 
data_2009src0463p21c
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C8 H5 N3 O2'
_chemical_formula_weight          175.15
 
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    P21/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                    19.7544(4)
_cell_length_b                    7.01690(10)
_cell_length_c                    11.6931(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  103.2100(10)
_cell_angle_gamma                 90.00
_cell_volume                      1577.95(5)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     13800
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             'pale orange'
_exptl_crystal_size_max           0.45
_exptl_crystal_size_mid           0.26
_exptl_crystal_size_min           0.14
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.475
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              720
_exptl_absorpt_coefficient_mu     0.111
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9518
_exptl_absorpt_correction_T_max   0.9846
_exptl_absorpt_process_details    'SADABS 2007/2 (Sheldrick, G.M., 2007)' 
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature           120(2)
_diffrn_radiation_wavelength           0.71073
_diffrn_radiation_type                      MoK\a
_diffrn_radiation_source                  'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator    'graphite'
_diffrn_measurement_device_type   
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   '9.091'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             18938
_diffrn_reflns_av_R_equivalents   0.0559
_diffrn_reflns_av_sigmaI/netI     0.0386
_diffrn_reflns_limit_h_min        -23
_diffrn_reflns_limit_h_max        23
_diffrn_reflns_limit_k_min        -8
_diffrn_reflns_limit_k_max        8
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          3.09
_diffrn_reflns_theta_max          25.00
_reflns_number_total              2769
_reflns_number_gt                 2265
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'  
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_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 > 2σ(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)+(0.0576P)²+0.9036P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          2769
_refine_ls_number_parameters      287
_refine_ls_number_restraints      166
_refine_ls_R_factor_all           0.0561
_refine_ls_R_factor_gt            0.0436
_refine_ls_wR_factor_ref          0.1206
_refine_ls_wR_factor_gt           0.1107
_refine_ls_goodness_of_fit_ref    1.035
_refine_ls_restrained_S_all       1.006
_refine_ls_shift/su_max           0.002
_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 -0.0337(3) 0.2237(18) 1.0155(6) 0.0248(13) Uani 0.843(6) 1 d PDU A 1
C2 C -0.0639(3) 0.2031(10) 1.1073(5) 0.0375(10) Uani 0.843(6) 1 d PDU A 1
H2 H -0.0428 0.2209 1.1881 0.045 Uiso 0.843(6) 1 calc PR A 1
C3 C -0.13389(18) 0.1489(7) 1.0576(3) 0.0412(11) Uani 0.843(6) 1 d PDU A 1
H3 H -0.1691 0.1251 1.0992 0.049 Uiso 0.843(6) 1 calc PR A 1
C4 C -0.14084(14) 0.1381(4) 0.9417(3) 0.0376(8) Uani 0.843(6) 1 d PDU A 1
H4 H -0.1826 0.1045 0.8870 0.045 Uiso 0.843(6) 1 calc PR A 1
O5 O -0.07980(15) 0.1819(6) 0.9124(2) 0.0330(7) Uani 0.843(6) 1 d PDU A 1
C1B C -0.0296(14) 0.204(11) 1.031(3) 0.025(6) Uani 0.157(6) 1 d PDU A 2
C2B C -0.0885(13) 0.168(4) 0.9492(17) 0.027(4) Uani 0.157(6) 1 d PDU A 2
H2B H -0.0944 0.1685 0.8663 0.033 Uiso 0.157(6) 1 calc PR A 2
C3B C -0.1397(11) 0.129(5) 1.014(2) 0.0412(11) Uani 0.157(6) 1 d PDU A 2
H3B H -0.1866 0.0920 0.9832 0.049 Uiso 0.157(6) 1 calc PR A 2
C4B C -0.1088(10) 0.156(2) 1.1283(17) 0.040(3) Uani 0.157(6) 1 d PDU A 2
H4B H -0.1308 0.1366 1.1916 0.048 Uiso 0.157(6) 1 calc PR A 2
O5B O -0.0424(9) 0.213(4) 1.1405(14) 0.034(4) Uani 0.157(6) 1 d PDU A 2
C6 C 0.03603(9) 0.2775(2) 1.01055(16) 0.0238(4) Uani 1 1 d . . .
C8 C 0.11817(9) 0.3410(3) 0.92014(15) 0.0235(4) Uani 1 1 d . . .
C9 C 0.14114(9) 0.3714(2) 1.03873(15) 0.0227(4) Uani 1 1 d . A .
C12 C 0.20672(9) 0.4388(3) 1.09957(15) 0.0250(4) Uani 1 1 d . . .
C21 C 0.42021(9) 0.1688(2) 1.01059(15) 0.0227(4) Uani 1 1 d . . .
C22 C 0.39350(10) 0.1384(3) 1.10518(16) 0.0306(5) Uani 1 1 d . . .
H22 H 0.4159 0.1563 1.1854 0.037 Uiso 1 1 calc R . .
C23 C 0.32369(11) 0.0730(3) 1.0582(2) 0.0386(5) Uani 1 1 d . . .
H23 H 0.2905 0.0394 1.1021 0.046 Uiso 1 1 calc R . .
C24 C 0.31405(10) 0.0683(3) 0.94189(19) 0.0361(5) Uani 1 1 d . . .
H24 H 0.2722 0.0298 0.8892 0.043 Uiso 1 1 calc R . .
C26 C 0.48764(9) 0.2380(2) 1.00320(15) 0.0215(4) Uani 1 1 d . . .
C28 C 0.56721(9) 0.3328(3) 0.91364(15) 0.0226(4) Uani 1 1 d . . .
C29 C 0.59159(9) 0.3444(3) 1.03349(15) 0.0220(4) Uani 1 1 d . . .
C32 C 0.65843(10) 0.4026(3) 1.09615(15) 0.0251(4) Uani 1 1 d . . .
O7 O 0.05070(6) 0.28163(18) 0.90065(10) 0.0252(3) Uani 1 1 d . A .
N11 N 0.14571(9) 0.3574(3) 0.82707(14) 0.0323(4) Uani 1 1 d D A .
N13 N 0.26028(8) 0.4951(3) 1.14879(14) 0.0349(4) Uani 1 1 d . A .
O27 O 0.50055(6) 0.26479(17) 0.89328(10) 0.0227(3) Uani 1 1 d . . .
N31 N 0.59216(8) 0.3760(3) 0.82133(13) 0.0302(4) Uani 1 1 d D . .
N33 N 0.71308(8) 0.4494(3) 1.14596(14) 0.0337(4) Uani 1 1 d . . .
N10 N 0.08710(8) 0.3290(2) 1.09475(13) 0.0245(4) Uani 1 1 d . A .
O25 O 0.37299(7) 0.12676(19) 0.90887(11) 0.0323(3) Uani 1 1 d . . .
N30 N 0.53921(7) 0.2823(2) 1.08853(13) 0.0230(4) Uani 1 1 d . . .
H11A H 0.1229(9) 0.308(3) 0.7575(14) 0.028 Uiso 1 1 d D . .
H11B H 0.1879(8) 0.399(3) 0.8364(17) 0.028 Uiso 1 1 d D . .
H31A H 0.5701(10) 0.330(3) 0.7509(14) 0.028 Uiso 1 1 d D . .
H31B H 0.6365(8) 0.412(3) 0.8348(17) 0.028 Uiso 1 1 d D . .
 
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.350(6) . ?
C1 O5 1.366(5) . ?
C1 C6 1.442(5) . ?
C2 C3 1.424(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.333(5) . ?
C3 H3 0.9500 . ?
C4 O5 1.361(4) . ?
C4 H4 0.9500 . ?
C1B C2B 1.35(2) . ?
C1B O5B 1.36(2) . ?
C1B C6 1.47(2) . ?
C2B C3B 1.424(17) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.347(18) . ?
C3B H3B 0.9500 . ?
C4B O5B 1.348(15) . ?
C4B H4B 0.9500 . ?
C6 N10 1.290(2) . ?
C6 O7 1.381(2) . ?
C8 N11 1.328(2) . ?
C8 O7 1.365(2) . ?
C8 C9 1.374(2) . ?
C9 N10 1.406(2) . ?
C9 C12 1.410(2) . ?
C12 N13 1.152(2) . ?
C21 C22 1.347(3) . ?
C21 O25 1.366(2) . ?
C21 C26 1.439(2) . ?
C22 C23 1.438(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.330(3) . ?
C23 H23 0.9500 . ?
C24 O25 1.370(2) . ?
C24 H24 0.9500 . ?
C26 N30 1.291(2) . ?
C26 O27 1.379(2) . ?
C28 N31 1.320(2) . ?
C28 O27 1.369(2) . ?
C28 C29 1.376(2) . ?
C29 N30 1.407(2) . ?
C29 C32 1.416(3) . ?
C32 N33 1.151(2) . ?
N11 H11A 0.904(15) . ?
N11 H11B 0.865(15) . ?
N31 H31A 0.899(14) . ?
N31 H31B 0.890(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
C2 C1 O5 110.6(4) . . ?
C2 C1 C6 131.3(5) . . ?
O5 C1 C6 118.2(4) . . ?
C1 C2 C3 105.6(4) . . ?
C1 C2 H2 127.2 . . ?
C3 C2 H2 127.2 . . ?
C4 C3 C2 107.1(3) . . ?
C4 C3 H3 126.4 . . ?
C2 C3 H3 126.4 . . ?
C3 C4 O5 110.5(3) . . ?
C3 C4 H4 124.7 . . ?
O5 C4 H4 124.7 . . ?
C4 O5 C1 106.1(3) . . ?
C2B C1B O5B 111.1(16) . . ?
C2B C1B C6 127(2) . . ?
O5B C1B C6 120(2) . . ?
C1B C2B C3B 105.1(15) . . ?
C1B C2B H2B 127.5 . . ?
C3B C2B H2B 127.5 . . ?
C4B C3B C2B 106.6(14) . . ?
C4B C3B H3B 126.7 . . ?
C2B C3B H3B 126.7 . . ?
C3B C4B O5B 110.9(14) . . ?
C3B C4B H4B 124.6 . . ?
O5B C4B H4B 124.6 . . ?
C4B O5B C1B 105.7(14) . . ?
N10 C6 O7 114.24(15) . . ?
N10 C6 C1 129.1(3) . . ?
O7 C6 C1 116.6(3) . . ?
N10 C6 C1B 122.8(11) . . ?
O7 C6 C1B 122.7(12) . . ?
C1 C6 C1B 9(3) . . ?
N11 C8 O7 117.19(15) . . ?
N11 C8 C9 135.31(17) . . ?
O7 C8 C9 107.50(15) . . ?
C8 C9 N10 109.06(15) . . ?
C8 C9 C12 127.97(16) . . ?
N10 C9 C12 122.96(16) . . ?
N13 C12 C9 179.5(2) . . ?
C22 C21 O25 111.30(16) . . ?
C22 C21 C26 130.14(17) . . ?
O25 C21 C26 118.56(15) . . ?
C21 C22 C23 104.95(17) . . ?
C21 C22 H22 127.5 . . ?
C23 C22 H22 127.5 . . ?
C24 C23 C22 107.43(17) . . ?
C24 C23 H23 126.3 . . ?
C22 C23 H23 126.3 . . ?
C23 C24 O25 110.38(17) . . ?
C23 C24 H24 124.8 . . ?
O25 C24 H24 124.8 . . ?
N30 C26 O27 113.97(15) . . ?
N30 C26 C21 127.80(16) . . ?
O27 C26 C21 118.23(15) . . ?
N31 C28 O27 117.49(15) . . ?
N31 C28 C29 135.23(17) . . ?
O27 C28 C29 107.24(15) . . ?
C28 C29 N30 108.96(15) . . ?
C28 C29 C32 127.72(16) . . ?
N30 C29 C32 123.30(15) . . ?
N33 C32 C29 179.2(2) . . ?
C8 O7 C6 104.82(13) . . ?
C8 N11 H11A 119.4(12) . . ?
C8 N11 H11B 119.2(13) . . ?
H11A N11 H11B 120.7(18) . . ?
C28 O27 C26 105.12(13) . . ?
C28 N31 H31A 118.2(13) . . ?
C28 N31 H31B 117.2(13) . . ?
H31A N31 H31B 121.0(18) . . ?
C6 N10 C9 104.39(15) . . ?
C21 O25 C24 105.93(15) . . ?
C26 N30 C29 104.72(14) . . ?
 
loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_site_symmetry_A
N11 H11A N10  0.904(15) 2.106(15) 2.999(2) 169.7(17) 4_565
N11 H11B N33  0.865(15) 2.195(15) 3.052(2) 170.6(18) 3_667
N31 H31A N30  0.899(14) 2.017(15) 2.905(2) 168.9(18) 4_565
N31 H31B N13  0.890(15) 2.107(15) 2.995(2) 175.0(18) 3_667
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              25.00
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    0.250
_refine_diff_density_min   -0.308
_refine_diff_density_rms    0.048
