# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_ydkr
_database_code_depnum_ccdc_archive 'CCDC 1457735'
_audit_update_record             
;
2016-03-04 deposited with the CCDC.
2017-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H17 N'
_chemical_formula_weight         343.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   8.2997(3)
_cell_length_b                   33.2041(4)
_cell_length_c                   12.4646(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3435.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    0.587
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8528
_exptl_absorpt_correction_T_max  0.9171
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Image plate'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28185
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.44
_diffrn_reflns_theta_max         66.96
_reflns_number_total             3051
_reflns_number_gt                2715
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3051
_refine_ls_number_parameters     312
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.1091
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_restrained_S_all      0.929
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H1 H 0.0604(14) 0.0813(4) 0.3953(9) 0.023(3) Uiso 1 1 d . . .
H2 H 0.0216(15) 0.0682(4) 0.2090(9) 0.030(3) Uiso 1 1 d . . .
H3 H 0.1458(17) 0.1125(4) 0.0842(11) 0.035(4) Uiso 1 1 d . . .
H4 H 0.3051(15) 0.1691(4) 0.1419(10) 0.027(3) Uiso 1 1 d . . .
H5 H 0.5288(18) 0.2489(4) 0.4025(12) 0.039(4) Uiso 1 1 d . . .
H6 H 0.5426(15) 0.2740(4) 0.5809(10) 0.030(3) Uiso 1 1 d . . .
H7 H 0.3941(16) 0.2405(4) 0.7189(10) 0.028(3) Uiso 1 1 d . . .
H8 H 0.2544(16) 0.1796(4) 0.6855(9) 0.029(3) Uiso 1 1 d . . .
H9 H 0.1958(14) 0.1257(3) 0.6477(9) 0.017(3) Uiso 1 1 d . . .
H10 H -0.0802(15) 0.1813(4) 0.5746(9) 0.023(3) Uiso 1 1 d . . .
C1 C 0.11300(14) 0.09863(3) 0.34359(9) 0.0218(3) Uani 1 1 d . . .
H11 H -0.3623(16) 0.1749(4) 0.6133(10) 0.028(3) Uiso 1 1 d . . .
H12 H -0.4751(18) 0.1116(4) 0.6597(10) 0.029(3) Uiso 1 1 d . . .
H13 H -0.3105(14) 0.0527(4) 0.6636(9) 0.023(3) Uiso 1 1 d . . .
H14 H -0.0732(17) -0.0028(4) 0.6582(10) 0.030(3) Uiso 1 1 d . . .
H15 H 0.1682(16) -0.0418(4) 0.6359(10) 0.032(3) Uiso 1 1 d . . .
H16 H 0.4073(17) -0.0096(4) 0.5763(10) 0.033(3) Uiso 1 1 d . . .
H17 H 0.4115(16) 0.0616(4) 0.5404(10) 0.028(3) Uiso 1 1 d . . .
C2 C 0.09316(14) 0.09189(3) 0.23691(9) 0.0249(3) Uani 1 1 d . . .
C3 C 0.16495(15) 0.11788(3) 0.15980(9) 0.0269(3) Uani 1 1 d . . .
C4 C 0.25367(14) 0.14996(3) 0.19189(9) 0.0254(3) Uani 1 1 d . . .
C5 C 0.27626(13) 0.15855(3) 0.30320(8) 0.0212(3) Uani 1 1 d . . .
C6 C 0.37851(13) 0.20035(3) 0.43388(8) 0.0220(3) Uani 1 1 d . . .
C7 C 0.47161(14) 0.23518(3) 0.46113(9) 0.0267(3) Uani 1 1 d . . .
C8 C 0.47698(14) 0.24908(4) 0.56376(10) 0.0288(3) Uani 1 1 d . . .
C9 C 0.39174(14) 0.22874(3) 0.64625(9) 0.0265(3) Uani 1 1 d . . .
C10 C 0.30983(13) 0.19405(3) 0.62464(9) 0.0229(3) Uani 1 1 d . . .
C11 C 0.30226(12) 0.17777(3) 0.51820(8) 0.0201(3) Uani 1 1 d . . .
C12 C 0.22079(12) 0.14198(3) 0.49084(8) 0.0191(2) Uani 1 1 d . . .
C13 C 0.20356(12) 0.13233(3) 0.38137(8) 0.0194(3) Uani 1 1 d . . .
C14 C 0.14844(13) 0.11601(3) 0.57876(8) 0.0194(3) Uani 1 1 d . . .
C15 C -0.03227(13) 0.11970(3) 0.59460(8) 0.0197(2) Uani 1 1 d . . .
C16 C -0.12759(13) 0.15395(3) 0.59234(8) 0.0225(3) Uani 1 1 d . . .
C17 C -0.29071(14) 0.15030(3) 0.61592(8) 0.0245(3) Uani 1 1 d . . .
C18 C -0.35641(14) 0.11292(3) 0.64289(8) 0.0246(3) Uani 1 1 d . . .
C19 C -0.26160(14) 0.07849(3) 0.64471(8) 0.0228(3) Uani 1 1 d . . .
C20 C -0.09834(13) 0.08187(3) 0.61970(7) 0.0199(3) Uani 1 1 d . . .
C21 C 0.02988(13) 0.05163(3) 0.61314(8) 0.0201(3) Uani 1 1 d . . .
C22 C 0.02716(14) 0.01027(3) 0.63404(8) 0.0237(3) Uani 1 1 d . . .
C23 C 0.16775(14) -0.01161(3) 0.62064(9) 0.0272(3) Uani 1 1 d . . .
C24 C 0.30846(15) 0.00697(3) 0.58511(9) 0.0271(3) Uani 1 1 d . . .
C25 C 0.31216(14) 0.04826(3) 0.56486(8) 0.0236(3) Uani 1 1 d . . .
C26 C 0.17292(13) 0.07056(3) 0.58042(7) 0.0201(3) Uani 1 1 d . . .
N1 N 0.36549(11) 0.19098(3) 0.32931(7) 0.0233(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3585(15) . ?
C1 C13 1.4276(15) . ?
C2 C3 1.4224(16) . ?
C3 C4 1.3554(17) . ?
C4 C5 1.4288(15) . ?
C5 N1 1.3469(14) . ?
C5 C13 1.4394(14) . ?
C6 N1 1.3444(14) . ?
C6 C7 1.4317(16) . ?
C6 C11 1.4378(15) . ?
C7 C8 1.3608(17) . ?
C8 C9 1.4192(17) . ?
C9 C10 1.3643(16) . ?
C10 C11 1.4340(15) . ?
C11 C12 1.4092(14) . ?
C12 C13 1.4089(14) . ?
C12 C14 1.5182(14) . ?
C14 C15 1.5177(15) . ?
C14 C26 1.5230(14) . ?
C15 C16 1.3855(15) . ?
C15 C20 1.4058(14) . ?
C16 C17 1.3907(16) . ?
C17 C18 1.3967(16) . ?
C18 C19 1.3881(16) . ?
C19 C20 1.3949(16) . ?
C20 C21 1.4655(14) . ?
C21 C22 1.3979(15) . ?
C21 C26 1.4038(15) . ?
C22 C23 1.3847(16) . ?
C23 C24 1.3930(17) . ?
C24 C25 1.3942(16) . ?
C25 C26 1.3862(15) . ?

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 C13 121.05(10) . . ?
C1 C2 C3 120.71(11) . . ?
C4 C3 C2 120.32(10) . . ?
C3 C4 C5 120.98(10) . . ?
N1 C5 C4 117.80(10) . . ?
N1 C5 C13 123.41(10) . . ?
C4 C5 C13 118.79(10) . . ?
N1 C6 C7 117.41(9) . . ?
N1 C6 C11 123.54(10) . . ?
C7 C6 C11 119.04(10) . . ?
C8 C7 C6 120.98(10) . . ?
C7 C8 C9 120.21(11) . . ?
C10 C9 C8 120.49(11) . . ?
C9 C10 C11 121.51(10) . . ?
C12 C11 C10 124.24(9) . . ?
C12 C11 C6 118.30(9) . . ?
C10 C11 C6 117.42(10) . . ?
C13 C12 C11 118.36(9) . . ?
C13 C12 C14 121.99(9) . . ?
C11 C12 C14 119.60(9) . . ?
C12 C13 C1 123.45(10) . . ?
C12 C13 C5 118.38(9) . . ?
C1 C13 C5 118.13(9) . . ?
C15 C14 C12 116.03(8) . . ?
C15 C14 C26 102.12(8) . . ?
C12 C14 C26 121.32(8) . . ?
C16 C15 C20 121.00(10) . . ?
C16 C15 C14 128.89(9) . . ?
C20 C15 C14 110.02(9) . . ?
C15 C16 C17 118.69(10) . . ?
C16 C17 C18 120.55(11) . . ?
C19 C18 C17 120.97(11) . . ?
C18 C19 C20 118.72(10) . . ?
C19 C20 C15 120.05(10) . . ?
C19 C20 C21 131.50(10) . . ?
C15 C20 C21 108.45(9) . . ?
C22 C21 C26 120.51(10) . . ?
C22 C21 C20 130.61(10) . . ?
C26 C21 C20 108.88(9) . . ?
C23 C22 C21 118.64(10) . . ?
C22 C23 C24 120.83(11) . . ?
C23 C24 C25 120.76(11) . . ?
C26 C25 C24 118.79(11) . . ?
C25 C26 C21 120.43(10) . . ?
C25 C26 C14 129.70(10) . . ?
C21 C26 C14 109.56(9) . . ?
C6 N1 C5 117.62(9) . . ?

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
C13 C1 C2 C3 1.23(17) . . . . ?
C1 C2 C3 C4 -0.39(17) . . . . ?
C2 C3 C4 C5 -0.39(17) . . . . ?
C3 C4 C5 N1 -179.83(10) . . . . ?
C3 C4 C5 C13 0.31(16) . . . . ?
N1 C6 C7 C8 173.15(10) . . . . ?
C11 C6 C7 C8 -5.84(16) . . . . ?
C6 C7 C8 C9 1.00(17) . . . . ?
C7 C8 C9 C10 3.07(18) . . . . ?
C8 C9 C10 C11 -2.16(17) . . . . ?
C9 C10 C11 C12 179.52(10) . . . . ?
C9 C10 C11 C6 -2.66(15) . . . . ?
N1 C6 C11 C12 5.57(15) . . . . ?
C7 C6 C11 C12 -175.52(9) . . . . ?
N1 C6 C11 C10 -172.39(10) . . . . ?
C7 C6 C11 C10 6.53(14) . . . . ?
C10 C11 C12 C13 171.25(9) . . . . ?
C6 C11 C12 C13 -6.56(14) . . . . ?
C10 C11 C12 C14 -6.19(15) . . . . ?
C6 C11 C12 C14 176.01(9) . . . . ?
C11 C12 C13 C1 -175.01(10) . . . . ?
C14 C12 C13 C1 2.36(15) . . . . ?
C11 C12 C13 C5 2.74(14) . . . . ?
C14 C12 C13 C5 -179.88(9) . . . . ?
C2 C1 C13 C12 176.48(10) . . . . ?
C2 C1 C13 C5 -1.28(16) . . . . ?
N1 C5 C13 C12 2.77(15) . . . . ?
C4 C5 C13 C12 -177.37(9) . . . . ?
N1 C5 C13 C1 -179.35(10) . . . . ?
C4 C5 C13 C1 0.50(14) . . . . ?
C13 C12 C14 C15 -75.68(12) . . . . ?
C11 C12 C14 C15 101.66(11) . . . . ?
C13 C12 C14 C26 49.12(14) . . . . ?
C11 C12 C14 C26 -133.54(10) . . . . ?
C12 C14 C15 C16 -40.66(14) . . . . ?
C26 C14 C15 C16 -174.82(10) . . . . ?
C12 C14 C15 C20 142.76(9) . . . . ?
C26 C14 C15 C20 8.60(10) . . . . ?
C20 C15 C16 C17 0.27(14) . . . . ?
C14 C15 C16 C17 -175.98(10) . . . . ?
C15 C16 C17 C18 0.94(15) . . . . ?
C16 C17 C18 C19 -1.31(16) . . . . ?
C17 C18 C19 C20 0.42(15) . . . . ?
C18 C19 C20 C15 0.79(14) . . . . ?
C18 C19 C20 C21 -178.93(9) . . . . ?
C16 C15 C20 C19 -1.15(14) . . . . ?
C14 C15 C20 C19 175.75(8) . . . . ?
C16 C15 C20 C21 178.63(9) . . . . ?
C14 C15 C20 C21 -4.48(10) . . . . ?
C19 C20 C21 C22 -2.65(18) . . . . ?
C15 C20 C21 C22 177.61(10) . . . . ?
C19 C20 C21 C26 177.68(10) . . . . ?
C15 C20 C21 C26 -2.07(11) . . . . ?
C26 C21 C22 C23 -0.71(15) . . . . ?
C20 C21 C22 C23 179.65(10) . . . . ?
C21 C22 C23 C24 -1.21(16) . . . . ?
C22 C23 C24 C25 1.68(17) . . . . ?
C23 C24 C25 C26 -0.19(16) . . . . ?
C24 C25 C26 C21 -1.72(15) . . . . ?
C24 C25 C26 C14 171.13(10) . . . . ?
C22 C21 C26 C25 2.20(15) . . . . ?
C20 C21 C26 C25 -178.09(9) . . . . ?
C22 C21 C26 C14 -171.97(9) . . . . ?
C20 C21 C26 C14 7.75(11) . . . . ?
C15 C14 C26 C25 176.68(10) . . . . ?
C12 C14 C26 C25 45.67(15) . . . . ?
C15 C14 C26 C21 -9.86(10) . . . . ?
C12 C14 C26 C21 -140.86(10) . . . . ?
C7 C6 N1 C5 -179.14(9) . . . . ?
C11 C6 N1 C5 -0.21(15) . . . . ?
C4 C5 N1 C6 176.12(9) . . . . ?
C13 C5 N1 C6 -4.02(15) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        66.96
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_mefa_p
_database_code_depnum_ccdc_archive 'CCDC 1457736'
_audit_update_record             
;
2016-03-04 deposited with the CCDC.
2017-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H19 N'
_chemical_formula_weight         357.43

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/a'

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

_cell_length_a                   7.379(6)
_cell_length_b                   22.716(16)
_cell_length_c                   9.381(7)
_cell_angle_alpha                90
_cell_angle_beta                 111.14(2)
_cell_angle_gamma                90
_cell_volume                     1466.51(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1729
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      23.24

_exptl_crystal_description       platelet
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Image plate'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1093
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         23.24
_reflns_number_total             623
_reflns_number_gt                621
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         623
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1219
_refine_ls_R_factor_gt           0.1217
_refine_ls_wR_factor_ref         0.3149
_refine_ls_wR_factor_gt          0.3147
_refine_ls_goodness_of_fit_ref   1.838
_refine_ls_restrained_S_all      1.838
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.021(3) 0.1872(7) 0.604(2) 0.060(6) Uani 1 1 d . . .
C25 C 0.089(4) 0.1440(10) 0.396(3) 0.076(9) Uani 1 1 d . . .
C21 C -0.114(4) 0.2299(9) 0.349(3) 0.099(13) Uani 1 1 d . . .
H16 H -0.1847 0.2572 0.3816 0.118 Uiso 1 1 calc R . .
C20 C -0.123(4) 0.2296(11) 0.200(3) 0.078(9) Uani 1 1 d . . .
H15 H -0.2010 0.2564 0.1303 0.093 Uiso 1 1 calc R . .
C26 C 0.005(3) 0.1881(11) 0.453(3) 0.072(9) Uani 1 1 d . . .
C27 C -0.088(4) 0.2298(11) 0.655(2) 0.082(9) Uani 1 1 d . . .
H18 H -0.0977 0.2168 0.7499 0.123 Uiso 1 1 calc R . .
H19 H -0.2164 0.2336 0.5796 0.123 Uiso 1 1 calc R . .
H17 H -0.0237 0.2672 0.6707 0.123 Uiso 1 1 calc R . .
C16 C 0.565(4) 0.1358(10) 0.905(3) 0.083(10) Uani 1 1 d . . .
H11 H 0.6899 0.1264 0.9699 0.100 Uiso 1 1 calc R . .
C18 C 0.094(3) 0.1467(11) 0.251(3) 0.081(9) Uani 1 1 d . . .
H13 H 0.1699 0.1203 0.2208 0.097 Uiso 1 1 calc R . .
C11 C 0.281(3) -0.0599(9) 0.467(2) 0.052(6) Uani 1 1 d . . .
C3 C 0.456(3) -0.1195(11) 0.681(3) 0.072(8) Uani 1 1 d . . .
H3 H 0.5045 -0.1558 0.7237 0.086 Uiso 1 1 calc R . .
C22 C 0.190(4) 0.1658(9) 0.712(3) 0.075(10) Uani 1 1 d . . .
C23 C 0.293(4) 0.1246(10) 0.661(3) 0.076(10) Uani 1 1 d . . .
C19 C -0.011(3) 0.1879(11) 0.155(3) 0.066(7) Uani 1 1 d . . .
H14 H -0.0105 0.1892 0.0556 0.079 Uiso 1 1 calc R . .
C17 C 0.490(4) 0.1076(11) 0.756(3) 0.080(9) Uani 1 1 d . . .
H12 H 0.5624 0.0807 0.7243 0.096 Uiso 1 1 calc R . .
C7 C -0.163(3) -0.0063(11) 0.068(2) 0.075(9) Uani 1 1 d . . .
H7 H -0.2699 0.0065 -0.0149 0.090 Uiso 1 1 calc R . .
C2 C 0.480(3) -0.0737(11) 0.777(3) 0.071(8) Uani 1 1 d . . .
H2 H 0.5439 -0.0790 0.8811 0.086 Uiso 1 1 calc R . .
C24 C 0.201(3) 0.0967(9) 0.510(2) 0.058(6) Uani 1 1 d . . .
C14 C 0.273(4) 0.1895(10) 0.860(2) 0.070(7) Uani 1 1 d . . .
H9 H 0.2013 0.2153 0.8959 0.084 Uiso 1 1 calc R . .
C10 C 0.309(3) -0.0114(10) 0.565(2) 0.057(7) Uani 1 1 d . . .
C6 C -0.097(3) -0.0643(10) 0.071(2) 0.065(7) Uani 1 1 d . . .
H6 H -0.1594 -0.0900 -0.0093 0.078 Uiso 1 1 calc R . .
C4 C 0.365(4) -0.1166(10) 0.524(3) 0.076(9) Uani 1 1 d . . .
H4 H 0.3578 -0.1486 0.4607 0.091 Uiso 1 1 calc R . .
C15 C 0.464(4) 0.1746(9) 0.954(3) 0.073(9) Uani 1 1 d . . .
H10 H 0.5198 0.1918 1.0499 0.087 Uiso 1 1 calc R . .
C12 C 0.143(3) -0.0478(10) 0.315(3) 0.065(8) Uani 1 1 d . . .
C8 C -0.070(3) 0.0334(12) 0.190(3) 0.079(8) Uani 1 1 d . . .
H8 H -0.1124 0.0721 0.1880 0.095 Uiso 1 1 calc R . .
C13 C 0.091(4) 0.0119(11) 0.317(3) 0.076(8) Uani 1 1 d . . .
C5 C 0.060(3) -0.0826(8) 0.192(2) 0.065(7) Uani 1 1 d . . .
H5 H 0.1112 -0.1199 0.1902 0.078 Uiso 1 1 calc R . .
C1 C 0.410(4) -0.0171(11) 0.719(2) 0.079(9) Uani 1 1 d . . .
H1 H 0.4311 0.0152 0.7841 0.095 Uiso 1 1 calc R . .
C9 C 0.200(3) 0.0384(9) 0.467(2) 0.062(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
N1 C22 1.37(2) . ?
N1 C26 1.38(3) . ?
N1 C27 1.45(3) . ?
C25 C18 1.38(4) . ?
C25 C26 1.38(4) . ?
C25 C24 1.53(3) . ?
C21 C20 1.38(4) . ?
C21 C26 1.41(3) . ?
C20 C19 1.42(4) . ?
C16 C15 1.34(4) . ?
C16 C17 1.45(3) . ?
C18 C19 1.34(3) . ?
C11 C10 1.40(3) . ?
C11 C4 1.45(3) . ?
C11 C12 1.45(3) . ?
C3 C2 1.34(3) . ?
C3 C4 1.38(3) . ?
C22 C23 1.39(4) . ?
C22 C14 1.41(3) . ?
C23 C17 1.46(3) . ?
C23 C24 1.48(3) . ?
C7 C6 1.40(3) . ?
C7 C8 1.43(3) . ?
C2 C1 1.42(3) . ?
C24 C9 1.38(3) . ?
C14 C15 1.41(3) . ?
C10 C1 1.37(3) . ?
C10 C9 1.50(3) . ?
C6 C5 1.36(2) . ?
C12 C5 1.35(3) . ?
C12 C13 1.41(3) . ?
C8 C13 1.43(3) . ?
C13 C9 1.48(3) . ?

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
C22 N1 C26 119(2) . . ?
C22 N1 C27 117.3(16) . . ?
C26 N1 C27 118.4(18) . . ?
C18 C25 C26 122(2) . . ?
C18 C25 C24 121(3) . . ?
C26 C25 C24 117(3) . . ?
C20 C21 C26 119(3) . . ?
C21 C20 C19 119(2) . . ?
N1 C26 C25 120(2) . . ?
N1 C26 C21 121(3) . . ?
C25 C26 C21 118(2) . . ?
C15 C16 C17 124(2) . . ?
C19 C18 C25 119(3) . . ?
C10 C11 C4 120.8(18) . . ?
C10 C11 C12 112.4(18) . . ?
C4 C11 C12 126.2(19) . . ?
C2 C3 C4 125(2) . . ?
N1 C22 C23 117(2) . . ?
N1 C22 C14 123(2) . . ?
C23 C22 C14 120(2) . . ?
C22 C23 C17 121(2) . . ?
C22 C23 C24 120(2) . . ?
C17 C23 C24 119(3) . . ?
C18 C19 C20 121(3) . . ?
C16 C17 C23 115(3) . . ?
C6 C7 C8 121(2) . . ?
C3 C2 C1 121(2) . . ?
C9 C24 C23 130.0(18) . . ?
C9 C24 C25 121.7(19) . . ?
C23 C24 C25 108.2(19) . . ?
C15 C14 C22 121(2) . . ?
C1 C10 C11 121(2) . . ?
C1 C10 C9 133(2) . . ?
C11 C10 C9 105.7(16) . . ?
C5 C6 C7 119.2(17) . . ?
C3 C4 C11 115(2) . . ?
C16 C15 C14 120(2) . . ?
C5 C12 C13 122(2) . . ?
C5 C12 C11 132(2) . . ?
C13 C12 C11 105.5(19) . . ?
C7 C8 C13 118(3) . . ?
C12 C13 C8 118(2) . . ?
C12 C13 C9 110.4(18) . . ?
C8 C13 C9 131(2) . . ?
C12 C5 C6 121(2) . . ?
C10 C1 C2 118(2) . . ?
C24 C9 C13 127.8(19) . . ?
C24 C9 C10 126.8(17) . . ?
C13 C9 C10 105.4(18) . . ?

_diffrn_measured_fraction_theta_max 0.297
_diffrn_reflns_theta_full        23.22
_diffrn_measured_fraction_theta_full 0.297
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.094
####################################################################### 
# 
# 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_ydkr_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1457738'
_audit_update_record             
;
2016-03-04 deposited with the CCDC.
2017-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H19 N'
_chemical_formula_weight         357.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/a

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

_cell_length_a                   8.5137(2)
_cell_length_b                   21.9630(6)
_cell_length_c                   9.8776(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.4061(17)
_cell_angle_gamma                90.00
_cell_volume                     1788.90(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.584
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8442
_exptl_absorpt_correction_T_max  0.8725
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Image plate'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18604
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.03
_diffrn_reflns_theta_max         67.00
_reflns_number_total             3190
_reflns_number_gt                2859
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0017(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3190
_refine_ls_number_parameters     330
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.1303
_refine_ls_wR_factor_gt          0.1242
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.29852(16) -0.01216(6) 0.26505(12) 0.0243(3) Uani 1 1 d . . .
H1 H 0.3373(17) -0.0534(6) 0.2995(13) 0.021(3) Uiso 1 1 d . . .
C2 C 0.27939(16) 0.02990(6) 0.36525(13) 0.0278(3) Uani 1 1 d . . .
H2 H 0.3078(18) 0.0198(6) 0.4664(15) 0.030(4) Uiso 1 1 d . . .
C3 C 0.21824(17) 0.08793(6) 0.32722(13) 0.0280(3) Uani 1 1 d . . .
H3 H 0.1988(19) 0.1178(6) 0.3971(15) 0.029(4) Uiso 1 1 d . . .
C4 C 0.17449(16) 0.10462(6) 0.18745(13) 0.0246(3) Uani 1 1 d . . .
H4 H 0.1244(18) 0.1457(6) 0.1587(14) 0.031(4) Uiso 1 1 d . . .
C5 C 0.07543(16) 0.11698(5) -0.14570(13) 0.0244(3) Uani 1 1 d . . .
H5 H 0.0486(18) 0.1544(6) -0.1010(14) 0.030(4) Uiso 1 1 d . . .
C6 C 0.03507(17) 0.11091(6) -0.29008(13) 0.0264(3) Uani 1 1 d . . .
H6 H -0.0207(18) 0.1450(6) -0.3502(15) 0.030(4) Uiso 1 1 d . . .
C7 C 0.06676(16) 0.05656(6) -0.35053(13) 0.0264(3) Uani 1 1 d . . .
H7 H 0.0355(17) 0.0505(6) -0.4553(14) 0.028(4) Uiso 1 1 d . . .
C8 C 0.14105(16) 0.00784(6) -0.26866(13) 0.0237(3) Uani 1 1 d . . .
H8 H 0.1571(17) -0.0309(6) -0.3166(13) 0.024(3) Uiso 1 1 d . . .
C9 C 0.26142(15) -0.02943(5) -0.00796(12) 0.0205(3) Uani 1 1 d . . .
C10 C 0.25883(15) 0.00423(5) 0.12360(12) 0.0209(3) Uani 1 1 d . . .
C11 C 0.19491(14) 0.06285(5) 0.08755(12) 0.0209(3) Uani 1 1 d . . .
C12 C 0.14985(15) 0.06863(5) -0.06408(12) 0.0213(3) Uani 1 1 d . . .
C13 C 0.18581(15) 0.01349(5) -0.12355(12) 0.0200(3) Uani 1 1 d . . .
C14 C 0.31894(16) -0.22740(6) 0.19811(13) 0.0242(3) Uani 1 1 d . . .
H9 H 0.2576(19) -0.2651(6) 0.1939(15) 0.032(4) Uiso 1 1 d . . .
C15 C 0.44515(17) -0.21495(6) 0.31381(13) 0.0273(3) Uani 1 1 d . . .
H10 H 0.4712(18) -0.2450(6) 0.3974(15) 0.030(4) Uiso 1 1 d . . .
C16 C 0.54104(17) -0.16351(6) 0.31799(13) 0.0273(3) Uani 1 1 d . . .
H11 H 0.6360(19) -0.1565(6) 0.3943(14) 0.027(4) Uiso 1 1 d . . .
C17 C 0.50169(16) -0.12142(6) 0.20994(12) 0.0235(3) Uani 1 1 d . . .
H12 H 0.5627(18) -0.0857(7) 0.2108(14) 0.031(4) Uiso 1 1 d . . .
C18 C 0.36749(16) -0.10362(6) -0.25917(13) 0.0239(3) Uani 1 1 d . . .
H13 H 0.4302(18) -0.0650(6) -0.2494(15) 0.028(4) Uiso 1 1 d . . .
C19 C 0.34574(17) -0.13780(6) -0.38064(13) 0.0281(3) Uani 1 1 d . . .
H14 H 0.3952(18) -0.1233(6) -0.4569(14) 0.027(4) Uiso 1 1 d . . .
C20 C 0.25286(16) -0.19055(6) -0.39531(13) 0.0281(3) Uani 1 1 d . . .
H15 H 0.2391(19) -0.2144(6) -0.4816(16) 0.033(4) Uiso 1 1 d . . .
C21 C 0.18900(16) -0.21123(6) -0.28762(13) 0.0244(3) Uani 1 1 d . . .
H16 H 0.1288(18) -0.2487(6) -0.2970(13) 0.026(3) Uiso 1 1 d . . .
C22 C 0.28460(15) -0.18669(5) 0.08545(12) 0.0199(3) Uani 1 1 d . . .
C23 C 0.36778(15) -0.13065(5) 0.09723(12) 0.0200(3) Uani 1 1 d . . .
C24 C 0.31100(14) -0.08770(5) -0.01997(12) 0.0194(3) Uani 1 1 d . . .
C25 C 0.29654(15) -0.12154(5) -0.15222(12) 0.0198(3) Uani 1 1 d . . .
C26 C 0.21652(15) -0.17815(5) -0.16264(12) 0.0204(3) Uani 1 1 d . . .
C27 C 0.08417(18) -0.25752(6) -0.05371(14) 0.0282(3) Uani 1 1 d . . .
H17 H -0.008(2) -0.2568(7) -0.1434(17) 0.041(4) Uiso 1 1 d . . .
H18 H 0.0441(19) -0.2623(6) 0.0299(16) 0.034(4) Uiso 1 1 d . . .
H19 H 0.1536(19) -0.2965(7) -0.0571(14) 0.034(4) Uiso 1 1 d . . .
N1 N 0.17478(12) -0.20068(4) -0.04255(10) 0.0216(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3927(17) . ?
C1 C10 1.4004(16) . ?
C1 H1 0.995(13) . ?
C2 C3 1.3925(19) . ?
C2 H2 0.993(14) . ?
C3 C4 1.3867(17) . ?
C3 H3 0.996(14) . ?
C4 C11 1.3895(17) . ?
C4 H4 1.008(14) . ?
C5 C12 1.3875(17) . ?
C5 C6 1.3877(18) . ?
C5 H5 0.986(14) . ?
C6 C7 1.3908(18) . ?
C6 H6 1.000(14) . ?
C7 C8 1.3943(18) . ?
C7 H7 1.011(13) . ?
C8 C13 1.3940(16) . ?
C8 H8 0.999(12) . ?
C9 C24 1.3619(17) . ?
C9 C13 1.4970(16) . ?
C9 C10 1.5001(15) . ?
C10 C11 1.4085(17) . ?
C11 C12 1.4563(16) . ?
C12 C13 1.4123(16) . ?
C14 C15 1.3873(19) . ?
C14 C22 1.4005(17) . ?
C14 H9 0.974(15) . ?
C15 C16 1.388(2) . ?
C15 H10 1.037(14) . ?
C16 C17 1.3885(18) . ?
C16 H11 0.971(15) . ?
C17 C23 1.3960(18) . ?
C17 H12 0.940(16) . ?
C18 C19 1.3881(17) . ?
C18 C25 1.3975(17) . ?
C18 H13 0.994(14) . ?
C19 C20 1.3897(19) . ?
C19 H14 1.002(14) . ?
C20 C21 1.3861(19) . ?
C20 H15 0.982(15) . ?
C21 C26 1.4010(17) . ?
C21 H16 0.963(14) . ?
C22 N1 1.4067(16) . ?
C22 C23 1.4102(16) . ?
C23 C24 1.4783(16) . ?
C24 C25 1.4812(15) . ?
C25 C26 1.4092(16) . ?
C26 N1 1.4101(15) . ?
C27 N1 1.4572(15) . ?
C27 H17 1.025(17) . ?
C27 H18 0.974(16) . ?
C27 H19 1.045(15) . ?

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 C10 119.78(12) . . ?
C2 C1 H1 116.6(7) . . ?
C10 C1 H1 123.6(7) . . ?
C3 C2 C1 121.15(12) . . ?
C3 C2 H2 117.2(8) . . ?
C1 C2 H2 121.7(8) . . ?
C4 C3 C2 120.01(11) . . ?
C4 C3 H3 117.8(8) . . ?
C2 C3 H3 122.1(8) . . ?
C3 C4 C11 118.85(12) . . ?
C3 C4 H4 120.4(8) . . ?
C11 C4 H4 120.7(8) . . ?
C12 C5 C6 118.95(11) . . ?
C12 C5 H5 120.0(8) . . ?
C6 C5 H5 121.0(8) . . ?
C5 C6 C7 119.92(12) . . ?
C5 C6 H6 119.9(8) . . ?
C7 C6 H6 120.2(8) . . ?
C6 C7 C8 121.20(12) . . ?
C6 C7 H7 121.6(8) . . ?
C8 C7 H7 117.2(8) . . ?
C13 C8 C7 119.78(11) . . ?
C13 C8 H8 121.9(7) . . ?
C7 C8 H8 118.3(7) . . ?
C24 C9 C13 127.53(10) . . ?
C24 C9 C10 127.61(10) . . ?
C13 C9 C10 104.72(9) . . ?
C1 C10 C11 117.99(11) . . ?
C1 C10 C9 133.29(11) . . ?
C11 C10 C9 108.64(10) . . ?
C4 C11 C10 122.18(11) . . ?
C4 C11 C12 128.71(11) . . ?
C10 C11 C12 109.02(10) . . ?
C5 C12 C13 121.97(11) . . ?
C5 C12 C11 129.03(11) . . ?
C13 C12 C11 108.92(10) . . ?
C8 C13 C12 118.15(11) . . ?
C8 C13 C9 133.15(11) . . ?
C12 C13 C9 108.62(10) . . ?
C15 C14 C22 119.64(12) . . ?
C15 C14 H9 120.0(9) . . ?
C22 C14 H9 120.3(9) . . ?
C14 C15 C16 120.94(12) . . ?
C14 C15 H10 119.9(8) . . ?
C16 C15 H10 119.1(8) . . ?
C15 C16 C17 119.42(12) . . ?
C15 C16 H11 121.4(8) . . ?
C17 C16 H11 119.2(8) . . ?
C16 C17 C23 120.61(12) . . ?
C16 C17 H12 121.4(9) . . ?
C23 C17 H12 117.9(9) . . ?
C19 C18 C25 120.75(12) . . ?
C19 C18 H13 119.9(8) . . ?
C25 C18 H13 119.3(8) . . ?
C18 C19 C20 119.40(12) . . ?
C18 C19 H14 119.2(8) . . ?
C20 C19 H14 121.4(8) . . ?
C21 C20 C19 120.99(11) . . ?
C21 C20 H15 120.4(9) . . ?
C19 C20 H15 118.5(9) . . ?
C20 C21 C26 119.65(12) . . ?
C20 C21 H16 120.5(8) . . ?
C26 C21 H16 119.8(8) . . ?
C14 C22 N1 122.36(11) . . ?
C14 C22 C23 119.36(11) . . ?
N1 C22 C23 118.21(10) . . ?
C17 C23 C22 119.10(11) . . ?
C17 C23 C24 125.09(11) . . ?
C22 C23 C24 115.64(10) . . ?
C9 C24 C23 125.41(10) . . ?
C9 C24 C25 126.06(11) . . ?
C23 C24 C25 108.04(9) . . ?
C18 C25 C26 119.03(10) . . ?
C18 C25 C24 124.66(11) . . ?
C26 C25 C24 116.09(10) . . ?
C21 C26 C25 119.59(11) . . ?
C21 C26 N1 122.50(11) . . ?
C25 C26 N1 117.82(10) . . ?
N1 C27 H17 109.1(8) . . ?
N1 C27 H18 108.6(9) . . ?
H17 C27 H18 112.4(13) . . ?
N1 C27 H19 114.2(8) . . ?
H17 C27 H19 107.5(11) . . ?
H18 C27 H19 105.0(11) . . ?
C22 N1 C26 115.41(10) . . ?
C22 N1 C27 118.44(10) . . ?
C26 N1 C27 118.46(10) . . ?

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
C10 C1 C2 C3 1.3(2) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C2 C3 C4 C11 -0.86(19) . . . . ?
C12 C5 C6 C7 1.14(19) . . . . ?
C5 C6 C7 C8 -1.0(2) . . . . ?
C6 C7 C8 C13 -0.5(2) . . . . ?
C2 C1 C10 C11 -2.18(18) . . . . ?
C2 C1 C10 C9 -178.50(13) . . . . ?
C24 C9 C10 C1 -2.1(2) . . . . ?
C13 C9 C10 C1 173.79(13) . . . . ?
C24 C9 C10 C11 -178.63(12) . . . . ?
C13 C9 C10 C11 -2.78(13) . . . . ?
C3 C4 C11 C10 -0.13(19) . . . . ?
C3 C4 C11 C12 176.20(12) . . . . ?
C1 C10 C11 C4 1.65(18) . . . . ?
C9 C10 C11 C4 178.82(11) . . . . ?
C1 C10 C11 C12 -175.33(11) . . . . ?
C9 C10 C11 C12 1.85(13) . . . . ?
C6 C5 C12 C13 0.05(19) . . . . ?
C6 C5 C12 C11 -176.20(12) . . . . ?
C4 C11 C12 C5 -0.2(2) . . . . ?
C10 C11 C12 C5 176.55(12) . . . . ?
C4 C11 C12 C13 -176.81(12) . . . . ?
C10 C11 C12 C13 -0.09(14) . . . . ?
C7 C8 C13 C12 1.62(18) . . . . ?
C7 C8 C13 C9 177.97(13) . . . . ?
C5 C12 C13 C8 -1.44(18) . . . . ?
C11 C12 C13 C8 175.49(11) . . . . ?
C5 C12 C13 C9 -178.63(11) . . . . ?
C11 C12 C13 C9 -1.70(13) . . . . ?
C24 C9 C13 C8 2.0(2) . . . . ?
C10 C9 C13 C8 -173.89(13) . . . . ?
C24 C9 C13 C12 178.58(12) . . . . ?
C10 C9 C13 C12 2.72(13) . . . . ?
C22 C14 C15 C16 -1.83(19) . . . . ?
C14 C15 C16 C17 5.37(19) . . . . ?
C15 C16 C17 C23 -0.47(19) . . . . ?
C25 C18 C19 C20 -0.3(2) . . . . ?
C18 C19 C20 C21 -3.5(2) . . . . ?
C19 C20 C21 C26 0.8(2) . . . . ?
C15 C14 C22 N1 170.54(11) . . . . ?
C15 C14 C22 C23 -6.50(18) . . . . ?
C16 C17 C23 C22 -7.78(18) . . . . ?
C16 C17 C23 C24 177.27(11) . . . . ?
C14 C22 C23 C17 11.22(17) . . . . ?
N1 C22 C23 C17 -165.94(10) . . . . ?
C14 C22 C23 C24 -173.36(10) . . . . ?
N1 C22 C23 C24 9.48(16) . . . . ?
C13 C9 C24 C23 -172.59(11) . . . . ?
C10 C9 C24 C23 2.3(2) . . . . ?
C13 C9 C24 C25 -1.5(2) . . . . ?
C10 C9 C24 C25 173.43(11) . . . . ?
C17 C23 C24 C9 -60.37(18) . . . . ?
C22 C23 C24 C9 124.52(13) . . . . ?
C17 C23 C24 C25 127.20(12) . . . . ?
C22 C23 C24 C25 -47.91(13) . . . . ?
C19 C18 C25 C26 6.59(19) . . . . ?
C19 C18 C25 C24 -179.15(11) . . . . ?
C9 C24 C25 C18 60.06(18) . . . . ?
C23 C24 C25 C18 -127.57(13) . . . . ?
C9 C24 C25 C26 -125.53(13) . . . . ?
C23 C24 C25 C26 46.84(14) . . . . ?
C20 C21 C26 C25 5.54(19) . . . . ?
C20 C21 C26 N1 -171.01(11) . . . . ?
C18 C25 C26 C21 -9.18(18) . . . . ?
C24 C25 C26 C21 176.08(11) . . . . ?
C18 C25 C26 N1 167.53(11) . . . . ?
C24 C25 C26 N1 -7.21(16) . . . . ?
C14 C22 N1 C26 -143.89(12) . . . . ?
C23 C22 N1 C26 33.18(15) . . . . ?
C14 C22 N1 C27 5.12(17) . . . . ?
C23 C22 N1 C27 -177.81(10) . . . . ?
C21 C26 N1 C22 142.29(12) . . . . ?
C25 C26 N1 C22 -34.31(15) . . . . ?
C21 C26 N1 C27 -6.71(18) . . . . ?
C25 C26 N1 C27 176.69(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        67.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.039
####################################################################### 
# 
# 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_f2plus
_database_code_depnum_ccdc_archive 'CCDC 1457737'
_audit_update_record             
;
2016-03-04 deposited with the CCDC.
2017-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H19 N'
_chemical_formula_weight         357.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   7.3384(2)
_cell_length_b                   18.5774(6)
_cell_length_c                   13.3299(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.1024(18)
_cell_angle_gamma                90.00
_cell_volume                     1817.24(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.575
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.7778
_exptl_absorpt_correction_T_max  0.9136
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Image plate'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20326
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0532
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.32
_diffrn_reflns_theta_max         66.99
_reflns_number_total             6277
_reflns_number_gt                5264
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0072(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.0(11)
_refine_ls_number_reflns         6277
_refine_ls_number_parameters     508
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0628
_refine_ls_wR_factor_ref         0.2075
_refine_ls_wR_factor_gt          0.1697
_refine_ls_goodness_of_fit_ref   1.451
_refine_ls_restrained_S_all      1.451
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3619(6) 0.3495(2) 0.4481(3) 0.0300(10) Uani 1 1 d . . .
H1 H 0.2694 0.3655 0.4926 0.036 Uiso 1 1 calc R . .
C2 C 0.4760(6) 0.3995(2) 0.3990(3) 0.0335(11) Uani 1 1 d . . .
H2 H 0.4595 0.4495 0.4107 0.040 Uiso 1 1 calc R . .
C3 C 0.6114(6) 0.3770(3) 0.3341(3) 0.0356(11) Uani 1 1 d . . .
H3 H 0.6853 0.4115 0.3009 0.043 Uiso 1 1 calc R . .
C4 C 0.6393(6) 0.3043(2) 0.3176(3) 0.0321(10) Uani 1 1 d . . .
H4 H 0.7333 0.2884 0.2740 0.038 Uiso 1 1 calc R . .
C5 C 0.6574(6) 0.1313(2) 0.3124(3) 0.0306(10) Uani 1 1 d . . .
H5 H 0.7458 0.1511 0.2683 0.037 Uiso 1 1 calc R . .
C6 C 0.6455(6) 0.0574(3) 0.3262(3) 0.0356(11) Uani 1 1 d . . .
H6 H 0.7246 0.0261 0.2906 0.043 Uiso 1 1 calc R . .
C7 C 0.5164(6) 0.0292(3) 0.3928(3) 0.0346(11) Uani 1 1 d . . .
H7 H 0.5090 -0.0214 0.4024 0.041 Uiso 1 1 calc R . .
C8 C 0.4005(6) 0.0739(2) 0.4445(3) 0.0296(10) Uani 1 1 d . . .
H8 H 0.3189 0.0540 0.4924 0.036 Uiso 1 1 calc R . .
C9 C 0.2935(5) 0.2109(2) 0.4684(3) 0.0256(9) Uani 1 1 d . . .
C10 C 0.3874(6) 0.2764(2) 0.4302(3) 0.0258(9) Uani 1 1 d . . .
C11 C 0.5279(6) 0.2552(2) 0.3657(3) 0.0258(9) Uani 1 1 d . . .
C12 C 0.5378(6) 0.1759(2) 0.3641(3) 0.0262(9) Uani 1 1 d . . .
C13 C 0.4011(6) 0.1489(2) 0.4273(3) 0.0262(9) Uani 1 1 d . . .
C14 C -0.0391(6) 0.3105(2) 0.7486(3) 0.0333(11) Uani 1 1 d . . .
H9 H -0.0423 0.3065 0.8196 0.040 Uiso 1 1 calc R . .
C15 C -0.1138(6) 0.3702(3) 0.7019(4) 0.0350(11) Uani 1 1 d . . .
H10 H -0.1647 0.4077 0.7414 0.042 Uiso 1 1 calc R . .
C16 C -0.1154(6) 0.3760(3) 0.5979(4) 0.0400(12) Uani 1 1 d . . .
H11 H -0.1750 0.4156 0.5668 0.048 Uiso 1 1 calc R . .
C17 C -0.0300(6) 0.3242(3) 0.5395(4) 0.0363(11) Uani 1 1 d . . .
H12 H -0.0288 0.3288 0.4685 0.044 Uiso 1 1 calc R . .
C18 C -0.0005(6) 0.0833(2) 0.5080(3) 0.0302(10) Uani 1 1 d . . .
H13 H -0.0082 0.0903 0.4375 0.036 Uiso 1 1 calc R . .
C19 C -0.0623(6) 0.0195(2) 0.5504(3) 0.0343(11) Uani 1 1 d . . .
H14 H -0.1152 -0.0166 0.5091 0.041 Uiso 1 1 calc R . .
C20 C -0.0471(6) 0.0089(2) 0.6511(3) 0.0335(11) Uani 1 1 d . . .
H15 H -0.0779 -0.0367 0.6784 0.040 Uiso 1 1 calc R . .
C21 C 0.0127(6) 0.0636(2) 0.7151(3) 0.0300(10) Uani 1 1 d . . .
H16 H 0.0169 0.0561 0.7856 0.036 Uiso 1 1 calc R . .
C22 C 0.0414(6) 0.2561(2) 0.6909(3) 0.0269(9) Uani 1 1 d . . .
C23 C 0.0538(5) 0.2656(2) 0.5855(3) 0.0233(9) Uani 1 1 d . . .
C24 C 0.1495(6) 0.2059(2) 0.5323(3) 0.0262(9) Uani 1 1 d . . .
C25 C 0.0736(5) 0.1373(2) 0.5694(3) 0.0245(9) Uani 1 1 d . . .
C26 C 0.0662(6) 0.1296(2) 0.6741(3) 0.0251(9) Uani 1 1 d . . .
C27 C 0.1078(6) 0.1833(3) 0.8400(3) 0.0355(11) Uani 1 1 d . . .
H17 H 0.1630 0.2264 0.8695 0.053 Uiso 1 1 calc R . .
H18 H 0.1811 0.1410 0.8574 0.053 Uiso 1 1 calc R . .
H19 H -0.0160 0.1773 0.8662 0.053 Uiso 1 1 calc R . .
C28 C -0.1036(6) 0.0995(2) 1.0853(3) 0.0296(10) Uani 1 1 d . . .
H20 H -0.1890 0.0747 1.0443 0.036 Uiso 1 1 calc R . .
C29 C 0.0197(6) 0.0604(3) 1.1463(3) 0.0358(11) Uani 1 1 d . . .
H21 H 0.0177 0.0093 1.1455 0.043 Uiso 1 1 calc R . .
C30 C 0.1447(6) 0.0966(3) 1.2079(3) 0.0358(11) Uani 1 1 d . . .
H22 H 0.2225 0.0700 1.2511 0.043 Uiso 1 1 calc R . .
C31 C 0.1553(6) 0.1707(3) 1.2060(3) 0.0338(11) Uani 1 1 d . . .
H23 H 0.2422 0.1954 1.2462 0.041 Uiso 1 1 calc R . .
C32 C 0.1461(6) 0.3394(2) 1.1588(3) 0.0351(11) Uani 1 1 d . . .
H24 H 0.2380 0.3288 1.2069 0.042 Uiso 1 1 calc R . .
C33 C 0.1249(6) 0.4092(3) 1.1229(3) 0.0335(10) Uani 1 1 d . . .
H25 H 0.2024 0.4468 1.1455 0.040 Uiso 1 1 calc R . .
C34 C -0.0118(6) 0.4227(3) 1.0536(3) 0.0347(11) Uani 1 1 d . . .
H26 H -0.0251 0.4703 1.0288 0.042 Uiso 1 1 calc R . .
C35 C -0.1309(6) 0.3699(2) 1.0184(3) 0.0291(10) Uani 1 1 d . . .
H27 H -0.2244 0.3817 0.9718 0.035 Uiso 1 1 calc R . .
C36 C -0.2060(6) 0.2297(2) 1.0315(3) 0.0268(10) Uani 1 1 d . . .
C37 C -0.0992(6) 0.1739(2) 1.0856(3) 0.0270(9) Uani 1 1 d . . .
C38 C 0.0368(6) 0.2088(2) 1.1442(3) 0.0277(10) Uani 1 1 d . . .
C39 C 0.0322(6) 0.2857(2) 1.1238(3) 0.0275(9) Uani 1 1 d . . .
C40 C -0.1101(6) 0.2986(2) 1.0532(3) 0.0271(9) Uani 1 1 d . . .
C41 C -0.4961(6) 0.0616(2) 0.8116(3) 0.0318(10) Uani 1 1 d . . .
H28 H -0.4924 0.0476 0.7431 0.038 Uiso 1 1 calc R . .
C42 C -0.5597(6) 0.0142(2) 0.8842(3) 0.0340(11) Uani 1 1 d . . .
H29 H -0.5988 -0.0326 0.8650 0.041 Uiso 1 1 calc R . .
C43 C -0.5671(7) 0.0343(2) 0.9854(3) 0.0366(11) Uani 1 1 d . . .
H30 H -0.6165 0.0025 1.0341 0.044 Uiso 1 1 calc R . .
C44 C -0.5020(6) 0.1006(2) 1.0132(3) 0.0320(10) Uani 1 1 d . . .
H31 H -0.5091 0.1147 1.0816 0.038 Uiso 1 1 calc R . .
C45 C -0.5234(6) 0.3360(2) 0.9378(3) 0.0293(10) Uani 1 1 d . . .
H32 H -0.5214 0.3471 1.0074 0.035 Uiso 1 1 calc R . .
C46 C -0.6080(6) 0.3826(2) 0.8706(4) 0.0353(11) Uani 1 1 d . . .
H33 H -0.6660 0.4252 0.8939 0.042 Uiso 1 1 calc R . .
C47 C -0.6066(6) 0.3661(2) 0.7688(3) 0.0329(10) Uani 1 1 d . . .
H34 H -0.6584 0.3991 0.7224 0.039 Uiso 1 1 calc R . .
C48 C -0.5323(6) 0.3034(2) 0.7341(3) 0.0295(10) Uani 1 1 d . . .
H35 H -0.5325 0.2935 0.6642 0.035 Uiso 1 1 calc R . .
C49 C -0.4374(6) 0.1306(2) 0.8407(3) 0.0262(9) Uani 1 1 d . . .
C50 C -0.4254(6) 0.1479(2) 0.9434(3) 0.0258(9) Uani 1 1 d . . .
C51 C -0.3521(5) 0.2191(2) 0.9665(3) 0.0251(9) Uani 1 1 d . . .
C52 C -0.4415(6) 0.2729(2) 0.9034(3) 0.0300(10) Uani 1 1 d . . .
C53 C -0.4560(6) 0.2538(2) 0.8008(3) 0.0268(9) Uani 1 1 d . . .
C54 C -0.3961(6) 0.1674(2) 0.6658(3) 0.0296(10) Uani 1 1 d . . .
H36 H -0.5218 0.1639 0.6413 0.044 Uiso 1 1 calc R . .
H37 H -0.3343 0.1212 0.6562 0.044 Uiso 1 1 calc R . .
H38 H -0.3316 0.2050 0.6284 0.044 Uiso 1 1 calc R . .
N1 N -0.3970(5) 0.18551(18) 0.7718(2) 0.0275(8) Uani 1 1 d . . .
N2 N 0.1007(5) 0.19085(18) 0.7325(2) 0.0281(8) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C10 1.392(6) . ?
C1 C2 1.412(6) . ?
C2 C3 1.383(6) . ?
C3 C4 1.384(6) . ?
C4 C11 1.383(6) . ?
C5 C6 1.387(6) . ?
C5 C12 1.391(6) . ?
C6 C7 1.401(6) . ?
C7 C8 1.375(6) . ?
C8 C13 1.413(6) . ?
C9 C24 1.362(6) . ?
C9 C10 1.488(6) . ?
C9 C13 1.501(6) . ?
C10 C11 1.400(6) . ?
C11 C12 1.475(6) . ?
C12 C13 1.405(6) . ?
C14 C15 1.385(6) . ?
C14 C22 1.401(6) . ?
C15 C16 1.390(7) . ?
C16 C17 1.388(7) . ?
C17 C23 1.393(6) . ?
C18 C19 1.389(6) . ?
C18 C25 1.405(6) . ?
C19 C20 1.361(6) . ?
C20 C21 1.398(6) . ?
C21 C26 1.398(5) . ?
C22 N2 1.402(5) . ?
C22 C23 1.420(6) . ?
C23 C24 1.492(6) . ?
C24 C25 1.476(6) . ?
C25 C26 1.403(5) . ?
C26 N2 1.402(5) . ?
C27 N2 1.440(5) . ?
C28 C37 1.382(6) . ?
C28 C29 1.416(6) . ?
C29 C30 1.402(7) . ?
C30 C31 1.379(6) . ?
C31 C38 1.389(6) . ?
C32 C39 1.382(6) . ?
C32 C33 1.390(6) . ?
C33 C34 1.386(6) . ?
C34 C35 1.395(6) . ?
C35 C40 1.411(6) . ?
C36 C51 1.391(5) . ?
C36 C37 1.486(6) . ?
C36 C40 1.489(6) . ?
C37 C38 1.423(6) . ?
C38 C39 1.455(6) . ?
C39 C40 1.426(6) . ?
C41 C42 1.390(6) . ?
C41 C49 1.406(6) . ?
C42 C43 1.401(6) . ?
C43 C44 1.371(6) . ?
C44 C50 1.399(6) . ?
C45 C46 1.392(6) . ?
C45 C52 1.395(6) . ?
C46 C47 1.391(6) . ?
C47 C48 1.367(6) . ?
C48 C53 1.397(6) . ?
C49 N1 1.405(5) . ?
C49 C50 1.409(5) . ?
C50 C51 1.461(6) . ?
C51 C52 1.461(6) . ?
C52 C53 1.416(6) . ?
C53 N1 1.396(5) . ?
C54 N1 1.452(5) . ?

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
C10 C1 C2 118.8(4) . . ?
C3 C2 C1 121.2(4) . . ?
C2 C3 C4 120.1(4) . . ?
C11 C4 C3 118.8(4) . . ?
C6 C5 C12 119.0(4) . . ?
C5 C6 C7 119.8(4) . . ?
C8 C7 C6 120.8(4) . . ?
C7 C8 C13 120.8(4) . . ?
C24 C9 C10 129.1(4) . . ?
C24 C9 C13 125.8(4) . . ?
C10 C9 C13 105.0(3) . . ?
C1 C10 C11 118.6(4) . . ?
C1 C10 C9 132.6(4) . . ?
C11 C10 C9 108.8(4) . . ?
C4 C11 C10 122.4(4) . . ?
C4 C11 C12 128.5(4) . . ?
C10 C11 C12 109.0(4) . . ?
C5 C12 C13 122.4(4) . . ?
C5 C12 C11 129.4(4) . . ?
C13 C12 C11 108.2(4) . . ?
C12 C13 C8 116.9(4) . . ?
C12 C13 C9 108.7(3) . . ?
C8 C13 C9 134.2(4) . . ?
C15 C14 C22 119.9(4) . . ?
C14 C15 C16 120.9(4) . . ?
C17 C16 C15 120.2(4) . . ?
C16 C17 C23 119.7(4) . . ?
C19 C18 C25 119.9(4) . . ?
C20 C19 C18 119.9(4) . . ?
C19 C20 C21 121.5(4) . . ?
C20 C21 C26 119.1(4) . . ?
C14 C22 N2 122.5(4) . . ?
C14 C22 C23 118.8(4) . . ?
N2 C22 C23 118.6(4) . . ?
C17 C23 C22 120.2(4) . . ?
C17 C23 C24 125.5(4) . . ?
C22 C23 C24 114.2(3) . . ?
C9 C24 C25 124.2(4) . . ?
C9 C24 C23 127.8(4) . . ?
C25 C24 C23 107.7(3) . . ?
C26 C25 C18 119.4(4) . . ?
C26 C25 C24 115.9(4) . . ?
C18 C25 C24 124.5(4) . . ?
C21 C26 N2 123.0(3) . . ?
C21 C26 C25 119.4(4) . . ?
N2 C26 C25 117.5(4) . . ?
C37 C28 C29 119.8(4) . . ?
C30 C29 C28 120.4(4) . . ?
C31 C30 C29 120.4(4) . . ?
C30 C31 C38 118.9(4) . . ?
C39 C32 C33 119.3(4) . . ?
C34 C33 C32 118.6(4) . . ?
C33 C34 C35 123.3(4) . . ?
C34 C35 C40 118.9(4) . . ?
C51 C36 C37 127.5(4) . . ?
C51 C36 C40 127.3(4) . . ?
C37 C36 C40 104.9(4) . . ?
C28 C37 C38 118.2(4) . . ?
C28 C37 C36 133.2(4) . . ?
C38 C37 C36 108.5(4) . . ?
C31 C38 C37 122.1(4) . . ?
C31 C38 C39 128.6(4) . . ?
C37 C38 C39 109.2(4) . . ?
C32 C39 C40 122.9(4) . . ?
C32 C39 C38 129.2(4) . . ?
C40 C39 C38 107.8(4) . . ?
C35 C40 C39 117.0(4) . . ?
C35 C40 C36 133.8(4) . . ?
C39 C40 C36 109.2(4) . . ?
C42 C41 C49 119.2(4) . . ?
C41 C42 C43 121.0(4) . . ?
C44 C43 C42 119.1(4) . . ?
C43 C44 C50 121.7(4) . . ?
C46 C45 C52 120.2(4) . . ?
C47 C46 C45 119.1(4) . . ?
C48 C47 C46 121.4(4) . . ?
C47 C48 C53 120.4(4) . . ?
N1 C49 C41 123.1(4) . . ?
N1 C49 C50 117.2(4) . . ?
C41 C49 C50 119.7(4) . . ?
C44 C50 C49 118.6(4) . . ?
C44 C50 C51 125.2(4) . . ?
C49 C50 C51 115.8(4) . . ?
C36 C51 C50 122.8(4) . . ?
C36 C51 C52 127.4(4) . . ?
C50 C51 C52 109.4(3) . . ?
C45 C52 C53 119.8(4) . . ?
C45 C52 C51 125.3(4) . . ?
C53 C52 C51 114.7(4) . . ?
N1 C53 C48 123.1(4) . . ?
N1 C53 C52 118.2(4) . . ?
C48 C53 C52 118.6(4) . . ?
C53 N1 C49 114.4(3) . . ?
C53 N1 C54 118.8(3) . . ?
C49 N1 C54 118.0(3) . . ?
C22 N2 C26 115.2(3) . . ?
C22 N2 C27 119.2(3) . . ?
C26 N2 C27 118.7(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
C10 C1 C2 C3 -0.1(7) . . . . ?
C1 C2 C3 C4 -1.1(7) . . . . ?
C2 C3 C4 C11 1.0(6) . . . . ?
C12 C5 C6 C7 -1.1(7) . . . . ?
C5 C6 C7 C8 0.3(7) . . . . ?
C6 C7 C8 C13 3.8(7) . . . . ?
C2 C1 C10 C11 1.3(6) . . . . ?
C2 C1 C10 C9 -179.9(4) . . . . ?
C24 C9 C10 C1 1.4(7) . . . . ?
C13 C9 C10 C1 -174.4(5) . . . . ?
C24 C9 C10 C11 -179.7(4) . . . . ?
C13 C9 C10 C11 4.6(4) . . . . ?
C3 C4 C11 C10 0.3(6) . . . . ?
C3 C4 C11 C12 -176.4(4) . . . . ?
C1 C10 C11 C4 -1.4(6) . . . . ?
C9 C10 C11 C4 179.5(4) . . . . ?
C1 C10 C11 C12 175.8(4) . . . . ?
C9 C10 C11 C12 -3.3(5) . . . . ?
C6 C5 C12 C13 -2.2(6) . . . . ?
C6 C5 C12 C11 177.1(4) . . . . ?
C4 C11 C12 C5 -1.8(8) . . . . ?
C10 C11 C12 C5 -178.8(4) . . . . ?
C4 C11 C12 C13 177.6(4) . . . . ?
C10 C11 C12 C13 0.6(5) . . . . ?
C5 C12 C13 C8 6.1(6) . . . . ?
C11 C12 C13 C8 -173.4(4) . . . . ?
C5 C12 C13 C9 -178.2(4) . . . . ?
C11 C12 C13 C9 2.3(4) . . . . ?
C7 C8 C13 C12 -6.8(6) . . . . ?
C7 C8 C13 C9 178.9(4) . . . . ?
C24 C9 C13 C12 179.9(4) . . . . ?
C10 C9 C13 C12 -4.2(4) . . . . ?
C24 C9 C13 C8 -5.5(7) . . . . ?
C10 C9 C13 C8 170.5(5) . . . . ?
C22 C14 C15 C16 2.0(7) . . . . ?
C14 C15 C16 C17 -4.6(7) . . . . ?
C15 C16 C17 C23 1.4(7) . . . . ?
C25 C18 C19 C20 -1.5(7) . . . . ?
C18 C19 C20 C21 6.6(7) . . . . ?
C19 C20 C21 C26 -3.1(7) . . . . ?
C15 C14 C22 N2 -172.6(4) . . . . ?
C15 C14 C22 C23 3.6(6) . . . . ?
C16 C17 C23 C22 4.3(6) . . . . ?
C16 C17 C23 C24 179.7(4) . . . . ?
C14 C22 C23 C17 -6.8(6) . . . . ?
N2 C22 C23 C17 169.5(4) . . . . ?
C14 C22 C23 C24 177.3(4) . . . . ?
N2 C22 C23 C24 -6.3(6) . . . . ?
C10 C9 C24 C25 -176.5(4) . . . . ?
C13 C9 C24 C25 -1.6(6) . . . . ?
C10 C9 C24 C23 -3.6(7) . . . . ?
C13 C9 C24 C23 171.3(4) . . . . ?
C17 C23 C24 C9 57.9(6) . . . . ?
C22 C23 C24 C9 -126.4(4) . . . . ?
C17 C23 C24 C25 -128.2(4) . . . . ?
C22 C23 C24 C25 47.4(5) . . . . ?
C19 C18 C25 C26 -6.9(6) . . . . ?
C19 C18 C25 C24 177.6(4) . . . . ?
C9 C24 C25 C26 123.9(4) . . . . ?
C23 C24 C25 C26 -50.3(4) . . . . ?
C9 C24 C25 C18 -60.5(6) . . . . ?
C23 C24 C25 C18 125.4(4) . . . . ?
C20 C21 C26 N2 169.8(4) . . . . ?
C20 C21 C26 C25 -5.4(6) . . . . ?
C18 C25 C26 C21 10.3(6) . . . . ?
C24 C25 C26 C21 -173.8(4) . . . . ?
C18 C25 C26 N2 -165.2(4) . . . . ?
C24 C25 C26 N2 10.7(5) . . . . ?
C37 C28 C29 C30 0.8(7) . . . . ?
C28 C29 C30 C31 -3.3(7) . . . . ?
C29 C30 C31 C38 1.8(7) . . . . ?
C39 C32 C33 C34 0.6(7) . . . . ?
C32 C33 C34 C35 0.6(7) . . . . ?
C33 C34 C35 C40 -1.3(6) . . . . ?
C29 C28 C37 C38 3.1(6) . . . . ?
C29 C28 C37 C36 179.6(4) . . . . ?
C51 C36 C37 C28 3.5(8) . . . . ?
C40 C36 C37 C28 -170.5(5) . . . . ?
C51 C36 C37 C38 -179.6(4) . . . . ?
C40 C36 C37 C38 6.3(4) . . . . ?
C30 C31 C38 C37 2.2(7) . . . . ?
C30 C31 C38 C39 -174.6(4) . . . . ?
C28 C37 C38 C31 -4.7(6) . . . . ?
C36 C37 C38 C31 178.0(4) . . . . ?
C28 C37 C38 C39 172.7(4) . . . . ?
C36 C37 C38 C39 -4.7(5) . . . . ?
C33 C32 C39 C40 -1.2(7) . . . . ?
C33 C32 C39 C38 174.9(4) . . . . ?
C31 C38 C39 C32 1.6(7) . . . . ?
C37 C38 C39 C32 -175.6(4) . . . . ?
C31 C38 C39 C40 178.1(4) . . . . ?
C37 C38 C39 C40 1.0(5) . . . . ?
C34 C35 C40 C39 0.7(6) . . . . ?
C34 C35 C40 C36 -178.5(4) . . . . ?
C32 C39 C40 C35 0.5(6) . . . . ?
C38 C39 C40 C35 -176.4(4) . . . . ?
C32 C39 C40 C36 179.9(4) . . . . ?
C38 C39 C40 C36 3.1(4) . . . . ?
C51 C36 C40 C35 -0.5(7) . . . . ?
C37 C36 C40 C35 173.6(4) . . . . ?
C51 C36 C40 C39 -179.8(4) . . . . ?
C37 C36 C40 C39 -5.7(4) . . . . ?
C49 C41 C42 C43 0.4(7) . . . . ?
C41 C42 C43 C44 -3.2(7) . . . . ?
C42 C43 C44 C50 -1.2(7) . . . . ?
C52 C45 C46 C47 -1.2(7) . . . . ?
C45 C46 C47 C48 3.4(7) . . . . ?
C46 C47 C48 C53 0.3(7) . . . . ?
C42 C41 C49 N1 -170.2(4) . . . . ?
C42 C41 C49 C50 6.7(6) . . . . ?
C43 C44 C50 C49 8.3(7) . . . . ?
C43 C44 C50 C51 -179.7(4) . . . . ?
N1 C49 C50 C44 166.1(4) . . . . ?
C41 C49 C50 C44 -11.0(6) . . . . ?
N1 C49 C50 C51 -6.7(5) . . . . ?
C41 C49 C50 C51 176.2(4) . . . . ?
C37 C36 C51 C50 1.2(6) . . . . ?
C40 C36 C51 C50 174.0(4) . . . . ?
C37 C36 C51 C52 -171.3(4) . . . . ?
C40 C36 C51 C52 1.5(7) . . . . ?
C44 C50 C51 C36 61.4(6) . . . . ?
C49 C50 C51 C36 -126.3(4) . . . . ?
C44 C50 C51 C52 -124.9(5) . . . . ?
C49 C50 C51 C52 47.4(5) . . . . ?
C46 C45 C52 C53 -4.6(7) . . . . ?
C46 C45 C52 C51 -178.6(4) . . . . ?
C36 C51 C52 C45 -58.2(7) . . . . ?
C50 C51 C52 C45 128.5(5) . . . . ?
C36 C51 C52 C53 127.5(5) . . . . ?
C50 C51 C52 C53 -45.8(5) . . . . ?
C47 C48 C53 N1 172.4(4) . . . . ?
C47 C48 C53 C52 -6.0(7) . . . . ?
C45 C52 C53 N1 -170.4(4) . . . . ?
C51 C52 C53 N1 4.3(6) . . . . ?
C45 C52 C53 C48 8.1(7) . . . . ?
C51 C52 C53 C48 -177.2(4) . . . . ?
C48 C53 N1 C49 -140.1(4) . . . . ?
C52 C53 N1 C49 38.4(6) . . . . ?
C48 C53 N1 C54 6.9(6) . . . . ?
C52 C53 N1 C54 -174.7(4) . . . . ?
C41 C49 N1 C53 140.0(4) . . . . ?
C50 C49 N1 C53 -37.0(5) . . . . ?
C41 C49 N1 C54 -7.3(6) . . . . ?
C50 C49 N1 C54 175.8(4) . . . . ?
C14 C22 N2 C26 140.1(4) . . . . ?
C23 C22 N2 C26 -36.1(5) . . . . ?
C14 C22 N2 C27 -10.5(6) . . . . ?
C23 C22 N2 C27 173.3(4) . . . . ?
C21 C26 N2 C22 -141.4(4) . . . . ?
C25 C26 N2 C22 33.9(5) . . . . ?
C21 C26 N2 C27 9.4(6) . . . . ?
C25 C26 N2 C27 -175.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        66.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.100
