# 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_sad
_database_code_depnum_ccdc_archive 'CCDC 1527952'
_audit_update_record             
;
2017-03-20 deposited with the CCDC.
2017-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 N2 O3'
_chemical_formula_weight         310.34

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   13.8048(3)
_cell_length_b                   15.2327(3)
_cell_length_c                   15.2102(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3198.47(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7244/2439
_cell_measurement_theta_min      5.21
_cell_measurement_theta_max      62.65

_exptl_crystal_description       plane
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8401
_exptl_absorpt_correction_T_max  0.8810
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SMART (Bruker, 1998)'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7244
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.21
_diffrn_reflns_theta_max         62.65
_reflns_number_total             2439
_reflns_number_gt                2126
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAIRT (Bruker, 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0544P)²+0.5863P] 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         2439
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1066
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
O1 O 0.39143(9) 0.72877(8) -0.02420(11) 0.0796(4) Uani 1 1 d . . .
O2 O 0.16696(7) 0.45592(9) 0.21384(7) 0.0626(3) Uani 1 1 d . . .
O3 O 0.32496(8) 0.43938(10) 0.18972(8) 0.0741(4) Uani 1 1 d . . .
N1 N 0.32825(8) 0.59334(8) 0.00933(9) 0.0490(3) Uani 1 1 d . . .
C1 C 0.39027(11) 0.64981(11) -0.03490(12) 0.0568(4) Uani 1 1 d . . .
C2 C 0.44985(11) 0.59624(10) -0.09742(11) 0.0558(4) Uani 1 1 d . . .
H2A H 0.4393 0.6148 -0.1577 0.067 Uiso 1 1 calc R . .
H2B H 0.5183 0.6010 -0.0838 0.067 Uiso 1 1 calc R . .
C3 C 0.41446(10) 0.50449(10) -0.08340(10) 0.0468(4) Uani 1 1 d . . .
C4 C 0.34042(9) 0.50545(10) -0.02087(9) 0.0429(3) Uani 1 1 d . . .
C5 C 0.29225(10) 0.42910(9) 0.00344(9) 0.0438(3) Uani 1 1 d . . .
C6 C 0.32185(11) 0.35260(10) -0.03916(10) 0.0502(4) Uani 1 1 d . . .
H6A H 0.2899 0.3006 -0.0256 0.060 Uiso 1 1 calc R . .
C7 C 0.39625(12) 0.34929(11) -0.10066(10) 0.0536(4) Uani 1 1 d . . .
C8 C 0.44258(11) 0.42747(11) -0.12241(10) 0.0528(4) Uani 1 1 d . . .
H8A H 0.4926 0.4275 -0.1634 0.063 Uiso 1 1 calc R . .
C9 C 0.42542(16) 0.26291(12) -0.14118(13) 0.0722(5) Uani 1 1 d . . .
H9A H 0.3854 0.2169 -0.1180 0.108 Uiso 1 1 calc R . .
H9B H 0.4920 0.2509 -0.1275 0.108 Uiso 1 1 calc R . .
H9C H 0.4175 0.2659 -0.2038 0.108 Uiso 1 1 calc R . .
C10 C 0.25453(11) 0.62743(9) 0.06522(11) 0.0494(4) Uani 1 1 d . . .
C11 C 0.27833(15) 0.66247(13) 0.14474(14) 0.0735(5) Uani 1 1 d . . .
H11A H 0.3418 0.6606 0.1652 0.088 Uiso 1 1 calc R . .
C12 C 0.20617(19) 0.70063(16) 0.19386(17) 0.0955(7) Uani 1 1 d . . .
H12A H 0.2200 0.7256 0.2482 0.115 Uiso 1 1 calc R . .
C13 C 0.11440(19) 0.70127(14) 0.16175(18) 0.0916(8) Uani 1 1 d . . .
H13A H 0.0644 0.7270 0.1936 0.110 Uiso 1 1 calc R . .
C14 C 0.09682(14) 0.66366(14) 0.08230(17) 0.0810(6) Uani 1 1 d . . .
H14A H 0.0335 0.6636 0.0614 0.097 Uiso 1 1 calc R . .
N2 N 0.16568(9) 0.62654(10) 0.03233(11) 0.0635(4) Uani 1 1 d . . .
C15 C 0.21207(10) 0.42382(10) 0.07035(10) 0.0461(4) Uani 1 1 d . . .
H15A H 0.1626 0.4663 0.0550 0.055 Uiso 1 1 calc R . .
H15B H 0.1829 0.3660 0.0672 0.055 Uiso 1 1 calc R . .
C16 C 0.24364(11) 0.44033(10) 0.16320(10) 0.0480(4) Uani 1 1 d . . .
C17 C 0.18487(13) 0.47420(15) 0.30585(11) 0.0700(5) Uani 1 1 d . . .
H17A H 0.2334 0.5199 0.3118 0.084 Uiso 1 1 calc R . .
H17B H 0.2082 0.4219 0.3354 0.084 Uiso 1 1 calc R . .
C18 C 0.09144(16) 0.5033(2) 0.34508(13) 0.0959(8) Uani 1 1 d . . .
H18A H 0.1009 0.5166 0.4062 0.144 Uiso 1 1 calc R . .
H18B H 0.0443 0.4574 0.3393 0.144 Uiso 1 1 calc R . .
H18C H 0.0689 0.5549 0.3150 0.144 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
O1 C1 1.214(2) . ?
O2 C16 1.3306(18) . ?
O2 C17 1.448(2) . ?
O3 C16 1.1930(18) . ?
N1 C1 1.388(2) . ?
N1 C10 1.4241(19) . ?
N1 C4 1.4253(19) . ?
C1 C2 1.499(2) . ?
C2 C3 1.496(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C8 1.371(2) . ?
C3 C4 1.396(2) . ?
C4 C5 1.390(2) . ?
C5 C6 1.395(2) . ?
C5 C15 1.506(2) . ?
C6 C7 1.390(2) . ?
C6 H6A 0.9300 . ?
C7 C8 1.392(2) . ?
C7 C9 1.508(2) . ?
C8 H8A 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N2 1.325(2) . ?
C10 C11 1.362(3) . ?
C11 C12 1.374(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.358(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.359(4) . ?
C13 H13A 0.9300 . ?
C14 N2 1.342(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.499(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C17 C18 1.489(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C16 O2 C17 117.25(12) . . ?
C1 N1 C10 120.29(13) . . ?
C1 N1 C4 110.69(12) . . ?
C10 N1 C4 128.25(12) . . ?
O1 C1 N1 123.87(16) . . ?
O1 C1 C2 128.12(15) . . ?
N1 C1 C2 107.98(13) . . ?
C3 C2 C1 103.82(12) . . ?
C3 C2 H2A 111.0 . . ?
C1 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
C1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
C8 C3 C4 120.73(14) . . ?
C8 C3 C2 130.20(14) . . ?
C4 C3 C2 109.06(13) . . ?
C5 C4 C3 121.51(14) . . ?
C5 C4 N1 130.09(13) . . ?
C3 C4 N1 108.40(12) . . ?
C4 C5 C6 115.82(13) . . ?
C4 C5 C15 125.18(13) . . ?
C6 C5 C15 119.00(13) . . ?
C7 C6 C5 124.01(14) . . ?
C7 C6 H6A 118.0 . . ?
C5 C6 H6A 118.0 . . ?
C6 C7 C8 117.94(14) . . ?
C6 C7 C9 120.26(15) . . ?
C8 C7 C9 121.79(15) . . ?
C3 C8 C7 119.95(14) . . ?
C3 C8 H8A 120.0 . . ?
C7 C8 H8A 120.0 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C11 124.23(16) . . ?
N2 C10 N1 115.63(15) . . ?
C11 C10 N1 120.04(15) . . ?
C10 C11 C12 118.3(2) . . ?
C10 C11 H11A 120.9 . . ?
C12 C11 H11A 120.9 . . ?
C13 C12 C11 118.9(2) . . ?
C13 C12 H12A 120.5 . . ?
C11 C12 H12A 120.5 . . ?
C12 C13 C14 118.90(19) . . ?
C12 C13 H13A 120.5 . . ?
C14 C13 H13A 120.5 . . ?
N2 C14 C13 123.7(2) . . ?
N2 C14 H14A 118.2 . . ?
C13 C14 H14A 118.2 . . ?
C10 N2 C14 115.96(18) . . ?
C16 C15 C5 114.46(12) . . ?
C16 C15 H15A 108.6 . . ?
C5 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C5 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
O3 C16 O2 123.71(15) . . ?
O3 C16 C15 126.16(14) . . ?
O2 C16 C15 110.12(12) . . ?
O2 C17 C18 107.26(15) . . ?
O2 C17 H17A 110.3 . . ?
C18 C17 H17A 110.3 . . ?
O2 C17 H17B 110.3 . . ?
C18 C17 H17B 110.3 . . ?
H17A C17 H17B 108.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C10 N1 C1 O1 6.0(3) . . . . ?
C4 N1 C1 O1 176.74(17) . . . . ?
C10 N1 C1 C2 -172.18(13) . . . . ?
C4 N1 C1 C2 -1.46(18) . . . . ?
O1 C1 C2 C3 -178.02(18) . . . . ?
N1 C1 C2 C3 0.07(17) . . . . ?
C1 C2 C3 C8 -179.89(16) . . . . ?
C1 C2 C3 C4 1.35(17) . . . . ?
C8 C3 C4 C5 -0.6(2) . . . . ?
C2 C3 C4 C5 178.33(13) . . . . ?
C8 C3 C4 N1 178.85(13) . . . . ?
C2 C3 C4 N1 -2.26(17) . . . . ?
C1 N1 C4 C5 -178.30(15) . . . . ?
C10 N1 C4 C5 -8.5(3) . . . . ?
C1 N1 C4 C3 2.36(17) . . . . ?
C10 N1 C4 C3 172.15(14) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
N1 C4 C5 C6 -179.99(14) . . . . ?
C3 C4 C5 C15 179.73(14) . . . . ?
N1 C4 C5 C15 0.5(2) . . . . ?
C4 C5 C6 C7 1.7(2) . . . . ?
C15 C5 C6 C7 -178.66(14) . . . . ?
C5 C6 C7 C8 -1.5(2) . . . . ?
C5 C6 C7 C9 177.98(16) . . . . ?
C4 C3 C8 C7 0.9(2) . . . . ?
C2 C3 C8 C7 -177.73(16) . . . . ?
C6 C7 C8 C3 0.1(2) . . . . ?
C9 C7 C8 C3 -179.35(16) . . . . ?
C1 N1 C10 N2 103.10(17) . . . . ?
C4 N1 C10 N2 -65.8(2) . . . . ?
C1 N1 C10 C11 -73.4(2) . . . . ?
C4 N1 C10 C11 117.68(19) . . . . ?
N2 C10 C11 C12 -1.0(3) . . . . ?
N1 C10 C11 C12 175.18(18) . . . . ?
C10 C11 C12 C13 0.5(4) . . . . ?
C11 C12 C13 C14 0.4(4) . . . . ?
C12 C13 C14 N2 -1.0(3) . . . . ?
C11 C10 N2 C14 0.4(3) . . . . ?
N1 C10 N2 C14 -175.89(14) . . . . ?
C13 C14 N2 C10 0.6(3) . . . . ?
C4 C5 C15 C16 -68.93(19) . . . . ?
C6 C5 C15 C16 111.52(16) . . . . ?
C17 O2 C16 O3 1.2(3) . . . . ?
C17 O2 C16 C15 -179.34(15) . . . . ?
C5 C15 C16 O3 -15.9(2) . . . . ?
C5 C15 C16 O2 164.64(13) . . . . ?
C16 O2 C17 C18 171.05(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.948
_diffrn_reflns_theta_full        62.65
_diffrn_measured_fraction_theta_full 0.948
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.026
