# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_hj44
_database_code_depnum_ccdc_archive 'CCDC 2001069'
loop_
_audit_author_name
_audit_author_address
'Dr. Nattamai Bhuvanesh'
;Texas AnM University, College Station, Texas, USA
United States of America
;
_audit_update_record             
;
2020-05-05 deposited with the CCDC.	2020-07-08 downloaded from the CCDC.
;
_audit_creation_date             2019-06-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C56 H52 Cl2 O4 Pd Se2'
_chemical_formula_sum            'C56 H52 Cl2 O4 Pd Se2'
_chemical_formula_weight         1124.19
_chemical_melting_point          ?
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2319(4)
_cell_length_b                   10.9599(5)
_cell_length_c                   14.1131(8)
_cell_angle_alpha                101.732(2)
_cell_angle_beta                 100.174(2)
_cell_angle_gamma                97.026(2)
_cell_volume                     1210.44(11)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    7141
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      27.493
_cell_measurement_theta_min      2.549
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.817
_exptl_absorpt_coefficient_mu    2.044
_exptl_absorpt_correction_T_max  0.3334
_exptl_absorpt_correction_T_min  0.2686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0929 before and 0.0421 after correction. The Ratio of minimum to maximum transmission is 0.8056. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.103
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.012
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11864
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.548
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3579
_reflns_number_total             4210
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'SAINT V8.38 Bruker AXS Inc., Madison, WI, USA.'
_computing_data_collection       ?
_computing_data_reduction        
'SAINT V8.38 Bruker AXS Inc., Madison, WI, USA.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0253
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0124P)²+1.0927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0491
_refine_ls_wR_factor_ref         0.0547
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C8(H8A,H8B), C15(H15A,H15B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C24(H24), C25(H25), C26(H26),
  C27(H27), C28(H28)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Pd1 Pd 0.500000 0.500000 0.500000 0.01856(8) Uani 1 2 d S T P . .
Se1 Se 0.55200(3) 0.64596(2) 0.39518(2) 0.02073(8) Uani 1 1 d . . . . .
Cl1 Cl 0.74305(8) 0.42319(6) 0.48648(5) 0.02809(16) Uani 1 1 d . . . . .
O1 O 0.6564(2) 0.95109(16) 0.41777(14) 0.0277(4) Uani 1 1 d . . . . .
O2 O 0.3452(2) 0.51157(18) 0.16211(14) 0.0307(5) Uani 1 1 d . . . . .
C1 C 0.7625(3) 0.7483(2) 0.4802(2) 0.0241(6) Uani 1 1 d . . . . .
H1A H 0.734783 0.807138 0.535969 0.029 Uiso 1 1 calc R . . . .
H1B H 0.831791 0.691338 0.508297 0.029 Uiso 1 1 calc R . . . .
C2 C 0.8620(3) 0.8224(2) 0.4264(2) 0.0241(6) Uani 1 1 d . . . . .
C3 C 1.0139(3) 0.7924(3) 0.4084(2) 0.0300(7) Uani 1 1 d . . . . .
H3 H 1.053801 0.723005 0.430383 0.036 Uiso 1 1 calc R . . . .
C4 C 1.1094(3) 0.8609(3) 0.3592(2) 0.0345(7) Uani 1 1 d . . . . .
H4 H 1.214011 0.839422 0.348367 0.041 Uiso 1 1 calc R . . . .
C5 C 1.0500(4) 0.9609(3) 0.3262(2) 0.0353(7) Uani 1 1 d . . . . .
H5 H 1.113332 1.007361 0.291251 0.042 Uiso 1 1 calc R . . . .
C6 C 0.8984(3) 0.9938(3) 0.3438(2) 0.0319(7) Uani 1 1 d . . . . .
H6 H 0.858286 1.062553 0.320975 0.038 Uiso 1 1 calc R . . . .
C7 C 0.8060(3) 0.9261(2) 0.3946(2) 0.0249(6) Uani 1 1 d . . . . .
C8 C 0.6044(4) 1.0687(2) 0.4071(2) 0.0306(7) Uani 1 1 d . . . . .
H8A H 0.705098 1.133656 0.419007 0.037 Uiso 1 1 calc R . . . .
H8B H 0.539824 1.095537 0.458312 0.037 Uiso 1 1 calc R . . . .
C9 C 0.4992(3) 1.0629(2) 0.3070(2) 0.0263(6) Uani 1 1 d . . . . .
C10 C 0.4360(3) 1.1714(3) 0.2906(2) 0.0297(7) Uani 1 1 d . . . . .
H10 H 0.464066 1.246772 0.341314 0.036 Uiso 1 1 calc R . . . .
C11 C 0.3341(4) 1.1702(3) 0.2021(2) 0.0360(7) Uani 1 1 d . . . . .
H11 H 0.292523 1.244709 0.191971 0.043 Uiso 1 1 calc R . . . .
C12 C 0.2916(4) 1.0609(3) 0.1276(2) 0.0434(8) Uani 1 1 d . . . . .
H12 H 0.220305 1.059559 0.066517 0.052 Uiso 1 1 calc R . . . .
C13 C 0.3543(4) 0.9538(3) 0.1433(2) 0.0444(8) Uani 1 1 d . . . . .
H13 H 0.326038 0.878603 0.092455 0.053 Uiso 1 1 calc R . . . .
C14 C 0.4581(4) 0.9547(3) 0.2324(2) 0.0360(7) Uani 1 1 d . . . . .
H14 H 0.501000 0.880517 0.241932 0.043 Uiso 1 1 calc R . . . .
C15 C 0.6486(3) 0.5526(2) 0.2887(2) 0.0256(6) Uani 1 1 d . . . . .
H15A H 0.769732 0.555806 0.313350 0.031 Uiso 1 1 calc R . . . .
H15B H 0.594497 0.462964 0.269805 0.031 Uiso 1 1 calc R . . . .
C16 C 0.6238(3) 0.6087(2) 0.1994(2) 0.0257(6) Uani 1 1 d . . . . .
C17 C 0.7538(4) 0.6834(3) 0.1770(2) 0.0330(7) Uani 1 1 d . . . . .
H17 H 0.861821 0.699008 0.218603 0.040 Uiso 1 1 calc R . . . .
C18 C 0.7293(4) 0.7356(3) 0.0952(2) 0.0390(8) Uani 1 1 d . . . . .
H18 H 0.819332 0.787829 0.081793 0.047 Uiso 1 1 calc R . . . .
C19 C 0.5749(4) 0.7116(3) 0.0335(2) 0.0375(7) Uani 1 1 d . . . . .
H19 H 0.558511 0.746976 -0.022937 0.045 Uiso 1 1 calc R . . . .
C20 C 0.4427(4) 0.6365(3) 0.0527(2) 0.0314(7) Uani 1 1 d . . . . .
H20 H 0.336089 0.619411 0.009494 0.038 Uiso 1 1 calc R . . . .
C21 C 0.4674(4) 0.5862(2) 0.1358(2) 0.0278(6) Uani 1 1 d . . . . .
C22 C 0.1779(4) 0.4968(3) 0.1060(2) 0.0343(7) Uani 1 1 d . . . . .
H22A H 0.172606 0.456326 0.035867 0.041 Uiso 1 1 calc R . . . .
H22B H 0.142104 0.580263 0.109122 0.041 Uiso 1 1 calc R . . . .
C23 C 0.0660(4) 0.4157(3) 0.1497(2) 0.0311(7) Uani 1 1 d . . . . .
C24 C -0.0429(4) 0.3115(3) 0.0901(2) 0.0403(8) Uani 1 1 d . . . . .
H24 H -0.043694 0.288581 0.021403 0.048 Uiso 1 1 calc R . . . .
C25 C -0.1520(4) 0.2398(3) 0.1311(3) 0.0508(9) Uani 1 1 d . . . . .
H25 H -0.228467 0.168750 0.090453 0.061 Uiso 1 1 calc R . . . .
C26 C -0.1470(4) 0.2738(4) 0.2312(3) 0.0502(10) Uani 1 1 d . . . . .
H26 H -0.223470 0.227483 0.259261 0.060 Uiso 1 1 calc R . . . .
C27 C -0.0340(4) 0.3726(3) 0.2903(3) 0.0448(9) Uani 1 1 d . . . . .
H27 H -0.028072 0.392021 0.359642 0.054 Uiso 1 1 calc R . . . .
C28 C 0.0719(4) 0.4446(3) 0.2502(2) 0.0385(8) Uani 1 1 d . . . . .
H28 H 0.149360 0.514449 0.291821 0.046 Uiso 1 1 calc R . . . .


_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
Pd1 Se1 2.4391(3) . ?
Pd1 Se1 2.4391(3) 2_666 ?
Pd1 Cl1 2.2869(6) 2_666 ?
Pd1 Cl1 2.2869(6) . ?
Se1 C1 1.986(3) . ?
Se1 C15 1.984(2) . ?
O1 C7 1.374(3) . ?
O1 C8 1.434(3) . ?
O2 C21 1.369(3) . ?
O2 C22 1.434(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.488(4) . ?
C2 C3 1.384(4) . ?
C2 C7 1.403(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.383(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.505(4) . ?
C9 C10 1.400(4) . ?
C9 C14 1.377(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.372(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(4) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.503(4) . ?
C16 C17 1.388(4) . ?
C16 C21 1.396(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.384(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.370(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.383(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.387(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.497(4) . ?
C23 C24 1.382(4) . ?
C23 C28 1.379(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.397(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.378(5) . ?
C26 H26 0.9500 . ?
C26 C27 1.359(5) . ?
C27 H27 0.9500 . ?
C27 C28 1.375(4) . ?
C28 H28 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
Se1 Pd1 Se1 180.0 2_666 . ?
Cl1 Pd1 Se1 92.149(17) . . ?
Cl1 Pd1 Se1 92.150(17) 2_666 2_666 ?
Cl1 Pd1 Se1 87.851(17) . 2_666 ?
Cl1 Pd1 Se1 87.850(17) 2_666 . ?
Cl1 Pd1 Cl1 180.0 . 2_666 ?
C1 Se1 Pd1 97.98(7) . . ?
C15 Se1 Pd1 105.94(7) . . ?
C15 Se1 C1 98.48(12) . . ?
C7 O1 C8 118.9(2) . . ?
C21 O2 C22 117.2(2) . . ?
Se1 C1 H1A 108.9 . . ?
Se1 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
C2 C1 Se1 113.27(18) . . ?
C2 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
C3 C2 C1 120.8(2) . . ?
C3 C2 C7 118.4(2) . . ?
C7 C2 C1 120.9(2) . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.7(3) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 119.1(3) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.5(3) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.8(3) . . ?
C7 C6 H6 120.1 . . ?
O1 C7 C2 114.4(2) . . ?
O1 C7 C6 125.0(2) . . ?
C6 C7 C2 120.5(2) . . ?
O1 C8 H8A 108.8 . . ?
O1 C8 H8B 108.8 . . ?
O1 C8 C9 113.9(2) . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C10 C9 C8 118.3(2) . . ?
C14 C9 C8 122.9(2) . . ?
C14 C9 C10 118.8(3) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.1(3) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
C9 C14 C13 120.2(3) . . ?
C9 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
Se1 C15 H15A 109.5 . . ?
Se1 C15 H15B 109.5 . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 Se1 110.94(17) . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C17 C16 C15 121.8(3) . . ?
C17 C16 C21 117.7(3) . . ?
C21 C16 C15 120.5(2) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 C16 121.4(3) . . ?
C18 C17 H17 119.3 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.5(3) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 120.3 . . ?
C19 C20 C21 119.4(3) . . ?
C21 C20 H20 120.3 . . ?
O2 C21 C16 114.7(2) . . ?
O2 C21 C20 124.2(3) . . ?
C20 C21 C16 121.2(3) . . ?
O2 C22 H22A 110.2 . . ?
O2 C22 H22B 110.2 . . ?
O2 C22 C23 107.7(2) . . ?
H22A C22 H22B 108.5 . . ?
C23 C22 H22A 110.2 . . ?
C23 C22 H22B 110.2 . . ?
C24 C23 C22 120.5(3) . . ?
C28 C23 C22 120.0(3) . . ?
C28 C23 C24 119.6(3) . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 119.9(3) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 120.5 . . ?
C26 C25 C24 119.0(3) . . ?
C26 C25 H25 120.5 . . ?
C25 C26 H26 119.6 . . ?
C27 C26 C25 120.8(3) . . ?
C27 C26 H26 119.6 . . ?
C26 C27 H27 119.8 . . ?
C26 C27 C28 120.4(3) . . ?
C28 C27 H27 119.8 . . ?
C23 C28 H28 119.9 . . ?
C27 C28 C23 120.2(3) . . ?
C27 C28 H28 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
Se1 C1 C2 C3 -111.3(3) . . . . ?
Se1 C1 C2 C7 70.2(3) . . . . ?
Se1 C15 C16 C17 104.3(3) . . . . ?
Se1 C15 C16 C21 -76.0(3) . . . . ?
O1 C8 C9 C10 177.3(2) . . . . ?
O1 C8 C9 C14 -0.6(4) . . . . ?
O2 C22 C23 C24 -129.2(3) . . . . ?
O2 C22 C23 C28 50.5(3) . . . . ?
C1 C2 C3 C4 -179.4(3) . . . . ?
C1 C2 C7 O1 0.2(4) . . . . ?
C1 C2 C7 C6 -179.4(3) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C3 C2 C7 O1 -178.4(2) . . . . ?
C3 C2 C7 C6 2.1(4) . . . . ?
C3 C4 C5 C6 1.3(5) . . . . ?
C4 C5 C6 C7 0.0(5) . . . . ?
C5 C6 C7 O1 178.8(3) . . . . ?
C5 C6 C7 C2 -1.7(4) . . . . ?
C7 O1 C8 C9 91.0(3) . . . . ?
C7 C2 C3 C4 -0.8(4) . . . . ?
C8 O1 C7 C2 167.5(2) . . . . ?
C8 O1 C7 C6 -13.0(4) . . . . ?
C8 C9 C10 C11 -177.5(3) . . . . ?
C8 C9 C14 C13 177.1(3) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
C10 C9 C14 C13 -0.8(4) . . . . ?
C10 C11 C12 C13 -0.6(5) . . . . ?
C11 C12 C13 C14 0.2(5) . . . . ?
C12 C13 C14 C9 0.5(5) . . . . ?
C14 C9 C10 C11 0.5(4) . . . . ?
C15 C16 C17 C18 -179.4(3) . . . . ?
C15 C16 C21 O2 0.1(4) . . . . ?
C15 C16 C21 C20 -179.5(2) . . . . ?
C16 C17 C18 C19 -1.3(4) . . . . ?
C17 C16 C21 O2 179.8(2) . . . . ?
C17 C16 C21 C20 0.2(4) . . . . ?
C17 C18 C19 C20 0.5(5) . . . . ?
C18 C19 C20 C21 0.6(4) . . . . ?
C19 C20 C21 O2 179.5(2) . . . . ?
C19 C20 C21 C16 -1.0(4) . . . . ?
C21 O2 C22 C23 -178.2(2) . . . . ?
C21 C16 C17 C18 0.9(4) . . . . ?
C22 O2 C21 C16 173.2(2) . . . . ?
C22 O2 C21 C20 -7.2(4) . . . . ?
C22 C23 C24 C25 -177.1(3) . . . . ?
C22 C23 C28 C27 178.1(3) . . . . ?
C23 C24 C25 C26 -0.9(5) . . . . ?
C24 C23 C28 C27 -2.2(4) . . . . ?
C24 C25 C26 C27 -2.3(5) . . . . ?
C25 C26 C27 C28 3.3(5) . . . . ?
C26 C27 C28 C23 -1.1(4) . . . . ?
C28 C23 C24 C25 3.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_nm262
_database_code_depnum_ccdc_archive 'CCDC 2001070'
loop_
_audit_author_name
_audit_author_address
'Dr. Nattamai Bhuvanesh'
;Texas AnM University, College Station, Texas, USA
United States of America
;
_audit_update_record             
;
2020-05-05 deposited with the CCDC.	2020-07-08 downloaded from the CCDC.
;
_audit_creation_date             2020-04-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H19 F N2'
_chemical_formula_sum            'C28 H19 F N2'
_chemical_formula_weight         402.45
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.8050(6)
_cell_length_b                   7.0310(3)
_cell_length_c                   24.4855(11)
_cell_angle_alpha                90
_cell_angle_beta                 103.258(2)
_cell_angle_gamma                90
_cell_volume                     1978.15(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8412
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      27.096
_cell_measurement_theta_min      2.763
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7398
_exptl_absorpt_correction_T_min  0.6886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0975 before and 0.0645 after correction. The Ratio of minimum to maximum transmission is 0.9308. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.032
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            19934
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.546
_diffrn_reflns_theta_min         2.763
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3131
_reflns_number_total             4525
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'SAINT V8.38 Bruker AXS Inc., Madison, WI, USA.'
_computing_data_collection       ?
_computing_data_reduction        
'SAINT V8.38 Bruker AXS Inc., Madison, WI, USA.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0105(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4525
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0333P)²+1.0378P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1128
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25), C27(H27), C28(H28)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.91726(9) 0.05284(16) 0.43330(4) 0.0302(3) Uani 1 1 d . . . . .
N1 N 0.35971(12) 0.3158(2) 0.52942(6) 0.0186(3) Uani 1 1 d . . . . .
N2 N 0.39946(12) 0.2503(2) 0.44782(6) 0.0205(3) Uani 1 1 d . . . . .
C1 C 0.31240(15) 0.2929(2) 0.47372(7) 0.0199(4) Uani 1 1 d . . . . .
C2 C 0.19218(15) 0.3104(3) 0.45889(7) 0.0232(4) Uani 1 1 d . . . . .
H2 H 0.150378 0.297775 0.420991 0.028 Uiso 1 1 calc R . . . .
C3 C 0.13500(16) 0.3474(2) 0.50161(7) 0.0227(4) Uani 1 1 d . . . . .
H3 H 0.052639 0.358489 0.491322 0.027 Uiso 1 1 calc R . . . .
C4 C 0.18923(15) 0.3695(2) 0.55879(7) 0.0212(4) Uani 1 1 d . . . . .
C5 C 0.31008(15) 0.3527(2) 0.57354(7) 0.0186(4) Uani 1 1 d . . . . .
C6 C 0.40778(15) 0.3465(2) 0.62126(7) 0.0192(4) Uani 1 1 d . . . . .
C7 C 0.50854(15) 0.3055(2) 0.60235(7) 0.0189(4) Uani 1 1 d . . . . .
C8 C 0.47601(14) 0.2860(2) 0.54240(7) 0.0183(4) Uani 1 1 d . . . . .
C9 C 0.49928(15) 0.2466(2) 0.48867(7) 0.0188(4) Uani 1 1 d . . . . .
C10 C 0.11751(16) 0.4057(3) 0.60120(7) 0.0260(4) Uani 1 1 d . . . . .
H10A H 0.144488 0.323058 0.633824 0.039 Uiso 1 1 calc GR . . . .
H10B H 0.035533 0.378519 0.584309 0.039 Uiso 1 1 calc GR . . . .
H10C H 0.125772 0.539043 0.613097 0.039 Uiso 1 1 calc GR . . . .
C11 C 0.40276(15) 0.3639(3) 0.68087(7) 0.0212(4) Uani 1 1 d . . . . .
C12 C 0.35292(16) 0.5209(3) 0.70085(8) 0.0264(4) Uani 1 1 d . . . . .
H12 H 0.320294 0.619702 0.675659 0.032 Uiso 1 1 calc R . . . .
C13 C 0.35019(17) 0.5352(3) 0.75710(8) 0.0310(5) Uani 1 1 d . . . . .
H13 H 0.315270 0.642710 0.770091 0.037 Uiso 1 1 calc R . . . .
C14 C 0.39835(16) 0.3929(3) 0.79419(8) 0.0333(5) Uani 1 1 d . . . . .
H14 H 0.397765 0.403452 0.832799 0.040 Uiso 1 1 calc R . . . .
C15 C 0.44726(16) 0.2355(3) 0.77497(8) 0.0316(5) Uani 1 1 d . . . . .
H15 H 0.479518 0.136905 0.800340 0.038 Uiso 1 1 calc R . . . .
C16 C 0.44948(15) 0.2207(3) 0.71869(7) 0.0241(4) Uani 1 1 d . . . . .
H16 H 0.483215 0.111690 0.705811 0.029 Uiso 1 1 calc R . . . .
C17 C 0.62708(15) 0.2939(3) 0.63915(7) 0.0199(4) Uani 1 1 d . . . . .
C18 C 0.67489(16) 0.4536(3) 0.66967(7) 0.0264(4) Uani 1 1 d . . . . .
H18 H 0.631176 0.568082 0.666797 0.032 Uiso 1 1 calc R . . . .
C19 C 0.78537(17) 0.4465(3) 0.70405(8) 0.0340(5) Uani 1 1 d . . . . .
H19 H 0.816989 0.555645 0.724974 0.041 Uiso 1 1 calc R . . . .
C20 C 0.85016(17) 0.2807(3) 0.70809(8) 0.0355(5) Uani 1 1 d . . . . .
H20 H 0.926584 0.276449 0.731299 0.043 Uiso 1 1 calc R . . . .
C21 C 0.80307(17) 0.1216(3) 0.67819(8) 0.0316(5) Uani 1 1 d . . . . .
H21 H 0.847151 0.007445 0.681212 0.038 Uiso 1 1 calc R . . . .
C22 C 0.69207(16) 0.1271(3) 0.64385(7) 0.0255(4) Uani 1 1 d . . . . .
H22 H 0.660317 0.017024 0.623500 0.031 Uiso 1 1 calc R . . . .
C23 C 0.60976(15) 0.2017(2) 0.47429(7) 0.0194(4) Uani 1 1 d . . . . .
C24 C 0.71484(15) 0.2120(3) 0.51390(7) 0.0225(4) Uani 1 1 d . . . . .
H24 H 0.715469 0.254096 0.550829 0.027 Uiso 1 1 calc R . . . .
C25 C 0.81875(16) 0.1618(3) 0.50045(7) 0.0242(4) Uani 1 1 d . . . . .
H25 H 0.890288 0.167730 0.527733 0.029 Uiso 1 1 calc R . . . .
C26 C 0.81538(15) 0.1034(3) 0.44674(7) 0.0227(4) Uani 1 1 d . . . . .
C27 C 0.71410(15) 0.0932(2) 0.40581(7) 0.0224(4) Uani 1 1 d . . . . .
H27 H 0.714849 0.052535 0.368892 0.027 Uiso 1 1 calc R . . . .
C28 C 0.61098(15) 0.1435(2) 0.41981(7) 0.0211(4) Uani 1 1 d . . . . .
H28 H 0.540113 0.138568 0.392040 0.025 Uiso 1 1 calc R . . . .


_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 C26 1.3648(19) . ?
N1 C1 1.360(2) . ?
N1 C5 1.367(2) . ?
N1 C8 1.353(2) . ?
N2 C1 1.359(2) . ?
N2 C9 1.360(2) . ?
C1 C2 1.387(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.408(2) . ?
C4 C5 1.394(2) . ?
C4 C10 1.504(2) . ?
C5 C6 1.442(2) . ?
C6 C7 1.402(2) . ?
C6 C11 1.479(2) . ?
C7 C8 1.436(2) . ?
C7 C17 1.483(2) . ?
C8 C9 1.431(2) . ?
C9 C23 1.461(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.391(2) . ?
C11 C16 1.394(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.389(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.380(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.394(2) . ?
C17 C22 1.391(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.382(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.385(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.382(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.386(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(2) . ?
C23 C28 1.398(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.387(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.369(2) . ?
C26 C27 1.375(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.384(2) . ?
C28 H28 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
C1 N1 C5 131.56(15) . . ?
C8 N1 C1 112.25(14) . . ?
C8 N1 C5 116.08(14) . . ?
C1 N2 C9 106.35(14) . . ?
N1 C1 C2 114.35(15) . . ?
N2 C1 N1 108.27(14) . . ?
N2 C1 C2 137.31(16) . . ?
C1 C2 H2 121.2 . . ?
C1 C2 C3 117.56(16) . . ?
C3 C2 H2 121.2 . . ?
C2 C3 H3 117.3 . . ?
C2 C3 C4 125.38(17) . . ?
C4 C3 H3 117.3 . . ?
C3 C4 C10 120.36(16) . . ?
C5 C4 C3 116.94(16) . . ?
C5 C4 C10 122.69(15) . . ?
N1 C5 C4 114.21(15) . . ?
N1 C5 C6 103.10(14) . . ?
C4 C5 C6 142.50(16) . . ?
C5 C6 C11 126.26(15) . . ?
C7 C6 C5 108.67(14) . . ?
C7 C6 C11 124.89(15) . . ?
C6 C7 C8 108.01(14) . . ?
C6 C7 C17 124.37(15) . . ?
C8 C7 C17 127.57(15) . . ?
N1 C8 C7 104.14(14) . . ?
N1 C8 C9 102.26(14) . . ?
C9 C8 C7 153.55(16) . . ?
N2 C9 C8 110.84(14) . . ?
N2 C9 C23 119.85(14) . . ?
C8 C9 C23 129.29(15) . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C6 121.90(16) . . ?
C12 C11 C16 118.33(16) . . ?
C16 C11 C6 119.77(16) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 120.94(18) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 119.95(18) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.85(17) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.21(19) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.71(18) . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C7 119.40(16) . . ?
C22 C17 C7 121.48(16) . . ?
C22 C17 C18 119.11(16) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.47(18) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.16(19) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.67(18) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.53(19) . . ?
C22 C21 H21 119.7 . . ?
C17 C22 H22 120.0 . . ?
C21 C22 C17 120.05(18) . . ?
C21 C22 H22 120.0 . . ?
C24 C23 C9 121.57(15) . . ?
C24 C23 C28 118.55(16) . . ?
C28 C23 C9 119.87(16) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 C23 121.16(16) . . ?
C25 C24 H24 119.4 . . ?
C24 C25 H25 120.9 . . ?
C26 C25 C24 118.15(17) . . ?
C26 C25 H25 120.9 . . ?
F1 C26 C25 118.46(16) . . ?
F1 C26 C27 118.54(15) . . ?
C25 C26 C27 123.00(17) . . ?
C26 C27 H27 120.9 . . ?
C26 C27 C28 118.25(16) . . ?
C28 C27 H27 120.9 . . ?
C23 C28 H28 119.6 . . ?
C27 C28 C23 120.87(16) . . ?
C27 C28 H28 119.6 . . ?

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
F1 C26 C27 C28 179.60(15) . . . . ?
N1 C1 C2 C3 -0.4(2) . . . . ?
N1 C5 C6 C7 -0.30(19) . . . . ?
N1 C5 C6 C11 -175.52(16) . . . . ?
N1 C8 C9 N2 -1.35(18) . . . . ?
N1 C8 C9 C23 -179.74(16) . . . . ?
N2 C1 C2 C3 176.2(2) . . . . ?
N2 C9 C23 C24 174.55(16) . . . . ?
N2 C9 C23 C28 -6.6(2) . . . . ?
C1 N1 C5 C4 0.1(3) . . . . ?
C1 N1 C5 C6 176.17(17) . . . . ?
C1 N1 C8 C7 -176.83(14) . . . . ?
C1 N1 C8 C9 1.64(18) . . . . ?
C1 N2 C9 C8 0.58(19) . . . . ?
C1 N2 C9 C23 179.14(15) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C2 C3 C4 C10 -178.90(17) . . . . ?
C3 C4 C5 N1 -0.1(2) . . . . ?
C3 C4 C5 C6 -173.8(2) . . . . ?
C4 C5 C6 C7 173.8(2) . . . . ?
C4 C5 C6 C11 -1.4(4) . . . . ?
C5 N1 C1 N2 -177.40(16) . . . . ?
C5 N1 C1 C2 0.2(3) . . . . ?
C5 N1 C8 C7 -0.16(19) . . . . ?
C5 N1 C8 C9 178.31(14) . . . . ?
C5 C6 C7 C8 0.22(19) . . . . ?
C5 C6 C7 C17 177.87(16) . . . . ?
C5 C6 C11 C12 -56.7(3) . . . . ?
C5 C6 C11 C16 123.64(19) . . . . ?
C6 C7 C8 N1 -0.05(18) . . . . ?
C6 C7 C8 C9 -176.7(3) . . . . ?
C6 C7 C17 C18 -60.9(2) . . . . ?
C6 C7 C17 C22 119.3(2) . . . . ?
C6 C11 C12 C13 -179.34(17) . . . . ?
C6 C11 C16 C15 179.03(16) . . . . ?
C7 C6 C11 C12 128.80(19) . . . . ?
C7 C6 C11 C16 -50.8(3) . . . . ?
C7 C8 C9 N2 175.3(3) . . . . ?
C7 C8 C9 C23 -3.1(5) . . . . ?
C7 C17 C18 C19 -179.71(17) . . . . ?
C7 C17 C22 C21 179.35(16) . . . . ?
C8 N1 C1 N2 -1.4(2) . . . . ?
C8 N1 C1 C2 176.19(15) . . . . ?
C8 N1 C5 C4 -175.78(15) . . . . ?
C8 N1 C5 C6 0.29(19) . . . . ?
C8 C7 C17 C18 116.3(2) . . . . ?
C8 C7 C17 C22 -63.5(2) . . . . ?
C8 C9 C23 C24 -7.2(3) . . . . ?
C8 C9 C23 C28 171.68(17) . . . . ?
C9 N2 C1 N1 0.44(19) . . . . ?
C9 N2 C1 C2 -176.3(2) . . . . ?
C9 C23 C24 C25 177.42(16) . . . . ?
C9 C23 C28 C27 -177.48(16) . . . . ?
C10 C4 C5 N1 178.63(16) . . . . ?
C10 C4 C5 C6 4.9(4) . . . . ?
C11 C6 C7 C8 175.53(16) . . . . ?
C11 C6 C7 C17 -6.8(3) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C12 C11 C16 C15 -0.6(3) . . . . ?
C12 C13 C14 C15 -1.1(3) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C14 C15 C16 C11 0.1(3) . . . . ?
C16 C11 C12 C13 0.3(3) . . . . ?
C17 C7 C8 N1 -177.60(16) . . . . ?
C17 C7 C8 C9 5.8(5) . . . . ?
C17 C18 C19 C20 0.6(3) . . . . ?
C18 C17 C22 C21 -0.5(3) . . . . ?
C18 C19 C20 C21 -0.9(3) . . . . ?
C19 C20 C21 C22 0.6(3) . . . . ?
C20 C21 C22 C17 0.1(3) . . . . ?
C22 C17 C18 C19 0.1(3) . . . . ?
C23 C24 C25 C26 0.7(3) . . . . ?
C24 C23 C28 C27 1.4(3) . . . . ?
C24 C25 C26 F1 -179.64(16) . . . . ?
C24 C25 C26 C27 0.2(3) . . . . ?
C25 C26 C27 C28 -0.3(3) . . . . ?
C26 C27 C28 C23 -0.6(3) . . . . ?
C28 C23 C24 C25 -1.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
