# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1508095'
_audit_update_record             
;
2016-10-04 deposited with the CCDC.
2016-11-29 downloaded from the CCDC.
;
_audit_creation_date             2016-01-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H16 N2 O3'
_chemical_formula_sum            'C19 H16 N2 O3'
_chemical_formula_weight         320.34
_chemical_melting_point          ?
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   6.1225(6)
_cell_length_b                   16.4269(15)
_cell_length_c                   15.5669(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.055(3)
_cell_angle_gamma                90.00
_cell_volume                     1563.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9963
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.137
_cell_measurement_theta_min      3.333
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0651 before and 0.0576 after correction.
The Ratio of minimum to maximum transmission is 0.9301.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.317
_exptl_crystal_size_mid          0.309
_exptl_crystal_size_min          0.112
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26832
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         3.33
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2065
_reflns_number_total             2751
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2751
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0455
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0779P)²+0.3510P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1390
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 C19(H19A,H19B,H19C)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C10(H10), C4(H4), C11(H11), C6(H6), C16(H16), C14(H14), C3(H3),
 C5(H5), C15(H15)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O2 O 0.1630(2) 0.61954(10) 0.56868(9) 0.0671(4) Uani 1 d . . .
O1 O 1.0738(3) 0.49540(9) 0.76221(11) 0.0740(5) Uani 1 d . . .
N1 N 0.9561(2) 0.62575(9) 0.76285(9) 0.0478(4) Uani 1 d . . .
H1 H 0.9904 0.6746 0.7823 0.057 Uiso 1 calc . . R
O3 O 0.3199(3) 0.62785(10) 0.44282(10) 0.0753(5) Uani 1 d . . .
N2 N 0.7045(3) 0.75841(9) 0.75294(10) 0.0541(4) Uani 1 d . . .
C7 C 1.2860(3) 0.58914(11) 0.84701(11) 0.0459(4) Uani 1 d . . .
C17 C 0.6314(3) 0.69182(11) 0.70744(11) 0.0458(4) Uani 1 d . . .
C13 C 0.4285(3) 0.69187(12) 0.65895(11) 0.0485(5) Uani 1 d . . .
C18 C 0.1581(3) 0.62357(11) 0.48182(13) 0.0551(5) Uani 1 d . . .
C9 C 0.7633(3) 0.62045(11) 0.71087(11) 0.0459(4) Uani 1 d . . .
C8 C 1.0971(3) 0.56536(12) 0.78717(12) 0.0496(5) Uani 1 d . . .
C10 C 0.6948(3) 0.55250(12) 0.66602(12) 0.0545(5) Uani 1 d . . .
H10 H 0.7825 0.5048 0.6681 0.065 Uiso 1 calc . . R
C12 C 0.3686(3) 0.62018(13) 0.61346(12) 0.0535(5) Uani 1 d . . .
C2 C 1.6459(3) 0.62156(13) 0.96134(12) 0.0559(5) Uani 1 d . . .
C4 C 1.3124(3) 0.66464(12) 0.88554(12) 0.0539(5) Uani 1 d . . .
H4 H 1.2079 0.7063 0.8731 0.065 Uiso 1 calc . . R
C11 C 0.4953(3) 0.55324(13) 0.61701(12) 0.0582(5) Uani 1 d . . .
H11 H 0.4494 0.5059 0.5860 0.070 Uiso 1 calc . . R
C6 C 1.4441(3) 0.53091(12) 0.86515(13) 0.0574(5) Uani 1 d . . .
H6 H 1.4310 0.4788 0.8388 0.069 Uiso 1 calc . . R
C16 C 0.5762(3) 0.82229(12) 0.75296(14) 0.0640(6) Uani 1 d . . .
H16 H 0.6262 0.8687 0.7846 0.077 Uiso 1 calc . . R
C14 C 0.2986(3) 0.76218(13) 0.66207(13) 0.0592(5) Uani 1 d . . .
H14 H 0.1609 0.7644 0.6310 0.071 Uiso 1 calc . . R
C3 C 1.4896(3) 0.68010(13) 0.94203(13) 0.0585(5) Uani 1 d . . .
H3 H 1.5039 0.7322 0.9681 0.070 Uiso 1 calc . . R
C5 C 1.6211(3) 0.54734(14) 0.92110(14) 0.0648(6) Uani 1 d . . .
H5 H 1.7285 0.5064 0.9321 0.078 Uiso 1 calc . . R
C15 C 0.3703(4) 0.82664(13) 0.70948(14) 0.0666(6) Uani 1 d . . .
H15 H 0.2827 0.8741 0.7133 0.080 Uiso 1 calc . . R
C1 C 1.8353(4) 0.63908(17) 1.02497(15) 0.0792(7) Uani 1 d . . .
H1A H 1.9423 0.6736 0.9977 0.119 Uiso 1 calc . . GR
H1B H 1.9049 0.5878 1.0433 0.119 Uiso 1 calc . . GR
H1C H 1.7815 0.6672 1.0752 0.119 Uiso 1 calc . . GR
C19 C -0.0703(4) 0.62165(15) 0.44424(17) 0.0804(7) Uani 1 d . . .
H19A H -0.1264 0.5672 0.4470 0.121 Uiso 1 d . . R
H19B H -0.0723 0.6390 0.3853 0.121 Uiso 1 d . . R
H19C H -0.1596 0.6575 0.4762 0.121 Uiso 1 d . . 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
O2 C18 1.352(2) . ?
O2 C12 1.406(2) . ?
O1 C8 1.219(2) . ?
N1 H1 0.8800 . ?
N1 C9 1.398(2) . ?
N1 C8 1.356(2) . ?
O3 C18 1.191(2) . ?
N2 C17 1.365(2) . ?
N2 C16 1.311(2) . ?
C7 C8 1.497(2) . ?
C7 C4 1.383(3) . ?
C7 C6 1.379(3) . ?
C17 C13 1.419(2) . ?
C17 C9 1.423(3) . ?
C13 C12 1.412(3) . ?
C13 C14 1.405(3) . ?
C18 C19 1.487(3) . ?
C9 C10 1.370(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.405(3) . ?
C12 C11 1.345(3) . ?
C2 C3 1.378(3) . ?
C2 C5 1.375(3) . ?
C2 C1 1.512(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.383(3) . ?
C11 H11 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.381(3) . ?
C16 H16 0.9500 . ?
C16 C15 1.400(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.351(3) . ?
C3 H3 0.9500 . ?
C5 H5 0.9500 . ?
C15 H15 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9599 . ?

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
C18 O2 C12 117.83(15) . . ?
C9 N1 H1 115.8 . . ?
C8 N1 H1 115.8 . . ?
C8 N1 C9 128.44(16) . . ?
C16 N2 C17 117.51(16) . . ?
C4 C7 C8 124.91(16) . . ?
C6 C7 C8 117.17(17) . . ?
C6 C7 C4 117.92(17) . . ?
N2 C17 C13 121.92(17) . . ?
N2 C17 C9 118.12(16) . . ?
C13 C17 C9 119.96(16) . . ?
C12 C13 C17 117.57(17) . . ?
C14 C13 C17 117.61(17) . . ?
C14 C13 C12 124.79(17) . . ?
O2 C18 C19 111.25(19) . . ?
O3 C18 O2 122.53(17) . . ?
O3 C18 C19 126.2(2) . . ?
N1 C9 C17 115.49(16) . . ?
C10 C9 N1 124.85(17) . . ?
C10 C9 C17 119.65(16) . . ?
O1 C8 N1 122.59(17) . . ?
O1 C8 C7 121.18(17) . . ?
N1 C8 C7 116.23(16) . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.19(19) . . ?
C11 C10 H10 119.9 . . ?
O2 C12 C13 117.16(17) . . ?
C11 C12 O2 120.89(18) . . ?
C11 C12 C13 121.81(17) . . ?
C3 C2 C1 120.6(2) . . ?
C5 C2 C3 117.44(18) . . ?
C5 C2 C1 121.94(19) . . ?
C7 C4 H4 119.7 . . ?
C3 C4 C7 120.67(18) . . ?
C3 C4 H4 119.7 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.80(19) . . ?
C12 C11 H11 119.6 . . ?
C7 C6 H6 119.6 . . ?
C7 C6 C5 120.83(19) . . ?
C5 C6 H6 119.6 . . ?
N2 C16 H16 117.8 . . ?
N2 C16 C15 124.38(19) . . ?
C15 C16 H16 117.8 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.69(18) . . ?
C15 C14 H14 120.2 . . ?
C2 C3 C4 121.49(19) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C2 C5 C6 121.62(19) . . ?
C2 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C16 C15 H15 120.6 . . ?
C14 C15 C16 118.8(2) . . ?
C14 C15 H15 120.6 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
O2 C12 C11 C10 -176.17(17) . . . . ?
N1 C9 C10 C11 178.64(17) . . . . ?
N2 C17 C13 C12 179.42(16) . . . . ?
N2 C17 C13 C14 -2.7(3) . . . . ?
N2 C17 C9 N1 1.1(2) . . . . ?
N2 C17 C9 C10 179.97(16) . . . . ?
N2 C16 C15 C14 -1.9(3) . . . . ?
C7 C4 C3 C2 0.5(3) . . . . ?
C7 C6 C5 C2 0.6(3) . . . . ?
C17 N2 C16 C15 -0.1(3) . . . . ?
C17 C13 C12 O2 177.27(15) . . . . ?
C17 C13 C12 C11 1.5(3) . . . . ?
C17 C13 C14 C15 0.7(3) . . . . ?
C17 C9 C10 C11 -0.1(3) . . . . ?
C13 C17 C9 N1 -177.77(15) . . . . ?
C13 C17 C9 C10 1.1(3) . . . . ?
C13 C12 C11 C10 -0.6(3) . . . . ?
C13 C14 C15 C16 1.5(3) . . . . ?
C18 O2 C12 C13 107.65(19) . . . . ?
C18 O2 C12 C11 -76.5(2) . . . . ?
C9 N1 C8 O1 2.8(3) . . . . ?
C9 N1 C8 C7 -177.23(16) . . . . ?
C9 C17 C13 C12 -1.7(2) . . . . ?
C9 C17 C13 C14 176.12(16) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C8 N1 C9 C17 170.57(16) . . . . ?
C8 N1 C9 C10 -8.2(3) . . . . ?
C8 C7 C4 C3 178.05(18) . . . . ?
C8 C7 C6 C5 -178.64(18) . . . . ?
C12 O2 C18 O3 -0.3(3) . . . . ?
C12 O2 C18 C19 179.57(17) . . . . ?
C12 C13 C14 C15 178.37(18) . . . . ?
C4 C7 C8 O1 -172.78(19) . . . . ?
C4 C7 C8 N1 7.3(3) . . . . ?
C4 C7 C6 C5 1.0(3) . . . . ?
C6 C7 C8 O1 6.8(3) . . . . ?
C6 C7 C8 N1 -173.14(16) . . . . ?
C6 C7 C4 C3 -1.5(3) . . . . ?
C16 N2 C17 C13 2.4(3) . . . . ?
C16 N2 C17 C9 -176.44(17) . . . . ?
C14 C13 C12 O2 -0.4(3) . . . . ?
C14 C13 C12 C11 -176.19(18) . . . . ?
C3 C2 C5 C6 -1.6(3) . . . . ?
C5 C2 C3 C4 1.1(3) . . . . ?
C1 C2 C3 C4 -178.5(2) . . . . ?
C1 C2 C5 C6 177.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
