# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 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 
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data_pere81
_audit_block_doi                 10.5517/ccdc.csd.cc25m69b
_database_code_depnum_ccdc_archive 'CCDC 2014451'
loop_
_audit_author_name
_audit_author_address
'Thierry Marris'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2020-07-06 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;
_audit_creation_date             2018-07-18
_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         'C22 H15 N3, C12 H6 O2'
_chemical_formula_sum            'C34 H21 N3 O2'
_chemical_formula_weight         503.54
_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 0.0139 0.0070 '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 0.0241 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0390 0.0250 '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                   7.2443(2)
_cell_length_b                   10.4949(3)
_cell_length_c                   16.0924(4)
_cell_angle_alpha                86.9990(10)
_cell_angle_beta                 78.0640(10)
_cell_angle_gamma                88.1360(10)
_cell_volume                     1195.09(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9969
_cell_measurement_temperature    150
_cell_measurement_theta_max      60.650
_cell_measurement_theta_min      3.671
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.915
_exptl_absorpt_coefficient_mu    0.451
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1312 before and 0.0425 after correction. The Ratio of minimum to maximum transmission is 0.8921. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            29192
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.675
_diffrn_reflns_theta_min         2.444
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5060
_reflns_number_total             5496
_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 (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       0.113(4)
_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   1.100
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5496
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0457
_refine_ls_restrained_S_all      1.100
_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)+(0.0662P)²+0.2342P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1160
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4B(H4B), C5B(H5B), C6B(H6B), C8B(H8B), C9B(H9B), C10B(H10B), C4A(H4A),
 C5A(H5A), C6A(H6A), C7A(H7A), C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A),
 C18A(H18A), C19A(H19A), C20A(H20A), C21A(H21A), C22A(H22A)
;
_atom_sites_solution_hydrogens   mixed
_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
O1B O 0.68638(14) 0.56129(11) 0.52289(6) 0.0513(3) Uani 1 1 d . . . . .
O2B O 0.87854(14) 0.35338(9) 0.42720(6) 0.0473(2) Uani 1 1 d . . . . .
C1B C 0.77684(16) 0.57629(13) 0.45077(7) 0.0362(3) Uani 1 1 d . . . . .
C2B C 0.88038(16) 0.46275(12) 0.39880(7) 0.0346(3) Uani 1 1 d . . . . .
C3B C 0.97301(15) 0.51996(11) 0.31586(7) 0.0303(2) Uani 1 1 d . . . . .
C4B C 1.07839(16) 0.47029(12) 0.24335(7) 0.0353(3) Uani 1 1 d . . . . .
H4B H 1.104908 0.381234 0.240073 0.042 Uiso 1 1 calc R . . . .
C5B C 1.14624(16) 0.55594(14) 0.17366(7) 0.0402(3) Uani 1 1 d . . . . .
H5B H 1.219253 0.522775 0.123099 0.048 Uiso 1 1 calc R . . . .
C6B C 1.11059(16) 0.68523(14) 0.17630(7) 0.0400(3) Uani 1 1 d . . . . .
H6B H 1.160337 0.739276 0.128210 0.048 Uiso 1 1 calc R . . . .
C7B C 1.00023(15) 0.73890(12) 0.25010(7) 0.0337(3) Uani 1 1 d . . . . .
C8B C 0.94988(18) 0.86905(13) 0.26323(9) 0.0423(3) Uani 1 1 d . . . . .
H8B H 0.995603 0.931769 0.219753 0.051 Uiso 1 1 calc R . . . .
C9B C 0.83577(19) 0.90614(13) 0.33794(10) 0.0451(3) Uani 1 1 d . . . . .
H9B H 0.803222 0.994027 0.344264 0.054 Uiso 1 1 calc R . . . .
C10B C 0.76581(17) 0.81817(13) 0.40522(8) 0.0402(3) Uani 1 1 d . . . . .
H10B H 0.685265 0.845313 0.455864 0.048 Uiso 1 1 calc R . . . .
C11B C 0.81748(15) 0.69184(12) 0.39548(7) 0.0325(2) Uani 1 1 d . . . . .
C12B C 0.93300(14) 0.65266(11) 0.31850(7) 0.0291(2) Uani 1 1 d . . . . .
N1A N 0.43190(11) 0.29008(8) 0.81870(5) 0.02296(19) Uani 1 1 d . . . . .
N2A N 0.46306(12) 0.57475(8) 0.69395(6) 0.0280(2) Uani 1 1 d . . . . .
H2A H 0.510(2) 0.6134(15) 0.6432(10) 0.046(4) Uiso 1 1 d . . . . .
N3A N 0.66552(12) 0.27862(9) 0.60541(5) 0.0263(2) Uani 1 1 d . . . . .
H3A H 0.713(2) 0.3213(16) 0.5540(11) 0.054(4) Uiso 1 1 d . . . . .
C1A C 0.49703(13) 0.44768(10) 0.71430(6) 0.0240(2) Uani 1 1 d . . . . .
C2A C 0.41543(13) 0.42026(9) 0.79937(6) 0.0231(2) Uani 1 1 d . . . . .
C3A C 0.32362(13) 0.53335(9) 0.83481(6) 0.0243(2) Uani 1 1 d . . . . .
C4A C 0.21031(14) 0.56603(10) 0.91294(6) 0.0273(2) Uani 1 1 d . . . . .
H4A H 0.186174 0.504828 0.959282 0.033 Uiso 1 1 calc R . . . .
C5A C 0.13411(15) 0.68863(10) 0.92162(7) 0.0324(2) Uani 1 1 d . . . . .
H5A H 0.057020 0.711226 0.974260 0.039 Uiso 1 1 calc R . . . .
C6A C 0.16940(16) 0.77985(10) 0.85360(8) 0.0351(3) Uani 1 1 d . . . . .
H6A H 0.115348 0.863219 0.861017 0.042 Uiso 1 1 calc R . . . .
C7A C 0.28157(15) 0.75081(10) 0.77577(8) 0.0328(2) Uani 1 1 d . . . . .
H7A H 0.305412 0.813152 0.730097 0.039 Uiso 1 1 calc R . . . .
C8A C 0.35808(14) 0.62793(10) 0.76649(7) 0.0268(2) Uani 1 1 d . . . . .
C9A C 0.56860(13) 0.33173(10) 0.67900(6) 0.0233(2) Uani 1 1 d . . . . .
C10A C 0.52713(13) 0.23671(9) 0.74339(6) 0.0227(2) Uani 1 1 d . . . . .
C11A C 0.60250(13) 0.11817(10) 0.71021(6) 0.0236(2) Uani 1 1 d . . . . .
C12A C 0.61060(14) -0.00891(10) 0.74080(7) 0.0276(2) Uani 1 1 d . . . . .
H12A H 0.552005 -0.032467 0.797717 0.033 Uiso 1 1 calc R . . . .
C13A C 0.70492(15) -0.10004(11) 0.68727(7) 0.0322(2) Uani 1 1 d . . . . .
H13A H 0.712874 -0.185909 0.708268 0.039 Uiso 1 1 calc R . . . .
C14A C 0.78860(15) -0.06726(11) 0.60268(7) 0.0333(2) Uani 1 1 d . . . . .
H14A H 0.853518 -0.131198 0.567417 0.040 Uiso 1 1 calc R . . . .
C15A C 0.77848(14) 0.05640(11) 0.56956(7) 0.0306(2) Uani 1 1 d . . . . .
H15A H 0.831924 0.077424 0.511625 0.037 Uiso 1 1 calc R . . . .
C16A C 0.68787(13) 0.14955(10) 0.62329(6) 0.0253(2) Uani 1 1 d . . . . .
C17A C 0.38189(13) 0.22758(9) 0.89982(6) 0.0236(2) Uani 1 1 d . . . . .
C18A C 0.41912(14) 0.28325(10) 0.97125(6) 0.0280(2) Uani 1 1 d . . . . .
H18A H 0.477810 0.363761 0.965787 0.034 Uiso 1 1 calc R . . . .
C19A C 0.36971(15) 0.22006(12) 1.05056(6) 0.0342(3) Uani 1 1 d . . . . .
H19A H 0.393840 0.257878 1.099496 0.041 Uiso 1 1 calc R . . . .
C20A C 0.28526(15) 0.10194(12) 1.05851(7) 0.0355(3) Uani 1 1 d . . . . .
H20A H 0.251397 0.059284 1.112841 0.043 Uiso 1 1 calc R . . . .
C21A C 0.25046(15) 0.04643(11) 0.98755(7) 0.0325(2) Uani 1 1 d . . . . .
H21A H 0.194395 -0.034976 0.993056 0.039 Uiso 1 1 calc R . . . .
C22A C 0.29719(14) 0.10926(10) 0.90799(6) 0.0269(2) Uani 1 1 d . . . . .
H22A H 0.271319 0.071468 0.859377 0.032 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
O1B C1B 1.2141(14) . ?
O2B C2B 1.2125(15) . ?
C1B C2B 1.5712(18) . ?
C1B C11B 1.4666(16) . ?
C2B C3B 1.4711(14) . ?
C3B C4B 1.3731(16) . ?
C3B C12B 1.4143(16) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.4151(17) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.374(2) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.4195(18) . ?
C7B C8B 1.4175(19) . ?
C7B C12B 1.4037(14) . ?
C8B H8B 0.9500 . ?
C8B C9B 1.377(2) . ?
C9B H9B 0.9500 . ?
C9B C10B 1.4072(19) . ?
C10B H10B 0.9500 . ?
C10B C11B 1.3740(18) . ?
C11B C12B 1.4164(15) . ?
N1A C2A 1.3920(12) . ?
N1A C10A 1.3993(12) . ?
N1A C17A 1.4128(11) . ?
N2A H2A 0.898(16) . ?
N2A C1A 1.3829(13) . ?
N2A C8A 1.3878(13) . ?
N3A H3A 0.926(17) . ?
N3A C9A 1.3806(12) . ?
N3A C16A 1.3813(13) . ?
C1A C2A 1.3934(13) . ?
C1A C9A 1.4078(14) . ?
C2A C3A 1.4279(14) . ?
C3A C4A 1.4044(13) . ?
C3A C8A 1.4299(13) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.3858(15) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.4037(16) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.3874(16) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.3900(15) . ?
C9A C10A 1.3932(13) . ?
C10A C11A 1.4268(13) . ?
C11A C12A 1.4009(14) . ?
C11A C16A 1.4333(13) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.3871(15) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.4006(16) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.3825(16) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.3951(14) . ?
C17A C18A 1.3943(14) . ?
C17A C22A 1.3909(14) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.3910(14) . ?
C19A H19A 0.9500 . ?
C19A C20A 1.3884(18) . ?
C20A H20A 0.9500 . ?
C20A C21A 1.3803(17) . ?
C21A H21A 0.9500 . ?
C21A C22A 1.3912(14) . ?
C22A H22A 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
O1B C1B C2B 122.51(12) . . ?
O1B C1B C11B 131.15(13) . . ?
C11B C1B C2B 106.34(9) . . ?
O2B C2B C1B 123.19(10) . . ?
O2B C2B C3B 131.07(12) . . ?
C3B C2B C1B 105.73(10) . . ?
C4B C3B C2B 133.38(11) . . ?
C4B C3B C12B 119.86(10) . . ?
C12B C3B C2B 106.75(10) . . ?
C3B C4B H4B 121.0 . . ?
C3B C4B C5B 117.90(12) . . ?
C5B C4B H4B 121.0 . . ?
C4B C5B H5B 118.7 . . ?
C6B C5B C4B 122.53(11) . . ?
C6B C5B H5B 118.7 . . ?
C5B C6B H6B 119.6 . . ?
C5B C6B C7B 120.72(10) . . ?
C7B C6B H6B 119.6 . . ?
C8B C7B C6B 127.91(11) . . ?
C12B C7B C6B 116.08(11) . . ?
C12B C7B C8B 116.01(11) . . ?
C7B C8B H8B 119.4 . . ?
C9B C8B C7B 121.12(11) . . ?
C9B C8B H8B 119.4 . . ?
C8B C9B H9B 118.9 . . ?
C8B C9B C10B 122.19(12) . . ?
C10B C9B H9B 118.9 . . ?
C9B C10B H10B 121.0 . . ?
C11B C10B C9B 118.00(12) . . ?
C11B C10B H10B 121.0 . . ?
C10B C11B C1B 133.32(11) . . ?
C10B C11B C12B 120.17(11) . . ?
C12B C11B C1B 106.51(10) . . ?
C3B C12B C11B 114.65(10) . . ?
C7B C12B C3B 122.89(11) . . ?
C7B C12B C11B 122.45(11) . . ?
C2A N1A C10A 105.78(7) . . ?
C2A N1A C17A 126.77(8) . . ?
C10A N1A C17A 127.09(8) . . ?
C1A N2A H2A 123.8(10) . . ?
C1A N2A C8A 107.45(8) . . ?
C8A N2A H2A 128.6(10) . . ?
C9A N3A H3A 126.9(11) . . ?
C9A N3A C16A 107.45(8) . . ?
C16A N3A H3A 125.6(11) . . ?
N2A C1A C2A 109.37(9) . . ?
N2A C1A C9A 143.11(9) . . ?
C2A C1A C9A 107.13(9) . . ?
N1A C2A C1A 110.11(8) . . ?
N1A C2A C3A 140.76(9) . . ?
C1A C2A C3A 108.58(9) . . ?
C2A C3A C8A 104.62(8) . . ?
C4A C3A C2A 136.29(9) . . ?
C4A C3A C8A 119.00(9) . . ?
C3A C4A H4A 120.4 . . ?
C5A C4A C3A 119.20(10) . . ?
C5A C4A H4A 120.4 . . ?
C4A C5A H5A 119.6 . . ?
C4A C5A C6A 120.83(10) . . ?
C6A C5A H5A 119.6 . . ?
C5A C6A H6A 119.3 . . ?
C7A C6A C5A 121.39(10) . . ?
C7A C6A H6A 119.3 . . ?
C6A C7A H7A 120.9 . . ?
C6A C7A C8A 118.12(10) . . ?
C8A C7A H7A 120.9 . . ?
N2A C8A C3A 109.97(9) . . ?
N2A C8A C7A 128.45(10) . . ?
C7A C8A C3A 121.47(10) . . ?
N3A C9A C1A 143.41(9) . . ?
N3A C9A C10A 109.56(9) . . ?
C10A C9A C1A 107.03(8) . . ?
N1A C10A C11A 141.58(9) . . ?
C9A C10A N1A 109.95(8) . . ?
C9A C10A C11A 108.42(8) . . ?
C10A C11A C16A 104.48(8) . . ?
C12A C11A C10A 136.78(9) . . ?
C12A C11A C16A 118.74(9) . . ?
C11A C12A H12A 120.3 . . ?
C13A C12A C11A 119.42(9) . . ?
C13A C12A H12A 120.3 . . ?
C12A C13A H13A 119.5 . . ?
C12A C13A C14A 120.94(10) . . ?
C14A C13A H13A 119.5 . . ?
C13A C14A H14A 119.4 . . ?
C15A C14A C13A 121.24(10) . . ?
C15A C14A H14A 119.4 . . ?
C14A C15A H15A 120.8 . . ?
C14A C15A C16A 118.37(10) . . ?
C16A C15A H15A 120.8 . . ?
N3A C16A C11A 110.09(9) . . ?
N3A C16A C15A 128.68(9) . . ?
C15A C16A C11A 121.24(10) . . ?
C18A C17A N1A 120.31(9) . . ?
C22A C17A N1A 119.62(9) . . ?
C22A C17A C18A 120.07(9) . . ?
C17A C18A H18A 120.2 . . ?
C19A C18A C17A 119.52(10) . . ?
C19A C18A H18A 120.2 . . ?
C18A C19A H19A 119.9 . . ?
C20A C19A C18A 120.28(10) . . ?
C20A C19A H19A 119.9 . . ?
C19A C20A H20A 120.0 . . ?
C21A C20A C19A 120.06(10) . . ?
C21A C20A H20A 120.0 . . ?
C20A C21A H21A 119.9 . . ?
C20A C21A C22A 120.24(10) . . ?
C22A C21A H21A 119.9 . . ?
C17A C22A C21A 119.82(10) . . ?
C17A C22A H22A 120.1 . . ?
C21A C22A H22A 120.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2A H2A O1B 0.898(16) 2.174(16) 2.8980(13) 137.3(13) . yes
N3A H3A O1B 0.926(17) 2.551(17) 3.1813(14) 125.7(13) . yes
N3A H3A O2B 0.926(17) 2.158(18) 3.0387(12) 158.6(15) . yes

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
O1B C1B C2B O2B -0.70(19) . . . . ?
O1B C1B C2B C3B -179.75(11) . . . . ?
O1B C1B C11B C10B -1.5(2) . . . . ?
O1B C1B C11B C12B 178.94(12) . . . . ?
O2B C2B C3B C4B 3.3(2) . . . . ?
O2B C2B C3B C12B -177.84(12) . . . . ?
C1B C2B C3B C4B -177.72(11) . . . . ?
C1B C2B C3B C12B 1.10(11) . . . . ?
C1B C11B C12B C3B 0.78(12) . . . . ?
C1B C11B C12B C7B -179.92(9) . . . . ?
C2B C1B C11B C10B 179.48(11) . . . . ?
C2B C1B C11B C12B -0.03(11) . . . . ?
C2B C3B C4B C5B 179.76(11) . . . . ?
C2B C3B C12B C7B 179.48(9) . . . . ?
C2B C3B C12B C11B -1.23(12) . . . . ?
C3B C4B C5B C6B 0.05(17) . . . . ?
C4B C3B C12B C7B -1.51(16) . . . . ?
C4B C3B C12B C11B 177.78(9) . . . . ?
C4B C5B C6B C7B -0.78(17) . . . . ?
C5B C6B C7B C8B -179.76(11) . . . . ?
C5B C6B C7B C12B 0.36(15) . . . . ?
C6B C7B C8B C9B 177.79(10) . . . . ?
C6B C7B C12B C3B 0.76(15) . . . . ?
C6B C7B C12B C11B -178.48(9) . . . . ?
C7B C8B C9B C10B 0.96(18) . . . . ?
C8B C7B C12B C3B -179.13(9) . . . . ?
C8B C7B C12B C11B 1.63(15) . . . . ?
C8B C9B C10B C11B 1.24(17) . . . . ?
C9B C10B C11B C1B 178.61(11) . . . . ?
C9B C10B C11B C12B -1.93(16) . . . . ?
C10B C11B C12B C3B -178.80(10) . . . . ?
C10B C11B C12B C7B 0.49(16) . . . . ?
C11B C1B C2B O2B 178.38(11) . . . . ?
C11B C1B C2B C3B -0.67(11) . . . . ?
C12B C3B C4B C5B 1.06(15) . . . . ?
C12B C7B C8B C9B -2.33(16) . . . . ?
N1A C2A C3A C4A 5.3(2) . . . . ?
N1A C2A C3A C8A -170.83(12) . . . . ?
N1A C10A C11A C12A 2.3(2) . . . . ?
N1A C10A C11A C16A -177.69(12) . . . . ?
N1A C17A C18A C19A -179.70(9) . . . . ?
N1A C17A C22A C21A 178.97(9) . . . . ?
N2A C1A C2A N1A 174.08(8) . . . . ?
N2A C1A C2A C3A 0.72(11) . . . . ?
N2A C1A C9A N3A 10.2(2) . . . . ?
N2A C1A C9A C10A -170.98(13) . . . . ?
N3A C9A C10A N1A 178.91(7) . . . . ?
N3A C9A C10A C11A 0.78(11) . . . . ?
C1A N2A C8A C3A -0.06(11) . . . . ?
C1A N2A C8A C7A -176.02(10) . . . . ?
C1A C2A C3A C4A 175.43(11) . . . . ?
C1A C2A C3A C8A -0.73(11) . . . . ?
C1A C9A C10A N1A -0.32(11) . . . . ?
C1A C9A C10A C11A -178.45(8) . . . . ?
C2A N1A C10A C9A 0.01(10) . . . . ?
C2A N1A C10A C11A 177.15(12) . . . . ?
C2A N1A C17A C18A -39.76(14) . . . . ?
C2A N1A C17A C22A 141.00(10) . . . . ?
C2A C1A C9A N3A -178.28(12) . . . . ?
C2A C1A C9A C10A 0.51(11) . . . . ?
C2A C3A C4A C5A -175.39(11) . . . . ?
C2A C3A C8A N2A 0.48(11) . . . . ?
C2A C3A C8A C7A 176.77(9) . . . . ?
C3A C4A C5A C6A -0.19(16) . . . . ?
C4A C3A C8A N2A -176.48(9) . . . . ?
C4A C3A C8A C7A -0.19(15) . . . . ?
C4A C5A C6A C7A -0.17(17) . . . . ?
C5A C6A C7A C8A 0.34(17) . . . . ?
C6A C7A C8A N2A 175.39(10) . . . . ?
C6A C7A C8A C3A -0.16(16) . . . . ?
C8A N2A C1A C2A -0.41(11) . . . . ?
C8A N2A C1A C9A 170.96(13) . . . . ?
C8A C3A C4A C5A 0.36(14) . . . . ?
C9A N3A C16A C11A 0.39(11) . . . . ?
C9A N3A C16A C15A -179.18(10) . . . . ?
C9A C1A C2A N1A -0.52(11) . . . . ?
C9A C1A C2A C3A -173.87(8) . . . . ?
C9A C10A C11A C12A 179.43(11) . . . . ?
C9A C10A C11A C16A -0.51(10) . . . . ?
C10A N1A C2A C1A 0.32(10) . . . . ?
C10A N1A C2A C3A 170.33(12) . . . . ?
C10A N1A C17A C18A 132.42(10) . . . . ?
C10A N1A C17A C22A -46.82(13) . . . . ?
C10A C11A C12A C13A -178.18(11) . . . . ?
C10A C11A C16A N3A 0.08(10) . . . . ?
C10A C11A C16A C15A 179.69(9) . . . . ?
C11A C12A C13A C14A -1.35(16) . . . . ?
C12A C11A C16A N3A -179.88(8) . . . . ?
C12A C11A C16A C15A -0.27(14) . . . . ?
C12A C13A C14A C15A -0.63(17) . . . . ?
C13A C14A C15A C16A 2.10(16) . . . . ?
C14A C15A C16A N3A 177.89(10) . . . . ?
C14A C15A C16A C11A -1.65(15) . . . . ?
C16A N3A C9A C1A 178.05(13) . . . . ?
C16A N3A C9A C10A -0.73(11) . . . . ?
C16A C11A C12A C13A 1.76(14) . . . . ?
C17A N1A C2A C1A 173.84(9) . . . . ?
C17A N1A C2A C3A -16.15(19) . . . . ?
C17A N1A C10A C9A -173.49(9) . . . . ?
C17A N1A C10A C11A 3.66(19) . . . . ?
C17A C18A C19A C20A 0.50(15) . . . . ?
C18A C17A C22A C21A -0.27(14) . . . . ?
C18A C19A C20A C21A 0.20(16) . . . . ?
C19A C20A C21A C22A -0.95(16) . . . . ?
C20A C21A C22A C17A 0.98(15) . . . . ?
C22A C17A C18A C19A -0.47(15) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a Cryoloop'
_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_per105
_audit_block_doi                 10.5517/ccdc.csd.cc25m6cd
_database_code_depnum_ccdc_archive 'CCDC 2014453'
loop_
_audit_author_name
_audit_author_address
'Thierry Marris'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2020-07-06 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;
_audit_creation_date             2019-04-15
_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         'C11 H6 N2 O, C22 H15 N3'
_chemical_formula_sum            'C33 H21 N5 O'
_chemical_formula_weight         503.55
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.6183(6)
_cell_length_b                   7.6738(4)
_cell_length_c                   24.7365(12)
_cell_angle_alpha                90
_cell_angle_beta                 97.705(2)
_cell_angle_gamma                90
_cell_volume                     2373.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.082
_cell_measurement_theta_min      6.043
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.861
_exptl_absorpt_coefficient_mu    0.699
_exptl_absorpt_correction_T_max  0.5220
_exptl_absorpt_correction_T_min  0.3799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1182 before and 0.0545 after correction. The Ratio of minimum to maximum transmission is 0.7278. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Smart diffractometer equipped with an APEX II CCD Detector,
an Incoatec IMuS source and a Quazar MX mirror. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 180.0 degree
scan in 180 frames over three different parts of the reciprocal space
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            51726
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.233
_diffrn_reflns_theta_min         6.042
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Microfocus Source'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4136
_reflns_number_total             4483
_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 (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0019(5)
_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   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4483
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0449
_refine_ls_restrained_S_all      1.056
_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)+(0.0832P)²+0.5687P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1257
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1B(H1B), C2B(H2B), C3B(H3B), C7B(H7B), C8B(H8B), C9B(H9B), C2A(H2AA),
 C3A(H3A), C4A(H4A), C5A(H5A), C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A),
 C18A(H18A), C19A(H19A), C20A(H20A), C21A(H21A), C22A(H22A)
;
_atom_sites_solution_hydrogens   mixed
_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
O1B O 0.93823(7) 0.41713(14) 0.58933(4) 0.0381(3) Uani 1 1 d . . . . .
N1B N 0.66763(9) 0.51973(15) 0.43866(5) 0.0317(3) Uani 1 1 d . . . . .
N2B N 0.59188(9) 0.67008(15) 0.54481(5) 0.0317(3) Uani 1 1 d . . . . .
C1B C 0.72218(11) 0.44953(18) 0.40057(6) 0.0349(3) Uani 1 1 d . . . . .
H1B H 0.688106 0.449338 0.363914 0.042 Uiso 1 1 calc R . . . .
C2B C 0.82367(11) 0.37780(19) 0.41053(6) 0.0360(3) Uani 1 1 d . . . . .
H2B H 0.857457 0.332814 0.381402 0.043 Uiso 1 1 calc R . . . .
C3B C 0.87541(11) 0.37264(18) 0.46388(6) 0.0341(3) Uani 1 1 d . . . . .
H3B H 0.944744 0.323618 0.472542 0.041 Uiso 1 1 calc R . . . .
C4B C 0.82084(10) 0.44235(17) 0.50351(6) 0.0310(3) Uani 1 1 d . . . . .
C5B C 0.85404(10) 0.46280(18) 0.56334(6) 0.0319(3) Uani 1 1 d . . . . .
C6B C 0.76348(10) 0.55480(17) 0.58386(5) 0.0311(3) Uani 1 1 d . . . . .
C7B C 0.75092(11) 0.60814(18) 0.63595(6) 0.0335(3) Uani 1 1 d . . . . .
H7B H 0.804742 0.588779 0.666069 0.040 Uiso 1 1 calc R . . . .
C8B C 0.65535(11) 0.69172(19) 0.64204(6) 0.0348(3) Uani 1 1 d . . . . .
H8B H 0.641443 0.729463 0.676988 0.042 Uiso 1 1 calc R . . . .
C9B C 0.58057(11) 0.71913(18) 0.59626(6) 0.0334(3) Uani 1 1 d . . . . .
H9B H 0.516205 0.777081 0.601510 0.040 Uiso 1 1 calc R . . . .
C10B C 0.68301(10) 0.58738(17) 0.54010(5) 0.0297(3) Uani 1 1 d . . . . .
C11B C 0.71901(10) 0.51567(17) 0.48933(6) 0.0299(3) Uani 1 1 d . . . . .
N1A N 0.48545(9) 0.68330(15) 0.36345(4) 0.0288(3) Uani 1 1 d . . . . .
N2A N 0.40267(9) 0.86303(15) 0.48523(4) 0.0280(3) Uani 1 1 d . . . . .
N3A N 0.23581(8) 0.88666(14) 0.36021(4) 0.0275(3) Uani 1 1 d . . . . .
C1A C 0.45405(10) 0.65310(17) 0.30829(5) 0.0278(3) Uani 1 1 d . . . . .
C2A C 0.50912(10) 0.56817(18) 0.27077(5) 0.0316(3) Uani 1 1 d . . . . .
H2AA H 0.578201 0.520622 0.281644 0.038 Uiso 1 1 calc R . . . .
C3A C 0.46075(11) 0.55468(18) 0.21721(6) 0.0326(3) Uani 1 1 d . . . . .
H3A H 0.497355 0.497320 0.191149 0.039 Uiso 1 1 calc R . . . .
C4A C 0.35894(11) 0.62410(18) 0.20087(5) 0.0313(3) Uani 1 1 d . . . . .
H4A H 0.327156 0.611676 0.164025 0.038 Uiso 1 1 calc R . . . .
C5A C 0.30384(10) 0.71052(17) 0.23750(5) 0.0290(3) Uani 1 1 d . . . . .
H5A H 0.234910 0.757630 0.225909 0.035 Uiso 1 1 calc R . . . .
C6A C 0.35069(10) 0.72788(16) 0.29187(5) 0.0270(3) Uani 1 1 d . . . . .
C7A C 0.32189(10) 0.80538(17) 0.34038(5) 0.0273(3) Uani 1 1 d . . . . .
C8A C 0.40347(9) 0.77303(17) 0.38262(5) 0.0269(3) Uani 1 1 d . . . . .
C9A C 0.36847(10) 0.83631(17) 0.43075(5) 0.0268(3) Uani 1 1 d . . . . .
C10A C 0.26659(10) 0.90494(17) 0.41652(5) 0.0269(3) Uani 1 1 d . . . . .
C11A C 0.23345(10) 0.98001(17) 0.46462(5) 0.0271(3) Uani 1 1 d . . . . .
C12A C 0.14249(10) 1.06610(17) 0.47867(5) 0.0297(3) Uani 1 1 d . . . . .
H12A H 0.082684 1.087064 0.451809 0.036 Uiso 1 1 calc R . . . .
C13A C 0.14092(11) 1.11996(17) 0.53201(5) 0.0311(3) Uani 1 1 d . . . . .
H13A H 0.078943 1.175673 0.541715 0.037 Uiso 1 1 calc R . . . .
C14A C 0.22945(11) 1.09351(17) 0.57188(5) 0.0316(3) Uani 1 1 d . . . . .
H14A H 0.226975 1.133548 0.608032 0.038 Uiso 1 1 calc R . . . .
C15A C 0.32038(10) 1.01004(17) 0.55946(5) 0.0299(3) Uani 1 1 d . . . . .
H15A H 0.380519 0.993955 0.586498 0.036 Uiso 1 1 calc R . . . .
C16A C 0.32168(10) 0.95018(17) 0.50642(5) 0.0279(3) Uani 1 1 d . . . . .
C17A C 0.14692(10) 0.96194(16) 0.32749(5) 0.0277(3) Uani 1 1 d . . . . .
C18A C 0.04578(10) 0.95895(17) 0.34397(5) 0.0300(3) Uani 1 1 d . . . . .
H18A H 0.035712 0.909392 0.378107 0.036 Uiso 1 1 calc R . . . .
C19A C -0.04040(10) 1.02909(19) 0.31007(6) 0.0337(3) Uani 1 1 d . . . . .
H19A H -0.109193 1.030126 0.321667 0.040 Uiso 1 1 calc R . . . .
C20A C -0.02720(11) 1.09768(19) 0.25946(6) 0.0369(3) Uani 1 1 d . . . . .
H20A H -0.086876 1.142839 0.236184 0.044 Uiso 1 1 calc R . . . .
C21A C 0.07384(12) 1.09979(18) 0.24312(6) 0.0350(3) Uani 1 1 d . . . . .
H21A H 0.083216 1.145921 0.208440 0.042 Uiso 1 1 calc R . . . .
C22A C 0.16108(10) 1.03492(17) 0.27716(5) 0.0306(3) Uani 1 1 d . . . . .
H22A H 0.230444 1.040024 0.266312 0.037 Uiso 1 1 calc R . . . .
H2A H 0.4611(15) 0.813(2) 0.5027(7) 0.048(5) Uiso 1 1 d . . . . .
H1A H 0.5424(14) 0.634(2) 0.3858(7) 0.043(5) Uiso 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
O1B C5B 1.2172(16) . ?
N1B C1B 1.3511(18) . ?
N1B C11B 1.3322(18) . ?
N2B C9B 1.3528(18) . ?
N2B C10B 1.3322(17) . ?
C1B H1B 0.9500 . ?
C1B C2B 1.385(2) . ?
C2B H2B 0.9500 . ?
C2B C3B 1.392(2) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.379(2) . ?
C4B C5B 1.4912(19) . ?
C4B C11B 1.4035(18) . ?
C5B C6B 1.4891(19) . ?
C6B C7B 1.3813(19) . ?
C6B C10B 1.4037(18) . ?
C7B H7B 0.9500 . ?
C7B C8B 1.392(2) . ?
C8B H8B 0.9500 . ?
C8B C9B 1.390(2) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.4962(19) . ?
N1A C1A 1.3883(17) . ?
N1A C8A 1.3786(16) . ?
N1A H1A 0.925(19) . ?
N2A C9A 1.3743(16) . ?
N2A C16A 1.3821(17) . ?
N2A H2A 0.89(2) . ?
N3A C7A 1.3972(16) . ?
N3A C10A 1.4019(16) . ?
N3A C17A 1.4154(16) . ?
C1A C2A 1.3936(18) . ?
C1A C6A 1.4329(17) . ?
C2A H2AA 0.9500 . ?
C2A C3A 1.3862(19) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.3995(19) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.3832(18) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.4010(18) . ?
C6A C7A 1.4292(17) . ?
C7A C8A 1.3873(18) . ?
C8A C9A 1.4104(17) . ?
C9A C10A 1.3901(18) . ?
C10A C11A 1.4339(17) . ?
C11A C12A 1.4077(18) . ?
C11A C16A 1.4325(18) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.3851(19) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.4024(19) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.3841(19) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.3922(18) . ?
C17A C18A 1.3910(18) . ?
C17A C22A 1.3984(18) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.3895(19) . ?
C19A H19A 0.9500 . ?
C19A C20A 1.389(2) . ?
C20A H20A 0.9500 . ?
C20A C21A 1.388(2) . ?
C21A H21A 0.9500 . ?
C21A C22A 1.3856(19) . ?
C22A H22A 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
C11B N1B C1B 114.69(12) . . ?
C10B N2B C9B 114.59(12) . . ?
N1B C1B H1B 117.3 . . ?
N1B C1B C2B 125.42(13) . . ?
C2B C1B H1B 117.3 . . ?
C1B C2B H2B 120.5 . . ?
C1B C2B C3B 119.00(13) . . ?
C3B C2B H2B 120.5 . . ?
C2B C3B H3B 121.7 . . ?
C4B C3B C2B 116.57(12) . . ?
C4B C3B H3B 121.7 . . ?
C3B C4B C5B 130.21(12) . . ?
C3B C4B C11B 120.36(13) . . ?
C11B C4B C5B 109.38(12) . . ?
O1B C5B C4B 127.09(13) . . ?
O1B C5B C6B 127.72(13) . . ?
C6B C5B C4B 105.18(11) . . ?
C7B C6B C5B 130.37(12) . . ?
C7B C6B C10B 120.34(13) . . ?
C10B C6B C5B 109.29(12) . . ?
C6B C7B H7B 121.7 . . ?
C6B C7B C8B 116.55(12) . . ?
C8B C7B H7B 121.7 . . ?
C7B C8B H8B 120.5 . . ?
C9B C8B C7B 119.02(13) . . ?
C9B C8B H8B 120.5 . . ?
N2B C9B C8B 125.37(13) . . ?
N2B C9B H9B 117.3 . . ?
C8B C9B H9B 117.3 . . ?
N2B C10B C6B 124.12(13) . . ?
N2B C10B C11B 127.69(12) . . ?
C6B C10B C11B 108.19(11) . . ?
N1B C11B C4B 123.94(12) . . ?
N1B C11B C10B 128.09(12) . . ?
C4B C11B C10B 107.97(11) . . ?
C1A N1A H1A 128.0(11) . . ?
C8A N1A C1A 107.04(10) . . ?
C8A N1A H1A 123.8(11) . . ?
C9A N2A C16A 107.04(11) . . ?
C9A N2A H2A 123.0(12) . . ?
C16A N2A H2A 129.0(12) . . ?
C7A N3A C10A 105.58(10) . . ?
C7A N3A C17A 125.11(10) . . ?
C10A N3A C17A 128.31(11) . . ?
N1A C1A C2A 129.09(12) . . ?
N1A C1A C6A 109.93(11) . . ?
C2A C1A C6A 120.97(12) . . ?
C1A C2A H2AA 120.8 . . ?
C3A C2A C1A 118.46(12) . . ?
C3A C2A H2AA 120.8 . . ?
C2A C3A H3A 119.4 . . ?
C2A C3A C4A 121.14(12) . . ?
C4A C3A H3A 119.4 . . ?
C3A C4A H4A 119.5 . . ?
C5A C4A C3A 121.06(12) . . ?
C5A C4A H4A 119.5 . . ?
C4A C5A H5A 120.3 . . ?
C4A C5A C6A 119.34(12) . . ?
C6A C5A H5A 120.3 . . ?
C5A C6A C1A 119.01(11) . . ?
C5A C6A C7A 136.35(12) . . ?
C7A C6A C1A 104.64(11) . . ?
N3A C7A C6A 141.05(12) . . ?
C8A C7A N3A 110.41(11) . . ?
C8A C7A C6A 108.14(11) . . ?
N1A C8A C7A 110.22(11) . . ?
N1A C8A C9A 142.81(12) . . ?
C7A C8A C9A 106.82(11) . . ?
N2A C9A C8A 141.85(12) . . ?
N2A C9A C10A 110.49(11) . . ?
C10A C9A C8A 107.48(11) . . ?
N3A C10A C11A 142.36(12) . . ?
C9A C10A N3A 109.71(11) . . ?
C9A C10A C11A 107.74(11) . . ?
C12A C11A C10A 137.02(12) . . ?
C12A C11A C16A 118.51(12) . . ?
C16A C11A C10A 104.47(11) . . ?
C11A C12A H12A 120.3 . . ?
C13A C12A C11A 119.43(12) . . ?
C13A C12A H12A 120.3 . . ?
C12A C13A H13A 119.5 . . ?
C12A C13A C14A 121.00(12) . . ?
C14A C13A H13A 119.5 . . ?
C13A C14A H14A 119.4 . . ?
C15A C14A C13A 121.11(12) . . ?
C15A C14A H14A 119.4 . . ?
C14A C15A H15A 120.8 . . ?
C14A C15A C16A 118.48(12) . . ?
C16A C15A H15A 120.8 . . ?
N2A C16A C11A 110.26(11) . . ?
N2A C16A C15A 128.30(12) . . ?
C15A C16A C11A 121.41(12) . . ?
C18A C17A N3A 120.90(12) . . ?
C18A C17A C22A 119.95(12) . . ?
C22A C17A N3A 119.11(11) . . ?
C17A C18A H18A 120.3 . . ?
C19A C18A C17A 119.43(12) . . ?
C19A C18A H18A 120.3 . . ?
C18A C19A H19A 119.6 . . ?
C20A C19A C18A 120.80(12) . . ?
C20A C19A H19A 119.6 . . ?
C19A C20A H20A 120.2 . . ?
C21A C20A C19A 119.53(13) . . ?
C21A C20A H20A 120.2 . . ?
C20A C21A H21A 119.8 . . ?
C22A C21A C20A 120.31(13) . . ?
C22A C21A H21A 119.8 . . ?
C17A C22A H22A 120.0 . . ?
C21A C22A C17A 119.93(12) . . ?
C21A C22A H22A 120.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C18A H18A O1B 0.95 2.64 3.3170(17) 128.7 3_666 yes
N2A H2A N2B 0.89(2) 2.13(2) 3.0201(16) 174.2(17) . yes
N1A H1A N1B 0.925(19) 2.104(19) 3.0289(16) 177.7(15) . yes

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
O1B C5B C6B C7B -1.1(2) . . . . ?
O1B C5B C6B C10B 178.35(13) . . . . ?
N1B C1B C2B C3B 1.2(2) . . . . ?
N2B C10B C11B N1B 0.0(2) . . . . ?
N2B C10B C11B C4B 178.98(13) . . . . ?
C1B N1B C11B C4B -1.15(19) . . . . ?
C1B N1B C11B C10B 177.67(12) . . . . ?
C1B C2B C3B C4B -0.6(2) . . . . ?
C2B C3B C4B C5B -177.72(13) . . . . ?
C2B C3B C4B C11B -0.75(19) . . . . ?
C3B C4B C5B O1B -1.4(2) . . . . ?
C3B C4B C5B C6B 177.18(14) . . . . ?
C3B C4B C11B N1B 1.7(2) . . . . ?
C3B C4B C11B C10B -177.28(12) . . . . ?
C4B C5B C6B C7B -179.65(13) . . . . ?
C4B C5B C6B C10B -0.20(14) . . . . ?
C5B C4B C11B N1B 179.29(12) . . . . ?
C5B C4B C11B C10B 0.26(14) . . . . ?
C5B C6B C7B C8B -179.78(13) . . . . ?
C5B C6B C10B N2B -179.03(12) . . . . ?
C5B C6B C10B C11B 0.36(14) . . . . ?
C6B C7B C8B C9B -1.20(19) . . . . ?
C6B C10B C11B N1B -179.37(12) . . . . ?
C6B C10B C11B C4B -0.39(14) . . . . ?
C7B C6B C10B N2B 0.5(2) . . . . ?
C7B C6B C10B C11B 179.87(12) . . . . ?
C7B C8B C9B N2B 0.4(2) . . . . ?
C9B N2B C10B C6B -1.29(19) . . . . ?
C9B N2B C10B C11B 179.43(12) . . . . ?
C10B N2B C9B C8B 0.9(2) . . . . ?
C10B C6B C7B C8B 0.83(19) . . . . ?
C11B N1B C1B C2B -0.3(2) . . . . ?
C11B C4B C5B O1B -178.61(13) . . . . ?
C11B C4B C5B C6B -0.05(14) . . . . ?
N1A C1A C2A C3A -179.75(13) . . . . ?
N1A C1A C6A C5A -179.46(11) . . . . ?
N1A C1A C6A C7A 0.17(14) . . . . ?
N1A C8A C9A N2A 11.3(3) . . . . ?
N1A C8A C9A C10A -174.54(17) . . . . ?
N2A C9A C10A N3A 176.19(10) . . . . ?
N2A C9A C10A C11A -0.01(14) . . . . ?
N3A C7A C8A N1A 176.32(10) . . . . ?
N3A C7A C8A C9A -0.26(14) . . . . ?
N3A C10A C11A C12A 6.6(3) . . . . ?
N3A C10A C11A C16A -174.11(16) . . . . ?
N3A C17A C18A C19A -177.96(12) . . . . ?
N3A C17A C22A C21A 176.13(12) . . . . ?
C1A N1A C8A C7A -1.88(14) . . . . ?
C1A N1A C8A C9A 172.70(17) . . . . ?
C1A C2A C3A C4A -0.1(2) . . . . ?
C1A C6A C7A N3A -172.80(16) . . . . ?
C1A C6A C7A C8A -1.30(14) . . . . ?
C2A C1A C6A C5A 1.72(19) . . . . ?
C2A C1A C6A C7A -178.64(12) . . . . ?
C2A C3A C4A C5A 0.9(2) . . . . ?
C3A C4A C5A C6A -0.3(2) . . . . ?
C4A C5A C6A C1A -0.95(19) . . . . ?
C4A C5A C6A C7A 179.57(14) . . . . ?
C5A C6A C7A N3A 6.7(3) . . . . ?
C5A C6A C7A C8A 178.23(14) . . . . ?
C6A C1A C2A C3A -1.18(19) . . . . ?
C6A C7A C8A N1A 2.01(15) . . . . ?
C6A C7A C8A C9A -174.57(10) . . . . ?
C7A N3A C10A C9A -0.17(14) . . . . ?
C7A N3A C10A C11A 173.90(16) . . . . ?
C7A N3A C17A C18A 146.76(13) . . . . ?
C7A N3A C17A C22A -31.14(18) . . . . ?
C7A C8A C9A N2A -174.05(16) . . . . ?
C7A C8A C9A C10A 0.15(14) . . . . ?
C8A N1A C1A C2A 179.71(13) . . . . ?
C8A N1A C1A C6A 1.02(14) . . . . ?
C8A C9A C10A N3A 0.02(14) . . . . ?
C8A C9A C10A C11A -176.19(10) . . . . ?
C9A N2A C16A C11A 0.04(14) . . . . ?
C9A N2A C16A C15A -178.00(13) . . . . ?
C9A C10A C11A C12A -179.21(15) . . . . ?
C9A C10A C11A C16A 0.03(14) . . . . ?
C10A N3A C7A C6A 171.64(16) . . . . ?
C10A N3A C7A C8A 0.27(14) . . . . ?
C10A N3A C17A C18A -46.30(19) . . . . ?
C10A N3A C17A C22A 135.80(13) . . . . ?
C10A C11A C12A C13A 179.49(14) . . . . ?
C10A C11A C16A N2A -0.04(14) . . . . ?
C10A C11A C16A C15A 178.15(12) . . . . ?
C11A C12A C13A C14A 1.4(2) . . . . ?
C12A C11A C16A N2A 179.37(11) . . . . ?
C12A C11A C16A C15A -2.44(19) . . . . ?
C12A C13A C14A C15A -1.2(2) . . . . ?
C13A C14A C15A C16A -0.9(2) . . . . ?
C14A C15A C16A N2A -179.44(12) . . . . ?
C14A C15A C16A C11A 2.72(19) . . . . ?
C16A N2A C9A C8A 174.07(16) . . . . ?
C16A N2A C9A C10A -0.02(14) . . . . ?
C16A C11A C12A C13A 0.32(19) . . . . ?
C17A N3A C7A C6A -19.0(2) . . . . ?
C17A N3A C7A C8A 169.66(11) . . . . ?
C17A N3A C10A C9A -169.11(12) . . . . ?
C17A N3A C10A C11A 5.0(3) . . . . ?
C17A C18A C19A C20A 1.7(2) . . . . ?
C18A C17A C22A C21A -1.8(2) . . . . ?
C18A C19A C20A C21A -1.5(2) . . . . ?
C19A C20A C21A C22A -0.4(2) . . . . ?
C20A C21A C22A C17A 2.0(2) . . . . ?
C22A C17A C18A C19A -0.1(2) . . . . ?

_olex2_date_sample_data_collection 2019-04-11
_olex2_date_sample_submission    2019-04-02
_olex2_exptl_crystal_mounting_method 'mounted on a cryollop'
_olex2_submission_original_sample_id PhDIP-co-Diazafluorenone
_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_pere92
_audit_block_doi                 10.5517/ccdc.csd.cc25m6bc
_database_code_depnum_ccdc_archive 'CCDC 2014452'
loop_
_audit_author_name
_audit_author_address
'Thierry Marris'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2020-07-06 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;
_audit_creation_date             2018-09-13
_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         'C12 H6 N2 O2, C22 H15 N3, C2 H4 Cl2'
_chemical_formula_sum            'C36 H25 Cl2 N5 O2'
_chemical_formula_weight         630.51
_chemical_absolute_configuration ?
_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 0.0137 0.0070 '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 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   8.1852(4)
_cell_length_b                   19.0716(8)
_cell_length_c                   37.1950(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5806.3(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9661
_cell_measurement_temperature    150
_cell_measurement_theta_max      53.917
_cell_measurement_theta_min      2.888
_shelx_estimated_absorpt_T_max   0.955
_shelx_estimated_absorpt_T_min   0.627
_exptl_absorpt_coefficient_mu    1.561
_exptl_absorpt_correction_T_max  0.7506
_exptl_absorpt_correction_T_min  0.5390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1649 before and 0.0922 after correction. The Ratio of minimum to maximum transmission is 0.7181. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2608
_exptl_crystal_recrystallization_method 'crystallized from C2H4Cl2'
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            62466
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.067
_diffrn_reflns_theta_min         2.015
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.955
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                8844
_reflns_number_total             10604
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.36(3)
_refine_ls_extinction_coef       0.00085(12)
_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   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     826
_refine_ls_number_reflns         10604
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0577
_refine_ls_restrained_S_all      1.030
_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)+(0.0917P)²+3.4552P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1453
_refine_ls_wR_factor_ref         0.1586
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.64(3)
 0.36(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
3. Restrained distances
 C1E-C2E \\sim C1F-C2F
 with sigma of 0.02
 C1E-Cl1 \\sim C1F-Cl1 \\sim C2E-Cl2 \\sim C2F-Cl2
 with sigma of 0.02
 C3E-C4E \\sim C3F-C4F
 with sigma of 0.02
 C3E-Cl3 \\sim C3F-Cl3 \\sim C4E-Cl4 \\sim C4F-Cl4
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C1E) = Uanis(C1F)
Uanis(C2E) = Uanis(C2F)
Uanis(C3E) = Uanis(C3F)
Uanis(C4E) = Uanis(C4F)
5. Others
 Sof(C1F)=Sof(H1FA)=Sof(H1FB)=Sof(C2F)=Sof(H2FA)=Sof(H2FB)=Sof(C3F)=Sof(H3FA)=
 Sof(H3FB)=Sof(C4F)=Sof(H4FB)=Sof(H4FA)=1-FVAR(1)
 Sof(C1E)=Sof(H1EA)=Sof(H1EB)=Sof(C2E)=Sof(H2EA)=Sof(H2EB)=Sof(C3E)=Sof(H3EA)=
 Sof(H3EB)=Sof(C4E)=Sof(H4EA)=Sof(H4EB)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C1E(H1EA,H1EB), C2E(H2EA,H2EB), C1F(H1FA,H1FB), C2F(H2FA,H2FB), C3E(H3EA,
 H3EB), C4E(H4EA,H4EB), C3F(H3FA,H3FB), C4F(H4FB,H4FA)
6.b Aromatic/amide H refined with riding coordinates:
 N1A(H1A), N2A(H2A), C1C(H1C), C2A(H2AA), C2C(H2C), C3A(H3A), C3C(H3C),
 C4A(H4A), C5A(H5A), C8C(H8C), C9C(H9C), C10C(H10C), C13A(H13A), C14A(H14A),
 C15A(H15A), C16A(H16A), C18A(H18A), C19A(H19A), C20A(H20A), C21A(H21A),
 C22A(H22A), N1B(H1B), N2B(H2B), C1D(H1D), C2B(H2BA), C2D(H2D), C3B(H3B),
 C3D(H3D), C4B(H4B), C5B(H5B), C8D(H8D), C9D(H9D), C10D(H10D), C13B(H13B),
 C14B(H14B), C15B(H15B), C16B(H16B), C18B(H18B), C19B(H19B), C20B(H20B),
 C21B(H21B), C22B(H22B)
;
_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
O1C O 0.4150(5) 0.3832(2) 0.52394(10) 0.0381(9) Uani 1 1 d . . . . .
O2C O 0.5930(5) 0.4497(2) 0.57507(12) 0.0455(10) Uani 1 1 d . . . . .
N1A N 0.3956(5) 0.5381(2) 0.52158(11) 0.0318(10) Uani 1 1 d . . . . .
H1A H 0.405009 0.494371 0.528908 0.038 Uiso 1 1 calc R . . . .
N1C N 0.8003(6) 0.2293(3) 0.61541(13) 0.0366(11) Uani 1 1 d . . . . .
N2A N 0.6672(6) 0.5920(3) 0.59244(12) 0.0346(10) Uani 1 1 d . . . . .
H2A H 0.676889 0.547899 0.598982 0.041 Uiso 1 1 calc R . . . .
N2C N 0.6257(6) 0.1634(3) 0.56321(14) 0.0396(11) Uani 1 1 d . . . . .
N3A N 0.4979(6) 0.7147(2) 0.53326(11) 0.0293(10) Uani 1 1 d . . . . .
C1A C 0.2988(6) 0.5613(3) 0.49375(14) 0.0326(12) Uani 1 1 d . . . . .
C1C C 0.8835(7) 0.2615(4) 0.64149(16) 0.0390(14) Uani 1 1 d . . . . .
H1C H 0.949338 0.233485 0.656841 0.047 Uiso 1 1 calc R . . . .
C2A C 0.1939(7) 0.5225(3) 0.47219(15) 0.0355(12) Uani 1 1 d . . . . .
H2AA H 0.186305 0.472999 0.474598 0.043 Uiso 1 1 calc R . . . .
C2C C 0.8802(7) 0.3333(4) 0.64765(17) 0.0422(15) Uani 1 1 d . . . . .
H2C H 0.938306 0.353492 0.667199 0.051 Uiso 1 1 calc R . . . .
C3A C 0.1005(7) 0.5582(3) 0.44703(15) 0.0395(13) Uani 1 1 d . . . . .
H3A H 0.026759 0.532812 0.432197 0.047 Uiso 1 1 calc R . . . .
C3C C 0.7902(7) 0.3744(3) 0.62458(15) 0.0394(13) Uani 1 1 d . . . . .
H3C H 0.787155 0.423863 0.627624 0.047 Uiso 1 1 calc R . . . .
C4A C 0.1132(7) 0.6309(3) 0.44314(15) 0.0376(13) Uani 1 1 d . . . . .
H4A H 0.046919 0.653995 0.425845 0.045 Uiso 1 1 calc R . . . .
C4C C 0.7027(6) 0.3425(3) 0.59643(15) 0.0331(12) Uani 1 1 d . . . . .
C5A C 0.2193(7) 0.6699(3) 0.46373(14) 0.0371(12) Uani 1 1 d . . . . .
H5A H 0.229328 0.719019 0.460151 0.045 Uiso 1 1 calc R . . . .
C5C C 0.7098(6) 0.2696(3) 0.59307(15) 0.0318(12) Uani 1 1 d . . . . .
C6A C 0.3128(6) 0.6355(3) 0.49026(14) 0.0307(11) Uani 1 1 d . . . . .
C6C C 0.6160(6) 0.2337(3) 0.56453(14) 0.0319(11) Uani 1 1 d . . . . .
C7A C 0.4283(6) 0.6554(3) 0.51748(14) 0.0312(11) Uani 1 1 d . . . . .
C7C C 0.5211(7) 0.2724(3) 0.54012(15) 0.0314(12) Uani 1 1 d . . . . .
C8A C 0.4751(7) 0.5951(3) 0.53592(14) 0.0327(12) Uani 1 1 d . . . . .
C8C C 0.4334(7) 0.2370(3) 0.51386(16) 0.0387(13) Uani 1 1 d . . . . .
H8C H 0.368628 0.262050 0.496992 0.046 Uiso 1 1 calc R . . . .
C9A C 0.5778(7) 0.6166(3) 0.56377(14) 0.0305(11) Uani 1 1 d . . . . .
C9C C 0.4420(7) 0.1645(3) 0.51272(17) 0.0422(13) Uani 1 1 d . . . . .
H9C H 0.382898 0.138570 0.495206 0.051 Uiso 1 1 calc R . . . .
C10A C 0.5907(6) 0.6899(3) 0.56211(14) 0.0301(11) Uani 1 1 d . . . . .
C10C C 0.5396(7) 0.1307(3) 0.53791(18) 0.0432(15) Uani 1 1 d . . . . .
H10C H 0.545173 0.080967 0.537014 0.052 Uiso 1 1 calc R . . . .
C11A C 0.6942(7) 0.7125(3) 0.59070(14) 0.0305(12) Uani 1 1 d . . . . .
C11C C 0.6043(7) 0.3857(4) 0.57208(16) 0.0366(14) Uani 1 1 d . . . . .
C12A C 0.7395(7) 0.6493(3) 0.60923(14) 0.0324(12) Uani 1 1 d . . . . .
C12C C 0.5058(6) 0.3487(3) 0.54313(15) 0.0329(12) Uani 1 1 d . . . . .
C13A C 0.8380(7) 0.6493(4) 0.63949(15) 0.0393(14) Uani 1 1 d . . . . .
H13A H 0.867727 0.606871 0.651130 0.047 Uiso 1 1 calc R . . . .
C14A C 0.8917(7) 0.7138(4) 0.65220(16) 0.0436(16) Uani 1 1 d . . . . .
H14A H 0.956923 0.715490 0.673313 0.052 Uiso 1 1 calc R . . . .
C15A C 0.8518(7) 0.7765(4) 0.63455(16) 0.0406(14) Uani 1 1 d . . . . .
H15A H 0.892520 0.819728 0.643503 0.049 Uiso 1 1 calc R . . . .
C16A C 0.7537(7) 0.7761(3) 0.60425(16) 0.0389(13) Uani 1 1 d . . . . .
H16A H 0.726706 0.818931 0.592646 0.047 Uiso 1 1 calc R . . . .
C17A C 0.5043(7) 0.7826(3) 0.51797(16) 0.0334(12) Uani 1 1 d . . . . .
C18A C 0.4945(7) 0.8415(3) 0.54007(16) 0.0360(13) Uani 1 1 d . . . . .
H18A H 0.482067 0.836144 0.565316 0.043 Uiso 1 1 calc R . . . .
C19A C 0.5029(8) 0.9078(3) 0.52513(17) 0.0442(14) Uani 1 1 d . . . . .
H19A H 0.496662 0.947960 0.540181 0.053 Uiso 1 1 calc R . . . .
C20A C 0.5203(8) 0.9160(4) 0.48832(18) 0.0497(16) Uani 1 1 d . . . . .
H20A H 0.526144 0.961610 0.478185 0.060 Uiso 1 1 calc R . . . .
C21A C 0.5290(8) 0.8581(4) 0.46652(17) 0.0472(15) Uani 1 1 d . . . . .
H21A H 0.538502 0.863987 0.441241 0.057 Uiso 1 1 calc R . . . .
C22A C 0.5240(7) 0.7912(3) 0.48097(15) 0.0377(12) Uani 1 1 d . . . . .
H22A H 0.533963 0.751394 0.465774 0.045 Uiso 1 1 calc R . . . .
O1D O 0.1450(5) 0.9495(2) 0.29752(11) 0.0434(10) Uani 1 1 d . . . . .
O2D O 0.3250(5) 0.8837(2) 0.34869(10) 0.0378(9) Uani 1 1 d . . . . .
N1B N 0.0787(5) 1.0920(2) 0.28031(11) 0.0331(10) Uani 1 1 d . . . . .
H1B H 0.069208 1.048178 0.273242 0.040 Uiso 1 1 calc R . . . .
N1D N 0.1109(6) 0.6632(3) 0.31107(13) 0.0375(11) Uani 1 1 d . . . . .
N2B N 0.3503(5) 1.0359(2) 0.35069(11) 0.0322(10) Uani 1 1 d . . . . .
H2B H 0.341376 0.992614 0.342791 0.039 Uiso 1 1 calc R . . . .
N2D N -0.0555(6) 0.7278(3) 0.25729(13) 0.0368(11) Uani 1 1 d . . . . .
N3B N 0.2479(6) 1.2133(2) 0.34084(12) 0.0320(10) Uani 1 1 d . . . . .
C1B C 0.0069(6) 1.1492(3) 0.26470(15) 0.0332(12) Uani 1 1 d . . . . .
C1D C 0.1959(8) 0.6314(3) 0.33703(16) 0.0430(14) Uani 1 1 d . . . . .
H1D H 0.187611 0.581783 0.338640 0.052 Uiso 1 1 calc R . . . .
C2B C -0.0944(7) 1.1515(3) 0.23389(16) 0.0364(13) Uani 1 1 d . . . . .
H2BA H -0.122674 1.109807 0.221345 0.044 Uiso 1 1 calc R . . . .
C2D C 0.2943(7) 0.6648(3) 0.36161(16) 0.0405(13) Uani 1 1 d . . . . .
H2D H 0.353085 0.638903 0.379197 0.049 Uiso 1 1 calc R . . . .
C3B C -0.1505(7) 1.2153(4) 0.22272(16) 0.0386(14) Uani 1 1 d . . . . .
H3B H -0.218399 1.217575 0.202037 0.046 Uiso 1 1 calc R . . . .
C3D C 0.3054(7) 0.7372(3) 0.36002(15) 0.0362(13) Uani 1 1 d . . . . .
H3D H 0.370545 0.762357 0.376773 0.043 Uiso 1 1 calc R . . . .
C4B C -0.1113(7) 1.2776(4) 0.24070(15) 0.0397(14) Uani 1 1 d . . . . .
H4B H -0.154214 1.320902 0.232261 0.048 Uiso 1 1 calc R . . . .
C4D C 0.2188(7) 0.7722(3) 0.33324(15) 0.0321(13) Uani 1 1 d . . . . .
C5B C -0.0108(7) 1.2769(3) 0.27064(15) 0.0340(12) Uani 1 1 d . . . . .
H5B H 0.016602 1.319264 0.282601 0.041 Uiso 1 1 calc R . . . .
C5D C 0.1216(6) 0.7339(3) 0.30909(14) 0.0298(11) Uani 1 1 d . . . . .
C6B C 0.0496(7) 1.2128(3) 0.28296(15) 0.0308(12) Uani 1 1 d . . . . .
C6D C 0.0307(6) 0.7690(3) 0.27968(14) 0.0293(12) Uani 1 1 d . . . . .
C7B C 0.1545(6) 1.1887(3) 0.31167(13) 0.0308(11) Uani 1 1 d . . . . .
C7D C 0.0373(6) 0.8426(3) 0.27580(15) 0.0305(12) Uani 1 1 d . . . . .
C8B C 0.1681(6) 1.1155(3) 0.30892(14) 0.0291(12) Uani 1 1 d . . . . .
C8D C -0.0482(7) 0.8733(3) 0.24732(15) 0.0374(13) Uani 1 1 d . . . . .
H8D H -0.047658 0.922713 0.244116 0.045 Uiso 1 1 calc R . . . .
C9B C 0.2717(6) 1.0941(3) 0.33711(13) 0.0300(11) Uani 1 1 d . . . . .
C9D C -0.1329(7) 0.8310(4) 0.22413(15) 0.0390(13) Uani 1 1 d . . . . .
H9D H -0.189847 0.850496 0.204246 0.047 Uiso 1 1 calc R . . . .
C10B C 0.3177(7) 1.1538(3) 0.35629(13) 0.0313(11) Uani 1 1 d . . . . .
C10D C -0.1341(7) 0.7597(4) 0.23011(17) 0.0416(15) Uani 1 1 d . . . . .
H10D H -0.194473 0.731121 0.213937 0.050 Uiso 1 1 calc R . . . .
C11B C 0.4305(6) 1.1331(3) 0.38356(13) 0.0292(11) Uani 1 1 d . . . . .
C11D C 0.2339(6) 0.8493(3) 0.32953(14) 0.0327(12) Uani 1 1 d . . . . .
C12B C 0.4462(6) 1.0587(3) 0.37923(13) 0.0294(11) Uani 1 1 d . . . . .
C12D C 0.1349(7) 0.8854(3) 0.30011(15) 0.0319(12) Uani 1 1 d . . . . .
C13B C 0.5510(7) 1.0193(3) 0.40054(14) 0.0343(11) Uani 1 1 d . . . . .
H13B H 0.559974 0.969959 0.397570 0.041 Uiso 1 1 calc R . . . .
C14B C 0.6420(7) 1.0543(3) 0.42628(15) 0.0385(13) Uani 1 1 d . . . . .
H14B H 0.715615 1.028489 0.440906 0.046 Uiso 1 1 calc R . . . .
C15B C 0.6283(7) 1.1273(3) 0.43134(15) 0.0391(13) Uani 1 1 d . . . . .
H15B H 0.691649 1.149695 0.449400 0.047 Uiso 1 1 calc R . . . .
C16B C 0.5235(7) 1.1666(3) 0.41025(13) 0.0340(12) Uani 1 1 d . . . . .
H16B H 0.514441 1.215746 0.413787 0.041 Uiso 1 1 calc R . . . .
C17B C 0.2363(7) 1.2809(3) 0.35682(14) 0.0329(12) Uani 1 1 d . . . . .
C18B C 0.2178(7) 1.2872(3) 0.39387(15) 0.0376(12) Uani 1 1 d . . . . .
H18B H 0.211420 1.246465 0.408526 0.045 Uiso 1 1 calc R . . . .
C19B C 0.2086(8) 1.3532(4) 0.40922(17) 0.0478(15) Uani 1 1 d . . . . .
H19B H 0.197166 1.357910 0.434526 0.057 Uiso 1 1 calc R . . . .
C20B C 0.2160(8) 1.4123(3) 0.38781(18) 0.0492(16) Uani 1 1 d . . . . .
H20B H 0.208551 1.457462 0.398413 0.059 Uiso 1 1 calc R . . . .
C21B C 0.2344(8) 1.4058(3) 0.35091(18) 0.0449(14) Uani 1 1 d . . . . .
H21B H 0.238946 1.446565 0.336239 0.054 Uiso 1 1 calc R . . . .
C22B C 0.2462(7) 1.3398(3) 0.33544(16) 0.0375(13) Uani 1 1 d . . . . .
H22B H 0.261009 1.335207 0.310221 0.045 Uiso 1 1 calc R . . . .
Cl1 Cl 0.7783(3) -0.02394(11) 0.60046(5) 0.0704(5) Uani 1 1 d D . . . .
Cl2 Cl 0.8384(3) -0.00662(10) 0.68919(6) 0.0645(5) Uani 1 1 d D . . . .
C1E C 0.7374(13) 0.0540(5) 0.6285(3) 0.056(2) Uani 0.746(7) 1 d D . P A 1
H1EA H 0.739049 0.096383 0.613157 0.067 Uiso 0.746(7) 1 calc R . P A 1
H1EB H 0.626898 0.049944 0.639149 0.067 Uiso 0.746(7) 1 calc R . P A 1
C2E C 0.8598(13) 0.0623(5) 0.6580(2) 0.054(2) Uani 0.746(7) 1 d D . P A 1
H2EA H 0.842968 0.107841 0.670268 0.065 Uiso 0.746(7) 1 calc R . P A 1
H2EB H 0.971547 0.061886 0.647825 0.065 Uiso 0.746(7) 1 calc R . P A 1
C1F C 0.836(4) 0.0571(11) 0.6187(7) 0.056(2) Uani 0.254(7) 1 d D . P A 2
H1FA H 0.956870 0.060437 0.620491 0.067 Uiso 0.254(7) 1 calc R . P A 2
H1FB H 0.796045 0.096157 0.603619 0.067 Uiso 0.254(7) 1 calc R . P A 2
C2F C 0.759(4) 0.0596(14) 0.6557(7) 0.054(2) Uani 0.254(7) 1 d D . P A 2
H2FA H 0.640087 0.052666 0.653051 0.065 Uiso 0.254(7) 1 calc R . P A 2
H2FB H 0.776306 0.107124 0.665814 0.065 Uiso 0.254(7) 1 calc R . P A 2
Cl3 Cl 0.6151(3) 0.49594(12) 0.68802(7) 0.0809(7) Uani 1 1 d D . . . .
Cl4 Cl 0.5504(3) 0.47333(11) 0.77671(6) 0.0716(5) Uani 1 1 d D . . . .
C3E C 0.6483(12) 0.5612(5) 0.7218(2) 0.051(2) Uani 0.746(7) 1 d D . P A 1
H3EA H 0.759126 0.555814 0.732069 0.061 Uiso 0.746(7) 1 calc R . P A 1
H3EB H 0.640157 0.608495 0.710963 0.061 Uiso 0.746(7) 1 calc R . P A 1
C4E C 0.5225(13) 0.5532(5) 0.7509(3) 0.054(2) Uani 0.746(7) 1 d D . P A 1
H4EA H 0.412309 0.552925 0.739913 0.065 Uiso 0.746(7) 1 calc R . P A 1
H4EB H 0.528918 0.594050 0.767268 0.065 Uiso 0.746(7) 1 calc R . P A 1
C3F C 0.536(4) 0.5576(13) 0.7227(6) 0.051(2) Uani 0.254(7) 1 d D . P A 2
H3FA H 0.547374 0.605916 0.713328 0.061 Uiso 0.254(7) 1 calc R . P A 2
H3FB H 0.417199 0.548590 0.725659 0.061 Uiso 0.254(7) 1 calc R . P A 2
C4F C 0.613(4) 0.5550(11) 0.7592(7) 0.054(2) Uani 0.254(7) 1 d D . P A 2
H4FB H 0.573884 0.594079 0.774485 0.065 Uiso 0.254(7) 1 calc R . P A 2
H4FA H 0.733581 0.557584 0.757380 0.065 Uiso 0.254(7) 1 calc R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1C C12C 1.223(7) . ?
O2C C11C 1.230(8) . ?
N1A H1A 0.8800 . ?
N1A C1A 1.377(7) . ?
N1A C8A 1.375(7) . ?
N1C C1C 1.335(8) . ?
N1C C5C 1.352(7) . ?
N2A H2A 0.8800 . ?
N2A C9A 1.375(7) . ?
N2A C12A 1.389(7) . ?
N2C C6C 1.344(8) . ?
N2C C10C 1.331(8) . ?
N3A C7A 1.397(7) . ?
N3A C10A 1.397(7) . ?
N3A C17A 1.416(7) . ?
C1A C2A 1.389(8) . ?
C1A C6A 1.426(8) . ?
C1C H1C 0.9500 . ?
C1C C2C 1.389(10) . ?
C2A H2AA 0.9500 . ?
C2A C3A 1.387(9) . ?
C2C H2C 0.9500 . ?
C2C C3C 1.376(9) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.399(9) . ?
C3C H3C 0.9500 . ?
C3C C4C 1.407(8) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.376(8) . ?
C4C C5C 1.398(9) . ?
C4C C11C 1.465(9) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.410(8) . ?
C5C C6C 1.478(8) . ?
C6A C7A 1.436(7) . ?
C6C C7C 1.405(8) . ?
C7A C8A 1.392(8) . ?
C7C C8C 1.387(8) . ?
C7C C12C 1.465(8) . ?
C8A C9A 1.396(8) . ?
C8C H8C 0.9500 . ?
C8C C9C 1.386(9) . ?
C9A C10A 1.402(8) . ?
C9C H9C 0.9500 . ?
C9C C10C 1.389(9) . ?
C10A C11A 1.426(8) . ?
C10C H10C 0.9500 . ?
C11A C12A 1.438(8) . ?
C11A C16A 1.400(8) . ?
C11C C12C 1.519(9) . ?
C12A C13A 1.385(8) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.389(10) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.402(10) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.384(9) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.394(8) . ?
C17A C22A 1.395(8) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.382(9) . ?
C19A H19A 0.9500 . ?
C19A C20A 1.385(9) . ?
C20A H20A 0.9500 . ?
C20A C21A 1.371(10) . ?
C21A H21A 0.9500 . ?
C21A C22A 1.385(8) . ?
C22A H22A 0.9500 . ?
O1D C12D 1.229(7) . ?
O2D C11D 1.222(7) . ?
N1B H1B 0.8800 . ?
N1B C1B 1.368(7) . ?
N1B C8B 1.367(7) . ?
N1D C1D 1.336(8) . ?
N1D C5D 1.354(7) . ?
N2B H2B 0.8800 . ?
N2B C9B 1.378(7) . ?
N2B C12B 1.389(7) . ?
N2D C6D 1.345(7) . ?
N2D C10D 1.344(8) . ?
N3B C7B 1.408(7) . ?
N3B C10B 1.395(7) . ?
N3B C17B 1.423(7) . ?
C1B C2B 1.415(8) . ?
C1B C6B 1.433(8) . ?
C1D H1D 0.9500 . ?
C1D C2D 1.375(9) . ?
C2B H2BA 0.9500 . ?
C2B C3B 1.367(9) . ?
C2D H2D 0.9500 . ?
C2D C3D 1.385(9) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.400(9) . ?
C3D H3D 0.9500 . ?
C3D C4D 1.393(8) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.385(8) . ?
C4D C5D 1.404(8) . ?
C4D C11D 1.482(8) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.396(8) . ?
C5D C6D 1.482(8) . ?
C6B C7B 1.445(8) . ?
C6D C7D 1.412(8) . ?
C7B C8B 1.403(8) . ?
C7D C8D 1.398(8) . ?
C7D C12D 1.457(8) . ?
C8B C9B 1.409(8) . ?
C8D H8D 0.9500 . ?
C8D C9D 1.369(9) . ?
C9B C10B 1.394(8) . ?
C9D H9D 0.9500 . ?
C9D C10D 1.379(10) . ?
C10B C11B 1.427(7) . ?
C10D H10D 0.9500 . ?
C11B C12B 1.435(8) . ?
C11B C16B 1.404(7) . ?
C11D C12D 1.526(8) . ?
C12B C13B 1.389(8) . ?
C13B H13B 0.9500 . ?
C13B C14B 1.385(8) . ?
C14B H14B 0.9500 . ?
C14B C15B 1.408(9) . ?
C15B H15B 0.9500 . ?
C15B C16B 1.383(8) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.392(8) . ?
C17B C22B 1.379(8) . ?
C18B H18B 0.9500 . ?
C18B C19B 1.385(9) . ?
C19B H19B 0.9500 . ?
C19B C20B 1.380(10) . ?
C20B H20B 0.9500 . ?
C20B C21B 1.386(9) . ?
C21B H21B 0.9500 . ?
C21B C22B 1.388(8) . ?
C22B H22B 0.9500 . ?
Cl1 C1E 1.847(10) . ?
Cl1 C1F 1.754(19) . ?
Cl2 C2E 1.762(9) . ?
Cl2 C2F 1.89(2) . ?
C1E H1EA 0.9900 . ?
C1E H1EB 0.9900 . ?
C1E C2E 1.494(13) . ?
C2E H2EA 0.9900 . ?
C2E H2EB 0.9900 . ?
C1F H1FA 0.9900 . ?
C1F H1FB 0.9900 . ?
C1F C2F 1.52(3) . ?
C2F H2FA 0.9900 . ?
C2F H2FB 0.9900 . ?
Cl3 C3E 1.788(9) . ?
Cl3 C3F 1.864(19) . ?
Cl4 C4E 1.816(10) . ?
Cl4 C4F 1.77(2) . ?
C3E H3EA 0.9900 . ?
C3E H3EB 0.9900 . ?
C3E C4E 1.502(12) . ?
C4E H4EA 0.9900 . ?
C4E H4EB 0.9900 . ?
C3F H3FA 0.9900 . ?
C3F H3FB 0.9900 . ?
C3F C4F 1.50(2) . ?
C4F H4FB 0.9900 . ?
C4F H4FA 0.9900 . ?

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
C1A N1A H1A 126.0 . . ?
C8A N1A H1A 126.0 . . ?
C8A N1A C1A 108.0(5) . . ?
C1C N1C C5C 117.7(5) . . ?
C9A N2A H2A 126.1 . . ?
C9A N2A C12A 107.9(5) . . ?
C12A N2A H2A 126.1 . . ?
C10C N2C C6C 117.5(5) . . ?
C7A N3A C10A 105.7(4) . . ?
C7A N3A C17A 126.0(4) . . ?
C10A N3A C17A 126.8(5) . . ?
N1A C1A C2A 128.2(5) . . ?
N1A C1A C6A 110.0(5) . . ?
C2A C1A C6A 121.7(5) . . ?
N1C C1C H1C 117.9 . . ?
N1C C1C C2C 124.3(6) . . ?
C2C C1C H1C 117.9 . . ?
C1A C2A H2AA 121.0 . . ?
C3A C2A C1A 118.0(6) . . ?
C3A C2A H2AA 121.0 . . ?
C1C C2C H2C 121.0 . . ?
C3C C2C C1C 118.0(6) . . ?
C3C C2C H2C 121.0 . . ?
C2A C3A H3A 119.5 . . ?
C2A C3A C4A 121.0(5) . . ?
C4A C3A H3A 119.5 . . ?
C2C C3C H3C 120.3 . . ?
C2C C3C C4C 119.4(6) . . ?
C4C C3C H3C 120.3 . . ?
C3A C4A H4A 119.2 . . ?
C5A C4A C3A 121.7(5) . . ?
C5A C4A H4A 119.2 . . ?
C3C C4C C11C 119.8(5) . . ?
C5C C4C C3C 118.4(5) . . ?
C5C C4C C11C 121.8(5) . . ?
C4A C5A H5A 120.6 . . ?
C4A C5A C6A 118.7(5) . . ?
C6A C5A H5A 120.6 . . ?
N1C C5C C4C 122.2(5) . . ?
N1C C5C C6C 117.6(5) . . ?
C4C C5C C6C 120.3(5) . . ?
C1A C6A C7A 104.5(4) . . ?
C5A C6A C1A 118.8(5) . . ?
C5A C6A C7A 136.7(5) . . ?
N2C C6C C5C 117.2(5) . . ?
N2C C6C C7C 122.2(5) . . ?
C7C C6C C5C 120.5(5) . . ?
N3A C7A C6A 141.1(5) . . ?
C8A C7A N3A 110.4(5) . . ?
C8A C7A C6A 108.1(5) . . ?
C6C C7C C12C 121.3(5) . . ?
C8C C7C C6C 119.1(5) . . ?
C8C C7C C12C 119.5(5) . . ?
N1A C8A C7A 109.4(5) . . ?
N1A C8A C9A 143.7(5) . . ?
C7A C8A C9A 106.8(5) . . ?
C7C C8C H8C 120.6 . . ?
C9C C8C C7C 118.7(6) . . ?
C9C C8C H8C 120.6 . . ?
N2A C9A C8A 142.7(6) . . ?
N2A C9A C10A 109.5(5) . . ?
C8A C9A C10A 107.8(5) . . ?
C8C C9C H9C 120.9 . . ?
C8C C9C C10C 118.1(6) . . ?
C10C C9C H9C 120.9 . . ?
N3A C10A C9A 109.3(5) . . ?
N3A C10A C11A 142.4(5) . . ?
C9A C10A C11A 108.3(5) . . ?
N2C C10C C9C 124.3(6) . . ?
N2C C10C H10C 117.8 . . ?
C9C C10C H10C 117.8 . . ?
C10A C11A C12A 104.9(5) . . ?
C16A C11A C10A 137.5(6) . . ?
C16A C11A C12A 117.7(5) . . ?
O2C C11C C4C 122.9(6) . . ?
O2C C11C C12C 119.1(5) . . ?
C4C C11C C12C 118.0(5) . . ?
N2A C12A C11A 109.5(5) . . ?
C13A C12A N2A 127.9(6) . . ?
C13A C12A C11A 122.6(6) . . ?
O1C C12C C7C 122.8(5) . . ?
O1C C12C C11C 119.1(5) . . ?
C7C C12C C11C 118.1(5) . . ?
C12A C13A H13A 121.2 . . ?
C12A C13A C14A 117.5(6) . . ?
C14A C13A H13A 121.2 . . ?
C13A C14A H14A 119.3 . . ?
C13A C14A C15A 121.4(6) . . ?
C15A C14A H14A 119.3 . . ?
C14A C15A H15A 119.6 . . ?
C16A C15A C14A 120.8(6) . . ?
C16A C15A H15A 119.6 . . ?
C11A C16A H16A 120.0 . . ?
C15A C16A C11A 120.0(6) . . ?
C15A C16A H16A 120.0 . . ?
C18A C17A N3A 119.9(5) . . ?
C18A C17A C22A 119.6(5) . . ?
C22A C17A N3A 120.5(5) . . ?
C17A C18A H18A 120.1 . . ?
C19A C18A C17A 119.8(6) . . ?
C19A C18A H18A 120.1 . . ?
C18A C19A H19A 119.8 . . ?
C18A C19A C20A 120.3(6) . . ?
C20A C19A H19A 119.8 . . ?
C19A C20A H20A 120.0 . . ?
C21A C20A C19A 120.0(6) . . ?
C21A C20A H20A 120.0 . . ?
C20A C21A H21A 119.7 . . ?
C20A C21A C22A 120.7(6) . . ?
C22A C21A H21A 119.7 . . ?
C17A C22A H22A 120.2 . . ?
C21A C22A C17A 119.6(6) . . ?
C21A C22A H22A 120.2 . . ?
C1B N1B H1B 126.3 . . ?
C8B N1B H1B 126.3 . . ?
C8B N1B C1B 107.4(5) . . ?
C1D N1D C5D 117.3(5) . . ?
C9B N2B H2B 126.5 . . ?
C9B N2B C12B 107.0(4) . . ?
C12B N2B H2B 126.5 . . ?
C10D N2D C6D 116.9(5) . . ?
C7B N3B C17B 126.0(5) . . ?
C10B N3B C7B 105.6(4) . . ?
C10B N3B C17B 126.3(4) . . ?
N1B C1B C2B 128.4(6) . . ?
N1B C1B C6B 111.6(5) . . ?
C2B C1B C6B 120.0(5) . . ?
N1D C1D H1D 117.4 . . ?
N1D C1D C2D 125.1(6) . . ?
C2D C1D H1D 117.4 . . ?
C1B C2B H2BA 121.0 . . ?
C3B C2B C1B 118.1(6) . . ?
C3B C2B H2BA 121.0 . . ?
C1D C2D H2D 120.9 . . ?
C1D C2D C3D 118.2(6) . . ?
C3D C2D H2D 120.9 . . ?
C2B C3B H3B 118.9 . . ?
C2B C3B C4B 122.3(6) . . ?
C4B C3B H3B 118.9 . . ?
C2D C3D H3D 120.8 . . ?
C2D C3D C4D 118.3(5) . . ?
C4D C3D H3D 120.8 . . ?
C3B C4B H4B 119.6 . . ?
C5B C4B C3B 120.7(6) . . ?
C5B C4B H4B 119.6 . . ?
C3D C4D C5D 119.8(5) . . ?
C3D C4D C11D 120.0(5) . . ?
C5D C4D C11D 120.2(5) . . ?
C4B C5B H5B 120.5 . . ?
C4B C5B C6B 118.9(6) . . ?
C6B C5B H5B 120.5 . . ?
N1D C5D C4D 121.3(5) . . ?
N1D C5D C6D 117.2(5) . . ?
C4D C5D C6D 121.5(5) . . ?
C1B C6B C7B 103.1(5) . . ?
C5B C6B C1B 119.9(5) . . ?
C5B C6B C7B 137.0(5) . . ?
N2D C6D C5D 117.2(5) . . ?
N2D C6D C7D 122.5(5) . . ?
C7D C6D C5D 120.3(5) . . ?
N3B C7B C6B 141.8(5) . . ?
C8B C7B N3B 110.2(5) . . ?
C8B C7B C6B 108.0(5) . . ?
C6D C7D C12D 121.0(5) . . ?
C8D C7D C6D 118.3(5) . . ?
C8D C7D C12D 120.7(5) . . ?
N1B C8B C7B 109.9(5) . . ?
N1B C8B C9B 143.7(5) . . ?
C7B C8B C9B 106.4(5) . . ?
C7D C8D H8D 120.5 . . ?
C9D C8D C7D 119.0(6) . . ?
C9D C8D H8D 120.5 . . ?
N2B C9B C8B 141.9(5) . . ?
N2B C9B C10B 110.1(5) . . ?
C10B C9B C8B 107.9(5) . . ?
C8D C9D H9D 120.6 . . ?
C8D C9D C10D 118.9(6) . . ?
C10D C9D H9D 120.6 . . ?
N3B C10B C11B 141.5(5) . . ?
C9B C10B N3B 110.0(4) . . ?
C9B C10B C11B 108.3(5) . . ?
N2D C10D C9D 124.3(6) . . ?
N2D C10D H10D 117.8 . . ?
C9D C10D H10D 117.8 . . ?
C10B C11B C12B 104.5(4) . . ?
C16B C11B C10B 136.7(5) . . ?
C16B C11B C12B 118.7(5) . . ?
O2D C11D C4D 121.9(5) . . ?
O2D C11D C12D 120.0(5) . . ?
C4D C11D C12D 118.1(5) . . ?
N2B C12B C11B 110.1(4) . . ?
C13B C12B N2B 128.1(5) . . ?
C13B C12B C11B 121.8(5) . . ?
O1D C12D C7D 123.1(5) . . ?
O1D C12D C11D 118.0(5) . . ?
C7D C12D C11D 118.9(5) . . ?
C12B C13B H13B 121.1 . . ?
C14B C13B C12B 117.8(6) . . ?
C14B C13B H13B 121.1 . . ?
C13B C14B H14B 119.1 . . ?
C13B C14B C15B 121.8(5) . . ?
C15B C14B H14B 119.1 . . ?
C14B C15B H15B 119.7 . . ?
C16B C15B C14B 120.6(5) . . ?
C16B C15B H15B 119.7 . . ?
C11B C16B H16B 120.3 . . ?
C15B C16B C11B 119.4(5) . . ?
C15B C16B H16B 120.3 . . ?
C18B C17B N3B 119.9(5) . . ?
C22B C17B N3B 119.6(5) . . ?
C22B C17B C18B 120.5(5) . . ?
C17B C18B H18B 120.3 . . ?
C19B C18B C17B 119.5(6) . . ?
C19B C18B H18B 120.3 . . ?
C18B C19B H19B 119.9 . . ?
C20B C19B C18B 120.1(6) . . ?
C20B C19B H19B 119.9 . . ?
C19B C20B H20B 119.9 . . ?
C19B C20B C21B 120.3(6) . . ?
C21B C20B H20B 119.9 . . ?
C20B C21B H21B 120.1 . . ?
C20B C21B C22B 119.9(6) . . ?
C22B C21B H21B 120.1 . . ?
C17B C22B C21B 119.8(5) . . ?
C17B C22B H22B 120.1 . . ?
C21B C22B H22B 120.1 . . ?
Cl1 C1E H1EA 109.2 . . ?
Cl1 C1E H1EB 109.2 . . ?
H1EA C1E H1EB 107.9 . . ?
C2E C1E Cl1 112.3(7) . . ?
C2E C1E H1EA 109.2 . . ?
C2E C1E H1EB 109.2 . . ?
Cl2 C2E H2EA 109.7 . . ?
Cl2 C2E H2EB 109.7 . . ?
C1E C2E Cl2 109.7(7) . . ?
C1E C2E H2EA 109.7 . . ?
C1E C2E H2EB 109.7 . . ?
H2EA C2E H2EB 108.2 . . ?
Cl1 C1F H1FA 110.6 . . ?
Cl1 C1F H1FB 110.6 . . ?
H1FA C1F H1FB 108.8 . . ?
C2F C1F Cl1 105.5(19) . . ?
C2F C1F H1FA 110.6 . . ?
C2F C1F H1FB 110.6 . . ?
Cl2 C2F H2FA 108.3 . . ?
Cl2 C2F H2FB 108.3 . . ?
C1F C2F Cl2 115.8(18) . . ?
C1F C2F H2FA 108.3 . . ?
C1F C2F H2FB 108.3 . . ?
H2FA C2F H2FB 107.4 . . ?
Cl3 C3E H3EA 109.8 . . ?
Cl3 C3E H3EB 109.8 . . ?
H3EA C3E H3EB 108.2 . . ?
C4E C3E Cl3 109.4(6) . . ?
C4E C3E H3EA 109.8 . . ?
C4E C3E H3EB 109.8 . . ?
Cl4 C4E H4EA 109.1 . . ?
Cl4 C4E H4EB 109.1 . . ?
C3E C4E Cl4 112.3(7) . . ?
C3E C4E H4EA 109.1 . . ?
C3E C4E H4EB 109.1 . . ?
H4EA C4E H4EB 107.9 . . ?
Cl3 C3F H3FA 108.0 . . ?
Cl3 C3F H3FB 108.0 . . ?
H3FA C3F H3FB 107.2 . . ?
C4F C3F Cl3 117.3(18) . . ?
C4F C3F H3FA 108.0 . . ?
C4F C3F H3FB 108.0 . . ?
Cl4 C4F H4FB 111.0 . . ?
Cl4 C4F H4FA 111.0 . . ?
C3F C4F Cl4 103.9(17) . . ?
C3F C4F H4FB 111.0 . . ?
C3F C4F H4FA 111.0 . . ?
H4FB C4F H4FA 109.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1A H1A O1C 0.88 2.13 2.960(6) 156.8 . yes
N1A H1A O2C 0.88 2.46 3.067(6) 126.8 . yes
N2A H2A O2C 0.88 2.18 2.856(6) 132.8 . yes
N1B H1B O1D 0.88 2.18 2.844(6) 132.2 . yes
N2B H2B O1D 0.88 2.47 3.074(6) 126.5 . yes
N2B H2B O2D 0.88 2.09 2.912(6) 154.4 . yes

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
O2C C11C C12C O1C -1.5(8) . . . . ?
O2C C11C C12C C7C -179.9(5) . . . . ?
N1A C1A C2A C3A 176.1(5) . . . . ?
N1A C1A C6A C5A -178.3(4) . . . . ?
N1A C1A C6A C7A 1.3(6) . . . . ?
N1A C8A C9A N2A 4.8(14) . . . . ?
N1A C8A C9A C10A -173.2(7) . . . . ?
N1C C1C C2C C3C -2.6(9) . . . . ?
N1C C5C C6C N2C 1.0(7) . . . . ?
N1C C5C C6C C7C -179.2(5) . . . . ?
N2A C9A C10A N3A -179.2(4) . . . . ?
N2A C9A C10A C11A 0.7(6) . . . . ?
N2A C12A C13A C14A -177.7(5) . . . . ?
N2C C6C C7C C8C 0.4(8) . . . . ?
N2C C6C C7C C12C 177.0(5) . . . . ?
N3A C7A C8A N1A 175.6(4) . . . . ?
N3A C7A C8A C9A -0.6(6) . . . . ?
N3A C10A C11A C12A 179.2(7) . . . . ?
N3A C10A C11A C16A 1.0(12) . . . . ?
N3A C17A C18A C19A 179.2(5) . . . . ?
N3A C17A C22A C21A 179.6(5) . . . . ?
C1A N1A C8A C7A 0.5(6) . . . . ?
C1A N1A C8A C9A 174.3(7) . . . . ?
C1A C2A C3A C4A 0.9(8) . . . . ?
C1A C6A C7A N3A -173.9(7) . . . . ?
C1A C6A C7A C8A -1.0(6) . . . . ?
C1C N1C C5C C4C 0.5(8) . . . . ?
C1C N1C C5C C6C -179.2(5) . . . . ?
C1C C2C C3C C4C 1.5(8) . . . . ?
C2A C1A C6A C5A -1.1(8) . . . . ?
C2A C1A C6A C7A 178.6(5) . . . . ?
C2A C3A C4A C5A 0.6(9) . . . . ?
C2C C3C C4C C5C 0.4(8) . . . . ?
C2C C3C C4C C11C 179.0(5) . . . . ?
C3A C4A C5A C6A -2.3(8) . . . . ?
C3C C4C C5C N1C -1.4(8) . . . . ?
C3C C4C C5C C6C 178.3(5) . . . . ?
C3C C4C C11C O2C -0.4(8) . . . . ?
C3C C4C C11C C12C -177.3(5) . . . . ?
C4A C5A C6A C1A 2.5(7) . . . . ?
C4A C5A C6A C7A -177.0(6) . . . . ?
C4C C5C C6C N2C -178.7(5) . . . . ?
C4C C5C C6C C7C 1.1(8) . . . . ?
C4C C11C C12C O1C 175.5(5) . . . . ?
C4C C11C C12C C7C -2.9(7) . . . . ?
C5A C6A C7A N3A 5.7(12) . . . . ?
C5A C6A C7A C8A 178.6(6) . . . . ?
C5C N1C C1C C2C 1.5(8) . . . . ?
C5C C4C C11C O2C 178.2(5) . . . . ?
C5C C4C C11C C12C 1.3(8) . . . . ?
C5C C6C C7C C8C -179.4(5) . . . . ?
C5C C6C C7C C12C -2.9(8) . . . . ?
C6A C1A C2A C3A -0.6(8) . . . . ?
C6A C7A C8A N1A 0.3(6) . . . . ?
C6A C7A C8A C9A -175.8(4) . . . . ?
C6C N2C C10C C9C 0.6(9) . . . . ?
C6C C7C C8C C9C 0.3(8) . . . . ?
C6C C7C C12C O1C -174.6(5) . . . . ?
C6C C7C C12C C11C 3.7(7) . . . . ?
C7A N3A C10A C9A 0.1(6) . . . . ?
C7A N3A C10A C11A -179.7(7) . . . . ?
C7A N3A C17A C18A 146.4(6) . . . . ?
C7A N3A C17A C22A -35.0(8) . . . . ?
C7A C8A C9A N2A 178.6(7) . . . . ?
C7A C8A C9A C10A 0.6(6) . . . . ?
C7C C8C C9C C10C -0.5(8) . . . . ?
C8A N1A C1A C2A -178.2(5) . . . . ?
C8A N1A C1A C6A -1.2(6) . . . . ?
C8A C9A C10A N3A -0.5(6) . . . . ?
C8A C9A C10A C11A 179.4(4) . . . . ?
C8C C7C C12C O1C 2.0(8) . . . . ?
C8C C7C C12C C11C -179.7(5) . . . . ?
C8C C9C C10C N2C 0.0(9) . . . . ?
C9A N2A C12A C11A 0.2(6) . . . . ?
C9A N2A C12A C13A 179.0(6) . . . . ?
C9A C10A C11A C12A -0.6(6) . . . . ?
C9A C10A C11A C16A -178.8(6) . . . . ?
C10A N3A C7A C6A 173.1(7) . . . . ?
C10A N3A C7A C8A 0.3(6) . . . . ?
C10A N3A C17A C18A -50.0(8) . . . . ?
C10A N3A C17A C22A 128.6(6) . . . . ?
C10A C11A C12A N2A 0.2(6) . . . . ?
C10A C11A C12A C13A -178.6(5) . . . . ?
C10A C11A C16A C15A 177.8(6) . . . . ?
C10C N2C C6C C5C 179.0(5) . . . . ?
C10C N2C C6C C7C -0.8(8) . . . . ?
C11A C12A C13A C14A 0.9(9) . . . . ?
C11C C4C C5C N1C 180.0(5) . . . . ?
C11C C4C C5C C6C -0.3(8) . . . . ?
C12A N2A C9A C8A -178.5(7) . . . . ?
C12A N2A C9A C10A -0.5(6) . . . . ?
C12A C11A C16A C15A -0.3(8) . . . . ?
C12A C13A C14A C15A -1.8(9) . . . . ?
C12C C7C C8C C9C -176.4(5) . . . . ?
C13A C14A C15A C16A 1.6(9) . . . . ?
C14A C15A C16A C11A -0.5(9) . . . . ?
C16A C11A C12A N2A 178.9(5) . . . . ?
C16A C11A C12A C13A 0.1(8) . . . . ?
C17A N3A C7A C6A -20.5(10) . . . . ?
C17A N3A C7A C8A 166.7(5) . . . . ?
C17A N3A C10A C9A -166.2(5) . . . . ?
C17A N3A C10A C11A 14.0(11) . . . . ?
C17A C18A C19A C20A 0.3(9) . . . . ?
C18A C17A C22A C21A -1.8(9) . . . . ?
C18A C19A C20A C21A 0.1(10) . . . . ?
C19A C20A C21A C22A -1.4(10) . . . . ?
C20A C21A C22A C17A 2.2(9) . . . . ?
C22A C17A C18A C19A 0.6(9) . . . . ?
O2D C11D C12D O1D -2.9(7) . . . . ?
O2D C11D C12D C7D 175.2(5) . . . . ?
N1B C1B C2B C3B -178.8(5) . . . . ?
N1B C1B C6B C5B 179.3(5) . . . . ?
N1B C1B C6B C7B -0.4(6) . . . . ?
N1B C8B C9B N2B 5.2(14) . . . . ?
N1B C8B C9B C10B 179.6(7) . . . . ?
N1D C1D C2D C3D 1.1(9) . . . . ?
N1D C5D C6D N2D 0.1(7) . . . . ?
N1D C5D C6D C7D -179.5(5) . . . . ?
N2B C9B C10B N3B 175.5(4) . . . . ?
N2B C9B C10B C11B -0.2(6) . . . . ?
N2B C12B C13B C14B 176.2(5) . . . . ?
N2D C6D C7D C8D -0.6(8) . . . . ?
N2D C6D C7D C12D -178.6(5) . . . . ?
N3B C7B C8B N1B -179.3(4) . . . . ?
N3B C7B C8B C9B 0.2(6) . . . . ?
N3B C10B C11B C12B -174.0(7) . . . . ?
N3B C10B C11B C16B 3.9(12) . . . . ?
N3B C17B C18B C19B 179.2(5) . . . . ?
N3B C17B C22B C21B 179.8(5) . . . . ?
C1B N1B C8B C7B -0.3(6) . . . . ?
C1B N1B C8B C9B -179.6(7) . . . . ?
C1B C2B C3B C4B -0.2(9) . . . . ?
C1B C6B C7B N3B 179.3(7) . . . . ?
C1B C6B C7B C8B 0.2(6) . . . . ?
C1D N1D C5D C4D 0.3(7) . . . . ?
C1D N1D C5D C6D 178.4(5) . . . . ?
C1D C2D C3D C4D -1.1(8) . . . . ?
C2B C1B C6B C5B 0.9(8) . . . . ?
C2B C1B C6B C7B -178.8(5) . . . . ?
C2B C3B C4B C5B 1.0(9) . . . . ?
C2D C3D C4D C5D 0.9(8) . . . . ?
C2D C3D C4D C11D -177.0(5) . . . . ?
C3B C4B C5B C6B -0.8(8) . . . . ?
C3D C4D C5D N1D -0.5(8) . . . . ?
C3D C4D C5D C6D -178.5(5) . . . . ?
C3D C4D C11D O2D 2.3(8) . . . . ?
C3D C4D C11D C12D -179.2(5) . . . . ?
C4B C5B C6B C1B -0.2(8) . . . . ?
C4B C5B C6B C7B 179.4(6) . . . . ?
C4D C5D C6D N2D 178.2(5) . . . . ?
C4D C5D C6D C7D -1.4(7) . . . . ?
C4D C11D C12D O1D 178.6(5) . . . . ?
C4D C11D C12D C7D -3.3(7) . . . . ?
C5B C6B C7B N3B -0.3(12) . . . . ?
C5B C6B C7B C8B -179.4(6) . . . . ?
C5D N1D C1D C2D -0.7(9) . . . . ?
C5D C4D C11D O2D -175.5(5) . . . . ?
C5D C4D C11D C12D 2.9(7) . . . . ?
C5D C6D C7D C8D 179.0(5) . . . . ?
C5D C6D C7D C12D 0.9(8) . . . . ?
C6B C1B C2B C3B -0.8(8) . . . . ?
C6B C7B C8B N1B 0.1(6) . . . . ?
C6B C7B C8B C9B 179.6(4) . . . . ?
C6D N2D C10D C9D -0.6(9) . . . . ?
C6D C7D C8D C9D -0.9(8) . . . . ?
C6D C7D C12D O1D 179.4(5) . . . . ?
C6D C7D C12D C11D 1.4(7) . . . . ?
C7B N3B C10B C9B 0.9(6) . . . . ?
C7B N3B C10B C11B 174.5(7) . . . . ?
C7B N3B C17B C18B 128.8(6) . . . . ?
C7B N3B C17B C22B -52.2(8) . . . . ?
C7B C8B C9B N2B -174.1(7) . . . . ?
C7B C8B C9B C10B 0.3(6) . . . . ?
C7D C8D C9D C10D 1.5(8) . . . . ?
C8B N1B C1B C2B 178.6(6) . . . . ?
C8B N1B C1B C6B 0.5(6) . . . . ?
C8B C9B C10B N3B -0.8(6) . . . . ?
C8B C9B C10B C11B -176.6(4) . . . . ?
C8D C7D C12D O1D 1.4(8) . . . . ?
C8D C7D C12D C11D -176.6(5) . . . . ?
C8D C9D C10D N2D -0.8(9) . . . . ?
C9B N2B C12B C11B -1.0(6) . . . . ?
C9B N2B C12B C13B -177.9(5) . . . . ?
C9B C10B C11B C12B -0.3(5) . . . . ?
C9B C10B C11B C16B 177.5(6) . . . . ?
C10B N3B C7B C6B -179.8(7) . . . . ?
C10B N3B C7B C8B -0.7(6) . . . . ?
C10B N3B C17B C18B -32.5(8) . . . . ?
C10B N3B C17B C22B 146.5(6) . . . . ?
C10B C11B C12B N2B 0.8(5) . . . . ?
C10B C11B C12B C13B 178.0(5) . . . . ?
C10B C11B C16B C15B -177.0(6) . . . . ?
C10D N2D C6D C5D -178.3(5) . . . . ?
C10D N2D C6D C7D 1.3(8) . . . . ?
C11B C12B C13B C14B -0.4(8) . . . . ?
C11D C4D C5D N1D 177.4(5) . . . . ?
C11D C4D C5D C6D -0.6(7) . . . . ?
C12B N2B C9B C8B 175.0(7) . . . . ?
C12B N2B C9B C10B 0.7(6) . . . . ?
C12B C11B C16B C15B 0.6(7) . . . . ?
C12B C13B C14B C15B 0.9(8) . . . . ?
C12D C7D C8D C9D 177.2(5) . . . . ?
C13B C14B C15B C16B -0.6(9) . . . . ?
C14B C15B C16B C11B -0.1(8) . . . . ?
C16B C11B C12B N2B -177.5(4) . . . . ?
C16B C11B C12B C13B -0.3(7) . . . . ?
C17B N3B C7B C6B 15.8(10) . . . . ?
C17B N3B C7B C8B -165.2(5) . . . . ?
C17B N3B C10B C9B 165.3(5) . . . . ?
C17B N3B C10B C11B -21.1(11) . . . . ?
C17B C18B C19B C20B 0.7(9) . . . . ?
C18B C17B C22B C21B -1.2(9) . . . . ?
C18B C19B C20B C21B -0.7(10) . . . . ?
C19B C20B C21B C22B -0.3(10) . . . . ?
C20B C21B C22B C17B 1.3(9) . . . . ?
C22B C17B C18B C19B 0.2(9) . . . . ?
Cl1 C1E C2E Cl2 -67.1(9) . . . . ?
Cl1 C1F C2F Cl2 66(3) . . . . ?
Cl3 C3E C4E Cl4 68.5(8) . . . . ?
Cl3 C3F C4F Cl4 -69(2) . . . . ?

_olex2_date_sample_data_collection 2018-09-12
_olex2_date_sample_submission    2018-09-11
_olex2_exptl_crystal_mounting_method 'mounted on a milar cryollop'
_olex2_submission_original_sample_id PhDIP-co-diaza
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.64(3)
2 0.36(3)

####################################################################### 
# 
# 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_pere76
_audit_block_doi                 10.5517/ccdc.csd.cc25m6gh
_database_code_depnum_ccdc_archive 'CCDC 2014456'
loop_
_audit_author_name
_audit_author_address
'Thierry Marris'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2020-07-06 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;
_audit_creation_date             2018-06-11
_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         'C16 H6 O4, 2(C22 H15 N3), 2(C2 H3 N)'
_chemical_formula_sum            'C64 H42 N8 O4'
_chemical_formula_weight         987.05
_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 0.0139 0.0070 '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 0.0240 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0390 0.0250 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   15.5498(8)
_cell_length_b                   15.4719(8)
_cell_length_c                   9.8900(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.929(3)
_cell_angle_gamma                90
_cell_volume                     2328.0(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    150
_cell_measurement_theta_max      54.032
_cell_measurement_theta_min      2.527
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.930
_exptl_absorpt_coefficient_mu    0.462
_exptl_absorpt_correction_T_max  0.5115
_exptl_absorpt_correction_T_min  0.3895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1380 before and 0.0793 after correction. The Ratio of minimum to maximum transmission is 0.7615. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             1028
_exptl_crystal_recrystallization_method MeCN
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            22621
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.104
_diffrn_reflns_theta_min         2.527
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3432
_reflns_number_total             4250
_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 (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.129
_refine_ls_extinction_coef       0.0084(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   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1186
_refine_ls_R_factor_gt           0.0986
_refine_ls_restrained_S_all      1.154
_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)+(0.0967P)²+6.2662P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2452
_refine_ls_wR_factor_ref         0.2607
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3B(H3B), C4B(H4B), C5B(H5B), N1A(H1A), N2A(H2A), C4A(H4A), C5A(H5A),
 C6A(H6A), C7A(H7A), C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A), C17A(H17A),
  C18A(H18A), C19A(H19A), C20A(H20A), C21A(H21A)
2.b Idealised Me refined as rotating group:
 C1C(H1CA,H1CB,H1CC)
;
_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
O1B O 0.36995(19) 0.13823(18) 0.2094(3) 0.0388(8) Uani 1 1 d . . . . .
O2B O 0.53687(19) -0.23902(18) -0.0681(3) 0.0377(7) Uani 1 1 d . . . . .
C1B C 0.4772(2) -0.0278(2) 0.0421(4) 0.0280(9) Uani 1 1 d . . . . .
C2B C 0.4241(2) 0.0089(3) 0.1268(4) 0.0294(9) Uani 1 1 d . . . . .
C3B C 0.3809(3) -0.0451(3) 0.2048(5) 0.0355(10) Uani 1 1 d . . . . .
H3B H 0.344539 -0.020199 0.260622 0.043 Uiso 1 1 calc R . . . .
C4B C 0.3899(3) -0.1340(3) 0.2023(5) 0.0389(10) Uani 1 1 d . . . . .
H4B H 0.361083 -0.169694 0.257282 0.047 Uiso 1 1 calc R . . . .
C5B C 0.4417(3) -0.1703(3) 0.1182(5) 0.0371(10) Uani 1 1 d . . . . .
H5B H 0.448130 -0.231291 0.115582 0.045 Uiso 1 1 calc R . . . .
C6B C 0.4841(2) -0.1183(2) 0.0382(4) 0.0299(9) Uani 1 1 d . . . . .
C7B C 0.4147(3) 0.1024(3) 0.1358(4) 0.0314(9) Uani 1 1 d . . . . .
C8B C 0.5349(2) -0.1602(2) -0.0533(4) 0.0290(9) Uani 1 1 d . . . . .
N1A N 0.2507(2) 0.1800(2) 0.3922(4) 0.0329(8) Uani 1 1 d . . . . .
H1A H 0.276187 0.139307 0.352070 0.039 Uiso 1 1 calc R . . . .
N2A N 0.3548(2) 0.3380(2) 0.2164(4) 0.0314(8) Uani 1 1 d . . . . .
H2A H 0.377337 0.295860 0.175125 0.038 Uiso 1 1 calc R . . . .
N3A N 0.2239(2) 0.4009(2) 0.4488(4) 0.0311(8) Uani 1 1 d . . . . .
C1A C 0.2654(3) 0.2672(3) 0.3866(4) 0.0313(9) Uani 1 1 d . . . . .
C2A C 0.2146(3) 0.3121(2) 0.4639(4) 0.0317(9) Uani 1 1 d . . . . .
C3A C 0.1626(3) 0.2496(3) 0.5198(5) 0.0330(9) Uani 1 1 d . . . . .
C4A C 0.0991(3) 0.2495(3) 0.6017(5) 0.0406(11) Uani 1 1 d . . . . .
H4A H 0.080752 0.302421 0.635381 0.049 Uiso 1 1 calc R . . . .
C5A C 0.0632(3) 0.1724(3) 0.6334(5) 0.0469(12) Uani 1 1 d . . . . .
H5A H 0.020150 0.172923 0.688934 0.056 Uiso 1 1 calc R . . . .
C6A C 0.0891(3) 0.0939(3) 0.5853(5) 0.0465(12) Uani 1 1 d . . . . .
H6A H 0.062491 0.041958 0.607680 0.056 Uiso 1 1 calc R . . . .
C7A C 0.1526(3) 0.0897(3) 0.5058(5) 0.0414(11) Uani 1 1 d . . . . .
H7A H 0.170996 0.035866 0.475178 0.050 Uiso 1 1 calc R . . . .
C8A C 0.1884(3) 0.1674(3) 0.4725(5) 0.0346(10) Uani 1 1 d . . . . .
C9A C 0.3059(2) 0.3291(2) 0.3168(4) 0.0285(9) Uani 1 1 d . . . . .
C10A C 0.2813(2) 0.4104(3) 0.3575(4) 0.0306(9) Uani 1 1 d . . . . .
C11A C 0.3182(2) 0.4743(3) 0.2815(4) 0.0301(9) Uani 1 1 d . . . . .
C12A C 0.3216(3) 0.5643(3) 0.2770(5) 0.0359(10) Uani 1 1 d . . . . .
H12A H 0.295144 0.598189 0.337431 0.043 Uiso 1 1 calc R . . . .
C13A C 0.3639(3) 0.6034(3) 0.1832(5) 0.0434(11) Uani 1 1 d . . . . .
H13A H 0.366442 0.664655 0.180078 0.052 Uiso 1 1 calc R . . . .
C14A C 0.4029(3) 0.5552(3) 0.0934(5) 0.0395(10) Uani 1 1 d . . . . .
H14A H 0.429778 0.584187 0.028287 0.047 Uiso 1 1 calc R . . . .
C15A C 0.4033(3) 0.4652(3) 0.0973(5) 0.0346(9) Uani 1 1 d . . . . .
H15A H 0.430782 0.432160 0.037182 0.041 Uiso 1 1 calc R . . . .
C16A C 0.3620(2) 0.4257(3) 0.1924(4) 0.0306(9) Uani 1 1 d . . . . .
C17A C 0.1524(3) 0.4651(3) 0.6205(5) 0.0391(10) Uani 1 1 d . . . . .
H17A H 0.173256 0.419009 0.682105 0.047 Uiso 1 1 calc R . . . .
C18A C 0.1009(3) 0.5308(3) 0.6599(5) 0.0464(12) Uani 1 1 d . . . . .
H18A H 0.085900 0.528842 0.748238 0.056 Uiso 1 1 calc R . . . .
C19A C 0.0715(3) 0.5989(3) 0.5704(6) 0.0520(13) Uani 1 1 d . . . . .
H19A H 0.036583 0.643549 0.597476 0.062 Uiso 1 1 calc R . . . .
C20A C 0.0932(3) 0.6011(3) 0.4427(5) 0.0458(12) Uani 1 1 d . . . . .
H20A H 0.074306 0.648258 0.382222 0.055 Uiso 1 1 calc R . . . .
C21A C 0.1424(3) 0.5354(3) 0.4012(5) 0.0359(10) Uani 1 1 d . . . . .
H21A H 0.155314 0.536533 0.311469 0.043 Uiso 1 1 calc R . . . .
C22A C 0.1728(2) 0.4679(3) 0.4909(5) 0.0325(9) Uani 1 1 d . . . . .
N1C N 0.2349(8) 0.7766(9) 0.3804(11) 0.180(5) Uani 1 1 d . . . . .
C1C C 0.1509(6) 0.8193(9) 0.5733(11) 0.135(4) Uani 1 1 d . . . . .
H1CA H 0.087692 0.810947 0.538913 0.202 Uiso 1 1 calc GR . . . .
H1CB H 0.162437 0.880049 0.598931 0.202 Uiso 1 1 calc GR . . . .
H1CC H 0.170869 0.782646 0.654552 0.202 Uiso 1 1 calc GR . . . .
C2C C 0.1976(8) 0.7962(8) 0.4667(12) 0.124(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
O1B C7B 1.237(5) . ?
O2B C8B 1.229(5) . ?
C1B C1B 1.476(7) 3_655 ?
C1B C2B 1.412(5) . ?
C1B C6B 1.404(5) . ?
C2B C3B 1.400(6) . ?
C2B C7B 1.458(5) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.382(6) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.390(6) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.387(6) . ?
C6B C8B 1.469(5) . ?
C7B C8B 1.532(5) 3_655 ?
N1A H1A 0.8800 . ?
N1A C1A 1.372(5) . ?
N1A C8A 1.388(5) . ?
N2A H2A 0.8800 . ?
N2A C9A 1.377(5) . ?
N2A C16A 1.386(5) . ?
N3A C2A 1.392(5) . ?
N3A C10A 1.403(5) . ?
N3A C22A 1.419(5) . ?
C1A C2A 1.393(6) . ?
C1A C9A 1.403(5) . ?
C2A C3A 1.443(5) . ?
C3A C4A 1.401(6) . ?
C3A C8A 1.439(6) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.379(6) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.394(7) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.385(7) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.394(6) . ?
C9A C10A 1.398(5) . ?
C10A C11A 1.432(5) . ?
C11A C12A 1.394(6) . ?
C11A C16A 1.433(5) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.383(6) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.391(6) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.393(6) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.385(6) . ?
C17A H17A 0.9500 . ?
C17A C18A 1.399(6) . ?
C17A C22A 1.382(6) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.392(7) . ?
C19A H19A 0.9500 . ?
C19A C20A 1.374(7) . ?
C20A H20A 0.9500 . ?
C20A C21A 1.384(6) . ?
C21A H21A 0.9500 . ?
C21A C22A 1.389(6) . ?
N1C C2C 1.167(13) . ?
C1C H1CA 0.9800 . ?
C1C H1CB 0.9800 . ?
C1C H1CC 0.9800 . ?
C1C C2C 1.444(14) . ?

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
C2B C1B C1B 120.5(4) . 3_655 ?
C6B C1B C1B 121.2(4) . 3_655 ?
C6B C1B C2B 118.3(4) . . ?
C1B C2B C7B 120.9(4) . . ?
C3B C2B C1B 119.5(4) . . ?
C3B C2B C7B 119.6(3) . . ?
C2B C3B H3B 119.3 . . ?
C4B C3B C2B 121.5(4) . . ?
C4B C3B H3B 119.3 . . ?
C3B C4B H4B 120.5 . . ?
C3B C4B C5B 119.1(4) . . ?
C5B C4B H4B 120.5 . . ?
C4B C5B H5B 119.7 . . ?
C6B C5B C4B 120.6(4) . . ?
C6B C5B H5B 119.7 . . ?
C1B C6B C8B 120.7(4) . . ?
C5B C6B C1B 121.0(4) . . ?
C5B C6B C8B 118.3(3) . . ?
O1B C7B C2B 123.8(4) . . ?
O1B C7B C8B 117.7(3) . 3_655 ?
C2B C7B C8B 118.5(3) . 3_655 ?
O2B C8B C6B 122.8(4) . . ?
O2B C8B C7B 119.1(3) . 3_655 ?
C6B C8B C7B 118.0(3) . 3_655 ?
C1A N1A H1A 126.2 . . ?
C1A N1A C8A 107.6(3) . . ?
C8A N1A H1A 126.2 . . ?
C9A N2A H2A 126.3 . . ?
C9A N2A C16A 107.3(3) . . ?
C16A N2A H2A 126.3 . . ?
C2A N3A C10A 105.4(3) . . ?
C2A N3A C22A 127.7(3) . . ?
C10A N3A C22A 125.6(3) . . ?
N1A C1A C2A 110.5(3) . . ?
N1A C1A C9A 141.9(4) . . ?
C2A C1A C9A 107.0(3) . . ?
N3A C2A C1A 110.5(3) . . ?
N3A C2A C3A 141.4(4) . . ?
C1A C2A C3A 107.6(3) . . ?
C4A C3A C2A 137.8(4) . . ?
C4A C3A C8A 117.7(4) . . ?
C8A C3A C2A 104.6(3) . . ?
C3A C4A H4A 120.0 . . ?
C5A C4A C3A 119.9(4) . . ?
C5A C4A H4A 120.0 . . ?
C4A C5A H5A 119.4 . . ?
C4A C5A C6A 121.2(4) . . ?
C6A C5A H5A 119.4 . . ?
C5A C6A H6A 119.2 . . ?
C7A C6A C5A 121.6(4) . . ?
C7A C6A H6A 119.2 . . ?
C6A C7A H7A 121.3 . . ?
C6A C7A C8A 117.4(4) . . ?
C8A C7A H7A 121.3 . . ?
N1A C8A C3A 109.7(3) . . ?
N1A C8A C7A 128.0(4) . . ?
C7A C8A C3A 122.3(4) . . ?
N2A C9A C1A 142.5(4) . . ?
N2A C9A C10A 110.0(3) . . ?
C10A C9A C1A 107.2(3) . . ?
N3A C10A C11A 142.0(4) . . ?
C9A C10A N3A 109.8(3) . . ?
C9A C10A C11A 107.9(3) . . ?
C10A C11A C16A 104.7(3) . . ?
C12A C11A C10A 136.7(4) . . ?
C12A C11A C16A 118.6(4) . . ?
C11A C12A H12A 120.5 . . ?
C13A C12A C11A 118.9(4) . . ?
C13A C12A H12A 120.5 . . ?
C12A C13A H13A 119.2 . . ?
C12A C13A C14A 121.7(4) . . ?
C14A C13A H13A 119.2 . . ?
C13A C14A H14A 119.4 . . ?
C13A C14A C15A 121.2(4) . . ?
C15A C14A H14A 119.4 . . ?
C14A C15A H15A 121.3 . . ?
C16A C15A C14A 117.3(4) . . ?
C16A C15A H15A 121.3 . . ?
N2A C16A C11A 110.1(3) . . ?
C15A C16A N2A 127.8(4) . . ?
C15A C16A C11A 122.2(4) . . ?
C18A C17A H17A 120.3 . . ?
C22A C17A H17A 120.3 . . ?
C22A C17A C18A 119.3(4) . . ?
C17A C18A H18A 119.8 . . ?
C19A C18A C17A 120.4(4) . . ?
C19A C18A H18A 119.8 . . ?
C18A C19A H19A 120.2 . . ?
C20A C19A C18A 119.5(4) . . ?
C20A C19A H19A 120.2 . . ?
C19A C20A H20A 119.7 . . ?
C19A C20A C21A 120.6(5) . . ?
C21A C20A H20A 119.7 . . ?
C20A C21A H21A 120.0 . . ?
C20A C21A C22A 120.0(4) . . ?
C22A C21A H21A 120.0 . . ?
C17A C22A N3A 119.9(4) . . ?
C17A C22A C21A 120.2(4) . . ?
C21A C22A N3A 119.9(4) . . ?
H1CA C1C H1CB 109.5 . . ?
H1CA C1C H1CC 109.5 . . ?
H1CB C1C H1CC 109.5 . . ?
C2C C1C H1CA 109.5 . . ?
C2C C1C H1CB 109.5 . . ?
C2C C1C H1CC 109.5 . . ?
N1C C2C C1C 179.2(15) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1A H1A O1B 0.88 2.23 2.917(4) 134.8 . yes
N2A H2A O1B 0.88 2.47 3.102(4) 129.4 . yes
N2A H2A O2B 0.88 2.06 2.891(4) 156.3 3_655 yes

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
C1B C1B C2B C3B 179.4(4) 3_655 . . . ?
C1B C1B C2B C7B -1.5(7) 3_655 . . . ?
C1B C1B C6B C5B 179.5(4) 3_655 . . . ?
C1B C1B C6B C8B -1.9(7) 3_655 . . . ?
C1B C2B C3B C4B 0.9(6) . . . . ?
C1B C2B C7B O1B -179.1(4) . . . . ?
C1B C2B C7B C8B -1.2(6) . . . 3_655 ?
C1B C6B C8B O2B -174.1(4) . . . . ?
C1B C6B C8B C7B 4.5(5) . . . 3_655 ?
C2B C1B C6B C5B -1.6(6) . . . . ?
C2B C1B C6B C8B 176.9(3) . . . . ?
C2B C3B C4B C5B -1.3(7) . . . . ?
C3B C2B C7B O1B 0.0(6) . . . . ?
C3B C2B C7B C8B 177.9(4) . . . 3_655 ?
C3B C4B C5B C6B 0.2(7) . . . . ?
C4B C5B C6B C1B 1.3(6) . . . . ?
C4B C5B C6B C8B -177.3(4) . . . . ?
C5B C6B C8B O2B 4.5(6) . . . . ?
C5B C6B C8B C7B -176.9(4) . . . 3_655 ?
C6B C1B C2B C3B 0.6(6) . . . . ?
C6B C1B C2B C7B 179.7(4) . . . . ?
C7B C2B C3B C4B -178.2(4) . . . . ?
N1A C1A C2A N3A -175.0(3) . . . . ?
N1A C1A C2A C3A -1.4(5) . . . . ?
N1A C1A C9A N2A -1.5(10) . . . . ?
N1A C1A C9A C10A 171.6(5) . . . . ?
N2A C9A C10A N3A 173.8(3) . . . . ?
N2A C9A C10A C11A -1.4(5) . . . . ?
N3A C2A C3A C4A -8.5(10) . . . . ?
N3A C2A C3A C8A 171.7(5) . . . . ?
N3A C10A C11A C12A 10.4(9) . . . . ?
N3A C10A C11A C16A -170.6(5) . . . . ?
C1A N1A C8A C3A 0.0(5) . . . . ?
C1A N1A C8A C7A 179.4(4) . . . . ?
C1A C2A C3A C4A -178.9(5) . . . . ?
C1A C2A C3A C8A 1.3(5) . . . . ?
C1A C9A C10A N3A -1.8(5) . . . . ?
C1A C9A C10A C11A -176.9(3) . . . . ?
C2A N3A C10A C9A 0.6(5) . . . . ?
C2A N3A C10A C11A 173.1(5) . . . . ?
C2A N3A C22A C17A 45.1(6) . . . . ?
C2A N3A C22A C21A -134.0(4) . . . . ?
C2A C1A C9A N2A -170.9(5) . . . . ?
C2A C1A C9A C10A 2.3(5) . . . . ?
C2A C3A C4A C5A 179.7(5) . . . . ?
C2A C3A C8A N1A -0.8(5) . . . . ?
C2A C3A C8A C7A 179.7(4) . . . . ?
C3A C4A C5A C6A 0.1(7) . . . . ?
C4A C3A C8A N1A 179.4(4) . . . . ?
C4A C3A C8A C7A -0.1(6) . . . . ?
C4A C5A C6A C7A 1.0(8) . . . . ?
C5A C6A C7A C8A -1.5(7) . . . . ?
C6A C7A C8A N1A -178.3(4) . . . . ?
C6A C7A C8A C3A 1.1(7) . . . . ?
C8A N1A C1A C2A 0.9(5) . . . . ?
C8A N1A C1A C9A -168.2(5) . . . . ?
C8A C3A C4A C5A -0.5(7) . . . . ?
C9A N2A C16A C11A 1.2(4) . . . . ?
C9A N2A C16A C15A -178.0(4) . . . . ?
C9A C1A C2A N3A -2.0(5) . . . . ?
C9A C1A C2A C3A 171.6(3) . . . . ?
C9A C10A C11A C12A -177.0(5) . . . . ?
C9A C10A C11A C16A 2.0(4) . . . . ?
C10A N3A C2A C1A 0.9(5) . . . . ?
C10A N3A C2A C3A -169.3(5) . . . . ?
C10A N3A C22A C17A -149.6(4) . . . . ?
C10A N3A C22A C21A 31.3(6) . . . . ?
C10A C11A C12A C13A -178.6(5) . . . . ?
C10A C11A C16A N2A -2.0(4) . . . . ?
C10A C11A C16A C15A 177.3(4) . . . . ?
C11A C12A C13A C14A 0.2(7) . . . . ?
C12A C11A C16A N2A 177.2(4) . . . . ?
C12A C11A C16A C15A -3.5(6) . . . . ?
C12A C13A C14A C15A -2.1(7) . . . . ?
C13A C14A C15A C16A 1.1(7) . . . . ?
C14A C15A C16A N2A -179.1(4) . . . . ?
C14A C15A C16A C11A 1.6(6) . . . . ?
C16A N2A C9A C1A 173.1(5) . . . . ?
C16A N2A C9A C10A 0.1(4) . . . . ?
C16A C11A C12A C13A 2.5(6) . . . . ?
C17A C18A C19A C20A 0.2(8) . . . . ?
C18A C17A C22A N3A -179.0(4) . . . . ?
C18A C17A C22A C21A 0.1(6) . . . . ?
C18A C19A C20A C21A 1.4(8) . . . . ?
C19A C20A C21A C22A -2.2(7) . . . . ?
C20A C21A C22A N3A -179.4(4) . . . . ?
C20A C21A C22A C17A 1.4(6) . . . . ?
C22A N3A C2A C1A 168.5(4) . . . . ?
C22A N3A C2A C3A -1.7(9) . . . . ?
C22A N3A C10A C9A -167.4(4) . . . . ?
C22A N3A C10A C11A 5.1(8) . . . . ?
C22A C17A C18A C19A -0.9(7) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a Mylar Croloop'
_olex2_submission_original_sample_id 'PhDIP-co-tetraone '
_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_pere75
_audit_block_doi                 10.5517/ccdc.csd.cc25m6df
_database_code_depnum_ccdc_archive 'CCDC 2014454'
loop_
_audit_author_name
_audit_author_address
'Thierry Marris'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2020-07-06 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;
_audit_creation_date             2018-06-07
_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         'C22 H15 N3, C16 H8 O2'
_chemical_formula_sum            'C38 H23 N3 O2'
_chemical_formula_weight         553.59
_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 0.0139 0.0070 '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 0.0245 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0390 0.0250 '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                   7.1180(3)
_cell_length_b                   19.2332(9)
_cell_length_c                   20.7789(10)
_cell_angle_alpha                65.341(2)
_cell_angle_beta                 88.276(2)
_cell_angle_gamma                84.507(2)
_cell_volume                     2573.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9816
_cell_measurement_temperature    150
_cell_measurement_theta_max      60.796
_cell_measurement_theta_min      3.740
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.914
_exptl_absorpt_coefficient_mu    0.455
_exptl_absorpt_correction_T_max  0.3108
_exptl_absorpt_correction_T_min  0.2211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1237 before and 0.0597 after correction. The Ratio of minimum to maximum transmission is 0.7114. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            63459
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.775
_diffrn_reflns_theta_min         2.035
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9938
_reflns_number_total             11837
_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 (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       0.0100(5)
_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   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     792
_refine_ls_number_reflns         11837
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0517
_refine_ls_restrained_S_all      1.048
_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)+(0.0712P)²+0.8482P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1375
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4C(H4C), C5C(H5C), C6C(H6C), C8C(H8C), C9C(H9C), C11C(H11C), C12C(H12C),
 C13C(H13C), C4A(H4A), C4B(H4B), C4D(H4D), C5A(H5A), C5B(H5B), C5D(H5D),
 C6A(H6A), C6B(H6B), C6D(H6D), C7A(H7A), C7B(H7B), C8D(H8D), C9D(H9D),
 C11D(H11D), C12A(H12A), C12B(H12B), C12D(H12D), C13A(H13A), C13B(H13B),
 C13D(H13D), C14A(H14A), C14B(H14B), C15A(H15A), C15B(H15B), C18A(H18A),
 C18B(H18B), C19A(H19A), C19B(H19B), C20A(H20A), C20B(H20B), C21A(H21A),
 C21B(H21B), C22A(H22A), C22B(H22B)
;
_atom_sites_solution_hydrogens   mixed
_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
O1C O 0.01821(17) 0.28816(6) 0.19945(7) 0.0484(3) Uani 1 1 d . . . . .
O2C O 0.16943(18) 0.22333(7) 0.33110(7) 0.0517(3) Uani 1 1 d . . . . .
C1C C 0.1029(2) 0.22410(8) 0.21943(8) 0.0361(3) Uani 1 1 d . . . . .
C2C C 0.1798(2) 0.18534(9) 0.29623(8) 0.0382(3) Uani 1 1 d . . . . .
C3C C 0.2593(2) 0.10503(9) 0.32270(8) 0.0366(3) Uani 1 1 d . . . . .
C4C C 0.3203(2) 0.06653(10) 0.39265(9) 0.0463(4) Uani 1 1 d . . . . .
H4C H 0.312564 0.092579 0.422838 0.056 Uiso 1 1 calc R . . . .
C5C C 0.3926(2) -0.01009(11) 0.41866(10) 0.0547(5) Uani 1 1 d . . . . .
H5C H 0.432859 -0.036374 0.466702 0.066 Uiso 1 1 calc R . . . .
C6C C 0.4061(2) -0.04788(10) 0.37502(11) 0.0528(4) Uani 1 1 d . . . . .
H6C H 0.455906 -0.100181 0.393449 0.063 Uiso 1 1 calc R . . . .
C7C C 0.3477(2) -0.01069(9) 0.30363(9) 0.0422(4) Uani 1 1 d . . . . .
C8C C 0.3630(2) -0.04900(9) 0.25721(11) 0.0501(4) Uani 1 1 d . . . . .
H8C H 0.411597 -0.101422 0.275270 0.060 Uiso 1 1 calc R . . . .
C9C C 0.3102(2) -0.01249(10) 0.18882(11) 0.0484(4) Uani 1 1 d . . . . .
H9C H 0.323881 -0.039391 0.159369 0.058 Uiso 1 1 calc R . . . .
C10C C 0.2336(2) 0.06616(9) 0.15939(9) 0.0397(3) Uani 1 1 d . . . . .
C11C C 0.1802(2) 0.10588(11) 0.08753(9) 0.0463(4) Uani 1 1 d . . . . .
H11C H 0.195067 0.079704 0.057488 0.056 Uiso 1 1 calc R . . . .
C12C C 0.1072(2) 0.18127(11) 0.05974(9) 0.0460(4) Uani 1 1 d . . . . .
H12C H 0.073452 0.206893 0.010971 0.055 Uiso 1 1 calc R . . . .
C13C C 0.0828(2) 0.22000(9) 0.10329(8) 0.0404(3) Uani 1 1 d . . . . .
H13C H 0.030993 0.272052 0.084375 0.048 Uiso 1 1 calc R . . . .
C14C C 0.13418(19) 0.18270(8) 0.17449(8) 0.0342(3) Uani 1 1 d . . . . .
C15C C 0.21290(18) 0.10554(8) 0.20372(8) 0.0332(3) Uani 1 1 d . . . . .
C16C C 0.27196(19) 0.06696(8) 0.27682(8) 0.0346(3) Uani 1 1 d . . . . .
O1D O 0.43290(18) 0.77494(7) 0.75842(7) 0.0494(3) Uani 1 1 d . . . . .
O2D O 0.44622(19) 0.65597(7) 0.88596(6) 0.0514(3) Uani 1 1 d . . . . .
N1A N 0.22342(17) 0.32182(7) 0.40993(6) 0.0342(3) Uani 1 1 d . . . . .
N1B N 0.21576(17) 0.92290(7) 0.70037(6) 0.0332(2) Uani 1 1 d . . . . .
N2A N 0.18514(17) 0.40635(7) 0.21953(6) 0.0346(3) Uani 1 1 d . . . . .
N2B N 0.36477(17) 0.82057(7) 0.88337(6) 0.0335(2) Uani 1 1 d . . . . .
N3A N 0.23999(16) 0.51965(6) 0.31209(6) 0.0313(2) Uani 1 1 d . . . . .
N3B N 0.19832(16) 1.01541(6) 0.81465(6) 0.0301(2) Uani 1 1 d . . . . .
C1A C 0.21327(19) 0.39111(8) 0.35108(7) 0.0319(3) Uani 1 1 d . . . . .
C1B C 0.23933(18) 0.93178(8) 0.76237(7) 0.0307(3) Uani 1 1 d . . . . .
C1D C 0.4027(2) 0.71172(8) 0.76139(8) 0.0373(3) Uani 1 1 d . . . . .
C2A C 0.23456(18) 0.45008(8) 0.37178(7) 0.0311(3) Uani 1 1 d . . . . .
C2B C 0.18281(18) 1.00718(8) 0.75146(7) 0.0298(3) Uani 1 1 d . . . . .
C2D C 0.4078(2) 0.64420(9) 0.83452(8) 0.0389(3) Uani 1 1 d . . . . .
C3A C 0.27022(19) 0.41679(8) 0.44646(7) 0.0324(3) Uani 1 1 d . . . . .
C3B C 0.12246(18) 1.04876(8) 0.67941(7) 0.0305(3) Uani 1 1 d . . . . .
C3D C 0.3631(2) 0.56965(8) 0.83861(8) 0.0375(3) Uani 1 1 d . . . . .
C4A C 0.3168(2) 0.44288(9) 0.49733(8) 0.0368(3) Uani 1 1 d . . . . .
H4A H 0.321340 0.496220 0.484570 0.044 Uiso 1 1 calc R . . . .
C4B C 0.0516(2) 1.12395(8) 0.63621(8) 0.0351(3) Uani 1 1 d . . . . .
H4B H 0.029980 1.161159 0.655199 0.042 Uiso 1 1 calc R . . . .
C4D C 0.3632(2) 0.50707(9) 0.90459(9) 0.0436(4) Uani 1 1 d . . . . .
H4D H 0.394352 0.512580 0.946251 0.052 Uiso 1 1 calc R . . . .
C5A C 0.3561(2) 0.38999(9) 0.56628(8) 0.0409(3) Uani 1 1 d . . . . .
H5A H 0.388244 0.407410 0.600755 0.049 Uiso 1 1 calc R . . . .
C5B C 0.0133(2) 1.14366(9) 0.56540(8) 0.0393(3) Uani 1 1 d . . . . .
H5B H -0.035468 1.194659 0.536091 0.047 Uiso 1 1 calc R . . . .
C5D C 0.3172(2) 0.43655(9) 0.90878(11) 0.0509(4) Uani 1 1 d . . . . .
H5D H 0.314461 0.394220 0.953712 0.061 Uiso 1 1 calc R . . . .
C6A C 0.3493(2) 0.31131(10) 0.58588(8) 0.0420(3) Uani 1 1 d . . . . .
H6A H 0.376827 0.276184 0.633505 0.050 Uiso 1 1 calc R . . . .
C6B C 0.0451(2) 1.08987(9) 0.53629(8) 0.0404(3) Uani 1 1 d . . . . .
H6B H 0.019234 1.105080 0.487459 0.048 Uiso 1 1 calc R . . . .
C6D C 0.2760(2) 0.42746(10) 0.84906(12) 0.0534(5) Uani 1 1 d . . . . .
H6D H 0.245625 0.378763 0.853125 0.064 Uiso 1 1 calc R . . . .
C7A C 0.3031(2) 0.28368(9) 0.53719(8) 0.0386(3) Uani 1 1 d . . . . .
H7A H 0.299118 0.230153 0.550826 0.046 Uiso 1 1 calc R . . . .
C7B C 0.1138(2) 1.01487(9) 0.57754(8) 0.0376(3) Uani 1 1 d . . . . .
H7B H 0.135061 0.978398 0.557684 0.045 Uiso 1 1 calc R . . . .
C7D C 0.2777(2) 0.48859(9) 0.78211(10) 0.0456(4) Uani 1 1 d . . . . .
C8A C 0.26268(19) 0.33609(8) 0.46793(8) 0.0338(3) Uani 1 1 d . . . . .
C8B C 0.15083(19) 0.99422(8) 0.64885(7) 0.0323(3) Uani 1 1 d . . . . .
C8D C 0.2375(2) 0.47925(11) 0.71828(12) 0.0538(5) Uani 1 1 d . . . . .
H8D H 0.207848 0.430740 0.721622 0.065 Uiso 1 1 calc R . . . .
C9A C 0.20405(18) 0.42415(8) 0.27677(7) 0.0313(3) Uani 1 1 d . . . . .
C9B C 0.29176(18) 0.89111(8) 0.83404(7) 0.0306(3) Uani 1 1 d . . . . .
C9D C 0.2420(2) 0.53906(12) 0.65405(11) 0.0537(5) Uani 1 1 d . . . . .
H9D H 0.217412 0.531344 0.612927 0.064 Uiso 1 1 calc R . . . .
C10A C 0.21999(18) 0.50241(8) 0.25374(7) 0.0308(3) Uani 1 1 d . . . . .
C10B C 0.26758(18) 0.94321(8) 0.86496(7) 0.0305(3) Uani 1 1 d . . . . .
C10D C 0.2825(2) 0.61313(11) 0.64621(10) 0.0462(4) Uani 1 1 d . . . . .
C11A C 0.20115(18) 0.53764(8) 0.17814(7) 0.0309(3) Uani 1 1 d . . . . .
C11B C 0.33705(18) 0.90569(8) 0.93621(7) 0.0312(3) Uani 1 1 d . . . . .
C11D C 0.2861(2) 0.67598(13) 0.57930(10) 0.0559(5) Uani 1 1 d . . . . .
H11D H 0.260668 0.668701 0.538022 0.067 Uiso 1 1 calc R . . . .
C12A C 0.20104(19) 0.61195(8) 0.12391(7) 0.0342(3) Uani 1 1 d . . . . .
H12A H 0.218864 0.654293 0.134658 0.041 Uiso 1 1 calc R . . . .
C12B C 0.3706(2) 0.92681(9) 0.99169(8) 0.0359(3) Uani 1 1 d . . . . .
H12B H 0.338606 0.978047 0.986332 0.043 Uiso 1 1 calc R . . . .
C12D C 0.3251(2) 0.74684(12) 0.57237(10) 0.0543(4) Uani 1 1 d . . . . .
H12D H 0.326116 0.788062 0.526685 0.065 Uiso 1 1 calc R . . . .
C13A C 0.1745(2) 0.62275(9) 0.05428(8) 0.0381(3) Uani 1 1 d . . . . .
H13A H 0.173401 0.673018 0.017421 0.046 Uiso 1 1 calc R . . . .
C13B C 0.4512(2) 0.87180(9) 1.05428(8) 0.0403(3) Uani 1 1 d . . . . .
H13B H 0.477006 0.886028 1.091525 0.048 Uiso 1 1 calc R . . . .
C13D C 0.3635(2) 0.75897(10) 0.63215(9) 0.0470(4) Uani 1 1 d . . . . .
H13D H 0.391369 0.808323 0.627061 0.056 Uiso 1 1 calc R . . . .
C14A C 0.1493(2) 0.56104(10) 0.03743(8) 0.0400(3) Uani 1 1 d . . . . .
H14A H 0.130603 0.570219 -0.010629 0.048 Uiso 1 1 calc R . . . .
C14B C 0.4952(2) 0.79559(9) 1.06363(8) 0.0409(3) Uani 1 1 d . . . . .
H14B H 0.545792 0.758636 1.107750 0.049 Uiso 1 1 calc R . . . .
C14D C 0.3611(2) 0.69910(9) 0.69900(8) 0.0381(3) Uani 1 1 d . . . . .
C15A C 0.1512(2) 0.48676(9) 0.08950(8) 0.0380(3) Uani 1 1 d . . . . .
H15A H 0.135789 0.444872 0.077790 0.046 Uiso 1 1 calc R . . . .
C15B C 0.4663(2) 0.77319(8) 1.00983(8) 0.0372(3) Uani 1 1 d . . . . .
H15B H 0.496199 0.721401 1.016500 0.045 Uiso 1 1 calc R . . . .
C15D C 0.3211(2) 0.62458(9) 0.70732(8) 0.0390(3) Uani 1 1 d . . . . .
C16A C 0.17636(19) 0.47538(8) 0.15940(8) 0.0332(3) Uani 1 1 d . . . . .
C16B C 0.39224(19) 0.82840(8) 0.94561(8) 0.0328(3) Uani 1 1 d . . . . .
C16D C 0.31998(19) 0.56122(8) 0.77632(8) 0.0358(3) Uani 1 1 d . . . . .
C17A C 0.24123(19) 0.59298(8) 0.31195(7) 0.0310(3) Uani 1 1 d . . . . .
C17B C 0.15780(18) 1.08302(8) 0.82563(7) 0.0305(3) Uani 1 1 d . . . . .
C18A C 0.1402(2) 0.60998(8) 0.36305(8) 0.0351(3) Uani 1 1 d . . . . .
H18A H 0.069055 0.572579 0.397368 0.042 Uiso 1 1 calc R . . . .
C18B C 0.06552(19) 1.07994(9) 0.88673(8) 0.0345(3) Uani 1 1 d . . . . .
H18B H 0.029656 1.032335 0.921165 0.041 Uiso 1 1 calc R . . . .
C19A C 0.1444(2) 0.68169(9) 0.36345(9) 0.0401(3) Uani 1 1 d . . . . .
H19A H 0.078563 0.692895 0.398945 0.048 Uiso 1 1 calc R . . . .
C19B C 0.0261(2) 1.14655(9) 0.89723(8) 0.0393(3) Uani 1 1 d . . . . .
H19B H -0.035669 1.144123 0.939195 0.047 Uiso 1 1 calc R . . . .
C20A C 0.2438(2) 0.73707(9) 0.31248(9) 0.0418(3) Uani 1 1 d . . . . .
H20A H 0.245211 0.786280 0.312754 0.050 Uiso 1 1 calc R . . . .
C20B C 0.0757(2) 1.21644(9) 0.84719(9) 0.0402(3) Uani 1 1 d . . . . .
H20B H 0.047855 1.261842 0.854589 0.048 Uiso 1 1 calc R . . . .
C21A C 0.3412(2) 0.72060(8) 0.26101(8) 0.0378(3) Uani 1 1 d . . . . .
H21A H 0.407124 0.759032 0.225432 0.045 Uiso 1 1 calc R . . . .
C21B C 0.1664(2) 1.21959(8) 0.78615(8) 0.0380(3) Uani 1 1 d . . . . .
H21B H 0.199749 1.267503 0.751447 0.046 Uiso 1 1 calc R . . . .
C22A C 0.34317(19) 0.64843(8) 0.26111(7) 0.0336(3) Uani 1 1 d . . . . .
H22A H 0.413632 0.636826 0.226709 0.040 Uiso 1 1 calc R . . . .
C22B C 0.20898(19) 1.15328(8) 0.77533(8) 0.0331(3) Uani 1 1 d . . . . .
H22B H 0.272873 1.155810 0.733712 0.040 Uiso 1 1 calc R . . . .
H2B H 0.402(3) 0.7765(12) 0.8768(10) 0.051(5) Uiso 1 1 d . . . . .
H1B H 0.276(3) 0.8826(11) 0.6928(10) 0.052(5) Uiso 1 1 d . . . . .
H2A H 0.134(3) 0.3634(11) 0.2220(10) 0.051(5) Uiso 1 1 d . . . . .
H1A H 0.226(3) 0.2760(13) 0.4080(11) 0.065(6) Uiso 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
O1C C1C 1.2247(18) . ?
O2C C2C 1.2219(18) . ?
C1C C2C 1.544(2) . ?
C1C C14C 1.4593(19) . ?
C2C C3C 1.467(2) . ?
C3C C4C 1.388(2) . ?
C3C C16C 1.421(2) . ?
C4C H4C 0.9500 . ?
C4C C5C 1.391(3) . ?
C5C H5C 0.9500 . ?
C5C C6C 1.375(3) . ?
C6C H6C 0.9500 . ?
C6C C7C 1.407(3) . ?
C7C C8C 1.434(2) . ?
C7C C16C 1.414(2) . ?
C8C H8C 0.9500 . ?
C8C C9C 1.343(3) . ?
C9C H9C 0.9500 . ?
C9C C10C 1.432(2) . ?
C10C C11C 1.409(2) . ?
C10C C15C 1.4130(19) . ?
C11C H11C 0.9500 . ?
C11C C12C 1.372(3) . ?
C12C H12C 0.9500 . ?
C12C C13C 1.390(2) . ?
C13C H13C 0.9500 . ?
C13C C14C 1.391(2) . ?
C14C C15C 1.412(2) . ?
C15C C16C 1.440(2) . ?
O1D C1D 1.2309(18) . ?
O2D C2D 1.2248(19) . ?
N1A C1A 1.3798(18) . ?
N1A C8A 1.3845(18) . ?
N1A H1A 0.90(2) . ?
N1B C1B 1.3852(17) . ?
N1B C8B 1.3871(18) . ?
N1B H1B 0.92(2) . ?
N2A C9A 1.3816(17) . ?
N2A C16A 1.3901(19) . ?
N2A H2A 0.92(2) . ?
N2B C9B 1.3777(18) . ?
N2B C16B 1.3845(18) . ?
N2B H2B 0.93(2) . ?
N3A C2A 1.3973(18) . ?
N3A C10A 1.3983(17) . ?
N3A C17A 1.4098(17) . ?
N3B C2B 1.3951(17) . ?
N3B C10B 1.3975(17) . ?
N3B C17B 1.4136(16) . ?
C1A C2A 1.3923(18) . ?
C1A C9A 1.4041(19) . ?
C1B C2B 1.3914(18) . ?
C1B C9B 1.4052(19) . ?
C1D C2D 1.531(2) . ?
C1D C14D 1.458(2) . ?
C2A C3A 1.4304(19) . ?
C2B C3B 1.4281(19) . ?
C2D C3D 1.466(2) . ?
C3A C4A 1.4052(19) . ?
C3A C8A 1.431(2) . ?
C3B C4B 1.3985(19) . ?
C3B C8B 1.4324(18) . ?
C3D C4D 1.397(2) . ?
C3D C16D 1.416(2) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.385(2) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.386(2) . ?
C4D H4D 0.9500 . ?
C4D C5D 1.392(2) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.399(2) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.399(2) . ?
C5D H5D 0.9500 . ?
C5D C6D 1.367(3) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.384(2) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.383(2) . ?
C6D H6D 0.9500 . ?
C6D C7D 1.398(3) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.389(2) . ?
C7B H7B 0.9500 . ?
C7B C8B 1.391(2) . ?
C7D C8D 1.451(3) . ?
C7D C16D 1.412(2) . ?
C8D H8D 0.9500 . ?
C8D C9D 1.352(3) . ?
C9A C10A 1.3915(19) . ?
C9B C10B 1.3943(18) . ?
C9D H9D 0.9500 . ?
C9D C10D 1.422(3) . ?
C10A C11A 1.4325(19) . ?
C10B C11B 1.4288(19) . ?
C10D C11D 1.413(3) . ?
C10D C15D 1.415(2) . ?
C11A C12A 1.403(2) . ?
C11A C16A 1.4318(19) . ?
C11B C12B 1.4061(19) . ?
C11B C16B 1.4327(19) . ?
C11D H11D 0.9500 . ?
C11D C12D 1.364(3) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.389(2) . ?
C12B H12B 0.9500 . ?
C12B C13B 1.386(2) . ?
C12D H12D 0.9500 . ?
C12D C13D 1.395(3) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.398(2) . ?
C13B H13B 0.9500 . ?
C13B C14B 1.401(2) . ?
C13D H13D 0.9500 . ?
C13D C14D 1.387(2) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.385(2) . ?
C14B H14B 0.9500 . ?
C14B C15B 1.382(2) . ?
C14D C15D 1.426(2) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.3901(19) . ?
C15B H15B 0.9500 . ?
C15B C16B 1.392(2) . ?
C15D C16D 1.444(2) . ?
C17A C18A 1.3965(19) . ?
C17A C22A 1.393(2) . ?
C17B C18B 1.3933(19) . ?
C17B C22B 1.394(2) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.386(2) . ?
C18B H18B 0.9500 . ?
C18B C19B 1.389(2) . ?
C19A H19A 0.9500 . ?
C19A C20A 1.384(2) . ?
C19B H19B 0.9500 . ?
C19B C20B 1.384(2) . ?
C20A H20A 0.9500 . ?
C20A C21A 1.386(2) . ?
C20B H20B 0.9500 . ?
C20B C21B 1.387(2) . ?
C21A H21A 0.9500 . ?
C21A C22A 1.386(2) . ?
C21B H21B 0.9500 . ?
C21B C22B 1.3893(19) . ?
C22A H22A 0.9500 . ?
C22B H22B 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
O1C C1C C2C 118.07(13) . . ?
O1C C1C C14C 123.38(14) . . ?
C14C C1C C2C 118.55(12) . . ?
O2C C2C C1C 117.96(14) . . ?
O2C C2C C3C 124.28(15) . . ?
C3C C2C C1C 117.76(12) . . ?
C4C C3C C2C 119.74(14) . . ?
C4C C3C C16C 120.43(15) . . ?
C16C C3C C2C 119.82(13) . . ?
C3C C4C H4C 119.9 . . ?
C3C C4C C5C 120.20(17) . . ?
C5C C4C H4C 119.9 . . ?
C4C C5C H5C 119.9 . . ?
C6C C5C C4C 120.19(17) . . ?
C6C C5C H5C 119.9 . . ?
C5C C6C H6C 119.3 . . ?
C5C C6C C7C 121.36(16) . . ?
C7C C6C H6C 119.3 . . ?
C6C C7C C8C 122.04(15) . . ?
C6C C7C C16C 118.94(16) . . ?
C16C C7C C8C 119.02(16) . . ?
C7C C8C H8C 119.2 . . ?
C9C C8C C7C 121.53(15) . . ?
C9C C8C H8C 119.2 . . ?
C8C C9C H9C 119.3 . . ?
C8C C9C C10C 121.31(15) . . ?
C10C C9C H9C 119.3 . . ?
C11C C10C C9C 122.21(15) . . ?
C11C C10C C15C 118.87(15) . . ?
C15C C10C C9C 118.91(16) . . ?
C10C C11C H11C 119.1 . . ?
C12C C11C C10C 121.85(14) . . ?
C12C C11C H11C 119.1 . . ?
C11C C12C H12C 120.2 . . ?
C11C C12C C13C 119.65(16) . . ?
C13C C12C H12C 120.2 . . ?
C12C C13C H13C 119.9 . . ?
C12C C13C C14C 120.13(15) . . ?
C14C C13C H13C 119.9 . . ?
C13C C14C C1C 119.02(13) . . ?
C13C C14C C15C 121.00(13) . . ?
C15C C14C C1C 119.97(13) . . ?
C10C C15C C16C 119.95(14) . . ?
C14C C15C C10C 118.47(14) . . ?
C14C C15C C16C 121.58(13) . . ?
C3C C16C C15C 121.86(13) . . ?
C7C C16C C3C 118.87(14) . . ?
C7C C16C C15C 119.27(14) . . ?
C1A N1A C8A 107.59(12) . . ?
C1A N1A H1A 124.0(14) . . ?
C8A N1A H1A 127.5(14) . . ?
C1B N1B C8B 107.27(11) . . ?
C1B N1B H1B 122.3(12) . . ?
C8B N1B H1B 126.5(12) . . ?
C9A N2A C16A 106.70(12) . . ?
C9A N2A H2A 124.1(12) . . ?
C16A N2A H2A 123.7(12) . . ?
C9B N2B C16B 107.19(11) . . ?
C9B N2B H2B 128.4(12) . . ?
C16B N2B H2B 124.2(12) . . ?
C2A N3A C10A 105.86(11) . . ?
C2A N3A C17A 126.28(11) . . ?
C10A N3A C17A 127.42(12) . . ?
C2B N3B C10B 105.82(10) . . ?
C2B N3B C17B 127.47(11) . . ?
C10B N3B C17B 126.69(11) . . ?
N1A C1A C2A 109.46(12) . . ?
N1A C1A C9A 143.14(13) . . ?
C2A C1A C9A 107.13(12) . . ?
N1B C1B C2B 109.76(12) . . ?
N1B C1B C9B 142.72(13) . . ?
C2B C1B C9B 107.43(12) . . ?
O1D C1D C2D 117.60(14) . . ?
O1D C1D C14D 123.00(15) . . ?
C14D C1D C2D 119.39(13) . . ?
N3A C2A C3A 140.92(12) . . ?
C1A C2A N3A 109.88(12) . . ?
C1A C2A C3A 108.37(12) . . ?
N3B C2B C3B 141.88(12) . . ?
C1B C2B N3B 109.86(12) . . ?
C1B C2B C3B 108.21(12) . . ?
O2D C2D C1D 118.16(14) . . ?
O2D C2D C3D 124.08(15) . . ?
C3D C2D C1D 117.75(13) . . ?
C2A C3A C8A 104.57(12) . . ?
C4A C3A C2A 136.62(13) . . ?
C4A C3A C8A 118.69(13) . . ?
C2B C3B C8B 104.91(11) . . ?
C4B C3B C2B 136.57(13) . . ?
C4B C3B C8B 118.52(13) . . ?
C4D C3D C2D 119.33(15) . . ?
C4D C3D C16D 120.37(14) . . ?
C16D C3D C2D 120.31(14) . . ?
C3A C4A H4A 120.4 . . ?
C5A C4A C3A 119.28(14) . . ?
C5A C4A H4A 120.4 . . ?
C3B C4B H4B 120.3 . . ?
C5B C4B C3B 119.35(13) . . ?
C5B C4B H4B 120.3 . . ?
C3D C4D H4D 120.3 . . ?
C5D C4D C3D 119.45(17) . . ?
C5D C4D H4D 120.3 . . ?
C4A C5A H5A 119.5 . . ?
C4A C5A C6A 120.98(14) . . ?
C6A C5A H5A 119.5 . . ?
C4B C5B H5B 119.4 . . ?
C4B C5B C6B 121.23(14) . . ?
C6B C5B H5B 119.4 . . ?
C4D C5D H5D 119.6 . . ?
C6D C5D C4D 120.84(17) . . ?
C6D C5D H5D 119.6 . . ?
C5A C6A H6A 119.4 . . ?
C7A C6A C5A 121.24(14) . . ?
C7A C6A H6A 119.4 . . ?
C5B C6B H6B 119.5 . . ?
C7B C6B C5B 121.00(14) . . ?
C7B C6B H6B 119.5 . . ?
C5D C6D H6D 119.4 . . ?
C5D C6D C7D 121.13(16) . . ?
C7D C6D H6D 119.4 . . ?
C6A C7A H7A 120.8 . . ?
C6A C7A C8A 118.40(14) . . ?
C8A C7A H7A 120.8 . . ?
C6B C7B H7B 120.9 . . ?
C6B C7B C8B 118.28(14) . . ?
C8B C7B H7B 120.9 . . ?
C6D C7D C8D 121.60(16) . . ?
C6D C7D C16D 119.32(16) . . ?
C16D C7D C8D 119.08(17) . . ?
N1A C8A C3A 109.88(12) . . ?
N1A C8A C7A 128.58(13) . . ?
C7A C8A C3A 121.40(13) . . ?
N1B C8B C3B 109.77(12) . . ?
N1B C8B C7B 128.62(13) . . ?
C7B C8B C3B 121.61(13) . . ?
C7D C8D H8D 119.7 . . ?
C9D C8D C7D 120.50(16) . . ?
C9D C8D H8D 119.7 . . ?
N2A C9A C1A 142.34(13) . . ?
N2A C9A C10A 110.25(12) . . ?
C10A C9A C1A 107.41(12) . . ?
N2B C9B C1B 143.27(13) . . ?
N2B C9B C10B 109.73(12) . . ?
C10B C9B C1B 106.91(12) . . ?
C8D C9D H9D 119.0 . . ?
C8D C9D C10D 121.98(17) . . ?
C10D C9D H9D 119.0 . . ?
N3A C10A C11A 142.09(13) . . ?
C9A C10A N3A 109.72(12) . . ?
C9A C10A C11A 108.10(12) . . ?
N3B C10B C11B 141.33(12) . . ?
C9B C10B N3B 109.97(12) . . ?
C9B C10B C11B 108.43(12) . . ?
C11D C10D C9D 122.26(17) . . ?
C11D C10D C15D 118.61(17) . . ?
C15D C10D C9D 119.13(17) . . ?
C12A C11A C10A 136.98(13) . . ?
C12A C11A C16A 118.54(12) . . ?
C16A C11A C10A 104.48(12) . . ?
C10B C11B C16B 104.20(12) . . ?
C12B C11B C10B 136.87(13) . . ?
C12B C11B C16B 118.80(13) . . ?
C10D C11D H11D 119.1 . . ?
C12D C11D C10D 121.79(17) . . ?
C12D C11D H11D 119.1 . . ?
C11A C12A H12A 120.5 . . ?
C13A C12A C11A 119.08(13) . . ?
C13A C12A H12A 120.5 . . ?
C11B C12B H12B 120.5 . . ?
C13B C12B C11B 119.03(14) . . ?
C13B C12B H12B 120.5 . . ?
C11D C12D H12D 119.9 . . ?
C11D C12D C13D 120.23(18) . . ?
C13D C12D H12D 119.9 . . ?
C12A C13A H13A 119.4 . . ?
C12A C13A C14A 121.25(14) . . ?
C14A C13A H13A 119.4 . . ?
C12B C13B H13B 119.4 . . ?
C12B C13B C14B 121.19(14) . . ?
C14B C13B H13B 119.4 . . ?
C12D C13D H13D 119.9 . . ?
C14D C13D C12D 120.11(17) . . ?
C14D C13D H13D 119.9 . . ?
C13A C14A H14A 119.4 . . ?
C15A C14A C13A 121.23(14) . . ?
C15A C14A H14A 119.4 . . ?
C13B C14B H14B 119.4 . . ?
C15B C14B C13B 121.19(14) . . ?
C15B C14B H14B 119.4 . . ?
C13D C14D C1D 120.04(15) . . ?
C13D C14D C15D 120.49(15) . . ?
C15D C14D C1D 119.46(14) . . ?
C14A C15A H15A 121.0 . . ?
C14A C15A C16A 117.99(14) . . ?
C16A C15A H15A 121.0 . . ?
C14B C15B H15B 120.8 . . ?
C14B C15B C16B 118.35(14) . . ?
C16B C15B H15B 120.8 . . ?
C10D C15D C14D 118.77(15) . . ?
C10D C15D C16D 119.81(15) . . ?
C14D C15D C16D 121.43(14) . . ?
N2A C16A C11A 110.34(12) . . ?
N2A C16A C15A 127.75(13) . . ?
C15A C16A C11A 121.90(14) . . ?
N2B C16B C11B 110.36(12) . . ?
N2B C16B C15B 128.34(13) . . ?
C15B C16B C11B 121.29(13) . . ?
C3D C16D C15D 121.63(13) . . ?
C7D C16D C3D 118.87(15) . . ?
C7D C16D C15D 119.49(15) . . ?
C18A C17A N3A 119.84(13) . . ?
C22A C17A N3A 120.24(12) . . ?
C22A C17A C18A 119.93(13) . . ?
C18B C17B N3B 120.17(12) . . ?
C18B C17B C22B 119.52(12) . . ?
C22B C17B N3B 120.32(12) . . ?
C17A C18A H18A 120.2 . . ?
C19A C18A C17A 119.65(14) . . ?
C19A C18A H18A 120.2 . . ?
C17B C18B H18B 120.0 . . ?
C19B C18B C17B 119.91(14) . . ?
C19B C18B H18B 120.0 . . ?
C18A C19A H19A 119.8 . . ?
C20A C19A C18A 120.42(14) . . ?
C20A C19A H19A 119.8 . . ?
C18B C19B H19B 119.7 . . ?
C20B C19B C18B 120.69(14) . . ?
C20B C19B H19B 119.7 . . ?
C19A C20A H20A 120.1 . . ?
C19A C20A C21A 119.87(14) . . ?
C21A C20A H20A 120.1 . . ?
C19B C20B H20B 120.3 . . ?
C19B C20B C21B 119.40(13) . . ?
C21B C20B H20B 120.3 . . ?
C20A C21A H21A 119.8 . . ?
C22A C21A C20A 120.43(14) . . ?
C22A C21A H21A 119.8 . . ?
C20B C21B H21B 119.7 . . ?
C20B C21B C22B 120.56(14) . . ?
C22B C21B H21B 119.7 . . ?
C17A C22A H22A 120.2 . . ?
C21A C22A C17A 119.65(13) . . ?
C21A C22A H22A 120.2 . . ?
C17B C22B H22B 120.0 . . ?
C21B C22B C17B 119.91(13) . . ?
C21B C22B H22B 120.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2B H2B O1D 0.93(2) 2.476(19) 3.0806(17) 123.1(15) . yes
N2B H2B O2D 0.93(2) 2.24(2) 3.1415(17) 165.0(17) . yes
N1B H1B O1D 0.92(2) 2.17(2) 2.8894(17) 135.1(16) . yes
N2A H2A O1C 0.92(2) 1.95(2) 2.8445(17) 164.4(17) . yes
N1A H1A O2C 0.90(2) 2.28(2) 3.0306(16) 140.7(19) . yes

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
O1C C1C C2C O2C -7.3(2) . . . . ?
O1C C1C C2C C3C 172.27(14) . . . . ?
O1C C1C C14C C13C 6.7(2) . . . . ?
O1C C1C C14C C15C -172.37(14) . . . . ?
O2C C2C C3C C4C 3.2(2) . . . . ?
O2C C2C C3C C16C -177.36(14) . . . . ?
C1C C2C C3C C4C -176.38(13) . . . . ?
C1C C2C C3C C16C 3.1(2) . . . . ?
C1C C14C C15C C10C 177.30(12) . . . . ?
C1C C14C C15C C16C -2.9(2) . . . . ?
C2C C1C C14C C13C -173.50(13) . . . . ?
C2C C1C C14C C15C 7.4(2) . . . . ?
C2C C3C C4C C5C 178.80(14) . . . . ?
C2C C3C C16C C7C -179.48(13) . . . . ?
C2C C3C C16C C15C 1.6(2) . . . . ?
C3C C4C C5C C6C 0.7(2) . . . . ?
C4C C3C C16C C7C 0.0(2) . . . . ?
C4C C3C C16C C15C -178.96(13) . . . . ?
C4C C5C C6C C7C -0.1(3) . . . . ?
C5C C6C C7C C8C 179.20(15) . . . . ?
C5C C6C C7C C16C -0.6(2) . . . . ?
C6C C7C C8C C9C -178.68(15) . . . . ?
C6C C7C C16C C3C 0.6(2) . . . . ?
C6C C7C C16C C15C 179.63(13) . . . . ?
C7C C8C C9C C10C -0.9(2) . . . . ?
C8C C7C C16C C3C -179.19(13) . . . . ?
C8C C7C C16C C15C -0.2(2) . . . . ?
C8C C9C C10C C11C 178.98(14) . . . . ?
C8C C9C C10C C15C -0.3(2) . . . . ?
C9C C10C C11C C12C -179.91(14) . . . . ?
C9C C10C C15C C14C -178.90(13) . . . . ?
C9C C10C C15C C16C 1.3(2) . . . . ?
C10C C11C C12C C13C -0.7(2) . . . . ?
C10C C15C C16C C3C 177.98(13) . . . . ?
C10C C15C C16C C7C -0.98(19) . . . . ?
C11C C10C C15C C14C 1.8(2) . . . . ?
C11C C10C C15C C16C -178.08(12) . . . . ?
C11C C12C C13C C14C 0.7(2) . . . . ?
C12C C13C C14C C1C -178.54(14) . . . . ?
C12C C13C C14C C15C 0.5(2) . . . . ?
C13C C14C C15C C10C -1.8(2) . . . . ?
C13C C14C C15C C16C 178.09(13) . . . . ?
C14C C1C C2C O2C 172.90(14) . . . . ?
C14C C1C C2C C3C -7.54(19) . . . . ?
C14C C15C C16C C3C -1.9(2) . . . . ?
C14C C15C C16C C7C 179.18(12) . . . . ?
C15C C10C C11C C12C -0.6(2) . . . . ?
C16C C3C C4C C5C -0.7(2) . . . . ?
C16C C7C C8C C9C 1.1(2) . . . . ?
O1D C1D C2D O2D -1.8(2) . . . . ?
O1D C1D C2D C3D 177.14(13) . . . . ?
O1D C1D C14D C13D 3.3(2) . . . . ?
O1D C1D C14D C15D -177.76(14) . . . . ?
O2D C2D C3D C4D 0.0(2) . . . . ?
O2D C2D C3D C16D 179.91(14) . . . . ?
N1A C1A C2A N3A 175.17(11) . . . . ?
N1A C1A C2A C3A 3.29(15) . . . . ?
N1A C1A C9A N2A 7.1(3) . . . . ?
N1A C1A C9A C10A -172.85(18) . . . . ?
N1B C1B C2B N3B 177.32(11) . . . . ?
N1B C1B C2B C3B -0.67(15) . . . . ?
N1B C1B C9B N2B 7.6(3) . . . . ?
N1B C1B C9B C10B -176.34(17) . . . . ?
N2A C9A C10A N3A -179.70(11) . . . . ?
N2A C9A C10A C11A 2.96(15) . . . . ?
N2B C9B C10B N3B 178.41(11) . . . . ?
N2B C9B C10B C11B 3.07(15) . . . . ?
N3A C2A C3A C4A 6.3(3) . . . . ?
N3A C2A C3A C8A -169.53(17) . . . . ?
N3A C10A C11A C12A 3.1(3) . . . . ?
N3A C10A C11A C16A -176.69(17) . . . . ?
N3A C17A C18A C19A 178.93(13) . . . . ?
N3A C17A C22A C21A 179.17(12) . . . . ?
N3B C2B C3B C4B 3.0(3) . . . . ?
N3B C2B C3B C8B -178.20(17) . . . . ?
N3B C10B C11B C12B -0.7(3) . . . . ?
N3B C10B C11B C16B -176.11(17) . . . . ?
N3B C17B C18B C19B -179.99(12) . . . . ?
N3B C17B C22B C21B 179.18(12) . . . . ?
C1A N1A C8A C3A 2.46(15) . . . . ?
C1A N1A C8A C7A -173.41(14) . . . . ?
C1A C2A C3A C4A 174.15(16) . . . . ?
C1A C2A C3A C8A -1.69(15) . . . . ?
C1A C9A C10A N3A 0.25(15) . . . . ?
C1A C9A C10A C11A -177.09(11) . . . . ?
C1B N1B C8B C3B -3.22(15) . . . . ?
C1B N1B C8B C7B 177.17(14) . . . . ?
C1B C2B C3B C4B 179.93(15) . . . . ?
C1B C2B C3B C8B -1.26(15) . . . . ?
C1B C9B C10B N3B 0.94(15) . . . . ?
C1B C9B C10B C11B -174.40(11) . . . . ?
C1D C2D C3D C4D -178.92(13) . . . . ?
C1D C2D C3D C16D 1.0(2) . . . . ?
C1D C14D C15D C10D -179.49(13) . . . . ?
C1D C14D C15D C16D 0.3(2) . . . . ?
C2A N3A C10A C9A -0.43(14) . . . . ?
C2A N3A C10A C11A 175.45(17) . . . . ?
C2A N3A C17A C18A -34.77(19) . . . . ?
C2A N3A C17A C22A 145.09(13) . . . . ?
C2A C1A C9A N2A 179.97(17) . . . . ?
C2A C1A C9A C10A 0.04(15) . . . . ?
C2A C3A C4A C5A -174.67(15) . . . . ?
C2A C3A C8A N1A -0.46(15) . . . . ?
C2A C3A C8A C7A 175.75(13) . . . . ?
C2B N3B C10B C9B -0.89(14) . . . . ?
C2B N3B C10B C11B 172.02(17) . . . . ?
C2B N3B C17B C18B 139.21(14) . . . . ?
C2B N3B C17B C22B -40.49(19) . . . . ?
C2B C1B C9B N2B -176.62(18) . . . . ?
C2B C1B C9B C10B -0.61(15) . . . . ?
C2B C3B C4B C5B 177.93(15) . . . . ?
C2B C3B C8B N1B 2.77(15) . . . . ?
C2B C3B C8B C7B -177.59(12) . . . . ?
C2D C1D C14D C13D -177.38(13) . . . . ?
C2D C1D C14D C15D 1.6(2) . . . . ?
C2D C3D C4D C5D 178.78(14) . . . . ?
C2D C3D C16D C7D 179.95(13) . . . . ?
C2D C3D C16D C15D 0.9(2) . . . . ?
C3A C4A C5A C6A -0.3(2) . . . . ?
C3B C4B C5B C6B -0.4(2) . . . . ?
C3D C4D C5D C6D 1.4(2) . . . . ?
C4A C3A C8A N1A -177.21(12) . . . . ?
C4A C3A C8A C7A -1.0(2) . . . . ?
C4A C5A C6A C7A 0.0(2) . . . . ?
C4B C3B C8B N1B -178.16(12) . . . . ?
C4B C3B C8B C7B 1.5(2) . . . . ?
C4B C5B C6B C7B 0.8(2) . . . . ?
C4D C3D C16D C7D -0.1(2) . . . . ?
C4D C3D C16D C15D -179.20(13) . . . . ?
C4D C5D C6D C7D -0.3(2) . . . . ?
C5A C6A C7A C8A -0.2(2) . . . . ?
C5B C6B C7B C8B -0.1(2) . . . . ?
C5D C6D C7D C8D 178.85(15) . . . . ?
C5D C6D C7D C16D -1.0(2) . . . . ?
C6A C7A C8A N1A 176.18(14) . . . . ?
C6A C7A C8A C3A 0.7(2) . . . . ?
C6B C7B C8B N1B 178.54(14) . . . . ?
C6B C7B C8B C3B -1.0(2) . . . . ?
C6D C7D C8D C9D -179.29(15) . . . . ?
C6D C7D C16D C3D 1.2(2) . . . . ?
C6D C7D C16D C15D -179.73(13) . . . . ?
C7D C8D C9D C10D -1.1(2) . . . . ?
C8A N1A C1A C2A -3.55(15) . . . . ?
C8A N1A C1A C9A 169.25(18) . . . . ?
C8A C3A C4A C5A 0.7(2) . . . . ?
C8B N1B C1B C2B 2.40(15) . . . . ?
C8B N1B C1B C9B 178.08(18) . . . . ?
C8B C3B C4B C5B -0.8(2) . . . . ?
C8D C7D C16D C3D -178.64(13) . . . . ?
C8D C7D C16D C15D 0.4(2) . . . . ?
C8D C9D C10D C11D -179.55(16) . . . . ?
C8D C9D C10D C15D 0.6(2) . . . . ?
C9A N2A C16A C11A 3.44(15) . . . . ?
C9A N2A C16A C15A -177.72(13) . . . . ?
C9A C1A C2A N3A -0.31(15) . . . . ?
C9A C1A C2A C3A -172.20(11) . . . . ?
C9A C10A C11A C12A 179.02(15) . . . . ?
C9A C10A C11A C16A -0.76(14) . . . . ?
C9B N2B C16B C11B -0.39(15) . . . . ?
C9B N2B C16B C15B -178.78(14) . . . . ?
C9B C1B C2B N3B 0.06(15) . . . . ?
C9B C1B C2B C3B -177.93(11) . . . . ?
C9B C10B C11B C12B 172.27(16) . . . . ?
C9B C10B C11B C16B -3.13(15) . . . . ?
C9D C10D C11D C12D -179.99(16) . . . . ?
C9D C10D C15D C14D -179.85(14) . . . . ?
C9D C10D C15D C16D 0.3(2) . . . . ?
C10A N3A C2A C1A 0.46(15) . . . . ?
C10A N3A C2A C3A 168.18(17) . . . . ?
C10A N3A C17A C18A 136.48(14) . . . . ?
C10A N3A C17A C22A -43.66(19) . . . . ?
C10A C11A C12A C13A -178.92(15) . . . . ?
C10A C11A C16A N2A -1.66(15) . . . . ?
C10A C11A C16A C15A 179.42(13) . . . . ?
C10B N3B C2B C1B 0.50(14) . . . . ?
C10B N3B C2B C3B 177.41(17) . . . . ?
C10B N3B C17B C18B -42.72(19) . . . . ?
C10B N3B C17B C22B 137.58(14) . . . . ?
C10B C11B C12B C13B -176.65(15) . . . . ?
C10B C11B C16B N2B 2.18(15) . . . . ?
C10B C11B C16B C15B -179.30(13) . . . . ?
C10D C11D C12D C13D 0.2(3) . . . . ?
C10D C15D C16D C3D 178.19(13) . . . . ?
C10D C15D C16D C7D -0.9(2) . . . . ?
C11A C12A C13A C14A -0.4(2) . . . . ?
C11B C12B C13B C14B -1.5(2) . . . . ?
C11D C10D C15D C14D 0.3(2) . . . . ?
C11D C10D C15D C16D -179.47(13) . . . . ?
C11D C12D C13D C14D -0.4(3) . . . . ?
C12A C11A C16A N2A 178.51(12) . . . . ?
C12A C11A C16A C15A -0.4(2) . . . . ?
C12A C13A C14A C15A -0.4(2) . . . . ?
C12B C11B C16B N2B -174.24(12) . . . . ?
C12B C11B C16B C15B 4.3(2) . . . . ?
C12B C13B C14B C15B 2.4(2) . . . . ?
C12D C13D C14D C1D 179.51(14) . . . . ?
C12D C13D C14D C15D 0.6(2) . . . . ?
C13A C14A C15A C16A 0.9(2) . . . . ?
C13B C14B C15B C16B 0.1(2) . . . . ?
C13D C14D C15D C10D -0.5(2) . . . . ?
C13D C14D C15D C16D 179.27(13) . . . . ?
C14A C15A C16A N2A -179.16(13) . . . . ?
C14A C15A C16A C11A -0.4(2) . . . . ?
C14B C15B C16B N2B 174.80(14) . . . . ?
C14B C15B C16B C11B -3.4(2) . . . . ?
C14D C1D C2D O2D 178.80(14) . . . . ?
C14D C1D C2D C3D -2.2(2) . . . . ?
C14D C15D C16D C3D -1.6(2) . . . . ?
C14D C15D C16D C7D 179.33(13) . . . . ?
C15D C10D C11D C12D -0.2(2) . . . . ?
C16A N2A C9A C1A 176.13(18) . . . . ?
C16A N2A C9A C10A -3.94(15) . . . . ?
C16A C11A C12A C13A 0.85(19) . . . . ?
C16B N2B C9B C1B 174.29(18) . . . . ?
C16B N2B C9B C10B -1.66(15) . . . . ?
C16B C11B C12B C13B -1.7(2) . . . . ?
C16D C3D C4D C5D -1.1(2) . . . . ?
C16D C7D C8D C9D 0.5(2) . . . . ?
C17A N3A C2A C1A 173.24(12) . . . . ?
C17A N3A C2A C3A -19.0(3) . . . . ?
C17A N3A C10A C9A -173.11(12) . . . . ?
C17A N3A C10A C11A 2.8(3) . . . . ?
C17A C18A C19A C20A 1.7(2) . . . . ?
C17B N3B C2B C1B 178.89(12) . . . . ?
C17B N3B C2B C3B -4.2(3) . . . . ?
C17B N3B C10B C9B -179.30(12) . . . . ?
C17B N3B C10B C11B -6.4(3) . . . . ?
C17B C18B C19B C20B 0.7(2) . . . . ?
C18A C17A C22A C21A -1.0(2) . . . . ?
C18A C19A C20A C21A -0.6(2) . . . . ?
C18B C17B C22B C21B -0.5(2) . . . . ?
C18B C19B C20B C21B -0.2(2) . . . . ?
C19A C20A C21A C22A -1.4(2) . . . . ?
C19B C20B C21B C22B -0.6(2) . . . . ?
C20A C21A C22A C17A 2.1(2) . . . . ?
C20B C21B C22B C17B 1.0(2) . . . . ?
C22A C17A C18A C19A -0.9(2) . . . . ?
C22B C17B C18B C19B -0.3(2) . . . . ?

_olex2_date_sample_data_collection 2018-06-06
_olex2_date_sample_submission    2018-06-06
_olex2_exptl_crystal_mounting_method 'mounted on a Mylar Cedit insryoloop'
_olex2_submission_original_sample_id PhDIP-co-dione
_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_pere792
_audit_block_doi                 10.5517/ccdc.csd.cc25m6fg
_database_code_depnum_ccdc_archive 'CCDC 2014455'
loop_
_audit_author_name
_audit_author_address
'Thierry Marris'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2020-07-06 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;
_audit_creation_date             2018-07-18
_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         'C22 H15 N3, C14 H8 O2'
_chemical_formula_sum            'C36 H23 N3 O2'
_chemical_formula_weight         529.57
_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 0.0139 0.0070 '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 0.0241 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0390 0.0250 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.7308(3)
_cell_length_b                   10.8063(3)
_cell_length_c                   19.0977(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.4560(10)
_cell_angle_gamma                90
_cell_volume                     2519.70(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9720
_cell_measurement_temperature    150
_cell_measurement_theta_max      60.728
_cell_measurement_theta_min      3.150
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.889
_exptl_absorpt_coefficient_mu    0.446
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1171 before and 0.0424 after correction. The Ratio of minimum to maximum transmission is 0.9279. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            35234
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.707
_diffrn_reflns_theta_min         4.132
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5482
_reflns_number_total             5798
_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 (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       0.0455(14)
_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   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         5798
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0482
_refine_ls_restrained_S_all      1.101
_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)+(0.0619P)²+0.8029P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1179
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2A(H2A), N3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A), C7A(H7A), C12A(H12A),
 C13A(H13A), C14A(H14A), C15A(H15A), C18A(H18A), C19A(H19A), C20A(H20A),
 C21A(H21A), C22A(H22A), C4B(H4B), C5B(H5B), C6B(H6B), C7B(H7B), C10B(H10B),
 C11B(H11B), C12B(H12B), C13B(H13B)
;
_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
N1A N 0.19384(7) 0.75706(9) 0.62992(5) 0.0224(2) Uani 1 1 d . . . . .
N2A N 0.40729(8) 0.56885(9) 0.60987(5) 0.0238(2) Uani 1 1 d . . . . .
H2A H 0.430025 0.515942 0.583828 0.029 Uiso 1 1 calc R . . . .
N3A N 0.14515(8) 0.56761(9) 0.47519(5) 0.0231(2) Uani 1 1 d . . . . .
H3A H 0.170237 0.514682 0.450367 0.028 Uiso 1 1 calc R . . . .
C1A C 0.30330(9) 0.61711(10) 0.59473(6) 0.0216(2) Uani 1 1 d . . . . .
C2A C 0.29715(9) 0.70050(10) 0.64887(6) 0.0216(2) Uani 1 1 d . . . . .
C3A C 0.40300(9) 0.70681(10) 0.70126(6) 0.0216(2) Uani 1 1 d . . . . .
C4A C 0.45224(9) 0.77190(11) 0.76577(6) 0.0256(2) Uani 1 1 d . . . . .
H4A H 0.411670 0.827782 0.784540 0.031 Uiso 1 1 calc R . . . .
C5A C 0.56218(10) 0.75201(11) 0.80130(6) 0.0283(2) Uani 1 1 d . . . . .
H5A H 0.594968 0.795367 0.843964 0.034 Uiso 1 1 calc R . . . .
C6A C 0.62482(9) 0.66773(11) 0.77408(6) 0.0276(2) Uani 1 1 d . . . . .
H6A H 0.698374 0.656368 0.798876 0.033 Uiso 1 1 calc R . . . .
C7A C 0.57879(9) 0.60142(11) 0.71099(6) 0.0250(2) Uani 1 1 d . . . . .
H7A H 0.620245 0.545166 0.693214 0.030 Uiso 1 1 calc R . . . .
C8A C 0.46851(9) 0.62105(10) 0.67465(6) 0.0220(2) Uani 1 1 d . . . . .
C9A C 0.20199(9) 0.62052(10) 0.54062(6) 0.0217(2) Uani 1 1 d . . . . .
C10A C 0.13647(9) 0.70602(10) 0.56256(6) 0.0210(2) Uani 1 1 d . . . . .
C11A C 0.03053(9) 0.70500(10) 0.51053(6) 0.0212(2) Uani 1 1 d . . . . .
C12A C -0.07080(9) 0.76260(10) 0.50249(6) 0.0242(2) Uani 1 1 d . . . . .
H12A H -0.079131 0.820652 0.536471 0.029 Uiso 1 1 calc R . . . .
C13A C -0.15860(9) 0.73186(11) 0.44312(6) 0.0266(2) Uani 1 1 d . . . . .
H13A H -0.226165 0.769272 0.437951 0.032 Uiso 1 1 calc R . . . .
C14A C -0.14767(9) 0.64580(11) 0.39088(6) 0.0270(2) Uani 1 1 d . . . . .
H14A H -0.207748 0.627565 0.351430 0.032 Uiso 1 1 calc R . . . .
C15A C -0.04852(9) 0.58738(11) 0.39712(6) 0.0251(2) Uani 1 1 d . . . . .
H15A H -0.041198 0.530566 0.362229 0.030 Uiso 1 1 calc R . . . .
C16A C 0.03969(9) 0.61587(10) 0.45687(6) 0.0222(2) Uani 1 1 d . . . . .
C17A C 0.15678(8) 0.85113(10) 0.66831(6) 0.0225(2) Uani 1 1 d . . . . .
C18A C 0.18003(10) 0.84434(12) 0.74407(6) 0.0295(3) Uani 1 1 d . . . . .
H18A H 0.218769 0.777310 0.769253 0.035 Uiso 1 1 calc R . . . .
C19A C 0.14487(11) 0.93853(14) 0.78175(7) 0.0383(3) Uani 1 1 d . . . . .
H19A H 0.161123 0.934703 0.832343 0.046 Uiso 1 1 calc R . . . .
C20A C 0.08598(11) 1.03778(13) 0.74466(8) 0.0378(3) Uani 1 1 d . . . . .
H20A H 0.062266 1.100019 0.770207 0.045 Uiso 1 1 calc R . . . .
C21A C 0.06240(10) 1.04418(11) 0.66925(8) 0.0321(3) Uani 1 1 d . . . . .
H21A H 0.022859 1.110896 0.644257 0.039 Uiso 1 1 calc R . . . .
C22A C 0.09758(9) 0.95145(11) 0.63098(6) 0.0259(2) Uani 1 1 d . . . . .
H22A H 0.081712 0.956154 0.580426 0.031 Uiso 1 1 calc R . . . .
O1B O 0.52887(8) 0.37763(9) 0.56307(5) 0.0365(2) Uani 1 1 d . . . . .
O2B O 0.32421(7) 0.39297(9) 0.47365(5) 0.0372(2) Uani 1 1 d . . . . .
C1B C 0.49998(10) 0.30155(11) 0.51425(6) 0.0268(2) Uani 1 1 d . . . . .
C2B C 0.38199(9) 0.30844(11) 0.46394(6) 0.0266(2) Uani 1 1 d . . . . .
C3B C 0.34570(10) 0.21276(11) 0.40767(6) 0.0270(2) Uani 1 1 d . . . . .
C4B C 0.23627(11) 0.21270(13) 0.36549(7) 0.0339(3) Uani 1 1 d . . . . .
H4B H 0.188021 0.271237 0.374357 0.041 Uiso 1 1 calc R . . . .
C5B C 0.19937(13) 0.12646(14) 0.31083(8) 0.0421(3) Uani 1 1 d . . . . .
H5B H 0.126239 0.125469 0.283409 0.050 Uiso 1 1 calc R . . . .
C6B C 0.27287(14) 0.04097(13) 0.29722(7) 0.0438(3) Uani 1 1 d . . . . .
H6B H 0.248747 -0.016308 0.259750 0.053 Uiso 1 1 calc R . . . .
C7B C 0.38146(13) 0.03993(12) 0.33867(7) 0.0375(3) Uani 1 1 d . . . . .
H7B H 0.429265 -0.017810 0.328461 0.045 Uiso 1 1 calc R . . . .
C8B C 0.42028(10) 0.12422(11) 0.39555(6) 0.0279(3) Uani 1 1 d . . . . .
C9B C 0.53471(10) 0.12041(11) 0.44275(7) 0.0277(3) Uani 1 1 d . . . . .
C10B C 0.61027(12) 0.03332(12) 0.43237(8) 0.0378(3) Uani 1 1 d . . . . .
H10B H 0.589425 -0.022150 0.393662 0.045 Uiso 1 1 calc R . . . .
C11B C 0.71592(12) 0.02860(13) 0.47906(10) 0.0446(4) Uani 1 1 d . . . . .
H11B H 0.764739 -0.029821 0.470828 0.054 Uiso 1 1 calc R . . . .
C12B C 0.75005(11) 0.10837(14) 0.53724(9) 0.0418(3) Uani 1 1 d . . . . .
H12B H 0.820614 0.102859 0.568642 0.050 Uiso 1 1 calc R . . . .
C13B C 0.67815(11) 0.19663(13) 0.54834(8) 0.0347(3) Uani 1 1 d . . . . .
H13B H 0.700499 0.251924 0.587029 0.042 Uiso 1 1 calc R . . . .
C14B C 0.57160(10) 0.20307(11) 0.50143(6) 0.0267(2) 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
N1A C2A 1.4016(13) . ?
N1A C10A 1.4000(13) . ?
N1A C17A 1.4104(13) . ?
N2A H2A 0.8600 . ?
N2A C1A 1.3752(14) . ?
N2A C8A 1.3821(14) . ?
N3A H3A 0.8600 . ?
N3A C9A 1.3783(13) . ?
N3A C16A 1.3895(14) . ?
C1A C2A 1.3905(15) . ?
C1A C9A 1.4062(15) . ?
C2A C3A 1.4345(14) . ?
C3A C4A 1.4028(15) . ?
C3A C8A 1.4327(15) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.3884(16) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.4037(17) . ?
C6A H6A 0.9300 . ?
C6A C7A 1.3815(16) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.3949(15) . ?
C9A C10A 1.3868(14) . ?
C10A C11A 1.4309(14) . ?
C11A C12A 1.4010(15) . ?
C11A C16A 1.4349(14) . ?
C12A H12A 0.9300 . ?
C12A C13A 1.3883(16) . ?
C13A H13A 0.9300 . ?
C13A C14A 1.3994(16) . ?
C14A H14A 0.9300 . ?
C14A C15A 1.3859(16) . ?
C15A H15A 0.9300 . ?
C15A C16A 1.3899(15) . ?
C17A C18A 1.3942(16) . ?
C17A C22A 1.3954(16) . ?
C18A H18A 0.9300 . ?
C18A C19A 1.3917(17) . ?
C19A H19A 0.9300 . ?
C19A C20A 1.383(2) . ?
C20A H20A 0.9300 . ?
C20A C21A 1.387(2) . ?
C21A H21A 0.9300 . ?
C21A C22A 1.3873(16) . ?
C22A H22A 0.9300 . ?
O1B C1B 1.2190(15) . ?
O2B C2B 1.2195(14) . ?
C1B C2B 1.5387(16) . ?
C1B C14B 1.4664(16) . ?
C2B C3B 1.4683(17) . ?
C3B C4B 1.3978(18) . ?
C3B C8B 1.4125(16) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.379(2) . ?
C5B H5B 0.9300 . ?
C5B C6B 1.391(2) . ?
C6B H6B 0.9300 . ?
C6B C7B 1.385(2) . ?
C7B H7B 0.9300 . ?
C7B C8B 1.3964(18) . ?
C8B C9B 1.4807(18) . ?
C9B C10B 1.3994(16) . ?
C9B C14B 1.4058(18) . ?
C10B H10B 0.9300 . ?
C10B C11B 1.388(2) . ?
C11B H11B 0.9300 . ?
C11B C12B 1.376(2) . ?
C12B H12B 0.9300 . ?
C12B C13B 1.3792(19) . ?
C13B H13B 0.9300 . ?
C13B C14B 1.3997(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
C2A N1A C17A 127.41(9) . . ?
C10A N1A C2A 105.83(8) . . ?
C10A N1A C17A 126.67(9) . . ?
C1A N2A H2A 126.3 . . ?
C1A N2A C8A 107.37(9) . . ?
C8A N2A H2A 126.3 . . ?
C9A N3A H3A 126.4 . . ?
C9A N3A C16A 107.11(9) . . ?
C16A N3A H3A 126.4 . . ?
N2A C1A C2A 110.06(9) . . ?
N2A C1A C9A 142.41(10) . . ?
C2A C1A C9A 107.24(9) . . ?
N1A C2A C3A 141.88(10) . . ?
C1A C2A N1A 109.69(9) . . ?
C1A C2A C3A 108.05(9) . . ?
C4A C3A C2A 137.24(10) . . ?
C4A C3A C8A 118.40(10) . . ?
C8A C3A C2A 104.36(9) . . ?
C3A C4A H4A 120.3 . . ?
C5A C4A C3A 119.30(10) . . ?
C5A C4A H4A 120.3 . . ?
C4A C5A H5A 119.4 . . ?
C4A C5A C6A 121.28(11) . . ?
C6A C5A H5A 119.4 . . ?
C5A C6A H6A 119.5 . . ?
C7A C6A C5A 120.96(10) . . ?
C7A C6A H6A 119.5 . . ?
C6A C7A H7A 120.9 . . ?
C6A C7A C8A 118.26(10) . . ?
C8A C7A H7A 120.9 . . ?
N2A C8A C3A 110.14(9) . . ?
N2A C8A C7A 128.04(10) . . ?
C7A C8A C3A 121.79(10) . . ?
N3A C9A C1A 142.37(10) . . ?
N3A C9A C10A 110.13(9) . . ?
C10A C9A C1A 107.48(9) . . ?
N1A C10A C11A 141.72(10) . . ?
C9A C10A N1A 109.77(9) . . ?
C9A C10A C11A 108.32(9) . . ?
C10A C11A C16A 104.47(9) . . ?
C12A C11A C10A 136.89(10) . . ?
C12A C11A C16A 118.59(10) . . ?
C11A C12A H12A 120.4 . . ?
C13A C12A C11A 119.11(10) . . ?
C13A C12A H12A 120.4 . . ?
C12A C13A H13A 119.3 . . ?
C12A C13A C14A 121.44(11) . . ?
C14A C13A H13A 119.3 . . ?
C13A C14A H14A 119.6 . . ?
C15A C14A C13A 120.90(10) . . ?
C15A C14A H14A 119.6 . . ?
C14A C15A H15A 120.8 . . ?
C14A C15A C16A 118.30(10) . . ?
C16A C15A H15A 120.8 . . ?
N3A C16A C11A 109.90(9) . . ?
N3A C16A C15A 128.46(10) . . ?
C15A C16A C11A 121.65(10) . . ?
C18A C17A N1A 119.84(10) . . ?
C18A C17A C22A 119.75(10) . . ?
C22A C17A N1A 120.41(10) . . ?
C17A C18A H18A 120.2 . . ?
C19A C18A C17A 119.56(12) . . ?
C19A C18A H18A 120.2 . . ?
C18A C19A H19A 119.7 . . ?
C20A C19A C18A 120.63(12) . . ?
C20A C19A H19A 119.7 . . ?
C19A C20A H20A 120.1 . . ?
C19A C20A C21A 119.79(11) . . ?
C21A C20A H20A 120.1 . . ?
C20A C21A H21A 119.9 . . ?
C20A C21A C22A 120.25(12) . . ?
C22A C21A H21A 119.9 . . ?
C17A C22A H22A 120.0 . . ?
C21A C22A C17A 120.02(11) . . ?
C21A C22A H22A 120.0 . . ?
O1B C1B C2B 118.33(10) . . ?
O1B C1B C14B 123.37(11) . . ?
C14B C1B C2B 118.29(10) . . ?
O2B C2B C1B 117.75(11) . . ?
O2B C2B C3B 124.08(11) . . ?
C3B C2B C1B 118.17(10) . . ?
C4B C3B C2B 118.53(11) . . ?
C4B C3B C8B 120.78(12) . . ?
C8B C3B C2B 120.68(11) . . ?
C3B C4B H4B 119.8 . . ?
C5B C4B C3B 120.45(13) . . ?
C5B C4B H4B 119.8 . . ?
C4B C5B H5B 120.4 . . ?
C4B C5B C6B 119.18(14) . . ?
C6B C5B H5B 120.4 . . ?
C5B C6B H6B 119.5 . . ?
C7B C6B C5B 120.93(13) . . ?
C7B C6B H6B 119.5 . . ?
C6B C7B H7B 119.5 . . ?
C6B C7B C8B 121.02(13) . . ?
C8B C7B H7B 119.5 . . ?
C3B C8B C9B 120.67(11) . . ?
C7B C8B C3B 117.59(12) . . ?
C7B C8B C9B 121.72(11) . . ?
C10B C9B C8B 121.98(12) . . ?
C10B C9B C14B 116.90(12) . . ?
C14B C9B C8B 121.10(10) . . ?
C9B C10B H10B 119.6 . . ?
C11B C10B C9B 120.89(13) . . ?
C11B C10B H10B 119.6 . . ?
C10B C11B H11B 119.2 . . ?
C12B C11B C10B 121.51(12) . . ?
C12B C11B H11B 119.2 . . ?
C11B C12B H12B 120.5 . . ?
C11B C12B C13B 119.07(14) . . ?
C13B C12B H12B 120.5 . . ?
C12B C13B H13B 120.0 . . ?
C12B C13B C14B 120.07(14) . . ?
C14B C13B H13B 120.0 . . ?
C9B C14B C1B 120.74(11) . . ?
C13B C14B C1B 117.70(11) . . ?
C13B C14B C9B 121.53(11) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2A H2A O1B 0.86 2.06 2.8721(13) 156.4 . yes
N2A H2A O2B 0.86 2.53 3.1527(13) 130.0 . yes
N3A H3A O2B 0.86 2.30 2.9660(12) 134.7 . yes

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
N1A C2A C3A C4A 6.7(2) . . . . ?
N1A C2A C3A C8A -172.73(14) . . . . ?
N1A C10A C11A C12A 2.4(2) . . . . ?
N1A C10A C11A C16A -175.04(14) . . . . ?
N1A C17A C18A C19A 178.89(11) . . . . ?
N1A C17A C22A C21A -179.35(10) . . . . ?
N2A C1A C2A N1A 175.00(9) . . . . ?
N2A C1A C2A C3A 0.45(12) . . . . ?
N2A C1A C9A N3A 9.5(3) . . . . ?
N2A C1A C9A C10A -172.33(14) . . . . ?
N3A C9A C10A N1A 178.54(9) . . . . ?
N3A C9A C10A C11A 2.49(12) . . . . ?
C1A N2A C8A C3A -1.10(12) . . . . ?
C1A N2A C8A C7A -179.04(11) . . . . ?
C1A C2A C3A C4A 178.37(13) . . . . ?
C1A C2A C3A C8A -1.07(12) . . . . ?
C1A C9A C10A N1A -0.25(12) . . . . ?
C1A C9A C10A C11A -176.30(9) . . . . ?
C2A N1A C10A C9A 0.12(12) . . . . ?
C2A N1A C10A C11A 174.06(14) . . . . ?
C2A N1A C17A C18A -43.34(16) . . . . ?
C2A N1A C17A C22A 136.23(11) . . . . ?
C2A C1A C9A N3A -177.85(14) . . . . ?
C2A C1A C9A C10A 0.28(12) . . . . ?
C2A C3A C4A C5A -178.96(12) . . . . ?
C2A C3A C8A N2A 1.34(12) . . . . ?
C2A C3A C8A C7A 179.42(10) . . . . ?
C3A C4A C5A C6A -0.26(18) . . . . ?
C4A C3A C8A N2A -178.23(10) . . . . ?
C4A C3A C8A C7A -0.14(16) . . . . ?
C4A C5A C6A C7A -0.20(18) . . . . ?
C5A C6A C7A C8A 0.48(17) . . . . ?
C6A C7A C8A N2A 177.41(11) . . . . ?
C6A C7A C8A C3A -0.31(16) . . . . ?
C8A N2A C1A C2A 0.39(12) . . . . ?
C8A N2A C1A C9A 172.88(14) . . . . ?
C8A C3A C4A C5A 0.42(16) . . . . ?
C9A N3A C16A C11A 2.21(12) . . . . ?
C9A N3A C16A C15A -177.56(11) . . . . ?
C9A C1A C2A N1A -0.21(12) . . . . ?
C9A C1A C2A C3A -174.76(9) . . . . ?
C9A C10A C11A C12A 176.40(12) . . . . ?
C9A C10A C11A C16A -1.05(12) . . . . ?
C10A N1A C2A C1A 0.06(12) . . . . ?
C10A N1A C2A C3A 171.64(14) . . . . ?
C10A N1A C17A C18A 140.61(11) . . . . ?
C10A N1A C17A C22A -39.82(16) . . . . ?
C10A C11A C12A C13A -177.27(12) . . . . ?
C10A C11A C16A N3A -0.72(12) . . . . ?
C10A C11A C16A C15A 179.07(10) . . . . ?
C11A C12A C13A C14A -0.72(17) . . . . ?
C12A C11A C16A N3A -178.73(9) . . . . ?
C12A C11A C16A C15A 1.06(16) . . . . ?
C12A C13A C14A C15A 0.58(18) . . . . ?
C13A C14A C15A C16A 0.39(17) . . . . ?
C14A C15A C16A N3A 178.55(11) . . . . ?
C14A C15A C16A C11A -1.20(16) . . . . ?
C16A N3A C9A C1A 175.20(14) . . . . ?
C16A N3A C9A C10A -2.90(12) . . . . ?
C16A C11A C12A C13A -0.08(16) . . . . ?
C17A N1A C2A C1A -176.65(10) . . . . ?
C17A N1A C2A C3A -5.1(2) . . . . ?
C17A N1A C10A C9A 176.86(10) . . . . ?
C17A N1A C10A C11A -9.2(2) . . . . ?
C17A C18A C19A C20A 0.8(2) . . . . ?
C18A C17A C22A C21A 0.22(17) . . . . ?
C18A C19A C20A C21A -0.5(2) . . . . ?
C19A C20A C21A C22A 0.05(19) . . . . ?
C20A C21A C22A C17A 0.10(18) . . . . ?
C22A C17A C18A C19A -0.68(18) . . . . ?
O1B C1B C2B O2B 2.77(17) . . . . ?
O1B C1B C2B C3B -176.83(11) . . . . ?
O1B C1B C14B C9B -177.94(11) . . . . ?
O1B C1B C14B C13B 0.44(18) . . . . ?
O2B C2B C3B C4B -4.47(18) . . . . ?
O2B C2B C3B C8B 174.34(11) . . . . ?
C1B C2B C3B C4B 175.11(10) . . . . ?
C1B C2B C3B C8B -6.09(15) . . . . ?
C2B C1B C14B C9B 2.64(16) . . . . ?
C2B C1B C14B C13B -178.98(10) . . . . ?
C2B C3B C4B C5B 178.35(11) . . . . ?
C2B C3B C8B C7B -176.76(10) . . . . ?
C2B C3B C8B C9B 4.38(16) . . . . ?
C3B C4B C5B C6B -1.2(2) . . . . ?
C3B C8B C9B C10B 179.60(11) . . . . ?
C3B C8B C9B C14B 1.08(16) . . . . ?
C4B C3B C8B C7B 2.02(17) . . . . ?
C4B C3B C8B C9B -176.84(10) . . . . ?
C4B C5B C6B C7B 1.3(2) . . . . ?
C5B C6B C7B C8B 0.3(2) . . . . ?
C6B C7B C8B C3B -1.94(18) . . . . ?
C6B C7B C8B C9B 176.90(11) . . . . ?
C7B C8B C9B C10B 0.79(17) . . . . ?
C7B C8B C9B C14B -177.72(11) . . . . ?
C8B C3B C4B C5B -0.45(18) . . . . ?
C8B C9B C10B C11B -177.53(11) . . . . ?
C8B C9B C14B C1B -4.58(16) . . . . ?
C8B C9B C14B C13B 177.10(10) . . . . ?
C9B C10B C11B C12B 0.4(2) . . . . ?
C10B C9B C14B C1B 176.83(10) . . . . ?
C10B C9B C14B C13B -1.49(17) . . . . ?
C10B C11B C12B C13B -1.4(2) . . . . ?
C11B C12B C13B C14B 0.9(2) . . . . ?
C12B C13B C14B C1B -177.85(11) . . . . ?
C12B C13B C14B C9B 0.52(18) . . . . ?
C14B C1B C2B O2B -177.78(11) . . . . ?
C14B C1B C2B C3B 2.62(15) . . . . ?
C14B C9B C10B C11B 1.05(18) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop'
_olex2_submission_original_sample_id PhDIP-co-phenanthrenequinone
_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_pere77
_audit_block_doi                 10.5517/ccdc.csd.cc25m768
_database_code_depnum_ccdc_archive 'CCDC 2014479'
loop_
_audit_author_name
_audit_author_address
'Thierry Marris'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2020-07-07 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;
_audit_creation_date             2018-06-14
_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         '2(C22 H15 N3), 2(C16 H6 O4), C2 H3 N'
_chemical_formula_sum            'C78 H45 N7 O8'
_chemical_formula_weight         1208.21
_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 0.0139 0.0070 '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 0.0241 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0390 0.0250 '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                   24.773(2)
_cell_length_b                   6.6680(6)
_cell_length_c                   33.537(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.035(4)
_cell_angle_gamma                90
_cell_volume                     5526.0(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9310
_cell_measurement_temperature    150
_cell_measurement_theta_max      53.945
_cell_measurement_theta_min      3.112
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.929
_exptl_absorpt_coefficient_mu    0.496
_exptl_absorpt_correction_T_max  0.3667
_exptl_absorpt_correction_T_min  0.1992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1467 before and 0.1046 after correction. The Ratio of minimum to maximum transmission is 0.5432. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light Colorless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2504
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            74598
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.105
_diffrn_reflns_theta_min         1.868
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7368
_reflns_number_total             10083
_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 (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       0.00075(14)
_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   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     856
_refine_ls_number_reflns         10083
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0805
_refine_ls_restrained_S_all      1.055
_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)+(0.1522P)²+6.5582P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2464
_refine_ls_wR_factor_ref         0.2703
_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:
 C4A(H4A), C5A(H5A), C6A(H6A), C7A(H7A), C12A(H12A), C13A(H13A), C14A(H14A),
 C15A(H15A), C18A(H18A), C19A(H19A), C20A(H20A), C21A(H21A), C22A(H22A),
 C13C(H13C), C12B(H12B), C15B(H15B), C11D(H11D), C19B(H19B), C12D(H12D),
 C21B(H21B), C11C(H11C), C12C(H12C), C4B(H4B), C13B(H13B), C4C(H4C), C13D(H13D),
  C4D(H4D), C14B(H14B), C5C(H5C), C5D(H5D), C5B(H5B), C6B(H6B), C18B(H18B),
 C6C(H6C), C20B(H20B), C6D(H6D), C22B(H22B), C7B(H7B)
2.b Idealised Me refined as rotating group:
 C2E(H2EA,H2EB,H2EC)
;
_atom_sites_solution_hydrogens   mixed
_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
N1A N 0.26043(12) 0.1739(4) 0.60396(9) 0.0428(7) Uani 1 1 d . . . . .
H1A H 0.2459(15) 0.183(6) 0.5797(12) 0.043(10) Uiso 1 1 d . . . . .
N2A N 0.39323(13) 0.2736(5) 0.56874(9) 0.0458(7) Uani 1 1 d . . . . .
H2A H 0.3847(16) 0.263(6) 0.5423(13) 0.051(11) Uiso 1 1 d . . . . .
N3A N 0.37539(11) 0.2052(4) 0.67040(8) 0.0391(7) Uani 1 1 d . . . . .
C1A C 0.31439(14) 0.1923(5) 0.61622(10) 0.0397(8) Uani 1 1 d . . . . .
C2A C 0.32137(13) 0.1689(5) 0.65736(10) 0.0387(8) Uani 1 1 d . . . . .
C3A C 0.26921(13) 0.1383(5) 0.67253(10) 0.0394(8) Uani 1 1 d . . . . .
C4A C 0.24878(14) 0.1098(6) 0.70967(10) 0.0462(9) Uani 1 1 d . . . . .
H4A H 0.272392 0.106957 0.733245 0.055 Uiso 1 1 calc R . . . .
C5A C 0.19329(15) 0.0856(6) 0.71184(12) 0.0534(10) Uani 1 1 d . . . . .
H5A H 0.179041 0.066207 0.737127 0.064 Uiso 1 1 calc R . . . .
C6A C 0.15827(15) 0.0894(6) 0.67738(12) 0.0509(9) Uani 1 1 d . . . . .
H6A H 0.120528 0.072987 0.679722 0.061 Uiso 1 1 calc R . . . .
C7A C 0.17701(14) 0.1164(6) 0.64013(11) 0.0458(9) Uani 1 1 d . . . . .
H7A H 0.152957 0.117584 0.616784 0.055 Uiso 1 1 calc R . . . .
C8A C 0.23250(14) 0.1419(5) 0.63782(10) 0.0417(8) Uani 1 1 d . . . . .
C9A C 0.36521(14) 0.2443(5) 0.60276(10) 0.0398(8) Uani 1 1 d . . . . .
C10A C 0.40159(14) 0.2486(5) 0.63617(10) 0.0404(8) Uani 1 1 d . . . . .
C11A C 0.45495(14) 0.2800(5) 0.62329(10) 0.0417(8) Uani 1 1 d . . . . .
C12A C 0.50717(15) 0.2944(6) 0.64201(11) 0.0488(9) Uani 1 1 d . . . . .
H12A H 0.512671 0.284743 0.670269 0.059 Uiso 1 1 calc R . . . .
C13A C 0.55041(16) 0.3227(7) 0.61901(13) 0.0572(10) Uani 1 1 d . . . . .
H13A H 0.585842 0.334333 0.631590 0.069 Uiso 1 1 calc R . . . .
C14A C 0.54284(17) 0.3345(7) 0.57738(13) 0.0593(11) Uani 1 1 d . . . . .
H14A H 0.573441 0.350577 0.562119 0.071 Uiso 1 1 calc R . . . .
C15A C 0.49152(17) 0.3231(6) 0.55777(12) 0.0537(10) Uani 1 1 d . . . . .
H15A H 0.486607 0.334411 0.529507 0.064 Uiso 1 1 calc R . . . .
C16A C 0.44741(15) 0.2946(6) 0.58097(11) 0.0453(8) Uani 1 1 d . . . . .
C17A C 0.39880(13) 0.2053(5) 0.71052(10) 0.0390(8) Uani 1 1 d . . . . .
C18A C 0.38787(13) 0.0475(5) 0.73585(10) 0.0412(8) Uani 1 1 d . . . . .
H18A H 0.364808 -0.059219 0.726689 0.049 Uiso 1 1 calc R . . . .
C19A C 0.41116(14) 0.0482(6) 0.77470(10) 0.0442(8) Uani 1 1 d . . . . .
H19A H 0.403328 -0.057322 0.792423 0.053 Uiso 1 1 calc R . . . .
C20A C 0.44587(13) 0.2020(6) 0.78796(10) 0.0447(9) Uani 1 1 d . . . . .
H20A H 0.461680 0.201384 0.814607 0.054 Uiso 1 1 calc R . . . .
C21A C 0.45725(14) 0.3556(6) 0.76221(10) 0.0442(8) Uani 1 1 d . . . . .
H21A H 0.481731 0.458727 0.771000 0.053 Uiso 1 1 calc R . . . .
C22A C 0.43315(13) 0.3603(6) 0.72357(10) 0.0406(8) Uani 1 1 d . . . . .
H22A H 0.440083 0.468436 0.706219 0.049 Uiso 1 1 calc R . . . .
O3C O 0.76686(11) 0.1989(5) 0.52628(7) 0.0577(7) Uani 1 1 d . . . . .
O1C O 0.66143(11) 0.3567(4) 0.30975(7) 0.0533(7) Uani 1 1 d . . . . .
O1D O 0.27090(11) 0.2805(5) 0.51660(8) 0.0579(7) Uani 1 1 d . . . . .
O4C O 0.84578(11) 0.3333(5) 0.48298(8) 0.0583(7) Uani 1 1 d . . . . .
O4D O 0.16478(11) 0.3475(4) 0.31323(7) 0.0512(7) Uani 1 1 d . . . . .
O2C O 0.57956(11) 0.2371(5) 0.35487(9) 0.0594(7) Uani 1 1 d . . . . .
O2D O 0.17431(12) 0.1572(5) 0.53782(8) 0.0615(8) Uani 1 1 d . . . . .
O3D O 0.06743(10) 0.2104(4) 0.33526(7) 0.0513(7) Uani 1 1 d . . . . .
N1B N 0.75685(11) 0.1581(5) 0.61031(8) 0.0403(7) Uani 1 1 d . . . . .
H1B H 0.7412(15) 0.159(6) 0.5825(12) 0.047(10) Uiso 1 1 d . . . . .
N1E N 0.41861(17) 0.2106(7) 0.46771(13) 0.0808(12) Uani 1 1 d . . . . .
N2B N 0.88333(11) 0.2917(4) 0.57042(9) 0.0382(7) Uani 1 1 d . . . . .
H2B H 0.8668(16) 0.301(6) 0.5458(13) 0.052(11) Uiso 1 1 d . . . . .
N3B N 0.87457(10) 0.2225(4) 0.67344(8) 0.0369(6) Uani 1 1 d . . . . .
C13C C 0.76936(15) 0.3700(6) 0.34092(10) 0.0454(8) Uani 1 1 d . . . . .
H13C H 0.762380 0.388831 0.312955 0.054 Uiso 1 1 calc R . . . .
C10B C 0.89783(13) 0.2731(5) 0.63781(9) 0.0356(7) Uani 1 1 d . . . . .
C12B C 1.00296(14) 0.3281(5) 0.63796(10) 0.0419(8) Uani 1 1 d . . . . .
H12B H 1.011620 0.316040 0.665904 0.050 Uiso 1 1 calc R . . . .
C15B C 0.97854(14) 0.3622(5) 0.55451(10) 0.0415(8) Uani 1 1 d . . . . .
H15B H 0.970542 0.373292 0.526480 0.050 Uiso 1 1 calc R . . . .
C11D C 0.25601(16) 0.3711(6) 0.36792(11) 0.0489(9) Uani 1 1 d . . . . .
H11D H 0.261286 0.394420 0.340527 0.059 Uiso 1 1 calc R . . . .
C16D C 0.14159(14) 0.2273(5) 0.43181(10) 0.0402(8) Uani 1 1 d . . . . .
C9C C 0.80139(14) 0.3020(5) 0.46562(10) 0.0423(8) Uani 1 1 d . . . . .
C19B C 0.91593(14) 0.0557(6) 0.77606(10) 0.0452(8) Uani 1 1 d . . . . .
H19B H 0.907870 -0.048711 0.793978 0.054 Uiso 1 1 calc R . . . .
C10C C 0.78928(14) 0.3209(5) 0.42281(10) 0.0411(8) Uani 1 1 d . . . . .
C7C C 0.70021(15) 0.2338(6) 0.47264(10) 0.0448(8) Uani 1 1 d . . . . .
C12D C 0.29932(16) 0.3877(6) 0.39614(12) 0.0520(9) Uani 1 1 d . . . . .
H12D H 0.334189 0.422126 0.388175 0.062 Uiso 1 1 calc R . . . .
C8C C 0.75516(15) 0.2397(6) 0.49136(10) 0.0441(8) Uani 1 1 d . . . . .
C8B C 0.73198(13) 0.1193(5) 0.64513(10) 0.0397(8) Uani 1 1 d . . . . .
C14C C 0.72639(14) 0.3337(5) 0.36476(10) 0.0418(8) Uani 1 1 d . . . . .
C1E C 0.43375(18) 0.1946(7) 0.43616(15) 0.0652(12) Uani 1 1 d . . . . .
C15D C 0.19621(14) 0.2835(5) 0.41976(10) 0.0418(8) Uani 1 1 d . . . . .
C1C C 0.67072(15) 0.3231(5) 0.34501(10) 0.0439(8) Uani 1 1 d . . . . .
C17B C 0.90079(13) 0.2186(5) 0.71257(9) 0.0391(8) Uani 1 1 d . . . . .
C1B C 0.81081(13) 0.1922(5) 0.62114(10) 0.0365(7) Uani 1 1 d . . . . .
C21B C 0.96424(14) 0.3558(6) 0.76254(10) 0.0445(8) Uani 1 1 d . . . . .
H21B H 0.990278 0.455011 0.770634 0.053 Uiso 1 1 calc R . . . .
C1D C 0.23441(15) 0.2642(6) 0.49029(11) 0.0460(9) Uani 1 1 d . . . . .
C7D C 0.09778(14) 0.2087(5) 0.40360(10) 0.0407(8) Uani 1 1 d . . . . .
C2C C 0.62451(14) 0.2649(5) 0.37051(11) 0.0454(8) Uani 1 1 d . . . . .
C8D C 0.10367(14) 0.2378(5) 0.36049(10) 0.0417(8) Uani 1 1 d . . . . .
C2B C 0.82068(13) 0.1760(5) 0.66227(10) 0.0366(7) Uani 1 1 d . . . . .
C9B C 0.85940(13) 0.2582(5) 0.60567(9) 0.0364(7) Uani 1 1 d . . . . .
C2D C 0.17823(15) 0.1995(6) 0.50278(10) 0.0460(9) Uani 1 1 d . . . . .
C9D C 0.15942(15) 0.3086(5) 0.34796(10) 0.0418(8) Uani 1 1 d . . . . .
C2E C 0.45272(19) 0.1808(8) 0.39624(14) 0.0716(13) Uani 1 1 d . . . . .
H2EA H 0.473857 0.057537 0.393993 0.107 Uiso 1 1 calc GR . . . .
H2EB H 0.475492 0.297049 0.391280 0.107 Uiso 1 1 calc GR . . . .
H2EC H 0.421608 0.178316 0.376506 0.107 Uiso 1 1 calc GR . . . .
C10D C 0.20458(15) 0.3202(5) 0.37935(10) 0.0422(8) Uani 1 1 d . . . . .
C3B C 0.77011(13) 0.1305(5) 0.67889(10) 0.0394(8) Uani 1 1 d . . . . .
C11C C 0.83156(15) 0.3558(6) 0.39822(11) 0.0459(8) Uani 1 1 d . . . . .
H11C H 0.867656 0.363833 0.409708 0.055 Uiso 1 1 calc R . . . .
C3C C 0.63737(14) 0.2473(5) 0.41453(11) 0.0438(8) Uani 1 1 d . . . . .
C11B C 0.94933(13) 0.3103(5) 0.62228(10) 0.0362(7) Uani 1 1 d . . . . .
C3D C 0.13313(14) 0.1910(5) 0.47210(10) 0.0422(8) Uani 1 1 d . . . . .
C12C C 0.82156(15) 0.3787(6) 0.35749(11) 0.0474(9) Uani 1 1 d . . . . .
H12C H 0.850660 0.400344 0.341001 0.057 Uiso 1 1 calc R . . . .
C4B C 0.75197(14) 0.1010(6) 0.71684(10) 0.0460(8) Uani 1 1 d . . . . .
H4B H 0.776444 0.109192 0.739897 0.055 Uiso 1 1 calc R . . . .
C13B C 1.04299(14) 0.3633(6) 0.61242(11) 0.0483(9) Uani 1 1 d . . . . .
H13B H 1.079486 0.374720 0.622914 0.058 Uiso 1 1 calc R . . . .
C4C C 0.59512(16) 0.2110(6) 0.43881(12) 0.0530(10) Uani 1 1 d . . . . .
H4C H 0.559148 0.202768 0.427088 0.064 Uiso 1 1 calc R . . . .
C13D C 0.29154(15) 0.3540(6) 0.43576(12) 0.0506(9) Uani 1 1 d . . . . .
H13D H 0.321243 0.366665 0.455105 0.061 Uiso 1 1 calc R . . . .
C4D C 0.08165(15) 0.1402(6) 0.48349(11) 0.0462(8) Uani 1 1 d . . . . .
H4D H 0.076512 0.112966 0.510766 0.055 Uiso 1 1 calc R . . . .
C14B C 1.03074(14) 0.3826(6) 0.57103(11) 0.0468(9) Uani 1 1 d . . . . .
H14B H 1.059021 0.410354 0.554120 0.056 Uiso 1 1 calc R . . . .
C5C C 0.60445(17) 0.1868(6) 0.47961(12) 0.0560(10) Uani 1 1 d . . . . .
H5C H 0.575131 0.164920 0.495884 0.067 Uiso 1 1 calc R . . . .
C15C C 0.73587(14) 0.3059(5) 0.40606(10) 0.0385(8) Uani 1 1 d . . . . .
C5D C 0.03847(15) 0.1295(6) 0.45558(11) 0.0477(9) Uani 1 1 d . . . . .
H5D H 0.003289 0.100931 0.463645 0.057 Uiso 1 1 calc R . . . .
C16C C 0.69061(14) 0.2625(5) 0.43116(10) 0.0398(8) Uani 1 1 d . . . . .
C5B C 0.69758(15) 0.0595(6) 0.72047(11) 0.0507(9) Uani 1 1 d . . . . .
H5B H 0.685122 0.039096 0.746317 0.061 Uiso 1 1 calc R . . . .
C16B C 0.93775(13) 0.3246(5) 0.58018(10) 0.0365(7) Uani 1 1 d . . . . .
C6B C 0.66106(15) 0.0470(6) 0.68733(12) 0.0528(9) Uani 1 1 d . . . . .
H6B H 0.624121 0.018459 0.690835 0.063 Uiso 1 1 calc R . . . .
C18B C 0.88991(14) 0.0609(6) 0.73797(10) 0.0431(8) Uani 1 1 d . . . . .
H18B H 0.865085 -0.041580 0.729425 0.052 Uiso 1 1 calc R . . . .
C6C C 0.65698(16) 0.1947(6) 0.49651(12) 0.0529(10) Uani 1 1 d . . . . .
H6C H 0.663886 0.173574 0.524414 0.063 Uiso 1 1 calc R . . . .
C20B C 0.95358(15) 0.2016(6) 0.78818(10) 0.0487(9) Uani 1 1 d . . . . .
H20B H 0.971890 0.195145 0.814010 0.058 Uiso 1 1 calc R . . . .
C6D C 0.04646(14) 0.1606(6) 0.41569(11) 0.0452(8) Uani 1 1 d . . . . .
H6D H 0.016786 0.149105 0.396285 0.054 Uiso 1 1 calc R . . . .
C22B C 0.93705(13) 0.3671(6) 0.72480(10) 0.0412(8) Uani 1 1 d . . . . .
H22B H 0.943430 0.476440 0.707589 0.049 Uiso 1 1 calc R . . . .
C7B C 0.67761(14) 0.0756(6) 0.64928(11) 0.0474(9) Uani 1 1 d . . . . .
H7B H 0.652626 0.065717 0.626543 0.057 Uiso 1 1 calc R . . . .
C14D C 0.24052(14) 0.3014(5) 0.44813(10) 0.0441(8) 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
N1A H1A 0.87(4) . ?
N1A C1A 1.376(4) . ?
N1A C8A 1.387(5) . ?
N2A H2A 0.90(4) . ?
N2A C9A 1.391(5) . ?
N2A C16A 1.383(5) . ?
N3A C2A 1.399(4) . ?
N3A C10A 1.389(4) . ?
N3A C17A 1.427(4) . ?
C1A C2A 1.387(5) . ?
C1A C9A 1.410(5) . ?
C2A C3A 1.436(5) . ?
C3A C4A 1.390(5) . ?
C3A C8A 1.426(5) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.391(5) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.396(5) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.375(5) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.393(5) . ?
C9A C10A 1.388(5) . ?
C10A C11A 1.435(5) . ?
C11A C12A 1.401(5) . ?
C11A C16A 1.422(5) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.376(6) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.398(6) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.392(6) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.398(5) . ?
C17A C18A 1.391(5) . ?
C17A C22A 1.390(5) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.387(5) . ?
C19A H19A 0.9500 . ?
C19A C20A 1.391(5) . ?
C20A H20A 0.9500 . ?
C20A C21A 1.382(5) . ?
C21A H21A 0.9500 . ?
C21A C22A 1.388(5) . ?
C22A H22A 0.9500 . ?
O3C C8C 1.217(4) . ?
O1C C1C 1.210(4) . ?
O1D C1D 1.223(4) . ?
O4C C9C 1.226(4) . ?
O4D C9D 1.210(4) . ?
O2C C2C 1.211(4) . ?
O2D C2D 1.219(4) . ?
O3D C8D 1.203(4) . ?
N1B H1B 0.98(4) . ?
N1B C8B 1.383(4) . ?
N1B C1B 1.379(4) . ?
N1E C1E 1.152(6) . ?
N2B H2B 0.90(4) . ?
N2B C9B 1.378(4) . ?
N2B C16B 1.382(4) . ?
N3B C10B 1.404(4) . ?
N3B C17B 1.423(4) . ?
N3B C2B 1.396(4) . ?
C13C H13C 0.9500 . ?
C13C C14C 1.397(5) . ?
C13C C12C 1.372(5) . ?
C10B C9B 1.391(4) . ?
C10B C11B 1.433(5) . ?
C12B H12B 0.9500 . ?
C12B C11B 1.399(5) . ?
C12B C13B 1.375(5) . ?
C15B H15B 0.9500 . ?
C15B C14B 1.377(5) . ?
C15B C16B 1.395(5) . ?
C11D H11D 0.9500 . ?
C11D C12D 1.384(5) . ?
C11D C10D 1.398(5) . ?
C16D C15D 1.487(5) . ?
C16D C7D 1.394(5) . ?
C16D C3D 1.403(5) . ?
C9C C10C 1.451(5) . ?
C9C C8C 1.539(5) . ?
C19B H19B 0.9500 . ?
C19B C18B 1.390(5) . ?
C19B C20B 1.389(5) . ?
C10C C11C 1.397(5) . ?
C10C C15C 1.404(5) . ?
C7C C8C 1.459(5) . ?
C7C C16C 1.408(5) . ?
C7C C6C 1.406(5) . ?
C12D H12D 0.9500 . ?
C12D C13D 1.374(5) . ?
C8B C3B 1.425(5) . ?
C8B C7B 1.395(5) . ?
C14C C1C 1.489(5) . ?
C14C C15C 1.401(5) . ?
C1E C2E 1.453(7) . ?
C15D C10D 1.407(5) . ?
C15D C14D 1.406(5) . ?
C1C C2C 1.526(5) . ?
C17B C18B 1.391(5) . ?
C17B C22B 1.380(5) . ?
C1B C2B 1.388(5) . ?
C1B C9B 1.414(5) . ?
C21B H21B 0.9500 . ?
C21B C20B 1.378(5) . ?
C21B C22B 1.393(5) . ?
C1D C2D 1.543(5) . ?
C1D C14D 1.454(5) . ?
C7D C8D 1.476(5) . ?
C7D C6D 1.399(5) . ?
C2C C3C 1.493(5) . ?
C8D C9D 1.546(5) . ?
C2B C3B 1.439(5) . ?
C2D C3D 1.466(5) . ?
C9D C10D 1.483(5) . ?
C2E H2EA 0.9800 . ?
C2E H2EB 0.9800 . ?
C2E H2EC 0.9800 . ?
C3B C4B 1.393(5) . ?
C11C H11C 0.9500 . ?
C11C C12C 1.379(5) . ?
C3C C4C 1.392(5) . ?
C3C C16C 1.399(5) . ?
C11B C16B 1.424(5) . ?
C3D C4D 1.398(5) . ?
C12C H12C 0.9500 . ?
C4B H4B 0.9500 . ?
C4B C5B 1.390(5) . ?
C13B H13B 0.9500 . ?
C13B C14B 1.406(5) . ?
C4C H4C 0.9500 . ?
C4C C5C 1.381(6) . ?
C13D H13D 0.9500 . ?
C13D C14D 1.402(5) . ?
C4D H4D 0.9500 . ?
C4D C5D 1.373(5) . ?
C14B H14B 0.9500 . ?
C5C H5C 0.9500 . ?
C5C C6C 1.383(6) . ?
C15C C16C 1.477(5) . ?
C5D H5D 0.9500 . ?
C5D C6D 1.381(5) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.385(5) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.381(5) . ?
C18B H18B 0.9500 . ?
C6C H6C 0.9500 . ?
C20B H20B 0.9500 . ?
C6D H6D 0.9500 . ?
C22B H22B 0.9500 . ?
C7B H7B 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
C1A N1A H1A 127(3) . . ?
C1A N1A C8A 107.4(3) . . ?
C8A N1A H1A 125(3) . . ?
C9A N2A H2A 135(3) . . ?
C16A N2A H2A 117(3) . . ?
C16A N2A C9A 107.5(3) . . ?
C2A N3A C17A 127.7(3) . . ?
C10A N3A C2A 105.7(3) . . ?
C10A N3A C17A 126.6(3) . . ?
N1A C1A C2A 109.7(3) . . ?
N1A C1A C9A 142.8(3) . . ?
C2A C1A C9A 107.1(3) . . ?
N3A C2A C3A 141.1(3) . . ?
C1A C2A N3A 109.9(3) . . ?
C1A C2A C3A 108.4(3) . . ?
C4A C3A C2A 136.9(3) . . ?
C4A C3A C8A 118.8(3) . . ?
C8A C3A C2A 104.3(3) . . ?
C3A C4A H4A 120.5 . . ?
C3A C4A C5A 119.1(3) . . ?
C5A C4A H4A 120.5 . . ?
C4A C5A H5A 119.6 . . ?
C4A C5A C6A 120.9(4) . . ?
C6A C5A H5A 119.6 . . ?
C5A C6A H6A 119.2 . . ?
C7A C6A C5A 121.7(4) . . ?
C7A C6A H6A 119.2 . . ?
C6A C7A H7A 121.2 . . ?
C6A C7A C8A 117.7(3) . . ?
C8A C7A H7A 121.2 . . ?
N1A C8A C3A 110.2(3) . . ?
N1A C8A C7A 128.0(3) . . ?
C7A C8A C3A 121.9(3) . . ?
N2A C9A C1A 143.7(3) . . ?
C10A C9A N2A 109.0(3) . . ?
C10A C9A C1A 106.9(3) . . ?
N3A C10A C11A 140.7(3) . . ?
C9A C10A N3A 110.4(3) . . ?
C9A C10A C11A 108.6(3) . . ?
C12A C11A C10A 135.8(3) . . ?
C12A C11A C16A 119.7(3) . . ?
C16A C11A C10A 104.6(3) . . ?
C11A C12A H12A 120.4 . . ?
C13A C12A C11A 119.2(4) . . ?
C13A C12A H12A 120.4 . . ?
C12A C13A H13A 119.6 . . ?
C12A C13A C14A 120.8(4) . . ?
C14A C13A H13A 119.6 . . ?
C13A C14A H14A 119.2 . . ?
C15A C14A C13A 121.5(4) . . ?
C15A C14A H14A 119.2 . . ?
C14A C15A H15A 121.0 . . ?
C14A C15A C16A 117.9(4) . . ?
C16A C15A H15A 121.0 . . ?
N2A C16A C11A 110.2(3) . . ?
N2A C16A C15A 129.0(3) . . ?
C15A C16A C11A 120.8(3) . . ?
C18A C17A N3A 119.5(3) . . ?
C22A C17A N3A 119.8(3) . . ?
C22A C17A C18A 120.7(3) . . ?
C17A C18A H18A 120.5 . . ?
C19A C18A C17A 119.0(3) . . ?
C19A C18A H18A 120.5 . . ?
C18A C19A H19A 119.7 . . ?
C18A C19A C20A 120.7(3) . . ?
C20A C19A H19A 119.7 . . ?
C19A C20A H20A 120.2 . . ?
C21A C20A C19A 119.7(3) . . ?
C21A C20A H20A 120.2 . . ?
C20A C21A H21A 119.8 . . ?
C20A C21A C22A 120.5(3) . . ?
C22A C21A H21A 119.8 . . ?
C17A C22A H22A 120.3 . . ?
C21A C22A C17A 119.4(3) . . ?
C21A C22A H22A 120.3 . . ?
C8B N1B H1B 129(2) . . ?
C1B N1B H1B 124(2) . . ?
C1B N1B C8B 106.8(3) . . ?
C9B N2B H2B 127(3) . . ?
C9B N2B C16B 107.1(3) . . ?
C16B N2B H2B 126(3) . . ?
C10B N3B C17B 127.0(3) . . ?
C2B N3B C10B 105.5(2) . . ?
C2B N3B C17B 127.5(3) . . ?
C14C C13C H13C 119.7 . . ?
C12C C13C H13C 119.7 . . ?
C12C C13C C14C 120.7(3) . . ?
N3B C10B C11B 141.3(3) . . ?
C9B C10B N3B 110.1(3) . . ?
C9B C10B C11B 108.0(3) . . ?
C11B C12B H12B 120.4 . . ?
C13B C12B H12B 120.4 . . ?
C13B C12B C11B 119.2(3) . . ?
C14B C15B H15B 121.0 . . ?
C14B C15B C16B 118.0(3) . . ?
C16B C15B H15B 121.0 . . ?
C12D C11D H11D 119.7 . . ?
C12D C11D C10D 120.6(4) . . ?
C10D C11D H11D 119.7 . . ?
C7D C16D C15D 121.2(3) . . ?
C7D C16D C3D 118.4(3) . . ?
C3D C16D C15D 120.4(3) . . ?
O4C C9C C10C 124.8(3) . . ?
O4C C9C C8C 117.2(3) . . ?
C10C C9C C8C 117.9(3) . . ?
C18B C19B H19B 119.7 . . ?
C20B C19B H19B 119.7 . . ?
C20B C19B C18B 120.7(3) . . ?
C11C C10C C9C 119.1(3) . . ?
C11C C10C C15C 120.0(3) . . ?
C15C C10C C9C 120.9(3) . . ?
C16C C7C C8C 120.6(3) . . ?
C6C C7C C8C 119.0(3) . . ?
C6C C7C C16C 120.4(3) . . ?
C11D C12D H12D 120.2 . . ?
C13D C12D C11D 119.5(4) . . ?
C13D C12D H12D 120.2 . . ?
O3C C8C C9C 117.6(3) . . ?
O3C C8C C7C 124.0(3) . . ?
C7C C8C C9C 118.3(3) . . ?
N1B C8B C3B 110.6(3) . . ?
N1B C8B C7B 127.9(3) . . ?
C7B C8B C3B 121.5(3) . . ?
C13C C14C C1C 118.2(3) . . ?
C13C C14C C15C 120.5(3) . . ?
C15C C14C C1C 121.3(3) . . ?
N1E C1E C2E 178.3(5) . . ?
C10D C15D C16D 120.3(3) . . ?
C14D C15D C16D 121.3(3) . . ?
C14D C15D C10D 118.4(3) . . ?
O1C C1C C14C 122.2(3) . . ?
O1C C1C C2C 119.7(3) . . ?
C14C C1C C2C 118.1(3) . . ?
C18B C17B N3B 118.9(3) . . ?
C22B C17B N3B 120.4(3) . . ?
C22B C17B C18B 120.7(3) . . ?
N1B C1B C2B 110.4(3) . . ?
N1B C1B C9B 142.1(3) . . ?
C2B C1B C9B 107.1(3) . . ?
C20B C21B H21B 119.8 . . ?
C20B C21B C22B 120.4(3) . . ?
C22B C21B H21B 119.8 . . ?
O1D C1D C2D 117.7(3) . . ?
O1D C1D C14D 124.4(4) . . ?
C14D C1D C2D 118.0(3) . . ?
C16D C7D C8D 121.8(3) . . ?
C16D C7D C6D 120.2(3) . . ?
C6D C7D C8D 118.0(3) . . ?
O2C C2C C1C 120.0(3) . . ?
O2C C2C C3C 122.8(4) . . ?
C3C C2C C1C 117.2(3) . . ?
O3D C8D C7D 123.3(3) . . ?
O3D C8D C9D 119.5(3) . . ?
C7D C8D C9D 117.3(3) . . ?
N3B C2B C3B 141.7(3) . . ?
C1B C2B N3B 110.4(3) . . ?
C1B C2B C3B 107.7(3) . . ?
N2B C9B C10B 109.9(3) . . ?
N2B C9B C1B 142.6(3) . . ?
C10B C9B C1B 107.0(3) . . ?
O2D C2D C1D 117.4(3) . . ?
O2D C2D C3D 124.0(3) . . ?
C3D C2D C1D 118.5(3) . . ?
O4D C9D C8D 119.2(3) . . ?
O4D C9D C10D 122.9(3) . . ?
C10D C9D C8D 117.8(3) . . ?
C1E C2E H2EA 109.5 . . ?
C1E C2E H2EB 109.5 . . ?
C1E C2E H2EC 109.5 . . ?
H2EA C2E H2EB 109.5 . . ?
H2EA C2E H2EC 109.5 . . ?
H2EB C2E H2EC 109.5 . . ?
C11D C10D C15D 120.3(3) . . ?
C11D C10D C9D 118.3(3) . . ?
C15D C10D C9D 121.3(3) . . ?
C8B C3B C2B 104.5(3) . . ?
C4B C3B C8B 118.7(3) . . ?
C4B C3B C2B 136.8(3) . . ?
C10C C11C H11C 119.6 . . ?
C12C C11C C10C 120.9(3) . . ?
C12C C11C H11C 119.6 . . ?
C4C C3C C2C 118.4(3) . . ?
C4C C3C C16C 120.4(3) . . ?
C16C C3C C2C 121.2(3) . . ?
C12B C11B C10B 136.4(3) . . ?
C12B C11B C16B 119.1(3) . . ?
C16B C11B C10B 104.5(3) . . ?
C16D C3D C2D 120.8(3) . . ?
C4D C3D C16D 120.4(3) . . ?
C4D C3D C2D 118.8(3) . . ?
C13C C12C C11C 119.6(3) . . ?
C13C C12C H12C 120.2 . . ?
C11C C12C H12C 120.2 . . ?
C3B C4B H4B 120.5 . . ?
C5B C4B C3B 119.0(3) . . ?
C5B C4B H4B 120.5 . . ?
C12B C13B H13B 119.5 . . ?
C12B C13B C14B 121.0(3) . . ?
C14B C13B H13B 119.5 . . ?
C3C C4C H4C 119.3 . . ?
C5C C4C C3C 121.3(4) . . ?
C5C C4C H4C 119.3 . . ?
C12D C13D H13D 119.4 . . ?
C12D C13D C14D 121.2(3) . . ?
C14D C13D H13D 119.4 . . ?
C3D C4D H4D 119.7 . . ?
C5D C4D C3D 120.5(3) . . ?
C5D C4D H4D 119.7 . . ?
C15B C14B C13B 121.3(3) . . ?
C15B C14B H14B 119.4 . . ?
C13B C14B H14B 119.4 . . ?
C4C C5C H5C 120.4 . . ?
C4C C5C C6C 119.2(4) . . ?
C6C C5C H5C 120.4 . . ?
C10C C15C C16C 121.2(3) . . ?
C14C C15C C10C 118.3(3) . . ?
C14C C15C C16C 120.5(3) . . ?
C4D C5D H5D 120.2 . . ?
C4D C5D C6D 119.7(3) . . ?
C6D C5D H5D 120.2 . . ?
C7C C16C C15C 120.5(3) . . ?
C3C C16C C7C 118.2(3) . . ?
C3C C16C C15C 121.3(3) . . ?
C4B C5B H5B 119.2 . . ?
C6B C5B C4B 121.6(3) . . ?
C6B C5B H5B 119.2 . . ?
N2B C16B C15B 128.2(3) . . ?
N2B C16B C11B 110.4(3) . . ?
C15B C16B C11B 121.3(3) . . ?
C5B C6B H6B 119.5 . . ?
C7B C6B C5B 120.9(3) . . ?
C7B C6B H6B 119.5 . . ?
C19B C18B C17B 119.0(3) . . ?
C19B C18B H18B 120.5 . . ?
C17B C18B H18B 120.5 . . ?
C7C C6C H6C 119.8 . . ?
C5C C6C C7C 120.4(4) . . ?
C5C C6C H6C 119.8 . . ?
C19B C20B H20B 120.2 . . ?
C21B C20B C19B 119.6(3) . . ?
C21B C20B H20B 120.2 . . ?
C7D C6D H6D 119.7 . . ?
C5D C6D C7D 120.7(3) . . ?
C5D C6D H6D 119.7 . . ?
C17B C22B C21B 119.6(3) . . ?
C17B C22B H22B 120.2 . . ?
C21B C22B H22B 120.2 . . ?
C8B C7B H7B 120.9 . . ?
C6B C7B C8B 118.2(3) . . ?
C6B C7B H7B 120.9 . . ?
C15D C14D C1D 120.9(3) . . ?
C13D C14D C15D 119.9(3) . . ?
C13D C14D C1D 119.2(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1A H1A O1D 0.87(4) 2.34(4) 3.044(4) 138(3) . yes
N1A H1A O2D 0.87(4) 2.19(4) 2.970(4) 149(3) . yes
N1B H1B O3C 0.98(4) 2.05(4) 2.859(4) 138(3) . yes
N2B H2B O3C 0.90(4) 2.61(4) 3.209(4) 125(3) . yes
N2B H2B O4C 0.90(4) 2.15(4) 3.026(4) 167(4) . yes

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
N1A C1A C2A N3A -174.7(3) . . . . ?
N1A C1A C2A C3A -1.3(4) . . . . ?
N1A C1A C9A N2A -16.1(9) . . . . ?
N1A C1A C9A C10A 172.7(5) . . . . ?
N2A C9A C10A N3A -175.7(3) . . . . ?
N2A C9A C10A C11A -0.5(4) . . . . ?
N3A C2A C3A C4A -8.6(8) . . . . ?
N3A C2A C3A C8A 171.1(4) . . . . ?
N3A C10A C11A C12A -5.8(8) . . . . ?
N3A C10A C11A C16A 173.1(5) . . . . ?
N3A C17A C18A C19A 179.5(3) . . . . ?
N3A C17A C22A C21A -177.7(3) . . . . ?
C1A N1A C8A C3A -0.4(4) . . . . ?
C1A N1A C8A C7A 179.4(4) . . . . ?
C1A C2A C3A C4A -178.6(4) . . . . ?
C1A C2A C3A C8A 1.0(4) . . . . ?
C1A C9A C10A N3A -1.2(4) . . . . ?
C1A C9A C10A C11A 173.9(3) . . . . ?
C2A N3A C10A C9A 1.3(4) . . . . ?
C2A N3A C10A C11A -171.4(5) . . . . ?
C2A N3A C17A C18A 47.8(5) . . . . ?
C2A N3A C17A C22A -133.7(4) . . . . ?
C2A C1A C9A N2A 171.8(5) . . . . ?
C2A C1A C9A C10A 0.6(4) . . . . ?
C2A C3A C4A C5A 179.7(4) . . . . ?
C2A C3A C8A N1A -0.4(4) . . . . ?
C2A C3A C8A C7A 179.8(3) . . . . ?
C3A C4A C5A C6A 0.1(6) . . . . ?
C4A C3A C8A N1A 179.4(3) . . . . ?
C4A C3A C8A C7A -0.4(5) . . . . ?
C4A C5A C6A C7A 0.2(6) . . . . ?
C5A C6A C7A C8A -0.6(6) . . . . ?
C6A C7A C8A N1A -179.1(3) . . . . ?
C6A C7A C8A C3A 0.7(5) . . . . ?
C8A N1A C1A C2A 1.1(4) . . . . ?
C8A N1A C1A C9A -170.9(5) . . . . ?
C8A C3A C4A C5A 0.1(5) . . . . ?
C9A N2A C16A C11A -0.3(4) . . . . ?
C9A N2A C16A C15A 178.7(4) . . . . ?
C9A C1A C2A N3A 0.2(4) . . . . ?
C9A C1A C2A C3A 173.6(3) . . . . ?
C9A C10A C11A C12A -178.6(4) . . . . ?
C9A C10A C11A C16A 0.3(4) . . . . ?
C10A N3A C2A C1A -0.9(4) . . . . ?
C10A N3A C2A C3A -170.9(5) . . . . ?
C10A N3A C17A C18A -134.7(4) . . . . ?
C10A N3A C17A C22A 43.8(5) . . . . ?
C10A C11A C12A C13A 178.8(4) . . . . ?
C10A C11A C16A N2A 0.0(4) . . . . ?
C10A C11A C16A C15A -179.1(4) . . . . ?
C11A C12A C13A C14A -0.8(6) . . . . ?
C12A C11A C16A N2A 179.1(3) . . . . ?
C12A C11A C16A C15A 0.0(6) . . . . ?
C12A C13A C14A C15A 1.6(7) . . . . ?
C13A C14A C15A C16A -1.5(6) . . . . ?
C14A C15A C16A N2A -178.2(4) . . . . ?
C14A C15A C16A C11A 0.7(6) . . . . ?
C16A N2A C9A C1A -170.6(5) . . . . ?
C16A N2A C9A C10A 0.5(4) . . . . ?
C16A C11A C12A C13A 0.0(6) . . . . ?
C17A N3A C2A C1A 177.1(3) . . . . ?
C17A N3A C2A C3A 7.1(7) . . . . ?
C17A N3A C10A C9A -176.7(3) . . . . ?
C17A N3A C10A C11A 10.6(7) . . . . ?
C17A C18A C19A C20A -1.4(5) . . . . ?
C18A C17A C22A C21A 0.8(5) . . . . ?
C18A C19A C20A C21A 0.0(5) . . . . ?
C19A C20A C21A C22A 1.7(5) . . . . ?
C20A C21A C22A C17A -2.1(5) . . . . ?
C22A C17A C18A C19A 1.0(5) . . . . ?
O1C C1C C2C O2C 5.8(5) . . . . ?
O1C C1C C2C C3C -173.5(3) . . . . ?
O1D C1D C2D O2D -4.1(5) . . . . ?
O1D C1D C2D C3D 176.3(3) . . . . ?
O1D C1D C14D C15D -178.6(4) . . . . ?
O1D C1D C14D C13D 1.9(6) . . . . ?
O4C C9C C10C C11C 7.4(6) . . . . ?
O4C C9C C10C C15C -172.1(3) . . . . ?
O4C C9C C8C O3C -9.8(5) . . . . ?
O4C C9C C8C C7C 170.0(3) . . . . ?
O4D C9D C10D C11D -2.5(5) . . . . ?
O4D C9D C10D C15D 176.8(3) . . . . ?
O2C C2C C3C C4C -4.6(6) . . . . ?
O2C C2C C3C C16C 174.1(4) . . . . ?
O2D C2D C3D C16D -175.2(4) . . . . ?
O2D C2D C3D C4D 3.0(6) . . . . ?
O3D C8D C9D O4D 4.6(5) . . . . ?
O3D C8D C9D C10D -173.8(3) . . . . ?
N1B C8B C3B C2B -0.9(4) . . . . ?
N1B C8B C3B C4B 178.3(3) . . . . ?
N1B C8B C7B C6B -178.2(4) . . . . ?
N1B C1B C2B N3B -176.4(3) . . . . ?
N1B C1B C2B C3B -0.5(4) . . . . ?
N1B C1B C9B N2B -16.4(9) . . . . ?
N1B C1B C9B C10B 173.3(4) . . . . ?
N3B C10B C9B N2B -175.1(3) . . . . ?
N3B C10B C9B C1B -1.3(4) . . . . ?
N3B C10B C11B C12B -6.4(8) . . . . ?
N3B C10B C11B C16B 171.6(4) . . . . ?
N3B C17B C18B C19B 179.3(3) . . . . ?
N3B C17B C22B C21B -177.0(3) . . . . ?
N3B C2B C3B C8B 174.6(4) . . . . ?
N3B C2B C3B C4B -4.3(8) . . . . ?
C13C C14C C1C O1C -4.5(5) . . . . ?
C13C C14C C1C C2C 174.6(3) . . . . ?
C13C C14C C15C C10C 1.7(5) . . . . ?
C13C C14C C15C C16C -178.5(3) . . . . ?
C10B N3B C17B C18B -138.1(3) . . . . ?
C10B N3B C17B C22B 40.8(5) . . . . ?
C10B N3B C2B C1B 1.4(4) . . . . ?
C10B N3B C2B C3B -172.4(4) . . . . ?
C10B C11B C16B N2B -1.9(4) . . . . ?
C10B C11B C16B C15B 179.5(3) . . . . ?
C12B C11B C16B N2B 176.5(3) . . . . ?
C12B C11B C16B C15B -2.0(5) . . . . ?
C12B C13B C14B C15B -1.6(6) . . . . ?
C11D C12D C13D C14D 0.6(6) . . . . ?
C16D C15D C10D C11D -179.3(3) . . . . ?
C16D C15D C10D C9D 1.3(5) . . . . ?
C16D C15D C14D C1D 0.4(5) . . . . ?
C16D C15D C14D C13D 179.8(3) . . . . ?
C16D C7D C8D O3D 175.2(3) . . . . ?
C16D C7D C8D C9D -5.3(5) . . . . ?
C16D C7D C6D C5D -0.4(5) . . . . ?
C16D C3D C4D C5D -1.4(5) . . . . ?
C9C C10C C11C C12C -178.7(3) . . . . ?
C9C C10C C15C C14C 177.4(3) . . . . ?
C9C C10C C15C C16C -2.5(5) . . . . ?
C10C C9C C8C O3C 170.7(3) . . . . ?
C10C C9C C8C C7C -9.5(5) . . . . ?
C10C C11C C12C C13C 0.9(6) . . . . ?
C10C C15C C16C C7C -0.4(5) . . . . ?
C10C C15C C16C C3C -179.9(3) . . . . ?
C12D C11D C10D C15D -0.5(6) . . . . ?
C12D C11D C10D C9D 178.8(3) . . . . ?
C12D C13D C14D C15D -0.4(6) . . . . ?
C12D C13D C14D C1D 179.1(4) . . . . ?
C8C C9C C10C C11C -173.1(3) . . . . ?
C8C C9C C10C C15C 7.3(5) . . . . ?
C8C C7C C16C C3C 177.4(3) . . . . ?
C8C C7C C16C C15C -2.1(5) . . . . ?
C8C C7C C6C C5C -179.6(4) . . . . ?
C8B N1B C1B C2B -0.1(4) . . . . ?
C8B N1B C1B C9B -171.1(5) . . . . ?
C8B C3B C4B C5B 0.7(5) . . . . ?
C14C C13C C12C C11C -1.5(6) . . . . ?
C14C C1C C2C O2C -173.3(3) . . . . ?
C14C C1C C2C C3C 7.4(5) . . . . ?
C14C C15C C16C C7C 179.7(3) . . . . ?
C14C C15C C16C C3C 0.2(5) . . . . ?
C15D C16D C7D C8D 1.8(5) . . . . ?
C15D C16D C7D C6D -178.4(3) . . . . ?
C15D C16D C3D C2D -2.5(5) . . . . ?
C15D C16D C3D C4D 179.3(3) . . . . ?
C1C C14C C15C C10C -179.0(3) . . . . ?
C1C C14C C15C C16C 0.8(5) . . . . ?
C1C C2C C3C C4C 174.7(3) . . . . ?
C1C C2C C3C C16C -6.6(5) . . . . ?
C17B N3B C10B C9B 179.6(3) . . . . ?
C17B N3B C10B C11B 10.7(7) . . . . ?
C17B N3B C2B C1B -178.3(3) . . . . ?
C17B N3B C2B C3B 8.0(7) . . . . ?
C1B N1B C8B C3B 0.6(4) . . . . ?
C1B N1B C8B C7B -179.8(4) . . . . ?
C1B C2B C3B C8B 0.8(4) . . . . ?
C1B C2B C3B C4B -178.1(4) . . . . ?
C1D C2D C3D C16D 4.3(5) . . . . ?
C1D C2D C3D C4D -177.5(3) . . . . ?
C7D C16D C15D C10D 0.4(5) . . . . ?
C7D C16D C15D C14D -179.7(3) . . . . ?
C7D C16D C3D C2D 177.2(3) . . . . ?
C7D C16D C3D C4D -0.9(5) . . . . ?
C7D C8D C9D O4D -174.9(3) . . . . ?
C7D C8D C9D C10D 6.7(5) . . . . ?
C2C C3C C4C C5C 177.9(4) . . . . ?
C2C C3C C16C C7C -176.7(3) . . . . ?
C2C C3C C16C C15C 2.8(5) . . . . ?
C8D C7D C6D C5D 179.4(3) . . . . ?
C8D C9D C10D C11D 175.8(3) . . . . ?
C8D C9D C10D C15D -4.9(5) . . . . ?
C2B N3B C10B C9B 0.0(4) . . . . ?
C2B N3B C10B C11B -168.9(4) . . . . ?
C2B N3B C17B C18B 41.4(5) . . . . ?
C2B N3B C17B C22B -139.6(4) . . . . ?
C2B C1B C9B N2B 172.4(4) . . . . ?
C2B C1B C9B C10B 2.1(4) . . . . ?
C2B C3B C4B C5B 179.5(4) . . . . ?
C9B N2B C16B C15B 179.0(3) . . . . ?
C9B N2B C16B C11B 0.6(4) . . . . ?
C9B C10B C11B C12B -175.5(4) . . . . ?
C9B C10B C11B C16B 2.5(4) . . . . ?
C9B C1B C2B N3B -2.2(4) . . . . ?
C9B C1B C2B C3B 173.8(3) . . . . ?
C2D C1D C14D C15D 1.5(5) . . . . ?
C2D C1D C14D C13D -177.9(3) . . . . ?
C2D C3D C4D C5D -179.6(3) . . . . ?
C10D C11D C12D C13D -0.1(6) . . . . ?
C10D C15D C14D C1D -179.7(3) . . . . ?
C10D C15D C14D C13D -0.2(5) . . . . ?
C3B C8B C7B C6B 1.3(6) . . . . ?
C3B C4B C5B C6B -0.1(6) . . . . ?
C11C C10C C15C C14C -2.1(5) . . . . ?
C11C C10C C15C C16C 178.0(3) . . . . ?
C3C C4C C5C C6C -1.3(6) . . . . ?
C11B C10B C9B N2B -2.3(4) . . . . ?
C11B C10B C9B C1B 171.4(3) . . . . ?
C11B C12B C13B C14B 0.4(6) . . . . ?
C3D C16D C15D C10D -179.9(3) . . . . ?
C3D C16D C15D C14D 0.1(5) . . . . ?
C3D C16D C7D C8D -177.9(3) . . . . ?
C3D C16D C7D C6D 1.8(5) . . . . ?
C3D C4D C5D C6D 2.8(6) . . . . ?
C12C C13C C14C C1C -179.2(3) . . . . ?
C12C C13C C14C C15C 0.1(5) . . . . ?
C4B C5B C6B C7B 0.0(6) . . . . ?
C13B C12B C11B C10B 179.2(4) . . . . ?
C13B C12B C11B C16B 1.4(5) . . . . ?
C4C C3C C16C C7C 2.0(5) . . . . ?
C4C C3C C16C C15C -178.5(3) . . . . ?
C4C C5C C6C C7C 2.2(6) . . . . ?
C4D C5D C6D C7D -1.9(6) . . . . ?
C14B C15B C16B N2B -177.4(3) . . . . ?
C14B C15B C16B C11B 0.8(5) . . . . ?
C15C C10C C11C C12C 0.9(5) . . . . ?
C15C C14C C1C O1C 176.2(3) . . . . ?
C15C C14C C1C C2C -4.7(5) . . . . ?
C16C C7C C8C O3C -173.3(4) . . . . ?
C16C C7C C8C C9C 7.0(5) . . . . ?
C16C C7C C6C C5C -0.9(6) . . . . ?
C16C C3C C4C C5C -0.8(6) . . . . ?
C5B C6B C7B C8B -0.6(6) . . . . ?
C16B N2B C9B C10B 1.1(4) . . . . ?
C16B N2B C9B C1B -169.1(5) . . . . ?
C16B C15B C14B C13B 1.0(6) . . . . ?
C18B C19B C20B C21B 1.6(6) . . . . ?
C18B C17B C22B C21B 1.9(5) . . . . ?
C6C C7C C8C O3C 5.4(6) . . . . ?
C6C C7C C8C C9C -174.4(3) . . . . ?
C6C C7C C16C C3C -1.2(5) . . . . ?
C6C C7C C16C C15C 179.3(3) . . . . ?
C20B C19B C18B C17B -2.2(5) . . . . ?
C20B C21B C22B C17B -2.5(5) . . . . ?
C6D C7D C8D O3D -4.6(5) . . . . ?
C6D C7D C8D C9D 174.9(3) . . . . ?
C22B C17B C18B C19B 0.4(5) . . . . ?
C22B C21B C20B C19B 0.7(5) . . . . ?
C7B C8B C3B C2B 179.5(3) . . . . ?
C7B C8B C3B C4B -1.4(5) . . . . ?
C14D C15D C10D C11D 0.7(5) . . . . ?
C14D C15D C10D C9D -178.6(3) . . . . ?
C14D C1D C2D O2D 175.7(3) . . . . ?
C14D C1D C2D C3D -3.8(5) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a Mylar Cryoloop'
_olex2_submission_original_sample_id (Octyl)/PhDIB-co-tetraone
_olex2_submission_special_instructions 'No special instructions were received'
