 
data_shelx
 
_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 H12 N2 O4'
_chemical_formula_sum
 'C16 H12 N2 O4' 
_chemical_formula_weight          296.28

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 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_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+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    10.4313(12)
_cell_length_b                    9.4929(10)
_cell_length_c                    14.4559(17)
_cell_angle_alpha                 90
_cell_angle_beta                  106.149(4)
_cell_angle_gamma                 90
_cell_volume                      1375.0(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     300(2)
_cell_measurement_reflns_used     9815
_cell_measurement_theta_min       2.60
_cell_measurement_theta_max       26.02
 
_exptl_crystal_description        BLOCK
_exptl_crystal_colour             PALE-YELLOW
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.431          
_exptl_crystal_F_000              616
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           ?
_exptl_crystal_size_mid           ?
_exptl_crystal_size_min           ?
_exptl_absorpt_coefficient_mu     0.105
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.7160
_exptl_absorpt_correction_T_max   0.7453
_exptl_absorpt_process_details    sadabs
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       300(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             91803
_diffrn_reflns_av_unetI/netI      0.0131
_diffrn_reflns_av_R_equivalents   0.0572
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          2.599
_diffrn_reflns_theta_max          26.299
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.996
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    0.996
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   0.996
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              2770
_reflns_number_gt                 2351
_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)+(0.0469P)²+0.6700P] 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      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          2770
_refine_ls_number_parameters      204
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0578
_refine_ls_R_factor_gt            0.0465
_refine_ls_wR_factor_ref          0.1182
_refine_ls_wR_factor_gt           0.1108
_refine_ls_goodness_of_fit_ref    1.125
_refine_ls_restrained_S_all       1.125
_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
H17 H 0.550(3) 0.237(3) 0.256(2) 0.070(8) Uiso 1 1 d . . . . .
O1 O 0.58272(14) 0.19406(17) 0.30967(10) 0.0483(4) Uani 1 1 d . . . . .
O4 O 0.09441(13) 0.26551(15) 0.44439(11) 0.0492(4) Uani 1 1 d . . . . .
N1 N 0.55251(14) 0.17463(16) 0.63319(9) 0.0330(3) Uani 1 1 d . . . . .
N2 N 0.32689(15) 0.3464(2) 0.58603(10) 0.0458(4) Uani 1 1 d . . . . .
O2 O 0.31518(17) 0.4727(2) 0.59855(12) 0.0717(5) Uani 1 1 d . . . . .
O3 O 0.29007(17) 0.2544(2) 0.63162(11) 0.0760(6) Uani 1 1 d . . . . .
C5 C 0.50382(15) 0.21729(17) 0.53925(11) 0.0279(3) Uani 1 1 d . . . . .
C6 C 0.38953(16) 0.30427(19) 0.51162(11) 0.0310(4) Uani 1 1 d . . . . .
C7 C 0.33720(16) 0.35171(18) 0.41851(11) 0.0298(4) Uani 1 1 d . . . . .
C4 C 0.56665(15) 0.17751(18) 0.46822(11) 0.0295(4) Uani 1 1 d . . . . .
C10 C 0.21223(16) 0.43553(18) 0.38439(11) 0.0309(4) Uani 1 1 d . . . . .
C9 C 0.51588(17) 0.23239(19) 0.37325(11) 0.0330(4) Uani 1 1 d . . . . .
C15 C 0.09055(16) 0.39049(19) 0.39740(12) 0.0331(4) Uani 1 1 d . . . . .
C8 C 0.40499(17) 0.31549(19) 0.35025(12) 0.0350(4) Uani 1 1 d . . . . .
H8 H 0.3732 0.3492 0.2876 0.042 Uiso 1 1 calc R U . . .
C3 C 0.67534(17) 0.08411(19) 0.49461(12) 0.0351(4) Uani 1 1 d . . . . .
H3 H 0.7173 0.0542 0.4491 0.042 Uiso 1 1 calc R U . . .
C2 C 0.71875(18) 0.0377(2) 0.58726(13) 0.0392(4) Uani 1 1 d . . . . .
H2 H 0.7892 -0.0257 0.6057 0.047 Uiso 1 1 calc R U . . .
C1 C 0.65505(17) 0.0876(2) 0.65379(12) 0.0374(4) Uani 1 1 d . . . . .
H1 H 0.6872 0.0573 0.7172 0.045 Uiso 1 1 calc R U . . .
C11 C 0.2131(2) 0.5586(2) 0.33317(14) 0.0435(5) Uani 1 1 d . . . . .
H11 H 0.2925 0.5891 0.3226 0.052 Uiso 1 1 calc R U . . .
C14 C -0.02392(18) 0.4690(2) 0.36146(13) 0.0436(5) Uani 1 1 d . . . . .
H14 H -0.1042 0.4386 0.3707 0.052 Uiso 1 1 calc R U . . .
C13 C -0.0196(2) 0.5922(2) 0.31187(15) 0.0519(5) Uani 1 1 d . . . . .
H13 H -0.0970 0.6449 0.2882 0.062 Uiso 1 1 calc R U . . .
C12 C 0.0979(2) 0.6375(2) 0.29727(15) 0.0545(6) Uani 1 1 d . . . . .
H12 H 0.1005 0.7204 0.2636 0.065 Uiso 1 1 calc R U . . .
C16 C -0.0229(2) 0.2187(3) 0.46688(17) 0.0612(6) Uani 1 1 d . . . . .
H16A H -0.0578 0.2937 0.4973 0.092 Uiso 1 1 calc R U . . .
H16B H -0.0017 0.1396 0.5098 0.092 Uiso 1 1 calc R U . . .
H16C H -0.0885 0.1913 0.4088 0.092 Uiso 1 1 calc R U . . .
 
 
_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 C9 1.349(2) . ?
O1 H17 0.86(3) . ?
O4 C15 1.362(2) . ?
O4 C16 1.422(2) . ?
N1 C1 1.318(2) . ?
N1 C5 1.372(2) . ?
N2 O3 1.219(2) . ?
N2 O2 1.224(2) . ?
N2 C6 1.461(2) . ?
C5 C6 1.413(2) . ?
C5 C4 1.415(2) . ?
C6 C7 1.380(2) . ?
C7 C8 1.407(2) . ?
C7 C10 1.489(2) . ?
C4 C3 1.406(2) . ?
C4 C9 1.426(2) . ?
C10 C11 1.385(2) . ?
C10 C15 1.401(2) . ?
C9 C8 1.363(2) . ?
C15 C14 1.381(3) . ?
C8 H8 0.9300 . ?
C3 C2 1.362(3) . ?
C3 H3 0.9300 . ?
C2 C1 1.395(3) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?
C11 C12 1.388(3) . ?
C11 H11 0.9300 . ?
C14 C13 1.379(3) . ?
C14 H14 0.9300 . ?
C13 C12 1.370(3) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C9 O1 H17 109.6(17) . . ?
C15 O4 C16 118.55(16) . . ?
C1 N1 C5 117.53(14) . . ?
O3 N2 O2 124.23(18) . . ?
O3 N2 C6 118.35(18) . . ?
O2 N2 C6 117.42(18) . . ?
N1 C5 C6 120.20(14) . . ?
N1 C5 C4 121.40(15) . . ?
C6 C5 C4 118.39(14) . . ?
C7 C6 C5 122.69(14) . . ?
C7 C6 N2 119.48(15) . . ?
C5 C6 N2 117.82(14) . . ?
C6 C7 C8 117.69(15) . . ?
C6 C7 C10 124.74(14) . . ?
C8 C7 C10 117.56(14) . . ?
C3 C4 C5 118.23(15) . . ?
C3 C4 C9 123.18(15) . . ?
C5 C4 C9 118.59(15) . . ?
C11 C10 C15 118.04(16) . . ?
C11 C10 C7 119.53(15) . . ?
C15 C10 C7 122.33(15) . . ?
O1 C9 C8 123.67(15) . . ?
O1 C9 C4 115.70(15) . . ?
C8 C9 C4 120.62(15) . . ?
O4 C15 C14 124.08(16) . . ?
O4 C15 C10 115.50(15) . . ?
C14 C15 C10 120.40(17) . . ?
C9 C8 C7 121.89(15) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C2 C3 C4 119.54(16) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C2 C1 118.44(17) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
N1 C1 C2 124.69(16) . . ?
N1 C1 H1 117.7 . . ?
C2 C1 H1 117.7 . . ?
C10 C11 C12 121.45(19) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C13 C14 C15 120.25(18) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C12 C13 C14 120.39(18) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C12 C11 119.5(2) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
 
_refine_diff_density_max    0.179
_refine_diff_density_min   -0.206
_refine_diff_density_rms    0.046



