#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/11/4021126.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_4021126
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_formula_sum            'C18 H27 N3 O10'
_chemical_formula_weight         445.43
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.4218(2)
_cell_length_b                   12.1169(3)
_cell_length_c                   8.5406(6)
_cell_measurement_temperature    293(2)
_cell_volume                     2113.36(16)
_diffrn_ambient_temperature      293(2)
_exptl_crystal_density_diffrn    1.400
_cod_database_code               4021126
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -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
O10 O 0.49751(5) 0.75727(10) 0.12943(12) 0.0259(3) Uani 1 1 d . . .
O12 O 0.38916(6) 0.74672(12) 0.06955(13) 0.0340(3) Uani 1 1 d . . .
O15 O 0.36639(5) 0.78000(11) 0.49147(13) 0.0298(3) Uani 1 1 d . . .
O17 O 0.26367(5) 0.77462(10) 0.38877(13) 0.0307(3) Uani 1 1 d . . .
O21 O 0.64299(7) 0.90389(11) 0.84504(15) 0.0368(3) Uani 1 1 d . . .
O41 O 0.65531(7) 0.52701(10) 0.86095(12) 0.0330(3) Uani 1 1 d . . .
O71 O 0.58214(6) 0.56193(9) 0.35095(13) 0.0270(3) Uani 1 1 d . . .
H71 H 0.5735 0.5211 0.4247 0.041 Uiso 1 1 calc R . .
O81 O 0.47017(6) 0.63461(11) 0.51320(13) 0.0324(3) Uani 1 1 d . . .
H81 H 0.4357 0.6625 0.5425 0.049 Uiso 1 1 calc R . .
O101 O 0.56915(8) 0.97350(11) 0.59996(16) 0.0458(4) Uani 1 1 d . . .
O102 O 0.61776(7) 0.90346(11) 0.39839(15) 0.0400(3) Uani 1 1 d . . .
N3 N 0.64830(6) 0.71556(12) 0.86073(15) 0.0262(3) Uani 1 1 d . . .
N5 N 0.61807(6) 0.60313(12) 0.64013(15) 0.0245(3) Uani 1 1 d . . .
N101 N 0.59867(7) 0.89946(12) 0.53504(16) 0.0297(3) Uani 1 1 d . . .
C1 C 0.61209(8) 0.79823(14) 0.62388(19) 0.0250(3) Uani 1 1 d . . .
C2 C 0.63419(8) 0.80482(15) 0.77820(19) 0.0259(4) Uani 1 1 d . . .
C4 C 0.64008(8) 0.61955(14) 0.78607(18) 0.0245(4) Uani 1 1 d . . .
C6 C 0.60380(7) 0.69420(14) 0.55811(17) 0.0222(3) Uani 1 1 d . . .
C7 C 0.57355(8) 0.67269(13) 0.39704(19) 0.0241(3) Uani 1 1 d . . .
H7 H 0.5957 0.7200 0.3205 0.029 Uiso 1 1 calc R . .
C8 C 0.50078(7) 0.70509(14) 0.40184(17) 0.0235(3) Uani 1 1 d . . .
H8 H 0.4961 0.7824 0.4337 0.028 Uiso 1 1 calc R . .
C9 C 0.46843(7) 0.68660(13) 0.24432(17) 0.0216(3) Uani 1 1 d . . .
H9 H 0.4745 0.6095 0.2128 0.026 Uiso 1 1 calc R . .
C11 C 0.45354(8) 0.75670(18) 0.0001(2) 0.0331(4) Uani 1 1 d . . .
C13 C 0.39563(8) 0.71676(14) 0.23132(17) 0.0235(3) Uani 1 1 d . . .
H13 H 0.3688 0.6514 0.2530 0.028 Uiso 1 1 calc R . .
C14 C 0.37149(8) 0.81309(14) 0.3294(2) 0.0272(4) Uani 1 1 d . . .
H14 H 0.4008 0.8767 0.3184 0.033 Uiso 1 1 calc R . .
C16 C 0.29786(8) 0.77021(16) 0.53274(19) 0.0322(4) Uani 1 1 d . . .
C18 C 0.30131(9) 0.84509(17) 0.2889(2) 0.0353(4) Uani 1 1 d . . .
H18A H 0.2931 0.9223 0.3118 0.042 Uiso 1 1 calc R . .
H18B H 0.2918 0.8311 0.1795 0.042 Uiso 1 1 calc R . .
C22 C 0.65970(13) 0.90365(19) 1.0103(2) 0.0501(6) Uani 1 1 d . . .
H22A H 0.7004 0.8654 1.0252 0.075 Uiso 1 1 calc R . .
H22B H 0.6258 0.8671 1.0684 0.075 Uiso 1 1 calc R . .
H22C H 0.6640 0.9783 1.0466 0.075 Uiso 1 1 calc R . .
C42 C 0.67351(11) 0.53495(18) 1.0236(2) 0.0434(5) Uani 1 1 d . . .
H42A H 0.6378 0.5658 1.0823 0.065 Uiso 1 1 calc R . .
H42B H 0.7113 0.5816 1.0337 0.065 Uiso 1 1 calc R . .
H42C H 0.6835 0.4627 1.0631 0.065 Uiso 1 1 calc R . .
C111 C 0.46503(10) 0.6587(2) -0.1049(2) 0.0477(6) Uani 1 1 d . . .
H11A H 0.4657 0.5925 -0.0432 0.072 Uiso 1 1 calc R . .
H11B H 0.5062 0.6671 -0.1578 0.072 Uiso 1 1 calc R . .
H11C H 0.4305 0.6541 -0.1808 0.072 Uiso 1 1 calc R . .
C112 C 0.45855(11) 0.8655(2) -0.0828(3) 0.0594(7) Uani 1 1 d . . .
H11D H 0.5013 0.8725 -0.1287 0.089 Uiso 1 1 calc R . .
H11E H 0.4517 0.9243 -0.0093 0.089 Uiso 1 1 calc R . .
H11F H 0.4259 0.8692 -0.1636 0.089 Uiso 1 1 calc R . .
C161 C 0.27892(10) 0.8652(2) 0.6372(3) 0.0581(7) Uani 1 1 d . . .
H16A H 0.2329 0.8616 0.6591 0.087 Uiso 1 1 calc R . .
H16B H 0.2888 0.9335 0.5856 0.087 Uiso 1 1 calc R . .
H16C H 0.3031 0.8608 0.7335 0.087 Uiso 1 1 calc R . .
C162 C 0.28674(10) 0.6590(2) 0.6059(3) 0.0574(6) Uani 1 1 d . . .
H16D H 0.3010 0.6023 0.5351 0.086 Uiso 1 1 calc R . .
H16E H 0.2410 0.6496 0.6276 0.086 Uiso 1 1 calc R . .
H16F H 0.3111 0.6539 0.7017 0.086 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
O10 C11 1.423(2) . ?
O10 C9 1.4313(18) . ?
O12 C13 1.4345(18) . ?
O12 C11 1.447(2) . ?
O15 C14 1.445(2) . ?
O15 C16 1.448(2) . ?
O17 C16 1.4150(19) . ?
O17 C18 1.431(2) . ?
O21 C2 1.341(2) . ?
O21 C22 1.452(2) . ?
O41 C4 1.328(2) . ?
O41 C42 1.441(2) . ?
O71 C7 1.4096(19) . ?
O81 C8 1.423(2) . ?
O101 N101 1.2147(19) . ?
O102 N101 1.2314(19) . ?
N3 C2 1.323(2) . ?
N3 C4 1.337(2) . ?
N5 C6 1.339(2) . ?
N5 C4 1.340(2) . ?
N101 C1 1.468(2) . ?
C1 C6 1.390(2) . ?
C1 C2 1.395(2) . ?
C6 C7 1.530(2) . ?
C7 C8 1.538(2) . ?
C8 C9 1.515(2) . ?
C9 C13 1.535(2) . ?
C11 C112 1.500(3) . ?
C11 C111 1.506(3) . ?
C13 C14 1.519(2) . ?
C14 C18 1.524(2) . ?
C16 C162 1.503(3) . ?
C16 C161 1.506(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9365110
