# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_881279
_database_code_depnum_ccdc_archive 'CCDC 881279'
_audit_update_record             
;
2014-12-22 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H21 N3 O3, C H4 O'
_chemical_formula_sum            'C26 H25 N3 O4'
_chemical_formula_weight         443.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   10.1589(11)
_cell_length_b                   11.3338(12)
_cell_length_c                   11.6688(14)
_cell_angle_alpha                68.3220(10)
_cell_angle_beta                 67.3960(10)
_cell_angle_gamma                82.841(2)
_cell_volume                     1152.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1791
_cell_measurement_theta_min      2.598
_cell_measurement_theta_max      22.967

_exptl_crystal_description       block
_exptl_crystal_colour            light-yellow
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             468
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9634
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_process_details   'sadabs (Sheldrick, 1996)'

_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            6007
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         25.02
_reflns_number_total             4003
_reflns_number_gt                2374
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  'SHELXTL (Bruker, 2000)'

_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)+(0.0953P)²+0.0881P] 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         4003
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1720
_refine_ls_wR_factor_gt          0.1346
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.973
_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 0.3181(2) 0.3281(2) 0.7493(2) 0.0507(6) Uani 1 1 d . . .
N2 N 0.5269(2) 0.5782(2) 0.8017(2) 0.0458(5) Uani 1 1 d . . .
N3 N 0.6671(2) 0.5421(2) 0.7475(2) 0.0505(6) Uani 1 1 d . . .
O1 O -0.0718(3) -0.1451(2) 0.6624(2) 0.0815(7) Uani 1 1 d . . .
H1 H -0.0523 -0.2205 0.6866 0.122 Uiso 1 1 calc R . .
O2 O -0.0153(4) -0.1510(2) 0.8272(3) 0.1067(10) Uani 1 1 d . . .
O3 O 0.30102(19) 0.51251(18) 0.83957(19) 0.0564(5) Uani 1 1 d . . .
O4 O 0.9330(2) 0.6099(2) 0.7295(2) 0.0794(7) Uani 1 1 d . . .
H4 H 0.8597 0.5862 0.7302 0.119 Uiso 1 1 calc R . .
C1 C -0.0477(3) -0.0915(3) 0.7343(3) 0.0618(8) Uani 1 1 d . . .
C2 C -0.0627(3) 0.0496(3) 0.6840(4) 0.0693(9) Uani 1 1 d . . .
H2A H -0.1595 0.0704 0.7304 0.083 Uiso 1 1 calc R . .
H2B H -0.0478 0.0778 0.5906 0.083 Uiso 1 1 calc R . .
C3 C 0.0396(3) 0.1218(3) 0.7010(3) 0.0507(7) Uani 1 1 d . . .
C4 C 0.1494(3) 0.1951(3) 0.5918(3) 0.0553(7) Uani 1 1 d . . .
H4A H 0.1605 0.1989 0.5076 0.066 Uiso 1 1 calc R . .
C5 C 0.2425(3) 0.2627(3) 0.6058(3) 0.0528(7) Uani 1 1 d . . .
H5 H 0.3149 0.3125 0.5313 0.063 Uiso 1 1 calc R . .
C6 C 0.2283(3) 0.2564(2) 0.7298(3) 0.0451(6) Uani 1 1 d . . .
C7 C 0.1196(3) 0.1843(3) 0.8392(3) 0.0539(7) Uani 1 1 d . . .
H7 H 0.1084 0.1809 0.9234 0.065 Uiso 1 1 calc R . .
C8 C 0.0270(3) 0.1170(3) 0.8238(3) 0.0572(7) Uani 1 1 d . . .
H8 H -0.0455 0.0674 0.8984 0.069 Uiso 1 1 calc R . .
C9 C 0.6637(3) 0.4547(2) 0.7003(3) 0.0473(6) Uani 1 1 d . . .
C10 C 0.5207(3) 0.4283(2) 0.7212(2) 0.0426(6) Uani 1 1 d . . .
C11 C 0.4341(3) 0.5077(2) 0.7923(2) 0.0442(6) Uani 1 1 d . . .
C12 C 0.4960(3) 0.6689(2) 0.8648(2) 0.0465(6) Uani 1 1 d . . .
C13 C 0.3662(3) 0.7288(3) 0.8853(4) 0.0740(9) Uani 1 1 d . . .
H13 H 0.2996 0.7102 0.8572 0.089 Uiso 1 1 calc R . .
C14 C 0.3365(4) 0.8161(3) 0.9475(4) 0.0878(11) Uani 1 1 d . . .
H14 H 0.2487 0.8557 0.9623 0.105 Uiso 1 1 calc R . .
C15 C 0.4336(4) 0.8461(3) 0.9884(3) 0.0771(10) Uani 1 1 d . . .
H15 H 0.4118 0.9043 1.0318 0.093 Uiso 1 1 calc R . .
C16 C 0.5614(4) 0.7896(3) 0.9643(3) 0.0714(9) Uani 1 1 d . . .
H16 H 0.6291 0.8111 0.9893 0.086 Uiso 1 1 calc R . .
C17 C 0.5936(3) 0.7006(3) 0.9032(3) 0.0595(8) Uani 1 1 d . . .
H17 H 0.6820 0.6620 0.8883 0.071 Uiso 1 1 calc R . .
C18 C 0.8004(3) 0.3963(3) 0.6392(3) 0.0697(9) Uani 1 1 d . . .
H18A H 0.8239 0.4236 0.5453 0.105 Uiso 1 1 calc R . .
H18B H 0.7899 0.3055 0.6768 0.105 Uiso 1 1 calc R . .
H18C H 0.8753 0.4223 0.6563 0.105 Uiso 1 1 calc R . .
C19 C 0.4598(3) 0.3398(2) 0.6979(2) 0.0425(6) Uani 1 1 d . . .
C20 C 0.5420(3) 0.2568(2) 0.6240(3) 0.0429(6) Uani 1 1 d . . .
C21 C 0.5230(3) 0.1261(3) 0.6847(3) 0.0537(7) Uani 1 1 d . . .
H21 H 0.4622 0.0911 0.7727 0.064 Uiso 1 1 calc R . .
C22 C 0.5944(4) 0.0482(3) 0.6142(4) 0.0696(9) Uani 1 1 d . . .
H22 H 0.5823 -0.0395 0.6550 0.084 Uiso 1 1 calc R . .
C23 C 0.6830(4) 0.0995(3) 0.4844(4) 0.0729(9) Uani 1 1 d . . .
H23 H 0.7291 0.0466 0.4366 0.088 Uiso 1 1 calc R . .
C24 C 0.7039(3) 0.2278(3) 0.4247(3) 0.0676(9) Uani 1 1 d . . .
H24 H 0.7655 0.2620 0.3369 0.081 Uiso 1 1 calc R . .
C25 C 0.6345(3) 0.3067(3) 0.4936(3) 0.0537(7) Uani 1 1 d . . .
H25 H 0.6496 0.3941 0.4525 0.064 Uiso 1 1 calc R . .
C26 C 0.9651(4) 0.5241(4) 0.8393(4) 0.1035(14) Uani 1 1 d . . .
H26A H 0.9100 0.5444 0.9170 0.155 Uiso 1 1 calc R . .
H26B H 1.0648 0.5309 0.8216 0.155 Uiso 1 1 calc R . .
H26C H 0.9421 0.4390 0.8535 0.155 Uiso 1 1 calc R . .
H1A H 0.273(3) 0.382(3) 0.800(3) 0.066(9) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C19 1.331(3) . ?
N1 C6 1.424(3) . ?
N1 H1A 0.96(3) . ?
N2 C11 1.368(3) . ?
N2 N3 1.396(3) . ?
N2 C12 1.414(3) . ?
N3 C9 1.308(3) . ?
O1 C1 1.305(3) . ?
O1 H1 0.8200 . ?
O2 C1 1.191(4) . ?
O3 C11 1.251(3) . ?
O4 C26 1.419(4) . ?
O4 H4 0.8200 . ?
C1 C2 1.496(4) . ?
C2 C3 1.510(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C8 1.369(4) . ?
C3 C4 1.384(4) . ?
C4 C5 1.378(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.373(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.374(4) . ?
C7 C8 1.382(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.429(3) . ?
C9 C18 1.495(4) . ?
C10 C19 1.396(3) . ?
C10 C11 1.437(3) . ?
C12 C17 1.366(4) . ?
C12 C13 1.383(4) . ?
C13 C14 1.373(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.350(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.379(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.475(3) . ?
C20 C25 1.384(4) . ?
C20 C21 1.388(4) . ?
C21 C22 1.379(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.370(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.365(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.372(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

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
C19 N1 C6 129.0(2) . . ?
C19 N1 H1A 113.2(17) . . ?
C6 N1 H1A 117.6(17) . . ?
C11 N2 N3 110.52(19) . . ?
C11 N2 C12 128.6(2) . . ?
N3 N2 C12 120.6(2) . . ?
C9 N3 N2 107.5(2) . . ?
C1 O1 H1 109.5 . . ?
C26 O4 H4 109.5 . . ?
O2 C1 O1 122.1(3) . . ?
O2 C1 C2 125.6(3) . . ?
O1 C1 C2 112.2(3) . . ?
C1 C2 C3 114.0(2) . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C8 C3 C4 118.1(2) . . ?
C8 C3 C2 121.4(3) . . ?
C4 C3 C2 120.5(3) . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 H4A 119.4 . . ?
C3 C4 H4A 119.4 . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 119.7(2) . . ?
C5 C6 N1 122.1(2) . . ?
C7 C6 N1 118.0(2) . . ?
C6 C7 C8 119.7(3) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C3 C8 C7 121.4(3) . . ?
C3 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
N3 C9 C10 111.0(2) . . ?
N3 C9 C18 118.8(2) . . ?
C10 C9 C18 130.2(2) . . ?
C19 C10 C9 133.4(2) . . ?
C19 C10 C11 121.4(2) . . ?
C9 C10 C11 104.8(2) . . ?
O3 C11 N2 125.4(2) . . ?
O3 C11 C10 128.6(2) . . ?
N2 C11 C10 106.0(2) . . ?
C17 C12 C13 119.3(3) . . ?
C17 C12 N2 121.0(2) . . ?
C13 C12 N2 119.6(2) . . ?
C14 C13 C12 119.3(3) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C15 C14 C13 121.3(3) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C16 C15 C14 118.7(3) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C15 C16 C17 121.2(3) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C12 C17 C16 120.1(3) . . ?
C12 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C9 C18 H18A 109.5 . . ?
C9 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C9 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 C10 117.2(2) . . ?
N1 C19 C20 118.5(2) . . ?
C10 C19 C20 124.3(2) . . ?
C25 C20 C21 119.1(2) . . ?
C25 C20 C19 121.3(2) . . ?
C21 C20 C19 119.5(2) . . ?
C22 C21 C20 119.8(3) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C23 C22 C21 120.2(3) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 120.3(3) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 120.2(3) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C20 120.3(3) . . ?
C24 C25 H25 119.9 . . ?
C20 C25 H25 119.9 . . ?
O4 C26 H26A 109.5 . . ?
O4 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O4 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N2 N3 C9 2.4(3) . . . . ?
C12 N2 N3 C9 177.8(2) . . . . ?
O2 C1 C2 C3 33.5(5) . . . . ?
O1 C1 C2 C3 -145.3(3) . . . . ?
C1 C2 C3 C8 -69.4(4) . . . . ?
C1 C2 C3 C4 110.7(3) . . . . ?
C8 C3 C4 C5 -0.7(4) . . . . ?
C2 C3 C4 C5 179.2(2) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
C4 C5 C6 C7 -1.1(4) . . . . ?
C4 C5 C6 N1 -177.5(2) . . . . ?
C19 N1 C6 C5 -48.9(4) . . . . ?
C19 N1 C6 C7 134.7(3) . . . . ?
C5 C6 C7 C8 1.2(4) . . . . ?
N1 C6 C7 C8 177.7(2) . . . . ?
C4 C3 C8 C7 0.7(4) . . . . ?
C2 C3 C8 C7 -179.2(2) . . . . ?
C6 C7 C8 C3 -1.0(4) . . . . ?
N2 N3 C9 C10 -0.1(3) . . . . ?
N2 N3 C9 C18 -178.4(2) . . . . ?
N3 C9 C10 C19 -175.2(3) . . . . ?
C18 C9 C10 C19 2.8(5) . . . . ?
N3 C9 C10 C11 -2.1(3) . . . . ?
C18 C9 C10 C11 176.0(3) . . . . ?
N3 N2 C11 O3 175.2(2) . . . . ?
C12 N2 C11 O3 0.3(4) . . . . ?
N3 N2 C11 C10 -3.6(3) . . . . ?
C12 N2 C11 C10 -178.6(2) . . . . ?
C19 C10 C11 O3 -1.2(4) . . . . ?
C9 C10 C11 O3 -175.4(3) . . . . ?
C19 C10 C11 N2 177.6(2) . . . . ?
C9 C10 C11 N2 3.4(3) . . . . ?
C11 N2 C12 C17 158.4(3) . . . . ?
N3 N2 C12 C17 -16.1(4) . . . . ?
C11 N2 C12 C13 -23.1(4) . . . . ?
N3 N2 C12 C13 162.4(3) . . . . ?
C17 C12 C13 C14 -2.0(5) . . . . ?
N2 C12 C13 C14 179.5(3) . . . . ?
C12 C13 C14 C15 0.8(6) . . . . ?
C13 C14 C15 C16 1.1(6) . . . . ?
C14 C15 C16 C17 -1.8(5) . . . . ?
C13 C12 C17 C16 1.3(4) . . . . ?
N2 C12 C17 C16 179.8(3) . . . . ?
C15 C16 C17 C12 0.6(5) . . . . ?
C6 N1 C19 C10 172.7(2) . . . . ?
C6 N1 C19 C20 -9.1(4) . . . . ?
C9 C10 C19 N1 169.4(3) . . . . ?
C11 C10 C19 N1 -2.9(4) . . . . ?
C9 C10 C19 C20 -8.7(4) . . . . ?
C11 C10 C19 C20 179.0(2) . . . . ?
N1 C19 C20 C25 122.4(3) . . . . ?
C10 C19 C20 C25 -59.5(3) . . . . ?
N1 C19 C20 C21 -55.4(3) . . . . ?
C10 C19 C20 C21 122.7(3) . . . . ?
C25 C20 C21 C22 -0.9(4) . . . . ?
C19 C20 C21 C22 176.9(2) . . . . ?
C20 C21 C22 C23 -0.5(4) . . . . ?
C21 C22 C23 C24 1.6(5) . . . . ?
C22 C23 C24 C25 -1.1(5) . . . . ?
C23 C24 C25 C20 -0.4(4) . . . . ?
C21 C20 C25 C24 1.4(4) . . . . ?
C19 C20 C25 C24 -176.5(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C26 H26B O3 0.96 2.47 3.400(4) 164.6 1_655
C2 H2B O1 0.97 2.57 3.503(4) 162.4 2_556
C7 H7 O2 0.93 2.59 3.502(4) 166.0 2_557
N1 H1A O3 0.96(3) 1.79(3) 2.628(3) 145(2) .
O4 H4 N3 0.82 2.00 2.810(3) 172.2 .
O1 H1 O4 0.82 1.81 2.591(3) 159.3 1_445

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_886801
_database_code_depnum_ccdc_archive 'CCDC 886801'
_audit_update_record             
;
2014-12-22 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H20 N4 O2, C H4 O'
_chemical_formula_sum            'C25 H24 N4 O3'
_chemical_formula_weight         428.48

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   7.3752(6)
_cell_length_b                   10.9275(9)
_cell_length_c                   14.5614(12)
_cell_angle_alpha                101.707(2)
_cell_angle_beta                 92.7690(10)
_cell_angle_gamma                98.5440(10)
_cell_volume                     1132.64(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1314
_cell_measurement_theta_min      2.666
_cell_measurement_theta_max      22.695

_exptl_crystal_description       block
_exptl_crystal_colour            light-yellow
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9654
_exptl_absorpt_correction_T_max  0.9809
_exptl_absorpt_process_details   'sadabs (Sheldrick, 1996)'

_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            5528
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.1075
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.64
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3936
_reflns_number_gt                2033
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  'SHELXTL (Bruker, 2000)'

_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)+(0.1111P)²+0.3412P] 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         3936
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1387
_refine_ls_R_factor_gt           0.0721
_refine_ls_wR_factor_ref         0.2453
_refine_ls_wR_factor_gt          0.1896
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.2937(5) 0.5161(3) 0.3126(2) 0.0508(9) Uani 1 1 d . . .
N2 N 0.2427(5) 0.4657(3) 0.3909(2) 0.0548(9) Uani 1 1 d . . .
N3 N 0.6936(5) 0.3035(3) 0.2243(3) 0.0549(10) Uani 1 1 d . . .
N4 N 1.3558(5) 0.1231(3) -0.0149(3) 0.0673(11) Uani 1 1 d . . .
H4A H 1.4451 0.0913 -0.0412 0.081 Uiso 1 1 calc R . .
H4B H 1.3067 0.1782 -0.0379 0.081 Uiso 1 1 calc R . .
O1 O 0.5018(4) 0.4865(3) 0.1967(2) 0.0631(9) Uani 1 1 d . . .
O2 O 1.3591(4) 0.0083(3) 0.0978(2) 0.0633(9) Uani 1 1 d . . .
O3 O 0.6596(6) 0.6296(4) 0.0632(3) 0.1116(14) Uani 1 1 d . . .
H3 H 0.5941 0.5974 0.0987 0.167 Uiso 1 1 calc R . .
C1 C 0.3499(6) 0.3825(4) 0.3989(3) 0.0501(10) Uani 1 1 d . . .
C2 C 0.4774(5) 0.3751(3) 0.3264(3) 0.0457(10) Uani 1 1 d . . .
C3 C 0.4355(6) 0.4630(4) 0.2701(3) 0.0494(10) Uani 1 1 d . . .
C4 C 0.3256(7) 0.3130(4) 0.4768(3) 0.0676(13) Uani 1 1 d . . .
H4C H 0.2190 0.3330 0.5082 0.101 Uiso 1 1 calc R . .
H4D H 0.4323 0.3376 0.5208 0.101 Uiso 1 1 calc R . .
H4E H 0.3100 0.2235 0.4514 0.101 Uiso 1 1 calc R . .
C5 C 0.1917(6) 0.6052(4) 0.2844(3) 0.0507(10) Uani 1 1 d . . .
C6 C 0.2737(6) 0.6951(4) 0.2385(3) 0.0602(12) Uani 1 1 d . . .
H6 H 0.3948 0.6956 0.2234 0.072 Uiso 1 1 calc R . .
C7 C 0.1754(7) 0.7847(4) 0.2150(3) 0.0688(13) Uani 1 1 d . . .
H7 H 0.2311 0.8457 0.1846 0.083 Uiso 1 1 calc R . .
C8 C -0.0056(7) 0.7833(5) 0.2367(3) 0.0724(14) Uani 1 1 d . . .
H8 H -0.0721 0.8431 0.2209 0.087 Uiso 1 1 calc R . .
C9 C -0.0856(7) 0.6933(5) 0.2816(4) 0.0731(14) Uani 1 1 d . . .
H9 H -0.2071 0.6925 0.2963 0.088 Uiso 1 1 calc R . .
C10 C 0.0102(6) 0.6032(4) 0.3058(3) 0.0601(12) Uani 1 1 d . . .
H10 H -0.0462 0.5422 0.3361 0.072 Uiso 1 1 calc R . .
C11 C 0.6106(5) 0.2962(3) 0.3033(3) 0.0455(10) Uani 1 1 d . . .
C12 C 0.6488(5) 0.2019(4) 0.3585(3) 0.0465(10) Uani 1 1 d . . .
C13 C 0.7413(6) 0.2386(4) 0.4475(3) 0.0576(12) Uani 1 1 d . . .
H13 H 0.7741 0.3241 0.4750 0.069 Uiso 1 1 calc R . .
C14 C 0.7849(7) 0.1482(5) 0.4954(3) 0.0713(14) Uani 1 1 d . . .
H14 H 0.8479 0.1729 0.5548 0.086 Uiso 1 1 calc R . .
C15 C 0.7349(8) 0.0223(5) 0.4551(4) 0.0812(16) Uani 1 1 d . . .
H15 H 0.7644 -0.0386 0.4870 0.097 Uiso 1 1 calc R . .
C16 C 0.6413(7) -0.0144(4) 0.3677(4) 0.0799(15) Uani 1 1 d . . .
H16 H 0.6064 -0.1002 0.3414 0.096 Uiso 1 1 calc R . .
C17 C 0.5985(6) 0.0735(4) 0.3186(3) 0.0592(12) Uani 1 1 d . . .
H17 H 0.5363 0.0475 0.2591 0.071 Uiso 1 1 calc R . .
C18 C 1.2938(6) 0.0874(4) 0.0612(3) 0.0504(10) Uani 1 1 d . . .
C19 C 1.1361(5) 0.1444(3) 0.1031(3) 0.0451(10) Uani 1 1 d . . .
C20 C 1.0026(6) 0.1831(4) 0.0487(3) 0.0570(11) Uani 1 1 d . . .
H21 H 1.0117 0.1758 -0.0156 0.068 Uiso 1 1 calc R . .
C21 C 0.8567(6) 0.2323(4) 0.0907(3) 0.0567(11) Uani 1 1 d . . .
H21A H 0.7671 0.2566 0.0542 0.068 Uiso 1 1 calc R . .
C22 C 0.8437(5) 0.2455(3) 0.1862(3) 0.0483(10) Uani 1 1 d . . .
C23 C 0.9761(6) 0.2080(4) 0.2407(3) 0.0633(12) Uani 1 1 d . . .
H23 H 0.9692 0.2184 0.3053 0.076 Uiso 1 1 calc R . .
C24 C 1.1188(6) 0.1549(4) 0.1982(3) 0.0546(11) Uani 1 1 d . . .
H24 H 1.2039 0.1260 0.2343 0.066 Uiso 1 1 calc R . .
C25 C 0.7769(10) 0.5462(6) 0.0251(5) 0.112(2) Uani 1 1 d . . .
H25A H 0.8271 0.5715 -0.0291 0.168 Uiso 1 1 calc R . .
H25B H 0.7089 0.4619 0.0068 0.168 Uiso 1 1 calc R . .
H25C H 0.8751 0.5480 0.0713 0.168 Uiso 1 1 calc R . .
H3A H 0.661(5) 0.359(4) 0.192(3) 0.053(12) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C3 1.383(5) . ?
N1 N2 1.406(4) . ?
N1 C5 1.426(5) . ?
N2 C1 1.309(5) . ?
N3 C11 1.340(5) . ?
N3 C22 1.435(5) . ?
N3 H3A 0.89(4) . ?
N4 C18 1.327(5) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
O1 C3 1.253(4) . ?
O2 C18 1.244(4) . ?
O3 C25 1.401(6) . ?
O3 H3 0.8200 . ?
C1 C2 1.445(5) . ?
C1 C4 1.492(5) . ?
C2 C11 1.410(5) . ?
C2 C3 1.439(5) . ?
C4 H4C 0.9600 . ?
C4 H4D 0.9600 . ?
C4 H4E 0.9600 . ?
C5 C6 1.380(6) . ?
C5 C10 1.387(6) . ?
C6 C7 1.388(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.386(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.368(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.384(6) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.479(5) . ?
C12 C13 1.389(6) . ?
C12 C17 1.391(5) . ?
C13 C14 1.385(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.372(6) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.498(5) . ?
C19 C24 1.380(5) . ?
C19 C20 1.400(5) . ?
C20 C21 1.387(5) . ?
C20 H21 0.9300 . ?
C21 C22 1.378(5) . ?
C21 H21A 0.9300 . ?
C22 C23 1.388(6) . ?
C23 C24 1.387(5) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

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
C3 N1 N2 112.1(3) . . ?
C3 N1 C5 129.0(3) . . ?
N2 N1 C5 118.8(3) . . ?
C1 N2 N1 106.8(3) . . ?
C11 N3 C22 130.5(4) . . ?
C11 N3 H3A 117(3) . . ?
C22 N3 H3A 112(3) . . ?
C18 N4 H4A 120.0 . . ?
C18 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C25 O3 H3 109.5 . . ?
N2 C1 C2 110.8(3) . . ?
N2 C1 C4 118.5(3) . . ?
C2 C1 C4 130.7(4) . . ?
C11 C2 C3 122.1(3) . . ?
C11 C2 C1 131.7(3) . . ?
C3 C2 C1 106.0(3) . . ?
O1 C3 N1 125.3(4) . . ?
O1 C3 C2 130.4(3) . . ?
N1 C3 C2 104.3(3) . . ?
C1 C4 H4C 109.5 . . ?
C1 C4 H4D 109.5 . . ?
H4C C4 H4D 109.5 . . ?
C1 C4 H4E 109.5 . . ?
H4C C4 H4E 109.5 . . ?
H4D C4 H4E 109.5 . . ?
C6 C5 C10 120.1(4) . . ?
C6 C5 N1 120.5(4) . . ?
C10 C5 N1 119.3(4) . . ?
C5 C6 C7 120.0(4) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 120.0(4) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C9 C8 C7 119.3(4) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 121.5(5) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C9 C10 C5 119.0(4) . . ?
C9 C10 H10 120.5 . . ?
C5 C10 H10 120.5 . . ?
N3 C11 C2 116.9(3) . . ?
N3 C11 C12 120.4(3) . . ?
C2 C11 C12 122.5(3) . . ?
C13 C12 C17 119.3(4) . . ?
C13 C12 C11 121.4(4) . . ?
C17 C12 C11 119.3(4) . . ?
C14 C13 C12 120.2(4) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 119.7(5) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.3(5) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C17 121.0(5) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C12 119.5(4) . . ?
C16 C17 H17 120.3 . . ?
C12 C17 H17 120.3 . . ?
O2 C18 N4 123.0(4) . . ?
O2 C18 C19 119.3(3) . . ?
N4 C18 C19 117.7(4) . . ?
C24 C19 C20 119.0(3) . . ?
C24 C19 C18 118.6(3) . . ?
C20 C19 C18 122.4(3) . . ?
C21 C20 C19 120.0(4) . . ?
C21 C20 H21 120.0 . . ?
C19 C20 H21 120.0 . . ?
C22 C21 C20 120.4(4) . . ?
C22 C21 H21A 119.8 . . ?
C20 C21 H21A 119.8 . . ?
C21 C22 C23 119.9(3) . . ?
C21 C22 N3 116.5(4) . . ?
C23 C22 N3 123.5(4) . . ?
C24 C23 C22 119.7(4) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C19 C24 C23 120.9(4) . . ?
C19 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
O3 C25 H25A 109.5 . . ?
O3 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O3 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 N2 C1 0.3(5) . . . . ?
C5 N1 N2 C1 176.7(3) . . . . ?
N1 N2 C1 C2 0.4(5) . . . . ?
N1 N2 C1 C4 -179.8(4) . . . . ?
N2 C1 C2 C11 -176.2(4) . . . . ?
C4 C1 C2 C11 4.0(8) . . . . ?
N2 C1 C2 C3 -1.0(5) . . . . ?
C4 C1 C2 C3 179.2(4) . . . . ?
N2 N1 C3 O1 176.6(4) . . . . ?
C5 N1 C3 O1 0.7(7) . . . . ?
N2 N1 C3 C2 -0.9(4) . . . . ?
C5 N1 C3 C2 -176.8(4) . . . . ?
C11 C2 C3 O1 -0.5(7) . . . . ?
C1 C2 C3 O1 -176.3(4) . . . . ?
C11 C2 C3 N1 176.9(4) . . . . ?
C1 C2 C3 N1 1.1(4) . . . . ?
C3 N1 C5 C6 -32.0(6) . . . . ?
N2 N1 C5 C6 152.3(4) . . . . ?
C3 N1 C5 C10 149.8(4) . . . . ?
N2 N1 C5 C10 -25.8(5) . . . . ?
C10 C5 C6 C7 0.9(7) . . . . ?
N1 C5 C6 C7 -177.2(4) . . . . ?
C5 C6 C7 C8 -0.6(7) . . . . ?
C6 C7 C8 C9 0.2(7) . . . . ?
C7 C8 C9 C10 -0.1(8) . . . . ?
C8 C9 C10 C5 0.4(7) . . . . ?
C6 C5 C10 C9 -0.8(7) . . . . ?
N1 C5 C10 C9 177.3(4) . . . . ?
C22 N3 C11 C2 173.8(4) . . . . ?
C22 N3 C11 C12 -10.9(7) . . . . ?
C3 C2 C11 N3 -2.0(6) . . . . ?
C1 C2 C11 N3 172.5(4) . . . . ?
C3 C2 C11 C12 -177.3(4) . . . . ?
C1 C2 C11 C12 -2.8(7) . . . . ?
N3 C11 C12 C13 112.5(4) . . . . ?
C2 C11 C12 C13 -72.4(5) . . . . ?
N3 C11 C12 C17 -64.5(5) . . . . ?
C2 C11 C12 C17 110.6(4) . . . . ?
C17 C12 C13 C14 0.8(6) . . . . ?
C11 C12 C13 C14 -176.2(4) . . . . ?
C12 C13 C14 C15 -0.6(7) . . . . ?
C13 C14 C15 C16 -0.3(8) . . . . ?
C14 C15 C16 C17 1.0(8) . . . . ?
C15 C16 C17 C12 -0.8(7) . . . . ?
C13 C12 C17 C16 -0.1(6) . . . . ?
C11 C12 C17 C16 177.0(4) . . . . ?
O2 C18 C19 C24 28.5(6) . . . . ?
N4 C18 C19 C24 -152.5(4) . . . . ?
O2 C18 C19 C20 -149.2(4) . . . . ?
N4 C18 C19 C20 29.8(6) . . . . ?
C24 C19 C20 C21 0.7(6) . . . . ?
C18 C19 C20 C21 178.4(4) . . . . ?
C19 C20 C21 C22 1.1(7) . . . . ?
C20 C21 C22 C23 -0.7(6) . . . . ?
C20 C21 C22 N3 176.8(4) . . . . ?
C11 N3 C22 C21 157.3(4) . . . . ?
C11 N3 C22 C23 -25.2(7) . . . . ?
C21 C22 C23 C24 -1.4(7) . . . . ?
N3 C22 C23 C24 -178.7(4) . . . . ?
C20 C19 C24 C23 -2.8(6) . . . . ?
C18 C19 C24 C23 179.4(4) . . . . ?
C22 C23 C24 C19 3.2(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O1 0.82 2.13 2.914(5) 161.2 .
N3 H3A O1 0.89(4) 1.95(4) 2.696(4) 141(3) .
N4 H4A O2 0.86 2.04 2.895(4) 171.5 2_855
N4 H4B O3 0.86 2.19 2.943(5) 146.8 2_765
C7 H7 O2 0.93 2.49 3.414(6) 176.1 1_465
C17 H17 O2 0.93 2.56 3.480(6) 172.0 1_455

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.060
####################################################################### 
# 
# 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_120612d
_database_code_depnum_ccdc_archive 'CCDC 887652'
_audit_update_record             
;
2014-12-22 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H21 N3 O2'
_chemical_formula_sum            'C24 H21 N3 O2'
_chemical_formula_weight         383.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   7.7356(7)
_cell_length_b                   10.8256(8)
_cell_length_c                   13.5508(11)
_cell_angle_alpha                112.683(2)
_cell_angle_beta                 90.9070(10)
_cell_angle_gamma                107.7410(10)
_cell_volume                     985.67(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1860
_cell_measurement_theta_min      2.797
_cell_measurement_theta_max      26.029

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9607
_exptl_absorpt_correction_T_max  0.9699
_exptl_absorpt_process_details   'sadabs (Sheldrick, 1996)'

_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            4952
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3429
_reflns_number_gt                2375
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  'SHELXTL (Bruker, 2000)'

_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)+(0.0558P)²+0.2693P] 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         3429
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1320
_refine_ls_wR_factor_gt          0.1076
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.6763(2) 0.41782(17) 0.14814(14) 0.0384(4) Uani 1 1 d . . .
N2 N 0.7369(3) 0.51431(18) 0.10055(14) 0.0418(5) Uani 1 1 d . . .
C18 C 0.2148(3) 0.6435(2) 0.41357(16) 0.0360(5) Uani 1 1 d . . .
O1 O 0.4841(2) 0.38469(15) 0.27346(11) 0.0430(4) Uani 1 1 d . . .
N3 N 0.3265(2) 0.59021(19) 0.33698(14) 0.0400(5) Uani 1 1 d . . .
O2 O 0.3844(2) 0.59202(19) 0.52722(13) 0.0583(5) Uani 1 1 d . . .
H2 H 0.3946 0.5951 0.5885 0.088 Uiso 1 1 calc R . .
C1 C 0.5500(3) 0.4481(2) 0.21466(16) 0.0359(5) Uani 1 1 d . . .
C2 C 0.5175(3) 0.5659(2) 0.20333(16) 0.0353(5) Uani 1 1 d . . .
C3 C 0.6419(3) 0.6009(2) 0.13288(16) 0.0373(5) Uani 1 1 d . . .
C4 C 0.6788(4) 0.7190(2) 0.0968(2) 0.0531(6) Uani 1 1 d . . .
H4C H 0.7770 0.7178 0.0543 0.080 Uiso 1 1 calc R . .
H4D H 0.7131 0.8082 0.1589 0.080 Uiso 1 1 calc R . .
H4E H 0.5702 0.7071 0.0538 0.080 Uiso 1 1 calc R . .
C5 C 0.7590(3) 0.3130(2) 0.13344(16) 0.0355(5) Uani 1 1 d . . .
C6 C 0.9456(3) 0.3458(2) 0.13466(18) 0.0467(6) Uani 1 1 d . . .
H6 H 1.0181 0.4355 0.1412 0.056 Uiso 1 1 calc R . .
C7 C 1.0243(4) 0.2436(3) 0.1260(2) 0.0566(7) Uani 1 1 d . . .
H7 H 1.1505 0.2650 0.1275 0.068 Uiso 1 1 calc R . .
C8 C 0.9161(4) 0.1104(3) 0.1151(2) 0.0581(7) Uani 1 1 d . . .
H8 H 0.9693 0.0423 0.1100 0.070 Uiso 1 1 calc R . .
C9 C 0.7307(4) 0.0785(3) 0.1116(2) 0.0567(7) Uani 1 1 d . . .
H9 H 0.6578 -0.0120 0.1032 0.068 Uiso 1 1 calc R . .
C10 C 0.6508(3) 0.1788(2) 0.12058(18) 0.0446(6) Uani 1 1 d . . .
H10 H 0.5243 0.1563 0.1180 0.054 Uiso 1 1 calc R . .
C11 C 0.4057(3) 0.6356(2) 0.26471(15) 0.0350(5) Uani 1 1 d . . .
C12 C 0.3768(3) 0.7612(2) 0.25633(16) 0.0354(5) Uani 1 1 d . . .
C13 C 0.2737(3) 0.7472(2) 0.16572(17) 0.0431(6) Uani 1 1 d . . .
H13 H 0.2252 0.6591 0.1075 0.052 Uiso 1 1 calc R . .
C14 C 0.2435(4) 0.8650(3) 0.1625(2) 0.0552(7) Uani 1 1 d . . .
H14 H 0.1724 0.8556 0.1024 0.066 Uiso 1 1 calc R . .
C15 C 0.3177(4) 0.9959(3) 0.2473(2) 0.0574(7) Uani 1 1 d . . .
H15 H 0.2962 1.0747 0.2447 0.069 Uiso 1 1 calc R . .
C16 C 0.4234(4) 1.0103(2) 0.3357(2) 0.0563(7) Uani 1 1 d . . .
H16 H 0.4750 1.0993 0.3926 0.068 Uiso 1 1 calc R . .
C17 C 0.4539(3) 0.8941(2) 0.34114(18) 0.0459(6) Uani 1 1 d . . .
H17 H 0.5259 0.9045 0.4014 0.055 Uiso 1 1 calc R . .
C19 C 0.2465(3) 0.6398(2) 0.51361(17) 0.0409(5) Uani 1 1 d . . .
C20 C 0.1404(3) 0.6855(3) 0.59138(19) 0.0521(6) Uani 1 1 d . . .
H20 H 0.1593 0.6823 0.6582 0.062 Uiso 1 1 calc R . .
C21 C 0.0070(3) 0.7356(3) 0.57083(19) 0.0541(6) Uani 1 1 d . . .
H21 H -0.0625 0.7669 0.6244 0.065 Uiso 1 1 calc R . .
C22 C -0.0262(3) 0.7406(2) 0.47180(18) 0.0470(6) Uani 1 1 d . . .
C23 C 0.0777(3) 0.6918(2) 0.39317(18) 0.0426(5) Uani 1 1 d . . .
H23 H 0.0550 0.6914 0.3254 0.051 Uiso 1 1 calc R . .
C24 C -0.1724(4) 0.7965(3) 0.4506(2) 0.0697(8) Uani 1 1 d . . .
H24A H -0.1778 0.7905 0.3780 0.105 Uiso 1 1 calc R . .
H24B H -0.1434 0.8938 0.5007 0.105 Uiso 1 1 calc R . .
H24C H -0.2891 0.7407 0.4595 0.105 Uiso 1 1 calc R . .
H3 H 0.364(3) 0.519(3) 0.3437(19) 0.061(7) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.368(3) . ?
N1 N2 1.399(2) . ?
N1 C5 1.417(2) . ?
N2 C3 1.313(3) . ?
C18 C23 1.384(3) . ?
C18 C19 1.392(3) . ?
C18 N3 1.424(3) . ?
O1 C1 1.260(2) . ?
N3 C11 1.335(3) . ?
N3 H3 0.94(2) . ?
O2 C19 1.357(2) . ?
O2 H2 0.8200 . ?
C1 C2 1.434(3) . ?
C2 C11 1.395(3) . ?
C2 C3 1.438(3) . ?
C3 C4 1.490(3) . ?
C4 H4C 0.9600 . ?
C4 H4D 0.9600 . ?
C4 H4E 0.9600 . ?
C5 C6 1.375(3) . ?
C5 C10 1.379(3) . ?
C6 C7 1.387(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.364(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.373(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.489(3) . ?
C12 C13 1.385(3) . ?
C12 C17 1.388(3) . ?
C13 C14 1.381(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.370(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.377(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C19 C20 1.379(3) . ?
C20 C21 1.373(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.387(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.382(3) . ?
C22 C24 1.506(3) . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 112.45(16) . . ?
C1 N1 C5 127.18(17) . . ?
N2 N1 C5 120.04(17) . . ?
C3 N2 N1 105.75(17) . . ?
C23 C18 C19 119.98(19) . . ?
C23 C18 N3 124.68(19) . . ?
C19 C18 N3 115.30(18) . . ?
C11 N3 C18 130.86(18) . . ?
C11 N3 H3 113.3(15) . . ?
C18 N3 H3 115.3(15) . . ?
C19 O2 H2 109.5 . . ?
O1 C1 N1 125.26(18) . . ?
O1 C1 C2 129.74(19) . . ?
N1 C1 C2 104.98(17) . . ?
C11 C2 C1 122.73(19) . . ?
C11 C2 C3 131.58(18) . . ?
C1 C2 C3 105.03(17) . . ?
N2 C3 C2 111.64(18) . . ?
N2 C3 C4 118.45(19) . . ?
C2 C3 C4 129.88(19) . . ?
C3 C4 H4C 109.5 . . ?
C3 C4 H4D 109.5 . . ?
H4C C4 H4D 109.5 . . ?
C3 C4 H4E 109.5 . . ?
H4C C4 H4E 109.5 . . ?
H4D C4 H4E 109.5 . . ?
C6 C5 C10 120.4(2) . . ?
C6 C5 N1 120.40(19) . . ?
C10 C5 N1 119.18(19) . . ?
C5 C6 C7 119.2(2) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C8 C7 C6 120.2(2) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 C7 119.9(2) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.6(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C5 119.7(2) . . ?
C9 C10 H10 120.2 . . ?
C5 C10 H10 120.2 . . ?
N3 C11 C2 118.20(18) . . ?
N3 C11 C12 118.67(18) . . ?
C2 C11 C12 123.08(18) . . ?
C13 C12 C17 119.8(2) . . ?
C13 C12 C11 121.04(18) . . ?
C17 C12 C11 119.19(19) . . ?
C14 C13 C12 119.5(2) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C15 C14 C13 120.6(2) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 120.6(2) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C12 119.7(2) . . ?
C16 C17 H17 120.1 . . ?
C12 C17 H17 120.1 . . ?
O2 C19 C20 124.8(2) . . ?
O2 C19 C18 116.21(19) . . ?
C20 C19 C18 119.0(2) . . ?
C21 C20 C19 120.4(2) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 121.4(2) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C23 C22 C21 118.1(2) . . ?
C23 C22 C24 121.1(2) . . ?
C21 C22 C24 120.8(2) . . ?
C22 C23 C18 121.1(2) . . ?
C22 C23 H23 119.5 . . ?
C18 C23 H23 119.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C3 -3.1(2) . . . . ?
C5 N1 N2 C3 -176.91(17) . . . . ?
C23 C18 N3 C11 41.4(3) . . . . ?
C19 C18 N3 C11 -141.0(2) . . . . ?
N2 N1 C1 O1 -174.35(19) . . . . ?
C5 N1 C1 O1 -1.0(3) . . . . ?
N2 N1 C1 C2 4.1(2) . . . . ?
C5 N1 C1 C2 177.46(18) . . . . ?
O1 C1 C2 C11 3.2(3) . . . . ?
N1 C1 C2 C11 -175.19(18) . . . . ?
O1 C1 C2 C3 174.9(2) . . . . ?
N1 C1 C2 C3 -3.5(2) . . . . ?
N1 N2 C3 C2 0.6(2) . . . . ?
N1 N2 C3 C4 178.79(18) . . . . ?
C11 C2 C3 N2 172.5(2) . . . . ?
C1 C2 C3 N2 1.8(2) . . . . ?
C11 C2 C3 C4 -5.4(4) . . . . ?
C1 C2 C3 C4 -176.1(2) . . . . ?
C1 N1 C5 C6 -133.4(2) . . . . ?
N2 N1 C5 C6 39.4(3) . . . . ?
C1 N1 C5 C10 45.0(3) . . . . ?
N2 N1 C5 C10 -142.1(2) . . . . ?
C10 C5 C6 C7 -1.9(3) . . . . ?
N1 C5 C6 C7 176.52(19) . . . . ?
C5 C6 C7 C8 0.7(3) . . . . ?
C6 C7 C8 C9 0.7(4) . . . . ?
C7 C8 C9 C10 -1.0(4) . . . . ?
C8 C9 C10 C5 -0.2(4) . . . . ?
C6 C5 C10 C9 1.6(3) . . . . ?
N1 C5 C10 C9 -176.8(2) . . . . ?
C18 N3 C11 C2 176.51(19) . . . . ?
C18 N3 C11 C12 -1.2(3) . . . . ?
C1 C2 C11 N3 0.1(3) . . . . ?
C3 C2 C11 N3 -169.1(2) . . . . ?
C1 C2 C11 C12 177.70(19) . . . . ?
C3 C2 C11 C12 8.5(3) . . . . ?
N3 C11 C12 C13 -111.3(2) . . . . ?
C2 C11 C12 C13 71.2(3) . . . . ?
N3 C11 C12 C17 68.4(3) . . . . ?
C2 C11 C12 C17 -109.1(2) . . . . ?
C17 C12 C13 C14 -2.3(3) . . . . ?
C11 C12 C13 C14 177.4(2) . . . . ?
C12 C13 C14 C15 1.3(4) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C14 C15 C16 C17 -0.9(4) . . . . ?
C15 C16 C17 C12 -0.1(4) . . . . ?
C13 C12 C17 C16 1.7(3) . . . . ?
C11 C12 C17 C16 -178.0(2) . . . . ?
C23 C18 C19 O2 -179.51(19) . . . . ?
N3 C18 C19 O2 2.8(3) . . . . ?
C23 C18 C19 C20 -0.3(3) . . . . ?
N3 C18 C19 C20 -178.08(19) . . . . ?
O2 C19 C20 C21 178.2(2) . . . . ?
C18 C19 C20 C21 -0.8(4) . . . . ?
C19 C20 C21 C22 0.6(4) . . . . ?
C20 C21 C22 C23 0.8(4) . . . . ?
C20 C21 C22 C24 -179.7(2) . . . . ?
C21 C22 C23 C18 -2.0(3) . . . . ?
C24 C22 C23 C18 178.5(2) . . . . ?
C19 C18 C23 C22 1.8(3) . . . . ?
N3 C18 C23 C22 179.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_889325
_database_code_depnum_ccdc_archive 'CCDC 889325'
_audit_update_record             
;
2014-12-22 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H26 N4 O, 2(C H4 O)'
_chemical_formula_sum            'C32 H34 N4 O3'
_chemical_formula_weight         522.63

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   9.5274(8)
_cell_length_b                   10.4205(9)
_cell_length_c                   14.7518(13)
_cell_angle_alpha                77.2540(10)
_cell_angle_beta                 82.0960(10)
_cell_angle_gamma                84.377(2)
_cell_volume                     1411.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1029
_cell_measurement_theta_min      2.445
_cell_measurement_theta_max      21.115

_exptl_crystal_description       needle
_exptl_crystal_colour            light-yellow
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             556
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9672
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_process_details   'sadabs (Sheldrick, 1996)'

_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            7082
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.2091
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         25.02
_reflns_number_total             4894
_reflns_number_gt                1814
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  'SHELXTL (Bruker, 2000)'

_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)+(0.0324P)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         4894
_refine_ls_number_parameters     359
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2033
_refine_ls_R_factor_gt           0.0729
_refine_ls_wR_factor_ref         0.2464
_refine_ls_wR_factor_gt          0.1616
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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 0.0514(4) 0.7245(4) 0.3541(3) 0.0448(11) Uani 1 1 d . . .
N2 N 0.0483(5) 0.6492(4) 0.2872(3) 0.0492(11) Uani 1 1 d . . .
N3 N 0.2636(5) 0.4546(5) 0.5443(3) 0.0485(12) Uani 1 1 d . . .
N4 N 0.5482(7) -0.3514(5) 0.9421(4) 0.111(2) Uani 1 1 d . . .
H4A H 0.4649 -0.3790 0.9612 0.133 Uiso 1 1 calc R . .
H4B H 0.6210 -0.4070 0.9406 0.133 Uiso 1 1 calc R . .
O1 O 0.1244(4) 0.6922(3) 0.5020(2) 0.0590(11) Uani 1 1 d . . .
O2 O 1.0313(6) 0.7134(6) 0.0927(3) 0.134(2) Uani 1 1 d . . .
H2 H 1.0490 0.7197 0.1443 0.201 Uiso 1 1 calc R . .
O3 O 0.2295(5) 0.5757(5) 0.9990(3) 0.1126(17) Uani 1 1 d . . .
H3 H 0.1683 0.6052 1.0352 0.169 Uiso 1 1 calc R . .
C1 C 0.1142(6) 0.5347(5) 0.3174(3) 0.0467(14) Uani 1 1 d . . .
C2 C 0.1628(5) 0.5287(5) 0.4060(3) 0.0440(13) Uani 1 1 d . . .
C3 C 0.1133(5) 0.6536(5) 0.4291(3) 0.0445(13) Uani 1 1 d . . .
C4 C -0.0089(5) 0.8556(5) 0.3376(3) 0.0429(13) Uani 1 1 d . . .
C5 C -0.1114(6) 0.8937(5) 0.2796(3) 0.0552(15) Uani 1 1 d . . .
H5 H -0.1423 0.8332 0.2502 0.066 Uiso 1 1 calc R . .
C6 C -0.1693(7) 1.0214(6) 0.2644(4) 0.0724(18) Uani 1 1 d . . .
H6 H -0.2385 1.0478 0.2241 0.087 Uiso 1 1 calc R . .
C7 C -0.1245(7) 1.1113(6) 0.3094(4) 0.0754(18) Uani 1 1 d . . .
H7 H -0.1649 1.1974 0.3007 0.090 Uiso 1 1 calc R . .
C8 C -0.0214(7) 1.0718(6) 0.3658(4) 0.0629(16) Uani 1 1 d . . .
H8 H 0.0100 1.1323 0.3950 0.075 Uiso 1 1 calc R . .
C9 C 0.0378(6) 0.9459(5) 0.3812(3) 0.0511(14) Uani 1 1 d . . .
H9 H 0.1087 0.9207 0.4204 0.061 Uiso 1 1 calc R . .
C10 C 0.1234(7) 0.4314(5) 0.2599(4) 0.0694(18) Uani 1 1 d . . .
H10A H 0.0678 0.4622 0.2087 0.104 Uiso 1 1 calc R . .
H10B H 0.0875 0.3518 0.2982 0.104 Uiso 1 1 calc R . .
H10C H 0.2206 0.4143 0.2358 0.104 Uiso 1 1 calc R . .
C11 C 0.2460(5) 0.4346(5) 0.4597(3) 0.0426(13) Uani 1 1 d . . .
C12 C 0.3163(5) 0.3198(5) 0.4265(3) 0.0405(13) Uani 1 1 d . . .
C13 C 0.4177(6) 0.3387(6) 0.3483(3) 0.0523(15) Uani 1 1 d . . .
H13 H 0.4396 0.4236 0.3178 0.063 Uiso 1 1 calc R . .
C14 C 0.4851(6) 0.2329(7) 0.3165(4) 0.0660(17) Uani 1 1 d . . .
H14 H 0.5526 0.2458 0.2641 0.079 Uiso 1 1 calc R . .
C15 C 0.4537(7) 0.1071(7) 0.3616(4) 0.0713(18) Uani 1 1 d . . .
H15 H 0.5004 0.0352 0.3398 0.086 Uiso 1 1 calc R . .
C16 C 0.3540(7) 0.0877(6) 0.4382(4) 0.0617(16) Uani 1 1 d . . .
H16 H 0.3323 0.0024 0.4679 0.074 Uiso 1 1 calc R . .
C17 C 0.2855(6) 0.1928(5) 0.4717(3) 0.0499(14) Uani 1 1 d . . .
H17 H 0.2188 0.1789 0.5246 0.060 Uiso 1 1 calc R . .
C18 C 0.3544(6) 0.3882(5) 0.6103(3) 0.0410(13) Uani 1 1 d . . .
C19 C 0.4790(6) 0.3189(5) 0.5894(3) 0.0510(14) Uani 1 1 d . . .
H19 H 0.5095 0.3135 0.5276 0.061 Uiso 1 1 calc R . .
C20 C 0.5605(6) 0.2569(5) 0.6590(3) 0.0530(15) Uani 1 1 d . . .
H20 H 0.6425 0.2059 0.6438 0.064 Uiso 1 1 calc R . .
C21 C 0.5228(6) 0.2688(5) 0.7510(3) 0.0490(14) Uani 1 1 d . . .
C22 C 0.3994(7) 0.3420(6) 0.7699(3) 0.0586(16) Uani 1 1 d . . .
H22 H 0.3712 0.3515 0.8311 0.070 Uiso 1 1 calc R . .
C23 C 0.3155(6) 0.4020(5) 0.7014(3) 0.0522(14) Uani 1 1 d . . .
H23 H 0.2327 0.4519 0.7165 0.063 Uiso 1 1 calc R . .
C24 C 0.6125(7) 0.1992(5) 0.8261(3) 0.0634(17) Uani 1 1 d . . .
H24A H 0.5867 0.2375 0.8808 0.076 Uiso 1 1 calc R . .
H24B H 0.7114 0.2141 0.8039 0.076 Uiso 1 1 calc R . .
C25 C 0.5970(7) 0.0527(6) 0.8544(3) 0.0505(14) Uani 1 1 d . . .
C26 C 0.4658(7) 0.0046(6) 0.8876(3) 0.0611(16) Uani 1 1 d . . .
H26 H 0.3863 0.0635 0.8911 0.073 Uiso 1 1 calc R . .
C27 C 0.4501(7) -0.1292(6) 0.9159(4) 0.0629(16) Uani 1 1 d . . .
H27 H 0.3600 -0.1591 0.9365 0.076 Uiso 1 1 calc R . .
C28 C 0.5651(8) -0.2184(6) 0.9138(4) 0.0639(17) Uani 1 1 d . . .
C29 C 0.6947(8) -0.1698(7) 0.8802(4) 0.0768(19) Uani 1 1 d . . .
H29 H 0.7745 -0.2285 0.8772 0.092 Uiso 1 1 calc R . .
C30 C 0.7107(7) -0.0358(7) 0.8504(4) 0.0658(17) Uani 1 1 d . . .
H30 H 0.8004 -0.0062 0.8274 0.079 Uiso 1 1 calc R . .
C31 C 0.9840(12) 0.8292(9) 0.0473(5) 0.173(5) Uani 1 1 d . . .
H31A H 0.8835 0.8416 0.0643 0.260 Uiso 1 1 calc R . .
H31B H 1.0032 0.8333 -0.0189 0.260 Uiso 1 1 calc R . .
H31C H 1.0309 0.8972 0.0632 0.260 Uiso 1 1 calc R . .
C32 C 0.1750(10) 0.5793(9) 0.9153(5) 0.151(4) Uani 1 1 d . . .
H32A H 0.2038 0.6564 0.8702 0.226 Uiso 1 1 calc R . .
H32B H 0.0732 0.5821 0.9263 0.226 Uiso 1 1 calc R . .
H32C H 0.2104 0.5019 0.8919 0.226 Uiso 1 1 calc R . .
H3A H 0.210(5) 0.529(5) 0.553(3) 0.044(15) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C3 1.361(6) . ?
N1 N2 1.395(5) . ?
N1 C4 1.412(6) . ?
N2 C1 1.308(6) . ?
N3 C11 1.344(6) . ?
N3 C18 1.412(6) . ?
N3 H3A 0.90(5) . ?
N4 C28 1.375(7) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
O1 C3 1.249(5) . ?
O2 C31 1.315(8) . ?
O2 H2 0.8200 . ?
O3 C32 1.395(8) . ?
O3 H3 0.8200 . ?
C1 C2 1.431(6) . ?
C1 C10 1.500(6) . ?
C2 C11 1.377(7) . ?
C2 C3 1.436(6) . ?
C4 C5 1.359(6) . ?
C4 C9 1.387(6) . ?
C5 C6 1.373(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.388(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.350(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.360(7) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.460(6) . ?
C12 C17 1.383(6) . ?
C12 C13 1.391(6) . ?
C13 C14 1.362(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.365(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(7) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.363(7) . ?
C18 C23 1.378(6) . ?
C19 C20 1.380(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.384(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.367(7) . ?
C21 C24 1.506(7) . ?
C22 C23 1.377(7) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C25 1.507(7) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C30 1.356(7) . ?
C25 C26 1.378(7) . ?
C26 C27 1.382(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.367(8) . ?
C27 H27 0.9300 . ?
C28 C29 1.368(8) . ?
C29 C30 1.386(8) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?

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
C3 N1 N2 111.2(4) . . ?
C3 N1 C4 129.9(4) . . ?
N2 N1 C4 118.9(4) . . ?
C1 N2 N1 106.9(4) . . ?
C11 N3 C18 131.1(5) . . ?
C11 N3 H3A 108(3) . . ?
C18 N3 H3A 121(3) . . ?
C28 N4 H4A 120.0 . . ?
C28 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C31 O2 H2 109.5 . . ?
C32 O3 H3 109.5 . . ?
N2 C1 C2 111.3(4) . . ?
N2 C1 C10 118.4(4) . . ?
C2 C1 C10 130.3(5) . . ?
C11 C2 C1 131.8(5) . . ?
C11 C2 C3 123.5(4) . . ?
C1 C2 C3 104.5(5) . . ?
O1 C3 N1 125.9(5) . . ?
O1 C3 C2 128.2(5) . . ?
N1 C3 C2 105.9(4) . . ?
C5 C4 C9 120.1(5) . . ?
C5 C4 N1 120.7(4) . . ?
C9 C4 N1 119.3(5) . . ?
C4 C5 C6 120.0(5) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C7 120.0(6) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 118.9(6) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C7 C8 C9 121.9(5) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C8 C9 C4 119.1(5) . . ?
C8 C9 H9 120.5 . . ?
C4 C9 H9 120.5 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 C2 116.9(5) . . ?
N3 C11 C12 120.7(5) . . ?
C2 C11 C12 122.3(4) . . ?
C17 C12 C13 119.4(5) . . ?
C17 C12 C11 121.5(4) . . ?
C13 C12 C11 119.1(5) . . ?
C14 C13 C12 120.0(5) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.3(5) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 120.0(6) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.6(6) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C12 119.6(5) . . ?
C16 C17 H17 120.2 . . ?
C12 C17 H17 120.2 . . ?
C19 C18 C23 118.8(5) . . ?
C19 C18 N3 124.8(4) . . ?
C23 C18 N3 116.3(5) . . ?
C18 C19 C20 120.6(5) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C21 121.4(5) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C22 C21 C20 117.0(5) . . ?
C22 C21 C24 122.5(5) . . ?
C20 C21 C24 120.5(6) . . ?
C21 C22 C23 122.2(5) . . ?
C21 C22 H22 118.9 . . ?
C23 C22 H22 118.9 . . ?
C22 C23 C18 120.0(5) . . ?
C22 C23 H23 120.0 . . ?
C18 C23 H23 120.0 . . ?
C21 C24 C25 113.8(4) . . ?
C21 C24 H24A 108.8 . . ?
C25 C24 H24A 108.8 . . ?
C21 C24 H24B 108.8 . . ?
C25 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
C30 C25 C26 117.8(6) . . ?
C30 C25 C24 121.6(6) . . ?
C26 C25 C24 120.5(6) . . ?
C25 C26 C27 121.3(6) . . ?
C25 C26 H26 119.3 . . ?
C27 C26 H26 119.3 . . ?
C28 C27 C26 120.9(6) . . ?
C28 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
C27 C28 C29 117.3(6) . . ?
C27 C28 N4 120.5(6) . . ?
C29 C28 N4 122.2(7) . . ?
C28 C29 C30 121.9(6) . . ?
C28 C29 H29 119.0 . . ?
C30 C29 H29 119.0 . . ?
C25 C30 C29 120.7(6) . . ?
C25 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
O2 C31 H31A 109.5 . . ?
O2 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O2 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O3 C32 H32A 109.5 . . ?
O3 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O3 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 N2 C1 -3.3(5) . . . . ?
C4 N1 N2 C1 178.0(4) . . . . ?
N1 N2 C1 C2 0.5(6) . . . . ?
N1 N2 C1 C10 178.3(4) . . . . ?
N2 C1 C2 C11 -173.7(5) . . . . ?
C10 C1 C2 C11 8.8(9) . . . . ?
N2 C1 C2 C3 2.2(6) . . . . ?
C10 C1 C2 C3 -175.3(5) . . . . ?
N2 N1 C3 O1 -175.9(4) . . . . ?
C4 N1 C3 O1 2.6(8) . . . . ?
N2 N1 C3 C2 4.6(5) . . . . ?
C4 N1 C3 C2 -176.9(5) . . . . ?
C11 C2 C3 O1 -7.2(8) . . . . ?
C1 C2 C3 O1 176.5(5) . . . . ?
C11 C2 C3 N1 172.3(5) . . . . ?
C1 C2 C3 N1 -4.1(5) . . . . ?
C3 N1 C4 C5 -154.2(5) . . . . ?
N2 N1 C4 C5 24.2(7) . . . . ?
C3 N1 C4 C9 26.1(8) . . . . ?
N2 N1 C4 C9 -155.6(4) . . . . ?
C9 C4 C5 C6 -0.4(8) . . . . ?
N1 C4 C5 C6 179.9(5) . . . . ?
C4 C5 C6 C7 -0.9(9) . . . . ?
C5 C6 C7 C8 1.7(9) . . . . ?
C6 C7 C8 C9 -1.2(9) . . . . ?
C7 C8 C9 C4 0.0(9) . . . . ?
C5 C4 C9 C8 0.8(8) . . . . ?
N1 C4 C9 C8 -179.5(5) . . . . ?
C18 N3 C11 C2 -170.9(5) . . . . ?
C18 N3 C11 C12 7.3(8) . . . . ?
C1 C2 C11 N3 -175.0(5) . . . . ?
C3 C2 C11 N3 9.7(7) . . . . ?
C1 C2 C11 C12 6.9(8) . . . . ?
C3 C2 C11 C12 -168.4(4) . . . . ?
N3 C11 C12 C17 63.5(6) . . . . ?
C2 C11 C12 C17 -118.4(5) . . . . ?
N3 C11 C12 C13 -115.6(5) . . . . ?
C2 C11 C12 C13 62.4(7) . . . . ?
C17 C12 C13 C14 0.5(7) . . . . ?
C11 C12 C13 C14 179.7(5) . . . . ?
C12 C13 C14 C15 -0.2(8) . . . . ?
C13 C14 C15 C16 0.4(9) . . . . ?
C14 C15 C16 C17 -0.8(9) . . . . ?
C15 C16 C17 C12 1.0(8) . . . . ?
C13 C12 C17 C16 -0.9(7) . . . . ?
C11 C12 C17 C16 180.0(5) . . . . ?
C11 N3 C18 C19 24.8(8) . . . . ?
C11 N3 C18 C23 -158.9(5) . . . . ?
C23 C18 C19 C20 4.0(7) . . . . ?
N3 C18 C19 C20 -179.8(4) . . . . ?
C18 C19 C20 C21 -3.6(8) . . . . ?
C19 C20 C21 C22 1.7(7) . . . . ?
C19 C20 C21 C24 179.4(5) . . . . ?
C20 C21 C22 C23 -0.2(8) . . . . ?
C24 C21 C22 C23 -177.9(5) . . . . ?
C21 C22 C23 C18 0.7(8) . . . . ?
C19 C18 C23 C22 -2.6(7) . . . . ?
N3 C18 C23 C22 -179.1(5) . . . . ?
C22 C21 C24 C25 103.1(6) . . . . ?
C20 C21 C24 C25 -74.5(6) . . . . ?
C21 C24 C25 C30 123.9(6) . . . . ?
C21 C24 C25 C26 -57.8(7) . . . . ?
C30 C25 C26 C27 -0.2(7) . . . . ?
C24 C25 C26 C27 -178.6(5) . . . . ?
C25 C26 C27 C28 1.6(8) . . . . ?
C26 C27 C28 C29 -2.0(8) . . . . ?
C26 C27 C28 N4 180.0(5) . . . . ?
C27 C28 C29 C30 0.9(9) . . . . ?
N4 C28 C29 C30 178.9(5) . . . . ?
C26 C25 C30 C29 -0.9(8) . . . . ?
C24 C25 C30 C29 177.5(5) . . . . ?
C28 C29 C30 C25 0.5(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A O1 0.90(5) 1.86(5) 2.679(6) 149(4) .
N4 H4A O3 0.86 2.30 3.158(8) 171.6 1_545
N4 H4B O3 0.86 2.25 3.056(8) 155.4 2_657
O2 H2 N2 0.82 2.07 2.822(6) 151.8 1_655
O3 H3 O2 0.82 1.88 2.677(7) 164.7 1_456
C17 H17 C4 0.93 2.64 3.564(7) 174.0 2_566

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_120813d
_database_code_depnum_ccdc_archive 'CCDC 912501'
_audit_update_record             
;
2014-12-22 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H21 N3 O2'
_chemical_formula_sum            'C24 H21 N3 O2'
_chemical_formula_weight         383.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   7.2287(6)
_cell_length_b                   11.0934(9)
_cell_length_c                   14.0509(14)
_cell_angle_alpha                107.981(2)
_cell_angle_beta                 99.5340(10)
_cell_angle_gamma                105.1460(10)
_cell_volume                     996.58(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1557
_cell_measurement_theta_min      2.413
_cell_measurement_theta_max      24.705

_exptl_crystal_description       block
_exptl_crystal_colour            light-yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9597
_exptl_absorpt_correction_T_max  0.9676
_exptl_absorpt_process_details   'sadabs (Sheldrick, 1996)'

_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            4993
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3457
_reflns_number_gt                2526
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  'SHELXTL (Bruker, 2000)'

_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)+(0.0597P)²+0.2951P] 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       0.044(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3457
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1258
_refine_ls_wR_factor_gt          0.1076
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.971
_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 0.5524(2) 0.26611(15) 0.85810(12) 0.0400(4) Uani 1 1 d . . .
N2 N 0.6549(2) 0.40471(16) 0.90211(12) 0.0440(4) Uani 1 1 d . . .
N3 N 0.0418(2) 0.26162(17) 0.67465(12) 0.0421(4) Uani 1 1 d . . .
O1 O 0.25647(18) 0.11902(13) 0.73385(10) 0.0456(4) Uani 1 1 d . . .
O2 O -0.4793(2) 0.02609(15) 0.35597(11) 0.0616(4) Uani 1 1 d . . .
H2 H -0.4002 -0.0136 0.3426 0.092 Uiso 1 1 calc R . .
C1 C 0.3718(3) 0.23572(19) 0.79114(14) 0.0372(4) Uani 1 1 d . . .
C2 C 0.3511(3) 0.36351(18) 0.79925(13) 0.0369(4) Uani 1 1 d . . .
C3 C 0.5360(3) 0.46202(19) 0.86796(14) 0.0398(4) Uani 1 1 d . . .
C4 C 0.6089(3) 0.6108(2) 0.90042(18) 0.0556(6) Uani 1 1 d . . .
H4A H 0.7466 0.6458 0.9385 0.083 Uiso 1 1 calc R . .
H4B H 0.5327 0.6485 0.9437 0.083 Uiso 1 1 calc R . .
H4C H 0.5943 0.6344 0.8400 0.083 Uiso 1 1 calc R . .
C5 C 0.1842(3) 0.37392(18) 0.74002(14) 0.0373(4) Uani 1 1 d . . .
C6 C 0.1661(3) 0.50587(19) 0.74418(14) 0.0392(4) Uani 1 1 d . . .
C7 C 0.1646(3) 0.5386(2) 0.65670(17) 0.0530(5) Uani 1 1 d . . .
H7 H 0.1779 0.4794 0.5970 0.064 Uiso 1 1 calc R . .
C8 C 0.1432(4) 0.6590(3) 0.6582(2) 0.0667(7) Uani 1 1 d . . .
H8 H 0.1442 0.6816 0.5998 0.080 Uiso 1 1 calc R . .
C9 C 0.1205(4) 0.7457(2) 0.7461(2) 0.0683(7) Uani 1 1 d . . .
H9 H 0.1034 0.8261 0.7464 0.082 Uiso 1 1 calc R . .
C10 C 0.1229(3) 0.7141(2) 0.83316(19) 0.0592(6) Uani 1 1 d . . .
H10 H 0.1089 0.7735 0.8926 0.071 Uiso 1 1 calc R . .
C11 C 0.1461(3) 0.5945(2) 0.83284(16) 0.0469(5) Uani 1 1 d . . .
H11 H 0.1483 0.5734 0.8921 0.056 Uiso 1 1 calc R . .
C12 C -0.1477(3) 0.24523(19) 0.61307(14) 0.0382(4) Uani 1 1 d . . .
C13 C -0.2194(3) 0.14430(18) 0.51542(14) 0.0381(4) Uani 1 1 d . . .
H13 H -0.1435 0.0912 0.4920 0.046 Uiso 1 1 calc R . .
C14 C -0.4031(3) 0.12209(19) 0.45262(14) 0.0402(4) Uani 1 1 d . . .
C15 C -0.5175(3) 0.2016(2) 0.48573(15) 0.0461(5) Uani 1 1 d . . .
C16 C -0.4434(3) 0.2996(2) 0.58378(16) 0.0516(5) Uani 1 1 d . . .
H16 H -0.5191 0.3528 0.6074 0.062 Uiso 1 1 calc R . .
C17 C -0.2616(3) 0.3227(2) 0.64876(15) 0.0482(5) Uani 1 1 d . . .
H17 H -0.2170 0.3888 0.7151 0.058 Uiso 1 1 calc R . .
C18 C -0.7149(3) 0.1792(3) 0.4147(2) 0.0734(7) Uani 1 1 d . . .
H18A H -0.7821 0.2339 0.4521 0.110 Uiso 1 1 calc R . .
H18B H -0.7953 0.0863 0.3904 0.110 Uiso 1 1 calc R . .
H18C H -0.6927 0.2034 0.3565 0.110 Uiso 1 1 calc R . .
C19 C 0.6490(3) 0.17523(19) 0.87411(14) 0.0390(4) Uani 1 1 d . . .
C20 C 0.5416(3) 0.0590(2) 0.88251(15) 0.0479(5) Uani 1 1 d . . .
H20 H 0.4085 0.0429 0.8819 0.057 Uiso 1 1 calc R . .
C21 C 0.6310(3) -0.0340(2) 0.89181(18) 0.0575(6) Uani 1 1 d . . .
H21 H 0.5577 -0.1132 0.8968 0.069 Uiso 1 1 calc R . .
C22 C 0.8273(4) -0.0100(2) 0.89362(18) 0.0608(6) Uani 1 1 d . . .
H22 H 0.8868 -0.0736 0.8982 0.073 Uiso 1 1 calc R . .
C23 C 0.9363(3) 0.1084(3) 0.88871(18) 0.0626(6) Uani 1 1 d . . .
H23 H 1.0707 0.1257 0.8919 0.075 Uiso 1 1 calc R . .
C24 C 0.8481(3) 0.2024(2) 0.87900(16) 0.0517(5) Uani 1 1 d . . .
H24 H 0.9223 0.2826 0.8758 0.062 Uiso 1 1 calc R . .
H3 H 0.064(3) 0.179(2) 0.6735(17) 0.061(6) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.367(2) . ?
N1 N2 1.400(2) . ?
N1 C19 1.418(2) . ?
N2 C3 1.308(2) . ?
N3 C5 1.329(2) . ?
N3 C12 1.427(2) . ?
N3 H3 0.96(2) . ?
O1 C1 1.261(2) . ?
O2 C14 1.354(2) . ?
O2 H2 0.8200 . ?
C1 C2 1.436(2) . ?
C2 C5 1.400(2) . ?
C2 C3 1.439(3) . ?
C3 C4 1.487(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.488(2) . ?
C6 C11 1.385(3) . ?
C6 C7 1.384(3) . ?
C7 C8 1.378(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.376(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.372(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.379(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.385(3) . ?
C12 C17 1.381(3) . ?
C13 C14 1.382(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.391(3) . ?
C15 C16 1.376(3) . ?
C15 C18 1.511(3) . ?
C16 C17 1.381(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.371(3) . ?
C19 C24 1.376(3) . ?
C20 C21 1.380(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.368(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.372(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.385(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 112.03(14) . . ?
C1 N1 C19 127.39(16) . . ?
N2 N1 C19 119.96(14) . . ?
C3 N2 N1 106.46(15) . . ?
C5 N3 C12 129.10(16) . . ?
C5 N3 H3 115.6(13) . . ?
C12 N3 H3 115.0(13) . . ?
C14 O2 H2 109.5 . . ?
O1 C1 N1 125.60(16) . . ?
O1 C1 C2 129.46(16) . . ?
N1 C1 C2 104.91(15) . . ?
C5 C2 C3 132.53(17) . . ?
C5 C2 C1 121.91(17) . . ?
C3 C2 C1 105.29(15) . . ?
N2 C3 C2 111.11(16) . . ?
N2 C3 C4 118.33(17) . . ?
C2 C3 C4 130.52(17) . . ?
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 . . ?
N3 C5 C2 118.51(16) . . ?
N3 C5 C6 119.17(16) . . ?
C2 C5 C6 122.24(17) . . ?
C11 C6 C7 119.70(18) . . ?
C11 C6 C5 121.23(16) . . ?
C7 C6 C5 119.05(17) . . ?
C8 C7 C6 119.9(2) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C9 C8 C7 120.1(2) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.2(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C6 119.87(19) . . ?
C10 C11 H11 120.1 . . ?
C6 C11 H11 120.1 . . ?
C13 C12 C17 119.93(17) . . ?
C13 C12 N3 117.53(16) . . ?
C17 C12 N3 122.50(17) . . ?
C14 C13 C12 120.32(16) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
O2 C14 C13 122.83(17) . . ?
O2 C14 C15 116.47(16) . . ?
C13 C14 C15 120.68(17) . . ?
C16 C15 C14 117.52(17) . . ?
C16 C15 C18 122.42(18) . . ?
C14 C15 C18 120.06(19) . . ?
C15 C16 C17 122.98(18) . . ?
C15 C16 H16 118.5 . . ?
C17 C16 H16 118.5 . . ?
C16 C17 C12 118.52(18) . . ?
C16 C17 H17 120.7 . . ?
C12 C17 H17 120.7 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C24 120.38(18) . . ?
C20 C19 N1 119.47(17) . . ?
C24 C19 N1 120.13(17) . . ?
C19 C20 C21 120.03(19) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 120.1(2) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 119.8(2) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C22 C23 C24 120.6(2) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C19 C24 C23 119.0(2) . . ?
C19 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C3 3.4(2) . . . . ?
C19 N1 N2 C3 175.08(16) . . . . ?
N2 N1 C1 O1 173.30(17) . . . . ?
C19 N1 C1 O1 2.4(3) . . . . ?
N2 N1 C1 C2 -4.74(19) . . . . ?
C19 N1 C1 C2 -175.60(16) . . . . ?
O1 C1 C2 C5 0.9(3) . . . . ?
N1 C1 C2 C5 178.83(16) . . . . ?
O1 C1 C2 C3 -173.84(18) . . . . ?
N1 C1 C2 C3 4.10(19) . . . . ?
N1 N2 C3 C2 -0.6(2) . . . . ?
N1 N2 C3 C4 -178.50(16) . . . . ?
C5 C2 C3 N2 -176.16(18) . . . . ?
C1 C2 C3 N2 -2.2(2) . . . . ?
C5 C2 C3 C4 1.4(3) . . . . ?
C1 C2 C3 C4 175.35(19) . . . . ?
C12 N3 C5 C2 174.18(17) . . . . ?
C12 N3 C5 C6 -8.8(3) . . . . ?
C3 C2 C5 N3 173.07(18) . . . . ?
C1 C2 C5 N3 0.0(3) . . . . ?
C3 C2 C5 C6 -3.9(3) . . . . ?
C1 C2 C5 C6 -176.97(16) . . . . ?
N3 C5 C6 C11 115.4(2) . . . . ?
C2 C5 C6 C11 -67.7(2) . . . . ?
N3 C5 C6 C7 -63.0(2) . . . . ?
C2 C5 C6 C7 113.9(2) . . . . ?
C11 C6 C7 C8 0.0(3) . . . . ?
C5 C6 C7 C8 178.49(19) . . . . ?
C6 C7 C8 C9 -1.0(3) . . . . ?
C7 C8 C9 C10 1.3(4) . . . . ?
C8 C9 C10 C11 -0.7(4) . . . . ?
C9 C10 C11 C6 -0.3(3) . . . . ?
C7 C6 C11 C10 0.6(3) . . . . ?
C5 C6 C11 C10 -177.83(18) . . . . ?
C5 N3 C12 C13 144.01(19) . . . . ?
C5 N3 C12 C17 -38.1(3) . . . . ?
C17 C12 C13 C14 1.1(3) . . . . ?
N3 C12 C13 C14 179.09(16) . . . . ?
C12 C13 C14 O2 179.08(18) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
O2 C14 C15 C16 179.82(18) . . . . ?
C13 C14 C15 C16 -1.9(3) . . . . ?
O2 C14 C15 C18 -0.4(3) . . . . ?
C13 C14 C15 C18 177.9(2) . . . . ?
C14 C15 C16 C17 0.9(3) . . . . ?
C18 C15 C16 C17 -178.9(2) . . . . ?
C15 C16 C17 C12 1.1(3) . . . . ?
C13 C12 C17 C16 -2.1(3) . . . . ?
N3 C12 C17 C16 -179.92(18) . . . . ?
C1 N1 C19 C20 -44.1(3) . . . . ?
N2 N1 C19 C20 145.68(18) . . . . ?
C1 N1 C19 C24 134.6(2) . . . . ?
N2 N1 C19 C24 -35.7(2) . . . . ?
C24 C19 C20 C21 -2.6(3) . . . . ?
N1 C19 C20 C21 176.09(18) . . . . ?
C19 C20 C21 C22 0.6(3) . . . . ?
C20 C21 C22 C23 1.6(3) . . . . ?
C21 C22 C23 C24 -1.8(4) . . . . ?
C20 C19 C24 C23 2.3(3) . . . . ?
N1 C19 C24 C23 -176.32(18) . . . . ?
C22 C23 C24 C19 -0.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 O1 0.96(2) 1.89(2) 2.6963(19) 140.3(19) .
O2 H2 O1 0.82 1.96 2.7482(19) 162.0 2_556

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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_130705d
_database_code_depnum_ccdc_archive 'CCDC 949389'
_audit_update_record             
;
2014-12-22 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H19 N3 O5, C2 H6 O'
_chemical_formula_sum            'C27 H25 N3 O6'
_chemical_formula_weight         487.50

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'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   8.4482(7)
_cell_length_b                   10.4238(11)
_cell_length_c                   13.9303(12)
_cell_angle_alpha                86.458(2)
_cell_angle_beta                 77.2390(10)
_cell_angle_gamma                86.317(2)
_cell_volume                     1192.54(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    876
_cell_measurement_theta_min      3.003
_cell_measurement_theta_max      22.299

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9603
_exptl_absorpt_correction_T_max  0.9742
_exptl_absorpt_process_details   'sadabs (Sheldrick, 1996)'

_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            6035
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.1193
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         25.02
_reflns_number_total             4140
_reflns_number_gt                1848
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  'SHELXTL (Bruker, 2000)'

_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)+(0.0737P)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         4140
_refine_ls_number_parameters     331
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1562
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.1892
_refine_ls_wR_factor_gt          0.1427
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_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 0.6674(4) 0.5671(3) 0.5603(3) 0.0399(9) Uani 1 1 d . . .
N2 N 0.4355(4) 0.8359(3) 0.4052(2) 0.0361(9) Uani 1 1 d . . .
N3 N 0.3312(4) 0.8971(3) 0.4829(2) 0.0415(9) Uani 1 1 d . . .
O1 O 0.8697(5) 0.4686(4) 0.8787(2) 0.0876(14) Uani 1 1 d . . .
O2 O 1.0621(4) 0.3168(3) 0.8393(2) 0.0730(11) Uani 1 1 d . . .
H2 H 1.0710 0.3249 0.8960 0.110 Uiso 1 1 calc R . .
O3 O 1.1392(4) 0.1149(3) 0.5342(2) 0.0662(10) Uani 1 1 d . . .
H3 H 1.1844 0.0624 0.4942 0.099 Uiso 1 1 calc R . .
O4 O 1.0631(4) 0.2109(3) 0.4039(2) 0.0607(10) Uani 1 1 d . . .
O5 O 0.6248(3) 0.6614(3) 0.38623(18) 0.0442(8) Uani 1 1 d . . .
O6 O 0.8861(4) 0.6766(4) 0.9831(2) 0.0771(11) Uani 1 1 d . . .
H6 H 0.8778 0.6047 0.9645 0.116 Uiso 1 1 calc R . .
C1 C 0.9482(6) 0.3979(5) 0.8192(3) 0.0531(13) Uani 1 1 d . . .
C2 C 1.0618(5) 0.2062(4) 0.4893(3) 0.0402(11) Uani 1 1 d . . .
C3 C 0.9215(5) 0.3921(4) 0.7181(3) 0.0398(11) Uani 1 1 d . . .
C4 C 1.0016(5) 0.3008(4) 0.6548(3) 0.0412(11) Uani 1 1 d . . .
H4 H 1.0754 0.2405 0.6747 0.049 Uiso 1 1 calc R . .
C5 C 0.9710(5) 0.2996(4) 0.5610(3) 0.0359(10) Uani 1 1 d . . .
C6 C 0.8591(5) 0.3889(4) 0.5333(3) 0.0360(10) Uani 1 1 d . . .
H6A H 0.8396 0.3886 0.4701 0.043 Uiso 1 1 calc R . .
C7 C 0.7759(5) 0.4782(4) 0.5972(3) 0.0364(10) Uani 1 1 d . . .
C8 C 0.8098(5) 0.4807(4) 0.6897(3) 0.0434(11) Uani 1 1 d . . .
H8 H 0.7572 0.5423 0.7329 0.052 Uiso 1 1 calc R . .
C9 C 0.5555(5) 0.6535(4) 0.6038(3) 0.0346(10) Uani 1 1 d . . .
C10 C 0.5107(5) 0.6539(4) 0.7128(3) 0.0326(10) Uani 1 1 d . . .
C11 C 0.5595(5) 0.7500(4) 0.7623(3) 0.0434(11) Uani 1 1 d . . .
H11 H 0.6153 0.8182 0.7272 0.052 Uiso 1 1 calc R . .
C12 C 0.5251(6) 0.7443(5) 0.8636(3) 0.0542(13) Uani 1 1 d . . .
H12 H 0.5580 0.8086 0.8972 0.065 Uiso 1 1 calc R . .
C13 C 0.4420(6) 0.6437(5) 0.9151(3) 0.0615(14) Uani 1 1 d . . .
H13 H 0.4188 0.6404 0.9837 0.074 Uiso 1 1 calc R . .
C14 C 0.3934(6) 0.5488(5) 0.8670(3) 0.0642(15) Uani 1 1 d . . .
H14 H 0.3369 0.4810 0.9023 0.077 Uiso 1 1 calc R . .
C15 C 0.4283(5) 0.5538(4) 0.7658(3) 0.0479(12) Uani 1 1 d . . .
H15 H 0.3959 0.4888 0.7328 0.058 Uiso 1 1 calc R . .
C16 C 0.5275(5) 0.7375(4) 0.4381(3) 0.0337(10) Uani 1 1 d . . .
C17 C 0.4850(5) 0.7398(4) 0.5440(3) 0.0330(10) Uani 1 1 d . . .
C18 C 0.3607(5) 0.8410(4) 0.5640(3) 0.0369(10) Uani 1 1 d . . .
C19 C 0.2665(5) 0.8845(4) 0.6611(3) 0.0550(13) Uani 1 1 d . . .
H19A H 0.1801 0.9446 0.6510 0.082 Uiso 1 1 calc R . .
H19B H 0.3372 0.9253 0.6939 0.082 Uiso 1 1 calc R . .
H19C H 0.2218 0.8115 0.7010 0.082 Uiso 1 1 calc R . .
C20 C 0.4147(5) 0.8623(4) 0.3076(3) 0.0385(11) Uani 1 1 d . . .
C21 C 0.2715(5) 0.9212(4) 0.2915(3) 0.0444(11) Uani 1 1 d . . .
H21 H 0.1895 0.9462 0.3443 0.053 Uiso 1 1 calc R . .
C22 C 0.2508(6) 0.9424(4) 0.1965(3) 0.0569(13) Uani 1 1 d . . .
H22 H 0.1538 0.9816 0.1856 0.068 Uiso 1 1 calc R . .
C23 C 0.3702(7) 0.9070(5) 0.1176(3) 0.0677(15) Uani 1 1 d . . .
H23 H 0.3543 0.9216 0.0538 0.081 Uiso 1 1 calc R . .
C24 C 0.5136(7) 0.8498(5) 0.1336(3) 0.0667(15) Uani 1 1 d . . .
H24 H 0.5956 0.8256 0.0805 0.080 Uiso 1 1 calc R . .
C25 C 0.5361(6) 0.8281(4) 0.2290(3) 0.0538(13) Uani 1 1 d . . .
H25 H 0.6337 0.7902 0.2398 0.065 Uiso 1 1 calc R . .
C26 C 0.9780(10) 0.7510(7) 0.9054(5) 0.124(3) Uani 1 1 d . . .
H26A H 1.0619 0.6952 0.8673 0.149 Uiso 1 1 calc R . .
H26B H 0.9076 0.7846 0.8624 0.149 Uiso 1 1 calc R . .
C27 C 1.0515(9) 0.8537(7) 0.9347(5) 0.127(3) Uani 1 1 d . . .
H27A H 0.9695 0.9114 0.9704 0.190 Uiso 1 1 calc R . .
H27B H 1.1122 0.8988 0.8775 0.190 Uiso 1 1 calc R . .
H27C H 1.1235 0.8216 0.9762 0.190 Uiso 1 1 calc R . .
H1 H 0.680(5) 0.569(4) 0.498(3) 0.062(15) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C9 1.334(4) . ?
N1 C7 1.416(5) . ?
N1 H1 0.84(4) . ?
N2 C16 1.365(4) . ?
N2 N3 1.396(4) . ?
N2 C20 1.417(4) . ?
N3 C18 1.305(4) . ?
O1 C1 1.200(5) . ?
O2 C1 1.306(5) . ?
O2 H2 0.8200 . ?
O3 C2 1.323(4) . ?
O3 H3 0.8200 . ?
O4 C2 1.186(4) . ?
O5 C16 1.245(4) . ?
O6 C26 1.407(7) . ?
O6 H6 0.8200 . ?
C1 C3 1.479(5) . ?
C2 C5 1.490(5) . ?
C3 C4 1.378(5) . ?
C3 C8 1.381(5) . ?
C4 C5 1.387(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(5) . ?
C6 C7 1.376(5) . ?
C6 H6A 0.9300 . ?
C7 C8 1.383(5) . ?
C8 H8 0.9300 . ?
C9 C17 1.384(5) . ?
C9 C10 1.482(5) . ?
C10 C15 1.374(6) . ?
C10 C11 1.383(5) . ?
C11 C12 1.374(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.362(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.442(5) . ?
C17 C18 1.434(5) . ?
C18 C19 1.490(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C25 1.372(5) . ?
C20 C21 1.378(5) . ?
C21 C22 1.375(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.369(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.372(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.387(5) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C27 1.396(8) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

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
C9 N1 C7 132.3(3) . . ?
C9 N1 H1 114(3) . . ?
C7 N1 H1 114(3) . . ?
C16 N2 N3 111.8(3) . . ?
C16 N2 C20 127.4(3) . . ?
N3 N2 C20 119.6(3) . . ?
C18 N3 N2 106.6(3) . . ?
C1 O2 H2 109.5 . . ?
C2 O3 H3 109.5 . . ?
C26 O6 H6 109.5 . . ?
O1 C1 O2 122.5(4) . . ?
O1 C1 C3 123.2(4) . . ?
O2 C1 C3 114.2(4) . . ?
O4 C2 O3 124.1(4) . . ?
O4 C2 C5 125.1(4) . . ?
O3 C2 C5 110.8(3) . . ?
C4 C3 C8 120.7(4) . . ?
C4 C3 C1 121.9(4) . . ?
C8 C3 C1 117.4(4) . . ?
C3 C4 C5 119.4(4) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 119.5(4) . . ?
C6 C5 C2 120.0(3) . . ?
C4 C5 C2 120.5(4) . . ?
C7 C6 C5 121.3(3) . . ?
C7 C6 H6A 119.3 . . ?
C5 C6 H6A 119.3 . . ?
C6 C7 C8 118.9(4) . . ?
C6 C7 N1 116.6(3) . . ?
C8 C7 N1 124.4(3) . . ?
C3 C8 C7 120.2(4) . . ?
C3 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
N1 C9 C17 117.8(3) . . ?
N1 C9 C10 119.6(3) . . ?
C17 C9 C10 122.6(3) . . ?
C15 C10 C11 119.4(4) . . ?
C15 C10 C9 119.8(4) . . ?
C11 C10 C9 120.7(4) . . ?
C12 C11 C10 119.7(4) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 120.0(4) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 120.7(4) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 119.5(5) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C14 C15 C10 120.8(4) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
O5 C16 N2 126.5(3) . . ?
O5 C16 C17 128.1(3) . . ?
N2 C16 C17 105.4(3) . . ?
C9 C17 C18 133.2(3) . . ?
C9 C17 C16 122.2(3) . . ?
C18 C17 C16 104.6(3) . . ?
N3 C18 C17 111.7(3) . . ?
N3 C18 C19 119.6(3) . . ?
C17 C18 C19 128.8(4) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C21 119.8(4) . . ?
C25 C20 N2 120.2(4) . . ?
C21 C20 N2 120.0(4) . . ?
C22 C21 C20 119.4(4) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C23 C22 C21 121.3(4) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C22 C23 C24 119.4(4) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C23 C24 C25 119.9(4) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C20 C25 C24 120.2(4) . . ?
C20 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C27 C26 O6 114.9(6) . . ?
C27 C26 H26A 108.6 . . ?
O6 C26 H26A 108.6 . . ?
C27 C26 H26B 108.6 . . ?
O6 C26 H26B 108.6 . . ?
H26A C26 H26B 107.5 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N2 N3 C18 2.1(4) . . . . ?
C20 N2 N3 C18 170.3(4) . . . . ?
O1 C1 C3 C4 -173.0(5) . . . . ?
O2 C1 C3 C4 5.2(7) . . . . ?
O1 C1 C3 C8 5.7(8) . . . . ?
O2 C1 C3 C8 -176.1(4) . . . . ?
C8 C3 C4 C5 1.0(7) . . . . ?
C1 C3 C4 C5 179.7(4) . . . . ?
C3 C4 C5 C6 -0.9(6) . . . . ?
C3 C4 C5 C2 177.0(4) . . . . ?
O4 C2 C5 C6 10.4(7) . . . . ?
O3 C2 C5 C6 -168.4(4) . . . . ?
O4 C2 C5 C4 -167.4(4) . . . . ?
O3 C2 C5 C4 13.7(6) . . . . ?
C4 C5 C6 C7 -0.7(6) . . . . ?
C2 C5 C6 C7 -178.6(4) . . . . ?
C5 C6 C7 C8 2.2(6) . . . . ?
C5 C6 C7 N1 178.4(4) . . . . ?
C9 N1 C7 C6 170.4(4) . . . . ?
C9 N1 C7 C8 -13.6(7) . . . . ?
C4 C3 C8 C7 0.5(7) . . . . ?
C1 C3 C8 C7 -178.2(4) . . . . ?
C6 C7 C8 C3 -2.1(6) . . . . ?
N1 C7 C8 C3 -178.0(4) . . . . ?
C7 N1 C9 C17 170.7(4) . . . . ?
C7 N1 C9 C10 -9.6(7) . . . . ?
N1 C9 C10 C15 -68.5(5) . . . . ?
C17 C9 C10 C15 111.2(5) . . . . ?
N1 C9 C10 C11 107.6(4) . . . . ?
C17 C9 C10 C11 -72.7(5) . . . . ?
C15 C10 C11 C12 0.0(6) . . . . ?
C9 C10 C11 C12 -176.1(4) . . . . ?
C10 C11 C12 C13 -0.3(6) . . . . ?
C11 C12 C13 C14 0.2(7) . . . . ?
C12 C13 C14 C15 0.2(7) . . . . ?
C13 C14 C15 C10 -0.4(7) . . . . ?
C11 C10 C15 C14 0.3(6) . . . . ?
C9 C10 C15 C14 176.5(4) . . . . ?
N3 N2 C16 O5 175.9(4) . . . . ?
C20 N2 C16 O5 8.9(7) . . . . ?
N3 N2 C16 C17 -2.9(4) . . . . ?
C20 N2 C16 C17 -170.0(4) . . . . ?
N1 C9 C17 C18 178.0(4) . . . . ?
C10 C9 C17 C18 -1.7(7) . . . . ?
N1 C9 C17 C16 0.7(6) . . . . ?
C10 C9 C17 C16 -179.0(4) . . . . ?
O5 C16 C17 C9 1.7(7) . . . . ?
N2 C16 C17 C9 -179.5(4) . . . . ?
O5 C16 C17 C18 -176.3(4) . . . . ?
N2 C16 C17 C18 2.5(4) . . . . ?
N2 N3 C18 C17 -0.3(5) . . . . ?
N2 N3 C18 C19 -179.5(4) . . . . ?
C9 C17 C18 N3 -179.1(4) . . . . ?
C16 C17 C18 N3 -1.4(5) . . . . ?
C9 C17 C18 C19 0.0(8) . . . . ?
C16 C17 C18 C19 177.7(4) . . . . ?
C16 N2 C20 C25 -29.2(6) . . . . ?
N3 N2 C20 C25 164.6(4) . . . . ?
C16 N2 C20 C21 150.0(4) . . . . ?
N3 N2 C20 C21 -16.2(6) . . . . ?
C25 C20 C21 C22 1.3(7) . . . . ?
N2 C20 C21 C22 -177.9(4) . . . . ?
C20 C21 C22 C23 -0.4(7) . . . . ?
C21 C22 C23 C24 -0.3(8) . . . . ?
C22 C23 C24 C25 0.2(8) . . . . ?
C21 C20 C25 C24 -1.5(7) . . . . ?
N2 C20 C25 C24 177.7(4) . . . . ?
C23 C24 C25 C20 0.7(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.056
