# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1553501'
_audit_update_record             
;
2017-06-01 deposited with the CCDC.
2017-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 N2 O'
_chemical_formula_weight         250.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   5.57110(10)
_cell_length_b                   14.4715(4)
_cell_length_c                   15.8198(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.691(2)
_cell_angle_gamma                90
_cell_volume                     1271.15(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    2685
_cell_measurement_theta_min      4.1330
_cell_measurement_theta_max      69.6820

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.320
_exptl_absorpt_coefficient_mu    0.660
_shelx_estimated_absorpt_T_min   0.783
_shelx_estimated_absorpt_T_max   0.817
_exptl_absorpt_correction_T_min  0.85002
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_reflns_number            5613
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.147
_diffrn_reflns_theta_max         70.040
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2369
_reflns_number_gt                2111
_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       'CrysAlisPro (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97

_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)+(0.0613P)²+0.1827P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2369
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1104
_refine_ls_wR_factor_gt          0.1050
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
O1 O -0.22000(17) 0.31226(7) 0.23513(7) 0.0529(3) Uani 1 1 d . . . . .
N1 N 0.26162(19) 0.27542(8) 0.16405(7) 0.0406(3) Uani 1 1 d . . . . .
H1 H 0.3913 0.2879 0.1952 0.049 Uiso 1 1 d R U . . .
N2 N -0.05871(19) 0.45805(8) 0.24070(7) 0.0418(3) Uani 1 1 d . . . . .
C9 C 0.2291(2) 0.44797(9) 0.14585(7) 0.0352(3) Uani 1 1 d . . . . .
C8 C 0.1033(2) 0.35559(9) 0.14447(8) 0.0361(3) Uani 1 1 d . . . . .
C1 C 0.2994(2) 0.23094(9) 0.08733(8) 0.0382(3) Uani 1 1 d . . . . .
C6 C 0.1310(2) 0.25907(9) 0.02259(8) 0.0403(3) Uani 1 1 d . . . . .
C14 C 0.1210(2) 0.50670(9) 0.20113(8) 0.0376(3) Uani 1 1 d . . . . .
C10 C 0.4189(2) 0.47949(10) 0.10292(8) 0.0414(3) Uani 1 1 d . . . . .
H10 H 0.4958 0.4404 0.0671 0.050 Uiso 1 1 calc R U . . .
C7 C -0.0304(2) 0.33028(9) 0.05701(8) 0.0414(3) Uani 1 1 d . . . . .
H7A H -0.1889 0.3050 0.0640 0.050 Uiso 1 1 calc R U . . .
H7B H -0.0469 0.3838 0.0201 0.050 Uiso 1 1 calc R U . . .
C15 C -0.0783(2) 0.36986(9) 0.21214(8) 0.0396(3) Uani 1 1 d . . . . .
C5 C 0.1314(3) 0.22074(11) -0.05749(9) 0.0532(4) Uani 1 1 d . . . . .
H5 H 0.0176 0.2387 -0.1007 0.064 Uiso 1 1 calc R U . . .
C2 C 0.4731(2) 0.16532(10) 0.07318(9) 0.0468(3) Uani 1 1 d . . . . .
H2 H 0.5853 0.1466 0.1165 0.056 Uiso 1 1 calc R U . . .
C13 C 0.1876(3) 0.59811(10) 0.21176(9) 0.0460(3) Uani 1 1 d . . . . .
H13 H 0.1099 0.6372 0.2474 0.055 Uiso 1 1 calc R U . . .
C11 C 0.4931(3) 0.57097(11) 0.11431(9) 0.0487(3) Uani 1 1 d . . . . .
H11 H 0.6222 0.5930 0.0864 0.058 Uiso 1 1 calc R U . . .
C16 C -0.1964(3) 0.49572(13) 0.30663(10) 0.0573(4) Uani 1 1 d . . . . .
H16A H -0.0902 0.5090 0.3560 0.086 Uiso 1 1 calc R U . . .
H16B H -0.3151 0.4515 0.3209 0.086 Uiso 1 1 calc R U . . .
H16C H -0.2749 0.5516 0.2867 0.086 Uiso 1 1 calc R U . . .
C12 C 0.3761(3) 0.62914(10) 0.16682(9) 0.0499(3) Uani 1 1 d . . . . .
H12 H 0.4247 0.6905 0.1722 0.060 Uiso 1 1 calc R U . . .
C3 C 0.4739(3) 0.12833(11) -0.00799(11) 0.0574(4) Uani 1 1 d . . . . .
H3 H 0.5904 0.0850 -0.0192 0.069 Uiso 1 1 calc R U . . .
C4 C 0.3049(3) 0.15485(12) -0.07235(11) 0.0618(4) Uani 1 1 d . . . . .
H4 H 0.3073 0.1285 -0.1259 0.074 Uiso 1 1 calc R U . . .


_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 C15 1.2235(16) . ?
N1 C1 1.4048(17) . ?
N1 C8 1.4749(16) . ?
N1 H1 0.8600 . ?
N2 C15 1.3554(17) . ?
N2 C14 1.4117(16) . ?
N2 C16 1.4505(17) . ?
C9 C10 1.3801(17) . ?
C9 C14 1.3912(17) . ?
C9 C8 1.5088(17) . ?
C8 C15 1.5458(17) . ?
C8 C7 1.5603(17) . ?
C1 C2 1.3870(19) . ?
C1 C6 1.3919(18) . ?
C6 C5 1.383(2) . ?
C6 C7 1.4991(18) . ?
C14 C13 1.3805(19) . ?
C10 C11 1.394(2) . ?
C10 H10 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C5 C4 1.391(2) . ?
C5 H5 0.9300 . ?
C2 C3 1.392(2) . ?
C2 H2 0.9300 . ?
C13 C12 1.390(2) . ?
C13 H13 0.9300 . ?
C11 C12 1.383(2) . ?
C11 H11 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C12 H12 0.9300 . ?
C3 C4 1.383(2) . ?
C3 H3 0.9300 . ?
C4 H4 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
C1 N1 C8 107.95(10) . . ?
C1 N1 H1 114.5 . . ?
C8 N1 H1 114.5 . . ?
C15 N2 C14 111.26(10) . . ?
C15 N2 C16 124.10(12) . . ?
C14 N2 C16 124.57(12) . . ?
C10 C9 C14 119.71(12) . . ?
C10 C9 C8 131.26(12) . . ?
C14 C9 C8 109.03(11) . . ?
N1 C8 C9 115.14(10) . . ?
N1 C8 C15 111.94(10) . . ?
C9 C8 C15 101.61(10) . . ?
N1 C8 C7 103.63(10) . . ?
C9 C8 C7 114.10(10) . . ?
C15 C8 C7 110.70(10) . . ?
C2 C1 C6 121.24(13) . . ?
C2 C1 N1 127.51(12) . . ?
C6 C1 N1 111.24(11) . . ?
C5 C6 C1 120.34(13) . . ?
C5 C6 C7 130.86(13) . . ?
C1 C6 C7 108.79(11) . . ?
C13 C14 C9 122.43(12) . . ?
C13 C14 N2 128.11(12) . . ?
C9 C14 N2 109.46(11) . . ?
C9 C10 C11 118.78(13) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
C6 C7 C8 103.08(10) . . ?
C6 C7 H7A 111.1 . . ?
C8 C7 H7A 111.1 . . ?
C6 C7 H7B 111.1 . . ?
C8 C7 H7B 111.1 . . ?
H7A C7 H7B 109.1 . . ?
O1 C15 N2 125.37(12) . . ?
O1 C15 C8 126.12(12) . . ?
N2 C15 C8 108.49(10) . . ?
C6 C5 C4 118.86(14) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C1 C2 C3 117.87(14) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C14 C13 C12 117.00(13) . . ?
C14 C13 H13 121.5 . . ?
C12 C13 H13 121.5 . . ?
C12 C11 C10 120.41(13) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 C12 C13 121.58(13) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C4 C3 C2 121.26(14) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.41(14) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 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
C1 N1 C8 C9 -102.43(12) . . . . ?
C1 N1 C8 C15 142.19(10) . . . . ?
C1 N1 C8 C7 22.87(12) . . . . ?
C10 C9 C8 N1 55.46(18) . . . . ?
C14 C9 C8 N1 -125.10(11) . . . . ?
C10 C9 C8 C15 176.64(13) . . . . ?
C14 C9 C8 C15 -3.92(12) . . . . ?
C10 C9 C8 C7 -64.20(17) . . . . ?
C14 C9 C8 C7 115.23(12) . . . . ?
C8 N1 C1 C2 165.37(12) . . . . ?
C8 N1 C1 C6 -16.15(14) . . . . ?
C2 C1 C6 C5 1.0(2) . . . . ?
N1 C1 C6 C5 -177.58(12) . . . . ?
C2 C1 C6 C7 -179.74(12) . . . . ?
N1 C1 C6 C7 1.68(15) . . . . ?
C10 C9 C14 C13 3.61(19) . . . . ?
C8 C9 C14 C13 -175.90(11) . . . . ?
C10 C9 C14 N2 -176.91(10) . . . . ?
C8 C9 C14 N2 3.58(14) . . . . ?
C15 N2 C14 C13 177.86(12) . . . . ?
C16 N2 C14 C13 -5.1(2) . . . . ?
C15 N2 C14 C9 -1.58(15) . . . . ?
C16 N2 C14 C9 175.41(12) . . . . ?
C14 C9 C10 C11 -1.90(19) . . . . ?
C8 C9 C10 C11 177.49(12) . . . . ?
C5 C6 C7 C8 -168.49(14) . . . . ?
C1 C6 C7 C8 12.36(14) . . . . ?
N1 C8 C7 C6 -20.96(12) . . . . ?
C9 C8 C7 C6 105.00(12) . . . . ?
C15 C8 C7 C6 -141.13(10) . . . . ?
C14 N2 C15 O1 -179.66(12) . . . . ?
C16 N2 C15 O1 3.3(2) . . . . ?
C14 N2 C15 C8 -1.05(14) . . . . ?
C16 N2 C15 C8 -178.06(12) . . . . ?
N1 C8 C15 O1 -55.04(16) . . . . ?
C9 C8 C15 O1 -178.42(12) . . . . ?
C7 C8 C15 O1 60.03(16) . . . . ?
N1 C8 C15 N2 126.37(11) . . . . ?
C9 C8 C15 N2 2.99(12) . . . . ?
C7 C8 C15 N2 -118.56(11) . . . . ?
C1 C6 C5 C4 -1.0(2) . . . . ?
C7 C6 C5 C4 179.94(14) . . . . ?
C6 C1 C2 C3 0.0(2) . . . . ?
N1 C1 C2 C3 178.34(13) . . . . ?
C9 C14 C13 C12 -2.36(19) . . . . ?
N2 C14 C13 C12 178.26(12) . . . . ?
C9 C10 C11 C12 -0.9(2) . . . . ?
C10 C11 C12 C13 2.1(2) . . . . ?
C14 C13 C12 C11 -0.5(2) . . . . ?
C1 C2 C3 C4 -1.0(2) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C6 C5 C4 C3 0.0(2) . . . . ?

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
N1 H1 O1 0.86 2.23 3.0590(14) 160.9 1_655

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.035

_shelxl_version_number           2013-4

