# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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 1442080'
_audit_update_record             
;
2015-12-12 deposited with the CCDC.
2016-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ebptpy
_chemical_name_common            ebp-terpyridine
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H23 N3 O2'
_chemical_formula_sum            'C30 H23 N3 O2'
_chemical_formula_weight         457.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 '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                   14.190(3)
_cell_length_b                   8.0680(16)
_cell_length_c                   22.427(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.06(3)
_cell_angle_gamma                90
_cell_volume                     2528.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    49225
_cell_measurement_theta_min      0.40
_cell_measurement_theta_max      29.54

_exptl_crystal_description       Cubic
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.993
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   'HKL3000 Scalepack'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.700
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24909
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.435
_diffrn_reflns_theta_max         29.533
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             7263
_reflns_number_gt                5456
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'PAL ADSC Quantum-210 ADX Program'
_computing_cell_refinement       HKL3000
_computing_data_reduction        HKL3000
_computing_structure_solution    'SHELXS-2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  WINGX
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1045P)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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.024(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7263
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1608
_refine_ls_wR_factor_gt          0.1508
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.127
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.76459(7) -0.09425(11) 0.60068(4) 0.0301(2) Uani 1 1 d . . . . .
N2 N 0.56380(6) 0.15785(10) 0.53318(4) 0.0255(2) Uani 1 1 d . . . . .
N3 N 0.40746(6) 0.41588(11) 0.42706(5) 0.0304(2) Uani 1 1 d . . . . .
O1 O 1.12332(5) 0.10379(11) 0.10115(4) 0.0354(2) Uani 1 1 d . . . . .
O2 O 0.99502(5) 0.22068(9) 0.04327(3) 0.02798(18) Uani 1 1 d . . . . .
C1 C 0.62538(8) -0.01511(14) 0.64105(6) 0.0329(3) Uani 1 1 d . . . . .
H1 H 0.5664 0.0432 0.6360 0.039 Uiso 1 1 calc R U . . .
C2 C 0.65790(10) -0.10124(16) 0.69375(6) 0.0406(3) Uani 1 1 d . . . . .
H2 H 0.6216 -0.1032 0.7256 0.049 Uiso 1 1 calc R U . . .
C3 C 0.74385(10) -0.18441(16) 0.69950(6) 0.0409(3) Uani 1 1 d . . . . .
H3 H 0.7677 -0.2454 0.7352 0.049 Uiso 1 1 calc R U . . .
C4 C 0.79452(9) -0.17720(14) 0.65232(6) 0.0364(3) Uani 1 1 d . . . . .
H4 H 0.8539 -0.2342 0.6567 0.044 Uiso 1 1 calc R U . . .
C5 C 0.68012(7) -0.01476(12) 0.59539(5) 0.0260(2) Uani 1 1 d . . . . .
C6 C 0.64581(7) 0.07260(11) 0.53714(5) 0.0238(2) Uani 1 1 d . . . . .
C7 C 0.69717(7) 0.06271(12) 0.48985(5) 0.0243(2) Uani 1 1 d . . . . .
H7 H 0.7559 0.0034 0.4948 0.029 Uiso 1 1 calc R U . . .
C8 C 0.66163(7) 0.14070(12) 0.43525(5) 0.0246(2) Uani 1 1 d . . . . .
C9 C 0.57531(7) 0.22668(12) 0.43071(5) 0.0255(2) Uani 1 1 d . . . . .
H9 H 0.5482 0.2795 0.3938 0.031 Uiso 1 1 calc R U . . .
C10 C 0.52930(7) 0.23450(12) 0.48049(5) 0.0248(2) Uani 1 1 d . . . . .
C11 C 0.43820(7) 0.32820(12) 0.47782(5) 0.0274(2) Uani 1 1 d . . . . .
C12 C 0.32495(8) 0.49916(13) 0.42368(6) 0.0351(3) Uani 1 1 d . . . . .
H12 H 0.3023 0.5604 0.3879 0.042 Uiso 1 1 calc R U . . .
C13 C 0.27089(8) 0.50115(14) 0.46926(7) 0.0375(3) Uani 1 1 d . . . . .
H13 H 0.2128 0.5620 0.4648 0.045 Uiso 1 1 calc R U . . .
C14 C 0.30345(8) 0.41243(14) 0.52142(7) 0.0372(3) Uani 1 1 d . . . . .
H14 H 0.2682 0.4114 0.5537 0.045 Uiso 1 1 calc R U . . .
C15 C 0.38846(8) 0.32485(13) 0.52591(6) 0.0322(3) Uani 1 1 d . . . . .
H15 H 0.4124 0.2633 0.5615 0.039 Uiso 1 1 calc R U . . .
C16 C 0.71491(7) 0.13711(13) 0.38394(5) 0.0254(2) Uani 1 1 d . . . . .
C17 C 0.76800(7) -0.00202(12) 0.37230(5) 0.0261(2) Uani 1 1 d . . . . .
H17 H 0.7683 -0.0981 0.3968 0.031 Uiso 1 1 calc R U . . .
C18 C 0.81999(8) -0.00128(12) 0.32559(5) 0.0265(2) Uani 1 1 d . . . . .
H18 H 0.8555 -0.0969 0.3185 0.032 Uiso 1 1 calc R U . . .
C19 C 0.82118(7) 0.13839(12) 0.28859(5) 0.0257(2) Uani 1 1 d . . . . .
C20 C 0.76713(8) 0.27616(13) 0.29999(5) 0.0275(2) Uani 1 1 d . . . . .
H20 H 0.7662 0.3718 0.2752 0.033 Uiso 1 1 calc R U . . .
C21 C 0.71511(8) 0.27585(12) 0.34668(5) 0.0270(2) Uani 1 1 d . . . . .
H21 H 0.6791 0.3711 0.3535 0.032 Uiso 1 1 calc R U . . .
C22 C 0.87732(7) 0.14130(12) 0.23855(5) 0.0253(2) Uani 1 1 d . . . . .
C23 C 0.96169(8) 0.04976(13) 0.24139(5) 0.0303(2) Uani 1 1 d . . . . .
H23 H 0.9835 -0.0172 0.2759 0.036 Uiso 1 1 calc R U . . .
C24 C 1.01384(8) 0.05503(13) 0.19491(5) 0.0305(2) Uani 1 1 d . . . . .
H24 H 1.0712 -0.0075 0.1978 0.037 Uiso 1 1 calc R U . . .
C25 C 0.98283(7) 0.15174(12) 0.14360(5) 0.0255(2) Uani 1 1 d . . . . .
C26 C 0.89904(7) 0.24388(12) 0.13994(5) 0.0256(2) Uani 1 1 d . . . . .
H26 H 0.8773 0.3101 0.1052 0.031 Uiso 1 1 calc R U . . .
C27 C 0.84733(7) 0.23890(13) 0.18695(5) 0.0261(2) Uani 1 1 d . . . . .
H27 H 0.7905 0.3028 0.1842 0.031 Uiso 1 1 calc R U . . .
C28 C 1.04197(7) 0.15488(12) 0.09506(5) 0.0265(2) Uani 1 1 d . . . . .
C29 C 1.04830(8) 0.22775(14) -0.00664(5) 0.0298(2) Uani 1 1 d . . . . .
H29A H 1.0675 0.1149 -0.0171 0.036 Uiso 1 1 calc R U . . .
H29B H 1.1067 0.2959 0.0047 0.036 Uiso 1 1 calc R U . . .
C30 C 0.98300(9) 0.30434(16) -0.05967(5) 0.0363(3) Uani 1 1 d . . . . .
H30A H 0.9256 0.2356 -0.0705 0.054 Uiso 1 1 calc R U . . .
H30B H 1.0165 0.3115 -0.0943 0.054 Uiso 1 1 calc R U . . .
H30C H 0.9645 0.4158 -0.0487 0.054 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C4 1.3409(15) . ?
N1 C5 1.3463(14) . ?
N2 C6 1.3413(13) . ?
N2 C10 1.3477(14) . ?
N3 C12 1.3405(14) . ?
N3 C11 1.3467(15) . ?
O1 C28 1.2108(12) . ?
O2 C28 1.3434(14) . ?
O2 C29 1.4572(14) . ?
C1 C2 1.3791(18) . ?
C1 C5 1.3892(17) . ?
C1 H1 0.9500 . ?
C2 C3 1.3782(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.3804(19) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C5 C6 1.4893(15) . ?
C6 C7 1.3901(16) . ?
C7 C8 1.3907(15) . ?
C7 H7 0.9500 . ?
C8 C9 1.3958(14) . ?
C8 C16 1.4833(15) . ?
C9 C10 1.3897(16) . ?
C9 H9 0.9500 . ?
C10 C11 1.4897(15) . ?
C11 C15 1.3885(16) . ?
C12 C13 1.3811(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.3864(16) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.3972(15) . ?
C16 C17 1.4016(15) . ?
C17 C18 1.3826(16) . ?
C17 H17 0.9500 . ?
C18 C19 1.4012(15) . ?
C18 H18 0.9500 . ?
C19 C20 1.3991(15) . ?
C19 C22 1.4855(15) . ?
C20 C21 1.3824(16) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.3987(15) . ?
C22 C27 1.4029(15) . ?
C23 C24 1.3805(17) . ?
C23 H23 0.9500 . ?
C24 C25 1.3963(16) . ?
C24 H24 0.9500 . ?
C25 C26 1.3924(14) . ?
C25 C28 1.4863(16) . ?
C26 C27 1.3863(16) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C29 C30 1.5066(17) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?

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 C5 117.17(11) . . ?
C6 N2 C10 118.13(10) . . ?
C12 N3 C11 117.50(11) . . ?
C28 O2 C29 115.73(8) . . ?
C2 C1 C5 119.09(11) . . ?
C2 C1 H1 120.5 . . ?
C5 C1 H1 120.5 . . ?
C3 C2 C1 118.94(12) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 118.59(11) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
N1 C4 C3 123.67(12) . . ?
N1 C4 H4 118.2 . . ?
C3 C4 H4 118.2 . . ?
N1 C5 C1 122.54(10) . . ?
N1 C5 C6 116.89(10) . . ?
C1 C5 C6 120.55(10) . . ?
N2 C6 C7 122.91(10) . . ?
N2 C6 C5 116.59(10) . . ?
C7 C6 C5 120.49(9) . . ?
C6 C7 C8 119.21(9) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C7 C8 C9 117.88(10) . . ?
C7 C8 C16 121.24(9) . . ?
C9 C8 C16 120.85(9) . . ?
C10 C9 C8 119.57(10) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
N2 C10 C9 122.26(9) . . ?
N2 C10 C11 116.61(10) . . ?
C9 C10 C11 121.12(10) . . ?
N3 C11 C15 122.24(10) . . ?
N3 C11 C10 116.82(10) . . ?
C15 C11 C10 120.94(10) . . ?
N3 C12 C13 123.82(12) . . ?
N3 C12 H12 118.1 . . ?
C13 C12 H12 118.1 . . ?
C14 C13 C12 118.31(10) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C13 C14 C15 118.96(12) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C14 C15 C11 119.17(11) . . ?
C14 C15 H15 120.4 . . ?
C11 C15 H15 120.4 . . ?
C21 C16 C17 118.22(10) . . ?
C21 C16 C8 120.19(9) . . ?
C17 C16 C8 121.57(9) . . ?
C18 C17 C16 120.87(9) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 121.02(10) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 117.83(10) . . ?
C20 C19 C22 120.60(9) . . ?
C18 C19 C22 121.57(9) . . ?
C21 C20 C19 121.29(10) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C16 120.77(10) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?
C23 C22 C27 117.90(10) . . ?
C23 C22 C19 121.66(9) . . ?
C27 C22 C19 120.44(9) . . ?
C24 C23 C22 121.12(10) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C25 120.41(10) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C26 C25 C24 119.34(10) . . ?
C26 C25 C28 122.23(10) . . ?
C24 C25 C28 118.43(9) . . ?
C27 C26 C25 119.97(10) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C27 C22 121.27(9) . . ?
C26 C27 H27 119.4 . . ?
C22 C27 H27 119.4 . . ?
O1 C28 O2 123.44(11) . . ?
O1 C28 C25 124.12(10) . . ?
O2 C28 C25 112.44(8) . . ?
O2 C29 C30 107.00(9) . . ?
O2 C29 H29A 110.3 . . ?
C30 C29 H29A 110.3 . . ?
O2 C29 H29B 110.3 . . ?
C30 C29 H29B 110.3 . . ?
H29A C29 H29B 108.6 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

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
C5 C1 C2 C3 0.02(18) . . . . ?
C1 C2 C3 C4 0.47(18) . . . . ?
C5 N1 C4 C3 -0.18(16) . . . . ?
C2 C3 C4 N1 -0.41(18) . . . . ?
C4 N1 C5 C1 0.70(15) . . . . ?
C4 N1 C5 C6 -178.10(9) . . . . ?
C2 C1 C5 N1 -0.63(16) . . . . ?
C2 C1 C5 C6 178.12(10) . . . . ?
C10 N2 C6 C7 1.21(14) . . . . ?
C10 N2 C6 C5 -178.15(8) . . . . ?
N1 C5 C6 N2 -177.05(8) . . . . ?
C1 C5 C6 N2 4.13(14) . . . . ?
N1 C5 C6 C7 3.58(14) . . . . ?
C1 C5 C6 C7 -175.25(9) . . . . ?
N2 C6 C7 C8 -1.61(14) . . . . ?
C5 C6 C7 C8 177.72(9) . . . . ?
C6 C7 C8 C9 0.29(14) . . . . ?
C6 C7 C8 C16 178.53(8) . . . . ?
C7 C8 C9 C10 1.31(14) . . . . ?
C16 C8 C9 C10 -176.94(8) . . . . ?
C6 N2 C10 C9 0.50(14) . . . . ?
C6 N2 C10 C11 -179.89(8) . . . . ?
C8 C9 C10 N2 -1.77(14) . . . . ?
C8 C9 C10 C11 178.64(9) . . . . ?
C12 N3 C11 C15 -1.20(14) . . . . ?
C12 N3 C11 C10 179.18(9) . . . . ?
N2 C10 C11 N3 174.82(8) . . . . ?
C9 C10 C11 N3 -5.56(14) . . . . ?
N2 C10 C11 C15 -4.80(14) . . . . ?
C9 C10 C11 C15 174.81(9) . . . . ?
C11 N3 C12 C13 0.68(16) . . . . ?
N3 C12 C13 C14 0.01(16) . . . . ?
C12 C13 C14 C15 -0.21(16) . . . . ?
C13 C14 C15 C11 -0.28(16) . . . . ?
N3 C11 C15 C14 1.02(15) . . . . ?
C10 C11 C15 C14 -179.37(10) . . . . ?
C7 C8 C16 C21 -142.97(10) . . . . ?
C9 C8 C16 C21 35.22(14) . . . . ?
C7 C8 C16 C17 35.40(14) . . . . ?
C9 C8 C16 C17 -146.42(10) . . . . ?
C21 C16 C17 C18 0.68(15) . . . . ?
C8 C16 C17 C18 -177.72(9) . . . . ?
C16 C17 C18 C19 0.03(15) . . . . ?
C17 C18 C19 C20 -0.77(15) . . . . ?
C17 C18 C19 C22 179.53(9) . . . . ?
C18 C19 C20 C21 0.81(15) . . . . ?
C22 C19 C20 C21 -179.49(9) . . . . ?
C19 C20 C21 C16 -0.10(15) . . . . ?
C17 C16 C21 C20 -0.64(15) . . . . ?
C8 C16 C21 C20 177.78(9) . . . . ?
C20 C19 C22 C23 150.26(10) . . . . ?
C18 C19 C22 C23 -30.05(15) . . . . ?
C20 C19 C22 C27 -28.88(14) . . . . ?
C18 C19 C22 C27 150.81(10) . . . . ?
C27 C22 C23 C24 -0.06(16) . . . . ?
C19 C22 C23 C24 -179.22(9) . . . . ?
C22 C23 C24 C25 -0.41(17) . . . . ?
C23 C24 C25 C26 0.46(16) . . . . ?
C23 C24 C25 C28 179.33(9) . . . . ?
C24 C25 C26 C27 -0.03(15) . . . . ?
C28 C25 C26 C27 -178.86(9) . . . . ?
C25 C26 C27 C22 -0.45(15) . . . . ?
C23 C22 C27 C26 0.49(15) . . . . ?
C19 C22 C27 C26 179.66(9) . . . . ?
C29 O2 C28 O1 0.00(15) . . . . ?
C29 O2 C28 C25 -179.86(8) . . . . ?
C26 C25 C28 O1 165.08(11) . . . . ?
C24 C25 C28 O1 -13.77(15) . . . . ?
C26 C25 C28 O2 -15.06(14) . . . . ?
C24 C25 C28 O2 166.10(9) . . . . ?
C28 O2 C29 C30 179.82(9) . . . . ?

_refine_diff_density_max         0.367
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.065



####################################################################### 
# 
# 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 1442081'
_audit_update_record             
;
2015-12-12 deposited with the CCDC.
2016-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        etptpy
_chemical_name_common            etp-terpyridine
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H27 N3 O2'
_chemical_formula_sum            'C36 H27 N3 O2'
_chemical_formula_weight         533.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 '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                   22.883(5)
_cell_length_b                   8.3520(17)
_cell_length_c                   14.445(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.61(3)
_cell_angle_gamma                90
_cell_volume                     2645.5(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    55177
_cell_measurement_theta_min      0.40
_cell_measurement_theta_max      29.54

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.992
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   'HKL3000 Scalepack'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.700
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27074
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.829
_diffrn_reflns_theta_max         29.535
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             7725
_reflns_number_gt                6600
_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       'PLA ADSC Quantum-210 ADX Program'
_computing_cell_refinement       HKL3000
_computing_data_reduction        HKL3000
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  WINGX
_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)+(0.1022P)²+0.3418P] 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         7725
_refine_ls_number_parameters     371
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1480
_refine_ls_wR_factor_gt          0.1422
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      2.639
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.48954(4) 0.37543(10) 0.15410(6) 0.02039(17) Uani 1 1 d . . . . .
N2 N 0.41635(4) 0.11853(9) -0.04649(5) 0.01546(16) Uani 1 1 d . . . . .
N3 N 0.30144(4) -0.12997(10) -0.20511(6) 0.01955(17) Uani 1 1 d . . . . .
O1 O -0.12787(3) 0.31809(9) 0.62321(5) 0.02130(16) Uani 1 1 d . . . . .
O2 O -0.17830(3) 0.11598(8) 0.53169(5) 0.01931(15) Uani 1 1 d . . . . .
C1 C 0.52682(4) 0.28765(12) 0.02300(7) 0.01752(18) Uani 1 1 d . . . . .
H1 H 0.5210 0.2250 -0.0338 0.021 Uiso 1 1 calc R U . . .
C2 C 0.57935(4) 0.37848(12) 0.05837(7) 0.02050(19) Uani 1 1 d . . . . .
H2 H 0.6101 0.3788 0.0260 0.025 Uiso 1 1 calc R U . . .
C3 C 0.58636(4) 0.46852(12) 0.14139(7) 0.0212(2) Uani 1 1 d . . . . .
H3 H 0.6216 0.5328 0.1666 0.025 Uiso 1 1 calc R U . . .
C4 C 0.54040(5) 0.46211(13) 0.18663(7) 0.0227(2) Uani 1 1 d . . . . .
H4 H 0.5454 0.5228 0.2440 0.027 Uiso 1 1 calc R U . . .
C5 C 0.48270(4) 0.29036(11) 0.07274(6) 0.01572(17) Uani 1 1 d . . . . .
C6 C 0.42432(4) 0.20087(11) 0.03615(6) 0.01479(17) Uani 1 1 d . . . . .
C7 C 0.38022(4) 0.20836(11) 0.08601(6) 0.01533(17) Uani 1 1 d . . . . .
H7 H 0.3883 0.2661 0.1450 0.018 Uiso 1 1 calc R U . . .
C8 C 0.32425(4) 0.13075(11) 0.04883(6) 0.01404(17) Uani 1 1 d . . . . .
C9 C 0.31618(4) 0.04608(11) -0.03747(6) 0.01518(17) Uani 1 1 d . . . . .
H9 H 0.2789 -0.0084 -0.0659 0.018 Uiso 1 1 calc DR U . . .
C10 C 0.36302(4) 0.04178(11) -0.08165(6) 0.01439(17) Uani 1 1 d . . . . .
C11 C 0.35436(4) -0.05007(11) -0.17295(6) 0.01502(17) Uani 1 1 d . . . . .
C12 C 0.29206(5) -0.21322(13) -0.28674(7) 0.0229(2) Uani 1 1 d . . . . .
H12 H 0.2547 -0.2698 -0.3100 0.028 Uiso 1 1 calc DR U . . .
C13 C 0.33413(5) -0.22184(13) -0.33998(7) 0.0219(2) Uani 1 1 d . . . . .
H13 H 0.3258 -0.2833 -0.3976 0.026 Uiso 1 1 calc R U . . .
C14 C 0.38843(5) -0.13807(12) -0.30632(7) 0.02049(19) Uani 1 1 d . . . . .
H14 H 0.4180 -0.1408 -0.3409 0.025 Uiso 1 1 calc R U . . .
C15 C 0.39901(4) -0.05025(11) -0.22166(6) 0.01752(18) Uani 1 1 d . . . . .
H15 H 0.4358 0.0084 -0.1974 0.021 Uiso 1 1 calc R U . . .
C16 C 0.27518(4) 0.13920(11) 0.09739(6) 0.01480(17) Uani 1 1 d . . . . .
C17 C 0.28107(5) 0.23696(13) 0.17785(7) 0.0239(2) Uani 1 1 d . . . . .
H17 H 0.3172 0.2985 0.2019 0.029 Uiso 1 1 calc R U . . .
C18 C 0.23550(5) 0.24642(13) 0.22355(7) 0.0237(2) Uani 1 1 d . . . . .
H18 H 0.2410 0.3145 0.2781 0.028 Uiso 1 1 calc R U . . .
C19 C 0.18163(4) 0.15803(11) 0.19125(6) 0.01515(17) Uani 1 1 d . . . . .
C20 C 0.17544(4) 0.06126(11) 0.11006(7) 0.01720(18) Uani 1 1 d . . . . .
H20 H 0.1393 0.0000 0.0858 0.021 Uiso 1 1 calc R U . . .
C21 C 0.22106(4) 0.05270(12) 0.06396(7) 0.01769(18) Uani 1 1 d . . . . .
H21 H 0.2152 -0.0134 0.0086 0.021 Uiso 1 1 calc R U . . .
C22 C 0.13387(4) 0.16549(11) 0.24229(6) 0.01457(17) Uani 1 1 d . . . . .
C23 C 0.12928(4) 0.29872(11) 0.29898(6) 0.01646(18) Uani 1 1 d . . . . .
H23 H 0.1561 0.3869 0.3026 0.020 Uiso 1 1 calc R U . . .
C24 C 0.08623(4) 0.30384(11) 0.34997(6) 0.01650(18) Uani 1 1 d . . . . .
H24 H 0.0843 0.3950 0.3883 0.020 Uiso 1 1 calc R U . . .
C25 C 0.04556(4) 0.17699(11) 0.34586(6) 0.01500(17) Uani 1 1 d . . . . .
C26 C 0.04950(4) 0.04464(11) 0.28824(6) 0.01611(17) Uani 1 1 d . . . . .
H26 H 0.0222 -0.0425 0.2837 0.019 Uiso 1 1 calc R U . . .
C27 C 0.09287(4) 0.03903(11) 0.23758(6) 0.01608(17) Uani 1 1 d . . . . .
H27 H 0.0947 -0.0521 0.1992 0.019 Uiso 1 1 calc R U . . .
C28 C -0.00015(4) 0.18394(11) 0.40066(6) 0.01521(17) Uani 1 1 d . . . . .
C29 C 0.01271(4) 0.26580(12) 0.48892(7) 0.01866(19) Uani 1 1 d . . . . .
H29 H 0.0515 0.3144 0.5146 0.022 Uiso 1 1 calc R U . . .
C30 C -0.03060(4) 0.27663(12) 0.53921(7) 0.01880(19) Uani 1 1 d . . . . .
H30 H -0.0216 0.3345 0.5982 0.023 Uiso 1 1 calc R U . . .
C31 C -0.08714(4) 0.20287(11) 0.50335(6) 0.01584(17) Uani 1 1 d . . . . .
C32 C -0.10028(4) 0.11839(12) 0.41648(7) 0.01868(19) Uani 1 1 d . . . . .
H32 H -0.1385 0.0661 0.3923 0.022 Uiso 1 1 calc R U . . .
C33 C -0.05725(4) 0.11088(12) 0.36528(7) 0.01831(18) Uani 1 1 d . . . . .
H33 H -0.0668 0.0553 0.3054 0.022 Uiso 1 1 calc R U . . .
C34 C -0.13212(4) 0.22001(11) 0.55952(6) 0.01596(17) Uani 1 1 d . . . . .
C35 C -0.22259(4) 0.12038(12) 0.58655(7) 0.01918(19) Uani 1 1 d . . . . .
H35A H -0.2475 0.2189 0.5715 0.023 Uiso 1 1 calc R U . . .
H35B H -0.2017 0.1181 0.6568 0.023 Uiso 1 1 calc R U . . .
C36 C -0.26205(5) -0.02555(13) 0.55709(7) 0.0227(2) Uani 1 1 d . . . . .
H36A H -0.2838 -0.0193 0.4881 0.034 Uiso 1 1 calc R U . . .
H36B H -0.2916 -0.0307 0.5944 0.034 Uiso 1 1 calc R U . . .
H36C H -0.2365 -0.1217 0.5696 0.034 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C4 1.3367(13) . ?
N1 C5 1.3436(12) . ?
N2 C10 1.3430(12) . ?
N2 C6 1.3441(11) . ?
N3 C12 1.3324(12) . ?
N3 C11 1.3440(12) . ?
O1 C34 1.2148(11) . ?
O2 C34 1.3381(11) . ?
O2 C35 1.4545(11) . ?
C1 C2 1.3894(13) . ?
C1 C5 1.3966(12) . ?
C1 H1 0.9500 . ?
C2 C3 1.3855(14) . ?
C2 H2 0.9500 . ?
C3 C4 1.3888(13) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C5 C6 1.4898(13) . ?
C6 C7 1.3987(12) . ?
C7 C8 1.3985(13) . ?
C7 H7 0.9500 . ?
C8 C9 1.3987(12) . ?
C8 C16 1.4861(12) . ?
C9 C10 1.3958(12) . ?
C9 H9 0.9500 . ?
C10 C11 1.4892(12) . ?
C11 C15 1.3965(12) . ?
C12 C13 1.3953(13) . ?
C12 H12 0.9500 . ?
C13 C14 1.3871(15) . ?
C13 H13 0.9500 . ?
C14 C15 1.3868(13) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.3949(13) . ?
C16 C21 1.3952(13) . ?
C17 C18 1.3869(12) . ?
C17 H17 0.9500 . ?
C18 C19 1.3976(13) . ?
C18 H18 0.9500 . ?
C19 C20 1.3978(12) . ?
C19 C22 1.4842(12) . ?
C20 C21 1.3912(12) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C27 1.4013(12) . ?
C22 C23 1.4033(13) . ?
C23 C24 1.3890(12) . ?
C23 H23 0.9500 . ?
C24 C25 1.4001(13) . ?
C24 H24 0.9500 . ?
C25 C26 1.4020(13) . ?
C25 C28 1.4824(12) . ?
C26 C27 1.3922(12) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C33 1.3996(13) . ?
C28 C29 1.4018(13) . ?
C29 C30 1.3892(12) . ?
C29 H29 0.9500 . ?
C30 C31 1.3924(13) . ?
C30 H30 0.9500 . ?
C31 C32 1.3953(13) . ?
C31 C34 1.4885(12) . ?
C32 C33 1.3916(12) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C35 C36 1.5042(14) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?

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 C5 117.77(8) . . ?
C10 N2 C6 117.25(8) . . ?
C12 N3 C11 117.79(8) . . ?
C34 O2 C35 115.68(7) . . ?
C2 C1 C5 118.60(8) . . ?
C2 C1 H1 120.7 . . ?
C5 C1 H1 120.7 . . ?
C3 C2 C1 119.24(9) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 118.07(9) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
N1 C4 C3 123.76(9) . . ?
N1 C4 H4 118.1 . . ?
C3 C4 H4 118.1 . . ?
N1 C5 C1 122.55(9) . . ?
N1 C5 C6 116.36(8) . . ?
C1 C5 C6 121.07(8) . . ?
N2 C6 C7 123.06(8) . . ?
N2 C6 C5 116.87(8) . . ?
C7 C6 C5 120.04(8) . . ?
C8 C7 C6 119.85(8) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 116.72(8) . . ?
C7 C8 C16 121.96(8) . . ?
C9 C8 C16 121.31(8) . . ?
C10 C9 C8 119.84(8) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
N2 C10 C9 123.25(8) . . ?
N2 C10 C11 117.20(8) . . ?
C9 C10 C11 119.54(8) . . ?
N3 C11 C15 122.83(8) . . ?
N3 C11 C10 116.13(8) . . ?
C15 C11 C10 121.03(8) . . ?
N3 C12 C13 123.56(9) . . ?
N3 C12 H12 118.2 . . ?
C13 C12 H12 118.2 . . ?
C14 C13 C12 118.08(9) . . ?
C14 C13 H13 121.0 . . ?
C12 C13 H13 121.0 . . ?
C15 C14 C13 119.28(9) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C11 118.45(9) . . ?
C14 C15 H15 120.8 . . ?
C11 C15 H15 120.8 . . ?
C17 C16 C21 117.15(8) . . ?
C17 C16 C8 120.99(8) . . ?
C21 C16 C8 121.85(8) . . ?
C18 C17 C16 121.54(9) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C19 121.50(9) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C18 C19 C20 116.97(8) . . ?
C18 C19 C22 121.10(8) . . ?
C20 C19 C22 121.92(8) . . ?
C21 C20 C19 121.43(8) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C21 C16 121.39(8) . . ?
C20 C21 H21 119.3 . . ?
C16 C21 H21 119.3 . . ?
C27 C22 C23 117.73(8) . . ?
C27 C22 C19 121.47(8) . . ?
C23 C22 C19 120.78(8) . . ?
C24 C23 C22 121.10(8) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C25 121.19(8) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C24 C25 C26 117.83(8) . . ?
C24 C25 C28 120.64(8) . . ?
C26 C25 C28 121.52(8) . . ?
C27 C26 C25 121.01(8) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C26 C27 C22 121.13(8) . . ?
C26 C27 H27 119.4 . . ?
C22 C27 H27 119.4 . . ?
C33 C28 C29 118.43(8) . . ?
C33 C28 C25 121.03(8) . . ?
C29 C28 C25 120.53(8) . . ?
C30 C29 C28 120.78(8) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C29 C30 C31 120.17(8) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C30 C31 C32 119.79(8) . . ?
C30 C31 C34 117.93(8) . . ?
C32 C31 C34 122.28(8) . . ?
C33 C32 C31 119.83(9) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C32 C33 C28 120.98(8) . . ?
C32 C33 H33 119.5 . . ?
C28 C33 H33 119.5 . . ?
O1 C34 O2 123.42(8) . . ?
O1 C34 C31 124.03(8) . . ?
O2 C34 C31 112.55(8) . . ?
O2 C35 C36 106.31(7) . . ?
O2 C35 H35A 110.5 . . ?
C36 C35 H35A 110.5 . . ?
O2 C35 H35B 110.5 . . ?
C36 C35 H35B 110.5 . . ?
H35A C35 H35B 108.7 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

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
C5 C1 C2 C3 -0.02(14) . . . . ?
C1 C2 C3 C4 0.84(14) . . . . ?
C5 N1 C4 C3 -0.24(15) . . . . ?
C2 C3 C4 N1 -0.74(16) . . . . ?
C4 N1 C5 C1 1.13(14) . . . . ?
C4 N1 C5 C6 -177.40(9) . . . . ?
C2 C1 C5 N1 -1.00(14) . . . . ?
C2 C1 C5 C6 177.45(8) . . . . ?
C10 N2 C6 C7 0.45(13) . . . . ?
C10 N2 C6 C5 -177.89(8) . . . . ?
N1 C5 C6 N2 178.41(8) . . . . ?
C1 C5 C6 N2 -0.14(13) . . . . ?
N1 C5 C6 C7 0.02(13) . . . . ?
C1 C5 C6 C7 -178.52(8) . . . . ?
N2 C6 C7 C8 -1.48(13) . . . . ?
C5 C6 C7 C8 176.80(8) . . . . ?
C6 C7 C8 C9 1.04(13) . . . . ?
C6 C7 C8 C16 -178.08(8) . . . . ?
C7 C8 C9 C10 0.29(13) . . . . ?
C16 C8 C9 C10 179.41(8) . . . . ?
C6 N2 C10 C9 0.99(13) . . . . ?
C6 N2 C10 C11 -179.70(7) . . . . ?
C8 C9 C10 N2 -1.37(13) . . . . ?
C8 C9 C10 C11 179.34(8) . . . . ?
C12 N3 C11 C15 0.47(14) . . . . ?
C12 N3 C11 C10 179.86(8) . . . . ?
N2 C10 C11 N3 177.98(8) . . . . ?
C9 C10 C11 N3 -2.68(12) . . . . ?
N2 C10 C11 C15 -2.62(13) . . . . ?
C9 C10 C11 C15 176.72(8) . . . . ?
C11 N3 C12 C13 0.14(15) . . . . ?
N3 C12 C13 C14 -0.52(16) . . . . ?
C12 C13 C14 C15 0.29(15) . . . . ?
C13 C14 C15 C11 0.27(14) . . . . ?
N3 C11 C15 C14 -0.67(14) . . . . ?
C10 C11 C15 C14 179.97(8) . . . . ?
C7 C8 C16 C17 5.70(14) . . . . ?
C9 C8 C16 C17 -173.38(9) . . . . ?
C7 C8 C16 C21 -175.44(9) . . . . ?
C9 C8 C16 C21 5.48(13) . . . . ?
C21 C16 C17 C18 0.81(15) . . . . ?
C8 C16 C17 C18 179.72(9) . . . . ?
C16 C17 C18 C19 0.19(17) . . . . ?
C17 C18 C19 C20 -0.79(15) . . . . ?
C17 C18 C19 C22 178.28(9) . . . . ?
C18 C19 C20 C21 0.39(14) . . . . ?
C22 C19 C20 C21 -178.67(8) . . . . ?
C19 C20 C21 C16 0.62(14) . . . . ?
C17 C16 C21 C20 -1.21(14) . . . . ?
C8 C16 C21 C20 179.89(8) . . . . ?
C18 C19 C22 C27 -154.46(10) . . . . ?
C20 C19 C22 C27 24.57(13) . . . . ?
C18 C19 C22 C23 24.01(13) . . . . ?
C20 C19 C22 C23 -156.97(9) . . . . ?
C27 C22 C23 C24 1.05(13) . . . . ?
C19 C22 C23 C24 -177.47(8) . . . . ?
C22 C23 C24 C25 -0.61(14) . . . . ?
C23 C24 C25 C26 -0.25(13) . . . . ?
C23 C24 C25 C28 179.97(8) . . . . ?
C24 C25 C26 C27 0.63(13) . . . . ?
C28 C25 C26 C27 -179.59(8) . . . . ?
C25 C26 C27 C22 -0.17(13) . . . . ?
C23 C22 C27 C26 -0.67(13) . . . . ?
C19 C22 C27 C26 177.84(8) . . . . ?
C24 C25 C28 C33 147.59(9) . . . . ?
C26 C25 C28 C33 -32.18(13) . . . . ?
C24 C25 C28 C29 -31.67(13) . . . . ?
C26 C25 C28 C29 148.56(9) . . . . ?
C33 C28 C29 C30 -1.15(14) . . . . ?
C25 C28 C29 C30 178.13(8) . . . . ?
C28 C29 C30 C31 1.41(14) . . . . ?
C29 C30 C31 C32 -0.22(14) . . . . ?
C29 C30 C31 C34 -179.25(8) . . . . ?
C30 C31 C32 C33 -1.21(14) . . . . ?
C34 C31 C32 C33 177.78(8) . . . . ?
C31 C32 C33 C28 1.47(14) . . . . ?
C29 C28 C33 C32 -0.29(14) . . . . ?
C25 C28 C33 C32 -179.57(8) . . . . ?
C35 O2 C34 O1 -3.35(13) . . . . ?
C35 O2 C34 C31 177.14(7) . . . . ?
C30 C31 C34 O1 15.12(14) . . . . ?
C32 C31 C34 O1 -163.89(9) . . . . ?
C30 C31 C34 O2 -165.37(8) . . . . ?
C32 C31 C34 O2 15.62(12) . . . . ?
C34 O2 C35 C36 -168.71(8) . . . . ?

_refine_diff_density_max         0.401
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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 1442082'
_audit_update_record             
;
2016-08-26 deposited with the CCDC.
2016-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        pfpatpy
_chemical_name_common            pfpatpy
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H10 F5 N3'
_chemical_formula_sum            'C23 H10 F5 N3'
_chemical_formula_weight         423.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0020 0.0010 '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 0.0050 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0140 0.0080 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   6.5270(13)
_cell_length_b                   7.9030(16)
_cell_length_c                   18.016(4)
_cell_angle_alpha                95.78(3)
_cell_angle_beta                 95.32(3)
_cell_angle_gamma                94.15(3)
_cell_volume                     917.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10804
_cell_measurement_theta_min      0.36
_cell_measurement_theta_max      29.48

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   'HKL3000 Scalepack'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8072
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.304
_diffrn_reflns_theta_max         29.517
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.616
_diffrn_measured_fraction_theta_full 0.755
_diffrn_reflns_Laue_measured_fraction_max 0.616
_diffrn_reflns_Laue_measured_fraction_full 0.755
_diffrn_reflns_point_group_measured_fraction_max 0.616
_diffrn_reflns_point_group_measured_fraction_full 0.755
_reflns_number_total             4530
_reflns_number_gt                3646
_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       'PAL ADSC Quantum-210 ADX program'
_computing_cell_refinement       HKL3000
_computing_data_reduction        HKL3000
_computing_structure_solution    'SHELXS-2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  WINGX
_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)+(0.1585P)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_number_reflns         4530
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0662
_refine_ls_wR_factor_ref         0.1991
_refine_ls_wR_factor_gt          0.1830
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
N1 N 0.6285(2) 1.17439(18) 0.57198(8) 0.0323(3) Uani 1 1 d . . . . .
N2 N 0.67576(16) 1.42249(15) 0.75176(7) 0.0215(3) Uani 1 1 d . . . . .
N3 N 0.55302(17) 1.62562(16) 0.92689(7) 0.0252(3) Uani 1 1 d . . . . .
F1 F -0.22827(14) 0.82162(13) 0.64470(6) 0.0335(2) Uani 1 1 d . . . . .
F2 F -0.60663(15) 0.65806(12) 0.64432(6) 0.0346(2) Uani 1 1 d . . . . .
F3 F -0.82807(12) 0.71612(12) 0.76283(6) 0.0328(2) Uani 1 1 d . . . . .
F4 F -0.67008(13) 0.93906(12) 0.88321(5) 0.0305(2) Uani 1 1 d . . . . .
F5 F -0.29180(13) 1.10107(11) 0.88483(5) 0.0283(2) Uani 1 1 d . . . . .
C1 C 0.8983(2) 1.38623(18) 0.62502(9) 0.0249(3) Uani 1 1 d . . . . .
H1 H 0.9506 1.4708 0.6648 0.030 Uiso 1 1 calc R U . . .
C2 C 1.0081(2) 1.35132(19) 0.56312(9) 0.0286(3) Uani 1 1 d . . . . .
H2 H 1.1374 1.4122 0.5600 0.034 Uiso 1 1 calc R U . . .
C3 C 0.9272(2) 1.2282(2) 0.50678(10) 0.0348(4) Uani 1 1 d . . . . .
H3 H 1.0001 1.2017 0.4644 0.042 Uiso 1 1 calc R U . . .
C4 C 0.7363(3) 1.1428(2) 0.51287(11) 0.0394(4) Uani 1 1 d . . . . .
H4 H 0.6799 1.0586 0.4735 0.047 Uiso 1 1 calc R U . . .
C5 C 0.70870(19) 1.29279(17) 0.62662(8) 0.0231(3) Uani 1 1 d . . . . .
C6 C 0.58846(18) 1.31835(17) 0.69307(8) 0.0212(3) Uani 1 1 d . . . . .
C7 C 0.39405(19) 1.22904(18) 0.69152(9) 0.0231(3) Uani 1 1 d . . . . .
H7 H 0.3355 1.1566 0.6483 0.028 Uiso 1 1 calc R U . . .
C8 C 0.28937(18) 1.25040(17) 0.75582(8) 0.0225(3) Uani 1 1 d . . . . .
C9 C 0.37697(18) 1.36170(17) 0.81677(8) 0.0227(3) Uani 1 1 d . . . . .
H9 H 0.3062 1.3814 0.8602 0.027 Uiso 1 1 calc R U . . .
C10 C 0.57231(19) 1.44444(17) 0.81286(8) 0.0214(3) Uani 1 1 d . . . . .
C11 C 0.67605(19) 1.55734(17) 0.87798(8) 0.0220(3) Uani 1 1 d . . . . .
C12 C 0.6437(2) 1.7280(2) 0.98601(9) 0.0288(3) Uani 1 1 d . . . . .
H12 H 0.5579 1.7789 1.0203 0.035 Uiso 1 1 calc R U . . .
C13 C 0.8566(2) 1.7649(2) 1.00063(9) 0.0292(3) Uani 1 1 d . . . . .
H13 H 0.9141 1.8380 1.0438 0.035 Uiso 1 1 calc R U . . .
C14 C 0.9822(2) 1.6918(2) 0.95027(9) 0.0308(3) Uani 1 1 d . . . . .
H14 H 1.1280 1.7133 0.9585 0.037 Uiso 1 1 calc R U . . .
C15 C 0.89152(19) 1.58730(19) 0.88800(8) 0.0263(3) Uani 1 1 d . . . . .
H15 H 0.9740 1.5366 0.8525 0.032 Uiso 1 1 calc R U . . .
C16 C 0.09750(19) 1.15175(18) 0.75912(9) 0.0246(3) Uani 1 1 d . . . . .
C17 C -0.05759(19) 1.06424(18) 0.76290(9) 0.0251(3) Uani 1 1 d . . . . .
C18 C -0.25026(18) 0.96717(17) 0.76411(8) 0.0227(3) Uani 1 1 d . . . . .
C19 C -0.3333(2) 0.85263(18) 0.70427(9) 0.0244(3) Uani 1 1 d . . . . .
C20 C -0.5283(2) 0.76783(18) 0.70274(9) 0.0256(3) Uani 1 1 d . . . . .
C21 C -0.64052(19) 0.79738(17) 0.76403(9) 0.0254(3) Uani 1 1 d . . . . .
C22 C -0.56094(19) 0.90838(17) 0.82469(9) 0.0238(3) Uani 1 1 d . . . . .
C23 C -0.36577(19) 0.99201(17) 0.82557(8) 0.0228(3) 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
N1 C5 1.329(2) . ?
N1 C4 1.3423(19) . ?
N2 C6 1.329(2) . ?
N2 C10 1.3469(16) . ?
N3 C12 1.334(2) . ?
N3 C11 1.3457(16) . ?
F1 C19 1.3375(15) . ?
F2 C20 1.3318(19) . ?
F3 C21 1.3379(14) . ?
F4 C22 1.3382(15) . ?
F5 C23 1.3321(19) . ?
C1 C2 1.3957(18) . ?
C1 C5 1.3984(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.372(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(2) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C5 C6 1.4961(18) . ?
C6 C7 1.4032(18) . ?
C7 C8 1.4006(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.386(2) . ?
C8 C16 1.4358(18) . ?
C9 C10 1.4012(17) . ?
C9 H9 0.9500 . ?
C10 C11 1.478(2) . ?
C11 C15 1.4009(17) . ?
C12 C13 1.394(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.1953(18) . ?
C17 C18 1.4280(17) . ?
C18 C19 1.378(2) . ?
C18 C23 1.4020(18) . ?
C19 C20 1.3918(19) . ?
C20 C21 1.390(2) . ?
C21 C22 1.367(2) . ?
C22 C23 1.3900(18) . ?

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
C5 N1 C4 118.05(13) . . ?
C6 N2 C10 118.48(11) . . ?
C12 N3 C11 117.36(12) . . ?
C2 C1 C5 117.91(15) . . ?
C2 C1 H1 121.0 . . ?
C5 C1 H1 121.0 . . ?
C3 C2 C1 119.30(13) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 118.76(13) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
N1 C4 C3 122.83(17) . . ?
N1 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
N1 C5 C1 123.16(12) . . ?
N1 C5 C6 116.35(12) . . ?
C1 C5 C6 120.45(14) . . ?
N2 C6 C7 123.37(12) . . ?
N2 C6 C5 117.45(11) . . ?
C7 C6 C5 119.16(14) . . ?
C8 C7 C6 117.70(15) . . ?
C8 C7 H7 121.2 . . ?
C6 C7 H7 121.2 . . ?
C9 C8 C7 119.39(12) . . ?
C9 C8 C16 120.80(12) . . ?
C7 C8 C16 119.76(14) . . ?
C8 C9 C10 118.49(12) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
N2 C10 C9 122.52(14) . . ?
N2 C10 C11 117.16(11) . . ?
C9 C10 C11 120.29(12) . . ?
N3 C11 C15 122.60(14) . . ?
N3 C11 C10 116.45(12) . . ?
C15 C11 C10 120.93(12) . . ?
N3 C12 C13 124.05(13) . . ?
N3 C12 H12 118.0 . . ?
C13 C12 H12 118.0 . . ?
C14 C13 C12 118.06(15) . . ?
C14 C13 H13 121.0 . . ?
C12 C13 H13 121.0 . . ?
C15 C14 C13 118.94(13) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C11 118.98(12) . . ?
C14 C15 H15 120.5 . . ?
C11 C15 H15 120.5 . . ?
C17 C16 C8 177.24(15) . . ?
C16 C17 C18 176.00(16) . . ?
C19 C18 C23 117.84(12) . . ?
C19 C18 C17 121.69(12) . . ?
C23 C18 C17 120.41(14) . . ?
F1 C19 C18 120.40(12) . . ?
F1 C19 C20 117.72(15) . . ?
C18 C19 C20 121.86(13) . . ?
F2 C20 C21 119.99(12) . . ?
F2 C20 C19 121.11(13) . . ?
C21 C20 C19 118.90(15) . . ?
F3 C21 C22 120.31(12) . . ?
F3 C21 C20 119.12(15) . . ?
C22 C21 C20 120.57(12) . . ?
F4 C22 C21 120.65(12) . . ?
F4 C22 C23 119.39(14) . . ?
C21 C22 C23 119.96(12) . . ?
F5 C23 C22 119.08(12) . . ?
F5 C23 C18 120.05(12) . . ?
C22 C23 C18 120.83(15) . . ?

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
C5 C1 C2 C3 0.0(2) . . . . ?
C1 C2 C3 C4 0.6(2) . . . . ?
C5 N1 C4 C3 0.2(3) . . . . ?
C2 C3 C4 N1 -0.7(3) . . . . ?
C4 N1 C5 C1 0.5(3) . . . . ?
C4 N1 C5 C6 -177.24(15) . . . . ?
C2 C1 C5 N1 -0.6(2) . . . . ?
C2 C1 C5 C6 177.07(12) . . . . ?
C10 N2 C6 C7 -0.4(2) . . . . ?
C10 N2 C6 C5 -178.53(11) . . . . ?
N1 C5 C6 N2 172.94(12) . . . . ?
C1 C5 C6 N2 -4.9(2) . . . . ?
N1 C5 C6 C7 -5.3(2) . . . . ?
C1 C5 C6 C7 176.85(12) . . . . ?
N2 C6 C7 C8 -0.8(2) . . . . ?
C5 C6 C7 C8 177.38(11) . . . . ?
C6 C7 C8 C9 2.2(2) . . . . ?
C6 C7 C8 C16 -175.19(12) . . . . ?
C7 C8 C9 C10 -2.4(2) . . . . ?
C16 C8 C9 C10 174.88(12) . . . . ?
C6 N2 C10 C9 0.06(19) . . . . ?
C6 N2 C10 C11 178.35(11) . . . . ?
C8 C9 C10 N2 1.4(2) . . . . ?
C8 C9 C10 C11 -176.88(11) . . . . ?
C12 N3 C11 C15 1.3(2) . . . . ?
C12 N3 C11 C10 -179.95(12) . . . . ?
N2 C10 C11 N3 157.69(12) . . . . ?
C9 C10 C11 N3 -23.98(18) . . . . ?
N2 C10 C11 C15 -23.53(18) . . . . ?
C9 C10 C11 C15 154.80(13) . . . . ?
C11 N3 C12 C13 -1.4(2) . . . . ?
N3 C12 C13 C14 0.5(2) . . . . ?
C12 C13 C14 C15 0.5(2) . . . . ?
C13 C14 C15 C11 -0.5(2) . . . . ?
N3 C11 C15 C14 -0.4(2) . . . . ?
C10 C11 C15 C14 -179.07(13) . . . . ?
C23 C18 C19 F1 -178.80(12) . . . . ?
C17 C18 C19 F1 4.1(2) . . . . ?
C23 C18 C19 C20 2.3(2) . . . . ?
C17 C18 C19 C20 -174.81(13) . . . . ?
F1 C19 C20 F2 0.8(2) . . . . ?
C18 C19 C20 F2 179.70(12) . . . . ?
F1 C19 C20 C21 179.82(12) . . . . ?
C18 C19 C20 C21 -1.2(2) . . . . ?
F2 C20 C21 F3 -0.9(2) . . . . ?
C19 C20 C21 F3 -179.98(12) . . . . ?
F2 C20 C21 C22 179.30(12) . . . . ?
C19 C20 C21 C22 0.2(2) . . . . ?
F3 C21 C22 F4 -0.9(2) . . . . ?
C20 C21 C22 F4 178.91(12) . . . . ?
F3 C21 C22 C23 179.86(12) . . . . ?
C20 C21 C22 C23 -0.4(2) . . . . ?
F4 C22 C23 F5 -0.01(19) . . . . ?
C21 C22 C23 F5 179.28(11) . . . . ?
F4 C22 C23 C18 -177.82(11) . . . . ?
C21 C22 C23 C18 1.5(2) . . . . ?
C19 C18 C23 F5 179.82(11) . . . . ?
C17 C18 C23 F5 -3.0(2) . . . . ?
C19 C18 C23 C22 -2.4(2) . . . . ?
C17 C18 C23 C22 174.75(12) . . . . ?

_refine_diff_density_max         0.481
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.076

####################################################################### 
# 
# 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 1442083'
_audit_update_record             
;
2015-12-12 deposited with the CCDC.
2016-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        bzotpy
_chemical_name_common            bzo-terpyridine
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H17 N3 O'
_chemical_formula_sum            'C22 H17 N3 O'
_chemical_formula_weight         339.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   5.7140(11)
_cell_length_b                   16.831(3)
_cell_length_c                   17.555(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.54(3)
_cell_angle_gamma                90
_cell_volume                     1686.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    34500
_cell_measurement_theta_min      0.40
_cell_measurement_theta_max      29.54

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   'HKL3000 Scalepack'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.700
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17300
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.652
_diffrn_reflns_theta_max         29.539
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4886
_reflns_number_gt                4273
_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       'PAL ADSC Quantum-210 ADX Program'
_computing_cell_refinement       HKL3000
_computing_data_reduction        HKL3000
_computing_structure_solution    'SHELXS-2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  WINGX
_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)+(0.0819P)²+0.3501P] 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         4886
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1307
_refine_ls_wR_factor_gt          0.1262
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.82032(14) 0.60465(5) 0.02128(4) 0.01673(17) Uani 1 1 d . . . . .
N2 N 0.64679(13) 0.77887(4) 0.12465(4) 0.01287(16) Uani 1 1 d . . . . .
N3 N 0.64868(14) 0.93385(5) 0.26658(4) 0.01675(17) Uani 1 1 d . . . . .
O1 O 1.24885(12) 0.71300(4) 0.24991(4) 0.01520(15) Uani 1 1 d . . . . .
C1 C 0.46739(15) 0.68207(6) 0.00513(5) 0.01538(18) Uani 1 1 d . . . . .
H1 H 0.3736 0.7248 0.0217 0.018 Uiso 1 1 calc R U . . .
C2 C 0.39141(16) 0.63444(6) -0.05586(5) 0.01746(19) Uani 1 1 d . . . . .
H2 H 0.2447 0.6442 -0.0817 0.021 Uiso 1 1 calc R U . . .
C3 C 0.53272(17) 0.57257(6) -0.07835(5) 0.01829(19) Uani 1 1 d . . . . .
H3 H 0.4868 0.5399 -0.1205 0.022 Uiso 1 1 calc R U . . .
C4 C 0.74355(17) 0.55956(6) -0.03759(5) 0.01887(19) Uani 1 1 d . . . . .
H4 H 0.8384 0.5163 -0.0523 0.023 Uiso 1 1 calc R U . . .
C5 C 0.68472(15) 0.66575(5) 0.04146(5) 0.01267(17) Uani 1 1 d . . . . .
C6 C 0.77750(15) 0.71578(5) 0.10619(5) 0.01212(17) Uani 1 1 d . . . . .
C7 C 0.98598(15) 0.69524(5) 0.14535(5) 0.01261(17) Uani 1 1 d . . . . .
H7 H 1.0782 0.6521 0.1287 0.015 Uiso 1 1 calc R U . . .
C8 C 1.05624(15) 0.73943(5) 0.20952(5) 0.01211(17) Uani 1 1 d . . . . .
C9 C 0.92444(15) 0.80521(5) 0.22947(5) 0.01276(17) Uani 1 1 d . . . . .
H9 H 0.9702 0.8373 0.2721 0.015 Uiso 1 1 calc R U . . .
C10 C 0.72263(15) 0.82250(5) 0.18467(5) 0.01191(17) Uani 1 1 d . . . . .
C11 C 0.57530(15) 0.89171(5) 0.20499(5) 0.01233(17) Uani 1 1 d . . . . .
C12 C 0.51439(18) 0.99448(6) 0.28763(5) 0.01863(19) Uani 1 1 d . . . . .
H12 H 0.5651 1.0247 0.3310 0.022 Uiso 1 1 calc R U . . .
C13 C 0.30494(16) 1.01585(6) 0.24971(5) 0.01699(18) Uani 1 1 d . . . . .
H13 H 0.2143 1.0590 0.2671 0.020 Uiso 1 1 calc R U . . .
C14 C 0.23194(16) 0.97245(6) 0.18572(5) 0.01703(19) Uani 1 1 d . . . . .
H14 H 0.0903 0.9856 0.1582 0.020 Uiso 1 1 calc R U . . .
C15 C 0.36935(16) 0.90956(5) 0.16263(5) 0.01498(18) Uani 1 1 d . . . . .
H15 H 0.3240 0.8792 0.1188 0.018 Uiso 1 1 calc R U . . .
C16 C 1.29094(17) 0.74465(5) 0.32556(5) 0.01582(18) Uani 1 1 d . . . . .
H16A H 1.1406 0.7523 0.3505 0.019 Uiso 1 1 calc R U . . .
H16B H 1.3709 0.7967 0.3230 0.019 Uiso 1 1 calc R U . . .
C17 C 1.44217(14) 0.68655(5) 0.37030(5) 0.01246(17) Uani 1 1 d . . . . .
C18 C 1.64515(16) 0.65531(6) 0.34092(5) 0.01696(19) Uani 1 1 d . . . . .
H18 H 1.6886 0.6699 0.2912 0.020 Uiso 1 1 calc R U . . .
C19 C 1.78457(16) 0.60281(6) 0.38418(6) 0.0205(2) Uani 1 1 d . . . . .
H19 H 1.9227 0.5816 0.3639 0.025 Uiso 1 1 calc R U . . .
C20 C 1.72237(18) 0.58138(6) 0.45689(6) 0.0223(2) Uani 1 1 d . . . . .
H20 H 1.8187 0.5461 0.4865 0.027 Uiso 1 1 calc R U . . .
C21 C 1.51916(18) 0.61165(6) 0.48620(5) 0.0205(2) Uani 1 1 d . . . . .
H21 H 1.4757 0.5968 0.5358 0.025 Uiso 1 1 calc R U . . .
C22 C 1.37887(15) 0.66386(6) 0.44281(5) 0.01524(18) Uani 1 1 d . . . . .
H22 H 1.2391 0.6841 0.4628 0.018 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C4 1.3402(12) . ?
N1 C5 1.3446(12) . ?
N2 C10 1.3404(11) . ?
N2 C6 1.3460(11) . ?
N3 C12 1.3386(12) . ?
N3 C11 1.3444(11) . ?
O1 C8 1.3574(11) . ?
O1 C16 1.4413(11) . ?
C1 C2 1.3915(12) . ?
C1 C5 1.3979(12) . ?
C1 H1 0.9500 . ?
C2 C3 1.3858(14) . ?
C2 H2 0.9500 . ?
C3 C4 1.3909(14) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C5 C6 1.4926(12) . ?
C6 C7 1.3923(12) . ?
C7 C8 1.3941(12) . ?
C7 H7 0.9500 . ?
C8 C9 1.3925(12) . ?
C9 C10 1.3973(12) . ?
C9 H9 0.9500 . ?
C10 C11 1.4899(12) . ?
C11 C15 1.3965(12) . ?
C12 C13 1.3907(13) . ?
C12 H12 0.9500 . ?
C13 C14 1.3885(13) . ?
C13 H13 0.9500 . ?
C14 C15 1.3891(13) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.5032(12) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C22 1.3921(12) . ?
C17 C18 1.3931(13) . ?
C18 C19 1.3924(14) . ?
C18 H18 0.9500 . ?
C19 C20 1.3877(15) . ?
C19 H19 0.9500 . ?
C20 C21 1.3876(14) . ?
C20 H20 0.9500 . ?
C21 C22 1.3930(13) . ?
C21 H21 0.9500 . ?
C22 H22 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
C4 N1 C5 117.62(8) . . ?
C10 N2 C6 117.25(8) . . ?
C12 N3 C11 117.52(8) . . ?
C8 O1 C16 117.29(7) . . ?
C2 C1 C5 118.58(9) . . ?
C2 C1 H1 120.7 . . ?
C5 C1 H1 120.7 . . ?
C3 C2 C1 119.09(8) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 118.30(8) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
N1 C4 C3 123.63(9) . . ?
N1 C4 H4 118.2 . . ?
C3 C4 H4 118.2 . . ?
N1 C5 C1 122.73(8) . . ?
N1 C5 C6 116.28(8) . . ?
C1 C5 C6 120.99(8) . . ?
N2 C6 C7 123.28(8) . . ?
N2 C6 C5 116.50(8) . . ?
C7 C6 C5 120.20(8) . . ?
C6 C7 C8 118.42(8) . . ?
C6 C7 H7 120.8 . . ?
C8 C7 H7 120.8 . . ?
O1 C8 C9 124.35(8) . . ?
O1 C8 C7 116.42(8) . . ?
C9 C8 C7 119.20(8) . . ?
C8 C9 C10 117.78(8) . . ?
C8 C9 H9 121.1 . . ?
C10 C9 H9 121.1 . . ?
N2 C10 C9 123.94(8) . . ?
N2 C10 C11 116.75(8) . . ?
C9 C10 C11 119.28(8) . . ?
N3 C11 C15 122.69(8) . . ?
N3 C11 C10 116.46(8) . . ?
C15 C11 C10 120.83(8) . . ?
N3 C12 C13 123.83(9) . . ?
N3 C12 H12 118.1 . . ?
C13 C12 H12 118.1 . . ?
C14 C13 C12 118.19(9) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
C13 C14 C15 118.92(8) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C14 C15 C11 118.84(8) . . ?
C14 C15 H15 120.6 . . ?
C11 C15 H15 120.6 . . ?
O1 C16 C17 108.03(7) . . ?
O1 C16 H16A 110.1 . . ?
C17 C16 H16A 110.1 . . ?
O1 C16 H16B 110.1 . . ?
C17 C16 H16B 110.1 . . ?
H16A C16 H16B 108.4 . . ?
C22 C17 C18 119.30(8) . . ?
C22 C17 C16 119.31(8) . . ?
C18 C17 C16 121.39(8) . . ?
C19 C18 C17 120.21(9) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C18 120.19(9) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 119.89(9) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 119.97(9) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C17 C22 C21 120.43(9) . . ?
C17 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?

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
C5 C1 C2 C3 0.16(14) . . . . ?
C1 C2 C3 C4 1.42(14) . . . . ?
C5 N1 C4 C3 -0.11(14) . . . . ?
C2 C3 C4 N1 -1.51(15) . . . . ?
C4 N1 C5 C1 1.84(13) . . . . ?
C4 N1 C5 C6 -178.78(8) . . . . ?
C2 C1 C5 N1 -1.88(14) . . . . ?
C2 C1 C5 C6 178.78(8) . . . . ?
C10 N2 C6 C7 -1.09(13) . . . . ?
C10 N2 C6 C5 177.28(7) . . . . ?
N1 C5 C6 N2 177.45(8) . . . . ?
C1 C5 C6 N2 -3.16(12) . . . . ?
N1 C5 C6 C7 -4.13(12) . . . . ?
C1 C5 C6 C7 175.26(8) . . . . ?
N2 C6 C7 C8 3.79(13) . . . . ?
C5 C6 C7 C8 -174.51(8) . . . . ?
C16 O1 C8 C9 13.22(12) . . . . ?
C16 O1 C8 C7 -164.84(8) . . . . ?
C6 C7 C8 O1 174.21(7) . . . . ?
C6 C7 C8 C9 -3.95(12) . . . . ?
O1 C8 C9 C10 -176.37(8) . . . . ?
C7 C8 C9 C10 1.65(12) . . . . ?
C6 N2 C10 C9 -1.45(13) . . . . ?
C6 N2 C10 C11 -179.43(7) . . . . ?
C8 C9 C10 N2 1.15(13) . . . . ?
C8 C9 C10 C11 179.08(7) . . . . ?
C12 N3 C11 C15 0.87(13) . . . . ?
C12 N3 C11 C10 -177.52(8) . . . . ?
N2 C10 C11 N3 178.12(8) . . . . ?
C9 C10 C11 N3 0.03(12) . . . . ?
N2 C10 C11 C15 -0.31(12) . . . . ?
C9 C10 C11 C15 -178.39(8) . . . . ?
C11 N3 C12 C13 0.17(15) . . . . ?
N3 C12 C13 C14 -0.81(15) . . . . ?
C12 C13 C14 C15 0.41(14) . . . . ?
C13 C14 C15 C11 0.54(14) . . . . ?
N3 C11 C15 C14 -1.24(14) . . . . ?
C10 C11 C15 C14 177.09(8) . . . . ?
C8 O1 C16 C17 157.04(7) . . . . ?
O1 C16 C17 C22 -131.57(8) . . . . ?
O1 C16 C17 C18 48.84(11) . . . . ?
C22 C17 C18 C19 -0.88(14) . . . . ?
C16 C17 C18 C19 178.71(8) . . . . ?
C17 C18 C19 C20 -0.11(15) . . . . ?
C18 C19 C20 C21 0.76(16) . . . . ?
C19 C20 C21 C22 -0.41(16) . . . . ?
C18 C17 C22 C21 1.22(14) . . . . ?
C16 C17 C22 C21 -178.37(9) . . . . ?
C20 C21 C22 C17 -0.58(15) . . . . ?

_refine_diff_density_max         0.406
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.066

