# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_191024_s4_zh
_audit_block_doi                 10.5517/ccdc.csd.cc244tfk
_database_code_depnum_ccdc_archive 'CCDC 1970838'
loop_
_audit_author_name
_audit_author_address
'hua zhang'
;Chinese Academy of Sciences University
China
;
_audit_update_record             
;
2019-12-09 deposited with the CCDC.	2020-04-23 downloaded from the CCDC.
;
_audit_creation_date             2019-10-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C36 H30 N2'
_chemical_formula_sum            'C36 H30 N2'
_chemical_formula_weight         490.62
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+3/4, x+1/4, z+1/4'
'-x, -y+1/2, z'
'y+1/4, -x+1/4, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'y+3/4, -x+3/4, z+3/4'
'-x, -y, -z'
'y-3/4, -x-1/4, -z-1/4'
'x, y-1/2, -z'
'-y-1/4, x-1/4, -z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'x+1/2, y, -z+1/2'
'-y+1/4, x+1/4, -z+1/4'

_cell_length_a                   20.2031(8)
_cell_length_b                   20.2031(8)
_cell_length_c                   13.2367(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5402.8(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1428
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4050
_cell_measurement_theta_min      3.3680
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92375
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7894
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.393
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -17.00   24.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -99.0000  -90.0000 41

#__ type_ start__ end____ width___ exp.time_
  2 omega  -62.00  -36.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106 -178.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega    1.00   77.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       16.8419   77.0000   30.0000 76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0260552000
_diffrn_orient_matrix_UB_12      0.0216052000
_diffrn_orient_matrix_UB_13      -0.0142523000
_diffrn_orient_matrix_UB_21      -0.0225544000
_diffrn_orient_matrix_UB_22      0.0268897000
_diffrn_orient_matrix_UB_23      -0.0009795000
_diffrn_orient_matrix_UB_31      0.0067630000
_diffrn_orient_matrix_UB_32      0.0064822000
_diffrn_orient_matrix_UB_33      0.0516479000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1284
_reflns_number_total             2769
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2769
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1507
_refine_ls_R_factor_gt           0.0756
_refine_ls_restrained_S_all      1.069
_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)+(0.1088P)²+0.2582P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2006
_refine_ls_wR_factor_ref         0.2523
_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 Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.02078(15) 0.11531(12) 0.74927(17) 0.0661(8) Uani 1 1 d . . . . .
C1 C 0.08836(19) 0.10905(18) 0.7455(2) 0.0697(9) Uani 1 1 d . . . . .
C2 C 0.1285(3) 0.0534(2) 0.7326(3) 0.0934(13) Uani 1 1 d . . . . .
H2 H 0.1105 0.0112 0.7254 0.112 Uiso 1 1 calc R . . . .
C3 C 0.1955(3) 0.0637(3) 0.7311(3) 0.1196(19) Uani 1 1 d . . . . .
H3 H 0.2233 0.0276 0.7220 0.143 Uiso 1 1 calc R . . . .
C4 C 0.2228(2) 0.1249(3) 0.7426(3) 0.1080(15) Uani 1 1 d . . . . .
H4 H 0.2687 0.1295 0.7422 0.130 Uiso 1 1 calc R . . . .
C5 C 0.18366(19) 0.1803(2) 0.7547(3) 0.0864(11) Uani 1 1 d . . . . .
H5 H 0.2027 0.2218 0.7629 0.104 Uiso 1 1 calc R . . . .
C6 C 0.11555(17) 0.17299(17) 0.7545(2) 0.0621(9) Uani 1 1 d . . . . .
C7 C 0.06141(15) 0.21839(15) 0.76307(19) 0.0550(8) Uani 1 1 d . . . . .
C8 C 0.00472(15) 0.18164(14) 0.76064(19) 0.0534(8) Uani 1 1 d . . . . .
C9 C -0.0257(2) 0.06008(17) 0.7462(3) 0.0883(12) Uani 1 1 d . . . . .
H9A H -0.0089 0.0262 0.7023 0.132 Uiso 1 1 calc GR . . . .
H9B H -0.0677 0.0753 0.7213 0.132 Uiso 1 1 calc GR . . . .
H9C H -0.0312 0.0424 0.8130 0.132 Uiso 1 1 calc GR . . . .
C10 C 0.06418(15) 0.29217(15) 0.7709(2) 0.0578(8) Uani 1 1 d . . . . .
H10 H 0.0902 0.3088 0.7138 0.069 Uiso 1 1 calc R . . . .
C11 C 0.09618(17) 0.31689(19) 0.8672(2) 0.0762(10) Uani 1 1 d . . . . .
H11 H 0.1091 0.3611 0.8671 0.091 Uiso 1 1 calc R . . . .
C12 C 0.10740(17) 0.28582(18) 0.9461(3) 0.0783(10) Uani 1 1 d . . . . .
H12 H 0.0950 0.2415 0.9460 0.094 Uiso 1 1 calc R . . . .
C13 C 0.13852(16) 0.31084(18) 1.0421(2) 0.0694(9) Uani 1 1 d . . . . .
C14 C 0.16866(19) 0.37106(19) 1.0496(3) 0.0849(11) Uani 1 1 d . . . . .
H14 H 0.1722 0.3976 0.9925 0.102 Uiso 1 1 calc R . . . .
C15 C 0.1940(2) 0.3934(2) 1.1405(3) 0.0991(13) Uani 1 1 d . . . . .
H15 H 0.2147 0.4344 1.1436 0.119 Uiso 1 1 calc R . . . .
C16 C 0.1890(2) 0.3558(3) 1.2254(3) 0.1025(14) Uani 1 1 d . . . . .
H16 H 0.2049 0.3709 1.2872 0.123 Uiso 1 1 calc R . . . .
C17 C 0.1601(2) 0.2954(3) 1.2165(3) 0.1136(15) Uani 1 1 d . . . . .
H17 H 0.1566 0.2685 1.2732 0.136 Uiso 1 1 calc R . . . .
C18 C 0.1358(2) 0.2732(2) 1.1255(3) 0.0922(13) Uani 1 1 d . . . . .
H18 H 0.1172 0.2312 1.1217 0.111 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 1.372(4) . ?
N1 C8 1.387(4) . ?
N1 C9 1.459(4) . ?
C1 C2 1.397(5) . ?
C1 C6 1.409(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.369(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.364(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(5) . ?
C6 C7 1.432(4) . ?
C7 C8 1.365(4) . ?
C7 C10 1.495(4) . ?
C8 C10 1.495(4) 3 ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C8 1.495(4) 3 ?
C10 H10 0.9800 . ?
C10 C11 1.514(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.239(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.505(5) . ?
C13 C14 1.364(5) . ?
C13 C18 1.342(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.384(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.360(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.358(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.376(5) . ?
C18 H18 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
C1 N1 C8 109.0(3) . . ?
C1 N1 C9 124.7(3) . . ?
C8 N1 C9 126.2(3) . . ?
N1 C1 C2 131.0(4) . . ?
N1 C1 C6 107.5(3) . . ?
C2 C1 C6 121.5(4) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 C1 116.9(4) . . ?
C3 C2 H2 121.5 . . ?
C2 C3 H3 118.7 . . ?
C4 C3 C2 122.5(5) . . ?
C4 C3 H3 118.7 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.0(5) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.0(4) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C7 107.2(3) . . ?
C5 C6 C1 119.0(3) . . ?
C5 C6 C7 133.7(3) . . ?
C6 C7 C10 128.0(3) . . ?
C8 C7 C6 106.9(3) . . ?
C8 C7 C10 125.1(3) . . ?
N1 C8 C10 124.7(3) . 3 ?
C7 C8 N1 109.4(3) . . ?
C7 C8 C10 125.9(3) . 3 ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 C8 108.2(2) . 3 ?
C7 C10 H10 107.9 . . ?
C7 C10 C11 113.8(2) . . ?
C8 C10 H10 107.9 3 . ?
C8 C10 C11 110.9(2) 3 . ?
C11 C10 H10 107.9 . . ?
C10 C11 H11 115.8 . . ?
C12 C11 C10 128.3(3) . . ?
C12 C11 H11 115.8 . . ?
C11 C12 H12 115.9 . . ?
C11 C12 C13 128.1(4) . . ?
C13 C12 H12 115.9 . . ?
C14 C13 C12 123.2(3) . . ?
C18 C13 C12 119.2(4) . . ?
C18 C13 C14 117.6(3) . . ?
C13 C14 H14 119.4 . . ?
C13 C14 C15 121.3(4) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.7(4) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 121.3 . . ?
C17 C16 C15 117.5(4) . . ?
C17 C16 H16 121.3 . . ?
C16 C17 H17 119.3 . . ?
C16 C17 C18 121.5(4) . . ?
C18 C17 H17 119.3 . . ?
C13 C18 C17 121.4(4) . . ?
C13 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?

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
N1 C1 C2 C3 179.3(3) . . . . ?
N1 C1 C6 C5 178.9(2) . . . . ?
N1 C1 C6 C7 -0.5(3) . . . . ?
C1 N1 C8 C7 0.7(3) . . . . ?
C1 N1 C8 C10 -178.0(2) . . . 3 ?
C1 C2 C3 C4 0.6(6) . . . . ?
C1 C6 C7 C8 0.9(3) . . . . ?
C1 C6 C7 C10 -177.8(2) . . . . ?
C2 C1 C6 C5 -2.6(4) . . . . ?
C2 C1 C6 C7 178.0(3) . . . . ?
C2 C3 C4 C5 -1.1(7) . . . . ?
C3 C4 C5 C6 -0.4(6) . . . . ?
C4 C5 C6 C1 2.2(4) . . . . ?
C4 C5 C6 C7 -178.7(3) . . . . ?
C5 C6 C7 C8 -178.3(3) . . . . ?
C5 C6 C7 C10 3.0(5) . . . . ?
C6 C1 C2 C3 1.2(5) . . . . ?
C6 C7 C8 N1 -1.0(3) . . . . ?
C6 C7 C8 C10 177.7(2) . . . 3 ?
C6 C7 C10 C8 170.5(2) . . . 3 ?
C6 C7 C10 C11 -65.7(4) . . . . ?
C7 C10 C11 C12 -16.0(5) . . . . ?
C8 N1 C1 C2 -178.4(3) . . . . ?
C8 N1 C1 C6 -0.1(3) . . . . ?
C8 C7 C10 C8 -8.0(3) . . . 3 ?
C8 C7 C10 C11 115.8(3) . . . . ?
C8 C10 C11 C12 106.2(4) 3 . . . ?
C9 N1 C1 C2 4.1(5) . . . . ?
C9 N1 C1 C6 -177.6(3) . . . . ?
C9 N1 C8 C7 178.2(3) . . . . ?
C9 N1 C8 C10 -0.5(4) . . . 3 ?
C10 C7 C8 N1 177.8(2) . . . . ?
C10 C7 C8 C10 -3.5(4) . . . 3 ?
C10 C11 C12 C13 -179.2(3) . . . . ?
C11 C12 C13 C14 -10.6(6) . . . . ?
C11 C12 C13 C18 168.1(4) . . . . ?
C12 C13 C14 C15 177.1(3) . . . . ?
C12 C13 C18 C17 -176.1(4) . . . . ?
C13 C14 C15 C16 -0.6(6) . . . . ?
C14 C13 C18 C17 2.6(6) . . . . ?
C14 C15 C16 C17 1.8(7) . . . . ?
C15 C16 C17 C18 -0.8(7) . . . . ?
C16 C17 C18 C13 -1.4(7) . . . . ?
C18 C13 C14 C15 -1.7(6) . . . . ?

_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_191030_s2_zh
_audit_block_doi                 10.5517/ccdc.csd.cc244tgl
_database_code_depnum_ccdc_archive 'CCDC 1970839'
loop_
_audit_author_name
_audit_author_address
'hua zhang'
;Chinese Academy of Sciences University
China
;
_audit_update_record             
;
2019-12-09 deposited with the CCDC.	2020-04-23 downloaded from the CCDC.
;
_audit_creation_date             2019-10-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C27 H21 N3'
_chemical_formula_sum            'C27 H21 N3'
_chemical_formula_weight         387.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.7508(9)
_cell_length_b                   5.6719(4)
_cell_length_c                   26.3268(15)
_cell_angle_alpha                90
_cell_angle_beta                 97.603(5)
_cell_angle_gamma                90
_cell_volume                     2035.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2880
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.6350
_cell_measurement_theta_min      3.5420
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11967
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.123
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -11.00   51.40   0.8000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   77.0000 -150.0000 78

#__ type_ start__ end____ width___ exp.time_
  2 omega  -60.00  -34.40   0.8000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  129.0000 -154.0000 32

#__ type_ start__ end____ width___ exp.time_
  3 omega  -67.00  -42.20   0.8000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  141.0000   17.0000 31

#__ type_ start__ end____ width___ exp.time_
  4 omega  -83.00    3.40   0.8000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -38.0000  -90.0000 108

#__ type_ start__ end____ width___ exp.time_
  5 omega  -23.00   21.00   0.8000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       16.9981  -99.0000 -150.0000 55

#__ type_ start__ end____ width___ exp.time_
  6 omega   19.00   43.80   0.8000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       16.9981 -141.0000  -39.0000 31

#__ type_ start__ end____ width___ exp.time_
  7 omega   46.00   70.80   0.8000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       16.9981 -129.0000  132.0000 31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0034153000
_diffrn_orient_matrix_UB_12      0.0009368000
_diffrn_orient_matrix_UB_13      -0.0266450000
_diffrn_orient_matrix_UB_21      0.0510529000
_diffrn_orient_matrix_UB_22      -0.0224601000
_diffrn_orient_matrix_UB_23      0.0052213000
_diffrn_orient_matrix_UB_31      -0.0092968000
_diffrn_orient_matrix_UB_32      -0.1231171000
_diffrn_orient_matrix_UB_33      -0.0011758000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2956
_reflns_number_total             4148
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0514
_refine_ls_restrained_S_all      1.018
_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)+(0.0412P)²+0.4790P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1173
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C10(H10), C11(H11), C12(H12),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23),
  C24(H24), C25(H25), C26(H26), C27(H27)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.47063(10) 0.3860(3) 0.37200(5) 0.0402(4) Uani 1 1 d . . . . .
N2 N 0.33773(11) 0.1290(3) 0.35744(6) 0.0496(4) Uani 1 1 d . . . . .
N3 N 0.45701(12) 0.0957(3) 0.43170(6) 0.0516(4) Uani 1 1 d . . . . .
C1 C 0.44808(12) 0.5306(3) 0.32869(6) 0.0383(4) Uani 1 1 d . . . . .
C2 C 0.37447(13) 0.5183(4) 0.28722(7) 0.0479(5) Uani 1 1 d . . . . .
H2 H 0.3286 0.3970 0.2843 0.057 Uiso 1 1 calc R . . . .
C3 C 0.37177(14) 0.6918(4) 0.25056(7) 0.0532(5) Uani 1 1 d . . . . .
H3 H 0.3232 0.6864 0.2224 0.064 Uiso 1 1 calc R . . . .
C4 C 0.43946(15) 0.8747(4) 0.25433(7) 0.0513(5) Uani 1 1 d . . . . .
H4 H 0.4347 0.9911 0.2293 0.062 Uiso 1 1 calc R . . . .
C5 C 0.51368(13) 0.8850(3) 0.29492(6) 0.0436(4) Uani 1 1 d . . . . .
H5 H 0.5594 1.0066 0.2973 0.052 Uiso 1 1 calc R . . . .
C6 C 0.51892(12) 0.7098(3) 0.33231(6) 0.0364(4) Uani 1 1 d . . . . .
C7 C 0.58679(12) 0.6705(3) 0.37808(6) 0.0362(4) Uani 1 1 d . . . . .
C8 C 0.55549(12) 0.4767(3) 0.40054(6) 0.0399(4) Uani 1 1 d . . . . .
H8 H 0.5861 0.4117 0.4309 0.048 Uiso 1 1 calc R . . . .
C9 C 0.41854(13) 0.1936(3) 0.38770(6) 0.0411(4) Uani 1 1 d . . . . .
C10 C 0.29378(15) -0.0621(4) 0.37316(8) 0.0582(6) Uani 1 1 d . . . . .
H10 H 0.2375 -0.1168 0.3532 0.070 Uiso 1 1 calc R . . . .
C11 C 0.32698(16) -0.1819(4) 0.41705(8) 0.0608(6) Uani 1 1 d . . . . .
H11 H 0.2953 -0.3159 0.4270 0.073 Uiso 1 1 calc R . . . .
C12 C 0.40923(17) -0.0942(4) 0.44555(8) 0.0586(6) Uani 1 1 d . . . . .
H12 H 0.4331 -0.1701 0.4760 0.070 Uiso 1 1 calc R . . . .
C13 C 0.67464(13) 0.8212(3) 0.39662(6) 0.0392(4) Uani 1 1 d . . . . .
H13 H 0.6496 0.9807 0.4009 0.047 Uiso 1 1 calc R . . . .
C14 C 0.74730(12) 0.8410(3) 0.35782(6) 0.0362(4) Uani 1 1 d . . . . .
C15 C 0.80729(15) 1.0390(3) 0.35863(7) 0.0512(5) Uani 1 1 d . . . . .
H15 H 0.8020 1.1578 0.3825 0.061 Uiso 1 1 calc R . . . .
C16 C 0.87460(15) 1.0607(4) 0.32434(8) 0.0585(6) Uani 1 1 d . . . . .
H16 H 0.9144 1.1937 0.3254 0.070 Uiso 1 1 calc R . . . .
C17 C 0.88332(14) 0.8884(4) 0.28886(7) 0.0539(5) Uani 1 1 d . . . . .
H17 H 0.9286 0.9037 0.2658 0.065 Uiso 1 1 calc R . . . .
C18 C 0.82448(14) 0.6929(4) 0.28778(7) 0.0519(5) Uani 1 1 d . . . . .
H18 H 0.8300 0.5749 0.2638 0.062 Uiso 1 1 calc R . . . .
C19 C 0.75717(13) 0.6695(3) 0.32196(6) 0.0434(4) Uani 1 1 d . . . . .
H19 H 0.7179 0.5357 0.3207 0.052 Uiso 1 1 calc R . . . .
C20 C 0.72240(14) 0.7434(3) 0.44884(6) 0.0468(5) Uani 1 1 d . . . . .
H20 H 0.6927 0.7919 0.4768 0.056 Uiso 1 1 calc R . . . .
C21 C 0.80099(14) 0.6151(3) 0.45849(7) 0.0456(5) Uani 1 1 d . . . . .
H21 H 0.8305 0.5677 0.4304 0.055 Uiso 1 1 calc R . . . .
C22 C 0.84841(13) 0.5365(3) 0.50926(6) 0.0426(4) Uani 1 1 d . . . . .
C23 C 0.84297(15) 0.6655(4) 0.55307(7) 0.0546(5) Uani 1 1 d . . . . .
H23 H 0.8072 0.8052 0.5511 0.065 Uiso 1 1 calc R . . . .
C24 C 0.88981(18) 0.5906(4) 0.59981(8) 0.0714(7) Uani 1 1 d . . . . .
H24 H 0.8852 0.6799 0.6290 0.086 Uiso 1 1 calc R . . . .
C25 C 0.94287(17) 0.3866(5) 0.60364(8) 0.0689(7) Uani 1 1 d . . . . .
H25 H 0.9747 0.3374 0.6352 0.083 Uiso 1 1 calc R . . . .
C26 C 0.94883(16) 0.2555(4) 0.56075(9) 0.0652(6) Uani 1 1 d . . . . .
H26 H 0.9843 0.1154 0.5631 0.078 Uiso 1 1 calc R . . . .
C27 C 0.90235(15) 0.3304(4) 0.51395(8) 0.0586(6) Uani 1 1 d . . . . .
H27 H 0.9074 0.2402 0.4849 0.070 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 1.406(2) . ?
N1 C8 1.399(2) . ?
N1 C9 1.398(2) . ?
N2 C9 1.330(2) . ?
N2 C10 1.333(2) . ?
N3 C9 1.330(2) . ?
N3 C12 1.337(2) . ?
C1 C2 1.389(2) . ?
C1 C6 1.402(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.389(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.394(2) . ?
C6 C7 1.440(2) . ?
C7 C8 1.346(2) . ?
C7 C13 1.508(2) . ?
C8 H8 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.366(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.366(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9800 . ?
C13 C14 1.525(2) . ?
C13 C20 1.509(2) . ?
C14 C15 1.392(2) . ?
C14 C19 1.374(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.381(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.368(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.371(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.380(2) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.300(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.477(2) . ?
C22 C23 1.376(2) . ?
C22 C27 1.381(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.378(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.364(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.364(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.378(3) . ?
C27 H27 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
C8 N1 C1 107.45(14) . . ?
C9 N1 C1 128.97(14) . . ?
C9 N1 C8 123.49(14) . . ?
C9 N2 C10 114.51(17) . . ?
C9 N3 C12 114.88(17) . . ?
C2 C1 N1 131.91(17) . . ?
C2 C1 C6 121.16(16) . . ?
C6 C1 N1 106.92(14) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 C1 117.71(18) . . ?
C3 C2 H2 121.1 . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 121.92(17) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.53(17) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.76(18) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C7 108.19(14) . . ?
C5 C6 C1 119.87(15) . . ?
C5 C6 C7 131.94(17) . . ?
C6 C7 C13 125.86(15) . . ?
C8 C7 C6 106.53(15) . . ?
C8 C7 C13 127.61(15) . . ?
N1 C8 H8 124.5 . . ?
C7 C8 N1 110.90(15) . . ?
C7 C8 H8 124.5 . . ?
N2 C9 N1 117.27(16) . . ?
N3 C9 N1 115.04(16) . . ?
N3 C9 N2 127.69(18) . . ?
N2 C10 H10 118.2 . . ?
N2 C10 C11 123.6(2) . . ?
C11 C10 H10 118.2 . . ?
C10 C11 H11 121.8 . . ?
C12 C11 C10 116.3(2) . . ?
C12 C11 H11 121.8 . . ?
N3 C12 C11 123.0(2) . . ?
N3 C12 H12 118.5 . . ?
C11 C12 H12 118.5 . . ?
C7 C13 H13 106.4 . . ?
C7 C13 C14 113.13(13) . . ?
C7 C13 C20 111.25(15) . . ?
C14 C13 H13 106.4 . . ?
C20 C13 H13 106.4 . . ?
C20 C13 C14 112.78(14) . . ?
C15 C14 C13 119.25(16) . . ?
C19 C14 C13 122.76(16) . . ?
C19 C14 C15 117.99(17) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.58(18) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.63(19) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.4 . . ?
C16 C17 C18 119.17(18) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.59(19) . . ?
C19 C18 H18 119.7 . . ?
C14 C19 C18 121.04(18) . . ?
C14 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C13 C20 H20 116.8 . . ?
C21 C20 C13 126.31(17) . . ?
C21 C20 H20 116.8 . . ?
C20 C21 H21 116.5 . . ?
C20 C21 C22 127.01(17) . . ?
C22 C21 H21 116.5 . . ?
C23 C22 C21 122.12(17) . . ?
C23 C22 C27 117.59(17) . . ?
C27 C22 C21 120.26(17) . . ?
C22 C23 H23 119.6 . . ?
C22 C23 C24 120.9(2) . . ?
C24 C23 H23 119.6 . . ?
C23 C24 H24 119.7 . . ?
C25 C24 C23 120.6(2) . . ?
C25 C24 H24 119.7 . . ?
C24 C25 H25 120.3 . . ?
C26 C25 C24 119.44(19) . . ?
C26 C25 H25 120.3 . . ?
C25 C26 H26 120.0 . . ?
C25 C26 C27 120.0(2) . . ?
C27 C26 H26 120.0 . . ?
C22 C27 H27 119.3 . . ?
C26 C27 C22 121.40(19) . . ?
C26 C27 H27 119.3 . . ?

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
N1 C1 C2 C3 179.48(17) . . . . ?
N1 C1 C6 C5 -178.32(14) . . . . ?
N1 C1 C6 C7 1.16(18) . . . . ?
N2 C10 C11 C12 0.7(3) . . . . ?
C1 N1 C8 C7 0.71(19) . . . . ?
C1 N1 C9 N2 2.4(3) . . . . ?
C1 N1 C9 N3 -177.87(16) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C1 C6 C7 C8 -0.74(18) . . . . ?
C1 C6 C7 C13 179.79(15) . . . . ?
C2 C1 C6 C5 2.7(2) . . . . ?
C2 C1 C6 C7 -177.83(15) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 C5 C6 C1 -1.4(2) . . . . ?
C4 C5 C6 C7 179.23(17) . . . . ?
C5 C6 C7 C8 178.66(18) . . . . ?
C5 C6 C7 C13 -0.8(3) . . . . ?
C6 C1 C2 C3 -1.8(3) . . . . ?
C6 C7 C8 N1 0.02(19) . . . . ?
C6 C7 C13 C14 -58.2(2) . . . . ?
C6 C7 C13 C20 173.62(15) . . . . ?
C7 C13 C14 C15 153.56(16) . . . . ?
C7 C13 C14 C19 -27.1(2) . . . . ?
C7 C13 C20 C21 100.8(2) . . . . ?
C8 N1 C1 C2 177.70(18) . . . . ?
C8 N1 C1 C6 -1.15(18) . . . . ?
C8 N1 C9 N2 178.46(15) . . . . ?
C8 N1 C9 N3 -1.8(2) . . . . ?
C8 C7 C13 C14 122.43(18) . . . . ?
C8 C7 C13 C20 -5.7(2) . . . . ?
C9 N1 C1 C2 -5.8(3) . . . . ?
C9 N1 C1 C6 175.39(16) . . . . ?
C9 N1 C8 C7 -176.06(15) . . . . ?
C9 N2 C10 C11 1.0(3) . . . . ?
C9 N3 C12 C11 -0.2(3) . . . . ?
C10 N2 C9 N1 176.99(16) . . . . ?
C10 N2 C9 N3 -2.7(3) . . . . ?
C10 C11 C12 N3 -1.1(3) . . . . ?
C12 N3 C9 N1 -177.38(16) . . . . ?
C12 N3 C9 N2 2.3(3) . . . . ?
C13 C7 C8 N1 179.47(15) . . . . ?
C13 C14 C15 C16 179.27(16) . . . . ?
C13 C14 C19 C18 -179.38(16) . . . . ?
C13 C20 C21 C22 -179.71(17) . . . . ?
C14 C13 C20 C21 -27.5(3) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
C15 C14 C19 C18 0.0(3) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C17 C18 C19 C14 0.1(3) . . . . ?
C19 C14 C15 C16 -0.1(3) . . . . ?
C20 C13 C14 C15 -79.1(2) . . . . ?
C20 C13 C14 C19 100.30(19) . . . . ?
C20 C21 C22 C23 -29.2(3) . . . . ?
C20 C21 C22 C27 152.3(2) . . . . ?
C21 C22 C23 C24 -178.5(2) . . . . ?
C21 C22 C27 C26 178.77(19) . . . . ?
C22 C23 C24 C25 0.1(4) . . . . ?
C23 C22 C27 C26 0.3(3) . . . . ?
C23 C24 C25 C26 -0.4(4) . . . . ?
C24 C25 C26 C27 0.7(4) . . . . ?
C25 C26 C27 C22 -0.6(3) . . . . ?
C27 C22 C23 C24 0.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
