##############################################################################
###                                                                        ###
###        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_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Ethyl 4-amino-5-cyano-6-[(2-hydroxyethyl)amino]-2-methylnicotinate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H16 N4 O3'
_chemical_formula_sum     'C12 H16 N4 O3'
_chemical_formula_iupac     'C12 H16 N4 O3'
_chemical_formula_weight     264.29
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P-1'
_symmetry_space_group_name_Hall     '-p 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.8350(7)
_cell_length_b     9.1368(9)
_cell_length_c     10.3272(10)
_cell_angle_alpha     79.720(2)
_cell_angle_beta     77.381(2)
_cell_angle_gamma     64.657(2)
_cell_volume     648.97(11)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1450
_cell_measurement_theta_min     3.24
_cell_measurement_theta_max     20.84
_cell_measurement_temperature     302(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.35
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.352
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     280
_exptl_absorpt_coefficient_mu     0.100
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2000)'
_exptl_absorpt_correction_T_min     0.9659
_exptl_absorpt_correction_T_max     0.9901
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     302(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD area detector'
_diffrn_measurement_method     'phi and omega scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4521
_diffrn_reflns_av_R_equivalents     0.0328
_diffrn_reflns_av_sigmaI/netI     0.0432
_diffrn_reflns_theta_min     2.03
_diffrn_reflns_theta_max     27.00
_diffrn_reflns_theta_full     27.00
_diffrn_measured_fraction_theta_max     0.980
_diffrn_measured_fraction_theta_full     0.980
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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     2767
_reflns_number_gt     1991
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0777
_refine_ls_R_factor_gt     0.0581
_refine_ls_wR_factor_gt     0.1572
_refine_ls_wR_factor_ref     0.1723
_refine_ls_goodness_of_fit_ref     1.062
_refine_ls_restrained_S_all     1.063
_refine_ls_number_reflns     2767
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0955P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.267
_refine_diff_density_min     -0.286
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'SMART (Bruker, 2000)'
_computing_cell_refinement     'SAINT (Bruker, 2000)'
_computing_data_reduction     'SAINT (Bruker, 2000)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 2000)'
_computing_publication_material     'SHELXTL (Bruker, 2000)'
loop_
    _atom_site_type_symbol
    _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
    C C1 0.4786(3) 0.2753(2) 0.45970(17) 0.0404(4) Uani d . 1 . .
    C C2 0.6483(2) 0.1345(2) 0.43570(17) 0.0372(4) Uani d . 1 . .
    C C3 0.7156(2) 0.0230(2) 0.54871(17) 0.0359(4) Uani d . 1 . .
    C C4 0.6070(2) 0.0620(2) 0.67547(17) 0.0377(4) Uani d . 1 . .
    C C5 0.4355(2) 0.2018(2) 0.68772(17) 0.0362(4) Uani d . 1 . .
    C C6 0.3927(3) 0.4091(3) 0.3547(2) 0.0642(7) Uani d . 1 . .
    H H6A 0.3536 0.3671 0.2930 0.096 Uiso calc R 1 . .
    H H6B 0.4861 0.4498 0.3080 0.096 Uiso calc R 1 . .
    H H6C 0.2837 0.4956 0.3963 0.096 Uiso calc R 1 . .
    C C7 0.6634(3) -0.0413(2) 0.79306(18) 0.0416(5) Uani d . 1 . .
    C C8 0.7589(3) 0.0936(2) 0.30234(18) 0.0419(5) Uani d . 1 . .
    C C9 0.7834(3) 0.1527(2) 0.06883(18) 0.0508(5) Uani d . 1 . .
    H H9A 0.7946 0.0472 0.0532 0.061 Uiso calc R 1 . .
    H H9B 0.9111 0.1486 0.0606 0.061 Uiso calc R 1 . .
    C C10 0.6766(3) 0.2811(3) -0.0303(2) 0.0607(6) Uani d . 1 . .
    H H10A 0.5483 0.2884 -0.0181 0.091 Uiso calc R 1 . .
    H H10B 0.7395 0.2536 -0.1188 0.091 Uiso calc R 1 . .
    H H10C 0.6734 0.3839 -0.0176 0.091 Uiso calc R 1 . .
    C C11 0.1222(3) 0.3504(2) 0.8233(2) 0.0510(5) Uani d . 1 . .
    H H11A 0.0591 0.3219 0.9096 0.061 Uiso calc R 1 . .
    H H11B 0.0634 0.3361 0.7558 0.061 Uiso calc R 1 . .
    C C12 0.0869(4) 0.5254(3) 0.8139(2) 0.0636(6) Uani d . 1 . .
    H H12A -0.0431 0.5853 0.8561 0.076 Uiso calc R 1 . .
    H H12B 0.1725 0.5358 0.8634 0.076 Uiso calc R 1 . .
    N N1 0.3761(2) 0.30703(18) 0.58156(14) 0.0422(4) Uani d . 1 . .
    N N2 0.8725(2) -0.11440(19) 0.53691(17) 0.0473(4) Uani d D 1 . .
    H H2B 0.928(3) -0.122(2) 0.4515(16) 0.057 Uiso d D 1 . .
    H H2A 0.900(3) -0.174(2) 0.6103(17) 0.057 Uiso d D 1 . .
    N N3 0.7004(3) -0.1181(2) 0.89125(17) 0.0560(5) Uani d . 1 . .
    N N4 0.3234(2) 0.23730(19) 0.80702(16) 0.0461(4) Uani d . 1 . .
    H H4A 0.372(3) 0.164(3) 0.866(2) 0.055 Uiso d . 1 . .
    O O1 0.9108(2) -0.02184(18) 0.28168(15) 0.0628(5) Uani d . 1 . .
    O O2 0.67814(19) 0.19305(16) 0.20107(12) 0.0496(4) Uani d . 1 . .
    O O3 0.1129(3) 0.59692(18) 0.68257(16) 0.0728(5) Uani d D 1 . .
    H H3A 0.111(5) 0.532(3) 0.633(3) 0.109 Uiso d D 1 . .
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
    C1 0.0431(10) 0.0397(9) 0.0313(10) -0.0113(8) -0.0064(8) 0.0004(7)
    C2 0.0384(10) 0.0388(9) 0.0303(9) -0.0129(8) -0.0036(7) -0.0026(7)
    C3 0.0368(9) 0.0315(8) 0.0367(10) -0.0112(7) -0.0068(7) -0.0023(7)
    C4 0.0415(10) 0.0340(9) 0.0330(10) -0.0117(8) -0.0089(8) 0.0019(7)
    C5 0.0379(9) 0.0355(9) 0.0310(9) -0.0115(7) -0.0052(7) -0.0018(7)
    C6 0.0650(14) 0.0540(12) 0.0347(11) 0.0083(11) -0.0050(10) 0.0024(9)
    C7 0.0395(10) 0.0347(9) 0.0383(10) -0.0056(8) -0.0027(8) -0.0018(8)
    C8 0.0452(11) 0.0421(10) 0.0360(10) -0.0155(9) -0.0056(8) -0.0050(8)
    C9 0.0582(13) 0.0539(12) 0.0309(10) -0.0174(10) 0.0040(9) -0.0084(9)
    C10 0.0656(15) 0.0747(15) 0.0353(11) -0.0241(12) -0.0067(10) -0.0024(10)
    C11 0.0446(11) 0.0516(11) 0.0409(11) -0.0098(9) 0.0026(8) -0.0024(9)
    C12 0.0740(15) 0.0466(11) 0.0450(13) -0.0019(10) -0.0076(11) -0.0041(9)
    N1 0.0429(9) 0.0391(8) 0.0318(8) -0.0065(7) -0.0040(7) -0.0007(6)
    N2 0.0499(10) 0.0387(8) 0.0378(9) -0.0058(7) -0.0049(8) 0.0002(7)
    N3 0.0602(11) 0.0499(10) 0.0359(9) -0.0054(8) -0.0073(8) 0.0056(8)
    N4 0.0455(10) 0.0412(9) 0.0321(9) -0.0025(7) -0.0042(7) 0.0027(7)
    O1 0.0578(9) 0.0564(9) 0.0436(8) 0.0027(7) 0.0005(7) -0.0081(7)
    O2 0.0509(8) 0.0531(8) 0.0286(7) -0.0074(6) -0.0020(6) -0.0051(6)
    O3 0.0843(12) 0.0443(8) 0.0532(10) -0.0013(8) 0.0004(8) 0.0061(7)
_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
    C1 N1 . 1.342(2) ?
    C1 C2 . 1.410(2) ?
    C1 C6 . 1.504(2) ?
    C2 C3 . 1.436(2) ?
    C2 C8 . 1.474(2) ?
    C3 N2 . 1.330(2) ?
    C3 C4 . 1.409(2) ?
    C4 C5 . 1.403(2) ?
    C4 C7 . 1.424(2) ?
    C5 N1 . 1.344(2) ?
    C5 N4 . 1.349(2) ?
    C6 H6A . 0.9600 ?
    C6 H6B . 0.9600 ?
    C6 H6C . 0.9600 ?
    C7 N3 . 1.142(2) ?
    C8 O1 . 1.212(2) ?
    C8 O2 . 1.333(2) ?
    C9 O2 . 1.452(2) ?
    C9 C10 . 1.493(3) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 H10A . 0.9600 ?
    C10 H10B . 0.9600 ?
    C10 H10C . 0.9600 ?
    C11 N4 . 1.461(2) ?
    C11 C12 . 1.490(3) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C12 O3 . 1.409(3) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    N2 H2B . 0.895(15) ?
    N2 H2A . 0.859(15) ?
    N4 H4A . 0.84(2) ?
    O3 H3A . 0.861(17) ?
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
    N1 C1 C2 . . 123.25(16) ?
    N1 C1 C6 . . 111.78(16) ?
    C2 C1 C6 . . 124.95(16) ?
    C1 C2 C3 . . 117.65(15) ?
    C1 C2 C8 . . 124.27(16) ?
    C3 C2 C8 . . 118.08(16) ?
    N2 C3 C4 . . 119.91(16) ?
    N2 C3 C2 . . 122.47(16) ?
    C4 C3 C2 . . 117.61(15) ?
    C5 C4 C3 . . 120.14(15) ?
    C5 C4 C7 . . 118.39(15) ?
    C3 C4 C7 . . 121.43(15) ?
    N1 C5 N4 . . 117.00(15) ?
    N1 C5 C4 . . 121.62(15) ?
    N4 C5 C4 . . 121.38(16) ?
    C1 C6 H6A . . 109.5 ?
    C1 C6 H6B . . 109.5 ?
    H6A C6 H6B . . 109.5 ?
    C1 C6 H6C . . 109.5 ?
    H6A C6 H6C . . 109.5 ?
    H6B C6 H6C . . 109.5 ?
    N3 C7 C4 . . 176.31(18) ?
    O1 C8 O2 . . 120.50(17) ?
    O1 C8 C2 . . 124.55(18) ?
    O2 C8 C2 . . 114.94(16) ?
    O2 C9 C10 . . 107.96(16) ?
    O2 C9 H9A . . 110.1 ?
    C10 C9 H9A . . 110.1 ?
    O2 C9 H9B . . 110.1 ?
    C10 C9 H9B . . 110.1 ?
    H9A C9 H9B . . 108.4 ?
    C9 C10 H10A . . 109.5 ?
    C9 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C9 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    N4 C11 C12 . . 115.13(18) ?
    N4 C11 H11A . . 108.5 ?
    C12 C11 H11A . . 108.5 ?
    N4 C11 H11B . . 108.5 ?
    C12 C11 H11B . . 108.5 ?
    H11A C11 H11B . . 107.5 ?
    O3 C12 C11 . . 114.25(18) ?
    O3 C12 H12A . . 108.7 ?
    C11 C12 H12A . . 108.7 ?
    O3 C12 H12B . . 108.7 ?
    C11 C12 H12B . . 108.7 ?
    H12A C12 H12B . . 107.6 ?
    C1 N1 C5 . . 119.62(15) ?
    C3 N2 H2B . . 110.1(13) ?
    C3 N2 H2A . . 115.4(15) ?
    H2B N2 H2A . . 134(2) ?
    C5 N4 C11 . . 123.93(15) ?
    C5 N4 H4A . . 109.6(16) ?
    C11 N4 H4A . . 123.3(16) ?
    C8 O2 C9 . . 115.70(15) ?
    C12 O3 H3A . . 105(2) ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    N1 C1 C2 C3 . . . . -1.8(3) ?
    C6 C1 C2 C3 . . . . 176.79(18) ?
    N1 C1 C2 C8 . . . . 177.27(16) ?
    C6 C1 C2 C8 . . . . -4.2(3) ?
    C1 C2 C3 N2 . . . . 179.06(17) ?
    C8 C2 C3 N2 . . . . -0.1(3) ?
    C1 C2 C3 C4 . . . . 0.2(2) ?
    C8 C2 C3 C4 . . . . -178.96(15) ?
    N2 C3 C4 C5 . . . . -176.27(17) ?
    C2 C3 C4 C5 . . . . 2.7(2) ?
    N2 C3 C4 C7 . . . . 1.3(3) ?
    C2 C3 C4 C7 . . . . -179.74(15) ?
    C3 C4 C5 N1 . . . . -4.2(3) ?
    C7 C4 C5 N1 . . . . 178.16(15) ?
    C3 C4 C5 N4 . . . . 176.30(16) ?
    C7 C4 C5 N4 . . . . -1.4(3) ?
    C1 C2 C8 O1 . . . . 175.22(19) ?
    C3 C2 C8 O1 . . . . -5.7(3) ?
    C1 C2 C8 O2 . . . . -5.8(3) ?
    C3 C2 C8 O2 . . . . 173.23(14) ?
    N4 C11 C12 O3 . . . . 78.5(3) ?
    C2 C1 N1 C5 . . . . 0.4(3) ?
    C6 C1 N1 C5 . . . . -178.30(17) ?
    N4 C5 N1 C1 . . . . -177.88(16) ?
    C4 C5 N1 C1 . . . . 2.6(3) ?
    N1 C5 N4 C11 . . . . 18.9(3) ?
    C4 C5 N4 C11 . . . . -161.55(17) ?
    C12 C11 N4 C5 . . . . -83.0(2) ?
    O1 C8 O2 C9 . . . . 0.1(3) ?
    C2 C8 O2 C9 . . . . -178.88(15) ?
    C10 C9 O2 C8 . . . . -177.24(15) ?
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
    O3 H3A N1 . 0.861(17) 2.25(3) 2.780(2) 120(3) yes
    N2 H2B O1 . 0.895(15) 1.832(17) 2.613(2) 144.6(19) yes
    N4 H4A N3 2_657 0.84(2) 2.45(2) 3.105(2) 136.1(19) yes
    N2 H2A O3 1_645 0.859(15) 2.175(18) 2.887(2) 140(2) yes
    C12 H12A N3 1_465 0.97 2.62 3.442(3) 142.2 ?
data_global
_journal_date_recd_electronic     2007-08-30
_journal_date_accepted     2007-09-04
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue     10
_journal_page_first     o4015
_journal_page_last     o4015
_journal_paper_category     QO
_journal_coeditor_code     CV2296
_publ_contact_author_name     'Dr. Qing-Yun Ren'
_publ_contact_author_address
;
Key Laboratory of Pesticides and Chemical Biology of Ministry of Education
College of Chemistry
Central China Normal University
Wuhan  430079
People's Republic of China
;
_publ_contact_author_email     he1208@yahoo.com.cn
_publ_contact_author_fax     '0086-027-67867960'
_publ_contact_author_phone     '0086-027-67867960'
_publ_section_title
;
Ethyl 4-amino-5-cyano-6-[(2-hydroxyethyl)amino]-2-methylnicotinate
;
loop_
    _publ_author_name
    _publ_author_address
    'Qing-Yun Ren'
;
Key Laboratory of Pesticides and Chemical Biology of the Ministry of Education
College of Chemistry
Central China Normal University
Wuhan  430079
People's Republic of China
;
    'Hong-Wu He'
;
Key Laboratory of Pesticides and Chemical Biology of the Ministry of Education
College of Chemistry
Central China Normal University
Wuhan  430079
People's Republic of China
;
    'Chuan-Fei Jin'
;
Key Laboratory of Pesticides and Chemical Biology of the Ministry of Education
College of Chemistry
Central China Normal University
Wuhan  430079
People's Republic of China
;
    'Yu-Cheng Gu'
;
Jealott's Hill International Research Centre,
Syngenta, Bracknell RG42 6EY
Berkshire
United Kingdom
;
