# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_20170728_wj_cb5_37
_database_code_depnum_ccdc_archive 'CCDC 1577009'
_audit_update_record             
;
2017-09-28 deposited with the CCDC.
2017-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 N2 O'
_chemical_formula_sum            'C16 H16 N2 O'
_chemical_formula_weight         252.31

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   14.4760(11)
_cell_length_b                   6.3544(5)
_cell_length_c                   14.6098(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.497(8)
_cell_angle_gamma                90.00
_cell_volume                     1321.41(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2068
_cell_measurement_theta_min      3.6210
_cell_measurement_theta_max      24.8290

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9685
_exptl_absorpt_correction_T_max  0.9763
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_measurement_method       'omega scans'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 15.9784
_diffrn_reflns_number            12149
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_sigmaI/netI    0.0795
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.51
_diffrn_reflns_theta_max         27.00
_reflns_number_total             2876
_reflns_number_gt                1794
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0282P)²+0.4025P] 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     SHELXL
_refine_ls_extinction_coef       0.0092(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2876
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1247
_refine_ls_wR_factor_gt          0.1061
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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 0.68341(15) 0.3163(4) 0.40683(16) 0.0489(6) Uani 1 1 d . . .
H1A H 0.7137 0.1924 0.4409 0.059 Uiso 1 1 calc R . .
H1B H 0.7318 0.4272 0.4089 0.059 Uiso 1 1 calc R . .
C2 C 0.64777(14) 0.2555(3) 0.30661(16) 0.0412(5) Uani 1 1 d . . .
C3 C 0.66362(17) 0.3917(4) 0.23687(18) 0.0543(7) Uani 1 1 d . . .
H3 H 0.6956 0.5205 0.2535 0.065 Uiso 1 1 calc R . .
C4 C 0.63430(19) 0.3450(5) 0.14442(19) 0.0654(8) Uani 1 1 d . . .
H4 H 0.6456 0.4404 0.0976 0.078 Uiso 1 1 calc R . .
C5 C 0.58859(18) 0.1588(5) 0.12072(18) 0.0658(8) Uani 1 1 d . . .
H5 H 0.5680 0.1245 0.0570 0.079 Uiso 1 1 calc R . .
C6 C 0.57233(16) 0.0209(4) 0.18886(17) 0.0523(6) Uani 1 1 d . . .
H6 H 0.5408 -0.1080 0.1711 0.063 Uiso 1 1 calc R . .
C7 C 0.60081(14) 0.0657(3) 0.28274(15) 0.0397(5) Uani 1 1 d . . .
C8 C 0.58440(15) -0.0934(3) 0.35498(16) 0.0443(6) Uani 1 1 d . . .
H8A H 0.6041 -0.0302 0.4174 0.053 Uiso 1 1 calc R . .
H8B H 0.6252 -0.2167 0.3510 0.053 Uiso 1 1 calc R . .
C9 C 0.48336(15) -0.1699(3) 0.34637(16) 0.0460(6) Uani 1 1 d . . .
H9A H 0.4609 -0.2163 0.2814 0.055 Uiso 1 1 calc R . .
H9B H 0.4829 -0.2942 0.3871 0.055 Uiso 1 1 calc R . .
C12 C 0.28648(14) 0.1527(3) 0.39809(14) 0.0393(5) Uani 1 1 d . . .
C11 C 0.31699(14) -0.0352(3) 0.36440(13) 0.0372(5) Uani 1 1 d . . .
C16 C 0.25238(16) -0.1958(4) 0.33519(15) 0.0485(6) Uani 1 1 d . . .
H16 H 0.2719 -0.3247 0.3118 0.058 Uiso 1 1 calc R . .
C15 C 0.16017(17) -0.1623(4) 0.34119(17) 0.0600(7) Uani 1 1 d . . .
H15 H 0.1152 -0.2696 0.3216 0.072 Uiso 1 1 calc R . .
C14 C 0.13105(17) 0.0278(5) 0.37575(17) 0.0596(7) Uani 1 1 d . . .
H14 H 0.0667 0.0455 0.3796 0.072 Uiso 1 1 calc R . .
C13 C 0.19258(16) 0.1885(4) 0.40414(16) 0.0519(6) Uani 1 1 d . . .
H13 H 0.1725 0.3176 0.4268 0.062 Uiso 1 1 calc R . .
N2 N 0.36359(12) 0.2776(3) 0.42029(12) 0.0428(5) Uani 1 1 d . . .
H2 H 0.3627 0.4069 0.4416 0.051 Uiso 1 1 calc R . .
N1 N 0.44274(12) 0.1757(3) 0.40511(12) 0.0409(5) Uani 1 1 d . . .
C10 C 0.41580(15) -0.0114(3) 0.37097(14) 0.0373(5) Uani 1 1 d . . .
O1 O 0.61101(10) 0.3909(2) 0.45242(11) 0.0521(5) Uani 1 1 d . . .
H1 H 0.5624 0.3178 0.4361 0.078 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0423(12) 0.0482(15) 0.0577(15) -0.0111(12) 0.0136(11) -0.0042(11)
C2 0.0360(11) 0.0406(13) 0.0502(14) -0.0033(11) 0.0165(10) 0.0042(10)
C3 0.0543(14) 0.0499(16) 0.0660(17) 0.0014(13) 0.0300(13) -0.0031(12)
C4 0.0688(18) 0.078(2) 0.0559(17) 0.0150(15) 0.0288(14) -0.0031(16)
C5 0.0595(16) 0.097(2) 0.0431(15) -0.0005(15) 0.0159(12) -0.0062(16)
C6 0.0463(13) 0.0614(17) 0.0511(15) -0.0104(13) 0.0139(11) -0.0070(12)
C7 0.0360(11) 0.0417(13) 0.0439(13) -0.0035(10) 0.0140(10) 0.0063(10)
C8 0.0470(13) 0.0384(13) 0.0495(14) 0.0008(11) 0.0145(11) 0.0057(10)
C9 0.0543(14) 0.0367(13) 0.0501(14) -0.0011(11) 0.0179(11) -0.0002(11)
C12 0.0391(12) 0.0449(14) 0.0339(12) 0.0009(10) 0.0062(9) -0.0013(10)
C11 0.0424(12) 0.0392(13) 0.0297(11) 0.0016(10) 0.0063(9) -0.0036(10)
C16 0.0557(15) 0.0488(15) 0.0400(13) -0.0026(11) 0.0059(11) -0.0095(12)
C15 0.0497(15) 0.0714(19) 0.0555(16) -0.0019(14) 0.0009(12) -0.0176(14)
C14 0.0390(13) 0.081(2) 0.0571(16) 0.0060(15) 0.0040(12) -0.0037(13)
C13 0.0478(14) 0.0623(17) 0.0469(14) 0.0008(12) 0.0125(11) 0.0064(12)
N2 0.0443(11) 0.0362(11) 0.0492(12) -0.0067(9) 0.0119(9) 0.0025(9)
N1 0.0422(10) 0.0387(11) 0.0433(11) -0.0062(9) 0.0116(8) 0.0000(9)
C10 0.0465(12) 0.0338(12) 0.0326(11) -0.0019(10) 0.0101(9) -0.0028(10)
O1 0.0485(9) 0.0506(11) 0.0602(11) -0.0212(8) 0.0180(8) -0.0064(8)

_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 O1 1.422(2) . ?
C1 C2 1.511(3) . ?
C2 C3 1.387(3) . ?
C2 C7 1.398(3) . ?
C3 C4 1.372(3) . ?
C4 C5 1.369(4) . ?
C5 C6 1.378(3) . ?
C6 C7 1.388(3) . ?
C7 C8 1.511(3) . ?
C8 C9 1.525(3) . ?
C9 C10 1.492(3) . ?
C12 N2 1.360(3) . ?
C12 C11 1.394(3) . ?
C12 C13 1.397(3) . ?
C11 C16 1.397(3) . ?
C11 C10 1.424(3) . ?
C16 C15 1.370(3) . ?
C15 C14 1.403(4) . ?
C14 C13 1.369(3) . ?
N2 N1 1.369(2) . ?
N1 C10 1.320(2) . ?

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
O1 C1 C2 112.86(18) . . ?
C3 C2 C7 119.5(2) . . ?
C3 C2 C1 118.6(2) . . ?
C7 C2 C1 121.8(2) . . ?
C4 C3 C2 121.7(2) . . ?
C5 C4 C3 119.0(2) . . ?
C4 C5 C6 120.3(2) . . ?
C5 C6 C7 121.6(2) . . ?
C6 C7 C2 117.8(2) . . ?
C6 C7 C8 119.8(2) . . ?
C2 C7 C8 122.3(2) . . ?
C7 C8 C9 115.22(18) . . ?
C10 C9 C8 115.21(18) . . ?
N2 C12 C11 106.56(18) . . ?
N2 C12 C13 131.0(2) . . ?
C11 C12 C13 122.5(2) . . ?
C12 C11 C16 119.7(2) . . ?
C12 C11 C10 105.33(18) . . ?
C16 C11 C10 134.9(2) . . ?
C15 C16 C11 118.2(2) . . ?
C16 C15 C14 121.1(2) . . ?
C13 C14 C15 122.0(2) . . ?
C14 C13 C12 116.5(2) . . ?
C12 N2 N1 111.11(17) . . ?
C10 N1 N2 106.79(17) . . ?
N1 C10 C11 110.18(19) . . ?
N1 C10 C9 122.47(19) . . ?
C11 C10 C9 127.33(19) . . ?

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
O1 C1 C2 C3 103.2(2) . . . . ?
O1 C1 C2 C7 -77.7(3) . . . . ?
C7 C2 C3 C4 0.0(3) . . . . ?
C1 C2 C3 C4 179.1(2) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C4 C5 C6 C7 0.4(4) . . . . ?
C5 C6 C7 C2 -0.6(3) . . . . ?
C5 C6 C7 C8 -178.0(2) . . . . ?
C3 C2 C7 C6 0.4(3) . . . . ?
C1 C2 C7 C6 -178.6(2) . . . . ?
C3 C2 C7 C8 177.7(2) . . . . ?
C1 C2 C7 C8 -1.4(3) . . . . ?
C6 C7 C8 C9 -53.5(3) . . . . ?
C2 C7 C8 C9 129.3(2) . . . . ?
C7 C8 C9 C10 -70.7(3) . . . . ?
N2 C12 C11 C16 -179.62(19) . . . . ?
C13 C12 C11 C16 0.0(3) . . . . ?
N2 C12 C11 C10 1.4(2) . . . . ?
C13 C12 C11 C10 -179.0(2) . . . . ?
C12 C11 C16 C15 -0.2(3) . . . . ?
C10 C11 C16 C15 178.4(2) . . . . ?
C11 C16 C15 C14 0.0(4) . . . . ?
C16 C15 C14 C13 0.6(4) . . . . ?
C15 C14 C13 C12 -0.8(4) . . . . ?
N2 C12 C13 C14 -180.0(2) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C11 C12 N2 N1 -1.9(2) . . . . ?
C13 C12 N2 N1 178.5(2) . . . . ?
C12 N2 N1 C10 1.7(2) . . . . ?
N2 N1 C10 C11 -0.7(2) . . . . ?
N2 N1 C10 C9 -179.38(18) . . . . ?
C12 C11 C10 N1 -0.4(2) . . . . ?
C16 C11 C10 N1 -179.2(2) . . . . ?
C12 C11 C10 C9 178.2(2) . . . . ?
C16 C11 C10 C9 -0.6(4) . . . . ?
C8 C9 C10 N1 -5.4(3) . . . . ?
C8 C9 C10 C11 176.19(19) . . . . ?

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
O1 H1 N1 0.84 1.93 2.769(2) 173.2 .
N2 H2 O1 0.88 1.99 2.790(2) 149.7 3_666

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.038
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
