##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.0.1.  #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
data_D4T-NMPO
_audit_creation_method     'PARSTCIF and SHELXL-97'
_journal_date_recd_electronic     2000-01-14
_journal_date_accepted     2000-01-26
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2000
_journal_volume     56
_journal_issue      5
_journal_page_first     580
_journal_page_last     581
_journal_paper_category     FO
_publ_contact_author_name     'Dr Davide Viterbo'
_publ_contact_author_address
; Dip. di Scienze e Tecnologie Avanzate,
  Univ. del Piemonte Orientale "A. Avogadro",
  Corso T. Borsalino 54,
  I-15100 Alessandria, Italy
;
_publ_contact_author_email     'viterbo@ch.unito.it'
_publ_contact_author_fax     '+39-011-6707855'
_publ_contact_author_phone     '+39-011-6707515'
_publ_section_title
;
2',3'-Didehydro-3'-deoxythymidine N-methyl-2-pyrrolidone solvate
(D4T.NMPO)
;
loop_
    _publ_author_name
    _publ_author_address
    'Viterbo, Davide'
; 	Dipartimento di Scienze e Tecnologie Avanzate,
	Univ. del Piemonte Orientale "A. Avogadro",
	Corso T. Borsalino 54,
	I-15100 Alessandria,  Italy
;
    'Milanesio, Marco'
; Dipartimento di Chimica IFM,
  Univ. di Torino,
  Via P, Giuria 7,
  I-10125 Torino, Italy
;
    "Pomés Hernández, Ramón "
;
  X Ray Laboratory
  National Center for Scientific Research
  PO Box 6880
  Havana, Cuba
;
    "Rodríguez Tanty, Chryslaine"
;
  Laboratory of Organic Synthesis
  National Center for Scientific Research
  PO Box 6880
  Havana
  Cuba
;
    "Colás González, Ivan"
;
 Laboratory of Organic Synthesis
  National Center for Scientific Research
  PO Box 6880
  Havana
  Cuba
;
    "Sablón Carrazana, Marquiza"
;
  Laboratory of Organic Synthesis
  National Center for Scientific Research
  PO Box 6880
  Havana
  Cuba
;
    "Duque Rodríguez, Julio"
;
  X-ray Laboratory
  National Center for Scientific Research
  PO Box 6880
  Havana
  Cuba
;
data_I
_chemical_name_systematic
;
1-(2',3'-dideoxy-β-D-glycero-pent-2-enofuranosyl)thimine
1-methylpyrrolidone
;
_chemical_name_common
;
2',3'-didehydro-2',3'-O-dideoxythymidine (D4T)
1-methylpyrrolidone (NMPO) solvate
;
_chemical_formula_moiety     'C10 H12 N2 O4 , C5 H9 N O'
_chemical_formula_sum     'C15 H21 N3 O5'
_chemical_formula_weight     323.35
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     ' P 21 21 21 '
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
_cell_length_a     7.4710(10)
_cell_length_b     13.9880(10)
_cell_length_c     15.739(2)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1644.8(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     30
_cell_measurement_theta_min     12
_cell_measurement_theta_max     26
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max      .65
_exptl_crystal_size_mid      .50
_exptl_crystal_size_min      .35
_exptl_crystal_density_diffrn     1.306
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     688
_exptl_absorpt_coefficient_mu      .099
_exptl_absorpt_correction_type     'none'
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71069
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'four circle diffractometer'
_diffrn_measurement_method     'ω scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     2807
_diffrn_reflns_av_R_equivalents      .0133
_diffrn_reflns_av_sigmaI/netI      .0407
_diffrn_reflns_theta_min     1.95
_diffrn_reflns_theta_max     27.48
_diffrn_measured_fraction_theta_max      .988
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     1
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     1
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     1
_diffrn_standards_number     2
_diffrn_standards_interval_count     98
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_reflns_number_total     2619
_reflns_number_gt     1674
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .0992
_refine_ls_R_factor_gt      .0584
_refine_ls_wR_factor_ref      .1553
_refine_ls_goodness_of_fit_ref      .998
_refine_ls_restrained_S_all      .998
_refine_ls_number_reflns     2619
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0936P)²+0.0334P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max      .006
_refine_ls_shift/su_mean      .000
_refine_diff_density_max      .26
_refine_diff_density_min      -.41
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details
; The absolute configuration was assumed
to agree with the known chirality of
D4T (Gurskaya et al., 1991; Harte et al., 1991;
Van Roey et al., 1993).
;
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C'  .0033  .0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H'  .0000  .0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N'  .0061  .0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O'  .0106  .0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'XSCANS (Siemens, 1996)'
_computing_cell_refinement     'XSCANS'
_computing_data_reduction     'XSCANS'
_computing_structure_solution     'SIR-97 (Altomare et al., 1999)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
            'SHELXTL/IRIS (Sheldrick, 1990) and MOLDRAW (Ugliengo et al., 1993)'
_computing_publication_material
;
 PARST (Nardelli, 1995), PARSTCIF (Nardelli, 1991) and SHELXL97
;
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
    O2  .6713(4)  .62562(17)  .35710(16)  .0662(8) Uani 1 d 1 . . O
    O4  .5578(6)  .69573(18)  .08198(15)  .0821(10) Uani 1 d 1 . . O
    N1  .6160(4)  .78208(18)  .32304(15)  .0450(7) Uani 1 d 1 . . N
    C2  .6367(5)  .6865(2)  .3035(2)  .0456(8) Uani 1 d 1 . . C
    N3  .6179(4)  .66464(19)  .21944(16)  .0507(7) Uani 1 d 1 . . N
    H3  .6346  .6058  .2056  .061 Uiso 1 calc 1 R . H
    C4  .5747(6)  .7267(2)  .1537(2)  .0529(9) Uani 1 d 1 . . C
    C5  .5527(5)  .8254(2)  .1790(2)  .0501(8) Uani 1 d 1 . . C
    C6  .5731(5)  .8469(2)  .2605(2)  .0487(8) Uani 1 d 1 . . C
    H6  .5573  .9104  .2765  .058 Uiso 1 calc 1 R . H
    C7  .5076(8)  .8973(3)  .1119(2)  .0768(14) Uani 1 d 1 . . C
    H7A  .6087  .9059  .0750  .092 Uiso 1 calc 1 R . H
    H7B  .4781  .9572  .1382  .092 Uiso 1 calc 1 R . H
    H7C  .4072  .8750  .0794  .092 Uiso 1 calc 1 R . H
    O4'  .4536(3)  .82655(15)  .44652(13)  .0496(6) Uani 1 d 1 . . O
    O5'  .2883(4)  .98244(16)  .34879(14)  .0552(7) Uani 1 d 1 . . O
    H5'  .2420  .9368  .3246  .066 Uiso 1 calc 1 R . H
    C1'  .6276(5)  .8124(2)  .4128(2)  .0484(8) Uani 1 d 1 . . C
    H1'  .6911  .7639  .4461  .058 Uiso 1 calc 1 R . H
    C2'  .7185(5)  .9070(3)  .4222(2)  .0550(9) Uani 1 d 1 . . C
    H2'1  .8352  .9205  .4055  .066 Uiso 1 calc 1 R . H
    C3'  .6084(5)  .9679(3)  .4578(2)  .0548(9) Uani 1 d 1 . . C
    H3'  .6369 1.0313  .4696  .066 Uiso 1 calc 1 R . H
    C4'  .4338(5)  .9239(2)  .47675(18)  .0460(8) Uani 1 d 1 . . C
    H4'  .4179  .9224  .5385  .055 Uiso 1 calc 1 R . H
    C5'  .2732(5)  .9703(3)  .4379(2)  .0550(9) Uani 1 d 1 . . C
    H5'1  .1685  .9316  .4500  .066 Uiso 1 calc 1 R . H
    H5'2  .2553 1.0323  .4641  .066 Uiso 1 calc 1 R . H
    O*  .0624(5)  .8601(2)  .2759(2)  .0833(9) Uani 1 d 1 . . O
    N1*  .0729(6)  .7285(3)  .1920(2)  .0943(14) Uani 1 d 1 . . N
    C2*  .1110(8)  .6253(4)  .1979(4)  .117(2) Uani 1 d 1 . . C
    H2*1  .2203  .6094  .1678  .141 Uiso 1 calc 1 R . H
    H2*2  .0133  .5881  .1743  .141 Uiso 1 calc 1 R . H
    C3*  .1308(11)  .6068(4)  .2916(5)  .125(2) Uani 1 d 1 . . C
    H3*1  .0332  .5673  .3120  .150 Uiso 1 calc 1 R . H
    H3*2  .2429  .5744  .3031  .150 Uiso 1 calc 1 R . H
    C4*  .1275(7)  .7020(3)  .3341(3)  .0818(13) Uani 1 d 1 . . C
    H4*1  .2427  .7162  .3596  .098 Uiso 1 calc 1 R . H
    H4*2  .0365  .7037  .3781  .098 Uiso 1 calc 1 R . H
    C5*  .0848(6)  .7725(3)  .2646(2)  .0679(12) Uani 1 d 1 . . C
    C6*  .0401(10)  .7775(6)  .1132(3)  .152(3) Uani 1 d 1 . . C
    H6*1  .1466  .7763  .0791  .182 Uiso 1 calc 1 R . H
    H6*2  .0074  .8426  .1247  .182 Uiso 1 calc 1 R . H
    H6*3  -.0555  .7464  .0833  .182 Uiso 1 calc 1 R . H
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
    O2  .098(2)  .0456(12)  .0553(14)  .0065(15)  -.0215(15)  .0077(11)
    O4  .146(3)  .0594(15)  .0410(13)  .006(2)  -.0088(18)  -.0052(11)
    N1  .0548(17)  .0415(13)  .0386(13)  .0032(15)  -.0050(14)  .0016(11)
    C2  .0478(19)  .0402(16)  .0489(17)  -.0002(17)  -.0069(16)  .0006(15)
    N3  .0672(19)  .0389(13)  .0462(15)  .0038(15)  -.0040(15)  .0009(11)
    C4  .068(3)  .0488(17)  .0418(17)  .003(2)  .0005(18)  .0010(15)
    C5  .063(2)  .0436(16)  .0442(17)  .0033(19)  .0006(17)  .0040(14)
    C6  .063(2)  .0390(16)  .0443(17)  .0041(16)  .0044(17)  .0013(13)
    C7  .124(4)  .057(2)  .0501(19)  .008(3)  -.006(2)  .0125(18)
    O4'  .0623(15)  .0422(11)  .0442(11)  -.0028(12)  .0040(12)  .0026(10)
    O5'  .0744(17)  .0463(12)  .0447(12)  -.0038(13)  -.0079(12)  .0052(10)
    C1'  .053(2)  .0511(18)  .0408(16)  .0056(18)  -.0054(16)  .0000(15)
    C2'  .0457(19)  .066(2)  .0536(19)  -.0070(19)  -.0018(17)  -.0099(19)
    C3'  .064(2)  .0538(19)  .0462(18)  -.010(2)  -.0083(19)  -.0061(16)
    C4'  .062(2)  .0437(16)  .0326(14)  -.0018(18)  .0054(16)  .0017(13)
    C5'  .062(2)  .054(2)  .0485(19)  .0050(19)  .0087(18)  -.0013(16)
    O*  .081(2)  .0755(19)  .094(2)  -.0141(18)  -.0086(19)  -.0160(17)
    N1*  .085(3)  .133(4)  .065(2)  -.036(3)  .015(2)  -.031(2)
    C2*  .085(4)  .111(4)  .156(6)  -.035(4)  .035(4)  -.082(4)
    C3*  .122(5)  .099(4)  .154(6)  .001(4)  .031(5)  -.007(4)
    C4*  .067(3)  .089(3)  .089(3)  -.011(3)  -.003(3)  .004(3)
    C5*  .056(3)  .087(3)  .060(2)  -.029(2)  .007(2)  -.017(2)
    C6*  .128(5)  .270(9)  .058(3)  -.065(7)  -.005(3)  .024(4)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between
esds in cell parameters are only
 used when they are defined by crystal symmetry.
An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    O2 C2 . 1.226(4) ?
    O4 C4 . 1.216(4) ?
    N1 C6 . 1.377(4) ?
    N1 C2 . 1.381(4) ?
    N1 C1' . 1.478(4) ?
    C2 N3 . 1.365(4) ?
    N3 C4 . 1.389(4) ?
    C4 C5 . 1.446(5) ?
    C5 C6 . 1.326(5) ?
    C5 C7 . 1.497(5) ?
    O4' C1' . 1.418(4) ?
    O4' C4' . 1.450(4) ?
    O5' C5' . 1.417(4) ?
    C1' C2' . 1.495(5) ?
    C2' C3' . 1.310(5) ?
    C3' C4' . 1.473(5) ?
    C4' C5' . 1.495(5) ?
    O* C5* . 1.249(5) ?
    N1* C5* . 1.301(5) ?
    N1* C6* . 1.437(7) ?
    N1* C2* . 1.475(7) ?
    C2* C3* . 1.505(9) ?
    C3* C4* . 1.490(8) ?
    C4* C5* . 1.507(6) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C6 N1 C2 . . 120.3(3) ?
    C6 N1 C1' . . 120.5(3) ?
    C2 N1 C1' . . 119.0(3) ?
    O2 C2 N3 . . 122.2(3) ?
    O2 C2 N1 . . 122.9(3) ?
    N3 C2 N1 . . 114.9(3) ?
    C2 N3 C4 . . 127.3(3) ?
    O4 C4 N3 . . 119.6(3) ?
    O4 C4 C5 . . 125.7(3) ?
    N3 C4 C5 . . 114.7(3) ?
    C6 C5 C4 . . 118.0(3) ?
    C6 C5 C7 . . 123.7(3) ?
    C4 C5 C7 . . 118.2(3) ?
    C5 C6 N1 . . 124.7(3) ?
    C1' O4' C4' . . 110.3(3) ?
    O4' C1' N1 . . 110.1(3) ?
    O4' C1' C2' . . 104.9(3) ?
    N1 C1' C2' . . 112.1(3) ?
    C3' C2' C1' . . 109.4(3) ?
    C2' C3' C4' . . 111.8(3) ?
    O4' C4' C3' . . 103.6(3) ?
    O4' C4' C5' . . 110.8(3) ?
    C3' C4' C5' . . 116.5(3) ?
    O5' C5' C4' . . 113.1(3) ?
    C5* N1* C6* . . 122.9(5) ?
    C5* N1* C2* . . 113.3(5) ?
    C6* N1* C2* . . 123.6(5) ?
    N1* C2* C3* . . 104.4(4) ?
    C4* C3* C2* . . 106.6(5) ?
    C3* C4* C5* . . 105.2(4) ?
    O* C5* N1* . . 125.4(5) ?
    O* C5* C4* . . 124.6(4) ?
    N1* C5* C4* . . 110.0(5) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    O5' H5' O* 1_555  .82 1.88 2.663(4) 159 ?
    N3 H3 O5' 4_645  .86 2.01 2.853(4) 166 ?
