# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_cb77ft
_database_code_depnum_ccdc_archive 'CCDC 1973164'
loop_
_audit_author_name
_audit_author_address
'Charlene Tsay'
;University of California, Riverside
United States of America
;
_audit_update_record             
;
2019-12-19 deposited with the CCDC.	2020-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H7 F N2'
_chemical_formula_weight         198.20

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2669(4)
_cell_length_b                   8.0255(5)
_cell_length_c                   9.8682(6)
_cell_angle_alpha                96.746(3)
_cell_angle_beta                 98.691(3)
_cell_angle_gamma                90.723(3)
_cell_volume                     486.99(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4611
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      32.20

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             204
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6515
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   'Bruker SADABS 2012/1'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15064
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.103
_diffrn_reflns_theta_max         30.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3100
_reflns_number_gt                2415
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2 2014.1-1, 2014'
_computing_cell_refinement       'Bruker SAINT 8.34a, 2013'
_computing_data_reduction        'Bruker SAINT 8.34a, 2013'
_computing_structure_solution    'Bruker SHELXTL 2018/2 (XT)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0649P)²+0.1128P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3100
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1240
_refine_ls_wR_factor_gt          0.1115
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.25183(17) -0.15551(14) -0.03589(10) 0.0269(2) Uani 1 1 d . . . . .
C1 C 0.24843(17) -0.09361(14) 0.07498(11) 0.0197(2) Uani 1 1 d . . . . .
N2 N -0.08761(16) -0.06743(13) 0.32839(10) 0.0255(2) Uani 1 1 d . . . . .
C2 C 0.05918(17) -0.04345(13) 0.27557(11) 0.0187(2) Uani 1 1 d . . . . .
C3 C 0.24776(16) -0.01477(13) 0.21337(10) 0.0170(2) Uani 1 1 d . . . . .
C4 C 0.41992(17) 0.08118(13) 0.28112(10) 0.0175(2) Uani 1 1 d . . . . .
H4 H 0.540658 0.090782 0.234467 0.021 Uiso 1 1 calc R U . . .
C5 C 0.43395(17) 0.16912(13) 0.41744(10) 0.0169(2) Uani 1 1 d . . . . .
H5 H 0.317467 0.161434 0.468051 0.020 Uiso 1 1 calc R U . . .
C6 C 0.61298(16) 0.26301(13) 0.47398(11) 0.0174(2) Uani 1 1 d . . . . .
H6 H 0.727575 0.261191 0.420900 0.021 Uiso 1 1 calc R U . . .
C7 C 0.64949(16) 0.36648(13) 0.60713(10) 0.0160(2) Uani 1 1 d . . . . .
C8 C 0.49027(17) 0.38935(14) 0.69337(11) 0.0182(2) Uani 1 1 d . . . . .
H8 H 0.353688 0.332826 0.666252 0.022 Uiso 1 1 calc R U . . .
C9 C 0.53022(17) 0.49316(14) 0.81719(11) 0.0201(2) Uani 1 1 d . . . . .
H9 H 0.421937 0.509386 0.874836 0.024 Uiso 1 1 calc R U . . .
C10 C 0.73114(18) 0.57300(14) 0.85549(11) 0.0205(2) Uani 1 1 d . . . . .
F1 F 0.76987(12) 0.67500(10) 0.97667(7) 0.02996(19) Uani 1 1 d . . . . .
C11 C 0.89418(17) 0.55322(14) 0.77517(12) 0.0220(2) Uani 1 1 d . . . . .
H11 H 1.031077 0.608735 0.804112 0.026 Uiso 1 1 calc R U . . .
C12 C 0.85062(16) 0.44961(14) 0.65112(11) 0.0199(2) Uani 1 1 d . . . . .
H12 H 0.960041 0.434418 0.594239 0.024 Uiso 1 1 calc R U . . .


_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 C1 1.1505(14) . ?
C1 C3 1.4368(14) . ?
N2 C2 1.1485(14) . ?
C2 C3 1.4394(14) . ?
C3 C4 1.3579(15) . ?
C4 C5 1.4336(14) . ?
C4 H4 0.9500 . ?
C5 C6 1.3523(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.4547(14) . ?
C6 H6 0.9500 . ?
C7 C12 1.4027(14) . ?
C7 C8 1.4065(14) . ?
C8 C9 1.3831(15) . ?
C8 H8 0.9500 . ?
C9 C10 1.3849(15) . ?
C9 H9 0.9500 . ?
C10 F1 1.3551(12) . ?
C10 C11 1.3844(15) . ?
C11 C12 1.3852(15) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

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 C3 178.98(11) . . ?
N2 C2 C3 178.10(12) . . ?
C4 C3 C1 120.55(9) . . ?
C4 C3 C2 122.34(9) . . ?
C1 C3 C2 117.11(9) . . ?
C3 C4 C5 125.19(9) . . ?
C3 C4 H4 117.4 . . ?
C5 C4 H4 117.4 . . ?
C6 C5 C4 120.01(9) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 127.18(9) . . ?
C5 C6 H6 116.4 . . ?
C7 C6 H6 116.4 . . ?
C12 C7 C8 118.22(9) . . ?
C12 C7 C6 118.93(9) . . ?
C8 C7 C6 122.84(9) . . ?
C9 C8 C7 120.77(9) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 118.70(9) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
F1 C10 C11 118.56(10) . . ?
F1 C10 C9 118.64(9) . . ?
C11 C10 C9 122.80(10) . . ?
C10 C11 C12 117.64(10) . . ?
C10 C11 H11 121.2 . . ?
C12 C11 H11 121.2 . . ?
C11 C12 C7 121.85(9) . . ?
C11 C12 H12 119.1 . . ?
C7 C12 H12 119.1 . . ?

_refine_diff_density_max         0.448
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_cb79ft
_database_code_depnum_ccdc_archive 'CCDC 1973165'
loop_
_audit_author_name
_audit_author_address
'Charlene Tsay'
;University of California, Riverside
United States of America
;
_audit_update_record             
;
2019-12-19 deposited with the CCDC.	2020-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H14 F2 N4'
_chemical_formula_weight         396.39

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.4702(2)
_cell_length_b                   13.0779(4)
_cell_length_c                   10.3353(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.4927(17)
_cell_angle_gamma                90
_cell_volume                     1003.23(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5060
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      31.46

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.037
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7057
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   'SADABS 2016/2 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19369
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.522
_diffrn_reflns_theta_max         30.505
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3067
_reflns_number_gt                2415
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX3 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT 8.38a (Bruker, 2017)'
_computing_data_reduction        'SAINT 8.38a (Bruker, 2017)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 The para-fluorophenyl group exhibited disorder that was modeled
 over two positions; the disorder ratio was refined freely and
 converged at 84:16. This disorder was refined with the help of
 similarity restraints on 1,2- and 1,3- distances; similarity and
 rigid-bond restraints on anisotropic displacement parameters;
 and flatness restraints on the aromatic rings. The anisotropic
 displacement parameters of the ipso- and ortho- carbons were
 constrained to be equivalent. The slightly smaller-than-typical
 average aromatic C-C distance (1.37 vs 1.395 expected) is likely
 due to the combination of the positional disorder and higher
 thermal motion.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0575P)²+0.2209P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3067
_refine_ls_number_parameters     182
_refine_ls_number_restraints     317
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1097
_refine_ls_wR_factor_gt          0.1009
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      0.996
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.18659(13) 0.29698(8) 0.17163(9) 0.0194(2) Uani 1 1 d . . . . .
N1 N 0.16296(13) 0.25029(8) 0.07767(9) 0.0287(2) Uani 1 1 d . . . . .
C2 C 0.04464(13) 0.39680(8) 0.32980(9) 0.0206(2) Uani 1 1 d . . . . .
N2 N -0.08586(13) 0.42879(9) 0.36108(10) 0.0319(2) Uani 1 1 d . . . . .
C3 C 0.20870(12) 0.35733(7) 0.28874(9) 0.01626(18) Uani 1 1 d . . . . .
C4 C 0.37047(13) 0.37754(7) 0.35428(9) 0.01634(18) Uani 1 1 d . . . . .
H4 H 0.474794 0.348369 0.324420 0.020 Uiso 1 1 calc R U . . .
C5 C 0.39223(12) 0.44364(7) 0.47140(9) 0.01559(18) Uani 1 1 d D . . . .
H5 H 0.290698 0.433711 0.525459 0.019 Uiso 1 1 calc R U . . .
C6 C 0.57699(12) 0.43836(7) 0.55631(9) 0.01640(18) Uani 1 1 d D U . . .
H6 H 0.663114 0.395883 0.511902 0.020 Uiso 0.839(14) 1 calc R U P A 1
H6A H 0.661080 0.398202 0.507217 0.020 Uiso 0.161(14) 1 calc R U P A 2
C7 C 0.5810(4) 0.40612(15) 0.6967(2) 0.0174(4) Uani 0.839(14) 1 d D U P A 1
C8 C 0.4387(5) 0.4242(3) 0.7706(2) 0.0202(4) Uani 0.839(14) 1 d D U P A 1
H8 H 0.330666 0.454053 0.730174 0.024 Uiso 0.839(14) 1 calc R U P A 1
C9 C 0.4522(5) 0.3993(3) 0.9021(2) 0.0237(5) Uani 0.839(14) 1 d D U P A 1
H9 H 0.354523 0.411291 0.951515 0.028 Uiso 0.839(14) 1 calc R U P A 1
C10 C 0.6105(6) 0.3569(2) 0.9591(2) 0.0258(6) Uani 0.839(14) 1 d D U P A 1
F1 F 0.6250(5) 0.33287(17) 1.08780(19) 0.0418(6) Uani 0.839(14) 1 d D U P A 1
C11 C 0.7544(5) 0.3373(3) 0.8917(3) 0.0293(6) Uani 0.839(14) 1 d D U P A 1
H11 H 0.861655 0.307385 0.933457 0.035 Uiso 0.839(14) 1 calc R U P A 1
C12 C 0.7385(5) 0.3627(2) 0.7595(3) 0.0239(5) Uani 0.839(14) 1 d D U P A 1
H12 H 0.837104 0.350163 0.711173 0.029 Uiso 0.839(14) 1 calc R U P A 1
C7A C 0.607(2) 0.4063(7) 0.6949(12) 0.0174(4) Uani 0.161(14) 1 d D U P A 2
C8A C 0.470(2) 0.4130(14) 0.7682(14) 0.0202(4) Uani 0.161(14) 1 d D U P A 2
H8A H 0.354828 0.437028 0.731681 0.024 Uiso 0.161(14) 1 calc R U P A 2
C9A C 0.499(3) 0.3835(14) 0.9016(13) 0.028(2) Uani 0.161(14) 1 d D U P A 2
H9A H 0.407218 0.386911 0.957614 0.033 Uiso 0.161(14) 1 calc R U P A 2
C10A C 0.667(3) 0.3503(12) 0.9432(14) 0.029(2) Uani 0.161(14) 1 d D U P A 2
F1A F 0.696(4) 0.3284(12) 1.0734(12) 0.062(4) Uani 0.161(14) 1 d D U P A 2
C11A C 0.801(3) 0.3433(17) 0.8688(17) 0.034(3) Uani 0.161(14) 1 d D U P A 2
H11A H 0.916187 0.321170 0.905979 0.041 Uiso 0.161(14) 1 calc R U P A 2
C12A C 0.774(2) 0.3673(13) 0.7406(15) 0.0239(5) Uani 0.161(14) 1 d D . P A 2
H12A H 0.865357 0.357722 0.684999 0.029 Uiso 0.161(14) 1 calc R U P A 2


_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 N1 1.1438(13) . ?
C1 C3 1.4387(13) . ?
C2 N2 1.1407(14) . ?
C2 C3 1.4374(14) . ?
C3 C4 1.3431(13) . ?
C4 C5 1.4814(12) . ?
C4 H4 0.9500 . ?
C5 C6 1.5511(12) . ?
C5 C6 1.5910(13) 3_666 ?
C5 H5 1.0000 . ?
C6 C7A 1.484(13) . ?
C6 C7 1.508(3) . ?
C6 H6 1.0000 . ?
C6 H6A 1.0000 . ?
C7 C8 1.397(3) . ?
C7 C12 1.398(2) . ?
C8 C9 1.390(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.377(2) . ?
C9 H9 0.9500 . ?
C10 F1 1.359(2) . ?
C10 C11 1.370(3) . ?
C11 C12 1.398(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C7A C8A 1.346(14) . ?
C7A C12A 1.380(14) . ?
C8A C9A 1.425(14) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.350(12) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.328(12) . ?
C10A F1A 1.369(12) . ?
C11A C12A 1.354(14) . ?
C11A H11A 0.9500 . ?
C12A H12A 0.9500 . ?

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 C3 177.59(10) . . ?
N2 C2 C3 179.20(12) . . ?
C4 C3 C2 121.94(8) . . ?
C4 C3 C1 122.91(9) . . ?
C2 C3 C1 115.13(8) . . ?
C3 C4 C5 122.43(8) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
C4 C5 C6 116.41(8) . . ?
C4 C5 C6 115.06(8) . 3_666 ?
C6 C5 C6 90.43(7) . 3_666 ?
C4 C5 H5 111.1 . . ?
C6 C5 H5 111.1 . . ?
C6 C5 H5 111.1 3_666 . ?
C7A C6 C5 125.9(6) . . ?
C7 C6 C5 118.45(14) . . ?
C7 C6 C5 117.18(10) . 3_666 ?
C5 C6 C5 89.57(7) . 3_666 ?
C7 C6 H6 110.0 . . ?
C5 C6 H6 110.0 . . ?
C5 C6 H6 110.0 3_666 . ?
C7A C6 H6A 107.8 . . ?
C5 C6 H6A 107.8 . . ?
C5 C6 H6A 107.8 3_666 . ?
C8 C7 C12 117.9(2) . . ?
C8 C7 C6 123.0(2) . . ?
C12 C7 C6 118.96(19) . . ?
C9 C8 C7 121.27(18) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C10 C9 C8 118.5(2) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
F1 C10 C11 118.3(2) . . ?
F1 C10 C9 118.8(2) . . ?
C11 C10 C9 122.90(19) . . ?
C10 C11 C12 117.9(2) . . ?
C10 C11 H11 121.1 . . ?
C12 C11 H11 121.1 . . ?
C11 C12 C7 121.6(2) . . ?
C11 C12 H12 119.2 . . ?
C7 C12 H12 119.2 . . ?
C8A C7A C12A 123.2(12) . . ?
C8A C7A C6 118.9(12) . . ?
C12A C7A C6 117.9(12) . . ?
C7A C8A C9A 118.8(12) . . ?
C7A C8A H8A 120.6 . . ?
C9A C8A H8A 120.6 . . ?
C10A C9A C8A 115.7(11) . . ?
C10A C9A H9A 122.1 . . ?
C8A C9A H9A 122.1 . . ?
C11A C10A C9A 124.6(12) . . ?
C11A C10A F1A 120.5(11) . . ?
C9A C10A F1A 114.8(11) . . ?
C10A C11A C12A 120.9(13) . . ?
C10A C11A H11A 119.6 . . ?
C12A C11A H11A 119.6 . . ?
C11A C12A C7A 116.7(12) . . ?
C11A C12A H12A 121.7 . . ?
C7A C12A H12A 121.7 . . ?

_refine_diff_density_max         0.391
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.043

