# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1525573'
_audit_update_record             
;
2017-01-04 deposited with the CCDC.
2017-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H13 N3 O'
_chemical_formula_sum            'C22 H13 N3 O'
_chemical_formula_weight         335.35

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   14.2849(4)
_cell_length_b                   11.9116(4)
_cell_length_c                   19.8778(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3382.33(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4398
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      23.40

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      1.316
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9826
_exptl_absorpt_correction_T_max  0.9900
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            15844
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_av_R_equivalents  0.1105
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.451
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3324
_reflns_number_gt                2162
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0594P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3324
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1086
_refine_ls_wR_factor_gt          0.0972
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_restrained_S_all      0.921
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.02233(11) 0.32474(13) 0.45107(7) 0.0496(4) Uani 1 1 d . . . . .
C2 C -0.00455(13) 0.34560(16) 0.51796(8) 0.0685(5) Uani 1 1 d . . . . .
H2 H 0.0391 0.3722 0.5488 0.082 Uiso 1 1 calc R U . . .
C3 C -0.09454(14) 0.32691(17) 0.53760(9) 0.0756(6) Uani 1 1 d . . . . .
H3 H -0.1118 0.3402 0.5820 0.091 Uiso 1 1 calc R U . . .
C4 C -0.16096(13) 0.28824(16) 0.49209(10) 0.0701(5) Uani 1 1 d . . . . .
H4 H -0.2221 0.2759 0.5064 0.084 Uiso 1 1 calc R U . . .
C5 C -0.13768(12) 0.26828(14) 0.42714(9) 0.0599(4) Uani 1 1 d . . . . .
H5 H -0.1826 0.2422 0.3971 0.072 Uiso 1 1 calc R U . . .
C6 C -0.04529(10) 0.28718(13) 0.40531(7) 0.0468(4) Uani 1 1 d . . . . .
C7 C 0.06533(10) 0.28368(13) 0.32363(7) 0.0442(4) Uani 1 1 d . . . . .
C8 C 0.14297(10) 0.18778(14) 0.23481(7) 0.0488(4) Uani 1 1 d . . . . .
C9 C 0.10527(12) 0.10942(17) 0.19225(8) 0.0678(5) Uani 1 1 d . . . . .
H9 H 0.0422 0.1126 0.1808 0.081 Uiso 1 1 calc R U . . .
C10 C 0.16140(15) 0.02604(18) 0.16654(10) 0.0801(6) Uani 1 1 d . . . . .
H10 H 0.1366 -0.0268 0.1371 0.096 Uiso 1 1 calc R U . . .
C11 C 0.25423(14) 0.02078(16) 0.18443(9) 0.0738(5) Uani 1 1 d . . . . .
H11 H 0.2919 -0.0365 0.1677 0.089 Uiso 1 1 calc R U . . .
C12 C 0.29130(11) 0.09954(14) 0.22676(8) 0.0586(4) Uani 1 1 d . . . . .
H12 H 0.3542 0.0949 0.2385 0.070 Uiso 1 1 calc R U . . .
C13 C 0.23712(10) 0.18655(12) 0.25264(7) 0.0438(4) Uani 1 1 d . . . . .
C14 C 0.27495(9) 0.27353(12) 0.29576(7) 0.0419(3) Uani 1 1 d . . . . .
C15 C 0.23274(9) 0.33258(12) 0.34746(6) 0.0416(4) Uani 1 1 d . . . . .
C16 C 0.13680(10) 0.31820(12) 0.36962(7) 0.0427(4) Uani 1 1 d . . . . .
C17 C 0.30345(10) 0.40326(12) 0.37696(7) 0.0456(4) Uani 1 1 d . . . . .
C18 C 0.30488(12) 0.47963(14) 0.42998(8) 0.0577(4) Uani 1 1 d . . . . .
H18 H 0.2512 0.4936 0.4551 0.069 Uiso 1 1 calc R U . . .
C19 C 0.38774(13) 0.53412(15) 0.44430(9) 0.0693(5) Uani 1 1 d . . . . .
H19 H 0.3896 0.5858 0.4793 0.083 Uiso 1 1 calc R U . . .
C20 C 0.46848(13) 0.51317(16) 0.40732(9) 0.0710(5) Uani 1 1 d . . . . .
H20 H 0.5235 0.5504 0.4187 0.085 Uiso 1 1 calc R U . . .
C21 C 0.46923(11) 0.43949(15) 0.35475(9) 0.0614(5) Uani 1 1 d . . . . .
H21 H 0.5232 0.4267 0.3297 0.074 Uiso 1 1 calc R U . . .
C22 C 0.38576(10) 0.38426(13) 0.34022(7) 0.0480(4) Uani 1 1 d . . . . .
N1 N 0.11386(8) 0.34061(11) 0.43251(6) 0.0503(3) Uani 1 1 d . . . . .
N2 N -0.02163(8) 0.26905(11) 0.33911(6) 0.0485(3) Uani 1 1 d . . . . .
N3 N 0.36723(8) 0.30425(11) 0.29230(6) 0.0500(3) Uani 1 1 d . . . . .
H3A H 0.4074 0.2775 0.2644 0.060 Uiso 1 1 calc R U . . .
O1 O 0.08493(7) 0.27569(10) 0.25568(5) 0.0534(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 N1 1.3716(18) . ?
C1 C6 1.400(2) . ?
C1 C2 1.406(2) . ?
C2 C3 1.362(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.354(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.408(2) . ?
C5 H5 0.9300 . ?
C6 N2 1.3756(19) . ?
C7 N2 1.2914(17) . ?
C7 O1 1.3828(16) . ?
C7 C16 1.4308(19) . ?
C8 C9 1.370(2) . ?
C8 C13 1.391(2) . ?
C8 O1 1.3985(18) . ?
C9 C10 1.375(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.392(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.4492(19) . ?
C14 N3 1.3698(17) . ?
C14 C15 1.3837(19) . ?
C15 C17 1.4398(19) . ?
C15 C16 1.4497(19) . ?
C16 N1 1.3196(17) . ?
C17 C18 1.392(2) . ?
C17 C22 1.402(2) . ?
C18 C19 1.380(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.390(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.365(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.392(2) . ?
C21 H21 0.9300 . ?
C22 N3 1.3732(19) . ?
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
N1 C1 C6 121.79(13) . . ?
N1 C1 C2 119.36(15) . . ?
C6 C1 C2 118.85(15) . . ?
C3 C2 C1 120.00(17) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.81(16) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 120.74(17) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.75(17) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
N2 C6 C1 120.14(13) . . ?
N2 C6 C5 120.02(14) . . ?
C1 C6 C5 119.84(14) . . ?
N2 C7 O1 114.72(12) . . ?
N2 C7 C16 124.95(13) . . ?
O1 C7 C16 119.96(12) . . ?
C9 C8 C13 122.02(15) . . ?
C9 C8 O1 117.40(14) . . ?
C13 C8 O1 120.37(13) . . ?
C8 C9 C10 119.50(16) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 119.96(17) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 120.12(17) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 121.54(16) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C8 C13 C12 116.83(14) . . ?
C8 C13 C14 120.25(13) . . ?
C12 C13 C14 122.93(13) . . ?
N3 C14 C15 108.72(12) . . ?
N3 C14 C13 121.34(12) . . ?
C15 C14 C13 129.81(13) . . ?
C14 C15 C17 107.10(12) . . ?
C14 C15 C16 125.28(12) . . ?
C17 C15 C16 127.49(13) . . ?
N1 C16 C7 119.09(13) . . ?
N1 C16 C15 119.91(12) . . ?
C7 C16 C15 120.96(12) . . ?
C18 C17 C22 119.16(14) . . ?
C18 C17 C15 134.48(14) . . ?
C22 C17 C15 106.36(12) . . ?
C19 C18 C17 118.44(16) . . ?
C19 C18 H18 120.8 . . ?
C17 C18 H18 120.8 . . ?
C18 C19 C20 121.21(16) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C21 C20 C19 121.79(16) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C20 C21 C22 117.13(16) . . ?
C20 C21 H21 121.4 . . ?
C22 C21 H21 121.4 . . ?
N3 C22 C21 129.56(14) . . ?
N3 C22 C17 108.16(12) . . ?
C21 C22 C17 122.26(15) . . ?
C16 N1 C1 117.63(12) . . ?
C7 N2 C6 116.30(12) . . ?
C14 N3 C22 109.63(12) . . ?
C14 N3 H3A 125.2 . . ?
C22 N3 H3A 125.2 . . ?
C7 O1 C8 117.48(11) . . ?

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
C21 H21 O1 0.93 2.63 3.370(2) 137.4 8_656
N3 H3A N2 0.86 2.30 3.0853(17) 152.8 8_656
N3 H3A O1 0.86 2.57 3.2705(15) 139.7 8_656
C21 H21 O1 0.93 2.63 3.370(2) 137.4 8_656
N3 H3A N2 0.86 2.30 3.0853(17) 152.8 8_656
N3 H3A O1 0.86 2.57 3.2705(15) 139.7 8_656

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.047

_shelxl_version_number           2014-3

