#------------------------------------------------------------------------------
#$Date: 2016-02-19 15:29:56 +0100 (vie 19 de feb de 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/51/2005123.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_2005123
loop_
_publ_author_name
'Kolb, V. M.'
'Colloton, P. A.'
'Robinson, P. D.'
'Lutfi, H. G.'
'Meyers, C. Y.'
_publ_section_title
(1R,2R)-4,4-Dimethylpyrazolidine-3,5-dione-α-<small>D</small>-pyranosyl-2-deoxyriboside
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1781
_journal_page_last               1784
_journal_paper_doi               10.1107/S0108270196004416
_journal_volume                  52
_journal_year                    1996
_chemical_formula_sum            'C10 H16 N2 O5'
_chemical_formula_weight         244.25
_chemical_name_systematic
;
1-(2-deoxy-α-D-erythropentopyranosyl) 1-(R),2-(R)-4,4-
dimethylpyrazolidine-3,5-dione
;
_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                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   9.802(7)
_cell_length_b                   21.172(5)
_cell_length_c                   5.504(5)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    296
_cell_measurement_theta_max      11.2
_cell_measurement_theta_min      10.1
_cell_volume                     1142.2(13)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software (Molecular Structure
Corporation, 1988)
;
_computing_data_reduction
;
TEXSAN PROCESS (Molecular Structure Corporation, 1985)
;
_computing_molecular_graphics    'TEXSAN ORTEP (Johnson, 1965)'
_computing_publication_material  'TEXSAN FINISH; PLATON (Spek, 1990)'
_computing_structure_refinement  'TEXSAN LS'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      296
_diffrn_measurement_device       'Rigaku AFC5S diffractometer'
_diffrn_measurement_method
'ω (rate 3° min⁻¹ in ω, 3 reps. maximum)'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         x-ray_tube
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.049
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2214
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         1.75
_diffrn_standards_decay_%        -0.2
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.11
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   '\y-scans (North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_meas      ?
_exptl_crystal_description       'platy fragment'
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.31
_refine_ls_abs_structure_details
;
The absolute molecular configuration of (2) was determined from the
known absolute chirality of the D-2-deoxyribopyranosyl moiety.
;
_refine_ls_extinction_coef       0.0
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.35
_refine_ls_hydrogen_treatment
;
noref (riding, C-H 0.95 \%A) except H2 (refxyz), and H7' & H8' (map
positions)
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1655
_refine_ls_R_factor_obs          0.058
_refine_ls_shift/esd_max         0.0001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 4Fₒ²/σ²(Fₒ²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.048
_reflns_number_observed          1655
_reflns_number_total             2191
_reflns_observed_criterion       '[I > \s(I)]'
_cod_data_source_file            fg1174.cif
_cod_data_source_block           default
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 4F~o~^2^/\s^2^(F~o~^2^)' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
4F~o~^2^/\s^2^(F~o~^2^)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1142(2)
_cod_database_code               2005123
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2+x,1/2-y,-z
-x,1/2+y,1/2-z
1/2-x,-y,1/2+z
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
O6 0.0228(14) 0.0434(15) 0.0460(16) -0.0037(12) -0.0044(14) 0.0049(13)
O7 0.0431(16) 0.0463(16) 0.066(2) -0.0060(15) -0.0242(16) 0.0181(16)
O6' 0.0351(15) 0.0322(13) 0.0258(13) 0.0006(13) 0.0018(12) 0.0064(11)
O7' 0.0287(14) 0.0548(16) 0.0262(13) -0.0075(13) -0.0011(13) 0.0116(13)
O8' 0.0461(16) 0.0513(16) 0.0251(12) -0.0180(15) -0.0004(14) 0.0006(13)
N1 0.0253(16) 0.0297(17) 0.0411(18) -0.0011(14) -0.0072(15) 0.0074(16)
N2 0.0235(17) 0.0356(18) 0.046(2) -0.0054(16) -0.0051(16) 0.0140(17)
C3 0.035(2) 0.031(2) 0.035(2) 0.0034(18) -0.006(2) 0.0037(18)
C4 0.033(2) 0.021(2) 0.032(2) 0.0006(18) -0.0035(17) 0.0027(15)
C5 0.030(2) 0.0234(18) 0.0291(18) -0.0032(17) 0.005(2) -0.0043(16)
C6 0.051(3) 0.080(3) 0.041(3) -0.006(3) -0.007(2) 0.021(2)
C7 0.070(3) 0.038(2) 0.073(3) 0.014(2) -0.028(3) -0.009(2)
C1' 0.026(2) 0.034(2) 0.030(2) -0.0059(18) -0.0060(17) 0.0037(17)
C2' 0.034(2) 0.031(2) 0.032(2) 0.0010(18) 0.0047(19) 0.0001(17)
C3' 0.024(2) 0.038(2) 0.0236(18) -0.0065(18) -0.0010(18) 0.0040(17)
C4' 0.039(2) 0.029(2) 0.028(2) 0.0032(19) -0.0005(19) 0.0081(17)
C5' 0.035(2) 0.036(2) 0.033(2) 0.0030(19) 0.004(2) 0.001(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_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
O6 0.2683(2) -0.14304(12) -0.0420(5) 0.0374(9) Uani ? ?
O7 0.6807(3) -0.18058(13) 0.3757(5) 0.0516(10) Uani ? ?
O6' 0.4188(2) 0.00173(11) 0.0606(4) 0.0311(8) Uani ? ?
O7' 0.6365(2) 0.08004(11) -0.5190(4) 0.0366(9) Uani ? ?
O8' 0.6016(3) 0.10399(11) -0.0084(4) 0.0408(9) Uani ? ?
N1 0.4834(3) -0.10046(14) -0.0405(6) 0.0320(10) Uani ? ?
N2 0.5997(3) -0.10746(14) 0.1118(6) 0.0350(11) Uani ? ?
C3 0.5913(4) -0.16052(17) 0.2413(6) 0.0337(12) Uani ? ?
C4 0.4544(4) -0.19169(15) 0.1905(6) 0.0288(11) Uani ? ?
C5 0.3865(4) -0.14408(15) 0.0249(6) 0.0275(11) Uani ? ?
C6 0.3712(5) -0.2029(2) 0.4182(7) 0.0573(17) Uani ? ?
C7 0.4807(5) -0.2535(2) 0.0540(9) 0.0603(16) Uani ? ?
C1' 0.4518(4) -0.03924(16) -0.1377(6) 0.0300(12) Uani ? ?
C2' 0.5656(4) -0.01262(17) -0.2931(6) 0.0323(12) Uani ? ?
C3' 0.5265(4) 0.05274(17) -0.3834(6) 0.0286(11) Uani ? ?
C4' 0.4892(4) 0.09436(17) -0.1693(6) 0.0320(11) Uani ? ?
C5' 0.3774(4) 0.06259(16) -0.0263(6) 0.0347(12) Uani ? ?
H2 0.678(4) -0.0945(17) 0.045(7) 0.0419 Uiso ? ?
H1' 0.3730 -0.0433 -0.2369 0.0356 Uiso calc C1'
H2'a 0.5807 -0.0397 -0.4281 0.0386 Uiso calc C2'
H2'b 0.6467 -0.0098 -0.1992 0.0386 Uiso calc C2'
H3' 0.4493 0.0490 -0.4867 0.0342 Uiso calc C3'
H4' 0.4577 0.1340 -0.2271 0.0383 Uiso calc C4'
H5'a 0.3544 0.0884 0.1088 0.0416 Uiso calc C5'
H5'b 0.2998 0.0577 -0.1278 0.0416 Uiso calc C5'
H6a 0.4148 -0.2340 0.5155 0.0685 Uiso calc C6
H6b 0.3640 -0.1646 0.5072 0.0685 Uiso calc C6
H6c 0.2826 -0.2171 0.3746 0.0685 Uiso calc C6
H7a 0.3961 -0.2715 0.0060 0.0719 Uiso calc C7
H7b 0.5345 -0.2451 -0.0860 0.0719 Uiso calc C7
H7c 0.5277 -0.2821 0.1571 0.0719 Uiso calc C7
H7' 0.6027 0.0819 -0.6873 0.0438 Uiso ? ?
H8' 0.6744 0.1332 -0.1017 0.0491 Uiso ? ?
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C .002 .002 International_Tables_Vol_IV_Table_2.3.1
H 0 0 International_Tables_Vol_IV_Table_2.3.1
O .008 .006 International_Tables_Vol_IV_Table_2.3.1
N .004 .003 International_Tables_Vol_IV_Table_2.3.1
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 4 0
2 0 0
1 2 1
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
C1' O6' C5' 110.8(2) yes
N2 N1 C5 109.2(3) yes
N2 N1 C1' 119.1(3) yes
C5 N1 C1' 123.8(3) yes
N1 N2 C3 110.7(3) yes
O7 C3 N2 124.9(4) yes
O7 C3 C4 126.4(3) yes
N2 C3 C4 108.8(3) yes
C3 C4 C5 102.1(3) yes
C3 C4 C6 113.0(3) yes
C3 C4 C7 108.2(3) yes
C5 C4 C6 111.5(3) yes
C5 C4 C7 110.3(3) yes
C6 C4 C7 111.3(3) yes
O6 C5 N1 124.6(3) yes
O6 C5 C4 127.8(3) yes
N1 C5 C4 107.6(3) yes
O6' C1' N1 108.2(3) yes
O6' C1' C2' 111.8(3) yes
N1 C1' C2' 112.8(3) yes
C1' C2' C3' 109.8(3) yes
O7' C3' C2' 110.4(3) yes
O7' C3' C4' 110.6(3) yes
C2' C3' C4' 109.6(3) yes
O8' C4' C3' 112.3(3) yes
O8' C4' C5' 107.5(3) yes
C3' C4' C5' 108.8(3) yes
O6' C5' C4' 111.7(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O6 C5 1.216(4) yes
O7 C3 1.224(4) yes
O6' C1' 1.431(4) yes
O6' C5' 1.433(4) yes
O7' C3' 1.433(4) yes
O8' C4' 1.428(4) yes
N1 N2 1.423(4) yes
N1 C5 1.373(4) yes
N1 C1' 1.436(4) yes
N2 C3 1.333(4) yes
C3 C4 1.521(5) yes
C4 C5 1.513(5) yes
C4 C6 1.514(5) yes
C4 C7 1.531(5) yes
C1' C2' 1.514(5) yes
C2' C3' 1.520(5) yes
C3' C4' 1.516(5) yes
C4' C5' 1.508(5) yes
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
O6 C5 N1 N2 166.8(3)
O6 C5 N1 C1' 18.2(5)
O6 C5 C4 C3 -169.7(4)
O6 C5 C4 C6 -48.8(5)
O6 C5 C4 C7 75.5(5)
O7 C3 N2 N1 175.1(4)
O7 C3 C4 C5 177.2(4)
O7 C3 C4 C6 57.3(5)
O7 C3 C4 C7 -66.5(5)
O6' C1' N1 N2 -64.6(4)
O6' C1' N1 C5 81.1(4)
O6' C1' C2' C3' -56.3(4)
O6' C5' C4' O8' -62.6(4)
O6' C5' C4' C3' 59.2(4)
O7' C3' C2' C1' 176.6(3)
O7' C3' C4' O8' -58.8(3)
O7' C3' C4' C5' -177.6(3)
O8' C4' C3' C2' 63.1(4)
N1 N2 C3 C4 -4.0(4)
N1 C5 C4 C3 10.3(3)
N1 C5 C4 C6 131.2(3)
N1 C5 C4 C7 -104.6(3)
N1 C1' O6' C5' -176.1(3)
N1 C1' C2' C3' -178.5(3)
N2 N1 C5 C4 -13.2(4)
N2 N1 C1' C2' 59.6(4)
N2 C3 C4 C5 -3.7(4)
N2 C3 C4 C6 -123.6(3)
N2 C3 C4 C7 112.7(3)
C3 N2 N1 C5 11.2(4)
C3 N2 N1 C1' 161.4(3)
C4 C5 N1 C1' -161.8(3)
C5 N1 C1' C2' -154.7(3)
C1' O6' C5' C4' -60.8(3)
C1' C2' C3' C4' 54.6(4)
C2' C1' O6' C5' 59.1(3)
C2' C3' C4' C5' -55.7(4)
