#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/03/1520366.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1520366
loop_
_publ_author_name
'Spencer, John'
'Patel, Hiren'
'Callear, Samantha K.'
'Hursthouse, Michael B.'
_publ_section_title
;
 C8H5N3O2
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              714
_journal_year                    2009
_chemical_formula_sum            'C8 H5 N3 O2'
_chemical_formula_weight         175.15
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 103.2100(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.7544(4)
_cell_length_b                   7.01690(10)
_cell_length_c                   11.6931(2)
_cell_measurement_reflns_used    13800
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1577.95(5)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18938
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9846
_exptl_absorpt_correction_T_min  0.9518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            'pale orange'
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         2769
_refine_ls_number_restraints     166
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0576P)²+0.9036P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1206
_reflns_number_gt                2265
_reflns_number_total             2769
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            eCrystal-714.cif
_cod_data_source_block           2009src0463p21c
_cod_depositor_comments
;
Citation :
Spencer, John and Patel, Hiren and Callear, Samantha K. and 
Hursthouse, Michael B. (2009) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/714)

More at:
http://ecrystals.chem.soton.ac.uk/714/
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1520366
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'
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 . .
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'
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
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
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_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
