#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/62/7206248.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7206248
loop_
_publ_author_name
'Zhang, Zhenfeng'
'Wu, Yanbo'
'Zhang, Guisheng'
_publ_section_title
;
 N⋯π and O⋯π interactions rather than
 “directed” hydrogen bonding in the crystal packing of
 ethyl (Z)-2-cyano-3-[(4-alkoxyphenyl)amino]prop-2-enoates
;
_journal_issue                   14
_journal_name_full               CrystEngComm
_journal_page_first              4496
_journal_paper_doi               10.1039/c1ce05199g
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C13 H14 N2 O3'
_chemical_formula_weight         246.26
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                76.294(4)
_cell_angle_beta                 86.681(4)
_cell_angle_gamma                89.165(4)
_cell_formula_units_Z            2
_cell_length_a                   4.4026(14)
_cell_length_b                   10.667(3)
_cell_length_c                   13.823(4)
_cell_measurement_temperature    296(2)
_cell_volume                     629.6(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0168
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4495
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.75
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9861
_exptl_absorpt_correction_T_min  0.9706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2273
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0686P)²+0.0628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1430
_reflns_number_gt                1402
_reflns_number_total             2273
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ce05199g.txt
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7206248
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1345(4) -0.06030(19) 0.80337(14) 0.0474(5) Uani 1 1 d . . .
C2 C -0.2303(5) -0.0715(2) 0.90071(15) 0.0548(5) Uani 1 1 d . . .
H2 H -0.1661 -0.0111 0.9338 0.066 Uiso 1 1 calc R . .
C3 C -0.4197(5) -0.1700(2) 0.95107(15) 0.0567(6) Uani 1 1 d . . .
H3 H -0.4778 -0.1770 1.0179 0.068 Uiso 1 1 calc R . .
C4 C -0.5229(4) -0.25845(19) 0.90210(15) 0.0495(5) Uani 1 1 d . . .
C5 C -0.4341(5) -0.2453(2) 0.80262(15) 0.0558(6) Uani 1 1 d . . .
H5 H -0.5069 -0.3031 0.7686 0.067 Uiso 1 1 calc R . .
C6 C -0.2392(5) -0.1479(2) 0.75293(15) 0.0556(6) Uani 1 1 d . . .
H6 H -0.1786 -0.1411 0.6863 0.067 Uiso 1 1 calc R . .
C13 C -0.7802(6) -0.3829(3) 1.04922(16) 0.0751(7) Uani 1 1 d . . .
H13A H -0.9124 -0.4562 1.0702 0.113 Uiso 1 1 calc R . .
H13B H -0.8795 -0.3084 1.0641 0.113 Uiso 1 1 calc R . .
H13C H -0.5957 -0.3994 1.0839 0.113 Uiso 1 1 calc R . .
C7 C 0.2164(5) 0.06074(19) 0.67062(15) 0.0513(5) Uani 1 1 d . . .
H7 H 0.1833 0.0024 0.6319 0.062 Uiso 1 1 calc R . .
C8 C 0.4181(5) 0.16045(19) 0.63194(15) 0.0524(4) Uani 1 1 d . . .
C9 C 0.4851(5) 0.2554(2) 0.68659(15) 0.0524(4) Uani 1 1 d . . .
C11 C 0.7475(7) 0.4483(2) 0.68695(19) 0.0808(8) Uani 1 1 d . . .
H11A H 0.5645 0.4813 0.7148 0.097 Uiso 1 1 calc R . .
H11B H 0.8767 0.4115 0.7410 0.097 Uiso 1 1 calc R . .
C12 C 0.9073(8) 0.5524(3) 0.6151(2) 0.1046(11) Uani 1 1 d . . .
H12A H 1.0811 0.5179 0.5850 0.157 Uiso 1 1 calc R . .
H12B H 0.9729 0.6155 0.6486 0.157 Uiso 1 1 calc R . .
H12C H 0.7729 0.5922 0.5644 0.157 Uiso 1 1 calc R . .
C10 C 0.5668(5) 0.16478(19) 0.53726(17) 0.0572(6) Uani 1 1 d . . .
N1 N 0.0682(4) 0.04217(16) 0.75786(12) 0.0536(5) Uani 1 1 d . . .
H1 H 0.0969 0.0987 0.7916 0.064 Uiso 1 1 calc R . .
N2 N 0.6885(5) 0.1655(2) 0.46152(16) 0.0855(7) Uani 1 1 d . . .
O3 O -0.7104(3) -0.35995(14) 0.94472(10) 0.0659(5) Uani 1 1 d . . .
O2 O 0.6688(4) 0.34977(14) 0.63474(11) 0.0663(5) Uani 1 1 d . . .
O1 O 0.3862(4) 0.25087(15) 0.77171(11) 0.0753(5) Uani 1 1 d . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.12(19) . . ?
C2 C1 N1 117.95(17) . . ?
C6 C1 N1 122.92(18) . . ?
C1 C2 C3 121.60(19) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C2 C3 C4 119.82(19) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
O3 C4 C3 124.74(18) . . ?
O3 C4 C5 116.43(18) . . ?
C3 C4 C5 118.84(19) . . ?
C6 C5 C4 121.17(19) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 119.41(18) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C7 C8 124.90(18) . . ?
N1 C7 H7 117.5 . . ?
C8 C7 H7 117.6 . . ?
C7 C8 C10 117.89(18) . . ?
C7 C8 C9 121.62(18) . . ?
C10 C8 C9 120.46(18) . . ?
O1 C9 O2 122.91(18) . . ?
O1 C9 C8 123.80(19) . . ?
O2 C9 C8 113.29(17) . . ?
C12 C11 O2 108.0(2) . . ?
C12 C11 H11A 110.1 . . ?
O2 C11 H11A 110.1 . . ?
C12 C11 H11B 110.1 . . ?
O2 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C10 C8 178.5(2) . . ?
C7 N1 C1 127.77(17) . . ?
C7 N1 H1 116.1 . . ?
C1 N1 H1 116.1 . . ?
C4 O3 C13 117.33(17) . . ?
C9 O2 C11 115.71(17) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.365(3) . ?
C1 C6 1.390(3) . ?
C1 N1 1.423(3) . ?
C2 C3 1.377(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9300 . ?
C4 O3 1.367(2) . ?
C4 C5 1.383(3) . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C13 O3 1.423(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C7 N1 1.311(2) . ?
C7 C8 1.382(3) . ?
C7 H7 0.9300 . ?
C8 C10 1.420(3) . ?
C8 C9 1.442(3) . ?
C9 O1 1.221(2) . ?
C9 O2 1.340(2) . ?
C11 C12 1.461(3) . ?
C11 O2 1.464(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C10 N2 1.147(3) . ?
N1 H1 0.8600 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 2.3(3) . . . . ?
N1 C1 C2 C3 -178.15(18) . . . . ?
C1 C2 C3 C4 -1.7(3) . . . . ?
C2 C3 C4 O3 179.82(18) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
O3 C4 C5 C6 -178.46(18) . . . . ?
C3 C4 C5 C6 1.7(3) . . . . ?
C4 C5 C6 C1 -1.1(3) . . . . ?
C2 C1 C6 C5 -0.9(3) . . . . ?
N1 C1 C6 C5 179.55(18) . . . . ?
N1 C7 C8 C10 178.2(2) . . . . ?
N1 C7 C8 C9 0.2(3) . . . . ?
C7 C8 C9 O1 4.6(3) . . . . ?
C10 C8 C9 O1 -173.3(2) . . . . ?
C7 C8 C9 O2 -175.57(18) . . . . ?
C10 C8 C9 O2 6.4(3) . . . . ?
C7 C8 C10 N2 -49(9) . . . . ?
C9 C8 C10 N2 129(9) . . . . ?
C8 C7 N1 C1 -177.84(19) . . . . ?
C2 C1 N1 C7 170.65(19) . . . . ?
C6 C1 N1 C7 -9.8(3) . . . . ?
C3 C4 O3 C13 -6.3(3) . . . . ?
C5 C4 O3 C13 173.90(19) . . . . ?
O1 C9 O2 C11 0.4(3) . . . . ?
C8 C9 O2 C11 -179.35(19) . . . . ?
C12 C11 O2 C9 -171.4(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2272280
