# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_stu7058
_database_code_depnum_ccdc_archive 'CCDC 1051008'
_audit_update_record             
;
2015-02-24 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H17 N4 O'
_chemical_formula_weight         377.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_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                   3.9114(4)
_cell_length_b                   20.5945(6)
_cell_length_c                   22.4580(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.758(6)
_cell_angle_gamma                90.00
_cell_volume                     1808.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    3201
_cell_measurement_theta_min      0.88
_cell_measurement_theta_max      68.25

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             788
_exptl_absorpt_coefficient_mu    0.700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7671
_exptl_absorpt_correction_T_max  0.9658
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22085
_diffrn_reflns_av_R_equivalents  0.044
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         67.07
_reflns_number_total             3192
_reflns_number_gt                2887
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0542P)²+0.4290P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3192
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1009
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_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
O1 O 0.1139(3) 0.26989(4) 0.64840(4) 0.0452(3) Uani 1 1 d . . .
N1 N 0.2407(3) 0.33338(5) 0.50431(4) 0.0328(3) Uani 1 1 d . . .
N2 N 0.1956(3) 0.33116(5) 0.56487(4) 0.0316(2) Uani 1 1 d . . .
N3 N 0.3701(3) 0.22333(5) 0.56864(4) 0.0332(3) Uani 1 1 d . . .
N4 N 0.4500(3) 0.22485(5) 0.50951(4) 0.0354(3) Uani 1 1 d . . .
C1 C 0.2182(3) 0.27433(6) 0.59827(5) 0.0333(3) Uani 1 1 d . . .
C2 C 0.3610(3) 0.27912(6) 0.48068(5) 0.0310(3) Uani 1 1 d . . .
C41 C 0.4126(3) 0.28024(6) 0.41536(5) 0.0310(3) Uani 1 1 d . . .
C42 C 0.5706(3) 0.33294(6) 0.39084(6) 0.0338(3) Uani 1 1 d . . .
H42 H 0.6382 0.3679 0.4155 0.041 Uiso 1 1 calc R . .
C43 C 0.6332(4) 0.33566(6) 0.32954(6) 0.0366(3) Uani 1 1 d . . .
H43 H 0.7383 0.3725 0.3135 0.044 Uiso 1 1 calc R . .
C44 C 0.5418(3) 0.28500(6) 0.29340(5) 0.0355(3) Uani 1 1 d . . .
H44 H 0.5906 0.2866 0.2527 0.043 Uiso 1 1 calc R . .
C45 C 0.3743(3) 0.22997(6) 0.31643(5) 0.0321(3) Uani 1 1 d . . .
C46 C 0.2764(3) 0.17740(7) 0.27894(6) 0.0375(3) Uani 1 1 d . . .
H46 H 0.3260 0.1788 0.2383 0.045 Uiso 1 1 calc R . .
C47 C 0.1113(4) 0.12482(7) 0.30107(6) 0.0403(3) Uani 1 1 d . . .
H47 H 0.0536 0.0897 0.2760 0.048 Uiso 1 1 calc R . .
C48 C 0.0272(4) 0.12312(7) 0.36147(6) 0.0399(3) Uani 1 1 d . . .
H48 H -0.0922 0.0873 0.3762 0.048 Uiso 1 1 calc R . .
C49 C 0.1168(3) 0.17288(6) 0.39891(6) 0.0353(3) Uani 1 1 d . . .
H49 H 0.0548 0.1712 0.4390 0.042 Uiso 1 1 calc R . .
C50 C 0.3025(3) 0.22719(6) 0.37819(5) 0.0305(3) Uani 1 1 d . . .
C21 C 0.0787(3) 0.39089(6) 0.59052(5) 0.0306(3) Uani 1 1 d . . .
C22 C -0.1036(3) 0.43414(6) 0.55439(6) 0.0350(3) Uani 1 1 d . . .
H22 H -0.1597 0.4233 0.5146 0.042 Uiso 1 1 calc R . .
C23 C -0.2024(4) 0.49346(6) 0.57729(6) 0.0394(3) Uani 1 1 d . . .
H23 H -0.3238 0.5231 0.5528 0.047 Uiso 1 1 calc R . .
C24 C -0.1236(4) 0.50939(6) 0.63590(6) 0.0398(3) Uani 1 1 d . . .
H24 H -0.1925 0.5496 0.6514 0.048 Uiso 1 1 calc R . .
C25 C 0.0570(4) 0.46594(6) 0.67158(6) 0.0395(3) Uani 1 1 d . . .
H25 H 0.1099 0.4767 0.7115 0.047 Uiso 1 1 calc R . .
C26 C 0.1615(3) 0.40664(6) 0.64937(6) 0.0354(3) Uani 1 1 d . . .
H26 H 0.2865 0.3775 0.6738 0.042 Uiso 1 1 calc R . .
C31 C 0.4220(3) 0.16106(6) 0.59699(6) 0.0349(3) Uani 1 1 d . . .
C32 C 0.5441(4) 0.15678(7) 0.65523(6) 0.0397(3) Uani 1 1 d . . .
H32 H 0.5895 0.1946 0.6776 0.048 Uiso 1 1 calc R . .
C33 C 0.5986(4) 0.09608(7) 0.68018(7) 0.0473(4) Uani 1 1 d . . .
H33 H 0.6815 0.0927 0.7198 0.057 Uiso 1 1 calc R . .
C34 C 0.5327(4) 0.04061(7) 0.64758(7) 0.0540(4) Uani 1 1 d . . .
H34 H 0.5688 -0.0004 0.6650 0.065 Uiso 1 1 calc R . .
C35 C 0.4135(5) 0.04544(7) 0.58935(7) 0.0571(4) Uani 1 1 d . . .
H35 H 0.3707 0.0076 0.5669 0.069 Uiso 1 1 calc R . .
C36 C 0.3568(4) 0.10563(7) 0.56374(7) 0.0471(4) Uani 1 1 d . . .
H36 H 0.2746 0.1089 0.5241 0.056 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 1.2126(15) . ?
N1 C2 1.3294(15) . ?
N1 N2 1.3774(14) . ?
N2 C1 1.3916(15) . ?
N2 C21 1.4387(15) . ?
N3 N4 1.3740(14) . ?
N3 C1 1.3869(16) . ?
N3 C31 1.4433(16) . ?
N4 C2 1.3325(16) . ?
C2 C41 1.4872(16) . ?
C41 C42 1.3726(17) . ?
C41 C50 1.4332(17) . ?
C42 C43 1.4068(17) . ?
C42 H42 0.9400 . ?
C43 C44 1.3629(18) . ?
C43 H43 0.9400 . ?
C44 C45 1.4151(18) . ?
C44 H44 0.9400 . ?
C45 C46 1.4169(18) . ?
C45 C50 1.4247(17) . ?
C46 C47 1.363(2) . ?
C46 H46 0.9400 . ?
C47 C48 1.4058(19) . ?
C47 H47 0.9400 . ?
C48 C49 1.3645(18) . ?
C48 H48 0.9400 . ?
C49 C50 1.4195(18) . ?
C49 H49 0.9400 . ?
C21 C22 1.3873(18) . ?
C21 C26 1.3894(18) . ?
C22 C23 1.3851(18) . ?
C22 H22 0.9400 . ?
C23 C24 1.3822(19) . ?
C23 H23 0.9400 . ?
C24 C25 1.381(2) . ?
C24 H24 0.9400 . ?
C25 C26 1.3855(18) . ?
C25 H25 0.9400 . ?
C26 H26 0.9400 . ?
C31 C32 1.3815(19) . ?
C31 C36 1.3834(19) . ?
C32 C33 1.3835(19) . ?
C32 H32 0.9400 . ?
C33 C34 1.377(2) . ?
C33 H33 0.9400 . ?
C34 C35 1.378(2) . ?
C34 H34 0.9400 . ?
C35 C36 1.382(2) . ?
C35 H35 0.9400 . ?
C36 H36 0.9400 . ?

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 N1 N2 115.08(10) . . ?
N1 N2 C1 123.52(10) . . ?
N1 N2 C21 114.77(9) . . ?
C1 N2 C21 121.26(10) . . ?
N4 N3 C1 124.07(10) . . ?
N4 N3 C31 114.42(10) . . ?
C1 N3 C31 121.18(10) . . ?
C2 N4 N3 115.13(10) . . ?
O1 C1 N3 123.35(11) . . ?
O1 C1 N2 123.12(11) . . ?
N3 C1 N2 113.54(10) . . ?
N1 C2 N4 126.98(11) . . ?
N1 C2 C41 116.18(10) . . ?
N4 C2 C41 116.80(10) . . ?
C42 C41 C50 120.02(11) . . ?
C42 C41 C2 118.97(11) . . ?
C50 C41 C2 121.01(11) . . ?
C41 C42 C43 121.20(12) . . ?
C41 C42 H42 119.4 . . ?
C43 C42 H42 119.4 . . ?
C44 C43 C42 120.14(12) . . ?
C44 C43 H43 119.9 . . ?
C42 C43 H43 119.9 . . ?
C43 C44 C45 120.75(11) . . ?
C43 C44 H44 119.6 . . ?
C45 C44 H44 119.6 . . ?
C44 C45 C46 120.96(11) . . ?
C44 C45 C50 119.70(11) . . ?
C46 C45 C50 119.34(12) . . ?
C47 C46 C45 120.87(12) . . ?
C47 C46 H46 119.6 . . ?
C45 C46 H46 119.6 . . ?
C46 C47 C48 119.94(12) . . ?
C46 C47 H47 120.0 . . ?
C48 C47 H47 120.0 . . ?
C49 C48 C47 120.84(13) . . ?
C49 C48 H48 119.6 . . ?
C47 C48 H48 119.6 . . ?
C48 C49 C50 120.93(12) . . ?
C48 C49 H49 119.5 . . ?
C50 C49 H49 119.5 . . ?
C49 C50 C45 117.96(11) . . ?
C49 C50 C41 123.87(11) . . ?
C45 C50 C41 118.14(11) . . ?
C22 C21 C26 120.46(11) . . ?
C22 C21 N2 118.60(11) . . ?
C26 C21 N2 120.86(11) . . ?
C23 C22 C21 119.57(12) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C24 C23 C22 120.41(13) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C25 C24 C23 119.61(12) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 120.90(12) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C25 C26 C21 119.05(12) . . ?
C25 C26 H26 120.5 . . ?
C21 C26 H26 120.5 . . ?
C32 C31 C36 120.72(12) . . ?
C32 C31 N3 120.94(12) . . ?
C36 C31 N3 118.30(12) . . ?
C31 C32 C33 119.05(13) . . ?
C31 C32 H32 120.5 . . ?
C33 C32 H32 120.5 . . ?
C34 C33 C32 120.68(14) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C33 C34 C35 119.80(14) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
C34 C35 C36 120.33(15) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C35 C36 C31 119.42(14) . . ?
C35 C36 H36 120.3 . . ?
C31 C36 H36 120.3 . . ?

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
C2 N1 N2 C1 -10.13(17) . . . . ?
C2 N1 N2 C21 177.57(11) . . . . ?
C1 N3 N4 C2 -2.05(18) . . . . ?
C31 N3 N4 C2 171.39(11) . . . . ?
N4 N3 C1 O1 171.37(13) . . . . ?
C31 N3 C1 O1 -1.6(2) . . . . ?
N4 N3 C1 N2 -8.42(18) . . . . ?
C31 N3 C1 N2 178.57(11) . . . . ?
N1 N2 C1 O1 -164.96(12) . . . . ?
C21 N2 C1 O1 6.8(2) . . . . ?
N1 N2 C1 N3 14.83(17) . . . . ?
C21 N2 C1 N3 -173.36(11) . . . . ?
N2 N1 C2 N4 -2.24(19) . . . . ?
N2 N1 C2 C41 -179.91(10) . . . . ?
N3 N4 C2 N1 8.02(19) . . . . ?
N3 N4 C2 C41 -174.33(11) . . . . ?
N1 C2 C41 C42 45.61(17) . . . . ?
N4 C2 C41 C42 -132.30(12) . . . . ?
N1 C2 C41 C50 -134.84(12) . . . . ?
N4 C2 C41 C50 47.25(17) . . . . ?
C50 C41 C42 C43 -1.16(18) . . . . ?
C2 C41 C42 C43 178.40(12) . . . . ?
C41 C42 C43 C44 -1.1(2) . . . . ?
C42 C43 C44 C45 1.87(19) . . . . ?
C43 C44 C45 C46 179.50(12) . . . . ?
C43 C44 C45 C50 -0.48(19) . . . . ?
C44 C45 C46 C47 -179.17(12) . . . . ?
C50 C45 C46 C47 0.81(19) . . . . ?
C45 C46 C47 C48 1.9(2) . . . . ?
C46 C47 C48 C49 -1.7(2) . . . . ?
C47 C48 C49 C50 -1.1(2) . . . . ?
C48 C49 C50 C45 3.68(18) . . . . ?
C48 C49 C50 C41 -178.28(12) . . . . ?
C44 C45 C50 C49 176.47(11) . . . . ?
C46 C45 C50 C49 -3.51(17) . . . . ?
C44 C45 C50 C41 -1.69(17) . . . . ?
C46 C45 C50 C41 178.34(11) . . . . ?
C42 C41 C50 C49 -175.55(12) . . . . ?
C2 C41 C50 C49 4.90(18) . . . . ?
C42 C41 C50 C45 2.49(17) . . . . ?
C2 C41 C50 C45 -177.06(11) . . . . ?
N1 N2 C21 C22 25.42(16) . . . . ?
C1 N2 C21 C22 -147.06(12) . . . . ?
N1 N2 C21 C26 -151.24(12) . . . . ?
C1 N2 C21 C26 36.28(17) . . . . ?
C26 C21 C22 C23 0.19(19) . . . . ?
N2 C21 C22 C23 -176.48(11) . . . . ?
C21 C22 C23 C24 -0.7(2) . . . . ?
C22 C23 C24 C25 0.5(2) . . . . ?
C23 C24 C25 C26 0.2(2) . . . . ?
C24 C25 C26 C21 -0.7(2) . . . . ?
C22 C21 C26 C25 0.49(19) . . . . ?
N2 C21 C26 C25 177.09(12) . . . . ?
N4 N3 C31 C32 142.76(13) . . . . ?
C1 N3 C31 C32 -43.60(18) . . . . ?
N4 N3 C31 C36 -35.18(17) . . . . ?
C1 N3 C31 C36 138.46(14) . . . . ?
C36 C31 C32 C33 -0.4(2) . . . . ?
N3 C31 C32 C33 -178.31(13) . . . . ?
C31 C32 C33 C34 0.0(2) . . . . ?
C32 C33 C34 C35 0.5(2) . . . . ?
C33 C34 C35 C36 -0.7(3) . . . . ?
C34 C35 C36 C31 0.3(3) . . . . ?
C32 C31 C36 C35 0.3(2) . . . . ?
N3 C31 C36 C35 178.21(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        67.07
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_stu7039
_database_code_depnum_ccdc_archive 'CCDC 1051009'
_audit_update_record             
;
2015-02-24 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H19 N4 O'
_chemical_formula_weight         427.47
_chemical_absolute_configuration .

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.7763(13)
_cell_length_b                   5.8280(3)
_cell_length_c                   16.1543(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.773(6)
_cell_angle_gamma                90.00
_cell_volume                     1072.06(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    2545
_cell_measurement_theta_min      0.88
_cell_measurement_theta_max      66.60

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             446
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7137
_exptl_absorpt_correction_T_max  0.9870
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10206
_diffrn_reflns_av_R_equivalents  0.080
_diffrn_reflns_av_sigmaI/netI    0.0466
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.88
_diffrn_reflns_theta_max         63.37
_reflns_number_total             3257
_reflns_number_gt                2635
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0987P)²+0.2609P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0041(10)
_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   -0.4(6)
_refine_ls_number_reflns         3257
_refine_ls_number_parameters     299
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1681
_refine_ls_wR_factor_gt          0.1505
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
O1 O 1.0602(2) 0.4805(5) 0.24459(17) 0.0595(7) Uani 1 1 d . . .
N1 N 0.8050(3) 0.6766(6) 0.30270(19) 0.0545(8) Uani 1 1 d . . .
C1 C 0.9584(3) 0.4981(6) 0.2465(2) 0.0485(8) Uani 1 1 d . . .
N2 N 0.9206(2) 0.6466(5) 0.30253(18) 0.0495(7) Uani 1 1 d . . .
C2 C 0.7283(3) 0.5524(7) 0.2454(2) 0.0541(9) Uani 1 1 d . . .
N3 N 0.8682(2) 0.3754(5) 0.19428(19) 0.0516(7) Uani 1 1 d . . .
N4 N 0.7513(3) 0.4030(6) 0.1898(2) 0.0596(8) Uani 1 1 d . . .
C21 C 0.9998(3) 0.7988(6) 0.3590(2) 0.0475(8) Uani 1 1 d . . .
C22 C 1.1146(3) 0.7351(7) 0.3979(2) 0.0551(9) Uani 1 1 d . . .
H22 H 1.1436 0.5914 0.3865 0.066 Uiso 1 1 calc R . .
C23 C 1.1856(4) 0.8872(8) 0.4539(3) 0.0640(10) Uani 1 1 d . . .
H23 H 1.2639 0.8468 0.4798 0.077 Uiso 1 1 calc R . .
C24 C 1.1438(4) 1.0967(7) 0.4725(3) 0.0660(11) Uani 1 1 d . . .
H24 H 1.1928 1.1969 0.5114 0.079 Uiso 1 1 calc R . .
C25 C 1.0299(4) 1.1582(7) 0.4337(2) 0.0612(10) Uani 1 1 d . . .
H25 H 1.0012 1.3015 0.4458 0.073 Uiso 1 1 calc R . .
C26 C 0.9570(3) 1.0102(6) 0.3767(2) 0.0535(9) Uani 1 1 d . . .
H26 H 0.8792 1.0528 0.3503 0.064 Uiso 1 1 calc R . .
C31 C 0.8907(3) 0.2110(6) 0.1334(2) 0.0514(9) Uani 1 1 d . . .
C32 C 0.8160(4) 0.2115(7) 0.0524(3) 0.0580(10) Uani 1 1 d . . .
H32 H 0.7574 0.3244 0.0367 0.070 Uiso 1 1 calc R . .
C33 C 0.8279(4) 0.0436(8) -0.0057(3) 0.0636(10) Uani 1 1 d . . .
H33 H 0.7777 0.0427 -0.0612 0.076 Uiso 1 1 calc R . .
C34 C 0.9140(4) -0.1224(8) 0.0183(3) 0.0658(11) Uani 1 1 d . . .
H34 H 0.9215 -0.2372 -0.0208 0.079 Uiso 1 1 calc R . .
C35 C 0.9887(4) -0.1202(7) 0.0991(3) 0.0650(11) Uani 1 1 d . . .
H35 H 1.0472 -0.2332 0.1147 0.078 Uiso 1 1 calc R . .
C36 C 0.9784(4) 0.0478(7) 0.1579(2) 0.0573(10) Uani 1 1 d . . .
H36 H 1.0297 0.0505 0.2130 0.069 Uiso 1 1 calc R . .
C41 C 0.6019(3) 0.5843(7) 0.2429(3) 0.0605(10) Uani 1 1 d . . .
C42 C 0.5383(3) 0.7603(7) 0.1930(3) 0.0646(11) Uani 1 1 d . . .
C43 C 0.5865(4) 0.9028(8) 0.1392(3) 0.0724(12) Uani 1 1 d . . .
H43 H 0.6648 0.8803 0.1371 0.087 Uiso 1 1 calc R . .
C44 C 0.5221(4) 1.0708(9) 0.0906(4) 0.0857(14) Uani 1 1 d . . .
H44 H 0.5561 1.1622 0.0554 0.103 Uiso 1 1 calc R . .
C45 C 0.4056(5) 1.1090(10) 0.0924(4) 0.0999(18) Uani 1 1 d . . .
H45 H 0.3620 1.2257 0.0585 0.120 Uiso 1 1 calc R . .
C46 C 0.3550(4) 0.9801(10) 0.1424(4) 0.0921(17) Uani 1 1 d . . .
H46 H 0.2771 1.0108 0.1439 0.111 Uiso 1 1 calc R . .
C47 C 0.4178(4) 0.7970(8) 0.1934(3) 0.0728(12) Uani 1 1 d . . .
C48 C 0.3678(4) 0.6568(11) 0.2435(4) 0.0836(15) Uani 1 1 d . . .
H48 H 0.2893 0.6827 0.2442 0.100 Uiso 1 1 calc R . .
C49 C 0.4289(4) 0.4788(10) 0.2928(3) 0.0768(14) Uani 1 1 d . . .
C50 C 0.3776(5) 0.3291(12) 0.3434(4) 0.0929(17) Uani 1 1 d . . .
H50 H 0.2991 0.3518 0.3448 0.111 Uiso 1 1 calc R . .
C51 C 0.4390(5) 0.1571(14) 0.3889(4) 0.1042(19) Uani 1 1 d . . .
H51 H 0.4032 0.0629 0.4221 0.125 Uiso 1 1 calc R . .
C52 C 0.5564(5) 0.1151(11) 0.3877(3) 0.0911(16) Uani 1 1 d . . .
H52 H 0.5978 -0.0081 0.4191 0.109 Uiso 1 1 calc R . .
C53 C 0.6097(4) 0.2527(8) 0.3412(3) 0.0742(12) Uani 1 1 d . . .
H53 H 0.6883 0.2240 0.3412 0.089 Uiso 1 1 calc R . .
C54 C 0.5492(4) 0.4404(8) 0.2922(3) 0.0636(11) 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
O1 C1 1.211(4) . ?
N1 C2 1.331(5) . ?
N1 N2 1.374(4) . ?
C1 N3 1.377(5) . ?
C1 N2 1.405(4) . ?
N2 C21 1.434(5) . ?
C2 N4 1.327(5) . ?
C2 C41 1.490(5) . ?
N3 N4 1.369(4) . ?
N3 C31 1.445(5) . ?
C21 C22 1.388(5) . ?
C21 C26 1.388(5) . ?
C22 C23 1.385(6) . ?
C22 H22 0.9400 . ?
C23 C24 1.378(6) . ?
C23 H23 0.9400 . ?
C24 C25 1.376(6) . ?
C24 H24 0.9400 . ?
C25 C26 1.387(5) . ?
C25 H25 0.9400 . ?
C26 H26 0.9400 . ?
C31 C32 1.378(5) . ?
C31 C36 1.386(5) . ?
C32 C33 1.388(6) . ?
C32 H32 0.9400 . ?
C33 C34 1.383(6) . ?
C33 H33 0.9400 . ?
C34 C35 1.376(6) . ?
C34 H34 0.9400 . ?
C35 C36 1.391(6) . ?
C35 H35 0.9400 . ?
C36 H36 0.9400 . ?
C41 C42 1.398(6) . ?
C41 C54 1.405(6) . ?
C42 C43 1.422(7) . ?
C42 C47 1.436(6) . ?
C43 C44 1.359(7) . ?
C43 H43 0.9400 . ?
C44 C45 1.398(8) . ?
C44 H44 0.9400 . ?
C45 C46 1.348(8) . ?
C45 H45 0.9400 . ?
C46 C47 1.433(7) . ?
C46 H46 0.9400 . ?
C47 C48 1.382(8) . ?
C48 C49 1.391(8) . ?
C48 H48 0.9400 . ?
C49 C50 1.430(8) . ?
C49 C54 1.437(6) . ?
C50 C51 1.341(9) . ?
C50 H50 0.9400 . ?
C51 C52 1.409(7) . ?
C51 H51 0.9400 . ?
C52 C53 1.357(7) . ?
C52 H52 0.9400 . ?
C53 C54 1.429(6) . ?
C53 H53 0.9400 . ?

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 N1 N2 115.3(3) . . ?
O1 C1 N3 123.7(3) . . ?
O1 C1 N2 123.2(3) . . ?
N3 C1 N2 113.1(3) . . ?
N1 N2 C1 123.9(3) . . ?
N1 N2 C21 113.9(3) . . ?
C1 N2 C21 122.0(3) . . ?
N4 C2 N1 127.5(3) . . ?
N4 C2 C41 116.0(3) . . ?
N1 C2 C41 116.5(3) . . ?
N4 N3 C1 125.5(3) . . ?
N4 N3 C31 113.5(3) . . ?
C1 N3 C31 120.9(3) . . ?
C2 N4 N3 114.7(3) . . ?
C22 C21 C26 120.5(4) . . ?
C22 C21 N2 121.5(3) . . ?
C26 C21 N2 117.9(3) . . ?
C23 C22 C21 118.7(4) . . ?
C23 C22 H22 120.7 . . ?
C21 C22 H22 120.7 . . ?
C24 C23 C22 121.4(4) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
C25 C24 C23 119.5(4) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 120.5(4) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 119.5(4) . . ?
C25 C26 H26 120.3 . . ?
C21 C26 H26 120.3 . . ?
C32 C31 C36 121.4(3) . . ?
C32 C31 N3 117.5(3) . . ?
C36 C31 N3 120.9(3) . . ?
C31 C32 C33 119.4(4) . . ?
C31 C32 H32 120.3 . . ?
C33 C32 H32 120.3 . . ?
C34 C33 C32 119.8(4) . . ?
C34 C33 H33 120.1 . . ?
C32 C33 H33 120.1 . . ?
C35 C34 C33 120.3(4) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C34 C35 C36 120.6(4) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 H35 119.7 . . ?
C31 C36 C35 118.5(4) . . ?
C31 C36 H36 120.8 . . ?
C35 C36 H36 120.8 . . ?
C42 C41 C54 121.0(4) . . ?
C42 C41 C2 119.5(4) . . ?
C54 C41 C2 119.5(4) . . ?
C41 C42 C43 122.8(4) . . ?
C41 C42 C47 119.4(4) . . ?
C43 C42 C47 117.7(4) . . ?
C44 C43 C42 121.5(4) . . ?
C44 C43 H43 119.3 . . ?
C42 C43 H43 119.3 . . ?
C43 C44 C45 120.6(6) . . ?
C43 C44 H44 119.7 . . ?
C45 C44 H44 119.7 . . ?
C46 C45 C44 120.7(6) . . ?
C46 C45 H45 119.6 . . ?
C44 C45 H45 119.6 . . ?
C45 C46 C47 121.1(5) . . ?
C45 C46 H46 119.4 . . ?
C47 C46 H46 119.4 . . ?
C48 C47 C46 122.8(5) . . ?
C48 C47 C42 118.9(5) . . ?
C46 C47 C42 118.3(5) . . ?
C47 C48 C49 122.8(4) . . ?
C47 C48 H48 118.6 . . ?
C49 C48 H48 118.6 . . ?
C48 C49 C50 123.4(5) . . ?
C48 C49 C54 118.6(5) . . ?
C50 C49 C54 118.0(5) . . ?
C51 C50 C49 121.4(5) . . ?
C51 C50 H50 119.3 . . ?
C49 C50 H50 119.3 . . ?
C50 C51 C52 121.1(5) . . ?
C50 C51 H51 119.4 . . ?
C52 C51 H51 119.4 . . ?
C53 C52 C51 119.9(6) . . ?
C53 C52 H52 120.1 . . ?
C51 C52 H52 120.1 . . ?
C52 C53 C54 121.5(4) . . ?
C52 C53 H53 119.2 . . ?
C54 C53 H53 119.2 . . ?
C41 C54 C53 122.7(4) . . ?
C41 C54 C49 119.3(4) . . ?
C53 C54 C49 118.0(4) . . ?

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
C2 N1 N2 C1 0.4(5) . . . . ?
C2 N1 N2 C21 174.2(3) . . . . ?
O1 C1 N2 N1 176.8(3) . . . . ?
N3 C1 N2 N1 -3.2(5) . . . . ?
O1 C1 N2 C21 3.4(5) . . . . ?
N3 C1 N2 C21 -176.6(3) . . . . ?
N2 N1 C2 N4 1.0(6) . . . . ?
N2 N1 C2 C41 -178.9(3) . . . . ?
O1 C1 N3 N4 -174.7(4) . . . . ?
N2 C1 N3 N4 5.4(5) . . . . ?
O1 C1 N3 C31 1.0(5) . . . . ?
N2 C1 N3 C31 -178.9(3) . . . . ?
N1 C2 N4 N3 0.8(6) . . . . ?
C41 C2 N4 N3 -179.3(3) . . . . ?
C1 N3 N4 C2 -4.3(5) . . . . ?
C31 N3 N4 C2 179.7(3) . . . . ?
N1 N2 C21 C22 149.7(3) . . . . ?
C1 N2 C21 C22 -36.3(5) . . . . ?
N1 N2 C21 C26 -27.7(4) . . . . ?
C1 N2 C21 C26 146.2(3) . . . . ?
C26 C21 C22 C23 -0.6(5) . . . . ?
N2 C21 C22 C23 -178.0(3) . . . . ?
C21 C22 C23 C24 1.1(6) . . . . ?
C22 C23 C24 C25 -1.1(6) . . . . ?
C23 C24 C25 C26 0.5(6) . . . . ?
C24 C25 C26 C21 0.0(5) . . . . ?
C22 C21 C26 C25 0.0(5) . . . . ?
N2 C21 C26 C25 177.5(3) . . . . ?
N4 N3 C31 C32 39.9(4) . . . . ?
C1 N3 C31 C32 -136.3(4) . . . . ?
N4 N3 C31 C36 -135.1(4) . . . . ?
C1 N3 C31 C36 48.7(5) . . . . ?
C36 C31 C32 C33 0.6(6) . . . . ?
N3 C31 C32 C33 -174.3(3) . . . . ?
C31 C32 C33 C34 0.3(6) . . . . ?
C32 C33 C34 C35 -0.8(6) . . . . ?
C33 C34 C35 C36 0.4(6) . . . . ?
C32 C31 C36 C35 -1.0(6) . . . . ?
N3 C31 C36 C35 173.7(3) . . . . ?
C34 C35 C36 C31 0.6(6) . . . . ?
N4 C2 C41 C42 -93.5(5) . . . . ?
N1 C2 C41 C42 86.4(5) . . . . ?
N4 C2 C41 C54 87.9(5) . . . . ?
N1 C2 C41 C54 -92.2(5) . . . . ?
C54 C41 C42 C43 -177.0(4) . . . . ?
C2 C41 C42 C43 4.5(6) . . . . ?
C54 C41 C42 C47 1.1(6) . . . . ?
C2 C41 C42 C47 -177.4(4) . . . . ?
C41 C42 C43 C44 179.1(4) . . . . ?
C47 C42 C43 C44 1.1(7) . . . . ?
C42 C43 C44 C45 0.2(8) . . . . ?
C43 C44 C45 C46 0.0(8) . . . . ?
C44 C45 C46 C47 -1.6(8) . . . . ?
C45 C46 C47 C48 -178.0(5) . . . . ?
C45 C46 C47 C42 2.8(7) . . . . ?
C41 C42 C47 C48 0.1(6) . . . . ?
C43 C42 C47 C48 178.3(4) . . . . ?
C41 C42 C47 C46 179.4(4) . . . . ?
C43 C42 C47 C46 -2.5(6) . . . . ?
C46 C47 C48 C49 179.9(5) . . . . ?
C42 C47 C48 C49 -0.9(7) . . . . ?
C47 C48 C49 C50 -178.6(5) . . . . ?
C47 C48 C49 C54 0.5(7) . . . . ?
C48 C49 C50 C51 178.8(6) . . . . ?
C54 C49 C50 C51 -0.2(8) . . . . ?
C49 C50 C51 C52 -0.9(10) . . . . ?
C50 C51 C52 C53 1.2(9) . . . . ?
C51 C52 C53 C54 -0.5(8) . . . . ?
C42 C41 C54 C53 177.4(4) . . . . ?
C2 C41 C54 C53 -4.1(6) . . . . ?
C42 C41 C54 C49 -1.5(6) . . . . ?
C2 C41 C54 C49 177.0(4) . . . . ?
C52 C53 C54 C41 -179.4(4) . . . . ?
C52 C53 C54 C49 -0.6(7) . . . . ?
C48 C49 C54 C41 0.7(6) . . . . ?
C50 C49 C54 C41 179.8(4) . . . . ?
C48 C49 C54 C53 -178.2(4) . . . . ?
C50 C49 C54 C53 0.9(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        63.37
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.145
_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_stu7023
_database_code_depnum_ccdc_archive 'CCDC 1051010'
_audit_update_record             
;
2015-02-24 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H26 N4 O'
_chemical_formula_weight         482.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   7.4740(8)
_cell_length_b                   9.2641(5)
_cell_length_c                   35.8650(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.227(5)
_cell_angle_gamma                90.00
_cell_volume                     2482.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    4251
_cell_measurement_theta_min      0.88
_cell_measurement_theta_max      68.25

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8744
_exptl_absorpt_correction_T_max  0.9574
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21885
_diffrn_reflns_av_R_equivalents  0.063
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         4.93
_diffrn_reflns_theta_max         66.81
_reflns_number_total             4280
_reflns_number_gt                3416
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0448P)²+0.6671P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4280
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1051
_refine_ls_wR_factor_gt          0.0967
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
O1 O 0.26050(15) 0.72027(14) 0.37729(3) 0.0483(3) Uani 1 1 d . . .
N1 N 0.70351(16) 0.75635(14) 0.34581(3) 0.0345(3) Uani 1 1 d . . .
N2 N 0.51857(16) 0.72570(15) 0.34379(3) 0.0364(3) Uani 1 1 d . . .
N3 N 0.49587(17) 0.86004(14) 0.39747(4) 0.0365(3) Uani 1 1 d . . .
N4 N 0.63577(17) 0.94927(15) 0.38582(4) 0.0390(3) Uani 1 1 d . . .
C1 C 0.4114(2) 0.76432(17) 0.37344(4) 0.0360(4) Uani 1 1 d . . .
C2 C 0.7408(2) 0.89312(17) 0.36193(4) 0.0341(4) Uani 1 1 d . . .
C3 C 0.8161(2) 0.63233(17) 0.35967(4) 0.0380(4) Uani 1 1 d . . .
H3 H 0.9422 0.6649 0.3592 0.046 Uiso 1 1 calc R . .
C4 C 0.7987(3) 0.5080(2) 0.33214(5) 0.0516(5) Uani 1 1 d . . .
H4A H 0.6759 0.4740 0.3313 0.077 Uiso 1 1 calc R . .
H4B H 0.8773 0.4299 0.3400 0.077 Uiso 1 1 calc R . .
H4C H 0.8317 0.5408 0.3075 0.077 Uiso 1 1 calc R . .
C11 C 0.7781(2) 0.59284(17) 0.39965(4) 0.0363(4) Uani 1 1 d . . .
C12 C 0.6437(2) 0.49663(19) 0.40924(5) 0.0457(4) Uani 1 1 d . . .
H12 H 0.5721 0.4541 0.3904 0.055 Uiso 1 1 calc R . .
C13 C 0.6140(3) 0.4628(2) 0.44599(5) 0.0534(5) Uani 1 1 d . . .
H13 H 0.5222 0.3980 0.4520 0.064 Uiso 1 1 calc R . .
C14 C 0.7185(3) 0.5236(2) 0.47391(5) 0.0550(5) Uani 1 1 d . . .
H14 H 0.6987 0.4997 0.4990 0.066 Uiso 1 1 calc R . .
C15 C 0.8519(3) 0.6193(2) 0.46512(5) 0.0506(5) Uani 1 1 d . . .
H15 H 0.9230 0.6613 0.4842 0.061 Uiso 1 1 calc R . .
C16 C 0.8816(2) 0.65393(18) 0.42806(4) 0.0413(4) Uani 1 1 d . . .
H16 H 0.9728 0.7195 0.4222 0.050 Uiso 1 1 calc R . .
C21 C 0.4427(2) 0.70958(17) 0.30678(4) 0.0350(4) Uani 1 1 d . . .
C22 C 0.2979(2) 0.61861(19) 0.30066(5) 0.0439(4) Uani 1 1 d . . .
H22 H 0.2503 0.5655 0.3205 0.053 Uiso 1 1 calc R . .
C23 C 0.2242(3) 0.6068(2) 0.26502(5) 0.0547(5) Uani 1 1 d . . .
H23 H 0.1258 0.5454 0.2607 0.066 Uiso 1 1 calc R . .
C24 C 0.2934(3) 0.6841(2) 0.23564(5) 0.0551(5) Uani 1 1 d . . .
H24 H 0.2421 0.6759 0.2116 0.066 Uiso 1 1 calc R . .
C25 C 0.4380(2) 0.7731(2) 0.24201(5) 0.0493(5) Uani 1 1 d . . .
H25 H 0.4860 0.8254 0.2221 0.059 Uiso 1 1 calc R . .
C26 C 0.5139(2) 0.78635(19) 0.27751(4) 0.0415(4) Uani 1 1 d . . .
H26 H 0.6131 0.8471 0.2816 0.050 Uiso 1 1 calc R . .
C31 C 0.4083(2) 0.90948(18) 0.43031(4) 0.0349(4) Uani 1 1 d . . .
C32 C 0.3376(2) 0.8100(2) 0.45478(5) 0.0450(4) Uani 1 1 d . . .
H32 H 0.3446 0.7107 0.4496 0.054 Uiso 1 1 calc R . .
C33 C 0.2566(2) 0.8576(2) 0.48682(5) 0.0501(5) Uani 1 1 d . . .
H33 H 0.2076 0.7901 0.5033 0.060 Uiso 1 1 calc R . .
C34 C 0.2469(2) 1.0026(2) 0.49489(5) 0.0481(4) Uani 1 1 d . . .
H34 H 0.1918 1.0345 0.5167 0.058 Uiso 1 1 calc R . .
C35 C 0.3188(2) 1.0996(2) 0.47063(5) 0.0502(5) Uani 1 1 d . . .
H35 H 0.3131 1.1988 0.4760 0.060 Uiso 1 1 calc R . .
C36 C 0.3999(2) 1.05448(19) 0.43829(5) 0.0444(4) Uani 1 1 d . . .
H36 H 0.4488 1.1224 0.4219 0.053 Uiso 1 1 calc R . .
C41 C 0.9013(2) 0.96854(17) 0.34825(4) 0.0355(4) Uani 1 1 d . . .
C42 C 0.9748(2) 0.91653(19) 0.31603(4) 0.0400(4) Uani 1 1 d . . .
H42 H 0.9212 0.8364 0.3042 0.048 Uiso 1 1 calc R . .
C43 C 1.1266(2) 0.9783(2) 0.30011(5) 0.0467(4) Uani 1 1 d . . .
H43 H 1.1740 0.9390 0.2783 0.056 Uiso 1 1 calc R . .
C44 C 1.2044(2) 1.0951(2) 0.31646(5) 0.0506(5) Uani 1 1 d . . .
H44 H 1.3058 1.1368 0.3057 0.061 Uiso 1 1 calc R . .
C45 C 1.1354(2) 1.15514(18) 0.34934(5) 0.0431(4) Uani 1 1 d . . .
C46 C 1.2152(2) 1.2796(2) 0.36558(6) 0.0531(5) Uani 1 1 d . . .
H46 H 1.3146 1.3216 0.3542 0.064 Uiso 1 1 calc R . .
C47 C 1.1517(2) 1.3396(2) 0.39718(6) 0.0535(5) Uani 1 1 d . . .
H47 H 1.2046 1.4235 0.4072 0.064 Uiso 1 1 calc R . .
C48 C 1.0066(2) 1.2750(2) 0.41463(5) 0.0498(4) Uani 1 1 d . . .
H48 H 0.9643 1.3151 0.4368 0.060 Uiso 1 1 calc R . .
C49 C 0.9246(2) 1.15478(19) 0.40013(5) 0.0430(4) Uani 1 1 d . . .
H49 H 0.8280 1.1135 0.4126 0.052 Uiso 1 1 calc R . .
C50 C 0.9835(2) 1.09143(17) 0.36646(5) 0.0382(4) 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
O1 C1 1.2098(18) . ?
N1 N2 1.4115(17) . ?
N1 C2 1.418(2) . ?
N1 C3 1.502(2) . ?
N2 C1 1.392(2) . ?
N2 C21 1.4401(19) . ?
N3 C1 1.380(2) . ?
N3 N4 1.4035(17) . ?
N3 C31 1.4350(19) . ?
N4 C2 1.284(2) . ?
C2 C41 1.481(2) . ?
C3 C11 1.513(2) . ?
C3 C4 1.521(2) . ?
C3 H3 0.9900 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4C 0.9700 . ?
C11 C16 1.387(2) . ?
C11 C12 1.392(2) . ?
C12 C13 1.377(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.377(3) . ?
C13 H13 0.9400 . ?
C14 C15 1.376(3) . ?
C14 H14 0.9400 . ?
C15 C16 1.390(2) . ?
C15 H15 0.9400 . ?
C16 H16 0.9400 . ?
C21 C26 1.384(2) . ?
C21 C22 1.385(2) . ?
C22 C23 1.385(2) . ?
C22 H22 0.9400 . ?
C23 C24 1.384(3) . ?
C23 H23 0.9400 . ?
C24 C25 1.374(3) . ?
C24 H24 0.9400 . ?
C25 C26 1.388(2) . ?
C25 H25 0.9400 . ?
C26 H26 0.9400 . ?
C31 C36 1.375(2) . ?
C31 C32 1.385(2) . ?
C32 C33 1.382(2) . ?
C32 H32 0.9400 . ?
C33 C34 1.377(3) . ?
C33 H33 0.9400 . ?
C34 C35 1.369(3) . ?
C34 H34 0.9400 . ?
C35 C36 1.385(2) . ?
C35 H35 0.9400 . ?
C36 H36 0.9400 . ?
C41 C42 1.378(2) . ?
C41 C50 1.443(2) . ?
C42 C43 1.403(2) . ?
C42 H42 0.9400 . ?
C43 C44 1.356(3) . ?
C43 H43 0.9400 . ?
C44 C45 1.411(3) . ?
C44 H44 0.9400 . ?
C45 C46 1.418(3) . ?
C45 C50 1.430(2) . ?
C46 C47 1.357(3) . ?
C46 H46 0.9400 . ?
C47 C48 1.398(3) . ?
C47 H47 0.9400 . ?
C48 C49 1.369(2) . ?
C48 H48 0.9400 . ?
C49 C50 1.421(2) . ?
C49 H49 0.9400 . ?

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
N2 N1 C2 112.59(12) . . ?
N2 N1 C3 113.82(12) . . ?
C2 N1 C3 116.41(12) . . ?
C1 N2 N1 119.23(12) . . ?
C1 N2 C21 120.61(12) . . ?
N1 N2 C21 115.71(12) . . ?
C1 N3 N4 121.78(12) . . ?
C1 N3 C31 120.45(12) . . ?
N4 N3 C31 114.35(12) . . ?
C2 N4 N3 115.45(13) . . ?
O1 C1 N3 124.11(14) . . ?
O1 C1 N2 123.62(14) . . ?
N3 C1 N2 112.26(13) . . ?
N4 C2 N1 121.10(14) . . ?
N4 C2 C41 122.74(14) . . ?
N1 C2 C41 116.10(13) . . ?
N1 C3 C11 112.54(13) . . ?
N1 C3 C4 108.97(13) . . ?
C11 C3 C4 114.65(14) . . ?
N1 C3 H3 106.7 . . ?
C11 C3 H3 106.7 . . ?
C4 C3 H3 106.7 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C16 C11 C12 118.30(15) . . ?
C16 C11 C3 118.99(14) . . ?
C12 C11 C3 122.71(15) . . ?
C13 C12 C11 120.95(17) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 120.15(17) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 119.97(17) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 119.92(17) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 120.72(16) . . ?
C11 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C26 C21 C22 120.28(15) . . ?
C26 C21 N2 119.72(14) . . ?
C22 C21 N2 119.99(14) . . ?
C21 C22 C23 119.22(17) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C24 C23 C22 120.93(18) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C25 C24 C23 119.29(16) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C26 120.67(17) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 119.60(16) . . ?
C21 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C36 C31 C32 119.89(15) . . ?
C36 C31 N3 120.42(14) . . ?
C32 C31 N3 119.65(15) . . ?
C33 C32 C31 119.61(17) . . ?
C33 C32 H32 120.2 . . ?
C31 C32 H32 120.2 . . ?
C34 C33 C32 120.81(17) . . ?
C34 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C35 C34 C33 118.93(16) . . ?
C35 C34 H34 120.5 . . ?
C33 C34 H34 120.5 . . ?
C34 C35 C36 121.27(17) . . ?
C34 C35 H35 119.4 . . ?
C36 C35 H35 119.4 . . ?
C31 C36 C35 119.48(16) . . ?
C31 C36 H36 120.3 . . ?
C35 C36 H36 120.3 . . ?
C42 C41 C50 118.80(15) . . ?
C42 C41 C2 116.98(15) . . ?
C50 C41 C2 124.22(14) . . ?
C41 C42 C43 122.64(17) . . ?
C41 C42 H42 118.7 . . ?
C43 C42 H42 118.7 . . ?
C44 C43 C42 119.53(17) . . ?
C44 C43 H43 120.2 . . ?
C42 C43 H43 120.2 . . ?
C43 C44 C45 120.96(16) . . ?
C43 C44 H44 119.5 . . ?
C45 C44 H44 119.5 . . ?
C44 C45 C46 120.35(16) . . ?
C44 C45 C50 120.27(16) . . ?
C46 C45 C50 119.38(17) . . ?
C47 C46 C45 121.63(17) . . ?
C47 C46 H46 119.2 . . ?
C45 C46 H46 119.2 . . ?
C46 C47 C48 119.14(18) . . ?
C46 C47 H47 120.4 . . ?
C48 C47 H47 120.4 . . ?
C49 C48 C47 121.57(18) . . ?
C49 C48 H48 119.2 . . ?
C47 C48 H48 119.2 . . ?
C48 C49 C50 121.00(16) . . ?
C48 C49 H49 119.5 . . ?
C50 C49 H49 119.5 . . ?
C49 C50 C45 117.22(16) . . ?
C49 C50 C41 125.02(15) . . ?
C45 C50 C41 117.76(15) . . ?

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
C2 N1 N2 C1 -39.95(18) . . . . ?
C3 N1 N2 C1 95.32(16) . . . . ?
C2 N1 N2 C21 116.56(14) . . . . ?
C3 N1 N2 C21 -108.17(14) . . . . ?
C1 N3 N4 C2 -35.5(2) . . . . ?
C31 N3 N4 C2 165.33(13) . . . . ?
N4 N3 C1 O1 -155.29(15) . . . . ?
C31 N3 C1 O1 2.7(2) . . . . ?
N4 N3 C1 N2 23.7(2) . . . . ?
C31 N3 C1 N2 -178.34(13) . . . . ?
N1 N2 C1 O1 -166.21(15) . . . . ?
C21 N2 C1 O1 38.5(2) . . . . ?
N1 N2 C1 N3 14.77(19) . . . . ?
C21 N2 C1 N3 -140.56(14) . . . . ?
N3 N4 C2 N1 6.6(2) . . . . ?
N3 N4 C2 C41 -176.37(13) . . . . ?
N2 N1 C2 N4 28.52(19) . . . . ?
C3 N1 C2 N4 -105.52(16) . . . . ?
N2 N1 C2 C41 -148.68(12) . . . . ?
C3 N1 C2 C41 77.28(16) . . . . ?
N2 N1 C3 C11 -64.90(16) . . . . ?
C2 N1 C3 C11 68.59(17) . . . . ?
N2 N1 C3 C4 63.44(17) . . . . ?
C2 N1 C3 C4 -163.07(14) . . . . ?
N1 C3 C11 C16 -93.17(17) . . . . ?
C4 C3 C11 C16 141.53(16) . . . . ?
N1 C3 C11 C12 87.23(18) . . . . ?
C4 C3 C11 C12 -38.1(2) . . . . ?
C16 C11 C12 C13 0.0(2) . . . . ?
C3 C11 C12 C13 179.60(16) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C12 C11 C16 C15 0.2(2) . . . . ?
C3 C11 C16 C15 -179.39(15) . . . . ?
C14 C15 C16 C11 -0.1(3) . . . . ?
C1 N2 C21 C26 125.32(16) . . . . ?
N1 N2 C21 C26 -30.8(2) . . . . ?
C1 N2 C21 C22 -54.1(2) . . . . ?
N1 N2 C21 C22 149.79(15) . . . . ?
C26 C21 C22 C23 -0.8(3) . . . . ?
N2 C21 C22 C23 178.61(16) . . . . ?
C21 C22 C23 C24 0.2(3) . . . . ?
C22 C23 C24 C25 0.4(3) . . . . ?
C23 C24 C25 C26 -0.4(3) . . . . ?
C22 C21 C26 C25 0.8(2) . . . . ?
N2 C21 C26 C25 -178.57(15) . . . . ?
C24 C25 C26 C21 -0.2(3) . . . . ?
C1 N3 C31 C36 -130.09(16) . . . . ?
N4 N3 C31 C36 29.4(2) . . . . ?
C1 N3 C31 C32 52.3(2) . . . . ?
N4 N3 C31 C32 -148.24(14) . . . . ?
C36 C31 C32 C33 1.0(3) . . . . ?
N3 C31 C32 C33 178.61(15) . . . . ?
C31 C32 C33 C34 -0.6(3) . . . . ?
C32 C33 C34 C35 0.0(3) . . . . ?
C33 C34 C35 C36 0.2(3) . . . . ?
C32 C31 C36 C35 -0.7(3) . . . . ?
N3 C31 C36 C35 -178.32(15) . . . . ?
C34 C35 C36 C31 0.1(3) . . . . ?
N4 C2 C41 C42 -162.95(15) . . . . ?
N1 C2 C41 C42 14.2(2) . . . . ?
N4 C2 C41 C50 17.0(2) . . . . ?
N1 C2 C41 C50 -165.85(13) . . . . ?
C50 C41 C42 C43 -0.1(2) . . . . ?
C2 C41 C42 C43 179.88(14) . . . . ?
C41 C42 C43 C44 -0.9(3) . . . . ?
C42 C43 C44 C45 0.2(3) . . . . ?
C43 C44 C45 C46 -178.32(17) . . . . ?
C43 C44 C45 C50 1.3(3) . . . . ?
C44 C45 C46 C47 -179.98(17) . . . . ?
C50 C45 C46 C47 0.4(3) . . . . ?
C45 C46 C47 C48 1.5(3) . . . . ?
C46 C47 C48 C49 -1.5(3) . . . . ?
C47 C48 C49 C50 -0.5(3) . . . . ?
C48 C49 C50 C45 2.4(2) . . . . ?
C48 C49 C50 C41 -177.36(15) . . . . ?
C44 C45 C50 C49 178.07(15) . . . . ?
C46 C45 C50 C49 -2.3(2) . . . . ?
C44 C45 C50 C41 -2.2(2) . . . . ?
C46 C45 C50 C41 177.44(14) . . . . ?
C42 C41 C50 C49 -178.70(15) . . . . ?
C2 C41 C50 C49 1.4(2) . . . . ?
C42 C41 C50 C45 1.6(2) . . . . ?
C2 C41 C50 C45 -178.39(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        66.81
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.200
_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_stu6996
_database_code_depnum_ccdc_archive 'CCDC 1051011'
_audit_update_record             
;
2015-02-24 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H28 N4 O'
_chemical_formula_weight         532.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   11.2158(3)
_cell_length_b                   10.0647(3)
_cell_length_c                   24.8459(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.414(2)
_cell_angle_gamma                90.00
_cell_volume                     2781.25(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    4618
_cell_measurement_theta_min      0.88
_cell_measurement_theta_max      68.25

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7579
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20096
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         4.75
_diffrn_reflns_theta_max         66.96
_reflns_number_total             4794
_reflns_number_gt                4370
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0917P)²+0.5986P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4794
_refine_ls_number_parameters     371
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1450
_refine_ls_wR_factor_gt          0.1397
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
O1 O 0.13851(11) 0.35217(16) 0.29825(4) 0.0654(4) Uani 1 1 d . . .
N1 N 0.11375(11) 0.31650(12) 0.15490(5) 0.0394(3) Uani 1 1 d . . .
C1 C 0.16033(15) 0.32716(16) 0.25271(6) 0.0473(4) Uani 1 1 d . . .
N2 N 0.07584(11) 0.31884(14) 0.20744(5) 0.0471(3) Uani 1 1 d . . .
C2 C 0.22060(13) 0.24199(14) 0.15463(6) 0.0389(3) Uani 1 1 d . . .
N3 N 0.27531(12) 0.30049(14) 0.24187(5) 0.0470(3) Uani 1 1 d . . .
C3 C 0.11595(14) 0.45077(15) 0.12844(7) 0.0481(4) Uani 1 1 d . . .
H3 H 0.1639 0.4394 0.0980 0.058 Uiso 1 1 calc R . .
N4 N 0.29824(11) 0.22687(13) 0.19647(5) 0.0447(3) Uani 1 1 d . . .
C4 C 0.18003(19) 0.55614(19) 0.16464(10) 0.0735(6) Uani 1 1 d . . .
H4A H 0.1363 0.5722 0.1952 0.110 Uiso 1 1 calc R . .
H4B H 0.1842 0.6377 0.1442 0.110 Uiso 1 1 calc R . .
H4C H 0.2608 0.5262 0.1778 0.110 Uiso 1 1 calc R . .
C11 C -0.00939(14) 0.48899(15) 0.10263(6) 0.0436(3) Uani 1 1 d . . .
C12 C -0.07966(16) 0.58347(17) 0.12398(7) 0.0534(4) Uani 1 1 d . . .
H12 H -0.0518 0.6249 0.1571 0.064 Uiso 1 1 calc R . .
C13 C -0.19145(16) 0.61727(19) 0.09649(9) 0.0659(5) Uani 1 1 d . . .
H13 H -0.2392 0.6811 0.1112 0.079 Uiso 1 1 calc R . .
C14 C -0.23235(17) 0.5575(2) 0.04783(9) 0.0676(5) Uani 1 1 d . . .
H14 H -0.3071 0.5819 0.0289 0.081 Uiso 1 1 calc R . .
C15 C -0.16406(17) 0.4625(2) 0.02700(8) 0.0658(5) Uani 1 1 d . . .
H15 H -0.1925 0.4204 -0.0059 0.079 Uiso 1 1 calc R . .
C16 C -0.05397(15) 0.42879(18) 0.05429(7) 0.0542(4) Uani 1 1 d . . .
H16 H -0.0079 0.3631 0.0397 0.065 Uiso 1 1 calc R . .
C21 C -0.05179(14) 0.31228(16) 0.20919(6) 0.0461(4) Uani 1 1 d . . .
C22 C -0.10299(17) 0.3804(2) 0.24875(8) 0.0662(5) Uani 1 1 d . . .
H22 H -0.0546 0.4310 0.2748 0.079 Uiso 1 1 calc R . .
C23 C -0.22566(19) 0.3738(3) 0.24971(8) 0.0785(6) Uani 1 1 d . . .
H23 H -0.2601 0.4195 0.2769 0.094 Uiso 1 1 calc R . .
C24 C -0.29768(18) 0.3022(2) 0.21199(10) 0.0760(6) Uani 1 1 d . . .
H24 H -0.3809 0.2970 0.2135 0.091 Uiso 1 1 calc R . .
C25 C -0.24688(17) 0.2374(2) 0.17156(10) 0.0726(6) Uani 1 1 d . . .
H25 H -0.2961 0.1895 0.1448 0.087 Uiso 1 1 calc R . .
C26 C -0.12408(15) 0.24239(19) 0.17007(8) 0.0595(4) Uani 1 1 d . . .
H26 H -0.0901 0.1981 0.1424 0.071 Uiso 1 1 calc R . .
C31 C 0.37395(14) 0.30513(16) 0.28477(6) 0.0457(4) Uani 1 1 d . . .
C32 C 0.4228(2) 0.4257(2) 0.30096(9) 0.0735(6) Uani 1 1 d . . .
H32 H 0.3906 0.5044 0.2847 0.088 Uiso 1 1 calc R . .
C33 C 0.5199(2) 0.4312(3) 0.34140(10) 0.0852(7) Uani 1 1 d . . .
H33 H 0.5530 0.5141 0.3525 0.102 Uiso 1 1 calc R . .
C34 C 0.56757(18) 0.3194(3) 0.36507(8) 0.0711(6) Uani 1 1 d . . .
H34 H 0.6337 0.3242 0.3924 0.085 Uiso 1 1 calc R . .
C35 C 0.51911(19) 0.1993(2) 0.34898(9) 0.0747(6) Uani 1 1 d . . .
H35 H 0.5519 0.1212 0.3656 0.090 Uiso 1 1 calc R . .
C36 C 0.42257(17) 0.1908(2) 0.30858(8) 0.0640(5) Uani 1 1 d . . .
H36 H 0.3904 0.1075 0.2975 0.077 Uiso 1 1 calc R . .
C40 C 0.24276(13) 0.17566(14) 0.10323(5) 0.0387(3) Uani 1 1 d . . .
C41 C 0.17072(13) 0.06617(14) 0.08434(5) 0.0391(3) Uani 1 1 d . . .
C42 C 0.07955(14) 0.01449(15) 0.11326(6) 0.0449(4) Uani 1 1 d . . .
H42 H 0.0651 0.0556 0.1458 0.054 Uiso 1 1 calc R . .
C43 C 0.01304(17) -0.09273(16) 0.09502(7) 0.0538(4) Uani 1 1 d . . .
H43 H -0.0471 -0.1244 0.1148 0.065 Uiso 1 1 calc R . .
C44 C 0.03368(18) -0.15724(17) 0.04639(7) 0.0577(4) Uani 1 1 d . . .
H44 H -0.0130 -0.2313 0.0340 0.069 Uiso 1 1 calc R . .
C45 C 0.12026(17) -0.11264(16) 0.01776(6) 0.0528(4) Uani 1 1 d . . .
H45 H 0.1329 -0.1562 -0.0145 0.063 Uiso 1 1 calc R . .
C46 C 0.19277(14) -0.00056(15) 0.03569(6) 0.0434(4) Uani 1 1 d . . .
C47 C 0.28540(15) 0.04404(16) 0.00796(6) 0.0473(4) Uani 1 1 d . . .
H47 H 0.2981 0.0020 -0.0246 0.057 Uiso 1 1 calc R . .
C48 C 0.35936(14) 0.14877(16) 0.02708(6) 0.0452(4) Uani 1 1 d . . .
C49 C 0.45761(16) 0.18977(19) -0.00036(7) 0.0577(4) Uani 1 1 d . . .
H49 H 0.4714 0.1464 -0.0325 0.069 Uiso 1 1 calc R . .
C50 C 0.53068(16) 0.2897(2) 0.01917(8) 0.0660(5) Uani 1 1 d . . .
H50 H 0.5955 0.3145 0.0008 0.079 Uiso 1 1 calc R . .
C51 C 0.51085(16) 0.3574(2) 0.06680(8) 0.0640(5) Uani 1 1 d . . .
H51 H 0.5622 0.4274 0.0798 0.077 Uiso 1 1 calc R . .
C52 C 0.41815(15) 0.32247(18) 0.09428(7) 0.0525(4) Uani 1 1 d . . .
H52 H 0.4064 0.3688 0.1260 0.063 Uiso 1 1 calc R . .
C53 C 0.33860(13) 0.21697(15) 0.07576(6) 0.0418(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
O1 C1 1.2146(19) . ?
N1 C2 1.4144(19) . ?
N1 N2 1.4242(16) . ?
N1 C3 1.5043(19) . ?
C1 N2 1.377(2) . ?
C1 N3 1.377(2) . ?
N2 C21 1.439(2) . ?
C2 N4 1.2761(19) . ?
C2 C40 1.4902(19) . ?
N3 N4 1.4008(17) . ?
N3 C31 1.4345(19) . ?
C3 C4 1.511(3) . ?
C3 C11 1.517(2) . ?
C3 H3 0.9900 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4C 0.9700 . ?
C11 C16 1.380(2) . ?
C11 C12 1.384(2) . ?
C12 C13 1.391(3) . ?
C12 H12 0.9400 . ?
C13 C14 1.375(3) . ?
C13 H13 0.9400 . ?
C14 C15 1.368(3) . ?
C14 H14 0.9400 . ?
C15 C16 1.372(3) . ?
C15 H15 0.9400 . ?
C16 H16 0.9400 . ?
C21 C26 1.376(2) . ?
C21 C22 1.383(2) . ?
C22 C23 1.381(3) . ?
C22 H22 0.9400 . ?
C23 C24 1.362(3) . ?
C23 H23 0.9400 . ?
C24 C25 1.381(3) . ?
C24 H24 0.9400 . ?
C25 C26 1.383(3) . ?
C25 H25 0.9400 . ?
C26 H26 0.9400 . ?
C31 C32 1.371(2) . ?
C31 C36 1.374(2) . ?
C32 C33 1.384(3) . ?
C32 H32 0.9400 . ?
C33 C34 1.348(4) . ?
C33 H33 0.9400 . ?
C34 C35 1.364(3) . ?
C34 H34 0.9400 . ?
C35 C36 1.381(3) . ?
C35 H35 0.9400 . ?
C36 H36 0.9400 . ?
C40 C53 1.408(2) . ?
C40 C41 1.411(2) . ?
C41 C42 1.422(2) . ?
C41 C46 1.432(2) . ?
C42 C43 1.356(2) . ?
C42 H42 0.9400 . ?
C43 C44 1.417(2) . ?
C43 H43 0.9400 . ?
C44 C45 1.352(3) . ?
C44 H44 0.9400 . ?
C45 C46 1.428(2) . ?
C45 H45 0.9400 . ?
C46 C47 1.393(2) . ?
C47 C48 1.387(2) . ?
C47 H47 0.9400 . ?
C48 C49 1.429(2) . ?
C48 C53 1.436(2) . ?
C49 C50 1.348(3) . ?
C49 H49 0.9400 . ?
C50 C51 1.408(3) . ?
C50 H50 0.9400 . ?
C51 C52 1.361(2) . ?
C51 H51 0.9400 . ?
C52 C53 1.425(2) . ?
C52 H52 0.9400 . ?

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 N1 N2 111.50(11) . . ?
C2 N1 C3 114.37(11) . . ?
N2 N1 C3 114.17(12) . . ?
O1 C1 N2 125.00(15) . . ?
O1 C1 N3 121.92(15) . . ?
N2 C1 N3 113.05(13) . . ?
C1 N2 N1 119.63(12) . . ?
C1 N2 C21 124.10(12) . . ?
N1 N2 C21 116.28(12) . . ?
N4 C2 N1 123.29(13) . . ?
N4 C2 C40 118.22(12) . . ?
N1 C2 C40 118.47(12) . . ?
C1 N3 N4 122.29(12) . . ?
C1 N3 C31 120.01(13) . . ?
N4 N3 C31 114.29(12) . . ?
N1 C3 C4 113.81(14) . . ?
N1 C3 C11 110.24(12) . . ?
C4 C3 C11 114.65(14) . . ?
N1 C3 H3 105.8 . . ?
C4 C3 H3 105.8 . . ?
C11 C3 H3 105.8 . . ?
C2 N4 N3 114.58(12) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C16 C11 C12 118.36(16) . . ?
C16 C11 C3 117.93(15) . . ?
C12 C11 C3 123.68(15) . . ?
C11 C12 C13 120.12(17) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 120.16(18) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 119.92(18) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 119.87(19) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C11 121.54(18) . . ?
C15 C16 H16 119.2 . . ?
C11 C16 H16 119.2 . . ?
C26 C21 C22 119.65(16) . . ?
C26 C21 N2 119.99(14) . . ?
C22 C21 N2 120.30(15) . . ?
C23 C22 C21 119.6(2) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C24 C23 C22 121.18(19) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C25 119.12(18) . . ?
C23 C24 H24 120.4 . . ?
C25 C24 H24 120.4 . . ?
C24 C25 C26 120.5(2) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 119.84(18) . . ?
C21 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C32 C31 C36 119.58(16) . . ?
C32 C31 N3 119.20(16) . . ?
C36 C31 N3 121.19(14) . . ?
C31 C32 C33 119.7(2) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 H32 120.1 . . ?
C34 C33 C32 120.9(2) . . ?
C34 C33 H33 119.5 . . ?
C32 C33 H33 119.5 . . ?
C33 C34 C35 119.44(18) . . ?
C33 C34 H34 120.3 . . ?
C35 C34 H34 120.3 . . ?
C34 C35 C36 120.9(2) . . ?
C34 C35 H35 119.6 . . ?
C36 C35 H35 119.6 . . ?
C31 C36 C35 119.47(18) . . ?
C31 C36 H36 120.3 . . ?
C35 C36 H36 120.3 . . ?
C53 C40 C41 120.63(13) . . ?
C53 C40 C2 120.35(13) . . ?
C41 C40 C2 118.91(12) . . ?
C40 C41 C42 122.40(13) . . ?
C40 C41 C46 119.57(13) . . ?
C42 C41 C46 117.96(13) . . ?
C43 C42 C41 121.50(14) . . ?
C43 C42 H42 119.3 . . ?
C41 C42 H42 119.3 . . ?
C42 C43 C44 120.42(15) . . ?
C42 C43 H43 119.8 . . ?
C44 C43 H43 119.8 . . ?
C45 C44 C43 120.26(16) . . ?
C45 C44 H44 119.9 . . ?
C43 C44 H44 119.9 . . ?
C44 C45 C46 121.11(15) . . ?
C44 C45 H45 119.4 . . ?
C46 C45 H45 119.4 . . ?
C47 C46 C45 122.10(14) . . ?
C47 C46 C41 119.17(14) . . ?
C45 C46 C41 118.72(14) . . ?
C48 C47 C46 121.80(14) . . ?
C48 C47 H47 119.1 . . ?
C46 C47 H47 119.1 . . ?
C47 C48 C49 121.33(15) . . ?
C47 C48 C53 119.81(14) . . ?
C49 C48 C53 118.86(15) . . ?
C50 C49 C48 120.94(17) . . ?
C50 C49 H49 119.5 . . ?
C48 C49 H49 119.5 . . ?
C49 C50 C51 120.60(16) . . ?
C49 C50 H50 119.7 . . ?
C51 C50 H50 119.7 . . ?
C52 C51 C50 120.70(18) . . ?
C52 C51 H51 119.7 . . ?
C50 C51 H51 119.7 . . ?
C51 C52 C53 121.15(16) . . ?
C51 C52 H52 119.4 . . ?
C53 C52 H52 119.4 . . ?
C40 C53 C52 123.29(14) . . ?
C40 C53 C48 118.95(14) . . ?
C52 C53 C48 117.75(14) . . ?

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 C1 N2 N1 166.94(16) . . . . ?
N3 C1 N2 N1 -14.7(2) . . . . ?
O1 C1 N2 C21 -13.0(3) . . . . ?
N3 C1 N2 C21 165.41(14) . . . . ?
C2 N1 N2 C1 37.77(18) . . . . ?
C3 N1 N2 C1 -93.74(16) . . . . ?
C2 N1 N2 C21 -142.30(13) . . . . ?
C3 N1 N2 C21 86.19(16) . . . . ?
N2 N1 C2 N4 -27.05(19) . . . . ?
C3 N1 C2 N4 104.35(16) . . . . ?
N2 N1 C2 C40 151.79(12) . . . . ?
C3 N1 C2 C40 -76.81(16) . . . . ?
O1 C1 N3 N4 156.36(16) . . . . ?
N2 C1 N3 N4 -22.1(2) . . . . ?
O1 C1 N3 C31 -1.6(2) . . . . ?
N2 C1 N3 C31 179.93(14) . . . . ?
C2 N1 C3 C4 -81.04(18) . . . . ?
N2 N1 C3 C4 49.06(18) . . . . ?
C2 N1 C3 C11 148.52(13) . . . . ?
N2 N1 C3 C11 -81.38(15) . . . . ?
N1 C2 N4 N3 -5.8(2) . . . . ?
C40 C2 N4 N3 175.36(12) . . . . ?
C1 N3 N4 C2 33.1(2) . . . . ?
C31 N3 N4 C2 -167.76(13) . . . . ?
N1 C3 C11 C16 -75.99(18) . . . . ?
C4 C3 C11 C16 154.01(17) . . . . ?
N1 C3 C11 C12 106.03(17) . . . . ?
C4 C3 C11 C12 -24.0(2) . . . . ?
C16 C11 C12 C13 -1.0(2) . . . . ?
C3 C11 C12 C13 177.00(15) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C12 C13 C14 C15 1.4(3) . . . . ?
C13 C14 C15 C16 -1.1(3) . . . . ?
C14 C15 C16 C11 -0.2(3) . . . . ?
C12 C11 C16 C15 1.3(3) . . . . ?
C3 C11 C16 C15 -176.80(16) . . . . ?
C1 N2 C21 C26 -148.08(17) . . . . ?
N1 N2 C21 C26 32.0(2) . . . . ?
C1 N2 C21 C22 34.6(2) . . . . ?
N1 N2 C21 C22 -145.34(16) . . . . ?
C26 C21 C22 C23 2.3(3) . . . . ?
N2 C21 C22 C23 179.63(19) . . . . ?
C21 C22 C23 C24 -0.7(3) . . . . ?
C22 C23 C24 C25 -1.2(4) . . . . ?
C23 C24 C25 C26 1.5(3) . . . . ?
C22 C21 C26 C25 -2.0(3) . . . . ?
N2 C21 C26 C25 -179.34(17) . . . . ?
C24 C25 C26 C21 0.1(3) . . . . ?
C1 N3 C31 C32 -80.5(2) . . . . ?
N4 N3 C31 C32 119.86(18) . . . . ?
C1 N3 C31 C36 101.6(2) . . . . ?
N4 N3 C31 C36 -58.0(2) . . . . ?
C36 C31 C32 C33 -0.5(3) . . . . ?
N3 C31 C32 C33 -178.44(19) . . . . ?
C31 C32 C33 C34 0.2(4) . . . . ?
C32 C33 C34 C35 -0.2(4) . . . . ?
C33 C34 C35 C36 0.5(3) . . . . ?
C32 C31 C36 C35 0.8(3) . . . . ?
N3 C31 C36 C35 178.65(18) . . . . ?
C34 C35 C36 C31 -0.8(3) . . . . ?
N4 C2 C40 C53 -67.39(18) . . . . ?
N1 C2 C40 C53 113.70(15) . . . . ?
N4 C2 C40 C41 108.97(16) . . . . ?
N1 C2 C40 C41 -69.93(17) . . . . ?
C53 C40 C41 C42 174.71(13) . . . . ?
C2 C40 C41 C42 -1.6(2) . . . . ?
C53 C40 C41 C46 -2.2(2) . . . . ?
C2 C40 C41 C46 -178.54(12) . . . . ?
C40 C41 C42 C43 -178.51(15) . . . . ?
C46 C41 C42 C43 -1.6(2) . . . . ?
C41 C42 C43 C44 0.5(3) . . . . ?
C42 C43 C44 C45 0.2(3) . . . . ?
C43 C44 C45 C46 0.2(3) . . . . ?
C44 C45 C46 C47 177.55(16) . . . . ?
C44 C45 C46 C41 -1.2(2) . . . . ?
C40 C41 C46 C47 0.1(2) . . . . ?
C42 C41 C46 C47 -176.94(14) . . . . ?
C40 C41 C46 C45 178.90(13) . . . . ?
C42 C41 C46 C45 1.9(2) . . . . ?
C45 C46 C47 C48 -176.69(15) . . . . ?
C41 C46 C47 C48 2.1(2) . . . . ?
C46 C47 C48 C49 177.08(15) . . . . ?
C46 C47 C48 C53 -2.1(2) . . . . ?
C47 C48 C49 C50 -178.50(17) . . . . ?
C53 C48 C49 C50 0.7(3) . . . . ?
C48 C49 C50 C51 -0.9(3) . . . . ?
C49 C50 C51 C52 0.5(3) . . . . ?
C50 C51 C52 C53 -0.1(3) . . . . ?
C41 C40 C53 C52 -176.81(14) . . . . ?
C2 C40 C53 C52 -0.5(2) . . . . ?
C41 C40 C53 C48 2.1(2) . . . . ?
C2 C40 C53 C48 178.43(12) . . . . ?
C51 C52 C53 C40 178.87(16) . . . . ?
C51 C52 C53 C48 -0.1(2) . . . . ?
C47 C48 C53 C40 0.0(2) . . . . ?
C49 C48 C53 C40 -179.22(14) . . . . ?
C47 C48 C53 C52 178.99(14) . . . . ?
C49 C48 C53 C52 -0.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        66.96
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.036
#=============================================================================
#  end of cif data for "stu6996" (compound 19) 
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================

