##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, 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 2.1.    #
#                                                                            #
# 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_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2001-04-05
_journal_date_accepted     2001-04-17
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2001
_journal_volume     57
_journal_issue      5
_journal_page_first     o451
_journal_page_last     o453
_journal_paper_category     EO
_publ_contact_author_name     'Dr E. R. T. Tiekink'
_publ_contact_author_address
;
Department of Chemistry,
The University of Adelaide,
Australia 5005
;
_publ_contact_author_email     edward.tiekink@adelaide.edu.au
_publ_contact_author_fax     '61 8 8303 4358'
_publ_contact_author_phone     '61 8 8303 5943'
_publ_section_title
;
Ethyl 3-methylimidazo[1,2-a]pyrimidine-2-carboxylate
;
loop_
    _publ_author_name
    _publ_author_address
    'Prager, Rolf H.'
;
School of Chemistry, Physics and Earth Sciences, Flinders University,
GPO Box 2100, Adelaide, 5001, Australia
;
    'Smith, Jason A.'
;
School of Chemistry, Physics and Earth Sciences, Flinders University,
GPO Box 2100, Adelaide, 5001, Australia
;
    'Tiekink, Edward R. T.'
;
Department of Chemistry, The University of Adelaide, Australia 5005
;
data_I
_chemical_formula_moiety     'C10 H11 N3 O2'
_chemical_formula_sum     'C10 H11 N3 O2'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C10 H11 N3 O2'
_chemical_formula_weight     205.22
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     ?
loop_
    _symmetry_equiv_pos_as_xyz
    '   +x,   +y,   +z'
    '   -x,   -y,   -z'
_cell_length_a     9.9100(10)
_cell_length_b     11.653(2)
_cell_length_c     9.000(2)
_cell_angle_alpha     100.930(10)
_cell_angle_beta     95.310(10)
_cell_angle_gamma     89.240(10)
_cell_volume     1016.0(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     19.8
_cell_measurement_theta_max     22.0
_cell_measurement_temperature     293
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max      .32
_exptl_crystal_size_mid      .32
_exptl_crystal_size_min      .24
_exptl_crystal_density_diffrn     1.341
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     432
_exptl_absorpt_coefficient_mu      .097
_exptl_absorpt_correction_type     none
_exptl_special_details
;
The scan width was (1.52+0.35tanθ)° with an ω
scan speed of 32° per minute
(up to 5 scans to achieve I/σ(I) > 20).
Stationary background counts were recorded at each end of the
scan, and the scan time:background time ratio was 2:1.
;
_diffrn_ambient_temperature     293
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'Rigaku rotating anode'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device     'Rigaku AFC-6R'
_diffrn_measurement_method     ω-2θ
_diffrn_reflns_number     4967
_diffrn_reflns_av_R_equivalents      .059
_diffrn_reflns_av_sigmaI/netI     ?
_diffrn_reflns_theta_min     3.2
_diffrn_reflns_theta_max     27.6
_diffrn_reflns_theta_full     27.6
_diffrn_measured_fraction_theta_max      .998
_diffrn_measured_fraction_theta_full      .998
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_diffrn_reflns_reduction_process     'Lp corrections applied'
_diffrn_standards_number     3
_diffrn_standards_interval_count     400
_diffrn_standards_decay_%     5.1
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    -2 0 2
    -2 1 2
    -1 1 2
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     4696
_reflns_number_gt     2373
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .147
_refine_ls_R_factor_gt      .058
_refine_ls_wR_factor_ref      .171
_refine_ls_goodness_of_fit_ref     1.03
_refine_ls_restrained_S_all     1.03
_refine_ls_number_reflns     4696
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0827P)²+0.0227P] where P = (Fo²+2Fc²)/3'
_refine_ls_shift/su_max     <0.001
_refine_ls_shift/su_mean      .000
_refine_diff_density_max      .18
_refine_diff_density_min      -.31
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C  .002  .002
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
    H  .000  .000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
    N  .004  .003
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
    O  .008  .006
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1992)
;
_computing_cell_refinement     'MSC/AFC Diffractometer Control Software'
_computing_data_reduction
                    'TEXSAN for Windows (Molecular Structure Corporation, 1997)'
_computing_structure_solution     'SIR88 (Burla et al., 1989)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_publication_material     '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
    O2A  -.5071(2)  .14140(17)  .3538(2)  .0832(6) Uani d . 1 . . O
    O2'A  -.31279(18)  .18219(14)  .5020(2)  .0658(5) Uani d . 1 . . O
    O2B  -.3865(2)  .19785(18)  -.0494(2)  .0879(7) Uani d . 1 . . O
    O2'B  -.2330(2)  .11494(16)  .0911(2)  .0801(6) Uani d . 1 . . O
    N1A  -.30835(18)  .40531(16)  .4586(2)  .0470(5) Uani d . 1 . . N
    N1B  -.23653(19)  .41172(18)  .0354(2)  .0539(5) Uani d . 1 . . N
    N4A  -.45032(17)  .49217(17)  .30469(19)  .0462(5) Uani d . 1 . . N
    N4B  -.05618(17)  .44123(17)  .20843(19)  .0463(5) Uani d . 1 . . N
    N8A  -.26319(19)  .60486(17)  .4486(2)  .0504(5) Uani d . 1 . . N
    N8B  -.1309(2)  .60075(18)  .0866(2)  .0563(5) Uani d . 1 . . N
    C2A  -.4091(2)  .3298(2)  .3855(2)  .0485(6) Uani d . 1 . . C
    C2'A  -.4171(3)  .2096(2)  .4099(3)  .0580(6) Uani d . 1 . . C
    C2B  -.2039(2)  .3120(2)  .0920(3)  .0498(6) Uani d . 1 . . C
    C2'B  -.2856(3)  .2049(2)  .0353(3)  .0579(6) Uani d . 1 . . C
    C3A  -.4980(2)  .3805(2)  .2899(2)  .0504(6) Uani d . 1 . . C
    C3'A  -.6195(3)  .3371(3)  .1860(3)  .0730(8) Uani d . 1 . . C
    H3A  -.6963  .3843  .2152  .132(3) Uiso calc R 1 . . H
    H3B  -.6371  .2574  .1922  .132(3) Uiso calc R 1 . . H
    H3C  -.6037  .3415  .0837  .132(3) Uiso calc R 1 . . H
    C3B  -.0932(2)  .3271(2)  .1982(2)  .0477(6) Uani d . 1 . . C
    C3'B  -.0188(3)  .2511(2)  .2947(3)  .0637(7) Uani d . 1 . . C
    H3D  -.0183  .2874  .3998  .132(3) Uiso calc R 1 . . H
    H3E  .0727  .2406  .2680  .132(3) Uiso calc R 1 . . H
    H3F  -.0632  .1764  .2782  .132(3) Uiso calc R 1 . . H
    C5A  -.4942(2)  .5849(2)  .2391(3)  .0582(7) Uani d . 1 . . C
    H5A  -.5702  .5785  .1691  .088(2) Uiso calc R 1 . . H
    C5B  .0464(2)  .5071(2)  .2948(3)  .0515(6) Uani d . 1 . . C
    H5B  .1044  .4762  .3644  .088(2) Uiso calc R 1 . . H
    C6A  -.4235(3)  .6847(2)  .2795(3)  .0615(7) Uani d . 1 . . C
    H6A  -.4505  .7497  .2383  .088(2) Uiso calc R 1 . . H
    C6B  .0605(2)  .6178(2)  .2757(3)  .0567(6) Uani d . 1 . . C
    H6B  .1290  .6655  .3319  .088(2) Uiso calc R 1 . . H
    C7A  -.3084(3)  .6913(2)  .3844(3)  .0602(7) Uani d . 1 . . C
    H7A  -.2612  .7617  .4098  .088(2) Uiso calc R 1 . . H
    C7B  -.0301(3)  .6602(2)  .1696(3)  .0595(7) Uani d . 1 . . C
    H7B  -.0176  .7367  .1571  .088(2) Uiso calc R 1 . . H
    C9A  -.3346(2)  .5029(2)  .4088(2)  .0437(5) Uani d . 1 . . C
    C9B  -.1452(2)  .4891(2)  .1064(2)  .0467(6) Uani d . 1 . . C
    C21A  -.3175(3)  .0668(3)  .5401(4)  .0852(9) Uani d . 1 . . C
    H21A  -.3320  .0078  .4483  .110(3) Uiso calc R 1 . . H
    H21B  -.3911  .0621  .6026  .110(3) Uiso calc R 1 . . H
    C21B  -.3027(3)  .0035(3)  .0465(4)  .0878(10) Uani d . 1 . . C
    H21C  -.3241  -.0144  -.0628  .110(3) Uiso calc R 1 . . H
    H21D  -.3864  .0054  .0950  .110(3) Uiso calc R 1 . . H
    C22A  -.1870(4)  .0475(3)  .6236(5)  .1085(12) Uani d . 1 . . C
    H22A  -.1873  -.0283  .6507  .132(3) Uiso calc R 1 . . H
    H22B  -.1737  .1063  .7141  .132(3) Uiso calc R 1 . . H
    H22C  -.1150  .0519  .5605  .132(3) Uiso calc R 1 . . H
    C22B  -.2103(4)  -.0845(3)  .0957(4)  .1154(14) Uani d . 1 . . C
    H22D  -.2528  -.1601  .0687  .132(3) Uiso calc R 1 . . H
    H22E  -.1896  -.0654  .2039  .132(3) Uiso calc R 1 . . H
    H22F  -.1282  -.0856  .0466  .132(3) Uiso calc R 1 . . 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
    O2A  .0802(14)  .0689(13)  .0963(15)  -.0273(11)  -.0163(12)  .0147(11)
    O2'A  .0608(11)  .0528(10)  .0861(13)  -.0072(8)  -.0054(10)  .0247(9)
    O2B  .0762(14)  .0844(14)  .0931(15)  -.0080(11)  -.0435(12)  .0153(12)
    O2'B  .0771(13)  .0618(12)  .0945(14)  -.0119(10)  -.0356(11)  .0169(10)
    N1A  .0434(10)  .0513(12)  .0459(11)  -.0034(9)  -.0031(8)  .0113(9)
    N1B  .0471(11)  .0668(13)  .0465(11)  .0054(10)  -.0057(9)  .0129(10)
    N4A  .0390(10)  .0604(13)  .0392(10)  .0013(9)  -.0026(8)  .0124(9)
    N4B  .0387(10)  .0599(13)  .0408(10)  .0036(9)  -.0024(8)  .0136(9)
    N8A  .0488(11)  .0530(12)  .0504(11)  -.0065(9)  -.0035(9)  .0157(9)
    N8B  .0540(13)  .0626(14)  .0531(12)  .0049(10)  -.0024(10)  .0169(10)
    C2A  .0413(12)  .0568(15)  .0462(13)  -.0050(11)  .0024(10)  .0068(11)
    C2'A  .0536(15)  .0578(16)  .0610(16)  -.0063(13)  .0031(13)  .0077(13)
    C2B  .0435(12)  .0605(15)  .0431(12)  .0028(11)  -.0026(10)  .0075(11)
    C2'B  .0530(15)  .0673(17)  .0504(14)  .0046(13)  -.0080(12)  .0097(12)
    C3A  .0393(12)  .0689(17)  .0409(12)  -.0043(11)  .0019(10)  .0056(11)
    C3'A  .0537(16)  .096(2)  .0622(17)  -.0135(14)  -.0177(13)  .0075(15)
    C3B  .0408(12)  .0593(15)  .0430(12)  .0009(11)  -.0013(10)  .0118(11)
    C3'B  .0581(16)  .0671(17)  .0668(16)  -.0024(13)  -.0153(13)  .0250(13)
    C5A  .0486(14)  .083(2)  .0459(13)  .0132(14)  -.0010(11)  .0229(13)
    C5B  .0404(12)  .0674(17)  .0460(13)  -.0004(11)  -.0046(10)  .0131(11)
    C6A  .0622(16)  .0680(18)  .0605(16)  .0083(14)  .0026(13)  .0296(13)
    C6B  .0495(14)  .0631(17)  .0566(15)  -.0017(12)  -.0008(12)  .0113(12)
    C7A  .0613(16)  .0625(16)  .0606(16)  -.0023(13)  .0044(13)  .0218(13)
    C7B  .0575(16)  .0611(16)  .0610(15)  .0054(13)  .0049(13)  .0145(13)
    C9A  .0363(11)  .0580(14)  .0366(11)  .0001(10)  -.0026(9)  .0109(10)
    C9B  .0416(12)  .0610(16)  .0366(12)  .0061(11)  -.0014(10)  .0097(11)
    C21A  .090(2)  .0572(18)  .112(3)  -.0054(16)  -.0045(19)  .0300(17)
    C21B  .090(2)  .069(2)  .094(2)  -.0205(17)  -.0293(18)  .0071(17)
    C22A  .106(3)  .082(2)  .145(3)  .008(2)  -.011(2)  .053(2)
    C22B  .139(3)  .065(2)  .133(3)  -.012(2)  -.043(3)  .021(2)
_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
    O2A C2'A . 1.210(3) ?
    O2'A C2'A . 1.338(3) ?
    O2'A C21A . 1.451(3) ?
    O2B C2'B . 1.194(3) ?
    O2'B C2'B . 1.326(3) ?
    O2'B C21B . 1.448(3) ?
    N1A C9A . 1.314(3) ?
    N1A C2A . 1.373(3) ?
    N1B C9B . 1.319(3) ?
    N1B C2B . 1.378(3) ?
    N4A C3A . 1.368(3) ?
    N4A C5A . 1.373(3) ?
    N4A C9A . 1.403(3) ?
    N4B C3B . 1.368(3) ?
    N4B C5B . 1.369(3) ?
    N4B C9B . 1.401(3) ?
    N8A C7A . 1.307(3) ?
    N8A C9A . 1.362(3) ?
    N8B C7B . 1.312(3) ?
    N8B C9B . 1.356(3) ?
    C2A C3A . 1.380(3) ?
    C2A C2'A . 1.462(3) ?
    C2B C3B . 1.377(3) ?
    C2B C2'B . 1.477(4) ?
    C3A C3'A . 1.487(3) ?
    C3B C3'B . 1.496(3) ?
    C5A C6A . 1.339(4) ?
    C5B C6B . 1.344(3) ?
    C6A C7A . 1.405(3) ?
    C6B C7B . 1.404(3) ?
    C21A C22A . 1.471(4) ?
    C21B C22B . 1.469(4) ?
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
    C2'A O2'A C21A . . 115.9(2) ?
    C2'B O2'B C21B . . 117.8(2) ?
    C9A N1A C2A . . 104.41(18) ?
    C9B N1B C2B . . 104.29(18) ?
    C3A N4A C5A . . 132.5(2) ?
    C3A N4A C9A . . 106.96(18) ?
    C5A N4A C9A . . 120.5(2) ?
    C3B N4B C5B . . 131.5(2) ?
    C3B N4B C9B . . 107.67(19) ?
    C5B N4B C9B . . 120.8(2) ?
    C7A N8A C9A . . 116.3(2) ?
    C7B N8B C9B . . 115.8(2) ?
    C3A C2A N1A . . 112.4(2) ?
    C3A C2A C2'A . . 125.5(2) ?
    N1A C2A C2'A . . 122.0(2) ?
    O2A C2'A O2'A . . 123.1(2) ?
    O2A C2'A C2A . . 124.5(2) ?
    O2'A C2'A C2A . . 112.4(2) ?
    C3B C2B N1B . . 112.7(2) ?
    C3B C2B C2'B . . 127.9(2) ?
    N1B C2B C2'B . . 119.3(2) ?
    O2B C2'B O2'B . . 123.1(3) ?
    O2B C2'B C2B . . 125.6(2) ?
    O2'B C2'B C2B . . 111.3(2) ?
    C2A C3A N4A . . 104.53(19) ?
    C2A C3A C3'A . . 133.5(2) ?
    N4A C3A C3'A . . 121.9(2) ?
    C2B C3B N4B . . 104.13(19) ?
    C2B C3B C3'B . . 134.7(2) ?
    N4B C3B C3'B . . 121.1(2) ?
    C6A C5A N4A . . 117.5(2) ?
    C6B C5B N4B . . 117.8(2) ?
    C5A C6A C7A . . 119.9(2) ?
    C5B C6B C7B . . 118.8(2) ?
    N8A C7A C6A . . 124.4(2) ?
    N8B C7B C6B . . 125.3(2) ?
    N1A C9A N8A . . 126.92(19) ?
    N1A C9A N4A . . 111.7(2) ?
    N8A C9A N4A . . 121.4(2) ?
    N1B C9B N8B . . 127.3(2) ?
    N1B C9B N4B . . 111.2(2) ?
    N8B C9B N4B . . 121.5(2) ?
    O2'A C21A C22A . . 107.6(3) ?
    O2'B C21B C22B . . 106.6(3) ?
