#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/68/2236848.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_2236848
loop_
_publ_author_name
'Smits, Rufus'
'Belyakov, Sergey'
'Vigante, Brigita'
'Duburs, Gunars'
_publ_section_title
;
 Methyl
 6-oxo-4-phenyl-2-[(Z)-2-(pyridin-2-yl)ethenyl]-1,4,5,6-tetrahydropyridine-3-carboxylate
;
_journal_coeditor_code           CV5365
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3489
_journal_paper_doi               10.1107/S1600536812048532
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C20 H18 N2 O3'
_chemical_formula_moiety         'C20 H18 N2 O3'
_chemical_formula_sum            'C20 H18 N2 O3'
_chemical_formula_weight         334.36
_chemical_melting_point          504
_chemical_name_systematic
;
Methyl 6-oxo-4-phenyl-2-[(Z)-2-(pyridin-2-yl)ethenyl]-
1,4,5,6-tetrahydropyridine-3-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 96.5018(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.5746(2)
_cell_length_b                   16.4083(6)
_cell_length_c                   18.0930(8)
_cell_measurement_reflns_used    2317
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      0.9
_cell_volume                     1644.32(11)
_computing_data_collection       'KappaCCD (Nonius, 1999)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'maXus (Mackay et al., 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_sigmaI/netI    0.0823
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7024
_diffrn_reflns_theta_full        28.6
_diffrn_reflns_theta_max         28.6
_diffrn_reflns_theta_min         1.6
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.217
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         4206
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.1197
_refine_ls_R_factor_gt           0.0603
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0562P)²+0.7901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1489
_reflns_number_gt                2483
_reflns_number_total             4206
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cv5365.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2236848
_cod_database_fobs_code          2236848
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
N N1 0.3841(3) 0.31397(11) 0.68159(10) 0.0317(4) Uani d . 1 1
H H1 0.249(4) 0.3452(16) 0.6900(13) 0.050(7) Uiso d . 1 1
C C2 0.4865(4) 0.26644(13) 0.73871(12) 0.0343(5) Uani d . 1 1
C C3 0.7199(4) 0.22630(13) 0.72613(12) 0.0349(5) Uani d . 1 1
H H3A 0.7385 0.1771 0.7559 0.042 Uiso calc R 1 1
H H3B 0.8519 0.2626 0.7433 0.042 Uiso calc R 1 1
C C4 0.7383(3) 0.20413(12) 0.64446(11) 0.0281(5) Uani d . 1 1
H H4 0.910(4) 0.1941(13) 0.6403(11) 0.030(5) Uiso d . 1 1
C C5 0.6556(3) 0.27567(12) 0.59458(11) 0.0275(4) Uani d . 1 1
C C6 0.4830(3) 0.32727(12) 0.61506(11) 0.0281(4) Uani d . 1 1
O O7 0.3935(3) 0.26137(10) 0.79683(9) 0.0471(4) Uani d . 1 1
C C8 0.6075(3) 0.12466(12) 0.62263(11) 0.0266(4) Uani d . 1 1
C C9 0.7212(4) 0.05100(13) 0.64153(13) 0.0357(5) Uani d . 1 1
H H9 0.8757 0.0510 0.6671 0.043 Uiso calc R 1 1
C C10 0.6078(4) -0.02244(14) 0.62283(14) 0.0429(6) Uani d . 1 1
H H10 0.6862 -0.0712 0.6360 0.052 Uiso calc R 1 1
C C11 0.3794(4) -0.02351(14) 0.58485(13) 0.0442(6) Uani d . 1 1
H H11 0.3044 -0.0728 0.5715 0.053 Uiso calc R 1 1
C C12 0.2630(4) 0.04892(15) 0.56682(13) 0.0411(5) Uani d . 1 1
H H12 0.1078 0.0484 0.5418 0.049 Uiso calc R 1 1
C C13 0.3754(4) 0.12274(13) 0.58566(12) 0.0327(5) Uani d . 1 1
H H13 0.2945 0.1713 0.5734 0.039 Uiso calc R 1 1
C C14 0.7626(4) 0.28495(13) 0.52436(12) 0.0320(5) Uani d . 1 1
O O15 0.7451(4) 0.34235(11) 0.48210(12) 0.0704(6) Uani d . 1 1
O O16 0.8913(3) 0.21953(9) 0.50878(8) 0.0371(4) Uani d . 1 1
C C17 1.0023(4) 0.22380(15) 0.44055(13) 0.0441(6) Uani d . 1 1
H H17A 1.0904 0.1745 0.4344 0.053 Uiso calc R 1 1
H H17B 1.1107 0.2694 0.4426 0.053 Uiso calc R 1 1
H H17C 0.8795 0.2304 0.3993 0.053 Uiso calc R 1 1
C C18 0.3926(4) 0.39772(13) 0.57107(13) 0.0357(5) Uani d . 1 1
H H18 0.468(4) 0.4026(15) 0.5270(14) 0.043(6) Uiso d . 1 1
C C19 0.2314(4) 0.45687(14) 0.58015(13) 0.0378(5) Uani d . 1 1
H H19 0.219(4) 0.4957(15) 0.5424(14) 0.045(7) Uiso d . 1 1
C C20 0.0609(4) 0.47713(12) 0.63325(12) 0.0323(5) Uani d . 1 1
N N21 0.0217(3) 0.42656(10) 0.68919(10) 0.0313(4) Uani d . 1 1
C C22 -0.1441(4) 0.44794(13) 0.73342(12) 0.0348(5) Uani d . 1 1
H H22 -0.1708 0.4131 0.7722 0.042 Uiso calc R 1 1
C C23 -0.2784(4) 0.51884(14) 0.72480(13) 0.0398(5) Uani d . 1 1
H H23 -0.3942 0.5307 0.7564 0.048 Uiso calc R 1 1
C C24 -0.2370(4) 0.57122(14) 0.66859(14) 0.0429(6) Uani d . 1 1
H H24 -0.3229 0.6197 0.6616 0.052 Uiso calc R 1 1
C C25 -0.0651(4) 0.55059(14) 0.62245(13) 0.0400(5) Uani d . 1 1
H H25 -0.0333 0.5855 0.5843 0.048 Uiso calc R 1 1
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C6 124.69(18) n
C2 N1 H1 117.6(15) n
C6 N1 H1 117.2(15) n
O7 C2 N1 120.4(2) n
O7 C2 C3 124.0(2) n
N1 C2 C3 115.55(19) n
C2 C3 C4 113.83(17) n
C2 C3 H3A 108.8 n
C4 C3 H3A 108.8 n
C2 C3 H3B 108.8 n
C4 C3 H3B 108.8 n
H3A C3 H3B 107.7 n
C5 C4 C8 113.75(16) n
C5 C4 C3 109.83(17) n
C8 C4 C3 111.70(16) n
C5 C4 H4 108.5(12) n
C8 C4 H4 106.1(12) n
C3 C4 H4 106.6(12) n
C6 C5 C14 122.53(18) n
C6 C5 C4 119.60(18) n
C14 C5 C4 117.85(17) n
C5 C6 N1 119.77(18) n
C5 C6 C18 123.61(19) n
N1 C6 C18 116.62(18) n
C13 C8 C9 118.24(19) n
C13 C8 C4 122.47(17) n
C9 C8 C4 119.28(17) n
C10 C9 C8 120.9(2) n
C10 C9 H9 119.5 n
C8 C9 H9 119.5 n
C11 C10 C9 120.3(2) n
C11 C10 H10 119.9 n
C9 C10 H10 119.9 n
C12 C11 C10 119.5(2) n
C12 C11 H11 120.3 n
C10 C11 H11 120.3 n
C11 C12 C13 120.5(2) n
C11 C12 H12 119.7 n
C13 C12 H12 119.7 n
C8 C13 C12 120.6(2) n
C8 C13 H13 119.7 n
C12 C13 H13 119.7 n
O15 C14 O16 119.9(2) n
O15 C14 C5 127.9(2) n
O16 C14 C5 112.22(17) n
C14 O16 C17 115.65(17) n
O16 C17 H17A 109.5 n
O16 C17 H17B 109.5 n
H17A C17 H17B 109.5 n
O16 C17 H17C 109.5 n
H17A C17 H17C 109.5 n
H17B C17 H17C 109.5 n
C19 C18 C6 134.3(2) n
C19 C18 H18 114.0(15) n
C6 C18 H18 111.6(15) n
C18 C19 C20 137.4(2) n
C18 C19 H19 113.4(15) n
C20 C19 H19 109.1(15) n
N21 C20 C25 121.03(19) n
N21 C20 C19 121.74(19) n
C25 C20 C19 117.21(19) n
C22 N21 C20 118.07(18) n
N21 C22 C23 123.8(2) n
N21 C22 H22 118.1 n
C23 C22 H22 118.1 n
C24 C23 C22 118.5(2) n
C24 C23 H23 120.8 n
C22 C23 H23 120.8 n
C23 C24 C25 118.8(2) n
C23 C24 H24 120.6 n
C25 C24 H24 120.6 n
C24 C25 C20 119.9(2) n
C24 C25 H25 120.1 n
C20 C25 H25 120.1 n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 1.367(3) n
N1 C6 1.397(3) n
N1 H1 0.94(3) n
C2 O7 1.227(3) n
C2 C3 1.498(3) n
C3 C4 1.537(3) n
C3 H3A 0.9700 n
C3 H3B 0.9700 n
C4 C5 1.520(3) n
C4 C8 1.524(3) n
C4 H4 0.98(2) n
C5 C6 1.364(3) n
C5 C14 1.471(3) n
C6 C18 1.460(3) n
C8 C13 1.388(3) n
C8 C9 1.389(3) n
C9 C10 1.385(3) n
C9 H9 0.9300 n
C10 C11 1.377(3) n
C10 H10 0.9300 n
C11 C12 1.375(3) n
C11 H11 0.9300 n
C12 C13 1.388(3) n
C12 H12 0.9300 n
C13 H13 0.9300 n
C14 O15 1.210(3) n
C14 O16 1.339(2) n
O16 C17 1.444(3) n
C17 H17A 0.9600 n
C17 H17B 0.9600 n
C17 H17C 0.9600 n
C18 C19 1.345(3) n
C18 H18 0.95(2) n
C19 C20 1.465(3) n
C19 H19 0.93(3) n
C20 N21 1.346(3) n
C20 C25 1.398(3) n
N21 C22 1.337(3) n
C22 C23 1.383(3) n
C22 H22 0.9300 n
C23 C24 1.371(3) n
C23 H23 0.9300 n
C24 C25 1.382(3) n
C24 H24 0.9300 n
C25 H25 0.9300 n
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
C25 H25 O15 3_666 0.93 2.42 3.257(3) 150 yes
C24 H24 O7 2_556 0.93 2.49 3.318(3) 149 yes
C13 H13 O16 1_455 0.93 2.54 3.300(3) 139 yes
C19 H19 O15 3_666 0.93(3) 2.71(3) 3.489(3) 142(2) no
C23 H23 Cg 2_556 0.93 2.66 3.480 147 yes
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
C6 N1 C2 O7 176.29(19) n
C6 N1 C2 C3 -0.7(3) n
O7 C2 C3 C4 151.0(2) n
N1 C2 C3 C4 -32.2(3) n
C2 C3 C4 C5 46.1(2) n
C2 C3 C4 C8 -81.1(2) n
C8 C4 C5 C6 95.1(2) n
C3 C4 C5 C6 -30.9(2) n
C8 C4 C5 C14 -83.3(2) n
C3 C4 C5 C14 150.69(18) n
C14 C5 C6 N1 178.39(18) n
C4 C5 C6 N1 0.1(3) n
C14 C5 C6 C18 -1.9(3) n
C4 C5 C6 C18 179.75(18) n
C2 N1 C6 C5 18.1(3) n
C2 N1 C6 C18 -161.56(19) n
C5 C4 C8 C13 -27.0(3) n
C3 C4 C8 C13 98.1(2) n
C5 C4 C8 C9 154.43(19) n
C3 C4 C8 C9 -80.6(2) n
C13 C8 C9 C10 1.1(3) n
C4 C8 C9 C10 179.8(2) n
C8 C9 C10 C11 0.1(3) n
C9 C10 C11 C12 -1.2(3) n
C10 C11 C12 C13 0.9(3) n
C9 C8 C13 C12 -1.4(3) n
C4 C8 C13 C12 179.99(19) n
C11 C12 C13 C8 0.4(3) n
C6 C5 C14 O15 11.9(4) n
C4 C5 C14 O15 -169.8(2) n
C6 C5 C14 O16 -167.78(17) n
C4 C5 C14 O16 10.6(2) n
O15 C14 O16 C17 0.2(3) n
C5 C14 O16 C17 179.93(18) n
C5 C6 C18 C19 -178.3(2) n
N1 C6 C18 C19 1.3(4) n
C6 C18 C19 C20 -4.9(5) n
C18 C19 C20 N21 -5.5(4) n
C18 C19 C20 C25 176.1(3) n
C25 C20 N21 C22 1.1(3) n
C19 C20 N21 C22 -177.3(2) n
C20 N21 C22 C23 0.3(3) n
N21 C22 C23 C24 -1.2(3) n
C22 C23 C24 C25 0.7(3) n
C23 C24 C25 C20 0.6(4) n
N21 C20 C25 C24 -1.6(3) n
C19 C20 C25 C24 176.9(2) n
