 
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          'C15 H10 N2 O3'
_chemical_formula_sum
 'C15 H10 N2 O3' 
_chemical_formula_weight          266.25

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                    9.2227(7)
_cell_length_b                    8.7759(7)
_cell_length_c                    15.2553(13)
_cell_angle_alpha                 90
_cell_angle_beta                  95.299(3)
_cell_angle_gamma                 90
_cell_volume                      1229.45(17)
_cell_formula_units_Z             4
_cell_measurement_temperature     299(2)
_cell_measurement_reflns_used     7249
_cell_measurement_theta_min       2.22
_cell_measurement_theta_max       25.00
 
_exptl_crystal_description        block
_exptl_crystal_colour             pale-yellow
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.438          
_exptl_crystal_F_000              552
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.220
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.180
_exptl_absorpt_coefficient_mu     0.103
_shelx_estimated_absorpt_T_min    0.980
_shelx_estimated_absorpt_T_max    0.982
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9798 
_exptl_absorpt_correction_T_max   0.9818 
_exptl_absorpt_process_details    sadabs
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       299(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             19005
_diffrn_reflns_av_unetI/netI      0.0275
_diffrn_reflns_av_R_equivalents   0.0493
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          2.218
_diffrn_reflns_theta_max          25.164
_diffrn_reflns_theta_full         25.164
_diffrn_measured_fraction_theta_max   0.992
_diffrn_measured_fraction_theta_full  0.992
_diffrn_reflns_Laue_measured_fraction_max    0.992
_diffrn_reflns_Laue_measured_fraction_full   0.992
_diffrn_reflns_point_group_measured_fraction_max   0.992
_diffrn_reflns_point_group_measured_fraction_full  0.992
_reflns_number_total              2190
_reflns_number_gt                 1825
_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)+(0.0578P)²+0.2475P] 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          2190
_refine_ls_number_parameters      185
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0487
_refine_ls_R_factor_gt            0.0386
_refine_ls_wR_factor_ref          0.1062
_refine_ls_wR_factor_gt           0.0996
_refine_ls_goodness_of_fit_ref    1.055
_refine_ls_restrained_S_all       1.055
_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
O1 O 0.07219(13) 0.21915(12) 0.58345(8) 0.0443(3) Uani 1 1 d . . . . .
O3 O 0.44936(14) 0.67785(14) 0.39058(9) 0.0586(4) Uani 1 1 d . . . . .
O2 O 0.23934(16) 0.72946(15) 0.32182(9) 0.0655(4) Uani 1 1 d . . . . .
N1 N 0.12437(14) 0.26652(16) 0.26169(8) 0.0434(3) Uani 1 1 d . . . . .
N2 N 0.31749(16) 0.66113(14) 0.37791(9) 0.0431(3) Uani 1 1 d . . . . .
C8 C 0.18537(14) 0.41880(16) 0.39135(9) 0.0318(3) Uani 1 1 d . . . . .
C3 C 0.12784(15) 0.30519(15) 0.44422(9) 0.0317(3) Uani 1 1 d . . . . .
C6 C 0.25640(15) 0.57243(16) 0.52263(9) 0.0334(3) Uani 1 1 d . . . . .
C5 C 0.19424(16) 0.45913(16) 0.57370(9) 0.0357(3) Uani 1 1 d . . . . .
H5 H 0.1957 0.4733 0.6342 0.043 Uiso 1 1 calc R U . . .
C4 C 0.13212(15) 0.32952(16) 0.53719(9) 0.0336(3) Uani 1 1 d . . . . .
C7 C 0.24875(16) 0.54991(16) 0.43307(9) 0.0341(3) Uani 1 1 d . . . . .
C9 C 0.17966(16) 0.39055(18) 0.29963(9) 0.0377(4) Uani 1 1 d . . . . .
H9 H 0.2173 0.4642 0.2642 0.045 Uiso 1 1 calc R U . . .
C2 C 0.07147(17) 0.17245(18) 0.40266(10) 0.0409(4) Uani 1 1 d . . . . .
H2 H 0.0337 0.0951 0.4355 0.049 Uiso 1 1 calc R U . . .
C10 C 0.32643(16) 0.70902(16) 0.56626(10) 0.0354(3) Uani 1 1 d . . . . .
C15 C 0.29572(17) 0.85577(17) 0.53514(11) 0.0427(4) Uani 1 1 d . . . . .
H15 H 0.2266 0.8704 0.4875 0.051 Uiso 1 1 calc R U . . .
C11 C 0.42641(17) 0.69093(18) 0.63900(10) 0.0425(4) Uani 1 1 d . . . . .
H11 H 0.4463 0.5940 0.6616 0.051 Uiso 1 1 calc R U . . .
C12 C 0.49690(19) 0.8158(2) 0.67831(11) 0.0489(4) Uani 1 1 d . . . . .
H12 H 0.5640 0.8023 0.7270 0.059 Uiso 1 1 calc R U . . .
C14 C 0.36727(19) 0.97968(18) 0.57454(11) 0.0500(4) Uani 1 1 d . . . . .
H14 H 0.3470 1.0771 0.5528 0.060 Uiso 1 1 calc R U . . .
C1 C 0.07253(18) 0.1580(2) 0.31387(11) 0.0473(4) Uani 1 1 d . . . . .
H1 H 0.0357 0.0688 0.2875 0.057 Uiso 1 1 calc R U . . .
C13 C 0.46816(19) 0.95998(19) 0.64563(11) 0.0495(4) Uani 1 1 d . . . . .
H13 H 0.5168 1.0437 0.6716 0.059 Uiso 1 1 calc R U . . .
H16 H 0.092(2) 0.234(2) 0.6402(16) 0.061(6) 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
O1 C4 1.3467(17) . ?
O1 H16 0.88(2) . ?
O3 N2 1.2225(18) . ?
O2 N2 1.2238(18) . ?
N1 C9 1.313(2) . ?
N1 C1 1.356(2) . ?
N2 C7 1.4701(19) . ?
C8 C7 1.415(2) . ?
C8 C3 1.4160(19) . ?
C8 C9 1.417(2) . ?
C3 C2 1.403(2) . ?
C3 C4 1.431(2) . ?
C6 C7 1.376(2) . ?
C6 C5 1.417(2) . ?
C6 C10 1.489(2) . ?
C5 C4 1.369(2) . ?
C5 H5 0.9300 . ?
C9 H9 0.9300 . ?
C2 C1 1.361(2) . ?
C2 H2 0.9300 . ?
C10 C11 1.385(2) . ?
C10 C15 1.393(2) . ?
C15 C14 1.381(2) . ?
C15 H15 0.9300 . ?
C11 C12 1.382(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.377(2) . ?
C12 H12 0.9300 . ?
C14 C13 1.373(2) . ?
C14 H14 0.9300 . ?
C1 H1 0.9300 . ?
C13 H13 0.9300 . ?
 
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
C4 O1 H16 110.8(13) . . ?
C9 N1 C1 117.83(13) . . ?
O3 N2 O2 124.39(14) . . ?
O3 N2 C7 117.68(13) . . ?
O2 N2 C7 117.92(13) . . ?
C7 C8 C3 118.52(12) . . ?
C7 C8 C9 124.23(13) . . ?
C3 C8 C9 117.22(13) . . ?
C2 C3 C8 118.03(13) . . ?
C2 C3 C4 123.15(13) . . ?
C8 C3 C4 118.81(13) . . ?
C7 C6 C5 117.33(13) . . ?
C7 C6 C10 122.67(13) . . ?
C5 C6 C10 120.00(12) . . ?
C4 C5 C6 122.34(13) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
O1 C4 C5 124.13(13) . . ?
O1 C4 C3 115.90(13) . . ?
C5 C4 C3 119.96(13) . . ?
C6 C7 C8 123.00(13) . . ?
C6 C7 N2 119.19(13) . . ?
C8 C7 N2 117.68(12) . . ?
N1 C9 C8 123.89(14) . . ?
N1 C9 H9 118.1 . . ?
C8 C9 H9 118.1 . . ?
C1 C2 C3 119.38(14) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C11 C10 C15 118.59(14) . . ?
C11 C10 C6 119.67(13) . . ?
C15 C10 C6 121.73(13) . . ?
C14 C15 C10 120.40(15) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
C12 C11 C10 120.57(15) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C11 120.28(16) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C13 C14 C15 120.43(15) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
N1 C1 C2 123.62(15) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C14 C13 C12 119.69(15) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
 
_refine_diff_density_max    0.151
_refine_diff_density_min   -0.190
_refine_diff_density_rms    0.043



