# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_52
_database_code_depnum_ccdc_archive 'CCDC 1008431'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2015-01-29T10:27:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 n 1'
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_Int_Tables_number      7
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   4.5622(6)
_cell_length_b                   9.9940(12)
_cell_length_c                   11.5383(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.826(6)
_cell_angle_gamma                90
_cell_volume                     526.03(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    1753
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      28.59

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

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_F_000             256

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

_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0374 before and 0.0257 after correction.
        The Ratio of minimum to maximum transmission is 0.9193.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.6856
_exptl_absorpt_correction_T_max  0.7458

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

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0099
_diffrn_reflns_number            2281
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.696
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_reflns_Laue_measured_fraction_full 0.99
_diffrn_reflns_Laue_measured_fraction_max 0.99
_diffrn_reflns_point_group_measured_fraction_full 0.734
_diffrn_reflns_point_group_measured_fraction_max 0.733
_reflns_number_total             1365
_reflns_number_gt                1335
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0480P)²+0.0783P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1365
_refine_ls_number_parameters     163
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0268
_refine_ls_wR_factor_ref         0.0722
_refine_ls_wR_factor_gt          0.0717
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.037

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'

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 0.6082(5) 0.1626(3) 0.76934(19) 0.0184(5) Uani 1 d . .
H1 H 0.5502 0.1541 0.8477 0.022 Uiso 1 calc . .
C2 C 0.8225(5) 0.2661(2) 0.73919(19) 0.0178(5) Uani 1 d . .
C7 C 0.9067(6) 0.2849(3) 0.6240(2) 0.0188(5) Uani 1 d . .
H7 H 0.8268 0.2307 0.5638 0.023 Uiso 1 calc . .
C6 C 1.1066(5) 0.3830(3) 0.6001(2) 0.0217(6) Uani 1 d . .
C5 C 1.2264(5) 0.4620(3) 0.6875(2) 0.0227(6) Uani 1 d . .
C4 C 1.1483(5) 0.4444(3) 0.8007(2) 0.0236(6) Uani 1 d . .
H4 H 1.2321 0.4982 0.8604 0.028 Uiso 1 calc . .
C3 C 0.9435(6) 0.3457(2) 0.8264(2) 0.0218(6) Uani 1 d . .
H3 H 0.8858 0.3327 0.9044 0.026 Uiso 1 calc . .
C8 C 0.2939(5) -0.0138(2) 0.72787(19) 0.0169(5) Uani 1 d . .
C13 C 0.1912(5) -0.0988(3) 0.6409(2) 0.0191(6) Uani 1 d . .
C12 C -0.0100(5) -0.1980(3) 0.6616(2) 0.0211(5) Uani 1 d . .
C11 C -0.1191(5) -0.2190(2) 0.7709(2) 0.0204(5) Uani 1 d . .
H11 H -0.2579 -0.2877 0.7851 0.025 Uiso 1 calc . .
C10 C -0.0185(5) -0.1359(2) 0.8595(2) 0.0199(5) Uani 1 d . .
H10 H -0.0899 -0.1484 0.9356 0.024 Uiso 1 calc . .
C9 C 0.1825(5) -0.0359(3) 0.83934(19) 0.0199(5) Uani 1 d . .
H9 H 0.247 0.0191 0.9018 0.024 Uiso 1 calc . .
N1 N 0.4980(4) 0.0840(2) 0.69398(17) 0.0187(5) Uani 1 d . .
F2 F 1.1920(3) 0.40492(16) 0.49030(13) 0.0319(4) Uani 1 d . .
F1 F 1.4259(3) 0.55568(15) 0.65836(14) 0.0305(4) Uani 1 d . .
F4 F 0.2913(3) -0.08539(15) 0.53169(12) 0.0296(4) Uani 1 d . .
F3 F -0.0995(4) -0.27541(15) 0.57136(13) 0.0326(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 H1 0.95 . ?
C1 C2 1.469(3) . ?
C1 N1 1.270(3) . ?
C2 C7 1.401(3) . ?
C2 C3 1.391(3) . ?
C7 H7 0.95 . ?
C7 C6 1.370(4) . ?
C6 C5 1.386(4) . ?
C6 F2 1.348(3) . ?
C5 C4 1.370(4) . ?
C5 F1 1.352(3) . ?
C4 H4 0.95 . ?
C4 C3 1.393(4) . ?
C3 H3 0.95 . ?
C8 C13 1.391(3) . ?
C8 C9 1.407(3) . ?
C8 N1 1.409(3) . ?
C13 C12 1.375(4) . ?
C13 F4 1.353(3) . ?
C12 C11 1.378(3) . ?
C12 F3 1.355(3) . ?
C11 H11 0.95 . ?
C11 C10 1.390(4) . ?
C10 H10 0.95 . ?
C10 C9 1.379(4) . ?
C9 H9 0.95 . ?

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
C2 C1 H1 118.9 . . ?
N1 C1 H1 118.9 . . ?
N1 C1 C2 122.1(2) . . ?
C7 C2 C1 120.8(2) . . ?
C3 C2 C1 119.3(2) . . ?
C3 C2 C7 119.9(2) . . ?
C2 C7 H7 120.7 . . ?
C6 C7 C2 118.7(2) . . ?
C6 C7 H7 120.7 . . ?
C7 C6 C5 121.1(2) . . ?
F2 C6 C7 120.5(2) . . ?
F2 C6 C5 118.3(2) . . ?
C4 C5 C6 121.0(2) . . ?
F1 C5 C6 118.3(2) . . ?
F1 C5 C4 120.7(2) . . ?
C5 C4 H4 120.7 . . ?
C5 C4 C3 118.6(2) . . ?
C3 C4 H4 120.7 . . ?
C2 C3 C4 120.7(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C13 C8 C9 116.2(2) . . ?
C13 C8 N1 116.13(19) . . ?
C9 C8 N1 127.7(2) . . ?
C12 C13 C8 122.3(2) . . ?
F4 C13 C8 119.8(2) . . ?
F4 C13 C12 118.0(2) . . ?
C13 C12 C11 121.3(2) . . ?
F3 C12 C13 118.2(2) . . ?
F3 C12 C11 120.5(2) . . ?
C12 C11 H11 121.2 . . ?
C12 C11 C10 117.5(2) . . ?
C10 C11 H11 121.2 . . ?
C11 C10 H10 119.2 . . ?
C9 C10 C11 121.5(2) . . ?
C9 C10 H10 119.2 . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.2(2) . . ?
C10 C9 H9 119.4 . . ?
C1 N1 C8 119.71(19) . . ?

# 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_53
_database_code_depnum_ccdc_archive 'CCDC 1008432'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2013-10-26T20:51:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_Int_Tables_number      33
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   13.5286(9)
_cell_length_b                   3.7803(3)
_cell_length_c                   21.0471(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1076.39(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    2288
_cell_measurement_theta_min      3.16
_cell_measurement_theta_max      29.96

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_F_000             512
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0719 before and 0.0395 after correction.
        The Ratio of minimum to maximum transmission is 0.6527.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.4869
_exptl_absorpt_correction_T_max  0.746

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

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_number            3984
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.935
_diffrn_reflns_theta_max         25.011
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 0.92
_diffrn_reflns_point_group_measured_fraction_max 0.919
_reflns_number_total             1757
_reflns_number_gt                1639
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_refinement  
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0690P)²+0.0121P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1757
_refine_ls_number_parameters     163
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.1006
_refine_ls_wR_factor_gt          0.098
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.051

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'

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
F3 F 0.62039(16) 0.3577(7) 0.19271(11) 0.0356(6) Uani 1 d . .
F1 F 0.09925(15) 1.3273(6) 0.60835(11) 0.0331(6) Uani 1 d . .
F4 F 0.29540(15) 0.4193(6) 0.26653(12) 0.0344(6) Uani 1 d . .
F2 F 0.05447(15) 1.3278(6) 0.48497(11) 0.0301(6) Uani 1 d . .
N1 N 0.34856(19) 0.7712(8) 0.37419(14) 0.0208(7) Uani 1 d . .
C11 C 0.5554(3) 0.4506(10) 0.23890(17) 0.0255(8) Uani 1 d . .
C12 C 0.4567(3) 0.3805(10) 0.22895(18) 0.0251(8) Uani 1 d . .
H12 H 0.4343 0.2663 0.1914 0.03 Uiso 1 calc . .
C13 C 0.3923(2) 0.4831(10) 0.27572(16) 0.0223(8) Uani 1 d . .
C8 C 0.4217(3) 0.6493(8) 0.33132(16) 0.0196(7) Uani 1 d . .
C1 C 0.3675(2) 0.7751(9) 0.43346(17) 0.0204(7) Uani 1 d . .
H1 H 0.4283 0.6791 0.448 0.024 Uiso 1 calc . .
C2 C 0.2982(2) 0.9231(9) 0.47975(17) 0.0182(7) Uani 1 d . .
C3 C 0.3207(3) 0.9235(10) 0.54392(18) 0.0235(8) Uani 1 d . .
H3 H 0.3824 0.8307 0.5577 0.028 Uiso 1 calc . .
C4 C 0.2544(2) 1.0579(10) 0.58887(17) 0.0238(8) Uani 1 d . .
H4 H 0.2698 1.0569 0.6329 0.029 Uiso 1 calc . .
C5 C 0.1660(3) 1.1919(9) 0.56700(18) 0.0228(8) Uani 1 d . .
C7 C 0.2074(2) 1.0640(9) 0.45875(17) 0.0199(7) Uani 1 d . .
H7 H 0.1913 1.0699 0.4148 0.024 Uiso 1 calc . .
C6 C 0.1433(2) 1.1918(9) 0.50336(18) 0.0207(8) Uani 1 d . .
C9 C 0.5228(3) 0.7149(9) 0.33867(17) 0.0212(7) Uani 1 d . .
H9 H 0.5455 0.8301 0.376 0.025 Uiso 1 calc . .
C10 C 0.5905(3) 0.6154(10) 0.29260(18) 0.0247(8) Uani 1 d . .
H10 H 0.6592 0.6596 0.298 0.03 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   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
F3 C11 1.357(4) . ?
F1 C5 1.355(4) . ?
F4 C13 1.346(4) . ?
F2 C6 1.363(4) . ?
N1 C8 1.416(4) . ?
N1 C1 1.273(5) . ?
C11 C12 1.377(5) . ?
C11 C10 1.375(6) . ?
C12 H12 0.95 . ?
C12 C13 1.371(5) . ?
C13 C8 1.387(5) . ?
C8 C9 1.399(5) . ?
C1 H1 0.95 . ?
C1 C2 1.463(5) . ?
C2 C3 1.385(5) . ?
C2 C7 1.409(4) . ?
C3 H3 0.95 . ?
C3 C4 1.399(5) . ?
C4 H4 0.95 . ?
C4 C5 1.378(5) . ?
C5 C6 1.374(5) . ?
C7 H7 0.95 . ?
C7 C6 1.367(5) . ?
C9 H9 0.95 . ?
C9 C10 1.386(5) . ?
C10 H10 0.95 . ?

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 N1 C8 119.2(3) . . ?
F3 C11 C12 118.0(3) . . ?
F3 C11 C10 118.8(3) . . ?
C10 C11 C12 123.2(3) . . ?
C11 C12 H12 121.5 . . ?
C13 C12 C11 116.9(3) . . ?
C13 C12 H12 121.5 . . ?
F4 C13 C12 117.7(3) . . ?
F4 C13 C8 118.8(3) . . ?
C12 C13 C8 123.5(3) . . ?
C13 C8 N1 119.0(3) . . ?
C13 C8 C9 117.0(3) . . ?
C9 C8 N1 123.7(3) . . ?
N1 C1 H1 119.1 . . ?
N1 C1 C2 121.9(3) . . ?
C2 C1 H1 119.1 . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 C7 119.8(3) . . ?
C7 C2 C1 119.6(3) . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 121.2 . . ?
C5 C4 C3 117.7(3) . . ?
C5 C4 H4 121.2 . . ?
F1 C5 C4 120.2(3) . . ?
F1 C5 C6 118.5(3) . . ?
C6 C5 C4 121.3(3) . . ?
C2 C7 H7 120.9 . . ?
C6 C7 C2 118.1(3) . . ?
C6 C7 H7 120.9 . . ?
F2 C6 C5 118.3(3) . . ?
F2 C6 C7 119.9(3) . . ?
C7 C6 C5 121.8(3) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.4(3) . . ?
C10 C9 H9 119.3 . . ?
C11 C10 C9 118.0(3) . . ?
C11 C10 H10 121 . . ?
C9 C10 H10 121 . . ?

# 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_54
_database_code_depnum_ccdc_archive 'CCDC 1008433'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2013-10-23T16:04:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.7990(19)
_cell_length_b                   6.5794(8)
_cell_length_c                   25.265(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.749(8)
_cell_angle_gamma                90
_cell_volume                     2116.9(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100
_cell_measurement_reflns_used    2880
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      28.43

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

_exptl_crystal_description       PLATE
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0479 before and 0.0321 after correction.
        The Ratio of minimum to maximum transmission is 0.8265.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.6164
_exptl_absorpt_correction_T_max  0.7458

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

_diffrn_source                   'fine-focus sealed tube'
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_number            5170
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             1868
_reflns_number_gt                1598
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;
        XL, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0515P)²+1.0382P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1868
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0887
_refine_ls_wR_factor_gt          0.0847
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.61100(8) 0.13353(14) 1.00629(3) 0.0364(3) Uani 1 1 d . . .
F3 F 0.66796(8) 0.17152(13) 0.59084(3) 0.0327(3) Uani 1 1 d . . .
F4 F 0.60275(7) 0.79222(12) 0.72430(3) 0.0292(2) Uani 1 1 d . . .
F2 F 0.64345(8) 0.50563(13) 0.96927(4) 0.0383(3) Uani 1 1 d . . .
N1 N 0.64276(9) 0.42449(18) 0.76896(5) 0.0207(3) Uani 1 1 d . . .
C5 C 0.61408(12) 0.1577(2) 0.95354(6) 0.0253(3) Uani 1 1 d . . .
C4 C 0.59956(12) -0.0046(2) 0.91963(6) 0.0255(3) Uani 1 1 d . . .
H4 H 0.588 -0.1369 0.9329 0.031 Uiso 1 1 calc R . .
C3 C 0.60210(11) 0.0282(2) 0.86529(6) 0.0220(3) Uani 1 1 d . . .
H3 H 0.5917 -0.0828 0.8413 0.026 Uiso 1 1 calc R . .
C2 C 0.61973(10) 0.2214(2) 0.84575(5) 0.0193(3) Uani 1 1 d . . .
C1 C 0.62069(10) 0.2526(2) 0.78845(6) 0.0198(3) Uani 1 1 d . . .
H1 H 0.6044 0.1415 0.765 0.024 Uiso 1 1 calc R . .
C8 C 0.63999(10) 0.4447(2) 0.71327(5) 0.0192(3) Uani 1 1 d . . .
C9 C 0.65824(11) 0.2868(2) 0.67803(6) 0.0212(3) Uani 1 1 d . . .
H9 H 0.6753 0.1543 0.6911 0.025 Uiso 1 1 calc R . .
C10 C 0.65115(11) 0.3266(2) 0.62438(6) 0.0221(3) Uani 1 1 d . . .
C13 C 0.61893(11) 0.6356(2) 0.69112(6) 0.0206(3) Uani 1 1 d . . .
C12 C 0.61379(11) 0.6739(2) 0.63733(6) 0.0230(3) Uani 1 1 d . . .
H12 H 0.5998 0.8073 0.6241 0.028 Uiso 1 1 calc R . .
C11 C 0.62930(11) 0.5159(2) 0.60274(6) 0.0231(3) Uani 1 1 d . . .
H11 H 0.625 0.5373 0.5654 0.028 Uiso 1 1 calc R . .
C7 C 0.63474(11) 0.3849(2) 0.88112(6) 0.0225(3) Uani 1 1 d . . .
H7 H 0.6471 0.5178 0.8684 0.027 Uiso 1 1 calc R . .
C6 C 0.63137(12) 0.3506(2) 0.93426(6) 0.0249(3) Uani 1 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
F1 C5 1.3466(17) . ?
F3 C10 1.3569(16) . ?
F4 C13 1.3571(16) . ?
F2 C6 1.3488(17) . ?
N1 C1 1.2765(19) . ?
N1 C8 1.4100(18) . ?
C5 C4 1.370(2) . ?
C5 C6 1.385(2) . ?
C4 H4 0.95 . ?
C4 C3 1.393(2) . ?
C3 H3 0.95 . ?
C3 C2 1.390(2) . ?
C2 C1 1.463(2) . ?
C2 C7 1.400(2) . ?
C1 H1 0.95 . ?
C8 C9 1.403(2) . ?
C8 C13 1.391(2) . ?
C9 H9 0.95 . ?
C9 C10 1.375(2) . ?
C10 C11 1.378(2) . ?
C13 C12 1.377(2) . ?
C12 H12 0.95 . ?
C12 C11 1.385(2) . ?
C11 H11 0.95 . ?
C7 H7 0.95 . ?
C7 C6 1.366(2) . ?

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 N1 C8 118.95(12) . . ?
F1 C5 C4 120.73(13) . . ?
F1 C5 C6 118.56(13) . . ?
C4 C5 C6 120.71(13) . . ?
C5 C4 H4 120.6 . . ?
C5 C4 C3 118.71(13) . . ?
C3 C4 H4 120.6 . . ?
C4 C3 H3 119.6 . . ?
C2 C3 C4 120.80(14) . . ?
C2 C3 H3 119.6 . . ?
C3 C2 C1 119.81(13) . . ?
C3 C2 C7 119.53(13) . . ?
C7 C2 C1 120.65(12) . . ?
N1 C1 C2 122.00(13) . . ?
N1 C1 H1 119 . . ?
C2 C1 H1 119 . . ?
C9 C8 N1 125.07(12) . . ?
C13 C8 N1 118.11(12) . . ?
C13 C8 C9 116.82(13) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 C8 119.12(13) . . ?
C10 C9 H9 120.4 . . ?
F3 C10 C9 118.29(12) . . ?
F3 C10 C11 118.07(13) . . ?
C9 C10 C11 123.63(13) . . ?
F4 C13 C8 118.21(12) . . ?
F4 C13 C12 118.39(12) . . ?
C12 C13 C8 123.41(13) . . ?
C13 C12 H12 120.3 . . ?
C13 C12 C11 119.30(13) . . ?
C11 C12 H12 120.3 . . ?
C10 C11 C12 117.69(13) . . ?
C10 C11 H11 121.2 . . ?
C12 C11 H11 121.2 . . ?
C2 C7 H7 120.5 . . ?
C6 C7 C2 118.99(13) . . ?
C6 C7 H7 120.5 . . ?
F2 C6 C5 118.29(13) . . ?
F2 C6 C7 120.44(13) . . ?
C7 C6 C5 121.26(13) . . ?

# 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_55
_database_code_depnum_ccdc_archive 'CCDC 1008434'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2013-10-23T23:54:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.9148(3)
_cell_length_b                   7.4926(4)
_cell_length_c                   23.9195(13)
_cell_angle_alpha                90
_cell_angle_beta                 93.722(2)
_cell_angle_gamma                90
_cell_volume                     1057.81(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    5032
_cell_measurement_theta_min      2.849
_cell_measurement_theta_max      32.208

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

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.59
_exptl_crystal_F_000             512
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        R(int) was 0.0382 before and 0.0293 after correction.
        The Ratio of minimum to maximum transmission is 0.9448.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.7053
_exptl_absorpt_correction_T_max  0.7465

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

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'MO K\a'
_diffrn_reflns_av_R_equivalents  0.0136
_diffrn_reflns_number            7170
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.849
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_number_total             1863
_reflns_number_gt                1687
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_refinement  
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        2008). A64, 112-122
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0429P)²+0.3392P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1863
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.078
_refine_ls_wR_factor_gt          0.0744
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.038

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'

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 1.0775(2) 0.05517(15) 0.25679(5) 0.0191(3) Uani 1 d . .
H1 H 1.1879 0.005 0.2343 0.023 Uiso 1 calc . .
C2 C 1.12961(19) 0.07256(15) 0.31712(5) 0.0188(3) Uani 1 d . .
C7 C 0.97203(19) 0.14507(15) 0.35204(5) 0.0187(3) Uani 1 d . .
H7 H 0.8293 0.1869 0.3369 0.022 Uiso 1 calc . .
C6 C 1.0278(2) 0.15446(16) 0.40833(5) 0.0204(3) Uani 1 d . .
C5 C 1.2361(2) 0.09488(16) 0.43089(5) 0.0221(3) Uani 1 d . .
C4 C 1.3932(2) 0.02349(17) 0.39736(5) 0.0230(3) Uani 1 d . .
H4 H 1.5356 -0.0174 0.413 0.028 Uiso 1 calc . .
C3 C 1.33900(19) 0.01259(16) 0.34009(5) 0.0208(3) Uani 1 d . .
H3 H 1.4456 -0.0362 0.3163 0.025 Uiso 1 calc . .
C8 C 0.85475(19) 0.08881(15) 0.17479(5) 0.0184(3) Uani 1 d . .
C9 C 0.99946(19) 0.15709(16) 0.13626(5) 0.0199(3) Uani 1 d . .
C10 C 0.9518(2) 0.15351(17) 0.07919(5) 0.0239(3) Uani 1 d . .
H10 H 1.0553 0.2021 0.0545 0.029 Uiso 1 calc . .
C11 C 0.7497(2) 0.07751(17) 0.05844(5) 0.0256(3) Uani 1 d . .
H11 H 0.7137 0.0743 0.0192 0.031 Uiso 1 calc . .
C12 C 0.5998(2) 0.00616(17) 0.09469(5) 0.0238(3) Uani 1 d . .
H12 H 0.4614 -0.0465 0.0807 0.029 Uiso 1 calc . .
C13 C 0.65573(19) 0.01335(16) 0.15128(5) 0.0200(3) Uani 1 d . .
N1 N 0.88830(16) 0.10538(13) 0.23348(4) 0.0196(2) Uani 1 d . .
F2 F 0.88007(12) 0.22329(10) 0.44363(3) 0.0261(2) Uani 1 d . .
F1 F 1.28225(13) 0.11051(11) 0.48665(3) 0.0312(2) Uani 1 d . .
F3 F 1.19413(11) 0.23702(9) 0.15651(3) 0.02421(19) Uani 1 d . .
F4 F 0.51227(11) -0.05987(10) 0.18683(3) 0.0249(2) 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 H1 0.95 . ?
C1 C2 1.4619(16) . ?
C1 N1 1.2741(15) . ?
C2 C7 1.4008(17) . ?
C2 C3 1.3961(16) . ?
C7 H7 0.95 . ?
C7 C6 1.3671(16) . ?
C6 C5 1.3865(17) . ?
C6 F2 1.3557(13) . ?
C5 C4 1.3748(18) . ?
C5 F1 1.3489(14) . ?
C4 H4 0.95 . ?
C4 C3 1.3890(17) . ?
C3 H3 0.95 . ?
C8 C9 1.3950(17) . ?
C8 C13 1.3914(17) . ?
C8 N1 1.4104(15) . ?
C9 C10 1.3762(17) . ?
C9 F3 1.3589(14) . ?
C10 H10 0.95 . ?
C10 C11 1.3865(18) . ?
C11 H11 0.95 . ?
C11 C12 1.3869(18) . ?
C12 H12 0.95 . ?
C12 C13 1.3734(17) . ?
C13 F4 1.3556(13) . ?

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
C2 C1 H1 119 . . ?
N1 C1 H1 119 . . ?
N1 C1 C2 121.91(10) . . ?
C7 C2 C1 121.15(10) . . ?
C3 C2 C1 118.98(11) . . ?
C3 C2 C7 119.86(11) . . ?
C2 C7 H7 120.7 . . ?
C6 C7 C2 118.68(11) . . ?
C6 C7 H7 120.7 . . ?
C7 C6 C5 121.21(11) . . ?
F2 C6 C7 120.59(10) . . ?
F2 C6 C5 118.19(10) . . ?
C4 C5 C6 121.03(11) . . ?
F1 C5 C6 118.33(11) . . ?
F1 C5 C4 120.63(11) . . ?
C5 C4 H4 120.8 . . ?
C5 C4 C3 118.47(11) . . ?
C3 C4 H4 120.8 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.75(11) . . ?
C4 C3 H3 119.6 . . ?
C9 C8 N1 124.93(11) . . ?
C13 C8 C9 114.91(10) . . ?
C13 C8 N1 119.92(10) . . ?
C10 C9 C8 123.60(11) . . ?
F3 C9 C8 117.92(10) . . ?
F3 C9 C10 118.44(10) . . ?
C9 C10 H10 120.7 . . ?
C9 C10 C11 118.64(11) . . ?
C11 C10 H10 120.7 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.39(11) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.7 . . ?
C13 C12 C11 118.56(11) . . ?
C13 C12 H12 120.7 . . ?
C12 C13 C8 123.90(11) . . ?
F4 C13 C8 117.29(10) . . ?
F4 C13 C12 118.80(11) . . ?
C1 N1 C8 118.19(10) . . ?

# 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_57
_database_code_depnum_ccdc_archive 'CCDC 1008435'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2013-10-25T18:46:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   25.7588(17)
_cell_length_b                   3.7207(3)
_cell_length_c                   22.6104(16)
_cell_angle_alpha                90
_cell_angle_beta                 90.424(4)
_cell_angle_gamma                90
_cell_volume                     2166.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5226
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      27.95

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       needle
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_F_000             1024
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.14
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0620 before and 0.0458 after correction.
        The Ratio of minimum to maximum transmission is 0.8045.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.6001
_exptl_absorpt_correction_T_max  0.7459

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

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_number            16221
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         0.901
_diffrn_reflns_theta_max         25.033
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1.004
_diffrn_measured_fraction_theta_max 1.004
_diffrn_reflns_Laue_measured_fraction_full 1.004
_diffrn_reflns_Laue_measured_fraction_max 1.004
_diffrn_reflns_point_group_measured_fraction_full 1.004
_diffrn_reflns_point_group_measured_fraction_max 1.004
_reflns_number_total             3832
_reflns_number_gt                3345
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_refinement  
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refined as a 2-component 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)+(0.1336P)²+4.0494P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3832
_refine_ls_number_parameters     332
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0698
_refine_ls_wR_factor_ref         0.2283
_refine_ls_wR_factor_gt          0.2005
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_restrained_S_all      1.136
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.071

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'

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
C14 C 0.57700(17) 0.9567(12) 0.6211(2) 0.0228(10) Uani 1 d . .
H14 H 0.5644 1.023 0.583 0.027 Uiso 1 calc . .
C15 C 0.63233(17) 1.0055(12) 0.6345(2) 0.0232(10) Uani 1 d . .
C20 C 0.65278(17) 0.9107(12) 0.6899(2) 0.0238(10) Uani 1 d . .
H20 H 0.6309 0.8165 0.7198 0.029 Uiso 1 calc . .
C19 C 0.70451(18) 0.9555(13) 0.7004(2) 0.0295(11) Uani 1 d . .
C18 C 0.73672(18) 1.0967(13) 0.6576(2) 0.0293(11) Uani 1 d . .
C17 C 0.71764(18) 1.1929(13) 0.6030(2) 0.0306(12) Uani 1 d . .
H17 H 0.74 1.288 0.5737 0.037 Uiso 1 calc . .
C16 C 0.66488(18) 1.1484(12) 0.5916(2) 0.0272(11) Uani 1 d . .
H16 H 0.651 1.2161 0.5543 0.033 Uiso 1 calc . .
C21 C 0.49318(16) 0.7738(12) 0.6398(2) 0.0217(10) Uani 1 d . .
C22 C 0.48108(18) 0.6331(12) 0.5838(2) 0.0242(10) Uani 1 d . .
H22 H 0.5077 0.5782 0.5563 0.029 Uiso 1 calc . .
C23 C 0.42970(18) 0.5770(12) 0.5695(2) 0.0254(10) Uani 1 d . .
C24 C 0.38921(17) 0.6572(12) 0.6068(2) 0.0248(10) Uani 1 d . .
H24 H 0.354 0.6187 0.5957 0.03 Uiso 1 calc . .
C25 C 0.40292(17) 0.7959(12) 0.6608(2) 0.0255(10) Uani 1 d . .
C26 C 0.45362(18) 0.8501(12) 0.6795(2) 0.0245(10) Uani 1 d . .
H26 H 0.4612 0.9365 0.7182 0.029 Uiso 1 calc . .
N2 N 0.54513(14) 0.8294(10) 0.65828(17) 0.0234(9) Uani 1 d . .
F6 F 0.72585(11) 0.8658(9) 0.75335(15) 0.0424(9) Uani 1 d . .
F5 F 0.78762(11) 1.1359(9) 0.67079(17) 0.0462(10) Uani 1 d . .
F7 F 0.41809(10) 0.4372(8) 0.51546(12) 0.0314(8) Uani 1 d . .
F8 F 0.36415(10) 0.8830(8) 0.69802(13) 0.0333(8) Uani 1 d . .
C1 C 0.08456(17) 0.8175(12) 0.6275(2) 0.0234(10) Uani 1 d . .
H1B H 0.0787 0.7146 0.6653 0.028 Uiso 0.055(6) calc A 2
H1A H 0.0787 0.7146 0.6653 0.028 Uiso 0.945(6) calc A 1
C2B C 0.13804(17) 0.9063(12) 0.6108(2) 0.0232(10) Uani 0.055(6) d A 2
C7B C 0.14851(17) 1.0539(12) 0.5553(2) 0.0228(10) Uani 0.055(6) d A 2
H7B H 0.1212 1.1032 0.528 0.027 Uiso 0.055(6) calc A 2
C6B C 0.19908(19) 1.1261(12) 0.5410(2) 0.0277(11) Uani 0.055(6) d A 2
H6B H 0.2069 1.2235 0.5032 0.033 Uiso 0.055(6) calc A 2
C5B C 0.23901(17) 1.0584(13) 0.5810(2) 0.0302(11) Uani 0.055(6) d A 2
C4B C 0.22935(18) 0.9159(13) 0.6357(2) 0.0294(11) Uani 0.055(6) d A 2
C3B C 0.17865(18) 0.8393(12) 0.6506(2) 0.0267(11) Uani 0.055(6) d A 2
H3B H 0.1713 0.7397 0.6883 0.032 Uiso 0.055(6) calc A 2
C8 C -0.00428(16) 0.7838(12) 0.6150(2) 0.0229(10) Uani 1 d . .
C9 C -0.01855(17) 0.8480(11) 0.6735(2) 0.0236(10) Uani 1 d . .
H9 H 0.0054 0.9499 0.7009 0.028 Uiso 1 calc . .
C10 C -0.06784(17) 0.7603(12) 0.6902(2) 0.0244(10) Uani 1 d . .
C11 C -0.10469(17) 0.6073(12) 0.6531(2) 0.0243(10) Uani 1 d . .
H11 H -0.1387 0.5489 0.6661 0.029 Uiso 1 calc . .
C12 C -0.08858(17) 0.5457(12) 0.5960(2) 0.0244(10) Uani 1 d . .
C13 C -0.04007(17) 0.6357(12) 0.5758(2) 0.0248(11) Uani 1 d . .
H13 H -0.0312 0.597 0.5356 0.03 Uiso 1 calc . .
N1 N 0.04584(14) 0.8725(10) 0.59353(18) 0.0244(9) Uani 1 d . .
F2A F 0.21178(11) 1.2627(9) 0.48823(14) 0.0349(9) Uani 0.945(6) d A 1
F3 F -0.08237(10) 0.8293(9) 0.74674(13) 0.0345(8) Uani 1 d . .
F4 F -0.12279(10) 0.3916(8) 0.55805(13) 0.0338(8) Uani 1 d . .
F2B F 0.268(2) 0.854(15) 0.659(2) 0.0349(9) Uani 0.055(6) d A 2
C6A C 0.19908(19) 1.1261(12) 0.5410(2) 0.0277(11) Uani 0.945(6) d A 1
C5A C 0.23901(17) 1.0584(13) 0.5810(2) 0.0302(11) Uani 0.945(6) d A 1
C4A C 0.22935(18) 0.9159(13) 0.6357(2) 0.0294(11) Uani 0.945(6) d A 1
H4A H 0.2569 0.8709 0.6629 0.035 Uiso 0.945(6) calc A 1
C3A C 0.17865(18) 0.8393(12) 0.6506(2) 0.0267(11) Uani 0.945(6) d A 1
H3A H 0.1713 0.7397 0.6883 0.032 Uiso 0.945(6) calc A 1
C2A C 0.13804(17) 0.9063(12) 0.6108(2) 0.0232(10) Uani 0.945(6) d A 1
C7A C 0.14851(17) 1.0539(12) 0.5553(2) 0.0228(10) Uani 0.945(6) d A 1
H7A H 0.1212 1.1032 0.528 0.027 Uiso 0.945(6) calc A 1
F1B F 0.28798(10) 1.1364(8) 0.56435(16) 0.0407(9) Uani 0.055(6) d A 2
F1A F 0.28798(10) 1.1364(8) 0.56435(16) 0.0407(9) Uani 0.945(6) d A 1



#----------------------------------------------------------------------------#
#                   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
C14 H14 0.95 . ?
C14 C15 1.466(6) . ?
C14 N2 1.272(6) . ?
C15 C20 1.401(7) . ?
C15 C16 1.391(7) . ?
C20 H20 0.95 . ?
C20 C19 1.362(6) . ?
C19 C18 1.384(7) . ?
C19 F6 1.355(6) . ?
C18 C17 1.371(8) . ?
C18 F5 1.350(5) . ?
C17 H17 0.95 . ?
C17 C16 1.391(7) . ?
C16 H16 0.95 . ?
C21 C22 1.404(7) . ?
C21 C26 1.392(7) . ?
C21 N2 1.414(6) . ?
C22 H22 0.95 . ?
C22 C23 1.375(6) . ?
C23 C24 1.378(7) . ?
C23 F7 1.360(6) . ?
C24 H24 0.95 . ?
C24 C25 1.370(7) . ?
C25 C26 1.385(6) . ?
C25 F8 1.350(5) . ?
C26 H26 0.95 . ?
C1 H1B 0.95 . ?
C1 H1A 0.95 . ?
C1 C2B 1.469(6) . ?
C1 N1 1.271(6) . ?
C2B C7B 1.398(7) . ?
C2B C3B 1.397(6) . ?
C7B H7B 0.95 . ?
C7B C6B 1.371(6) . ?
C6B H6B 0.95 . ?
C6B C5B 1.389(7) . ?
C5B C4B 1.370(8) . ?
C5B F1B 1.351(5) . ?
C4B C3B 1.380(7) . ?
C4B F2B 1.15(5) . ?
C3B H3B 0.95 . ?
C8 C9 1.397(7) . ?
C8 C13 1.388(7) . ?
C8 N1 1.421(6) . ?
C9 H9 0.95 . ?
C9 C10 1.367(6) . ?
C10 C11 1.384(7) . ?
C10 F3 1.359(5) . ?
C11 H11 0.95 . ?
C11 C12 1.378(7) . ?
C12 C13 1.375(6) . ?
C12 F4 1.354(5) . ?
C13 H13 0.95 . ?

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
C15 C14 H14 118.6 . . ?
N2 C14 H14 118.6 . . ?
N2 C14 C15 122.7(4) . . ?
C20 C15 C14 120.8(4) . . ?
C16 C15 C14 119.5(4) . . ?
C16 C15 C20 119.6(4) . . ?
C15 C20 H20 120.5 . . ?
C19 C20 C15 119.1(4) . . ?
C19 C20 H20 120.5 . . ?
C20 C19 C18 121.0(5) . . ?
F6 C19 C20 120.9(5) . . ?
F6 C19 C18 118.1(4) . . ?
C17 C18 C19 121.1(4) . . ?
F5 C18 C19 118.2(5) . . ?
F5 C18 C17 120.8(5) . . ?
C18 C17 H17 120.7 . . ?
C18 C17 C16 118.6(5) . . ?
C16 C17 H17 120.7 . . ?
C15 C16 C17 120.6(5) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C22 C21 N2 121.6(4) . . ?
C26 C21 C22 119.9(4) . . ?
C26 C21 N2 118.4(4) . . ?
C21 C22 H22 120.8 . . ?
C23 C22 C21 118.3(4) . . ?
C23 C22 H22 120.8 . . ?
C22 C23 C24 123.8(4) . . ?
F7 C23 C22 118.2(4) . . ?
F7 C23 C24 118.0(4) . . ?
C23 C24 H24 122.1 . . ?
C25 C24 C23 115.8(4) . . ?
C25 C24 H24 122.1 . . ?
C24 C25 C26 124.3(4) . . ?
F8 C25 C24 117.4(4) . . ?
F8 C25 C26 118.3(4) . . ?
C21 C26 H26 121.1 . . ?
C25 C26 C21 117.8(4) . . ?
C25 C26 H26 121.1 . . ?
C14 N2 C21 118.2(4) . . ?
C2B C1 H1B 118.6 . . ?
N1 C1 H1B 118.6 . . ?
N1 C1 H1A 118.6 . . ?
N1 C1 C2B 122.8(4) . . ?
C7B C2B C1 120.5(4) . . ?
C3B C2B C1 119.5(4) . . ?
C3B C2B C7B 120.0(4) . . ?
C2B C7B H7B 120.7 . . ?
C6B C7B C2B 118.6(4) . . ?
C6B C7B H7B 120.7 . . ?
C7B C6B H6B 119.7 . . ?
C7B C6B C5B 120.7(5) . . ?
C5B C6B H6B 119.7 . . ?
C4B C5B C6B 121.4(4) . . ?
F1B C5B C6B 117.8(5) . . ?
F1B C5B C4B 120.8(4) . . ?
C5B C4B C3B 118.5(4) . . ?
F2B C4B C5B 109(3) . . ?
F2B C4B C3B 132(3) . . ?
C2B C3B H3B 119.6 . . ?
C4B C3B C2B 120.8(4) . . ?
C4B C3B H3B 119.6 . . ?
C9 C8 N1 122.0(4) . . ?
C13 C8 C9 119.6(4) . . ?
C13 C8 N1 118.4(4) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 C8 118.2(4) . . ?
C10 C9 H9 120.9 . . ?
C9 C10 C11 124.4(4) . . ?
F3 C10 C9 118.6(4) . . ?
F3 C10 C11 117.1(4) . . ?
C10 C11 H11 122.4 . . ?
C12 C11 C10 115.2(4) . . ?
C12 C11 H11 122.4 . . ?
C13 C12 C11 123.5(4) . . ?
F4 C12 C11 117.8(4) . . ?
F4 C12 C13 118.7(4) . . ?
C8 C13 H13 120.5 . . ?
C12 C13 C8 119.0(4) . . ?
C12 C13 H13 120.5 . . ?
C1 N1 C8 117.8(4) . . ?

# 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_58
_database_code_depnum_ccdc_archive 'CCDC 1008436'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2013-10-24T00:38:44-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 c 1'
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_Int_Tables_number      7
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   12.496(5)
_cell_length_b                   3.7100(14)
_cell_length_c                   22.745(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.123(5)
_cell_angle_gamma                90
_cell_volume                     1052.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    1261
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      26.92

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

_exptl_crystal_description       RECTANGULAR
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_F_000             512
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0769 before and 0.0494 after correction.
        The Ratio of minimum to maximum transmission is 0.6334.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.4725
_exptl_absorpt_correction_T_max  0.746
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.986

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

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_number            5417
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.358
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.86
_diffrn_reflns_point_group_measured_fraction_max 0.832
_reflns_number_total             3878
_reflns_number_gt                2852
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_solution    
;
        SHELXS, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_computing_structure_refinement  
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;

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

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0716P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3878
_refine_ls_number_parameters     325
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.081
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1396
_refine_ls_wR_factor_gt          0.1247
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.065

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'

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
F5 F 1.1885(3) 0.3728(10) 0.38280(15) 0.0402(9) Uani 1 d . .
F7 F 0.3823(3) 0.7994(11) 0.24840(15) 0.0418(10) Uani 1 d . .
F6 F 1.0758(3) -0.0527(10) 0.19634(14) 0.0372(9) Uani 1 d . .
F8 F 0.5751(3) 0.6087(10) 0.21526(14) 0.0407(10) Uani 1 d . .
F2 F 0.8418(2) 0.9323(9) 0.44683(13) 0.0340(8) Uani 1 d . .
F1 F 0.9069(3) 1.4206(10) 0.63457(14) 0.0351(9) Uani 1 d . .
F3 F 0.1129(3) 0.8291(11) 0.49116(15) 0.0407(9) Uani 1 d . .
F4 F 0.3170(3) 0.9514(10) 0.46491(14) 0.0359(8) Uani 1 d . .
N2 N 0.7319(3) 0.3368(13) 0.29199(19) 0.0250(11) Uani 1 d . .
N1 N 0.4861(4) 0.8354(13) 0.5428(2) 0.0245(11) Uani 1 d . .
C17 C 1.1089(5) 0.2999(16) 0.3424(3) 0.0272(13) Uani 1 d . .
C16 C 1.0049(4) 0.3794(16) 0.3548(3) 0.0238(12) Uani 1 d . .
H16 H 0.989 0.4807 0.3917 0.029 Uiso 1 calc . .
C15 C 0.9239(4) 0.3088(14) 0.3125(2) 0.0209(12) Uani 1 d . .
C14 C 0.8126(4) 0.4026(14) 0.3258(2) 0.0200(12) Uani 1 d . .
H14 H 0.8015 0.5196 0.3621 0.024 Uiso 1 calc . .
C21 C 0.6306(4) 0.4336(16) 0.3125(2) 0.0226(12) Uani 1 d . .
C22 C 0.6020(4) 0.3899(15) 0.3699(2) 0.0250(13) Uani 1 d . .
H22 H 0.653 0.2951 0.3983 0.03 Uiso 1 calc . .
C23 C 0.5013(5) 0.4804(16) 0.3870(3) 0.0296(13) Uani 1 d . .
H23 H 0.4837 0.4436 0.4267 0.036 Uiso 1 calc . .
C24 C 0.4257(5) 0.6244(16) 0.3469(3) 0.0301(14) Uani 1 d . .
H24 H 0.357 0.6951 0.3587 0.036 Uiso 1 calc . .
C25 C 0.4532(4) 0.6616(17) 0.2897(3) 0.0279(13) Uani 1 d . .
C26 C 0.5529(4) 0.5666(17) 0.2723(2) 0.0260(13) Uani 1 d . .
C20 C 0.9458(5) 0.1598(15) 0.2582(2) 0.0242(13) Uani 1 d . .
H20 H 0.8904 0.1069 0.2292 0.029 Uiso 1 calc . .
C19 C 1.0525(5) 0.0929(15) 0.2488(3) 0.0266(13) Uani 1 d . .
C18 C 1.1358(5) 0.1553(16) 0.2886(3) 0.0286(14) Uani 1 d . .
H18 H 1.2078 0.1033 0.2803 0.034 Uiso 1 calc . .
C5 C 0.8775(5) 1.1740(15) 0.5407(2) 0.0243(12) Uani 1 d . .
H5 H 0.9499 1.2186 0.532 0.029 Uiso 1 calc . .
C4 C 0.8391(4) 1.2589(15) 0.5943(2) 0.0227(12) Uani 1 d . .
C3 C 0.7355(4) 1.1900(15) 0.6087(2) 0.0237(12) Uani 1 d . .
H3 H 0.7123 1.2494 0.6465 0.028 Uiso 1 calc . .
C2 C 0.6656(4) 1.0315(14) 0.5666(2) 0.0193(11) Uani 1 d . .
C1 C 0.5540(4) 0.9620(14) 0.5806(2) 0.0216(12) Uani 1 d . .
H1 H 0.5323 1.0136 0.6191 0.026 Uiso 1 calc . .
C8 C 0.3811(4) 0.7678(14) 0.5596(2) 0.0218(12) Uani 1 d . .
C9 C 0.3570(4) 0.6362(16) 0.6152(2) 0.0233(13) Uani 1 d . .
H9 H 0.4133 0.5944 0.6441 0.028 Uiso 1 calc . .
C10 C 0.2520(4) 0.5667(16) 0.6282(3) 0.0280(13) Uani 1 d . .
H10 H 0.2368 0.4745 0.6658 0.034 Uiso 1 calc . .
C11 C 0.1692(5) 0.6309(16) 0.5868(3) 0.0290(14) Uani 1 d . .
H11 H 0.097 0.5875 0.5958 0.035 Uiso 1 calc . .
C6 C 0.8061(4) 1.0219(15) 0.5002(2) 0.0243(13) Uani 1 d . .
C12 C 0.1927(4) 0.7578(16) 0.5326(3) 0.0276(14) Uani 1 d . .
C13 C 0.2969(5) 0.8226(14) 0.5187(2) 0.0219(12) Uani 1 d . .
C7 C 0.7006(4) 0.9462(15) 0.5106(2) 0.0229(12) Uani 1 d . .
H7 H 0.6536 0.8409 0.4811 0.027 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   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
F5 C17 1.343(7) . ?
F7 C25 1.356(7) . ?
F6 C19 1.355(6) . ?
F8 C26 1.350(6) . ?
F2 C6 1.358(6) . ?
F1 C4 1.353(6) . ?
F3 C12 1.359(6) . ?
F4 C13 1.349(6) . ?
N2 C14 1.258(7) . ?
N2 C21 1.419(6) . ?
N1 C1 1.265(7) . ?
N1 C8 1.410(7) . ?
C17 C16 1.378(8) . ?
C17 C18 1.393(8) . ?
C16 H16 0.95 . ?
C16 C15 1.383(7) . ?
C15 C14 1.481(7) . ?
C15 C20 1.393(7) . ?
C14 H14 0.95 . ?
C21 C22 1.383(7) . ?
C21 C26 1.389(7) . ?
C22 H22 0.95 . ?
C22 C23 1.378(8) . ?
C23 H23 0.95 . ?
C23 C24 1.384(9) . ?
C24 H24 0.95 . ?
C24 C25 1.371(8) . ?
C25 C26 1.374(7) . ?
C20 H20 0.95 . ?
C20 C19 1.384(8) . ?
C19 C18 1.363(9) . ?
C18 H18 0.95 . ?
C5 H5 0.95 . ?
C5 C4 1.372(7) . ?
C5 C6 1.368(8) . ?
C4 C3 1.376(7) . ?
C3 H3 0.95 . ?
C3 C2 1.391(8) . ?
C2 C1 1.470(7) . ?
C2 C7 1.404(7) . ?
C1 H1 0.95 . ?
C8 C9 1.402(7) . ?
C8 C13 1.381(7) . ?
C9 H9 0.95 . ?
C9 C10 1.385(8) . ?
C10 H10 0.95 . ?
C10 C11 1.382(8) . ?
C11 H11 0.95 . ?
C11 C12 1.367(8) . ?
C6 C7 1.381(7) . ?
C12 C13 1.378(8) . ?
C7 H7 0.95 . ?

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
C14 N2 C21 116.7(4) . . ?
C1 N1 C8 118.8(5) . . ?
F5 C17 C16 119.2(5) . . ?
F5 C17 C18 118.2(5) . . ?
C16 C17 C18 122.5(6) . . ?
C17 C16 H16 120.7 . . ?
C17 C16 C15 118.6(5) . . ?
C15 C16 H16 120.7 . . ?
C16 C15 C14 118.2(5) . . ?
C16 C15 C20 121.4(5) . . ?
C20 C15 C14 120.4(5) . . ?
N2 C14 C15 124.1(5) . . ?
N2 C14 H14 118 . . ?
C15 C14 H14 118 . . ?
C22 C21 N2 124.3(5) . . ?
C22 C21 C26 117.1(5) . . ?
C26 C21 N2 118.6(5) . . ?
C21 C22 H22 119.1 . . ?
C23 C22 C21 121.7(6) . . ?
C23 C22 H22 119.1 . . ?
C22 C23 H23 119.7 . . ?
C22 C23 C24 120.6(6) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 H24 121.1 . . ?
C25 C24 C23 117.9(5) . . ?
C25 C24 H24 121.1 . . ?
F7 C25 C24 120.6(5) . . ?
F7 C25 C26 117.7(5) . . ?
C24 C25 C26 121.8(5) . . ?
F8 C26 C21 120.1(5) . . ?
F8 C26 C25 119.0(5) . . ?
C25 C26 C21 120.9(5) . . ?
C15 C20 H20 121.7 . . ?
C19 C20 C15 116.5(5) . . ?
C19 C20 H20 121.7 . . ?
F6 C19 C20 117.6(5) . . ?
F6 C19 C18 117.4(5) . . ?
C18 C19 C20 125.0(5) . . ?
C17 C18 H18 122 . . ?
C19 C18 C17 116.0(5) . . ?
C19 C18 H18 122 . . ?
C4 C5 H5 121.8 . . ?
C6 C5 H5 121.8 . . ?
C6 C5 C4 116.4(5) . . ?
F1 C4 C5 117.8(5) . . ?
F1 C4 C3 119.0(5) . . ?
C5 C4 C3 123.2(5) . . ?
C4 C3 H3 120.7 . . ?
C4 C3 C2 118.6(5) . . ?
C2 C3 H3 120.7 . . ?
C3 C2 C1 119.5(5) . . ?
C3 C2 C7 120.3(5) . . ?
C7 C2 C1 120.2(5) . . ?
N1 C1 C2 121.8(5) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C9 C8 N1 123.7(5) . . ?
C13 C8 N1 118.5(5) . . ?
C13 C8 C9 117.8(5) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.7(5) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.3(5) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.1(5) . . ?
C12 C11 H11 120.5 . . ?
F2 C6 C5 117.9(5) . . ?
F2 C6 C7 117.8(5) . . ?
C5 C6 C7 124.3(5) . . ?
F3 C12 C11 120.5(5) . . ?
F3 C12 C13 118.3(5) . . ?
C11 C12 C13 121.2(5) . . ?
F4 C13 C8 119.4(5) . . ?
F4 C13 C12 119.6(5) . . ?
C12 C13 C8 121.0(5) . . ?
C2 C7 H7 121.4 . . ?
C6 C7 C2 117.1(5) . . ?
C6 C7 H7 121.4 . . ?

# 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_59
_database_code_depnum_ccdc_archive 'CCDC 1008437'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2013-10-24T00:40:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   25.983(2)
_cell_length_b                   7.3160(6)
_cell_length_c                   24.834(2)
_cell_angle_alpha                90
_cell_angle_beta                 113.707(5)
_cell_angle_gamma                90
_cell_volume                     4322.3(6)
_cell_formula_units_Z            16
_cell_measurement_temperature    100
_cell_measurement_reflns_used    4131
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      26.57

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

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_F_000             2048
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.14
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0551 before and 0.0483 after correction.
        The Ratio of minimum to maximum transmission is 0.9233.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.6883
_exptl_absorpt_correction_T_max  0.7455

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

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_number            24110
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.913
_diffrn_reflns_theta_max         27.323
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_reflns_number_total             4848
_reflns_number_gt                3235
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_solution    
;
        SHELXS, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_computing_structure_refinement  
;
        XL, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;

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

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0476P)²+2.1179P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4848
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.111
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.055

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'

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
F3 F 0.01056(4) 0.50972(14) 0.08318(5) 0.0284(3) Uani 1 d . .
F2 F 0.44058(5) 0.17248(15) 0.24569(5) 0.0293(3) Uani 1 d . .
F1 F 0.42000(5) 0.36030(15) 0.05775(5) 0.0292(3) Uani 1 d . .
F4 F 0.19768(5) 0.51731(16) 0.22061(5) 0.0330(3) Uani 1 d . .
F7 F 0.48666(5) -0.25751(16) 0.15898(5) 0.0333(3) Uani 1 d . .
F5 F 0.09148(5) 0.04871(15) 0.19841(5) 0.0304(3) Uani 1 d . .
F6 F 0.04482(4) -0.15338(14) 0.00543(5) 0.0257(3) Uani 1 d . .
F8 F 0.30806(5) -0.07694(15) 0.02414(5) 0.0300(3) Uani 1 d . .
N1 N 0.23630(6) 0.36490(19) 0.14439(7) 0.0193(3) Uani 1 d . .
N2 N 0.25936(6) -0.14930(18) 0.10027(7) 0.0181(3) Uani 1 d . .
C11 C 0.06582(8) 0.4712(2) 0.09711(9) 0.0205(4) Uani 1 d . .
C10 C 0.08107(8) 0.3970(2) 0.05489(9) 0.0205(4) Uani 1 d . .
H10 H 0.0537 0.3693 0.0167 0.025 Uiso 1 calc . .
C9 C 0.13784(8) 0.3637(2) 0.06976(8) 0.0197(4) Uani 1 d . .
H9 H 0.1492 0.3123 0.0412 0.024 Uiso 1 calc . .
C8 C 0.17838(8) 0.4039(2) 0.12546(8) 0.0180(4) Uani 1 d . .
C1 C 0.25920(8) 0.3862(2) 0.10812(8) 0.0189(4) Uani 1 d . .
H1 H 0.2373 0.4331 0.0701 0.023 Uiso 1 calc . .
C2 C 0.31830(8) 0.3404(2) 0.12341(8) 0.0178(4) Uani 1 d . .
C3 C 0.34126(8) 0.3698(2) 0.08188(8) 0.0192(4) Uani 1 d . .
H3 H 0.3188 0.4151 0.0438 0.023 Uiso 1 calc . .
C4 C 0.39742(8) 0.3310(2) 0.09790(8) 0.0211(4) Uani 1 d . .
C5 C 0.43210(8) 0.2650(2) 0.15217(9) 0.0214(4) Uani 1 d . .
H5 H 0.4707 0.2398 0.1621 0.026 Uiso 1 calc . .
C7 C 0.35202(8) 0.2725(2) 0.17912(8) 0.0186(4) Uani 1 d . .
H7 H 0.3369 0.2512 0.2076 0.022 Uiso 1 calc . .
C6 C 0.40745(8) 0.2376(2) 0.19150(8) 0.0202(4) Uani 1 d . .
C13 C 0.15921(8) 0.4754(2) 0.16593(8) 0.0209(4) Uani 1 d . .
C12 C 0.10374(8) 0.5107(2) 0.15324(9) 0.0223(4) Uani 1 d . .
H12 H 0.092 0.5601 0.1819 0.027 Uiso 1 calc . .
C18 C 0.06624(8) -0.0476(2) 0.10120(8) 0.0203(4) Uani 1 d . .
H18 H 0.0275 -0.0345 0.0931 0.024 Uiso 1 calc . .
C17 C 0.10762(8) -0.0075(2) 0.15538(9) 0.0210(4) Uani 1 d . .
C16 C 0.16413(8) -0.0232(2) 0.16871(8) 0.0195(4) Uani 1 d . .
H16 H 0.1912 0.0053 0.2069 0.023 Uiso 1 calc . .
C15 C 0.18070(8) -0.0822(2) 0.12463(8) 0.0174(4) Uani 1 d . .
C14 C 0.24098(8) -0.0964(2) 0.13824(8) 0.0184(4) Uani 1 d . .
H14 H 0.2672 -0.0652 0.1766 0.022 Uiso 1 calc . .
C21 C 0.31813(8) -0.1705(2) 0.11884(8) 0.0170(4) Uani 1 d . .
C22 C 0.35443(8) -0.2324(2) 0.17421(8) 0.0195(4) Uani 1 d . .
H22 H 0.3399 -0.256 0.203 0.023 Uiso 1 calc . .
C23 C 0.41116(8) -0.2606(2) 0.18847(9) 0.0223(4) Uani 1 d . .
H23 H 0.4354 -0.3024 0.2264 0.027 Uiso 1 calc . .
C24 C 0.43130(8) -0.2262(2) 0.14595(9) 0.0227(4) Uani 1 d . .
C19 C 0.08457(8) -0.1082(2) 0.05912(8) 0.0192(4) Uani 1 d . .
C20 C 0.14017(8) -0.1266(2) 0.06886(8) 0.0176(4) Uani 1 d . .
H20 H 0.1509 -0.1683 0.0386 0.021 Uiso 1 calc . .
C26 C 0.34180(8) -0.1390(2) 0.07828(8) 0.0186(4) Uani 1 d . .
C25 C 0.39788(8) -0.1655(2) 0.09035(9) 0.0208(4) Uani 1 d . .
H25 H 0.4127 -0.143 0.0617 0.025 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   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
F3 C11 1.364(2) . ?
F2 C6 1.359(2) . ?
F1 C4 1.362(2) . ?
F4 C13 1.359(2) . ?
F7 C24 1.361(2) . ?
F5 C17 1.359(2) . ?
F6 C19 1.359(2) . ?
F8 C26 1.355(2) . ?
N1 C8 1.413(2) . ?
N1 C1 1.273(2) . ?
N2 C14 1.276(2) . ?
N2 C21 1.415(2) . ?
C11 C10 1.373(3) . ?
C11 C12 1.376(3) . ?
C10 H10 0.95 . ?
C10 C9 1.390(3) . ?
C9 H9 0.95 . ?
C9 C8 1.392(3) . ?
C8 C13 1.391(2) . ?
C1 H1 0.95 . ?
C1 C2 1.465(3) . ?
C2 C3 1.400(2) . ?
C2 C7 1.398(3) . ?
C3 H3 0.95 . ?
C3 C4 1.379(3) . ?
C4 C5 1.373(3) . ?
C5 H5 0.95 . ?
C5 C6 1.381(3) . ?
C7 H7 0.95 . ?
C7 C6 1.370(3) . ?
C13 C12 1.370(3) . ?
C12 H12 0.95 . ?
C18 H18 0.95 . ?
C18 C17 1.374(3) . ?
C18 C19 1.384(2) . ?
C17 C16 1.374(3) . ?
C16 H16 0.95 . ?
C16 C15 1.396(2) . ?
C15 C14 1.467(3) . ?
C15 C20 1.400(3) . ?
C14 H14 0.95 . ?
C21 C22 1.394(3) . ?
C21 C26 1.394(2) . ?
C22 H22 0.95 . ?
C22 C23 1.386(3) . ?
C23 H23 0.95 . ?
C23 C24 1.377(3) . ?
C24 C25 1.376(3) . ?
C19 C20 1.372(3) . ?
C20 H20 0.95 . ?
C26 C25 1.378(3) . ?
C25 H25 0.95 . ?

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 N1 C8 118.55(16) . . ?
C14 N2 C21 117.87(16) . . ?
F3 C11 C10 119.04(17) . . ?
F3 C11 C12 117.73(17) . . ?
C10 C11 C12 123.22(18) . . ?
C11 C10 H10 121.1 . . ?
C11 C10 C9 117.87(18) . . ?
C9 C10 H10 121.1 . . ?
C10 C9 H9 119.2 . . ?
C10 C9 C8 121.68(17) . . ?
C8 C9 H9 119.2 . . ?
C9 C8 N1 124.55(16) . . ?
C13 C8 N1 118.57(17) . . ?
C13 C8 C9 116.71(17) . . ?
N1 C1 H1 119.1 . . ?
N1 C1 C2 121.88(17) . . ?
C2 C1 H1 119.1 . . ?
C3 C2 C1 119.13(17) . . ?
C7 C2 C1 120.83(16) . . ?
C7 C2 C3 120.02(17) . . ?
C2 C3 H3 121 . . ?
C4 C3 C2 118.09(18) . . ?
C4 C3 H3 121 . . ?
F1 C4 C3 118.29(17) . . ?
F1 C4 C5 117.90(17) . . ?
C5 C4 C3 123.81(17) . . ?
C4 C5 H5 122 . . ?
C4 C5 C6 115.93(18) . . ?
C6 C5 H5 122 . . ?
C2 C7 H7 120.9 . . ?
C6 C7 C2 118.19(17) . . ?
C6 C7 H7 120.9 . . ?
F2 C6 C5 117.51(17) . . ?
F2 C6 C7 118.53(16) . . ?
C7 C6 C5 123.96(18) . . ?
F4 C13 C8 118.27(17) . . ?
F4 C13 C12 118.07(16) . . ?
C12 C13 C8 123.64(18) . . ?
C11 C12 H12 121.6 . . ?
C13 C12 C11 116.86(18) . . ?
C13 C12 H12 121.6 . . ?
C17 C18 H18 122.1 . . ?
C17 C18 C19 115.86(17) . . ?
C19 C18 H18 122.1 . . ?
F5 C17 C18 117.84(17) . . ?
F5 C17 C16 118.26(17) . . ?
C16 C17 C18 123.90(17) . . ?
C17 C16 H16 120.9 . . ?
C17 C16 C15 118.26(18) . . ?
C15 C16 H16 120.9 . . ?
C16 C15 C14 118.59(17) . . ?
C16 C15 C20 120.07(17) . . ?
C20 C15 C14 121.34(16) . . ?
N2 C14 C15 122.22(18) . . ?
N2 C14 H14 118.9 . . ?
C15 C14 H14 118.9 . . ?
C22 C21 N2 124.80(16) . . ?
C22 C21 C26 116.50(17) . . ?
C26 C21 N2 118.56(16) . . ?
C21 C22 H22 119 . . ?
C23 C22 C21 121.93(17) . . ?
C23 C22 H22 119 . . ?
C22 C23 H23 121 . . ?
C24 C23 C22 118.02(18) . . ?
C24 C23 H23 121 . . ?
F7 C24 C23 118.55(18) . . ?
F7 C24 C25 118.24(17) . . ?
C25 C24 C23 123.19(18) . . ?
F6 C19 C18 117.54(16) . . ?
F6 C19 C20 118.68(16) . . ?
C20 C19 C18 123.78(18) . . ?
C15 C20 H20 120.9 . . ?
C19 C20 C15 118.12(17) . . ?
C19 C20 H20 120.9 . . ?
F8 C26 C21 118.36(16) . . ?
F8 C26 C25 117.95(16) . . ?
C25 C26 C21 123.68(17) . . ?
C24 C25 C26 116.69(17) . . ?
C24 C25 H25 121.7 . . ?
C26 C25 H25 121.7 . . ?

# 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_60
_database_code_depnum_ccdc_archive 'CCDC 1008438'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2013-10-24T00:41:33-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.2368(5)
_cell_length_b                   6.6503(5)
_cell_length_c                   22.2218(14)
_cell_angle_alpha                90
_cell_angle_beta                 97.167(3)
_cell_angle_gamma                90
_cell_volume                     1061.11(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    5590
_cell_measurement_theta_min      2.837
_cell_measurement_theta_max      29.997

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

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_F_000             512
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        R(int) was 0.0347 before and 0.0262 after correction.
        The Ratio of minimum to maximum transmission is 0.9395.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.7009
_exptl_absorpt_correction_T_max  0.746

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

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'MO K\a'
_diffrn_reflns_av_R_equivalents  0.015
_diffrn_reflns_number            7190
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.847
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.98
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.98
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_number_total             1870
_reflns_number_gt                1755
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_refinement  
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        2008). A64, 112-122
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0397P)²+0.4088P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1870
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.0748
_refine_ls_wR_factor_gt          0.0733
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.039

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'

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
F2 F 0.21448(11) -0.01758(12) 0.48551(3) 0.0298(2) Uani 1 d . .
F3 F 0.47742(10) 0.18164(11) 0.06829(3) 0.0263(2) Uani 1 d . .
F1 F 0.05548(10) 0.63139(11) 0.41514(3) 0.0262(2) Uani 1 d . .
F4 F 0.24002(10) -0.39941(10) 0.21189(3) 0.02428(19) Uani 1 d . .
N1 N 0.30246(14) -0.02793(15) 0.26125(4) 0.0183(2) Uani 1 d . .
C11 C 0.37723(16) -0.15189(19) 0.07934(5) 0.0198(3) Uani 1 d . .
H11 H 0.3907 -0.1791 0.0382 0.024 Uiso 1 calc . .
C12 C 0.31872(16) -0.30046(19) 0.11673(5) 0.0198(3) Uani 1 d . .
H12 H 0.2927 -0.4324 0.1016 0.024 Uiso 1 calc . .
C13 C 0.29898(16) -0.25355(18) 0.17591(5) 0.0183(3) Uani 1 d . .
C8 C 0.33130(16) -0.06190(18) 0.20028(5) 0.0168(3) Uani 1 d . .
C1 C 0.23269(16) 0.14126(18) 0.27375(5) 0.0174(3) Uani 1 d . .
H1 H 0.201 0.2352 0.2419 0.021 Uiso 1 calc . .
C2 C 0.19987(15) 0.19558(18) 0.33549(5) 0.0171(3) Uani 1 d . .
C7 C 0.22376(16) 0.05491(19) 0.38255(5) 0.0193(3) Uani 1 d . .
H7 H 0.2616 -0.079 0.3755 0.023 Uiso 1 calc . .
C6 C 0.19090(16) 0.11609(19) 0.43922(5) 0.0205(3) Uani 1 d . .
C10 C 0.41494(16) 0.03587(19) 0.10392(5) 0.0192(3) Uani 1 d . .
C9 C 0.39472(16) 0.08553(18) 0.16293(5) 0.0187(3) Uani 1 d . .
H9 H 0.4232 0.2171 0.1779 0.022 Uiso 1 calc . .
C3 C 0.14360(16) 0.39184(18) 0.34644(5) 0.0179(3) Uani 1 d . .
H3 H 0.1272 0.4884 0.3147 0.021 Uiso 1 calc . .
C4 C 0.11257(16) 0.44139(18) 0.40446(5) 0.0188(3) Uani 1 d . .
C5 C 0.13539(16) 0.30862(19) 0.45226(5) 0.0203(3) Uani 1 d . .
H5 H 0.1142 0.347 0.492 0.024 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   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 C6 1.3541(14) . ?
F3 C10 1.3639(14) . ?
F1 C4 1.3594(14) . ?
F4 C13 1.3591(14) . ?
N1 C8 1.4144(15) . ?
N1 C1 1.2780(16) . ?
C11 H11 0.95 . ?
C11 C12 1.3905(18) . ?
C11 C10 1.3764(18) . ?
C12 H12 0.95 . ?
C12 C13 1.3763(17) . ?
C13 C8 1.3931(17) . ?
C8 C9 1.3984(17) . ?
C1 H1 0.95 . ?
C1 C2 1.4665(16) . ?
C2 C7 1.3976(17) . ?
C2 C3 1.3976(17) . ?
C7 H7 0.95 . ?
C7 C6 1.3721(17) . ?
C6 C5 1.3834(18) . ?
C10 C9 1.3778(17) . ?
C9 H9 0.95 . ?
C3 H3 0.95 . ?
C3 C4 1.3761(17) . ?
C4 C5 1.3752(17) . ?
C5 H5 0.95 . ?

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 N1 C8 117.29(10) . . ?
C12 C11 H11 121.1 . . ?
C10 C11 H11 121.1 . . ?
C10 C11 C12 117.88(11) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 119.04(11) . . ?
C13 C12 H12 120.5 . . ?
F4 C13 C12 118.55(11) . . ?
F4 C13 C8 118.30(10) . . ?
C12 C13 C8 123.12(11) . . ?
C13 C8 N1 118.74(11) . . ?
C13 C8 C9 117.54(11) . . ?
C9 C8 N1 123.71(11) . . ?
N1 C1 H1 118.8 . . ?
N1 C1 C2 122.33(11) . . ?
C2 C1 H1 118.8 . . ?
C7 C2 C1 121.05(11) . . ?
C3 C2 C1 118.53(11) . . ?
C3 C2 C7 120.43(11) . . ?
C2 C7 H7 121 . . ?
C6 C7 C2 117.95(11) . . ?
C6 C7 H7 121 . . ?
F2 C6 C7 118.86(11) . . ?
F2 C6 C5 117.44(10) . . ?
C7 C6 C5 123.70(11) . . ?
F3 C10 C11 118.57(10) . . ?
F3 C10 C9 117.67(11) . . ?
C11 C10 C9 123.76(11) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 C8 118.59(11) . . ?
C10 C9 H9 120.7 . . ?
C2 C3 H3 120.9 . . ?
C4 C3 C2 118.15(11) . . ?
C4 C3 H3 120.9 . . ?
F1 C4 C3 118.35(11) . . ?
F1 C4 C5 118.15(10) . . ?
C5 C4 C3 123.51(11) . . ?
C6 C5 H5 121.9 . . ?
C4 C5 C6 116.26(11) . . ?
C4 C5 H5 121.9 . . ?

# 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_61
_database_code_depnum_ccdc_archive 'CCDC 1008439'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2013-10-24T00:42:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   5.4757(11)
_cell_length_b                   7.7423(15)
_cell_length_c                   24.406(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1034.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    3396
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      28.9

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

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_F_000             512
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0449 before and 0.0358 after correction.
        The Ratio of minimum to maximum transmission is 0.9163.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.6835
_exptl_absorpt_correction_T_max  0.7459

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

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_number            5704
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.669
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.99
_reflns_number_total             1812
_reflns_number_gt                1688
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_refinement  
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0578P)²+0.1008P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1812
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.0945
_refine_ls_wR_factor_gt          0.0779
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_restrained_S_all      1.184
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 640 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.24
_refine_diff_density_rms         0.071

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'

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 0.4057(4) 0.5280(2) 0.28238(8) 0.0166(5) Uani 1 d . .
H1 H 0.2646 0.5727 0.2647 0.02 Uiso 1 calc . .
C2 C 0.4097(4) 0.5127(2) 0.34272(9) 0.0160(5) Uani 1 d . .
C3 C 0.2207(4) 0.5886(3) 0.37251(9) 0.0176(5) Uani 1 d . .
H3 H 0.0882 0.6437 0.3545 0.021 Uiso 1 calc . .
C4 C 0.2321(4) 0.5811(3) 0.42901(9) 0.0188(5) Uani 1 d . .
C5 C 0.4162(4) 0.4981(2) 0.45719(9) 0.0190(5) Uani 1 d . .
H5 H 0.4191 0.4932 0.4961 0.023 Uiso 1 calc . .
C6 C 0.5957(4) 0.4225(3) 0.42569(9) 0.0179(5) Uani 1 d . .
C7 C 0.6014(4) 0.4283(3) 0.36933(9) 0.0166(5) Uani 1 d . .
H7 H 0.731 0.3767 0.3493 0.02 Uiso 1 calc . .
C8 C 0.5744(4) 0.4974(2) 0.19595(9) 0.0162(5) Uani 1 d . .
C9 C 0.3937(4) 0.4227(3) 0.16392(9) 0.0172(5) Uani 1 d . .
C10 C 0.3963(4) 0.4246(3) 0.10733(9) 0.0195(5) Uani 1 d . .
H10 H 0.2702 0.3697 0.087 0.023 Uiso 1 calc . .
C11 C 0.5857(4) 0.5076(2) 0.08082(9) 0.0202(5) Uani 1 d . .
H11 H 0.5897 0.5107 0.0419 0.024 Uiso 1 calc . .
C12 C 0.7700(4) 0.5866(3) 0.11068(9) 0.0202(5) Uani 1 d . .
H12 H 0.8998 0.6449 0.0927 0.024 Uiso 1 calc . .
C13 C 0.7607(4) 0.5784(3) 0.16717(9) 0.0179(5) Uani 1 d . .
N1 N 0.5887(3) 0.4820(2) 0.25375(7) 0.0171(4) Uani 1 d . .
F1 F 0.0546(2) 0.66064(17) 0.45824(5) 0.0249(3) Uani 1 d . .
F2 F 0.7768(3) 0.33694(17) 0.45233(5) 0.0231(4) Uani 1 d . .
F3 F 0.2106(2) 0.33742(16) 0.18996(5) 0.0210(3) Uani 1 d . .
F4 F 0.9373(2) 0.65885(16) 0.19649(5) 0.0220(3) 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 H1 0.95 . ?
C1 C2 1.478(3) . ?
C1 N1 1.272(3) . ?
C2 C3 1.394(3) . ?
C2 C7 1.397(3) . ?
C3 H3 0.95 . ?
C3 C4 1.381(3) . ?
C4 C5 1.380(3) . ?
C4 F1 1.354(2) . ?
C5 H5 0.95 . ?
C5 C6 1.378(3) . ?
C6 C7 1.377(3) . ?
C6 F2 1.359(2) . ?
C7 H7 0.95 . ?
C8 C9 1.387(3) . ?
C8 C13 1.388(3) . ?
C8 N1 1.418(3) . ?
C9 C10 1.381(3) . ?
C9 F3 1.359(2) . ?
C10 H10 0.95 . ?
C10 C11 1.381(3) . ?
C11 H11 0.95 . ?
C11 C12 1.387(3) . ?
C12 H12 0.95 . ?
C12 C13 1.381(3) . ?
C13 F4 1.355(2) . ?

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
C2 C1 H1 119.6 . . ?
N1 C1 H1 119.6 . . ?
N1 C1 C2 120.87(19) . . ?
C3 C2 C1 118.34(19) . . ?
C3 C2 C7 120.8(2) . . ?
C7 C2 C1 120.8(2) . . ?
C2 C3 H3 121 . . ?
C4 C3 C2 118.0(2) . . ?
C4 C3 H3 121 . . ?
C5 C4 C3 123.4(2) . . ?
F1 C4 C3 118.4(2) . . ?
F1 C4 C5 118.28(19) . . ?
C4 C5 H5 121.9 . . ?
C6 C5 C4 116.2(2) . . ?
C6 C5 H5 121.9 . . ?
C7 C6 C5 124.1(2) . . ?
F2 C6 C5 117.43(18) . . ?
F2 C6 C7 118.51(19) . . ?
C2 C7 H7 121.2 . . ?
C6 C7 C2 117.6(2) . . ?
C6 C7 H7 121.2 . . ?
C9 C8 C13 115.29(19) . . ?
C9 C8 N1 124.40(19) . . ?
C13 C8 N1 120.07(18) . . ?
C10 C9 C8 123.5(2) . . ?
F3 C9 C8 117.75(18) . . ?
F3 C9 C10 118.70(19) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 C9 118.7(2) . . ?
C11 C10 H10 120.6 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.7 . . ?
C13 C12 C11 118.5(2) . . ?
C13 C12 H12 120.7 . . ?
C12 C13 C8 123.6(2) . . ?
F4 C13 C8 117.71(18) . . ?
F4 C13 C12 118.7(2) . . ?
C1 N1 C8 118.65(17) . . ?

# 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_63
_database_code_depnum_ccdc_archive 'CCDC 1008440'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2013-10-24T00:44:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_Int_Tables_number      29
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   27.6959(14)
_cell_length_b                   3.68490(10)
_cell_length_c                   21.5993(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2204.35(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    100
_cell_measurement_reflns_used    3285
_cell_measurement_theta_min      3.088
_cell_measurement_theta_max      25.593

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

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_F_000             1024
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        R(int) was 0.0552 before and 0.0465 after correction.
        The Ratio of minimum to maximum transmission is 0.8856.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.6608
_exptl_absorpt_correction_T_max  0.7462

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

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'MO K\a'
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_number            13533
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         25.693
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.984
_reflns_number_total             4145
_reflns_number_gt                3432
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_refinement  
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        2008). A64, 112-122
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0473P)²+0.7973P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4145
_refine_ls_number_parameters     325
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1039
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.046

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'

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
F5 F 0.27330(10) 0.2336(7) 0.60648(10) 0.0381(6) Uani 1 d . .
F6 F 0.16228(9) -0.1922(7) 0.46026(11) 0.0333(6) Uani 1 d . .
F8 F 0.34992(10) 0.5610(8) 0.13192(10) 0.0426(7) Uani 1 d . .
F7 F 0.47253(10) 0.1451(8) 0.26278(12) 0.0434(7) Uani 1 d . .
F4 F 0.52802(11) 1.1385(7) 0.59080(11) 0.0418(7) Uani 1 d . .
F3 F 0.40365(10) 0.7244(7) 0.46319(13) 0.0433(7) Uani 1 d . .
F2 F 0.71345(9) 0.1856(7) 0.27363(11) 0.0343(6) Uani 1 d . .
F1 F 0.60200(10) 0.5357(7) 0.12284(10) 0.0412(7) Uani 1 d . .
C1 C 0.55765(15) 0.6401(12) 0.33554(18) 0.0264(10) Uani 1 d . .
H1 H 0.5251 0.674 0.323 0.032 Uiso 1 calc . .
N1 N 0.56783(15) 0.6776(12) 0.39023(18) 0.0424(10) Uani 1 d . .
C24 C 0.41223(18) 0.3586(11) 0.19573(19) 0.0302(10) Uani 1 d . .
H24 H 0.435 0.3896 0.1633 0.036 Uiso 1 calc . .
C25 C 0.36466(18) 0.4369(11) 0.18822(17) 0.0274(10) Uani 1 d . .
C26 C 0.33038(17) 0.3948(11) 0.2336(2) 0.0291(10) Uani 1 d . .
H26 H 0.2974 0.4501 0.2259 0.035 Uiso 1 calc . .
C21 C 0.34524(16) 0.2690(10) 0.29124(18) 0.0244(9) Uani 1 d . .
N2 N 0.30905(15) 0.2134(12) 0.3382(2) 0.0468(11) Uani 1 d . .
C14 C 0.31899(15) 0.1991(12) 0.39349(18) 0.0255(9) Uani 1 d . .
H14 H 0.3518 0.2277 0.4055 0.031 Uiso 1 calc . .
C15 C 0.28388(15) 0.1420(11) 0.44049(18) 0.0239(9) Uani 1 d . .
C20 C 0.23845(14) 0.0029(11) 0.42657(18) 0.0223(8) Uani 1 d . .
H20 H 0.2297 -0.0534 0.3851 0.027 Uiso 1 calc . .
C19 C 0.20690(15) -0.0501(11) 0.47391(19) 0.0259(9) Uani 1 d . .
C18 C 0.21652(15) 0.0239(11) 0.53470(19) 0.0256(9) Uani 1 d . .
H18 H 0.1934 -0.0142 0.5666 0.031 Uiso 1 calc . .
C17 C 0.26201(16) 0.1575(11) 0.54644(18) 0.0256(9) Uani 1 d . .
C16 C 0.29630(16) 0.2153(10) 0.50181(18) 0.0250(9) Uani 1 d . .
H16 H 0.3275 0.3024 0.5123 0.03 Uiso 1 calc . .
C23 C 0.42542(15) 0.2307(11) 0.25358(18) 0.0268(9) Uani 1 d . .
C22 C 0.39350(16) 0.1855(10) 0.30142(18) 0.0249(9) Uani 1 d . .
H22 H 0.4041 0.0993 0.3406 0.03 Uiso 1 calc . .
C5 C 0.65847(16) 0.3565(11) 0.19700(18) 0.0251(9) Uani 1 d . .
H5 H 0.6807 0.2909 0.1655 0.03 Uiso 1 calc . .
C6 C 0.66936(15) 0.3211(11) 0.25887(18) 0.0239(9) Uani 1 d . .
C7 C 0.63840(15) 0.4134(10) 0.30564(18) 0.0228(9) Uani 1 d . .
H7 H 0.6476 0.3874 0.3478 0.027 Uiso 1 calc . .
C2 C 0.59289(15) 0.5469(11) 0.28960(19) 0.0252(9) Uani 1 d . .
C8 C 0.53154(15) 0.7721(10) 0.43591(17) 0.0243(9) Uani 1 d . .
C13 C 0.54690(16) 0.9154(11) 0.49177(18) 0.0278(10) Uani 1 d . .
H13 H 0.5802 0.9576 0.4993 0.033 Uiso 1 calc . .
C12 C 0.51306(16) 0.9950(11) 0.53590(18) 0.0271(10) Uani 1 d . .
C11 C 0.46487(17) 0.9381(11) 0.52852(19) 0.0278(10) Uani 1 d . .
H11 H 0.4422 0.9962 0.56 0.033 Uiso 1 calc . .
C10 C 0.45099(15) 0.7907(11) 0.47253(19) 0.0266(10) Uani 1 d . .
C9 C 0.48252(15) 0.7083(10) 0.42600(17) 0.0241(9) Uani 1 d . .
H9 H 0.4714 0.6102 0.3879 0.029 Uiso 1 calc . .
C4 C 0.61361(16) 0.4923(12) 0.18367(17) 0.0252(10) Uani 1 d . .
C3 C 0.58020(16) 0.5862(11) 0.22738(19) 0.0262(9) Uani 1 d . .
H3 H 0.5493 0.6754 0.2158 0.031 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   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
F5 C17 1.363(4) . ?
F6 C19 1.374(5) . ?
F8 C25 1.362(4) . ?
F7 C23 1.357(5) . ?
F4 C12 1.363(5) . ?
F3 C10 1.349(5) . ?
F2 C6 1.357(5) . ?
F1 C4 1.362(4) . ?
C1 H1 0.95 . ?
C1 N1 1.222(5) . ?
C1 C2 1.434(6) . ?
N1 C8 1.451(6) . ?
C24 H24 0.95 . ?
C24 C25 1.358(7) . ?
C24 C23 1.385(6) . ?
C25 C26 1.374(6) . ?
C26 H26 0.95 . ?
C26 C21 1.390(6) . ?
C21 N2 1.441(6) . ?
C21 C22 1.389(6) . ?
N2 C14 1.226(5) . ?
C14 H14 0.95 . ?
C14 C15 1.422(6) . ?
C15 C20 1.392(6) . ?
C15 C16 1.395(6) . ?
C20 H20 0.95 . ?
C20 C19 1.359(6) . ?
C19 C18 1.367(6) . ?
C18 H18 0.95 . ?
C18 C17 1.376(6) . ?
C17 C16 1.370(6) . ?
C16 H16 0.95 . ?
C23 C22 1.370(6) . ?
C22 H22 0.95 . ?
C5 H5 0.95 . ?
C5 C6 1.376(5) . ?
C5 C4 1.370(6) . ?
C6 C7 1.368(5) . ?
C7 H7 0.95 . ?
C7 C2 1.397(6) . ?
C2 C3 1.397(6) . ?
C8 C13 1.384(6) . ?
C8 C9 1.395(6) . ?
C13 H13 0.95 . ?
C13 C12 1.369(6) . ?
C12 C11 1.360(6) . ?
C11 H11 0.95 . ?
C11 C10 1.380(6) . ?
C10 C9 1.366(6) . ?
C9 H9 0.95 . ?
C4 C3 1.367(6) . ?
C3 H3 0.95 . ?

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
N1 C1 H1 118.7 . . ?
N1 C1 C2 122.6(4) . . ?
C2 C1 H1 118.7 . . ?
C1 N1 C8 121.6(4) . . ?
C25 C24 H24 122.1 . . ?
C25 C24 C23 115.9(4) . . ?
C23 C24 H24 122.1 . . ?
F8 C25 C26 117.9(4) . . ?
C24 C25 F8 118.0(4) . . ?
C24 C25 C26 124.1(4) . . ?
C25 C26 H26 120.9 . . ?
C25 C26 C21 118.2(4) . . ?
C21 C26 H26 120.9 . . ?
C26 C21 N2 118.2(4) . . ?
C22 C21 C26 120.0(4) . . ?
C22 C21 N2 121.8(4) . . ?
C14 N2 C21 122.4(4) . . ?
N2 C14 H14 118.4 . . ?
N2 C14 C15 123.2(4) . . ?
C15 C14 H14 118.4 . . ?
C20 C15 C14 121.3(4) . . ?
C20 C15 C16 120.0(4) . . ?
C16 C15 C14 118.7(4) . . ?
C15 C20 H20 120.9 . . ?
C19 C20 C15 118.1(4) . . ?
C19 C20 H20 120.9 . . ?
C20 C19 F6 118.1(4) . . ?
C20 C19 C18 124.7(4) . . ?
C18 C19 F6 117.2(4) . . ?
C19 C18 H18 122.4 . . ?
C19 C18 C17 115.2(4) . . ?
C17 C18 H18 122.4 . . ?
F5 C17 C18 117.3(4) . . ?
F5 C17 C16 118.6(4) . . ?
C16 C17 C18 124.1(4) . . ?
C15 C16 H16 121.1 . . ?
C17 C16 C15 117.8(4) . . ?
C17 C16 H16 121.1 . . ?
F7 C23 C24 117.7(4) . . ?
F7 C23 C22 118.8(4) . . ?
C22 C23 C24 123.5(4) . . ?
C21 C22 H22 120.8 . . ?
C23 C22 C21 118.3(4) . . ?
C23 C22 H22 120.8 . . ?
C6 C5 H5 122 . . ?
C4 C5 H5 122 . . ?
C4 C5 C6 115.9(4) . . ?
F2 C6 C5 117.4(4) . . ?
F2 C6 C7 118.8(3) . . ?
C7 C6 C5 123.8(4) . . ?
C6 C7 H7 121 . . ?
C6 C7 C2 118.0(4) . . ?
C2 C7 H7 121 . . ?
C7 C2 C1 121.8(4) . . ?
C3 C2 C1 118.0(4) . . ?
C3 C2 C7 120.1(4) . . ?
C13 C8 N1 118.1(4) . . ?
C13 C8 C9 119.8(4) . . ?
C9 C8 N1 122.0(4) . . ?
C8 C13 H13 120.7 . . ?
C12 C13 C8 118.6(4) . . ?
C12 C13 H13 120.7 . . ?
F4 C12 C13 118.7(4) . . ?
C11 C12 F4 117.4(4) . . ?
C11 C12 C13 123.9(4) . . ?
C12 C11 H11 122.1 . . ?
C12 C11 C10 115.9(4) . . ?
C10 C11 H11 122.1 . . ?
F3 C10 C11 118.2(4) . . ?
F3 C10 C9 118.1(4) . . ?
C9 C10 C11 123.7(4) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 C8 118.2(4) . . ?
C10 C9 H9 120.9 . . ?
F1 C4 C5 117.4(4) . . ?
F1 C4 C3 118.5(4) . . ?
C3 C4 C5 124.1(4) . . ?
C2 C3 H3 121 . . ?
C4 C3 C2 117.9(4) . . ?
C4 C3 H3 121 . . ?

# 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_64
_database_code_depnum_ccdc_archive 'CCDC 1008441'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2015-01-29T10:46:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8244(6)
_cell_length_b                   7.6412(7)
_cell_length_c                   10.8203(10)
_cell_angle_alpha                79.604(6)
_cell_angle_beta                 83.948(6)
_cell_angle_gamma                69.737(6)
_cell_volume                     520.07(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    2480
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      30.05

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

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_F_000             256

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

_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0508 before and 0.0303 after correction.
        The Ratio of minimum to maximum transmission is 0.8350.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.6229
_exptl_absorpt_correction_T_max  0.746

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

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_number            3815
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.916
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.026
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_number_total             1821
_reflns_number_gt                1597
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0797P)²+0.1595P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1821
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1299
_refine_ls_wR_factor_gt          0.1149
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.071

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'

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
F1 F -0.07730(15) 0.69955(13) 0.45958(9) 0.0252(3) Uani 1 d . .
F3 F 0.80563(15) 0.51094(14) 0.76041(9) 0.0264(3) Uani 1 d . .
F4 F 0.91356(16) 0.26197(16) 0.96893(10) 0.0319(3) Uani 1 d . .
F2 F -0.18327(16) 0.96230(15) 0.25858(10) 0.0303(3) Uani 1 d . .
N1 N 0.4248(2) 0.61868(19) 0.66196(13) 0.0204(4) Uani 1 d . .
C8 C 0.4679(3) 0.4822(2) 0.77132(15) 0.0188(4) Uani 1 d . .
C13 C 0.6640(3) 0.4338(2) 0.81997(16) 0.0202(4) Uani 1 d . .
C3 C 0.0514(3) 0.8000(2) 0.41716(16) 0.0199(4) Uani 1 d . .
C1 C 0.2858(3) 0.6233(2) 0.59026(16) 0.0196(4) Uani 1 d . .
H1 H 0.2162 0.5327 0.6097 0.024 Uiso 1 calc . .
C4 C -0.0037(3) 0.9372(2) 0.31343(16) 0.0217(4) Uani 1 d . .
C9 C 0.3273(3) 0.3994(2) 0.83875(16) 0.0228(4) Uani 1 d . .
H9 H 0.1912 0.431 0.8092 0.027 Uiso 1 calc . .
C2 C 0.2325(3) 0.7670(2) 0.47822(15) 0.0192(4) Uani 1 d . .
C12 C 0.7186(3) 0.3057(2) 0.92790(16) 0.0223(4) Uani 1 d . .
C10 C 0.3842(3) 0.2723(3) 0.94768(16) 0.0252(4) Uani 1 d . .
H10 H 0.2866 0.2175 0.992 0.03 Uiso 1 calc . .
C11 C 0.5819(3) 0.2233(2) 0.99362(16) 0.0247(4) Uani 1 d . .
H11 H 0.6211 0.1353 1.0684 0.03 Uiso 1 calc . .
C7 C 0.3576(3) 0.8775(2) 0.43004(16) 0.0219(4) Uani 1 d . .
H7 H 0.4838 0.8566 0.4691 0.026 Uiso 1 calc . .
C5 C 0.1174(3) 1.0479(2) 0.26731(16) 0.0247(4) Uani 1 d . .
H5 H 0.0769 1.1439 0.1965 0.03 Uiso 1 calc . .
C6 C 0.3007(3) 1.0163(2) 0.32670(16) 0.0244(4) Uani 1 d . .
H6 H 0.3869 1.0907 0.2959 0.029 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   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 C3 1.3514(19) . ?
F3 C13 1.3501(19) . ?
F4 C12 1.3570(19) . ?
F2 C4 1.3566(19) . ?
N1 C8 1.411(2) . ?
N1 C1 1.275(2) . ?
C8 C13 1.393(2) . ?
C8 C9 1.400(2) . ?
C13 C12 1.374(3) . ?
C3 C4 1.375(2) . ?
C3 C2 1.387(2) . ?
C1 H1 0.95 . ?
C1 C2 1.464(2) . ?
C4 C5 1.376(3) . ?
C9 H9 0.95 . ?
C9 C10 1.380(2) . ?
C2 C7 1.400(2) . ?
C12 C11 1.370(3) . ?
C10 H10 0.95 . ?
C10 C11 1.390(3) . ?
C11 H11 0.95 . ?
C7 H7 0.95 . ?
C7 C6 1.380(2) . ?
C5 H5 0.95 . ?
C5 C6 1.393(3) . ?
C6 H6 0.95 . ?

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 N1 C8 119.17(15) . . ?
C13 C8 N1 116.82(15) . . ?
C13 C8 C9 117.34(15) . . ?
C9 C8 N1 125.74(15) . . ?
F3 C13 C8 120.24(15) . . ?
F3 C13 C12 118.65(14) . . ?
C12 C13 C8 121.10(16) . . ?
F1 C3 C4 118.29(15) . . ?
F1 C3 C2 120.59(14) . . ?
C4 C3 C2 121.11(16) . . ?
N1 C1 H1 119.7 . . ?
N1 C1 C2 120.55(16) . . ?
C2 C1 H1 119.7 . . ?
F2 C4 C3 117.97(15) . . ?
F2 C4 C5 120.74(15) . . ?
C3 C4 C5 121.29(16) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.74(16) . . ?
C10 C9 H9 119.6 . . ?
C3 C2 C1 120.26(15) . . ?
C3 C2 C7 117.62(15) . . ?
C7 C2 C1 122.11(15) . . ?
F4 C12 C13 118.14(15) . . ?
F4 C12 C11 120.18(15) . . ?
C11 C12 C13 121.68(16) . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 121.08(16) . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 118.03(16) . . ?
C12 C11 H11 121 . . ?
C10 C11 H11 121 . . ?
C2 C7 H7 119.5 . . ?
C6 C7 C2 121.07(16) . . ?
C6 C7 H7 119.5 . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.55(15) . . ?
C6 C5 H5 120.7 . . ?
C7 C6 C5 120.35(16) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?

# 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_65
_database_code_depnum_ccdc_archive 'CCDC 1008442'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2013-10-24T00:47:53-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2
_chemical_absolute_configuration unk

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.0553(15)
_cell_length_b                   3.6976(4)
_cell_length_c                   13.0135(14)
_cell_angle_alpha                90
_cell_angle_beta                 98.716(4)
_cell_angle_gamma                90
_cell_volume                     525.82(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        R(int) was 0.0581 before and 0.0403 after correction.
        The Ratio of minimum to maximum transmission is 0.8374.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.6249
_exptl_absorpt_correction_T_max  0.7462

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

_diffrn_source                   'fine-focus sealed tube'
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_number            2304
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             1766
_reflns_number_gt                1394
_reflns_threshold_expression     >2sigma(I)

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

_computing_structure_solution    
;
        XS, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_computing_structure_refinement  
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        2008). A64, 112-122
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1201P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1766
_refine_ls_number_parameters     163
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0716
_refine_ls_wR_factor_ref         0.1845
_refine_ls_wR_factor_gt          0.1691
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.96
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.107

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.2727(4) -0.0801(14) -1.4027(4) 0.0178(11) Uani 1 1 d . . .
H1 H -0.349 -0.1822 -1.393 0.021 Uiso 1 1 calc R . .
C2 C -0.2515(4) 0.0143(13) -1.5088(3) 0.0157(11) Uani 1 1 d . . .
C3 C -0.3422(4) -0.0549(15) -1.5930(4) 0.0172(11) Uani 1 1 d . . .
C4 C -0.3229(5) 0.0198(14) -1.6932(4) 0.0185(12) Uani 1 1 d . . .
C5 C -0.2148(4) 0.1630(15) -1.7134(4) 0.0178(11) Uani 1 1 d . . .
H5 H -0.2029 0.2184 -1.7825 0.021 Uiso 1 1 calc R . .
C6 C -0.1232(4) 0.2247(14) -1.6300(3) 0.0166(11) Uani 1 1 d . . .
H6 H -0.0455 0.3092 -1.6425 0.02 Uiso 1 1 calc R . .
C7 C -0.1428(4) 0.1659(14) -1.5301(3) 0.0156(10) Uani 1 1 d . . .
H7 H -0.081 0.2298 -1.4741 0.019 Uiso 1 1 calc R . .
C8 C -0.2228(5) -0.1060(14) -1.2249(4) 0.0210(12) Uani 1 1 d . . .
C13 C -0.1337(5) -0.2547(15) -1.1474(4) 0.0213(12) Uani 1 1 d . . .
C12 C -0.1573(5) -0.3358(16) -1.0499(3) 0.0204(11) Uani 1 1 d . . .
H12 H -0.0956 -0.4353 -0.999 0.024 Uiso 1 1 calc R . .
C11 C -0.2720(5) -0.2695(16) -1.0277(4) 0.0252(13) Uani 1 1 d . . .
C10 C -0.3640(5) -0.1162(16) -1.0987(4) 0.0264(13) Uani 1 1 d . . .
H10 H -0.4422 -0.0644 -1.0804 0.032 Uiso 1 1 calc R . .
C9 C -0.3377(5) -0.0414(15) -1.1973(4) 0.0210(12) Uani 1 1 d . . .
H9 H -0.4002 0.0572 -1.2477 0.025 Uiso 1 1 calc R . .
N1 N -0.1914(4) -0.0282(12) -1.3241(3) 0.0192(10) Uani 1 1 d . . .
F1 F -0.4514(3) -0.2031(8) -1.5783(2) 0.0245(8) Uani 1 1 d . . .
F2 F -0.4163(3) -0.0568(10) -1.7711(2) 0.0293(8) Uani 1 1 d . . .
F4 F -0.0213(2) -0.3181(9) -1.1699(2) 0.0247(7) Uani 1 1 d . . .
F3 F -0.2977(3) -0.3560(10) -0.93142(19) 0.0311(8) Uani 1 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 C2 1.477(6) . ?
C1 N1 1.269(6) . ?
C2 C3 1.392(6) . ?
C2 C7 1.391(7) . ?
C3 C4 1.381(6) . ?
C3 F1 1.366(6) . ?
C4 C5 1.369(7) . ?
C4 F2 1.363(6) . ?
C5 C6 1.387(7) . ?
C6 C7 1.368(6) . ?
C8 C13 1.411(7) . ?
C8 C9 1.393(7) . ?
C8 N1 1.416(6) . ?
C13 C12 1.367(7) . ?
C13 F4 1.340(6) . ?
C12 C11 1.365(7) . ?
C11 C10 1.387(7) . ?
C11 F3 1.364(5) . ?
C10 C9 1.385(7) . ?

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
N1 C1 C2 121.6(5) . . ?
C3 C2 C1 119.7(4) . . ?
C7 C2 C1 123.1(4) . . ?
C7 C2 C3 117.3(4) . . ?
C4 C3 C2 120.7(5) . . ?
F1 C3 C2 120.7(4) . . ?
F1 C3 C4 118.6(4) . . ?
C5 C4 C3 121.6(5) . . ?
F2 C4 C3 116.9(4) . . ?
F2 C4 C5 121.5(4) . . ?
C4 C5 C6 117.9(4) . . ?
C7 C6 C5 121.0(4) . . ?
C6 C7 C2 121.3(4) . . ?
C13 C8 N1 119.4(4) . . ?
C9 C8 C13 116.6(4) . . ?
C9 C8 N1 124.1(4) . . ?
C12 C13 C8 122.6(5) . . ?
F4 C13 C8 118.8(4) . . ?
F4 C13 C12 118.6(5) . . ?
C11 C12 C13 118.1(5) . . ?
C12 C11 C10 122.9(4) . . ?
F3 C11 C12 118.8(5) . . ?
F3 C11 C10 118.3(5) . . ?
C9 C10 C11 117.6(5) . . ?
C10 C9 C8 122.2(5) . . ?
C1 N1 C8 117.5(4) . . ?

# 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_66
_database_code_depnum_ccdc_archive 'CCDC 1008443'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2013-10-24T00:48:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8223(8)
_cell_length_b                   7.5505(8)
_cell_length_c                   11.2975(14)
_cell_angle_alpha                80.541(7)
_cell_angle_beta                 86.409(7)
_cell_angle_gamma                66.173(7)
_cell_volume                     525.11(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    2068
_cell_measurement_theta_min      2.984
_cell_measurement_theta_max      31.011

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

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_F_000             256
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        R(int) was 0.0466 before and 0.0331 after correction.
        The Ratio of minimum to maximum transmission is 0.9181.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.6851
_exptl_absorpt_correction_T_max  0.7462

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

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'MO K\a'
_diffrn_reflns_av_R_equivalents  0.02
_diffrn_reflns_number            4918
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.984
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.994
_reflns_number_total             1840
_reflns_number_gt                1467
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_refinement  
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        2008). A64, 112-122
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0462P)²+0.1373P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1840
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0909
_refine_ls_wR_factor_gt          0.0831
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.046

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'

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 0.7268(3) 0.8669(2) 0.41881(15) 0.0173(4) Uani 1 d . .
H1 H 0.7993 0.9524 0.4047 0.021 Uiso 1 calc . .
C2 C 0.7694(3) 0.7246(2) 0.52965(14) 0.0164(4) Uani 1 d . .
C3 C 0.9412(3) 0.6860(2) 0.60273(15) 0.0184(4) Uani 1 d . .
C4 C 0.9854(3) 0.5488(2) 0.70549(15) 0.0217(4) Uani 1 d . .
C5 C 0.8595(3) 0.4458(2) 0.73825(16) 0.0241(4) Uani 1 d . .
H5 H 0.8915 0.3505 0.8085 0.029 Uiso 1 calc . .
C6 C 0.6848(3) 0.4831(2) 0.66690(15) 0.0236(4) Uani 1 d . .
H6 H 0.5955 0.4138 0.6888 0.028 Uiso 1 calc . .
C7 C 0.6401(3) 0.6205(2) 0.56431(15) 0.0195(4) Uani 1 d . .
H7 H 0.5196 0.6448 0.5164 0.023 Uiso 1 calc . .
C8 C 0.5637(3) 1.0092(2) 0.23367(14) 0.0164(4) Uani 1 d . .
C13 C 0.3699(3) 1.0748(2) 0.17288(15) 0.0179(4) Uani 1 d . .
C12 C 0.3224(3) 1.2020(2) 0.06638(15) 0.0205(4) Uani 1 d . .
H12 H 0.1858 1.2462 0.0297 0.025 Uiso 1 calc . .
C11 C 0.4768(3) 1.2646(2) 0.01328(15) 0.0210(4) Uani 1 d . .
H11 H 0.4497 1.3516 -0.0605 0.025 Uiso 1 calc . .
C10 C 0.6706(3) 1.1961(2) 0.07154(15) 0.0207(4) Uani 1 d . .
C9 C 0.7180(3) 1.0726(2) 0.17883(15) 0.0195(4) Uani 1 d . .
H9 H 0.8543 1.0306 0.2155 0.023 Uiso 1 calc . .
N1 N 0.5937(2) 0.87664(19) 0.34155(12) 0.0175(3) Uani 1 d . .
F1 F 1.07141(15) 0.78221(14) 0.57400(9) 0.0254(3) Uani 1 d . .
F2 F 1.15384(17) 0.51912(15) 0.77403(9) 0.0319(3) Uani 1 d . .
F4 F 0.21899(15) 1.01103(14) 0.22250(9) 0.0253(3) Uani 1 d . .
F3 F 0.82560(16) 1.25222(15) 0.01833(9) 0.0315(3) 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 H1 0.95 . ?
C1 C2 1.469(2) . ?
C1 N1 1.271(2) . ?
C2 C3 1.381(2) . ?
C2 C7 1.402(2) . ?
C3 C4 1.381(2) . ?
C3 F1 1.3525(18) . ?
C4 C5 1.373(2) . ?
C4 F2 1.348(2) . ?
C5 H5 0.95 . ?
C5 C6 1.387(3) . ?
C6 H6 0.95 . ?
C6 C7 1.380(2) . ?
C7 H7 0.95 . ?
C8 C13 1.392(2) . ?
C8 C9 1.396(2) . ?
C8 N1 1.412(2) . ?
C13 C12 1.376(2) . ?
C13 F4 1.3585(18) . ?
C12 H12 0.95 . ?
C12 C11 1.387(2) . ?
C11 H11 0.95 . ?
C11 C10 1.376(3) . ?
C10 C9 1.370(2) . ?
C10 F3 1.3630(18) . ?
C9 H9 0.95 . ?

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
C2 C1 H1 119.7 . . ?
N1 C1 H1 119.7 . . ?
N1 C1 C2 120.66(15) . . ?
C3 C2 C1 121.06(15) . . ?
C3 C2 C7 117.45(15) . . ?
C7 C2 C1 121.49(15) . . ?
C2 C3 C4 121.34(15) . . ?
F1 C3 C2 120.11(14) . . ?
F1 C3 C4 118.55(15) . . ?
C5 C4 C3 120.93(16) . . ?
F2 C4 C3 118.66(15) . . ?
F2 C4 C5 120.41(16) . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.83(16) . . ?
C6 C5 H5 120.6 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.35(16) . . ?
C7 C6 H6 119.8 . . ?
C2 C7 H7 119.5 . . ?
C6 C7 C2 121.09(17) . . ?
C6 C7 H7 119.5 . . ?
C13 C8 C9 116.70(15) . . ?
C13 C8 N1 118.10(14) . . ?
C9 C8 N1 125.10(15) . . ?
C12 C13 C8 123.61(15) . . ?
F4 C13 C8 117.96(14) . . ?
F4 C13 C12 118.42(15) . . ?
C13 C12 H12 120.5 . . ?
C13 C12 C11 119.02(16) . . ?
C11 C12 H12 120.5 . . ?
C12 C11 H11 121.2 . . ?
C10 C11 C12 117.52(16) . . ?
C10 C11 H11 121.2 . . ?
C9 C10 C11 123.91(15) . . ?
F3 C10 C11 117.95(15) . . ?
F3 C10 C9 118.13(15) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 C8 119.18(15) . . ?
C10 C9 H9 120.4 . . ?
C1 N1 C8 119.11(14) . . ?

# 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_68
_database_code_depnum_ccdc_archive 'CCDC 1008444'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2013-10-24T00:50:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2
_chemical_absolute_configuration unk

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.756(3)
_cell_length_b                   4.6737(15)
_cell_length_c                   11.257(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.132(17)
_cell_angle_gamma                90
_cell_volume                     506.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    1941
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      28.68

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.15
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0544 before and 0.0402 after correction.
        The Ratio of minimum to maximum transmission is 0.8986.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.6702
_exptl_absorpt_correction_T_max  0.7458

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

_diffrn_source                   'fine-focus sealed tube'
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.02
_diffrn_reflns_number            3341
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             1386
_reflns_number_gt                1276
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;
        XL, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0425P)²+0.2963P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1386
_refine_ls_number_parameters     163
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0911
_refine_ls_wR_factor_gt          0.0889
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.048

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5856(3) 0.7705(6) 0.7747(2) 0.0204(7) Uani 1 1 d . . .
H1 H 0.6045 0.7028 0.8553 0.024 Uiso 1 1 calc R . .
C2 C 0.4772(3) 0.9860(7) 0.7438(2) 0.0170(6) Uani 1 1 d . . .
C3 C 0.4069(3) 1.0876(7) 0.8331(2) 0.0186(6) Uani 1 1 d . . .
C4 C 0.3048(3) 1.2929(6) 0.8100(2) 0.0204(7) Uani 1 1 d . . .
C5 C 0.2662(3) 1.4014(7) 0.6961(2) 0.0219(7) Uani 1 1 d . . .
H5 H 0.1947 1.5407 0.6797 0.026 Uiso 1 1 calc R . .
C6 C 0.3352(3) 1.3002(7) 0.6057(2) 0.0207(7) Uani 1 1 d . . .
H6 H 0.3106 1.3727 0.5264 0.025 Uiso 1 1 calc R . .
C7 C 0.4384(3) 1.0973(6) 0.6283(2) 0.0189(6) Uani 1 1 d . . .
H7 H 0.4836 1.0324 0.5646 0.023 Uiso 1 1 calc R . .
C8 C 0.7588(3) 0.4599(7) 0.7354(2) 0.0190(6) Uani 1 1 d . . .
C13 C 0.8203(3) 0.3394(7) 0.6441(2) 0.0209(6) Uani 1 1 d . . .
H13 H 0.7929 0.3986 0.5631 0.025 Uiso 1 1 calc R . .
C12 C 0.9212(3) 0.1334(7) 0.6720(3) 0.0215(7) Uani 1 1 d . . .
C11 C 0.9625(3) 0.0463(6) 0.7880(3) 0.0207(7) Uani 1 1 d . . .
C10 C 0.9038(3) 0.1620(7) 0.8800(3) 0.0239(7) Uani 1 1 d . . .
H10 H 0.9326 0.1014 0.9606 0.029 Uiso 1 1 calc R . .
C9 C 0.8020(3) 0.3680(7) 0.8536(2) 0.0234(7) Uani 1 1 d . . .
H9 H 0.7606 0.4487 0.9168 0.028 Uiso 1 1 calc R . .
N1 N 0.6552(2) 0.6706(6) 0.6985(2) 0.0202(6) Uani 1 1 d . . .
F1 F 0.43582(16) 0.9814(4) 0.94592(13) 0.0281(4) Uani 1 1 d . . .
F2 F 0.24186(17) 1.3793(4) 0.90213(14) 0.0293(5) Uani 1 1 d . . .
F4 F 0.97974(18) 0.0108(5) 0.58402(15) 0.0355(5) Uani 1 1 d . . .
F3 F 1.06264(16) -0.1550(4) 0.81225(15) 0.0291(4) Uani 1 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 H1 0.95 . ?
C1 C2 1.462(4) . ?
C1 N1 1.265(3) . ?
C2 C3 1.388(4) . ?
C2 C7 1.396(4) . ?
C3 C4 1.377(4) . ?
C3 F1 1.351(3) . ?
C4 C5 1.375(4) . ?
C4 F2 1.349(3) . ?
C5 H5 0.95 . ?
C5 C6 1.388(4) . ?
C6 H6 0.95 . ?
C6 C7 1.377(4) . ?
C7 H7 0.95 . ?
C8 C13 1.389(4) . ?
C8 C9 1.398(4) . ?
C8 N1 1.425(4) . ?
C13 H13 0.95 . ?
C13 C12 1.377(4) . ?
C12 C11 1.367(4) . ?
C12 F4 1.347(3) . ?
C11 C10 1.371(4) . ?
C11 F3 1.352(3) . ?
C10 H10 0.95 . ?
C10 C9 1.381(4) . ?
C9 H9 0.95 . ?

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
C2 C1 H1 118.7 . . ?
N1 C1 H1 118.7 . . ?
N1 C1 C2 122.6(2) . . ?
C3 C2 C1 119.0(2) . . ?
C3 C2 C7 117.0(3) . . ?
C7 C2 C1 123.9(2) . . ?
C4 C3 C2 121.8(3) . . ?
F1 C3 C2 120.1(3) . . ?
F1 C3 C4 118.1(2) . . ?
C5 C4 C3 121.1(3) . . ?
F2 C4 C3 117.8(2) . . ?
F2 C4 C5 121.1(3) . . ?
C4 C5 H5 121.2 . . ?
C4 C5 C6 117.7(3) . . ?
C6 C5 H5 121.2 . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.6(3) . . ?
C7 C6 H6 119.2 . . ?
C2 C7 H7 119.6 . . ?
C6 C7 C2 120.8(3) . . ?
C6 C7 H7 119.6 . . ?
C13 C8 C9 118.7(3) . . ?
C13 C8 N1 115.7(2) . . ?
C9 C8 N1 125.6(2) . . ?
C8 C13 H13 120.3 . . ?
C12 C13 C8 119.5(3) . . ?
C12 C13 H13 120.3 . . ?
C11 C12 C13 121.2(3) . . ?
F4 C12 C13 120.1(3) . . ?
F4 C12 C11 118.7(3) . . ?
C12 C11 C10 120.6(3) . . ?
F3 C11 C12 119.6(2) . . ?
F3 C11 C10 119.8(3) . . ?
C11 C10 H10 120.5 . . ?
C11 C10 C9 119.0(3) . . ?
C9 C10 H10 120.5 . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.1(3) . . ?
C10 C9 H9 119.4 . . ?
C1 N1 C8 119.3(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_69
_database_code_depnum_ccdc_archive 'CCDC 1008445'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2013-10-24T00:51:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   16.497(2)
_cell_length_b                   3.7422(4)
_cell_length_c                   17.009(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.425(8)
_cell_angle_gamma                90
_cell_volume                     1047.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    2032
_cell_measurement_theta_min      2.402
_cell_measurement_theta_max      27.474

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

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_F_000             512
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        R(int) was 0.0602 before and 0.0387 after correction.
        The Ratio of minimum to maximum transmission is 0.7724.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.5762
_exptl_absorpt_correction_T_max  0.746

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

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'MO K\a'
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_number            5300
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_number_total             1854
_reflns_number_gt                1501
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_refinement  
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        2008). A64, 112-122
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0461P)²+0.3596P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1854
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0887
_refine_ls_wR_factor_gt          0.0819
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.046

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'

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
F2 F 0.55796(6) 0.3700(3) 0.11465(6) 0.0270(3) Uani 1 d . .
F3 F 1.08243(6) 0.3718(3) 0.35647(6) 0.0273(3) Uani 1 d . .
F1 F 0.69638(6) 0.1887(3) 0.19605(5) 0.0231(3) Uani 1 d . .
F4 F 1.18822(6) -0.1410(3) 0.13525(6) 0.0273(3) Uani 1 d . .
N1 N 0.91958(9) 0.3317(4) 0.11004(8) 0.0189(3) Uani 1 d . .
C4 C 0.62913(10) 0.4413(5) 0.08259(10) 0.0191(4) Uani 1 d . .
C3 C 0.70066(11) 0.3460(4) 0.12435(9) 0.0175(4) Uani 1 d . .
C2 C 0.77528(10) 0.4026(4) 0.09446(9) 0.0167(4) Uani 1 d . .
C1 C 0.85105(10) 0.2956(4) 0.13911(10) 0.0176(4) Uani 1 d . .
H1 H 0.849 0.1978 0.1905 0.021 Uiso 1 calc . .
C8 C 0.99110(10) 0.2492(4) 0.15834(9) 0.0177(4) Uani 1 d . .
C9 C 0.99983(10) 0.3421(4) 0.23796(10) 0.0183(4) Uani 1 d . .
H9 H 0.9565 0.4518 0.2627 0.022 Uiso 1 calc . .
C10 C 1.07293(11) 0.2705(4) 0.27972(9) 0.0189(4) Uani 1 d . .
C11 C 1.13761(11) 0.1089(4) 0.24760(10) 0.0205(4) Uani 1 d . .
H11 H 1.1873 0.0613 0.2778 0.025 Uiso 1 calc . .
C12 C 1.12570(10) 0.0203(5) 0.16884(10) 0.0200(4) Uani 1 d . .
C13 C 1.05530(10) 0.0890(4) 0.12269(10) 0.0195(4) Uani 1 d . .
H13 H 1.0505 0.0292 0.0683 0.023 Uiso 1 calc . .
C7 C 0.77497(11) 0.5652(4) 0.02021(10) 0.0184(4) Uani 1 d . .
H7 H 0.8251 0.6103 -0.0019 0.022 Uiso 1 calc . .
C6 C 0.70305(11) 0.6607(5) -0.02125(10) 0.0198(4) Uani 1 d . .
H6 H 0.7043 0.7696 -0.0716 0.024 Uiso 1 calc . .
C5 C 0.62893(11) 0.5996(4) 0.00978(10) 0.0202(4) Uani 1 d . .
H5 H 0.5793 0.6656 -0.0186 0.024 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   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 C4 1.3587(19) . ?
F3 C10 1.3569(19) . ?
F1 C3 1.3609(18) . ?
F4 C12 1.3585(19) . ?
N1 C1 1.276(2) . ?
N1 C8 1.419(2) . ?
C4 C3 1.377(2) . ?
C4 C5 1.372(2) . ?
C3 C2 1.384(2) . ?
C2 C1 1.467(2) . ?
C2 C7 1.401(2) . ?
C1 H1 0.95 . ?
C8 C9 1.395(2) . ?
C8 C13 1.396(2) . ?
C9 H9 0.95 . ?
C9 C10 1.378(2) . ?
C10 C11 1.376(2) . ?
C11 H11 0.95 . ?
C11 C12 1.379(2) . ?
C12 C13 1.375(2) . ?
C13 H13 0.95 . ?
C7 H7 0.95 . ?
C7 C6 1.380(2) . ?
C6 H6 0.95 . ?
C6 C5 1.388(2) . ?
C5 H5 0.95 . ?

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 N1 C8 118.34(14) . . ?
F2 C4 C3 118.35(15) . . ?
F2 C4 C5 120.33(15) . . ?
C5 C4 C3 121.31(16) . . ?
F1 C3 C4 118.22(15) . . ?
F1 C3 C2 120.30(15) . . ?
C4 C3 C2 121.47(15) . . ?
C3 C2 C1 120.96(15) . . ?
C3 C2 C7 117.12(16) . . ?
C7 C2 C1 121.92(15) . . ?
N1 C1 C2 121.03(15) . . ?
N1 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C9 C8 N1 121.81(15) . . ?
C9 C8 C13 120.26(15) . . ?
C13 C8 N1 117.84(15) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 C8 118.22(16) . . ?
C10 C9 H9 120.9 . . ?
F3 C10 C9 118.24(15) . . ?
F3 C10 C11 118.00(15) . . ?
C11 C10 C9 123.75(16) . . ?
C10 C11 H11 122.1 . . ?
C10 C11 C12 115.76(16) . . ?
C12 C11 H11 122.1 . . ?
F4 C12 C11 117.34(15) . . ?
F4 C12 C13 118.57(15) . . ?
C13 C12 C11 124.08(16) . . ?
C8 C13 H13 121 . . ?
C12 C13 C8 117.92(16) . . ?
C12 C13 H13 121 . . ?
C2 C7 H7 119.5 . . ?
C6 C7 C2 121.09(16) . . ?
C6 C7 H7 119.5 . . ?
C7 C6 H6 119.6 . . ?
C7 C6 C5 120.73(16) . . ?
C5 C6 H6 119.6 . . ?
C4 C5 C6 118.26(16) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?

# 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_70
_database_code_depnum_ccdc_archive 'CCDC 1008446'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2013-10-25T19:01:14-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7242(6)
_cell_length_b                   8.3077(7)
_cell_length_c                   10.3309(9)
_cell_angle_alpha                74.956(4)
_cell_angle_beta                 73.491(4)
_cell_angle_gamma                74.437(4)
_cell_volume                     522.43(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    2544
_cell_measurement_theta_min      2.596
_cell_measurement_theta_max      30.93

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

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.61
_exptl_crystal_F_000             256
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        R(int) was 0.0426 before and 0.0308 after correction.
        The Ratio of minimum to maximum transmission is 0.9192.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.686
_exptl_absorpt_correction_T_max  0.7463

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

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'MO K\a'
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_number            5125
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.098
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_number_total             1835
_reflns_number_gt                1556
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
        H. Puschmann, in preparation, 2011)
;
_computing_structure_refinement  
;
        XL, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;

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

_atom_sites_solution_primary     other
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0599P)²+0.0677P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1835
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0961
_refine_ls_wR_factor_gt          0.0913
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.048

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'

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 0.3148(2) 0.78726(16) 0.75353(13) 0.0170(3) Uani 1 d . .
H1 H 0.4077 0.7387 0.8143 0.02 Uiso 1 calc . .
C2 C 0.3056(2) 0.96407(16) 0.67906(13) 0.0171(3) Uani 1 d . .
C3 C 0.4563(2) 1.05347(17) 0.67382(13) 0.0178(3) Uani 1 d . .
C4 C 0.4554(2) 1.21893(17) 0.60324(13) 0.0197(3) Uani 1 d . .
H4 H 0.5615 1.2766 0.6003 0.024 Uiso 1 calc . .
C5 C 0.2929(2) 1.29608(17) 0.53735(14) 0.0213(3) Uani 1 d . .
C6 C 0.1355(2) 1.21737(17) 0.53868(14) 0.0217(3) Uani 1 d . .
H6 H 0.0257 1.2753 0.4918 0.026 Uiso 1 calc . .
C7 C 0.1435(2) 1.05086(17) 0.61078(14) 0.0198(3) Uani 1 d . .
H7 H 0.0363 0.9943 0.6139 0.024 Uiso 1 calc . .
C8 C 0.2075(2) 0.52943(16) 0.81430(13) 0.0165(3) Uani 1 d . .
C13 C 0.0335(2) 0.45938(16) 0.83017(13) 0.0162(3) Uani 1 d . .
C12 C 0.0243(2) 0.29690(17) 0.90488(13) 0.0183(3) Uani 1 d . .
C11 C 0.1846(2) 0.19706(17) 0.96590(13) 0.0191(3) Uani 1 d . .
H11 H 0.175 0.0861 1.0187 0.023 Uiso 1 calc . .
C10 C 0.3618(2) 0.26377(17) 0.94778(13) 0.0186(3) Uani 1 d . .
H10 H 0.476 0.1966 0.9879 0.022 Uiso 1 calc . .
C9 C 0.3747(2) 0.42589(16) 0.87256(13) 0.0186(3) Uani 1 d . .
H9 H 0.4985 0.4678 0.8602 0.022 Uiso 1 calc . .
N1 N 0.19981(18) 0.69819(13) 0.73764(11) 0.0176(3) Uani 1 d . .
F1 F 0.61470(12) 0.97370(10) 0.73976(8) 0.0243(2) Uani 1 d . .
F2 F 0.28824(14) 1.45880(9) 0.46684(8) 0.0291(3) Uani 1 d . .
F4 F -0.13099(12) 0.55083(9) 0.77476(8) 0.0228(2) Uani 1 d . .
F3 F -0.15107(12) 0.23708(10) 0.91847(8) 0.0250(2) 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 C2 1.4645(19) . ?
C1 N1 1.2709(19) . ?
C2 C3 1.390(2) . ?
C2 C7 1.3990(19) . ?
C3 C4 1.378(2) . ?
C3 F1 1.3554(15) . ?
C4 C5 1.374(2) . ?
C5 C6 1.381(2) . ?
C5 F2 1.3558(15) . ?
C6 C7 1.3855(19) . ?
C8 C13 1.394(2) . ?
C8 C9 1.4008(19) . ?
C8 N1 1.4154(17) . ?
C13 C12 1.378(2) . ?
C13 F4 1.3459(15) . ?
C12 C11 1.372(2) . ?
C12 F3 1.3570(16) . ?
C11 C10 1.391(2) . ?
C10 C9 1.3806(19) . ?

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
N1 C1 C2 120.62(13) . . ?
C3 C2 C1 121.60(13) . . ?
C3 C2 C7 117.06(12) . . ?
C7 C2 C1 121.34(13) . . ?
C4 C3 C2 123.49(13) . . ?
F1 C3 C2 118.62(12) . . ?
F1 C3 C4 117.88(12) . . ?
C5 C4 C3 116.44(13) . . ?
C4 C5 C6 123.82(13) . . ?
F2 C5 C4 117.74(13) . . ?
F2 C5 C6 118.44(13) . . ?
C5 C6 C7 117.60(13) . . ?
C6 C7 C2 121.58(13) . . ?
C13 C8 C9 117.34(12) . . ?
C13 C8 N1 116.39(12) . . ?
C9 C8 N1 126.25(12) . . ?
C12 C13 C8 120.84(13) . . ?
F4 C13 C8 120.44(12) . . ?
F4 C13 C12 118.71(12) . . ?
C11 C12 C13 121.97(13) . . ?
F3 C12 C13 118.00(12) . . ?
F3 C12 C11 120.03(12) . . ?
C12 C11 C10 117.76(12) . . ?
C9 C10 C11 121.13(13) . . ?
C10 C9 C8 120.88(13) . . ?
C1 N1 C8 119.25(12) . . ?

# 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_71
_database_code_depnum_ccdc_archive 'CCDC 1008447'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2013-10-24T00:53:31-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2
_chemical_absolute_configuration unk

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   3.8029(4)
_cell_length_b                   11.4621(14)
_cell_length_c                   12.2186(15)
_cell_angle_alpha                90
_cell_angle_beta                 94.778(6)
_cell_angle_gamma                90
_cell_volume                     530.75(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    4010
_cell_measurement_theta_min      2.441
_cell_measurement_theta_max      29.82

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        R(int) was 0.0538 before and 0.0260 after correction.
        The Ratio of minimum to maximum transmission is 0.8877.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.6622
_exptl_absorpt_correction_T_max  0.746

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

_diffrn_source                   'fine-focus sealed tube'
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0129
_diffrn_reflns_number            4729
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         27.1
_diffrn_reflns_theta_full        27.1
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             1976
_reflns_number_gt                1936
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;
        XL, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0421P)²+0.0808P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1976
_refine_ls_number_parameters     163
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.025
_refine_ls_R_factor_gt           0.0244
_refine_ls_wR_factor_ref         0.0674
_refine_ls_wR_factor_gt          0.0669
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.036

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5217(3) 0.38985(13) 0.17286(11) 0.0204(3) Uani 1 1 d . . .
H1 H 0.478 0.3105 0.1538 0.024 Uiso 1 1 calc R . .
C2 C 0.4416(3) 0.43124(13) 0.28149(11) 0.0186(3) Uani 1 1 d . . .
C3 C 0.2946(4) 0.35565(13) 0.35477(12) 0.0229(3) Uani 1 1 d . . .
C4 C 0.2179(4) 0.38853(15) 0.45919(12) 0.0242(3) Uani 1 1 d . . .
H4 H 0.1179 0.3353 0.5075 0.029 Uiso 1 1 calc R . .
C5 C 0.2935(4) 0.50193(15) 0.48958(11) 0.0248(3) Uani 1 1 d . . .
C6 C 0.4371(3) 0.58178(14) 0.42103(11) 0.0234(3) Uani 1 1 d . . .
H6 H 0.4846 0.6596 0.4446 0.028 Uiso 1 1 calc R . .
C7 C 0.5101(3) 0.54529(14) 0.31710(11) 0.0205(3) Uani 1 1 d . . .
H7 H 0.6088 0.5991 0.2691 0.025 Uiso 1 1 calc R . .
C8 C 0.7303(3) 0.40957(12) 0.00143(10) 0.0182(3) Uani 1 1 d . . .
C13 C 0.7075(3) 0.48125(13) -0.09151(11) 0.0190(3) Uani 1 1 d . . .
C12 C 0.7951(4) 0.44451(14) -0.19344(11) 0.0211(3) Uani 1 1 d . . .
H12 H 0.7758 0.495 -0.2553 0.025 Uiso 1 1 calc R . .
C11 C 0.9118(3) 0.33136(13) -0.20107(11) 0.0213(3) Uani 1 1 d . . .
C10 C 0.9437(3) 0.25500(14) -0.11324(11) 0.0208(3) Uani 1 1 d . . .
H10 H 1.0255 0.1775 -0.1216 0.025 Uiso 1 1 calc R . .
C9 C 0.8518(3) 0.29575(13) -0.01220(11) 0.0187(3) Uani 1 1 d . . .
H9 H 0.8721 0.2448 0.0493 0.022 Uiso 1 1 calc R . .
N1 N 0.6475(3) 0.45701(11) 0.10357(9) 0.0225(3) Uani 1 1 d . . .
F1 F 0.2168(3) 0.24474(9) 0.32282(8) 0.0344(2) Uani 1 1 d . . .
F2 F 0.2189(2) 0.53734(10) 0.59089(7) 0.0333(2) Uani 1 1 d . . .
F4 F 0.5915(2) 0.59203(8) -0.08170(7) 0.0271(2) Uani 1 1 d . . .
F3 F 1.0034(2) 0.29299(9) -0.30049(7) 0.0302(2) Uani 1 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 H1 0.95 . ?
C1 C2 1.4653(17) . ?
C1 N1 1.2672(18) . ?
C2 C3 1.3958(19) . ?
C2 C7 1.395(2) . ?
C3 C4 1.385(2) . ?
C3 F1 1.3553(19) . ?
C4 H4 0.95 . ?
C4 C5 1.376(2) . ?
C5 C6 1.383(2) . ?
C5 F2 1.3551(16) . ?
C6 H6 0.95 . ?
C6 C7 1.3868(18) . ?
C7 H7 0.95 . ?
C8 C13 1.3984(19) . ?
C8 C9 1.398(2) . ?
C8 N1 1.4205(16) . ?
C13 C12 1.3816(18) . ?
C13 F4 1.3529(17) . ?
C12 H12 0.95 . ?
C12 C11 1.376(2) . ?
C11 C10 1.382(2) . ?
C11 F3 1.3642(15) . ?
C10 H10 0.95 . ?
C10 C9 1.3917(18) . ?
C9 H9 0.95 . ?

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
C2 C1 H1 119.1 . . ?
N1 C1 H1 119.1 . . ?
N1 C1 C2 121.80(13) . . ?
C3 C2 C1 120.31(14) . . ?
C7 C2 C1 122.57(12) . . ?
C7 C2 C3 117.12(12) . . ?
C4 C3 C2 123.27(14) . . ?
F1 C3 C2 119.14(13) . . ?
F1 C3 C4 117.59(13) . . ?
C3 C4 H4 121.6 . . ?
C5 C4 C3 116.78(14) . . ?
C5 C4 H4 121.6 . . ?
C4 C5 C6 123.09(13) . . ?
F2 C5 C4 118.34(14) . . ?
F2 C5 C6 118.57(14) . . ?
C5 C6 H6 120.9 . . ?
C5 C6 C7 118.29(15) . . ?
C7 C6 H6 120.9 . . ?
C2 C7 H7 119.3 . . ?
C6 C7 C2 121.45(13) . . ?
C6 C7 H7 119.3 . . ?
C13 C8 C9 116.75(12) . . ?
C13 C8 N1 119.03(13) . . ?
C9 C8 N1 124.14(12) . . ?
C12 C13 C8 123.35(14) . . ?
F4 C13 C8 118.56(12) . . ?
F4 C13 C12 118.09(13) . . ?
C13 C12 H12 121.6 . . ?
C11 C12 C13 116.84(13) . . ?
C11 C12 H12 121.6 . . ?
C12 C11 C10 123.51(12) . . ?
F3 C11 C12 118.15(12) . . ?
F3 C11 C10 118.34(13) . . ?
C11 C10 H10 121.2 . . ?
C11 C10 C9 117.64(14) . . ?
C9 C10 H10 121.2 . . ?
C8 C9 H9 119 . . ?
C10 C9 C8 121.91(13) . . ?
C10 C9 H9 119 . . ?
C1 N1 C8 118.56(12) . . ?

# 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_73
_database_code_depnum_ccdc_archive 'CCDC 1008448'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2013-10-24T00:54:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   3.7270(7)
_cell_length_b                   11.656(2)
_cell_length_c                   25.035(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1087.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    1082
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      25.9

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

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_F_000             512
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.14
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0826 before and 0.0501 after correction.
        The Ratio of minimum to maximum transmission is 0.8140.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.6071
_exptl_absorpt_correction_T_max  0.7458

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

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_number            4534
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.627
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.919
_diffrn_reflns_point_group_measured_fraction_max 0.918
_reflns_number_total             1771
_reflns_number_gt                1340
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_refinement  
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0832P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1771
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1375
_refine_ls_wR_factor_gt          0.1245
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.062

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'

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
F2 F 0.2908(9) 0.4799(3) 0.37232(12) 0.0485(10) Uani 1 d . .
F1 F 0.1813(8) 0.3349(2) 0.54614(12) 0.0384(8) Uani 1 d . .
F3 F 0.8844(7) 0.4401(2) 0.67833(11) 0.0359(8) Uani 1 d . .
F4 F 0.4341(8) 0.8174(2) 0.66571(11) 0.0375(8) Uani 1 d . .
N1 N 0.6050(11) 0.6216(3) 0.61271(16) 0.0291(10) Uani 1 d . .
C5 C 0.3312(13) 0.4935(5) 0.4260(2) 0.0302(13) Uani 1 d . .
C4 C 0.2328(14) 0.4042(4) 0.4585(2) 0.0335(13) Uani 1 d . .
H4 H 0.136 0.3349 0.4447 0.04 Uiso 1 calc . .
C3 C 0.2831(13) 0.4212(4) 0.5125(2) 0.0270(12) Uani 1 d . .
C2 C 0.4271(12) 0.5205(4) 0.53475(19) 0.0235(11) Uani 1 d . .
C1 C 0.4743(12) 0.5314(4) 0.59227(18) 0.0254(12) Uani 1 d . .
H1 H 0.4057 0.4697 0.6149 0.031 Uiso 1 calc . .
C8 C 0.6501(12) 0.6281(4) 0.66883(19) 0.0249(11) Uani 1 d . .
C9 C 0.7886(12) 0.5423(4) 0.70176(19) 0.0257(12) Uani 1 d . .
C10 C 0.8465(12) 0.5544(4) 0.75510(19) 0.0312(13) Uani 1 d . .
H10 H 0.9408 0.4927 0.7755 0.037 Uiso 1 calc . .
C11 C 0.7658(13) 0.6583(5) 0.7791(2) 0.0324(13) Uani 1 d . .
H11 H 0.8064 0.6685 0.8163 0.039 Uiso 1 calc . .
C12 C 0.6253(13) 0.7476(5) 0.74887(19) 0.0308(12) Uani 1 d . .
H12 H 0.5661 0.8189 0.765 0.037 Uiso 1 calc . .
C13 C 0.5740(13) 0.7307(4) 0.69515(19) 0.0257(12) Uani 1 d . .
C7 C 0.5258(12) 0.6066(4) 0.4993(2) 0.0275(12) Uani 1 d . .
H7 H 0.6279 0.6754 0.5128 0.033 Uiso 1 calc . .
C6 C 0.4787(13) 0.5945(4) 0.4445(2) 0.0285(12) Uani 1 d . .
H6 H 0.5461 0.6539 0.4205 0.034 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   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 C5 1.361(5) . ?
F1 C3 1.365(5) . ?
F3 C9 1.375(5) . ?
F4 C13 1.355(5) . ?
N1 C1 1.267(6) . ?
N1 C8 1.417(6) . ?
C5 C4 1.371(7) . ?
C5 C6 1.380(7) . ?
C4 H4 0.95 . ?
C4 C3 1.380(7) . ?
C3 C2 1.392(7) . ?
C2 C1 1.456(6) . ?
C2 C7 1.389(6) . ?
C1 H1 0.95 . ?
C8 C9 1.396(7) . ?
C8 C13 1.394(7) . ?
C9 C10 1.360(6) . ?
C10 H10 0.95 . ?
C10 C11 1.386(7) . ?
C11 H11 0.95 . ?
C11 C12 1.390(7) . ?
C12 H12 0.95 . ?
C12 C13 1.373(6) . ?
C7 H7 0.95 . ?
C7 C6 1.390(7) . ?
C6 H6 0.95 . ?

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 N1 C8 119.4(4) . . ?
F2 C5 C4 117.9(5) . . ?
F2 C5 C6 118.4(5) . . ?
C4 C5 C6 123.6(5) . . ?
C5 C4 H4 122 . . ?
C5 C4 C3 115.9(5) . . ?
C3 C4 H4 122 . . ?
F1 C3 C4 117.4(4) . . ?
F1 C3 C2 118.3(4) . . ?
C4 C3 C2 124.3(5) . . ?
C3 C2 C1 120.9(4) . . ?
C7 C2 C3 116.6(4) . . ?
C7 C2 C1 122.5(4) . . ?
N1 C1 C2 121.2(4) . . ?
N1 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C9 C8 N1 126.2(4) . . ?
C13 C8 N1 119.4(4) . . ?
C13 C8 C9 114.3(4) . . ?
F3 C9 C8 117.7(4) . . ?
C10 C9 F3 117.9(4) . . ?
C10 C9 C8 124.3(5) . . ?
C9 C10 H10 120.6 . . ?
C9 C10 C11 118.9(5) . . ?
C11 C10 H10 120.6 . . ?
C10 C11 H11 120 . . ?
C10 C11 C12 120.0(5) . . ?
C12 C11 H11 120 . . ?
C11 C12 H12 120.7 . . ?
C13 C12 C11 118.6(5) . . ?
C13 C12 H12 120.7 . . ?
F4 C13 C8 117.4(4) . . ?
F4 C13 C12 118.6(4) . . ?
C12 C13 C8 123.9(4) . . ?
C2 C7 H7 119.2 . . ?
C2 C7 C6 121.5(5) . . ?
C6 C7 H7 119.2 . . ?
C5 C6 C7 118.0(5) . . ?
C5 C6 H6 121 . . ?
C7 C6 H6 121 . . ?

# 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_74
_database_code_depnum_ccdc_archive 'CCDC 1008449'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2013-10-24T00:55:44-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
3,4-difluoro-N-(2,4-difluorobenzylidene)aniline
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.7169(6)
_cell_length_b                   11.5058(19)
_cell_length_c                   12.530(2)
_cell_angle_alpha                97.022(11)
_cell_angle_beta                 93.644(11)
_cell_angle_gamma                91.313(12)
_cell_volume                     530.52(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    1156
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      26.93

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

_exptl_crystal_description       'THIN needle'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_F_000             256
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0653 before and 0.0255 after correction.
        The Ratio of minimum to maximum transmission is 0.9041.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.6743
_exptl_absorpt_correction_T_max  0.7458
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.986

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

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.013
_diffrn_reflns_number            2973
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.641
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.985
_reflns_number_total             1861
_reflns_number_gt                1371
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_solution    
;
        SHELXS, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_computing_structure_refinement  
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;

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

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0538P)²+0.3899P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1861
_refine_ls_number_parameters     167
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1223
_refine_ls_wR_factor_gt          0.1103
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.052

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'

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 0.2890(6) 0.2250(2) 0.56804(19) 0.0215(5) Uani 1 d . .
H1 H 0.3485 0.1481 0.5817 0.026 Uiso 1 calc . .
C2 C 0.3489(6) 0.26242(14) 0.46353(15) 0.0188(5) Uani 1 d . .
C7 C 0.2749(6) 0.37561(15) 0.44251(15) 0.0206(5) Uani 1 d . .
H7 H 0.1833 0.4287 0.4977 0.025 Uiso 1 calc . .
C6 C 0.3302(6) 0.41384(17) 0.34385(13) 0.0239(5) Uani 1 d . .
H6 H 0.2781 0.4915 0.3308 0.029 Uiso 1 calc . .
C5 C 0.4644(6) 0.33437(15) 0.26494(15) 0.0234(5) Uani 1 d . .
C4 C 0.5428(6) 0.21988(16) 0.27970(14) 0.0237(5) Uani 1 d . .
H4 H 0.6308 0.1665 0.2242 0.028 Uiso 1 calc . .
C3 C 0.4846(6) 0.18831(17) 0.38070(13) 0.0210(5) Uani 1 d . .
C8A C 0.0873(6) 0.25686(14) 0.74107(15) 0.0208(5) Uani 0.712(3) d A 1
C8B C 0.0873(6) 0.25686(14) 0.74107(15) 0.0208(5) Uani 0.288(3) d A 2
C13A C 0.1055(6) 0.34219(17) 0.83005(12) 0.0255(6) Uani 0.712(3) d A 1
H13A H 0.1674 0.421 0.8218 0.031 Uiso 0.712(3) calc A 1
C13B C 0.1055(6) 0.34219(17) 0.83005(12) 0.0255(6) Uani 0.288(3) d A 2
H13B H 0.1674 0.421 0.8218 0.031 Uiso 0.288(3) calc A 2
C12A C 0.0336(7) 0.31285(17) 0.93102(15) 0.0294(6) Uani 0.712(3) d A 1
H12A H 0.0525 0.3709 0.9921 0.035 Uiso 0.712(3) calc A 1
C12B C 0.0336(7) 0.31285(17) 0.93102(15) 0.0294(6) Uani 0.288(3) d A 2
C11A C -0.0661(6) 0.19813(15) 0.94202(16) 0.0297(6) Uani 0.712(3) d A 1
C11B C -0.0661(6) 0.19813(15) 0.94202(16) 0.0297(6) Uani 0.288(3) d A 2
C10A C -0.0925(7) 0.11357(18) 0.85257(13) 0.0299(6) Uani 0.712(3) d A 1
C10B C -0.0925(7) 0.11357(18) 0.85257(13) 0.0299(6) Uani 0.288(3) d A 2
H10B H -0.164 0.0354 0.8604 0.036 Uiso 0.288(3) calc A 2
C9A C -0.0153(6) 0.14215(15) 0.75179(15) 0.0248(6) Uani 0.712(3) d A 1
H9A H -0.0324 0.0839 0.6908 0.03 Uiso 0.712(3) calc A 1
C9B C -0.0153(6) 0.14215(15) 0.75179(15) 0.0248(6) Uani 0.288(3) d A 2
H9B H -0.0324 0.0839 0.6908 0.03 Uiso 0.288(3) calc A 2
N1 N 0.1575(5) 0.29484(17) 0.64113(15) 0.0216(5) Uani 1 d . .
F3B F -0.1434(5) 0.16848(14) 1.03778(12) 0.0458(5) Uani 0.712(3) d A 2
F1 F 0.5657(4) 0.07766(11) 0.39849(11) 0.0318(4) Uani 1 d . .
F4A F -0.2098(6) 0.00620(18) 0.86268(17) 0.0426(6) Uani 0.712(3) d A 1
F4B F -0.0022(16) 0.3971(4) 1.0092(4) 0.0426(6) Uani 0.288(3) d A 2
F2 F 0.5233(4) 0.36975(13) 0.16926(11) 0.0347(4) Uani 1 d . .
F3A F -0.1434(5) 0.16848(14) 1.03778(12) 0.0458(5) Uani 0.288(3) d A 1



#----------------------------------------------------------------------------#
#                   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 H1 0.95 . ?
C1 C2 1.456(3) . ?
C1 N1 1.272(3) . ?
C2 C7 1.3899(10) . ?
C2 C3 1.3888(10) . ?
C7 H7 0.95 . ?
C7 C6 1.3875(10) . ?
C6 H6 0.95 . ?
C6 C5 1.3875(10) . ?
C5 C4 1.3873(10) . ?
C5 F2 1.342(2) . ?
C4 H4 0.95 . ?
C4 C3 1.3871(10) . ?
C3 F1 1.356(2) . ?
C8A C13A 1.3898(8) . ?
C8A C9A 1.3901(8) . ?
C8A N1 1.413(3) . ?
C13A H13A 0.95 . ?
C13A C12A 1.3890(8) . ?
C12A H12A 0.95 . ?
C12A C11A 1.3882(8) . ?
C11A C10A 1.3884(8) . ?
C10A C9A 1.3887(8) . ?
C10A F4A 1.324(3) . ?
C9A H9A 0.95 . ?

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
C2 C1 H1 119.8 . . ?
N1 C1 H1 119.8 . . ?
N1 C1 C2 120.3(2) . . ?
C7 C2 C1 121.03(16) . . ?
C3 C2 C1 122.24(16) . . ?
C3 C2 C7 116.73(18) . . ?
C2 C7 H7 118.8 . . ?
C6 C7 C2 122.33(18) . . ?
C6 C7 H7 118.8 . . ?
C7 C6 H6 121.3 . . ?
C5 C6 C7 117.50(19) . . ?
C5 C6 H6 121.3 . . ?
C4 C5 C6 123.49(19) . . ?
F2 C5 C6 118.54(15) . . ?
F2 C5 C4 117.97(15) . . ?
C5 C4 H4 122.1 . . ?
C3 C4 C5 115.77(18) . . ?
C3 C4 H4 122.1 . . ?
C4 C3 C2 124.16(18) . . ?
F1 C3 C2 118.59(15) . . ?
F1 C3 C4 117.24(15) . . ?
C13A C8A C9A 120.17(19) . . ?
C13A C8A N1 116.57(16) . . ?
C9A C8A N1 123.16(16) . . ?
C8A C13A H13A 119.8 . . ?
C12A C13A C8A 120.35(19) . . ?
C12A C13A H13A 119.8 . . ?
C13A C12A H12A 120.2 . . ?
C11A C12A C13A 119.5(2) . . ?
C11A C12A H12A 120.2 . . ?
C12A C11A C10A 120.0(2) . . ?
C11A C10A C9A 120.6(2) . . ?
F4A C10A C11A 119.52(17) . . ?
F4A C10A C9A 119.78(18) . . ?
C8A C9A H9A 120.4 . . ?
C10A C9A C8A 119.27(19) . . ?
C10A C9A H9A 120.4 . . ?
C1 N1 C8A 120.18(19) . . ?

# 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_75
_database_code_depnum_ccdc_archive 'CCDC 1008450'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2013-10-24T00:57:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   3.6872(3)
_cell_length_b                   12.9017(8)
_cell_length_c                   22.262(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1059.02(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    1002
_cell_measurement_theta_min      2.416
_cell_measurement_theta_max      25.063

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

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_F_000             512
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        R(int) was 0.0546 before and 0.0445 after correction.
        The Ratio of minimum to maximum transmission is 0.7899.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.5894
_exptl_absorpt_correction_T_max  0.7462

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

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'MO K\a'
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_number            3637
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.824
_diffrn_reflns_theta_max         25.022
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.953
_reflns_number_total             1796
_reflns_number_gt                1539
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_refinement  
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        2008). A64, 112-122
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0333P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1796
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0794
_refine_ls_wR_factor_gt          0.0746
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.046

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'

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 0.2225(8) 0.8456(2) 0.09905(12) 0.0159(7) Uani 1 d . .
H1 H 0.3281 0.786 0.0812 0.019 Uiso 1 calc . .
C2 C 0.1218(9) 0.9334(2) 0.06091(13) 0.0141(7) Uani 1 d . .
C3 C 0.1691(9) 0.9292(2) -0.00142(13) 0.0152(7) Uani 1 d . .
C4 C 0.0805(9) 1.0089(2) -0.03941(14) 0.0175(7) Uani 1 d . .
H4 H 0.1163 1.0038 -0.0816 0.021 Uiso 1 calc . .
C5 C -0.0630(9) 1.0967(2) -0.01340(14) 0.0203(7) Uani 1 d . .
C6 C -0.1146(9) 1.1080(2) 0.04787(14) 0.0196(7) Uani 1 d . .
H6 H -0.2111 1.1701 0.0643 0.023 Uiso 1 calc . .
C7 C -0.0201(9) 1.0251(2) 0.08438(14) 0.0164(7) Uani 1 d . .
H7 H -0.053 1.0309 0.1266 0.02 Uiso 1 calc . .
C8 C 0.2550(9) 0.7568(2) 0.18920(12) 0.0161(7) Uani 1 d . .
C9 C 0.1863(9) 0.6577(2) 0.16725(13) 0.0174(7) Uani 1 d . .
H9 H 0.0874 0.6481 0.1282 0.021 Uiso 1 calc . .
C10 C 0.2644(10) 0.5741(2) 0.20316(13) 0.0185(7) Uani 1 d . .
C11 C 0.4121(9) 0.5826(3) 0.26010(14) 0.0210(8) Uani 1 d . .
H11 H 0.4689 0.5236 0.2838 0.025 Uiso 1 calc . .
C12 C 0.4710(9) 0.6818(3) 0.28000(13) 0.0191(8) Uani 1 d . .
C13 C 0.3951(9) 0.7690(2) 0.24723(13) 0.0182(7) Uani 1 d . .
H13 H 0.4364 0.8361 0.2635 0.022 Uiso 1 calc . .
N1 N 0.1712(7) 0.84747(19) 0.15625(11) 0.0184(6) Uani 1 d . .
F1 F 0.3082(5) 0.84101(12) -0.02579(7) 0.0217(4) Uani 1 d . .
F2 F -0.1558(5) 1.17633(13) -0.04996(8) 0.0273(5) Uani 1 d . .
F3 F 0.1874(6) 0.47765(13) 0.18168(8) 0.0290(5) Uani 1 d . .
F4 F 0.6146(6) 0.69380(13) 0.33600(7) 0.0286(5) 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 H1 0.95 . ?
C1 C2 1.463(4) . ?
C1 N1 1.288(4) . ?
C2 C3 1.400(4) . ?
C2 C7 1.395(4) . ?
C3 C4 1.371(4) . ?
C3 F1 1.361(3) . ?
C4 H4 0.95 . ?
C4 C5 1.378(4) . ?
C5 C6 1.385(4) . ?
C5 F2 1.354(3) . ?
C6 H6 0.95 . ?
C6 C7 1.388(4) . ?
C7 H7 0.95 . ?
C8 C9 1.392(4) . ?
C8 C13 1.400(4) . ?
C8 N1 1.415(4) . ?
C9 H9 0.95 . ?
C9 C10 1.373(4) . ?
C10 C11 1.384(4) . ?
C10 F3 1.363(3) . ?
C11 H11 0.95 . ?
C11 C12 1.372(4) . ?
C12 C13 1.370(4) . ?
C12 F4 1.363(3) . ?
C13 H13 0.95 . ?

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
C2 C1 H1 119.2 . . ?
N1 C1 H1 119.2 . . ?
N1 C1 C2 121.5(3) . . ?
C3 C2 C1 120.9(3) . . ?
C7 C2 C1 122.3(3) . . ?
C7 C2 C3 116.8(3) . . ?
C4 C3 C2 123.6(3) . . ?
F1 C3 C2 118.3(3) . . ?
F1 C3 C4 118.1(3) . . ?
C3 C4 H4 121.7 . . ?
C3 C4 C5 116.7(3) . . ?
C5 C4 H4 121.7 . . ?
C4 C5 C6 123.6(3) . . ?
F2 C5 C4 117.9(3) . . ?
F2 C5 C6 118.5(3) . . ?
C5 C6 H6 121.2 . . ?
C5 C6 C7 117.5(3) . . ?
C7 C6 H6 121.2 . . ?
C2 C7 H7 119.1 . . ?
C6 C7 C2 121.9(3) . . ?
C6 C7 H7 119.1 . . ?
C9 C8 C13 119.6(3) . . ?
C9 C8 N1 122.5(3) . . ?
C13 C8 N1 117.8(3) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 C8 118.6(3) . . ?
C10 C9 H9 120.7 . . ?
C9 C10 C11 123.6(3) . . ?
F3 C10 C9 118.0(3) . . ?
F3 C10 C11 118.4(3) . . ?
C10 C11 H11 122.2 . . ?
C12 C11 C10 115.6(3) . . ?
C12 C11 H11 122.2 . . ?
C13 C12 C11 124.2(3) . . ?
F4 C12 C11 117.5(3) . . ?
F4 C12 C13 118.2(3) . . ?
C8 C13 H13 120.8 . . ?
C12 C13 C8 118.3(3) . . ?
C12 C13 H13 120.8 . . ?
C1 N1 C8 117.7(3) . . ?

# 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_76
_database_code_depnum_ccdc_archive 'CCDC 1008462'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2013-10-24T01:00:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.8363(4)
_cell_length_b                   13.8701(8)
_cell_length_c                   11.6974(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.915(3)
_cell_angle_gamma                90
_cell_volume                     1066.64(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2585
_cell_measurement_theta_min      3.43
_cell_measurement_theta_max      29.968

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

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        R(int) was 0.0427 before and 0.0375 after correction.
        The Ratio of minimum to maximum transmission is 0.9054.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.6754
_exptl_absorpt_correction_T_max  0.746

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

_diffrn_source                   'fine-focus sealed tube'
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_number            8250
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         28.7
_diffrn_reflns_theta_full        28.7
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             2757
_reflns_number_gt                2196
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;
        XL, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0421P)²+0.3086P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2757
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0975
_refine_ls_wR_factor_gt          0.0909
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.047

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.65538(19) 0.56150(9) 0.39051(11) 0.0202(3) Uani 1 1 d . . .
H1 H 0.7902 0.5666 0.4408 0.024 Uiso 1 1 calc R . .
C2 C 0.61508(19) 0.50345(9) 0.28149(11) 0.0193(2) Uani 1 1 d . . .
C3 C 0.77427(19) 0.46697(9) 0.24115(12) 0.0227(3) Uani 1 1 d . . .
C4 C 0.7450(2) 0.41188(10) 0.13931(13) 0.0262(3) Uani 1 1 d . . .
H4 H 0.8578 0.3888 0.1145 0.031 Uiso 1 1 calc R . .
C5 C 0.5479(2) 0.39112(10) 0.07425(12) 0.0265(3) Uani 1 1 d . . .
H5 H 0.5223 0.3534 0.0039 0.032 Uiso 1 1 calc R . .
C6 C 0.3886(2) 0.42667(10) 0.11401(12) 0.0241(3) Uani 1 1 d . . .
C7 C 0.41613(19) 0.48202(9) 0.21454(11) 0.0204(3) Uani 1 1 d . . .
H7 H 0.3026 0.5053 0.2383 0.024 Uiso 1 1 calc R . .
C8 C 0.55283(18) 0.66373(9) 0.52075(10) 0.0175(2) Uani 1 1 d . . .
C13 C 0.38647(18) 0.69194(9) 0.56031(11) 0.0184(2) Uani 1 1 d . . .
C12 C 0.40959(19) 0.75317(9) 0.65648(11) 0.0198(3) Uani 1 1 d . . .
C11 C 0.5970(2) 0.78822(9) 0.71775(11) 0.0217(3) Uani 1 1 d . . .
H11 H 0.6115 0.8301 0.7838 0.026 Uiso 1 1 calc R . .
C10 C 0.7652(2) 0.76052(10) 0.68002(12) 0.0238(3) Uani 1 1 d . . .
H10 H 0.8964 0.7835 0.7213 0.029 Uiso 1 1 calc R . .
C9 C 0.74362(19) 0.69985(9) 0.58306(11) 0.0215(3) Uani 1 1 d . . .
H9 H 0.8603 0.6825 0.5585 0.026 Uiso 1 1 calc R . .
N1 N 0.51060(16) 0.60499(7) 0.41805(9) 0.0189(2) Uani 1 1 d . . .
F1 F 0.96843(11) 0.48720(6) 0.30528(8) 0.0307(2) Uani 1 1 d . . .
F2 F 0.19504(13) 0.40592(7) 0.04964(8) 0.0346(2) Uani 1 1 d . . .
F4 F 0.19742(11) 0.65911(6) 0.50502(7) 0.02505(19) Uani 1 1 d . . .
F3 F 0.24039(11) 0.77875(6) 0.68844(7) 0.0276(2) Uani 1 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 H1 0.95 . ?
C1 C2 1.4690(17) . ?
C1 N1 1.2736(16) . ?
C2 C3 1.3945(17) . ?
C2 C7 1.4026(18) . ?
C3 C4 1.3829(19) . ?
C3 F1 1.3629(15) . ?
C4 H4 0.95 . ?
C4 C5 1.384(2) . ?
C5 H5 0.95 . ?
C5 C6 1.3868(19) . ?
C6 C7 1.3734(18) . ?
C6 F2 1.3615(15) . ?
C7 H7 0.95 . ?
C8 C13 1.3962(16) . ?
C8 C9 1.4007(17) . ?
C8 N1 1.4142(16) . ?
C13 C12 1.3836(18) . ?
C13 F4 1.3556(13) . ?
C12 C11 1.3739(18) . ?
C12 F3 1.3567(13) . ?
C11 H11 0.95 . ?
C11 C10 1.3938(18) . ?
C10 H10 0.95 . ?
C10 C9 1.3873(18) . ?
C9 H9 0.95 . ?

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
C2 C1 H1 119.8 . . ?
N1 C1 H1 119.8 . . ?
N1 C1 C2 120.36(11) . . ?
C3 C2 C1 120.98(11) . . ?
C3 C2 C7 117.47(11) . . ?
C7 C2 C1 121.55(11) . . ?
C4 C3 C2 123.38(12) . . ?
F1 C3 C2 118.14(11) . . ?
F1 C3 C4 118.48(11) . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.52(12) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.52(12) . . ?
C6 C5 H5 120.7 . . ?
C7 C6 C5 123.36(12) . . ?
F2 C6 C5 118.21(12) . . ?
F2 C6 C7 118.43(12) . . ?
C2 C7 H7 120.6 . . ?
C6 C7 C2 118.75(12) . . ?
C6 C7 H7 120.6 . . ?
C13 C8 C9 117.01(11) . . ?
C13 C8 N1 116.61(11) . . ?
C9 C8 N1 126.31(11) . . ?
C12 C13 C8 121.31(11) . . ?
F4 C13 C8 120.29(11) . . ?
F4 C13 C12 118.39(11) . . ?
C11 C12 C13 121.58(11) . . ?
F3 C12 C13 117.94(11) . . ?
F3 C12 C11 120.48(11) . . ?
C12 C11 H11 121 . . ?
C12 C11 C10 117.99(12) . . ?
C10 C11 H11 121 . . ?
C11 C10 H10 119.5 . . ?
C9 C10 C11 120.95(12) . . ?
C9 C10 H10 119.5 . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.15(11) . . ?
C10 C9 H9 119.4 . . ?
C1 N1 C8 119.73(11) . . ?

# 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_77
_database_code_depnum_ccdc_archive 'CCDC 1008463'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2013-10-24T01:02:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3598(10)
_cell_length_b                   12.5972(14)
_cell_length_c                   12.6690(16)
_cell_angle_alpha                70.079(7)
_cell_angle_beta                 75.851(8)
_cell_angle_gamma                78.418(7)
_cell_volume                     1061.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       needle
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_F_000             512
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        R(int) was 0.0427 before and 0.0375 after correction.
        The Ratio of minimum to maximum transmission is 0.9054.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.632
_exptl_absorpt_correction_T_max  0.726

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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_number            9688
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.734
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_number_total             3727
_reflns_number_gt                2465
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0489P)²+0.2986P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3727
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1096
_refine_ls_wR_factor_gt          0.094
_refine_ls_goodness_of_fit_ref   1.01
_refine_ls_restrained_S_all      1.01
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.05

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'

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
F7 F 0.60470(19) 0.02823(10) 0.83237(12) 0.0364(4) Uani 1 d . .
F6 F 0.17264(19) 0.90324(10) 0.50727(11) 0.0312(4) Uani 1 d . .
F8 F 0.4157(2) 0.36669(10) 0.56111(11) 0.0324(4) Uani 1 d . .
F5 F -0.05970(18) 0.63039(10) 0.93613(10) 0.0293(3) Uani 1 d . .
F3 F 0.38511(18) 0.98245(10) 0.67160(11) 0.0297(3) Uani 1 d . .
F2 F 0.9859(2) 0.13683(10) 0.98957(11) 0.0331(4) Uani 1 d . .
F1 F 0.92058(19) 0.35991(10) 0.54900(10) 0.0306(3) Uani 1 d . .
F4 F 0.46261(19) 0.61809(11) 0.93237(11) 0.0322(4) Uani 1 d . .
N2 N 0.3132(2) 0.48402(14) 0.71492(15) 0.0191(4) Uani 1 d . .
N1 N 0.7268(2) 0.53587(14) 0.77904(15) 0.0203(4) Uani 1 d . .
C18 C -0.0128(3) 0.88180(18) 0.69171(19) 0.0211(5) Uani 1 d . .
H18 H -0.058 0.9608 0.6697 0.025 Uiso 1 calc . .
C19 C 0.1128(3) 0.83327(18) 0.61505(18) 0.0211(5) Uani 1 d . .
C20 C 0.1808(3) 0.72009(17) 0.64095(18) 0.0188(5) Uani 1 d . .
H20 H 0.2667 0.6906 0.5852 0.023 Uiso 1 calc . .
C15 C 0.1216(3) 0.64859(17) 0.75109(18) 0.0181(5) Uani 1 d . .
C14 C 0.1884(3) 0.52644(17) 0.78403(19) 0.0190(5) Uani 1 d . .
H14 H 0.1384 0.4785 0.8573 0.023 Uiso 1 calc . .
C21 C 0.3789(3) 0.36647(17) 0.75179(19) 0.0188(5) Uani 1 d . .
C26 C 0.4367(3) 0.30939(18) 0.67015(19) 0.0209(5) Uani 1 d . .
C25 C 0.5117(3) 0.19692(18) 0.6946(2) 0.0251(5) Uani 1 d . .
H25 H 0.5498 0.1601 0.6371 0.03 Uiso 1 calc . .
C24 C 0.5291(3) 0.14000(18) 0.8059(2) 0.0262(6) Uani 1 d . .
C23 C 0.4771(3) 0.19070(18) 0.8915(2) 0.0250(5) Uani 1 d . .
H23 H 0.4918 0.1487 0.9677 0.03 Uiso 1 calc . .
C22 C 0.4031(3) 0.30415(18) 0.86330(19) 0.0228(5) Uani 1 d . .
H22 H 0.3678 0.3408 0.9209 0.027 Uiso 1 calc . .
C16 C -0.0027(3) 0.69816(18) 0.82818(18) 0.0198(5) Uani 1 d . .
C17 C -0.0707(3) 0.81224(18) 0.80102(19) 0.0216(5) Uani 1 d . .
H17 H -0.1558 0.8425 0.8565 0.026 Uiso 1 calc . .
C5 C 1.0392(3) 0.13618(19) 0.7990(2) 0.0239(5) Uani 1 d . .
H5 H 1.0955 0.0591 0.8209 0.029 Uiso 1 calc . .
C4 C 1.0220(3) 0.19355(19) 0.6867(2) 0.0253(5) Uani 1 d . .
H4 H 1.0676 0.1569 0.6293 0.03 Uiso 1 calc . .
C3 C 0.9376(3) 0.30492(18) 0.65974(18) 0.0201(5) Uani 1 d . .
C2 C 0.8695(3) 0.36347(17) 0.73897(18) 0.0185(5) Uani 1 d . .
C1 C 0.7743(3) 0.48078(17) 0.70663(19) 0.0191(5) Uani 1 d . .
H1 H 0.748 0.5157 0.6317 0.023 Uiso 1 calc . .
C8 C 0.6393(3) 0.64956(17) 0.74425(19) 0.0188(5) Uani 1 d . .
C13 C 0.5101(3) 0.69066(18) 0.82654(18) 0.0203(5) Uani 1 d . .
C12 C 0.4234(3) 0.80098(18) 0.8052(2) 0.0231(5) Uani 1 d . .
H12 H 0.3352 0.8265 0.8628 0.028 Uiso 1 calc . .
C11 C 0.4710(3) 0.87221(17) 0.6964(2) 0.0218(5) Uani 1 d . .
C6 C 0.9719(3) 0.19452(18) 0.87806(19) 0.0218(5) Uani 1 d . .
C7 C 0.8894(3) 0.30500(18) 0.85206(19) 0.0207(5) Uani 1 d . .
H7 H 0.8462 0.3416 0.9097 0.025 Uiso 1 calc . .
C10 C 0.5995(3) 0.83920(18) 0.6106(2) 0.0228(5) Uani 1 d . .
H10 H 0.6301 0.8917 0.5365 0.027 Uiso 1 calc . .
C9 C 0.6825(3) 0.72707(18) 0.63578(19) 0.0218(5) Uani 1 d . .
H9 H 0.771 0.7023 0.5778 0.026 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   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
F7 C24 1.364(2) . ?
F6 C19 1.370(2) . ?
F8 C26 1.354(2) . ?
F5 C16 1.358(2) . ?
F3 C11 1.369(2) . ?
F2 C6 1.370(2) . ?
F1 C3 1.361(2) . ?
F4 C13 1.349(2) . ?
N2 C14 1.274(3) . ?
N2 C21 1.413(3) . ?
N1 C1 1.275(3) . ?
N1 C8 1.414(3) . ?
C18 H18 0.95 . ?
C18 C19 1.382(3) . ?
C18 C17 1.379(3) . ?
C19 C20 1.366(3) . ?
C20 H20 0.95 . ?
C20 C15 1.397(3) . ?
C15 C14 1.464(3) . ?
C15 C16 1.389(3) . ?
C14 H14 0.95 . ?
C21 C26 1.392(3) . ?
C21 C22 1.398(3) . ?
C26 C25 1.371(3) . ?
C25 H25 0.95 . ?
C25 C24 1.372(3) . ?
C24 C23 1.379(3) . ?
C23 H23 0.95 . ?
C23 C22 1.379(3) . ?
C22 H22 0.95 . ?
C16 C17 1.376(3) . ?
C17 H17 0.95 . ?
C5 H5 0.95 . ?
C5 C4 1.382(3) . ?
C5 C6 1.379(3) . ?
C4 H4 0.95 . ?
C4 C3 1.378(3) . ?
C3 C2 1.383(3) . ?
C2 C1 1.468(3) . ?
C2 C7 1.399(3) . ?
C1 H1 0.95 . ?
C8 C13 1.394(3) . ?
C8 C9 1.393(3) . ?
C13 C12 1.373(3) . ?
C12 H12 0.95 . ?
C12 C11 1.369(3) . ?
C11 C10 1.378(3) . ?
C6 C7 1.364(3) . ?
C7 H7 0.95 . ?
C10 H10 0.95 . ?
C10 C9 1.383(3) . ?
C9 H9 0.95 . ?

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
C14 N2 C21 118.52(18) . . ?
C1 N1 C8 118.53(19) . . ?
C19 C18 H18 120.9 . . ?
C17 C18 H18 120.9 . . ?
C17 C18 C19 118.10(19) . . ?
F6 C19 C18 117.81(18) . . ?
C20 C19 F6 118.45(19) . . ?
C20 C19 C18 123.7(2) . . ?
C19 C20 H20 120.7 . . ?
C19 C20 C15 118.7(2) . . ?
C15 C20 H20 120.7 . . ?
C20 C15 C14 121.33(19) . . ?
C16 C15 C20 117.33(19) . . ?
C16 C15 C14 121.35(19) . . ?
N2 C14 C15 120.4(2) . . ?
N2 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C26 C21 N2 118.1(2) . . ?
C26 C21 C22 116.93(19) . . ?
C22 C21 N2 124.86(19) . . ?
F8 C26 C21 118.79(19) . . ?
F8 C26 C25 117.83(19) . . ?
C25 C26 C21 123.4(2) . . ?
C26 C25 H25 121.6 . . ?
C26 C25 C24 116.9(2) . . ?
C24 C25 H25 121.6 . . ?
F7 C24 C25 118.1(2) . . ?
F7 C24 C23 118.6(2) . . ?
C25 C24 C23 123.3(2) . . ?
C24 C23 H23 121 . . ?
C22 C23 C24 118.0(2) . . ?
C22 C23 H23 121 . . ?
C21 C22 H22 119.2 . . ?
C23 C22 C21 121.5(2) . . ?
C23 C22 H22 119.2 . . ?
F5 C16 C15 118.21(18) . . ?
F5 C16 C17 118.28(19) . . ?
C17 C16 C15 123.5(2) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 C18 118.7(2) . . ?
C16 C17 H17 120.7 . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C6 C5 C4 117.8(2) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 C5 118.7(2) . . ?
C3 C4 H4 120.6 . . ?
F1 C3 C4 117.98(19) . . ?
F1 C3 C2 118.47(19) . . ?
C4 C3 C2 123.6(2) . . ?
C3 C2 C1 121.4(2) . . ?
C3 C2 C7 117.25(19) . . ?
C7 C2 C1 121.30(19) . . ?
N1 C1 C2 120.0(2) . . ?
N1 C1 H1 120 . . ?
C2 C1 H1 120 . . ?
C13 C8 N1 117.93(19) . . ?
C9 C8 N1 125.00(19) . . ?
C9 C8 C13 116.88(19) . . ?
F4 C13 C8 118.81(18) . . ?
F4 C13 C12 117.57(19) . . ?
C12 C13 C8 123.6(2) . . ?
C13 C12 H12 121.8 . . ?
C11 C12 C13 116.4(2) . . ?
C11 C12 H12 121.8 . . ?
F3 C11 C12 118.0(2) . . ?
F3 C11 C10 118.2(2) . . ?
C12 C11 C10 123.8(2) . . ?
F2 C6 C5 117.69(19) . . ?
C7 C6 F2 118.40(19) . . ?
C7 C6 C5 123.9(2) . . ?
C2 C7 H7 120.6 . . ?
C6 C7 C2 118.7(2) . . ?
C6 C7 H7 120.6 . . ?
C11 C10 H10 121.1 . . ?
C11 C10 C9 117.8(2) . . ?
C9 C10 H10 121.1 . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.5(2) . . ?
C10 C9 H9 119.2 . . ?

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
F7 C24 C23 C22 179.18(19) . . . . ?
F6 C19 C20 C15 179.40(18) . . . . ?
F8 C26 C25 C24 -179.06(19) . . . . ?
F5 C16 C17 C18 179.71(19) . . . . ?
F3 C11 C10 C9 -178.63(19) . . . . ?
F2 C6 C7 C2 -178.14(19) . . . . ?
F1 C3 C2 C1 2.3(3) . . . . ?
F1 C3 C2 C7 -179.79(18) . . . . ?
F4 C13 C12 C11 -178.58(19) . . . . ?
N2 C21 C26 F8 -4.4(3) . . . . ?
N2 C21 C26 C25 176.7(2) . . . . ?
N2 C21 C22 C23 -176.7(2) . . . . ?
N1 C8 C13 F4 -5.6(3) . . . . ?
N1 C8 C13 C12 176.4(2) . . . . ?
N1 C8 C9 C10 -175.55(19) . . . . ?
C18 C19 C20 C15 -0.3(3) . . . . ?
C19 C18 C17 C16 -0.7(3) . . . . ?
C19 C20 C15 C14 179.63(19) . . . . ?
C19 C20 C15 C16 -0.6(3) . . . . ?
C20 C15 C14 N2 5.1(3) . . . . ?
C20 C15 C16 F5 -179.05(19) . . . . ?
C20 C15 C16 C17 0.8(3) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C14 N2 C21 C26 149.4(2) . . . . ?
C14 N2 C21 C22 -35.4(3) . . . . ?
C14 C15 C16 F5 0.7(3) . . . . ?
C14 C15 C16 C17 -179.4(2) . . . . ?
C21 N2 C14 C15 177.60(18) . . . . ?
C21 C26 C25 C24 -0.1(3) . . . . ?
C26 C21 C22 C23 -1.3(3) . . . . ?
C26 C25 C24 F7 -179.50(19) . . . . ?
C26 C25 C24 C23 -0.6(4) . . . . ?
C25 C24 C23 C22 0.3(4) . . . . ?
C24 C23 C22 C21 0.7(3) . . . . ?
C22 C21 C26 F8 180.00(19) . . . . ?
C22 C21 C26 C25 1.0(3) . . . . ?
C16 C15 C14 N2 -174.7(2) . . . . ?
C17 C18 C19 F6 -178.73(19) . . . . ?
C17 C18 C19 C20 1.0(3) . . . . ?
C5 C4 C3 F1 -179.54(19) . . . . ?
C5 C4 C3 C2 0.5(3) . . . . ?
C5 C6 C7 C2 0.5(3) . . . . ?
C4 C5 C6 F2 178.8(2) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C4 C3 C2 C1 -177.7(2) . . . . ?
C4 C3 C2 C7 0.2(3) . . . . ?
C3 C2 C1 N1 -174.2(2) . . . . ?
C3 C2 C7 C6 -0.7(3) . . . . ?
C1 N1 C8 C13 149.4(2) . . . . ?
C1 N1 C8 C9 -35.8(3) . . . . ?
C1 C2 C7 C6 177.2(2) . . . . ?
C8 N1 C1 C2 178.56(18) . . . . ?
C8 C13 C12 C11 -0.5(3) . . . . ?
C13 C8 C9 C10 -0.7(3) . . . . ?
C13 C12 C11 F3 179.03(18) . . . . ?
C13 C12 C11 C10 -0.7(3) . . . . ?
C12 C11 C10 C9 1.1(3) . . . . ?
C11 C10 C9 C8 -0.3(3) . . . . ?
C6 C5 C4 C3 -0.6(3) . . . . ?
C7 C2 C1 N1 8.0(3) . . . . ?
C9 C8 C13 F4 179.22(19) . . . . ?
C9 C8 C13 C12 1.1(3) . . . . ?

# 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_78
_database_code_depnum_ccdc_archive 'CCDC 1008464'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2013-10-24T01:03:33-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.6472(4)
_cell_length_b                   15.8920(9)
_cell_length_c                   10.0448(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.712(3)
_cell_angle_gamma                90
_cell_volume                     1059.92(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    2581
_cell_measurement_theta_min      2.401
_cell_measurement_theta_max      25.038

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

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_F_000             512
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        R(int) was 0.0484 before and 0.0315 after correction.
        The Ratio of minimum to maximum transmission is 0.9071.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.676
_exptl_absorpt_correction_T_max  0.7452

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

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'MO K\a'
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_number            5694
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.401
_diffrn_reflns_theta_max         25.038
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_number_total             1864
_reflns_number_gt                1610
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_refinement  
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        2008). A64, 112-122
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0382P)²+0.4595P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1864
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0835
_refine_ls_wR_factor_gt          0.0796
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'

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 0.2423(2) 0.40794(9) 0.43561(14) 0.0180(3) Uani 1 d . .
H1 H 0.1304 0.4439 0.4166 0.022 Uiso 1 calc . .
C2 C 0.2301(2) 0.34306(9) 0.53864(14) 0.0177(3) Uani 1 d . .
C3 C 0.0517(2) 0.32758(9) 0.60093(15) 0.0198(3) Uani 1 d . .
C4 C 0.0345(2) 0.26921(10) 0.70093(15) 0.0221(4) Uani 1 d . .
H4 H -0.0906 0.2608 0.741 0.027 Uiso 1 calc . .
C5 C 0.2026(2) 0.22293(10) 0.74221(15) 0.0221(4) Uani 1 d . .
H5 H 0.1958 0.1822 0.811 0.026 Uiso 1 calc . .
C6 C 0.3803(2) 0.23771(9) 0.68052(15) 0.0208(4) Uani 1 d . .
C7 C 0.3985(2) 0.29603(9) 0.58058(14) 0.0198(3) Uani 1 d . .
H7 H 0.5238 0.3041 0.5408 0.024 Uiso 1 calc . .
C8 C 0.4051(2) 0.47855(9) 0.27063(14) 0.0188(3) Uani 1 d . .
C13 C 0.5908(2) 0.51196(9) 0.23970(15) 0.0190(3) Uani 1 d . .
C12 C 0.6129(3) 0.57235(10) 0.14308(15) 0.0223(4) Uani 1 d . .
H12 H 0.7423 0.5941 0.1261 0.027 Uiso 1 calc . .
C11 C 0.4440(2) 0.60082(9) 0.07123(15) 0.0229(4) Uani 1 d . .
H11 H 0.4541 0.643 0.0048 0.027 Uiso 1 calc . .
C10 C 0.2607(2) 0.56633(10) 0.09876(15) 0.0222(4) Uani 1 d . .
C9 C 0.2361(2) 0.50623(10) 0.19500(15) 0.0212(3) Uani 1 d . .
H9 H 0.1064 0.4839 0.2098 0.025 Uiso 1 calc . .
N1 N 0.4008(2) 0.41655(8) 0.37171(12) 0.0203(3) Uani 1 d . .
F1 F -0.11503(13) 0.37225(6) 0.56052(9) 0.0265(2) Uani 1 d . .
F2 F 0.54661(14) 0.19318(6) 0.72132(9) 0.0296(3) Uani 1 d . .
F4 F 0.75832(13) 0.48447(5) 0.30978(9) 0.0243(2) Uani 1 d . .
F3 F 0.09392(14) 0.59191(6) 0.02531(9) 0.0314(3) 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 H1 0.95 . ?
C1 C2 1.466(2) . ?
C1 N1 1.267(2) . ?
C2 C3 1.389(2) . ?
C2 C7 1.394(2) . ?
C3 C4 1.376(2) . ?
C3 F1 1.3617(17) . ?
C4 H4 0.95 . ?
C4 C5 1.385(2) . ?
C5 H5 0.95 . ?
C5 C6 1.379(2) . ?
C6 C7 1.376(2) . ?
C6 F2 1.3596(17) . ?
C7 H7 0.95 . ?
C8 C13 1.392(2) . ?
C8 C9 1.397(2) . ?
C8 N1 1.4160(19) . ?
C13 C12 1.378(2) . ?
C13 F4 1.3611(17) . ?
C12 H12 0.95 . ?
C12 C11 1.382(2) . ?
C11 H11 0.95 . ?
C11 C10 1.376(2) . ?
C10 C9 1.374(2) . ?
C10 F3 1.3644(18) . ?
C9 H9 0.95 . ?

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
C2 C1 H1 119.7 . . ?
N1 C1 H1 119.7 . . ?
N1 C1 C2 120.59(14) . . ?
C3 C2 C1 121.32(14) . . ?
C3 C2 C7 117.34(14) . . ?
C7 C2 C1 121.32(14) . . ?
C4 C3 C2 123.41(14) . . ?
F1 C3 C2 118.27(13) . . ?
F1 C3 C4 118.32(14) . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.85(15) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 H5 121 . . ?
C6 C5 C4 118.10(14) . . ?
C6 C5 H5 121 . . ?
C7 C6 C5 123.31(14) . . ?
F2 C6 C5 118.50(13) . . ?
F2 C6 C7 118.19(14) . . ?
C2 C7 H7 120.5 . . ?
C6 C7 C2 118.99(14) . . ?
C6 C7 H7 120.5 . . ?
C13 C8 C9 117.20(14) . . ?
C13 C8 N1 118.26(14) . . ?
C9 C8 N1 124.47(14) . . ?
C12 C13 C8 123.25(15) . . ?
F4 C13 C8 118.32(13) . . ?
F4 C13 C12 118.42(14) . . ?
C13 C12 H12 120.5 . . ?
C13 C12 C11 119.00(15) . . ?
C11 C12 H12 120.5 . . ?
C12 C11 H11 121 . . ?
C10 C11 C12 118.03(14) . . ?
C10 C11 H11 121 . . ?
C9 C10 C11 123.68(15) . . ?
F3 C10 C11 118.51(14) . . ?
F3 C10 C9 117.80(14) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 C8 118.79(15) . . ?
C10 C9 H9 120.6 . . ?
C1 N1 C8 118.93(13) . . ?

# 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_80
_database_code_depnum_ccdc_archive 'CCDC 1008465'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2013-10-25T19:07:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.7505(4)
_cell_length_b                   3.75740(10)
_cell_length_c                   26.3533(7)
_cell_angle_alpha                90
_cell_angle_beta                 130.149(2)
_cell_angle_gamma                90
_cell_volume                     1040.74(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    3159
_cell_measurement_theta_min      3
_cell_measurement_theta_max      28.26

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0613 before and 0.0424 after correction.
        The Ratio of minimum to maximum transmission is 0.7912.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.5902
_exptl_absorpt_correction_T_max  0.746

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

_diffrn_source                   'fine-focus sealed tube'
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_number            7150
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_reflns_number_total             1827
_reflns_number_gt                1533
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_solution    
;
        XS, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_computing_structure_refinement  
;
        XL, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0522P)²+0.3542P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1827
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0957
_refine_ls_wR_factor_gt          0.0872
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.046

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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 0.0061 0.0033 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F3 F 0.03468(9) 0.7139(3) 0.21153(4) 0.0323(3) Uani 1 1 d . . .
F1 F 0.04508(8) 0.6672(3) -0.03761(4) 0.0272(3) Uani 1 1 d . . .
F2 F 0.48782(9) 1.2504(3) 0.04517(4) 0.0302(3) Uani 1 1 d . . .
F4 F 0.21622(9) 0.9697(3) 0.33473(4) 0.0313(3) Uani 1 1 d . . .
C4 C 0.17693(15) 0.8376(4) -0.06136(8) 0.0231(4) Uani 1 1 d . . .
H4 H 0.115 0.7531 -0.1055 0.028 Uiso 1 1 calc R . .
C7 C 0.35629(15) 1.0861(4) 0.06905(8) 0.0207(3) Uani 1 1 d . . .
H7 H 0.4182 1.1732 0.113 0.025 Uiso 1 1 calc R . .
C9 C 0.15664(15) 0.8565(4) 0.18035(8) 0.0221(4) Uani 1 1 d . . .
H9 H 0.0916 0.7672 0.1369 0.027 Uiso 1 1 calc R . .
C2 C 0.24252(14) 0.9351(4) 0.04861(7) 0.0194(3) Uani 1 1 d . . .
C10 C 0.14157(14) 0.8495(4) 0.22696(8) 0.0224(4) Uani 1 1 d . . .
C6 C 0.37673(15) 1.1061(4) 0.02452(8) 0.0223(4) Uani 1 1 d . . .
C12 C 0.34559(15) 1.1205(4) 0.30779(8) 0.0233(4) Uani 1 1 d . . .
H12 H 0.4096 1.2109 0.3513 0.028 Uiso 1 1 calc R . .
C1 C 0.21635(15) 0.9037(4) 0.09426(8) 0.0208(3) Uani 1 1 d . . .
H1 H 0.1397 0.7945 0.0795 0.025 Uiso 1 1 calc R . .
C3 C 0.15637(14) 0.8158(4) -0.01652(7) 0.0204(3) Uani 1 1 d . . .
N1 N 0.29520(12) 1.0212(3) 0.15339(6) 0.0220(3) Uani 1 1 d . . .
C8 C 0.26894(15) 0.9966(4) 0.19736(8) 0.0203(3) Uani 1 1 d . . .
C13 C 0.36288(15) 1.1282(4) 0.26125(8) 0.0223(4) Uani 1 1 d . . .
H13 H 0.4391 1.2236 0.2731 0.027 Uiso 1 1 calc R . .
C11 C 0.23529(16) 0.9812(4) 0.29032(8) 0.0226(4) Uani 1 1 d . . .
C5 C 0.29014(15) 0.9860(4) -0.04030(8) 0.0242(4) Uani 1 1 d . . .
H5 H 0.3077 1.0047 -0.0696 0.029 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   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
F3 C10 1.3471(17) . ?
F1 C3 1.3658(17) . ?
F2 C6 1.3609(18) . ?
F4 C11 1.3552(17) . ?
C4 C3 1.383(2) . ?
C4 C5 1.389(2) . ?
C7 C2 1.404(2) . ?
C7 C6 1.374(2) . ?
C9 C10 1.371(2) . ?
C9 C8 1.404(2) . ?
C2 C1 1.466(2) . ?
C2 C3 1.389(2) . ?
C10 C11 1.385(2) . ?
C6 C5 1.384(2) . ?
C12 C13 1.392(2) . ?
C12 C11 1.373(2) . ?
C1 N1 1.273(2) . ?
N1 C8 1.4216(19) . ?
C8 C13 1.394(2) . ?

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
C3 C4 C5 118.45(14) . . ?
C6 C7 C2 119.03(14) . . ?
C10 C9 C8 119.44(14) . . ?
C7 C2 C1 121.32(14) . . ?
C3 C2 C7 117.14(13) . . ?
C3 C2 C1 121.54(14) . . ?
F3 C10 C9 120.15(14) . . ?
F3 C10 C11 119.02(13) . . ?
C9 C10 C11 120.83(14) . . ?
F2 C6 C7 118.39(13) . . ?
F2 C6 C5 118.28(13) . . ?
C7 C6 C5 123.33(14) . . ?
C11 C12 C13 119.45(14) . . ?
N1 C1 C2 120.72(14) . . ?
F1 C3 C4 117.98(13) . . ?
F1 C3 C2 118.30(13) . . ?
C4 C3 C2 123.72(14) . . ?
C1 N1 C8 120.79(14) . . ?
C9 C8 N1 124.71(14) . . ?
C13 C8 C9 119.38(14) . . ?
C13 C8 N1 115.90(13) . . ?
C12 C13 C8 120.35(14) . . ?
F4 C11 C10 118.81(14) . . ?
F4 C11 C12 120.64(14) . . ?
C12 C11 C10 120.55(14) . . ?
C6 C5 C4 118.33(14) . . ?

# 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_81
_database_code_depnum_ccdc_archive 'CCDC 1008466'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2015-01-29T11:40:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   3.7226(6)
_cell_length_b                   13.105(2)
_cell_length_c                   21.768(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1062.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100

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

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_F_000             512
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0644 before and 0.0552 after correction.
        The Ratio of minimum to maximum transmission is 0.9036.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.6738
_exptl_absorpt_correction_T_max  0.7457

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

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_number            5829
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.814
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_reflns_number_total             1852
_reflns_number_gt                1542
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0164P)²+0.3562P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1852
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0711
_refine_ls_wR_factor_gt          0.0654
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.045

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'

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 0.2418(9) 0.3598(2) 0.59571(15) 0.0194(8) Uani 1 d . .
H1 H 0.3318 0.2972 0.5801 0.023 Uiso 1 calc . .
C2 C 0.1500(9) 0.4417(2) 0.55257(14) 0.0179(8) Uani 1 d . .
C3 C 0.1679(9) 0.4266(2) 0.48942(15) 0.0190(8) Uani 1 d . .
C4 C 0.0758(9) 0.4994(2) 0.44648(15) 0.0226(8) Uani 1 d . .
H4 H 0.0941 0.4853 0.4038 0.027 Uiso 1 calc . .
C5 C -0.0438(9) 0.5934(2) 0.46700(15) 0.0215(8) Uani 1 d . .
H5 H -0.115 0.6449 0.4388 0.026 Uiso 1 calc . .
C6 C -0.0567(9) 0.6102(2) 0.52980(16) 0.0214(8) Uani 1 d . .
C7 C 0.0346(9) 0.5376(2) 0.57234(15) 0.0211(9) Uani 1 d . .
H7 H 0.0195 0.5525 0.615 0.025 Uiso 1 calc . .
C8 C 0.2737(9) 0.2833(2) 0.69141(14) 0.0197(8) Uani 1 d . .
C9 C 0.1775(10) 0.1847(2) 0.67362(14) 0.0200(8) Uani 1 d . .
H9 H 0.0699 0.1724 0.6347 0.024 Uiso 1 calc . .
C10 C 0.2420(9) 0.1058(2) 0.71367(15) 0.0216(8) Uani 1 d . .
C11 C 0.4015(10) 0.1181(3) 0.77030(15) 0.0223(8) Uani 1 d . .
H11 H 0.4479 0.0621 0.7968 0.027 Uiso 1 calc . .
C12 C 0.4893(9) 0.2167(3) 0.78602(14) 0.0228(8) Uani 1 d . .
C13 C 0.4265(9) 0.2997(2) 0.74934(15) 0.0213(8) Uani 1 d . .
H13 H 0.485 0.3666 0.7628 0.026 Uiso 1 calc . .
N1 N 0.2045(8) 0.37022(18) 0.65382(12) 0.0201(7) Uani 1 d . .
F1 F 0.2865(5) 0.33363(13) 0.46838(8) 0.0269(5) Uani 1 d . .
F2 F -0.1670(5) 0.70305(13) 0.55001(8) 0.0304(5) Uani 1 d . .
F3 F 0.1398(6) 0.00992(13) 0.69627(8) 0.0302(5) Uani 1 d . .
F4 F 0.6490(6) 0.23262(14) 0.84151(8) 0.0319(5) 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 H1 0.95 . ?
C1 C2 1.466(4) . ?
C1 N1 1.280(4) . ?
C2 C3 1.391(4) . ?
C2 C7 1.397(4) . ?
C3 C4 1.379(4) . ?
C3 F1 1.374(3) . ?
C4 H4 0.95 . ?
C4 C5 1.384(4) . ?
C5 H5 0.95 . ?
C5 C6 1.386(5) . ?
C6 C7 1.370(4) . ?
C6 F2 1.358(4) . ?
C7 H7 0.95 . ?
C8 C9 1.396(4) . ?
C8 C13 1.400(4) . ?
C8 N1 1.426(4) . ?
C9 H9 0.95 . ?
C9 C10 1.373(4) . ?
C10 C11 1.378(5) . ?
C10 F3 1.367(3) . ?
C11 H11 0.95 . ?
C11 C12 1.376(5) . ?
C12 C13 1.370(4) . ?
C12 F4 1.362(3) . ?
C13 H13 0.95 . ?

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
C2 C1 H1 119 . . ?
N1 C1 H1 119 . . ?
N1 C1 C2 122.0(3) . . ?
C3 C2 C1 121.2(3) . . ?
C3 C2 C7 116.6(3) . . ?
C7 C2 C1 122.2(3) . . ?
C4 C3 C2 124.0(3) . . ?
F1 C3 C2 118.1(3) . . ?
F1 C3 C4 117.9(3) . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.5(3) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 H5 120.9 . . ?
C4 C5 C6 118.1(3) . . ?
C6 C5 H5 120.9 . . ?
C7 C6 C5 123.2(3) . . ?
F2 C6 C5 118.2(3) . . ?
F2 C6 C7 118.6(3) . . ?
C2 C7 H7 120.2 . . ?
C6 C7 C2 119.5(3) . . ?
C6 C7 H7 120.2 . . ?
C9 C8 C13 119.8(3) . . ?
C9 C8 N1 122.3(3) . . ?
C13 C8 N1 117.9(3) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 C8 118.4(3) . . ?
C10 C9 H9 120.8 . . ?
C9 C10 C11 123.7(3) . . ?
F3 C10 C9 117.9(3) . . ?
F3 C10 C11 118.4(3) . . ?
C10 C11 H11 122.1 . . ?
C12 C11 C10 115.8(3) . . ?
C12 C11 H11 122.1 . . ?
C13 C12 C11 124.1(3) . . ?
F4 C12 C11 117.9(3) . . ?
F4 C12 C13 118.0(3) . . ?
C8 C13 H13 120.9 . . ?
C12 C13 C8 118.2(3) . . ?
C12 C13 H13 120.9 . . ?
C1 N1 C8 117.5(3) . . ?

# 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_82
_database_code_depnum_ccdc_archive 'CCDC 1008467'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2015-01-29T11:16:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_Int_Tables_number      9
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   7.004(3)
_cell_length_b                   30.750(13)
_cell_length_c                   10.041(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.000(5)
_cell_angle_gamma                90
_cell_volume                     2135.9(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    100
_cell_measurement_reflns_used    1881
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      24.43

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

_exptl_crystal_description       THIN
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_F_000             1024

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

_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0556 before and 0.0443 after correction.
        The Ratio of minimum to maximum transmission is 0.9133.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.6814
_exptl_absorpt_correction_T_max  0.7461
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.986

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

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_number            5980
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.444
_diffrn_reflns_theta_max         25.023
_diffrn_reflns_theta_full        25.023
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.717
_diffrn_reflns_point_group_measured_fraction_max 0.717
_reflns_number_total             2697
_reflns_number_gt                2393
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0363P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2697
_refine_ls_number_parameters     325
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0704
_refine_ls_wR_factor_gt          0.0671
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'

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
F2 F 0.4396(3) 0.47040(6) 0.23456(19) 0.0272(5) Uani 1 d . .
F1 F 0.7394(3) 0.45896(6) 0.68518(18) 0.0259(5) Uani 1 d . .
F4 F 0.1649(3) 0.59122(6) 0.4325(2) 0.0341(5) Uani 1 d . .
C3 C 0.6631(5) 0.44013(11) 0.5662(3) 0.0201(8) Uani 1 d . .
F3 F 0.1894(3) 0.67652(7) 0.4797(3) 0.0463(7) Uani 1 d . .
C6 C 0.5130(5) 0.40219(11) 0.3284(4) 0.0237(8) Uani 1 d . .
H6 H 0.4623 0.3892 0.2444 0.028 Uiso 1 calc . .
C2 C 0.5887(5) 0.46777(11) 0.4617(4) 0.0182(7) Uani 1 d . .
C4 C 0.6640(5) 0.39550(11) 0.5594(4) 0.0239(8) Uani 1 d . .
H4 H 0.7154 0.3783 0.6351 0.029 Uiso 1 calc . .
C11 C 0.5269(6) 0.67545(12) 0.4873(4) 0.0325(9) Uani 1 d . .
H11 H 0.5345 0.7058 0.5046 0.039 Uiso 1 calc . .
C10 C 0.6910(6) 0.65134(12) 0.4776(4) 0.0314(10) Uani 1 d . .
H10 H 0.8132 0.6654 0.4873 0.038 Uiso 1 calc . .
C1 C 0.5964(5) 0.51502(11) 0.4814(3) 0.0203(8) Uani 1 d . .
H1 H 0.6927 0.5268 0.5489 0.024 Uiso 1 calc . .
C8 C 0.5027(5) 0.58571(10) 0.4387(3) 0.0184(8) Uani 1 d . .
C12 C 0.3536(6) 0.65417(12) 0.4713(4) 0.0292(9) Uani 1 d . .
C7 C 0.5139(5) 0.44631(11) 0.3432(4) 0.0202(8) Uani 1 d . .
C13 C 0.3406(5) 0.61038(12) 0.4465(4) 0.0249(8) Uani 1 d . .
N1 N 0.4784(4) 0.54088(9) 0.4113(3) 0.0197(6) Uani 1 d . .
C5 C 0.5871(5) 0.37671(11) 0.4376(3) 0.0228(8) Uani 1 d . .
H5 H 0.5852 0.3459 0.429 0.027 Uiso 1 calc . .
C9 C 0.6791(5) 0.60715(11) 0.4540(3) 0.0248(8) Uani 1 d . .
H9 H 0.7935 0.5912 0.4481 0.03 Uiso 1 calc . .
F5 F -0.0603(3) 0.43734(6) 0.21015(19) 0.0290(5) Uani 1 d . .
F6 F 0.1939(3) 0.37352(6) 0.62402(19) 0.0292(5) Uani 1 d . .
C14 C 0.0308(5) 0.36121(10) 0.3439(4) 0.0204(7) Uani 1 d . .
H14 H -0.0653 0.36 0.2659 0.024 Uiso 1 calc . .
C20 C 0.1482(5) 0.40903(10) 0.5464(3) 0.0198(8) Uani 1 d . .
F8 F 0.3852(3) 0.27735(7) 0.2769(2) 0.0406(6) Uani 1 d . .
F7 F 0.2880(3) 0.20705(8) 0.1267(3) 0.0504(7) Uani 1 d . .
C15 C 0.0666(5) 0.40319(10) 0.4125(3) 0.0182(7) Uani 1 d . .
C17 C 0.0456(5) 0.48233(11) 0.3949(4) 0.0201(8) Uani 1 d . .
H17 H 0.0098 0.5074 0.3415 0.024 Uiso 1 calc . .
C19 C 0.1790(5) 0.44891(10) 0.6060(3) 0.0195(8) Uani 1 d . .
H19 H 0.2343 0.4514 0.6983 0.023 Uiso 1 calc . .
C21 C 0.0610(5) 0.28900(10) 0.3052(3) 0.0220(8) Uani 1 d . .
C18 C 0.1273(5) 0.48575(11) 0.5281(4) 0.0221(8) Uani 1 d . .
H18 H 0.1489 0.5137 0.5677 0.027 Uiso 1 calc . .
C25 C 0.1478(6) 0.22878(12) 0.1765(4) 0.0306(9) Uani 1 d . .
N2 N 0.1197(4) 0.32667(9) 0.3822(3) 0.0228(7) Uani 1 d . .
C23 C -0.1780(6) 0.23810(11) 0.2014(4) 0.0282(9) Uani 1 d . .
H23 H -0.3089 0.2288 0.1849 0.034 Uiso 1 calc . .
C16 C 0.0180(5) 0.44143(11) 0.3422(3) 0.0203(8) Uani 1 d . .
C24 C -0.0405(6) 0.21488(12) 0.1491(4) 0.0301(9) Uani 1 d . .
H24 H -0.0744 0.1898 0.0952 0.036 Uiso 1 calc . .
C26 C 0.1987(5) 0.26454(11) 0.2549(4) 0.0255(8) Uani 1 d . .
C22 C -0.1289(5) 0.27487(11) 0.2779(4) 0.0260(9) Uani 1 d . .
H22 H -0.2268 0.2908 0.3123 0.031 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   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 C7 1.354(4) . ?
F1 C3 1.360(4) . ?
F4 C13 1.352(4) . ?
C3 C2 1.387(5) . ?
C3 C4 1.374(5) . ?
F3 C12 1.354(4) . ?
C6 C7 1.365(5) . ?
C6 C5 1.381(5) . ?
C2 C1 1.466(5) . ?
C2 C7 1.389(5) . ?
C4 C5 1.383(5) . ?
C11 C10 1.384(5) . ?
C11 C12 1.366(5) . ?
C10 C9 1.380(5) . ?
C1 N1 1.276(4) . ?
C8 C13 1.378(5) . ?
C8 N1 1.411(4) . ?
C8 C9 1.388(5) . ?
C12 C13 1.370(5) . ?
F5 C16 1.359(4) . ?
F6 C20 1.350(4) . ?
C14 C15 1.466(4) . ?
C14 N2 1.260(4) . ?
C20 C15 1.388(4) . ?
C20 C19 1.367(4) . ?
F8 C26 1.349(4) . ?
F7 C25 1.347(4) . ?
C15 C16 1.386(5) . ?
C17 C18 1.374(5) . ?
C17 C16 1.366(5) . ?
C19 C18 1.392(5) . ?
C21 N2 1.417(4) . ?
C21 C26 1.380(5) . ?
C21 C22 1.385(5) . ?
C25 C24 1.373(5) . ?
C25 C26 1.366(5) . ?
C23 C24 1.368(5) . ?
C23 C22 1.380(5) . ?

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 C3 C2 117.0(3) . . ?
F1 C3 C4 117.7(3) . . ?
C4 C3 C2 125.3(3) . . ?
C7 C6 C5 118.8(3) . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 C7 113.8(3) . . ?
C7 C2 C1 126.0(3) . . ?
C3 C4 C5 117.2(3) . . ?
C12 C11 C10 117.9(3) . . ?
C9 C10 C11 120.8(3) . . ?
N1 C1 C2 122.4(3) . . ?
C13 C8 N1 118.3(3) . . ?
C13 C8 C9 117.3(3) . . ?
C9 C8 N1 124.3(3) . . ?
F3 C12 C11 119.8(3) . . ?
F3 C12 C13 118.5(3) . . ?
C11 C12 C13 121.7(4) . . ?
F2 C7 C6 117.5(3) . . ?
F2 C7 C2 118.4(3) . . ?
C6 C7 C2 124.1(3) . . ?
F4 C13 C8 119.9(3) . . ?
F4 C13 C12 118.7(3) . . ?
C12 C13 C8 121.3(3) . . ?
C1 N1 C8 117.0(3) . . ?
C6 C5 C4 120.7(3) . . ?
C10 C9 C8 121.0(3) . . ?
N2 C14 C15 124.0(3) . . ?
F6 C20 C15 118.6(3) . . ?
F6 C20 C19 117.8(3) . . ?
C19 C20 C15 123.6(3) . . ?
C20 C15 C14 125.7(3) . . ?
C16 C15 C14 119.9(3) . . ?
C16 C15 C20 114.5(3) . . ?
C16 C17 C18 117.3(3) . . ?
C20 C19 C18 118.4(3) . . ?
C26 C21 N2 119.0(3) . . ?
C26 C21 C22 117.4(3) . . ?
C22 C21 N2 123.5(3) . . ?
C17 C18 C19 121.1(3) . . ?
F7 C25 C24 120.3(3) . . ?
F7 C25 C26 118.2(3) . . ?
C26 C25 C24 121.5(3) . . ?
C14 N2 C21 115.8(3) . . ?
C24 C23 C22 120.8(4) . . ?
F5 C16 C15 116.6(3) . . ?
F5 C16 C17 118.3(3) . . ?
C17 C16 C15 125.1(3) . . ?
C23 C24 C25 118.2(3) . . ?
F8 C26 C21 119.7(3) . . ?
F8 C26 C25 119.2(3) . . ?
C25 C26 C21 121.0(3) . . ?
C23 C22 C21 121.0(3) . . ?

# 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_83
_database_code_depnum_ccdc_archive 'CCDC 1008468'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2013-10-25T20:43:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.0995(3)
_cell_length_b                   9.0827(3)
_cell_length_c                   18.1054(4)
_cell_angle_alpha                90
_cell_angle_beta                 141.5290(10)
_cell_angle_gamma                90
_cell_volume                     1033.23(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    2640
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      28.3

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0389 before and 0.0301 after correction.
        The Ratio of minimum to maximum transmission is 0.9253.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.7457

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

_diffrn_source                   'fine-focus sealed tube'
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_number            5467
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             1822
_reflns_number_gt                1532
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_solution    
;
        XS, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_computing_structure_refinement  
;
        XL, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0492P)²+0.3304P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1822
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0918
_refine_ls_wR_factor_gt          0.0864
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.053

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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 0.0061 0.0033 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.48479(13) 0.54995(10) 0.35820(8) 0.0252(3) Uani 1 1 d . . .
F4 F 1.45259(13) 0.24823(10) 0.77174(7) 0.0215(2) Uani 1 1 d . . .
F2 F 1.15227(14) 0.53641(10) 0.76841(8) 0.0263(3) Uani 1 1 d . . .
F3 F 1.28557(14) -0.05934(10) 0.49894(8) 0.0265(3) Uani 1 1 d . . .
C2 C 0.8203(2) 0.53159(16) 0.56173(13) 0.0164(3) Uani 1 1 d . . .
C12 C 1.3755(2) 0.09267(17) 0.63853(13) 0.0184(4) Uani 1 1 d . . .
H12 H 1.5141 0.0511 0.7013 0.022 Uiso 1 1 calc R . .
C10 C 1.0268(2) 0.10643(17) 0.42938(13) 0.0180(4) Uani 1 1 d . . .
H10 H 0.9301 0.0738 0.3503 0.022 Uiso 1 1 calc R . .
C13 C 1.3112(2) 0.20072(16) 0.65879(13) 0.0159(3) Uani 1 1 d . . .
C4 C 0.5399(2) 0.69175(17) 0.48860(15) 0.0214(4) Uani 1 1 d . . .
H4 H 0.3997 0.73 0.4234 0.026 Uiso 1 1 calc R . .
C8 C 1.1092(2) 0.26434(16) 0.57004(13) 0.0163(3) Uani 1 1 d . . .
C7 C 0.9483(2) 0.58344(17) 0.67539(13) 0.0189(4) Uani 1 1 d . . .
N1 N 1.0678(2) 0.37429(15) 0.60566(11) 0.0231(3) Uani 1 1 d . . .
C6 C 0.8798(3) 0.68066(18) 0.69821(14) 0.0221(4) Uani 1 1 d . . .
H6 H 0.972 0.7104 0.7773 0.027 Uiso 1 1 calc R . .
C3 C 0.6159(2) 0.59214(17) 0.47132(13) 0.0180(4) Uani 1 1 d . . .
C9 C 0.9688(2) 0.21406(17) 0.45418(13) 0.0188(4) Uani 1 1 d . . .
H9 H 0.8299 0.255 0.3909 0.023 Uiso 1 1 calc R . .
C1 C 0.8818(2) 0.42134(18) 0.53356(13) 0.0203(4) Uani 1 1 d . . .
H1 H 0.7733 0.3827 0.4552 0.024 Uiso 1 1 calc R . .
C11 C 1.2286(2) 0.04778(16) 0.52244(14) 0.0182(4) Uani 1 1 d . . .
C5 C 0.6733(3) 0.73514(18) 0.60383(15) 0.0232(4) Uani 1 1 d . . .
H5 H 0.6235 0.8023 0.6184 0.028 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   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 C3 1.3597(17) . ?
F4 C13 1.3544(16) . ?
F2 C7 1.3526(17) . ?
F3 C11 1.3574(17) . ?
C2 C7 1.401(2) . ?
C2 C3 1.397(2) . ?
C2 C1 1.465(2) . ?
C12 C13 1.376(2) . ?
C12 C11 1.379(2) . ?
C10 C9 1.383(2) . ?
C10 C11 1.378(2) . ?
C13 C8 1.395(2) . ?
C4 C3 1.371(2) . ?
C4 C5 1.386(2) . ?
C8 N1 1.418(2) . ?
C8 C9 1.401(2) . ?
C7 C6 1.370(2) . ?
N1 C1 1.255(2) . ?
C6 C5 1.391(2) . ?

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
C7 C2 C1 125.88(14) . . ?
C3 C2 C7 113.99(14) . . ?
C3 C2 C1 120.11(14) . . ?
C13 C12 C11 116.62(14) . . ?
C11 C10 C9 118.24(14) . . ?
F4 C13 C12 118.04(13) . . ?
F4 C13 C8 118.01(13) . . ?
C12 C13 C8 123.95(13) . . ?
C3 C4 C5 118.21(15) . . ?
C13 C8 N1 117.01(13) . . ?
C13 C8 C9 116.28(14) . . ?
C9 C8 N1 126.71(14) . . ?
F2 C7 C2 118.52(13) . . ?
F2 C7 C6 117.67(14) . . ?
C6 C7 C2 123.81(14) . . ?
C1 N1 C8 120.06(13) . . ?
C7 C6 C5 118.98(15) . . ?
F1 C3 C2 117.17(13) . . ?
F1 C3 C4 118.09(13) . . ?
C4 C3 C2 124.73(14) . . ?
C10 C9 C8 121.83(14) . . ?
N1 C1 C2 124.61(15) . . ?
F3 C11 C12 118.37(13) . . ?
F3 C11 C10 118.55(13) . . ?
C10 C11 C12 123.07(14) . . ?
C4 C5 C6 120.23(15) . . ?

# 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_86
_database_code_depnum_ccdc_archive 'CCDC 1008469'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2013-10-24T01:08:45-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7897(10)
_cell_length_b                   6.8031(12)
_cell_length_c                   12.0624(18)
_cell_angle_alpha                84.037(10)
_cell_angle_beta                 85.232(10)
_cell_angle_gamma                72.402(10)
_cell_volume                     527.44(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    1113
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      27.59

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

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_F_000             256
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0600 before and 0.0426 after correction.
        The Ratio of minimum to maximum transmission is 0.8346.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.6226
_exptl_absorpt_correction_T_max  0.746

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

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_number            5009
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.7
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_number_total             1848
_reflns_number_gt                1361
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_refinement  
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1660P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1848
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0807
_refine_ls_wR_factor_ref         0.2452
_refine_ls_wR_factor_gt          0.2227
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.859
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.14

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'

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 0.0943(5) 0.2082(5) 0.4330(3) 0.0195(8) Uani 1 d . .
H1 H 0.1925 0.1257 0.4836 0.023 Uiso 1 calc . .
C2 C 0.1564(5) 0.2191(5) 0.3138(3) 0.0198(8) Uani 1 d . .
C3 C 0.3665(5) 0.1701(5) 0.2784(3) 0.0212(8) Uani 1 d . .
C4 C 0.4391(6) 0.1751(5) 0.1695(3) 0.0246(9) Uani 1 d . .
H4 H 0.5833 0.1434 0.1508 0.029 Uiso 1 calc . .
C5 C 0.2980(5) 0.2272(5) 0.0868(3) 0.0231(9) Uani 1 d . .
H5 H 0.3452 0.2303 0.0104 0.028 Uiso 1 calc . .
C6 C 0.0879(6) 0.2749(5) 0.1154(3) 0.0239(9) Uani 1 d . .
H6 H -0.0099 0.3099 0.0592 0.029 Uiso 1 calc . .
C7 C 0.0234(5) 0.2707(5) 0.2266(3) 0.0201(8) Uani 1 d . .
C8 C -0.1291(5) 0.2899(5) 0.5888(3) 0.0193(8) Uani 1 d . .
C9 C 0.0226(5) 0.2485(5) 0.6665(3) 0.0220(8) Uani 1 d . .
H9 H 0.1641 0.2251 0.6425 0.026 Uiso 1 calc . .
C10 C -0.0361(6) 0.2422(5) 0.7779(3) 0.0227(8) Uani 1 d . .
C11 C -0.2417(6) 0.2765(5) 0.8148(3) 0.0231(9) Uani 1 d . .
C12 C -0.3920(6) 0.3188(5) 0.7393(3) 0.0235(9) Uani 1 d . .
H12 H -0.5331 0.3414 0.7641 0.028 Uiso 1 calc . .
C13 C -0.3354(5) 0.3281(5) 0.6267(3) 0.0209(8) Uani 1 d . .
H13 H -0.4395 0.3612 0.574 0.025 Uiso 1 calc . .
N1 N -0.0857(4) 0.3045(4) 0.4718(2) 0.0211(7) Uani 1 d . .
F1 F 0.5040(3) 0.1143(3) 0.36014(17) 0.0302(6) Uani 1 d . .
F2 F -0.1820(3) 0.3164(3) 0.25195(17) 0.0303(6) Uani 1 d . .
F3 F 0.1072(3) 0.2055(3) 0.85472(18) 0.0330(7) Uani 1 d . .
F4 F -0.2910(3) 0.2697(3) 0.92551(17) 0.0292(6) 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 H1 0.95 . ?
C1 C2 1.464(5) . ?
C1 N1 1.276(5) . ?
C2 C3 1.403(5) . ?
C2 C7 1.392(5) . ?
C3 C4 1.365(5) . ?
C3 F1 1.359(4) . ?
C4 H4 0.95 . ?
C4 C5 1.385(5) . ?
C5 H5 0.95 . ?
C5 C6 1.386(5) . ?
C6 H6 0.95 . ?
C6 C7 1.376(5) . ?
C7 F2 1.350(4) . ?
C8 C9 1.396(5) . ?
C8 C13 1.391(5) . ?
C8 N1 1.417(4) . ?
C9 H9 0.95 . ?
C9 C10 1.369(5) . ?
C10 C11 1.387(5) . ?
C10 F3 1.350(4) . ?
C11 C12 1.369(5) . ?
C11 F4 1.349(4) . ?
C12 H12 0.95 . ?
C12 C13 1.381(5) . ?
C13 H13 0.95 . ?

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
C2 C1 H1 118.5 . . ?
N1 C1 H1 118.5 . . ?
N1 C1 C2 122.9(3) . . ?
C3 C2 C1 120.4(3) . . ?
C7 C2 C1 125.8(3) . . ?
C7 C2 C3 113.7(3) . . ?
C4 C3 C2 124.6(3) . . ?
F1 C3 C2 116.3(3) . . ?
F1 C3 C4 119.0(3) . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.6(3) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 120 . . ?
C4 C5 C6 120.0(3) . . ?
C6 C5 H5 120 . . ?
C5 C6 H6 120.6 . . ?
C7 C6 C5 118.9(3) . . ?
C7 C6 H6 120.6 . . ?
C6 C7 C2 124.2(3) . . ?
F2 C7 C2 118.3(3) . . ?
F2 C7 C6 117.6(3) . . ?
C9 C8 N1 123.4(3) . . ?
C13 C8 C9 119.2(3) . . ?
C13 C8 N1 117.4(3) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 C8 118.8(3) . . ?
C10 C9 H9 120.6 . . ?
C9 C10 C11 121.6(3) . . ?
F3 C10 C9 120.0(3) . . ?
F3 C10 C11 118.4(3) . . ?
C12 C11 C10 120.1(3) . . ?
F4 C11 C10 119.1(3) . . ?
F4 C11 C12 120.8(3) . . ?
C11 C12 H12 120.5 . . ?
C11 C12 C13 119.0(3) . . ?
C13 C12 H12 120.5 . . ?
C8 C13 H13 119.3 . . ?
C12 C13 C8 121.4(3) . . ?
C12 C13 H13 119.3 . . ?
C1 N1 C8 118.8(3) . . ?

# 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_87
_database_code_depnum_ccdc_archive 'CCDC 1008470'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2013-10-24T01:09:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.345(2)
_cell_length_b                   21.755(6)
_cell_length_c                   13.731(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.313(3)
_cell_angle_gamma                90
_cell_volume                     2158.6(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    100
_cell_measurement_reflns_used    2732
_cell_measurement_theta_min      3.016
_cell_measurement_theta_max      26.584

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

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_F_000             1024
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        R(int) was 0.0549 before and 0.0435 after correction.
        The Ratio of minimum to maximum transmission is 0.9307.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.6942
_exptl_absorpt_correction_T_max  0.7459

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

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'MO K\a'
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_number            12186
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.404
_diffrn_reflns_theta_max         25.022
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_number_total             3800
_reflns_number_gt                2846
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_refinement  
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        2008). A64, 112-122
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0361P)²+0.6037P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3800
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.037
_refine_ls_wR_factor_ref         0.0878
_refine_ls_wR_factor_gt          0.0788
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.047

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'

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
F3 F 0.82304(17) 0.03229(5) 0.33844(8) 0.0294(3) Uani 1 d . .
F1 F 0.42610(17) 0.27020(5) 0.46482(8) 0.0325(3) Uani 1 d . .
F2 F 0.64403(16) 0.20170(5) 0.79002(8) 0.0285(3) Uani 1 d . .
F4 F 0.73154(16) -0.08800(5) 0.60902(9) 0.0303(3) Uani 1 d . .
F7 F -0.04518(16) -0.00570(5) 0.89607(9) 0.0331(3) Uani 1 d . .
F8 F 0.58307(15) 0.00705(5) 0.87540(9) 0.0298(3) Uani 1 d . .
F5 F 0.00501(17) 0.31176(5) 0.80693(8) 0.0309(3) Uani 1 d . .
F6 F 0.03792(17) 0.20059(5) 0.51702(8) 0.0310(3) Uani 1 d . .
N1 N 0.6678(2) 0.12916(7) 0.62729(11) 0.0198(4) Uani 1 d . .
N2 N 0.1687(2) 0.15455(7) 0.70473(12) 0.0206(4) Uani 1 d . .
C11 C 0.7755(3) -0.03052(9) 0.47093(15) 0.0211(4) Uani 1 d . .
H11 H 0.7986 -0.0667 0.4364 0.025 Uiso 1 calc . .
C10 C 0.7796(3) 0.02733(9) 0.42998(14) 0.0204(4) Uani 1 d . .
C9 C 0.7449(3) 0.08067(9) 0.47730(14) 0.0200(4) Uani 1 d . .
H9 H 0.7497 0.1195 0.4461 0.024 Uiso 1 calc . .
C8 C 0.7026(2) 0.07649(9) 0.57189(14) 0.0176(4) Uani 1 d . .
C1 C 0.5745(3) 0.17289(9) 0.57946(14) 0.0190(4) Uani 1 d . .
H1 H 0.5274 0.167 0.511 0.023 Uiso 1 calc . .
C2 C 0.5364(3) 0.23159(9) 0.62452(14) 0.0187(4) Uani 1 d . .
C7 C 0.5697(3) 0.24554(9) 0.72540(14) 0.0202(4) Uani 1 d . .
C6 C 0.5317(3) 0.30160(9) 0.76348(15) 0.0246(5) Uani 1 d . .
H6 H 0.556 0.3087 0.8329 0.03 Uiso 1 calc . .
C5 C 0.4572(3) 0.34770(9) 0.69839(16) 0.0273(5) Uani 1 d . .
H5 H 0.4303 0.3867 0.7234 0.033 Uiso 1 calc . .
C3 C 0.4606(3) 0.28007(9) 0.56367(14) 0.0228(5) Uani 1 d . .
C4 C 0.4218(3) 0.33714(9) 0.59726(15) 0.0261(5) Uani 1 d . .
H4 H 0.3719 0.3686 0.5523 0.031 Uiso 1 calc . .
C13 C 0.7015(3) 0.01914(9) 0.61758(14) 0.0208(4) Uani 1 d . .
H13 H 0.6778 0.0157 0.6831 0.025 Uiso 1 calc . .
C12 C 0.7356(3) -0.03218(9) 0.56496(15) 0.0201(4) Uani 1 d . .
C18 C -0.1034(3) 0.35645(10) 0.55114(16) 0.0282(5) Uani 1 d . .
H18 H -0.1477 0.3912 0.512 0.034 Uiso 1 calc . .
C19 C -0.0617(3) 0.30287(10) 0.50529(15) 0.0262(5) Uani 1 d . .
H19 H -0.0762 0.3006 0.4352 0.031 Uiso 1 calc . .
C20 C 0.0008(3) 0.25300(9) 0.56311(15) 0.0214(5) Uani 1 d . .
C15 C 0.0246(3) 0.25311(9) 0.66597(14) 0.0188(4) Uani 1 d . .
C14 C 0.0782(3) 0.19986(9) 0.73017(14) 0.0195(4) Uani 1 d . .
H14 H 0.0438 0.1992 0.7936 0.023 Uiso 1 calc . .
C21 C 0.2003(3) 0.10410(9) 0.77089(14) 0.0186(4) Uani 1 d . .
C22 C 0.0556(3) 0.07602(9) 0.80727(14) 0.0208(4) Uani 1 d . .
H22 H -0.0665 0.0922 0.7931 0.025 Uiso 1 calc . .
C23 C 0.0955(3) 0.02396(9) 0.86456(14) 0.0225(5) Uani 1 d . .
C25 C 0.4079(3) 0.02966(9) 0.85263(14) 0.0206(5) Uani 1 d . .
C24 C 0.2703(3) -0.00038(9) 0.89026(14) 0.0224(5) Uani 1 d . .
H24 H 0.2948 -0.0356 0.9313 0.027 Uiso 1 calc . .
C26 C 0.3788(3) 0.08039(8) 0.79266(14) 0.0199(4) Uani 1 d . .
H26 H 0.4774 0.0988 0.7668 0.024 Uiso 1 calc . .
C17 C -0.0813(3) 0.36002(10) 0.65301(16) 0.0268(5) Uani 1 d . .
H17 H -0.1091 0.3968 0.6848 0.032 Uiso 1 calc . .
C16 C -0.0180(3) 0.30876(9) 0.70688(14) 0.0227(5) 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
F3 C10 1.355(2) . ?
F1 C3 1.353(2) . ?
F2 C7 1.350(2) . ?
F4 C12 1.359(2) . ?
F7 C23 1.353(2) . ?
F8 C25 1.360(2) . ?
F5 C16 1.355(2) . ?
F6 C20 1.355(2) . ?
N1 C8 1.424(2) . ?
N1 C1 1.282(2) . ?
N2 C14 1.272(2) . ?
N2 C21 1.417(2) . ?
C11 H11 0.95 . ?
C11 C10 1.381(3) . ?
C11 C12 1.375(3) . ?
C10 C9 1.376(3) . ?
C9 H9 0.95 . ?
C9 C8 1.391(3) . ?
C8 C13 1.397(3) . ?
C1 H1 0.95 . ?
C1 C2 1.467(3) . ?
C2 C7 1.396(3) . ?
C2 C3 1.398(3) . ?
C7 C6 1.375(3) . ?
C6 H6 0.95 . ?
C6 C5 1.389(3) . ?
C5 H5 0.95 . ?
C5 C4 1.385(3) . ?
C3 C4 1.372(3) . ?
C4 H4 0.95 . ?
C13 H13 0.95 . ?
C13 C12 1.377(3) . ?
C18 H18 0.95 . ?
C18 C19 1.385(3) . ?
C18 C17 1.381(3) . ?
C19 H19 0.95 . ?
C19 C20 1.374(3) . ?
C20 C15 1.392(3) . ?
C15 C14 1.466(3) . ?
C15 C16 1.394(3) . ?
C14 H14 0.95 . ?
C21 C22 1.394(3) . ?
C21 C26 1.391(3) . ?
C22 H22 0.95 . ?
C22 C23 1.380(3) . ?
C23 C24 1.375(3) . ?
C25 C24 1.379(3) . ?
C25 C26 1.371(3) . ?
C24 H24 0.95 . ?
C26 H26 0.95 . ?
C17 H17 0.95 . ?
C17 C16 1.373(3) . ?

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 N1 C8 117.01(16) . . ?
C14 N2 C21 117.23(17) . . ?
C10 C11 H11 122.3 . . ?
C12 C11 H11 122.3 . . ?
C12 C11 C10 115.49(18) . . ?
F3 C10 C11 118.43(17) . . ?
F3 C10 C9 117.72(17) . . ?
C9 C10 C11 123.84(18) . . ?
C10 C9 H9 120.8 . . ?
C10 C9 C8 118.48(18) . . ?
C8 C9 H9 120.8 . . ?
C9 C8 N1 122.53(17) . . ?
C9 C8 C13 119.85(18) . . ?
C13 C8 N1 117.56(17) . . ?
N1 C1 H1 118.2 . . ?
N1 C1 C2 123.66(18) . . ?
C2 C1 H1 118.2 . . ?
C7 C2 C1 126.49(18) . . ?
C7 C2 C3 114.15(17) . . ?
C3 C2 C1 119.35(17) . . ?
F2 C7 C2 118.49(17) . . ?
F2 C7 C6 117.55(17) . . ?
C6 C7 C2 123.96(19) . . ?
C7 C6 H6 120.7 . . ?
C7 C6 C5 118.63(19) . . ?
C5 C6 H6 120.7 . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.47(19) . . ?
C4 C5 H5 119.8 . . ?
F1 C3 C2 117.58(17) . . ?
F1 C3 C4 117.91(18) . . ?
C4 C3 C2 124.50(19) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 C5 118.3(2) . . ?
C3 C4 H4 120.9 . . ?
C8 C13 H13 120.9 . . ?
C12 C13 C8 118.18(18) . . ?
C12 C13 H13 120.9 . . ?
F4 C12 C11 117.83(17) . . ?
F4 C12 C13 118.05(17) . . ?
C11 C12 C13 124.11(18) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.82(19) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 C18 118.70(19) . . ?
C20 C19 H19 120.6 . . ?
F6 C20 C19 117.96(18) . . ?
F6 C20 C15 118.44(17) . . ?
C19 C20 C15 123.58(18) . . ?
C20 C15 C14 125.45(17) . . ?
C20 C15 C16 114.47(17) . . ?
C16 C15 C14 119.98(17) . . ?
N2 C14 C15 122.98(18) . . ?
N2 C14 H14 118.5 . . ?
C15 C14 H14 118.5 . . ?
C22 C21 N2 121.42(17) . . ?
C26 C21 N2 117.71(17) . . ?
C26 C21 C22 120.70(18) . . ?
C21 C22 H22 121.1 . . ?
C23 C22 C21 117.78(18) . . ?
C23 C22 H22 121.1 . . ?
F7 C23 C22 118.50(18) . . ?
F7 C23 C24 117.75(18) . . ?
C24 C23 C22 123.74(18) . . ?
F8 C25 C24 117.95(17) . . ?
F8 C25 C26 117.94(17) . . ?
C26 C25 C24 124.09(19) . . ?
C23 C24 C25 115.75(18) . . ?
C23 C24 H24 122.1 . . ?
C25 C24 H24 122.1 . . ?
C21 C26 H26 121.1 . . ?
C25 C26 C21 117.88(18) . . ?
C25 C26 H26 121.1 . . ?
C18 C17 H17 121.1 . . ?
C16 C17 C18 117.8(2) . . ?
C16 C17 H17 121.1 . . ?
F5 C16 C15 117.01(17) . . ?
F5 C16 C17 118.41(18) . . ?
C17 C16 C15 124.58(19) . . ?

# 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_84
_database_code_depnum_ccdc_archive 'CCDC 1008471'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_date             2014-06-06T14:32:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H7 F4 N'
_chemical_formula_sum            'C13 H7 F4 N'
_chemical_formula_weight         253.2

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.092(2)
_cell_length_b                   30.276(10)
_cell_length_c                   10.124(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.046(4)
_cell_angle_gamma                90
_cell_volume                     2146.6(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    100
_cell_measurement_reflns_used    3678
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      26.97

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

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0963 before and 0.0557 after correction.
        The Ratio of minimum to maximum transmission is 0.5910.
        The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_correction_T_min  0.4409
_exptl_absorpt_correction_T_max  0.746

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

_diffrn_source                   'fine-focus sealed tube'
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.049
_diffrn_reflns_number            13669
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         27.1
_diffrn_reflns_theta_full        27.1
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             4719
_reflns_number_gt                3430
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0554P)²+0.3098P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4719
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1149
_refine_ls_wR_factor_gt          0.103
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.057

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'

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
F3 F 0.20707(16) 0.33112(4) 0.71910(13) 0.0373(3) Uani 1 d . .
F1 F 0.36535(15) 0.54537(3) 0.51989(10) 0.0246(3) Uani 1 d . .
F2 F 0.65390(15) 0.53408(3) 0.97079(10) 0.0234(3) Uani 1 d . .
F4 F 0.90761(15) 0.40753(4) 0.77494(13) 0.0344(3) Uani 1 d . .
F7 F 0.39097(16) 0.21887(4) 0.52876(15) 0.0472(4) Uani 1 d . .
F8 F -0.33540(16) 0.28001(4) 0.41195(14) 0.0414(3) Uani 1 d . .
F6 F -0.14481(15) 0.37720(3) 0.08968(10) 0.0239(3) Uani 1 d . .
F5 F 0.14770(16) 0.44001(3) 0.49752(10) 0.0258(3) Uani 1 d . .
N1 N 0.6057(2) 0.46101(5) 0.79637(15) 0.0193(3) Uani 1 d . .
N2 N -0.0575(2) 0.32831(5) 0.32436(15) 0.0212(3) Uani 1 d . .
C10 C 0.3834(3) 0.35019(6) 0.73147(19) 0.0259(4) Uani 1 d . .
C9 C 0.3959(3) 0.39526(6) 0.75350(18) 0.0224(4) Uani 1 d . .
H9 H 0.2846 0.4122 0.7585 0.027 Uiso 1 calc . .
C8 C 0.5747(3) 0.41534(6) 0.76824(17) 0.0194(4) Uani 1 d . .
C1 C 0.4963(2) 0.48833(6) 0.72561(17) 0.0179(4) Uani 1 d . .
H1 H 0.3997 0.4771 0.6583 0.021 Uiso 1 calc . .
C2 C 0.5128(2) 0.53659(6) 0.74338(17) 0.0176(4) Uani 1 d . .
C3 C 0.4451(2) 0.56451(6) 0.63699(17) 0.0187(4) Uani 1 d . .
C4 C 0.4530(3) 0.61003(6) 0.64212(18) 0.0207(4) Uani 1 d . .
H4 H 0.4078 0.6274 0.5656 0.025 Uiso 1 calc . .
C5 C 0.5292(3) 0.62958(6) 0.76271(18) 0.0218(4) Uani 1 d . .
H5 H 0.5343 0.6609 0.7696 0.026 Uiso 1 calc . .
C11 C 0.5386(3) 0.32394(6) 0.7220(2) 0.0283(4) Uani 1 d . .
H11 H 0.5239 0.2931 0.7058 0.034 Uiso 1 calc . .
C12 C 0.7176(3) 0.34356(6) 0.7366(2) 0.0281(4) Uani 1 d . .
H12 H 0.8282 0.3265 0.7303 0.034 Uiso 1 calc . .
C13 C 0.7317(3) 0.38849(6) 0.76047(19) 0.0236(4) Uani 1 d . .
C6 C 0.5978(3) 0.60395(6) 0.87329(18) 0.0211(4) Uani 1 d . .
H6 H 0.6493 0.6174 0.9559 0.025 Uiso 1 calc . .
C7 C 0.5901(2) 0.55834(6) 0.86146(17) 0.0181(4) Uani 1 d . .
C24 C 0.0661(3) 0.21057(6) 0.5439(2) 0.0261(4) Uani 1 d . .
H24 H 0.0938 0.1841 0.5934 0.031 Uiso 1 calc . .
C25 C -0.1192(3) 0.22610(6) 0.5144(2) 0.0275(4) Uani 1 d . .
H25 H -0.2211 0.2105 0.5439 0.033 Uiso 1 calc . .
C26 C -0.1537(3) 0.26449(6) 0.4416(2) 0.0244(4) Uani 1 d . .
C21 C -0.0089(3) 0.28908(6) 0.39936(18) 0.0206(4) Uani 1 d . .
C14 C 0.0333(3) 0.36316(6) 0.36618(17) 0.0190(4) Uani 1 d . .
H14 H 0.1257 0.3614 0.4448 0.023 Uiso 1 calc . .
C15 C 0.0016(2) 0.40599(6) 0.29849(17) 0.0180(4) Uani 1 d . .
C16 C 0.0607(3) 0.44458(6) 0.36830(17) 0.0183(4) Uani 1 d . .
C17 C 0.0365(2) 0.48652(6) 0.31594(18) 0.0199(4) Uani 1 d . .
H17 H 0.0781 0.5117 0.3684 0.024 Uiso 1 calc . .
C18 C -0.0506(2) 0.49070(6) 0.18388(18) 0.0198(4) Uani 1 d . .
H18 H -0.0677 0.5193 0.145 0.024 Uiso 1 calc . .
C23 C 0.2084(3) 0.23421(6) 0.5002(2) 0.0279(4) Uani 1 d . .
C19 C -0.1133(2) 0.45382(6) 0.10742(18) 0.0192(4) Uani 1 d . .
H19 H -0.1734 0.4568 0.0171 0.023 Uiso 1 calc . .
C20 C -0.0859(2) 0.41272(6) 0.16633(17) 0.0179(4) Uani 1 d . .
C22 C 0.1770(3) 0.27338(6) 0.4291(2) 0.0264(4) Uani 1 d . .
H22 H 0.28 0.2891 0.4015 0.032 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   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
F3 C10 1.365(2) . ?
F1 C3 1.360(2) . ?
F2 C7 1.346(2) . ?
F4 C13 1.361(2) . ?
F7 C23 1.363(2) . ?
F8 C26 1.360(2) . ?
F6 C20 1.353(2) . ?
F5 C16 1.363(2) . ?
N1 C8 1.422(2) . ?
N1 C1 1.275(2) . ?
N2 C21 1.422(2) . ?
N2 C14 1.273(2) . ?
C10 C9 1.383(3) . ?
C10 C11 1.373(3) . ?
C9 H9 0.95 . ?
C9 C8 1.393(3) . ?
C8 C13 1.391(3) . ?
C1 H1 0.95 . ?
C1 C2 1.475(2) . ?
C2 C3 1.394(2) . ?
C2 C7 1.399(2) . ?
C3 C4 1.380(2) . ?
C4 H4 0.95 . ?
C4 C5 1.387(3) . ?
C5 H5 0.95 . ?
C5 C6 1.386(3) . ?
C11 H11 0.95 . ?
C11 C12 1.388(3) . ?
C12 H12 0.95 . ?
C12 C13 1.382(3) . ?
C6 H6 0.95 . ?
C6 C7 1.387(2) . ?
C24 H24 0.95 . ?
C24 C25 1.383(3) . ?
C24 C23 1.366(3) . ?
C25 H25 0.95 . ?
C25 C26 1.377(3) . ?
C26 C21 1.389(3) . ?
C21 C22 1.389(3) . ?
C14 H14 0.95 . ?
C14 C15 1.467(2) . ?
C15 C16 1.395(2) . ?
C15 C20 1.398(2) . ?
C16 C17 1.376(3) . ?
C17 H17 0.95 . ?
C17 C18 1.388(3) . ?
C18 H18 0.95 . ?
C18 C19 1.391(3) . ?
C23 C22 1.387(3) . ?
C19 H19 0.95 . ?
C19 C20 1.380(2) . ?
C22 H22 0.95 . ?

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 N1 C8 117.19(15) . . ?
C14 N2 C21 116.55(15) . . ?
F3 C10 C9 117.81(17) . . ?
F3 C10 C11 118.80(17) . . ?
C11 C10 C9 123.39(18) . . ?
C10 C9 H9 120.6 . . ?
C10 C9 C8 118.84(18) . . ?
C8 C9 H9 120.6 . . ?
C9 C8 N1 123.76(17) . . ?
C13 C8 N1 118.67(16) . . ?
C13 C8 C9 117.52(17) . . ?
N1 C1 H1 118.5 . . ?
N1 C1 C2 123.00(16) . . ?
C2 C1 H1 118.5 . . ?
C3 C2 C1 119.71(15) . . ?
C3 C2 C7 114.59(16) . . ?
C7 C2 C1 125.70(16) . . ?
F1 C3 C2 117.43(16) . . ?
F1 C3 C4 117.85(15) . . ?
C4 C3 C2 124.72(16) . . ?
C3 C4 H4 121.1 . . ?
C3 C4 C5 117.84(17) . . ?
C5 C4 H4 121.1 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.70(17) . . ?
C6 C5 H5 119.6 . . ?
C10 C11 H11 120.8 . . ?
C10 C11 C12 118.32(18) . . ?
C12 C11 H11 120.8 . . ?
C11 C12 H12 120.7 . . ?
C13 C12 C11 118.65(19) . . ?
C13 C12 H12 120.7 . . ?
F4 C13 C8 118.33(16) . . ?
F4 C13 C12 118.39(17) . . ?
C12 C13 C8 123.27(18) . . ?
C5 C6 H6 120.5 . . ?
C5 C6 C7 118.93(17) . . ?
C7 C6 H6 120.5 . . ?
F2 C7 C2 118.80(16) . . ?
F2 C7 C6 117.96(15) . . ?
C6 C7 C2 123.19(16) . . ?
C25 C24 H24 120.8 . . ?
C23 C24 H24 120.8 . . ?
C23 C24 C25 118.49(18) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 C24 119.03(18) . . ?
C26 C25 H25 120.5 . . ?
F8 C26 C25 119.48(17) . . ?
F8 C26 C21 117.88(16) . . ?
C25 C26 C21 122.62(17) . . ?
C26 C21 N2 118.88(16) . . ?
C26 C21 C22 118.17(17) . . ?
C22 C21 N2 122.92(17) . . ?
N2 C14 H14 118.5 . . ?
N2 C14 C15 123.01(16) . . ?
C15 C14 H14 118.5 . . ?
C16 C15 C14 119.45(16) . . ?
C16 C15 C20 114.54(16) . . ?
C20 C15 C14 126.01(16) . . ?
F5 C16 C15 117.11(15) . . ?
F5 C16 C17 118.27(15) . . ?
C17 C16 C15 124.62(16) . . ?
C16 C17 H17 121.1 . . ?
C16 C17 C18 117.70(16) . . ?
C18 C17 H17 121.1 . . ?
C17 C18 H18 119.4 . . ?
C17 C18 C19 121.19(16) . . ?
C19 C18 H18 119.4 . . ?
F7 C23 C24 118.57(17) . . ?
F7 C23 C22 118.14(18) . . ?
C24 C23 C22 123.29(18) . . ?
C18 C19 H19 120.9 . . ?
C20 C19 C18 118.17(16) . . ?
C20 C19 H19 120.9 . . ?
F6 C20 C15 118.90(15) . . ?
F6 C20 C19 117.32(15) . . ?
C19 C20 C15 123.77(16) . . ?
C21 C22 H22 120.8 . . ?
C23 C22 C21 118.36(18) . . ?
C23 C22 H22 120.8 . . ?

# 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
