# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20160504a
_database_code_depnum_ccdc_archive 'CCDC 1877543'
loop_
_audit_author_name
_audit_author_address
'Haiyan Tian'
;Beijing Normal University
China
;
_audit_update_record             
;
2018-11-07 deposited with the CCDC.	2020-05-19 downloaded from the CCDC.
;
_audit_creation_date             2016-05-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H19 N3'
_chemical_formula_sum            'C28 H19 N3'
_chemical_formula_weight         397.46
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         c1h1n1
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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.12125(15)
_cell_length_b                   8.87819(17)
_cell_length_c                   29.0812(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2096.81(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5233
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.7890
_cell_measurement_theta_min      4.5670
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.582
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41k (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            7175
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.403
_diffrn_reflns_theta_min         5.209
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -94.00  -2.00   1.00    1.00    --  -41.49 125.00  90.00   92
  2  ω   -112.00 -20.00   1.00    1.00    --  -41.49 -37.00 150.00   92
  3  ω     94.00 167.00   1.00    1.00    --  107.19 125.00-150.00   73
  4  ω    102.00 163.00   1.00    1.00    --  107.19 125.00   0.00   61
  5  ω     83.00 169.00   1.00    1.00    --  107.19  30.00-180.00   86
  6  ω     45.00 108.00   1.00    1.00    --  107.19 -77.00 -90.00   63
  7  ω     32.00 129.00   1.00    1.00    --  107.19 -30.00-150.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0416460000
_diffrn_orient_matrix_UB_12      0.0295198000
_diffrn_orient_matrix_UB_13      0.0508681000
_diffrn_orient_matrix_UB_21      -0.0766152000
_diffrn_orient_matrix_UB_22      -0.1582828000
_diffrn_orient_matrix_UB_23      0.0036361000
_diffrn_orient_matrix_UB_31      0.1685553000
_diffrn_orient_matrix_UB_32      -0.0647520000
_diffrn_orient_matrix_UB_33      0.0142256000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                3931
_reflns_number_total             4071
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.38.41k (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41k (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41k (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1586 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4071
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.033
_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)+(0.0555P)²+0.0830P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.0987
_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:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25),
  C26(H26), C27(H27), C28(H28)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1344(3) 1.1497(2) 0.50304(7) 0.0404(5) Uani 1 1 d . . . . .
N2 N 0.3142(3) 1.0501(2) 0.63659(6) 0.0411(5) Uani 1 1 d . . . . .
N3 N 0.2493(2) 0.53989(17) 0.36703(5) 0.0235(4) Uani 1 1 d . . . . .
C1 C 0.1791(3) 1.0528(2) 0.52610(6) 0.0273(4) Uani 1 1 d . . . . .
C2 C 0.2775(3) 0.9977(2) 0.60177(7) 0.0285(5) Uani 1 1 d . . . . .
C3 C 0.2333(2) 0.9381(2) 0.55748(6) 0.0235(4) Uani 1 1 d . . . . .
C4 C 0.2458(2) 0.7879(2) 0.54724(6) 0.0208(4) Uani 1 1 d . . . . .
C5 C 0.2777(2) 0.6780(2) 0.58452(6) 0.0213(4) Uani 1 1 d . . . . .
C6 C 0.1945(2) 0.6867(2) 0.62668(6) 0.0245(4) Uani 1 1 d . . . . .
H6 H 0.1190 0.7638 0.6318 0.029 Uiso 1 1 calc R . . . .
C7 C 0.2239(3) 0.5812(3) 0.66080(7) 0.0311(5) Uani 1 1 d . . . . .
H7 H 0.1690 0.5881 0.6888 0.037 Uiso 1 1 calc R . . . .
C8 C 0.3356(3) 0.4649(3) 0.65332(7) 0.0333(5) Uani 1 1 d . . . . .
H8 H 0.3540 0.3934 0.6761 0.040 Uiso 1 1 calc R . . . .
C9 C 0.4194(3) 0.4554(3) 0.61190(7) 0.0315(5) Uani 1 1 d . . . . .
H9 H 0.4950 0.3785 0.6070 0.038 Uiso 1 1 calc R . . . .
C10 C 0.3902(3) 0.5607(2) 0.57780(6) 0.0257(4) Uani 1 1 d . . . . .
H10 H 0.4461 0.5533 0.5500 0.031 Uiso 1 1 calc R . . . .
C11 C 0.2340(2) 0.7286(2) 0.50024(6) 0.0202(4) Uani 1 1 d . . . . .
C12 C 0.2852(2) 0.8132(2) 0.46192(6) 0.0214(4) Uani 1 1 d . . . . .
H12 H 0.3194 0.9123 0.4660 0.026 Uiso 1 1 calc R . . . .
C13 C 0.2856(2) 0.7519(2) 0.41836(6) 0.0217(4) Uani 1 1 d . . . . .
H13 H 0.3184 0.8108 0.3935 0.026 Uiso 1 1 calc R . . . .
C14 C 0.2376(2) 0.6028(2) 0.41092(6) 0.0201(4) Uani 1 1 d . . . . .
C15 C 0.1818(2) 0.5180(2) 0.44859(6) 0.0227(4) Uani 1 1 d . . . . .
H15 H 0.1451 0.4198 0.4442 0.027 Uiso 1 1 calc R . . . .
C16 C 0.1813(2) 0.5800(2) 0.49204(6) 0.0220(4) Uani 1 1 d . . . . .
H16 H 0.1450 0.5220 0.5167 0.026 Uiso 1 1 calc R . . . .
C17 C 0.2463(2) 0.6351(2) 0.32721(6) 0.0214(4) Uani 1 1 d . . . . .
C18 C 0.1089(3) 0.7223(2) 0.31793(6) 0.0234(4) Uani 1 1 d . . . . .
H18 H 0.0208 0.7234 0.3384 0.028 Uiso 1 1 calc R . . . .
C19 C 0.1030(3) 0.8080(2) 0.27810(7) 0.0287(4) Uani 1 1 d . . . . .
H19 H 0.0107 0.8665 0.2719 0.034 Uiso 1 1 calc R . . . .
C20 C 0.2336(3) 0.8069(2) 0.24753(7) 0.0322(5) Uani 1 1 d . . . . .
H20 H 0.2289 0.8640 0.2208 0.039 Uiso 1 1 calc R . . . .
C21 C 0.3715(3) 0.7203(3) 0.25696(7) 0.0324(5) Uani 1 1 d . . . . .
H21 H 0.4597 0.7201 0.2366 0.039 Uiso 1 1 calc R . . . .
C22 C 0.3788(3) 0.6336(2) 0.29681(7) 0.0270(4) Uani 1 1 d . . . . .
H22 H 0.4712 0.5753 0.3031 0.032 Uiso 1 1 calc R . . . .
C23 C 0.2719(2) 0.3836(2) 0.35914(6) 0.0210(4) Uani 1 1 d . . . . .
C24 C 0.1961(3) 0.3175(2) 0.32106(6) 0.0245(4) Uani 1 1 d . . . . .
H24 H 0.1241 0.3737 0.3031 0.029 Uiso 1 1 calc R . . . .
C25 C 0.2276(3) 0.1691(2) 0.31006(7) 0.0249(4) Uani 1 1 d . . . . .
H25 H 0.1787 0.1267 0.2842 0.030 Uiso 1 1 calc R . . . .
C26 C 0.3314(3) 0.0824(2) 0.33713(7) 0.0259(4) Uani 1 1 d . . . . .
H26 H 0.3528 -0.0174 0.3295 0.031 Uiso 1 1 calc R . . . .
C27 C 0.4031(3) 0.1469(2) 0.37582(7) 0.0274(4) Uani 1 1 d . . . . .
H27 H 0.4709 0.0888 0.3946 0.033 Uiso 1 1 calc R . . . .
C28 C 0.3749(3) 0.2964(2) 0.38680(6) 0.0252(4) Uani 1 1 d . . . . .
H28 H 0.4244 0.3387 0.4126 0.030 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
N1 C1 1.149(3) . ?
N2 C2 1.153(3) . ?
N3 C14 1.397(2) . ?
N3 C17 1.434(2) . ?
N3 C23 1.419(2) . ?
C1 C3 1.437(3) . ?
C2 C3 1.438(3) . ?
C3 C4 1.371(3) . ?
C4 C5 1.481(3) . ?
C4 C11 1.468(2) . ?
C5 C6 1.402(3) . ?
C5 C10 1.399(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.386(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.391(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.386(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.383(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.407(3) . ?
C11 C16 1.407(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.379(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.397(3) . ?
C14 C15 1.404(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.378(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.385(3) . ?
C17 C22 1.392(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.386(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.384(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.385(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.393(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.397(3) . ?
C23 C28 1.394(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.380(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.386(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.390(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.385(3) . ?
C28 H28 0.9300 . ?

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
C14 N3 C17 120.07(15) . . ?
C14 N3 C23 123.24(15) . . ?
C23 N3 C17 116.63(14) . . ?
N1 C1 C3 176.2(2) . . ?
N2 C2 C3 177.7(2) . . ?
C1 C3 C2 112.64(17) . . ?
C4 C3 C1 125.06(17) . . ?
C4 C3 C2 122.30(18) . . ?
C3 C4 C5 119.65(16) . . ?
C3 C4 C11 123.12(17) . . ?
C11 C4 C5 117.20(17) . . ?
C6 C5 C4 121.27(18) . . ?
C10 C5 C4 120.14(16) . . ?
C10 C5 C6 118.57(18) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.17(19) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.0(2) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.9(2) . . ?
C10 C9 H9 120.1 . . ?
C5 C10 H10 119.5 . . ?
C9 C10 C5 120.97(19) . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C4 121.81(17) . . ?
C12 C11 C16 117.15(16) . . ?
C16 C11 C4 120.90(17) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.19(18) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 121.03(17) . . ?
C14 C13 H13 119.5 . . ?
N3 C14 C13 120.11(17) . . ?
N3 C14 C15 121.34(17) . . ?
C13 C14 C15 118.53(16) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.11(18) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 H16 119.0 . . ?
C15 C16 C11 121.93(17) . . ?
C15 C16 H16 119.0 . . ?
C18 C17 N3 120.03(17) . . ?
C18 C17 C22 120.29(18) . . ?
C22 C17 N3 119.60(18) . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.81(19) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.4(2) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C21 119.75(18) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.38(19) . . ?
C22 C21 H21 119.8 . . ?
C17 C22 H22 120.3 . . ?
C21 C22 C17 119.4(2) . . ?
C21 C22 H22 120.3 . . ?
C24 C23 N3 118.81(17) . . ?
C28 C23 N3 121.82(17) . . ?
C28 C23 C24 119.27(17) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.18(18) . . ?
C25 C24 H24 119.9 . . ?
C24 C25 H25 119.6 . . ?
C24 C25 C26 120.75(18) . . ?
C26 C25 H25 119.6 . . ?
C25 C26 H26 120.5 . . ?
C25 C26 C27 119.08(18) . . ?
C27 C26 H26 120.5 . . ?
C26 C27 H27 119.6 . . ?
C28 C27 C26 120.77(19) . . ?
C28 C27 H27 119.6 . . ?
C23 C28 H28 120.1 . . ?
C27 C28 C23 119.90(18) . . ?
C27 C28 H28 120.1 . . ?

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
N3 C14 C15 C16 175.90(17) . . . . ?
N3 C17 C18 C19 -176.53(17) . . . . ?
N3 C17 C22 C21 176.65(17) . . . . ?
N3 C23 C24 C25 174.11(18) . . . . ?
N3 C23 C28 C27 -175.15(19) . . . . ?
C1 C3 C4 C5 -170.30(19) . . . . ?
C1 C3 C4 C11 11.7(3) . . . . ?
C2 C3 C4 C5 10.8(3) . . . . ?
C2 C3 C4 C11 -167.20(18) . . . . ?
C3 C4 C5 C6 43.8(3) . . . . ?
C3 C4 C5 C10 -137.6(2) . . . . ?
C3 C4 C11 C12 30.4(3) . . . . ?
C3 C4 C11 C16 -154.0(2) . . . . ?
C4 C5 C6 C7 178.82(18) . . . . ?
C4 C5 C10 C9 -178.80(19) . . . . ?
C4 C11 C12 C13 174.83(18) . . . . ?
C4 C11 C16 C15 -174.71(18) . . . . ?
C5 C4 C11 C12 -147.69(19) . . . . ?
C5 C4 C11 C16 27.9(3) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C6 C5 C10 C9 -0.1(3) . . . . ?
C6 C7 C8 C9 0.9(3) . . . . ?
C7 C8 C9 C10 -0.8(3) . . . . ?
C8 C9 C10 C5 0.5(3) . . . . ?
C10 C5 C6 C7 0.2(3) . . . . ?
C11 C4 C5 C6 -138.05(19) . . . . ?
C11 C4 C5 C10 40.6(3) . . . . ?
C11 C12 C13 C14 -1.0(3) . . . . ?
C12 C11 C16 C15 1.0(3) . . . . ?
C12 C13 C14 N3 -175.74(18) . . . . ?
C12 C13 C14 C15 2.7(3) . . . . ?
C13 C14 C15 C16 -2.5(3) . . . . ?
C14 N3 C17 C18 -62.1(3) . . . . ?
C14 N3 C17 C22 121.1(2) . . . . ?
C14 N3 C23 C24 144.78(19) . . . . ?
C14 N3 C23 C28 -38.9(3) . . . . ?
C14 C15 C16 C11 0.7(3) . . . . ?
C16 C11 C12 C13 -0.9(3) . . . . ?
C17 N3 C14 C13 -24.7(3) . . . . ?
C17 N3 C14 C15 156.91(18) . . . . ?
C17 N3 C23 C24 -38.1(3) . . . . ?
C17 N3 C23 C28 138.25(19) . . . . ?
C17 C18 C19 C20 0.0(3) . . . . ?
C18 C17 C22 C21 -0.2(3) . . . . ?
C18 C19 C20 C21 -0.4(3) . . . . ?
C19 C20 C21 C22 0.5(3) . . . . ?
C20 C21 C22 C17 -0.2(3) . . . . ?
C22 C17 C18 C19 0.3(3) . . . . ?
C23 N3 C14 C13 152.35(19) . . . . ?
C23 N3 C14 C15 -26.1(3) . . . . ?
C23 N3 C17 C18 120.7(2) . . . . ?
C23 N3 C17 C22 -56.1(2) . . . . ?
C23 C24 C25 C26 1.6(3) . . . . ?
C24 C23 C28 C27 1.2(3) . . . . ?
C24 C25 C26 C27 0.3(3) . . . . ?
C25 C26 C27 C28 -1.5(3) . . . . ?
C26 C27 C28 C23 0.7(3) . . . . ?
C28 C23 C24 C25 -2.3(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.725
_oxdiff_exptl_absorpt_empirical_full_min 0.659
####################################################################### 
# 
# 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_20160504b
_database_code_depnum_ccdc_archive 'CCDC 1877544'
loop_
_audit_author_name
_audit_author_address
'Haiyan Tian'
;Beijing Normal University
China
;
_audit_update_record             
;
2018-11-07 deposited with the CCDC.	2020-05-19 downloaded from the CCDC.
;
_audit_creation_date             2016-05-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C28 H19 N3)'
_chemical_formula_sum            'C56 H38 N6'
_chemical_formula_weight         794.92
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         c1h1n1
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'

_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                   28.5615(4)
_cell_length_b                   8.12800(10)
_cell_length_c                   17.5584(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4076.15(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13246
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.0200
_cell_measurement_theta_min      5.0490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41k (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            31408
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.734
_diffrn_reflns_theta_min         3.990
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -55.00  33.00   1.00    1.00    --  -41.49  37.00 -30.00   88
  2  ω     79.00 107.00   1.00    1.00    --   41.49  37.00   0.00   28
  3  ω    116.00 167.00   1.00    1.00    --  107.19  85.00-115.00   51
  4  ω    142.00 175.00   1.00    1.00    --  107.19  77.00 -90.00   33
  5  ω    140.00 172.00   1.00    1.00    --  107.19  77.00-180.00   32
  6  ω     82.00 107.00   1.00    1.00    --  107.19  45.00 -90.00   25
  7  ω     82.00 152.00   1.00    1.00    --  107.19  30.00 -60.00   70
  8  ω    139.00 174.00   1.00    1.00    --  107.19  45.00  60.00   35
  9  ω    124.00 162.00   1.00    1.00    --  107.19 125.00 150.00   38
 10  ω     99.00 129.00   1.00    1.00    --  107.19  45.00  60.00   30
 11  ω    100.00 177.00   1.00    1.00    --  107.19 125.00   0.00   77
 12  ω     78.00 105.00   1.00    1.00    --  107.19  61.00-150.00   27
 13  ω     78.00 104.00   1.00    1.00    --  107.19  61.00-120.00   26
 14  ω     76.00 101.00   1.00    1.00    --  107.19  77.00-150.00   25
 15  ω     75.00 101.00   1.00    1.00    --  107.19  77.00-180.00   26
 16  ω     81.00 108.00   1.00    1.00    --  107.19  45.00-120.00   27
 17  ω     39.00 132.00   1.00    1.00    --  107.19 -45.00-120.00   93
 18  ω     64.00 140.00   1.00    1.00    --  107.19 -77.00 -90.00   76
 19  ω     36.00  66.00   1.00    1.00    --   41.49 -99.00 -30.00   30
 20  ω     25.00 107.00   1.00    1.00    --  107.19 -94.00  90.00   82
 21  ω     45.00  95.00   1.00    1.00    --   41.49-125.00 150.00   50
 22  ω     19.00 168.00   1.00    1.00    --  107.19   0.00-120.00  149
 23  ω    -65.00 -38.00   1.00    1.00    --  -41.49 -37.00-150.00   27
 24  ω   -115.00 -23.00   1.00    1.00    --  -41.49 -57.00-180.00   92
 25  ω    -65.00  32.00   1.00    1.00    --  -41.49  37.00 120.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0638612000
_diffrn_orient_matrix_UB_12      -0.0477714000
_diffrn_orient_matrix_UB_13      0.0281006000
_diffrn_orient_matrix_UB_21      -0.1476008000
_diffrn_orient_matrix_UB_22      -0.0038292000
_diffrn_orient_matrix_UB_23      0.0546441000
_diffrn_orient_matrix_UB_31      -0.1001424000
_diffrn_orient_matrix_UB_32      -0.0247830000
_diffrn_orient_matrix_UB_33      -0.0626513000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.919
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                7686
_reflns_number_total             8064
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.38.41k (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41k (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41k (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 
;
 Flack x determined using 3448 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         8064
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0371
_refine_ls_restrained_S_all      1.040
_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)+(0.0492P)²+0.2838P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0949
_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:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25),
  C26(H26), C27(H27), C28(H28), C34(H34), C35(H35), C36(H36), C37(H37),
 C38(H38), C40(H40), C41(H41), C43(H43), C44(H44), C46(H46), C47(H47), C48(H48),
  C49(H49), C50(H50), C52(H52), C53(H53), C54(H54), C55(H55), C56(H56)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.79277(8) 0.6054(3) 0.52216(15) 0.0388(6) Uani 1 1 d . . . . .
N2 N 0.67584(8) 0.3620(3) 0.63170(12) 0.0290(5) Uani 1 1 d . . . . .
N3 N 0.48329(7) 0.4287(3) 0.45791(12) 0.0236(4) Uani 1 1 d . . . . .
C1 C 0.75514(9) 0.5572(3) 0.51466(15) 0.0262(5) Uani 1 1 d . . . . .
C2 C 0.68947(8) 0.4267(3) 0.57784(13) 0.0226(5) Uani 1 1 d . . . . .
C3 C 0.70744(8) 0.5014(3) 0.50970(14) 0.0210(5) Uani 1 1 d . . . . .
C4 C 0.68069(8) 0.5172(3) 0.44485(13) 0.0191(4) Uani 1 1 d . . . . .
C5 C 0.70298(8) 0.5559(3) 0.37095(13) 0.0197(5) Uani 1 1 d . . . . .
C6 C 0.74492(8) 0.4790(3) 0.35040(14) 0.0216(5) Uani 1 1 d . . . . .
H6 H 0.7595 0.4076 0.3843 0.026 Uiso 1 1 calc R . . . .
C7 C 0.76488(9) 0.5086(3) 0.27967(14) 0.0248(5) Uani 1 1 d . . . . .
H7 H 0.7929 0.4575 0.2665 0.030 Uiso 1 1 calc R . . . .
C8 C 0.74327(9) 0.6137(3) 0.22888(15) 0.0270(5) Uani 1 1 d . . . . .
H8 H 0.7565 0.6319 0.1812 0.032 Uiso 1 1 calc R . . . .
C9 C 0.70181(9) 0.6925(3) 0.24886(15) 0.0296(5) Uani 1 1 d . . . . .
H9 H 0.6876 0.7648 0.2149 0.035 Uiso 1 1 calc R . . . .
C10 C 0.68163(8) 0.6633(3) 0.31937(14) 0.0243(5) Uani 1 1 d . . . . .
H10 H 0.6538 0.7154 0.3324 0.029 Uiso 1 1 calc R . . . .
C11 C 0.62999(8) 0.4920(3) 0.44741(13) 0.0181(4) Uani 1 1 d . . . . .
C12 C 0.60549(8) 0.4210(3) 0.38633(13) 0.0198(5) Uani 1 1 d . . . . .
H12 H 0.6218 0.3899 0.3428 0.024 Uiso 1 1 calc R . . . .
C13 C 0.55766(8) 0.3966(3) 0.38964(13) 0.0208(5) Uani 1 1 d . . . . .
H13 H 0.5424 0.3469 0.3489 0.025 Uiso 1 1 calc R . . . .
C14 C 0.53161(8) 0.4462(3) 0.45404(14) 0.0196(5) Uani 1 1 d . . . . .
C15 C 0.55637(8) 0.5161(3) 0.51518(13) 0.0203(5) Uani 1 1 d . . . . .
H15 H 0.5402 0.5472 0.5589 0.024 Uiso 1 1 calc R . . . .
C16 C 0.60388(8) 0.5393(3) 0.51157(13) 0.0191(4) Uani 1 1 d . . . . .
H16 H 0.6192 0.5876 0.5526 0.023 Uiso 1 1 calc R . . . .
C17 C 0.45470(8) 0.4245(3) 0.39090(13) 0.0207(5) Uani 1 1 d . . . . .
C18 C 0.46443(8) 0.5244(3) 0.32847(14) 0.0231(5) Uani 1 1 d . . . . .
H18 H 0.4899 0.5957 0.3298 0.028 Uiso 1 1 calc R . . . .
C19 C 0.43617(9) 0.5177(3) 0.26406(15) 0.0269(5) Uani 1 1 d . . . . .
H19 H 0.4433 0.5817 0.2217 0.032 Uiso 1 1 calc R . . . .
C20 C 0.39716(9) 0.4150(3) 0.26297(15) 0.0283(5) Uani 1 1 d . . . . .
H20 H 0.3779 0.4116 0.2203 0.034 Uiso 1 1 calc R . . . .
C21 C 0.38721(9) 0.3185(3) 0.32531(16) 0.0309(6) Uani 1 1 d . . . . .
H21 H 0.3610 0.2507 0.3247 0.037 Uiso 1 1 calc R . . . .
C22 C 0.41585(8) 0.3211(3) 0.38901(15) 0.0262(5) Uani 1 1 d . . . . .
H22 H 0.4091 0.2538 0.4304 0.031 Uiso 1 1 calc R . . . .
C23 C 0.46033(8) 0.4331(3) 0.53059(13) 0.0206(5) Uani 1 1 d . . . . .
C24 C 0.42408(9) 0.5437(3) 0.54329(16) 0.0281(5) Uani 1 1 d . . . . .
H24 H 0.4147 0.6155 0.5050 0.034 Uiso 1 1 calc R . . . .
C25 C 0.40207(10) 0.5461(4) 0.61391(17) 0.0368(7) Uani 1 1 d . . . . .
H25 H 0.3772 0.6175 0.6223 0.044 Uiso 1 1 calc R . . . .
C26 C 0.41688(10) 0.4431(4) 0.67191(16) 0.0368(7) Uani 1 1 d . . . . .
H26 H 0.4023 0.4465 0.7193 0.044 Uiso 1 1 calc R . . . .
C27 C 0.45349(10) 0.3348(3) 0.65902(14) 0.0320(6) Uani 1 1 d . . . . .
H27 H 0.4637 0.2662 0.6980 0.038 Uiso 1 1 calc R . . . .
C28 C 0.47499(9) 0.3281(3) 0.58825(14) 0.0259(5) Uani 1 1 d . . . . .
H28 H 0.4991 0.2537 0.5795 0.031 Uiso 1 1 calc R . . . .
N4 N 0.45430(8) -0.0470(3) 0.47672(14) 0.0345(5) Uani 1 1 d . . . . .
N5 N 0.57450(7) -0.1516(3) 0.34937(12) 0.0294(5) Uani 1 1 d . . . . .
N6 N 0.76967(7) 0.0419(3) 0.52584(11) 0.0218(4) Uani 1 1 d . . . . .
C29 C 0.49432(8) -0.0570(3) 0.48232(14) 0.0226(5) Uani 1 1 d . . . . .
C30 C 0.56316(8) -0.1113(3) 0.40945(14) 0.0227(5) Uani 1 1 d . . . . .
C31 C 0.54462(8) -0.0678(3) 0.48282(13) 0.0201(5) Uani 1 1 d . . . . .
C32 C 0.57184(8) -0.0471(3) 0.54684(14) 0.0193(5) Uani 1 1 d . . . . .
C33 C 0.55030(8) -0.0474(3) 0.62354(13) 0.0192(5) Uani 1 1 d . . . . .
C34 C 0.51263(8) -0.1521(3) 0.64028(14) 0.0211(5) Uani 1 1 d . . . . .
H34 H 0.4996 -0.2166 0.6020 0.025 Uiso 1 1 calc R . . . .
C35 C 0.49479(8) -0.1599(3) 0.71342(14) 0.0242(5) Uani 1 1 d . . . . .
H35 H 0.4698 -0.2294 0.7240 0.029 Uiso 1 1 calc R . . . .
C36 C 0.51394(9) -0.0651(3) 0.77090(14) 0.0260(5) Uani 1 1 d . . . . .
H36 H 0.5023 -0.0731 0.8203 0.031 Uiso 1 1 calc R . . . .
C37 C 0.55045(9) 0.0420(3) 0.75494(14) 0.0264(5) Uani 1 1 d . . . . .
H37 H 0.5628 0.1077 0.7934 0.032 Uiso 1 1 calc R . . . .
C38 C 0.56850(8) 0.0513(3) 0.68178(14) 0.0228(5) Uani 1 1 d . . . . .
H38 H 0.5929 0.1236 0.6713 0.027 Uiso 1 1 calc R . . . .
C39 C 0.62286(8) -0.0286(3) 0.54113(13) 0.0193(4) Uani 1 1 d . . . . .
C40 C 0.65343(8) -0.0882(3) 0.59743(13) 0.0195(5) Uani 1 1 d . . . . .
H40 H 0.6411 -0.1429 0.6394 0.023 Uiso 1 1 calc R . . . .
C41 C 0.70135(8) -0.0677(3) 0.59218(13) 0.0198(4) Uani 1 1 d . . . . .
H41 H 0.7206 -0.1102 0.6301 0.024 Uiso 1 1 calc R . . . .
C42 C 0.72137(8) 0.0166(3) 0.53036(13) 0.0186(4) Uani 1 1 d . . . . .
C43 C 0.69102(8) 0.0770(3) 0.47370(13) 0.0208(5) Uani 1 1 d . . . . .
H43 H 0.7033 0.1327 0.4320 0.025 Uiso 1 1 calc R . . . .
C44 C 0.64334(8) 0.0546(3) 0.47929(13) 0.0201(5) Uani 1 1 d . . . . .
H44 H 0.6241 0.0957 0.4410 0.024 Uiso 1 1 calc R . . . .
C45 C 0.79129(8) 0.0730(3) 0.45343(13) 0.0210(5) Uani 1 1 d . . . . .
C46 C 0.77950(9) -0.0213(3) 0.39039(15) 0.0265(5) Uani 1 1 d . . . . .
H46 H 0.7589 -0.1092 0.3954 0.032 Uiso 1 1 calc R . . . .
C47 C 0.79873(10) 0.0164(3) 0.31963(15) 0.0315(6) Uani 1 1 d . . . . .
H47 H 0.7899 -0.0438 0.2769 0.038 Uiso 1 1 calc R . . . .
C48 C 0.83102(9) 0.1434(4) 0.31235(16) 0.0340(6) Uani 1 1 d . . . . .
H48 H 0.8437 0.1687 0.2650 0.041 Uiso 1 1 calc R . . . .
C49 C 0.84419(8) 0.2323(3) 0.37637(15) 0.0309(6) Uani 1 1 d . . . . .
H49 H 0.8666 0.3148 0.3721 0.037 Uiso 1 1 calc R . . . .
C50 C 0.82412(8) 0.1988(3) 0.44663(14) 0.0250(5) Uani 1 1 d . . . . .
H50 H 0.8326 0.2603 0.4891 0.030 Uiso 1 1 calc R . . . .
C51 C 0.79841(8) 0.0529(3) 0.59251(13) 0.0200(5) Uani 1 1 d . . . . .
C52 C 0.84314(8) -0.0169(3) 0.59163(15) 0.0242(5) Uani 1 1 d . . . . .
H52 H 0.8533 -0.0758 0.5493 0.029 Uiso 1 1 calc R . . . .
C53 C 0.87228(9) 0.0023(3) 0.65412(16) 0.0268(5) Uani 1 1 d . . . . .
H53 H 0.9023 -0.0416 0.6530 0.032 Uiso 1 1 calc R . . . .
C54 C 0.85708(9) 0.0864(3) 0.71841(15) 0.0271(5) Uani 1 1 d . . . . .
H54 H 0.8767 0.0974 0.7604 0.033 Uiso 1 1 calc R . . . .
C55 C 0.81247(9) 0.1540(3) 0.71964(15) 0.0277(5) Uani 1 1 d . . . . .
H55 H 0.8020 0.2089 0.7628 0.033 Uiso 1 1 calc R . . . .
C56 C 0.78337(8) 0.1397(3) 0.65642(14) 0.0241(5) Uani 1 1 d . . . . .
H56 H 0.7539 0.1881 0.6568 0.029 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
N1 C1 1.151(3) . ?
N2 C2 1.150(3) . ?
N3 C14 1.389(3) . ?
N3 C17 1.433(3) . ?
N3 C23 1.435(3) . ?
C1 C3 1.438(3) . ?
C2 C3 1.437(3) . ?
C3 C4 1.377(3) . ?
C4 C5 1.479(3) . ?
C4 C11 1.463(3) . ?
C5 C6 1.398(3) . ?
C5 C10 1.398(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.387(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.381(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.391(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.386(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.404(3) . ?
C11 C16 1.405(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.382(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.412(3) . ?
C14 C15 1.406(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.371(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.392(3) . ?
C17 C22 1.392(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.391(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.392(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.376(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.386(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.390(3) . ?
C23 C28 1.388(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.390(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.385(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.385(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.387(4) . ?
C28 H28 0.9300 . ?
N4 C29 1.150(3) . ?
N5 C30 1.151(3) . ?
N6 C42 1.397(3) . ?
N6 C45 1.436(3) . ?
N6 C51 1.433(3) . ?
C29 C31 1.439(3) . ?
C30 C31 1.437(3) . ?
C31 C32 1.377(3) . ?
C32 C33 1.481(3) . ?
C32 C39 1.468(3) . ?
C33 C34 1.403(3) . ?
C33 C38 1.400(3) . ?
C34 H34 0.9300 . ?
C34 C35 1.383(3) . ?
C35 H35 0.9300 . ?
C35 C36 1.383(4) . ?
C36 H36 0.9300 . ?
C36 C37 1.387(4) . ?
C37 H37 0.9300 . ?
C37 C38 1.386(3) . ?
C38 H38 0.9300 . ?
C39 C40 1.405(3) . ?
C39 C44 1.406(3) . ?
C40 H40 0.9300 . ?
C40 C41 1.382(3) . ?
C41 H41 0.9300 . ?
C41 C42 1.405(3) . ?
C42 C43 1.408(3) . ?
C43 H43 0.9300 . ?
C43 C44 1.377(3) . ?
C44 H44 0.9300 . ?
C45 C46 1.388(4) . ?
C45 C50 1.393(3) . ?
C46 H46 0.9300 . ?
C46 C47 1.393(4) . ?
C47 H47 0.9300 . ?
C47 C48 1.390(4) . ?
C48 H48 0.9300 . ?
C48 C49 1.388(4) . ?
C49 H49 0.9300 . ?
C49 C50 1.387(3) . ?
C50 H50 0.9300 . ?
C51 C52 1.398(3) . ?
C51 C56 1.393(3) . ?
C52 H52 0.9300 . ?
C52 C53 1.386(4) . ?
C53 H53 0.9300 . ?
C53 C54 1.389(4) . ?
C54 H54 0.9300 . ?
C54 C55 1.387(4) . ?
C55 H55 0.9300 . ?
C55 C56 1.392(3) . ?
C56 H56 0.9300 . ?

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
C14 N3 C17 121.9(2) . . ?
C14 N3 C23 119.7(2) . . ?
C17 N3 C23 118.06(18) . . ?
N1 C1 C3 176.5(3) . . ?
N2 C2 C3 177.7(3) . . ?
C2 C3 C1 114.9(2) . . ?
C4 C3 C1 123.1(2) . . ?
C4 C3 C2 122.0(2) . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 C11 120.7(2) . . ?
C11 C4 C5 118.9(2) . . ?
C6 C5 C4 120.0(2) . . ?
C10 C5 C4 120.9(2) . . ?
C10 C5 C6 119.1(2) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.1(2) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.2(2) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H9 120.0 . . ?
C5 C10 H10 119.9 . . ?
C9 C10 C5 120.3(2) . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C4 121.8(2) . . ?
C12 C11 C16 117.4(2) . . ?
C16 C11 C4 120.8(2) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.3(2) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 120.9(2) . . ?
C14 C13 H13 119.5 . . ?
N3 C14 C13 122.2(2) . . ?
N3 C14 C15 120.3(2) . . ?
C15 C14 C13 117.5(2) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.2(2) . . ?
C16 C15 H15 119.4 . . ?
C11 C16 H16 119.2 . . ?
C15 C16 C11 121.6(2) . . ?
C15 C16 H16 119.2 . . ?
C18 C17 N3 121.2(2) . . ?
C18 C17 C22 119.5(2) . . ?
C22 C17 N3 119.2(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.1(2) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.0(2) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.7(2) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 119.6 . . ?
C20 C21 C22 120.8(2) . . ?
C22 C21 H21 119.6 . . ?
C17 C22 H22 120.0 . . ?
C21 C22 C17 119.9(2) . . ?
C21 C22 H22 120.0 . . ?
C24 C23 N3 119.9(2) . . ?
C28 C23 N3 119.7(2) . . ?
C28 C23 C24 120.4(2) . . ?
C23 C24 H24 120.4 . . ?
C23 C24 C25 119.3(3) . . ?
C25 C24 H24 120.4 . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.6(3) . . ?
C26 C25 H25 119.7 . . ?
C25 C26 H26 120.2 . . ?
C25 C26 C27 119.6(2) . . ?
C27 C26 H26 120.2 . . ?
C26 C27 H27 119.8 . . ?
C26 C27 C28 120.4(3) . . ?
C28 C27 H27 119.8 . . ?
C23 C28 H28 120.1 . . ?
C27 C28 C23 119.7(2) . . ?
C27 C28 H28 120.1 . . ?
C42 N6 C45 120.06(19) . . ?
C42 N6 C51 121.91(19) . . ?
C51 N6 C45 117.79(18) . . ?
N4 C29 C31 175.4(3) . . ?
N5 C30 C31 174.4(3) . . ?
C30 C31 C29 112.2(2) . . ?
C32 C31 C29 124.1(2) . . ?
C32 C31 C30 123.6(2) . . ?
C31 C32 C33 120.5(2) . . ?
C31 C32 C39 121.1(2) . . ?
C39 C32 C33 118.3(2) . . ?
C34 C33 C32 120.7(2) . . ?
C38 C33 C32 120.6(2) . . ?
C38 C33 C34 118.7(2) . . ?
C33 C34 H34 119.8 . . ?
C35 C34 C33 120.3(2) . . ?
C35 C34 H34 119.8 . . ?
C34 C35 H35 119.8 . . ?
C36 C35 C34 120.4(2) . . ?
C36 C35 H35 119.8 . . ?
C35 C36 H36 120.0 . . ?
C35 C36 C37 120.0(2) . . ?
C37 C36 H36 120.0 . . ?
C36 C37 H37 120.0 . . ?
C38 C37 C36 120.1(2) . . ?
C38 C37 H37 120.0 . . ?
C33 C38 H38 119.7 . . ?
C37 C38 C33 120.5(2) . . ?
C37 C38 H38 119.7 . . ?
C40 C39 C32 122.2(2) . . ?
C40 C39 C44 116.8(2) . . ?
C44 C39 C32 121.0(2) . . ?
C39 C40 H40 119.1 . . ?
C41 C40 C39 121.8(2) . . ?
C41 C40 H40 119.1 . . ?
C40 C41 H41 119.6 . . ?
C40 C41 C42 120.9(2) . . ?
C42 C41 H41 119.6 . . ?
N6 C42 C41 121.2(2) . . ?
N6 C42 C43 121.1(2) . . ?
C41 C42 C43 117.7(2) . . ?
C42 C43 H43 119.6 . . ?
C44 C43 C42 120.8(2) . . ?
C44 C43 H43 119.6 . . ?
C39 C44 H44 119.0 . . ?
C43 C44 C39 122.0(2) . . ?
C43 C44 H44 119.0 . . ?
C46 C45 N6 120.3(2) . . ?
C46 C45 C50 120.0(2) . . ?
C50 C45 N6 119.6(2) . . ?
C45 C46 H46 120.2 . . ?
C45 C46 C47 119.6(2) . . ?
C47 C46 H46 120.2 . . ?
C46 C47 H47 119.8 . . ?
C48 C47 C46 120.5(3) . . ?
C48 C47 H47 119.8 . . ?
C47 C48 H48 120.3 . . ?
C49 C48 C47 119.5(2) . . ?
C49 C48 H48 120.3 . . ?
C48 C49 H49 119.8 . . ?
C50 C49 C48 120.4(2) . . ?
C50 C49 H49 119.8 . . ?
C45 C50 H50 120.0 . . ?
C49 C50 C45 119.9(2) . . ?
C49 C50 H50 120.0 . . ?
C52 C51 N6 119.3(2) . . ?
C56 C51 N6 120.9(2) . . ?
C56 C51 C52 119.7(2) . . ?
C51 C52 H52 120.2 . . ?
C53 C52 C51 119.6(2) . . ?
C53 C52 H52 120.2 . . ?
C52 C53 H53 119.6 . . ?
C52 C53 C54 120.7(2) . . ?
C54 C53 H53 119.6 . . ?
C53 C54 H54 120.2 . . ?
C55 C54 C53 119.6(2) . . ?
C55 C54 H54 120.2 . . ?
C54 C55 H55 119.9 . . ?
C54 C55 C56 120.2(2) . . ?
C56 C55 H55 119.9 . . ?
C51 C56 H56 120.0 . . ?
C55 C56 C51 120.0(2) . . ?
C55 C56 H56 120.0 . . ?

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
N3 C14 C15 C16 -177.9(2) . . . . ?
N3 C17 C18 C19 179.9(2) . . . . ?
N3 C17 C22 C21 178.5(2) . . . . ?
N3 C23 C24 C25 179.8(2) . . . . ?
N3 C23 C28 C27 178.6(2) . . . . ?
C1 C3 C4 C5 15.0(4) . . . . ?
C1 C3 C4 C11 -166.6(2) . . . . ?
C2 C3 C4 C5 -164.8(2) . . . . ?
C2 C3 C4 C11 13.6(3) . . . . ?
C3 C4 C5 C6 41.8(3) . . . . ?
C3 C4 C5 C10 -141.1(2) . . . . ?
C3 C4 C11 C12 -145.2(2) . . . . ?
C3 C4 C11 C16 35.2(3) . . . . ?
C4 C5 C6 C7 176.9(2) . . . . ?
C4 C5 C10 C9 -177.0(2) . . . . ?
C4 C11 C12 C13 179.5(2) . . . . ?
C4 C11 C16 C15 -179.7(2) . . . . ?
C5 C4 C11 C12 33.2(3) . . . . ?
C5 C4 C11 C16 -146.4(2) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C6 C5 C10 C9 0.2(4) . . . . ?
C6 C7 C8 C9 1.1(4) . . . . ?
C7 C8 C9 C10 -1.2(4) . . . . ?
C8 C9 C10 C5 0.5(4) . . . . ?
C10 C5 C6 C7 -0.3(3) . . . . ?
C11 C4 C5 C6 -136.6(2) . . . . ?
C11 C4 C5 C10 40.5(3) . . . . ?
C11 C12 C13 C14 1.6(3) . . . . ?
C12 C11 C16 C15 0.6(3) . . . . ?
C12 C13 C14 N3 177.6(2) . . . . ?
C12 C13 C14 C15 -1.9(3) . . . . ?
C13 C14 C15 C16 1.7(3) . . . . ?
C14 N3 C17 C18 -38.1(3) . . . . ?
C14 N3 C17 C22 143.3(2) . . . . ?
C14 N3 C23 C24 125.3(2) . . . . ?
C14 N3 C23 C28 -53.7(3) . . . . ?
C14 C15 C16 C11 -1.1(3) . . . . ?
C16 C11 C12 C13 -0.9(3) . . . . ?
C17 N3 C14 C13 -25.9(3) . . . . ?
C17 N3 C14 C15 153.7(2) . . . . ?
C17 N3 C23 C24 -48.0(3) . . . . ?
C17 N3 C23 C28 133.0(2) . . . . ?
C17 C18 C19 C20 2.2(4) . . . . ?
C18 C17 C22 C21 -0.1(4) . . . . ?
C18 C19 C20 C21 -1.1(4) . . . . ?
C19 C20 C21 C22 -0.6(4) . . . . ?
C20 C21 C22 C17 1.2(4) . . . . ?
C22 C17 C18 C19 -1.6(4) . . . . ?
C23 N3 C14 C13 161.2(2) . . . . ?
C23 N3 C14 C15 -19.3(3) . . . . ?
C23 N3 C17 C18 134.9(2) . . . . ?
C23 N3 C17 C22 -43.6(3) . . . . ?
C23 C24 C25 C26 2.0(4) . . . . ?
C24 C23 C28 C27 -0.4(4) . . . . ?
C24 C25 C26 C27 -1.1(4) . . . . ?
C25 C26 C27 C28 -0.6(4) . . . . ?
C26 C27 C28 C23 1.3(4) . . . . ?
C28 C23 C24 C25 -1.2(4) . . . . ?
N6 C42 C43 C44 -178.6(2) . . . . ?
N6 C45 C46 C47 176.3(2) . . . . ?
N6 C45 C50 C49 -178.2(2) . . . . ?
N6 C51 C52 C53 175.9(2) . . . . ?
N6 C51 C56 C55 -177.7(2) . . . . ?
C29 C31 C32 C33 13.3(3) . . . . ?
C29 C31 C32 C39 -168.3(2) . . . . ?
C30 C31 C32 C33 -163.3(2) . . . . ?
C30 C31 C32 C39 15.1(3) . . . . ?
C31 C32 C33 C34 36.6(3) . . . . ?
C31 C32 C33 C38 -146.4(2) . . . . ?
C31 C32 C39 C40 -147.0(2) . . . . ?
C31 C32 C39 C44 34.8(3) . . . . ?
C32 C33 C34 C35 175.5(2) . . . . ?
C32 C33 C38 C37 -175.3(2) . . . . ?
C32 C39 C40 C41 -178.9(2) . . . . ?
C32 C39 C44 C43 178.4(2) . . . . ?
C33 C32 C39 C40 31.4(3) . . . . ?
C33 C32 C39 C44 -146.8(2) . . . . ?
C33 C34 C35 C36 -0.2(4) . . . . ?
C34 C33 C38 C37 1.8(3) . . . . ?
C34 C35 C36 C37 1.8(4) . . . . ?
C35 C36 C37 C38 -1.5(4) . . . . ?
C36 C37 C38 C33 -0.3(4) . . . . ?
C38 C33 C34 C35 -1.5(3) . . . . ?
C39 C32 C33 C34 -141.8(2) . . . . ?
C39 C32 C33 C38 35.2(3) . . . . ?
C39 C40 C41 C42 1.0(3) . . . . ?
C40 C39 C44 C43 0.0(3) . . . . ?
C40 C41 C42 N6 178.1(2) . . . . ?
C40 C41 C42 C43 -0.9(3) . . . . ?
C41 C42 C43 C44 0.4(3) . . . . ?
C42 N6 C45 C46 -45.0(3) . . . . ?
C42 N6 C45 C50 134.8(2) . . . . ?
C42 N6 C51 C52 142.2(2) . . . . ?
C42 N6 C51 C56 -41.4(3) . . . . ?
C42 C43 C44 C39 0.0(4) . . . . ?
C44 C39 C40 C41 -0.6(3) . . . . ?
C45 N6 C42 C41 157.8(2) . . . . ?
C45 N6 C42 C43 -23.2(3) . . . . ?
C45 N6 C51 C52 -43.5(3) . . . . ?
C45 N6 C51 C56 133.0(2) . . . . ?
C45 C46 C47 C48 2.6(4) . . . . ?
C46 C45 C50 C49 1.5(4) . . . . ?
C46 C47 C48 C49 0.3(4) . . . . ?
C47 C48 C49 C50 -2.3(4) . . . . ?
C48 C49 C50 C45 1.4(4) . . . . ?
C50 C45 C46 C47 -3.5(4) . . . . ?
C51 N6 C42 C41 -28.0(3) . . . . ?
C51 N6 C42 C43 151.0(2) . . . . ?
C51 N6 C45 C46 140.6(2) . . . . ?
C51 N6 C45 C50 -39.6(3) . . . . ?
C51 C52 C53 C54 1.7(4) . . . . ?
C52 C51 C56 C55 -1.2(4) . . . . ?
C52 C53 C54 C55 -0.9(4) . . . . ?
C53 C54 C55 C56 -1.0(4) . . . . ?
C54 C55 C56 C51 2.0(4) . . . . ?
C56 C51 C52 C53 -0.6(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.710
_oxdiff_exptl_absorpt_empirical_full_min 0.607
