# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_mo_41009a
_audit_block_doi                 10.5517/cc13zlc1
_database_code_depnum_ccdc_archive 'CCDC 1042293'
_audit_update_record             
;
2015-01-06 deposited with the CCDC.
2015-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 N3 O'
_chemical_formula_weight         275.30

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 0.0016 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.2120(10)
_cell_length_b                   17.471(3)
_cell_length_c                   15.196(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.267(3)
_cell_angle_gamma                90
_cell_volume                     1382.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    3536
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      26.60

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.590
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.666
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9321
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.777
_diffrn_reflns_theta_max         26.739
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2932
_reflns_number_gt                2364
_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    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0986P)²+0.1823P] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2932
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1547
_refine_ls_wR_factor_gt          0.1313
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
N1 N 0.7192(2) 0.45002(7) 0.09084(7) 0.0294(3) Uani 1 1 d . . . . .
N2 N 1.0412(2) 0.53952(7) 0.14432(8) 0.0303(3) Uani 1 1 d . . . . .
N3 N 0.7544(3) 0.57071(8) 0.03154(9) 0.0357(3) Uani 1 1 d . . . . .
O1 O 0.6354(3) 0.30056(7) 0.23438(8) 0.0599(4) Uani 1 1 d . . . . .
C1 C 0.8080(3) 0.40074(8) 0.15237(9) 0.0310(3) Uani 1 1 d . . . . .
C2 C 0.8418(3) 0.51848(8) 0.09086(9) 0.0286(3) Uani 1 1 d . . . . .
C3 C 1.1256(3) 0.48873(8) 0.20469(9) 0.0298(3) Uani 1 1 d . . . . .
C4 C 1.0113(3) 0.41681(8) 0.21064(10) 0.0341(4) Uani 1 1 d . . . . .
H4 H 1.0709 0.3803 0.2531 0.041 Uiso 1 1 calc R U . . .
C5 C 0.6619(3) 0.32669(9) 0.16105(9) 0.0357(4) Uani 1 1 d . . . . .
C6 C 0.5497(3) 0.28715(8) 0.08183(9) 0.0301(3) Uani 1 1 d . . . . .
C7 C 0.6544(3) 0.29390(8) -0.00047(10) 0.0365(4) Uani 1 1 d . . . . .
H7 H 0.7952 0.3274 -0.0085 0.044 Uiso 1 1 calc R U . . .
C8 C 0.5528(4) 0.25167(9) -0.07103(10) 0.0442(4) Uani 1 1 d . . . . .
H8 H 0.6278 0.2551 -0.1269 0.053 Uiso 1 1 calc R U . . .
C9 C 0.3431(4) 0.20462(9) -0.06034(11) 0.0452(4) Uani 1 1 d . . . . .
H9 H 0.2716 0.1768 -0.1091 0.054 Uiso 1 1 calc R U . . .
C10 C 0.2372(3) 0.19805(9) 0.02139(11) 0.0424(4) Uani 1 1 d . . . . .
H10 H 0.0931 0.1657 0.0286 0.051 Uiso 1 1 calc R U . . .
C11 C 0.3399(3) 0.23826(9) 0.09230(10) 0.0359(4) Uani 1 1 d . . . . .
H11 H 0.2684 0.2329 0.1485 0.043 Uiso 1 1 calc R U . . .
C12 C 1.3415(3) 0.51404(8) 0.26498(9) 0.0313(3) Uani 1 1 d . . . . .
C13 C 1.4703(3) 0.58216(9) 0.24837(10) 0.0378(4) Uani 1 1 d . . . . .
H13 H 1.4182 0.6123 0.1988 0.045 Uiso 1 1 calc R U . . .
C14 C 1.6730(3) 0.60650(10) 0.30298(11) 0.0437(4) Uani 1 1 d . . . . .
H14 H 1.7596 0.6528 0.2903 0.052 Uiso 1 1 calc R U . . .
C15 C 1.7499(3) 0.56382(10) 0.37578(11) 0.0449(4) Uani 1 1 d . . . . .
H15 H 1.8889 0.5806 0.4133 0.054 Uiso 1 1 calc R U . . .
C16 C 1.6230(4) 0.49660(10) 0.39352(12) 0.0488(5) Uani 1 1 d . . . . .
H16 H 1.6750 0.4671 0.4437 0.059 Uiso 1 1 calc R U . . .
C17 C 1.4203(3) 0.47151(10) 0.33903(11) 0.0435(4) Uani 1 1 d . . . . .
H17 H 1.3346 0.4251 0.3522 0.052 Uiso 1 1 calc R U . . .
H3A H 0.805(3) 0.6187(11) 0.0377(11) 0.039(5) Uiso 1 1 d . . . . .
H3B H 0.615(4) 0.5629(11) -0.0032(13) 0.049(5) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.3398(18) . ?
N1 C2 1.3561(18) . ?
N2 C3 1.3381(19) . ?
N2 C2 1.3446(18) . ?
N3 C2 1.3493(19) . ?
N3 H3A 0.884(19) . ?
N3 H3B 0.89(2) . ?
O1 C5 1.2170(18) . ?
C1 C4 1.383(2) . ?
C1 C5 1.510(2) . ?
C3 C4 1.395(2) . ?
C3 C12 1.490(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.4875(19) . ?
C6 C7 1.389(2) . ?
C6 C11 1.402(2) . ?
C7 C8 1.389(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.394(2) . ?
C12 C17 1.396(2) . ?
C13 C14 1.384(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 114.64(12) . . ?
C3 N2 C2 117.26(12) . . ?
C2 N3 H3A 118.6(11) . . ?
C2 N3 H3B 122.6(13) . . ?
H3A N3 H3B 116.2(17) . . ?
N1 C1 C4 123.45(13) . . ?
N1 C1 C5 116.76(13) . . ?
C4 C1 C5 119.64(13) . . ?
N2 C2 N3 116.83(13) . . ?
N2 C2 N1 126.46(13) . . ?
N3 C2 N1 116.72(13) . . ?
N2 C3 C4 120.81(13) . . ?
N2 C3 C12 116.39(13) . . ?
C4 C3 C12 122.79(13) . . ?
C1 C4 C3 117.37(14) . . ?
C1 C4 H4 121.3 . . ?
C3 C4 H4 121.3 . . ?
O1 C5 C6 120.77(14) . . ?
O1 C5 C1 118.51(13) . . ?
C6 C5 C1 120.71(12) . . ?
C7 C6 C11 119.33(13) . . ?
C7 C6 C5 122.25(14) . . ?
C11 C6 C5 118.33(13) . . ?
C8 C7 C6 119.92(15) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C9 C8 C7 120.26(15) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 120.01(15) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 120.24(15) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C6 120.20(14) . . ?
C10 C11 H11 119.9 . . ?
C6 C11 H11 119.9 . . ?
C13 C12 C17 118.14(14) . . ?
C13 C12 C3 119.96(13) . . ?
C17 C12 C3 121.90(14) . . ?
C14 C13 C12 121.01(15) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C13 120.34(16) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 119.34(15) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 120.80(17) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C12 120.36(16) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?

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
C2 N1 C1 C4 -1.2(2) . . . . ?
C2 N1 C1 C5 174.22(12) . . . . ?
C3 N2 C2 N3 178.54(12) . . . . ?
C3 N2 C2 N1 -1.2(2) . . . . ?
C1 N1 C2 N2 1.5(2) . . . . ?
C1 N1 C2 N3 -178.26(12) . . . . ?
C2 N2 C3 C4 0.6(2) . . . . ?
C2 N2 C3 C12 -178.23(12) . . . . ?
N1 C1 C4 C3 0.8(2) . . . . ?
C5 C1 C4 C3 -174.55(13) . . . . ?
N2 C3 C4 C1 -0.4(2) . . . . ?
C12 C3 C4 C1 178.35(13) . . . . ?
N1 C1 C5 O1 -141.78(16) . . . . ?
C4 C1 C5 O1 33.8(2) . . . . ?
N1 C1 C5 C6 37.4(2) . . . . ?
C4 C1 C5 C6 -147.00(15) . . . . ?
O1 C5 C6 C7 -152.74(17) . . . . ?
C1 C5 C6 C7 28.1(2) . . . . ?
O1 C5 C6 C11 23.7(2) . . . . ?
C1 C5 C6 C11 -155.44(14) . . . . ?
C11 C6 C7 C8 -0.8(2) . . . . ?
C5 C6 C7 C8 175.61(14) . . . . ?
C6 C7 C8 C9 1.9(2) . . . . ?
C7 C8 C9 C10 -1.5(3) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C9 C10 C11 C6 1.1(2) . . . . ?
C7 C6 C11 C10 -0.7(2) . . . . ?
C5 C6 C11 C10 -177.25(14) . . . . ?
N2 C3 C12 C13 -9.9(2) . . . . ?
C4 C3 C12 C13 171.30(13) . . . . ?
N2 C3 C12 C17 169.82(14) . . . . ?
C4 C3 C12 C17 -9.0(2) . . . . ?
C17 C12 C13 C14 0.9(2) . . . . ?
C3 C12 C13 C14 -179.40(14) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
C15 C16 C17 C12 0.1(3) . . . . ?
C13 C12 C17 C16 -0.6(2) . . . . ?
C3 C12 C17 C16 179.68(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3B N1 0.89(2) 2.16(2) 3.0527(19) 176.9(18) 3_665

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.061

_shelxl_version_number           2013-2

