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

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

data_zxy2_0m
_database_code_depnum_ccdc_archive 'CCDC 1520915'
_audit_update_record             
;
2016-12-06 deposited with the CCDC.
2017-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H13 N3 O2'
_chemical_formula_sum            'C21 H13 N3 O2'
_chemical_formula_weight         339.34

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                   7.617(12)
_cell_length_b                   10.617(17)
_cell_length_c                   11.452(18)
_cell_angle_alpha                64.336(15)
_cell_angle_beta                 72.042(17)
_cell_angle_gamma                88.506(18)
_cell_volume                     788(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2193
_cell_measurement_theta_min      2.228
_cell_measurement_theta_max      27.323

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9822
_exptl_absorpt_correction_T_max  0.9841
_exptl_absorpt_process_details   
; 
CrysAlis Pro (Agilent, 2013)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6049
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         27.42
_reflns_number_total             3533
_reflns_number_gt                2807
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_cell_refinement       
;
CrysAlis Pro (Agilent, 2013)
;
_computing_data_reduction        
;
CrysAlis Pro (Agilent, 2013)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    '(K. Brandenburg, Diamond 3.1, 2009)'
_computing_publication_material  '(K. Brandenburg, Diamond 3.1, 2009)'


_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)+(0.1200P)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         3309
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0682
_refine_ls_wR_factor_ref         0.1672
_refine_ls_wR_factor_gt          0.1250
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5452(3) 0.28652(19) 0.58926(18) 0.0563(6) Uani 1 1 d . . .
O2 O 0.8800(3) -0.22659(17) 0.64637(17) 0.0523(5) Uani 1 1 d . . .
N1 N 0.7695(3) -0.00387(19) 0.46502(18) 0.0383(5) Uani 1 1 d . . .
N2 N 0.7122(2) 0.09915(19) 0.61696(17) 0.0340(5) Uani 1 1 d . . .
N3 N 0.7208(3) 0.09958(19) 0.73856(17) 0.0373(5) Uani 1 1 d . . .
C1 C 0.8233(3) 0.2284(2) 0.7139(2) 0.0356(5) Uani 1 1 d . . .
C2 C 0.7300(3) 0.3148(3) 0.7679(2) 0.0450(6) Uani 1 1 d . . .
H2 H 0.6033 0.2928 0.8167 0.054 Uiso 1 1 calc R . .
C3 C 0.8275(4) 0.4343(3) 0.7482(2) 0.0490(6) Uani 1 1 d . . .
H3 H 0.7662 0.4926 0.7847 0.059 Uiso 1 1 calc R . .
C4 C 1.1066(3) 0.3813(3) 0.6217(2) 0.0455(6) Uani 1 1 d . . .
H4 H 1.2333 0.4038 0.5729 0.055 Uiso 1 1 calc R . .
C5 C 1.0108(3) 0.2607(2) 0.6405(2) 0.0394(6) Uani 1 1 d . . .
H5 H 1.0724 0.2024 0.6041 0.047 Uiso 1 1 calc R . .
C6 C 1.0138(4) 0.4675(2) 0.6753(2) 0.0464(6) Uani 1 1 d . . .
H6 H 1.0780 0.5486 0.6618 0.056 Uiso 1 1 calc R . .
C7 C 0.6222(3) 0.2092(2) 0.5431(2) 0.0385(5) Uani 1 1 d . . .
C8 C 0.6376(3) 0.2174(2) 0.4098(2) 0.0377(5) Uani 1 1 d . . .
C9 C 0.5780(3) 0.3318(3) 0.3168(3) 0.0494(6) Uani 1 1 d . . .
H9 H 0.5270 0.4015 0.3403 0.059 Uiso 1 1 calc R . .
C10 C 0.5956(4) 0.3399(3) 0.1904(3) 0.0561(7) Uani 1 1 d . . .
H10 H 0.5576 0.4162 0.1279 0.067 Uiso 1 1 calc R . .
C11 C 0.6696(4) 0.2352(3) 0.1554(3) 0.0580(7) Uani 1 1 d . . .
H11 H 0.6816 0.2423 0.0694 0.070 Uiso 1 1 calc R . .
C12 C 0.7255(4) 0.1210(3) 0.2467(2) 0.0494(6) Uani 1 1 d . . .
H12 H 0.7723 0.0503 0.2232 0.059 Uiso 1 1 calc R . .
C13 C 0.7117(3) 0.1115(2) 0.3750(2) 0.0383(5) Uani 1 1 d . . .
C14 C 0.7700(3) -0.0056(2) 0.5780(2) 0.0327(5) Uani 1 1 d . . .
C15 C 0.8208(3) -0.1359(2) 0.6794(2) 0.0360(5) Uani 1 1 d . . .
C16 C 0.7922(3) -0.1437(2) 0.8144(2) 0.0377(5) Uani 1 1 d . . .
C17 C 0.8173(4) -0.2680(3) 0.9195(2) 0.0494(6) Uani 1 1 d . . .
H17 H 0.8408 -0.3473 0.9047 0.059 Uiso 1 1 calc R . .
C18 C 0.8077(4) -0.2738(3) 1.0427(3) 0.0566(7) Uani 1 1 d . . .
H18 H 0.8237 -0.3565 1.1118 0.068 Uiso 1 1 calc R . .
C19 C 0.7738(4) -0.1554(3) 1.0637(2) 0.0570(7) Uani 1 1 d . . .
H19 H 0.7687 -0.1589 1.1473 0.068 Uiso 1 1 calc R . .
C20 C 0.7474(4) -0.0323(3) 0.9632(2) 0.0526(7) Uani 1 1 d . . .
H20 H 0.7257 0.0466 0.9788 0.063 Uiso 1 1 calc R . .
C21 C 0.7532(3) -0.0262(2) 0.8371(2) 0.0364(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
O1 C7 1.206(3) . ?
O2 C15 1.208(3) . ?
N1 C14 1.287(3) . ?
N1 C13 1.384(3) . ?
N2 C14 1.383(3) . ?
N2 N3 1.416(3) . ?
N2 C7 1.418(3) . ?
N3 C21 1.403(3) . ?
N3 C1 1.465(3) . ?
C1 C5 1.378(4) . ?
C1 C2 1.384(3) . ?
C2 C3 1.382(4) . ?
C2 H2 0.9300 . ?
C3 C6 1.369(4) . ?
C3 H3 0.9300 . ?
C4 C6 1.378(4) . ?
C4 C5 1.389(4) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.459(4) . ?
C8 C13 1.399(4) . ?
C8 C9 1.401(3) . ?
C9 C10 1.375(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.389(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.377(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.398(4) . ?
C12 H12 0.9300 . ?
C14 C15 1.506(3) . ?
C15 C16 1.459(4) . ?
C16 C21 1.388(4) . ?
C16 C17 1.407(3) . ?
C17 C18 1.365(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.383(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.379(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.403(4) . ?
C20 H20 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
C14 N1 C13 118.1(2) . . ?
C14 N2 N3 123.84(17) . . ?
C14 N2 C7 121.7(2) . . ?
N3 N2 C7 114.21(17) . . ?
C21 N3 N2 117.12(19) . . ?
C21 N3 C1 115.6(2) . . ?
N2 N3 C1 113.32(16) . . ?
C5 C1 C2 120.9(2) . . ?
C5 C1 N3 120.07(19) . . ?
C2 C1 N3 119.0(2) . . ?
C3 C2 C1 119.2(2) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C6 C3 C2 120.5(2) . . ?
C6 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C6 C4 C5 120.0(2) . . ?
C6 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C1 C5 C4 119.2(2) . . ?
C1 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C3 C6 C4 120.3(2) . . ?
C3 C6 H6 119.8 . . ?
C4 C6 H6 119.8 . . ?
O1 C7 N2 121.3(2) . . ?
O1 C7 C8 125.9(2) . . ?
N2 C7 C8 112.79(19) . . ?
C13 C8 C9 120.2(2) . . ?
C13 C8 C7 120.1(2) . . ?
C9 C8 C7 119.7(2) . . ?
C10 C9 C8 119.4(3) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 120.5(2) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 120.7(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 119.8(3) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
N1 C13 C12 118.9(2) . . ?
N1 C13 C8 121.7(2) . . ?
C12 C13 C8 119.4(2) . . ?
N1 C14 N2 124.16(19) . . ?
N1 C14 C15 117.6(2) . . ?
N2 C14 C15 118.0(2) . . ?
O2 C15 C16 124.2(2) . . ?
O2 C15 C14 119.7(2) . . ?
C16 C15 C14 116.2(2) . . ?
C21 C16 C17 119.7(2) . . ?
C21 C16 C15 120.42(19) . . ?
C17 C16 C15 119.7(2) . . ?
C18 C17 C16 120.8(3) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 119.3(2) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C20 C19 C18 121.2(3) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C19 C20 C21 119.8(3) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C16 C21 N3 122.7(2) . . ?
C16 C21 C20 119.0(2) . . ?
N3 C21 C20 118.3(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 N2 N3 C21 -13.6(3) . . . . ?
C7 N2 N3 C21 160.70(19) . . . . ?
C14 N2 N3 C1 125.0(2) . . . . ?
C7 N2 N3 C1 -60.7(3) . . . . ?
C21 N3 C1 C5 74.5(3) . . . . ?
N2 N3 C1 C5 -64.8(2) . . . . ?
C21 N3 C1 C2 -104.2(3) . . . . ?
N2 N3 C1 C2 116.6(2) . . . . ?
C5 C1 C2 C3 -0.5(3) . . . . ?
N3 C1 C2 C3 178.15(19) . . . . ?
C1 C2 C3 C6 0.5(4) . . . . ?
C2 C1 C5 C4 0.4(3) . . . . ?
N3 C1 C5 C4 -178.18(18) . . . . ?
C6 C4 C5 C1 -0.5(3) . . . . ?
C2 C3 C6 C4 -0.6(4) . . . . ?
C5 C4 C6 C3 0.5(3) . . . . ?
C14 N2 C7 O1 167.7(2) . . . . ?
N3 N2 C7 O1 -6.7(3) . . . . ?
C14 N2 C7 C8 -13.3(3) . . . . ?
N3 N2 C7 C8 172.24(17) . . . . ?
O1 C7 C8 C13 -172.6(2) . . . . ?
N2 C7 C8 C13 8.5(3) . . . . ?
O1 C7 C8 C9 7.5(4) . . . . ?
N2 C7 C8 C9 -171.4(2) . . . . ?
C13 C8 C9 C10 -0.9(4) . . . . ?
C7 C8 C9 C10 179.0(2) . . . . ?
C8 C9 C10 C11 0.8(4) . . . . ?
C9 C10 C11 C12 0.4(4) . . . . ?
C10 C11 C12 C13 -1.5(4) . . . . ?
C14 N1 C13 C12 174.50(19) . . . . ?
C14 N1 C13 C8 -6.5(3) . . . . ?
C11 C12 C13 N1 -179.7(2) . . . . ?
C11 C12 C13 C8 1.3(4) . . . . ?
C9 C8 C13 N1 -179.1(2) . . . . ?
C7 C8 C13 N1 1.0(3) . . . . ?
C9 C8 C13 C12 -0.1(4) . . . . ?
C7 C8 C13 C12 -180.0(2) . . . . ?
C13 N1 C14 N2 1.6(3) . . . . ?
C13 N1 C14 C15 176.00(17) . . . . ?
N3 N2 C14 N1 -177.11(19) . . . . ?
C7 N2 C14 N1 9.0(3) . . . . ?
N3 N2 C14 C15 8.5(3) . . . . ?
C7 N2 C14 C15 -165.35(19) . . . . ?
N1 C14 C15 O2 8.7(3) . . . . ?
N2 C14 C15 O2 -176.6(2) . . . . ?
N1 C14 C15 C16 -170.77(18) . . . . ?
N2 C14 C15 C16 4.0(3) . . . . ?
O2 C15 C16 C21 169.3(2) . . . . ?
C14 C15 C16 C21 -11.3(3) . . . . ?
O2 C15 C16 C17 -6.1(4) . . . . ?
C14 C15 C16 C17 173.28(19) . . . . ?
C21 C16 C17 C18 -1.4(4) . . . . ?
C15 C16 C17 C18 174.1(2) . . . . ?
C16 C17 C18 C19 -0.4(4) . . . . ?
C17 C18 C19 C20 0.8(4) . . . . ?
C18 C19 C20 C21 0.5(4) . . . . ?
C17 C16 C21 N3 -177.9(2) . . . . ?
C15 C16 C21 N3 6.6(3) . . . . ?
C17 C16 C21 C20 2.7(4) . . . . ?
C15 C16 C21 C20 -172.8(2) . . . . ?
N2 N3 C21 C16 5.7(3) . . . . ?
C1 N3 C21 C16 -131.9(2) . . . . ?
N2 N3 C21 C20 -174.90(19) . . . . ?
C1 N3 C21 C20 47.5(3) . . . . ?
C19 C20 C21 C16 -2.3(4) . . . . ?
C19 C20 C21 N3 178.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.42
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.088
