# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1460279'
_audit_update_record             
;
2016-03-08 deposited with the CCDC.
2016-03-10 downloaded from the CCDC.
;
_audit_creation_date             2016-02-29
_audit_creation_method           'by CrystalStructure 4.2'


_chemical_formula_sum            'C5 H6 F4'
_chemical_formula_moiety         'C5 H6 F4'
_chemical_formula_weight         142.10
_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                   10.1150(19)
_cell_length_b                   4.5875(11)
_cell_length_c                   11.876(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.026(18)
_cell_angle_gamma                90.0000
_cell_volume                     551.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1504
_cell_measurement_theta_min      2.00
_cell_measurement_theta_max      27.58
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288.00
_exptl_absorpt_coefficient_mu    0.194
_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  0.606
_exptl_absorpt_correction_T_max  0.994

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

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_reflns_number            2971
_diffrn_reflns_av_R_equivalents  0.0922
_diffrn_reflns_theta_max         25.195
_diffrn_reflns_theta_min         2.013
_diffrn_reflns_theta_full        25.195
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             987
_reflns_number_gt                898
_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          0.0638
_refine_ls_R_factor_gt           0.0605
_refine_ls_wR_factor_ref         0.1610
_refine_ls_wR_factor_gt          0.1575
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         987
_refine_ls_number_parameters     83
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0695P)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         0.37
_refine_diff_density_min         -0.39
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0000000

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
(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 0.0171 0.0103
;
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
F1 F 0.76155(18) 0.0439(4) 0.9837(2) 0.0427(6) Uani 1 1 d . . . . .
F2 F 0.98770(16) 0.2752(4) 0.91316(18) 0.0371(5) Uani 1 1 d . . . . .
F3 F 0.82840(18) 0.0525(4) 0.75088(17) 0.0393(6) Uani 1 1 d . . . . .
F4 F 0.60053(19) 0.2811(5) 0.69819(19) 0.0521(7) Uani 1 1 d . . . . .
C1 C 0.7583(3) 0.3459(7) 0.9627(3) 0.0303(8) Uani 1 1 d . . . . .
H1 H 0.7615 0.4605 1.0342 0.036 Uiso 1 1 calc R U . . .
C2 C 0.8719(3) 0.4256(6) 0.8850(3) 0.0301(7) Uani 1 1 d . . . . .
H2 H 0.8888 0.6398 0.8907 0.036 Uiso 1 1 calc R U . . .
C3 C 0.8235(3) 0.3555(7) 0.7663(3) 0.0300(7) Uani 1 1 d . . . . .
H3 H 0.8747 0.4625 0.7074 0.036 Uiso 1 1 calc R U . . .
C4 C 0.6777(3) 0.4521(7) 0.7703(3) 0.0312(8) Uani 1 1 d . . . . .
H4 H 0.6711 0.6611 0.7470 0.037 Uiso 1 1 calc R U . . .
C5 C 0.6353(3) 0.4226(7) 0.8926(3) 0.0355(8) Uani 1 1 d . . . . .
H5A H 0.5680 0.2672 0.9001 0.043 Uiso 1 1 calc R U . . .
H5B H 0.5964 0.6080 0.9195 0.043 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0370(11) 0.0331(13) 0.0581(14) 0.0049(9) 0.0131(10) 0.0033(8)
F2 0.0177(8) 0.0413(10) 0.0524(12) -0.0021(10) -0.0013(9) 0.0086(6)
F3 0.0388(10) 0.0303(12) 0.0488(12) -0.0045(8) 0.0002(10) 0.0032(7)
F4 0.0256(10) 0.0769(15) 0.0538(14) -0.0139(11) -0.0002(11) -0.0153(8)
C1 0.0226(15) 0.0264(18) 0.0420(19) -0.0003(14) 0.0060(13) 0.0040(12)
C2 0.0131(12) 0.0289(16) 0.0482(18) 0.0017(15) 0.0014(12) 0.0044(11)
C3 0.0215(13) 0.0234(16) 0.0449(19) -0.0033(14) 0.0029(13) 0.0000(12)
C4 0.0183(12) 0.0291(19) 0.0464(19) -0.0011(14) -0.0036(12) -0.0036(11)
C5 0.0176(14) 0.0407(19) 0.0481(19) -0.0074(16) 0.0021(13) 0.0020(12)

#==============================================================================
_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    SIR97
_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
F1 C1 1.408(4) . ?
F2 C2 1.400(3) . ?
F3 C3 1.403(3) . ?
F4 C4 1.399(4) . ?
C1 C2 1.518(4) . ?
C1 C5 1.537(4) . ?
C1 H1 1.0000 . ?
C2 C3 1.526(5) . ?
C2 H2 1.0000 . ?
C3 C4 1.541(4) . ?
C3 H3 1.0000 . ?
C4 C5 1.521(5) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?

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
F1 C1 C2 109.1(2) . . ?
F1 C1 C5 109.9(3) . . ?
C2 C1 C5 103.2(3) . . ?
F1 C1 H1 111.5 . . ?
C2 C1 H1 111.5 . . ?
C5 C1 H1 111.5 . . ?
F2 C2 C1 111.7(3) . . ?
F2 C2 C3 112.7(3) . . ?
C1 C2 C3 105.6(2) . . ?
F2 C2 H2 109.0 . . ?
C1 C2 H2 109.0 . . ?
C3 C2 H2 109.0 . . ?
F3 C3 C2 108.5(3) . . ?
F3 C3 C4 108.9(2) . . ?
C2 C3 C4 102.6(2) . . ?
F3 C3 H3 112.1 . . ?
C2 C3 H3 112.1 . . ?
C4 C3 H3 112.1 . . ?
F4 C4 C5 112.2(2) . . ?
F4 C4 C3 110.7(3) . . ?
C5 C4 C3 105.9(3) . . ?
F4 C4 H4 109.3 . . ?
C5 C4 H4 109.3 . . ?
C3 C4 H4 109.3 . . ?
C4 C5 C1 108.0(2) . . ?
C4 C5 H5A 110.1 . . ?
C1 C5 H5A 110.1 . . ?
C4 C5 H5B 110.1 . . ?
C1 C5 H5B 110.1 . . ?
H5A C5 H5B 108.4 . . ?

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
F1 C1 C2 F2 -40.6(3) . . . . ?
C5 C1 C2 F2 -157.3(2) . . . . ?
F1 C1 C2 C3 82.2(3) . . . . ?
C5 C1 C2 C3 -34.6(3) . . . . ?
F2 C2 C3 F3 45.9(3) . . . . ?
C1 C2 C3 F3 -76.2(3) . . . . ?
F2 C2 C3 C4 161.0(2) . . . . ?
C1 C2 C3 C4 38.9(3) . . . . ?
F3 C3 C4 F4 -34.5(4) . . . . ?
C2 C3 C4 F4 -149.3(3) . . . . ?
F3 C3 C4 C5 87.4(3) . . . . ?
C2 C3 C4 C5 -27.5(3) . . . . ?
F4 C4 C5 C1 127.6(2) . . . . ?
C3 C4 C5 C1 6.7(3) . . . . ?
F1 C1 C5 C4 -99.3(3) . . . . ?
C2 C1 C5 C4 16.9(3) . . . . ?

#==============================================================================

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

_shelx_res_file                  
;

    shelxl.res created by SHELXL-2014/7

TITL xcalibur
CELL  0.71075 10.11500 4.58750 11.87600 90.000 90.026 90.000
ZERR  4 0.00190 0.00110 0.00300 0.000 0.018 0.000
LATT 1
SYMM    -X, 1/2+Y, 1/2-Z
SFAC C H F
UNIT 20 24 16
SHEL 99999.000000 0.834642
L.S. 20
FMAP 2
PLAN -5
WPDB -2
HTAB
BOND $H
CONF
LIST 4
TEMP -180.0
ACTA
SIZE 0.150 0.030 0.030
TWIN -1 0 0 0 -1 0 0 0 1

WGHT    0.069500
BASF   0.45363
FVAR       3.04065
F1    3    0.761551    0.043948    0.983674    11.00000    0.03695    0.03307 =
         0.05808    0.00488    0.01306    0.00334
F2    3    0.987696    0.275186    0.913161    11.00000    0.01765    0.04134 =
         0.05244   -0.00205   -0.00131    0.00856
F3    3    0.828405    0.052468    0.750878    11.00000    0.03880    0.03028 =
         0.04881   -0.00449    0.00021    0.00322
F4    3    0.600534    0.281126    0.698191    11.00000    0.02560    0.07695 =
         0.05381   -0.01388   -0.00021   -0.01531
C1    1    0.758309    0.345949    0.962661    11.00000    0.02264    0.02639 =
         0.04201   -0.00026    0.00604    0.00397
AFIX  13
H1    2    0.761537    0.460533    1.034241    11.00000   -1.20000
AFIX   0
C2    1    0.871863    0.425593    0.884953    11.00000    0.01313    0.02889 =
         0.04817    0.00169    0.00139    0.00442
AFIX  13
H2    2    0.888796    0.639844    0.890677    11.00000   -1.20000
AFIX   0
C3    1    0.823460    0.355492    0.766285    11.00000    0.02151    0.02342 =
         0.04493   -0.00331    0.00291   -0.00002
AFIX  13
H3    2    0.874708    0.462525    0.707351    11.00000   -1.20000
AFIX   0
C4    1    0.677654    0.452133    0.770270    11.00000    0.01827    0.02906 =
         0.04635   -0.00106   -0.00359   -0.00362
AFIX  13
H4    2    0.671057    0.661090    0.746954    11.00000   -1.20000
AFIX   0
C5    1    0.635315    0.422613    0.892638    11.00000    0.01764    0.04068 =
         0.04807   -0.00740    0.00205    0.00202
AFIX  23
H5A   2    0.567963    0.267237    0.900104    11.00000   -1.20000
H5B   2    0.596431    0.608006    0.919525    11.00000   -1.20000
AFIX   0
HKLF 4

REM  xcalibur
REM R1 =  0.0605 for     898 Fo > 4sig(Fo)  and  0.0638 for all     987 data
REM     83 parameters refined using      0 restraints

END

WGHT      0.0688      0.0000

REM Instructions for potential hydrogen bonds
EQIV $1 x, y+1, z
HTAB C2 F1_$1
HTAB C2 F3_$1
EQIV $2 -x+2, y+1/2, -z+3/2
HTAB C3 F2_$2
HTAB C4 F3_$1
EQIV $3 -x+1, y+1/2, -z+3/2
HTAB C5 F4_$3

REM Highest difference peak  0.373,  deepest hole -0.395,  1-sigma level  0.091
Q1    1   0.8428 -0.0008  0.6595  11.00000  0.05    0.33
Q2    1   0.8391  0.2679  0.6882  11.00000  0.05    0.32
Q3    1   0.7709  0.0015  0.8954  11.00000  0.05    0.30
Q4    1   0.6460  0.5881  0.8409  11.00000  0.05    0.30
Q5    1   0.7552  0.1889  1.0358  11.00000  0.05    0.29
;

_shelx_res_checksum              39685
