#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/93/2229324.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_2229324
loop_
_publ_author_name
'Kim, Young Hyun'
'Kim, Hyung Jin'
'Otgonbaatar, Enkhzul'
'Kwak, Chee-Hun'
_publ_section_title
;
 2-(2-Methyl-6-phenyl-1-propyl-1,4-dihydropyridin-4-ylidene)propanedinitrile
;
_journal_coeditor_code           BQ2278
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o670
_journal_paper_doi               10.1107/S1600536811005587
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C18 H17 N3'
_chemical_formula_moiety         'C18 H17 N3'
_chemical_formula_sum            'C18 H17 N3'
_chemical_formula_weight         275.35
_chemical_name_systematic
;
2-(2-Methyl-6-phenyl-1-propyl-1,4-dihydropyridin-4-ylidene)propanedinitrile
;
_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_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.0000
_cell_angle_beta                 105.707(2)
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   11.5580(7)
_cell_length_b                   9.9179(6)
_cell_length_c                   13.9268(7)
_cell_measurement_reflns_used    15051
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      3.04
_cell_measurement_theta_min      27.45
_cell_volume                     1536.83(15)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 2008)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 2008)'
_computing_data_reduction        'RAPID-AUTO (Rigaku, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID II-S'
_diffrn_measurement_method       ω
_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  0.0773
_diffrn_reflns_av_sigmaI/netI    0.0646
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13505
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         3.04
_diffrn_standards_number         14613
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(RAPID-AUTO; Rigaku, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.195
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3185
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0717
_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)+(0.0522P)²+0.3213P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1339
_reflns_number_gt                2321
_reflns_number_total             3185
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bq2278.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229324
_cod_database_fobs_code          2229324
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_disorder_assembly
_atom_site_disorder_group
C C1 0.86513(14) 0.37654(15) 0.41005(10) 0.0322(4) Uani d . 1 . .
C C2 0.94627(14) 0.43142(16) 0.36078(11) 0.0350(4) Uani d . 1 . .
H H2 1.0277 0.4120 0.3851 0.042 Uiso calc R 1 . .
C C3 0.90918(14) 0.51234(16) 0.27834(11) 0.0345(4) Uani d . 1 . .
C C4 0.70719(14) 0.49082(15) 0.28609(10) 0.0311(4) Uani d . 1 . .
C C5 0.74344(14) 0.41302(16) 0.36931(11) 0.0332(4) Uani d . 1 . .
H H5 0.6864 0.3829 0.4004 0.040 Uiso calc R 1 . .
C C6 0.57636(14) 0.51915(15) 0.24329(11) 0.0325(4) Uani d . 1 . .
C C7 0.51068(15) 0.45459(18) 0.15657(12) 0.0402(4) Uani d . 1 . .
H H7 0.5498 0.3993 0.1214 0.048 Uiso calc R 1 . .
C C8 0.38795(16) 0.4724(2) 0.12290(13) 0.0466(4) Uani d . 1 . .
H H8 0.3443 0.4281 0.0657 0.056 Uiso calc R 1 . .
C C9 0.32989(16) 0.55609(19) 0.17404(13) 0.0467(5) Uani d . 1 . .
H H9 0.2473 0.5686 0.1506 0.056 Uiso calc R 1 . .
C C10 0.39303(17) 0.62090(19) 0.25902(14) 0.0478(5) Uani d . 1 . .
H H10 0.3534 0.6773 0.2931 0.057 Uiso calc R 1 . .
C C11 0.51660(15) 0.60193(18) 0.29407(12) 0.0409(4) Uani d . 1 . .
H H11 0.5594 0.6452 0.3521 0.049 Uiso calc R 1 . .
C C12 0.90262(14) 0.28936(16) 0.49335(11) 0.0357(4) Uani d . 1 . .
C C13 0.82087(16) 0.24072(17) 0.54461(12) 0.0399(4) Uani d . 1 . .
C C14 1.02361(17) 0.24658(18) 0.52802(12) 0.0436(4) Uani d . 1 . .
C C15 0.74831(15) 0.63071(16) 0.15180(11) 0.0366(4) Uani d . 1 . .
H H15A 0.6704 0.5997 0.1122 0.044 Uiso calc R 1 . .
H H15B 0.8041 0.6235 0.1110 0.044 Uiso calc R 1 . .
C C16 0.73834(19) 0.77697(18) 0.17897(12) 0.0481(5) Uani d . 1 . .
H H16A 0.8174 0.8115 0.2129 0.058 Uiso calc R 1 . .
H H16B 0.6877 0.7844 0.2241 0.058 Uiso calc R 1 . .
C C17 0.6847(2) 0.8605(2) 0.08532(15) 0.0669(6) Uani d . 1 . .
H H17A 0.6826 0.9537 0.1032 0.100 Uiso calc R 1 . .
H H17B 0.6045 0.8298 0.0542 0.100 Uiso calc R 1 . .
H H17C 0.7333 0.8503 0.0397 0.100 Uiso calc R 1 . .
C C18 0.99893(17) 0.5697(2) 0.22903(14) 0.0500(5) Uani d . 1 . .
H H18A 0.9884 0.6655 0.2224 0.075 Uiso calc R 1 . .
H H18B 0.9869 0.5300 0.1642 0.075 Uiso calc R 1 . .
H H18C 1.0788 0.5500 0.2690 0.075 Uiso calc R 1 . .
N N1 0.78979(11) 0.54168(13) 0.24021(9) 0.0320(3) Uani d . 1 . .
N N2 0.75433(16) 0.20179(18) 0.58685(12) 0.0569(5) Uani d . 1 . .
N N3 1.12223(16) 0.2122(2) 0.55469(12) 0.0672(5) Uani d . 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'
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 C1 C5 . . 115.20(13) ?
C2 C1 C12 . . 122.45(14) ?
C5 C1 C12 . . 122.34(14) ?
C3 C2 C1 . . 122.29(15) ?
C3 C2 H2 . . 118.9 ?
C1 C2 H2 . . 118.9 ?
N1 C3 C2 . . 120.21(14) ?
N1 C3 C18 . . 119.37(14) ?
C2 C3 C18 . . 120.42(15) ?
C5 C4 N1 . . 120.64(14) ?
C5 C4 C6 . . 119.44(13) ?
N1 C4 C6 . . 119.92(12) ?
C4 C5 C1 . . 122.03(14) ?
C4 C5 H5 . . 119.0 ?
C1 C5 H5 . . 119.0 ?
C11 C6 C7 . . 118.97(15) ?
C11 C6 C4 . . 119.92(14) ?
C7 C6 C4 . . 120.90(14) ?
C8 C7 C6 . . 120.24(16) ?
C8 C7 H7 . . 119.9 ?
C6 C7 H7 . . 119.9 ?
C7 C8 C9 . . 120.04(16) ?
C7 C8 H8 . . 120.0 ?
C9 C8 H8 . . 120.0 ?
C10 C9 C8 . . 120.53(17) ?
C10 C9 H9 . . 119.7 ?
C8 C9 H9 . . 119.7 ?
C9 C10 C11 . . 119.70(16) ?
C9 C10 H10 . . 120.1 ?
C11 C10 H10 . . 120.1 ?
C6 C11 C10 . . 120.52(15) ?
C6 C11 H11 . . 119.7 ?
C10 C11 H11 . . 119.7 ?
C13 C12 C14 . . 117.32(14) ?
C13 C12 C1 . . 121.55(14) ?
C14 C12 C1 . . 121.13(15) ?
N2 C13 C12 . . 179.5(2) ?
N3 C14 C12 . . 178.88(18) ?
N1 C15 C16 . . 113.11(12) ?
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 ?
C15 C16 C17 . . 110.33(14) ?
C15 C16 H16A . . 109.6 ?
C17 C16 H16A . . 109.6 ?
C15 C16 H16B . . 109.6 ?
C17 C16 H16B . . 109.6 ?
H16A C16 H16B . . 108.1 ?
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 ?
C3 C18 H18A . . 109.5 ?
C3 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C3 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C3 N1 C4 . . 119.59(12) ?
C3 N1 C15 . . 120.88(13) ?
C4 N1 C15 . . 119.51(13) ?
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 C2 . 1.412(2) ?
C1 C5 . 1.414(2) ?
C1 C12 . 1.417(2) ?
C2 C3 . 1.371(2) ?
C2 H2 . 0.9300 ?
C3 N1 . 1.369(2) ?
C3 C18 . 1.502(2) ?
C4 C5 . 1.361(2) ?
C4 N1 . 1.3801(19) ?
C4 C6 . 1.494(2) ?
C5 H5 . 0.9300 ?
C6 C11 . 1.384(2) ?
C6 C7 . 1.396(2) ?
C7 C8 . 1.380(2) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.380(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.371(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.391(2) ?
C10 H10 . 0.9300 ?
C11 H11 . 0.9300 ?
C12 C13 . 1.414(2) ?
C12 C14 . 1.415(2) ?
C13 N2 . 1.154(2) ?
C14 N3 . 1.151(2) ?
C15 N1 . 1.4852(18) ?
C15 C16 . 1.511(2) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 C17 . 1.527(2) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
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
C5 C1 C2 C3 . . . . -1.1(2) ?
C12 C1 C2 C3 . . . . 177.93(14) ?
C1 C2 C3 N1 . . . . -0.6(2) ?
C1 C2 C3 C18 . . . . 179.35(15) ?
N1 C4 C5 C1 . . . . -2.5(2) ?
C6 C4 C5 C1 . . . . 176.43(14) ?
C2 C1 C5 C4 . . . . 2.6(2) ?
C12 C1 C5 C4 . . . . -176.36(14) ?
C5 C4 C6 C11 . . . . 69.6(2) ?
N1 C4 C6 C11 . . . . -111.43(17) ?
C5 C4 C6 C7 . . . . -105.08(17) ?
N1 C4 C6 C7 . . . . 73.9(2) ?
C11 C6 C7 C8 . . . . -0.6(2) ?
C4 C6 C7 C8 . . . . 174.15(15) ?
C6 C7 C8 C9 . . . . 1.1(3) ?
C7 C8 C9 C10 . . . . -0.7(3) ?
C8 C9 C10 C11 . . . . -0.1(3) ?
C7 C6 C11 C10 . . . . -0.2(2) ?
C4 C6 C11 C10 . . . . -175.04(15) ?
C9 C10 C11 C6 . . . . 0.6(3) ?
C2 C1 C12 C13 . . . . 176.88(15) ?
C5 C1 C12 C13 . . . . -4.2(2) ?
C2 C1 C12 C14 . . . . -3.7(2) ?
C5 C1 C12 C14 . . . . 175.28(15) ?
N1 C15 C16 C17 . . . . -174.92(16) ?
C2 C3 N1 C4 . . . . 0.9(2) ?
C18 C3 N1 C4 . . . . -179.09(15) ?
C2 C3 N1 C15 . . . . 179.15(14) ?
C18 C3 N1 C15 . . . . -0.8(2) ?
C5 C4 N1 C3 . . . . 0.7(2) ?
C6 C4 N1 C3 . . . . -178.28(13) ?
C5 C4 N1 C15 . . . . -177.62(13) ?
C6 C4 N1 C15 . . . . 3.4(2) ?
C16 C15 N1 C3 . . . . -93.10(18) ?
C16 C15 N1 C4 . . . . 85.16(18) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656511
