15) 0.59490(9) 0.61535(5) 0.0283(2) Uani 1 1 d . . . . .
F3 F 0.4974(2) 0.76389(10) 0.54222(5) 0.0355(2) Uani 1 1 d . . . . .
O5 O 0.7353(2) 0.28970(12) 0.51335(6) 0.0321(3) Uani 1 1 d D . . . .
C1 C 0.5534(3) 0.48650(14) 0.66677(7) 0.0228(3) Uani 1 1 d . . . . .
H1 H 0.7291 0.5066 0.6828 0.027 Uiso 1 1 calc R U . . .
C2 C 0.4557(3) 0.61604(15) 0.63297(7) 0.0229(3) Uani 1 1 d . . . . .
H2 H 0.4676 0.6954 0.6637 0.027 Uiso 1 1 calc R U . . .
C3 C 0.6042(3) 0.64776(15) 0.57146(7) 0.0246(3) Uani 1 1 d . . . . .
H3 H 0.7839 0.6691 0.5838 0.030 Uiso 1 1 calc R U . . .
C4 C 0.6052(3) 0.52892(16) 0.52369(7) 0.0269(3) Uani 1 1 d . . . . .
H4A H 0.7055 0.5534 0.4845 0.032 Uiso 1 1 calc R U . . .
H4B H 0.4292 0.5079 0.5097 0.032 Uiso 1 1 calc R U . . .
C5 C 0.7217(3) 0.40441(15) 0.55699(7) 0.0248(3) Uani 1 1 d . . . . .
H5 H 0.8990 0.4287 0.5704 0.030 Uiso 1 1 calc R U . . .
C6 C 0.5735(3) 0.36703(15) 0.61814(7) 0.0253(3) Uani 1 1 d . . . . .
H6A H 0.6577 0.2885 0.6399 0.030 Uiso 1 1 calc R U . . .
H6B H 0.4002 0.3376 0.6055 0.030 Uiso 1 1 calc R U . . .
C7 C 0.3914(3) 0.45267(15) 0.72625(7) 0.0259(3) Uani 1 1 d . . . . .
C8 C 0.1889(3) 0.36066(19) 0.72322(8) 0.0325(4) Uani 1 1 d . . . . .
H8 H 0.1528 0.3153 0.6832 0.039 Uiso 1 1 calc R U . . .
C9 C 0.0390(3) 0.3342(2) 0.77771(9) 0.0383(4) Uani 1 1 d . . . . .
H9 H -0.0971 0.2704 0.7747 0.046 Uiso 1 1 calc R U . . .
C10 C 0.0869(4) 0.40001(19) 0.83623(9) 0.0403(4) Uani 1 1 d . . . . .
H10 H -0.0178 0.3833 0.8732 0.048 Uiso 1 1 calc R U . . .
C11 C 0.2897(4) 0.49084(19) 0.84042(9) 0.0423(5) Uani 1 1 d . . . . .
H11 H 0.3256 0.5354 0.8806 0.051 Uiso 1 1 calc R U . . .
C12 C 0.4409(4) 0.51683(16) 0.78583(8) 0.0346(4) Uani 1 1 d . . . . .
H12 H 0.5793 0.5790 0.7892 0.042 Uiso 1 1 calc R U . . .
H5O H 0.563(2) 0.261(3) 0.5028(14) 0.074(8) Uiso 1 1 d D . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
F2 C2 1.4127(16) . ?
F3 C3 1.3987(17) . ?
O5 C5 1.4333(17) . ?
O5 H5O 0.972(7) . ?
C1 C7 1.522(2) . ?
C1 C2 1.5292(19) . ?
C1 C6 1.5362(19) . ?
C1 H1 1.0000 . ?
C2 C3 1.514(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.516(2) . ?
C3 H3 1.0000 . ?
C4 C5 1.521(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.519(2) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.394(2) . ?
C7 C12 1.395(2) . ?
C8 C9 1.390(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.395(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

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
C5 O5 H5O 108.6(19) . . ?
C7 C1 C2 110.67(11) . . ?
C7 C1 C6 113.11(12) . . ?
C2 C1 C6 110.88(11) . . ?
C7 C1 H1 107.3 . . ?
C2 C1 H1 107.3 . . ?
C6 C1 H1 107.3 . . ?
F2 C2 C3 108.10(11) . . ?
F2 C2 C1 108.42(12) . . ?
C3 C2 C1 111.83(11) . . ?
F2 C2 H2 109.5 . . ?
C3 C2 H2 109.5 . . ?
C1 C2 H2 109.5 . . ?
F3 C3 C2 108.31(12) . . ?
F3 C3 C4 110.14(12) . . ?
C2 C3 C4 112.45(12) . . ?
F3 C3 H3 108.6 . . ?
C2 C3 H3 108.6 . . ?
C4 C3 H3 108.6 . . ?
C3 C4 C5 108.81(12) . . ?
C3 C4 H4A 109.9 . . ?
C5 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
C5 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
O5 C5 C6 110.60(12) . . ?
O5 C5 C4 111.33(12) . . ?
C6 C5 C4 110.73(12) . . ?
O5 C5 H5 108.0 . . ?
C6 C5 H5 108.0 . . ?
C4 C5 H5 108.0 . . ?
C5 C6 C1 112.79(12) . . ?
C5 C6 H6A 109.0 . . ?
C1 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C1 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C12 118.04(15) . . ?
C8 C7 C1 122.10(14) . . ?
C12 C7 C1 119.85(15) . . ?
C9 C8 C7 121.15(17) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C10 C9 C8 120.36(18) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 119.32(16) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C12 120.26(17) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 120.85(17) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C1 C2 F2 -57.74(15) . . . . ?
C6 C1 C2 F2 68.62(14) . . . . ?
C7 C1 C2 C3 -176.83(12) . . . . ?
C6 C1 C2 C3 -50.47(16) . . . . ?
F2 C2 C3 F3 58.42(15) . . . . ?
C1 C2 C3 F3 177.71(12) . . . . ?
F2 C2 C3 C4 -63.52(15) . . . . ?
C1 C2 C3 C4 55.76(16) . . . . ?
F3 C3 C4 C5 -179.87(12) . . . . ?
C2 C3 C4 C5 -58.97(16) . . . . ?
C3 C4 C5 O5 -178.12(12) . . . . ?
C3 C4 C5 C6 58.41(16) . . . . ?
O5 C5 C6 C1 179.92(12) . . . . ?
C4 C5 C6 C1 -56.19(16) . . . . ?
C7 C1 C6 C5 176.46(12) . . . . ?
C2 C1 C6 C5 51.46(16) . . . . ?
C2 C1 C7 C8 94.88(16) . . . . ?
C6 C1 C7 C8 -30.2(2) . . . . ?
C2 C1 C7 C12 -83.77(17) . . . . ?
C6 C1 C7 C12 151.11(14) . . . . ?
C12 C7 C8 C9 0.5(2) . . . . ?
C1 C7 C8 C9 -178.18(14) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
C8 C9 C10 C11 -1.3(3) . . . . ?
C9 C10 C11 C12 1.0(3) . . . . ?
C10 C11 C12 C7 0.1(3) . . . . ?
C8 C7 C12 C11 -0.8(2) . . . . ?
C1 C7 C12 C11 177.87(15) . . . . ?

#==============================================================================
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
O5 H5O O5 . . 3_456 2.7950(16) 0.972(17) 1.824(16) 177(3) no

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


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_11
_database_code_depnum_ccdc_archive 'CCDC 1817388'
_audit_update_record             
;
2018-01-16 deposited with the CCDC.
2018-02-19 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT084_11                  
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.46 Report
RESPONSE: Poor crystals- best result presented - good enough to show
 conformation.
;
# end Validation Reply Form


_audit_creation_date             2016-11-30
_audit_creation_method           'by CrystalStructure 4.2'

_chemical_formula_sum            'C12 H14 F2 O'
_chemical_formula_moiety         'C12 H14 F2 O'
_chemical_formula_weight         212.24
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/a 1'
_space_group_name_Hall           '-P 2yab'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,+Z
#------------------------------------------------------------------------------
_cell_length_a                   13.5173(3)
_cell_length_b                   5.57303(15)
_cell_length_c                   27.4909(9)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.469(2)
_cell_angle_gamma                90.0000
_cell_volume                     2070.88(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9672
_cell_measurement_theta_min      3.66
_cell_measurement_theta_max      73.85
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896.00
_exptl_absorpt_coefficient_mu    0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.577
_exptl_absorpt_correction_T_max  0.991

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

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            22453
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_theta_max         75.614
_diffrn_reflns_theta_min         3.215
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       33
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4191
_reflns_number_gt                3710
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1345
_refine_ls_R_factor_gt           0.1282
_refine_ls_wR_factor_ref         0.4562
_refine_ls_wR_factor_gt          0.4485
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         4191
_refine_ls_number_parameters     279
_refine_ls_goodness_of_fit_ref   2.205
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.2000P)²] 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         1.65
_refine_diff_density_min         -1.16
_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 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 0.4612(2) 1.1946(5) 0.38074(13) 0.0709(10) Uani 1 1 d . . . . .
F3 F 0.2670(2) 1.1568(7) 0.39943(12) 0.0792(11) Uani 1 1 d . . . . .
F22 F 0.7593(4) 0.4943(7) 0.8999(2) 0.139(3) Uani 1 1 d . . . . .
F23 F 0.8231(3) 0.5428(18) 0.9922(3) 0.197(4) Uani 1 1 d . . . . .
O4 O 0.2753(2) 0.9040(6) 0.48702(13) 0.0611(10) Uani 1 1 d D . . . .
O24 O 1.0037(3) 0.7600(9) 0.97730(15) 0.0779(13) Uani 1 1 d D . . . .
C1 C 0.4835(3) 0.7726(6) 0.37514(14) 0.0384(9) Uani 1 1 d . . . . .
H1 H 0.4440 0.6261 0.3670 0.046 Uiso 1 1 calc R U . . .
C2 C 0.4133(3) 0.9844(8) 0.37032(15) 0.0459(9) Uani 1 1 d . . . . .
H2 H 0.3878 0.9914 0.3361 0.055 Uiso 1 1 calc R U . . .
C3 C 0.3265(3) 0.9620(10) 0.40447(15) 0.0535(11) Uani 1 1 d . . . . .
H3 H 0.2878 0.8157 0.3953 0.064 Uiso 1 1 calc R U . . .
C4 C 0.3593(3) 0.9382(7) 0.45621(14) 0.0431(9) Uani 1 1 d . . . . .
H4A H 0.3947 1.0880 0.4663 0.052 Uiso 1 1 calc R U . . .
C5 C 0.4287(3) 0.7261(8) 0.46204(17) 0.0548(11) Uani 1 1 d . . . . .
H5A H 0.4519 0.7176 0.4962 0.066 Uiso 1 1 calc R U . . .
H5B H 0.3921 0.5763 0.4547 0.066 Uiso 1 1 calc R U . . .
C6 C 0.5175(3) 0.7443(8) 0.42877(16) 0.0511(11) Uani 1 1 d . . . . .
H6A H 0.5586 0.5981 0.4321 0.061 Uiso 1 1 calc R U . . .
H6B H 0.5584 0.8841 0.4384 0.061 Uiso 1 1 calc R U . . .
C7 C 0.5698(2) 0.7760(6) 0.34053(12) 0.0350(8) Uani 1 1 d . . . . .
C8 C 0.6401(2) 0.9608(7) 0.34042(13) 0.0376(8) Uani 1 1 d . . . . .
H8 H 0.6338 1.0913 0.3624 0.045 Uiso 1 1 calc R U . . .
C9 C 0.7190(3) 0.9544(7) 0.30837(15) 0.0432(9) Uani 1 1 d . . . . .
H9 H 0.7658 1.0817 0.3084 0.052 Uiso 1 1 calc R U . . .
C10 C 0.7302(3) 0.7651(7) 0.27645(15) 0.0449(9) Uani 1 1 d . . . . .
H10 H 0.7844 0.7619 0.2547 0.054 Uiso 1 1 calc R U . . .
C11 C 0.6618(3) 0.5796(7) 0.27641(14) 0.0441(9) Uani 1 1 d . . . . .
H11 H 0.6690 0.4490 0.2545 0.053 Uiso 1 1 calc R U . . .
C12 C 0.5830(3) 0.5848(6) 0.30838(13) 0.0392(8) Uani 1 1 d . . . . .
H12 H 0.5370 0.4559 0.3084 0.047 Uiso 1 1 calc R U . . .
C21 C 0.7567(3) 0.9068(6) 0.88563(14) 0.0423(9) Uani 1 1 d . . . . .
H21 H 0.7502 1.0595 0.9044 0.051 Uiso 1 1 calc R U . . .
C22 C 0.7504(3) 0.7043(14) 0.9212(2) 0.082(2) Uani 1 1 d . . . . .
H22 H 0.6846 0.7113 0.9375 0.098 Uiso 1 1 calc R U . . .
C23 C 0.8311(4) 0.7244(17) 0.9599(2) 0.091(3) Uani 1 1 d . . . . .
H23 H 0.8199 0.8776 0.9780 0.109 Uiso 1 1 calc R U . . .
C24 C 0.9313(3) 0.7354(8) 0.93929(17) 0.0521(11) Uani 1 1 d . . . . .
H24A H 0.9437 0.5777 0.9231 0.062 Uiso 1 1 calc R U . . .
C25 C 0.9418(4) 0.9242(11) 0.9014(2) 0.0720(16) Uani 1 1 d . . . . .
H25A H 1.0073 0.9082 0.8859 0.086 Uiso 1 1 calc R U . . .
H25B H 0.9388 1.0842 0.9170 0.086 Uiso 1 1 calc R U . . .
C26 C 0.8606(3) 0.9064(12) 0.8624(2) 0.0713(17) Uani 1 1 d . . . . .
H26A H 0.8695 0.7570 0.8434 0.086 Uiso 1 1 calc R U . . .
H26B H 0.8662 1.0438 0.8397 0.086 Uiso 1 1 calc R U . . .
C27 C 0.6757(2) 0.9058(6) 0.84692(13) 0.0373(8) Uani 1 1 d . . . . .
C28 C 0.6685(3) 0.7247(7) 0.81181(15) 0.0454(9) Uani 1 1 d . . . . .
H28 H 0.7146 0.5960 0.8120 0.054 Uiso 1 1 calc R U . . .
C29 C 0.5943(3) 0.7328(8) 0.77673(16) 0.0503(10) Uani 1 1 d . . . . .
H29 H 0.5899 0.6084 0.7532 0.060 Uiso 1 1 calc R U . . .
C30 C 0.5265(3) 0.9188(7) 0.77545(14) 0.0430(9) Uani 1 1 d . . . . .
H30 H 0.4754 0.9224 0.7515 0.052 Uiso 1 1 calc R U . . .
C31 C 0.5346(3) 1.0995(8) 0.80985(16) 0.0490(10) Uani 1 1 d . . . . .
H31 H 0.4892 1.2297 0.8091 0.059 Uiso 1 1 calc R U . . .
C32 C 0.6077(3) 1.0930(7) 0.84521(16) 0.0459(9) Uani 1 1 d . . . . .
H32 H 0.6117 1.2179 0.8687 0.055 Uiso 1 1 calc R U . . .
H4O H 0.263(4) 1.037(7) 0.5095(17) 0.068(16) Uiso 1 1 d D . . . .
H24O H 0.946(4) 0.722(15) 0.997(3) 0.11(3) Uiso 1 1 d D . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'Superflip (Palatinus, et al., 2007)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
F2 C2 1.367(5) . ?
F3 C3 1.358(6) . ?
F22 C22 1.315(10) . ?
F23 C23 1.352(8) . ?
O4 C4 1.435(4) . ?
O4 H4O 0.980(5) . ?
O24 C24 1.433(6) . ?
O24 H24O 0.980(5) . ?
C1 C7 1.512(5) . ?
C1 C2 1.519(5) . ?
C1 C6 1.549(6) . ?
C1 H1 1.0000 . ?
C2 C3 1.514(5) . ?
C2 H2 1.0000 . ?
C3 C4 1.492(6) . ?
C3 H3 1.0000 . ?
C4 C5 1.516(6) . ?
C4 H4A 1.0000 . ?
C5 C6 1.519(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C12 1.397(5) . ?
C7 C8 1.401(5) . ?
C8 C9 1.389(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.387(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C21 C22 1.496(7) . ?
C21 C27 1.521(5) . ?
C21 C26 1.548(6) . ?
C21 H21 1.0000 . ?
C22 C23 1.521(8) . ?
C22 H22 1.0000 . ?
C23 C24 1.473(6) . ?
C23 H23 1.0000 . ?
C24 C25 1.488(7) . ?
C24 H24A 1.0000 . ?
C25 C26 1.533(7) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C32 1.390(5) . ?
C27 C28 1.399(5) . ?
C28 C29 1.387(6) . ?
C28 H28 0.9500 . ?
C29 C30 1.384(6) . ?
C29 H29 0.9500 . ?
C30 C31 1.385(6) . ?
C30 H30 0.9500 . ?
C31 C32 1.381(6) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?

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
C4 O4 H4O 114(4) . . ?
C24 O24 H24O 81(5) . . ?
C7 C1 C2 114.8(3) . . ?
C7 C1 C6 112.1(3) . . ?
C2 C1 C6 110.0(3) . . ?
C7 C1 H1 106.4 . . ?
C2 C1 H1 106.4 . . ?
C6 C1 H1 106.4 . . ?
F2 C2 C3 108.0(3) . . ?
F2 C2 C1 110.7(3) . . ?
C3 C2 C1 111.6(3) . . ?
F2 C2 H2 108.8 . . ?
C3 C2 H2 108.8 . . ?
C1 C2 H2 108.8 . . ?
F3 C3 C4 109.8(4) . . ?
F3 C3 C2 109.4(4) . . ?
C4 C3 C2 111.9(3) . . ?
F3 C3 H3 108.6 . . ?
C4 C3 H3 108.6 . . ?
C2 C3 H3 108.6 . . ?
O4 C4 C3 110.1(3) . . ?
O4 C4 C5 109.0(3) . . ?
C3 C4 C5 110.4(3) . . ?
O4 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
C6 C5 C4 112.1(3) . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C5 C6 C1 110.5(4) . . ?
C5 C6 H6A 109.6 . . ?
C1 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C1 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C12 C7 C8 118.0(3) . . ?
C12 C7 C1 119.4(3) . . ?
C8 C7 C1 122.5(3) . . ?
C9 C8 C7 120.4(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 120.7(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.6(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 120.0(3) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C7 121.3(3) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
C22 C21 C27 114.2(3) . . ?
C22 C21 C26 109.0(4) . . ?
C27 C21 C26 111.2(3) . . ?
C22 C21 H21 107.4 . . ?
C27 C21 H21 107.4 . . ?
C26 C21 H21 107.4 . . ?
F22 C22 C21 112.0(5) . . ?
F22 C22 C23 108.0(6) . . ?
C21 C22 C23 110.9(5) . . ?
F22 C22 H22 108.6 . . ?
C21 C22 H22 108.6 . . ?
C23 C22 H22 108.6 . . ?
F23 C23 C24 111.3(5) . . ?
F23 C23 C22 110.1(6) . . ?
C24 C23 C22 113.0(5) . . ?
F23 C23 H23 107.4 . . ?
C24 C23 H23 107.4 . . ?
C22 C23 H23 107.4 . . ?
O24 C24 C23 110.4(4) . . ?
O24 C24 C25 111.9(4) . . ?
C23 C24 C25 113.1(4) . . ?
O24 C24 H24A 107.0 . . ?
C23 C24 H24A 107.0 . . ?
C25 C24 H24A 107.0 . . ?
C24 C25 C26 111.9(4) . . ?
C24 C25 H25A 109.2 . . ?
C26 C25 H25A 109.2 . . ?
C24 C25 H25B 109.2 . . ?
C26 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
C25 C26 C21 110.9(4) . . ?
C25 C26 H26A 109.4 . . ?
C21 C26 H26A 109.4 . . ?
C25 C26 H26B 109.4 . . ?
C21 C26 H26B 109.4 . . ?
H26A C26 H26B 108.0 . . ?
C32 C27 C28 118.4(3) . . ?
C32 C27 C21 119.5(3) . . ?
C28 C27 C21 122.0(3) . . ?
C29 C28 C27 120.1(3) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C30 C29 C28 121.1(4) . . ?
C30 C29 H29 119.4 . . ?
C28 C29 H29 119.4 . . ?
C31 C30 C29 118.6(4) . . ?
C31 C30 H30 120.7 . . ?
C29 C30 H30 120.7 . . ?
C32 C31 C30 120.9(4) . . ?
C32 C31 H31 119.6 . . ?
C30 C31 H31 119.6 . . ?
C31 C32 C27 120.8(4) . . ?
C31 C32 H32 119.6 . . ?
C27 C32 H32 119.6 . . ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C1 C2 F2 -62.4(4) . . . . ?
C6 C1 C2 F2 65.2(4) . . . . ?
C7 C1 C2 C3 177.3(3) . . . . ?
C6 C1 C2 C3 -55.1(4) . . . . ?
F2 C2 C3 F3 57.1(4) . . . . ?
C1 C2 C3 F3 179.0(3) . . . . ?
F2 C2 C3 C4 -64.9(5) . . . . ?
C1 C2 C3 C4 57.0(5) . . . . ?
F3 C3 C4 O4 61.5(5) . . . . ?
C2 C3 C4 O4 -176.8(3) . . . . ?
F3 C3 C4 C5 -178.1(3) . . . . ?
C2 C3 C4 C5 -56.4(5) . . . . ?
O4 C4 C5 C6 177.5(4) . . . . ?
C3 C4 C5 C6 56.4(5) . . . . ?
C4 C5 C6 C1 -55.6(5) . . . . ?
C7 C1 C6 C5 -176.5(3) . . . . ?
C2 C1 C6 C5 54.5(4) . . . . ?
C2 C1 C7 C12 -121.5(4) . . . . ?
C6 C1 C7 C12 111.9(4) . . . . ?
C2 C1 C7 C8 60.8(4) . . . . ?
C6 C1 C7 C8 -65.7(4) . . . . ?
C12 C7 C8 C9 1.4(5) . . . . ?
C1 C7 C8 C9 179.1(3) . . . . ?
C7 C8 C9 C10 -0.7(6) . . . . ?
C8 C9 C10 C11 0.0(6) . . . . ?
C9 C10 C11 C12 -0.1(6) . . . . ?
C10 C11 C12 C7 0.9(6) . . . . ?
C8 C7 C12 C11 -1.5(5) . . . . ?
C1 C7 C12 C11 -179.3(3) . . . . ?
C27 C21 C22 F22 61.8(5) . . . . ?
C26 C21 C22 F22 -63.3(5) . . . . ?
C27 C21 C22 C23 -177.5(5) . . . . ?
C26 C21 C22 C23 57.4(7) . . . . ?
F22 C22 C23 F23 -58.1(8) . . . . ?
C21 C22 C23 F23 178.8(7) . . . . ?
F22 C22 C23 C24 67.0(8) . . . . ?
C21 C22 C23 C24 -56.0(9) . . . . ?
F23 C23 C24 O24 -56.9(9) . . . . ?
C22 C23 C24 O24 178.6(6) . . . . ?
F23 C23 C24 C25 176.8(7) . . . . ?
C22 C23 C24 C25 52.3(9) . . . . ?
O24 C24 C25 C26 -176.7(5) . . . . ?
C23 C24 C25 C26 -51.2(8) . . . . ?
C24 C25 C26 C21 53.6(7) . . . . ?
C22 C21 C26 C25 -56.9(6) . . . . ?
C27 C21 C26 C25 176.2(4) . . . . ?
C22 C21 C27 C32 115.7(5) . . . . ?
C26 C21 C27 C32 -120.4(4) . . . . ?
C22 C21 C27 C28 -66.0(5) . . . . ?
C26 C21 C27 C28 57.9(5) . . . . ?
C32 C27 C28 C29 -0.7(6) . . . . ?
C21 C27 C28 C29 -179.1(4) . . . . ?
C27 C28 C29 C30 0.3(6) . . . . ?
C28 C29 C30 C31 0.6(6) . . . . ?
C29 C30 C31 C32 -1.0(6) . . . . ?
C30 C31 C32 C27 0.6(6) . . . . ?
C28 C27 C32 C31 0.3(6) . . . . ?
C21 C27 C32 C31 178.7(4) . . . . ?

#==============================================================================
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
O4 H4O O4 . . 2_556 2.958(5) 0.98(4) 2.11(4) 143(4) no
O24 H24O F23 . . . 2.759(7) 0.98(6) 1.95(6) 139(6) no

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


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_12b
_database_code_depnum_ccdc_archive 'CCDC 1817390'
_audit_update_record             
;
2018-01-16 deposited with the CCDC.
2018-02-19 downloaded from the CCDC.
;
_audit_creation_date             2016-10-11
_audit_creation_method           'by CrystalStructure 4.2'


_chemical_formula_sum            'C12 H14 F2 O'
_chemical_formula_moiety         'C12 H14 F2 O'
_chemical_formula_weight         212.24
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   10.536(3)
_cell_length_b                   19.983(6)
_cell_length_c                   10.272(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 107.972(7)
_cell_angle_gamma                90.0000
_cell_volume                     2057.2(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1824
_cell_measurement_theta_min      39.80
_cell_measurement_theta_max      67.80
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896.00
_exptl_absorpt_coefficient_mu    0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.741
_exptl_absorpt_correction_T_max  0.955

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

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            20733
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_theta_max         68.003
_diffrn_reflns_theta_min         4.412
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3703
_reflns_number_gt                3343
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.1055
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3703
_refine_ls_number_parameters     279
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0637P)²+0.5449P] 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         0.23
_refine_diff_density_min         -0.19
_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 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 0.77363(8) 0.12131(4) 0.11193(9) 0.0439(2) Uani 1 1 d . . . . .
F3 F 0.51712(8) 0.07444(5) 0.04870(9) 0.0441(2) Uani 1 1 d . . . . .
F22 F 0.40054(8) 0.27108(4) 0.78789(9) 0.0375(2) Uani 1 1 d . . . . .
F23 F 0.66391(8) 0.23983(4) 0.90492(8) 0.0348(2) Uani 1 1 d . . . . .
O5 O 0.68218(11) 0.02218(6) 0.46446(10) 0.0442(3) Uani 1 1 d D . . . .
O25 O 0.51430(10) 0.07323(5) 0.65685(11) 0.0364(3) Uani 1 1 d D . . . .
C1 C 0.85880(12) 0.04011(6) 0.28701(12) 0.0227(3) Uani 1 1 d . . . . .
H1 H 0.8402 -0.0062 0.3134 0.027 Uiso 1 1 calc R U . . .
C2 C 0.74985(13) 0.05706(7) 0.15321(13) 0.0273(3) Uani 1 1 d . . . . .
H2 H 0.7525 0.0240 0.0811 0.033 Uiso 1 1 calc R U . . .
C3 C 0.61369(13) 0.05592(7) 0.17270(13) 0.0272(3) Uani 1 1 d . . . . .
H3 H 0.5943 0.0094 0.1969 0.033 Uiso 1 1 calc R U . . .
C4 C 0.60433(15) 0.10277(7) 0.28420(17) 0.0376(3) Uani 1 1 d . . . . .
H4A H 0.5150 0.0988 0.2964 0.045 Uiso 1 1 calc R U . . .
H4B H 0.6156 0.1495 0.2575 0.045 Uiso 1 1 calc R U . . .
C5 C 0.71125(15) 0.08654(7) 0.41872(15) 0.0352(3) Uani 1 1 d . . . . .
H5A H 0.7080 0.1209 0.4884 0.042 Uiso 1 1 calc R U . . .
C6 C 0.84962(14) 0.08697(7) 0.40167(14) 0.0293(3) Uani 1 1 d . . . . .
H6A H 0.9160 0.0731 0.4888 0.035 Uiso 1 1 calc R U . . .
H6B H 0.8719 0.1331 0.3810 0.035 Uiso 1 1 calc R U . . .
C7 C 0.99444(12) 0.03829(6) 0.26428(12) 0.0236(3) Uani 1 1 d . . . . .
C8 C 1.07728(14) 0.09392(7) 0.28217(14) 0.0298(3) Uani 1 1 d . . . . .
H8 H 1.0512 0.1347 0.3142 0.036 Uiso 1 1 calc R U . . .
C9 C 1.19799(14) 0.09056(7) 0.25367(15) 0.0347(3) Uani 1 1 d . . . . .
H9 H 1.2538 0.1289 0.2669 0.042 Uiso 1 1 calc R U . . .
C10 C 1.23731(14) 0.03199(8) 0.20631(15) 0.0344(3) Uani 1 1 d . . . . .
H10 H 1.3192 0.0300 0.1859 0.041 Uiso 1 1 calc R U . . .
C11 C 1.15636(15) -0.02375(7) 0.18890(16) 0.0364(3) Uani 1 1 d . . . . .
H11 H 1.1827 -0.0644 0.1566 0.044 Uiso 1 1 calc R U . . .
C12 C 1.03666(14) -0.02052(7) 0.21848(14) 0.0309(3) Uani 1 1 d . . . . .
H12 H 0.9824 -0.0594 0.2072 0.037 Uiso 1 1 calc R U . . .
C20 C 0.09032(13) 0.19758(7) 0.68254(14) 0.0309(3) Uani 1 1 d . . . . .
H20 H 0.0979 0.2034 0.5934 0.037 Uiso 1 1 calc R U . . .
C21 C 0.33217(12) 0.15726(6) 0.76631(12) 0.0214(3) Uani 1 1 d . . . . .
H21 H 0.3607 0.1123 0.8078 0.026 Uiso 1 1 calc R U . . .
C22 C 0.43699(13) 0.20749(6) 0.84465(13) 0.0246(3) Uani 1 1 d . . . . .
H22 H 0.4406 0.2079 0.9431 0.030 Uiso 1 1 calc R U . . .
C23 C 0.57280(12) 0.19055(6) 0.83396(13) 0.0244(3) Uani 1 1 d . . . . .
H23 H 0.6012 0.1461 0.8781 0.029 Uiso 1 1 calc R U . . .
C24 C 0.57371(13) 0.18756(7) 0.68716(13) 0.0279(3) Uani 1 1 d . . . . .
H24A H 0.6631 0.1735 0.6848 0.033 Uiso 1 1 calc R U . . .
H24B H 0.5549 0.2326 0.6454 0.033 Uiso 1 1 calc R U . . .
C25 C 0.46916(13) 0.13827(7) 0.60526(13) 0.0281(3) Uani 1 1 d . . . . .
H25A H 0.4651 0.1407 0.5068 0.034 Uiso 1 1 calc R U . . .
C26 C 0.33112(12) 0.15373(6) 0.61702(12) 0.0257(3) Uani 1 1 d . . . . .
H26A H 0.2677 0.1186 0.5688 0.031 Uiso 1 1 calc R U . . .
H26B H 0.2996 0.1970 0.5716 0.031 Uiso 1 1 calc R U . . .
C27 C 0.19822(12) 0.17265(6) 0.78665(13) 0.0230(3) Uani 1 1 d . . . . .
C28 C 0.18288(13) 0.16295(7) 0.91531(14) 0.0292(3) Uani 1 1 d . . . . .
H28 H 0.2550 0.1454 0.9875 0.035 Uiso 1 1 calc R U . . .
C29 C 0.06376(14) 0.17851(7) 0.93947(15) 0.0349(3) Uani 1 1 d . . . . .
H29 H 0.0545 0.1710 1.0274 0.042 Uiso 1 1 calc R U . . .
C30 C -0.04167(14) 0.20502(7) 0.83574(16) 0.0366(3) Uani 1 1 d . . . . .
H30 H -0.1223 0.2169 0.8529 0.044 Uiso 1 1 calc R U . . .
C31 C -0.02860(14) 0.21407(7) 0.70713(16) 0.0372(3) Uani 1 1 d . . . . .
H31 H -0.1010 0.2316 0.6352 0.045 Uiso 1 1 calc R U . . .
H25O H 0.4495(16) 0.0390(8) 0.612(2) 0.064(6) Uiso 1 1 d D . . . .
H5O H 0.682(4) 0.0250(18) 0.5594(13) 0.143(13) Uiso 1 1 d D . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
F2 C2 1.3987(16) . ?
F3 C3 1.4124(15) . ?
F22 C22 1.4014(15) . ?
F23 C23 1.4110(14) . ?
O5 C5 1.4344(19) . ?
O5 H5O 0.976(5) . ?
O25 C25 1.4285(17) . ?
O25 H25O 0.975(5) . ?
C1 C7 1.5179(17) . ?
C1 C6 1.5308(17) . ?
C1 C2 1.5322(17) . ?
C1 H1 1.0000 . ?
C2 C3 1.5085(19) . ?
C2 H2 1.0000 . ?
C3 C4 1.506(2) . ?
C3 H3 1.0000 . ?
C4 C5 1.524(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5211(19) . ?
C5 H5A 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C12 1.3891(19) . ?
C7 C8 1.3900(18) . ?
C8 C9 1.392(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.387(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C20 C27 1.3907(18) . ?
C20 C31 1.392(2) . ?
C20 H20 0.9500 . ?
C21 C27 1.5204(17) . ?
C21 C22 1.5253(17) . ?
C21 C26 1.5318(17) . ?
C21 H21 1.0000 . ?
C22 C23 1.5070(18) . ?
C22 H22 1.0000 . ?
C23 C24 1.5121(18) . ?
C23 H23 1.0000 . ?
C24 C25 1.5230(19) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.5275(18) . ?
C25 H25A 1.0000 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.3936(19) . ?
C28 C29 1.388(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.385(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.382(2) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?

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
C5 O5 H5O 110(2) . . ?
C25 O25 H25O 111.0(13) . . ?
C7 C1 C6 114.77(10) . . ?
C7 C1 C2 110.34(10) . . ?
C6 C1 C2 110.32(11) . . ?
C7 C1 H1 107.0 . . ?
C6 C1 H1 107.0 . . ?
C2 C1 H1 107.0 . . ?
F2 C2 C3 108.71(10) . . ?
F2 C2 C1 108.67(10) . . ?
C3 C2 C1 110.95(10) . . ?
F2 C2 H2 109.5 . . ?
C3 C2 H2 109.5 . . ?
C1 C2 H2 109.5 . . ?
F3 C3 C4 108.96(11) . . ?
F3 C3 C2 109.05(10) . . ?
C4 C3 C2 112.31(11) . . ?
F3 C3 H3 108.8 . . ?
C4 C3 H3 108.8 . . ?
C2 C3 H3 108.8 . . ?
C3 C4 C5 110.71(11) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
O5 C5 C6 110.61(12) . . ?
O5 C5 C4 108.36(11) . . ?
C6 C5 C4 111.16(12) . . ?
O5 C5 H5A 108.9 . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5A 108.9 . . ?
C5 C6 C1 112.05(11) . . ?
C5 C6 H6A 109.2 . . ?
C1 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C1 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C12 C7 C8 117.88(12) . . ?
C12 C7 C1 119.18(11) . . ?
C8 C7 C1 122.89(11) . . ?
C7 C8 C9 120.72(13) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 120.56(13) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 119.31(13) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C12 120.08(13) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C7 121.43(12) . . ?
C11 C12 H12 119.3 . . ?
C7 C12 H12 119.3 . . ?
C27 C20 C31 120.89(13) . . ?
C27 C20 H20 119.6 . . ?
C31 C20 H20 119.6 . . ?
C27 C21 C22 110.25(10) . . ?
C27 C21 C26 115.25(10) . . ?
C22 C21 C26 109.81(10) . . ?
C27 C21 H21 107.0 . . ?
C22 C21 H21 107.0 . . ?
C26 C21 H21 107.0 . . ?
F22 C22 C23 108.53(10) . . ?
F22 C22 C21 108.44(10) . . ?
C23 C22 C21 111.28(10) . . ?
F22 C22 H22 109.5 . . ?
C23 C22 H22 109.5 . . ?
C21 C22 H22 109.5 . . ?
F23 C23 C22 108.40(10) . . ?
F23 C23 C24 109.27(10) . . ?
C22 C23 C24 112.32(10) . . ?
F23 C23 H23 108.9 . . ?
C22 C23 H23 108.9 . . ?
C24 C23 H23 108.9 . . ?
C23 C24 C25 110.51(10) . . ?
C23 C24 H24A 109.5 . . ?
C25 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C25 C24 H24B 109.5 . . ?
H24A C24 H24B 108.1 . . ?
O25 C25 C24 106.39(10) . . ?
O25 C25 C26 111.76(11) . . ?
C24 C25 C26 111.69(11) . . ?
O25 C25 H25A 109.0 . . ?
C24 C25 H25A 109.0 . . ?
C26 C25 H25A 109.0 . . ?
C25 C26 C21 112.06(10) . . ?
C25 C26 H26A 109.2 . . ?
C21 C26 H26A 109.2 . . ?
C25 C26 H26B 109.2 . . ?
C21 C26 H26B 109.2 . . ?
H26A C26 H26B 107.9 . . ?
C20 C27 C28 118.20(12) . . ?
C20 C27 C21 122.68(11) . . ?
C28 C27 C21 119.10(11) . . ?
C29 C28 C27 120.96(13) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C30 C29 C28 120.19(13) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C31 C30 C29 119.51(13) . . ?
C31 C30 H30 120.2 . . ?
C29 C30 H30 120.2 . . ?
C30 C31 C20 120.22(14) . . ?
C30 C31 H31 119.9 . . ?
C20 C31 H31 119.9 . . ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C1 C2 F2 -63.15(13) . . . . ?
C6 C1 C2 F2 64.71(13) . . . . ?
C7 C1 C2 C3 177.38(10) . . . . ?
C6 C1 C2 C3 -54.76(14) . . . . ?
F2 C2 C3 F3 58.18(13) . . . . ?
C1 C2 C3 F3 177.63(10) . . . . ?
F2 C2 C3 C4 -62.70(14) . . . . ?
C1 C2 C3 C4 56.74(15) . . . . ?
F3 C3 C4 C5 -177.41(11) . . . . ?
C2 C3 C4 C5 -56.48(15) . . . . ?
C3 C4 C5 O5 -66.85(15) . . . . ?
C3 C4 C5 C6 54.89(16) . . . . ?
O5 C5 C6 C1 65.63(14) . . . . ?
C4 C5 C6 C1 -54.79(15) . . . . ?
C7 C1 C6 C5 179.85(11) . . . . ?
C2 C1 C6 C5 54.46(15) . . . . ?
C6 C1 C7 C12 148.59(12) . . . . ?
C2 C1 C7 C12 -86.03(14) . . . . ?
C6 C1 C7 C8 -33.98(16) . . . . ?
C2 C1 C7 C8 91.39(14) . . . . ?
C12 C7 C8 C9 0.58(19) . . . . ?
C1 C7 C8 C9 -176.87(12) . . . . ?
C7 C8 C9 C10 0.4(2) . . . . ?
C8 C9 C10 C11 -0.8(2) . . . . ?
C9 C10 C11 C12 0.2(2) . . . . ?
C10 C11 C12 C7 0.8(2) . . . . ?
C8 C7 C12 C11 -1.2(2) . . . . ?
C1 C7 C12 C11 176.39(12) . . . . ?
C27 C21 C22 F22 -64.54(13) . . . . ?
C26 C21 C22 F22 63.49(12) . . . . ?
C27 C21 C22 C23 176.15(10) . . . . ?
C26 C21 C22 C23 -55.81(13) . . . . ?
F22 C22 C23 F23 59.04(12) . . . . ?
C21 C22 C23 F23 178.30(10) . . . . ?
F22 C22 C23 C24 -61.79(13) . . . . ?
C21 C22 C23 C24 57.46(14) . . . . ?
F23 C23 C24 C25 -175.99(10) . . . . ?
C22 C23 C24 C25 -55.66(14) . . . . ?
C23 C24 C25 O25 -68.52(13) . . . . ?
C23 C24 C25 C26 53.69(14) . . . . ?
O25 C25 C26 C21 64.73(14) . . . . ?
C24 C25 C26 C21 -54.34(14) . . . . ?
C27 C21 C26 C25 179.86(10) . . . . ?
C22 C21 C26 C25 54.65(14) . . . . ?
C31 C20 C27 C28 1.7(2) . . . . ?
C31 C20 C27 C21 -176.86(12) . . . . ?
C22 C21 C27 C20 110.00(13) . . . . ?
C26 C21 C27 C20 -14.98(17) . . . . ?
C22 C21 C27 C28 -68.52(14) . . . . ?
C26 C21 C27 C28 166.50(11) . . . . ?
C20 C27 C28 C29 -0.78(19) . . . . ?
C21 C27 C28 C29 177.81(12) . . . . ?
C27 C28 C29 C30 -1.0(2) . . . . ?
C28 C29 C30 C31 1.8(2) . . . . ?
C29 C30 C31 C20 -0.9(2) . . . . ?
C27 C20 C31 C30 -0.8(2) . . . . ?

#==============================================================================
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
O25 H25o O5 . . 3_656 2.8074(16) 0.974(16) 1.835(16) 175.1(18) no

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


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_13
_database_code_depnum_ccdc_archive 'CCDC 1817389'
_audit_update_record             
;
2018-01-16 deposited with the CCDC.
2018-02-19 downloaded from the CCDC.
;
_audit_creation_date             2016-12-01
_audit_creation_method           'by CrystalStructure 4.2'


_chemical_formula_sum            'C12 H15 F O'
_chemical_formula_moiety         'C12 H15 F O'
_chemical_formula_weight         194.25
_chemical_melting_point          ?
_chemical_absolute_configuration ' ad '

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   5.33024(13)
_cell_length_b                   9.6528(3)
_cell_length_c                   20.0332(7)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1030.74(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7965
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      75.27
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416.00
_exptl_absorpt_coefficient_mu    0.735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.716
_exptl_absorpt_correction_T_max  0.993

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

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            11679
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_theta_max         75.375
_diffrn_reflns_theta_min         4.414
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2104
_reflns_number_gt                2017
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.667
_reflns_Friedel_fraction_max     0.976
_reflns_Friedel_fraction_full    0.999

#==============================================================================
# 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).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1496
_refine_ls_wR_factor_gt          0.1485
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         2104
_refine_ls_number_parameters     135
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0961P)²+0.4402P] 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         0.38
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 779 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(11)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 0.2818(3) 1.1143(2) 0.89389(9) 0.0450(5) Uani 1 1 d . . . A 1
O5 O -0.2673(5) 0.7943(3) 0.98741(12) 0.0342(6) Uani 0.8 1 d D . P A 1
C1 C -0.0554(6) 1.0022(3) 0.83665(14) 0.0346(6) Uani 1 1 d . . . A 1
H1 H -0.2263 1.0219 0.8184 0.041 Uiso 1 1 calc R U . A 1
C2 C 0.0290(5) 1.1324(3) 0.87342(15) 0.0356(6) Uani 1 1 d . . . A 1
H2 H 0.0189 1.2133 0.8423 0.043 Uiso 1 1 calc R U . A 1
C3 C -0.1267(6) 1.1626(3) 0.93491(15) 0.0386(7) Uani 1 1 d . . . A 1
H3A H -0.0516 1.2415 0.9593 0.046 Uiso 1 1 calc R U . A 1
H3B H -0.2980 1.1899 0.9210 0.046 Uiso 1 1 calc R U . A 1
C4 C -0.1435(6) 1.0380(3) 0.98158(15) 0.0418(7) Uani 1 1 d . . . A 1
H4A H 0.0251 1.0163 0.9995 0.050 Uiso 1 1 calc R U . A 1
H4B H -0.2548 1.0603 1.0197 0.050 Uiso 1 1 calc R U . A 1
C5 C -0.2455(6) 0.9135(3) 0.94460(15) 0.0376(6) Uani 1 1 d . . . A 1
H5A H -0.4171 0.9374 0.9280 0.045 Uiso 1 1 calc R U . A 1
C6 C -0.0834(6) 0.8799(3) 0.88468(15) 0.0374(6) Uani 1 1 d . . . A 1
H6A H -0.1582 0.8007 0.8604 0.045 Uiso 1 1 calc R U . A 1
H6B H 0.0850 0.8513 0.9003 0.045 Uiso 1 1 calc R U . A 1
C7 C 0.1124(6) 0.9693(3) 0.77720(14) 0.0366(6) Uani 1 1 d . . . A 1
C8 C 0.3126(6) 0.8759(4) 0.78173(15) 0.0422(7) Uani 1 1 d . . . A 1
H8 H 0.3435 0.8298 0.8228 0.051 Uiso 1 1 calc R U . A 1
C9 C 0.4675(7) 0.8491(4) 0.72708(17) 0.0490(8) Uani 1 1 d . . . A 1
H9 H 0.6016 0.7848 0.7310 0.059 Uiso 1 1 calc R U . A 1
C10 C 0.4254(7) 0.9162(4) 0.66735(17) 0.0495(8) Uani 1 1 d . . . A 1
H10 H 0.5323 0.8996 0.6303 0.059 Uiso 1 1 calc R U . A 1
C11 C 0.2260(9) 1.0081(3) 0.66162(17) 0.0539(9) Uani 1 1 d . . . A 1
H11 H 0.1956 1.0537 0.6204 0.065 Uiso 1 1 calc R U . A 1
C12 C 0.0710(8) 1.0337(3) 0.71596(15) 0.0465(8) Uani 1 1 d . . . A 1
H12 H -0.0656 1.0961 0.7113 0.056 Uiso 1 1 calc R U . A 1
H5O H -0.113(6) 0.748(6) 1.001(3) 0.057(14) Uiso 0.8 1 d D . P B 1
O5' O -0.052(3) 1.2779(18) 0.9613(8) 0.074(4) Uiso 0.2 1 d . . P C 2


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
F2 C2 1.420(3) . ?
O5 C5 1.439(3) . ?
O5 H5O 0.975(7) . ?
C1 C7 1.523(4) . ?
C1 C2 1.525(4) . ?
C1 C6 1.530(4) . ?
C1 H1 1.0000 . ?
C2 C3 1.514(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.526(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.513(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.514(4) . ?
C5 H5A 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C12 1.393(4) . ?
C7 C8 1.400(4) . ?
C8 C9 1.395(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

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
C5 O5 H5O 118(4) . . ?
C7 C1 C2 112.1(2) . . ?
C7 C1 C6 112.8(2) . . ?
C2 C1 C6 111.2(2) . . ?
C7 C1 H1 106.8 . . ?
C2 C1 H1 106.8 . . ?
C6 C1 H1 106.8 . . ?
F2 C2 C3 108.0(2) . . ?
F2 C2 C1 108.5(2) . . ?
C3 C2 C1 113.0(2) . . ?
F2 C2 H2 109.1 . . ?
C3 C2 H2 109.1 . . ?
C1 C2 H2 109.1 . . ?
C4 C3 C2 112.3(2) . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C3 110.3(2) . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
O5 C5 C4 111.8(2) . . ?
O5 C5 C6 110.3(2) . . ?
C4 C5 C6 110.7(3) . . ?
O5 C5 H5A 107.9 . . ?
C4 C5 H5A 107.9 . . ?
C6 C5 H5A 107.9 . . ?
C5 C6 C1 112.9(2) . . ?
C5 C6 H6A 109.0 . . ?
C1 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C1 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C12 C7 C8 117.7(3) . . ?
C12 C7 C1 120.2(3) . . ?
C8 C7 C1 122.1(3) . . ?
C9 C8 C7 121.3(3) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 119.7(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C12 120.2(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C11 121.1(3) . . ?
C7 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C1 C2 F2 -57.1(3) . . . . ?
C6 C1 C2 F2 70.2(3) . . . . ?
C7 C1 C2 C3 -176.9(2) . . . . ?
C6 C1 C2 C3 -49.5(3) . . . . ?
F2 C2 C3 C4 -67.6(3) . . . . ?
C1 C2 C3 C4 52.5(3) . . . . ?
C2 C3 C4 C5 -55.9(3) . . . . ?
C3 C4 C5 O5 -179.2(2) . . . . ?
C3 C4 C5 C6 57.4(3) . . . . ?
O5 C5 C6 C1 179.3(2) . . . . ?
C4 C5 C6 C1 -56.4(3) . . . . ?
C7 C1 C6 C5 178.7(2) . . . . ?
C2 C1 C6 C5 51.8(3) . . . . ?
C2 C1 C7 C12 -83.9(4) . . . . ?
C6 C1 C7 C12 149.6(3) . . . . ?
C2 C1 C7 C8 95.5(3) . . . . ?
C6 C1 C7 C8 -30.9(4) . . . . ?
C12 C7 C8 C9 0.8(5) . . . . ?
C1 C7 C8 C9 -178.7(3) . . . . ?
C7 C8 C9 C10 0.5(5) . . . . ?
C8 C9 C10 C11 -1.2(5) . . . . ?
C9 C10 C11 C12 0.7(5) . . . . ?
C8 C7 C12 C11 -1.3(5) . . . . ?
C1 C7 C12 C11 178.2(3) . . . . ?
C10 C11 C12 C7 0.6(6) . . . . ?

#==============================================================================
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
O5 H5O O5 . . 3_567 2.844(3) 0.97(4) 1.90(3) 162(4) no

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


