# Electronic Supplementary Material (ESI) for ChemComm.
# 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_en07310-73
_database_code_depnum_ccdc_archive 'CCDC 1437250'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2016-06-03 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_DENSX01_en07310-73          
;
PROBLEM: The ratio of the calculated to measured crystal density
RESPONSE: No measurement for crystal density.
;

# Added during the CSD deposition process: Monday 16th of November 2015 03:48:44 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-97
_chemical_name_systematic        en07310-73
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H20 N2 O4'
_chemical_formula_weight         340.37

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                   7.7910(4)
_cell_length_b                   13.1164(6)
_cell_length_c                   16.9526(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.8950(10)
_cell_angle_gamma                90.00
_cell_volume                     1719.85(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5922
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      24.14

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            27526
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         30.57
_reflns_number_total             5271
_reflns_number_gt                3532
_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)+(0.0730P)²+0.4280P] 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         5271
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1659
_refine_ls_wR_factor_gt          0.1438
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.44072(19) 0.69842(13) 0.23788(8) 0.0723(4) Uani 1 1 d . . .
O2 O 0.64491(19) 0.69177(17) 0.16474(10) 0.0948(6) Uani 1 1 d . . .
O3 O 0.33723(17) 0.66457(9) -0.02425(7) 0.0547(3) Uani 1 1 d . . .
O4 O 0.3292(2) 0.56238(9) 0.08126(9) 0.0723(4) Uani 1 1 d . . .
N1 N 0.21924(17) 0.87782(10) 0.16585(8) 0.0455(3) Uani 1 1 d . . .
N2 N 0.49657(19) 0.70873(11) 0.17494(8) 0.0509(3) Uani 1 1 d . . .
C1 C 0.4638(2) 0.82751(11) 0.06087(9) 0.0405(3) Uani 1 1 d . . .
H1A H 0.5753 0.8041 0.0481 0.049 Uiso 1 1 calc R . .
H1B H 0.3942 0.8464 0.0117 0.049 Uiso 1 1 calc R . .
C2 C 0.48807(18) 0.91848(11) 0.11468(8) 0.0386(3) Uani 1 1 d . . .
C3 C 0.6307(2) 0.98169(13) 0.11460(10) 0.0493(4) Uani 1 1 d . . .
H3A H 0.7128 0.9670 0.0807 0.059 Uiso 1 1 calc R . .
C4 C 0.6539(2) 1.06593(14) 0.16362(12) 0.0578(4) Uani 1 1 d . . .
H4A H 0.7490 1.1084 0.1622 0.069 Uiso 1 1 calc R . .
C5 C 0.5335(2) 1.08564(13) 0.21451(11) 0.0558(4) Uani 1 1 d . . .
H5A H 0.5482 1.1420 0.2480 0.067 Uiso 1 1 calc R . .
C6 C 0.3912(2) 1.02379(12) 0.21708(10) 0.0475(4) Uani 1 1 d . . .
H6A H 0.3122 1.0384 0.2525 0.057 Uiso 1 1 calc R . .
C7 C 0.36469(18) 0.93888(11) 0.16656(8) 0.0375(3) Uani 1 1 d . . .
C8 C 0.0937(2) 0.89671(16) 0.22055(12) 0.0596(5) Uani 1 1 d . . .
H8A H 0.1125 0.9633 0.2435 0.089 Uiso 1 1 calc R . .
H8B H 0.1062 0.8463 0.2619 0.089 Uiso 1 1 calc R . .
H8C H -0.0207 0.8931 0.1925 0.089 Uiso 1 1 calc R . .
C9 C 0.20185(18) 0.77832(11) 0.12706(8) 0.0382(3) Uani 1 1 d . . .
H9A H 0.1692 0.7292 0.1662 0.046 Uiso 1 1 calc R . .
C10 C 0.06010(18) 0.77730(11) 0.05701(8) 0.0383(3) Uani 1 1 d . . .
C11 C -0.0437(2) 0.69173(13) 0.04254(11) 0.0492(4) Uani 1 1 d . . .
H11A H -0.0301 0.6368 0.0774 0.059 Uiso 1 1 calc R . .
C12 C -0.1676(2) 0.68740(16) -0.02339(12) 0.0601(5) Uani 1 1 d . . .
H12A H -0.2355 0.6294 -0.0329 0.072 Uiso 1 1 calc R . .
C13 C -0.1902(2) 0.76880(17) -0.07475(11) 0.0622(5) Uani 1 1 d . . .
H13A H -0.2728 0.7657 -0.1191 0.075 Uiso 1 1 calc R . .
C14 C -0.0903(3) 0.85470(15) -0.06022(11) 0.0584(5) Uani 1 1 d . . .
H14A H -0.1062 0.9100 -0.0947 0.070 Uiso 1 1 calc R . .
C15 C 0.0338(2) 0.85944(12) 0.00538(10) 0.0472(4) Uani 1 1 d . . .
H15A H 0.1000 0.9181 0.0149 0.057 Uiso 1 1 calc R . .
C16 C 0.37519(19) 0.74247(11) 0.10109(8) 0.0383(3) Uani 1 1 d . . .
C17 C 0.3463(2) 0.64470(12) 0.05197(10) 0.0470(4) Uani 1 1 d . . .
C18 C 0.2853(3) 0.58193(16) -0.07991(13) 0.0729(6) Uani 1 1 d . . .
H18A H 0.1887 0.5445 -0.0630 0.087 Uiso 1 1 calc R . .
H18B H 0.3806 0.5350 -0.0828 0.087 Uiso 1 1 calc R . .
C19 C 0.2348(4) 0.6301(2) -0.15787(14) 0.0907(8) Uani 1 1 d . . .
H19A H 0.1994 0.5784 -0.1965 0.136 Uiso 1 1 calc R . .
H19B H 0.3315 0.6668 -0.1738 0.136 Uiso 1 1 calc R . .
H19C H 0.1407 0.6763 -0.1540 0.136 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 N2 1.2074(19) . ?
O2 N2 1.210(2) . ?
O3 C17 1.312(2) . ?
O3 C18 1.462(2) . ?
O4 C17 1.203(2) . ?
N1 C7 1.3865(19) . ?
N1 C8 1.447(2) . ?
N1 C9 1.4604(19) . ?
N2 C16 1.5405(19) . ?
C1 C2 1.500(2) . ?
C1 C16 1.516(2) . ?
C2 C3 1.387(2) . ?
C2 C7 1.404(2) . ?
C3 C4 1.381(3) . ?
C4 C5 1.373(3) . ?
C5 C6 1.378(3) . ?
C6 C7 1.405(2) . ?
C9 C10 1.522(2) . ?
C9 C16 1.543(2) . ?
C10 C15 1.388(2) . ?
C10 C11 1.388(2) . ?
C11 C12 1.388(2) . ?
C12 C13 1.376(3) . ?
C13 C14 1.375(3) . ?
C14 C15 1.384(2) . ?
C16 C17 1.531(2) . ?
C18 C19 1.475(4) . ?

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
C17 O3 C18 117.81(15) . . ?
C7 N1 C8 120.66(13) . . ?
C7 N1 C9 123.48(12) . . ?
C8 N1 C9 114.09(13) . . ?
O1 N2 O2 123.89(15) . . ?
O1 N2 C16 119.95(14) . . ?
O2 N2 C16 116.14(14) . . ?
C2 C1 C16 110.04(12) . . ?
C3 C2 C7 119.71(14) . . ?
C3 C2 C1 121.17(14) . . ?
C7 C2 C1 119.12(13) . . ?
C4 C3 C2 121.64(16) . . ?
C5 C4 C3 118.61(16) . . ?
C4 C5 C6 121.44(16) . . ?
C5 C6 C7 120.48(16) . . ?
N1 C7 C2 120.31(13) . . ?
N1 C7 C6 121.56(14) . . ?
C2 C7 C6 118.11(14) . . ?
N1 C9 C10 112.25(12) . . ?
N1 C9 C16 111.33(12) . . ?
C10 C9 C16 110.65(11) . . ?
C15 C10 C11 118.52(14) . . ?
C15 C10 C9 121.60(13) . . ?
C11 C10 C9 119.86(13) . . ?
C12 C11 C10 120.65(16) . . ?
C13 C12 C11 120.12(17) . . ?
C14 C13 C12 119.73(16) . . ?
C13 C14 C15 120.43(17) . . ?
C14 C15 C10 120.53(16) . . ?
C1 C16 C17 114.64(12) . . ?
C1 C16 N2 107.97(12) . . ?
C17 C16 N2 103.73(12) . . ?
C1 C16 C9 111.44(12) . . ?
C17 C16 C9 109.50(12) . . ?
N2 C16 C9 109.18(11) . . ?
O4 C17 O3 126.13(16) . . ?
O4 C17 C16 122.95(15) . . ?
O3 C17 C16 110.88(13) . . ?
O3 C18 C19 106.51(18) . . ?

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
C16 C1 C2 C3 146.62(14) . . . . ?
C16 C1 C2 C7 -32.65(18) . . . . ?
C7 C2 C3 C4 -1.1(2) . . . . ?
C1 C2 C3 C4 179.67(15) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
C8 N1 C7 C2 178.38(15) . . . . ?
C9 N1 C7 C2 14.5(2) . . . . ?
C8 N1 C7 C6 -3.3(2) . . . . ?
C9 N1 C7 C6 -167.20(14) . . . . ?
C3 C2 C7 N1 178.37(14) . . . . ?
C1 C2 C7 N1 -2.4(2) . . . . ?
C3 C2 C7 C6 0.0(2) . . . . ?
C1 C2 C7 C6 179.25(13) . . . . ?
C5 C6 C7 N1 -177.47(15) . . . . ?
C5 C6 C7 C2 0.9(2) . . . . ?
C7 N1 C9 C10 -114.38(15) . . . . ?
C8 N1 C9 C10 80.74(17) . . . . ?
C7 N1 C9 C16 10.28(19) . . . . ?
C8 N1 C9 C16 -154.59(14) . . . . ?
N1 C9 C10 C15 39.36(19) . . . . ?
C16 C9 C10 C15 -85.68(17) . . . . ?
N1 C9 C10 C11 -142.22(14) . . . . ?
C16 C9 C10 C11 92.74(16) . . . . ?
C15 C10 C11 C12 1.8(2) . . . . ?
C9 C10 C11 C12 -176.65(15) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C13 C14 C15 C10 0.6(3) . . . . ?
C11 C10 C15 C14 -1.7(2) . . . . ?
C9 C10 C15 C14 176.74(15) . . . . ?
C2 C1 C16 C17 -179.03(12) . . . . ?
C2 C1 C16 N2 -64.00(15) . . . . ?
C2 C1 C16 C9 55.90(15) . . . . ?
O1 N2 C16 C1 132.59(17) . . . . ?
O2 N2 C16 C1 -49.1(2) . . . . ?
O1 N2 C16 C17 -105.38(18) . . . . ?
O2 N2 C16 C17 73.0(2) . . . . ?
O1 N2 C16 C9 11.3(2) . . . . ?
O2 N2 C16 C9 -170.38(17) . . . . ?
N1 C9 C16 C1 -45.24(16) . . . . ?
C10 C9 C16 C1 80.32(14) . . . . ?
N1 C9 C16 C17 -173.13(12) . . . . ?
C10 C9 C16 C17 -47.57(15) . . . . ?
N1 C9 C16 N2 73.94(15) . . . . ?
C10 C9 C16 N2 -160.50(12) . . . . ?
C18 O3 C17 O4 6.3(3) . . . . ?
C18 O3 C17 C16 -171.39(15) . . . . ?
C1 C16 C17 O4 156.34(17) . . . . ?
N2 C16 C17 O4 38.9(2) . . . . ?
C9 C16 C17 O4 -77.6(2) . . . . ?
C1 C16 C17 O3 -25.87(18) . . . . ?
N2 C16 C17 O3 -143.35(13) . . . . ?
C9 C16 C17 O3 100.21(15) . . . . ?
C17 O3 C18 C19 163.28(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        30.57
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.041
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
