# Electronic Supplementary Material (ESI) for Chemical Science.
# 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 
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data_6928oota
_database_code_depnum_ccdc_archive 'CCDC 1544882'
_audit_update_record             
;
2017-04-19 deposited with the CCDC.
2017-06-15 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         'C16 H10 N2 O3'
_chemical_formula_sum            'C16 H10 N2 O3'
_chemical_formula_weight         278.26

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      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'F d d 2'

_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, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   23.536(12)
_cell_length_b                   42.75(2)
_cell_length_c                   5.126(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5158(5)
_cell_formula_units_Z            16
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2015
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_F_000             2304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.799
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            11161
_diffrn_reflns_av_unetI/netI     0.0754
_diffrn_reflns_av_R_equivalents  0.0934
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -51
_diffrn_reflns_limit_k_max       51
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.343
_diffrn_reflns_theta_max         25.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2364
_reflns_number_gt                1918
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_fraction_full    0.980

_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       'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXTL-v6.1
_computing_publication_material  YADOKARI-XG
_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)+(0.0340P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 707 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.0(10)
_chemical_absolute_configuration .
_refine_ls_number_reflns         2364
_refine_ls_number_parameters     191
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0816
_refine_ls_wR_factor_gt          0.0805
_refine_ls_goodness_of_fit_ref   0.889
_refine_ls_restrained_S_all      0.889
_refine_ls_shift/su_max          0.001
_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
N1 N 0.31360(11) 0.69916(6) -0.0513(7) 0.0363(8) Uani 1 1 d . . . . .
C1 C 0.34374(13) 0.68924(7) 0.1032(8) 0.0269(8) Uani 1 1 d . . . . .
C2 C 0.38150(12) 0.67662(7) 0.2992(7) 0.0233(7) Uani 1 1 d . . . . .
C3 C 0.36596(12) 0.65038(7) 0.4439(7) 0.0250(8) Uani 1 1 d . . . . .
H1 H 0.3301 0.6408 0.4138 0.030 Uiso 1 1 calc R U . . .
C4 C 0.40205(12) 0.63808(6) 0.6310(7) 0.0239(7) Uani 1 1 d . . . . .
H2 H 0.3911 0.6202 0.7293 0.029 Uiso 1 1 calc R U . . .
C5 C 0.45465(12) 0.65215(6) 0.6737(7) 0.0229(7) Uani 1 1 d . . . . .
C6 C 0.46973(11) 0.67874(6) 0.5276(7) 0.0208(7) Uani 1 1 d . . . . .
C7 C 0.43418(12) 0.69096(6) 0.3439(7) 0.0212(7) Uani 1 1 d . . . . .
H3 H 0.4450 0.7090 0.2475 0.025 Uiso 1 1 calc R U . . .
O1 O 0.49395(8) 0.64262(4) 0.8496(5) 0.0279(5) Uani 1 1 d . . . . .
C8 C 0.48010(14) 0.61647(7) 1.0137(7) 0.0316(8) Uani 1 1 d . . . . .
H4 H 0.4444 0.6207 1.1055 0.047 Uiso 1 1 calc R U . . .
H5 H 0.5106 0.6133 1.1412 0.047 Uiso 1 1 calc R U . . .
H6 H 0.4759 0.5976 0.9064 0.047 Uiso 1 1 calc R U . . .
N2 N 0.52273(9) 0.69381(5) 0.5893(5) 0.0195(6) Uani 1 1 d . . . . .
C9 C 0.57651(12) 0.68216(7) 0.5165(7) 0.0221(7) Uani 1 1 d . . . . .
O2 O 0.58432(8) 0.66184(5) 0.3565(5) 0.0293(6) Uani 1 1 d . . . . .
C10 C 0.61804(12) 0.69952(6) 0.6789(7) 0.0223(7) Uani 1 1 d . . . . .
C11 C 0.67649(12) 0.69742(7) 0.6922(8) 0.0303(8) Uani 1 1 d . . . . .
H7 H 0.6971 0.6843 0.5767 0.036 Uiso 1 1 calc R U . . .
C12 C 0.70422(13) 0.71523(7) 0.8804(8) 0.0326(9) Uani 1 1 d . . . . .
H8 H 0.7444 0.7140 0.8939 0.039 Uiso 1 1 calc R U . . .
C13 C 0.67474(12) 0.73467(7) 1.0484(7) 0.0274(8) Uani 1 1 d . . . . .
H9 H 0.6948 0.7464 1.1760 0.033 Uiso 1 1 calc R U . . .
C14 C 0.61579(12) 0.73718(7) 1.0320(7) 0.0237(7) Uani 1 1 d . . . . .
H10 H 0.5951 0.7506 1.1452 0.028 Uiso 1 1 calc R U . . .
C15 C 0.58851(11) 0.71942(6) 0.8451(7) 0.0203(7) Uani 1 1 d . . . . .
C16 C 0.52701(12) 0.71619(6) 0.7901(6) 0.0212(7) Uani 1 1 d . . . . .
O3 O 0.48680(8) 0.72907(4) 0.8896(4) 0.0235(5) Uani 1 1 d . . . . .


_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 C1 1.145(4) . ?
C1 C2 1.446(5) . ?
C2 C3 1.394(4) . ?
C2 C7 1.402(4) . ?
C3 C4 1.385(5) . ?
C3 H1 0.9500 . ?
C4 C5 1.394(4) . ?
C4 H2 0.9500 . ?
C5 O1 1.354(4) . ?
C5 C6 1.407(4) . ?
C6 C7 1.364(4) . ?
C6 N2 1.439(4) . ?
C7 H3 0.9500 . ?
O1 C8 1.437(4) . ?
C8 H4 0.9800 . ?
C8 H5 0.9800 . ?
C8 H6 0.9800 . ?
N2 C16 1.409(4) . ?
N2 C9 1.410(4) . ?
C9 O2 1.209(4) . ?
C9 C10 1.483(4) . ?
C10 C11 1.380(4) . ?
C10 C15 1.390(4) . ?
C11 C12 1.392(5) . ?
C11 H7 0.9500 . ?
C12 C13 1.383(5) . ?
C12 H8 0.9500 . ?
C13 C14 1.394(4) . ?
C13 H9 0.9500 . ?
C14 C15 1.380(4) . ?
C14 H10 0.9500 . ?
C15 C16 1.481(4) . ?
C16 O3 1.208(3) . ?

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
N1 C1 C2 179.6(4) . . ?
C3 C2 C7 119.8(3) . . ?
C3 C2 C1 120.6(3) . . ?
C7 C2 C1 119.6(3) . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H1 119.6 . . ?
C2 C3 H1 119.6 . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 H2 120.4 . . ?
C5 C4 H2 120.4 . . ?
O1 C5 C4 125.5(3) . . ?
O1 C5 C6 115.1(3) . . ?
C4 C5 C6 119.3(3) . . ?
C7 C6 C5 121.5(3) . . ?
C7 C6 N2 120.8(3) . . ?
C5 C6 N2 117.6(3) . . ?
C6 C7 C2 119.2(3) . . ?
C6 C7 H3 120.4 . . ?
C2 C7 H3 120.4 . . ?
C5 O1 C8 118.0(2) . . ?
O1 C8 H4 109.5 . . ?
O1 C8 H5 109.5 . . ?
H4 C8 H5 109.5 . . ?
O1 C8 H6 109.5 . . ?
H4 C8 H6 109.5 . . ?
H5 C8 H6 109.5 . . ?
C16 N2 C9 111.7(2) . . ?
C16 N2 C6 121.8(2) . . ?
C9 N2 C6 124.2(2) . . ?
O2 C9 N2 124.7(3) . . ?
O2 C9 C10 129.8(3) . . ?
N2 C9 C10 105.4(3) . . ?
C11 C10 C15 120.5(3) . . ?
C11 C10 C9 130.7(3) . . ?
C15 C10 C9 108.7(3) . . ?
C10 C11 C12 117.8(3) . . ?
C10 C11 H7 121.1 . . ?
C12 C11 H7 121.1 . . ?
C13 C12 C11 121.7(3) . . ?
C13 C12 H8 119.2 . . ?
C11 C12 H8 119.2 . . ?
C12 C13 C14 120.5(3) . . ?
C12 C13 H9 119.7 . . ?
C14 C13 H9 119.7 . . ?
C15 C14 C13 117.5(3) . . ?
C15 C14 H10 121.2 . . ?
C13 C14 H10 121.2 . . ?
C14 C15 C10 122.0(3) . . ?
C14 C15 C16 129.6(3) . . ?
C10 C15 C16 108.3(3) . . ?
O3 C16 N2 124.2(3) . . ?
O3 C16 C15 130.0(3) . . ?
N2 C16 C15 105.8(2) . . ?

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 C2 C3 C4 -0.4(5) . . . . ?
C1 C2 C3 C4 179.7(3) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C4 C5 O1 -180.0(3) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
O1 C5 C6 C7 -179.8(3) . . . . ?
C4 C5 C6 C7 -0.4(4) . . . . ?
O1 C5 C6 N2 -3.5(4) . . . . ?
C4 C5 C6 N2 176.0(3) . . . . ?
C5 C6 C7 C2 -0.2(4) . . . . ?
N2 C6 C7 C2 -176.5(3) . . . . ?
C3 C2 C7 C6 0.6(4) . . . . ?
C1 C2 C7 C6 -179.4(3) . . . . ?
C4 C5 O1 C8 -2.3(4) . . . . ?
C6 C5 O1 C8 177.2(3) . . . . ?
C7 C6 N2 C16 91.4(4) . . . . ?
C5 C6 N2 C16 -85.0(3) . . . . ?
C7 C6 N2 C9 -107.7(3) . . . . ?
C5 C6 N2 C9 75.9(4) . . . . ?
C16 N2 C9 O2 176.9(3) . . . . ?
C6 N2 C9 O2 14.3(5) . . . . ?
C16 N2 C9 C10 -2.1(3) . . . . ?
C6 N2 C9 C10 -164.7(3) . . . . ?
O2 C9 C10 C11 0.2(6) . . . . ?
N2 C9 C10 C11 179.0(3) . . . . ?
O2 C9 C10 C15 -176.6(3) . . . . ?
N2 C9 C10 C15 2.3(3) . . . . ?
C15 C10 C11 C12 1.5(5) . . . . ?
C9 C10 C11 C12 -175.0(3) . . . . ?
C10 C11 C12 C13 -0.5(5) . . . . ?
C11 C12 C13 C14 -0.6(5) . . . . ?
C12 C13 C14 C15 0.6(5) . . . . ?
C13 C14 C15 C10 0.4(4) . . . . ?
C13 C14 C15 C16 177.0(3) . . . . ?
C11 C10 C15 C14 -1.5(5) . . . . ?
C9 C10 C15 C14 175.7(3) . . . . ?
C11 C10 C15 C16 -178.8(3) . . . . ?
C9 C10 C15 C16 -1.6(3) . . . . ?
C9 N2 C16 O3 -178.3(3) . . . . ?
C6 N2 C16 O3 -15.3(4) . . . . ?
C9 N2 C16 C15 1.2(3) . . . . ?
C6 N2 C16 C15 164.3(3) . . . . ?
C14 C15 C16 O3 2.8(5) . . . . ?
C10 C15 C16 O3 179.8(3) . . . . ?
C14 C15 C16 N2 -176.7(3) . . . . ?
C10 C15 C16 N2 0.3(3) . . . . ?

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.043

