# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1022936'
_audit_update_record             
;
2014-09-04 deposited with the CCDC.
2015-09-16 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            RRC4F
_chemical_formula_moiety         'C14 H12 F14 N2 O2'
_chemical_formula_sum            'C14 H12 F14 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         506.26
_chemical_absolute_configuration rm

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.0662(7)
_cell_length_b                   16.484(2)
_cell_length_c                   10.9207(14)
_cell_angle_alpha                90
_cell_angle_beta                 100.049(2)
_cell_angle_gamma                90
_cell_volume                     898.0(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2801
_cell_measurement_theta_min      2.4711
_cell_measurement_theta_max      30.2585
_cell_measurement_temperature    93.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear pale white'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.872
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504

_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.54
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      93.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scan'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            4732
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_reflns_number_total             2671
_reflns_number_gt                2552
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0930
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.042
_refine_ls_number_reflns         2671
_refine_ls_number_parameters     289
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0596P)²+0.1290P] 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          0.026
_refine_ls_shift/su_mean         0.005
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.273
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(7)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XSELL V6. 3. 1'
_computing_publication_material  'Generate Report'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.8275(4) 0.51709(11) 0.36491(16) 0.0350(5) Uani d . 1 . .
F F2 0.4494(4) 0.07212(12) 0.40578(17) 0.0327(5) Uani d . 1 . .
F F3 0.7931(4) 0.14729(11) 0.46730(16) 0.0306(5) Uani d . 1 . .
F F4 0.8282(4) 0.04159(11) 0.35447(16) 0.0306(4) Uani d . 1 . .
F F5 0.8276(4) 0.19360(11) 0.24021(16) 0.0241(4) Uani d . 1 . .
F F6 0.2855(3) 0.06237(10) 0.15706(15) 0.0209(4) Uani d . 1 . .
F F7 0.6808(3) 0.06315(10) 0.10441(15) 0.0216(4) Uani d . 1 . .
F F8 0.7001(3) 0.50201(10) 0.10656(14) 0.0208(4) Uani d . 1 . .
F F9 1.1375(3) 0.50854(10) 0.13942(15) 0.0214(4) Uani d . 1 . .
F F10 0.9651(4) 0.40706(12) 0.46064(16) 0.0320(5) Uani d . 1 . .
F F11 1.2438(4) 0.48337(13) 0.38654(17) 0.0356(5) Uani d . 1 . .
F F12 1.1266(4) 0.35036(11) 0.24885(17) 0.0270(4) Uani d . 1 . .
F F13 0.6970(4) 0.37061(10) 0.23864(16) 0.0253(4) Uani d . 1 . .
F F14 0.4224(4) 0.21155(10) 0.27865(16) 0.0260(4) Uani d . 1 . .
O O1 1.1553(4) 0.39199(13) -0.02295(19) 0.0225(5) Uani d . 1 . .
O O2 0.1347(4) 0.18123(13) 0.00073(19) 0.0225(5) Uani d . 1 . .
N N1 0.7069(5) 0.37011(13) -0.0415(2) 0.0150(5) Uani d . 1 . .
H H1 0.5633 0.3805 -0.009 0.018 Uiso calc R 1 . .
N N2 0.5605(5) 0.20008(14) -0.0328(2) 0.0162(5) Uani d . 1 . .
H H2 0.7315 0.1909 -0.0046 0.019 Uiso calc R 1 . .
C C1 0.9939(6) 0.45552(18) 0.3663(3) 0.0218(7) Uani d . 1 . .
C C2 0.9368(5) 0.40732(18) 0.2438(2) 0.0170(6) Uani d . 1 . .
C C3 0.9288(6) 0.45685(17) 0.1236(3) 0.0161(6) Uani d . 1 . .
C C4 0.9411(6) 0.40250(17) 0.0097(2) 0.0147(6) Uani d . 1 . .
C C5 0.6836(6) 0.31757(17) -0.1510(2) 0.0149(6) Uani d . 1 . .
H H5 0.8626 0.2925 -0.153 0.018 Uiso calc R 1 . .
C C6 0.4812(6) 0.24999(17) -0.1443(2) 0.0156(6) Uani d . 1 . .
H H6 0.3049 0.2758 -0.1389 0.019 Uiso calc R 1 . .
C C7 0.3768(6) 0.16865(17) 0.0259(3) 0.0171(6) Uani d . 1 . .
C C8 0.4868(6) 0.11076(17) 0.1347(3) 0.0163(6) Uani d . 1 . .
C C9 0.6002(6) 0.15588(18) 0.2558(3) 0.0178(6) Uani d . 1 . .
C C10 0.6687(7) 0.10198(19) 0.3726(3) 0.0228(7) Uani d . 1 . .
C C11 0.6010(6) 0.36805(18) -0.2701(3) 0.0205(6) Uani d . 1 . .
H H11A 0.4332 0.3976 -0.2652 0.025 Uiso calc R 1 . .
H H11B 0.7421 0.4086 -0.2763 0.025 Uiso calc R 1 . .
C C12 0.5584(7) 0.31497(19) -0.3865(3) 0.0226(7) Uani d . 1 . .
H H12A 0.4928 0.3489 -0.4604 0.027 Uiso calc R 1 . .
H H12B 0.7314 0.2906 -0.3974 0.027 Uiso calc R 1 . .
C C13 0.3573(6) 0.24811(19) -0.3767(3) 0.0218(7) Uani d . 1 . .
H H13A 0.3401 0.2129 -0.4511 0.026 Uiso calc R 1 . .
H H13B 0.1796 0.2725 -0.3743 0.026 Uiso calc R 1 . .
C C14 0.4432(6) 0.19700(18) -0.2603(3) 0.0201(7) Uani d . 1 . .
H H14A 0.3052 0.1553 -0.2546 0.024 Uiso calc R 1 . .
H H14B 0.6133 0.1688 -0.2658 0.024 Uiso calc R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C1 . 1.318(4) ?
F2 C10 . 1.323(4) ?
F3 C10 . 1.340(4) ?
F4 C10 . 1.319(4) ?
F5 C9 . 1.346(4) ?
F6 C8 . 1.350(3) ?
F7 C8 . 1.343(3) ?
F8 C3 . 1.362(3) ?
F9 C3 . 1.346(3) ?
F10 C1 . 1.332(4) ?
F11 C1 . 1.329(4) ?
F12 C2 . 1.338(4) ?
F13 C2 . 1.349(3) ?
F14 C9 . 1.340(3) ?
O1 C4 . 1.213(3) ?
O2 C7 . 1.227(4) ?
N1 C4 . 1.332(4) ?
N1 C5 . 1.464(3) ?
N1 H1 . 0.88 ?
N2 C7 . 1.324(4) ?
N2 C6 . 1.466(3) ?
N2 H2 . 0.88 ?
C1 C2 . 1.539(4) ?
C2 C3 . 1.541(4) ?
C3 C4 . 1.543(4) ?
C5 C6 . 1.525(4) ?
C5 C11 . 1.540(4) ?
C5 H5 . 1.0 ?
C6 C14 . 1.523(4) ?
C6 H6 . 1.0 ?
C7 C8 . 1.550(4) ?
C8 C9 . 1.539(4) ?
C9 C10 . 1.544(4) ?
C11 C12 . 1.527(4) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 C13 . 1.518(4) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 C14 . 1.523(4) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 N1 C5 . . 121.3(2) ?
C4 N1 H1 . . 119.4 ?
C5 N1 H1 . . 119.4 ?
C7 N2 C6 . . 120.5(2) ?
C7 N2 H2 . . 119.7 ?
C6 N2 H2 . . 119.7 ?
F11 C1 F1 . . 109.0(3) ?
F11 C1 F10 . . 108.0(2) ?
F1 C1 F10 . . 108.3(3) ?
F11 C1 C2 . . 110.6(3) ?
F1 C1 C2 . . 111.4(2) ?
F10 C1 C2 . . 109.5(2) ?
F12 C2 F13 . . 108.8(2) ?
F12 C2 C1 . . 107.6(2) ?
F13 C2 C1 . . 107.4(2) ?
F12 C2 C3 . . 108.6(2) ?
F13 C2 C3 . . 108.2(2) ?
C1 C2 C3 . . 116.1(2) ?
F9 C3 F8 . . 107.6(2) ?
F9 C3 C2 . . 108.8(2) ?
F8 C3 C2 . . 107.5(2) ?
F9 C3 C4 . . 109.3(2) ?
F8 C3 C4 . . 111.1(2) ?
C2 C3 C4 . . 112.4(2) ?
O1 C4 N1 . . 126.6(3) ?
O1 C4 C3 . . 119.0(2) ?
N1 C4 C3 . . 114.4(2) ?
N1 C5 C6 . . 110.6(2) ?
N1 C5 C11 . . 110.0(2) ?
C6 C5 C11 . . 110.5(2) ?
N1 C5 H5 . . 108.6 ?
C6 C5 H5 . . 108.6 ?
C11 C5 H5 . . 108.6 ?
N2 C6 C5 . . 111.2(2) ?
N2 C6 C14 . . 110.2(2) ?
C5 C6 C14 . . 111.6(2) ?
N2 C6 H6 . . 107.9 ?
C5 C6 H6 . . 107.9 ?
C14 C6 H6 . . 107.9 ?
O2 C7 N2 . . 125.8(3) ?
O2 C7 C8 . . 119.2(3) ?
N2 C7 C8 . . 115.0(2) ?
F7 C8 F6 . . 107.9(2) ?
F7 C8 C9 . . 108.3(2) ?
F6 C8 C9 . . 108.1(2) ?
F7 C8 C7 . . 110.6(2) ?
F6 C8 C7 . . 108.7(2) ?
C9 C8 C7 . . 113.1(2) ?
F14 C9 F5 . . 109.0(2) ?
F14 C9 C8 . . 109.2(2) ?
F5 C9 C8 . . 108.3(2) ?
F14 C9 C10 . . 107.6(2) ?
F5 C9 C10 . . 107.2(2) ?
C8 C9 C10 . . 115.4(2) ?
F4 C10 F2 . . 109.1(3) ?
F4 C10 F3 . . 108.6(3) ?
F2 C10 F3 . . 107.5(2) ?
F4 C10 C9 . . 111.4(2) ?
F2 C10 C9 . . 111.2(3) ?
F3 C10 C9 . . 108.9(2) ?
C12 C11 C5 . . 111.8(2) ?
C12 C11 H11A . . 109.3 ?
C5 C11 H11A . . 109.3 ?
C12 C11 H11B . . 109.3 ?
C5 C11 H11B . . 109.3 ?
H11A C11 H11B . . 107.9 ?
C13 C12 C11 . . 110.9(3) ?
C13 C12 H12A . . 109.5 ?
C11 C12 H12A . . 109.5 ?
C13 C12 H12B . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 108.0 ?
C12 C13 C14 . . 111.3(2) ?
C12 C13 H13A . . 109.4 ?
C14 C13 H13A . . 109.4 ?
C12 C13 H13B . . 109.4 ?
C14 C13 H13B . . 109.4 ?
H13A C13 H13B . . 108.0 ?
C6 C14 C13 . . 110.7(2) ?
C6 C14 H14A . . 109.5 ?
C13 C14 H14A . . 109.5 ?
C6 C14 H14B . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 108.1 ?

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_CF4racemi2_1
_database_code_depnum_ccdc_archive 'CCDC 1040719'
_audit_update_record             
;
2014-12-22 deposited with the CCDC.
2015-09-16 downloaded from the CCDC.
;
_audit_creation_date             2014-10-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_formula_moiety         'C14 H12 F14 N2 O2'
_chemical_formula_sum            'C14 H12 F14 N2 O2'
_chemical_formula_weight         506.24
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y,-z+1/2
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y+1/2,z
5 -x,-y,-z
6 -x-1/2,y,z-1/2
7 x,-y-1/2,z-1/2
8 x-1/2,y-1/2,-z

_symmetry_Int_Tables_number      56
_cell_length_a                   18.5495(14)
_cell_length_b                   21.0121(16)
_cell_length_c                   9.5700(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3730.0(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6477
_cell_measurement_theta_min      2.5836
_cell_measurement_theta_max      28.9221
_cell_measurement_temperature    93.15
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_description       needle
_exptl_crystal_colour            'clear pale white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   pale
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.8028
_exptl_crystal_F_000             2018.4192
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            27365
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         31.14
_diffrn_reflns_theta_min         1.46
_diffrn_ambient_temperature      93.15
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9518
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              26
_reflns_limit_h_min              0
_reflns_limit_k_max              30
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                4282
_reflns_number_total             5725
_reflns_threshold_expression     I>=2u(I)
_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc.)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc.)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.6886
_refine_diff_density_min         -0.6562
_refine_diff_density_rms         0.0887
_refine_ls_d_res_high            0.6873
_refine_ls_d_res_low             13.9060
_refine_ls_goodness_of_fit_ref   1.0572
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     288
_refine_ls_number_reflns         5725
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.0572
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1362
_refine_ls_wR_factor_ref         0.1531
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C20(H20), C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C25(H25a,H25b), C26(H26a,H26b), C28(H28a,H28b), C31(H31a,H31b)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
F10 F 0.43919(5) 0.35811(4) 0.29701(9) 0.0202(2) Uani 1.000000 .
F9 F 0.40715(6) 0.39731(4) 0.09529(10) 0.0250(2) Uani 1.000000 .
F12 F 0.31908(5) 0.29224(5) 0.31978(12) 0.0299(2) Uani 1.000000 .
F8 F 0.70446(5) 0.30876(5) 0.06736(11) 0.0274(2) Uani 1.000000 .
F7 F 0.72700(5) 0.34021(5) 0.27963(12) 0.0319(3) Uani 1.000000 .
F11 F 0.28665(5) 0.31355(6) 0.10626(12) 0.0343(3) Uani 1.000000 .
F14 F 0.31822(6) 0.42411(6) 0.37120(13) 0.0365(3) Uani 1.000000 .
O2 O 0.43850(6) 0.28884(5) -0.02584(11) 0.0214(2) Uani 1.000000 .
F5 F 0.57285(6) 0.37086(5) 0.08085(14) 0.0381(3) Uani 1.000000 .
O1 O 0.60920(7) 0.27758(6) 0.37440(11) 0.0243(3) Uani 1.000000 .
N2 N 0.45585(7) 0.24105(6) 0.18603(12) 0.0158(2) Uani 1.000000 .
F15 F 0.21808(6) 0.37975(6) 0.31834(14) 0.0413(3) Uani 1.000000 .
F13 F 0.27225(8) 0.43661(6) 0.16605(13) 0.0469(3) Uani 1.000000 .
F4 F 0.60367(8) 0.40940(5) 0.28227(13) 0.0447(3) Uani 1.000000 .
N1 N 0.60966(7) 0.22626(6) 0.16475(13) 0.0161(2) Uani 1.000000 .
F1 F 0.68683(9) 0.42657(6) -0.03977(13) 0.0521(4) Uani 1.000000 .
F3 F 0.62605(8) 0.49214(5) 0.08032(15) 0.0472(3) Uani 1.000000 .
F2 F 0.72669(8) 0.45851(6) 0.15727(18) 0.0642(5) Uani 1.000000 .
C19 C 0.43482(7) 0.28758(7) 0.10122(15) 0.0141(3) Uani 1.000000 .
C20 C 0.48832(8) 0.18195(7) 0.13536(14) 0.0146(3) Uani 1.000000 .
C21 C 0.32217(8) 0.33592(7) 0.21766(16) 0.0186(3) Uani 1.000000 .
C22 C 0.62701(8) 0.27268(7) 0.25204(15) 0.0155(3) Uani 1.000000 .
C23 C 0.56240(8) 0.17319(7) 0.20412(15) 0.0150(3) Uani 1.000000 .
C24 C 0.40213(8) 0.34605(7) 0.17781(14) 0.0155(3) Uani 1.000000 .
C25 C 0.43892(8) 0.12551(7) 0.16520(16) 0.0193(3) Uani 1.000000 .
C26 C 0.54646(10) 0.05420(7) 0.19290(18) 0.0238(3) Uani 1.000000 .
C27 C 0.67391(8) 0.32633(7) 0.18914(15) 0.0171(3) Uani 1.000000 .
C28 C 0.59653(9) 0.11000(7) 0.16065(17) 0.0200(3) Uani 1.000000 .
C29 C 0.62951(9) 0.38705(7) 0.16171(16) 0.0206(3) Uani 1.000000 .
C30 C 0.28210(9) 0.39597(8) 0.26945(18) 0.0249(3) Uani 1.000000 .
C31 C 0.47404(9) 0.06306(7) 0.12045(18) 0.0227(3) Uani 1.000000 .
C32 C 0.66916(10) 0.44225(8) 0.08776(18) 0.0255(3) Uani 1.000000 .
H2 H 0.45012(7) 0.24590(6) 0.27456(12) 0.0189(3) Uiso 1.000000 R
H1 H 0.62683(7) 0.22725(6) 0.08131(13) 0.0193(3) Uiso 1.000000 R
H20 H 0.49507(8) 0.18535(7) 0.03407(14) 0.0175(3) Uiso 1.000000 R
H23 H 0.55626(8) 0.17336(7) 0.30583(15) 0.0180(3) Uiso 1.000000 R
H25a H 0.42822(8) 0.12394(7) 0.26435(16) 0.0232(4) Uiso 1.000000 R
H25b H 0.39385(8) 0.13104(7) 0.11528(16) 0.0232(4) Uiso 1.000000 R
H26a H 0.56852(10) 0.01488(7) 0.16138(18) 0.0286(4) Uiso 1.000000 R
H26b H 0.53916(10) 0.05119(7) 0.29305(18) 0.0286(4) Uiso 1.000000 R
H28a H 0.60686(9) 0.11086(7) 0.06130(17) 0.0241(4) Uiso 1.000000 R
H28b H 0.64173(9) 0.10431(7) 0.21006(17) 0.0241(4) Uiso 1.000000 R
H31a H 0.44248(9) 0.02783(7) 0.14385(18) 0.0272(4) Uiso 1.000000 R
H31b H 0.48101(9) 0.06312(7) 0.01999(18) 0.0272(4) Uiso 1.000000 R


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
F10 C24 1.3558(16) . ?
F9 C24 1.3389(16) . ?
F12 C21 1.3419(18) . ?
F8 C27 1.3475(17) . ?
F7 C27 1.3433(17) . ?
F11 C21 1.3385(17) . ?
F14 C30 1.322(2) . ?
O2 C19 1.2182(18) . ?
F5 C29 1.349(2) . ?
O1 C22 1.2211(18) . ?
N2 C19 1.3292(18) . ?
N2 C20 1.4628(18) . ?
N2 H2 0.8600 . ?
F15 C30 1.321(2) . ?
F13 C30 1.320(2) . ?
F4 C29 1.3347(18) . ?
N1 C22 1.3239(18) . ?
N1 C23 1.4676(18) . ?
N1 H1 0.8600 . ?
F1 C32 1.306(2) . ?
F3 C32 1.320(2) . ?
F2 C32 1.303(2) . ?
C19 C24 1.5539(19) . ?
C20 C23 1.535(2) . ?
C20 C25 1.526(2) . ?
C20 H20 0.9800 . ?
C21 C24 1.546(2) . ?
C21 C30 1.546(2) . ?
C22 C27 1.546(2) . ?
C23 C28 1.529(2) . ?
C23 H23 0.9800 . ?
C25 C31 1.526(2) . ?
C25 H25a 0.9700 . ?
C25 H25b 0.9700 . ?
C26 C28 1.527(2) . ?
C26 C31 1.523(2) . ?
C26 H26a 0.9700 . ?
C26 H26b 0.9700 . ?
C27 C29 1.541(2) . ?
C28 H28a 0.9700 . ?
C28 H28b 0.9700 . ?
C29 C32 1.545(2) . ?
C31 H31a 0.9700 . ?
C31 H31b 0.9700 . ?

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
C20 N2 C19 122.88(12) . . ?
H2 N2 C19 118.56(8) . . ?
H2 N2 C20 118.56(7) . . ?
C23 N1 C22 122.89(12) . . ?
H1 N1 C22 118.55(8) . . ?
H1 N1 C23 118.55(7) . . ?
N2 C19 O2 127.52(13) . . ?
C24 C19 O2 118.39(12) . . ?
C24 C19 N2 114.09(12) . . ?
C23 C20 N2 109.16(11) . . ?
C25 C20 N2 110.52(12) . . ?
C25 C20 C23 111.37(12) . . ?
H20 C20 N2 108.58(7) . . ?
H20 C20 C23 108.58(7) . . ?
H20 C20 C25 108.58(8) . . ?
F11 C21 F12 108.60(13) . . ?
C24 C21 F12 108.34(12) . . ?
C24 C21 F11 108.92(12) . . ?
C30 C21 F12 107.71(13) . . ?
C30 C21 F11 107.77(12) . . ?
C30 C21 C24 115.33(13) . . ?
N1 C22 O1 126.97(14) . . ?
C27 C22 O1 117.66(13) . . ?
C27 C22 N1 115.36(12) . . ?
C20 C23 N1 109.49(11) . . ?
C28 C23 N1 110.04(12) . . ?
C28 C23 C20 110.99(12) . . ?
H23 C23 N1 108.76(7) . . ?
H23 C23 C20 108.76(7) . . ?
H23 C23 C28 108.76(8) . . ?
F9 C24 F10 108.10(12) . . ?
C19 C24 F10 110.29(11) . . ?
C19 C24 F9 109.31(11) . . ?
C21 C24 F10 107.74(11) . . ?
C21 C24 F9 108.85(12) . . ?
C21 C24 C19 112.45(11) . . ?
C31 C25 C20 111.06(12) . . ?
H25a C25 C20 109.42(8) . . ?
H25a C25 C31 109.42(9) . . ?
H25b C25 C20 109.42(8) . . ?
H25b C25 C31 109.42(9) . . ?
H25b C25 H25a 108.0 . . ?
C31 C26 C28 110.52(13) . . ?
H26a C26 C28 109.55(9) . . ?
H26a C26 C31 109.55(8) . . ?
H26b C26 C28 109.55(9) . . ?
H26b C26 C31 109.55(9) . . ?
H26b C26 H26a 108.1 . . ?
F7 C27 F8 107.98(12) . . ?
C22 C27 F8 111.94(12) . . ?
C22 C27 F7 108.65(12) . . ?
C29 C27 F8 107.72(12) . . ?
C29 C27 F7 108.78(12) . . ?
C29 C27 C22 111.67(12) . . ?
C26 C28 C23 111.09(13) . . ?
H28a C28 C23 109.42(8) . . ?
H28a C28 C26 109.42(9) . . ?
H28b C28 C23 109.42(8) . . ?
H28b C28 C26 109.42(9) . . ?
H28b C28 H28a 108.0 . . ?
F4 C29 F5 107.76(14) . . ?
C27 C29 F5 107.78(12) . . ?
C27 C29 F4 109.63(13) . . ?
C32 C29 F5 107.31(13) . . ?
C32 C29 F4 107.63(13) . . ?
C32 C29 C27 116.42(13) . . ?
F15 C30 F14 108.07(14) . . ?
F13 C30 F14 109.45(16) . . ?
F13 C30 F15 107.93(14) . . ?
C21 C30 F14 110.96(13) . . ?
C21 C30 F15 109.58(14) . . ?
C21 C30 F13 110.75(14) . . ?
C26 C31 C25 110.72(13) . . ?
H31a C31 C25 109.50(8) . . ?
H31a C31 C26 109.50(8) . . ?
H31b C31 C25 109.50(9) . . ?
H31b C31 C26 109.50(9) . . ?
H31b C31 H31a 108.1 . . ?
F3 C32 F1 107.57(15) . . ?
F2 C32 F1 109.74(17) . . ?
F2 C32 F3 108.38(15) . . ?
C29 C32 F1 110.99(14) . . ?
C29 C32 F3 109.41(14) . . ?
C29 C32 F2 110.66(15) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_name_systematic        'racemic CF4'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
