data_exp_236
_audit_creation_date              2014-10-10
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_name         ''
_publ_contact_author_phone        ?
_chemical_name_common             ?
_chemical_name_systematic
;
 ? 
;
_chemical_formula_moiety          'C20 H15 N3 O4'
_chemical_formula_sum             'C20 H15 N3 O4'
_chemical_formula_weight          361.35
_chemical_melting_point           ?
_chemical_oxdiff_formula          C20H10NO
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 1 21/c 1'
_space_group_name_Hall            '-P 2ybc'
loop_
  _space_group_symop_id
  _space_group_symop_operation_xyz
 1 'x, y, z'
 2 '-x, y+1/2, -z+1/2'
 3 '-x, -y, -z'
 4 'x, -y-1/2, z-1/2'

_cell_length_a                    8.9292(3)
_cell_length_b                    12.2608(4)
_cell_length_c                    15.9631(6)
_cell_angle_alpha                 90.00
_cell_angle_beta                  101.183(3)
_cell_angle_gamma                 90.00
_cell_volume                      1714.45(10)
_cell_formula_units_Z             4
_cell_measurement_reflns_used     3353
_cell_measurement_temperature     150.00(10)
_cell_measurement_theta_max       30.7490
_cell_measurement_theta_min       2.2090
_exptl_absorpt_coefficient_mu     0.100
_exptl_absorpt_correction_T_max   1.00000
_exptl_absorpt_correction_T_min   0.88742
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour             colourless
_exptl_crystal_colour_primary     colourless
_exptl_crystal_density_diffrn     1.400
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_description        prism
_exptl_crystal_F_000              752
_exptl_crystal_size_max           0.25
_exptl_crystal_size_mid           0.2
_exptl_crystal_size_min           0.15
_exptl_special_details
;
 ? 
;
_diffrn_reflns_av_R_equivalents   0.0263
_diffrn_reflns_av_unetI/netI      0.0419
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_k_max        8
_diffrn_reflns_limit_k_min        -17
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_number             8807
_diffrn_reflns_theta_full         28.00
_diffrn_reflns_theta_max          30.76
_diffrn_reflns_theta_min          2.33
_diffrn_ambient_temperature       150.00(10)
_diffrn_detector_area_resol_mean  15.9555
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.8778
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   37.00   80.00   1.0000    9.1600
omega____ theta____ kappa____ phi______ frames
    -       23.2924  178.0000  -90.0000 43

#__ type_ start__ end____ width___ exp.time_
  2 omega  -37.00   92.00   1.0000    9.1600
omega____ theta____ kappa____ phi______ frames
    -       23.2924    0.0000 -180.0000 129

#__ type_ start__ end____ width___ exp.time_
  3 omega    2.00   60.00   1.0000    9.1600
omega____ theta____ kappa____ phi______ frames
    -       23.2924   57.0000   60.0000 58
;
_diffrn_measurement_device_type   'Xcalibur, Eos'
_diffrn_measurement_method        'ω scans'
_diffrn_orient_matrix_UB_11       -0.0714724000
_diffrn_orient_matrix_UB_12       0.0186745000
_diffrn_orient_matrix_UB_13       0.0074186000
_diffrn_orient_matrix_UB_21       0.0364687000
_diffrn_orient_matrix_UB_22       0.0217943000
_diffrn_orient_matrix_UB_23       0.0399053000
_diffrn_orient_matrix_UB_31       0.0107957000
_diffrn_orient_matrix_UB_32       0.0502522000
_diffrn_orient_matrix_UB_33       -0.0200669000
_diffrn_radiation_monochromator   graphite
_diffrn_radiation_type            'Mo K\a'
_diffrn_radiation_wavelength      0.7107
_diffrn_source                    'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%         ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_number          ?
_reflns_number_gt                 3759
_reflns_number_total              4683
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric  1
_reflns_odcompleteness_theta      28.22
_reflns_threshold_expression      >2sigma(I)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution     'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max          0.313
_refine_diff_density_min          -0.278
_refine_diff_density_rms          0.058
_refine_ls_extinction_coef        ?
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.008
_refine_ls_hydrogen_treatment     mixed
_refine_ls_matrix_type            full
_refine_ls_number_parameters      285
_refine_ls_number_reflns          4683
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0589
_refine_ls_R_factor_gt            0.0453
_refine_ls_restrained_S_all       1.008
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0830P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.1209
_refine_ls_wR_factor_ref          0.1333
_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. 
;
_atom_sites_solution_hydrogens    geom
_atom_sites_solution_primary      iterative
_atom_sites_solution_secondary    difmap
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
 O25 O 0.43216(9) 0.29086(7) 0.30730(5) 0.0229(2) Uani 1 1 d . . .
 O13 O 0.81432(9) 0.39097(7) 0.21738(5) 0.0247(2) Uani 1 1 d . . .
 O9 O 0.40711(11) 0.41762(8) 0.03603(5) 0.0287(2) Uani 1 1 d . . .
 O24 O 0.58281(10) 0.29521(9) 0.43796(6) 0.0329(2) Uani 1 1 d . . .
 N14 N 0.92573(11) 0.36354(9) 0.28975(7) 0.0255(2) Uani 1 1 d . . .
 N1 N 0.46869(12) 0.54263(9) 0.30889(7) 0.0256(2) Uani 1 1 d . . .
 N8 N 0.33199(12) 0.47761(8) 0.09031(6) 0.0250(2) Uani 1 1 d . . .
 C16 C 0.68832(12) 0.33172(9) 0.31546(7) 0.0172(2) Uani 1 1 d . . .
 C15 C 0.84988(12) 0.33006(9) 0.34780(7) 0.0193(2) Uani 1 1 d . . .
 C12 C 0.67411(13) 0.37167(9) 0.23471(7) 0.0189(2) Uani 1 1 d . . .
 C17 C 0.56509(12) 0.30384(9) 0.36138(7) 0.0185(2) Uani 1 1 d . . .
 C6 C 0.36171(13) 0.52081(9) 0.23961(7) 0.0195(2) Uani 1 1 d . . .
 C11 C 0.54739(13) 0.40119(9) 0.16622(7) 0.0193(2) Uani 1 1 d . . .
 C7 C 0.41479(13) 0.46703(9) 0.16729(7) 0.0193(2) Uani 1 1 d . . .
 C18 C 0.93773(13) 0.29927(10) 0.43303(8) 0.0211(2) Uani 1 1 d . . .
 C10 C 0.53473(15) 0.37466(10) 0.08273(8) 0.0243(3) Uani 1 1 d . . .
 C19 C 1.05339(14) 0.36848(11) 0.47432(9) 0.0274(3) Uani 1 1 d . . .
 C23 C 0.90899(15) 0.20148(10) 0.47200(8) 0.0257(3) Uani 1 1 d . . .
 C5 C 0.20717(14) 0.54518(10) 0.23330(8) 0.0241(3) Uani 1 1 d . . .
 C26 C 0.29654(13) 0.27286(10) 0.34443(8) 0.0247(3) Uani 1 1 d . . .
 H26A H 0.2139 0.3189 0.3159 0.030 Uiso 1 1 calc R . .
 H26B H 0.3187 0.2922 0.4045 0.030 Uiso 1 1 calc R . .
 C4 C 0.16067(14) 0.59384(10) 0.30230(9) 0.0269(3) Uani 1 1 d . . .
 C3 C 0.26831(16) 0.61582(11) 0.37474(9) 0.0280(3) Uani 1 1 d . . .
 C2 C 0.42010(16) 0.58881(11) 0.37488(9) 0.0299(3) Uani 1 1 d . . .
 C20 C 1.13798(16) 0.34002(14) 0.55390(9) 0.0369(3) Uani 1 1 d . . .
 C22 C 0.99535(17) 0.17365(13) 0.55104(9) 0.0354(3) Uani 1 1 d . . .
 C28 C 0.24919(15) 0.15569(11) 0.33474(9) 0.0307(3) Uani 1 1 d . . .
 H28A H 0.2376 0.1347 0.2759 0.046 Uiso 1 1 calc R . .
 H28B H 0.1538 0.1463 0.3531 0.046 Uiso 1 1 calc R . .
 H28C H 0.3258 0.1110 0.3690 0.046 Uiso 1 1 calc R . .
 C21 C 1.10963(18) 0.24260(14) 0.59187(9) 0.0406(4) Uani 1 1 d . . .
 H4 H 0.054(2) 0.6118(13) 0.2974(11) 0.040(4) Uiso 1 1 d . . .
 H3 H 0.2435(18) 0.6489(13) 0.4259(10) 0.036(4) Uiso 1 1 d . . .
 H2 H 0.4989(19) 0.6013(13) 0.4259(10) 0.037(4) Uiso 1 1 d . . .
 H10 H 0.5970(18) 0.3314(13) 0.0520(9) 0.031(4) Uiso 1 1 d . . .
 H5 H 0.1349(18) 0.5258(12) 0.1821(9) 0.031(4) Uiso 1 1 d . . .
 H23 H 0.8248(18) 0.1516(13) 0.4444(9) 0.031(4) Uiso 1 1 d . . .
 H19 H 1.0697(19) 0.4358(15) 0.4469(10) 0.041(4) Uiso 1 1 d . . .
 H20 H 1.219(2) 0.3887(14) 0.5827(12) 0.051(5) Uiso 1 1 d . . .
 H22 H 0.9753(19) 0.1008(14) 0.5778(10) 0.041(5) Uiso 1 1 d . . .
 H21 H 1.170(2) 0.2259(16) 0.6500(12) 0.060(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
 O25 C17 1.3348(14) . ?
 O25 C26 1.4645(13) . ?
 O13 N14 1.4111(13) . ?
 O13 C12 1.3543(13) . ?
 O9 N8 1.4026(13) . ?
 O9 C10 1.3425(15) . ?
 O24 C17 1.2064(14) . ?
 N14 C15 1.3150(15) . ?
 N1 C6 1.3406(15) . ?
 N1 C2 1.3401(16) . ?
 N8 C7 1.3119(15) . ?
 C16 C15 1.4350(15) . ?
 C16 C12 1.3617(16) . ?
 C16 C17 1.4758(15) . ?
 C15 C18 1.4816(16) . ?
 C12 C11 1.4584(16) . ?
 C6 C7 1.4847(15) . ?
 C6 C5 1.3963(16) . ?
 C11 C7 1.4359(16) . ?
 C11 C10 1.3551(17) . ?
 C18 C19 1.3989(17) . ?
 C18 C23 1.3972(18) . ?
 C19 C20 1.391(2) . ?
 C23 C22 1.3877(19) . ?
 C5 C4 1.3853(18) . ?
 C26 C28 1.4970(18) . ?
 C4 C3 1.3793(19) . ?
 C3 C2 1.3949(19) . ?
 C20 C21 1.385(3) . ?
 C22 C21 1.387(2) . ?

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
 C17 O25 C26 117.23(9) . . ?
 C12 O13 N14 108.91(8) . . ?
 C10 O9 N8 108.59(9) . . ?
 C15 N14 O13 105.88(9) . . ?
 C2 N1 C6 116.44(10) . . ?
 C7 N8 O9 106.06(9) . . ?
 C15 C16 C17 127.76(10) . . ?
 C12 C16 C15 104.38(10) . . ?
 C12 C16 C17 127.73(10) . . ?
 N14 C15 C16 111.17(10) . . ?
 N14 C15 C18 118.25(10) . . ?
 C16 C15 C18 130.56(10) . . ?
 O13 C12 C16 109.63(10) . . ?
 O13 C12 C11 114.66(9) . . ?
 C16 C12 C11 135.66(10) . . ?
 O25 C17 C16 111.20(10) . . ?
 O24 C17 O25 124.77(11) . . ?
 O24 C17 C16 124.03(11) . . ?
 N1 C6 C7 116.50(10) . . ?
 N1 C6 C5 123.57(11) . . ?
 C5 C6 C7 119.93(11) . . ?
 C7 C11 C12 130.72(10) . . ?
 C10 C11 C12 125.61(11) . . ?
 C10 C11 C7 103.59(11) . . ?
 N8 C7 C6 118.53(10) . . ?
 N8 C7 C11 111.14(10) . . ?
 C11 C7 C6 130.34(11) . . ?
 C19 C18 C15 119.28(11) . . ?
 C23 C18 C15 121.15(11) . . ?
 C23 C18 C19 119.56(12) . . ?
 O9 C10 C11 110.60(11) . . ?
 C20 C19 C18 119.92(14) . . ?
 C22 C23 C18 119.88(13) . . ?
 C4 C5 C6 118.64(12) . . ?
 O25 C26 C28 110.00(10) . . ?
 C3 C4 C5 118.89(11) . . ?
 C4 C3 C2 118.29(11) . . ?
 N1 C2 C3 124.17(12) . . ?
 C21 C20 C19 120.22(14) . . ?
 C21 C22 C23 120.40(15) . . ?
 C20 C21 C22 120.03(14) . . ?

