# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_c3f7
_database_code_depnum_ccdc_archive 'CCDC 1511340'
_audit_update_record             
;
2016-10-24 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;

_audit_creation_date             2016-10-20T14:47:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C10 H1 F11 N2'
_chemical_formula_sum            'C10 H1 F11 N2'
_chemical_formula_weight         358.13
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_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_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
_cell_length_a                   5.1207(5)
_cell_length_b                   9.1029(8)
_cell_length_c                   24.816(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1156.75(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7274
_cell_measurement_theta_min      3.56
_cell_measurement_theta_max      72.1
_cell_measurement_wavelength     1.54178

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       'plate stick'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    2.056
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_T_max  0.992

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source         micro-source
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       ω-φ
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_number            10865
_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       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.562
_diffrn_reflns_theta_max         72.48
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_number_total             2277
_reflns_number_gt                2092
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0560P)²+3.0962P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2277
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0625
_refine_ls_wR_factor_ref         0.1542
_refine_ls_wR_factor_gt          0.1506
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_restrained_S_all      1.161
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.111

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3125(12) 0.3835(7) 0.4094(2) 0.0124(12) Uani 1 d . .
C2 C 0.1170(13) 0.3219(7) 0.3699(2) 0.0160(12) Uani 1 d . .
C3 C 0.2551(13) 0.2375(7) 0.3241(2) 0.0172(13) Uani 1 d . .
C4 C 0.0823(15) 0.1836(7) 0.2770(2) 0.0208(14) Uani 1 d . .
C5 C 0.4595(13) 0.5138(6) 0.4063(2) 0.0130(12) Uani 1 d . .
C6 C 0.4832(13) 0.6366(6) 0.3716(2) 0.0152(12) Uani 1 d . .
C7 C 0.6692(15) 0.7400(7) 0.3820(2) 0.0206(14) Uani 1 d . .
C8 C 0.8405(14) 0.7251(7) 0.4260(3) 0.0197(13) Uani 1 d . .
C9 C 0.8207(13) 0.6100(7) 0.4604(2) 0.0169(13) Uani 1 d . .
C10 C 0.6291(13) 0.5047(7) 0.4505(2) 0.0140(12) Uani 1 d . .
N1 N 0.5697(11) 0.3793(6) 0.47725(19) 0.0160(11) Uani 1 d . .
H1 H 0.645507 0.350518 0.507261 0.019 Uiso 1 calc . .
N2 N 0.3777(11) 0.3043(6) 0.45161(19) 0.0167(11) Uani 1 d . .
F1 F -0.0286(7) 0.4303(4) 0.34789(13) 0.0183(8) Uani 1 d . .
F2 F -0.0463(7) 0.2278(4) 0.39528(14) 0.0211(8) Uani 1 d . .
F3 F 0.3737(8) 0.1201(4) 0.34548(15) 0.0257(9) Uani 1 d . .
F4 F 0.4383(8) 0.3270(4) 0.30271(14) 0.0218(8) Uani 1 d . .
F5 F -0.0184(9) 0.2973(4) 0.25045(14) 0.0252(9) Uani 1 d . .
F6 F -0.1078(8) 0.0997(4) 0.29450(15) 0.0263(9) Uani 1 d . .
F7 F 0.2289(9) 0.1078(5) 0.24270(15) 0.0288(10) Uani 1 d . .
F8 F 0.3226(7) 0.6532(4) 0.32960(14) 0.0217(9) Uani 1 d . .
F9 F 0.6929(9) 0.8578(4) 0.35044(15) 0.0271(9) Uani 1 d . .
F10 F 1.0209(9) 0.8292(4) 0.43363(16) 0.0272(9) Uani 1 d . .
F11 F 0.9861(8) 0.5944(4) 0.50223(13) 0.0226(9) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   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
C1 N2 1.314(8) . ?
C1 C5 1.407(9) . ?
C1 C2 1.510(8) . ?
C2 F1 1.351(7) . ?
C2 F2 1.353(7) . ?
C2 C3 1.543(9) . ?
C3 F3 1.338(7) . ?
C3 F4 1.352(7) . ?
C3 C4 1.545(9) . ?
C4 F6 1.311(8) . ?
C4 F7 1.329(8) . ?
C4 F5 1.331(8) . ?
C5 C10 1.401(9) . ?
C5 C6 1.417(8) . ?
C6 F8 1.335(7) . ?
C6 C7 1.364(9) . ?
C7 F9 1.334(7) . ?
C7 C8 1.406(10) . ?
C8 F10 1.337(8) . ?
C8 C9 1.356(9) . ?
C9 F11 1.347(7) . ?
C9 C10 1.394(9) . ?
C10 N1 1.355(8) . ?
N1 N2 1.356(8) . ?

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
N2 C1 C5 111.7(5) . . ?
N2 C1 C2 118.9(5) . . ?
C5 C1 C2 129.2(5) . . ?
F1 C2 F2 108.0(5) . . ?
F1 C2 C1 110.9(5) . . ?
F2 C2 C1 110.0(5) . . ?
F1 C2 C3 108.6(5) . . ?
F2 C2 C3 108.1(5) . . ?
C1 C2 C3 111.1(5) . . ?
F3 C3 F4 108.8(5) . . ?
F3 C3 C2 108.3(5) . . ?
F4 C3 C2 107.9(5) . . ?
F3 C3 C4 107.8(5) . . ?
F4 C3 C4 107.0(5) . . ?
C2 C3 C4 116.9(6) . . ?
F6 C4 F7 109.2(5) . . ?
F6 C4 F5 109.2(6) . . ?
F7 C4 F5 107.7(5) . . ?
F6 C4 C3 111.1(5) . . ?
F7 C4 C3 109.0(6) . . ?
F5 C4 C3 110.5(5) . . ?
C10 C5 C1 103.8(5) . . ?
C10 C5 C6 118.0(6) . . ?
C1 C5 C6 138.1(6) . . ?
F8 C6 C7 120.0(5) . . ?
F8 C6 C5 120.7(5) . . ?
C7 C6 C5 119.2(6) . . ?
F9 C7 C6 120.4(6) . . ?
F9 C7 C8 118.5(6) . . ?
C6 C7 C8 121.1(6) . . ?
F10 C8 C9 120.7(6) . . ?
F10 C8 C7 118.2(6) . . ?
C9 C8 C7 121.1(6) . . ?
F11 C9 C8 121.3(6) . . ?
F11 C9 C10 120.4(5) . . ?
C8 C9 C10 118.2(6) . . ?
N1 C10 C9 130.6(6) . . ?
N1 C10 C5 107.1(5) . . ?
C9 C10 C5 122.3(6) . . ?
C10 N1 N2 110.9(5) . . ?
C1 N2 N1 106.4(5) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of 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_CF2CF3
_database_code_depnum_ccdc_archive 'CCDC 1511341'
_audit_update_record             
;
2016-10-24 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;

_audit_creation_date             2016-09-23T10:52:32-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C9 H1 F9 N2'
_chemical_formula_sum            'C9 H F9 N2'
_chemical_formula_weight         308.12
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   'P 32'
_symmetry_space_group_name_Hall  'P 32'
_symmetry_Int_Tables_number      145
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
_cell_length_a                   12.4065(3)
_cell_length_b                   12.4065(3)
_cell_length_c                   5.5725(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     742.81(4)
_cell_formula_units_Z            3
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    4151
_cell_measurement_theta_min      4.09
_cell_measurement_theta_max      61.695
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    2.066
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             450

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.4019
_exptl_absorpt_correction_T_max  0.7715

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed X-ray tube'
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1978
_diffrn_orient_matrix_ub_11      0.0998001
_diffrn_orient_matrix_ub_12      -0.023889
_diffrn_orient_matrix_ub_13      -0.1115391
_diffrn_orient_matrix_ub_21      0.0378752
_diffrn_orient_matrix_ub_22      0.1100283
_diffrn_orient_matrix_ub_23      -0.1729617
_diffrn_orient_matrix_ub_31      0.0957184
_diffrn_orient_matrix_ub_32      0.0886477
_diffrn_orient_matrix_ub_33      0.1847869
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_number            7626
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         4.115
_diffrn_reflns_theta_max         61.664
_diffrn_reflns_theta_full        61.664
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_reflns_number_total             1527
_reflns_number_gt                1497
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0417P)²+0.0136P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1527
_refine_ls_number_parameters     185
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.023
_refine_ls_wR_factor_ref         0.0606
_refine_ls_wR_factor_gt          0.0593
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.14(16)
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.043

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0994(3) 0.7087(3) 0.8905(5) 0.0216(7) Uani 1 d . .
C2 C 1.1144(3) 0.8015(3) 1.0772(5) 0.0233(7) Uani 1 d . .
C3 C 1.1479(3) 0.9298(3) 0.9755(6) 0.0265(7) Uani 1 d . .
C4 C 0.9969(3) 0.6372(3) 0.7341(5) 0.0212(6) Uani 1 d . .
C5 C 1.0408(3) 0.5770(3) 0.5809(5) 0.0215(6) Uani 1 d . .
C6 C 0.9696(3) 0.5028(3) 0.3895(6) 0.0240(7) Uani 1 d . .
C7 C 0.8539(3) 0.4873(3) 0.3578(6) 0.0238(7) Uani 1 d . .
C8 C 0.8075(3) 0.5440(3) 0.5131(6) 0.0239(7) Uani 1 d . .
C9 C 0.8757(3) 0.6170(3) 0.6992(6) 0.0224(7) Uani 1 d . .
N2 N 1.1945(2) 0.6920(2) 0.8388(5) 0.0239(6) Uani 1 d . .
N1 N 1.1583(2) 0.6124(2) 0.6510(5) 0.0234(6) Uani 1 d . .
H1 H 1.206(4) 0.582(4) 0.596(6) 0.028 Uiso 1 d . .
F1 F 1.00752(17) 0.76122(16) 1.2032(3) 0.0291(4) Uani 1 d . .
F2 F 1.20491(18) 0.81949(17) 1.2344(3) 0.0321(5) Uani 1 d . .
F3 F 1.06409(19) 0.91868(17) 0.8158(3) 0.0374(5) Uani 1 d . .
F4 F 1.1530(2) 1.00515(17) 1.1482(4) 0.0398(5) Uani 1 d . .
F5 F 1.2583(2) 0.9802(2) 0.8686(4) 0.0419(6) Uani 1 d . .
F6 F 1.01603(18) 0.45249(18) 0.2369(3) 0.0310(5) Uani 1 d . .
F7 F 0.78197(17) 0.42010(16) 0.1748(3) 0.0310(5) Uani 1 d . .
F8 F 0.69322(16) 0.52577(18) 0.4686(4) 0.0306(4) Uani 1 d . .
F9 F 0.82896(17) 0.66924(18) 0.8432(3) 0.0286(4) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   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
C1 N2 1.328(4) . ?
C1 C4 1.426(4) . ?
C1 C2 1.493(4) . ?
C2 F2 1.352(4) . ?
C2 F1 1.355(4) . ?
C2 C3 1.538(4) . ?
C3 F4 1.321(4) . ?
C3 F3 1.322(4) . ?
C3 F5 1.329(4) . ?
C4 C9 1.409(4) . ?
C4 C5 1.411(4) . ?
C5 N1 1.353(4) . ?
C5 C6 1.397(5) . ?
C6 F6 1.343(4) . ?
C6 C7 1.362(5) . ?
C7 F7 1.337(4) . ?
C7 C8 1.407(5) . ?
C8 F8 1.343(4) . ?
C8 C9 1.358(5) . ?
C9 F9 1.333(4) . ?
N2 N1 1.352(4) . ?
N1 H1 0.89(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 C4 110.8(3) . . ?
N2 C1 C2 119.6(3) . . ?
C4 C1 C2 129.3(3) . . ?
F2 C2 F1 107.7(2) . . ?
F2 C2 C1 110.6(3) . . ?
F1 C2 C1 110.8(3) . . ?
F2 C2 C3 107.2(2) . . ?
F1 C2 C3 106.3(2) . . ?
C1 C2 C3 114.0(2) . . ?
F4 C3 F3 108.7(3) . . ?
F4 C3 F5 108.7(3) . . ?
F3 C3 F5 108.6(3) . . ?
F4 C3 C2 110.9(3) . . ?
F3 C3 C2 110.4(2) . . ?
F5 C3 C2 109.5(3) . . ?
C9 C4 C5 118.8(3) . . ?
C9 C4 C1 137.4(3) . . ?
C5 C4 C1 103.8(3) . . ?
N1 C5 C6 131.1(3) . . ?
N1 C5 C4 107.0(3) . . ?
C6 C5 C4 121.8(3) . . ?
F6 C6 C7 121.3(3) . . ?
F6 C6 C5 120.9(3) . . ?
C7 C6 C5 117.8(3) . . ?
F7 C7 C6 121.0(3) . . ?
F7 C7 C8 118.0(3) . . ?
C6 C7 C8 121.0(3) . . ?
F8 C8 C9 120.4(3) . . ?
F8 C8 C7 117.6(3) . . ?
C9 C8 C7 121.9(3) . . ?
F9 C9 C8 120.4(3) . . ?
F9 C9 C4 121.0(3) . . ?
C8 C9 C4 118.5(3) . . ?
C1 N2 N1 106.6(3) . . ?
N2 N1 C5 111.8(3) . . ?
N2 N1 H1 122(2) . . ?
C5 N1 H1 126(2) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of 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_CF2CF3microCu
_database_code_depnum_ccdc_archive 'CCDC 1511342'
_audit_update_record             
;
2016-10-24 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;


_refine_special_details          
; 
? 
;

_cell_length_a                   12.3863(7)
_cell_length_b                   12.3863(7)
_cell_length_c                   5.5727(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     740.42(7)

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   'P 32 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-y,x-y,z+2/3
-x+y,-x,z+1/3

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_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            3

# Given Formula = C9 H0.33 F2.33 N0.67 
# Dc =      1.09 Fooo =    450.00 Mu =      8.45 M =    162.10
# Found Formula = C9 H1 F9 N2 
# Dc =      2.07 FOOO =    450.00 Mu =     22.84 M =    308.10

_chemical_formula_sum            'C9 H1 F9 N2'
_chemical_formula_moiety         'C9 H1 F9 N2'
_chemical_compound_source        ?
_chemical_formula_weight         308.10


_cell_measurement_reflns_used    9865
_cell_measurement_theta_min      4
_cell_measurement_theta_max      72
_cell_measurement_temperature    100

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.250

_exptl_crystal_density_diffrn    2.073
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             450
_exptl_absorpt_coefficient_mu    2.284

# Sheldrick geometric approximatio 0.63 0.80 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.41
_exptl_absorpt_correction_T_max  0.80
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      100
_diffrn_reflns_number            16067
_reflns_number_total             1926
_diffrn_reflns_av_R_equivalents  0.056
# Number of reflections without Friedels Law is 1926 
# Number of reflections with Friedels Law is 974 
# Theoretical number of reflections is about 975 


_diffrn_reflns_theta_min         4.121
_diffrn_reflns_theta_max         72.292
_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        72.292
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_reflns_limit_h_min              -15
_reflns_limit_h_max              7
_reflns_limit_k_min              0
_reflns_limit_k_max              15
_reflns_limit_l_min              -6
_reflns_limit_l_max              6


_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.26
_refine_diff_density_max         0.24


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_refine_ls_number_reflns         1919
_refine_ls_number_restraints     1
_refine_ls_number_parameters     182
_refine_ls_wR_factor_ref         0.0688
_refine_ls_goodness_of_fit_ref   0.9188
_refine_ls_shift/su_max          0.0074740
_refine_ls_shift/su_mean         0.0006432


# The values computed with all filters except I/sigma  
_refine_ls_R_factor_all          0.0278
_refine_ls_wR_factor_all         0.0688

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1904
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_gt          0.0686

_refine_ls_abs_structure_Flack   0.22(10)
_refine_ls_abs_structure_details 'Flack (1983), 952 Friedel-pairs'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    noref #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 0.42P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
F1 F 0.32672(10) 0.42085(10) 0.9813(2) 0.0194 1.0000 Uani . . . . . .
F2 F 0.50513(10) 0.50765(10) 1.3410(2) 0.0196 1.0000 Uani . . . . . .
C3 C 0.45773(17) 0.40788(17) 1.4850(3) 0.0149 1.0000 Uani . . . . . .
C4 C 0.52705(17) 0.40412(18) 1.6714(4) 0.0153 1.0000 Uani . . . . . .
F5 F 0.64110(10) 0.49959(10) 1.7154(2) 0.0213 1.0000 Uani . . . . . .
C6 C 0.47992(17) 0.30001(18) 1.8263(3) 0.0154 1.0000 Uani . . . . . .
F7 F 0.55190(11) 0.30508(11) 2.0092(2) 0.0218 1.0000 Uani . . . . . .
F8 F 0.12870(11) 0.28126(11) 0.9496(2) 0.0225 1.0000 Uani . . . . . .
F9 F 0.26955(12) 0.52182(12) 1.3688(2) 0.0276 1.0000 Uani . . . . . .
F10 F 0.31709(11) 0.10283(10) 1.9467(2) 0.0211 1.0000 Uani . . . . . .
F11 F 0.18072(13) 0.51941(12) 1.0352(3) 0.0295 1.0000 Uani . . . . . .
N12 N 0.13908(14) 0.16412(14) 1.3455(3) 0.0151 1.0000 Uani . . . . . .
N13 N 0.17485(14) 0.12061(14) 1.5328(3) 0.0158 1.0000 Uani . . . . . .
F14 F 0.07473(12) 0.38844(13) 1.3147(3) 0.0310 1.0000 Uani . . . . . .
C1 C 0.33683(16) 0.30716(16) 1.4504(3) 0.0133 1.0000 Uani . . . . . .
C7 C 0.21946(16) 0.35421(18) 1.1072(3) 0.0155 1.0000 Uani . . . . . .
C2 C 0.29286(16) 0.20303(16) 1.6027(3) 0.0137 1.0000 Uani . . . . . .
C10 C 0.18529(18) 0.44890(18) 1.2086(4) 0.0191 1.0000 Uani . . . . . .
C5 C 0.23396(16) 0.27588(16) 1.2938(3) 0.0133 1.0000 Uani . . . . . .
C8 C 0.36369(17) 0.19966(17) 1.7944(3) 0.0152 1.0000 Uani . . . . . .
H1 H 0.1240 0.0452 1.5683 0.0500 1.0000 Uiso . . . . . .

_refine_ls_extinction_method     None
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 . C7 . 1.357(2) yes
F2 . C3 . 1.338(2) yes
C3 . C4 . 1.363(3) yes
C3 . C1 . 1.403(3) yes
C4 . F5 . 1.336(2) yes
C4 . C6 . 1.413(3) yes
C6 . F7 . 1.335(2) yes
C6 . C8 . 1.364(3) yes
F8 . C7 . 1.355(2) yes
F9 . C10 . 1.326(2) yes
F10 . C8 . 1.342(2) yes
F11 . C10 . 1.323(2) yes
N12 . N13 . 1.347(2) yes
N12 . C5 . 1.324(2) yes
N13 . C2 . 1.356(2) yes
N13 . H1 . 0.848 no
F14 . C10 . 1.327(2) yes
C1 . C2 . 1.406(2) yes
C1 . C5 . 1.429(2) yes
C7 . C10 . 1.540(2) yes
C7 . C5 . 1.493(3) yes
C2 . C8 . 1.396(3) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F2 . C3 . C4 . 119.70(16) yes
F2 . C3 . C1 . 121.30(16) yes
C4 . C3 . C1 . 118.99(17) yes
C3 . C4 . F5 . 121.00(17) yes
C3 . C4 . C6 . 121.12(17) yes
F5 . C4 . C6 . 117.87(16) yes
C4 . C6 . F7 . 117.53(16) yes
C4 . C6 . C8 . 121.22(17) yes
F7 . C6 . C8 . 121.22(17) yes
N13 . N12 . C5 . 106.82(15) yes
N12 . N13 . C2 . 111.57(15) yes
N12 . N13 . H1 . 114.2 no
C2 . N13 . H1 . 133.6 no
C3 . C1 . C2 . 118.98(17) yes
C3 . C1 . C5 . 137.36(17) yes
C2 . C1 . C5 . 103.65(15) yes
F1 . C7 . F8 . 107.69(15) yes
F1 . C7 . C10 . 106.54(15) yes
F8 . C7 . C10 . 107.06(14) yes
F1 . C7 . C5 . 110.86(14) yes
F8 . C7 . C5 . 110.33(15) yes
C10 . C7 . C5 . 114.06(16) yes
C1 . C2 . N13 . 107.14(16) yes
C1 . C2 . C8 . 121.88(16) yes
N13 . C2 . C8 . 130.86(17) yes
C7 . C10 . F14 . 109.44(15) yes
C7 . C10 . F9 . 110.08(15) yes
F14 . C10 . F9 . 108.86(17) yes
C7 . C10 . F11 . 110.70(17) yes
F14 . C10 . F11 . 109.00(16) yes
F9 . C10 . F11 . 108.72(16) yes
C7 . C5 . C1 . 129.04(16) yes
C7 . C5 . N12 . 119.91(16) yes
C1 . C5 . N12 . 110.82(16) yes
C2 . C8 . F10 . 120.99(16) yes
C2 . C8 . C6 . 117.73(17) yes
F10 . C8 . C6 . 121.23(17) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N13 . H1 . N12 3_555 170.55(11) 0.848 2.073 2.913(3) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 06/10/16 at 14:44:26
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
END                                                                             
;


_iucr_refine_instructions_details_restraints 
;
#
# Punched on 06/10/16 at 14:44:26
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;


