# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

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

data_dzw
_database_code_depnum_ccdc_archive 'CCDC 1032969'
_audit_update_record             
;
2014-11-06 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 N2 O2'
_chemical_formula_weight         278.30

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   5.834(16)
_cell_length_b                   12.53(4)
_cell_length_c                   19.70(5)
_cell_angle_alpha                87.16(4)
_cell_angle_beta                 86.36(4)
_cell_angle_gamma                88.79(4)
_cell_volume                     1436(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9915
_exptl_absorpt_correction_T_max  0.9974
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7424
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         25.05
_reflns_number_total             4973
_reflns_number_gt                2892
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1710P)²+0.3553P] 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         4973
_refine_ls_number_parameters     369
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1325
_refine_ls_R_factor_gt           0.0873
_refine_ls_wR_factor_ref         0.3065
_refine_ls_wR_factor_gt          0.2588
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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 0.2790(7) 0.2505(3) 0.4135(2) 0.0620(10) Uani 1 1 d . . .
C2 C 0.4570(9) 0.1847(4) 0.3911(3) 0.0909(15) Uani 1 1 d . . .
H2 H 0.5908 0.1796 0.4144 0.109 Uiso 1 1 calc R . .
C3 C 0.4374(12) 0.1255(5) 0.3336(3) 0.1109(19) Uani 1 1 d . . .
H3 H 0.5576 0.0806 0.3190 0.133 Uiso 1 1 calc R . .
C4 C 0.2446(12) 0.1332(5) 0.2992(3) 0.0991(17) Uani 1 1 d . . .
H4 H 0.2332 0.0947 0.2604 0.119 Uiso 1 1 calc R . .
C5 C 0.0668(11) 0.1974(5) 0.3211(3) 0.1032(17) Uani 1 1 d . . .
H5 H -0.0658 0.2030 0.2973 0.124 Uiso 1 1 calc R . .
C6 C 0.0837(9) 0.2540(4) 0.3787(3) 0.0902(15) Uani 1 1 d . . .
H6 H -0.0408 0.2956 0.3942 0.108 Uiso 1 1 calc R . .
C7 C 0.3002(7) 0.3156(3) 0.47164(19) 0.0599(10) Uani 1 1 d . . .
C8 C 0.4562(6) 0.3177(3) 0.52106(19) 0.0571(10) Uani 1 1 d . . .
C9 C 0.3955(7) 0.3999(3) 0.56304(19) 0.0597(10) Uani 1 1 d . . .
C10 C 0.4997(7) 0.4398(3) 0.62261(19) 0.0605(10) Uani 1 1 d . . .
C11 C 0.3877(8) 0.5192(4) 0.6592(2) 0.0763(12) Uani 1 1 d . . .
H11 H 0.2455 0.5451 0.6463 0.092 Uiso 1 1 calc R . .
C12 C 0.4828(10) 0.5603(4) 0.7140(2) 0.0889(15) Uani 1 1 d . . .
H12 H 0.4049 0.6138 0.7376 0.107 Uiso 1 1 calc R . .
C13 C 0.6909(9) 0.5233(4) 0.7342(2) 0.0853(14) Uani 1 1 d . . .
H13 H 0.7549 0.5512 0.7714 0.102 Uiso 1 1 calc R . .
C14 C 0.8040(9) 0.4445(4) 0.6989(3) 0.0856(14) Uani 1 1 d . . .
H14 H 0.9456 0.4187 0.7122 0.103 Uiso 1 1 calc R . .
C15 C 0.7084(8) 0.4027(4) 0.6430(2) 0.0771(12) Uani 1 1 d . . .
H15 H 0.7868 0.3493 0.6195 0.092 Uiso 1 1 calc R . .
C16 C 0.6258(10) 0.1569(4) 0.5622(3) 0.0939(16) Uani 1 1 d . . .
C17 C 0.8455(10) 0.0938(5) 0.5602(3) 0.122(2) Uani 1 1 d . . .
H17A H 0.8318 0.0337 0.5922 0.183 Uiso 1 1 calc R . .
H17B H 0.9680 0.1381 0.5717 0.183 Uiso 1 1 calc R . .
H17C H 0.8782 0.0689 0.5152 0.183 Uiso 1 1 calc R . .
C18 C -0.0183(7) 1.0329(3) 0.85307(19) 0.0586(10) Uani 1 1 d . . .
C19 C 0.1974(8) 1.0269(4) 0.8214(2) 0.0818(13) Uani 1 1 d . . .
H19 H 0.3062 0.9796 0.8389 0.098 Uiso 1 1 calc R . .
C20 C 0.2553(10) 1.0912(5) 0.7633(3) 0.0950(16) Uani 1 1 d . . .
H20 H 0.4007 1.0845 0.7415 0.114 Uiso 1 1 calc R . .
C21 C 0.1006(10) 1.1638(5) 0.7380(3) 0.0942(15) Uani 1 1 d . . .
H21 H 0.1401 1.2076 0.6997 0.113 Uiso 1 1 calc R . .
C22 C -0.1093(11) 1.1706(5) 0.7696(3) 0.113(2) Uani 1 1 d . . .
H22 H -0.2160 1.2197 0.7529 0.135 Uiso 1 1 calc R . .
C23 C -0.1700(8) 1.1058(4) 0.8265(3) 0.0901(15) Uani 1 1 d . . .
H23 H -0.3172 1.1120 0.8471 0.108 Uiso 1 1 calc R . .
C24 C -0.0901(6) 0.9641(3) 0.91221(19) 0.0578(10) Uani 1 1 d . . .
C25 C 0.0085(6) 0.8718(3) 0.94229(19) 0.0588(10) Uani 1 1 d . . .
C26 C -0.1389(7) 0.8340(3) 0.99516(19) 0.0593(10) Uani 1 1 d . . .
C27 C -0.1318(6) 0.7391(3) 1.04154(16) 0.0688(11) Uani 1 1 d G . .
C28 C -0.3132(7) 0.7205(3) 1.0896(3) 0.187(5) Uani 1 1 d G . .
H28 H -0.4363 0.7688 1.0926 0.224 Uiso 1 1 calc R . .
C29 C -0.3106(9) 0.6298(4) 1.1331(3) 0.189(4) Uani 1 1 d G . .
H29 H -0.4320 0.6174 1.1652 0.226 Uiso 1 1 calc R . .
C30 C -0.1266(10) 0.5577(3) 1.1286(2) 0.119(2) Uani 1 1 d G . .
H30 H -0.1249 0.4970 1.1577 0.142 Uiso 1 1 calc R . .
C31 C 0.0548(9) 0.5763(4) 1.0805(3) 0.283(9) Uani 1 1 d G . .
H31 H 0.1779 0.5280 1.0775 0.339 Uiso 1 1 calc R . .
C32 C 0.0522(7) 0.6670(4) 1.0370(2) 0.275(8) Uani 1 1 d G . .
H32 H 0.1736 0.6794 1.0049 0.330 Uiso 1 1 calc R . .
C33 C 0.2533(7) 0.7579(3) 0.8788(2) 0.0657(11) Uani 1 1 d . . .
C34 C 0.4964(8) 0.7201(5) 0.8718(3) 0.0980(17) Uani 1 1 d . . .
H34A H 0.5121 0.6670 0.8382 0.147 Uiso 1 1 calc R . .
H34B H 0.5410 0.6896 0.9147 0.147 Uiso 1 1 calc R . .
H34C H 0.5931 0.7793 0.8578 0.147 Uiso 1 1 calc R . .
N1 N 0.1516(6) 0.3966(3) 0.48555(17) 0.0667(9) Uani 1 1 d . . .
H1 H 0.0352 0.4130 0.4622 0.080 Uiso 1 1 calc R . .
N2 N 0.2064(6) 0.4492(3) 0.54022(17) 0.0653(9) Uani 1 1 d . . .
N3 N -0.3165(5) 0.9054(3) 0.99585(17) 0.0667(9) Uani 1 1 d . . .
H3A H -0.4333 0.9013 1.0247 0.080 Uiso 1 1 calc R . .
N4 N -0.2909(6) 0.9829(3) 0.94692(18) 0.0644(9) Uani 1 1 d . . .
O1 O 0.6491(5) 0.2510(2) 0.52549(14) 0.0676(8) Uani 1 1 d . . .
O2 O 0.4521(9) 0.1332(4) 0.5914(3) 0.167(2) Uani 1 1 d . . .
O3 O 0.0999(6) 0.7306(3) 0.84701(18) 0.0967(11) Uani 1 1 d . . .
O4 O 0.2253(4) 0.8292(2) 0.92704(13) 0.0653(8) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.366(7) . ?
C1 C2 1.376(7) . ?
C1 C7 1.452(6) . ?
C2 C3 1.398(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.349(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.360(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.349(6) . ?
C7 C8 1.376(6) . ?
C8 C9 1.380(6) . ?
C8 O1 1.392(5) . ?
C9 N2 1.345(6) . ?
C9 C10 1.470(6) . ?
C10 C15 1.371(6) . ?
C10 C11 1.385(6) . ?
C11 C12 1.372(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.366(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.393(7) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 O2 1.170(7) . ?
C16 O1 1.356(6) . ?
C16 C17 1.491(7) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C23 1.367(7) . ?
C18 C19 1.371(7) . ?
C18 C24 1.460(6) . ?
C19 C20 1.395(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.367(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.341(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.383(8) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 N4 1.341(6) . ?
C24 C25 1.402(6) . ?
C25 C26 1.380(6) . ?
C25 O4 1.384(6) . ?
C26 N3 1.354(6) . ?
C26 C27 1.466(6) . ?
C27 C28 1.3900 . ?
C27 C32 1.3900 . ?
C28 C29 1.3900 . ?
C28 H28 0.9300 . ?
C29 C30 1.3900 . ?
C29 H29 0.9300 . ?
C30 C31 1.3900 . ?
C30 H30 0.9300 . ?
C31 C32 1.3900 . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 O3 1.189(5) . ?
C33 O4 1.337(5) . ?
C33 C34 1.486(7) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
N1 N2 1.349(5) . ?
N1 H1 0.8600 . ?
N3 N4 1.338(5) . ?
N3 H3A 0.8600 . ?

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
C6 C1 C2 118.0(5) . . ?
C6 C1 C7 121.1(4) . . ?
C2 C1 C7 120.9(4) . . ?
C1 C2 C3 120.3(5) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 120.2(6) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.0(6) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 119.9(6) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 121.6(5) . . ?
C1 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
N1 C7 C8 104.5(4) . . ?
N1 C7 C1 121.8(4) . . ?
C8 C7 C1 133.7(4) . . ?
C7 C8 C9 108.6(4) . . ?
C7 C8 O1 125.3(4) . . ?
C9 C8 O1 126.0(4) . . ?
N2 C9 C8 108.3(4) . . ?
N2 C9 C10 119.3(4) . . ?
C8 C9 C10 132.4(4) . . ?
C15 C10 C11 118.1(4) . . ?
C15 C10 C9 122.2(4) . . ?
C11 C10 C9 119.7(4) . . ?
C12 C11 C10 121.2(5) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C13 C12 C11 120.6(5) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.0(5) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C13 C14 C15 120.5(5) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C10 C15 C14 120.5(5) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
O2 C16 O1 121.8(5) . . ?
O2 C16 C17 127.0(5) . . ?
O1 C16 C17 111.2(5) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 117.4(5) . . ?
C23 C18 C24 119.9(4) . . ?
C19 C18 C24 122.6(4) . . ?
C18 C19 C20 120.6(5) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C21 C20 C19 120.7(5) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C22 C21 C20 118.5(5) . . ?
C22 C21 H21 120.7 . . ?
C20 C21 H21 120.7 . . ?
C21 C22 C23 121.2(5) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C18 C23 C22 121.4(5) . . ?
C18 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
N4 C24 C25 107.3(4) . . ?
N4 C24 C18 120.2(4) . . ?
C25 C24 C18 132.5(4) . . ?
C26 C25 O4 124.1(4) . . ?
C26 C25 C24 108.6(4) . . ?
O4 C25 C24 127.0(4) . . ?
N3 C26 C25 104.0(4) . . ?
N3 C26 C27 123.2(4) . . ?
C25 C26 C27 132.7(4) . . ?
C28 C27 C32 120.0 . . ?
C28 C27 C26 119.4(3) . . ?
C32 C27 C26 120.6(3) . . ?
C29 C28 C27 120.0 . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C30 120.0 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C29 C30 C31 120.0 . . ?
C29 C30 H30 120.0 . . ?
C31 C30 H30 120.0 . . ?
C30 C31 C32 120.0 . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C31 C32 C27 120.0 . . ?
C31 C32 H32 120.0 . . ?
C27 C32 H32 120.0 . . ?
O3 C33 O4 122.8(4) . . ?
O3 C33 C34 126.6(4) . . ?
O4 C33 C34 110.6(4) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C7 N1 N2 112.4(4) . . ?
C7 N1 H1 123.8 . . ?
N2 N1 H1 123.8 . . ?
C9 N2 N1 106.2(3) . . ?
N4 N3 C26 112.9(3) . . ?
N4 N3 H3A 123.6 . . ?
C26 N3 H3A 123.6 . . ?
N3 N4 C24 107.2(4) . . ?
C16 O1 C8 118.0(4) . . ?
C33 O4 C25 119.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.713
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.057
