# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_131225a
_database_code_depnum_ccdc_archive 'CCDC 1561315'
_audit_update_record             
;
2017-07-10 deposited with the CCDC.
2017-08-30 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 H23 N3 O'
_chemical_formula_weight         405.48

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'
O O 0.0106 0.0060 '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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.8840(9)
_cell_length_b                   14.4830(13)
_cell_length_c                   14.9970(12)
_cell_angle_alpha                104.061(2)
_cell_angle_beta                 106.620(2)
_cell_angle_gamma                100.8970(10)
_cell_volume                     2110.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2118
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      26.227

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9706
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10773
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0666
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         25.02
_reflns_number_total             7310
_reflns_number_gt                3564
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0255P)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         7310
_refine_ls_number_parameters     563
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1069
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 0.35324(17) 0.07712(13) 0.53590(13) 0.0430(5) Uani 1 1 d . . .
N2 N 0.38174(18) 0.09942(13) 0.70647(13) 0.0470(5) Uani 1 1 d . . .
N3 N 0.4846(2) 0.14466(14) 0.79610(13) 0.0539(6) Uani 1 1 d . . .
N4 N 0.35701(18) 0.57625(13) 0.44947(14) 0.0482(5) Uani 1 1 d . . .
N5 N 0.3039(2) 0.54720(14) 0.27537(14) 0.0526(6) Uani 1 1 d . . .
N6 N 0.3737(2) 0.56299(15) 0.21328(14) 0.0603(6) Uani 1 1 d . . .
O1 O 0.34264(14) 0.06286(11) 0.38248(10) 0.0513(4) Uani 1 1 d . . .
O2 O 0.42218(15) 0.60895(11) 0.61179(11) 0.0566(5) Uani 1 1 d . . .
C1 C 0.3977(2) 0.07766(16) 0.31169(16) 0.0444(6) Uani 1 1 d . . .
C2 C 0.5282(2) 0.12393(16) 0.33324(16) 0.0414(6) Uani 1 1 d . . .
C3 C 0.6247(2) 0.16271(16) 0.43746(15) 0.0456(6) Uani 1 1 d . . .
H3A H 0.6657 0.2330 0.4535 0.055 Uiso 1 1 calc R . .
H3B H 0.6950 0.1297 0.4426 0.055 Uiso 1 1 calc R . .
C4 C 0.5594(2) 0.14723(15) 0.51119(16) 0.0388(6) Uani 1 1 d . . .
C5 C 0.4236(2) 0.09775(16) 0.48024(16) 0.0412(6) Uani 1 1 d . . .
C6 C 0.4275(2) 0.11039(16) 0.63192(16) 0.0409(6) Uani 1 1 d . . .
C7 C 0.5627(2) 0.16223(16) 0.67402(16) 0.0418(6) Uani 1 1 d . . .
C8 C 0.5914(2) 0.18157(17) 0.77728(17) 0.0501(7) Uani 1 1 d . . .
C9 C 0.7184(2) 0.23800(18) 0.86151(15) 0.0694(8) Uani 1 1 d . . .
H9A H 0.7401 0.3063 0.8644 0.104 Uiso 1 1 calc R . .
H9B H 0.7894 0.2106 0.8525 0.104 Uiso 1 1 calc R . .
H9C H 0.7072 0.2333 0.9216 0.104 Uiso 1 1 calc R . .
C10 C 0.6318(2) 0.18158(16) 0.61144(16) 0.0411(6) Uani 1 1 d . . .
C11 C 0.7781(2) 0.23669(17) 0.65212(16) 0.0486(7) Uani 1 1 d . . .
H11A H 0.7965 0.2864 0.7143 0.058 Uiso 1 1 calc R . .
H11B H 0.7976 0.2710 0.6076 0.058 Uiso 1 1 calc R . .
C12 C 0.8716(2) 0.17113(18) 0.66785(18) 0.0635(8) Uani 1 1 d . . .
H12A H 0.8497 0.1340 0.7097 0.076 Uiso 1 1 calc R . .
H12B H 0.8581 0.1241 0.6052 0.076 Uiso 1 1 calc R . .
C13 C 1.0171(2) 0.2314(2) 0.71449(19) 0.0838(10) Uani 1 1 d . . .
H13A H 1.0396 0.2672 0.6726 0.126 Uiso 1 1 calc R . .
H13B H 1.0726 0.1877 0.7233 0.126 Uiso 1 1 calc R . .
H13C H 1.0311 0.2773 0.7770 0.126 Uiso 1 1 calc R . .
C14 C 0.3038(2) 0.03965(17) 0.21538(17) 0.0543(7) Uani 1 1 d . . .
H14 H 0.2157 0.0072 0.2036 0.065 Uiso 1 1 calc R . .
C15 C 0.3442(3) 0.05125(18) 0.13994(17) 0.0584(7) Uani 1 1 d . . .
H15 H 0.2825 0.0275 0.0764 0.070 Uiso 1 1 calc R . .
C16 C 0.4784(3) 0.09873(17) 0.15658(17) 0.0518(7) Uani 1 1 d . . .
C17 C 0.5713(2) 0.13590(16) 0.25445(17) 0.0465(6) Uani 1 1 d . . .
C18 C 0.7043(3) 0.18373(18) 0.26936(18) 0.0579(7) Uani 1 1 d . . .
H18 H 0.7665 0.2084 0.3328 0.070 Uiso 1 1 calc R . .
C19 C 0.7446(3) 0.1949(2) 0.1933(2) 0.0711(8) Uani 1 1 d . . .
H19 H 0.8331 0.2267 0.2053 0.085 Uiso 1 1 calc R . .
C20 C 0.6522(3) 0.1582(2) 0.0972(2) 0.0763(9) Uani 1 1 d . . .
H20 H 0.6796 0.1654 0.0454 0.092 Uiso 1 1 calc R . .
C21 C 0.5228(3) 0.11219(19) 0.07963(19) 0.0670(8) Uani 1 1 d . . .
H21 H 0.4623 0.0891 0.0157 0.080 Uiso 1 1 calc R . .
C22 C 0.2549(2) 0.05035(17) 0.70564(17) 0.0449(6) Uani 1 1 d . . .
C23 C 0.1494(2) 0.00237(17) 0.61830(17) 0.0554(7) Uani 1 1 d . . .
H23 H 0.1603 0.0018 0.5589 0.067 Uiso 1 1 calc R . .
C24 C 0.0274(3) -0.04487(19) 0.6201(2) 0.0645(8) Uani 1 1 d . . .
H24 H -0.0438 -0.0763 0.5614 0.077 Uiso 1 1 calc R . .
C25 C 0.0095(3) -0.04636(19) 0.7067(2) 0.0674(8) Uani 1 1 d . . .
H25 H -0.0724 -0.0791 0.7072 0.081 Uiso 1 1 calc R . .
C26 C 0.1156(3) 0.0017(2) 0.7929(2) 0.0696(8) Uani 1 1 d . . .
H26 H 0.1047 0.0015 0.8521 0.084 Uiso 1 1 calc R . .
C27 C 0.2376(3) 0.05011(19) 0.79323(18) 0.0599(7) Uani 1 1 d . . .
H27 H 0.3080 0.0825 0.8522 0.072 Uiso 1 1 calc R . .
C28 C 0.5185(2) 0.64362(17) 0.70604(17) 0.0486(7) Uani 1 1 d . . .
C29 C 0.6495(2) 0.68451(17) 0.72510(17) 0.0475(6) Uani 1 1 d . . .
C30 C 0.7009(2) 0.69419(17) 0.64436(16) 0.0554(7) Uani 1 1 d . . .
H30A H 0.7689 0.6594 0.6452 0.067 Uiso 1 1 calc R . .
H30B H 0.7428 0.7636 0.6569 0.067 Uiso 1 1 calc R . .
C31 C 0.5948(2) 0.65420(16) 0.54403(17) 0.0451(6) Uani 1 1 d . . .
C32 C 0.4614(3) 0.61401(17) 0.53319(18) 0.0474(6) Uani 1 1 d . . .
C33 C 0.3907(2) 0.58025(16) 0.37077(18) 0.0464(6) Uani 1 1 d . . .
C34 C 0.5189(2) 0.61697(16) 0.37010(17) 0.0474(6) Uani 1 1 d . . .
C35 C 0.5007(3) 0.60429(18) 0.26896(19) 0.0566(7) Uani 1 1 d . . .
C36 C 0.5998(3) 0.6292(2) 0.22029(18) 0.0767(9) Uani 1 1 d . . .
H36A H 0.5551 0.6076 0.1505 0.115 Uiso 1 1 calc R . .
H36B H 0.6680 0.5964 0.2360 0.115 Uiso 1 1 calc R . .
H36C H 0.6395 0.6996 0.2432 0.115 Uiso 1 1 calc R . .
C37 C 0.6250(2) 0.65600(16) 0.46020(18) 0.0474(6) Uani 1 1 d . . .
C38 C 0.7676(2) 0.69368(18) 0.46743(17) 0.0597(7) Uani 1 1 d . . .
H38A H 0.8151 0.7473 0.5285 0.072 Uiso 1 1 calc R . .
H38B H 0.7689 0.7200 0.4140 0.072 Uiso 1 1 calc R . .
C39 C 0.8397(2) 0.6119(2) 0.46341(19) 0.0724(8) Uani 1 1 d . . .
H39A H 0.8096 0.5690 0.4981 0.087 Uiso 1 1 calc R . .
H39B H 0.8152 0.5720 0.3956 0.087 Uiso 1 1 calc R . .
C40 C 0.9889(3) 0.6515(2) 0.5074(2) 0.1024(11) Uani 1 1 d . . .
H40A H 1.0190 0.6970 0.4759 0.154 Uiso 1 1 calc R . .
H40B H 1.0284 0.5977 0.4981 0.154 Uiso 1 1 calc R . .
H40C H 1.0145 0.6853 0.5762 0.154 Uiso 1 1 calc R . .
C41 C 0.4648(3) 0.63270(18) 0.77930(18) 0.0578(7) Uani 1 1 d . . .
H41 H 0.3740 0.6042 0.7631 0.069 Uiso 1 1 calc R . .
C42 C 0.5489(3) 0.66481(18) 0.87436(19) 0.0649(8) Uani 1 1 d . . .
H42 H 0.5150 0.6570 0.9232 0.078 Uiso 1 1 calc R . .
C43 C 0.6862(3) 0.70963(19) 0.90004(18) 0.0592(7) Uani 1 1 d . . .
C44 C 0.7376(3) 0.72010(17) 0.82492(18) 0.0528(7) Uani 1 1 d . . .
C45 C 0.8751(3) 0.76747(19) 0.85206(19) 0.0676(8) Uani 1 1 d . . .
H45 H 0.9104 0.7745 0.8036 0.081 Uiso 1 1 calc R . .
C46 C 0.9572(3) 0.8032(2) 0.9483(2) 0.0841(10) Uani 1 1 d . . .
H46 H 1.0469 0.8352 0.9649 0.101 Uiso 1 1 calc R . .
C47 C 0.9061(4) 0.7915(2) 1.0219(2) 0.0948(11) Uani 1 1 d . . .
H47 H 0.9626 0.8146 1.0870 0.114 Uiso 1 1 calc R . .
C48 C 0.7737(3) 0.7463(2) 0.9987(2) 0.0835(10) Uani 1 1 d . . .
H48 H 0.7409 0.7396 1.0484 0.100 Uiso 1 1 calc R . .
C49 C 0.1638(3) 0.50460(17) 0.23400(18) 0.0543(7) Uani 1 1 d . . .
C50 C 0.0878(3) 0.49291(19) 0.29191(19) 0.0642(8) Uani 1 1 d . . .
H50 H 0.1286 0.5123 0.3597 0.077 Uiso 1 1 calc R . .
C51 C -0.0491(3) 0.4525(2) 0.2497(2) 0.0773(9) Uani 1 1 d . . .
H51 H -0.0996 0.4443 0.2892 0.093 Uiso 1 1 calc R . .
C52 C -0.1108(3) 0.4244(2) 0.1498(2) 0.0868(10) Uani 1 1 d . . .
H52 H -0.2030 0.3984 0.1215 0.104 Uiso 1 1 calc R . .
C53 C -0.0341(3) 0.4352(2) 0.0922(2) 0.0917(11) Uani 1 1 d . . .
H53 H -0.0752 0.4153 0.0244 0.110 Uiso 1 1 calc R . .
C54 C 0.1023(3) 0.47503(19) 0.13322(19) 0.0751(9) Uani 1 1 d . . .
H54 H 0.1528 0.4820 0.0934 0.090 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.331(3) . ?
N1 C6 1.345(2) . ?
N2 C6 1.378(3) . ?
N2 N3 1.387(2) . ?
N2 C22 1.423(3) . ?
N3 C8 1.320(3) . ?
N4 C32 1.335(3) . ?
N4 C33 1.343(3) . ?
N5 C33 1.375(3) . ?
N5 N6 1.392(3) . ?
N5 C49 1.417(3) . ?
N6 C35 1.323(3) . ?
O1 C5 1.383(2) . ?
O1 C1 1.399(2) . ?
O2 C32 1.377(3) . ?
O2 C28 1.399(2) . ?
C1 C2 1.358(3) . ?
C1 C14 1.411(3) . ?
C2 C17 1.425(3) . ?
C2 C3 1.508(3) . ?
C3 C4 1.513(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C10 1.393(3) . ?
C4 C5 1.400(3) . ?
C6 C7 1.396(3) . ?
C7 C10 1.406(3) . ?
C7 C8 1.433(3) . ?
C8 C9 1.499(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.507(3) . ?
C11 C12 1.526(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.519(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.361(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.413(3) . ?
C15 H15 0.9300 . ?
C16 C21 1.413(3) . ?
C16 C17 1.424(3) . ?
C17 C18 1.409(3) . ?
C18 C19 1.366(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.403(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.358(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C27 1.380(3) . ?
C22 C23 1.383(3) . ?
C23 C24 1.384(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.372(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.376(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.377(3) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.352(3) . ?
C28 C41 1.411(3) . ?
C29 C44 1.429(3) . ?
C29 C30 1.496(3) . ?
C30 C31 1.504(3) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C37 1.392(3) . ?
C31 C32 1.405(3) . ?
C33 C34 1.401(3) . ?
C34 C37 1.403(3) . ?
C34 C35 1.433(3) . ?
C35 C36 1.502(3) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 C38 1.508(3) . ?
C38 C39 1.539(3) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 C40 1.500(3) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 C42 1.363(3) . ?
C41 H41 0.9300 . ?
C42 C43 1.409(3) . ?
C42 H42 0.9300 . ?
C43 C48 1.414(3) . ?
C43 C44 1.420(3) . ?
C44 C45 1.416(3) . ?
C45 C46 1.369(3) . ?
C45 H45 0.9300 . ?
C46 C47 1.400(4) . ?
C46 H46 0.9300 . ?
C47 C48 1.368(4) . ?
C47 H47 0.9300 . ?
C48 H48 0.9300 . ?
C49 C50 1.377(3) . ?
C49 C54 1.384(3) . ?
C50 C51 1.383(3) . ?
C50 H50 0.9300 . ?
C51 C52 1.373(3) . ?
C51 H51 0.9300 . ?
C52 C53 1.378(4) . ?
C52 H52 0.9300 . ?
C53 C54 1.377(3) . ?
C53 H53 0.9300 . ?
C54 H54 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C6 112.44(19) . . ?
C6 N2 N3 109.67(19) . . ?
C6 N2 C22 131.94(19) . . ?
N3 N2 C22 118.37(19) . . ?
C8 N3 N2 106.80(19) . . ?
C32 N4 C33 112.7(2) . . ?
C33 N5 N6 109.7(2) . . ?
C33 N5 C49 131.7(2) . . ?
N6 N5 C49 118.6(2) . . ?
C35 N6 N5 107.03(19) . . ?
C5 O1 C1 119.14(18) . . ?
C32 O2 C28 119.10(19) . . ?
C2 C1 O1 123.6(2) . . ?
C2 C1 C14 123.3(2) . . ?
O1 C1 C14 113.2(2) . . ?
C1 C2 C17 118.0(2) . . ?
C1 C2 C3 121.1(2) . . ?
C17 C2 C3 120.8(2) . . ?
C2 C3 C4 113.11(19) . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C10 C4 C5 118.0(2) . . ?
C10 C4 C3 121.3(2) . . ?
C5 C4 C3 120.66(19) . . ?
N1 C5 O1 110.19(19) . . ?
N1 C5 C4 127.5(2) . . ?
O1 C5 C4 122.3(2) . . ?
N1 C6 N2 125.3(2) . . ?
N1 C6 C7 126.7(2) . . ?
N2 C6 C7 107.93(19) . . ?
C6 C7 C10 118.2(2) . . ?
C6 C7 C8 104.2(2) . . ?
C10 C7 C8 137.6(2) . . ?
N3 C8 C7 111.4(2) . . ?
N3 C8 C9 118.8(2) . . ?
C7 C8 C9 129.8(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C10 C7 117.1(2) . . ?
C4 C10 C11 122.0(2) . . ?
C7 C10 C11 120.87(19) . . ?
C10 C11 C12 114.34(19) . . ?
C10 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
C10 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 C11 111.9(2) . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C1 118.9(2) . . ?
C15 C14 H14 120.5 . . ?
C1 C14 H14 120.5 . . ?
C14 C15 C16 121.1(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C15 C16 C21 122.2(2) . . ?
C15 C16 C17 118.8(2) . . ?
C21 C16 C17 118.9(3) . . ?
C18 C17 C16 117.8(2) . . ?
C18 C17 C2 122.3(2) . . ?
C16 C17 C2 119.8(2) . . ?
C19 C18 C17 121.9(2) . . ?
C19 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
C18 C19 C20 119.8(3) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C21 C20 C19 120.2(3) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C16 121.3(3) . . ?
C20 C21 H21 119.4 . . ?
C16 C21 H21 119.4 . . ?
C27 C22 C23 119.7(2) . . ?
C27 C22 N2 119.4(2) . . ?
C23 C22 N2 120.9(2) . . ?
C22 C23 C24 119.4(2) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C25 C24 C23 121.4(2) . . ?
C25 C24 H24 119.3 . . ?
C23 C24 H24 119.3 . . ?
C24 C25 C26 118.4(3) . . ?
C24 C25 H25 120.8 . . ?
C26 C25 H25 120.8 . . ?
C25 C26 C27 121.4(3) . . ?
C25 C26 H26 119.3 . . ?
C27 C26 H26 119.3 . . ?
C26 C27 C22 119.7(2) . . ?
C26 C27 H27 120.1 . . ?
C22 C27 H27 120.1 . . ?
C29 C28 O2 123.5(2) . . ?
C29 C28 C41 123.4(2) . . ?
O2 C28 C41 113.1(2) . . ?
C28 C29 C44 118.2(2) . . ?
C28 C29 C30 121.1(2) . . ?
C44 C29 C30 120.7(2) . . ?
C29 C30 C31 113.8(2) . . ?
C29 C30 H30A 108.8 . . ?
C31 C30 H30A 108.8 . . ?
C29 C30 H30B 108.8 . . ?
C31 C30 H30B 108.8 . . ?
H30A C30 H30B 107.7 . . ?
C37 C31 C32 118.3(2) . . ?
C37 C31 C30 121.7(2) . . ?
C32 C31 C30 120.0(2) . . ?
N4 C32 O2 110.7(2) . . ?
N4 C32 C31 126.8(2) . . ?
O2 C32 C31 122.4(2) . . ?
N4 C33 N5 125.5(2) . . ?
N4 C33 C34 126.8(2) . . ?
N5 C33 C34 107.7(2) . . ?
C33 C34 C37 118.0(2) . . ?
C33 C34 C35 104.7(2) . . ?
C37 C34 C35 137.2(2) . . ?
N6 C35 C34 110.9(2) . . ?
N6 C35 C36 118.4(2) . . ?
C34 C35 C36 130.8(2) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C31 C37 C34 117.2(2) . . ?
C31 C37 C38 120.3(2) . . ?
C34 C37 C38 122.4(2) . . ?
C37 C38 C39 112.1(2) . . ?
C37 C38 H38A 109.2 . . ?
C39 C38 H38A 109.2 . . ?
C37 C38 H38B 109.2 . . ?
C39 C38 H38B 109.2 . . ?
H38A C38 H38B 107.9 . . ?
C40 C39 C38 113.2(2) . . ?
C40 C39 H39A 108.9 . . ?
C38 C39 H39A 108.9 . . ?
C40 C39 H39B 108.9 . . ?
C38 C39 H39B 108.9 . . ?
H39A C39 H39B 107.7 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C42 C41 C28 118.5(3) . . ?
C42 C41 H41 120.7 . . ?
C28 C41 H41 120.7 . . ?
C41 C42 C43 121.2(3) . . ?
C41 C42 H42 119.4 . . ?
C43 C42 H42 119.4 . . ?
C42 C43 C48 121.8(3) . . ?
C42 C43 C44 119.1(2) . . ?
C48 C43 C44 119.1(3) . . ?
C45 C44 C43 118.4(2) . . ?
C45 C44 C29 122.1(2) . . ?
C43 C44 C29 119.5(2) . . ?
C46 C45 C44 121.2(3) . . ?
C46 C45 H45 119.4 . . ?
C44 C45 H45 119.4 . . ?
C45 C46 C47 120.1(3) . . ?
C45 C46 H46 120.0 . . ?
C47 C46 H46 120.0 . . ?
C48 C47 C46 120.6(3) . . ?
C48 C47 H47 119.7 . . ?
C46 C47 H47 119.7 . . ?
C47 C48 C43 120.7(3) . . ?
C47 C48 H48 119.7 . . ?
C43 C48 H48 119.7 . . ?
C50 C49 C54 119.5(3) . . ?
C50 C49 N5 121.5(2) . . ?
C54 C49 N5 119.0(3) . . ?
C49 C50 C51 120.3(2) . . ?
C49 C50 H50 119.9 . . ?
C51 C50 H50 119.9 . . ?
C52 C51 C50 120.5(3) . . ?
C52 C51 H51 119.8 . . ?
C50 C51 H51 119.8 . . ?
C51 C52 C53 119.0(3) . . ?
C51 C52 H52 120.5 . . ?
C53 C52 H52 120.5 . . ?
C54 C53 C52 121.1(3) . . ?
C54 C53 H53 119.4 . . ?
C52 C53 H53 119.4 . . ?
C53 C54 C49 119.6(3) . . ?
C53 C54 H54 120.2 . . ?
C49 C54 H54 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N2 N3 C8 -0.7(2) . . . . ?
C22 N2 N3 C8 178.0(2) . . . . ?
C33 N5 N6 C35 0.4(3) . . . . ?
C49 N5 N6 C35 179.0(2) . . . . ?
C5 O1 C1 C2 0.8(3) . . . . ?
C5 O1 C1 C14 -179.17(18) . . . . ?
O1 C1 C2 C17 -178.9(2) . . . . ?
C14 C1 C2 C17 1.1(3) . . . . ?
O1 C1 C2 C3 0.4(3) . . . . ?
C14 C1 C2 C3 -179.6(2) . . . . ?
C1 C2 C3 C4 -1.9(3) . . . . ?
C17 C2 C3 C4 177.4(2) . . . . ?
C2 C3 C4 C10 -177.57(19) . . . . ?
C2 C3 C4 C5 2.4(3) . . . . ?
C6 N1 C5 O1 -179.48(17) . . . . ?
C6 N1 C5 C4 0.4(3) . . . . ?
C1 O1 C5 N1 179.66(19) . . . . ?
C1 O1 C5 C4 -0.3(3) . . . . ?
C10 C4 C5 N1 -1.4(3) . . . . ?
C3 C4 C5 N1 178.7(2) . . . . ?
C10 C4 C5 O1 178.53(19) . . . . ?
C3 C4 C5 O1 -1.4(3) . . . . ?
C5 N1 C6 N2 -179.7(2) . . . . ?
C5 N1 C6 C7 0.8(3) . . . . ?
N3 N2 C6 N1 -178.6(2) . . . . ?
C22 N2 C6 N1 2.9(4) . . . . ?
N3 N2 C6 C7 0.9(2) . . . . ?
C22 N2 C6 C7 -177.5(2) . . . . ?
N1 C6 C7 C10 -1.0(3) . . . . ?
N2 C6 C7 C10 179.4(2) . . . . ?
N1 C6 C7 C8 178.8(2) . . . . ?
N2 C6 C7 C8 -0.8(2) . . . . ?
N2 N3 C8 C7 0.2(3) . . . . ?
N2 N3 C8 C9 178.2(2) . . . . ?
C6 C7 C8 N3 0.4(3) . . . . ?
C10 C7 C8 N3 -179.9(3) . . . . ?
C6 C7 C8 C9 -177.4(2) . . . . ?
C10 C7 C8 C9 2.3(5) . . . . ?
C5 C4 C10 C7 1.0(3) . . . . ?
C3 C4 C10 C7 -179.0(2) . . . . ?
C5 C4 C10 C11 -179.3(2) . . . . ?
C3 C4 C10 C11 0.6(3) . . . . ?
C6 C7 C10 C4 0.0(3) . . . . ?
C8 C7 C10 C4 -179.7(2) . . . . ?
C6 C7 C10 C11 -179.64(19) . . . . ?
C8 C7 C10 C11 0.6(4) . . . . ?
C4 C10 C11 C12 -93.2(3) . . . . ?
C7 C10 C11 C12 86.4(3) . . . . ?
C10 C11 C12 C13 -176.61(19) . . . . ?
C2 C1 C14 C15 -1.4(4) . . . . ?
O1 C1 C14 C15 178.6(2) . . . . ?
C1 C14 C15 C16 1.2(4) . . . . ?
C14 C15 C16 C21 -179.7(2) . . . . ?
C14 C15 C16 C17 -0.9(4) . . . . ?
C15 C16 C17 C18 -179.5(2) . . . . ?
C21 C16 C17 C18 -0.6(3) . . . . ?
C15 C16 C17 C2 0.6(3) . . . . ?
C21 C16 C17 C2 179.4(2) . . . . ?
C1 C2 C17 C18 179.4(2) . . . . ?
C3 C2 C17 C18 0.1(3) . . . . ?
C1 C2 C17 C16 -0.7(3) . . . . ?
C3 C2 C17 C16 -179.9(2) . . . . ?
C16 C17 C18 C19 0.1(3) . . . . ?
C2 C17 C18 C19 -180.0(2) . . . . ?
C17 C18 C19 C20 0.1(4) . . . . ?
C18 C19 C20 C21 0.4(4) . . . . ?
C19 C20 C21 C16 -1.0(4) . . . . ?
C15 C16 C21 C20 179.9(2) . . . . ?
C17 C16 C21 C20 1.1(4) . . . . ?
C6 N2 C22 C27 179.1(2) . . . . ?
N3 N2 C22 C27 0.7(3) . . . . ?
C6 N2 C22 C23 -0.4(4) . . . . ?
N3 N2 C22 C23 -178.8(2) . . . . ?
C27 C22 C23 C24 0.3(4) . . . . ?
N2 C22 C23 C24 179.8(2) . . . . ?
C22 C23 C24 C25 -1.0(4) . . . . ?
C23 C24 C25 C26 0.9(4) . . . . ?
C24 C25 C26 C27 -0.2(4) . . . . ?
C25 C26 C27 C22 -0.4(4) . . . . ?
C23 C22 C27 C26 0.3(4) . . . . ?
N2 C22 C27 C26 -179.2(2) . . . . ?
C32 O2 C28 C29 1.6(3) . . . . ?
C32 O2 C28 C41 -179.2(2) . . . . ?
O2 C28 C29 C44 178.0(2) . . . . ?
C41 C28 C29 C44 -1.2(3) . . . . ?
O2 C28 C29 C30 -0.8(3) . . . . ?
C41 C28 C29 C30 180.0(2) . . . . ?
C28 C29 C30 C31 -0.4(3) . . . . ?
C44 C29 C30 C31 -179.3(2) . . . . ?
C29 C30 C31 C37 -179.2(2) . . . . ?
C29 C30 C31 C32 1.0(3) . . . . ?
C33 N4 C32 O2 179.62(19) . . . . ?
C33 N4 C32 C31 -0.5(3) . . . . ?
C28 O2 C32 N4 178.95(18) . . . . ?
C28 O2 C32 C31 -1.0(3) . . . . ?
C37 C31 C32 N4 0.0(3) . . . . ?
C30 C31 C32 N4 179.8(2) . . . . ?
C37 C31 C32 O2 179.9(2) . . . . ?
C30 C31 C32 O2 -0.3(3) . . . . ?
C32 N4 C33 N5 -179.8(2) . . . . ?
C32 N4 C33 C34 1.2(3) . . . . ?
N6 N5 C33 N4 -179.9(2) . . . . ?
C49 N5 C33 N4 1.7(4) . . . . ?
N6 N5 C33 C34 -0.7(2) . . . . ?
C49 N5 C33 C34 -179.1(2) . . . . ?
N4 C33 C34 C37 -1.4(4) . . . . ?
N5 C33 C34 C37 179.4(2) . . . . ?
N4 C33 C34 C35 179.9(2) . . . . ?
N5 C33 C34 C35 0.7(2) . . . . ?
N5 N6 C35 C34 0.1(3) . . . . ?
N5 N6 C35 C36 179.8(2) . . . . ?
C33 C34 C35 N6 -0.5(3) . . . . ?
C37 C34 C35 N6 -178.8(3) . . . . ?
C33 C34 C35 C36 179.9(3) . . . . ?
C37 C34 C35 C36 1.6(5) . . . . ?
C32 C31 C37 C34 -0.1(3) . . . . ?
C30 C31 C37 C34 -179.9(2) . . . . ?
C32 C31 C37 C38 -176.9(2) . . . . ?
C30 C31 C37 C38 3.2(3) . . . . ?
C33 C34 C37 C31 0.8(3) . . . . ?
C35 C34 C37 C31 178.9(3) . . . . ?
C33 C34 C37 C38 177.5(2) . . . . ?
C35 C34 C37 C38 -4.3(4) . . . . ?
C31 C37 C38 C39 86.4(3) . . . . ?
C34 C37 C38 C39 -90.3(3) . . . . ?
C37 C38 C39 C40 -158.1(2) . . . . ?
C29 C28 C41 C42 -0.1(4) . . . . ?
O2 C28 C41 C42 -179.3(2) . . . . ?
C28 C41 C42 C43 1.1(4) . . . . ?
C41 C42 C43 C48 177.8(3) . . . . ?
C41 C42 C43 C44 -0.8(4) . . . . ?
C42 C43 C44 C45 178.5(2) . . . . ?
C48 C43 C44 C45 -0.2(4) . . . . ?
C42 C43 C44 C29 -0.4(4) . . . . ?
C48 C43 C44 C29 -179.1(2) . . . . ?
C28 C29 C44 C45 -177.5(2) . . . . ?
C30 C29 C44 C45 1.4(3) . . . . ?
C28 C29 C44 C43 1.4(3) . . . . ?
C30 C29 C44 C43 -179.8(2) . . . . ?
C43 C44 C45 C46 -0.5(4) . . . . ?
C29 C44 C45 C46 178.4(2) . . . . ?
C44 C45 C46 C47 1.2(4) . . . . ?
C45 C46 C47 C48 -1.3(5) . . . . ?
C46 C47 C48 C43 0.6(5) . . . . ?
C42 C43 C48 C47 -178.5(3) . . . . ?
C44 C43 C48 C47 0.1(4) . . . . ?
C33 N5 C49 C50 2.6(4) . . . . ?
N6 N5 C49 C50 -175.8(2) . . . . ?
C33 N5 C49 C54 -178.0(2) . . . . ?
N6 N5 C49 C54 3.6(3) . . . . ?
C54 C49 C50 C51 -0.4(4) . . . . ?
N5 C49 C50 C51 179.0(2) . . . . ?
C49 C50 C51 C52 -0.6(4) . . . . ?
C50 C51 C52 C53 1.2(5) . . . . ?
C51 C52 C53 C54 -1.0(5) . . . . ?
C52 C53 C54 C49 0.1(4) . . . . ?
C50 C49 C54 C53 0.6(4) . . . . ?
N5 C49 C54 C53 -178.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_130930d
_database_code_depnum_ccdc_archive 'CCDC 1561314'
_audit_update_record             
;
2017-08-25 deposited with the CCDC.
2017-08-30 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 H21 N3 O2'
_chemical_formula_weight         419.47

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'
O O 0.0106 0.0060 '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   P2(1)/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                   10.0070(9)
_cell_length_b                   11.0039(11)
_cell_length_c                   18.1201(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.024(2)
_cell_angle_gamma                90.00
_cell_volume                     1927.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    887
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      19.495

_exptl_crystal_description       white
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9835
_exptl_absorpt_correction_T_max  0.9880
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9567
_diffrn_reflns_av_R_equivalents  0.1236
_diffrn_reflns_av_sigmaI/netI    0.1758
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.70
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3374
_reflns_number_gt                1374
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0859P)²+0.7378P] 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       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3374
_refine_ls_number_parameters     321
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1874
_refine_ls_R_factor_gt           0.0752
_refine_ls_wR_factor_ref         0.2666
_refine_ls_wR_factor_gt          0.1788
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
N1 N 0.5021(5) 0.6382(4) 0.3942(2) 0.0450(12) Uani 1 1 d . A .
N2 N 0.5167(5) 0.5779(4) 0.3327(2) 0.0473(12) Uani 1 1 d . A .
N3 N 0.6085(5) 0.6427(4) 0.5253(3) 0.0553(14) Uani 1 1 d . A .
O1 O 1.0194(4) 0.4162(4) 0.5866(2) 0.0547(11) Uani 1 1 d . . .
O2 O 0.9789(5) 0.5333(4) 0.6721(3) 0.0797(15) Uani 1 1 d . . .
C1 C 0.9332(6) 0.4886(6) 0.6119(4) 0.0552(16) Uani 1 1 d . . .
C2 C 0.8010(6) 0.5113(5) 0.5604(3) 0.0476(15) Uani 1 1 d . A .
C3 C 0.7669(5) 0.4506(5) 0.4919(3) 0.0413(14) Uani 1 1 d . . .
C4 C 0.8420(6) 0.3440(5) 0.4847(3) 0.0421(14) Uani 1 1 d . . .
C5 C 0.9720(6) 0.3359(5) 0.5305(3) 0.0467(14) Uani 1 1 d . . .
C6 C 1.0630(6) 0.2485(6) 0.5224(3) 0.0557(16) Uani 1 1 d . . .
H6 H 1.1542 0.2504 0.5517 0.067 Uiso 1 1 calc R . .
C7 C 1.0196(7) 0.1612(6) 0.4723(3) 0.0590(17) Uani 1 1 d . . .
H7 H 1.0827 0.1039 0.4644 0.071 Uiso 1 1 calc R . .
C8 C 0.8830(7) 0.1523(5) 0.4313(3) 0.0512(15) Uani 1 1 d . . .
C9 C 0.7910(6) 0.2433(5) 0.4388(3) 0.0448(15) Uani 1 1 d . . .
C10 C 0.6527(6) 0.2239(5) 0.4079(3) 0.0504(15) Uani 1 1 d . . .
H10 H 0.5890 0.2807 0.4158 0.061 Uiso 1 1 calc R . .
C11 C 0.6078(7) 0.1239(6) 0.3661(3) 0.0633(18) Uani 1 1 d . . .
H11 H 0.5135 0.1123 0.3452 0.076 Uiso 1 1 calc R . .
C12 C 0.6994(8) 0.0396(6) 0.3541(4) 0.0680(19) Uani 1 1 d . . .
H12 H 0.6678 -0.0272 0.3231 0.082 Uiso 1 1 calc R . .
C13 C 0.8325(8) 0.0523(6) 0.3862(3) 0.0647(19) Uani 1 1 d . . .
H13 H 0.8938 -0.0070 0.3785 0.078 Uiso 1 1 calc R . .
C14 C 0.7150(6) 0.5986(6) 0.5763(3) 0.0582(17) Uani 1 1 d . . .
C15 C 0.7196(10) 0.6362(11) 0.6565(8) 0.049(4) Uani 0.75(3) 1 d P A 1
H15A H 0.6265 0.6443 0.6625 0.059 Uiso 0.75(3) 1 calc PR A 1
H15B H 0.7679 0.5753 0.6924 0.059 Uiso 0.75(3) 1 calc PR A 1
C16 C 0.7939(11) 0.7554(12) 0.6717(8) 0.061(4) Uani 0.75(3) 1 d P A 1
H16A H 0.7451 0.8159 0.6358 0.073 Uiso 0.75(3) 1 calc PR A 1
H16B H 0.8866 0.7470 0.6651 0.073 Uiso 0.75(3) 1 calc PR A 1
C17 C 0.801(3) 0.796(2) 0.7529(11) 0.082(6) Uani 0.75(3) 1 d P A 1
H17A H 0.7096 0.7997 0.7599 0.123 Uiso 0.75(3) 1 calc PR A 1
H17B H 0.8438 0.8744 0.7617 0.123 Uiso 0.75(3) 1 calc PR A 1
H17C H 0.8554 0.7384 0.7883 0.123 Uiso 0.75(3) 1 calc PR A 1
C15' C 0.766(4) 0.699(4) 0.635(2) 0.053(11) Uani 0.25(3) 1 d P A 2
H15C H 0.8655 0.7070 0.6460 0.064 Uiso 0.25(3) 1 calc PR A 2
H15D H 0.7245 0.7765 0.6151 0.064 Uiso 0.25(3) 1 calc PR A 2
C16' C 0.723(3) 0.665(3) 0.707(3) 0.058(13) Uani 0.25(3) 1 d P A 2
H16C H 0.6226 0.6631 0.6950 0.070 Uiso 0.25(3) 1 calc PR A 2
H16D H 0.7560 0.5835 0.7220 0.070 Uiso 0.25(3) 1 calc PR A 2
C17' C 0.776(7) 0.749(5) 0.774(3) 0.063(13) Uani 0.25(3) 1 d P A 2
H17D H 0.8749 0.7522 0.7865 0.095 Uiso 0.25(3) 1 calc PR A 2
H17E H 0.7466 0.7199 0.8174 0.095 Uiso 0.25(3) 1 calc PR A 2
H17F H 0.7390 0.8294 0.7611 0.095 Uiso 0.25(3) 1 calc PR A 2
C18 C 0.5943(6) 0.5983(5) 0.4565(3) 0.0428(14) Uani 1 1 d . . .
C19 C 0.6635(5) 0.5038(5) 0.4357(3) 0.0413(14) Uani 1 1 d . A .
C20 C 0.6119(5) 0.4968(5) 0.3561(3) 0.0411(14) Uani 1 1 d . . .
C21 C 0.6563(6) 0.4277(5) 0.2985(3) 0.0537(16) Uani 1 1 d . A .
H21A H 0.6094 0.3507 0.2911 0.081 Uiso 1 1 calc R . .
H21B H 0.7543 0.4145 0.3150 0.081 Uiso 1 1 calc R . .
H21C H 0.6343 0.4720 0.2512 0.081 Uiso 1 1 calc R . .
C22 C 0.4025(6) 0.7270(5) 0.3846(3) 0.0455(14) Uani 1 1 d . . .
C23 C 0.4241(7) 0.8278(6) 0.4299(3) 0.0603(17) Uani 1 1 d . A .
H23 H 0.5065 0.8375 0.4675 0.072 Uiso 1 1 calc R . .
C24 C 0.3229(8) 0.9147(6) 0.4192(4) 0.073(2) Uani 1 1 d . . .
H24 H 0.3365 0.9835 0.4500 0.087 Uiso 1 1 calc R A .
C25 C 0.2025(8) 0.9012(7) 0.3638(4) 0.071(2) Uani 1 1 d . A .
H25 H 0.1341 0.9605 0.3567 0.085 Uiso 1 1 calc R . .
C26 C 0.1831(7) 0.8000(6) 0.3188(4) 0.0645(19) Uani 1 1 d . . .
H26 H 0.1013 0.7908 0.2806 0.077 Uiso 1 1 calc R A .
C27 C 0.2823(6) 0.7122(5) 0.3292(3) 0.0518(16) Uani 1 1 d . A .
H27 H 0.2681 0.6429 0.2988 0.062 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C18 1.333(6) . ?
N1 N2 1.337(5) . ?
N1 C22 1.375(6) . ?
N2 C20 1.294(6) . ?
N3 C14 1.309(7) . ?
N3 C18 1.313(6) . ?
O1 C5 1.337(6) . ?
O1 C1 1.340(7) . ?
O2 C1 1.175(6) . ?
C1 C2 1.429(8) . ?
C2 C14 1.370(7) . ?
C2 C3 1.371(7) . ?
C3 C19 1.380(7) . ?
C3 C4 1.418(7) . ?
C4 C5 1.352(7) . ?
C4 C9 1.400(7) . ?
C5 C6 1.358(8) . ?
C6 C7 1.315(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.380(8) . ?
C7 H7 0.9300 . ?
C8 C13 1.386(8) . ?
C8 C9 1.390(7) . ?
C9 C10 1.368(8) . ?
C10 C11 1.346(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.360(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.315(9) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.501(16) . ?
C14 C15' 1.53(5) . ?
C15 C16 1.50(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.52(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C15' C16' 1.53(7) . ?
C15' H15C 0.9700 . ?
C15' H15D 0.9700 . ?
C16' C17' 1.51(7) . ?
C16' H16C 0.9700 . ?
C16' H16D 0.9700 . ?
C17' H17D 0.9600 . ?
C17' H17E 0.9600 . ?
C17' H17F 0.9600 . ?
C18 C19 1.356(7) . ?
C19 C20 1.402(6) . ?
C20 C21 1.452(7) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C27 1.362(8) . ?
C22 C23 1.363(8) . ?
C23 C24 1.369(8) . ?
C23 H23 0.9300 . ?
C24 C25 1.362(9) . ?
C24 H24 0.9300 . ?
C25 C26 1.364(9) . ?
C25 H25 0.9300 . ?
C26 C27 1.363(8) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 N1 N2 110.0(4) . . ?
C18 N1 C22 131.4(5) . . ?
N2 N1 C22 118.7(4) . . ?
C20 N2 N1 107.4(4) . . ?
C14 N3 C18 113.6(5) . . ?
C5 O1 C1 121.4(5) . . ?
O2 C1 O1 115.9(6) . . ?
O2 C1 C2 127.2(6) . . ?
O1 C1 C2 116.6(5) . . ?
C14 C2 C3 120.6(5) . . ?
C14 C2 C1 120.7(5) . . ?
C3 C2 C1 118.5(5) . . ?
C2 C3 C19 115.1(5) . . ?
C2 C3 C4 118.2(5) . . ?
C19 C3 C4 126.6(5) . . ?
C5 C4 C9 117.2(5) . . ?
C5 C4 C3 116.5(5) . . ?
C9 C4 C3 126.1(5) . . ?
O1 C5 C4 121.2(5) . . ?
O1 C5 C6 115.7(5) . . ?
C4 C5 C6 123.1(6) . . ?
C7 C6 C5 118.7(6) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C6 C7 C8 121.8(6) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C7 C8 C13 122.2(6) . . ?
C7 C8 C9 119.0(6) . . ?
C13 C8 C9 118.7(6) . . ?
C10 C9 C8 118.2(6) . . ?
C10 C9 C4 122.7(5) . . ?
C8 C9 C4 118.7(5) . . ?
C11 C10 C9 120.8(6) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 120.4(7) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 120.3(6) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C8 121.1(6) . . ?
C12 C13 H13 119.4 . . ?
C8 C13 H13 119.4 . . ?
N3 C14 C2 123.6(5) . . ?
N3 C14 C15 113.4(6) . . ?
C2 C14 C15 122.3(6) . . ?
N3 C14 C15' 106.5(12) . . ?
C2 C14 C15' 122.8(12) . . ?
C15 C14 C15' 37.4(13) . . ?
C16 C15 C14 108.0(12) . . ?
C16 C15 H15A 110.1 . . ?
C14 C15 H15A 110.1 . . ?
C16 C15 H15B 110.1 . . ?
C14 C15 H15B 110.1 . . ?
H15A C15 H15B 108.4 . . ?
C15 C16 C17 109.4(15) . . ?
C15 C16 H16A 109.8 . . ?
C17 C16 H16A 109.8 . . ?
C15 C16 H16B 109.8 . . ?
C17 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
C16' C15' C14 107(4) . . ?
C16' C15' H15C 110.2 . . ?
C14 C15' H15C 110.2 . . ?
C16' C15' H15D 110.2 . . ?
C14 C15' H15D 110.2 . . ?
H15C C15' H15D 108.5 . . ?
C17' C16' C15' 115(4) . . ?
C17' C16' H16C 108.6 . . ?
C15' C16' H16C 108.6 . . ?
C17' C16' H16D 108.6 . . ?
C15' C16' H16D 108.6 . . ?
H16C C16' H16D 107.5 . . ?
C16' C17' H17D 109.5 . . ?
C16' C17' H17E 109.5 . . ?
H17D C17' H17E 109.5 . . ?
C16' C17' H17F 109.5 . . ?
H17D C17' H17F 109.5 . . ?
H17E C17' H17F 109.5 . . ?
N3 C18 N1 124.2(5) . . ?
N3 C18 C19 127.8(5) . . ?
N1 C18 C19 107.9(4) . . ?
C18 C19 C3 117.3(5) . . ?
C18 C19 C20 104.4(5) . . ?
C3 C19 C20 137.9(5) . . ?
N2 C20 C19 110.1(5) . . ?
N2 C20 C21 117.5(5) . . ?
C19 C20 C21 131.9(5) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C27 C22 C23 120.9(5) . . ?
C27 C22 N1 118.7(5) . . ?
C23 C22 N1 120.4(5) . . ?
C22 C23 C24 119.1(6) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C25 C24 C23 120.6(7) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C26 119.5(6) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C27 C26 C25 120.6(6) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C22 C27 C26 119.3(6) . . ?
C22 C27 H27 120.3 . . ?
C26 C27 H27 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
C18 N1 N2 C20 3.2(6) . . . . ?
C22 N1 N2 C20 -177.6(5) . . . . ?
C5 O1 C1 O2 161.9(6) . . . . ?
C5 O1 C1 C2 -23.3(8) . . . . ?
O2 C1 C2 C14 4.4(10) . . . . ?
O1 C1 C2 C14 -169.7(5) . . . . ?
O2 C1 C2 C3 179.3(6) . . . . ?
O1 C1 C2 C3 5.2(8) . . . . ?
C14 C2 C3 C19 15.8(8) . . . . ?
C1 C2 C3 C19 -159.1(5) . . . . ?
C14 C2 C3 C4 -166.2(5) . . . . ?
C1 C2 C3 C4 18.9(8) . . . . ?
C2 C3 C4 C5 -26.1(7) . . . . ?
C19 C3 C4 C5 151.6(5) . . . . ?
C2 C3 C4 C9 149.1(5) . . . . ?
C19 C3 C4 C9 -33.1(9) . . . . ?
C1 O1 C5 C4 16.3(8) . . . . ?
C1 O1 C5 C6 -164.6(5) . . . . ?
C9 C4 C5 O1 -166.7(5) . . . . ?
C3 C4 C5 O1 8.9(8) . . . . ?
C9 C4 C5 C6 14.3(8) . . . . ?
C3 C4 C5 C6 -170.1(5) . . . . ?
O1 C5 C6 C7 174.7(5) . . . . ?
C4 C5 C6 C7 -6.3(9) . . . . ?
C5 C6 C7 C8 -3.8(9) . . . . ?
C6 C7 C8 C13 -171.2(6) . . . . ?
C6 C7 C8 C9 5.0(9) . . . . ?
C7 C8 C9 C10 -169.6(5) . . . . ?
C13 C8 C9 C10 6.8(8) . . . . ?
C7 C8 C9 C4 3.3(8) . . . . ?
C13 C8 C9 C4 179.7(5) . . . . ?
C5 C4 C9 C10 160.2(5) . . . . ?
C3 C4 C9 C10 -15.0(9) . . . . ?
C5 C4 C9 C8 -12.4(7) . . . . ?
C3 C4 C9 C8 172.4(5) . . . . ?
C8 C9 C10 C11 -5.2(8) . . . . ?
C4 C9 C10 C11 -177.8(5) . . . . ?
C9 C10 C11 C12 0.3(9) . . . . ?
C10 C11 C12 C13 3.2(10) . . . . ?
C11 C12 C13 C8 -1.5(10) . . . . ?
C7 C8 C13 C12 172.7(6) . . . . ?
C9 C8 C13 C12 -3.5(9) . . . . ?
C18 N3 C14 C2 -2.2(9) . . . . ?
C18 N3 C14 C15 -171.9(7) . . . . ?
C18 N3 C14 C15' 148.8(16) . . . . ?
C3 C2 C14 N3 -10.6(10) . . . . ?
C1 C2 C14 N3 164.2(6) . . . . ?
C3 C2 C14 C15 158.3(7) . . . . ?
C1 C2 C14 C15 -26.9(10) . . . . ?
C3 C2 C14 C15' -156.9(18) . . . . ?
C1 C2 C14 C15' 18(2) . . . . ?
N3 C14 C15 C16 -87.2(8) . . . . ?
C2 C14 C15 C16 102.9(9) . . . . ?
C15' C14 C15 C16 -0.4(19) . . . . ?
C14 C15 C16 C17 -179.6(11) . . . . ?
N3 C14 C15' C16' 106.1(19) . . . . ?
C2 C14 C15' C16' -103(2) . . . . ?
C15 C14 C15' C16' -1.0(13) . . . . ?
C14 C15' C16' C17' 175(3) . . . . ?
C14 N3 C18 N1 -173.1(6) . . . . ?
C14 N3 C18 C19 9.5(9) . . . . ?
N2 N1 C18 N3 177.6(5) . . . . ?
C22 N1 C18 N3 -1.5(10) . . . . ?
N2 N1 C18 C19 -4.5(6) . . . . ?
C22 N1 C18 C19 176.4(5) . . . . ?
N3 C18 C19 C3 -3.7(9) . . . . ?
N1 C18 C19 C3 178.6(5) . . . . ?
N3 C18 C19 C20 -178.3(6) . . . . ?
N1 C18 C19 C20 3.9(6) . . . . ?
C2 C3 C19 C18 -9.2(7) . . . . ?
C4 C3 C19 C18 173.1(5) . . . . ?
C2 C3 C19 C20 163.1(6) . . . . ?
C4 C3 C19 C20 -14.7(11) . . . . ?
N1 N2 C20 C19 -0.6(6) . . . . ?
N1 N2 C20 C21 -173.9(5) . . . . ?
C18 C19 C20 N2 -2.1(6) . . . . ?
C3 C19 C20 N2 -175.0(6) . . . . ?
C18 C19 C20 C21 169.9(6) . . . . ?
C3 C19 C20 C21 -3.0(11) . . . . ?
C18 N1 C22 C27 -147.0(6) . . . . ?
N2 N1 C22 C27 34.0(7) . . . . ?
C18 N1 C22 C23 33.0(9) . . . . ?
N2 N1 C22 C23 -146.0(5) . . . . ?
C27 C22 C23 C24 0.2(9) . . . . ?
N1 C22 C23 C24 -179.8(5) . . . . ?
C22 C23 C24 C25 -0.5(10) . . . . ?
C23 C24 C25 C26 0.1(10) . . . . ?
C24 C25 C26 C27 0.6(10) . . . . ?
C23 C22 C27 C26 0.4(9) . . . . ?
N1 C22 C27 C26 -179.5(5) . . . . ?
C25 C26 C27 C22 -0.8(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.064
