#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/93/2009316.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2009316
loop_
_publ_author_name
'Low, John Nicolson'
'Cobo, Justo'
'Molina, Sebastián'
'Sánchez, Adolfo'
'Nogueras, Manuel'
'Ferguson, George'
_publ_section_title
;Two polyacetylated
 6-amino-5-[N-(β-<small>D</small>-glucopyranosyl)amino]-3-methylpyrimidine-2,4(1H,3H)-diones
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              IUC9900164
_journal_paper_doi               10.1107/S0108270199098285
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C23 H30 N4 O13'
_chemical_formula_sum            'C23 H30 N4 O13'
_chemical_formula_weight         570.51
_chemical_name_systematic
;
6-Acetamido-5-N-acetyl-N-(β-D-2,3,4,6-tetra-O-acetylglucopyranosyl)amino-
2,4-dioxo-1,2,3,4-tetrahydro-3-methyl-pyrimidine
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0315(8)
_cell_length_b                   17.0918(13)
_cell_length_c                   18.1487(13)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294.0(10)
_cell_measurement_theta_max      11.31
_cell_measurement_theta_min      5.55
_cell_volume                     2801.5(4)
_computing_cell_refinement       'SET4 and CELDIM (Enraf-Nonius, 1992)'
_computing_data_collection       'CAD-4-PC Software (Enraf-Nonius, 1992)'
_computing_data_reduction        'DATRD2 in NRCVAX96 (Gabe et al., 1989)'
_computing_molecular_graphics
'NRCVAX96, ORTEPII (Johnson, 1976) and PLATON (Spek, 1999)'
_computing_publication_material
'NRCVAX96, SHELXL97  and WordPerfect macro PREP8 (Ferguson, 1998)'
_computing_structure_refinement  'NRCVAX96 and SHELXL97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      294.0(10)
_diffrn_measured_fraction_theta_full .995
_diffrn_measured_fraction_theta_max .995
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5189
_diffrn_reflns_theta_full        25.5
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_min         2.24
_diffrn_standards_decay_%        'no decay, variation 1.0'
_diffrn_standards_interval_time  180
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.173
_refine_ls_extinction_coef       0.0109(10)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         2942
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.074
_refine_ls_R_factor_gt           0.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0556P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.099
_reflns_number_gt                1840
_reflns_number_total             2942
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qa0191.cif
_cod_data_source_block           II
_cod_database_code               2009316
_cod_database_fobs_code          2009316
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
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
N1 0.4235(3) 0.4812(2) 0.40846(17) 0.0661(9) Uani d . 1 . . N
C2 0.2851(4) 0.5070(3) 0.4266(2) 0.0750(13) Uani d . 1 . . C
N3 0.2791(3) 0.56059(19) 0.48267(17) 0.0534(8) Uani d . 1 . . N
C4 0.4015(4) 0.5860(2) 0.52290(19) 0.0482(9) Uani d . 1 . . C
C5 0.5420(4) 0.54954(19) 0.50407(18) 0.0435(8) Uani d . 1 . . C
C6 0.5499(4) 0.5001(2) 0.44572(18) 0.0467(8) Uani d . 1 . . C
O2 0.1771(3) 0.4840(3) 0.3943(2) 0.1334(18) Uani d . 1 . . O
C31 0.1317(4) 0.5900(3) 0.5035(2) 0.0692(12) Uani d . 1 . . C
O4 0.3878(3) 0.63725(15) 0.56942(14) 0.0603(7) Uani d . 1 . . O
N5 0.6695(3) 0.57136(15) 0.54482(14) 0.0427(7) Uani d . 1 . . N
C51 0.7381(4) 0.6433(2) 0.5339(2) 0.0518(9) Uani d . 1 . . C
O52 0.8410(3) 0.66364(16) 0.57152(17) 0.0747(8) Uani d . 1 . . O
C52 0.6801(5) 0.6914(2) 0.4713(2) 0.0727(12) Uani d . 1 . . C
N6 0.6791(3) 0.46520(17) 0.42376(15) 0.0492(7) Uani d . 1 . . N
C61 0.7080(4) 0.4321(2) 0.35586(19) 0.0506(9) Uani d . 1 . . C
O62 0.6173(3) 0.43281(18) 0.30634(13) 0.0719(8) Uani d . 1 . . O
C62 0.8579(4) 0.3971(2) 0.3488(2) 0.0663(11) Uani d . 1 . . C
C1' 0.7296(3) 0.52097(18) 0.60133(17) 0.0404(7) Uani d . 1 . . C
C2' 0.6158(3) 0.47136(19) 0.64087(17) 0.0415(8) Uani d . 1 . . C
O21' 0.5185(3) 0.52179(14) 0.68201(12) 0.0521(6) Uani d . 1 . . O
C21' 0.3693(4) 0.5093(3) 0.6752(2) 0.0609(10) Uani d . 1 . . C
O22' 0.3186(3) 0.46071(19) 0.63625(17) 0.0779(9) Uani d . 1 . . O
C22' 0.2881(4) 0.5659(3) 0.7219(2) 0.0893(15) Uani d . 1 . . C
C3' 0.6923(4) 0.4181(2) 0.69545(17) 0.0460(8) Uani d . 1 . . C
O31' 0.5845(3) 0.36388(14) 0.72332(13) 0.0594(7) Uani d . 1 . . O
C31' 0.5627(5) 0.3584(3) 0.7962(2) 0.0692(11) Uani d . 1 . . C
O32' 0.6282(5) 0.3986(2) 0.83938(15) 0.1016(12) Uani d . 1 . . O
C32' 0.4511(7) 0.2975(3) 0.8146(3) 0.114(2) Uani d . 1 . . C
C4' 0.8141(4) 0.3712(2) 0.65923(18) 0.0498(9) Uani d . 1 . . C
O41' 0.9026(3) 0.33449(14) 0.71608(13) 0.0597(7) Uani d . 1 . . O
C41' 0.9001(6) 0.2557(2) 0.7217(3) 0.0733(12) Uani d . 1 . . C
O42' 0.8301(5) 0.21538(19) 0.6819(2) 0.1273(16) Uani d . 1 . . O
C42' 0.9988(6) 0.2300(3) 0.7826(2) 0.0908(15) Uani d . 1 . . C
C5' 0.9177(4) 0.4236(2) 0.61575(18) 0.0468(8) Uani d . 1 . . C
C6' 1.0332(4) 0.3796(2) 0.5728(2) 0.0598(10) Uani d . 1 . . C
O61' 0.9636(3) 0.32346(15) 0.52550(15) 0.0661(7) Uani d . 1 . . O
C61' 1.0092(6) 0.2501(3) 0.5281(3) 0.0851(15) Uani d . 1 . . C
O62' 1.1020(5) 0.2282(2) 0.5706(3) 0.1466(19) Uani d . 1 . . O
C62' 0.9317(2) 0.19943(11) 0.47592(11) 0.144(3) Uani d . 1 . . C
O6' 0.8316(2) 0.46883(11) 0.56494(11) 0.0453(6) Uani d R 1 . . O
H1 0.4316 0.4508 0.3709 0.079 Uiso calc R 1 . . H
H31A 0.1414 0.6268 0.5432 0.104 Uiso calc PR 0.50 . . H
H31B 0.0707 0.5470 0.5191 0.104 Uiso calc PR 0.50 . . H
H31C 0.0868 0.6153 0.4619 0.104 Uiso calc PR 0.50 . . H
H31D 0.0578 0.5659 0.4730 0.104 Uiso calc PR 0.50 . . H
H31E 0.1286 0.6457 0.4971 0.104 Uiso calc PR 0.50 . . H
H31F 0.1125 0.5775 0.5542 0.104 Uiso calc PR 0.50 . . H
H41A 0.7440 0.7355 0.4634 0.109 Uiso calc R 1 . . H
H41B 0.5822 0.7095 0.4828 0.109 Uiso calc R 1 . . H
H41C 0.6769 0.6601 0.4274 0.109 Uiso calc R 1 . . H
H6 0.7496 0.4638 0.4556 0.059 Uiso calc R 1 . . H
H62A 0.9104 0.4030 0.3945 0.099 Uiso calc PR 0.50 . . H
H62B 0.9112 0.4231 0.3102 0.099 Uiso calc PR 0.50 . . H
H62C 0.8489 0.3425 0.3373 0.099 Uiso calc PR 0.50 . . H
H62D 0.8700 0.3761 0.3002 0.099 Uiso calc PR 0.50 . . H
H62E 0.8691 0.3560 0.3844 0.099 Uiso calc PR 0.50 . . H
H62F 0.9314 0.4366 0.3574 0.099 Uiso calc PR 0.50 . . H
H1' 0.7835 0.5527 0.6374 0.048 Uiso calc R 1 . . H
H2' 0.5589 0.4404 0.6053 0.050 Uiso calc R 1 . . H
H22A 0.3576 0.5984 0.7477 0.134 Uiso calc PR 0.50 . . H
H22B 0.2284 0.5380 0.7569 0.134 Uiso calc PR 0.50 . . H
H22C 0.2257 0.5978 0.6915 0.134 Uiso calc PR 0.50 . . H
H22D 0.1835 0.5577 0.7164 0.134 Uiso calc PR 0.50 . . H
H22E 0.3128 0.6182 0.7071 0.134 Uiso calc PR 0.50 . . H
H22F 0.3154 0.5583 0.7726 0.134 Uiso calc PR 0.50 . . H
H3' 0.7333 0.4491 0.7361 0.055 Uiso calc R 1 . . H
H32A 0.4161 0.2735 0.7701 0.171 Uiso calc PR 0.50 . . H
H32B 0.3695 0.3212 0.8401 0.171 Uiso calc PR 0.50 . . H
H32C 0.4956 0.2585 0.8456 0.171 Uiso calc PR 0.50 . . H
H32D 0.4381 0.2953 0.8671 0.171 Uiso calc PR 0.50 . . H
H32E 0.4846 0.2476 0.7971 0.171 Uiso calc PR 0.50 . . H
H32F 0.3585 0.3103 0.7916 0.171 Uiso calc PR 0.50 . . H
H4' 0.7713 0.3312 0.6269 0.060 Uiso calc R 1 . . H
H42A 1.0705 0.1936 0.7640 0.136 Uiso calc R 1 . . H
H42B 0.9408 0.2053 0.8203 0.136 Uiso calc R 1 . . H
H42C 1.0489 0.2747 0.8029 0.136 Uiso calc R 1 . . H
H5' 0.9675 0.4593 0.6500 0.056 Uiso calc R 1 . . H
H6'A 1.0911 0.4159 0.5436 0.072 Uiso calc R 1 . . H
H6'B 1.0996 0.3530 0.6066 0.072 Uiso calc R 1 . . H
H62G 0.8621 0.2299 0.4481 0.215 Uiso calc PR 0.50 . . H
H62H 0.8801 0.1591 0.5023 0.215 Uiso calc PR 0.50 . . H
H62I 1.0022 0.1760 0.4430 0.215 Uiso calc PR 0.50 . . H
H62J 0.9675 0.1468 0.4809 0.215 Uiso calc PR 0.50 . . H
H62K 0.9495 0.2175 0.4266 0.215 Uiso calc PR 0.50 . . H
H62L 0.8274 0.2007 0.4859 0.215 Uiso calc PR 0.50 . . H
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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 2 -4
1 -2 -4
0 -2 -4
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C6 N1 C2 124.7(3) no
O2 C2 N1 121.2(4) no
O2 C2 N3 123.2(4) no
N1 C2 N3 115.5(3) no
C2 N3 C4 124.5(3) no
C2 N3 C31 117.0(3) no
C4 N3 C31 118.4(3) no
O4 C4 N3 120.3(3) no
O4 C4 C5 123.9(3) no
N3 C4 C5 115.8(3) no
C6 C5 N5 121.9(3) no
C6 C5 C4 119.7(3) no
N5 C5 C4 118.2(3) no
C5 C6 N1 119.4(3) no
C5 C6 N6 122.9(3) no
N1 C6 N6 117.7(3) no
C51 N5 C5 121.3(3) no
C51 N5 C1' 117.4(3) no
C5 N5 C1' 121.2(3) no
O52 C51 N5 121.2(4) no
O52 C51 C52 122.8(3) no
N5 C51 C52 116.0(3) no
C6 N6 C61 126.8(3) no
O62 C61 N6 121.8(3) no
O62 C61 C62 123.7(3) no
N6 C61 C62 114.5(3) no
O6' C1' N5 106.5(2) no
O6' C1' C2' 107.8(2) no
N5 C1' C2' 114.5(3) no
O21' C2' C1' 109.0(2) no
O21' C2' C3' 107.4(2) no
C1' C2' C3' 109.7(3) no
C21' O21' C2' 117.4(3) no
O22' C21' O21' 123.0(4) no
O22' C21' C22' 127.5(4) no
O21' C21' C22' 109.5(4) no
O31' C3' C4' 107.7(3) no
O31' C3' C2' 108.0(3) no
C4' C3' C2' 111.5(3) no
C31' O31' C3' 119.5(3) no
O32' C31' O31' 122.2(4) no
O32' C31' C32' 126.1(4) no
O31' C31' C32' 111.7(4) no
O41' C4' C3' 108.7(3) no
O41' C4' C5' 106.6(3) no
C3' C4' C5' 111.2(3) no
C41' O41' C4' 118.5(3) no
O42' C41' O41' 123.0(4) no
O42' C41' C42' 127.1(4) no
O41' C41' C42' 109.9(4) no
O6' C5' C6' 108.3(3) no
O6' C5' C4' 108.6(2) no
C6' C5' C4' 113.6(3) no
O61' C6' C5' 110.0(3) no
C61' O61' C6' 118.5(4) no
O62' C61' O61' 122.5(5) no
O62' C61' C62' 124.5(4) no
O61' C61' C62' 113.0(4) no
C5' O6' C1' 112.7(2) no
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
N1 C6 . 1.366(4) no
N1 C2 . 1.366(5) no
C2 O2 . 1.204(5) no
C2 N3 . 1.370(6) no
N3 C4 . 1.394(4) no
N3 C31 . 1.473(5) no
C4 O4 . 1.222(4) no
C4 C5 . 1.455(5) no
C5 C6 . 1.357(4) no
C5 N5 . 1.418(4) no
C6 N6 . 1.370(4) no
N5 C51 . 1.391(4) no
N5 C1' . 1.445(4) no
C51 O52 . 1.204(4) no
C51 C52 . 1.498(5) no
N6 C61 . 1.381(4) no
C61 O62 . 1.217(4) no
C61 C62 . 1.485(5) no
C1' O6' . 1.442(4) no
C1' C2' . 1.514(4) no
C2' O21' . 1.439(4) no
C2' C3' . 1.513(4) no
O21' C21' . 1.370(5) no
C21' O22' . 1.183(5) no
C21' C22' . 1.480(6) no
C3' O31' . 1.436(4) no
C3' C4' . 1.511(5) no
O31' C31' . 1.341(5) no
C31' O32' . 1.198(5) no
C31' C32' . 1.487(6) no
C4' O41' . 1.448(4) no
C4' C5' . 1.517(5) no
O41' C41' . 1.351(5) no
C41' O42' . 1.181(5) no
C41' C42' . 1.486(6) no
C5' O6' . 1.432(4) no
C5' C6' . 1.504(5) no
C6' O61' . 1.433(4) no
O61' C61' . 1.321(5) no
C61' O62' . 1.199(6) no
C61' C62' . 1.462(6) no
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_publ_flag
N6 H6 O6' 0.86 2.12 2.910(4) 152 n
N1 H1 O62 0.86 2.07 2.680(4) 127 n
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
_geom_torsion_publ_flag
C6 N1 C2 O2 -175.1(5) no
C6 N1 C2 N3 5.5(7) no
O2 C2 N3 C4 177.4(5) no
N1 C2 N3 C4 -3.2(6) no
O2 C2 N3 C31 0.5(7) no
N1 C2 N3 C31 179.8(4) no
C2 N3 C4 O4 176.0(4) no
C31 N3 C4 O4 -7.1(5) no
C2 N3 C4 C5 -2.4(5) no
C31 N3 C4 C5 174.6(3) no
O4 C4 C5 C6 -172.0(3) no
N3 C4 C5 C6 6.3(5) no
O4 C4 C5 N5 3.7(5) no
N3 C4 C5 N5 -178.0(3) no
N5 C5 C6 N1 -180.0(3) no
C4 C5 C6 N1 -4.4(5) no
N5 C5 C6 N6 2.8(5) no
C4 C5 C6 N6 178.4(3) no
C2 N1 C6 C5 -1.8(6) no
C2 N1 C6 N6 175.6(4) no
C6 C5 N5 C51 101.2(4) no
C4 C5 N5 C51 -74.4(4) no
C6 C5 N5 C1' -81.2(4) no
C4 C5 N5 C1' 103.2(4) no
C5 N5 C51 O52 175.6(3) no
C1' N5 C51 O52 -2.1(5) no
C5 N5 C51 C52 -6.7(5) no
C1' N5 C51 C52 175.6(3) no
C5 C6 N6 C61 -161.2(3) no
N1 C6 N6 C61 21.6(5) no
C6 N6 C61 O62 1.9(6) no
C6 N6 C61 C62 -178.8(3) no
C51 N5 C1' O6' -94.4(3) no
C5 N5 C1' O6' 87.9(3) no
C51 N5 C1' C2' 146.6(3) no
C5 N5 C1' C2' -31.0(4) no
O6' C1' C2' O21' 176.0(2) no
N5 C1' C2' O21' -65.8(3) no
O6' C1' C2' C3' 58.6(3) no
N5 C1' C2' C3' 176.9(3) no
C1' C2' O21' C21' 132.2(3) no
C3' C2' O21' C21' -109.1(3) no
C2' O21' C21' O22' -1.8(6) no
C2' O21' C21' C22' 179.4(3) no
O21' C2' C3' O31' 70.5(3) no
C1' C2' C3' O31' -171.2(2) no
O21' C2' C3' C4' -171.3(3) no
C1' C2' C3' C4' -53.0(4) no
C4' C3' O31' C31' 114.9(3) no
C2' C3' O31' C31' -124.5(3) no
C3' O31' C31' O32' 1.6(6) no
C3' O31' C31' C32' -178.0(3) no
O31' C3' C4' O41' -73.6(3) no
C2' C3' C4' O41' 168.0(3) no
O31' C3' C4' C5' 169.2(2) no
C2' C3' C4' C5' 50.9(4) no
C3' C4' O41' C41' 113.4(4) no
C5' C4' O41' C41' -126.6(4) no
C4' O41' C41' O42' 0.7(7) no
C4' O41' C41' C42' 179.5(3) no
O41' C4' C5' O6' -172.7(2) no
C3' C4' C5' O6' -54.3(3) no
O41' C4' C5' C6' 66.8(3) no
C3' C4' C5' C6' -174.8(3) no
O6' C5' C6' O61' -65.5(3) no
C4' C5' C6' O61' 55.2(4) no
C5' C6' O61' C61' -128.1(4) no
C6' O61' C61' O62' 3.1(7) no
C6' O61' C61' C62' -178.6(3) no
C6' C5' O6' C1' -172.7(3) no
C4' C5' O6' C1' 63.5(3) no
N5 C1' O6' C5' 170.6(2) no
C2' C1' O6' C5' -66.1(3) no
