##############################################################################
###                                                                        ###
###        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_2
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Ethyl
4-(2-amino-1-cyano-2-oxoethyl)-2-oxo-1-propyl-1,2-dihydroquinoline-3-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H19 N3 O4'
_chemical_formula_sum     'C18 H19 N3 O4'
_chemical_formula_iupac     'C18 H19 N3 O4'
_chemical_formula_weight     341.36
_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     8.2279(15)
_cell_length_b     10.555(2)
_cell_length_c     11.701(3)
_cell_angle_alpha     116.092(15)
_cell_angle_beta     94.213(16)
_cell_angle_gamma     104.475(15)
_cell_volume     863.8(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     36
_cell_measurement_theta_min     8
_cell_measurement_theta_max     24
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.312
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     360
_exptl_absorpt_coefficient_mu     0.09
_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     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Siemens P3/PC'
_diffrn_measurement_method     'ω--2θ'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3365
_diffrn_reflns_av_R_equivalents     0.037
_diffrn_reflns_av_sigmaI/netI     0.033
_diffrn_reflns_theta_min     2.2
_diffrn_reflns_theta_max     25.5
_diffrn_reflns_theta_full     25.5
_diffrn_measured_fraction_theta_max     0.974
_diffrn_measured_fraction_theta_full     0.974
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     2
_diffrn_standards_interval_count     98
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     5
_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     3132
_reflns_number_gt     2139
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.089
_refine_ls_R_factor_gt     0.056
_refine_ls_wR_factor_gt     0.147
_refine_ls_wR_factor_ref     0.164
_refine_ls_goodness_of_fit_ref     1.02
_refine_ls_restrained_S_all     1.02
_refine_ls_number_reflns     3132
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
           'calc w=1/[σ²(Fo²)+(0.094P)²+0.213P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_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     0.52
_refine_diff_density_min     -0.26
_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     'P3 (Siemens,1989)'
_computing_cell_refinement     P3
_computing_data_reduction     'XDISK (Siemens, 1991)'
_computing_structure_solution     'SHELXTL (Sheldrick, 1998)'
_computing_structure_refinement     SHELXTL
_computing_molecular_graphics     SHELXTL
_computing_publication_material     SHELXTL
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
    N N1 0.4269(2) 0.1405(2) 0.31504(18) 0.0410(4) Uani d . 1 . .
    N N2 0.5266(4) -0.4346(3) 0.1965(3) 0.0750(7) Uani d . 1 . .
    N N3 0.8710(2) -0.0775(3) 0.1015(2) 0.0580(6) Uani d . 1 . .
    H H3NB 0.9789 -0.0413 0.1066 0.070 Uiso calc R 1 . .
    H H3NA 0.7980 -0.0486 0.0707 0.070 Uiso calc R 1 . .
    O O1 0.2368(2) 0.0504(2) 0.12648(17) 0.0538(5) Uani d . 1 . .
    O O2 0.3621(4) -0.1814(3) -0.0987(2) 0.1245(12) Uani d . 1 . .
    O O3 0.2182(3) -0.3121(2) -0.01570(17) 0.0717(6) Uani d . 1 . .
    O O4 0.9106(2) -0.2244(2) 0.18545(18) 0.0615(5) Uani d . 1 . .
    C C2 0.3539(3) 0.0371(3) 0.1888(2) 0.0404(5) Uani d . 1 . .
    C C3 0.4195(2) -0.0875(2) 0.1303(2) 0.0368(5) Uani d . 1 . .
    C C4 0.5491(2) -0.1016(2) 0.1958(2) 0.0348(5) Uani d . 1 . .
    C C4A 0.6183(2) 0.0043(2) 0.3316(2) 0.0353(5) Uani d . 1 . .
    C C5 0.7433(3) -0.0088(3) 0.4097(2) 0.0413(5) Uani d . 1 . .
    H H5 0.7885 -0.0866 0.3725 0.050 Uiso calc R 1 . .
    C C6 0.8006(3) 0.0897(3) 0.5392(2) 0.0501(6) Uani d . 1 . .
    H H6 0.8844 0.0789 0.5890 0.060 Uiso calc R 1 . .
    C C7 0.7341(3) 0.2048(3) 0.5960(2) 0.0522(6) Uani d . 1 . .
    H H7 0.7722 0.2707 0.6845 0.063 Uiso calc R 1 . .
    C C8 0.6115(3) 0.2235(3) 0.5231(2) 0.0489(6) Uani d . 1 . .
    H H8 0.5680 0.3021 0.5624 0.059 Uiso calc R 1 . .
    C C8A 0.5529(3) 0.1246(2) 0.3904(2) 0.0380(5) Uani d . 1 . .
    C C9 0.3326(3) -0.1954(3) -0.0084(2) 0.0440(5) Uani d . 1 . .
    C C10 0.1106(4) -0.4237(3) -0.1440(3) 0.0758(9) Uani d . 1 . .
    H H10A 0.1715 -0.4226 -0.2116 0.091 Uiso calc R 1 . .
    H H10B 0.0848 -0.5218 -0.1508 0.091 Uiso calc R 1 . .
    C C11 -0.0464(6) -0.3909(5) -0.1609(4) 0.1269(19) Uani d . 1 . .
    H H11A -0.0205 -0.2958 -0.1585 0.190 Uiso calc R 1 . .
    H H11B -0.1045 -0.3891 -0.0922 0.190 Uiso calc R 1 . .
    H H11C -0.1190 -0.4661 -0.2433 0.190 Uiso calc R 1 . .
    C C12 0.6210(3) -0.2290(2) 0.1266(2) 0.0409(5) Uani d . 1 . .
    H H12 0.5699 -0.2763 0.0336 0.049 Uiso calc R 1 . .
    C C13 0.8180(3) -0.1765(3) 0.1407(2) 0.0438(5) Uani d . 1 . .
    C C14 0.5705(3) -0.3438(3) 0.1682(2) 0.0506(6) Uani d . 1 . .
    C C15 0.3675(3) 0.2719(3) 0.3701(3) 0.0542(6) Uani d . 1 . .
    H H15A 0.3366 0.2949 0.3015 0.065 Uiso calc R 1 . .
    H H15B 0.4610 0.3563 0.4352 0.065 Uiso calc R 1 . .
    C C16 0.2145(4) 0.2492(3) 0.4318(3) 0.0608(7) Uani d . 1 . .
    H H16A 0.1182 0.1691 0.3656 0.073 Uiso calc R 1 . .
    H H16B 0.2426 0.2202 0.4969 0.073 Uiso calc R 1 . .
    C C17 0.1631(6) 0.3883(4) 0.4949(4) 0.0980(12) Uani d . 1 . .
    H H17A 0.1419 0.4207 0.4320 0.147 Uiso calc R 1 . .
    H H17B 0.2541 0.4651 0.5661 0.147 Uiso calc R 1 . .
    H H17C 0.0608 0.3676 0.5268 0.147 Uiso calc R 1 . .
_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
    N1 C2 . 1.363(3) yes
    N1 C8A . 1.402(3) yes
    N1 C15 . 1.475(3) yes
    N2 C14 . 1.132(3) no
    N3 C13 . 1.310(3) no
    N3 H3NB . 0.8600 no
    N3 H3NA . 0.8600 no
    O1 C2 . 1.239(3) yes
    O2 C9 . 1.164(3) no
    O3 C9 . 1.313(3) no
    O3 C10 . 1.467(3) no
    O4 C13 . 1.215(3) no
    C2 C3 . 1.451(3) yes
    C3 C4 . 1.344(3) yes
    C3 C9 . 1.496(3) yes
    C4 C4A . 1.444(3) yes
    C4 C12 . 1.525(3) yes
    C4A C5 . 1.399(3) no
    C4A C8A . 1.415(3) no
    C5 C6 . 1.365(3) no
    C5 H5 . 0.9300 no
    C6 C7 . 1.375(4) no
    C6 H6 . 0.9300 no
    C7 C8 . 1.381(4) no
    C7 H7 . 0.9300 no
    C8 C8A . 1.394(3) no
    C8 H8 . 0.9300 no
    C10 C11 . 1.440(5) no
    C10 H10A . 0.9700 no
    C10 H10B . 0.9700 no
    C11 H11A . 0.9600 no
    C11 H11B . 0.9600 no
    C11 H11C . 0.9600 no
    C12 C14 . 1.474(3) no
    C12 C13 . 1.547(3) yes
    C12 H12 . 0.9800 no
    C15 C16 . 1.516(4) no
    C15 H15A . 0.9700 no
    C15 H15B . 0.9700 no
    C16 C17 . 1.511(4) no
    C16 H16A . 0.9700 no
    C16 H16B . 0.9700 no
    C17 H17A . 0.9600 no
    C17 H17B . 0.9600 no
    C17 H17C . 0.9600 no
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 N1 C8A . . 122.21(18) ?
    C2 N1 C15 . . 116.97(19) ?
    C8A N1 C15 . . 120.82(19) ?
    C13 N3 H3NB . . 120.0 ?
    C13 N3 H3NA . . 120.0 ?
    H3NB N3 H3NA . . 120.0 ?
    C9 O3 C10 . . 117.7(2) ?
    O1 C2 N1 . . 120.8(2) ?
    O1 C2 C3 . . 121.6(2) ?
    N1 C2 C3 . . 117.66(18) ?
    C4 C3 C2 . . 122.17(19) ?
    C4 C3 C9 . . 123.6(2) ?
    C2 C3 C9 . . 114.18(18) ?
    C3 C4 C4A . . 119.38(19) ?
    C3 C4 C12 . . 119.92(19) ?
    C4A C4 C12 . . 120.70(17) ?
    C5 C4A C8A . . 118.01(19) ?
    C5 C4A C4 . . 123.13(19) ?
    C8A C4A C4 . . 118.82(18) ?
    C6 C5 C4A . . 121.7(2) ?
    C6 C5 H5 . . 119.1 ?
    C4A C5 H5 . . 119.1 ?
    C5 C6 C7 . . 119.8(2) ?
    C5 C6 H6 . . 120.1 ?
    C7 C6 H6 . . 120.1 ?
    C6 C7 C8 . . 120.8(2) ?
    C6 C7 H7 . . 119.6 ?
    C8 C7 H7 . . 119.6 ?
    C7 C8 C8A . . 120.0(2) ?
    C7 C8 H8 . . 120.0 ?
    C8A C8 H8 . . 120.0 ?
    C8 C8A N1 . . 120.9(2) ?
    C8 C8A C4A . . 119.6(2) ?
    N1 C8A C4A . . 119.46(19) ?
    O2 C9 O3 . . 123.7(2) ?
    O2 C9 C3 . . 125.7(2) ?
    O3 C9 C3 . . 110.53(19) ?
    C11 C10 O3 . . 109.4(3) ?
    C11 C10 H10A . . 109.8 ?
    O3 C10 H10A . . 109.8 ?
    C11 C10 H10B . . 109.8 ?
    O3 C10 H10B . . 109.8 ?
    H10A C10 H10B . . 108.3 ?
    C10 C11 H11A . . 109.5 ?
    C10 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C10 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C14 C12 C4 . . 111.94(18) ?
    C14 C12 C13 . . 110.57(19) ?
    C4 C12 C13 . . 113.15(18) ?
    C14 C12 H12 . . 106.9 ?
    C4 C12 H12 . . 106.9 ?
    C13 C12 H12 . . 106.9 ?
    O4 C13 N3 . . 125.0(2) ?
    O4 C13 C12 . . 121.3(2) ?
    N3 C13 C12 . . 113.63(19) ?
    N2 C14 C12 . . 177.5(3) ?
    N1 C15 C16 . . 112.9(2) ?
    N1 C15 H15A . . 109.0 ?
    C16 C15 H15A . . 109.0 ?
    N1 C15 H15B . . 109.0 ?
    C16 C15 H15B . . 109.0 ?
    H15A C15 H15B . . 107.8 ?
    C17 C16 C15 . . 111.8(2) ?
    C17 C16 H16A . . 109.2 ?
    C15 C16 H16A . . 109.2 ?
    C17 C16 H16B . . 109.2 ?
    C15 C16 H16B . . 109.2 ?
    H16A C16 H16B . . 107.9 ?
    C16 C17 H17A . . 109.5 ?
    C16 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C16 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
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
    C8A N1 C2 O1 . . . . 176.43(19) ?
    C15 N1 C2 O1 . . . . -3.7(3) ?
    C8A N1 C2 C3 . . . . -4.2(3) ?
    C15 N1 C2 C3 . . . . 175.68(18) ?
    O1 C2 C3 C4 . . . . 178.45(19) ?
    N1 C2 C3 C4 . . . . -0.9(3) ?
    O1 C2 C3 C9 . . . . -0.6(3) ?
    N1 C2 C3 C9 . . . . -179.90(18) ?
    C2 C3 C4 C4A . . . . 4.4(3) ?
    C9 C3 C4 C4A . . . . -176.64(19) ?
    C2 C3 C4 C12 . . . . -175.83(18) ?
    C9 C3 C4 C12 . . . . 3.1(3) ?
    C3 C4 C4A C5 . . . . 174.7(2) ?
    C12 C4 C4A C5 . . . . -5.0(3) ?
    C3 C4 C4A C8A . . . . -3.0(3) ?
    C12 C4 C4A C8A . . . . 177.23(18) ?
    C8A C4A C5 C6 . . . . 0.7(3) ?
    C4 C4A C5 C6 . . . . -177.1(2) ?
    C4A C5 C6 C7 . . . . 0.4(3) ?
    C5 C6 C7 C8 . . . . -1.0(4) ?
    C6 C7 C8 C8A . . . . 0.4(4) ?
    C7 C8 C8A N1 . . . . 179.1(2) ?
    C7 C8 C8A C4A . . . . 0.7(3) ?
    C2 N1 C8A C8 . . . . -172.86(19) ?
    C15 N1 C8A C8 . . . . 7.2(3) ?
    C2 N1 C8A C4A . . . . 5.6(3) ?
    C15 N1 C8A C4A . . . . -174.36(18) ?
    C5 C4A C8A C8 . . . . -1.2(3) ?
    C4 C4A C8A C8 . . . . 176.62(19) ?
    C5 C4A C8A N1 . . . . -179.66(18) ?
    C4 C4A C8A N1 . . . . -1.8(3) ?
    C10 O3 C9 O2 . . . . -6.1(4) ?
    C10 O3 C9 C3 . . . . 175.0(2) ?
    C4 C3 C9 O2 . . . . -98.0(4) ?
    C2 C3 C9 O2 . . . . 80.9(4) ?
    C4 C3 C9 O3 . . . . 80.8(3) ?
    C2 C3 C9 O3 . . . . -100.2(2) ?
    C9 O3 C10 C11 . . . . -93.1(4) ?
    C3 C4 C12 C14 . . . . -107.3(2) ?
    C4A C4 C12 C14 . . . . 72.4(2) ?
    C3 C4 C12 C13 . . . . 127.0(2) ?
    C4A C4 C12 C13 . . . . -53.3(3) ?
    C14 C12 C13 O4 . . . . -2.6(3) ?
    C4 C12 C13 O4 . . . . 123.9(2) ?
    C14 C12 C13 N3 . . . . 178.1(2) ?
    C4 C12 C13 N3 . . . . -55.5(3) ?
    C2 N1 C15 C16 . . . . 89.3(3) ?
    C8A N1 C15 C16 . . . . -90.8(3) ?
    N1 C15 C16 C17 . . . . 176.4(3) ?
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
    N3 H3NA O1 2_655 0.86 2.30 2.904(3) 127.9 yes
    N3 H3NB O1 1_655 0.86 2.05 2.908(3) 177.7 yes
data_global
_journal_date_recd_electronic     2006-09-11
_journal_date_accepted     2006-10-28
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue     12
_journal_page_first     o5386
_journal_page_last     o5387
_journal_paper_category     EO
_journal_coeditor_code     YA2028
_publ_contact_author_name     'Shishkina, S. V.'
_publ_contact_author_address
; STC "Institute for Single Crystals"
 National Academy of Sciences of Ukraine
 60 Lenina ave.
 Kharkiv 61001
 Ukraine
;
_publ_contact_author_email     sveta@xray.isc.kharkov.com
_publ_contact_author_fax     '+(380) 57-3409343'
_publ_contact_author_phone     '+(380) 57-3410258'
_publ_section_title
;\
Ethyl
4-(2-amino-1-cyano-2-oxoethyl)-2-oxo-1-propyl-1,2-dihydroquinoline-3-\
carboxylate
;
loop_
    _publ_author_name
    _publ_author_address
    'Shishkina, Svetlana V.'
;    STC `Institute for Single Crystals'
     National Academy of Sciences of Ukraine
     60 Lenina ave.
     Kharkiv 61001
     Ukraine
;
    'Shishkin, Oleg V.'
;    STC `Institute for Single Crystals'
     National Academy of Sciences of Ukraine
     60 Lenina ave.
     Kharkiv 61001
     Ukraine
;
    'Ukrainets, Igor V.'
;    Department of Pharmaceutical Chemistry
     National University of Pharmacy
     4 Blyukhera ave.
     Kharkiv 61002
     Ukraine
;
    'Bereznyakova, Natalya L.'
;    Department of Pharmaceutical Chemistry
     National University of Pharmacy
     4 Blyukhera ave.
     Kharkiv 61002
     Ukraine
;
