# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1039655'
_audit_update_record             
;
2014-12-16 deposited with the CCDC.
2015-06-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 N2 O2'
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   12.0978(3)
_cell_length_b                   3.97900(10)
_cell_length_c                   15.5788(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.0550(10)
_cell_angle_gamma                90
_cell_volume                     738.40(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5834
_cell_measurement_theta_min      2.6557
_cell_measurement_theta_max      24.6960

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             308
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   (SADABS;Sheldrick,2003)
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX2 CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13647
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.401
_diffrn_reflns_theta_max         26.048
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2873
_reflns_number_gt                2503
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    0.986

_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       'SMART (Bruker, 2003)'
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury (Macrae et al., 2006) and PLATON (Spek, 2009)
;
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0550P)²+0.0436P] 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_abs_structure_details 
;
 Flack x determined using 953 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2873
_refine_ls_number_parameters     201
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0924
_refine_ls_wR_factor_gt          0.0877
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.039
_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 0.21179(12) 0.4711(5) 0.76395(10) 0.0526(5) Uani 1 1 d . . . . .
O2 O 0.20048(13) 0.6957(6) 0.62946(11) 0.0720(6) Uani 1 1 d . . . . .
N1 N 0.88759(14) 0.0379(5) 0.65775(12) 0.0500(5) Uani 1 1 d . . . . .
N2 N 0.38702(14) 0.2584(5) 0.78770(11) 0.0452(4) Uani 1 1 d . . . . .
C1 C 0.9515(2) -0.1153(8) 0.73453(16) 0.0616(7) Uani 1 1 d . . . . .
H1A H 0.9223 -0.3356 0.7422 0.092 Uiso 1 1 calc R U . . .
H1B H 0.9461 0.0202 0.7846 0.092 Uiso 1 1 calc R U . . .
H1C H 1.0288 -0.1327 0.7280 0.092 Uiso 1 1 calc R U . . .
C2 C 0.9452(2) 0.1201(8) 0.58612(18) 0.0653(8) Uani 1 1 d . . . . .
H2A H 0.9505 0.3598 0.5811 0.098 Uiso 1 1 calc R U . . .
H2B H 0.9041 0.0298 0.5329 0.098 Uiso 1 1 calc R U . . .
H2C H 1.0193 0.0250 0.5970 0.098 Uiso 1 1 calc R U . . .
C3 C 0.77797(16) 0.1258(5) 0.65420(13) 0.0395(5) Uani 1 1 d . . . . .
C4 C 0.72070(17) 0.0416(6) 0.72296(13) 0.0419(5) Uani 1 1 d . . . . .
H4 H 0.7583 -0.0762 0.7709 0.050 Uiso 1 1 calc R U . . .
C5 C 0.61069(16) 0.1308(5) 0.72026(13) 0.0417(5) Uani 1 1 d . . . . .
H5 H 0.5751 0.0702 0.7662 0.050 Uiso 1 1 calc R U . . .
C6 C 0.55067(16) 0.3106(5) 0.65007(12) 0.0381(5) Uani 1 1 d . . . . .
C7 C 0.60770(17) 0.3890(6) 0.58175(13) 0.0420(5) Uani 1 1 d . . . . .
H7 H 0.5698 0.5066 0.5339 0.050 Uiso 1 1 calc R U . . .
C8 C 0.71736(17) 0.2989(5) 0.58275(13) 0.0423(5) Uani 1 1 d . . . . .
H8 H 0.7518 0.3531 0.5357 0.051 Uiso 1 1 calc R U . . .
C9 C 0.43727(17) 0.4252(6) 0.64534(14) 0.0429(5) Uani 1 1 d . . . . .
H9 H 0.4069 0.5318 0.5934 0.051 Uiso 1 1 calc R U . . .
C10 C 0.36766(17) 0.4032(6) 0.70400(13) 0.0438(5) Uani 1 1 d . . . . .
C11 C 0.25521(18) 0.5429(7) 0.68868(14) 0.0510(6) Uani 1 1 d . . . . .
C12 C 0.29679(16) 0.3043(6) 0.81865(13) 0.0440(5) Uani 1 1 d . . . . .
C13 C 0.27432(17) 0.2063(6) 0.90362(14) 0.0455(5) Uani 1 1 d . . . . .
C14 C 0.3582(2) 0.0507(7) 0.96232(15) 0.0559(6) Uani 1 1 d . . . . .
H14 H 0.4272 0.0054 0.9462 0.067 Uiso 1 1 calc R U . . .
C15 C 0.3400(3) -0.0374(7) 1.04438(16) 0.0653(7) Uani 1 1 d . . . . .
H15 H 0.3970 -0.1370 1.0840 0.078 Uiso 1 1 calc R U . . .
C16 C 0.2365(3) 0.0236(7) 1.06731(17) 0.0661(7) Uani 1 1 d . . . . .
H16 H 0.2232 -0.0405 1.1220 0.079 Uiso 1 1 calc R U . . .
C17 C 0.1532(2) 0.1782(8) 1.00971(16) 0.0634(7) Uani 1 1 d . . . . .
H17 H 0.0842 0.2210 1.0260 0.076 Uiso 1 1 calc R U . . .
C18 C 0.17092(19) 0.2707(7) 0.92783(15) 0.0541(6) Uani 1 1 d . . . . .
H18 H 0.1141 0.3753 0.8891 0.065 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 C12 1.385(2) . ?
O1 C11 1.396(3) . ?
O2 C11 1.202(3) . ?
N1 C3 1.363(3) . ?
N1 C1 1.441(3) . ?
N1 C2 1.453(3) . ?
N2 C12 1.281(3) . ?
N2 C10 1.407(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C8 1.402(3) . ?
C3 C4 1.414(3) . ?
C4 C5 1.371(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.401(3) . ?
C6 C9 1.435(3) . ?
C7 C8 1.372(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.349(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.450(3) . ?
C12 C13 1.450(3) . ?
C13 C14 1.387(3) . ?
C13 C18 1.392(3) . ?
C14 C15 1.380(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.372(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(3) . ?
C17 H17 0.9300 . ?
C18 H18 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
C12 O1 C11 105.50(15) . . ?
C3 N1 C1 121.29(19) . . ?
C3 N1 C2 120.35(19) . . ?
C1 N1 C2 118.20(18) . . ?
C12 N2 C10 105.99(17) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C8 121.90(19) . . ?
N1 C3 C4 120.70(18) . . ?
C8 C3 C4 117.40(17) . . ?
C5 C4 C3 121.14(19) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 121.66(19) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C7 116.78(18) . . ?
C5 C6 C9 124.31(19) . . ?
C7 C6 C9 118.89(18) . . ?
C8 C7 C6 122.46(19) . . ?
C8 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
C7 C8 C3 120.54(19) . . ?
C7 C8 H8 119.7 . . ?
C3 C8 H8 119.7 . . ?
C10 C9 C6 130.4(2) . . ?
C10 C9 H9 114.8 . . ?
C6 C9 H9 114.8 . . ?
C9 C10 N2 129.16(18) . . ?
C9 C10 C11 122.83(19) . . ?
N2 C10 C11 108.00(18) . . ?
O2 C11 O1 120.71(19) . . ?
O2 C11 C10 134.0(2) . . ?
O1 C11 C10 105.25(18) . . ?
N2 C12 O1 115.26(18) . . ?
N2 C12 C13 127.80(19) . . ?
O1 C12 C13 116.94(17) . . ?
C14 C13 C18 119.5(2) . . ?
C14 C13 C12 119.3(2) . . ?
C18 C13 C12 121.2(2) . . ?
C15 C14 C13 120.5(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.5(3) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 120.3(2) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.6(2) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C13 119.6(2) . . ?
C17 C18 H18 120.2 . . ?
C13 C18 H18 120.2 . . ?

_refine_diff_density_max         0.135
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.051



