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#$Date: 2016-03-21 02:26:29 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178389 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/11/4021125.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_4021125
loop_
_publ_author_name
'Jinhua Chen'
'Thota Sambaiah'
'Boris Illarionov'
'Markus Fischer'
'Adelbert Bacher'
'Mark Cushman'
_publ_section_title
;
 Design, Synthesis, and Evaluation of Acyclic C-Nucleoside and
 N-Methylated Derivatives of the Ribitylaminopyrimidine
 Substrate of Lumazine Synthase as Potential Enzyme Inhibitors
 and Mechanistic Probes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6996
_journal_page_last               7003
_journal_paper_doi               10.1021/jo048975f
_journal_volume                  69
_journal_year                    2004
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C10 H15 N3 O8'
_chemical_formula_sum            'C10 H15 N3 O8'
_chemical_formula_weight         305.25
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 95.39(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.230(5)
_cell_length_b                   7.452(3)
_cell_length_c                   18.389(9)
_cell_measurement_temperature    150
_cell_volume                     1259.3(10)
_diffrn_ambient_temperature      150
_exptl_crystal_density_diffrn    1.61
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4021125
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
O(13) O 0.7021(3) -0.0467(4) 0.28412(12) 0.0352(6) Uani 1 1 d . . .
O(15) O 0.3792(2) 0.4093(3) 0.30166(12) 0.0314(6) Uani 1 1 d . . .
O(23) O 0.3216(3) -0.1440(4) 0.20698(13) 0.0364(6) Uani 1 1 d . . .
O(25) O 0.6642(3) -0.5805(3) 0.19778(12) 0.0344(6) Uani 1 1 d . . .
O(113) O -0.0103(3) -0.1185(3) 0.44769(12) 0.0304(6) Uani 1 1 d . . .
O(114) O -0.0641(2) -0.3219(3) 0.31180(11) 0.0287(5) Uani 1 1 d . . .
O(115) O 0.1443(2) -0.6376(3) 0.42841(11) 0.0282(5) Uani 1 1 d . . .
O(116) O -0.0118(3) -0.8911(3) 0.33762(13) 0.0367(6) Uani 1 1 d . . .
O(121) O 0.6287(3) -0.3518(4) 0.35431(14) 0.0385(6) Uani 1 1 d . . .
O(122) O 0.5695(4) -0.2871(5) 0.46145(15) 0.0618(10) Uani 1 1 d . . .
O(213) O 1.0202(3) -0.0380(4) 0.09051(13) 0.0347(6) Uani 1 1 d . . .
O(214) O 1.0916(3) 0.1825(4) 0.20866(12) 0.0328(6) Uani 1 1 d . . .
O(215) O 0.9150(3) 0.4416(3) 0.05648(11) 0.0324(6) Uani 1 1 d . . .
O(216) O 1.0114(3) 0.6510(3) 0.16854(12) 0.0329(6) Uani 1 1 d . . .
O(221) O 0.3930(3) 0.1649(4) 0.13282(14) 0.0445(7) Uani 1 1 d . . .
O(222) O 0.4247(4) 0.0682(5) 0.02486(14) 0.0568(9) Uani 1 1 d . . .
N(12) N 0.5773(3) -0.2476(4) 0.39733(16) 0.0318(7) Uani 1 1 d . . .
N(14) N 0.5456(3) 0.1820(4) 0.29671(15) 0.0281(6) Uani 1 1 d . . .
N(16) N 0.3620(3) 0.1637(4) 0.37353(14) 0.0258(6) Uani 1 1 d . . .
N(22) N 0.4357(3) 0.0526(4) 0.09149(15) 0.0347(7) Uani 1 1 d . . .
N(24) N 0.4897(3) -0.3639(4) 0.19919(16) 0.0293(7) Uani 1 1 d . . .
N(26) N 0.6803(3) -0.3332(4) 0.12637(14) 0.0289(7) Uani 1 1 d . . .
C(11) C 0.4073(4) 0.0004(5) 0.39824(16) 0.0258(8) Uani 1 1 d . . .
C(12) C 0.5263(4) -0.0750(5) 0.37183(16) 0.0264(7) Uani 1 1 d . . .
C(13) C 0.6008(4) 0.0128(5) 0.31532(18) 0.0275(8) Uani 1 1 d . . .
C(15) C 0.4272(4) 0.2623(5) 0.32204(18) 0.0270(8) Uani 1 1 d . . .
C(21) C 0.6245(4) -0.1785(5) 0.09670(17) 0.0274(8) Uani 1 1 d . . .
C(22) C 0.5018(4) -0.1110(5) 0.12228(17) 0.0289(8) Uani 1 1 d . . .
C(23) C 0.4287(4) -0.1984(5) 0.17887(18) 0.0303(8) Uani 1 1 d . . .
C(25) C 0.6139(4) -0.4349(5) 0.17630(17) 0.0279(8) Uani 1 1 d . . .
C(111) C 0.3035(4) -0.0906(5) 0.44466(16) 0.0269(8) Uani 1 1 d . . .
C(112) C 0.2093(4) -0.2216(5) 0.39566(18) 0.0279(8) Uani 1 1 d . . .
C(113) C 0.0721(4) -0.2736(5) 0.43010(17) 0.0261(7) Uani 1 1 d . . .
C(114) C -0.0255(4) -0.3987(5) 0.38258(16) 0.0254(7) Uani 1 1 d . . .
C(115) C 0.0439(3) -0.5804(5) 0.36909(16) 0.0249(7) Uani 1 1 d . . .
C(116) C -0.0718(4) -0.7197(5) 0.35173(18) 0.0294(8) Uani 1 1 d . . .
C(211) C 0.7101(4) -0.0916(5) 0.04065(17) 0.0307(8) Uani 1 1 d . . .
C(212) C 0.7797(4) 0.0890(5) 0.06432(18) 0.0317(8) Uani 1 1 d . . .
C(213) C 0.9076(4) 0.0638(5) 0.12138(17) 0.0295(8) Uani 1 1 d . . .
C(214) C 0.9750(4) 0.2348(5) 0.15522(18) 0.0289(8) Uani 1 1 d . . .
C(215) C 1.0335(4) 0.3707(5) 0.10271(17) 0.0297(8) Uani 1 1 d . . .
C(216) C 1.1131(4) 0.5259(5) 0.14284(19) 0.0331(8) Uani 1 1 d . . .
H(14) H 0.588(5) 0.263(7) 0.263(2) 0.063(14) Uiso 1 1 d . . .
H(16) H 0.285(5) 0.213(8) 0.388(3) 0.064(15) Uiso 1 1 d . . .
H(24) H 0.461(5) -0.430(7) 0.237(2) 0.052(12) Uiso 1 1 d . . .
H(26) H 0.762(4) -0.381(5) 0.1099(19) 0.030(10) Uiso 1 1 d . . .
H(113) H -0.0205 -0.0497 0.4114 0.046 Uiso 1 1 calc R . .
H(114) H -0.1470 -0.2752 0.3108 0.043 Uiso 1 1 calc R . .
H(115) H 0.1004 -0.6496 0.4661 0.042 Uiso 1 1 calc R . .
H(116) H 0.0168 -0.8917 0.2956 0.055 Uiso 1 1 calc R . .
H(11A) H 0.2410 -0.0003 0.4659 0.032 Uiso 1 1 calc R . .
H(11B) H 0.3582 -0.1567 0.4851 0.032 Uiso 1 1 calc R . .
H(11C) H 0.1824 -0.1648 0.3476 0.033 Uiso 1 1 calc R . .
H(11D) H 0.2665 -0.3309 0.3874 0.033 Uiso 1 1 calc R . .
H(11E) H 0.1024 -0.3380 0.4768 0.031 Uiso 1 1 calc R . .
H(11F) H -0.1166 -0.4195 0.4068 0.031 Uiso 1 1 calc R . .
H(11G) H 0.0992 -0.5676 0.3252 0.030 Uiso 1 1 calc R . .
H(11H) H -0.1321 -0.7298 0.3933 0.035 Uiso 1 1 calc R . .
H(11I) H -0.1360 -0.6809 0.3084 0.035 Uiso 1 1 calc R . .
H(213) H 1.0403 -0.1294 0.1163 0.052 Uiso 1 1 calc R . .
H(214) H 1.1496 0.1152 0.1890 0.049 Uiso 1 1 calc R . .
H(215) H 0.9371 0.4444 0.0132 0.049 Uiso 1 1 calc R . .
H(216) H 1.0115 0.6413 0.2141 0.049 Uiso 1 1 calc R . .
H(21A) H 0.6448 -0.0729 -0.0046 0.037 Uiso 1 1 calc R . .
H(21B) H 0.7880 -0.1751 0.0289 0.037 Uiso 1 1 calc R . .
H(21C) H 0.8131 0.1504 0.0212 0.038 Uiso 1 1 calc R . .
H(21D) H 0.7059 0.1662 0.0845 0.038 Uiso 1 1 calc R . .
H(21E) H 0.8728 -0.0094 0.1619 0.035 Uiso 1 1 calc R . .
H(21F) H 0.8992 0.2966 0.1816 0.035 Uiso 1 1 calc R . .
H(21G) H 1.1019 0.3083 0.0720 0.036 Uiso 1 1 calc R . .
H(21H) H 1.1771 0.4789 0.1848 0.040 Uiso 1 1 calc R . .
H(21I) H 1.1749 0.5879 0.1095 0.040 Uiso 1 1 calc R . .
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
O(13) C(13) 1.224(4) . ?
O(15) C(15) 1.226(4) . ?
O(23) C(23) 1.227(4) . ?
O(25) C(25) 1.231(4) . ?
O(113) C(113) 1.438(4) . ?
O(114) C(114) 1.436(4) . ?
O(115) C(115) 1.429(4) . ?
O(116) C(116) 1.425(4) . ?
O(121) N(12) 1.235(4) . ?
O(122) N(12) 1.224(4) . ?
O(213) C(213) 1.445(4) . ?
O(214) C(214) 1.441(4) . ?
O(215) C(215) 1.423(4) . ?
O(216) C(216) 1.434(4) . ?
O(221) N(22) 1.220(4) . ?
O(222) N(22) 1.226(4) . ?
N(12) C(12) 1.434(5) . ?
N(14) C(15) 1.366(5) . ?
N(14) C(13) 1.390(5) . ?
N(14) H(14) 0.98(5) . ?
N(16) C(11) 1.352(5) . ?
N(16) C(15) 1.381(4) . ?
N(16) H(16) 0.86(5) . ?
N(22) C(22) 1.454(5) . ?
N(24) C(25) 1.364(5) . ?
N(24) C(23) 1.392(5) . ?
N(24) H(24) 0.91(5) . ?
N(26) C(21) 1.356(5) . ?
N(26) C(25) 1.378(4) . ?
N(26) H(26) 0.92(4) . ?
C(11) C(12) 1.363(5) . ?
C(11) C(111) 1.503(5) . ?
C(12) C(13) 1.455(5) . ?
C(21) C(22) 1.362(5) . ?
C(21) C(211) 1.503(5) . ?
C(22) C(23) 1.448(5) . ?
C(111) C(112) 1.540(5) . ?
C(112) C(113) 1.519(5) . ?
C(113) C(114) 1.515(5) . ?
C(114) C(115) 1.527(5) . ?
C(115) C(116) 1.502(5) . ?
C(211) C(212) 1.536(5) . ?
C(212) C(213) 1.516(5) . ?
C(213) C(214) 1.525(5) . ?
C(214) C(215) 1.533(5) . ?
C(215) C(216) 1.523(5) . ?
