data_d19966
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C15 H14 N2 O3'

_chemical_formula_sum             'C15 H14 N2 O3'

_chemical_formula_weight          270.28
 
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'
 
_symmetry_cell_setting            monoclinic
_symmetry_space_group_name_H-M    'P 21/c'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    8.0850(4)
_cell_length_b                    16.9819(9)
_cell_length_c                    10.0705(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  110.1300(10)
_cell_angle_gamma                 90.00
_cell_volume                      1298.20(11)
_cell_formula_units_Z             4
_cell_measurement_temperature     200(2)
_cell_measurement_reflns_used     9603
_cell_measurement_theta_min       2.939
_cell_measurement_theta_max       24.943
 
_exptl_crystal_description        prism
_exptl_crystal_colour             yellow
_exptl_crystal_size_max           0.56
_exptl_crystal_size_mid           0.41
_exptl_crystal_size_min           0.08
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.383
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              568
_exptl_absorpt_coefficient_mu     0.098
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9472
_exptl_absorpt_correction_T_max   0.9922
_exptl_absorpt_process_details    'SADABS'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       200(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   'D8 Venture'
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             20862
_diffrn_reflns_av_R_equivalents   0.0509
_diffrn_reflns_av_sigmaI/netI     0.0243
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -20
_diffrn_reflns_limit_k_max        20
_diffrn_reflns_limit_l_min        -11
_diffrn_reflns_limit_l_max        10
_diffrn_reflns_theta_min          2.47
_diffrn_reflns_theta_max          25.06
_reflns_number_total              2272
_reflns_number_gt                 1962
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement   'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material   'WinGX publication routines (Farrugia, 2005)'
 
_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)+(0.0415P)²+0.3360P] 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_number_reflns          2272
_refine_ls_number_parameters      181
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0412
_refine_ls_R_factor_gt            0.0338
_refine_ls_wR_factor_ref          0.0900
_refine_ls_wR_factor_gt           0.0846
_refine_ls_goodness_of_fit_ref    1.034
_refine_ls_restrained_S_all       1.034
_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
C1 C 0.34351(18) 0.28884(7) 0.63491(14) 0.0347(3) Uani 1 1 d . . .
C2 C 0.13519(19) 0.29039(9) 0.41361(15) 0.0423(4) Uani 1 1 d . . .
H2A H 0.0063 0.2992 0.3792 0.051 Uiso 1 1 calc R . .
H2B H 0.1654 0.2575 0.3441 0.051 Uiso 1 1 calc R . .
C3 C 0.23356(18) 0.36812(9) 0.43669(14) 0.0407(3) Uani 1 1 d . . .
H3A H 0.2736 0.3810 0.3568 0.049 Uiso 1 1 calc R . .
H3B H 0.1608 0.4119 0.4513 0.049 Uiso 1 1 calc R . .
C4 C 0.51262(16) 0.40783(7) 0.63221(13) 0.0285(3) Uani 1 1 d . . .
C5 C 0.68031(17) 0.40561(7) 0.60458(14) 0.0329(3) Uani 1 1 d . . .
H5 H 0.7502 0.4555 0.6276 0.039 Uiso 1 1 calc R . .
C6 C 0.69963(19) 0.35978(9) 0.48284(15) 0.0424(4) Uani 1 1 d . . .
H6A H 0.5961 0.3298 0.4223 0.051 Uiso 1 1 calc R . .
H6B H 0.7738 0.3828 0.4324 0.051 Uiso 1 1 calc R . .
C7 C 0.7894(2) 0.33131(8) 0.63008(16) 0.0434(4) Uani 1 1 d . . .
H7A H 0.9191 0.3368 0.6708 0.052 Uiso 1 1 calc R . .
H7B H 0.7413 0.2838 0.6607 0.052 Uiso 1 1 calc R . .
C8 C 0.47937(16) 0.46220(7) 0.71638(13) 0.0288(3) Uani 1 1 d . . .
C9 C 0.56312(16) 0.57015(7) 0.86188(13) 0.0305(3) Uani 1 1 d . . .
H9 H 0.6493 0.6083 0.9089 0.037 Uiso 1 1 calc R . .
C10 C 0.39493(16) 0.57280(7) 0.88234(13) 0.0291(3) Uani 1 1 d . . .
C11 C 0.34889(18) 0.62914(8) 0.96402(14) 0.0367(3) Uani 1 1 d . . .
H11 H 0.4315 0.6683 1.0126 0.044 Uiso 1 1 calc R . .
C12 C 0.1829(2) 0.62798(9) 0.97418(16) 0.0434(4) Uani 1 1 d . . .
H12 H 0.1509 0.6665 1.0293 0.052 Uiso 1 1 calc R . .
C13 C 0.06335(19) 0.57078(9) 0.90414(16) 0.0433(4) Uani 1 1 d . . .
H13 H -0.0511 0.5707 0.9107 0.052 Uiso 1 1 calc R . .
C14 C 0.10776(17) 0.51328(9) 0.82419(15) 0.0385(3) Uani 1 1 d . . .
H14 H 0.0259 0.4734 0.7776 0.046 Uiso 1 1 calc R . .
C15 C 0.27337(16) 0.51539(7) 0.81409(13) 0.0305(3) Uani 1 1 d . . .
N1 N 0.38111(14) 0.35058(6) 0.56494(11) 0.0304(3) Uani 1 1 d . . .
N2 N 0.60263(13) 0.51889(6) 0.78331(11) 0.0304(3) Uani 1 1 d . . .
O1 O 0.19328(13) 0.25347(5) 0.55137(11) 0.0439(3) Uani 1 1 d . . .
O2 O 0.42512(15) 0.26503(6) 0.75128(12) 0.0558(3) Uani 1 1 d . . .
O3 O 0.31592(12) 0.45839(5) 0.73405(10) 0.0386(3) 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 O2 1.2000(17) . ?
C1 N1 1.3549(16) . ?
C1 O1 1.3566(16) . ?
C2 O1 1.4456(18) . ?
C2 C3 1.5171(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N1 1.4558(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C8 1.3417(18) . ?
C4 N1 1.4279(15) . ?
C4 C5 1.4753(18) . ?
C5 C6 1.5050(18) . ?
C5 C7 1.5099(18) . ?
C5 H5 1.0000 . ?
C6 C7 1.489(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N2 1.3826(16) . ?
C8 O3 1.3943(15) . ?
C9 N2 1.2883(16) . ?
C9 C10 1.4444(17) . ?
C9 H9 0.9500 . ?
C10 C15 1.3870(18) . ?
C10 C11 1.3934(18) . ?
C11 C12 1.381(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.3777(18) . ?
C14 H14 0.9500 . ?
C15 O3 1.3770(15) . ?
 
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
O2 C1 N1 128.48(13) . . ?
O2 C1 O1 122.04(12) . . ?
N1 C1 O1 109.47(11) . . ?
O1 C2 C3 104.49(11) . . ?
O1 C2 H2A 110.9 . . ?
C3 C2 H2A 110.9 . . ?
O1 C2 H2B 110.9 . . ?
C3 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
N1 C3 C2 100.61(11) . . ?
N1 C3 H3A 111.7 . . ?
C2 C3 H3A 111.7 . . ?
N1 C3 H3B 111.7 . . ?
C2 C3 H3B 111.7 . . ?
H3A C3 H3B 109.4 . . ?
C8 C4 N1 119.33(11) . . ?
C8 C4 C5 122.25(11) . . ?
N1 C4 C5 118.41(11) . . ?
C4 C5 C6 121.77(11) . . ?
C4 C5 C7 120.67(11) . . ?
C6 C5 C7 59.21(9) . . ?
C4 C5 H5 114.7 . . ?
C6 C5 H5 114.7 . . ?
C7 C5 H5 114.7 . . ?
C7 C6 C5 60.56(9) . . ?
C7 C6 H6A 117.7 . . ?
C5 C6 H6A 117.7 . . ?
C7 C6 H6B 117.7 . . ?
C5 C6 H6B 117.7 . . ?
H6A C6 H6B 114.8 . . ?
C6 C7 C5 60.23(9) . . ?
C6 C7 H7A 117.7 . . ?
C5 C7 H7A 117.7 . . ?
C6 C7 H7B 117.7 . . ?
C5 C7 H7B 117.7 . . ?
H7A C7 H7B 114.9 . . ?
C4 C8 N2 121.31(11) . . ?
C4 C8 O3 116.96(11) . . ?
N2 C8 O3 121.73(11) . . ?
N2 C9 C10 123.58(11) . . ?
N2 C9 H9 118.2 . . ?
C10 C9 H9 118.2 . . ?
C15 C10 C11 119.17(12) . . ?
C15 C10 C9 116.67(11) . . ?
C11 C10 C9 124.16(12) . . ?
C12 C11 C10 119.86(13) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 119.96(13) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 121.04(13) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 118.44(13) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
O3 C15 C14 118.03(12) . . ?
O3 C15 C10 120.46(11) . . ?
C14 C15 C10 121.51(12) . . ?
C1 N1 C4 122.95(10) . . ?
C1 N1 C3 110.96(10) . . ?
C4 N1 C3 122.05(10) . . ?
C9 N2 C8 118.71(11) . . ?
C1 O1 C2 109.21(10) . . ?
C15 O3 C8 118.74(10) . . ?
 
_diffrn_measured_fraction_theta_max    0.989
_diffrn_reflns_theta_full              25.06
_diffrn_measured_fraction_theta_full   0.989
_refine_diff_density_max    0.169
_refine_diff_density_min   -0.149
_refine_diff_density_rms    0.030
