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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ch15606a
_audit_block_doi                 10.5517/ccdc.csd.cc1mvl79
_database_code_depnum_ccdc_archive 'CCDC 1515101'
_audit_update_record             
;
2017-01-06 deposited with the CCDC.
2017-01-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 N2 O'
_chemical_formula_sum            'C24 H18 N2 O'
_chemical_formula_weight         350.40

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           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   13.365(2)
_cell_length_b                   17.037(3)
_cell_length_c                   16.781(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.932(3)
_cell_angle_gamma                90.00
_cell_volume                     3774.6(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3502
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      24.71

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1472
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9746
_exptl_absorpt_correction_T_max  0.9842
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'Bruker APEX2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23348
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_sigmaI/netI    0.0550
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         25.09
_reflns_number_total             6606
_reflns_number_gt                4543
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0814P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6606
_refine_ls_number_parameters     487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1512
_refine_ls_wR_factor_gt          0.1344
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.38425(18) 0.12011(17) 1.36106(14) 0.0487(7) Uani 1 1 d . . .
H1A H 0.4345 0.1158 1.4100 0.073 Uiso 1 1 calc R . .
H1B H 0.3926 0.1705 1.3347 0.073 Uiso 1 1 calc R . .
H1C H 0.3940 0.0772 1.3241 0.073 Uiso 1 1 calc R . .
C2 C 0.20433(18) 0.12056(13) 1.32004(12) 0.0333(6) Uani 1 1 d . . .
C3 C 0.21397(17) 0.12638(13) 1.23918(11) 0.0302(5) Uani 1 1 d . . .
H3 H 0.2792 0.1272 1.2233 0.036 Uiso 1 1 calc R . .
C4 C 0.12719(16) 0.13099(12) 1.18135(12) 0.0275(5) Uani 1 1 d . . .
C5 C 0.03258(18) 0.12893(14) 1.20422(13) 0.0373(6) Uani 1 1 d . . .
H5 H -0.0266 0.1315 1.1648 0.045 Uiso 1 1 calc R . .
C6 C 0.02453(18) 0.12311(14) 1.28575(13) 0.0390(6) Uani 1 1 d . . .
H6 H -0.0405 0.1221 1.3019 0.047 Uiso 1 1 calc R . .
C7 C 0.10951(18) 0.11877(14) 1.34308(13) 0.0374(6) Uani 1 1 d . . .
H7 H 0.1032 0.1145 1.3985 0.045 Uiso 1 1 calc R . .
C8 C 0.13996(15) 0.14170(13) 1.09507(11) 0.0260(5) Uani 1 1 d . . .
C9 C 0.16217(16) 0.08040(13) 1.04604(12) 0.0294(5) Uani 1 1 d . . .
H9 H 0.1655 0.0284 1.0667 0.035 Uiso 1 1 calc R . .
C10 C 0.17985(15) 0.09342(12) 0.96625(11) 0.0262(5) Uani 1 1 d . . .
C11 C 0.20320(15) 0.02783(13) 0.91419(12) 0.0282(5) Uani 1 1 d . . .
C12 C 0.23717(19) -0.04543(14) 0.94499(13) 0.0415(6) Uani 1 1 d . . .
H12 H 0.2468 -0.0540 1.0016 0.050 Uiso 1 1 calc R . .
C13 C 0.2570(2) -0.10582(15) 0.89402(14) 0.0477(7) Uani 1 1 d . . .
H13 H 0.2790 -0.1553 0.9162 0.057 Uiso 1 1 calc R . .
C14 C 0.24511(19) -0.09480(15) 0.81211(14) 0.0440(6) Uani 1 1 d . . .
H14 H 0.2594 -0.1362 0.7776 0.053 Uiso 1 1 calc R . .
C15 C 0.21203(17) -0.02268(14) 0.78033(13) 0.0375(6) Uani 1 1 d . . .
H15 H 0.2037 -0.0145 0.7237 0.045 Uiso 1 1 calc R . .
C16 C 0.19110(16) 0.03734(13) 0.83040(12) 0.0295(5) Uani 1 1 d . . .
H16 H 0.1679 0.0863 0.8075 0.035 Uiso 1 1 calc R . .
C17 C 0.15209(15) 0.22514(12) 0.97992(11) 0.0245(5) Uani 1 1 d . . .
C18 C 0.13446(15) 0.21569(12) 1.05984(11) 0.0243(5) Uani 1 1 d . . .
C19 C 0.12307(16) 0.34463(13) 1.03297(12) 0.0275(5) Uani 1 1 d . . .
C20 C 0.11371(18) 0.42539(14) 1.03800(13) 0.0360(6) Uani 1 1 d . . .
H20 H 0.0993 0.4497 1.0859 0.043 Uiso 1 1 calc R . .
C21 C 0.12606(18) 0.46948(15) 0.97100(13) 0.0409(6) Uani 1 1 d . . .
H21 H 0.1218 0.5251 0.9735 0.049 Uiso 1 1 calc R . .
C22 C 0.14467(18) 0.43405(14) 0.89969(14) 0.0407(6) Uani 1 1 d . . .
H22 H 0.1512 0.4657 0.8542 0.049 Uiso 1 1 calc R . .
C23 C 0.15370(17) 0.35379(14) 0.89457(12) 0.0351(6) Uani 1 1 d . . .
H23 H 0.1665 0.3300 0.8459 0.042 Uiso 1 1 calc R . .
C24 C 0.14378(15) 0.30760(12) 0.96180(11) 0.0256(5) Uani 1 1 d . . .
C25 C 0.4856(3) 0.03220(17) 1.16262(16) 0.0672(9) Uani 1 1 d . . .
H25A H 0.4939 0.0007 1.2121 0.101 Uiso 1 1 calc R . .
H25B H 0.5487 0.0315 1.1397 0.101 Uiso 1 1 calc R . .
H25C H 0.4307 0.0102 1.1235 0.101 Uiso 1 1 calc R . .
C26 C 0.44602(19) 0.16354(16) 1.11824(13) 0.0409(6) Uani 1 1 d . . .
C27 C 0.47029(17) 0.14841(14) 1.04220(12) 0.0356(6) Uani 1 1 d . . .
H27 H 0.4999 0.0997 1.0312 0.043 Uiso 1 1 calc R . .
C28 C 0.45067(15) 0.20573(14) 0.98194(12) 0.0295(5) Uani 1 1 d . . .
C29 C 0.40576(17) 0.27613(14) 0.99799(12) 0.0348(6) Uani 1 1 d . . .
H29 H 0.3895 0.3140 0.9564 0.042 Uiso 1 1 calc R . .
C30 C 0.38472(17) 0.29109(16) 1.07490(13) 0.0412(6) Uani 1 1 d . . .
H30 H 0.3562 0.3401 1.0863 0.049 Uiso 1 1 calc R . .
C31 C 0.40462(18) 0.23570(16) 1.13481(13) 0.0418(6) Uani 1 1 d . . .
H31 H 0.3902 0.2466 1.1874 0.050 Uiso 1 1 calc R . .
C32 C 0.48255(15) 0.19147(13) 0.90219(11) 0.0266(5) Uani 1 1 d . . .
C33 C 0.58271(16) 0.17664(13) 0.89556(12) 0.0287(5) Uani 1 1 d . . .
H33 H 0.6310 0.1736 0.9434 0.034 Uiso 1 1 calc R . .
C34 C 0.61582(16) 0.16597(12) 0.82097(12) 0.0267(5) Uani 1 1 d . . .
C35 C 0.72396(16) 0.14811(13) 0.81787(12) 0.0290(5) Uani 1 1 d . . .
C36 C 0.80041(17) 0.17634(15) 0.87605(14) 0.0428(6) Uani 1 1 d . . .
H36 H 0.7836 0.2101 0.9171 0.051 Uiso 1 1 calc R . .
C37 C 0.89986(19) 0.15656(18) 0.87568(17) 0.0592(8) Uani 1 1 d . . .
H37 H 0.9511 0.1768 0.9160 0.071 Uiso 1 1 calc R . .
C38 C 0.92519(19) 0.10766(18) 0.81718(18) 0.0591(8) Uani 1 1 d . . .
H38 H 0.9940 0.0935 0.8175 0.071 Uiso 1 1 calc R . .
C39 C 0.85133(19) 0.07896(15) 0.75789(16) 0.0478(7) Uani 1 1 d . . .
H39 H 0.8691 0.0456 0.7169 0.057 Uiso 1 1 calc R . .
C40 C 0.75112(17) 0.09904(14) 0.75840(13) 0.0372(6) Uani 1 1 d . . .
H40 H 0.7002 0.0791 0.7177 0.045 Uiso 1 1 calc R . .
C41 C 0.45323(15) 0.18091(12) 0.75619(11) 0.0243(5) Uani 1 1 d . . .
C42 C 0.41696(15) 0.19322(12) 0.82931(11) 0.0246(5) Uani 1 1 d . . .
C43 C 0.28189(16) 0.19551(12) 0.73171(11) 0.0257(5) Uani 1 1 d . . .
C44 C 0.18337(16) 0.19791(13) 0.68878(12) 0.0307(5) Uani 1 1 d . . .
H44 H 0.1266 0.2066 0.7154 0.037 Uiso 1 1 calc R . .
C45 C 0.17195(17) 0.18723(13) 0.60661(13) 0.0351(6) Uani 1 1 d . . .
H45 H 0.1058 0.1879 0.5761 0.042 Uiso 1 1 calc R . .
C46 C 0.25526(17) 0.17536(14) 0.56684(13) 0.0361(6) Uani 1 1 d . . .
H46 H 0.2446 0.1684 0.5100 0.043 Uiso 1 1 calc R . .
C47 C 0.35250(17) 0.17356(13) 0.60865(12) 0.0303(5) Uani 1 1 d . . .
H47 H 0.4088 0.1661 0.5812 0.036 Uiso 1 1 calc R . .
C48 C 0.36635(15) 0.18306(12) 0.69281(11) 0.0258(5) Uani 1 1 d . . .
N1 N 0.17551(13) 0.16575(10) 0.93344(9) 0.0263(4) Uani 1 1 d . . .
N2 N 0.11701(13) 0.28804(10) 1.09148(9) 0.0287(4) Uani 1 1 d . . .
H2 H 0.1042 0.2969 1.1406 0.034 Uiso 1 1 calc R . .
N3 N 0.55151(13) 0.16800(10) 0.75023(9) 0.0266(4) Uani 1 1 d . . .
N4 N 0.31304(12) 0.20400(10) 0.81407(9) 0.0281(4) Uani 1 1 d . . .
H4 H 0.2737 0.2144 0.8502 0.034 Uiso 1 1 calc R . .
O1 O 0.28495(13) 0.11550(11) 1.38182(8) 0.0478(5) Uani 1 1 d . . .
O2 O 0.46145(16) 0.11082(11) 1.18081(9) 0.0589(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.426(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O1 1.377(3) . ?
C2 C7 1.381(3) . ?
C2 C3 1.386(3) . ?
C3 C4 1.394(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.378(3) . ?
C4 C8 1.495(3) . ?
C5 C6 1.393(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.372(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C18 1.389(3) . ?
C8 C9 1.390(3) . ?
C9 C10 1.413(3) . ?
C9 H9 0.9500 . ?
C10 N1 1.347(3) . ?
C10 C11 1.481(3) . ?
C11 C12 1.399(3) . ?
C11 C16 1.400(3) . ?
C12 C13 1.390(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.372(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 N1 1.344(3) . ?
C17 C18 1.407(3) . ?
C17 C24 1.438(3) . ?
C18 N2 1.376(3) . ?
C19 N2 1.387(3) . ?
C19 C20 1.385(3) . ?
C19 C24 1.416(3) . ?
C20 C21 1.383(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.397(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.376(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.399(3) . ?
C23 H23 0.9500 . ?
C25 O2 1.422(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 O2 1.373(3) . ?
C26 C27 1.389(3) . ?
C26 C31 1.394(3) . ?
C27 C28 1.401(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.386(3) . ?
C28 C32 1.486(3) . ?
C29 C30 1.387(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.374(3) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 C33 1.384(3) . ?
C32 C42 1.390(3) . ?
C33 C34 1.403(3) . ?
C33 H33 0.9500 . ?
C34 N3 1.354(2) . ?
C34 C35 1.486(3) . ?
C35 C36 1.385(3) . ?
C35 C40 1.392(3) . ?
C36 C37 1.372(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.369(4) . ?
C37 H37 0.9500 . ?
C38 C39 1.378(4) . ?
C38 H38 0.9500 . ?
C39 C40 1.384(3) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C41 N3 1.351(3) . ?
C41 C42 1.403(3) . ?
C41 C48 1.448(3) . ?
C42 N4 1.385(3) . ?
C43 N4 1.388(2) . ?
C43 C44 1.400(3) . ?
C43 C48 1.405(3) . ?
C44 C45 1.376(3) . ?
C44 H44 0.9500 . ?
C45 C46 1.399(3) . ?
C45 H45 0.9500 . ?
C46 C47 1.378(3) . ?
C46 H46 0.9500 . ?
C47 C48 1.405(3) . ?
C47 H47 0.9500 . ?
N2 H2 0.8800 . ?
N4 H4 0.8800 . ?

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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C7 115.62(18) . . ?
O1 C2 C3 124.1(2) . . ?
C7 C2 C3 120.3(2) . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 120.33(19) . . ?
C5 C4 C8 121.37(18) . . ?
C3 C4 C8 118.25(19) . . ?
C4 C5 C6 119.3(2) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C7 C6 C5 120.7(2) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C2 119.9(2) . . ?
C6 C7 H7 120.1 . . ?
C2 C7 H7 120.1 . . ?
C18 C8 C9 115.59(19) . . ?
C18 C8 C4 121.09(18) . . ?
C9 C8 C4 123.26(19) . . ?
C8 C9 C10 121.7(2) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
N1 C10 C9 121.87(19) . . ?
N1 C10 C11 116.65(18) . . ?
C9 C10 C11 121.48(19) . . ?
C12 C11 C16 117.0(2) . . ?
C12 C11 C10 122.75(18) . . ?
C16 C11 C10 120.22(19) . . ?
C13 C12 C11 121.0(2) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 119.2(2) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C11 121.6(2) . . ?
C15 C16 H16 119.2 . . ?
C11 C16 H16 119.2 . . ?
N1 C17 C18 123.78(19) . . ?
N1 C17 C24 129.05(18) . . ?
C18 C17 C24 107.13(17) . . ?
N2 C18 C8 130.49(18) . . ?
N2 C18 C17 109.20(18) . . ?
C8 C18 C17 120.26(19) . . ?
N2 C19 C20 129.1(2) . . ?
N2 C19 C24 109.14(19) . . ?
C20 C19 C24 121.7(2) . . ?
C21 C20 C19 117.8(2) . . ?
C21 C20 H20 121.1 . . ?
C19 C20 H20 121.1 . . ?
C20 C21 C22 121.4(2) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C23 C22 C21 120.8(2) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 119.2(2) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C23 C24 C19 119.0(2) . . ?
C23 C24 C17 134.9(2) . . ?
C19 C24 C17 106.01(17) . . ?
O2 C25 H25A 109.5 . . ?
O2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O2 C26 C27 123.5(2) . . ?
O2 C26 C31 116.2(2) . . ?
C27 C26 C31 120.2(2) . . ?
C26 C27 C28 119.3(2) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 H27 120.3 . . ?
C29 C28 C27 120.1(2) . . ?
C29 C28 C32 120.6(2) . . ?
C27 C28 C32 119.2(2) . . ?
C30 C29 C28 119.8(2) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C31 C30 C29 120.7(2) . . ?
C31 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?
C30 C31 C26 119.8(2) . . ?
C30 C31 H31 120.1 . . ?
C26 C31 H31 120.1 . . ?
C33 C32 C42 114.77(19) . . ?
C33 C32 C28 121.24(17) . . ?
C42 C32 C28 123.98(19) . . ?
C32 C33 C34 122.59(17) . . ?
C32 C33 H33 118.7 . . ?
C34 C33 H33 118.7 . . ?
N3 C34 C33 122.27(19) . . ?
N3 C34 C35 117.60(19) . . ?
C33 C34 C35 120.08(17) . . ?
C36 C35 C40 117.9(2) . . ?
C36 C35 C34 121.3(2) . . ?
C40 C35 C34 120.75(19) . . ?
C37 C36 C35 121.4(2) . . ?
C37 C36 H36 119.3 . . ?
C35 C36 H36 119.3 . . ?
C38 C37 C36 120.0(2) . . ?
C38 C37 H37 120.0 . . ?
C36 C37 H37 120.0 . . ?
C37 C38 C39 120.3(2) . . ?
C37 C38 H38 119.9 . . ?
C39 C38 H38 119.9 . . ?
C38 C39 C40 119.6(3) . . ?
C38 C39 H39 120.2 . . ?
C40 C39 H39 120.2 . . ?
C39 C40 C35 120.9(2) . . ?
C39 C40 H40 119.6 . . ?
C35 C40 H40 119.6 . . ?
N3 C41 C42 124.12(17) . . ?
N3 C41 C48 128.89(18) . . ?
C42 C41 C48 106.97(18) . . ?
N4 C42 C32 130.0(2) . . ?
N4 C42 C41 109.33(16) . . ?
C32 C42 C41 120.65(19) . . ?
N4 C43 C44 128.5(2) . . ?
N4 C43 C48 109.88(17) . . ?
C44 C43 C48 121.64(18) . . ?
C45 C44 C43 117.5(2) . . ?
C45 C44 H44 121.3 . . ?
C43 C44 H44 121.3 . . ?
C44 C45 C46 121.6(2) . . ?
C44 C45 H45 119.2 . . ?
C46 C45 H45 119.2 . . ?
C47 C46 C45 121.19(19) . . ?
C47 C46 H46 119.4 . . ?
C45 C46 H46 119.4 . . ?
C46 C47 C48 118.4(2) . . ?
C46 C47 H47 120.8 . . ?
C48 C47 H47 120.8 . . ?
C47 C48 C43 119.64(18) . . ?
C47 C48 C41 134.5(2) . . ?
C43 C48 C41 105.84(17) . . ?
C17 N1 C10 116.78(17) . . ?
C18 N2 C19 108.51(17) . . ?
C18 N2 H2 125.7 . . ?
C19 N2 H2 125.7 . . ?
C41 N3 C34 115.57(18) . . ?
C42 N4 C43 107.90(17) . . ?
C42 N4 H4 126.0 . . ?
C43 N4 H4 126.0 . . ?
C2 O1 C1 117.50(17) . . ?
C26 O2 C25 117.67(19) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.089
####################################################################### 
# 
# 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_d18452
_audit_block_doi                 10.5517/ccdc.csd.cc1mvl8b
_database_code_depnum_ccdc_archive 'CCDC 1515102'
_audit_update_record             
;
2017-01-06 deposited with the CCDC.
2017-01-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 N2 O'
_chemical_formula_sum            'C24 H18 N2 O'
_chemical_formula_weight         350.40

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'

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

_cell_length_a                   9.4800(12)
_cell_length_b                   13.2295(16)
_cell_length_c                   15.0067(19)
_cell_angle_alpha                88.685(4)
_cell_angle_beta                 73.346(4)
_cell_angle_gamma                86.478(4)
_cell_volume                     1799.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9847
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      24.98

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9635
_exptl_absorpt_correction_T_max  0.9952
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            62260
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         25.03
_reflns_number_total             6332
_reflns_number_gt                5125
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0417P)²+0.6138P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6332
_refine_ls_number_parameters     489
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.1040
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5769(2) 0.76190(16) 0.88918(13) 0.0571(5) Uani 1 1 d . . .
H1A H 0.6739 0.7464 0.8451 0.086 Uiso 1 1 calc R . .
H1B H 0.5327 0.6987 0.9151 0.086 Uiso 1 1 calc R . .
H1C H 0.5881 0.8036 0.9396 0.086 Uiso 1 1 calc R . .
C2 C 0.45352(17) 0.76651(12) 0.77097(11) 0.0378(4) Uani 1 1 d . . .
C3 C 0.51081(18) 0.67118(12) 0.73955(11) 0.0377(4) Uani 1 1 d . . .
H3 H 0.5794 0.6357 0.7660 0.045 Uiso 1 1 calc R . .
C4 C 0.46763(17) 0.62745(12) 0.66908(10) 0.0352(4) Uani 1 1 d . . .
H4 H 0.5053 0.5610 0.6491 0.042 Uiso 1 1 calc R . .
C5 C 0.37107(16) 0.67815(11) 0.62706(10) 0.0315(3) Uani 1 1 d . . .
C6 C 0.31897(18) 0.77579(12) 0.65741(12) 0.0394(4) Uani 1 1 d . . .
H6 H 0.2556 0.8133 0.6283 0.047 Uiso 1 1 calc R . .
C7 C 0.35797(19) 0.81884(12) 0.72915(12) 0.0427(4) Uani 1 1 d . . .
H7 H 0.3191 0.8848 0.7501 0.051 Uiso 1 1 calc R . .
C8 C 0.32077(16) 0.62787(11) 0.55519(10) 0.0325(3) Uani 1 1 d . . .
C9 C 0.31471(17) 0.67676(12) 0.47241(10) 0.0346(3) Uani 1 1 d . . .
H9 H 0.3456 0.7440 0.4607 0.042 Uiso 1 1 calc R . .
C10 C 0.26408(16) 0.62838(11) 0.40711(10) 0.0322(3) Uani 1 1 d . . .
C11 C 0.21583(16) 0.53097(11) 0.42895(10) 0.0312(3) Uani 1 1 d . . .
C12 C 0.23264(16) 0.48682(11) 0.51236(10) 0.0310(3) Uani 1 1 d . . .
C13 C 0.14647(17) 0.36768(12) 0.44203(10) 0.0337(3) Uani 1 1 d . . .
C14 C 0.09828(18) 0.27753(13) 0.41867(11) 0.0412(4) Uani 1 1 d . . .
H14 H 0.0918 0.2194 0.4577 0.049 Uiso 1 1 calc R . .
C15 C 0.06021(19) 0.27573(14) 0.33649(12) 0.0457(4) Uani 1 1 d . . .
H15 H 0.0285 0.2148 0.3183 0.055 Uiso 1 1 calc R . .
C16 C 0.06723(18) 0.36131(14) 0.27949(11) 0.0441(4) Uani 1 1 d . . .
H16 H 0.0383 0.3580 0.2241 0.053 Uiso 1 1 calc R . .
C17 C 0.11554(17) 0.45041(13) 0.30256(10) 0.0386(4) Uani 1 1 d . . .
H17 H 0.1200 0.5084 0.2635 0.046 Uiso 1 1 calc R . .
C18 C 0.15803(16) 0.45432(12) 0.38432(10) 0.0326(3) Uani 1 1 d . . .
C19 C 0.27133(17) 0.67287(11) 0.31378(10) 0.0319(3) Uani 1 1 d . . .
C20 C 0.3983(2) 0.65569(15) 0.24146(12) 0.0518(5) Uani 1 1 d . . .
H20 H 0.4811 0.6193 0.2528 0.062 Uiso 1 1 calc R . .
C21 C 0.4065(2) 0.69088(16) 0.15253(12) 0.0555(5) Uani 1 1 d . . .
H21 H 0.4944 0.6783 0.1034 0.067 Uiso 1 1 calc R . .
C22 C 0.28820(19) 0.74376(12) 0.13546(11) 0.0394(4) Uani 1 1 d . . .
H22 H 0.2934 0.7678 0.0745 0.047 Uiso 1 1 calc R . .
C23 C 0.16211(19) 0.76175(14) 0.20696(12) 0.0463(4) Uani 1 1 d . . .
H23 H 0.0798 0.7984 0.1953 0.056 Uiso 1 1 calc R . .
C24 C 0.15345(18) 0.72702(14) 0.29603(11) 0.0438(4) Uani 1 1 d . . .
H24 H 0.0658 0.7406 0.3451 0.053 Uiso 1 1 calc R . .
C25 C 0.3823(2) -0.05292(16) 0.29602(12) 0.0594(5) Uani 1 1 d . . .
H25A H 0.3763 -0.1025 0.2499 0.089 Uiso 1 1 calc R . .
H25B H 0.4783 -0.0623 0.3085 0.089 Uiso 1 1 calc R . .
H25C H 0.3710 0.0157 0.2720 0.089 Uiso 1 1 calc R . .
C26 C 0.26351(18) -0.00644(12) 0.45353(11) 0.0369(4) Uani 1 1 d . . .
C27 C 0.35535(19) 0.07132(13) 0.44985(11) 0.0429(4) Uani 1 1 d . . .
H27 H 0.4286 0.0857 0.3937 0.051 Uiso 1 1 calc R . .
C28 C 0.34009(18) 0.12854(13) 0.52883(11) 0.0406(4) Uani 1 1 d . . .
H28 H 0.4028 0.1826 0.5257 0.049 Uiso 1 1 calc R . .
C29 C 0.23558(17) 0.10865(11) 0.61221(10) 0.0322(3) Uani 1 1 d . . .
C30 C 0.14355(18) 0.02975(12) 0.61416(11) 0.0372(4) Uani 1 1 d . . .
H30 H 0.0709 0.0146 0.6704 0.045 Uiso 1 1 calc R . .
C31 C 0.15640(19) -0.02661(12) 0.53567(11) 0.0398(4) Uani 1 1 d . . .
H31 H 0.0917 -0.0793 0.5379 0.048 Uiso 1 1 calc R . .
C32 C 0.22199(16) 0.17063(11) 0.69556(10) 0.0313(3) Uani 1 1 d . . .
C33 C 0.20636(17) 0.12661(12) 0.78310(10) 0.0334(3) Uani 1 1 d . . .
H33 H 0.2035 0.0551 0.7894 0.040 Uiso 1 1 calc R . .
C34 C 0.19481(16) 0.18471(11) 0.86152(10) 0.0317(3) Uani 1 1 d . . .
C35 C 0.19876(16) 0.28958(11) 0.84877(10) 0.0306(3) Uani 1 1 d . . .
C36 C 0.21445(16) 0.32660(11) 0.75683(10) 0.0306(3) Uani 1 1 d . . .
C37 C 0.20730(17) 0.46243(11) 0.84424(10) 0.0320(3) Uani 1 1 d . . .
C38 C 0.20838(18) 0.56083(12) 0.87420(11) 0.0373(4) Uani 1 1 d . . .
H38 H 0.2127 0.6169 0.8330 0.045 Uiso 1 1 calc R . .
C39 C 0.2029(2) 0.57416(13) 0.96606(11) 0.0445(4) Uani 1 1 d . . .
H39 H 0.2041 0.6406 0.9884 0.053 Uiso 1 1 calc R . .
C40 C 0.1957(2) 0.49193(14) 1.02669(11) 0.0467(4) Uani 1 1 d . . .
H40 H 0.1935 0.5034 1.0894 0.056 Uiso 1 1 calc R . .
C41 C 0.19164(18) 0.39441(13) 0.99755(10) 0.0396(4) Uani 1 1 d . . .
H41 H 0.1854 0.3391 1.0398 0.047 Uiso 1 1 calc R . .
C42 C 0.19683(16) 0.37796(11) 0.90458(10) 0.0319(3) Uani 1 1 d . . .
C43 C 0.18012(17) 0.13358(11) 0.95272(10) 0.0339(3) Uani 1 1 d . . .
C44 C 0.06576(19) 0.16148(13) 1.03109(11) 0.0439(4) Uani 1 1 d . . .
H44 H -0.0034 0.2151 1.0269 0.053 Uiso 1 1 calc R . .
C45 C 0.0519(2) 0.11175(15) 1.11511(12) 0.0534(5) Uani 1 1 d . . .
H45 H -0.0271 0.1311 1.1681 0.064 Uiso 1 1 calc R . .
C46 C 0.1523(2) 0.03437(15) 1.12197(13) 0.0569(5) Uani 1 1 d . . .
H46 H 0.1431 0.0007 1.1798 0.068 Uiso 1 1 calc R . .
C47 C 0.2657(2) 0.00590(14) 1.04505(13) 0.0540(5) Uani 1 1 d . . .
H47 H 0.3351 -0.0473 1.0500 0.065 Uiso 1 1 calc R . .
C48 C 0.27950(19) 0.05425(12) 0.96047(12) 0.0419(4) Uani 1 1 d . . .
H48 H 0.3572 0.0332 0.9074 0.050 Uiso 1 1 calc R . .
N1 N 0.28307(14) 0.53133(9) 0.57502(8) 0.0321(3) Uani 1 1 d . . .
N2 N 0.19134(15) 0.38903(10) 0.51929(8) 0.0354(3) Uani 1 1 d . . .
H2 H 0.1930 0.3468 0.5652 0.042 Uiso 1 1 calc R . .
N3 N 0.22654(14) 0.27148(9) 0.68132(8) 0.0318(3) Uani 1 1 d . . .
N4 N 0.21704(14) 0.42952(9) 0.75540(8) 0.0335(3) Uani 1 1 d . . .
H4A H 0.2238 0.4686 0.7063 0.040 Uiso 1 1 calc R . .
O1 O 0.48387(14) 0.81572(10) 0.84233(9) 0.0532(3) Uani 1 1 d . . .
O2 O 0.26802(14) -0.06698(9) 0.37978(8) 0.0501(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.426(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O1 1.3730(19) . ?
C2 C3 1.380(2) . ?
C2 C7 1.387(2) . ?
C3 C4 1.388(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(2) . ?
C5 C8 1.483(2) . ?
C6 C7 1.379(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 N1 1.3509(19) . ?
C8 C9 1.402(2) . ?
C9 C10 1.392(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.394(2) . ?
C10 C19 1.4917(19) . ?
C11 C12 1.4152(19) . ?
C11 C18 1.445(2) . ?
C12 N1 1.3332(19) . ?
C12 N2 1.368(2) . ?
C13 N2 1.3848(19) . ?
C13 C14 1.390(2) . ?
C13 C18 1.411(2) . ?
C14 C15 1.382(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.397(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.377(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.400(2) . ?
C17 H17 0.9500 . ?
C19 C24 1.377(2) . ?
C19 C20 1.381(2) . ?
C20 C21 1.386(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.369(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.371(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.385(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 O2 1.422(2) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 O2 1.3702(19) . ?
C26 C27 1.378(2) . ?
C26 C31 1.386(2) . ?
C27 C28 1.389(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.387(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.395(2) . ?
C29 C32 1.482(2) . ?
C30 C31 1.380(2) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 N3 1.3477(19) . ?
C32 C33 1.397(2) . ?
C33 C34 1.395(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.397(2) . ?
C34 C43 1.487(2) . ?
C35 C36 1.423(2) . ?
C35 C42 1.450(2) . ?
C36 N3 1.3350(19) . ?
C36 N4 1.3629(19) . ?
C37 N4 1.3880(18) . ?
C37 C38 1.389(2) . ?
C37 C42 1.412(2) . ?
C38 C39 1.380(2) . ?
C38 H38 0.9500 . ?
C39 C40 1.394(2) . ?
C39 H39 0.9500 . ?
C40 C41 1.378(2) . ?
C40 H40 0.9500 . ?
C41 C42 1.404(2) . ?
C41 H41 0.9500 . ?
C43 C44 1.391(2) . ?
C43 C48 1.392(2) . ?
C44 C45 1.385(2) . ?
C44 H44 0.9500 . ?
C45 C46 1.377(3) . ?
C45 H45 0.9500 . ?
C46 C47 1.375(3) . ?
C46 H46 0.9500 . ?
C47 C48 1.384(2) . ?
C47 H47 0.9500 . ?
C48 H48 0.9500 . ?
N2 H2 0.8800 . ?
N4 H4A 0.8800 . ?

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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 124.78(15) . . ?
O1 C2 C7 115.78(14) . . ?
C3 C2 C7 119.44(15) . . ?
C2 C3 C4 119.60(15) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 121.77(14) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 117.67(14) . . ?
C4 C5 C8 120.72(13) . . ?
C6 C5 C8 121.56(13) . . ?
C7 C6 C5 121.00(15) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C2 120.45(15) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
N1 C8 C9 122.66(14) . . ?
N1 C8 C5 115.03(12) . . ?
C9 C8 C5 122.30(14) . . ?
C10 C9 C8 121.01(14) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 117.20(13) . . ?
C9 C10 C19 122.77(14) . . ?
C11 C10 C19 119.84(14) . . ?
C10 C11 C12 117.24(14) . . ?
C10 C11 C18 136.38(13) . . ?
C12 C11 C18 106.21(13) . . ?
N1 C12 N2 124.06(13) . . ?
N1 C12 C11 126.28(14) . . ?
N2 C12 C11 109.65(13) . . ?
N2 C13 C14 128.78(14) . . ?
N2 C13 C18 109.31(13) . . ?
C14 C13 C18 121.91(14) . . ?
C15 C14 C13 117.42(16) . . ?
C15 C14 H14 121.3 . . ?
C13 C14 H14 121.3 . . ?
C14 C15 C16 121.63(16) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C17 C16 C15 120.85(15) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 119.05(15) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C17 C18 C13 119.10(15) . . ?
C17 C18 C11 134.65(15) . . ?
C13 C18 C11 106.25(12) . . ?
C24 C19 C20 118.64(14) . . ?
C24 C19 C10 122.29(14) . . ?
C20 C19 C10 119.02(13) . . ?
C19 C20 C21 120.79(16) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C22 C21 C20 120.09(16) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 119.49(15) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C22 C23 C24 120.67(15) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C19 C24 C23 120.31(15) . . ?
C19 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
O2 C25 H25A 109.5 . . ?
O2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O2 C26 C27 124.43(15) . . ?
O2 C26 C31 115.69(14) . . ?
C27 C26 C31 119.88(15) . . ?
C26 C27 C28 119.55(15) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
C29 C28 C27 121.62(15) . . ?
C29 C28 H28 119.2 . . ?
C27 C28 H28 119.2 . . ?
C28 C29 C30 117.78(14) . . ?
C28 C29 C32 120.53(14) . . ?
C30 C29 C32 121.68(14) . . ?
C31 C30 C29 121.03(15) . . ?
C31 C30 H30 119.5 . . ?
C29 C30 H30 119.5 . . ?
C30 C31 C26 120.12(15) . . ?
C30 C31 H31 119.9 . . ?
C26 C31 H31 119.9 . . ?
N3 C32 C33 122.42(14) . . ?
N3 C32 C29 115.85(12) . . ?
C33 C32 C29 121.73(13) . . ?
C34 C33 C32 121.85(14) . . ?
C34 C33 H33 119.1 . . ?
C32 C33 H33 119.1 . . ?
C33 C34 C35 116.92(13) . . ?
C33 C34 C43 119.47(13) . . ?
C35 C34 C43 123.62(14) . . ?
C34 C35 C36 116.70(13) . . ?
C34 C35 C42 137.50(13) . . ?
C36 C35 C42 105.75(13) . . ?
N3 C36 N4 123.38(13) . . ?
N3 C36 C35 126.75(13) . . ?
N4 C36 C35 109.87(13) . . ?
N4 C37 C38 128.30(14) . . ?
N4 C37 C42 109.26(13) . . ?
C38 C37 C42 122.44(14) . . ?
C39 C38 C37 117.52(15) . . ?
C39 C38 H38 121.2 . . ?
C37 C38 H38 121.2 . . ?
C38 C39 C40 121.23(16) . . ?
C38 C39 H39 119.4 . . ?
C40 C39 H39 119.4 . . ?
C41 C40 C39 121.32(15) . . ?
C41 C40 H40 119.3 . . ?
C39 C40 H40 119.3 . . ?
C40 C41 C42 119.03(15) . . ?
C40 C41 H41 120.5 . . ?
C42 C41 H41 120.5 . . ?
C41 C42 C37 118.42(14) . . ?
C41 C42 C35 135.15(14) . . ?
C37 C42 C35 106.40(12) . . ?
C44 C43 C48 118.58(14) . . ?
C44 C43 C34 121.30(14) . . ?
C48 C43 C34 120.10(14) . . ?
C45 C44 C43 120.61(16) . . ?
C45 C44 H44 119.7 . . ?
C43 C44 H44 119.7 . . ?
C46 C45 C44 120.11(17) . . ?
C46 C45 H45 119.9 . . ?
C44 C45 H45 119.9 . . ?
C47 C46 C45 119.90(16) . . ?
C47 C46 H46 120.0 . . ?
C45 C46 H46 120.0 . . ?
C46 C47 C48 120.44(17) . . ?
C46 C47 H47 119.8 . . ?
C48 C47 H47 119.8 . . ?
C47 C48 C43 120.34(17) . . ?
C47 C48 H48 119.8 . . ?
C43 C48 H48 119.8 . . ?
C12 N1 C8 115.40(12) . . ?
C12 N2 C13 108.57(12) . . ?
C12 N2 H2 125.7 . . ?
C13 N2 H2 125.7 . . ?
C36 N3 C32 115.36(12) . . ?
C36 N4 C37 108.69(12) . . ?
C36 N4 H4A 125.7 . . ?
C37 N4 H4A 125.7 . . ?
C2 O1 C1 116.94(14) . . ?
C26 O2 C25 117.35(14) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.035
####################################################################### 
# 
# 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_ch18179
_audit_block_doi                 10.5517/ccdc.csd.cc1mw7xn
_database_code_depnum_ccdc_archive 'CCDC 1515742'
_audit_update_record             
;
2017-01-06 deposited with the CCDC.
2017-01-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H20 N2 O2'
_chemical_formula_sum            'C25 H20 N2 O2'
_chemical_formula_weight         380.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   8.2571(7)
_cell_length_b                   16.8590(15)
_cell_length_c                   17.1654(15)
_cell_angle_alpha                66.416(5)
_cell_angle_beta                 86.395(5)
_cell_angle_gamma                89.790(5)
_cell_volume                     2185.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    6484
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      25.31

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9717
_exptl_absorpt_correction_T_max  0.9919
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'Bruker APEX2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19218
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_sigmaI/netI    0.0728
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.32
_diffrn_reflns_theta_max         25.46
_reflns_number_total             7965
_reflns_number_gt                5294
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.1650P)²+1.4896P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7965
_refine_ls_number_parameters     523
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1235
_refine_ls_R_factor_gt           0.0921
_refine_ls_wR_factor_ref         0.2855
_refine_ls_wR_factor_gt          0.2654
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1795(5) 0.4657(2) 1.0724(2) 0.0327(8) Uani 1 1 d . . .
C2 C 0.2780(6) 0.5326(3) 1.0850(3) 0.0472(11) Uani 1 1 d . . .
H2A H 0.3545 0.5605 1.0353 0.071 Uiso 1 1 calc R . .
H2B H 0.3383 0.5054 1.1361 0.071 Uiso 1 1 calc R . .
H2C H 0.2062 0.5762 1.0918 0.071 Uiso 1 1 calc R . .
C3 C 0.1691(4) 0.4150(2) 0.8988(2) 0.0299(8) Uani 1 1 d . . .
C4 C 0.0885(4) 0.3545(2) 0.8696(2) 0.0300(8) Uani 1 1 d . . .
C5 C 0.0794(5) 0.2661(3) 0.9194(3) 0.0410(10) Uani 1 1 d . . .
H5 H 0.1266 0.2438 0.9729 0.049 Uiso 1 1 calc R . .
C6 C 0.0021(6) 0.2104(3) 0.8918(3) 0.0493(11) Uani 1 1 d . . .
H6 H -0.0024 0.1500 0.9260 0.059 Uiso 1 1 calc R . .
C7 C -0.0680(6) 0.2420(3) 0.8153(3) 0.0521(12) Uani 1 1 d . . .
H7 H -0.1199 0.2036 0.7960 0.063 Uiso 1 1 calc R . .
C8 C -0.0628(6) 0.3297(3) 0.7664(3) 0.0496(11) Uani 1 1 d . . .
H8 H -0.1144 0.3518 0.7143 0.060 Uiso 1 1 calc R . .
C9 C 0.0164(5) 0.3860(3) 0.7923(3) 0.0419(10) Uani 1 1 d . . .
H9 H 0.0217 0.4462 0.7573 0.050 Uiso 1 1 calc R . .
C10 C 0.2686(5) 0.4895(2) 0.8375(2) 0.0318(8) Uani 1 1 d . . .
H10 H 0.2524 0.5445 0.8395 0.038 Uiso 1 1 calc R . .
C11 C 0.3801(4) 0.4842(2) 0.7793(2) 0.0262(8) Uani 1 1 d . . .
C12 C 0.4569(5) 0.5640(2) 0.7130(2) 0.0322(8) Uani 1 1 d . . .
C13 C 0.3716(5) 0.6401(2) 0.6809(3) 0.0397(10) Uani 1 1 d . . .
H13 H 0.2621 0.6412 0.7010 0.048 Uiso 1 1 calc R . .
C14 C 0.4457(6) 0.7156(3) 0.6189(3) 0.0522(12) Uani 1 1 d . . .
H14 H 0.3861 0.7673 0.5966 0.063 Uiso 1 1 calc R . .
C15 C 0.6034(6) 0.7146(3) 0.5905(3) 0.0515(12) Uani 1 1 d . . .
H15 H 0.6539 0.7662 0.5494 0.062 Uiso 1 1 calc R . .
C16 C 0.6905(6) 0.6394(3) 0.6210(3) 0.0458(11) Uani 1 1 d . . .
H16 H 0.7995 0.6389 0.5999 0.055 Uiso 1 1 calc R . .
C17 C 0.6186(5) 0.5651(3) 0.6820(2) 0.0360(9) Uani 1 1 d . . .
H17 H 0.6794 0.5137 0.7034 0.043 Uiso 1 1 calc R . .
C18 C 0.4357(4) 0.3999(2) 0.7823(2) 0.0273(8) Uani 1 1 d . . .
C19 C 0.4635(4) 0.3291(2) 0.8548(2) 0.0298(8) Uani 1 1 d . . .
H19 H 0.4523 0.3278 0.9107 0.036 Uiso 1 1 calc R . .
C20 C 0.5115(4) 0.2859(2) 0.7489(2) 0.0294(8) Uani 1 1 d . . .
C21 C 0.5528(5) 0.2400(2) 0.6995(3) 0.0358(9) Uani 1 1 d . . .
H21 H 0.5864 0.1817 0.7245 0.043 Uiso 1 1 calc R . .
C22 C 0.5430(5) 0.2817(3) 0.6138(3) 0.0433(10) Uani 1 1 d . . .
H22 H 0.5711 0.2517 0.5785 0.052 Uiso 1 1 calc R . .
C23 C 0.4929(6) 0.3678(3) 0.5757(3) 0.0447(10) Uani 1 1 d . . .
H23 H 0.4846 0.3943 0.5158 0.054 Uiso 1 1 calc R . .
C24 C 0.4557(5) 0.4140(2) 0.6251(2) 0.0380(9) Uani 1 1 d . . .
H24 H 0.4235 0.4725 0.5993 0.046 Uiso 1 1 calc R . .
C25 C 0.4657(4) 0.3738(2) 0.7134(2) 0.0286(8) Uani 1 1 d . . .
C26 C 0.3098(5) 0.9662(2) 1.0678(2) 0.0301(8) Uani 1 1 d . . .
C27 C 0.2148(6) 1.0343(3) 1.0814(3) 0.0447(10) Uani 1 1 d . . .
H27A H 0.1448 1.0612 1.0341 0.067 Uiso 1 1 calc R . .
H27B H 0.2888 1.0784 1.0841 0.067 Uiso 1 1 calc R . .
H27C H 0.1477 1.0087 1.1350 0.067 Uiso 1 1 calc R . .
C28 C 0.3510(4) 0.9126(2) 0.8961(2) 0.0290(8) Uani 1 1 d . . .
C29 C 0.4378(4) 0.8509(2) 0.8664(2) 0.0307(8) Uani 1 1 d . . .
C30 C 0.4352(5) 0.7634(3) 0.9158(3) 0.0398(10) Uani 1 1 d . . .
H30 H 0.3769 0.7412 0.9699 0.048 Uiso 1 1 calc R . .
C31 C 0.5175(6) 0.7073(3) 0.8869(3) 0.0544(12) Uani 1 1 d . . .
H31 H 0.5133 0.6468 0.9206 0.065 Uiso 1 1 calc R . .
C32 C 0.6051(6) 0.7394(3) 0.8094(3) 0.0516(12) Uani 1 1 d . . .
H32 H 0.6614 0.7010 0.7897 0.062 Uiso 1 1 calc R . .
C33 C 0.6111(6) 0.8258(3) 0.7609(3) 0.0527(12) Uani 1 1 d . . .
H33 H 0.6736 0.8481 0.7079 0.063 Uiso 1 1 calc R . .
C34 C 0.5259(5) 0.8814(3) 0.7888(3) 0.0420(10) Uani 1 1 d . . .
H34 H 0.5282 0.9417 0.7539 0.050 Uiso 1 1 calc R . .
C35 C 0.2626(5) 0.9852(2) 0.8375(2) 0.0307(8) Uani 1 1 d . . .
H35 H 0.2781 1.0400 0.8398 0.037 Uiso 1 1 calc R . .
C36 C 0.1612(4) 0.9812(2) 0.7806(2) 0.0265(8) Uani 1 1 d . . .
C37 C 0.0932(4) 1.0617(2) 0.7184(2) 0.0284(8) Uani 1 1 d . . .
C38 C 0.1810(5) 1.1397(3) 0.6867(3) 0.0423(10) Uani 1 1 d . . .
H38 H 0.2880 1.1412 0.7034 0.051 Uiso 1 1 calc R . .
C39 C 0.1154(6) 1.2146(3) 0.6316(3) 0.0482(11) Uani 1 1 d . . .
H39 H 0.1773 1.2672 0.6103 0.058 Uiso 1 1 calc R . .
C40 C -0.0411(6) 1.2135(3) 0.6071(3) 0.0504(12) Uani 1 1 d . . .
H40 H -0.0878 1.2655 0.5702 0.061 Uiso 1 1 calc R . .
C41 C -0.1273(6) 1.1374(3) 0.6362(3) 0.0433(10) Uani 1 1 d . . .
H41 H -0.2332 1.1366 0.6179 0.052 Uiso 1 1 calc R . .
C42 C -0.0637(5) 1.0609(2) 0.6920(2) 0.0355(9) Uani 1 1 d . . .
H42 H -0.1260 1.0084 0.7122 0.043 Uiso 1 1 calc R . .
C43 C 0.1069(4) 0.8981(2) 0.7809(2) 0.0268(8) Uani 1 1 d . . .
C44 C 0.0677(4) 0.8242(2) 0.8525(2) 0.0295(8) Uani 1 1 d . . .
H44 H 0.0706 0.8198 0.9093 0.035 Uiso 1 1 calc R . .
C45 C 0.0335(4) 0.7888(2) 0.7435(2) 0.0303(8) Uani 1 1 d . . .
C46 C -0.0021(5) 0.7462(3) 0.6914(3) 0.0364(9) Uani 1 1 d . . .
H46 H -0.0364 0.6871 0.7148 0.044 Uiso 1 1 calc R . .
C47 C 0.0147(6) 0.7935(3) 0.6049(3) 0.0448(10) Uani 1 1 d . . .
H47 H -0.0087 0.7662 0.5679 0.054 Uiso 1 1 calc R . .
C48 C 0.0654(5) 0.8806(3) 0.5696(3) 0.0421(10) Uani 1 1 d . . .
H48 H 0.0741 0.9115 0.5094 0.050 Uiso 1 1 calc R . .
C49 C 0.1027(5) 0.9221(3) 0.6211(2) 0.0353(9) Uani 1 1 d . . .
H49 H 0.1402 0.9807 0.5970 0.042 Uiso 1 1 calc R . .
C50 C 0.0842(4) 0.8762(2) 0.7099(2) 0.0275(8) Uani 1 1 d . . .
N1 N 0.5095(4) 0.26052(19) 0.83590(19) 0.0315(7) Uani 1 1 d . . .
H1' H 0.5436 0.2072 0.8751 0.038 Uiso 1 1 d R . .
N2 N 0.1358(4) 0.4013(2) 0.9772(2) 0.0339(7) Uani 1 1 d . . .
N3 N 0.3696(4) 0.89771(19) 0.97486(19) 0.0324(7) Uani 1 1 d . . .
N4 N 0.0246(4) 0.75901(19) 0.83088(19) 0.0327(7) Uani 1 1 d . . .
H4' H 0.0028 0.7030 0.8669 0.039 Uiso 1 1 d R . .
O1 O 0.2260(3) 0.46434(16) 0.99568(16) 0.0356(6) Uani 1 1 d . . .
O2 O 0.0760(4) 0.41984(17) 1.12137(17) 0.0433(7) Uani 1 1 d . . .
O3 O 0.2735(3) 0.96125(16) 0.99456(15) 0.0343(6) Uani 1 1 d . . .
O4 O 0.4066(4) 0.92103(18) 1.11466(17) 0.0453(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.196(4) . ?
C1 O1 1.358(5) . ?
C1 C2 1.485(6) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 N2 1.283(5) . ?
C3 C4 1.480(5) . ?
C3 C10 1.483(5) . ?
C4 C5 1.389(5) . ?
C4 C9 1.390(5) . ?
C5 C6 1.384(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.371(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.377(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.379(6) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.344(5) . ?
C10 H10 0.9500 . ?
C11 C18 1.475(5) . ?
C11 C12 1.482(5) . ?
C12 C13 1.387(5) . ?
C12 C17 1.403(6) . ?
C13 C14 1.402(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.364(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.377(5) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.367(5) . ?
C18 C25 1.427(5) . ?
C19 N1 1.368(5) . ?
C19 H19 0.9500 . ?
C20 N1 1.378(5) . ?
C20 C21 1.386(5) . ?
C20 C25 1.418(5) . ?
C21 C22 1.361(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.405(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.384(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.399(5) . ?
C24 H24 0.9500 . ?
C26 O4 1.205(4) . ?
C26 O3 1.345(4) . ?
C26 C27 1.475(6) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 N3 1.291(4) . ?
C28 C35 1.465(5) . ?
C28 C29 1.493(5) . ?
C29 C30 1.375(5) . ?
C29 C34 1.379(6) . ?
C30 C31 1.390(6) . ?
C30 H30 0.9500 . ?
C31 C32 1.375(7) . ?
C31 H31 0.9500 . ?
C32 C33 1.358(7) . ?
C32 H32 0.9500 . ?
C33 C34 1.384(6) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 C36 1.347(5) . ?
C35 H35 0.9500 . ?
C36 C43 1.472(5) . ?
C36 C37 1.486(5) . ?
C37 C38 1.392(5) . ?
C37 C42 1.400(5) . ?
C38 C39 1.373(6) . ?
C38 H38 0.9500 . ?
C39 C40 1.386(7) . ?
C39 H39 0.9500 . ?
C40 C41 1.361(7) . ?
C40 H40 0.9500 . ?
C41 C42 1.388(5) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C43 C44 1.376(5) . ?
C43 C50 1.430(5) . ?
C44 N4 1.349(5) . ?
C44 H44 0.9500 . ?
C45 N4 1.375(5) . ?
C45 C46 1.397(5) . ?
C45 C50 1.405(5) . ?
C46 C47 1.374(6) . ?
C46 H46 0.9500 . ?
C47 C48 1.400(6) . ?
C47 H47 0.9500 . ?
C48 C49 1.378(6) . ?
C48 H48 0.9500 . ?
C49 C50 1.404(5) . ?
C49 H49 0.9500 . ?
N1 H1' 0.9373 . ?
N2 O1 1.446(4) . ?
N3 O3 1.463(4) . ?
N4 H4' 0.9090 . ?

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
O2 C1 O1 124.8(4) . . ?
O2 C1 C2 126.2(4) . . ?
O1 C1 C2 109.0(3) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 C4 115.1(3) . . ?
N2 C3 C10 124.3(3) . . ?
C4 C3 C10 120.4(3) . . ?
C5 C4 C9 118.9(4) . . ?
C5 C4 C3 121.0(3) . . ?
C9 C4 C3 120.0(3) . . ?
C6 C5 C4 120.5(4) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 120.2(4) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 119.6(4) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C9 120.9(4) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C4 119.9(4) . . ?
C8 C9 H9 120.1 . . ?
C4 C9 H9 120.1 . . ?
C11 C10 C3 124.3(3) . . ?
C11 C10 H10 117.9 . . ?
C3 C10 H10 117.9 . . ?
C10 C11 C18 121.4(3) . . ?
C10 C11 C12 120.3(3) . . ?
C18 C11 C12 118.3(3) . . ?
C13 C12 C17 118.1(3) . . ?
C13 C12 C11 120.8(4) . . ?
C17 C12 C11 121.0(3) . . ?
C12 C13 C14 120.5(4) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 119.9(4) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.7(4) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 119.7(4) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C12 121.1(4) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
C19 C18 C25 106.2(3) . . ?
C19 C18 C11 125.3(3) . . ?
C25 C18 C11 128.4(3) . . ?
C18 C19 N1 110.8(3) . . ?
C18 C19 H19 124.6 . . ?
N1 C19 H19 124.6 . . ?
N1 C20 C21 129.9(3) . . ?
N1 C20 C25 107.4(3) . . ?
C21 C20 C25 122.7(3) . . ?
C22 C21 C20 117.3(4) . . ?
C22 C21 H21 121.3 . . ?
C20 C21 H21 121.3 . . ?
C21 C22 C23 122.2(4) . . ?
C21 C22 H22 118.9 . . ?
C23 C22 H22 118.9 . . ?
C24 C23 C22 120.2(4) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 119.4(4) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C24 C25 C20 118.1(3) . . ?
C24 C25 C18 134.7(3) . . ?
C20 C25 C18 107.2(3) . . ?
O4 C26 O3 124.1(4) . . ?
O4 C26 C27 125.7(4) . . ?
O3 C26 C27 110.1(3) . . ?
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 . . ?
N3 C28 C35 125.1(3) . . ?
N3 C28 C29 113.7(3) . . ?
C35 C28 C29 121.1(3) . . ?
C30 C29 C34 118.6(4) . . ?
C30 C29 C28 121.4(3) . . ?
C34 C29 C28 120.0(3) . . ?
C29 C30 C31 120.4(4) . . ?
C29 C30 H30 119.8 . . ?
C31 C30 H30 119.8 . . ?
C32 C31 C30 120.0(4) . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C33 C32 C31 120.2(4) . . ?
C33 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
C32 C33 C34 119.8(4) . . ?
C32 C33 H33 120.1 . . ?
C34 C33 H33 120.1 . . ?
C29 C34 C33 121.1(4) . . ?
C29 C34 H34 119.4 . . ?
C33 C34 H34 119.4 . . ?
C36 C35 C28 125.8(3) . . ?
C36 C35 H35 117.1 . . ?
C28 C35 H35 117.1 . . ?
C35 C36 C43 121.8(3) . . ?
C35 C36 C37 120.2(3) . . ?
C43 C36 C37 117.9(3) . . ?
C38 C37 C42 118.5(3) . . ?
C38 C37 C36 121.2(3) . . ?
C42 C37 C36 120.3(3) . . ?
C39 C38 C37 121.1(4) . . ?
C39 C38 H38 119.5 . . ?
C37 C38 H38 119.5 . . ?
C38 C39 C40 120.0(4) . . ?
C38 C39 H39 120.0 . . ?
C40 C39 H39 120.0 . . ?
C41 C40 C39 119.6(4) . . ?
C41 C40 H40 120.2 . . ?
C39 C40 H40 120.2 . . ?
C40 C41 C42 121.4(4) . . ?
C40 C41 H41 119.3 . . ?
C42 C41 H41 119.3 . . ?
C41 C42 C37 119.4(4) . . ?
C41 C42 H42 120.3 . . ?
C37 C42 H42 120.3 . . ?
C44 C43 C50 106.0(3) . . ?
C44 C43 C36 125.4(3) . . ?
C50 C43 C36 128.7(3) . . ?
N4 C44 C43 110.7(3) . . ?
N4 C44 H44 124.7 . . ?
C43 C44 H44 124.7 . . ?
N4 C45 C46 129.9(3) . . ?
N4 C45 C50 108.0(3) . . ?
C46 C45 C50 122.1(3) . . ?
C47 C46 C45 117.1(4) . . ?
C47 C46 H46 121.4 . . ?
C45 C46 H46 121.4 . . ?
C46 C47 C48 122.0(4) . . ?
C46 C47 H47 119.0 . . ?
C48 C47 H47 119.0 . . ?
C49 C48 C47 120.7(4) . . ?
C49 C48 H48 119.7 . . ?
C47 C48 H48 119.7 . . ?
C48 C49 C50 118.8(4) . . ?
C48 C49 H49 120.6 . . ?
C50 C49 H49 120.6 . . ?
C49 C50 C45 119.2(3) . . ?
C49 C50 C43 134.1(3) . . ?
C45 C50 C43 106.7(3) . . ?
C19 N1 C20 108.4(3) . . ?
C19 N1 H1' 125.4 . . ?
C20 N1 H1' 126.0 . . ?
C3 N2 O1 108.1(3) . . ?
C28 N3 O3 106.9(3) . . ?
C44 N4 C45 108.7(3) . . ?
C44 N4 H4' 126.7 . . ?
C45 N4 H4' 124.3 . . ?
C1 O1 N2 113.2(3) . . ?
C26 O3 N3 113.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.46
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.086

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.000 0.500 0.500 130.9 31.0
2 0.500 0.000 0.500 121.3 28.7
_platon_squeeze_details          
;
;
