#------------------------------------------------------------------------------
#$Date: 2008-01-13 23:15:36 +0100 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2100375.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_2100375
_journal_coeditor_code         GP5001
_journal_date_accepted         2005-08-22
_journal_date_recd_electronic  2005-03-29
_journal_issue                 1
_journal_name_full             'Acta Crystallographica, Section B'
_journal_page_first            102
_journal_page_last             108
_journal_paper_category        FA
_journal_volume                62
_journal_year                  2006
_chemical_formula_moiety       'C10 H9 N5 0, H3 O4 P'
_chemical_formula_sum          'C10 H12 N5 O5 P'
_chemical_formula_weight       313.22
_chemical_name_common          'KINETINE ORTOPHOSPHATE ACID'
_chemical_name_systematic
;
 ?
;
_symmetry_cell_setting         TRICLINIC
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary   direct
_atom_sites_solution_secondary difmap
_audit_creation_method         SHELXL-97
_cell_angle_alpha              91.00(3)
_cell_angle_beta               100.92(3)
_cell_angle_gamma              108.47(3)
_cell_formula_units_Z          2
_cell_length_a                 4.4923(9)
_cell_length_b                 10.736(2)
_cell_length_c                 14.455(3)
_cell_measurement_reflns_used  3615
_cell_measurement_temperature  293(2)
_cell_measurement_theta_max    20.13
_cell_measurement_theta_min    2.16
_cell_volume                   647.0(2)
_computing_cell_refinement     'CRYSaLIS PROCEDURE'
_computing_data_collection     'CRYSaLIS PROCEDURE'
_computing_data_reduction      'CRYSaLIS PROCEDURE'
_computing_molecular_graphics  'DIAMOND 2'
_computing_publication_material ?
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution  'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature    293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.932
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device_type KM4CCD
_diffrn_measurement_method     CCD
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source       'fine-focus sealed tube'
_diffrn_radiation_type         MoK\a
_diffrn_radiation_wavelength   0.71073
_diffrn_reflns_av_R_equivalents 0.042
_diffrn_reflns_av_sigmaI/netI  0.0520
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_k_min     -17
_diffrn_reflns_limit_l_max     25
_diffrn_reflns_limit_l_min     -24
_diffrn_reflns_number          14205
_diffrn_reflns_theta_full      30.50
_diffrn_reflns_theta_max       40.3
_diffrn_reflns_theta_min       4.15
_diffrn_standards_decay_%      ?
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time ?
_diffrn_standards_number       2
_exptl_absorpt_coefficient_mu  0.245
_exptl_absorpt_correction_T_max 0.9823
_exptl_absorpt_correction_T_min 0.9152
_exptl_absorpt_correction_type 'ANALYTICAL- CrysAlis Ver170.26'
_exptl_crystal_colour          COLOURLRSS
_exptl_crystal_density_diffrn  1.608
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     'THIN NEEDLE'
_exptl_crystal_F_000           324
_exptl_crystal_size_max        0.41
_exptl_crystal_size_mid        0.09
_exptl_crystal_size_min        0.09
_refine_diff_density_max       0.423
_refine_diff_density_min       -0.415
_refine_ls_extinction_coef     0.0051(6)
_refine_ls_extinction_method   SHELXL
_refine_ls_goodness_of_fit_ref 1.212
_refine_ls_hydrogen_treatment  mixed
_refine_ls_matrix_type         full
_refine_ls_number_parameters   230
_refine_ls_number_reflns       3704
_refine_ls_number_restraints   6
_refine_ls_restrained_S_all    1.214
_refine_ls_R_factor_all        0.0816
_refine_ls_R_factor_gt         0.056
_refine_ls_shift/su_max        1.110
_refine_ls_shift/su_mean       0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.1P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_gt        0.1222
_refine_ls_wR_factor_ref       0.1373
_reflns_number_gt              3704
_reflns_number_total           5349
_reflns_threshold_expression   >2sigma(I)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
P1 0.50152(5) 0.41820(2) 0.650206(16) 0.03131(6) Uani d . 1 . . P
O11 0.84100(14) 0.49848(6) 0.69833(5) 0.03952(19) Uani d . 1 . . O
O14 0.28906(14) 0.39684(7) 0.72484(5) 0.04474(19) Uani d . 1 . . O
O12 0.37165(17) 0.49211(8) 0.57185(5) 0.0535(2) Uani d . 1 . . O
O13 0.49328(19) 0.28368(7) 0.61236(6) 0.0673(3) Uani d . 1 . . O
N7A 0.89979(18) 0.27033(7) 0.37875(5) 0.0354(2) Uani d . 1 . . N
C5A 0.9620(2) 0.17194(8) 0.33073(6) 0.0304(2) Uani d . 1 . . C
C6A 1.1143(2) 0.16831(9) 0.25398(6) 0.0329(2) Uani d . 1 . . C
N6A 1.23787(18) 0.27477(8) 0.20996(5) 0.0377(2) Uani d . 1 . . N
N1A 1.13127(19) 0.05008(8) 0.22584(6) 0.0408(2) Uani d . 1 . . N
N3A 0.84149(19) -0.06057(8) 0.33987(6) 0.0402(2) Uani d . 1 . . N
C4A 0.8292(2) 0.05723(9) 0.37032(6) 0.0325(2) Uani d . 1 . . C
N9A 0.68896(18) 0.08407(8) 0.44098(6) 0.0393(2) Uani d D 1 . . N
C2A 0.9964(2) -0.05447(10) 0.26902(8) 0.0447(3) Uani d . 1 . . C
C8A 0.7386(2) 0.21350(10) 0.44356(7) 0.0415(3) Uani d . 1 . . C
C10A 1.3657(2) 0.27000(11) 0.12400(7) 0.0450(3) Uani d . 1 . . C
C11A 1.1203(2) 0.25788(11) 0.03733(7) 0.0453(3) Uani d D 1 . . C
O15A 0.8842(3) 0.14556(10) 0.00751(8) 0.0966(4) Uani d D 1 . . O
C14A 0.6949(4) 0.16948(19) -0.07229(11) 0.1018(6) Uani d D 1 . . C
C13A 0.8047(4) 0.29113(19) -0.08774(11) 0.1101(6) Uani d D 1 . . C
C12A 1.0819(3) 0.35400(12) -0.01366(11) 0.0762(5) Uani d D 1 . . C
H8A 0.671(2) 0.2572(10) 0.4879(7) 0.038(3) Uiso d . 1 . . H
H7A 0.952(2) 0.3632(11) 0.3627(8) 0.061(3) Uiso d . 1 . . H
H6A 1.208(2) 0.3477(10) 0.2296(8) 0.051(3) Uiso d . 1 . . H
H2A 0.999(2) -0.1410(10) 0.2454(7) 0.041(3) Uiso d . 1 . . H
H14 0.143(3) 0.4282(11) 0.7195(8) 0.058(3) Uiso d . 1 . . H
H10A 1.450(2) 0.1871(11) 0.1228(7) 0.057(3) Uiso d . 1 . . H
H10B 1.528(2) 0.3468(11) 0.1265(8) 0.057(3) Uiso d . 1 . . H
H12 0.460(5) 0.481(2) 0.5268(14) 0.059(7) Uiso d P 0.50 . . H
H9A 0.573(4) 0.0306(17) 0.4720(11) 0.034(5) Uiso d PD 0.50 . . H
H3 0.685(4) -0.1663(19) 0.3579(14) 0.155(8) Uiso d . 1 . . H
H14A 0.4887 0.0997 -0.1122 0.105 Uiso d . 1 . . H
H13A 0.7194 0.3454 -0.1398 0.111 Uiso d . 1 . . H
H12A 1.2254 0.4512 -0.0100 0.121 Uiso d . 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
P1 0.03355(9) 0.03164(10) 0.03291(11) 0.01117(8) 0.01541(8) 0.00763(8)
O11 0.0319(3) 0.0347(3) 0.0553(4) 0.0121(2) 0.0140(3) 0.0103(3)
O14 0.0415(3) 0.0672(4) 0.0448(3) 0.0333(2) 0.0261(2) 0.0279(3)
O12 0.0564(4) 0.0705(4) 0.0384(4) 0.0244(3) 0.0128(3) 0.0220(3)
O13 0.0984(5) 0.0280(3) 0.0827(5) 0.0072(3) 0.0598(4) -0.0006(3)
N7A 0.0393(3) 0.0333(4) 0.0350(4) 0.0111(3) 0.0114(3) 0.0070(3)
C5A 0.0305(4) 0.0292(4) 0.0296(4) 0.0072(3) 0.0059(3) 0.0049(3)
C6A 0.0313(4) 0.0349(4) 0.0301(4) 0.0082(3) 0.0050(3) 0.0051(3)
N6A 0.0439(4) 0.0346(4) 0.0352(4) 0.0091(3) 0.0154(3) 0.0057(3)
N1A 0.0466(4) 0.0359(4) 0.0427(4) 0.0133(3) 0.0161(3) 0.0047(3)
N3A 0.0449(4) 0.0291(4) 0.0459(4) 0.0099(3) 0.0113(4) 0.0070(3)
C4A 0.0314(4) 0.0331(4) 0.0311(4) 0.0078(3) 0.0058(3) 0.0074(3)
N9A 0.0394(4) 0.0438(4) 0.0350(4) 0.0102(3) 0.0132(3) 0.0097(3)
C2A 0.0531(5) 0.0343(5) 0.0493(6) 0.0150(4) 0.0150(4) 0.0060(4)
C8A 0.0405(4) 0.0477(5) 0.0376(5) 0.0120(4) 0.0152(4) 0.0059(4)
C10A 0.0454(4) 0.0516(5) 0.0420(5) 0.0136(4) 0.0218(4) 0.0130(4)
C11A 0.0521(5) 0.0541(6) 0.0380(5) 0.0204(4) 0.0232(4) 0.0076(4)
O15A 0.0969(7) 0.0757(6) 0.0971(8) 0.0207(6) -0.0157(7) 0.0065(6)
C14A 0.1030(9) 0.1377(12) 0.0633(9) 0.0626(8) -0.0238(8) -0.0238(9)
C13A 0.1290(8) 0.1903(12) 0.0632(8) 0.1129(7) 0.0348(7) 0.0598(8)
C12A 0.0803(8) 0.0632(6) 0.0918(9) 0.0337(6) 0.0136(7) 0.0388(6)
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'
P P 0.1023 0.0942 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O11 P1 O13 . . 109.90(5) ?
O11 P1 O12 . . 110.41(5) ?
O13 P1 O12 . . 111.52(5) ?
O11 P1 O14 . . 108.18(4) ?
O13 P1 O14 . . 108.06(5) ?
O12 P1 O14 . . 108.67(5) ?
O11 P1 H12 . . 103.1(6) ?
O13 P1 H12 . . 92.8(8) ?
O12 P1 H12 . . 25.5(8) ?
O14 P1 H12 . . 132.9(8) ?
P1 O14 H14 . . 120.0(8) ?
P1 O12 H12 . . 103.9(17) ?
C8A N7A C5A . . 106.79(8) ?
C8A N7A H7A . . 128.1(7) ?
C5A N7A H7A . . 124.9(7) ?
C4A C5A N7A . . 106.31(8) ?
C4A C5A C6A . . 119.52(9) ?
N7A C5A C6A . . 134.15(8) ?
N6A C6A N1A . . 120.17(9) ?
N6A C6A C5A . . 122.78(9) ?
N1A C6A C5A . . 117.06(8) ?
C6A N6A C10A . . 123.30(9) ?
C6A N6A H6A . . 115.5(7) ?
C10A N6A H6A . . 120.4(7) ?
C2A N1A C6A . . 118.57(9) ?
C2A N3A C4A . . 113.87(8) ?
C2A N3A H3 . . 118.4(10) ?
C4A N3A H3 . . 126.3(10) ?
N3A C4A N9A . . 128.19(9) ?
N3A C4A C5A . . 122.65(9) ?
N9A C4A C5A . . 109.15(9) ?
C8A N9A C4A . . 105.61(9) ?
C8A N9A H9A . . 125.5(13) ?
C4A N9A H9A . . 128.4(13) ?
N1A C2A N3A . . 128.28(10) ?
N1A C2A H2A . . 117.9(6) ?
N3A C2A H2A . . 113.7(6) ?
N7A C8A N9A . . 112.14(10) ?
N7A C8A H8A . . 125.5(6) ?
N9A C8A H8A . . 122.3(6) ?
N6A C10A C11A . . 111.86(9) ?
N6A C10A H10A . . 109.4(6) ?
C11A C10A H10A . . 108.8(5) ?
N6A C10A H10B . . 106.6(7) ?
C11A C10A H10B . . 109.2(7) ?
H10A C10A H10B . . 111.0(9) ?
C12A C11A O15A . . 111.26(10) ?
C12A C11A C10A . . 126.62(10) ?
O15A C11A C10A . . 121.75(11) ?
C11A O15A C14A . . 106.75(12) ?
C13A C14A O15A . . 109.34(13) ?
C13A C14A H14A . . 125.6 ?
O15A C14A H14A . . 125.0 ?
C14A C13A C12A . . 107.81(14) ?
C14A C13A H13A . . 131.0 ?
C12A C13A H13A . . 121.2 ?
C11A C12A C13A . . 104.61(12) ?
C11A C12A H12A . . 130.2 ?
C13A C12A H12A . . 124.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O11 . 1.5155(9) ?
P1 O13 . 1.5222(9) ?
P1 O12 . 1.5256(9) ?
P1 O14 . 1.5452(8) ?
P1 H12 . 1.92(2) ?
O14 H14 . 0.818(13) ?
O12 H12 . 0.85(2) ?
N7A C8A . 1.3309(13) ?
N7A C5A . 1.3822(13) ?
N7A H7A . 0.992(12) ?
C5A C4A . 1.3743(13) ?
C5A C6A . 1.4154(14) ?
C6A N6A . 1.3329(13) ?
C6A N1A . 1.3555(13) ?
N6A C10A . 1.4708(14) ?
N6A H6A . 0.886(12) ?
N1A C2A . 1.3242(14) ?
N3A C2A . 1.3346(15) ?
N3A C4A . 1.3528(13) ?
N3A H3 . 1.193(19) ?
C4A N9A . 1.3683(14) ?
N9A C8A . 1.3344(14) ?
N9A H9A . 0.843(15) ?
C2A H2A . 0.988(10) ?
C8A H8A . 0.937(11) ?
C10A C11A . 1.4772(15) ?
C10A H10A . 1.074(12) ?
C10A H10B . 0.907(10) ?
C11A C12A . 1.3150(18) ?
C11A O15A . 1.3278(14) ?
O15A C14A . 1.377(2) ?
C14A C13A . 1.282(3) ?
C14A H14A . 1.0463 ?
C13A C12A . 1.446(2) ?
C13A H13A . 1.0487 ?
C12A H12A . 1.0326 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N7A H7A O11 2_766 0.992(12) 1.825(11) 2.7414(13) 152.2(11)
N6A H6A O11 2_766 0.886(12) 2.030(12) 2.9019(13) 168.0(10)
O14 H14 O11 1_455 0.818(13) 1.734(13) 2.5501(12) 174.9(12)
O12 H12 O12 2_666 0.85(2) 1.72(2) 2.5435(17) 162(3)
N3A H3 O13 2_656 1.193(19) 1.388(19) 2.5777(14) 174.4(17)
N9A H9A N9A 2_656 0.843(15) 2.044(16) 2.8837(19) 173.9(15)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8A N7A C5A C4A . . . . 0.24(9) ?
C8A N7A C5A C6A . . . . 178.17(9) ?
C4A C5A C6A N6A . . . . 177.51(8) ?
N7A C5A C6A N6A . . . . -0.20(15) ?
C4A C5A C6A N1A . . . . -2.51(12) ?
N7A C5A C6A N1A . . . . 179.78(9) ?
N1A C6A N6A C10A . . . . 6.77(13) ?
C5A C6A N6A C10A . . . . -173.25(8) ?
N6A C6A N1A C2A . . . . -177.72(8) ?
C5A C6A N1A C2A . . . . 2.30(12) ?
C2A N3A C4A N9A . . . . 179.89(9) ?
C2A N3A C4A C5A . . . . 0.67(12) ?
N7A C5A C4A N3A . . . . 179.30(8) ?
C6A C5A C4A N3A . . . . 1.02(13) ?
N7A C5A C4A N9A . . . . -0.05(9) ?
C6A C5A C4A N9A . . . . -178.33(7) ?
N3A C4A N9A C8A . . . . -179.47(9) ?
C5A C4A N9A C8A . . . . -0.17(10) ?
C6A N1A C2A N3A . . . . -0.62(15) ?
C4A N3A C2A N1A . . . . -0.93(15) ?
C5A N7A C8A N9A . . . . -0.37(10) ?
C4A N9A C8A N7A . . . . 0.34(10) ?
C6A N6A C10A C11A . . . . 92.95(12) ?
N6A C10A C11A C12A . . . . 98.20(15) ?
N6A C10A C11A O15A . . . . -74.12(15) ?
C12A C11A O15A C14A . . . . 4.64(17) ?
C10A C11A O15A C14A . . . . 178.02(13) ?
C11A O15A C14A C13A . . . . -2.2(2) ?
O15A C14A C13A C12A . . . . -0.7(2) ?
O15A C11A C12A C13A . . . . -4.94(17) ?
C10A C11A C12A C13A . . . . -177.94(13) ?
C14A C13A C12A C11A . . . . 3.4(2) ?