# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1503692'
_audit_update_record             
;
2016-09-09 deposited with the CCDC.
2016-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 N2 O3'
_chemical_formula_weight         286.32

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           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3821(12)
_cell_length_b                   9.8440(17)
_cell_length_c                   10.9083(18)
_cell_angle_alpha                94.965(2)
_cell_angle_beta                 103.154(2)
_cell_angle_gamma                109.687(2)
_cell_volume                     715.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1197
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      21.93

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9727
_exptl_absorpt_correction_T_max  0.9835
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5725
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         25.15
_reflns_number_total             2541
_reflns_number_gt                1650
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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)+(0.0720P)²+0.4929P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2541
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0633
_refine_ls_wR_factor_ref         0.1910
_refine_ls_wR_factor_gt          0.1611
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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
N1 N -0.0834(4) 0.6086(3) -0.2439(2) 0.0591(7) Uani 1 1 d . . .
N2 N -0.3527(4) 0.5239(3) -0.1753(3) 0.0651(8) Uani 1 1 d . . .
H2 H -0.4240 0.4984 -0.1229 0.078 Uiso 1 1 calc R . .
O1 O 0.1692(4) 0.6453(3) -0.3357(2) 0.0829(9) Uani 1 1 d . . .
O2 O -0.2979(3) 0.6128(3) 0.0809(2) 0.0696(7) Uani 1 1 d . . .
O3 O 0.3320(4) 1.1068(3) 0.5394(2) 0.0699(7) Uani 1 1 d . . .
C1 C -0.4308(7) 0.4770(5) -0.3125(4) 0.0941(15) Uani 1 1 d . . .
H1A H -0.5205 0.5251 -0.3483 0.113 Uiso 1 1 calc R . .
H1B H -0.5015 0.3717 -0.3346 0.113 Uiso 1 1 calc R . .
C2 C -0.2426(6) 0.5239(5) -0.3606(3) 0.0790(12) Uani 1 1 d . . .
H2A H -0.2186 0.4393 -0.3951 0.095 Uiso 1 1 calc R . .
H2B H -0.2536 0.5841 -0.4257 0.095 Uiso 1 1 calc R . .
C3 C 0.1156(6) 0.6581(3) -0.2383(3) 0.0605(9) Uani 1 1 d . . .
C4 C 0.2559(5) 0.7188(4) -0.1056(3) 0.0702(10) Uani 1 1 d . . .
H4 H 0.2678 0.6323 -0.0716 0.084 Uiso 1 1 calc R . .
C5 C 0.1720(5) 0.7838(4) -0.0178(3) 0.0687(10) Uani 1 1 d . . .
H5A H 0.1798 0.8797 -0.0366 0.082 Uiso 1 1 calc R . .
H5B H 0.2550 0.7980 0.0687 0.082 Uiso 1 1 calc R . .
C6 C -0.0427(4) 0.6959(3) -0.0218(3) 0.0499(8) Uani 1 1 d . . .
C7 C -0.1600(5) 0.6104(3) -0.1379(3) 0.0513(8) Uani 1 1 d . . .
C8 C -0.1269(4) 0.6984(3) 0.0835(3) 0.0499(8) Uani 1 1 d . . .
C9 C -0.0066(4) 0.8076(3) 0.2047(3) 0.0463(7) Uani 1 1 d . . .
C10 C 0.0921(4) 0.9560(3) 0.2055(3) 0.0498(8) Uani 1 1 d . . .
H10 H 0.0860 0.9900 0.1283 0.060 Uiso 1 1 calc R . .
C11 C 0.1981(5) 1.0527(4) 0.3178(3) 0.0532(8) Uani 1 1 d . . .
H11 H 0.2593 1.1517 0.3162 0.064 Uiso 1 1 calc R . .
C12 C 0.2145(4) 1.0038(4) 0.4334(3) 0.0511(8) Uani 1 1 d . . .
C13 C 0.1178(5) 0.8561(4) 0.4357(3) 0.0563(9) Uani 1 1 d . . .
H13 H 0.1289 0.8216 0.5128 0.068 Uiso 1 1 calc R . .
C14 C 0.0052(5) 0.7615(4) 0.3218(3) 0.0527(8) Uani 1 1 d . . .
H14 H -0.0649 0.6639 0.3238 0.063 Uiso 1 1 calc R . .
C15 C 0.3585(6) 1.0593(5) 0.6602(3) 0.0821(12) Uani 1 1 d . . .
H15A H 0.2322 1.0235 0.6797 0.123 Uiso 1 1 calc R . .
H15B H 0.4508 1.1402 0.7256 0.123 Uiso 1 1 calc R . .
H15C H 0.4105 0.9823 0.6564 0.123 Uiso 1 1 calc R . .
C16 C 0.4655(5) 0.8100(4) -0.1046(4) 0.0685(10) Uani 1 1 d . . .
H16A H 0.4679 0.9008 -0.1315 0.103 Uiso 1 1 calc R . .
H16B H 0.5103 0.7577 -0.1621 0.103 Uiso 1 1 calc R . .
H16C H 0.5522 0.8299 -0.0197 0.103 Uiso 1 1 calc R . .


_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 C3 1.368(4) . ?
N1 C7 1.399(4) . ?
N1 C2 1.474(4) . ?
N2 C7 1.332(4) . ?
N2 C1 1.447(5) . ?
N2 H2 0.8600 . ?
O1 C3 1.226(4) . ?
O2 C8 1.253(4) . ?
O3 C12 1.366(4) . ?
O3 C15 1.429(4) . ?
C1 C2 1.535(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.509(5) . ?
C4 C5 1.463(5) . ?
C4 C16 1.501(5) . ?
C4 H4 0.9800 . ?
C5 C6 1.517(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.374(4) . ?
C6 C8 1.426(4) . ?
C8 C9 1.506(4) . ?
C9 C14 1.387(4) . ?
C9 C10 1.393(4) . ?
C10 C11 1.371(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.392(5) . ?
C13 C14 1.382(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C3 N1 C7 124.9(3) . . ?
C3 N1 C2 123.2(3) . . ?
C7 N1 C2 111.1(3) . . ?
C7 N2 C1 113.6(3) . . ?
C7 N2 H2 123.2 . . ?
C1 N2 H2 123.2 . . ?
C12 O3 C15 117.7(3) . . ?
N2 C1 C2 103.5(3) . . ?
N2 C1 H1A 111.1 . . ?
C2 C1 H1A 111.1 . . ?
N2 C1 H1B 111.1 . . ?
C2 C1 H1B 111.1 . . ?
H1A C1 H1B 109.0 . . ?
N1 C2 C1 102.8(3) . . ?
N1 C2 H2A 111.2 . . ?
C1 C2 H2A 111.2 . . ?
N1 C2 H2B 111.2 . . ?
C1 C2 H2B 111.2 . . ?
H2A C2 H2B 109.1 . . ?
O1 C3 N1 120.4(3) . . ?
O1 C3 C4 124.5(4) . . ?
N1 C3 C4 115.0(3) . . ?
C5 C4 C16 115.1(3) . . ?
C5 C4 C3 113.4(3) . . ?
C16 C4 C3 113.5(3) . . ?
C5 C4 H4 104.4 . . ?
C16 C4 H4 104.4 . . ?
C3 C4 H4 104.4 . . ?
C4 C5 C6 115.7(3) . . ?
C4 C5 H5A 108.4 . . ?
C6 C5 H5A 108.4 . . ?
C4 C5 H5B 108.4 . . ?
C6 C5 H5B 108.4 . . ?
H5A C5 H5B 107.4 . . ?
C7 C6 C8 119.8(3) . . ?
C7 C6 C5 115.3(3) . . ?
C8 C6 C5 124.9(3) . . ?
N2 C7 C6 130.9(3) . . ?
N2 C7 N1 107.9(3) . . ?
C6 C7 N1 121.1(3) . . ?
O2 C8 C6 123.1(3) . . ?
O2 C8 C9 117.5(3) . . ?
C6 C8 C9 119.4(3) . . ?
C14 C9 C10 117.5(3) . . ?
C14 C9 C8 119.6(3) . . ?
C10 C9 C8 122.9(3) . . ?
C11 C10 C9 121.3(3) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 120.4(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
O3 C12 C11 116.1(3) . . ?
O3 C12 C13 124.2(3) . . ?
C11 C12 C13 119.6(3) . . ?
C14 C13 C12 119.0(3) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C9 122.0(3) . . ?
C13 C14 H14 119.0 . . ?
C9 C14 H14 119.0 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 C16 H16A 109.5 . . ?
C4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
C7 N2 C1 C2 10.7(5) . . . . ?
C3 N1 C2 C1 172.1(3) . . . . ?
C7 N1 C2 C1 1.7(4) . . . . ?
N2 C1 C2 N1 -6.9(4) . . . . ?
C7 N1 C3 O1 176.2(3) . . . . ?
C2 N1 C3 O1 7.1(5) . . . . ?
C7 N1 C3 C4 -0.5(5) . . . . ?
C2 N1 C3 C4 -169.6(3) . . . . ?
O1 C3 C4 C5 153.8(4) . . . . ?
N1 C3 C4 C5 -29.6(5) . . . . ?
O1 C3 C4 C16 20.0(5) . . . . ?
N1 C3 C4 C16 -163.4(3) . . . . ?
C16 C4 C5 C6 177.5(3) . . . . ?
C3 C4 C5 C6 44.4(5) . . . . ?
C4 C5 C6 C7 -29.4(5) . . . . ?
C4 C5 C6 C8 151.3(3) . . . . ?
C1 N2 C7 C6 167.3(4) . . . . ?
C1 N2 C7 N1 -10.0(4) . . . . ?
C8 C6 C7 N2 1.2(6) . . . . ?
C5 C6 C7 N2 -178.1(3) . . . . ?
C8 C6 C7 N1 178.2(3) . . . . ?
C5 C6 C7 N1 -1.1(5) . . . . ?
C3 N1 C7 N2 -165.5(3) . . . . ?
C2 N1 C7 N2 4.8(4) . . . . ?
C3 N1 C7 C6 16.9(5) . . . . ?
C2 N1 C7 C6 -172.8(3) . . . . ?
C7 C6 C8 O2 8.8(5) . . . . ?
C5 C6 C8 O2 -171.9(3) . . . . ?
C7 C6 C8 C9 -171.6(3) . . . . ?
C5 C6 C8 C9 7.7(5) . . . . ?
O2 C8 C9 C14 46.4(4) . . . . ?
C6 C8 C9 C14 -133.2(3) . . . . ?
O2 C8 C9 C10 -132.3(3) . . . . ?
C6 C8 C9 C10 48.1(4) . . . . ?
C14 C9 C10 C11 0.4(4) . . . . ?
C8 C9 C10 C11 179.1(3) . . . . ?
C9 C10 C11 C12 2.0(5) . . . . ?
C15 O3 C12 C11 -177.7(3) . . . . ?
C15 O3 C12 C13 0.6(5) . . . . ?
C10 C11 C12 O3 176.5(3) . . . . ?
C10 C11 C12 C13 -1.8(5) . . . . ?
O3 C12 C13 C14 -179.0(3) . . . . ?
C11 C12 C13 C14 -0.8(5) . . . . ?
C12 C13 C14 C9 3.3(5) . . . . ?
C10 C9 C14 C13 -3.1(5) . . . . ?
C8 C9 C14 C13 178.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.15
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.047
