# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_2696RKM_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2246524'
_audit_update_record             
;
2023-03-04 deposited with the CCDC.	2023-05-19 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         'C22 H14 Cl N3'
_chemical_formula_sum            'C22 H14 Cl N3'
_chemical_formula_weight         355.81

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'
Cl Cl 0.1484 0.1585 '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'

_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                   17.4509(7)
_cell_length_b                   12.4727(5)
_cell_length_c                   17.6236(7)
_cell_angle_alpha                90
_cell_angle_beta                 112.121(2)
_cell_angle_gamma                90
_cell_volume                     3553.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    5660
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      25.35

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.225
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.989
_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      273(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            20048
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.062
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3136
_reflns_number_gt                2226
_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'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.1000P)²+0.6677P] 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         3136
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.1607
_refine_ls_wR_factor_gt          0.1464
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
Cl1 Cl 0.41033(7) 0.70621(8) 0.64293(6) 0.0844(4) Uani 1 1 d . . . . .
N2 N 0.66752(12) 0.60315(16) 0.50920(12) 0.0355(5) Uani 1 1 d . . . . .
N1 N 0.60486(12) 0.58078(17) 0.33564(12) 0.0382(5) Uani 1 1 d . . . . .
N3 N 0.47305(12) 0.61052(18) 0.34595(13) 0.0457(6) Uani 1 1 d . . . . .
H004 H 0.441336 0.604753 0.295157 0.055 Uiso 1 1 calc R U . . .
C16 C 0.58717(15) 0.61085(19) 0.46371(15) 0.0338(6) Uani 1 1 d . . . . .
C7 C 0.71763(14) 0.58154(18) 0.46849(15) 0.0340(6) Uani 1 1 d . . . . .
C8 C 0.68643(15) 0.57365(19) 0.38184(14) 0.0346(6) Uani 1 1 d . . . . .
C15 C 0.55675(14) 0.5969(2) 0.37756(15) 0.0354(6) Uani 1 1 d . . . . .
C17 C 0.51610(15) 0.63499(19) 0.48399(15) 0.0383(6) Uani 1 1 d . . . . .
C9 C 0.74034(15) 0.5643(2) 0.33320(15) 0.0376(6) Uani 1 1 d . . . . .
C6 C 0.80704(15) 0.5688(2) 0.51975(15) 0.0373(6) Uani 1 1 d . . . . .
C18 C 0.44779(15) 0.6352(2) 0.40966(16) 0.0403(6) Uani 1 1 d . . . . .
C10 C 0.80192(16) 0.6382(2) 0.34064(16) 0.0450(7) Uani 1 1 d . . . . .
H00D H 0.813541 0.692190 0.379752 0.054 Uiso 1 1 calc R U . . .
C1 C 0.84551(16) 0.6414(2) 0.58196(16) 0.0446(7) Uani 1 1 d . . . . .
H00E H 0.815093 0.697143 0.591823 0.054 Uiso 1 1 calc R U . . .
C22 C 0.50566(17) 0.6562(2) 0.55752(17) 0.0450(7) Uani 1 1 d . . . . .
H00F H 0.550380 0.655508 0.607383 0.054 Uiso 1 1 calc R U . . .
C11 C 0.84650(17) 0.6320(2) 0.28996(18) 0.0518(7) Uani 1 1 d . . . . .
H00G H 0.887415 0.682417 0.294955 0.062 Uiso 1 1 calc R U . . .
C19 C 0.36827(18) 0.6586(2) 0.4062(2) 0.0541(8) Uani 1 1 d . . . . .
H00H H 0.323231 0.660067 0.356564 0.065 Uiso 1 1 calc R U . . .
C12 C 0.83041(18) 0.5518(3) 0.23247(17) 0.0536(8) Uani 1 1 d . . . . .
H00I H 0.860245 0.547965 0.198557 0.064 Uiso 1 1 calc R U . . .
C5 C 0.85382(18) 0.4842(2) 0.50738(18) 0.0539(8) Uani 1 1 d . . . . .
H00J H 0.829016 0.434042 0.466387 0.065 Uiso 1 1 calc R U . . .
C14 C 0.72465(17) 0.4838(2) 0.27471(17) 0.0510(7) Uani 1 1 d . . . . .
H00K H 0.683249 0.433821 0.268669 0.061 Uiso 1 1 calc R U . . .
C21 C 0.4270(2) 0.6779(2) 0.55343(19) 0.0525(8) Uani 1 1 d . . . . .
C13 C 0.7702(2) 0.4777(3) 0.22544(18) 0.0590(8) Uani 1 1 d . . . . .
H00M H 0.759850 0.422779 0.187190 0.071 Uiso 1 1 calc R U . . .
C20 C 0.3591(2) 0.6795(2) 0.4791(2) 0.0596(8) Uani 1 1 d . . . . .
H00N H 0.306891 0.694805 0.478822 0.072 Uiso 1 1 calc R U . . .
C2 C 0.92879(19) 0.6317(3) 0.6295(2) 0.0657(10) Uani 1 1 d . . . . .
H00O H 0.954223 0.681226 0.670798 0.079 Uiso 1 1 calc R U . . .
C4 C 0.9367(2) 0.4751(3) 0.5560(2) 0.0699(10) Uani 1 1 d . . . . .
H00P H 0.967531 0.418518 0.547996 0.084 Uiso 1 1 calc R U . . .
C3 C 0.97372(19) 0.5495(3) 0.6161(2) 0.0751(11) Uani 1 1 d . . . . .
H00Q H 1.029851 0.543824 0.647843 0.090 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
Cl1 C21 1.745(3) . ?
N2 C16 1.331(3) . ?
N2 C7 1.351(3) . ?
N1 C15 1.326(3) . ?
N1 C8 1.351(3) . ?
N3 C15 1.364(3) . ?
N3 C18 1.387(3) . ?
C16 C15 1.418(3) . ?
C16 C17 1.446(3) . ?
C7 C8 1.418(3) . ?
C7 C6 1.488(3) . ?
C8 C9 1.497(3) . ?
C17 C22 1.400(3) . ?
C17 C18 1.400(4) . ?
C9 C10 1.384(4) . ?
C9 C14 1.390(4) . ?
C6 C1 1.385(4) . ?
C6 C5 1.401(4) . ?
C18 C19 1.396(4) . ?
C10 C11 1.390(4) . ?
C1 C2 1.383(4) . ?
C22 C21 1.374(4) . ?
C11 C12 1.375(4) . ?
C19 C20 1.378(4) . ?
C12 C13 1.370(4) . ?
C5 C4 1.380(4) . ?
C14 C13 1.382(4) . ?
C21 C20 1.397(5) . ?
C2 C3 1.365(5) . ?
C4 C3 1.372(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
C16 N2 C7 116.1(2) . . ?
C15 N1 C8 114.8(2) . . ?
C15 N3 C18 108.4(2) . . ?
N2 C16 C15 121.4(2) . . ?
N2 C16 C17 132.3(2) . . ?
C15 C16 C17 106.3(2) . . ?
N2 C7 C8 121.5(2) . . ?
N2 C7 C6 116.1(2) . . ?
C8 C7 C6 122.4(2) . . ?
N1 C8 C7 122.3(2) . . ?
N1 C8 C9 114.0(2) . . ?
C7 C8 C9 123.6(2) . . ?
N1 C15 N3 126.6(2) . . ?
N1 C15 C16 123.7(2) . . ?
N3 C15 C16 109.5(2) . . ?
C22 C17 C18 120.2(2) . . ?
C22 C17 C16 133.7(2) . . ?
C18 C17 C16 106.1(2) . . ?
C10 C9 C14 118.7(2) . . ?
C10 C9 C8 121.8(2) . . ?
C14 C9 C8 119.4(2) . . ?
C1 C6 C5 118.6(2) . . ?
C1 C6 C7 119.7(2) . . ?
C5 C6 C7 121.7(2) . . ?
N3 C18 C19 128.6(2) . . ?
N3 C18 C17 109.8(2) . . ?
C19 C18 C17 121.6(2) . . ?
C9 C10 C11 120.3(3) . . ?
C2 C1 C6 120.5(3) . . ?
C21 C22 C17 117.7(3) . . ?
C12 C11 C10 120.3(3) . . ?
C20 C19 C18 117.4(3) . . ?
C13 C12 C11 119.6(3) . . ?
C4 C5 C6 120.1(3) . . ?
C13 C14 C9 120.4(3) . . ?
C22 C21 C20 122.0(3) . . ?
C22 C21 Cl1 119.7(2) . . ?
C20 C21 Cl1 118.3(2) . . ?
C12 C13 C14 120.6(3) . . ?
C19 C20 C21 121.1(3) . . ?
C3 C2 C1 120.1(3) . . ?
C3 C4 C5 120.2(3) . . ?
C2 C3 C4 120.5(3) . . ?

_refine_diff_density_max         0.283
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.042



####################################################################### 
# 
# 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_2697RKM_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2246525'
_audit_update_record             
;
2023-03-04 deposited with the CCDC.	2023-05-19 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         'C22 H13 F2 N3'
_chemical_formula_sum            'C22 H13 F2 N3'
_chemical_formula_weight         357.35

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.5735(4)
_cell_length_b                   12.6239(5)
_cell_length_c                   28.8448(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.918(2)
_cell_angle_gamma                90
_cell_volume                     3477.9(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9993
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      23.86

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.995
_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      273(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            50271
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.146
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6482
_reflns_number_gt                4570
_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'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.1000P)²+0.8195P] 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         6482
_refine_ls_number_parameters     487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1741
_refine_ls_wR_factor_gt          0.1561
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 1.1868(2) -0.01368(17) 0.97251(7) 0.1002(7) Uani 1 1 d . . . . .
N2 N 0.8198(2) 0.15187(14) 0.80321(6) 0.0445(5) Uani 1 1 d . . . . .
N5 N 0.6865(2) 0.74849(14) 0.66696(7) 0.0481(5) Uani 1 1 d . . . . .
N1 N 0.7456(2) 0.36921(15) 0.80304(7) 0.0483(5) Uani 1 1 d . . . . .
N4 N 0.5962(2) 0.54870(15) 0.69823(7) 0.0482(5) Uani 1 1 d . . . . .
N3 N 0.6121(2) 0.32377(15) 0.73188(7) 0.0553(6) Uani 1 1 d . . . . .
H3 H 0.575473 0.384387 0.724856 0.066 Uiso 1 1 calc R U . . .
F2 F 1.0431(2) 0.62713(16) 0.96641(7) 0.1111(8) Uani 1 1 d . . . . .
N6 N 0.7524(2) 0.58612(16) 0.76520(7) 0.0570(6) Uani 1 1 d . . . . .
H6 H 0.738795 0.530527 0.781531 0.068 Uiso 1 1 calc R U . . .
F3 F 0.2132(2) 0.30339(17) 0.55028(8) 0.1183(8) Uani 1 1 d . . . . .
F4 F 0.4296(3) 0.8815(2) 0.47107(7) 0.1291(9) Uani 1 1 d . . . . .
C7 C 0.8350(2) 0.32731(18) 0.83660(8) 0.0431(5) Uani 1 1 d . . . . .
C16 C 0.7338(2) 0.19345(17) 0.77036(8) 0.0432(5) Uani 1 1 d . . . . .
C8 C 0.8705(2) 0.21819(18) 0.83727(8) 0.0417(5) Uani 1 1 d . . . . .
C9 C 0.9609(2) 0.16431(18) 0.87417(8) 0.0423(5) Uani 1 1 d . . . . .
C17 C 0.6656(2) 0.14758(18) 0.72898(8) 0.0438(5) Uani 1 1 d . . . . .
C38 C 0.7332(2) 0.70883(18) 0.70788(8) 0.0452(6) Uani 1 1 d . . . . .
C15 C 0.6964(2) 0.30168(18) 0.77064(8) 0.0454(6) Uani 1 1 d . . . . .
C37 C 0.6851(3) 0.60971(18) 0.72328(8) 0.0468(6) Uani 1 1 d . . . . .
C29 C 0.5515(2) 0.58740(18) 0.65608(8) 0.0444(5) Uani 1 1 d . . . . .
C30 C 0.5941(2) 0.68819(18) 0.64075(8) 0.0457(6) Uani 1 1 d . . . . .
C6 C 0.8933(2) 0.40544(18) 0.87154(8) 0.0467(6) Uani 1 1 d . . . . .
C28 C 0.4606(2) 0.51430(18) 0.62726(8) 0.0468(6) Uani 1 1 d . . . . .
C18 C 0.5951(2) 0.23141(18) 0.70551(8) 0.0487(6) Uani 1 1 d . . . . .
C39 C 0.8367(3) 0.74560(18) 0.74270(8) 0.0490(6) Uani 1 1 d . . . . .
C31 C 0.5465(3) 0.73544(18) 0.59521(8) 0.0481(6) Uani 1 1 d . . . . .
C14 C 1.0409(3) 0.07813(19) 0.86141(9) 0.0512(6) Uani 1 1 d . . . . .
H00Q H 1.042868 0.060562 0.830144 0.061 Uiso 1 1 calc R U . . .
C44 C 0.8465(3) 0.66682(19) 0.77709(8) 0.0523(6) Uani 1 1 d . . . . .
C5 C 1.0366(3) 0.4206(2) 0.88020(9) 0.0551(6) Uani 1 1 d . . . . .
H00S H 1.098969 0.380268 0.864274 0.066 Uiso 1 1 calc R U . . .
C22 C 0.6601(3) 0.04648(19) 0.70961(9) 0.0547(6) Uani 1 1 d . . . . .
H00T H 0.703800 -0.010235 0.725220 0.066 Uiso 1 1 calc R U . . .
C10 C 0.9613(3) 0.1888(2) 0.92123(8) 0.0548(7) Uani 1 1 d . . . . .
H00U H 0.909776 0.246504 0.930539 0.066 Uiso 1 1 calc R U . . .
C40 C 0.9260(3) 0.8337(2) 0.74733(9) 0.0567(7) Uani 1 1 d . . . . .
H00V H 0.920716 0.887459 0.725219 0.068 Uiso 1 1 calc R U . . .
C27 C 0.4926(3) 0.4845(2) 0.58284(9) 0.0586(7) Uani 1 1 d . . . . .
H00W H 0.571638 0.512740 0.570427 0.070 Uiso 1 1 calc R U . . .
C23 C 0.3433(3) 0.47002(19) 0.64527(11) 0.0593(7) Uani 1 1 d . . . . .
H00X H 0.321177 0.486960 0.675277 0.071 Uiso 1 1 calc R U . . .
C21 C 0.5895(3) 0.0319(2) 0.66732(9) 0.0619(7) Uani 1 1 d . . . . .
H00Y H 0.584836 -0.035313 0.654109 0.074 Uiso 1 1 calc R U . . .
C12 C 1.1125(3) 0.0455(2) 0.94021(10) 0.0657(8) Uani 1 1 d . . . . .
C13 C 1.1174(3) 0.0182(2) 0.89430(10) 0.0619(7) Uani 1 1 d . . . . .
H010 H 1.170739 -0.039044 0.885527 0.074 Uiso 1 1 calc R U . . .
C1 C 0.8025(3) 0.4684(2) 0.89485(9) 0.0597(7) Uani 1 1 d . . . . .
H011 H 0.706351 0.460635 0.888854 0.072 Uiso 1 1 calc R U . . .
C11 C 1.0363(3) 0.1294(3) 0.95425(9) 0.0676(8) Uani 1 1 d . . . . .
H012 H 1.034978 0.146228 0.985612 0.081 Uiso 1 1 calc R U . . .
C19 C 0.5250(3) 0.2166(2) 0.66233(9) 0.0620(7) Uani 1 1 d . . . . .
H013 H 0.479914 0.272437 0.646503 0.074 Uiso 1 1 calc R U . . .
C41 C 1.0216(3) 0.8393(2) 0.78511(10) 0.0642(7) Uani 1 1 d . . . . .
H41 H 1.081432 0.897233 0.788369 0.077 Uiso 1 1 calc R U . . .
C43 C 0.9433(3) 0.6728(2) 0.81518(9) 0.0648(7) Uani 1 1 d . . . . .
H015 H 0.949022 0.619892 0.837661 0.078 Uiso 1 1 calc R U . . .
C20 C 0.5244(3) 0.1167(2) 0.64383(10) 0.0629(7) Uani 1 1 d . . . . .
H016 H 0.479181 0.105158 0.614702 0.076 Uiso 1 1 calc R U . . .
C3 C 0.9941(4) 0.5539(2) 0.93488(10) 0.0701(8) Uani 1 1 d . . . . .
C4 C 1.0872(3) 0.4950(2) 0.91219(10) 0.0675(8) Uani 1 1 d . . . . .
H018 H 1.183067 0.504660 0.918143 0.081 Uiso 1 1 calc R U . . .
C42 C 1.0302(3) 0.7595(2) 0.81854(10) 0.0678(8) Uani 1 1 d . . . . .
H019 H 1.096049 0.765048 0.843647 0.081 Uiso 1 1 calc R U . . .
C32 C 0.4107(3) 0.7298(2) 0.57613(10) 0.0703(8) Uani 1 1 d . . . . .
H01A H 0.344172 0.692925 0.591743 0.084 Uiso 1 1 calc R U . . .
C36 C 0.6431(3) 0.7893(2) 0.57067(9) 0.0705(8) Uani 1 1 d . . . . .
H01B H 0.735987 0.792289 0.582339 0.085 Uiso 1 1 calc R U . . .
C24 C 0.2586(3) 0.4004(2) 0.61864(13) 0.0740(9) Uani 1 1 d . . . . .
H01C H 0.178301 0.372155 0.630254 0.089 Uiso 1 1 calc R U . . .
C25 C 0.2949(4) 0.3743(2) 0.57556(13) 0.0756(9) Uani 1 1 d . . . . .
C2 C 0.8533(4) 0.5429(2) 0.92697(10) 0.0738(9) Uani 1 1 d . . . . .
H01E H 0.792218 0.584578 0.942840 0.089 Uiso 1 1 calc R U . . .
C26 C 0.4105(4) 0.4144(2) 0.55684(10) 0.0735(9) Uani 1 1 d . . . . .
H01F H 0.433283 0.394796 0.527200 0.088 Uiso 1 1 calc R U . . .
C34 C 0.4686(4) 0.8328(3) 0.51206(10) 0.0800(10) Uani 1 1 d . . . . .
C33 C 0.3713(3) 0.7784(3) 0.53393(11) 0.0827(10) Uani 1 1 d . . . . .
H01H H 0.279740 0.773444 0.521089 0.099 Uiso 1 1 calc R U . . .
C35 C 0.6041(4) 0.8389(3) 0.52911(11) 0.0907(11) Uani 1 1 d . . . . .
H01I H 0.669574 0.875936 0.513062 0.109 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 C12 1.357(3) . ?
N2 C16 1.320(3) . ?
N2 C8 1.355(3) . ?
N5 C38 1.331(3) . ?
N5 C30 1.357(3) . ?
N1 C15 1.327(3) . ?
N1 C7 1.355(3) . ?
N4 C37 1.325(3) . ?
N4 C29 1.352(3) . ?
N3 C15 1.363(3) . ?
N3 C18 1.396(3) . ?
F2 C3 1.358(3) . ?
N6 C37 1.364(3) . ?
N6 C44 1.387(3) . ?
F3 C25 1.366(3) . ?
F4 C34 1.362(3) . ?
C7 C8 1.419(3) . ?
C7 C6 1.491(3) . ?
C16 C15 1.413(3) . ?
C16 C17 1.442(3) . ?
C8 C9 1.490(3) . ?
C9 C10 1.392(3) . ?
C9 C14 1.394(3) . ?
C17 C22 1.393(3) . ?
C17 C18 1.404(3) . ?
C38 C37 1.415(3) . ?
C38 C39 1.439(3) . ?
C29 C30 1.416(3) . ?
C29 C28 1.484(3) . ?
C30 C31 1.486(3) . ?
C6 C1 1.386(3) . ?
C6 C5 1.391(4) . ?
C28 C23 1.387(3) . ?
C28 C27 1.390(3) . ?
C18 C19 1.387(3) . ?
C39 C44 1.403(3) . ?
C39 C40 1.404(4) . ?
C31 C32 1.379(4) . ?
C31 C36 1.381(4) . ?
C14 C13 1.383(3) . ?
C44 C43 1.390(4) . ?
C5 C4 1.381(4) . ?
C22 C21 1.366(4) . ?
C10 C11 1.375(4) . ?
C40 C41 1.376(4) . ?
C27 C26 1.372(4) . ?
C23 C24 1.392(4) . ?
C21 C20 1.391(4) . ?
C12 C11 1.364(4) . ?
C12 C13 1.372(4) . ?
C1 C2 1.384(4) . ?
C19 C20 1.369(4) . ?
C41 C42 1.393(4) . ?
C43 C42 1.374(4) . ?
C3 C2 1.359(4) . ?
C3 C4 1.362(4) . ?
C32 C33 1.392(4) . ?
C36 C35 1.381(4) . ?
C24 C25 1.354(5) . ?
C25 C26 1.363(5) . ?
C34 C33 1.348(5) . ?
C34 C35 1.357(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
C16 N2 C8 116.70(19) . . ?
C38 N5 C30 116.7(2) . . ?
C15 N1 C7 115.39(19) . . ?
C37 N4 C29 115.61(19) . . ?
C15 N3 C18 108.46(19) . . ?
C37 N6 C44 108.6(2) . . ?
N1 C7 C8 121.8(2) . . ?
N1 C7 C6 114.43(19) . . ?
C8 C7 C6 123.7(2) . . ?
N2 C16 C15 121.8(2) . . ?
N2 C16 C17 131.2(2) . . ?
C15 C16 C17 106.99(18) . . ?
N2 C8 C7 121.1(2) . . ?
N2 C8 C9 113.44(19) . . ?
C7 C8 C9 125.4(2) . . ?
C10 C9 C14 117.8(2) . . ?
C10 C9 C8 123.9(2) . . ?
C14 C9 C8 118.1(2) . . ?
C22 C17 C18 119.6(2) . . ?
C22 C17 C16 134.6(2) . . ?
C18 C17 C16 105.8(2) . . ?
N5 C38 C37 120.9(2) . . ?
N5 C38 C39 132.2(2) . . ?
C37 C38 C39 106.8(2) . . ?
N1 C15 N3 127.5(2) . . ?
N1 C15 C16 123.2(2) . . ?
N3 C15 C16 109.2(2) . . ?
N4 C37 N6 127.1(2) . . ?
N4 C37 C38 123.6(2) . . ?
N6 C37 C38 109.1(2) . . ?
N4 C29 C30 121.7(2) . . ?
N4 C29 C28 114.62(19) . . ?
C30 C29 C28 123.7(2) . . ?
N5 C30 C29 121.4(2) . . ?
N5 C30 C31 114.6(2) . . ?
C29 C30 C31 124.0(2) . . ?
C1 C6 C5 118.5(2) . . ?
C1 C6 C7 119.3(2) . . ?
C5 C6 C7 122.1(2) . . ?
C23 C28 C27 118.1(2) . . ?
C23 C28 C29 120.0(2) . . ?
C27 C28 C29 121.8(2) . . ?
C19 C18 N3 129.3(2) . . ?
C19 C18 C17 121.2(2) . . ?
N3 C18 C17 109.4(2) . . ?
C44 C39 C40 118.9(2) . . ?
C44 C39 C38 105.9(2) . . ?
C40 C39 C38 135.1(2) . . ?
C32 C31 C36 117.8(2) . . ?
C32 C31 C30 123.8(2) . . ?
C36 C31 C30 118.4(2) . . ?
C13 C14 C9 121.3(2) . . ?
N6 C44 C43 128.5(2) . . ?
N6 C44 C39 109.6(2) . . ?
C43 C44 C39 121.9(2) . . ?
C4 C5 C6 120.7(2) . . ?
C21 C22 C17 119.0(2) . . ?
C11 C10 C9 121.4(3) . . ?
C41 C40 C39 118.9(3) . . ?
C26 C27 C28 121.6(3) . . ?
C28 C23 C24 120.3(3) . . ?
C22 C21 C20 120.6(3) . . ?
F1 C12 C11 119.3(3) . . ?
F1 C12 C13 118.3(3) . . ?
C11 C12 C13 122.4(2) . . ?
C12 C13 C14 118.2(3) . . ?
C2 C1 C6 120.7(3) . . ?
C12 C11 C10 118.8(3) . . ?
C20 C19 C18 117.6(2) . . ?
C40 C41 C42 121.1(3) . . ?
C42 C43 C44 117.8(3) . . ?
C19 C20 C21 122.0(2) . . ?
F2 C3 C2 118.4(3) . . ?
F2 C3 C4 119.1(3) . . ?
C2 C3 C4 122.5(3) . . ?
C3 C4 C5 118.7(3) . . ?
C43 C42 C41 121.4(3) . . ?
C31 C32 C33 121.2(3) . . ?
C35 C36 C31 121.2(3) . . ?
C25 C24 C23 119.0(3) . . ?
C24 C25 C26 122.7(3) . . ?
C24 C25 F3 118.4(3) . . ?
C26 C25 F3 118.9(3) . . ?
C3 C2 C1 118.7(3) . . ?
C25 C26 C27 118.3(3) . . ?
C33 C34 C35 122.2(3) . . ?
C33 C34 F4 118.6(3) . . ?
C35 C34 F4 119.1(3) . . ?
C34 C33 C32 118.6(3) . . ?
C34 C35 C36 118.9(3) . . ?

_refine_diff_density_max         0.188
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.035



