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

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1046891'
_audit_update_record             
;
2015-02-02 deposited with the CCDC.
2015-04-08 downloaded from the CCDC.
;

_audit_creation_date             2015-02-02T15:16:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C15 H11 N5 O2'
_chemical_formula_weight         293.29

#----------------------------------------------------------------------------#
#                   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                   6.8520(10)
_cell_length_b                   9.607(5)
_cell_length_c                   10.857(7)
_cell_angle_alpha                102.68(4)
_cell_angle_beta                 93.21(3)
_cell_angle_gamma                92.50(3)
_cell_volume                     695.0(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.99

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

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'graded mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_ub_11      0.01
_diffrn_orient_matrix_ub_12      0
_diffrn_orient_matrix_ub_13      0
_diffrn_orient_matrix_ub_21      0
_diffrn_orient_matrix_ub_22      0.01
_diffrn_orient_matrix_ub_23      0
_diffrn_orient_matrix_ub_31      0
_diffrn_orient_matrix_ub_32      0
_diffrn_orient_matrix_ub_33      0.01
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.071
_diffrn_reflns_number            3200
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.982
_diffrn_reflns_theta_max         26.69
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.624
_diffrn_measured_fraction_theta_max 0.636
_diffrn_reflns_Laue_measured_fraction_full 0.624
_diffrn_reflns_Laue_measured_fraction_max 0.636
_diffrn_reflns_point_group_measured_fraction_full 0.624
_diffrn_reflns_point_group_measured_fraction_max 0.636
_reflns_number_total             1872
_reflns_number_gt                898
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

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

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   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)+(0.1825P)²+0.8926P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.02(5)
_refine_ls_number_reflns         1872
_refine_ls_number_parameters     212
_refine_ls_number_restraints     6
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.2353
_refine_ls_R_factor_gt           0.1313
_refine_ls_wR_factor_ref         0.3824
_refine_ls_wR_factor_gt          0.3112
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.083

#----------------------------------------------------------------------------#
#                   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'
O O 0.0106 0.006 '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
N1 N 0.7211(10) -0.1803(8) 0.5871(6) 0.0452(17) Uani 1 d . .
N2 N 0.8432(11) 0.3787(8) 0.5617(7) 0.0515(19) Uani 1 d . .
N3 N 0.7105(9) -0.1131(7) 0.4006(6) 0.0384(15) Uani 1 d . .
N4 N 0.7757(9) 0.1419(7) 0.4750(6) 0.0402(16) Uani 1 d . .
N5 N 0.6191(13) -0.3051(13) -0.0428(9) 0.079(3) Uani 1 d . .
C1 C 0.8145(10) 0.2422(8) 0.5784(7) 0.0352(17) Uani 1 d . .
C2 C 0.7962(10) 0.0719(9) 0.7204(7) 0.0382(18) Uani 1 d . .
C3 C 0.8221(10) 0.2143(9) 0.7045(7) 0.0386(18) Uani 1 d . .
C4 C 0.8453(14) 0.1546(12) 0.9457(8) 0.057(2) Uani 1 d . .
H4 H 0.8563 0.1355 1.0261 0.069 Uiso 1 calc . .
C5 C 0.8674(13) 0.2931(11) 0.9316(8) 0.055(2) Uani 1 d . .
H5 H 0.8894 0.3669 1.0032 0.066 Uiso 1 calc . .
C6 C 0.6902(11) -0.1339(10) 0.2706(7) 0.044(2) Uani 1 d . .
H6 H 0.7004 -0.0561 0.2329 0.053 Uiso 1 calc . .
C7 C 0.8579(12) 0.3247(10) 0.8149(8) 0.047(2) Uani 1 d . .
H7 H 0.875 0.4191 0.8078 0.056 Uiso 1 calc . .
C8 C 0.6342(13) -0.3848(11) 0.2573(9) 0.058(2) Uani 1 d . .
H8 H 0.6064 -0.4765 0.208 0.069 Uiso 1 calc . .
C9 C 0.7513(10) 0.0074(9) 0.4939(7) 0.0396(19) Uani 1 d . .
C10 C 0.6926(11) -0.2260(9) 0.4633(8) 0.045(2) Uani 1 d . .
C11 C 0.7571(11) -0.0360(8) 0.6055(7) 0.0384(18) Uani 1 d . .
C12 C 0.6546(12) -0.3629(10) 0.3879(9) 0.053(2) Uani 1 d . .
H12 H 0.6428 -0.4405 0.4258 0.063 Uiso 1 calc . .
C13 C 0.6374(14) -0.2883(13) 0.0660(10) 0.065(3) Uani 1 d . .
C14 C 0.8068(12) 0.0444(10) 0.8415(7) 0.047(2) Uani 1 d . .
H14 H 0.7879 -0.0488 0.8516 0.056 Uiso 1 calc . .
C15 C 0.6558(11) -0.2662(10) 0.1985(8) 0.048(2) Uani 1 d . .
O1W O 0.9867(13) -0.3482(7) 0.7189(7) 0.071(2) Uani 1 d . .
H1W H 1.104(5) -0.314(10) 0.744(11) 0.086 Uiso 1 d . .
H2W H 0.918(12) -0.275(7) 0.725(12) 0.086 Uiso 1 d . .
O2W O 0.3632(15) -0.2261(12) -0.2382(8) 0.106(4) Uani 1 d . .
H3W H 0.345(18) -0.311(8) -0.287(14) 0.127 Uiso 1 d . .
H4W H 0.485(8) -0.221(15) -0.209(14) 0.127 Uiso 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
N1 C10 1.320(11) . ?
N1 C11 1.366(11) . ?
N2 C1 1.370(11) . ?
N3 C9 1.367(10) . ?
N3 C6 1.379(10) . ?
N3 C10 1.405(11) . ?
N4 C1 1.315(10) . ?
N4 C9 1.357(11) . ?
N5 C13 1.155(13) . ?
C1 C3 1.450(11) . ?
C2 C14 1.396(11) . ?
C2 C3 1.420(12) . ?
C2 C11 1.440(11) . ?
C3 C7 1.417(11) . ?
C4 C14 1.374(13) . ?
C4 C5 1.375(15) . ?
C4 H4 0.93 . ?
C5 C7 1.365(13) . ?
C5 H5 0.93 . ?
C6 C15 1.341(13) . ?
C6 H6 0.93 . ?
C7 H7 0.93 . ?
C8 C12 1.385(14) . ?
C8 C15 1.430(16) . ?
C8 H8 0.93 . ?
C9 C11 1.364(11) . ?
C10 C12 1.394(12) . ?
C12 H12 0.93 . ?
C13 C15 1.405(13) . ?
C14 H14 0.93 . ?
O1W H1W 0.86(2) . ?
O1W H2W 0.85(2) . ?
O2W H3W 0.87(2) . ?
O2W H4W 0.87(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
C10 N1 C11 104.8(7) . . ?
C9 N3 C6 131.8(7) . . ?
C9 N3 C10 105.6(6) . . ?
C6 N3 C10 122.6(7) . . ?
C1 N4 C9 115.0(6) . . ?
N4 C1 N2 116.2(7) . . ?
N4 C1 C3 123.3(7) . . ?
N2 C1 C3 120.5(7) . . ?
C14 C2 C3 120.1(8) . . ?
C14 C2 C11 124.3(8) . . ?
C3 C2 C11 115.6(7) . . ?
C7 C3 C2 117.7(7) . . ?
C7 C3 C1 122.4(8) . . ?
C2 C3 C1 120.0(7) . . ?
C14 C4 C5 120.2(8) . . ?
C14 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C7 C5 C4 121.5(9) . . ?
C7 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C15 C6 N3 120.2(8) . . ?
C15 C6 H6 119.9 . . ?
N3 C6 H6 119.9 . . ?
C5 C7 C3 120.3(9) . . ?
C5 C7 H7 119.8 . . ?
C3 C7 H7 119.8 . . ?
C12 C8 C15 119.8(9) . . ?
C12 C8 H8 120.1 . . ?
C15 C8 H8 120.1 . . ?
N4 C9 C11 128.5(7) . . ?
N4 C9 N3 125.2(7) . . ?
C11 C9 N3 106.3(7) . . ?
N1 C10 C12 131.4(8) . . ?
N1 C10 N3 111.6(7) . . ?
C12 C10 N3 117.0(8) . . ?
C9 C11 N1 111.8(7) . . ?
C9 C11 C2 117.6(7) . . ?
N1 C11 C2 130.6(7) . . ?
C8 C12 C10 120.8(9) . . ?
C8 C12 H12 119.6 . . ?
C10 C12 H12 119.6 . . ?
N5 C13 C15 178.7(11) . . ?
C4 C14 C2 120.1(9) . . ?
C4 C14 H14 119.9 . . ?
C2 C14 H14 119.9 . . ?
C6 C15 C13 120.5(9) . . ?
C6 C15 C8 119.5(8) . . ?
C13 C15 C8 120.0(9) . . ?
H1W O1W H2W 105(3) . . ?
H3W O2W H4W 104(3) . . ?

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
C9 N4 C1 N2 178.9(7) . . . . ?
C9 N4 C1 C3 -2.8(10) . . . . ?
C14 C2 C3 C7 -0.2(10) . . . . ?
C11 C2 C3 C7 179.0(6) . . . . ?
C14 C2 C3 C1 178.9(7) . . . . ?
C11 C2 C3 C1 -1.9(10) . . . . ?
N4 C1 C3 C7 -177.9(7) . . . . ?
N2 C1 C3 C7 0.3(11) . . . . ?
N4 C1 C3 C2 3.1(11) . . . . ?
N2 C1 C3 C2 -178.6(7) . . . . ?
C14 C4 C5 C7 -2.0(14) . . . . ?
C9 N3 C6 C15 177.7(8) . . . . ?
C10 N3 C6 C15 -1.3(10) . . . . ?
C4 C5 C7 C3 0.8(13) . . . . ?
C2 C3 C7 C5 0.2(11) . . . . ?
C1 C3 C7 C5 -178.8(8) . . . . ?
C1 N4 C9 C11 1.8(12) . . . . ?
C1 N4 C9 N3 -179.9(6) . . . . ?
C6 N3 C9 N4 2.4(13) . . . . ?
C10 N3 C9 N4 -178.4(7) . . . . ?
C6 N3 C9 C11 -178.9(7) . . . . ?
C10 N3 C9 C11 0.2(8) . . . . ?
C11 N1 C10 C12 178.3(8) . . . . ?
C11 N1 C10 N3 0.3(8) . . . . ?
C9 N3 C10 N1 -0.3(8) . . . . ?
C6 N3 C10 N1 178.9(7) . . . . ?
C9 N3 C10 C12 -178.7(7) . . . . ?
C6 N3 C10 C12 0.6(10) . . . . ?
N4 C9 C11 N1 178.5(8) . . . . ?
N3 C9 C11 N1 -0.1(9) . . . . ?
N4 C9 C11 C2 -0.8(12) . . . . ?
N3 C9 C11 C2 -179.4(6) . . . . ?
C10 N1 C11 C9 -0.1(8) . . . . ?
C10 N1 C11 C2 179.1(8) . . . . ?
C14 C2 C11 C9 -180.0(7) . . . . ?
C3 C2 C11 C9 0.9(10) . . . . ?
C14 C2 C11 N1 0.8(13) . . . . ?
C3 C2 C11 N1 -178.3(7) . . . . ?
C15 C8 C12 C10 1.2(13) . . . . ?
N1 C10 C12 C8 -178.5(8) . . . . ?
N3 C10 C12 C8 -0.5(11) . . . . ?
C5 C4 C14 C2 2.0(13) . . . . ?
C3 C2 C14 C4 -1.0(11) . . . . ?
C11 C2 C14 C4 179.9(8) . . . . ?
N3 C6 C15 C13 -179.2(7) . . . . ?
N3 C6 C15 C8 2.0(11) . . . . ?
C12 C8 C15 C6 -1.9(13) . . . . ?
C12 C8 C15 C13 179.3(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1W O2W 0.86(2) 1.92(4) 2.759(13) 166(12) 1_656
O1W H2W N1 0.85(2) 2.32(9) 2.989(11) 136(11) .
O2W H4W N5 0.87(2) 2.30(15) 2.925(13) 129(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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1046892'
_audit_update_record             
;
2015-02-02 deposited with the CCDC.
2015-04-08 downloaded from the CCDC.
;

_audit_creation_date             2015-02-02T14:37:36-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C23 H14 F3 N4 O'
_chemical_formula_weight         419.38

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_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                   43.065(3)
_cell_length_b                   5.4072(11)
_cell_length_c                   17.347(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.73(2)
_cell_angle_gamma                90
_cell_volume                     4038(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       plate
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.38
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1720
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.997

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

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'graded mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_ub_11      0.01
_diffrn_orient_matrix_ub_12      0
_diffrn_orient_matrix_ub_13      0
_diffrn_orient_matrix_ub_21      0
_diffrn_orient_matrix_ub_22      0.01
_diffrn_orient_matrix_ub_23      0
_diffrn_orient_matrix_ub_31      0
_diffrn_orient_matrix_ub_32      0
_diffrn_orient_matrix_ub_33      0.01
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.1316
_diffrn_reflns_number            7600
_diffrn_reflns_limit_h_min       -53
_diffrn_reflns_limit_h_max       53
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.349
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        25.242
_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             4120
_reflns_number_gt                1387
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

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

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   mixed

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

_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4120
_refine_ls_number_parameters     246
_refine_ls_number_restraints     15
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.3147
_refine_ls_R_factor_gt           0.1407
_refine_ls_wR_factor_ref         0.4492
_refine_ls_wR_factor_gt          0.3764
_refine_ls_goodness_of_fit_ref   1.221
_refine_ls_restrained_S_all      1.282
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.921
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.109

#----------------------------------------------------------------------------#
#                   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'
O O 0.0106 0.006 '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
N1 N 0.12581(13) 0.3676(11) 0.0286(3) 0.0585(18) Uani 1 d . .
H1 H 0.1407 0.2808 0.0109 0.07 Uiso 1 calc . .
N2 N 0.11522(13) 0.6997(11) 0.1055(3) 0.0516(16) Uani 1 d . .
N3 N 0.10798(14) 1.0311(12) 0.1982(3) 0.0555(17) Uani 1 d . .
N4 N 0.15105(14) 0.9908(13) 0.2709(4) 0.0595(17) Uani 1 d . .
C4 C 0.16357(16) 0.4759(14) 0.1295(4) 0.0520(19) Uani 1 d . .
C6 C 0.13471(16) 0.5239(13) 0.0887(4) 0.0475(18) Uani 1 d . .
C7 C 0.12442(16) 0.8381(14) 0.1675(4) 0.0490(19) Uani 1 d . .
C8 C 0.17194(16) 0.6288(13) 0.1930(4) 0.051(2) Uani 1 d . .
C9 C 0.15043(16) 0.8136(14) 0.2125(4) 0.050(2) Uani 1 d . .
C10 C 0.09730(15) 0.3261(13) -0.0079(4) 0.0447(18) Uani 1 d . .
C11 C 0.12522(17) 1.1202(15) 0.2604(4) 0.0514(19) Uani 1 d . .
C12 C 0.04347(17) 0.4168(15) -0.0369(4) 0.061(2) Uani 1 d . .
H12 H 0.0265 0.5213 -0.0311 0.073 Uiso 1 calc . .
C13 C 0.07894(19) 1.1230(15) 0.1741(5) 0.064(2) Uani 1 d . .
H13 H 0.0677 1.0538 0.133 0.077 Uiso 1 calc . .
C14 C 0.20004(17) 0.5787(16) 0.2336(5) 0.066(2) Uani 1 d . .
H14 H 0.2052 0.6759 0.2763 0.079 Uiso 1 calc . .
C15 C 0.03977(18) 0.2059(15) -0.0822(4) 0.059(2) Uani 1 d . .
C17 C 0.09354(18) 0.1136(14) -0.0512(4) 0.059(2) Uani 1 d . .
H17 H 0.1101 0.0046 -0.0549 0.071 Uiso 1 calc . .
C18 C 0.06609(18) 0.0596(15) -0.0885(4) 0.062(2) Uani 1 d . .
H18 H 0.0649 -0.0809 -0.1194 0.075 Uiso 1 calc . .
C19 C 0.07130(17) 0.4766(14) -0.0002(4) 0.060(2) Uani 1 d . .
H19 H 0.0727 0.6185 0.03 0.072 Uiso 1 calc . .
C20 C 0.18443(18) 0.2862(15) 0.1089(5) 0.063(2) Uani 1 d . .
H20 H 0.1798 0.1844 0.067 0.075 Uiso 1 calc . .
C21 C 0.0681(2) 1.3195(16) 0.2144(5) 0.076(3) Uani 1 d . .
H21 H 0.0487 1.3858 0.2014 0.091 Uiso 1 calc . .
C22 C 0.1141(2) 1.3214(17) 0.2980(5) 0.065(2) Uani 1 d . .
H22 H 0.1258 1.3879 0.3389 0.078 Uiso 1 calc . .
C23 C 0.21227(18) 0.2527(18) 0.1526(5) 0.078(3) Uani 1 d . .
H23 H 0.2258 0.1273 0.1388 0.094 Uiso 1 calc . .
C24 C 0.21991(19) 0.3984(17) 0.2142(5) 0.077(3) Uani 1 d . .
H24 H 0.2384 0.374 0.2423 0.093 Uiso 1 calc . .
C25 C 0.0867(2) 1.4269(15) 0.2778(5) 0.071(2) Uani 1 d . .
H28 H 0.0798 1.5657 0.3038 0.086 Uiso 1 calc . .
C27 C 0.01009(9) 0.1502(9) -0.1205(3) 0.087(3) Uani 1 d . .
F1A F -0.00387(13) 0.3398(10) -0.1462(3) 0.148(2) Uani 0.5 d . .
F1B F 0.00287(14) 0.3244(11) -0.1715(3) 0.148(2) Uani 0.5 d . .
F2A F -0.01326(8) 0.1782(13) -0.0758(3) 0.148(2) Uani 0.5 d . .
F2B F -0.01069(11) 0.0667(13) -0.0694(3) 0.148(2) Uani 0.5 d . .
F3A F 0.00900(12) -0.0688(10) -0.1527(3) 0.148(2) Uani 0.5 d . .
F3B F 0.01256(10) -0.0125(12) -0.1762(3) 0.148(2) Uani 0.5 d . .
O1 O 0.17144(13) 0.9628(12) 0.4284(2) 0.111(3) Uani 1 d . .
H1A H 0.1617 0.9466 0.3759 0.133 Uiso 1 d . .
C1A C 0.18390(16) 1.2104(12) 0.4436(3) 0.141(7) Uiso 0.6 d . .
C1B C 0.20209(14) 0.8763(14) 0.4361(3) 0.28(3) Uiso 0.4 d . .
C2 C 0.21525(14) 1.1339(17) 0.4306(3) 0.283(11) Uiso 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
N1 C10 1.383(8) . ?
N1 C6 1.387(8) . ?
N1 H1 0.86 . ?
N2 C6 1.307(8) . ?
N2 C7 1.359(8) . ?
N3 C7 1.377(9) . ?
N3 C11 1.378(8) . ?
N3 C13 1.398(9) . ?
N4 C11 1.322(9) . ?
N4 C9 1.394(9) . ?
C4 C8 1.415(10) . ?
C4 C20 1.416(10) . ?
C4 C6 1.435(10) . ?
C7 C9 1.352(9) . ?
C8 C14 1.408(10) . ?
C8 C9 1.411(10) . ?
C10 C17 1.379(9) . ?
C10 C19 1.394(9) . ?
C11 C22 1.363(10) . ?
C12 C19 1.379(10) . ?
C12 C15 1.392(10) . ?
C12 H12 0.93 . ?
C13 C21 1.362(11) . ?
C13 H13 0.93 . ?
C14 C24 1.347(10) . ?
C14 H14 0.93 . ?
C15 C18 1.389(10) . ?
C15 C27 1.454(8) . ?
C17 C18 1.362(10) . ?
C17 H17 0.93 . ?
C18 H18 0.93 . ?
C19 H19 0.93 . ?
C20 C23 1.410(10) . ?
C20 H20 0.93 . ?
C21 C25 1.463(11) . ?
C21 H21 0.93 . ?
C22 C25 1.347(11) . ?
C22 H22 0.93 . ?
C23 C24 1.361(11) . ?
C23 H23 0.93 . ?
C24 H24 0.93 . ?
C25 H28 0.93 . ?
C27 F1A 1.2629 . ?
C27 F2A 1.2974 . ?
C27 F3A 1.3094 . ?
C27 F3B 1.3133 . ?
C27 F1B 1.3231 . ?
C27 F2B 1.3558 . ?
F1A F1B 0.5409 . ?
F1A F2A 1.5645 . ?
F2A F2B 0.6225 . ?
F3A F3B 0.535 . ?
O1 C1B 1.4027 . ?
O1 C1A 1.4633 . ?
O1 H1A 0.9957 . ?
C1A C2 1.4361 . ?
C1A C1B 1.9745 . ?
C1B C2 1.5077 . ?

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
C10 N1 C6 131.7(6) . . ?
C10 N1 H1 114.2 . . ?
C6 N1 H1 114.2 . . ?
C6 N2 C7 113.8(6) . . ?
C7 N3 C11 107.2(6) . . ?
C7 N3 C13 128.3(6) . . ?
C11 N3 C13 124.4(7) . . ?
C11 N4 C9 105.4(6) . . ?
C8 C4 C20 118.1(7) . . ?
C8 C4 C6 118.3(7) . . ?
C20 C4 C6 123.6(7) . . ?
N2 C6 N1 116.5(6) . . ?
N2 C6 C4 125.0(7) . . ?
N1 C6 C4 118.4(7) . . ?
C9 C7 N2 128.3(7) . . ?
C9 C7 N3 106.1(7) . . ?
N2 C7 N3 125.6(6) . . ?
C14 C8 C9 125.2(7) . . ?
C14 C8 C4 118.2(7) . . ?
C9 C8 C4 116.6(6) . . ?
C7 C9 N4 110.5(7) . . ?
C7 C9 C8 118.0(7) . . ?
N4 C9 C8 131.5(6) . . ?
C17 C10 N1 118.2(6) . . ?
C17 C10 C19 117.2(6) . . ?
N1 C10 C19 124.4(6) . . ?
N4 C11 C22 131.5(7) . . ?
N4 C11 N3 110.7(7) . . ?
C22 C11 N3 117.7(7) . . ?
C19 C12 C15 122.4(7) . . ?
C19 C12 H12 118.8 . . ?
C15 C12 H12 118.8 . . ?
C21 C13 N3 116.3(8) . . ?
C21 C13 H13 121.9 . . ?
N3 C13 H13 121.9 . . ?
C24 C14 C8 123.9(8) . . ?
C24 C14 H14 118.1 . . ?
C8 C14 H14 118.1 . . ?
C18 C15 C12 115.6(7) . . ?
C18 C15 C27 123.7(7) . . ?
C12 C15 C27 120.8(6) . . ?
C18 C17 C10 121.6(7) . . ?
C18 C17 H17 119.2 . . ?
C10 C17 H17 119.2 . . ?
C17 C18 C15 122.6(7) . . ?
C17 C18 H18 118.7 . . ?
C15 C18 H18 118.7 . . ?
C12 C19 C10 120.5(7) . . ?
C12 C19 H19 119.7 . . ?
C10 C19 H19 119.7 . . ?
C23 C20 C4 119.6(8) . . ?
C23 C20 H20 120.2 . . ?
C4 C20 H20 120.2 . . ?
C13 C21 C25 120.4(8) . . ?
C13 C21 H21 119.8 . . ?
C25 C21 H21 119.8 . . ?
C25 C22 C11 122.1(8) . . ?
C25 C22 H22 119 . . ?
C11 C22 H22 119 . . ?
C24 C23 C20 121.9(8) . . ?
C24 C23 H23 119 . . ?
C20 C23 H23 119 . . ?
C14 C24 C23 118.4(8) . . ?
C14 C24 H24 120.8 . . ?
C23 C24 H24 120.8 . . ?
C22 C25 C21 118.9(8) . . ?
C22 C25 H28 120.5 . . ?
C21 C25 H28 120.5 . . ?
F1A C27 F2A 75.3 . . ?
F1A C27 F3A 125 . . ?
F2A C27 F3A 110 . . ?
F1A C27 F3B 109.4 . . ?
F2A C27 F3B 126.8 . . ?
F3A C27 F3B 23.5 . . ?
F1A C27 F1B 24 . . ?
F2A C27 F1B 98.4 . . ?
F3A C27 F1B 110.7 . . ?
F3B C27 F1B 90.4 . . ?
F1A C27 F2B 100.6 . . ?
F2A C27 F2B 27 . . ?
F3A C27 F2B 87.8 . . ?
F3B C27 F2B 109.1 . . ?
F1B C27 F2B 121.9 . . ?
F1A C27 C15 113.3(4) . . ?
F2A C27 C15 112.9(4) . . ?
F3A C27 C15 113.7(4) . . ?
F3B C27 C15 112.7(4) . . ?
F1B C27 C15 110.1(4) . . ?
F2B C27 C15 111.0(4) . . ?
F1B F1A C27 84.2 . . ?
F1B F1A F2A 134.9 . . ?
C27 F1A F2A 53.3 . . ?
F1A F1B C27 71.8 . . ?
F2B F2A C27 81.7 . . ?
F2B F2A F1A 129.1 . . ?
C27 F2A F1A 51.3 . . ?
F2A F2B C27 71.3 . . ?
F3B F3A C27 78.6 . . ?
F3A F3B C27 77.8 . . ?
C1B O1 C1A 87.1 . . ?
C1B O1 H1A 115.4 . . ?
C1A O1 H1A 112.8 . . ?
C2 C1A O1 92.9 . . ?
C2 C1A C1B 49.4 . . ?
O1 C1A C1B 45.2 . . ?
O1 C1B C2 92.3 . . ?
O1 C1B C1A 47.7 . . ?
C2 C1B C1A 46.4 . . ?
C1A C2 C1B 84.2 . . ?

# 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
