data_exp_907
_audit_creation_date              2016-04-07
_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          '0.8(C13 H10 N4 O3)'
_chemical_formula_sum             'C10.40 H8 N3.20 O2.40'
_chemical_formula_weight          216.20
_chemical_absolute_configuration  unk
_chemical_melting_point           ?
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       'orthorhombic'
_space_group_IT_number            19
_space_group_name_H-M_alt         'P 21 21 21'
_space_group_name_Hall            'P 2ac 2ab'
loop_
  _space_group_symop_id
  _space_group_symop_operation_xyz
 1 'x, y, z'
 2 '-x+1/2, -y, z+1/2'
 3 'x+1/2, -y+1/2, -z'
 4 '-x, y+1/2, -z+1/2'

_cell_length_a                    6.5200(9)
_cell_length_b                    10.4602(5)
_cell_length_c                    17.7675(8)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1211.76(18)
_cell_formula_units_Z             5
_cell_measurement_reflns_used     1546
_cell_measurement_temperature     295(2)
_cell_measurement_theta_max       30.4020
_cell_measurement_theta_min       2.3310
_exptl_absorpt_coefficient_mu     0.109
_exptl_absorpt_correction_T_max   1.00000
_exptl_absorpt_correction_T_min   0.89735
_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             red
_exptl_crystal_colour_primary     red
_exptl_crystal_density_diffrn     1.481
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_description        prism
_exptl_crystal_F_000              560
_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   0.0169
_diffrn_reflns_av_unetI/netI      0.0324
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_l_max        25
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_number             4288
_diffrn_reflns_theta_full         26.00
_diffrn_reflns_theta_max          30.61
_diffrn_reflns_theta_min          2.26
_diffrn_ambient_temperature       295(2)
_diffrn_detector_area_resol_mean  15.9555
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.8106
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -90.00  -63.00   1.0000   17.0400
omega____ theta____ kappa____ phi______ frames
    -      -20.7924 -178.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -40.00   86.00   1.0000   17.0400
omega____ theta____ kappa____ phi______ frames
    -       23.2924    0.0000  120.0000 126
;
_diffrn_measurement_device_type   'Xcalibur, Eos'
_diffrn_measurement_method        'ω scans'
_diffrn_orient_matrix_UB_11       -0.0054641000
_diffrn_orient_matrix_UB_12       0.0257887000
_diffrn_orient_matrix_UB_13       -0.0368415000
_diffrn_orient_matrix_UB_21       -0.1015460000
_diffrn_orient_matrix_UB_22       0.0211825000
_diffrn_orient_matrix_UB_23       0.0071514000
_diffrn_orient_matrix_UB_31       0.0388723000
_diffrn_orient_matrix_UB_32       0.0590439000
_diffrn_orient_matrix_UB_33       0.0135414000
_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                 2489
_reflns_number_total              3018
_reflns_odcompleteness_completeness 99.94
_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
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max          0.147
_refine_diff_density_min          -0.238
_refine_diff_density_rms          0.045
_refine_ls_abs_structure_details  'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    -1.1(16)
_refine_ls_extinction_coef        ?
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.003
_refine_ls_hydrogen_treatment     mixed
_refine_ls_matrix_type            full
_refine_ls_number_parameters      182
_refine_ls_number_reflns          3018
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0564
_refine_ls_R_factor_gt            0.0440
_refine_ls_restrained_S_all       1.003
_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)+(0.0690P)²+0.0330P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.1098
_refine_ls_wR_factor_ref          0.1188
_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      direct
_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
 N1 N 0.0208(2) 0.68383(13) 0.12662(9) 0.0430(4) Uani 1 1 d . . .
 C5 C -0.0712(3) 0.72973(16) 0.19095(9) 0.0403(4) Uani 1 1 d . . .
 C13 C -0.5907(3) 1.00192(15) 0.11223(9) 0.0377(4) Uani 1 1 d . . .
 N4 N 0.0159(3) 0.70912(18) 0.26299(10) 0.0553(4) Uani 1 1 d . . .
 N3 N -0.2687(2) 0.78072(14) 0.09363(8) 0.0428(4) Uani 1 1 d . . .
 O10 O -0.6239(3) 0.91050(17) 0.30484(8) 0.0694(5) Uani 1 1 d . . .
 C18 C -0.4317(3) 1.06049(16) 0.07377(10) 0.0421(4) Uani 1 1 d . . .
 H18 H -0.3008 1.0627 0.0945 0.051 Uiso 1 1 calc R . .
 C12 C -0.5582(3) 0.94489(16) 0.18753(10) 0.0406(4) Uani 1 1 d . . .
 C14 C -0.7857(3) 1.00001(19) 0.08118(12) 0.0490(5) Uani 1 1 d . . .
 H14 H -0.8937 0.9628 0.1074 0.059 Uiso 1 1 calc R . .
 C16 C -0.6611(4) 1.11118(19) -0.02709(11) 0.0560(5) Uani 1 1 d . . .
 H16 H -0.6844 1.1471 -0.0742 0.067 Uiso 1 1 calc R . .
 C8 C -0.4090(3) 0.85433(16) 0.21380(9) 0.0402(4) Uani 1 1 d . . .
 C4 C -0.2501(3) 0.79017(15) 0.17014(9) 0.0361(4) Uani 1 1 d . . .
 C17 C -0.4683(3) 1.11578(17) 0.00434(11) 0.0479(5) Uani 1 1 d . . .
 H17 H -0.3622 1.1563 -0.0212 0.057 Uiso 1 1 calc R . .
 C9 C -0.4631(4) 0.8377(2) 0.28673(11) 0.0553(5) Uani 1 1 d . . .
 H9 H -0.3968 0.7827 0.3199 0.066 Uiso 1 1 calc R . .
 C6 C 0.2160(4) 0.6172(2) 0.11529(15) 0.0649(6) Uani 1 1 d . . .
 H6A H 0.3260 0.6686 0.1346 0.097 Uiso 1 1 calc R . .
 H6B H 0.2368 0.6025 0.0625 0.097 Uiso 1 1 calc R . .
 H6C H 0.2131 0.5368 0.1413 0.097 Uiso 1 1 calc R . .
 O1 O 0.1678(3) 0.6416(2) 0.26807(10) 0.0907(6) Uani 1 1 d . . .
 C2 C -0.1045(3) 0.71785(17) 0.07063(10) 0.0450(4) Uani 1 1 d . . .
 H2 H -0.0786 0.6991 0.0203 0.054 Uiso 1 1 calc R . .
 O2 O -0.0639(3) 0.75962(19) 0.31714(8) 0.0744(5) Uani 1 1 d . . .
 N11 N -0.6847(3) 0.97971(18) 0.24094(10) 0.0600(5) Uani 1 1 d . . .
 C15 C -0.8190(4) 1.0536(2) 0.01112(13) 0.0591(6) Uani 1 1 d . . .
 H15 H -0.9491 1.0506 -0.0102 0.071 Uiso 1 1 calc R . .


_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
 N1 C5 1.377(2) . ?
 N1 C6 1.465(3) . ?
 N1 C2 1.335(2) . ?
 C5 N4 1.417(2) . ?
 C5 C4 1.377(3) . ?
 C13 C18 1.384(3) . ?
 C13 C12 1.480(2) . ?
 C13 C14 1.386(3) . ?
 N4 O1 1.220(2) . ?
 N4 O2 1.215(2) . ?
 N3 C4 1.368(2) . ?
 N3 C2 1.321(2) . ?
 O10 C9 1.336(3) . ?
 O10 N11 1.404(2) . ?
 C18 H18 0.9300 . ?
 C18 C17 1.383(3) . ?
 C12 C8 1.436(3) . ?
 C12 N11 1.309(2) . ?
 C14 H14 0.9300 . ?
 C14 C15 1.382(3) . ?
 C16 H16 0.9300 . ?
 C16 C17 1.376(3) . ?
 C16 C15 1.372(3) . ?
 C8 C4 1.458(2) . ?
 C8 C9 1.354(3) . ?
 C17 H17 0.9300 . ?
 C9 H9 0.9300 . ?
 C6 H6A 0.9600 . ?
 C6 H6B 0.9600 . ?
 C6 H6C 0.9600 . ?
 C2 H2 0.9300 . ?
 C15 H15 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
 C5 N1 C6 131.18(17) . . ?
 C2 N1 C5 105.00(15) . . ?
 C2 N1 C6 123.76(18) . . ?
 N1 C5 N4 121.45(17) . . ?
 C4 C5 N1 107.83(14) . . ?
 C4 C5 N4 130.70(17) . . ?
 C18 C13 C12 121.16(16) . . ?
 C18 C13 C14 119.78(17) . . ?
 C14 C13 C12 119.03(17) . . ?
 O1 N4 C5 118.73(19) . . ?
 O2 N4 C5 118.52(18) . . ?
 O2 N4 O1 122.75(18) . . ?
 C2 N3 C4 105.75(15) . . ?
 C9 O10 N11 108.72(15) . . ?
 C13 C18 H18 120.1 . . ?
 C17 C18 C13 119.74(18) . . ?
 C17 C18 H18 120.1 . . ?
 C8 C12 C13 131.05(16) . . ?
 N11 C12 C13 116.94(17) . . ?
 N11 C12 C8 112.01(17) . . ?
 C13 C14 H14 120.1 . . ?
 C15 C14 C13 119.8(2) . . ?
 C15 C14 H14 120.1 . . ?
 C17 C16 H16 120.0 . . ?
 C15 C16 H16 120.0 . . ?
 C15 C16 C17 119.98(19) . . ?
 C12 C8 C4 127.75(15) . . ?
 C9 C8 C12 102.68(18) . . ?
 C9 C8 C4 129.42(18) . . ?
 C5 C4 C8 132.09(15) . . ?
 N3 C4 C5 107.98(16) . . ?
 N3 C4 C8 119.92(16) . . ?
 C18 C17 H17 119.8 . . ?
 C16 C17 C18 120.3(2) . . ?
 C16 C17 H17 119.8 . . ?
 O10 C9 C8 111.20(19) . . ?
 O10 C9 H9 124.4 . . ?
 C8 C9 H9 124.4 . . ?
 N1 C6 H6A 109.5 . . ?
 N1 C6 H6B 109.5 . . ?
 N1 C6 H6C 109.5 . . ?
 H6A C6 H6B 109.5 . . ?
 H6A C6 H6C 109.5 . . ?
 H6B C6 H6C 109.5 . . ?
 N1 C2 H2 123.3 . . ?
 N3 C2 N1 113.44(16) . . ?
 N3 C2 H2 123.3 . . ?
 C12 N11 O10 105.36(17) . . ?
 C14 C15 H15 119.8 . . ?
 C16 C15 C14 120.4(2) . . ?
 C16 C15 H15 119.8 . . ?

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 C5 N4 O1 -5.2(3) . . . . ?
 N1 C5 N4 O2 174.75(18) . . . . ?
 N1 C5 C4 N3 0.42(18) . . . . ?
 N1 C5 C4 C8 179.13(16) . . . . ?
 C5 N1 C2 N3 -0.4(2) . . . . ?
 C13 C18 C17 C16 -0.9(3) . . . . ?
 C13 C12 C8 C4 -2.4(3) . . . . ?
 C13 C12 C8 C9 -178.21(18) . . . . ?
 C13 C12 N11 O10 178.63(15) . . . . ?
 C13 C14 C15 C16 -1.5(3) . . . . ?
 N4 C5 C4 N3 -177.96(18) . . . . ?
 N4 C5 C4 C8 0.8(3) . . . . ?
 C18 C13 C12 C8 -52.3(3) . . . . ?
 C18 C13 C12 N11 128.23(19) . . . . ?
 C18 C13 C14 C15 1.7(3) . . . . ?
 C12 C13 C18 C17 -178.34(15) . . . . ?
 C12 C13 C14 C15 179.59(16) . . . . ?
 C12 C8 C4 C5 160.64(18) . . . . ?
 C12 C8 C4 N3 -20.8(3) . . . . ?
 C12 C8 C9 O10 -1.1(2) . . . . ?
 C14 C13 C18 C17 -0.5(3) . . . . ?
 C14 C13 C12 C8 129.9(2) . . . . ?
 C14 C13 C12 N11 -49.6(2) . . . . ?
 C8 C12 N11 O10 -0.9(2) . . . . ?
 C4 C5 N4 O1 173.00(19) . . . . ?
 C4 C5 N4 O2 -7.1(3) . . . . ?
 C4 N3 C2 N1 0.6(2) . . . . ?
 C4 C8 C9 O10 -176.83(18) . . . . ?
 C17 C16 C15 C14 0.0(3) . . . . ?
 C9 O10 N11 C12 0.2(2) . . . . ?
 C9 C8 C4 C5 -24.6(3) . . . . ?
 C9 C8 C4 N3 153.9(2) . . . . ?
 C6 N1 C5 N4 -4.3(3) . . . . ?
 C6 N1 C5 C4 177.17(17) . . . . ?
 C6 N1 C2 N3 -177.85(16) . . . . ?
 C2 N1 C5 N4 178.50(16) . . . . ?
 C2 N1 C5 C4 -0.06(18) . . . . ?
 C2 N3 C4 C5 -0.62(19) . . . . ?
 C2 N3 C4 C8 -179.51(15) . . . . ?
 N11 O10 C9 C8 0.6(2) . . . . ?
 N11 C12 C8 C4 177.11(18) . . . . ?
 N11 C12 C8 C9 1.3(2) . . . . ?
 C15 C16 C17 C18 1.2(3) . . . . ?

