# 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_57
_database_code_depnum_ccdc_archive 'CCDC 1425851'
_audit_update_record             
;
2015-09-18 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        Iminoquinone
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H18 N2 O3'
_chemical_formula_weight         406.42

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.0241(4)
_cell_length_b                   9.7102(4)
_cell_length_c                   12.2998(5)
_cell_angle_alpha                84.499(2)
_cell_angle_beta                 84.789(2)
_cell_angle_gamma                74.1251(16)
_cell_volume                     1029.55(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2402
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      21.77

_exptl_crystal_description       Hexagonal
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14199
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.667
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             3588
_reflns_number_gt                2271
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0597P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3588
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1219
_refine_ls_wR_factor_gt          0.1015
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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_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
C1 C 0.0818(2) 0.3120(2) 0.83522(14) 0.0392(5) Uani 1 1 d . . . . .
C2 C 0.0271(2) 0.4684(2) 0.82722(16) 0.0472(5) Uani 1 1 d . . . . .
H2 H -0.0591 0.5125 0.7882 0.057 Uiso 1 1 calc R U . . .
C3 C 0.0960(3) 0.5499(2) 0.87355(16) 0.0513(6) Uani 1 1 d . . . . .
H3 H 0.0560 0.6491 0.8678 0.062 Uiso 1 1 calc R U . . .
C4 C 0.2332(3) 0.4862(2) 0.93323(16) 0.0463(5) Uani 1 1 d . . . . .
C5 C 0.2887(2) 0.3254(2) 0.94586(15) 0.0404(5) Uani 1 1 d . . . . .
C6 C 0.2182(2) 0.2438(2) 0.89505(14) 0.0388(5) Uani 1 1 d . . . . .
C7 C 0.2828(2) 0.0852(2) 0.90203(16) 0.0456(5) Uani 1 1 d . . . . .
C8 C 0.3067(2) 0.0042(2) 0.80300(16) 0.0425(5) Uani 1 1 d . . . . .
C9 C 0.3132(2) -0.1406(2) 0.81422(19) 0.0542(6) Uani 1 1 d . . . . .
H9 H 0.2954 -0.1844 0.8830 0.065 Uiso 1 1 calc R U . . .
C10 C 0.3458(3) -0.2199(3) 0.7237(2) 0.0713(7) Uani 1 1 d . . . . .
H10 H 0.3513 -0.3174 0.7317 0.086 Uiso 1 1 calc R U . . .
C11 C 0.3702(3) -0.1556(3) 0.6222(2) 0.0741(8) Uani 1 1 d . . . . .
H11 H 0.3929 -0.2098 0.5614 0.089 Uiso 1 1 calc R U . . .
C12 C 0.3612(2) -0.0118(3) 0.60949(18) 0.0650(7) Uani 1 1 d . . . . .
H12 H 0.3761 0.0317 0.5401 0.078 Uiso 1 1 calc R U . . .
C13 C 0.3300(2) 0.0686(2) 0.69978(17) 0.0512(6) Uani 1 1 d . . . . .
H13 H 0.3245 0.1660 0.6912 0.061 Uiso 1 1 calc R U . . .
C14 C -0.2482(2) 0.3698(2) 0.56658(17) 0.0476(5) Uani 1 1 d . . . . .
H14 H -0.2431 0.3937 0.4915 0.057 Uiso 1 1 calc R U . . .
C15 C -0.3903(3) 0.3784(2) 0.62142(18) 0.0568(6) Uani 1 1 d . . . . .
H15 H -0.4803 0.4097 0.5845 0.068 Uiso 1 1 calc R U . . .
C16 C -0.3960(3) 0.3397(3) 0.73164(19) 0.0646(7) Uani 1 1 d . . . . .
H16 H -0.4911 0.3438 0.7693 0.078 Uiso 1 1 calc R U . . .
C17 C -0.2638(3) 0.2950(3) 0.78765(17) 0.0572(6) Uani 1 1 d . . . . .
H17 H -0.2706 0.2678 0.8621 0.069 Uiso 1 1 calc R U . . .
C18 C -0.1212(2) 0.2901(2) 0.73435(15) 0.0416(5) Uani 1 1 d . . . . .
C19 C -0.1118(2) 0.3261(2) 0.62073(15) 0.0420(5) Uani 1 1 d . . . . .
C20 C 0.0393(2) 0.3239(2) 0.55850(16) 0.0433(5) Uani 1 1 d . . . . .
C21 C 0.0804(2) 0.2519(2) 0.45417(15) 0.0425(5) Uani 1 1 d . . . . .
C22 C 0.2047(2) 0.2752(2) 0.38667(17) 0.0524(6) Uani 1 1 d . . . . .
H22 H 0.2581 0.3379 0.4058 0.063 Uiso 1 1 calc R U . . .
C23 C 0.2493(3) 0.2058(3) 0.29133(18) 0.0637(7) Uani 1 1 d . . . . .
H23 H 0.3320 0.2225 0.2462 0.076 Uiso 1 1 calc R U . . .
C24 C 0.1719(3) 0.1121(3) 0.26279(19) 0.0671(7) Uani 1 1 d . . . . .
H24 H 0.2021 0.0658 0.1984 0.081 Uiso 1 1 calc R U . . .
C25 C 0.0498(3) 0.0867(3) 0.32938(18) 0.0615(6) Uani 1 1 d . . . . .
H25 H -0.0021 0.0229 0.3104 0.074 Uiso 1 1 calc R U . . .
C26 C 0.0043(2) 0.1566(2) 0.42485(17) 0.0511(6) Uani 1 1 d . . . . .
H26 H -0.0783 0.1392 0.4697 0.061 Uiso 1 1 calc R U . . .
N1 N 0.01189(19) 0.23220(18) 0.79335(12) 0.0447(4) Uani 1 1 d . . . . .
O1 O 0.30428(19) 0.55848(16) 0.97160(13) 0.0671(5) Uani 1 1 d . . . . .
O3 O 0.3274(2) 0.02106(17) 0.98861(12) 0.0778(5) Uani 1 1 d . . . . .
O4 O 0.12850(17) 0.38095(16) 0.59418(11) 0.0557(4) Uani 1 1 d . . . . .
N2 N 0.4124(2) 0.2779(3) 1.00549(15) 0.0564(5) Uani 1 1 d . . . . .
H2N H 0.453(3) 0.344(3) 1.0205(19) 0.072(8) Uiso 1 1 d . . . . .
H1N H 0.460(3) 0.180(3) 1.020(2) 0.094(9) Uiso 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
C1 N1 1.291(2) . ?
C1 C6 1.457(3) . ?
C1 C2 1.459(3) . ?
C2 C3 1.326(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.454(3) . ?
C3 H3 0.9300 . ?
C4 O1 1.221(2) . ?
C4 C5 1.501(3) . ?
C5 N2 1.342(3) . ?
C5 C6 1.365(3) . ?
C6 C7 1.488(3) . ?
C7 O3 1.224(2) . ?
C7 C8 1.481(3) . ?
C8 C9 1.385(3) . ?
C8 C13 1.385(3) . ?
C9 C10 1.378(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.369(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.379(3) . ?
C14 C19 1.395(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.377(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.381(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.408(3) . ?
C18 N1 1.413(2) . ?
C19 C20 1.498(3) . ?
C20 O4 1.226(2) . ?
C20 C21 1.489(3) . ?
C21 C26 1.384(3) . ?
C21 C22 1.390(3) . ?
C22 C23 1.382(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.376(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.375(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.386(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
N2 H2N 0.86(3) . ?
N2 H1N 0.94(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 C6 118.99(18) . . ?
N1 C1 C2 122.46(18) . . ?
C6 C1 C2 118.53(18) . . ?
C3 C2 C1 122.3(2) . . ?
C3 C2 H2 118.8 . . ?
C1 C2 H2 118.8 . . ?
C2 C3 C4 120.9(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
O1 C4 C3 122.5(2) . . ?
O1 C4 C5 119.7(2) . . ?
C3 C4 C5 117.78(19) . . ?
N2 C5 C6 126.8(2) . . ?
N2 C5 C4 112.94(19) . . ?
C6 C5 C4 120.15(18) . . ?
C5 C6 C1 120.13(18) . . ?
C5 C6 C7 119.03(18) . . ?
C1 C6 C7 120.84(17) . . ?
O3 C7 C8 118.89(19) . . ?
O3 C7 C6 120.11(18) . . ?
C8 C7 C6 120.79(17) . . ?
C9 C8 C13 119.28(19) . . ?
C9 C8 C7 119.34(18) . . ?
C13 C8 C7 121.31(19) . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.4(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C13 120.0(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C8 120.1(2) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C15 C14 C19 121.7(2) . . ?
C15 C14 H14 119.1 . . ?
C19 C14 H14 119.1 . . ?
C16 C15 C14 118.6(2) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C15 C16 C17 121.3(2) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C18 120.7(2) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C19 119.13(19) . . ?
C17 C18 N1 118.41(18) . . ?
C19 C18 N1 122.00(17) . . ?
C14 C19 C18 118.55(18) . . ?
C14 C19 C20 119.80(18) . . ?
C18 C19 C20 121.61(18) . . ?
O4 C20 C21 120.50(18) . . ?
O4 C20 C19 119.67(18) . . ?
C21 C20 C19 119.83(18) . . ?
C26 C21 C22 118.79(19) . . ?
C26 C21 C20 122.20(18) . . ?
C22 C21 C20 118.92(19) . . ?
C23 C22 C21 120.3(2) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 120.3(2) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C25 C24 C23 120.1(2) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 119.8(2) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C21 C26 C25 120.7(2) . . ?
C21 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C1 N1 C18 122.39(17) . . ?
C5 N2 H2N 114.2(17) . . ?
C5 N2 H1N 122.3(16) . . ?
H2N N2 H1N 123(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
N1 C1 C2 C3 177.59(19) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
C1 C2 C3 C4 1.4(3) . . . . ?
C2 C3 C4 O1 175.8(2) . . . . ?
C2 C3 C4 C5 -3.4(3) . . . . ?
O1 C4 C5 N2 3.1(3) . . . . ?
C3 C4 C5 N2 -177.72(18) . . . . ?
O1 C4 C5 C6 -174.18(19) . . . . ?
C3 C4 C5 C6 5.0(3) . . . . ?
N2 C5 C6 C1 178.51(18) . . . . ?
C4 C5 C6 C1 -4.7(3) . . . . ?
N2 C5 C6 C7 -1.4(3) . . . . ?
C4 C5 C6 C7 175.45(16) . . . . ?
N1 C1 C6 C5 -175.95(16) . . . . ?
C2 C1 C6 C5 2.6(3) . . . . ?
N1 C1 C6 C7 3.9(3) . . . . ?
C2 C1 C6 C7 -177.51(16) . . . . ?
C5 C6 C7 O3 41.8(3) . . . . ?
C1 C6 C7 O3 -138.1(2) . . . . ?
C5 C6 C7 C8 -132.9(2) . . . . ?
C1 C6 C7 C8 47.2(3) . . . . ?
O3 C7 C8 C9 28.1(3) . . . . ?
C6 C7 C8 C9 -157.15(19) . . . . ?
O3 C7 C8 C13 -148.8(2) . . . . ?
C6 C7 C8 C13 25.9(3) . . . . ?
C13 C8 C9 C10 1.5(3) . . . . ?
C7 C8 C9 C10 -175.57(19) . . . . ?
C8 C9 C10 C11 -0.8(4) . . . . ?
C9 C10 C11 C12 -0.5(4) . . . . ?
C10 C11 C12 C13 1.1(4) . . . . ?
C11 C12 C13 C8 -0.4(3) . . . . ?
C9 C8 C13 C12 -0.8(3) . . . . ?
C7 C8 C13 C12 176.12(18) . . . . ?
C19 C14 C15 C16 -1.5(3) . . . . ?
C14 C15 C16 C17 0.9(4) . . . . ?
C15 C16 C17 C18 1.1(4) . . . . ?
C16 C17 C18 C19 -2.5(3) . . . . ?
C16 C17 C18 N1 -174.8(2) . . . . ?
C15 C14 C19 C18 0.0(3) . . . . ?
C15 C14 C19 C20 -177.63(18) . . . . ?
C17 C18 C19 C14 1.9(3) . . . . ?
N1 C18 C19 C14 173.95(17) . . . . ?
C17 C18 C19 C20 179.54(19) . . . . ?
N1 C18 C19 C20 -8.4(3) . . . . ?
C14 C19 C20 O4 130.4(2) . . . . ?
C18 C19 C20 O4 -47.2(3) . . . . ?
C14 C19 C20 C21 -49.9(3) . . . . ?
C18 C19 C20 C21 132.5(2) . . . . ?
O4 C20 C21 C26 163.4(2) . . . . ?
C19 C20 C21 C26 -16.4(3) . . . . ?
O4 C20 C21 C22 -13.1(3) . . . . ?
C19 C20 C21 C22 167.15(18) . . . . ?
C26 C21 C22 C23 1.0(3) . . . . ?
C20 C21 C22 C23 177.58(19) . . . . ?
C21 C22 C23 C24 -0.5(3) . . . . ?
C22 C23 C24 C25 -0.2(4) . . . . ?
C23 C24 C25 C26 0.5(4) . . . . ?
C22 C21 C26 C25 -0.7(3) . . . . ?
C20 C21 C26 C25 -177.21(19) . . . . ?
C24 C25 C26 C21 0.0(3) . . . . ?
C6 C1 N1 C18 179.91(16) . . . . ?
C2 C1 N1 C18 1.4(3) . . . . ?
C17 C18 N1 C1 -99.5(2) . . . . ?
C19 C18 N1 C1 88.4(2) . . . . ?

_refine_diff_density_max         0.178
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.036


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane-ethyl acetate'
####################################################################### 
# 
# 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_VII92
_database_code_depnum_ccdc_archive 'CCDC 1425852'
_audit_update_record             
;
2015-09-18 deposited with the CCDC.
2016-02-09 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         ?
_chemical_formula_sum            'C16 H14 N2 O3'
_chemical_formula_weight         282.29

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.9893(3)
_cell_length_b                   8.2086(3)
_cell_length_c                   11.5040(4)
_cell_angle_alpha                106.6689(18)
_cell_angle_beta                 104.7153(17)
_cell_angle_gamma                96.4618(19)
_cell_volume                     684.90(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9014
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.938
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2405
_reflns_number_gt                1943
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0437P)²+0.2177P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       .
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2405
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1038
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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_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
C1 C 0.0627(2) 0.1555(2) 0.32853(15) 0.0472(4) Uani 1 1 d . . . . .
C2 C 0.1151(2) 0.3511(2) 0.38467(14) 0.0398(4) Uani 1 1 d . . . . .
C3 C 0.2280(2) 0.4319(2) 0.50651(14) 0.0372(4) Uani 1 1 d . . . . .
C4 C 0.2889(2) 0.32352(19) 0.58398(13) 0.0353(4) Uani 1 1 d . . . . .
C5 C 0.2397(2) 0.1339(2) 0.52435(15) 0.0431(4) Uani 1 1 d . . . . .
H5 H 0.2856 0.0655 0.5715 0.052 Uiso 1 1 calc R U . . .
C6 C 0.1335(2) 0.0553(2) 0.40702(15) 0.0469(4) Uani 1 1 d . . . . .
H6 H 0.1043 -0.0653 0.3750 0.056 Uiso 1 1 calc R U . . .
C7 C 0.4524(2) 0.2978(2) 0.77859(14) 0.0407(4) Uani 1 1 d . . . . .
C8 C 0.3962(2) 0.27715(19) 0.88092(14) 0.0375(4) Uani 1 1 d . . . . .
C9 C 0.5032(2) 0.2099(2) 0.96449(15) 0.0449(4) Uani 1 1 d . . . . .
H9 H 0.4688 0.1970 1.0332 0.054 Uiso 1 1 calc R U . . .
C10 C 0.6574(2) 0.1623(2) 0.94873(16) 0.0507(5) Uani 1 1 d . . . . .
H10 H 0.7266 0.1193 1.0066 0.061 Uiso 1 1 calc R U . . .
C11 C 0.7082(2) 0.1788(2) 0.84652(17) 0.0520(5) Uani 1 1 d . . . . .
H11 H 0.8113 0.1448 0.8341 0.062 Uiso 1 1 calc R U . . .
C12 C 0.6070(2) 0.2456(2) 0.76232(16) 0.0508(4) Uani 1 1 d . . . . .
H12 H 0.6427 0.2560 0.6934 0.061 Uiso 1 1 calc R U . . .
C13 C 0.2830(2) 0.6227(2) 0.55216(15) 0.0440(4) Uani 1 1 d . . . . .
C14 C 0.4246(3) 0.7183(3) 0.6735(2) 0.0735(6) Uani 1 1 d . . . . .
H14A H 0.4649 0.8336 0.6746 0.110 Uiso 1 1 calc R U . . .
H14B H 0.5214 0.6586 0.6803 0.110 Uiso 1 1 calc R U . . .
H14C H 0.3789 0.7245 0.7438 0.110 Uiso 1 1 calc R U . . .
C15 C 0.2275(2) 0.3208(2) 0.89932(15) 0.0432(4) Uani 1 1 d . . . . .
C16 C 0.1872(3) 0.3213(3) 1.01973(16) 0.0555(5) Uani 1 1 d . . . . .
H16A H 0.0884 0.3762 1.0262 0.083 Uiso 1 1 calc R U . . .
H16B H 0.2883 0.3840 1.0914 0.083 Uiso 1 1 calc R U . . .
H16C H 0.1590 0.2040 1.0188 0.083 Uiso 1 1 calc R U . . .
N1 N 0.0421(2) 0.4284(2) 0.30396(13) 0.0530(4) Uani 1 1 d . . . . .
H1A H 0.0637 0.5398 0.3259 0.064 Uiso 1 1 calc R U . . .
H1B H -0.0269 0.3673 0.2296 0.064 Uiso 1 1 calc R U . . .
N2 N 0.3715(2) 0.39197(17) 0.70298(12) 0.0464(4) Uani 1 1 d . . . . .
O1 O -0.0346(2) 0.09041(18) 0.22030(12) 0.0770(5) Uani 1 1 d . . . . .
O2 O 0.2145(2) 0.70878(16) 0.48841(12) 0.0656(4) Uani 1 1 d . . . . .
O3 O 0.11943(18) 0.3517(2) 0.81741(13) 0.0674(4) 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
C1 O1 1.214(2) . ?
C1 C6 1.443(2) . ?
C1 C2 1.512(2) . ?
C2 N1 1.3235(19) . ?
C2 C3 1.381(2) . ?
C3 C4 1.468(2) . ?
C3 C13 1.476(2) . ?
C4 N2 1.2813(19) . ?
C4 C5 1.470(2) . ?
C5 C6 1.324(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.391(2) . ?
C7 C8 1.408(2) . ?
C7 N2 1.409(2) . ?
C8 C9 1.398(2) . ?
C8 C15 1.483(2) . ?
C9 C10 1.372(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 O2 1.2317(19) . ?
C13 C14 1.487(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 O3 1.2126(19) . ?
C15 C16 1.499(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?

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
O1 C1 C6 123.24(16) . . ?
O1 C1 C2 119.01(15) . . ?
C6 C1 C2 117.75(14) . . ?
N1 C2 C3 126.44(15) . . ?
N1 C2 C1 112.16(14) . . ?
C3 C2 C1 121.40(14) . . ?
C2 C3 C4 118.36(14) . . ?
C2 C3 C13 118.51(14) . . ?
C4 C3 C13 123.13(14) . . ?
N2 C4 C3 120.83(14) . . ?
N2 C4 C5 120.62(13) . . ?
C3 C4 C5 118.35(13) . . ?
C6 C5 C4 123.50(15) . . ?
C6 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
C5 C6 C1 120.44(15) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C12 C7 C8 119.21(14) . . ?
C12 C7 N2 118.29(15) . . ?
C8 C7 N2 121.87(15) . . ?
C9 C8 C7 117.76(15) . . ?
C9 C8 C15 120.35(14) . . ?
C7 C8 C15 121.88(14) . . ?
C10 C9 C8 122.37(15) . . ?
C10 C9 H9 118.8 . . ?
C8 C9 H9 118.8 . . ?
C9 C10 C11 119.26(15) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C10 C11 C12 120.21(17) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 121.15(16) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
O2 C13 C3 120.42(15) . . ?
O2 C13 C14 117.37(16) . . ?
C3 C13 C14 122.19(15) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 C8 121.26(15) . . ?
O3 C15 C16 119.31(16) . . ?
C8 C15 C16 119.40(14) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C2 N1 H1A 120.0 . . ?
C2 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C4 N2 C7 123.36(14) . . ?

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
O1 C1 C2 N1 0.7(2) . . . . ?
C6 C1 C2 N1 -179.98(15) . . . . ?
O1 C1 C2 C3 -178.83(17) . . . . ?
C6 C1 C2 C3 0.5(2) . . . . ?
N1 C2 C3 C4 177.12(15) . . . . ?
C1 C2 C3 C4 -3.4(2) . . . . ?
N1 C2 C3 C13 -3.5(3) . . . . ?
C1 C2 C3 C13 175.96(14) . . . . ?
C2 C3 C4 N2 -169.47(15) . . . . ?
C13 C3 C4 N2 11.2(2) . . . . ?
C2 C3 C4 C5 5.4(2) . . . . ?
C13 C3 C4 C5 -173.97(14) . . . . ?
N2 C4 C5 C6 170.15(17) . . . . ?
C3 C4 C5 C6 -4.7(2) . . . . ?
C4 C5 C6 C1 1.8(3) . . . . ?
O1 C1 C6 C5 179.73(19) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
C12 C7 C8 C9 2.2(2) . . . . ?
N2 C7 C8 C9 -168.55(15) . . . . ?
C12 C7 C8 C15 -176.45(15) . . . . ?
N2 C7 C8 C15 12.8(2) . . . . ?
C7 C8 C9 C10 -0.9(2) . . . . ?
C15 C8 C9 C10 177.77(15) . . . . ?
C8 C9 C10 C11 -0.8(3) . . . . ?
C9 C10 C11 C12 1.2(3) . . . . ?
C10 C11 C12 C7 0.1(3) . . . . ?
C8 C7 C12 C11 -1.8(3) . . . . ?
N2 C7 C12 C11 169.24(15) . . . . ?
C2 C3 C13 O2 8.0(2) . . . . ?
C4 C3 C13 O2 -172.68(16) . . . . ?
C2 C3 C13 C14 -170.43(17) . . . . ?
C4 C3 C13 C14 8.9(3) . . . . ?
C9 C8 C15 O3 -167.67(16) . . . . ?
C7 C8 C15 O3 10.9(2) . . . . ?
C9 C8 C15 C16 10.4(2) . . . . ?
C7 C8 C15 C16 -171.01(15) . . . . ?
C3 C4 N2 C7 -171.68(15) . . . . ?
C5 C4 N2 C7 13.6(2) . . . . ?
C12 C7 N2 C4 72.6(2) . . . . ?
C8 C7 N2 C4 -116.59(18) . . . . ?

_refine_diff_density_max         0.261
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.030

