#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006378.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_2006378
loop_
_publ_author_name
'Audette, G. F.'
'Zoghaib, W. M.'
'Tourigny, G.'
'Gupta, S. V.'
'Delbaere, L. T. J.'
_publ_contact_author
;
Louis T. J. Delbaere
Department of Biochemistry
University of Saskatchewan
Saskatoon, Saskatchewan
Canada S7N 5E5
;
_publ_section_title
;
 3,4-Etheno-5-methoxymethyl-2'-deoxycytidine
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1099
_journal_page_last               1101
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety         'C13 H17 N3 O5 '
_chemical_formula_sum            'C13 H17 N3 O5'
_chemical_formula_weight         295.29
_chemical_name_systematic
;
 ?  #Insert the chemical name here.
;
_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                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   7.122(2)
_cell_length_b                   18.113(4)
_cell_length_c                   10.389(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      12.70
_cell_measurement_theta_min      8.30
_cell_volume                     1340.2(7)
_diffrn_ambient_temperature      293
_diffrn_measurement_device       'Nonius CAD-4'
_diffrn_measurement_method       '\w scan b/P/b'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'xray tube'
_diffrn_radiation_type           'Molybdenum K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.017
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2609
_diffrn_reflns_theta_max         24.93
_diffrn_reflns_theta_min         0.00
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count '100 min'
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.11
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             624.31
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.46
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.43
_refine_ls_hydrogen_treatment    'H-atom coordinates and U~iso~ not refined'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2333
_refine_ls_R_factor_all          0.095
_refine_ls_R_factor_obs          0.094
_refine_ls_shift/esd_max         0.000
_refine_ls_structure_factor_coef F^2^
_refine_ls_weighting_scheme      'w = 1/[\s^2^(F) + 0.0010F^2^]'
_refine_ls_wR_factor_all         0.076
_refine_ls_wR_factor_obs         0.076
_reflns_number_observed          2342
_reflns_number_total             2342
_reflns_observed_criterion       'Inet > 0.0\s(Inet)'
_[local]_cod_data_source_file    fg1253.cif
_[local]_cod_data_source_block   global
_[local]_cod_chemical_formula_sum_orig 'C13 H17 N3 O5 '
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2006378
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2+x,1/2-y,-z
1/2-x,1/2+y,-z
-x,-y,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
_atom_site_aniso_type_symbol
O52 0.172(3) 0.0354(10) 0.0243(8) -0.0142(15) 0.0053(14) -0.0018(8) O
O2 0.118(2) 0.0395(10) 0.0269(9) -0.0135(14) 0.0043(13) 0.0040(8) O
N1 0.0638(19) 0.0195(9) 0.0224(10) -0.0010(11) 0.0000(12) 0.0008(9) N
N3 0.0599(19) 0.0256(10) 0.0257(10) -0.0014(14) 0.0013(13) -0.0023(9) N
N4 0.067(2) 0.0219(10) 0.0378(12) -0.0018(12) 0.0026(13) -0.0029(10) N
C2 0.066(2) 0.0295(14) 0.0309(13) -0.0016(17) 0.0054(18) 0.0016(12) C
C4 0.048(2) 0.0262(12) 0.0274(12) -0.0001(15) 0.0059(16) 0.0016(10) C
C5 0.047(2) 0.0257(14) 0.0242(11) 0.0034(15) 0.0002(16) 0.0003(9) C
C6 0.058(2) 0.0256(12) 0.0256(12) 0.0006(15) 0.0015(15) -0.0014(10) C
C31 0.106(3) 0.0334(15) 0.0297(13) -0.005(2) 0.003(2) -0.0090(12) C
C32 0.097(3) 0.0315(15) 0.0415(15) -0.0072(19) 0.0057(19) -0.0103(13) C
C51 0.070(3) 0.0263(13) 0.0307(12) -0.0009(18) 0.0017(18) 0.0019(12) C
C53 0.139(4) 0.0627(19) 0.0213(12) -0.009(2) -0.001(2) 0.0064(12) C
C1' 0.051(2) 0.0276(13) 0.0275(13) -0.0049(15) 0.0063(15) 0.0027(11) C
C2' 0.046(2) 0.0303(14) 0.0478(16) -0.0035(15) -0.0033(15) 0.0049(13) C
C3' 0.066(2) 0.0215(13) 0.0328(13) -0.0047(14) -0.0092(16) -0.0002(12) C
C4' 0.061(2) 0.0200(13) 0.0310(13) -0.0007(14) 0.0018(16) 0.0003(12) C
C5' 0.066(3) 0.0339(16) 0.0570(18) -0.0033(17) 0.0093(19) -0.0013(14) C
O3' 0.113(2) 0.0333(9) 0.0470(11) -0.0094(12) -0.0273(13) -0.0117(9) O
O4' 0.0545(15) 0.0327(9) 0.0300(9) 0.0025(10) -0.0072(10) -0.0032(8) O
O5' 0.0825(18) 0.0380(10) 0.0366(9) -0.0126(12) 0.0109(11) -0.0013(9) O
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_type_symbol
O52 0.7417(5) 0.45166(9) 0.98658(14) 0.0772(17) Uani O
O2 0.7209(4) 0.39692(9) 1.56920(14) 0.0615(15) Uani O
N1 0.7066(3) 0.37860(9) 1.35115(17) 0.0352(13) Uani N
N3 0.7508(4) 0.49514(11) 1.43407(15) 0.0371(14) Uani N
N4 0.7937(4) 0.59822(10) 1.32184(18) 0.0423(15) Uani N
C2 0.7242(5) 0.42000(13) 1.4608(2) 0.0422(18) Uani C
C4 0.7639(4) 0.52692(11) 1.3134(2) 0.0339(15) Uani C
C5 0.7436(5) 0.47974(12) 1.2053(2) 0.0325(16) Uani C
C6 0.7176(5) 0.40834(13) 1.22948(19) 0.0366(16) Uani C
C31 0.7774(7) 0.55205(14) 1.5217(2) 0.056(2) Uani C
C32 0.8031(5) 0.61256(14) 1.4518(3) 0.056(2) Uani C
C51 0.7506(5) 0.51115(13) 1.0720(2) 0.0424(18) Uani C
C53 0.7525(6) 0.46989(14) 0.8548(2) 0.074(2) Uani C
C1' 0.6875(4) 0.29803(13) 1.3699(2) 0.0356(16) Uani C
C2' 0.5672(4) 0.25964(13) 1.2703(2) 0.0416(16) Uani C
C3' 0.7057(5) 0.22798(12) 1.1750(2) 0.0403(17) Uani C
C4' 0.8817(4) 0.21528(11) 1.2545(2) 0.0375(17) Uani C
C5' 1.0631(5) 0.22664(14) 1.1875(3) 0.052(2) Uani C
O3' 0.6453(3) 0.16072(9) 1.11947(16) 0.0645(14) Uani O
O4' 0.8683(3) 0.26522(8) 1.36281(15) 0.0391(11) Uani O
O5' 1.0798(3) 0.29916(9) 1.13433(15) 0.0524(12) Uani O
H6 0.697 0.371 1.160 0.0457 Uiso H
H51a 0.871 0.538 1.054 0.0529 Uiso H
H51b 0.645 0.547 1.060 0.0529 Uiso H
H31 0.768 0.545 1.617 0.0661 Uiso H
H32 0.827 0.665 1.478 0.0665 Uiso H
H1' 0.633 0.292 1.458 0.0449 Uiso H
H2'a 0.462 0.291 1.239 0.0519 Uiso H
H2'b 0.499 0.218 1.312 0.0519 Uiso H
H3' 0.739 0.264 1.107 0.0503 Uiso H
H4' 0.869 0.165 1.293 0.0476 Uiso H
H5'a 1.080 0.192 1.114 0.0621 Uiso H
H5'b 1.164 0.217 1.253 0.0621 Uiso H
H3" 0.611 0.166 1.036 0.0738 Uiso H
H5" 1.113 0.327 1.203 0.0618 Uiso H
H53a 0.767 0.425 0.799 0.0871 Uiso H
H53b 0.836 0.514 0.840 0.0871 Uiso H
H53c 0.663 0.510 0.829 0.0871 Uiso H
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.002 0.002 'International Tables Vol. IV Table 2.2B'
H 0.000 0.000 'International Tables Vol. IV Table 2.2B'
O 0.008 0.006 'International Tables Vol. IV Table 2.2B'
N 0.004 0.003 'International Tables Vol. IV Table 2.2B'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-4 3 0
-1 -5 -4
-1 -5 4
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3' H3" O5' 2_457 164.69(13) no
O5' H5" N4 4_765 166.97(12) no
C51 O52 C53 ? 115.69(18) yes
C2 N1 C6 ? 122.99(18) no
C2 N1 C1' ? 116.02(18) no
C6 N1 C1' ? 120.87(18) no
C2 N3 C4 ? 126.38(18) no
C2 N3 C31 ? 127.52(18) yes
C4 N3 C31 ? 106.06(19) yes
C4 N4 C32 ? 105.00(19) yes
O2 C2 N1 ? 125.9(2) no
O2 C2 N3 ? 121.7(2) no
N1 C2 N3 ? 112.27(18) no
N3 C4 N4 ? 111.13(19) no
N3 C4 C5 ? 117.39(19) no
N4 C4 C5 ? 131.4(2) no
C4 C5 C6 ? 116.80(19) no
C4 C5 C51 ? 119.99(19) yes
C6 C5 C51 ? 123.21(19) yes
N1 C6 C5 ? 124.15(19) no
N3 C31 C32 ? 105.8(2) yes
N4 C32 C31 ? 111.9(2) yes
O52 C51 C5 ? 107.04(18) yes
N1 C1' C2' ? 114.5(2) no
N1 C1' O4' ? 108.8(2) no
C2' C1' O4' ? 106.5(2) no
C1' C2' C3' ? 104.6(2) no
C2' C3' C4' ? 103.9(2) no
C2' C3' O3' ? 113.2(2) no
C4' C3' O3' ? 110.0(2) no
C3' C4' C5' ? 116.2(2) no
C3' C4' O4' ? 105.8(2) no
C5' C4' O4' ? 109.6(2) no
C4' C5' O5' ? 112.4(2) no
C1' O4' C4' ? 111.25(19) 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
O3' O5' 2_457 2.775(2) no
H3" O5' 2_457 1.8930(10) no
O5' N4 4_765 2.839(2) no
H5" N4 4_765 1.9540(10) no
O52 C51 ? 1.397(3) yes
O52 C53 ? 1.410(3) yes
O2 C2 ? 1.201(3) no
N1 C2 ? 1.370(3) no
N1 C6 ? 1.376(3) no
N1 C1' ? 1.479(3) no
N3 C2 ? 1.402(3) no
N3 C4 ? 1.382(3) no
N3 C31 ? 1.389(3) yes
N4 C4 ? 1.312(3) no
N4 C32 ? 1.377(3) yes
C4 C5 ? 1.418(3) no
C5 C6 ? 1.330(3) no
C5 C51 ? 1.499(3) yes
C31 C32 ? 1.328(4) yes
C1' C2' ? 1.513(4) no
C1' O4' ? 1.420(4) no
C2' C3' ? 1.511(4) no
C3' C4' ? 1.519(4) no
C3' O3' ? 1.415(3) no
C4' C5' ? 1.482(4) no
C4' O4' ? 1.446(3) no
C5' O5' ? 1.430(3) no
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
C53 O52 C51 C5 -178.1(6) ?
C6 N1 C2 O2 -177.9(6) ?
C6 N1 C2 N3 1.1(2) ?
C1' N1 C2 O2 -1.9(2) ?
C1' N1 C2 N3 177.1(5) ?
C2 N1 C6 C5 -1.0(3) ?
C1' N1 C6 C5 -176.7(5) ?
C2 N1 C1' C2' 147.6(5) ?
C2 N1 C1' O4' -93.2(4) yes
C6 N1 C1' C2' -36.3(3) ?
C6 N1 C1' O4' 82.8(4) ?
C4 N3 C2 O2 177.4(6) ?
C4 N3 C2 N1 -1.6(2) ?
C31 N3 C2 O2 0.4(3) ?
C31 N3 C2 N1 -178.6(6) ?
C2 N3 C4 N4 -178.3(5) ?
C2 N3 C4 C5 1.8(3) ?
C31 N3 C4 N4 -0.8(3) ?
C31 N3 C4 C5 179.3(6) ?
C2 N3 C31 C32 177.7(7) ?
C4 N3 C31 C32 0.3(3) ?
C32 N4 C4 N3 0.9(3) ?
C32 N4 C4 C5 -179.2(5) ?
C4 N4 C32 C31 -0.8(3) ?
N3 C4 C5 C6 -1.4(3) ?
N3 C4 C5 C51 178.2(5) ?
N4 C4 C5 C6 178.7(6) ?
N4 C4 C5 C51 -1.7(2) ?
C4 C5 C6 N1 1.0(2) ?
C51 C5 C6 N1 -178.5(6) ?
C4 C5 C51 O52 175.5(6) ?
C6 C5 C51 O52 -5.1(3) yes
N3 C31 C32 N4 0.3(2) ?
N1 C1' C2' C3' 98.0(4) ?
O4' C1' C2' C3' -22.3(2) yes
N1 C1' O4' C4' -116.3(4) ?
C2' C1' O4' C4' 7.6(2) yes
C1' C2' C3' C4' 27.8(3) yes
C1' C2' C3' O3' 147.2(5) ?
C2' C3' C4' C5' -145.6(5) ?
C2' C3' C4' O4' -23.5(2) yes
O3' C3' C4' C5' 92.8(4) ?
O3' C3' C4' O4' -145.2(5) ?
C3' C4' C5' O5' 57.2(3) yes
O4' C4' C5' O5' -62.8(3) ?
C3' C4' O4' C1' 10.2(3) yes
C5' C4' O4' C1' 136.3(5) ?