# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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 2053442'
loop_
_audit_author_name
_audit_author_address
'Anjaneyulu Putta'
;University of South Dakota
United States of America
;
_audit_update_record             
;
2021-01-01 deposited with the CCDC.	2022-02-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        10,13-DiBromo-dibenzo[a,c]phenazine
_chemical_name_common            10,13-DiBromo-dibenzo[a,c]phenazine
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H10 Br2 N2'
_chemical_formula_sum            'C20 H10 Br2 N2'
_chemical_formula_weight         438.12

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   4.2682(2)
_cell_length_b                   18.1897(10)
_cell_length_c                   19.6942(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1529.00(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5852
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      31.32

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.903
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   0.12
_exptl_transmission_factor_max   0.62
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    5.304
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26358
_diffrn_reflns_av_unetI/netI     0.0982
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.068
_diffrn_reflns_theta_max         37.808
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8214
_reflns_number_gt                5153
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.995

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.0292P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1647 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8214
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.0847
_refine_ls_wR_factor_gt          0.0693
_refine_ls_goodness_of_fit_ref   0.924
_refine_ls_restrained_S_all      0.924
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.003

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
Br1 Br -0.38400(10) 0.79330(2) 0.37694(2) 0.01883(8) Uani 1 1 d . . . . .
Br2 Br 0.11337(10) 0.46193(2) 0.45559(2) 0.02058(8) Uani 1 1 d . . . . .
N1 N 0.2739(7) 0.55219(16) 0.32939(15) 0.0139(6) Uani 1 1 d . . . . .
N2 N 0.0628(7) 0.69442(15) 0.29491(15) 0.0153(6) Uani 1 1 d . . . . .
C1 C -0.2194(9) 0.5947(2) 0.47545(19) 0.0195(8) Uani 1 1 d . . . . .
H1 H -0.283377 0.572758 0.516995 0.023 Uiso 1 1 calc R U . . .
C2 C -0.0267(8) 0.55755(19) 0.43296(19) 0.0155(7) Uani 1 1 d . . . . .
C3 C 0.0775(8) 0.58919(17) 0.37039(17) 0.0149(6) Uani 1 1 d . . . . .
C4 C 0.3653(9) 0.58542(17) 0.27257(16) 0.0133(6) Uani 1 1 d . . . . .
C5 C 0.5779(8) 0.54628(18) 0.22730(17) 0.0145(6) Uani 1 1 d . . . . .
C6 C 0.6817(8) 0.58065(18) 0.16712(17) 0.0145(7) Uani 1 1 d . . . . .
C7 C 0.5754(8) 0.65528(18) 0.14935(17) 0.0149(7) Uani 1 1 d . . . . .
C8 C 0.6753(9) 0.6914(2) 0.09026(18) 0.0183(7) Uani 1 1 d . . . . .
H10 H 0.808101 0.666381 0.059200 0.022 Uiso 1 1 calc R U . . .
C9 C 0.5840(10) 0.76259(19) 0.07648(18) 0.0192(7) Uani 1 1 d . . . . .
H2 H 0.654490 0.785902 0.036109 0.023 Uiso 1 1 calc R U . . .
C10 C -0.3262(9) 0.6661(2) 0.45820(19) 0.0192(7) Uani 1 1 d . . . . .
H3 H -0.461354 0.691742 0.488301 0.023 Uiso 1 1 calc R U . . .
C11 C -0.2362(8) 0.69819(19) 0.39870(19) 0.0161(7) Uani 1 1 d . . . . .
C12 C -0.0320(8) 0.66128(19) 0.35319(18) 0.0154(7) Uani 1 1 d . . . . .
C13 C 0.8905(9) 0.54149(18) 0.12514(17) 0.0172(6) Uani 1 1 d . . . . .
H7 H 0.963789 0.563393 0.084324 0.021 Uiso 1 1 calc R U . . .
C14 C 0.9902(8) 0.4717(2) 0.14246(18) 0.0179(7) Uani 1 1 d . . . . .
H4 H 1.133586 0.446526 0.113821 0.021 Uiso 1 1 calc R U . . .
C15 C 0.8828(10) 0.43801(18) 0.20140(17) 0.0184(6) Uani 1 1 d . . . . .
H5 H 0.949283 0.389669 0.212614 0.022 Uiso 1 1 calc R U . . .
C16 C 0.6798(9) 0.47515(19) 0.24331(18) 0.0172(7) Uani 1 1 d . . . . .
H6 H 0.607389 0.452244 0.283725 0.021 Uiso 1 1 calc R U . . .
C17 C 0.3906(11) 0.80053(18) 0.12091(17) 0.0199(6) Uani 1 1 d . . . . .
H8 H 0.332531 0.849932 0.111590 0.024 Uiso 1 1 calc R U . . .
C18 C 0.2830(9) 0.7659(2) 0.1788(2) 0.0196(7) Uani 1 1 d . . . . .
H9 H 0.145796 0.791295 0.208670 0.023 Uiso 1 1 calc R U . . .
C19 C 0.3740(9) 0.69384(17) 0.19389(16) 0.0149(6) Uani 1 1 d . . . . .
C20 C 0.2609(8) 0.65798(19) 0.25594(18) 0.0145(7) Uani 1 1 d . . . . .


_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
Br1 C11 1.890(4) . ?
Br2 C2 1.893(3) . ?
N1 C4 1.330(4) . ?
N1 C3 1.345(4) . ?
N2 C20 1.320(5) . ?
N2 C12 1.358(5) . ?
C1 C2 1.353(5) . ?
C1 C10 1.418(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.431(5) . ?
C3 C12 1.433(5) . ?
C4 C20 1.431(5) . ?
C4 C5 1.458(5) . ?
C5 C16 1.401(5) . ?
C5 C6 1.411(5) . ?
C6 C13 1.409(5) . ?
C6 C7 1.474(5) . ?
C7 C8 1.403(5) . ?
C7 C19 1.414(5) . ?
C8 C9 1.379(5) . ?
C8 H10 0.9500 . ?
C9 C17 1.387(5) . ?
C9 H2 0.9500 . ?
C10 C11 1.365(5) . ?
C10 H3 0.9500 . ?
C11 C12 1.419(5) . ?
C13 C14 1.381(5) . ?
C13 H7 0.9500 . ?
C14 C15 1.391(5) . ?
C14 H4 0.9500 . ?
C15 C16 1.374(5) . ?
C15 H5 0.9500 . ?
C16 H6 0.9500 . ?
C17 C18 1.381(5) . ?
C17 H8 0.9500 . ?
C18 C19 1.399(5) . ?
C18 H9 0.9500 . ?
C19 C20 1.467(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
C4 N1 C3 117.4(3) . . ?
C20 N2 C12 117.3(3) . . ?
C2 C1 C10 120.3(4) . . ?
C2 C1 H1 119.9 . . ?
C10 C1 H1 119.9 . . ?
C1 C2 C3 121.4(3) . . ?
C1 C2 Br2 120.3(3) . . ?
C3 C2 Br2 118.3(3) . . ?
N1 C3 C12 121.3(3) . . ?
N1 C3 C2 120.6(3) . . ?
C12 C3 C2 118.1(3) . . ?
N1 C4 C20 121.4(3) . . ?
N1 C4 C5 118.4(3) . . ?
C20 C4 C5 120.3(3) . . ?
C16 C5 C6 120.0(3) . . ?
C16 C5 C4 120.4(3) . . ?
C6 C5 C4 119.5(3) . . ?
C5 C6 C13 117.9(3) . . ?
C5 C6 C7 120.7(3) . . ?
C13 C6 C7 121.4(3) . . ?
C8 C7 C19 117.8(3) . . ?
C8 C7 C6 122.3(3) . . ?
C19 C7 C6 119.8(3) . . ?
C9 C8 C7 121.1(3) . . ?
C9 C8 H10 119.4 . . ?
C7 C8 H10 119.4 . . ?
C8 C9 C17 120.7(3) . . ?
C8 C9 H2 119.6 . . ?
C17 C9 H2 119.6 . . ?
C11 C10 C1 120.5(3) . . ?
C11 C10 H3 119.7 . . ?
C1 C10 H3 119.7 . . ?
C10 C11 C12 120.8(3) . . ?
C10 C11 Br1 119.5(3) . . ?
C12 C11 Br1 119.6(3) . . ?
N2 C12 C11 120.5(3) . . ?
N2 C12 C3 120.6(3) . . ?
C11 C12 C3 118.9(3) . . ?
C14 C13 C6 121.0(3) . . ?
C14 C13 H7 119.5 . . ?
C6 C13 H7 119.5 . . ?
C13 C14 C15 120.6(3) . . ?
C13 C14 H4 119.7 . . ?
C15 C14 H4 119.7 . . ?
C16 C15 C14 119.5(3) . . ?
C16 C15 H5 120.2 . . ?
C14 C15 H5 120.2 . . ?
C15 C16 C5 121.0(3) . . ?
C15 C16 H6 119.5 . . ?
C5 C16 H6 119.5 . . ?
C18 C17 C9 119.5(3) . . ?
C18 C17 H8 120.3 . . ?
C9 C17 H8 120.3 . . ?
C17 C18 C19 120.7(4) . . ?
C17 C18 H9 119.7 . . ?
C19 C18 H9 119.7 . . ?
C18 C19 C7 120.1(3) . . ?
C18 C19 C20 120.2(3) . . ?
C7 C19 C20 119.8(3) . . ?
N2 C20 C4 122.0(3) . . ?
N2 C20 C19 118.2(3) . . ?
C4 C20 C19 119.9(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
C10 C1 C2 C3 0.8(6) . . . . ?
C10 C1 C2 Br2 -179.5(3) . . . . ?
C4 N1 C3 C12 0.7(5) . . . . ?
C4 N1 C3 C2 -178.9(3) . . . . ?
C1 C2 C3 N1 178.6(3) . . . . ?
Br2 C2 C3 N1 -1.1(4) . . . . ?
C1 C2 C3 C12 -1.0(5) . . . . ?
Br2 C2 C3 C12 179.3(2) . . . . ?
C3 N1 C4 C20 0.5(5) . . . . ?
C3 N1 C4 C5 -179.9(3) . . . . ?
N1 C4 C5 C16 0.6(5) . . . . ?
C20 C4 C5 C16 -179.8(3) . . . . ?
N1 C4 C5 C6 -179.2(3) . . . . ?
C20 C4 C5 C6 0.4(5) . . . . ?
C16 C5 C6 C13 -0.7(5) . . . . ?
C4 C5 C6 C13 179.1(3) . . . . ?
C16 C5 C6 C7 179.6(3) . . . . ?
C4 C5 C6 C7 -0.5(5) . . . . ?
C5 C6 C7 C8 179.5(3) . . . . ?
C13 C6 C7 C8 -0.1(5) . . . . ?
C5 C6 C7 C19 1.7(5) . . . . ?
C13 C6 C7 C19 -177.9(3) . . . . ?
C19 C7 C8 C9 1.0(5) . . . . ?
C6 C7 C8 C9 -176.8(3) . . . . ?
C7 C8 C9 C17 0.1(6) . . . . ?
C2 C1 C10 C11 0.0(6) . . . . ?
C1 C10 C11 C12 -0.6(5) . . . . ?
C1 C10 C11 Br1 179.7(3) . . . . ?
C20 N2 C12 C11 177.8(3) . . . . ?
C20 N2 C12 C3 -0.9(5) . . . . ?
C10 C11 C12 N2 -178.3(3) . . . . ?
Br1 C11 C12 N2 1.4(4) . . . . ?
C10 C11 C12 C3 0.4(5) . . . . ?
Br1 C11 C12 C3 -179.9(2) . . . . ?
N1 C3 C12 N2 -0.6(5) . . . . ?
C2 C3 C12 N2 179.0(3) . . . . ?
N1 C3 C12 C11 -179.3(3) . . . . ?
C2 C3 C12 C11 0.3(5) . . . . ?
C5 C6 C13 C14 0.0(5) . . . . ?
C7 C6 C13 C14 179.6(3) . . . . ?
C6 C13 C14 C15 1.0(6) . . . . ?
C13 C14 C15 C16 -1.1(6) . . . . ?
C14 C15 C16 C5 0.4(6) . . . . ?
C6 C5 C16 C15 0.5(5) . . . . ?
C4 C5 C16 C15 -179.3(3) . . . . ?
C8 C9 C17 C18 -1.4(6) . . . . ?
C9 C17 C18 C19 1.7(6) . . . . ?
C17 C18 C19 C7 -0.7(6) . . . . ?
C17 C18 C19 C20 179.3(4) . . . . ?
C8 C7 C19 C18 -0.6(5) . . . . ?
C6 C7 C19 C18 177.2(3) . . . . ?
C8 C7 C19 C20 179.4(3) . . . . ?
C6 C7 C19 C20 -2.8(5) . . . . ?
C12 N2 C20 C4 2.1(5) . . . . ?
C12 N2 C20 C19 -178.1(3) . . . . ?
N1 C4 C20 N2 -2.0(5) . . . . ?
C5 C4 C20 N2 178.4(3) . . . . ?
N1 C4 C20 C19 178.1(3) . . . . ?
C5 C4 C20 C19 -1.4(5) . . . . ?
C18 C19 C20 N2 2.8(5) . . . . ?
C7 C19 C20 N2 -177.2(3) . . . . ?
C18 C19 C20 C4 -177.3(3) . . . . ?
C7 C19 C20 C4 2.7(5) . . . . ?

_refine_diff_density_max         0.611
_refine_diff_density_min         -0.784
_refine_diff_density_rms         0.145

####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2053444'
loop_
_audit_author_name
_audit_author_address
'Anjaneyulu Putta'
;University of South Dakota
United States of America
;
_audit_update_record             
;
2021-01-01 deposited with the CCDC.	2022-02-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'3,6-bis(perfluoropropyl)-dibenzo[a, c] phenazine'
_chemical_name_common            
'3,6-bis(perfluoropropyl)-dibenzo[a, c] phenazine'
_chemical_melting_point          184-186\^A\%C
_chemical_formula_moiety         'C13 H5 F7 N'
_chemical_formula_sum            'C13 H5 F7 N'
_chemical_formula_weight         308.18

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+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                   23.9534(17)
_cell_length_b                   13.3698(9)
_cell_length_c                   7.2037(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.922(3)
_cell_angle_gamma                90
_cell_volume                     2301.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8737
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      34.33

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.779
_exptl_crystal_F_000             1224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.185
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30658
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.977
_diffrn_reflns_theta_max         34.900
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4856
_reflns_number_gt                3129
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.0705P)²+2.0670P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4856
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1581
_refine_ls_wR_factor_gt          0.1309
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
F1 F 0.32975(4) 0.24631(7) 0.55271(14) 0.0272(2) Uani 1 1 d . . . . .
F2 F 0.39371(4) 0.16410(7) 0.41200(15) 0.0268(2) Uani 1 1 d . . . . .
F3 F 0.27145(4) 0.28208(7) 0.23432(15) 0.0282(2) Uani 1 1 d . . . . .
F4 F 0.33814(4) 0.22497(8) 0.07138(14) 0.0305(2) Uani 1 1 d . . . . .
F7 F 0.24632(5) 0.10221(8) 0.10933(17) 0.0384(3) Uani 1 1 d . . . . .
F5 F 0.26884(5) 0.09121(8) 0.40304(17) 0.0397(3) Uani 1 1 d . . . . .
F6 F 0.32600(5) 0.04110(8) 0.2050(2) 0.0439(3) Uani 1 1 d . . . . .
N10 N 0.44664(5) 0.69726(9) 0.32322(18) 0.0200(2) Uani 1 1 d . . . . .
C009 C 0.44438(6) 0.51772(10) 0.31546(19) 0.0175(2) Uani 1 1 d . . . . .
C20 C 0.47127(6) 0.42661(10) 0.28066(19) 0.0172(2) Uani 1 1 d . . . . .
C1 C 0.38976(6) 0.51845(10) 0.3762(2) 0.0201(3) Uani 1 1 d . . . . .
H1 H 0.372101 0.580333 0.399911 0.024 Uiso 1 1 calc R U . . .
C3 C 0.38807(6) 0.33915(10) 0.3663(2) 0.0193(3) Uani 1 1 d . . . . .
C4 C 0.44162(6) 0.33710(10) 0.3046(2) 0.0185(3) Uani 1 1 d . . . . .
H4 H 0.458451 0.274816 0.278182 0.022 Uiso 1 1 calc R U . . .
C16 C 0.47287(6) 0.61264(10) 0.28573(19) 0.0176(2) Uani 1 1 d . . . . .
C2 C 0.36170(6) 0.42991(11) 0.4017(2) 0.0208(3) Uani 1 1 d . . . . .
H2 H 0.324860 0.430555 0.442793 0.025 Uiso 1 1 calc R U . . .
C21 C 0.35749(6) 0.24259(10) 0.3947(2) 0.0205(3) Uani 1 1 d . . . . .
C14 C 0.47324(6) 0.78381(10) 0.2882(2) 0.0200(3) Uani 1 1 d . . . . .
C23 C 0.28836(7) 0.10991(12) 0.2390(3) 0.0283(3) Uani 1 1 d . . . . .
C22 C 0.31388(6) 0.21631(11) 0.2338(2) 0.0222(3) Uani 1 1 d . . . . .
C13 C 0.44712(7) 0.87653(11) 0.3255(2) 0.0252(3) Uani 1 1 d . . . . .
H13 H 0.411528 0.877524 0.376112 0.030 Uiso 1 1 calc R U . . .
C12 C 0.47349(7) 0.96426(11) 0.2881(2) 0.0275(3) Uani 1 1 d . . . . .
H12 H 0.456023 1.026088 0.313482 0.033 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
F1 C21 1.3574(17) . ?
F2 C21 1.3619(17) . ?
F3 C22 1.3440(17) . ?
F4 C22 1.3466(18) . ?
F7 C23 1.330(2) . ?
F5 C23 1.324(2) . ?
F6 C23 1.323(2) . ?
N10 C16 1.3307(17) . ?
N10 C14 1.3529(18) . ?
C009 C1 1.4078(19) . ?
C009 C20 1.4084(18) . ?
C009 C16 1.4636(18) . ?
C20 C4 1.4082(18) . ?
C20 C20 1.474(3) 2_655 ?
C1 C2 1.380(2) . ?
C1 H1 0.9500 . ?
C3 C4 1.386(2) . ?
C3 C2 1.3994(19) . ?
C3 C21 1.5053(19) . ?
C4 H4 0.9500 . ?
C16 C16 1.430(3) 2_655 ?
C2 H2 0.9500 . ?
C21 C22 1.547(2) . ?
C14 C13 1.422(2) . ?
C14 C14 1.430(3) 2_655 ?
C23 C22 1.550(2) . ?
C13 C12 1.368(2) . ?
C13 H13 0.9500 . ?
C12 C12 1.417(3) 2_655 ?
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
C16 N10 C14 117.04(12) . . ?
C1 C009 C20 120.49(12) . . ?
C1 C009 C16 119.48(12) . . ?
C20 C009 C16 120.03(12) . . ?
C4 C20 C009 118.21(12) . . ?
C4 C20 C20 121.72(8) . 2_655 ?
C009 C20 C20 120.07(8) . 2_655 ?
C2 C1 C009 120.46(13) . . ?
C2 C1 H1 119.8 . . ?
C009 C1 H1 119.8 . . ?
C4 C3 C2 120.97(13) . . ?
C4 C3 C21 119.75(12) . . ?
C2 C3 C21 119.28(12) . . ?
C3 C4 C20 120.52(12) . . ?
C3 C4 H4 119.7 . . ?
C20 C4 H4 119.7 . . ?
N10 C16 C16 121.75(8) . 2_655 ?
N10 C16 C009 118.44(12) . . ?
C16 C16 C009 119.79(7) 2_655 . ?
C1 C2 C3 119.33(13) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
F1 C21 F2 107.27(12) . . ?
F1 C21 C3 110.69(12) . . ?
F2 C21 C3 111.13(12) . . ?
F1 C21 C22 107.01(12) . . ?
F2 C21 C22 106.67(12) . . ?
C3 C21 C22 113.75(12) . . ?
N10 C14 C13 119.44(13) . . ?
N10 C14 C14 121.19(8) . 2_655 ?
C13 C14 C14 119.36(9) . 2_655 ?
F6 C23 F5 108.70(14) . . ?
F6 C23 F7 108.01(14) . . ?
F5 C23 F7 108.40(14) . . ?
F6 C23 C22 111.04(13) . . ?
F5 C23 C22 111.02(14) . . ?
F7 C23 C22 109.58(13) . . ?
F3 C22 F4 108.51(12) . . ?
F3 C22 C21 108.75(12) . . ?
F4 C22 C21 108.80(12) . . ?
F3 C22 C23 107.51(12) . . ?
F4 C22 C23 107.11(13) . . ?
C21 C22 C23 115.96(13) . . ?
C12 C13 C14 119.68(14) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C12 C12 120.96(9) . 2_655 ?
C13 C12 H12 119.5 . . ?
C12 C12 H12 119.5 2_655 . ?

_refine_diff_density_max         0.468
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2053443'
loop_
_audit_author_name
_audit_author_address
'Anjaneyulu Putta'
;University of South Dakota
United States of America
;
_audit_update_record             
;
2021-01-01 deposited with the CCDC.	2022-02-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'10,13-bis(perfluoropropyl)-dibenzo[a, c] phenazine'
_chemical_name_common            ParaC3F7dibenzphenazine
_chemical_melting_point          248\%C
_chemical_formula_moiety         'C26 H10 F14 N2'
_chemical_formula_sum            'C26 H10 F14 N2'
_chemical_formula_weight         616.36

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                   16.0011(17)
_cell_length_b                   5.2318(5)
_cell_length_c                   27.377(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.533(4)
_cell_angle_gamma                90
_cell_volume                     2245.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5892
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      25.98

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_F_000             1224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.190
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38876
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_av_R_equivalents  0.0871
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.187
_diffrn_reflns_theta_max         26.032
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4440
_reflns_number_gt                3383
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.0340P)²+3.4015P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4440
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1221
_refine_ls_wR_factor_gt          0.1112
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_restrained_S_all      1.135
_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
F7 F 0.19009(14) 0.3199(4) 0.82704(6) 0.0427(5) Uani 1 1 d . . . . .
F12 F 0.24431(11) 0.9765(4) 0.43246(7) 0.0320(4) Uani 1 1 d . . . . .
F5 F 0.22526(13) 0.0011(4) 0.78625(7) 0.0377(5) Uani 1 1 d . . . . .
F6 F 0.09214(13) 0.0705(4) 0.78701(7) 0.0402(5) Uani 1 1 d . . . . .
F4 F 0.10755(12) 0.5512(3) 0.74589(7) 0.0320(4) Uani 1 1 d . . . . .
F3 F 0.23816(11) 0.4518(3) 0.74124(6) 0.0275(4) Uani 1 1 d . . . . .
F1 F 0.16026(11) -0.0007(3) 0.68762(6) 0.0252(4) Uani 1 1 d . . . . .
F2 F 0.03989(11) 0.1915(3) 0.68617(6) 0.0297(4) Uani 1 1 d . . . . .
F9 F 0.09922(11) 1.0862(3) 0.51783(6) 0.0250(4) Uani 1 1 d . . . . .
F8 F 0.23643(10) 1.0386(3) 0.52969(6) 0.0228(4) Uani 1 1 d . . . . .
F10 F 0.20159(11) 0.5532(3) 0.47919(6) 0.0253(4) Uani 1 1 d . . . . .
F11 F 0.06807(11) 0.6711(3) 0.46402(6) 0.0277(4) Uani 1 1 d . . . . .
F14 F 0.14517(13) 0.7502(3) 0.38792(6) 0.0340(5) Uani 1 1 d . . . . .
F13 F 0.11435(12) 1.1082(3) 0.41886(6) 0.0331(4) Uani 1 1 d . . . . .
N1 N 0.28097(15) 0.2521(4) 0.65044(8) 0.0185(5) Uani 1 1 d . . . . .
N2 N 0.30409(15) 0.6045(4) 0.57667(8) 0.0180(5) Uani 1 1 d . . . . .
C18 C 0.6131(2) 0.5595(6) 0.56628(12) 0.0298(7) Uani 1 1 d . . . . .
H1 H 0.668188 0.582960 0.558966 0.036 Uiso 1 1 calc R U . . .
C17 C 0.59964(19) 0.3668(6) 0.59840(11) 0.0265(7) Uani 1 1 d . . . . .
H3 H 0.646001 0.260688 0.613191 0.032 Uiso 1 1 calc R U . . .
C10 C 0.51924(19) 0.3249(6) 0.60958(10) 0.0223(6) Uani 1 1 d . . . . .
C11 C 0.50444(18) 0.1217(5) 0.64448(10) 0.0207(6) Uani 1 1 d . . . . .
C12 C 0.42302(18) 0.0943(5) 0.65634(10) 0.0195(6) Uani 1 1 d . . . . .
C7 C 0.35423(17) 0.2689(5) 0.63509(10) 0.0172(6) Uani 1 1 d . . . . .
C6 C 0.21712(18) 0.4102(5) 0.62935(10) 0.0180(6) Uani 1 1 d . . . . .
C1 C 0.13699(18) 0.4000(5) 0.64523(10) 0.0189(6) Uani 1 1 d . . . . .
C21 C 0.12455(18) 0.2338(5) 0.68835(10) 0.0209(6) Uani 1 1 d . . . . .
C22 C 0.15966(19) 0.3559(6) 0.74008(10) 0.0221(6) Uani 1 1 d . . . . .
C23 C 0.1668(2) 0.1802(6) 0.78571(11) 0.0291(7) Uani 1 1 d . . . . .
C26 C 0.16389(19) 0.9027(6) 0.42759(10) 0.0232(6) Uani 1 1 d . . . . .
C25 C 0.14935(18) 0.7574(5) 0.47416(10) 0.0198(6) Uani 1 1 d . . . . .
C24 C 0.16215(17) 0.9074(5) 0.52376(10) 0.0190(6) Uani 1 1 d . . . . .
C4 C 0.15717(18) 0.7367(5) 0.56754(10) 0.0188(6) Uani 1 1 d . . . . .
C3 C 0.08130(18) 0.7172(5) 0.58299(10) 0.0208(6) Uani 1 1 d . . . . .
H10 H 0.034140 0.816571 0.566802 0.025 Uiso 1 1 calc R U . . .
C2 C 0.07111(19) 0.5528(6) 0.62248(10) 0.0232(6) Uani 1 1 d . . . . .
H9 H 0.018247 0.548386 0.633250 0.028 Uiso 1 1 calc R U . . .
C9 C 0.45164(18) 0.4855(5) 0.58683(10) 0.0201(6) Uani 1 1 d . . . . .
C20 C 0.46627(19) 0.6812(6) 0.55446(10) 0.0233(6) Uani 1 1 d . . . . .
H4 H 0.420503 0.788269 0.539206 0.028 Uiso 1 1 calc R U . . .
C19 C 0.5465(2) 0.7189(6) 0.54466(11) 0.0270(7) Uani 1 1 d . . . . .
H2 H 0.556203 0.853518 0.523182 0.032 Uiso 1 1 calc R U . . .
C8 C 0.36734(18) 0.4547(5) 0.59888(10) 0.0175(6) Uani 1 1 d . . . . .
C5 C 0.22796(17) 0.5836(5) 0.59102(10) 0.0174(6) Uani 1 1 d . . . . .
C16 C 0.5688(2) -0.0484(6) 0.66625(11) 0.0251(7) Uani 1 1 d . . . . .
H8 H 0.624459 -0.030340 0.659550 0.030 Uiso 1 1 calc R U . . .
C15 C 0.5524(2) -0.2421(6) 0.69730(11) 0.0273(7) Uani 1 1 d . . . . .
H5 H 0.596748 -0.356580 0.711479 0.033 Uiso 1 1 calc R U . . .
C14 C 0.4713(2) -0.2708(6) 0.70800(11) 0.0251(7) Uani 1 1 d . . . . .
H6 H 0.460286 -0.405895 0.729026 0.030 Uiso 1 1 calc R U . . .
C13 C 0.40731(19) -0.1036(5) 0.68809(10) 0.0221(6) Uani 1 1 d . . . . .
H7 H 0.352299 -0.121660 0.695793 0.027 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
F7 C23 1.336(3) . ?
F12 C26 1.324(3) . ?
F5 C23 1.322(4) . ?
F6 C23 1.332(4) . ?
F4 C22 1.348(3) . ?
F3 C22 1.347(3) . ?
F1 C21 1.355(3) . ?
F2 C21 1.362(3) . ?
F9 C24 1.360(3) . ?
F8 C24 1.354(3) . ?
F10 C25 1.347(3) . ?
F11 C25 1.352(3) . ?
F14 C26 1.333(3) . ?
F13 C26 1.329(3) . ?
N1 C7 1.325(4) . ?
N1 C6 1.351(4) . ?
N2 C8 1.327(4) . ?
N2 C5 1.357(3) . ?
C18 C17 1.383(4) . ?
C18 C19 1.390(4) . ?
C18 H1 0.9500 . ?
C17 C10 1.398(4) . ?
C17 H3 0.9500 . ?
C10 C9 1.412(4) . ?
C10 C11 1.480(4) . ?
C11 C16 1.400(4) . ?
C11 C12 1.411(4) . ?
C12 C13 1.407(4) . ?
C12 C7 1.459(4) . ?
C7 C8 1.433(4) . ?
C6 C5 1.424(4) . ?
C6 C1 1.435(4) . ?
C1 C2 1.369(4) . ?
C1 C21 1.511(4) . ?
C21 C22 1.553(4) . ?
C22 C23 1.537(4) . ?
C26 C25 1.541(4) . ?
C25 C24 1.546(4) . ?
C24 C4 1.510(4) . ?
C4 C3 1.367(4) . ?
C4 C5 1.430(4) . ?
C3 C2 1.416(4) . ?
C3 H10 0.9500 . ?
C2 H9 0.9500 . ?
C9 C20 1.404(4) . ?
C9 C8 1.460(4) . ?
C20 C19 1.377(4) . ?
C20 H4 0.9500 . ?
C19 H2 0.9500 . ?
C16 C15 1.381(4) . ?
C16 H8 0.9500 . ?
C15 C14 1.395(4) . ?
C15 H5 0.9500 . ?
C14 C13 1.374(4) . ?
C14 H6 0.9500 . ?
C13 H7 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
C7 N1 C6 117.7(2) . . ?
C8 N2 C5 117.8(2) . . ?
C17 C18 C19 120.3(3) . . ?
C17 C18 H1 119.8 . . ?
C19 C18 H1 119.8 . . ?
C18 C17 C10 121.4(3) . . ?
C18 C17 H3 119.3 . . ?
C10 C17 H3 119.3 . . ?
C17 C10 C9 117.8(3) . . ?
C17 C10 C11 121.8(3) . . ?
C9 C10 C11 120.3(3) . . ?
C16 C11 C12 118.1(3) . . ?
C16 C11 C10 122.2(3) . . ?
C12 C11 C10 119.7(3) . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 C7 119.6(3) . . ?
C11 C12 C7 120.2(3) . . ?
N1 C7 C8 121.7(3) . . ?
N1 C7 C12 118.5(2) . . ?
C8 C7 C12 119.8(2) . . ?
N1 C6 C5 120.8(2) . . ?
N1 C6 C1 119.5(2) . . ?
C5 C6 C1 119.7(3) . . ?
C2 C1 C6 119.6(3) . . ?
C2 C1 C21 118.8(3) . . ?
C6 C1 C21 121.6(2) . . ?
F1 C21 F2 105.7(2) . . ?
F1 C21 C1 112.8(2) . . ?
F2 C21 C1 110.2(2) . . ?
F1 C21 C22 108.0(2) . . ?
F2 C21 C22 106.4(2) . . ?
C1 C21 C22 113.3(2) . . ?
F3 C22 F4 108.1(2) . . ?
F3 C22 C23 106.6(2) . . ?
F4 C22 C23 107.7(2) . . ?
F3 C22 C21 109.9(2) . . ?
F4 C22 C21 107.4(2) . . ?
C23 C22 C21 116.7(2) . . ?
F5 C23 F6 109.3(3) . . ?
F5 C23 F7 107.5(3) . . ?
F6 C23 F7 108.2(2) . . ?
F5 C23 C22 111.7(2) . . ?
F6 C23 C22 111.0(3) . . ?
F7 C23 C22 108.9(3) . . ?
F12 C26 F13 108.4(2) . . ?
F12 C26 F14 108.2(2) . . ?
F13 C26 F14 108.0(2) . . ?
F12 C26 C25 111.4(2) . . ?
F13 C26 C25 111.4(2) . . ?
F14 C26 C25 109.4(2) . . ?
F10 C25 F11 107.9(2) . . ?
F10 C25 C26 106.4(2) . . ?
F11 C25 C26 107.0(2) . . ?
F10 C25 C24 110.0(2) . . ?
F11 C25 C24 107.6(2) . . ?
C26 C25 C24 117.4(2) . . ?
F8 C24 F9 106.1(2) . . ?
F8 C24 C4 112.9(2) . . ?
F9 C24 C4 110.3(2) . . ?
F8 C24 C25 108.8(2) . . ?
F9 C24 C25 106.2(2) . . ?
C4 C24 C25 112.3(2) . . ?
C3 C4 C5 119.4(3) . . ?
C3 C4 C24 118.7(2) . . ?
C5 C4 C24 121.7(2) . . ?
C4 C3 C2 121.8(3) . . ?
C4 C3 H10 119.1 . . ?
C2 C3 H10 119.1 . . ?
C1 C2 C3 120.4(3) . . ?
C1 C2 H9 119.8 . . ?
C3 C2 H9 119.8 . . ?
C20 C9 C10 120.2(3) . . ?
C20 C9 C8 120.1(3) . . ?
C10 C9 C8 119.7(3) . . ?
C19 C20 C9 120.5(3) . . ?
C19 C20 H4 119.8 . . ?
C9 C20 H4 119.8 . . ?
C20 C19 C18 119.8(3) . . ?
C20 C19 H2 120.1 . . ?
C18 C19 H2 120.1 . . ?
N2 C8 C7 120.9(2) . . ?
N2 C8 C9 119.1(2) . . ?
C7 C8 C9 120.0(2) . . ?
N2 C5 C6 120.9(2) . . ?
N2 C5 C4 120.1(2) . . ?
C6 C5 C4 119.1(2) . . ?
C15 C16 C11 121.0(3) . . ?
C15 C16 H8 119.5 . . ?
C11 C16 H8 119.5 . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H5 119.8 . . ?
C14 C15 H5 119.8 . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H6 120.0 . . ?
C15 C14 H6 120.0 . . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 H7 119.9 . . ?
C12 C13 H7 119.9 . . ?

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
C19 C18 C17 C10 0.7(5) . . . . ?
C18 C17 C10 C9 0.2(4) . . . . ?
C18 C17 C10 C11 -179.1(3) . . . . ?
C17 C10 C11 C16 -3.4(4) . . . . ?
C9 C10 C11 C16 177.3(3) . . . . ?
C17 C10 C11 C12 177.1(3) . . . . ?
C9 C10 C11 C12 -2.2(4) . . . . ?
C16 C11 C12 C13 -1.7(4) . . . . ?
C10 C11 C12 C13 177.8(2) . . . . ?
C16 C11 C12 C7 179.2(2) . . . . ?
C10 C11 C12 C7 -1.3(4) . . . . ?
C6 N1 C7 C8 2.5(4) . . . . ?
C6 N1 C7 C12 -178.1(2) . . . . ?
C13 C12 C7 N1 6.9(4) . . . . ?
C11 C12 C7 N1 -174.1(2) . . . . ?
C13 C12 C7 C8 -173.8(2) . . . . ?
C11 C12 C7 C8 5.3(4) . . . . ?
C7 N1 C6 C5 1.6(4) . . . . ?
C7 N1 C6 C1 -179.4(2) . . . . ?
N1 C6 C1 C2 -177.4(3) . . . . ?
C5 C6 C1 C2 1.7(4) . . . . ?
N1 C6 C1 C21 5.7(4) . . . . ?
C5 C6 C1 C21 -175.3(2) . . . . ?
C2 C1 C21 F1 140.5(3) . . . . ?
C6 C1 C21 F1 -42.5(4) . . . . ?
C2 C1 C21 F2 22.6(4) . . . . ?
C6 C1 C21 F2 -160.4(2) . . . . ?
C2 C1 C21 C22 -96.4(3) . . . . ?
C6 C1 C21 C22 80.6(3) . . . . ?
F1 C21 C22 F3 79.6(3) . . . . ?
F2 C21 C22 F3 -167.3(2) . . . . ?
C1 C21 C22 F3 -46.1(3) . . . . ?
F1 C21 C22 F4 -163.0(2) . . . . ?
F2 C21 C22 F4 -49.9(3) . . . . ?
C1 C21 C22 F4 71.3(3) . . . . ?
F1 C21 C22 C23 -42.0(3) . . . . ?
F2 C21 C22 C23 71.1(3) . . . . ?
C1 C21 C22 C23 -167.7(2) . . . . ?
F3 C22 C23 F5 -56.1(3) . . . . ?
F4 C22 C23 F5 -171.9(2) . . . . ?
C21 C22 C23 F5 67.2(3) . . . . ?
F3 C22 C23 F6 -178.4(2) . . . . ?
F4 C22 C23 F6 65.8(3) . . . . ?
C21 C22 C23 F6 -55.1(3) . . . . ?
F3 C22 C23 F7 62.6(3) . . . . ?
F4 C22 C23 F7 -53.3(3) . . . . ?
C21 C22 C23 F7 -174.2(2) . . . . ?
F12 C26 C25 F10 -59.5(3) . . . . ?
F13 C26 C25 F10 179.4(2) . . . . ?
F14 C26 C25 F10 60.0(3) . . . . ?
F12 C26 C25 F11 -174.7(2) . . . . ?
F13 C26 C25 F11 64.2(3) . . . . ?
F14 C26 C25 F11 -55.2(3) . . . . ?
F12 C26 C25 C24 64.2(3) . . . . ?
F13 C26 C25 C24 -56.9(3) . . . . ?
F14 C26 C25 C24 -176.2(2) . . . . ?
F10 C25 C24 F8 74.9(3) . . . . ?
F11 C25 C24 F8 -167.8(2) . . . . ?
C26 C25 C24 F8 -47.0(3) . . . . ?
F10 C25 C24 F9 -171.3(2) . . . . ?
F11 C25 C24 F9 -54.0(3) . . . . ?
C26 C25 C24 F9 66.8(3) . . . . ?
F10 C25 C24 C4 -50.8(3) . . . . ?
F11 C25 C24 C4 66.6(3) . . . . ?
C26 C25 C24 C4 -172.7(2) . . . . ?
F8 C24 C4 C3 140.8(3) . . . . ?
F9 C24 C4 C3 22.4(3) . . . . ?
C25 C24 C4 C3 -95.8(3) . . . . ?
F8 C24 C4 C5 -43.2(3) . . . . ?
F9 C24 C4 C5 -161.6(2) . . . . ?
C25 C24 C4 C5 80.2(3) . . . . ?
C5 C4 C3 C2 1.3(4) . . . . ?
C24 C4 C3 C2 177.4(3) . . . . ?
C6 C1 C2 C3 0.9(4) . . . . ?
C21 C1 C2 C3 178.0(3) . . . . ?
C4 C3 C2 C1 -2.5(4) . . . . ?
C17 C10 C9 C20 -0.5(4) . . . . ?
C11 C10 C9 C20 178.8(3) . . . . ?
C17 C10 C9 C8 -177.7(3) . . . . ?
C11 C10 C9 C8 1.6(4) . . . . ?
C10 C9 C20 C19 -0.2(4) . . . . ?
C8 C9 C20 C19 177.0(3) . . . . ?
C9 C20 C19 C18 1.1(4) . . . . ?
C17 C18 C19 C20 -1.4(5) . . . . ?
C5 N2 C8 C7 2.9(4) . . . . ?
C5 N2 C8 C9 -175.6(2) . . . . ?
N1 C7 C8 N2 -5.1(4) . . . . ?
C12 C7 C8 N2 175.6(2) . . . . ?
N1 C7 C8 C9 173.5(2) . . . . ?
C12 C7 C8 C9 -5.8(4) . . . . ?
C20 C9 C8 N2 3.8(4) . . . . ?
C10 C9 C8 N2 -179.0(2) . . . . ?
C20 C9 C8 C7 -174.8(2) . . . . ?
C10 C9 C8 C7 2.4(4) . . . . ?
C8 N2 C5 C6 1.2(4) . . . . ?
C8 N2 C5 C4 -178.7(2) . . . . ?
N1 C6 C5 N2 -3.7(4) . . . . ?
C1 C6 C5 N2 177.3(2) . . . . ?
N1 C6 C5 C4 176.2(2) . . . . ?
C1 C6 C5 C4 -2.8(4) . . . . ?
C3 C4 C5 N2 -178.8(3) . . . . ?
C24 C4 C5 N2 5.2(4) . . . . ?
C3 C4 C5 C6 1.3(4) . . . . ?
C24 C4 C5 C6 -174.6(2) . . . . ?
C12 C11 C16 C15 1.8(4) . . . . ?
C10 C11 C16 C15 -177.7(3) . . . . ?
C11 C16 C15 C14 -0.6(4) . . . . ?
C16 C15 C14 C13 -0.9(4) . . . . ?
C15 C14 C13 C12 1.0(4) . . . . ?
C11 C12 C13 C14 0.4(4) . . . . ?
C7 C12 C13 C14 179.4(3) . . . . ?

_refine_diff_density_max         0.286
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.064

