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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_a
_database_code_depnum_ccdc_archive 'CCDC 1420026'
_audit_update_record             
;
2016-04-16 deposited with the CCDC.
2016-07-07 downloaded from the CCDC.
;
_audit_creation_date             2016-01-17
_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 H20 N2 O'
_chemical_formula_sum            'C28 H20 N2 O'
_chemical_formula_weight         400.46
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   16.599(4)
_cell_length_b                   7.731(2)
_cell_length_c                   17.121(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.991(4)
_cell_angle_gamma                90
_cell_volume                     2037.1(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1898
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.40
_cell_measurement_theta_min      2.65
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9850
_exptl_absorpt_correction_T_min  0.9834
_exptl_absorpt_correction_type   'Semi-empirical from equivalents'
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.003
_diffrn_reflns_theta_max         25.003
_diffrn_reflns_theta_min         1.458
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2450
_reflns_number_total             3591
_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 v7.60A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_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    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3591
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.021
_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)+(0.0597P)²+0.1406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1188
_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 Me refined with riding coordinates:
 C1(H1A,H1B,H1C)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C12(H12), C13(H13), C16(H16),
 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
O1 O 1.47346(8) -0.04336(19) 0.58760(8) 0.0584(4) Uani 1 1 d . . . . .
N1 N 1.05196(11) 0.2724(3) 0.34623(10) 0.0634(5) Uani 1 1 d . . . . .
N2 N 0.75148(9) 0.3879(2) 0.53139(8) 0.0429(4) Uani 1 1 d . . . . .
C1 C 1.52089(13) -0.1143(3) 0.66882(13) 0.0668(6) Uani 1 1 d . . . . .
H1A H 1.5786 -0.1435 0.6729 0.100 Uiso 1 1 calc R . . . .
H1B H 1.5240 -0.0307 0.7113 0.100 Uiso 1 1 calc R . . . .
H1C H 1.4920 -0.2165 0.6769 0.100 Uiso 1 1 calc R . . . .
C2 C 1.38924(11) 0.0055(2) 0.57124(11) 0.0429(5) Uani 1 1 d . . . . .
C3 C 1.34604(12) -0.0187(3) 0.62428(12) 0.0527(5) Uani 1 1 d . . . . .
H3 H 1.3740 -0.0715 0.6763 0.063 Uiso 1 1 calc R . . . .
C4 C 1.26110(12) 0.0351(3) 0.60086(12) 0.0533(5) Uani 1 1 d . . . . .
H4 H 1.2328 0.0178 0.6379 0.064 Uiso 1 1 calc R . . . .
C5 C 1.21647(11) 0.1137(2) 0.52429(10) 0.0392(4) Uani 1 1 d . . . . .
C6 C 1.26121(12) 0.1334(3) 0.47085(11) 0.0472(5) Uani 1 1 d . . . . .
H6 H 1.2331 0.1835 0.4182 0.057 Uiso 1 1 calc R . . . .
C7 C 1.34618(12) 0.0808(3) 0.49355(11) 0.0495(5) Uani 1 1 d . . . . .
H7 H 1.3747 0.0960 0.4565 0.059 Uiso 1 1 calc R . . . .
C8 C 1.12580(11) 0.1760(2) 0.50092(10) 0.0389(4) Uani 1 1 d . . . . .
C9 C 1.08438(11) 0.1850(2) 0.55502(11) 0.0455(5) Uani 1 1 d . . . . .
H9 H 1.1184 0.1494 0.6093 0.055 Uiso 1 1 calc R . . . .
C10 C 1.08368(11) 0.2301(3) 0.41505(12) 0.0456(5) Uani 1 1 d . . . . .
C11 C 0.99742(11) 0.2388(2) 0.54619(10) 0.0413(4) Uani 1 1 d . . . . .
C12 C 0.97539(11) 0.2160(3) 0.61737(11) 0.0460(5) Uani 1 1 d . . . . .
H12 H 1.0168 0.1688 0.6657 0.055 Uiso 1 1 calc R . . . .
C13 C 0.89611(11) 0.2599(3) 0.61889(11) 0.0450(5) Uani 1 1 d . . . . .
H13 H 0.8833 0.2417 0.6667 0.054 Uiso 1 1 calc R . . . .
C14 C 0.83549(11) 0.3324(2) 0.54651(10) 0.0393(4) Uani 1 1 d . . . . .
C15 C 0.85426(10) 0.3546(2) 0.47363(10) 0.0385(4) Uani 1 1 d . . . . .
C16 C 0.93470(11) 0.3087(2) 0.47344(10) 0.0419(4) Uani 1 1 d . . . . .
H16 H 0.9470 0.3242 0.4252 0.050 Uiso 1 1 calc R . . . .
C17 C 0.77682(11) 0.4275(2) 0.41059(10) 0.0398(4) Uani 1 1 d . . . . .
C18 C 0.71527(11) 0.4454(2) 0.44791(10) 0.0399(4) Uani 1 1 d . . . . .
C19 C 0.63369(11) 0.5154(3) 0.40445(11) 0.0467(5) Uani 1 1 d . . . . .
H19 H 0.5932 0.5270 0.4297 0.056 Uiso 1 1 calc R . . . .
C20 C 0.61506(12) 0.5670(3) 0.32280(11) 0.0520(5) Uani 1 1 d . . . . .
H20 H 0.5608 0.6140 0.2922 0.062 Uiso 1 1 calc R . . . .
C21 C 0.67514(13) 0.5507(3) 0.28501(11) 0.0546(5) Uani 1 1 d . . . . .
H21 H 0.6606 0.5874 0.2297 0.066 Uiso 1 1 calc R . . . .
C22 C 0.75635(12) 0.4807(3) 0.32792(11) 0.0491(5) Uani 1 1 d . . . . .
H22 H 0.7964 0.4696 0.3021 0.059 Uiso 1 1 calc R . . . .
C23 C 0.71343(11) 0.4033(2) 0.59317(10) 0.0399(4) Uani 1 1 d . . . . .
C24 C 0.75786(11) 0.4904(2) 0.66771(11) 0.0459(5) Uani 1 1 d . . . . .
H24 H 0.8117 0.5399 0.6769 0.055 Uiso 1 1 calc R . . . .
C25 C 0.72190(13) 0.5031(3) 0.72819(12) 0.0530(5) Uani 1 1 d . . . . .
H25 H 0.7518 0.5610 0.7784 0.064 Uiso 1 1 calc R . . . .
C26 C 0.64210(13) 0.4308(3) 0.71477(13) 0.0559(5) Uani 1 1 d . . . . .
H26 H 0.6181 0.4396 0.7557 0.067 Uiso 1 1 calc R . . . .
C27 C 0.59810(12) 0.3456(3) 0.64059(13) 0.0528(5) Uani 1 1 d . . . . .
H27 H 0.5441 0.2970 0.6315 0.063 Uiso 1 1 calc R . . . .
C28 C 0.63317(11) 0.3314(2) 0.57955(12) 0.0478(5) Uani 1 1 d . . . . .
H28 H 0.6029 0.2737 0.5294 0.057 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
O1 C1 1.426(2) . ?
O1 C2 1.372(2) . ?
N1 C10 1.144(2) . ?
N2 C14 1.388(2) . ?
N2 C18 1.399(2) . ?
N2 C23 1.426(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.364(2) . ?
C2 C7 1.381(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(2) . ?
C5 C6 1.386(2) . ?
C5 C8 1.485(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.377(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.346(2) . ?
C8 C10 1.434(3) . ?
C9 H9 0.9300 . ?
C9 C11 1.455(2) . ?
C11 C12 1.408(2) . ?
C11 C16 1.399(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.368(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.389(2) . ?
C14 C15 1.405(2) . ?
C15 C16 1.383(2) . ?
C15 C17 1.448(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.400(2) . ?
C17 C22 1.388(2) . ?
C18 C19 1.388(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.373(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.383(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.381(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.386(2) . ?
C23 C28 1.380(2) . ?
C24 H24 0.9300 . ?
C24 C25 1.379(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.376(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.373(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.378(2) . ?
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
C2 O1 C1 116.95(14) . . ?
C14 N2 C18 107.82(13) . . ?
C14 N2 C23 125.51(14) . . ?
C18 N2 C23 126.25(14) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C7 115.66(15) . . ?
C3 C2 O1 125.15(17) . . ?
C3 C2 C7 119.17(16) . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.05(18) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 118.8 . . ?
C3 C4 C5 122.38(17) . . ?
C5 C4 H4 118.8 . . ?
C4 C5 C6 116.43(16) . . ?
C4 C5 C8 121.84(15) . . ?
C6 C5 C8 121.72(16) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 C5 121.79(17) . . ?
C7 C6 H6 119.1 . . ?
C2 C7 H7 119.9 . . ?
C6 C7 C2 120.16(16) . . ?
C6 C7 H7 119.9 . . ?
C9 C8 C5 123.95(16) . . ?
C9 C8 C10 120.78(16) . . ?
C10 C8 C5 115.27(14) . . ?
C8 C9 H9 113.3 . . ?
C8 C9 C11 133.30(17) . . ?
C11 C9 H9 113.3 . . ?
N1 C10 C8 178.27(18) . . ?
C12 C11 C9 116.31(15) . . ?
C16 C11 C9 125.57(15) . . ?
C16 C11 C12 118.11(16) . . ?
C11 C12 H12 118.4 . . ?
C13 C12 C11 123.26(16) . . ?
C13 C12 H12 118.4 . . ?
C12 C13 H13 121.2 . . ?
C12 C13 C14 117.62(16) . . ?
C14 C13 H13 121.2 . . ?
N2 C14 C13 129.28(15) . . ?
N2 C14 C15 109.75(14) . . ?
C13 C14 C15 120.95(16) . . ?
C14 C15 C17 106.23(15) . . ?
C16 C15 C14 120.40(15) . . ?
C16 C15 C17 133.37(16) . . ?
C11 C16 H16 120.2 . . ?
C15 C16 C11 119.63(15) . . ?
C15 C16 H16 120.2 . . ?
C18 C17 C15 107.10(15) . . ?
C22 C17 C15 133.27(16) . . ?
C22 C17 C18 119.61(16) . . ?
N2 C18 C17 109.09(14) . . ?
C19 C18 N2 129.14(15) . . ?
C19 C18 C17 121.74(16) . . ?
C18 C19 H19 121.2 . . ?
C20 C19 C18 117.51(16) . . ?
C20 C19 H19 121.2 . . ?
C19 C20 H20 119.2 . . ?
C19 C20 C21 121.53(17) . . ?
C21 C20 H20 119.2 . . ?
C20 C21 H21 119.4 . . ?
C22 C21 C20 121.20(18) . . ?
C22 C21 H21 119.4 . . ?
C17 C22 H22 120.8 . . ?
C21 C22 C17 118.42(17) . . ?
C21 C22 H22 120.8 . . ?
C24 C23 N2 119.52(16) . . ?
C28 C23 N2 120.59(16) . . ?
C28 C23 C24 119.89(16) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 C23 119.71(17) . . ?
C25 C24 H24 120.1 . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.40(19) . . ?
C26 C25 H25 119.8 . . ?
C25 C26 H26 120.2 . . ?
C27 C26 C25 119.66(17) . . ?
C27 C26 H26 120.2 . . ?
C26 C27 H27 119.7 . . ?
C26 C27 C28 120.68(18) . . ?
C28 C27 H27 119.7 . . ?
C23 C28 H28 120.2 . . ?
C27 C28 C23 119.66(18) . . ?
C27 C28 H28 120.2 . . ?

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
O1 C2 C3 C4 -179.64(19) . . . . ?
O1 C2 C7 C6 179.60(17) . . . . ?
N2 C14 C15 C16 179.80(16) . . . . ?
N2 C14 C15 C17 -0.2(2) . . . . ?
N2 C18 C19 C20 177.97(18) . . . . ?
N2 C23 C24 C25 -178.98(17) . . . . ?
N2 C23 C28 C27 179.07(17) . . . . ?
C1 O1 C2 C3 -4.4(3) . . . . ?
C1 O1 C2 C7 177.23(18) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C2 C7 C6 1.2(3) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C3 C4 C5 C8 -178.04(18) . . . . ?
C4 C5 C6 C7 -1.3(3) . . . . ?
C4 C5 C8 C9 10.0(3) . . . . ?
C4 C5 C8 C10 -170.80(18) . . . . ?
C5 C6 C7 C2 0.2(3) . . . . ?
C5 C8 C9 C11 -179.26(18) . . . . ?
C6 C5 C8 C9 -169.09(19) . . . . ?
C6 C5 C8 C10 10.1(3) . . . . ?
C7 C2 C3 C4 -1.4(3) . . . . ?
C8 C5 C6 C7 177.84(17) . . . . ?
C8 C9 C11 C12 174.9(2) . . . . ?
C8 C9 C11 C16 -4.4(3) . . . . ?
C9 C11 C12 C13 -179.84(18) . . . . ?
C9 C11 C16 C15 -179.98(17) . . . . ?
C10 C8 C9 C11 1.6(3) . . . . ?
C11 C12 C13 C14 -0.9(3) . . . . ?
C12 C11 C16 C15 0.7(3) . . . . ?
C12 C13 C14 N2 -179.94(18) . . . . ?
C12 C13 C14 C15 2.0(3) . . . . ?
C13 C14 C15 C16 -1.8(3) . . . . ?
C13 C14 C15 C17 178.27(17) . . . . ?
C14 N2 C18 C17 -0.5(2) . . . . ?
C14 N2 C18 C19 -178.64(19) . . . . ?
C14 N2 C23 C24 49.6(3) . . . . ?
C14 N2 C23 C28 -130.00(19) . . . . ?
C14 C15 C16 C11 0.4(3) . . . . ?
C14 C15 C17 C18 -0.2(2) . . . . ?
C14 C15 C17 C22 178.3(2) . . . . ?
C15 C17 C18 N2 0.4(2) . . . . ?
C15 C17 C18 C19 178.70(17) . . . . ?
C15 C17 C22 C21 -178.2(2) . . . . ?
C16 C11 C12 C13 -0.5(3) . . . . ?
C16 C15 C17 C18 179.9(2) . . . . ?
C16 C15 C17 C22 -1.6(4) . . . . ?
C17 C15 C16 C11 -179.66(19) . . . . ?
C17 C18 C19 C20 0.1(3) . . . . ?
C18 N2 C14 C13 -177.84(18) . . . . ?
C18 N2 C14 C15 0.4(2) . . . . ?
C18 N2 C23 C24 -122.0(2) . . . . ?
C18 N2 C23 C28 58.4(3) . . . . ?
C18 C17 C22 C21 0.2(3) . . . . ?
C18 C19 C20 C21 -0.2(3) . . . . ?
C19 C20 C21 C22 0.3(3) . . . . ?
C20 C21 C22 C17 -0.3(3) . . . . ?
C22 C17 C18 N2 -178.32(16) . . . . ?
C22 C17 C18 C19 0.0(3) . . . . ?
C23 N2 C14 C13 9.3(3) . . . . ?
C23 N2 C14 C15 -172.48(17) . . . . ?
C23 N2 C18 C17 172.31(16) . . . . ?
C23 N2 C18 C19 -5.8(3) . . . . ?
C23 C24 C25 C26 -0.3(3) . . . . ?
C24 C23 C28 C27 -0.5(3) . . . . ?
C24 C25 C26 C27 -0.1(3) . . . . ?
C25 C26 C27 C28 0.2(3) . . . . ?
C26 C27 C28 C23 0.1(3) . . . . ?
C28 C23 C24 C25 0.6(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_www
_database_code_depnum_ccdc_archive 'CCDC 1420027'
_audit_update_record             
;
2016-04-16 deposited with the CCDC.
2016-07-07 downloaded from the CCDC.
;
_audit_creation_date             2016-04-15
_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         'C27 H17 Cl N2'
_chemical_formula_sum            'C27 H17 Cl N2'
_chemical_formula_weight         404.88
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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/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                   16.672(12)
_cell_length_b                   13.929(10)
_cell_length_c                   8.865(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.965(8)
_cell_angle_gamma                90
_cell_volume                     2006(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4727
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.58
_cell_measurement_theta_min      2.51
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15752
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.008
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_min         2.774
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2775
_reflns_number_total             3544
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.114
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3544
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.031
_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)+(0.0455P)²+0.4702P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.1004
_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:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C10(H10), C11(H11), C14(H14),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C23(H23), C24(H24), C26(H26),
  C27(H27)
;
_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
Cl1 Cl 0.78141(4) 0.12247(4) 1.36597(7) 0.0905(2) Uani 1 1 d . . . . .
N1 N 0.16590(8) 0.18722(9) 0.27036(15) 0.0432(3) Uani 1 1 d . . . . .
N2 N 0.49471(10) -0.07546(11) 0.67345(19) 0.0620(4) Uani 1 1 d . . . . .
C1 C 0.16379(10) 0.09547(11) 0.20547(18) 0.0423(4) Uani 1 1 d . . . . .
C2 C 0.10868(11) 0.05716(13) 0.07760(19) 0.0503(4) Uani 1 1 d . . . . .
H2 H 0.0635 0.0921 0.0250 0.060 Uiso 1 1 calc R . . . .
C3 C 0.12391(12) -0.03432(13) 0.0325(2) 0.0565(5) Uani 1 1 d . . . . .
H3 H 0.0883 -0.0613 -0.0529 0.068 Uiso 1 1 calc R . . . .
C4 C 0.19109(12) -0.08768(13) 0.1110(2) 0.0560(5) Uani 1 1 d . . . . .
H4 H 0.1989 -0.1498 0.0788 0.067 Uiso 1 1 calc R . . . .
C5 C 0.24596(11) -0.04905(12) 0.2359(2) 0.0507(4) Uani 1 1 d . . . . .
H5 H 0.2911 -0.0845 0.2875 0.061 Uiso 1 1 calc R . . . .
C6 C 0.23296(10) 0.04373(11) 0.28404(18) 0.0410(4) Uani 1 1 d . . . . .
C7 C 0.27919(9) 0.10677(11) 0.40196(18) 0.0393(4) Uani 1 1 d . . . . .
C8 C 0.35132(10) 0.09512(11) 0.51393(18) 0.0427(4) Uani 1 1 d . . . . .
H8 H 0.3793 0.0369 0.5228 0.051 Uiso 1 1 calc R . . . .
C9 C 0.38202(10) 0.17103(11) 0.61361(18) 0.0417(4) Uani 1 1 d . . . . .
C10 C 0.33774(10) 0.25853(11) 0.59513(19) 0.0434(4) Uani 1 1 d . . . . .
H10 H 0.3580 0.3094 0.6606 0.052 Uiso 1 1 calc R . . . .
C11 C 0.26599(10) 0.27191(11) 0.48458(18) 0.0430(4) Uani 1 1 d . . . . .
H11 H 0.2384 0.3304 0.4747 0.052 Uiso 1 1 calc R . . . .
C12 C 0.23639(9) 0.19496(11) 0.38832(18) 0.0391(4) Uani 1 1 d . . . . .
C13 C 0.10140(10) 0.25661(12) 0.23231(18) 0.0443(4) Uani 1 1 d . . . . .
C14 C 0.11723(11) 0.34721(12) 0.18291(19) 0.0510(4) Uani 1 1 d . . . . .
H14 H 0.1697 0.3632 0.1714 0.061 Uiso 1 1 calc R . . . .
C15 C 0.05400(13) 0.41417(14) 0.1506(2) 0.0631(5) Uani 1 1 d . . . . .
H15 H 0.0645 0.4759 0.1199 0.076 Uiso 1 1 calc R . . . .
C16 C -0.02446(13) 0.38967(16) 0.1637(2) 0.0695(6) Uani 1 1 d . . . . .
H16 H -0.0668 0.4345 0.1407 0.083 Uiso 1 1 calc R . . . .
C17 C -0.03983(12) 0.29908(17) 0.2107(3) 0.0699(6) Uani 1 1 d . . . . .
H17 H -0.0928 0.2824 0.2183 0.084 Uiso 1 1 calc R . . . .
C18 C 0.02284(11) 0.23246(14) 0.2468(2) 0.0586(5) Uani 1 1 d . . . . .
H18 H 0.0124 0.1715 0.2808 0.070 Uiso 1 1 calc R . . . .
C19 C 0.45509(10) 0.16670(12) 0.74012(19) 0.0456(4) Uani 1 1 d . . . . .
H19 H 0.4677 0.2243 0.7931 0.055 Uiso 1 1 calc R . . . .
C20 C 0.50780(10) 0.09443(11) 0.79460(18) 0.0424(4) Uani 1 1 d . . . . .
C21 C 0.49890(10) 0.00054(12) 0.72402(19) 0.0458(4) Uani 1 1 d . . . . .
C22 C 0.57628(10) 0.10268(11) 0.93435(19) 0.0444(4) Uani 1 1 d . . . . .
C23 C 0.61592(10) 0.02126(12) 1.0052(2) 0.0474(4) Uani 1 1 d . . . . .
H23 H 0.5999 -0.0387 0.9628 0.057 Uiso 1 1 calc R . . . .
C24 C 0.67841(11) 0.02678(13) 1.1369(2) 0.0527(4) Uani 1 1 d . . . . .
H24 H 0.7040 -0.0288 1.1821 0.063 Uiso 1 1 calc R . . . .
C25 C 0.70224(11) 0.11420(13) 1.2000(2) 0.0570(5) Uani 1 1 d . . . . .
C26 C 0.66477(14) 0.19628(14) 1.1332(3) 0.0779(7) Uani 1 1 d . . . . .
H26 H 0.6812 0.2558 1.1771 0.093 Uiso 1 1 calc R . . . .
C27 C 0.60271(13) 0.19073(13) 1.0010(2) 0.0687(6) Uani 1 1 d . . . . .
H27 H 0.5782 0.2468 0.9557 0.082 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
Cl1 C25 1.746(2) . ?
N1 C1 1.399(2) . ?
N1 C12 1.391(2) . ?
N1 C13 1.429(2) . ?
N2 C21 1.146(2) . ?
C1 C2 1.395(2) . ?
C1 C6 1.405(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.393(2) . ?
C6 C7 1.448(2) . ?
C7 C8 1.386(2) . ?
C7 C12 1.412(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.399(2) . ?
C9 C10 1.415(2) . ?
C9 C19 1.460(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.379(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.390(2) . ?
C13 C14 1.381(2) . ?
C13 C18 1.386(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.388(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.382(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.371(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.380(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.352(2) . ?
C20 C21 1.443(2) . ?
C20 C22 1.489(2) . ?
C22 C23 1.390(2) . ?
C22 C27 1.389(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.382(2) . ?
C24 H24 0.9300 . ?
C24 C25 1.361(3) . ?
C25 C26 1.372(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.381(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
C1 N1 C13 124.95(13) . . ?
C12 N1 C1 108.60(12) . . ?
C12 N1 C13 126.11(13) . . ?
N1 C1 C6 108.83(14) . . ?
C2 C1 N1 129.40(15) . . ?
C2 C1 C6 121.62(16) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 C1 117.35(17) . . ?
C3 C2 H2 121.3 . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 121.92(17) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.50(17) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.18(17) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C7 106.95(14) . . ?
C5 C6 C1 119.40(15) . . ?
C5 C6 C7 133.60(15) . . ?
C8 C7 C6 132.97(14) . . ?
C8 C7 C12 120.24(14) . . ?
C12 C7 C6 106.79(14) . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 119.95(14) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C10 118.06(15) . . ?
C8 C9 C19 125.28(14) . . ?
C10 C9 C19 116.62(14) . . ?
C9 C10 H10 118.5 . . ?
C11 C10 C9 123.06(15) . . ?
C11 C10 H10 118.5 . . ?
C10 C11 H11 121.2 . . ?
C10 C11 C12 117.66(14) . . ?
C12 C11 H11 121.2 . . ?
N1 C12 C7 108.81(13) . . ?
C11 C12 N1 130.16(14) . . ?
C11 C12 C7 121.02(15) . . ?
C14 C13 N1 120.39(16) . . ?
C14 C13 C18 120.21(16) . . ?
C18 C13 N1 119.39(16) . . ?
C13 C14 H14 120.4 . . ?
C13 C14 C15 119.29(19) . . ?
C15 C14 H14 120.4 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.86(18) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.4(2) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 H18 120.1 . . ?
C17 C18 C13 119.82(19) . . ?
C17 C18 H18 120.1 . . ?
C9 C19 H19 114.0 . . ?
C20 C19 C9 131.95(16) . . ?
C20 C19 H19 114.0 . . ?
C19 C20 C21 121.63(15) . . ?
C19 C20 C22 123.74(15) . . ?
C21 C20 C22 114.56(13) . . ?
N2 C21 C20 176.83(18) . . ?
C23 C22 C20 120.75(15) . . ?
C27 C22 C20 122.18(15) . . ?
C27 C22 C23 117.07(16) . . ?
C22 C23 H23 119.0 . . ?
C24 C23 C22 121.90(16) . . ?
C24 C23 H23 119.0 . . ?
C23 C24 H24 120.3 . . ?
C25 C24 C23 119.48(16) . . ?
C25 C24 H24 120.3 . . ?
C24 C25 Cl1 120.05(14) . . ?
C24 C25 C26 120.37(18) . . ?
C26 C25 Cl1 119.57(15) . . ?
C25 C26 H26 119.9 . . ?
C25 C26 C27 120.11(18) . . ?
C27 C26 H26 119.9 . . ?
C22 C27 H27 119.5 . . ?
C26 C27 C22 121.06(17) . . ?
C26 C27 H27 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C25 C26 C27 179.28(19) . . . . ?
N1 C1 C2 C3 176.07(16) . . . . ?
N1 C1 C6 C5 -177.60(14) . . . . ?
N1 C1 C6 C7 0.01(17) . . . . ?
N1 C13 C14 C15 -178.29(15) . . . . ?
N1 C13 C18 C17 179.85(16) . . . . ?
C1 N1 C12 C7 -1.29(17) . . . . ?
C1 N1 C12 C11 178.99(16) . . . . ?
C1 N1 C13 C14 -124.84(18) . . . . ?
C1 N1 C13 C18 55.8(2) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C1 C6 C7 C8 179.33(17) . . . . ?
C1 C6 C7 C12 -0.78(17) . . . . ?
C2 C1 C6 C5 -1.6(2) . . . . ?
C2 C1 C6 C7 175.97(14) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C1 0.7(2) . . . . ?
C4 C5 C6 C7 -176.13(17) . . . . ?
C5 C6 C7 C8 -3.5(3) . . . . ?
C5 C6 C7 C12 176.34(17) . . . . ?
C6 C1 C2 C3 1.0(2) . . . . ?
C6 C7 C8 C9 179.70(16) . . . . ?
C6 C7 C12 N1 1.28(17) . . . . ?
C6 C7 C12 C11 -178.97(14) . . . . ?
C7 C8 C9 C10 -0.5(2) . . . . ?
C7 C8 C9 C19 177.23(15) . . . . ?
C8 C7 C12 N1 -178.82(14) . . . . ?
C8 C7 C12 C11 0.9(2) . . . . ?
C8 C9 C10 C11 0.4(2) . . . . ?
C8 C9 C19 C20 -1.8(3) . . . . ?
C9 C10 C11 C12 0.4(2) . . . . ?
C9 C19 C20 C21 1.6(3) . . . . ?
C9 C19 C20 C22 -175.32(16) . . . . ?
C10 C9 C19 C20 175.93(18) . . . . ?
C10 C11 C12 N1 178.69(15) . . . . ?
C10 C11 C12 C7 -1.0(2) . . . . ?
C12 N1 C1 C2 -174.76(16) . . . . ?
C12 N1 C1 C6 0.79(17) . . . . ?
C12 N1 C13 C14 62.7(2) . . . . ?
C12 N1 C13 C18 -116.73(19) . . . . ?
C12 C7 C8 C9 -0.2(2) . . . . ?
C13 N1 C1 C2 11.6(3) . . . . ?
C13 N1 C1 C6 -172.81(14) . . . . ?
C13 N1 C12 C7 172.21(15) . . . . ?
C13 N1 C12 C11 -7.5(3) . . . . ?
C13 C14 C15 C16 -1.7(3) . . . . ?
C14 C13 C18 C17 0.4(3) . . . . ?
C14 C15 C16 C17 0.8(3) . . . . ?
C15 C16 C17 C18 0.8(3) . . . . ?
C16 C17 C18 C13 -1.4(3) . . . . ?
C18 C13 C14 C15 1.1(3) . . . . ?
C19 C9 C10 C11 -177.52(15) . . . . ?
C19 C20 C22 C23 164.91(17) . . . . ?
C19 C20 C22 C27 -14.2(3) . . . . ?
C20 C22 C23 C24 -178.57(16) . . . . ?
C20 C22 C27 C26 178.1(2) . . . . ?
C21 C20 C22 C23 -12.2(2) . . . . ?
C21 C20 C22 C27 168.72(18) . . . . ?
C22 C23 C24 C25 0.0(3) . . . . ?
C23 C22 C27 C26 -1.0(3) . . . . ?
C23 C24 C25 Cl1 -179.75(14) . . . . ?
C23 C24 C25 C26 -0.2(3) . . . . ?
C24 C25 C26 C27 -0.3(4) . . . . ?
C25 C26 C27 C22 0.9(4) . . . . ?
C27 C22 C23 C24 0.6(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_chenhe
_database_code_depnum_ccdc_archive 'CCDC 1474497'
_audit_update_record             
;
2016-04-16 deposited with the CCDC.
2016-07-07 downloaded from the CCDC.
;
_audit_creation_date             2016-01-16
_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         'C27 H18 N2'
_chemical_formula_sum            'C27 H18 N2'
_chemical_formula_weight         370.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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/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                   18.495(4)
_cell_length_b                   13.396(3)
_cell_length_c                   7.8586(17)
_cell_angle_alpha                90
_cell_angle_beta                 96.436(4)
_cell_angle_gamma                90
_cell_volume                     1934.7(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3171
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      6.11
_cell_measurement_theta_min      57.86
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9852
_exptl_absorpt_correction_T_min  0.9830
_exptl_absorpt_correction_type   'Semi-empirical from equivalents'
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11027
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.063
_diffrn_reflns_theta_max         25.063
_diffrn_reflns_theta_min         1.108
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2231
_reflns_number_total             3374
_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       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3374
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0506
_refine_ls_restrained_S_all      1.019
_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)+(0.0692P)²+0.0644P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1412
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H2(0.066) H3(0.076) H4(0.079) H5(0.07) H8(0.057) H10(0.059)
 H11(0.061) H16(0.071) H17(0.08) H18(0.078) H19(0.075) H20(0.068) H21(0.06)
 H23(0.069) H24(0.081) H25(0.087) H26(0.078) H27(0.064)
 Fixed X: H2(0.4276) H3(0.4222) H4(0.3242) H5(0.2256) H8(0.1249) H10(0.1228)
 H11(0.2372) H16(-0.1404) H17(-0.2531) H18(-0.2699) H19(-0.1743) H20(-0.0617)
 H21(0.0244) H23(0.4547) H24(0.5409) H25(0.5088) H26(0.3907) H27(0.3046)
 Fixed Y: H2(0.5734) H3(0.4056) H4(0.3102) H5(0.3826) H8(0.5157) H10(0.8065)
 H11(0.8287) H16(0.4952) H17(0.5175) H18(0.6361) H19(0.7366) H20(0.7163)
 H21(0.7166) H23(0.6744) H24(0.7988) H25(0.9538) H26(0.9856) H27(0.8595)
 Fixed Z: H2(-0.0054) H3(-0.0694) H4(-0.0127) H5(0.0939) H8(0.2144)
 H10(0.3383) H11(0.2591) H16(0.2327) H17(0.3248) H18(0.5283) H19(0.6341)
 H20(0.5417) H21(0.3868) H23(0.2529) H24(0.2528) H25(0.1458) H26(0.0318)
 H27(0.0184)
;
_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
C1 C 0.32918(11) 0.57809(14) 0.0849(3) 0.0458(5) Uani 1 1 d . . . . .
C2 C 0.38737(11) 0.53545(16) 0.0154(3) 0.0548(6) Uani 1 1 d . . . . .
H2 H 0.4276 0.5734 -0.0054 0.066 Uiso 1 1 calc R . . . .
C3 C 0.38385(12) 0.43564(18) -0.0217(3) 0.0634(7) Uani 1 1 d . . . . .
H3 H 0.4222 0.4056 -0.0694 0.076 Uiso 1 1 calc R . . . .
C4 C 0.32437(12) 0.37831(17) 0.0102(4) 0.0657(7) Uani 1 1 d . . . . .
H4 H 0.3242 0.3102 -0.0127 0.079 Uiso 1 1 calc R . . . .
C5 C 0.26582(12) 0.42103(15) 0.0752(3) 0.0580(6) Uani 1 1 d . . . . .
H5 H 0.2256 0.3826 0.0939 0.070 Uiso 1 1 calc R . . . .
C6 C 0.26752(10) 0.52224(14) 0.1126(3) 0.0458(5) Uani 1 1 d . . . . .
C7 C 0.21587(10) 0.59059(14) 0.1743(3) 0.0436(5) Uani 1 1 d . . . . .
C8 C 0.14692(10) 0.57822(14) 0.2217(3) 0.0472(5) Uani 1 1 d . . . . .
H8 H 0.1249 0.5157 0.2144 0.057 Uiso 1 1 calc R . . . .
C9 C 0.11026(10) 0.66006(14) 0.2808(3) 0.0461(5) Uani 1 1 d . . . . .
C10 C 0.14645(10) 0.75242(15) 0.2952(3) 0.0494(6) Uani 1 1 d . . . . .
H10 H 0.1228 0.8065 0.3383 0.059 Uiso 1 1 calc R . . . .
C11 C 0.21479(11) 0.76648(15) 0.2487(3) 0.0505(6) Uani 1 1 d . . . . .
H11 H 0.2372 0.8287 0.2591 0.061 Uiso 1 1 calc R . . . .
C12 C 0.24962(10) 0.68500(14) 0.1855(3) 0.0429(5) Uani 1 1 d . . . . .
C13 C -0.00622(11) 0.49578(16) 0.2314(3) 0.0494(5) Uani 1 1 d . . . . .
C14 C -0.01591(10) 0.58892(14) 0.3156(3) 0.0452(5) Uani 1 1 d . . . . .
C15 C -0.08817(10) 0.60296(14) 0.3768(3) 0.0462(5) Uani 1 1 d . . . . .
C16 C -0.14670(11) 0.54413(16) 0.3137(4) 0.0592(6) Uani 1 1 d . . . . .
H16 H -0.1404 0.4952 0.2327 0.071 Uiso 1 1 calc R . . . .
C17 C -0.21427(12) 0.55720(17) 0.3694(4) 0.0668(7) Uani 1 1 d . . . . .
H17 H -0.2531 0.5175 0.3248 0.080 Uiso 1 1 calc R . . . .
C18 C -0.22453(13) 0.62829(17) 0.4898(4) 0.0649(7) Uani 1 1 d . . . . .
H18 H -0.2699 0.6361 0.5283 0.078 Uiso 1 1 calc R . . . .
C19 C -0.16741(13) 0.68778(17) 0.5533(4) 0.0624(7) Uani 1 1 d . . . . .
H19 H -0.1743 0.7366 0.6341 0.075 Uiso 1 1 calc R . . . .
C20 C -0.09997(12) 0.67552(16) 0.4978(3) 0.0570(6) Uani 1 1 d . . . . .
H20 H -0.0617 0.7163 0.5417 0.068 Uiso 1 1 calc R . . . .
C21 C 0.03704(11) 0.65862(15) 0.3323(3) 0.0502(6) Uani 1 1 d . . . . .
H21 H 0.0244 0.7166 0.3868 0.060 Uiso 1 1 calc R . . . .
C22 C 0.37103(11) 0.75467(16) 0.1350(3) 0.0481(5) Uani 1 1 d . . . . .
C23 C 0.44188(11) 0.73659(18) 0.2063(3) 0.0577(6) Uani 1 1 d . . . . .
H23 H 0.4547 0.6744 0.2529 0.069 Uiso 1 1 calc R . . . .
C24 C 0.49311(12) 0.8112(2) 0.2077(3) 0.0674(7) Uani 1 1 d . . . . .
H24 H 0.5409 0.7988 0.2528 0.081 Uiso 1 1 calc R . . . .
C25 C 0.47400(14) 0.9035(2) 0.1431(4) 0.0721(8) Uani 1 1 d . . . . .
H25 H 0.5088 0.9538 0.1458 0.087 Uiso 1 1 calc R . . . .
C26 C 0.40350(14) 0.92241(18) 0.0741(3) 0.0648(7) Uani 1 1 d . . . . .
H26 H 0.3907 0.9856 0.0318 0.078 Uiso 1 1 calc R . . . .
C27 C 0.35186(12) 0.84754(16) 0.0676(3) 0.0536(6) Uani 1 1 d . . . . .
H27 H 0.3046 0.8595 0.0184 0.064 Uiso 1 1 calc R . . . .
N1 N 0.31826(9) 0.67764(12) 0.1314(2) 0.0478(5) Uani 1 1 d . . . . .
N2 N -0.00171(10) 0.42019(15) 0.1649(3) 0.0668(6) 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
C1 C2 1.384(3) . ?
C1 C6 1.401(3) . ?
C1 N1 1.403(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.368(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(3) . ?
C6 C7 1.446(3) . ?
C7 C8 1.378(3) . ?
C7 C12 1.409(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.396(3) . ?
C9 C10 1.405(3) . ?
C9 C21 1.456(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.367(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(3) . ?
C12 N1 1.387(3) . ?
C13 C14 1.433(3) . ?
C13 N2 1.147(3) . ?
C14 C15 1.482(3) . ?
C14 C21 1.349(3) . ?
C15 C16 1.385(3) . ?
C15 C20 1.394(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.381(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.371(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.372(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.377(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.387(3) . ?
C22 C27 1.383(3) . ?
C22 N1 1.418(2) . ?
C23 H23 0.9300 . ?
C23 C24 1.376(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.368(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.378(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.382(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
C2 C1 C6 121.56(19) . . ?
C2 C1 N1 129.50(19) . . ?
C6 C1 N1 108.88(17) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 C1 117.8(2) . . ?
C3 C2 H2 121.1 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.5(2) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.1(2) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C7 107.09(17) . . ?
C5 C6 C1 119.25(19) . . ?
C5 C6 C7 133.63(18) . . ?
C8 C7 C6 132.92(18) . . ?
C8 C7 C12 120.54(18) . . ?
C12 C7 C6 106.53(17) . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 119.63(17) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 C10 118.25(17) . . ?
C8 C9 C21 125.71(17) . . ?
C10 C9 C21 116.04(18) . . ?
C9 C10 H10 118.4 . . ?
C11 C10 C9 123.11(19) . . ?
C11 C10 H10 118.4 . . ?
C10 C11 H11 121.1 . . ?
C10 C11 C12 117.86(18) . . ?
C12 C11 H11 121.1 . . ?
C11 C12 C7 120.55(18) . . ?
N1 C12 C7 109.37(16) . . ?
N1 C12 C11 130.05(17) . . ?
N2 C13 C14 176.8(2) . . ?
C13 C14 C15 115.11(17) . . ?
C21 C14 C13 121.35(19) . . ?
C21 C14 C15 123.51(19) . . ?
C16 C15 C14 120.6(2) . . ?
C16 C15 C20 117.7(2) . . ?
C20 C15 C14 121.70(18) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.9(2) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.5(2) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.6(2) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.3(2) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 H20 119.5 . . ?
C19 C20 C15 121.1(2) . . ?
C19 C20 H20 119.5 . . ?
C9 C21 H21 114.0 . . ?
C14 C21 C9 132.1(2) . . ?
C14 C21 H21 114.0 . . ?
C23 C22 N1 119.85(19) . . ?
C27 C22 C23 120.11(18) . . ?
C27 C22 N1 120.04(19) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.7(2) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.3(2) . . ?
C25 C24 H24 119.9 . . ?
C24 C25 H25 119.8 . . ?
C24 C25 C26 120.4(2) . . ?
C26 C25 H25 119.8 . . ?
C25 C26 H26 120.0 . . ?
C25 C26 C27 120.0(2) . . ?
C27 C26 H26 120.0 . . ?
C22 C27 H27 120.2 . . ?
C26 C27 C22 119.5(2) . . ?
C26 C27 H27 120.2 . . ?
C1 N1 C22 125.29(17) . . ?
C12 N1 C1 108.11(15) . . ?
C12 N1 C22 126.42(17) . . ?

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
C1 C2 C3 C4 -0.5(4) . . . . ?
C1 C6 C7 C8 179.9(2) . . . . ?
C1 C6 C7 C12 -1.5(2) . . . . ?
C2 C1 C6 C5 2.4(3) . . . . ?
C2 C1 C6 C7 -176.1(2) . . . . ?
C2 C1 N1 C12 176.4(2) . . . . ?
C2 C1 N1 C22 -8.3(4) . . . . ?
C2 C3 C4 C5 2.2(4) . . . . ?
C3 C4 C5 C6 -1.5(4) . . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
C4 C5 C6 C7 177.2(2) . . . . ?
C5 C6 C7 C8 1.8(4) . . . . ?
C5 C6 C7 C12 -179.6(3) . . . . ?
C6 C1 C2 C3 -1.7(4) . . . . ?
C6 C1 N1 C12 -1.0(2) . . . . ?
C6 C1 N1 C22 174.4(2) . . . . ?
C6 C7 C8 C9 178.7(2) . . . . ?
C6 C7 C12 C11 -177.1(2) . . . . ?
C6 C7 C12 N1 0.9(2) . . . . ?
C7 C8 C9 C10 -2.1(3) . . . . ?
C7 C8 C9 C21 178.8(2) . . . . ?
C7 C12 N1 C1 0.0(2) . . . . ?
C7 C12 N1 C22 -175.27(19) . . . . ?
C8 C7 C12 C11 1.7(3) . . . . ?
C8 C7 C12 N1 179.76(19) . . . . ?
C8 C9 C10 C11 2.2(3) . . . . ?
C8 C9 C21 C14 -10.7(4) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C10 C9 C21 C14 170.2(2) . . . . ?
C10 C11 C12 C7 -1.6(3) . . . . ?
C10 C11 C12 N1 -179.2(2) . . . . ?
C11 C12 N1 C1 177.8(2) . . . . ?
C11 C12 N1 C22 2.5(4) . . . . ?
C12 C7 C8 C9 0.2(3) . . . . ?
C13 C14 C15 C16 -17.5(3) . . . . ?
C13 C14 C15 C20 162.9(2) . . . . ?
C13 C14 C21 C9 -1.3(4) . . . . ?
C14 C15 C16 C17 -179.6(2) . . . . ?
C14 C15 C20 C19 179.9(2) . . . . ?
C15 C14 C21 C9 -179.5(2) . . . . ?
C15 C16 C17 C18 -0.6(4) . . . . ?
C16 C15 C20 C19 0.4(3) . . . . ?
C16 C17 C18 C19 1.0(4) . . . . ?
C17 C18 C19 C20 -0.7(4) . . . . ?
C18 C19 C20 C15 0.0(4) . . . . ?
C20 C15 C16 C17 -0.1(3) . . . . ?
C21 C9 C10 C11 -178.6(2) . . . . ?
C21 C14 C15 C16 160.7(2) . . . . ?
C21 C14 C15 C20 -18.8(3) . . . . ?
C22 C23 C24 C25 1.6(4) . . . . ?
C23 C22 C27 C26 -0.9(3) . . . . ?
C23 C22 N1 C1 -44.5(3) . . . . ?
C23 C22 N1 C12 130.0(2) . . . . ?
C23 C24 C25 C26 -0.8(4) . . . . ?
C24 C25 C26 C27 -0.9(4) . . . . ?
C25 C26 C27 C22 1.7(4) . . . . ?
C27 C22 C23 C24 -0.8(3) . . . . ?
C27 C22 N1 C1 135.5(2) . . . . ?
C27 C22 N1 C12 -50.0(3) . . . . ?
N1 C1 C2 C3 -178.7(2) . . . . ?
N1 C1 C6 C5 179.9(2) . . . . ?
N1 C1 C6 C7 1.5(2) . . . . ?
N1 C22 C23 C24 179.2(2) . . . . ?
N1 C22 C27 C26 179.1(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_c
_database_code_depnum_ccdc_archive 'CCDC 1474499'
_audit_update_record             
;
2016-04-16 deposited with the CCDC.
2016-07-07 downloaded from the CCDC.
;
_audit_creation_date             2016-01-16
_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 H20 N2'
_chemical_formula_sum            'C28 H20 N2'
_chemical_formula_weight         384.46
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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/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                   16.517(4)
_cell_length_b                   13.934(3)
_cell_length_c                   9.048(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.642(4)
_cell_angle_gamma                90
_cell_volume                     2023.7(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2958
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      6.21
_cell_measurement_theta_min      54.77
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9839
_exptl_absorpt_correction_T_min  0.9803
_exptl_absorpt_correction_type   'Semi-empirical from equivalents'
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11762
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.192
_diffrn_reflns_theta_max         25.192
_diffrn_reflns_theta_min         1.269
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2062
_reflns_number_total             3637
_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       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_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    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0096(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3637
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1029
_refine_ls_R_factor_gt           0.0516
_refine_ls_restrained_S_all      0.954
_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)+(0.0659P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1429
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C16(H16),
 C17(H17), C19(H19), C20(H20), C22(H22), C24(H24), C25(H25), C26(H26), C27(H27),
  C28(H28)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_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
C1 C 0.26417(13) 0.80336(16) 1.1092(3) 0.0429(6) Uani 1 1 d . . . . .
C2 C 0.23537(14) 0.72663(17) 1.0141(3) 0.0487(6) Uani 1 1 d . . . . .
H2 H 0.2638 0.6685 1.0248 0.058 Uiso 1 1 calc R . . . .
C3 C 0.16332(14) 0.73943(16) 0.9031(3) 0.0488(6) Uani 1 1 d . . . . .
H3 H 0.1438 0.6889 0.8373 0.059 Uiso 1 1 calc R . . . .
C4 C 0.11765(13) 0.82604(16) 0.8849(3) 0.0457(6) Uani 1 1 d . . . . .
C5 C 0.14707(14) 0.90133(16) 0.9844(3) 0.0468(6) Uani 1 1 d . . . . .
H5 H 0.1179 0.9590 0.9753 0.056 Uiso 1 1 calc R . . . .
C6 C 0.21972(14) 0.89056(16) 1.0971(3) 0.0441(6) Uani 1 1 d . . . . .
C7 C 0.26527(14) 0.95304(16) 1.2147(3) 0.0457(6) Uani 1 1 d . . . . .
C8 C 0.25036(16) 1.04406(18) 1.2651(3) 0.0561(7) Uani 1 1 d . . . . .
H8 H 0.2038 1.0787 1.2150 0.067 Uiso 1 1 calc R . . . .
C9 C 0.30497(17) 1.0825(2) 1.3895(3) 0.0631(8) Uani 1 1 d . . . . .
H9 H 0.2954 1.1436 1.4231 0.076 Uiso 1 1 calc R . . . .
C10 C 0.37431(17) 1.0310(2) 1.4655(3) 0.0631(8) Uani 1 1 d . . . . .
H10 H 0.4102 1.0581 1.5501 0.076 Uiso 1 1 calc R . . . .
C11 C 0.39122(15) 0.94083(19) 1.4189(3) 0.0559(7) Uani 1 1 d . . . . .
H11 H 0.4378 0.9066 1.4701 0.067 Uiso 1 1 calc R . . . .
C12 C 0.33590(14) 0.90265(17) 1.2921(3) 0.0470(6) Uani 1 1 d . . . . .
C13 C -0.00099(15) 0.99542(19) 0.7727(3) 0.0515(7) Uani 1 1 d . . . . .
C14 C -0.00788(14) 0.90215(16) 0.7012(3) 0.0464(6) Uani 1 1 d . . . . .
C15 C -0.07557(14) 0.89547(17) 0.5599(3) 0.0479(6) Uani 1 1 d . . . . .
C16 C -0.09970(17) 0.80831(19) 0.4893(4) 0.0720(9) Uani 1 1 d . . . . .
H16 H -0.0746 0.7519 0.5322 0.086 Uiso 1 1 calc R . . . .
C17 C -0.16085(18) 0.8048(2) 0.3555(4) 0.0780(9) Uani 1 1 d . . . . .
H17 H -0.1755 0.7454 0.3102 0.094 Uiso 1 1 calc R . . . .
C18 C -0.20080(15) 0.8852(2) 0.2867(3) 0.0594(7) Uani 1 1 d . . . . .
C19 C -0.17677(15) 0.97117(19) 0.3573(3) 0.0563(7) Uani 1 1 d . . . . .
H19 H -0.2023 1.0273 0.3141 0.068 Uiso 1 1 calc R . . . .
C20 C -0.11552(14) 0.97667(18) 0.4912(3) 0.0524(7) Uani 1 1 d . . . . .
H20 H -0.1010 1.0363 0.5358 0.063 Uiso 1 1 calc R . . . .
C21 C -0.26746(18) 0.8793(2) 0.1408(4) 0.0853(10) Uani 1 1 d . . . . .
H21A H -0.2754 0.9414 0.0938 0.128 Uiso 1 1 calc GR . . . .
H21B H -0.3187 0.8581 0.1626 0.128 Uiso 1 1 calc GR . . . .
H21C H -0.2507 0.8345 0.0730 0.128 Uiso 1 1 calc GR . . . .
C22 C 0.04519(14) 0.83034(17) 0.7569(3) 0.0504(6) Uani 1 1 d . . . . .
H22 H 0.0334 0.7729 0.7038 0.061 Uiso 1 1 calc R . . . .
C23 C 0.40066(15) 0.74227(18) 1.2663(3) 0.0510(6) Uani 1 1 d . . . . .
C24 C 0.38527(16) 0.65279(19) 1.3154(3) 0.0604(7) Uani 1 1 d . . . . .
H24 H 0.3322 0.6368 1.3257 0.072 Uiso 1 1 calc R . . . .
C25 C 0.44914(19) 0.5860(2) 1.3497(3) 0.0740(9) Uani 1 1 d . . . . .
H25 H 0.4387 0.5248 1.3817 0.089 Uiso 1 1 calc R . . . .
C26 C 0.5279(2) 0.6100(3) 1.3365(4) 0.0797(10) Uani 1 1 d . . . . .
H26 H 0.5705 0.5650 1.3590 0.096 Uiso 1 1 calc R . . . .
C27 C 0.54338(18) 0.7001(3) 1.2905(4) 0.0823(10) Uani 1 1 d . . . . .
H27 H 0.5970 0.7168 1.2842 0.099 Uiso 1 1 calc R . . . .
C28 C 0.47986(16) 0.7664(2) 1.2532(4) 0.0686(8) Uani 1 1 d . . . . .
H28 H 0.4903 0.8272 1.2193 0.082 Uiso 1 1 calc R . . . .
N1 N 0.33539(11) 0.81122(13) 1.2269(2) 0.0498(5) Uani 1 1 d . . . . .
N2 N 0.00182(14) 1.07064(17) 0.8256(3) 0.0675(7) 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
C1 C2 1.385(3) . ?
C1 C6 1.410(3) . ?
C1 N1 1.393(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.412(3) . ?
C4 C5 1.393(3) . ?
C4 C22 1.457(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(3) . ?
C6 C7 1.442(3) . ?
C7 C8 1.389(3) . ?
C7 C12 1.400(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.374(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.389(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.374(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.393(3) . ?
C12 N1 1.403(3) . ?
C13 C14 1.444(3) . ?
C13 N2 1.148(3) . ?
C14 C15 1.490(3) . ?
C14 C22 1.347(3) . ?
C15 C16 1.387(3) . ?
C15 C20 1.381(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.373(4) . ?
C18 C19 1.372(4) . ?
C18 C21 1.509(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.385(3) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22 0.9300 . ?
C23 C24 1.367(3) . ?
C23 C28 1.383(3) . ?
C23 N1 1.425(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.386(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.375(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.366(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.379(4) . ?
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
C2 C1 C6 121.4(2) . . ?
C2 C1 N1 129.8(2) . . ?
N1 C1 C6 108.8(2) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 C1 117.7(2) . . ?
C3 C2 H2 121.2 . . ?
C2 C3 H3 118.6 . . ?
C2 C3 C4 122.9(2) . . ?
C4 C3 H3 118.6 . . ?
C3 C4 C22 116.4(2) . . ?
C5 C4 C3 118.2(2) . . ?
C5 C4 C22 125.4(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C7 106.9(2) . . ?
C5 C6 C1 119.6(2) . . ?
C5 C6 C7 133.4(2) . . ?
C8 C7 C6 133.7(2) . . ?
C8 C7 C12 119.0(2) . . ?
C12 C7 C6 107.1(2) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.6(3) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 121.3 . . ?
C10 C11 C12 117.4(3) . . ?
C12 C11 H11 121.3 . . ?
C7 C12 N1 108.9(2) . . ?
C11 C12 C7 121.9(2) . . ?
C11 C12 N1 129.1(2) . . ?
N2 C13 C14 177.4(3) . . ?
C13 C14 C15 113.9(2) . . ?
C22 C14 C13 121.7(2) . . ?
C22 C14 C15 124.4(2) . . ?
C16 C15 C14 121.8(2) . . ?
C20 C15 C14 121.1(2) . . ?
C20 C15 C16 117.1(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.4(3) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 118.6 . . ?
C18 C17 C16 122.8(3) . . ?
C18 C17 H17 118.6 . . ?
C17 C18 C21 121.7(3) . . ?
C19 C18 C17 116.5(2) . . ?
C19 C18 C21 121.8(3) . . ?
C18 C19 H19 119.1 . . ?
C18 C19 C20 121.8(2) . . ?
C20 C19 H19 119.1 . . ?
C15 C20 C19 121.4(2) . . ?
C15 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C4 C22 H22 114.1 . . ?
C14 C22 C4 131.9(2) . . ?
C14 C22 H22 114.1 . . ?
C24 C23 C28 120.1(2) . . ?
C24 C23 N1 120.5(2) . . ?
C28 C23 N1 119.3(2) . . ?
C23 C24 H24 120.2 . . ?
C23 C24 C25 119.7(3) . . ?
C25 C24 H24 120.2 . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.2(3) . . ?
C26 C25 H25 119.9 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 C25 120.0(3) . . ?
C27 C26 H26 120.0 . . ?
C26 C27 H27 119.9 . . ?
C26 C27 C28 120.3(3) . . ?
C28 C27 H27 119.9 . . ?
C23 C28 H28 120.1 . . ?
C27 C28 C23 119.8(3) . . ?
C27 C28 H28 120.1 . . ?
C1 N1 C12 108.25(18) . . ?
C1 N1 C23 126.2(2) . . ?
C12 N1 C23 125.3(2) . . ?

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
C1 C2 C3 C4 -1.1(4) . . . . ?
C1 C6 C7 C8 -175.3(3) . . . . ?
C1 C6 C7 C12 0.9(3) . . . . ?
C2 C1 C6 C5 -2.2(3) . . . . ?
C2 C1 C6 C7 178.3(2) . . . . ?
C2 C1 N1 C12 -178.4(2) . . . . ?
C2 C1 N1 C23 6.9(4) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C2 C3 C4 C22 176.7(2) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C3 C4 C22 C14 -175.0(2) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C4 C5 C6 C7 -179.9(2) . . . . ?
C5 C4 C22 C14 1.6(4) . . . . ?
C5 C6 C7 C8 5.3(5) . . . . ?
C5 C6 C7 C12 -178.5(2) . . . . ?
C6 C1 C2 C3 2.4(3) . . . . ?
C6 C1 N1 C12 1.1(3) . . . . ?
C6 C1 N1 C23 -173.6(2) . . . . ?
C6 C7 C8 C9 175.8(3) . . . . ?
C6 C7 C12 C11 -176.3(2) . . . . ?
C6 C7 C12 N1 -0.3(3) . . . . ?
C7 C8 C9 C10 -0.5(4) . . . . ?
C7 C12 N1 C1 -0.5(3) . . . . ?
C7 C12 N1 C23 174.3(2) . . . . ?
C8 C7 C12 C11 0.6(4) . . . . ?
C8 C7 C12 N1 176.6(2) . . . . ?
C8 C9 C10 C11 0.6(4) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C10 C11 C12 C7 -0.5(4) . . . . ?
C10 C11 C12 N1 -175.6(2) . . . . ?
C11 C12 N1 C1 175.2(2) . . . . ?
C11 C12 N1 C23 -10.1(4) . . . . ?
C12 C7 C8 C9 -0.1(4) . . . . ?
C13 C14 C15 C16 -169.9(2) . . . . ?
C13 C14 C15 C20 11.9(3) . . . . ?
C13 C14 C22 C4 -2.3(4) . . . . ?
C14 C15 C16 C17 -177.9(3) . . . . ?
C14 C15 C20 C19 178.0(2) . . . . ?
C15 C14 C22 C4 174.9(2) . . . . ?
C15 C16 C17 C18 -0.4(5) . . . . ?
C16 C15 C20 C19 -0.2(4) . . . . ?
C16 C17 C18 C19 0.3(5) . . . . ?
C16 C17 C18 C21 -179.9(3) . . . . ?
C17 C18 C19 C20 -0.1(4) . . . . ?
C18 C19 C20 C15 0.1(4) . . . . ?
C20 C15 C16 C17 0.4(4) . . . . ?
C21 C18 C19 C20 -179.9(3) . . . . ?
C22 C4 C5 C6 -176.2(2) . . . . ?
C22 C14 C15 C16 12.6(4) . . . . ?
C22 C14 C15 C20 -165.6(2) . . . . ?
C23 C24 C25 C26 1.0(4) . . . . ?
C24 C23 C28 C27 -0.3(4) . . . . ?
C24 C23 N1 C1 -63.4(3) . . . . ?
C24 C23 N1 C12 122.8(3) . . . . ?
C24 C25 C26 C27 0.4(5) . . . . ?
C25 C26 C27 C28 -1.7(5) . . . . ?
C26 C27 C28 C23 1.7(5) . . . . ?
C28 C23 C24 C25 -1.0(4) . . . . ?
C28 C23 N1 C1 116.1(3) . . . . ?
C28 C23 N1 C12 -57.7(3) . . . . ?
N1 C1 C2 C3 -178.2(2) . . . . ?
N1 C1 C6 C5 178.3(2) . . . . ?
N1 C1 C6 C7 -1.2(3) . . . . ?
N1 C23 C24 C25 178.5(2) . . . . ?
N1 C23 C28 C27 -179.8(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_2c
_database_code_depnum_ccdc_archive 'CCDC 1480866'
_audit_update_record             
;
2016-05-19 deposited with the CCDC.
2016-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H17 N3 O2'
_chemical_formula_sum            'C27 H17 N3 O2'
_chemical_formula_weight         415.43

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.245(11)
_cell_length_b                   13.979(9)
_cell_length_c                   8.714(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.290(10)
_cell_angle_gamma                90
_cell_volume                     2044(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3715
_cell_measurement_theta_min      1.213
_cell_measurement_theta_max      25.471

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10303
_diffrn_reflns_av_unetI/netI     0.1842
_diffrn_reflns_av_R_equivalents  0.1010
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.213
_diffrn_reflns_theta_max         25.471
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3715
_reflns_number_gt                1490
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0757P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3715
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1947
_refine_ls_R_factor_gt           0.0857
_refine_ls_wR_factor_ref         0.2691
_refine_ls_wR_factor_gt          0.2015
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_restrained_S_all      0.969
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1623(3) 0.6835(2) 0.2707(5) 0.0669(12) Uani 1 1 d . . . . .
N2 N 0.4857(3) 0.4217(3) 0.6593(6) 0.0900(15) Uani 1 1 d . . . . .
N3 N 0.7567(4) 0.6111(4) 1.3305(8) 0.1061(18) Uani 1 1 d . . . . .
C1 C 0.2288(3) 0.5418(3) 0.2739(6) 0.0658(14) Uani 1 1 d . . . . .
C2 C 0.2391(3) 0.4501(3) 0.2192(7) 0.0787(16) Uani 1 1 d . . . . .
H2A H 0.2838 0.4144 0.2661 0.094 Uiso 1 1 calc R U . . .
C3 C 0.1831(4) 0.4126(4) 0.0960(8) 0.0811(16) Uani 1 1 d . . . . .
H3A H 0.1890 0.3504 0.0622 0.097 Uiso 1 1 calc R U . . .
C4 C 0.1183(4) 0.4663(4) 0.0220(7) 0.0859(17) Uani 1 1 d . . . . .
H4A H 0.0827 0.4408 -0.0649 0.103 Uiso 1 1 calc R U . . .
C5 C 0.1046(3) 0.5569(4) 0.0729(7) 0.0755(15) Uani 1 1 d . . . . .
H5A H 0.0600 0.5920 0.0238 0.091 Uiso 1 1 calc R U . . .
C6 C 0.1605(3) 0.5935(3) 0.2010(7) 0.0689(14) Uani 1 1 d . . . . .
C7 C 0.2325(3) 0.6912(3) 0.3860(6) 0.0629(13) Uani 1 1 d . . . . .
C8 C 0.2621(3) 0.7659(3) 0.4839(7) 0.0695(14) Uani 1 1 d . . . . .
H8A H 0.2346 0.8236 0.4773 0.083 Uiso 1 1 calc R U . . .
C9 C 0.3331(3) 0.7537(3) 0.5921(7) 0.0699(14) Uani 1 1 d . . . . .
H9A H 0.3530 0.8038 0.6600 0.084 Uiso 1 1 calc R U . . .
C10 C 0.3772(3) 0.6674(3) 0.6038(7) 0.0675(14) Uani 1 1 d . . . . .
C11 C 0.3463(3) 0.5928(3) 0.4995(6) 0.0687(14) Uani 1 1 d . . . . .
H11A H 0.3743 0.5357 0.5031 0.082 Uiso 1 1 calc R U . . .
C12 C 0.2749(3) 0.6041(3) 0.3924(6) 0.0631(13) Uani 1 1 d . . . . .
C13 C 0.0993(3) 0.7521(3) 0.2340(6) 0.0705(14) Uani 1 1 d . . . . .
C14 C 0.0248(3) 0.7261(4) 0.2535(7) 0.0832(17) Uani 1 1 d . . . . .
H14A H 0.0169 0.6657 0.2918 0.100 Uiso 1 1 calc R U . . .
C15 C -0.0383(4) 0.7903(5) 0.2161(8) 0.101(2) Uani 1 1 d . . . . .
H15A H -0.0888 0.7727 0.2268 0.121 Uiso 1 1 calc R U . . .
C16 C -0.0252(4) 0.8795(5) 0.1632(8) 0.100(2) Uani 1 1 d . . . . .
H16A H -0.0673 0.9226 0.1368 0.120 Uiso 1 1 calc R U . . .
C17 C 0.0493(4) 0.9064(4) 0.1486(7) 0.0912(19) Uani 1 1 d . . . . .
H17A H 0.0577 0.9681 0.1157 0.109 Uiso 1 1 calc R U . . .
C18 C 0.1124(3) 0.8418(4) 0.1830(6) 0.0767(15) Uani 1 1 d . . . . .
H18A H 0.1628 0.8594 0.1714 0.092 Uiso 1 1 calc R U . . .
C19 C 0.4491(3) 0.6634(3) 0.7288(7) 0.0720(15) Uani 1 1 d . . . . .
H19A H 0.4622 0.7211 0.7818 0.086 Uiso 1 1 calc R U . . .
C20 C 0.5011(3) 0.5908(3) 0.7829(7) 0.0678(14) Uani 1 1 d . . . . .
C21 C 0.4907(3) 0.4975(4) 0.7101(6) 0.0714(15) Uani 1 1 d . . . . .
C22 C 0.5680(3) 0.5980(3) 0.9217(7) 0.0675(14) Uani 1 1 d . . . . .
C23 C 0.5911(4) 0.6841(4) 0.9986(9) 0.101(2) Uani 1 1 d . . . . .
H23A H 0.5648 0.7400 0.9585 0.121 Uiso 1 1 calc R U . . .
C24 C 0.6515(4) 0.6891(4) 1.1320(9) 0.110(2) Uani 1 1 d . . . . .
H24A H 0.6651 0.7473 1.1828 0.132 Uiso 1 1 calc R U . . .
C25 C 0.6919(3) 0.6069(4) 1.1897(8) 0.0785(16) Uani 1 1 d . . . . .
C26 C 0.6720(3) 0.5217(4) 1.1183(8) 0.0829(17) Uani 1 1 d . . . . .
H26A H 0.6999 0.4667 1.1577 0.100 Uiso 1 1 calc R U . . .
C27 C 0.6099(3) 0.5168(3) 0.9862(7) 0.0773(15) Uani 1 1 d . . . . .
H27A H 0.5956 0.4577 0.9392 0.093 Uiso 1 1 calc R U . . .
O1 O 0.7654(4) 0.6839(4) 1.4079(9) 0.192(3) Uani 1 1 d . . . . .
O2 O 0.7977(3) 0.5422(3) 1.3715(6) 0.1210(17) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.388(6) . ?
N1 C6 1.395(6) . ?
N1 C13 1.430(6) . ?
N2 C21 1.145(6) . ?
N3 O2 1.199(6) . ?
N3 O1 1.212(7) . ?
N3 C25 1.459(8) . ?
C1 C2 1.394(6) . ?
C1 C6 1.403(7) . ?
C1 C12 1.441(7) . ?
C2 C3 1.373(8) . ?
C2 H2A 0.9300 . ?
C3 C4 1.378(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.379(7) . ?
C4 H4A 0.9300 . ?
C5 C6 1.393(7) . ?
C5 H5A 0.9300 . ?
C7 C8 1.371(6) . ?
C7 C12 1.414(6) . ?
C8 C9 1.374(7) . ?
C8 H8A 0.9300 . ?
C9 C10 1.417(6) . ?
C9 H9A 0.9300 . ?
C10 C11 1.405(7) . ?
C10 C19 1.452(7) . ?
C11 C12 1.373(7) . ?
C11 H11A 0.9300 . ?
C13 C18 1.367(7) . ?
C13 C14 1.382(7) . ?
C14 C15 1.391(7) . ?
C14 H14A 0.9300 . ?
C15 C16 1.366(8) . ?
C15 H15A 0.9300 . ?
C16 C17 1.373(8) . ?
C16 H16A 0.9300 . ?
C17 C18 1.393(7) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C19 C20 1.365(6) . ?
C19 H19A 0.9300 . ?
C20 C21 1.443(7) . ?
C20 C22 1.472(7) . ?
C22 C23 1.391(7) . ?
C22 C27 1.393(6) . ?
C23 C24 1.373(8) . ?
C23 H23A 0.9300 . ?
C24 C25 1.378(7) . ?
C24 H24A 0.9300 . ?
C25 C26 1.351(7) . ?
C26 C27 1.382(7) . ?
C26 H26A 0.9300 . ?
C27 H27A 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
C7 N1 C6 108.3(4) . . ?
C7 N1 C13 127.0(4) . . ?
C6 N1 C13 124.6(5) . . ?
O2 N3 O1 121.3(7) . . ?
O2 N3 C25 120.2(6) . . ?
O1 N3 C25 118.3(6) . . ?
C2 C1 C6 118.6(5) . . ?
C2 C1 C12 135.1(5) . . ?
C6 C1 C12 106.3(4) . . ?
C3 C2 C1 119.8(5) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C2 C3 C4 120.4(5) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C3 C4 C5 122.0(6) . . ?
C3 C4 H4A 119.0 . . ?
C5 C4 H4A 119.0 . . ?
C4 C5 C6 117.2(5) . . ?
C4 C5 H5A 121.4 . . ?
C6 C5 H5A 121.4 . . ?
C5 C6 N1 128.5(5) . . ?
C5 C6 C1 121.9(5) . . ?
N1 C6 C1 109.5(5) . . ?
C8 C7 N1 130.3(4) . . ?
C8 C7 C12 121.1(5) . . ?
N1 C7 C12 108.6(4) . . ?
C7 C8 C9 118.5(5) . . ?
C7 C8 H8A 120.7 . . ?
C9 C8 H8A 120.7 . . ?
C8 C9 C10 122.3(5) . . ?
C8 C9 H9A 118.9 . . ?
C10 C9 H9A 118.9 . . ?
C11 C10 C9 117.9(5) . . ?
C11 C10 C19 126.1(4) . . ?
C9 C10 C19 116.0(5) . . ?
C12 C11 C10 120.1(4) . . ?
C12 C11 H11A 119.9 . . ?
C10 C11 H11A 119.9 . . ?
C11 C12 C7 120.0(5) . . ?
C11 C12 C1 132.7(4) . . ?
C7 C12 C1 107.3(5) . . ?
C18 C13 C14 120.6(5) . . ?
C18 C13 N1 120.9(5) . . ?
C14 C13 N1 118.5(5) . . ?
C13 C14 C15 120.1(5) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C16 C15 C14 119.2(6) . . ?
C16 C15 H15A 120.4 . . ?
C14 C15 H15A 120.4 . . ?
C15 C16 C17 120.8(6) . . ?
C15 C16 H16A 119.6 . . ?
C17 C16 H16A 119.6 . . ?
C16 C17 C18 120.3(6) . . ?
C16 C17 H17A 119.9 . . ?
C18 C17 H17A 119.9 . . ?
C13 C18 C17 119.0(6) . . ?
C13 C18 H18A 120.5 . . ?
C17 C18 H18A 120.5 . . ?
C20 C19 C10 131.8(5) . . ?
C20 C19 H19A 114.1 . . ?
C10 C19 H19A 114.1 . . ?
C19 C20 C21 121.0(5) . . ?
C19 C20 C22 124.2(5) . . ?
C21 C20 C22 114.7(4) . . ?
N2 C21 C20 176.1(6) . . ?
C23 C22 C27 116.6(6) . . ?
C23 C22 C20 122.6(5) . . ?
C27 C22 C20 120.8(5) . . ?
C24 C23 C22 121.9(6) . . ?
C24 C23 H23A 119.0 . . ?
C22 C23 H23A 119.0 . . ?
C23 C24 C25 119.2(6) . . ?
C23 C24 H24A 120.4 . . ?
C25 C24 H24A 120.4 . . ?
C26 C25 C24 120.9(6) . . ?
C26 C25 N3 119.1(5) . . ?
C24 C25 N3 119.9(6) . . ?
C25 C26 C27 119.6(5) . . ?
C25 C26 H26A 120.2 . . ?
C27 C26 H26A 120.2 . . ?
C26 C27 C22 121.7(5) . . ?
C26 C27 H27A 119.1 . . ?
C22 C27 H27A 119.1 . . ?

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
C6 C1 C2 C3 0.3(7) . . . . ?
C12 C1 C2 C3 -177.1(6) . . . . ?
C1 C2 C3 C4 2.5(8) . . . . ?
C2 C3 C4 C5 -3.5(9) . . . . ?
C3 C4 C5 C6 1.6(8) . . . . ?
C4 C5 C6 N1 177.2(5) . . . . ?
C4 C5 C6 C1 1.3(8) . . . . ?
C7 N1 C6 C5 -174.9(5) . . . . ?
C13 N1 C6 C5 8.8(8) . . . . ?
C7 N1 C6 C1 1.4(5) . . . . ?
C13 N1 C6 C1 -174.9(4) . . . . ?
C2 C1 C6 C5 -2.3(7) . . . . ?
C12 C1 C6 C5 175.9(5) . . . . ?
C2 C1 C6 N1 -178.9(4) . . . . ?
C12 C1 C6 N1 -0.7(5) . . . . ?
C6 N1 C7 C8 178.6(5) . . . . ?
C13 N1 C7 C8 -5.3(8) . . . . ?
C6 N1 C7 C12 -1.5(5) . . . . ?
C13 N1 C7 C12 174.7(4) . . . . ?
N1 C7 C8 C9 178.3(5) . . . . ?
C12 C7 C8 C9 -1.7(7) . . . . ?
C7 C8 C9 C10 1.0(8) . . . . ?
C8 C9 C10 C11 0.4(7) . . . . ?
C8 C9 C10 C19 -177.1(5) . . . . ?
C9 C10 C11 C12 -1.1(7) . . . . ?
C19 C10 C11 C12 176.1(5) . . . . ?
C10 C11 C12 C7 0.5(7) . . . . ?
C10 C11 C12 C1 -179.5(5) . . . . ?
C8 C7 C12 C11 1.0(7) . . . . ?
N1 C7 C12 C11 -179.0(4) . . . . ?
C8 C7 C12 C1 -179.0(4) . . . . ?
N1 C7 C12 C1 1.0(5) . . . . ?
C2 C1 C12 C11 -2.5(10) . . . . ?
C6 C1 C12 C11 179.8(5) . . . . ?
C2 C1 C12 C7 177.5(5) . . . . ?
C6 C1 C12 C7 -0.2(5) . . . . ?
C7 N1 C13 C18 61.5(7) . . . . ?
C6 N1 C13 C18 -122.9(6) . . . . ?
C7 N1 C13 C14 -117.5(6) . . . . ?
C6 N1 C13 C14 58.0(7) . . . . ?
C18 C13 C14 C15 2.2(9) . . . . ?
N1 C13 C14 C15 -178.7(5) . . . . ?
C13 C14 C15 C16 -1.4(9) . . . . ?
C14 C15 C16 C17 -0.7(10) . . . . ?
C15 C16 C17 C18 2.0(10) . . . . ?
C14 C13 C18 C17 -0.9(8) . . . . ?
N1 C13 C18 C17 -180.0(5) . . . . ?
C16 C17 C18 C13 -1.2(9) . . . . ?
C11 C10 C19 C20 -3.9(9) . . . . ?
C9 C10 C19 C20 173.3(5) . . . . ?
C10 C19 C20 C21 2.0(9) . . . . ?
C10 C19 C20 C22 -174.5(5) . . . . ?
C19 C20 C22 C23 -8.9(8) . . . . ?
C21 C20 C22 C23 174.4(5) . . . . ?
C19 C20 C22 C27 168.7(5) . . . . ?
C21 C20 C22 C27 -8.0(7) . . . . ?
C27 C22 C23 C24 -0.5(9) . . . . ?
C20 C22 C23 C24 177.2(6) . . . . ?
C22 C23 C24 C25 1.5(11) . . . . ?
C23 C24 C25 C26 -1.0(10) . . . . ?
C23 C24 C25 N3 179.5(6) . . . . ?
O2 N3 C25 C26 8.6(9) . . . . ?
O1 N3 C25 C26 -168.0(7) . . . . ?
O2 N3 C25 C24 -171.8(6) . . . . ?
O1 N3 C25 C24 11.6(10) . . . . ?
C24 C25 C26 C27 -0.5(9) . . . . ?
N3 C25 C26 C27 179.0(5) . . . . ?
C25 C26 C27 C22 1.6(9) . . . . ?
C23 C22 C27 C26 -1.1(8) . . . . ?
C20 C22 C27 C26 -178.8(5) . . . . ?

_refine_diff_density_max         0.335
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.057

_shelxl_version_number           2014-3



