#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/43/2224377.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_2224377
loop_
_publ_author_name
'Ha, Kwang'
'Heo, Joon'
'Kim, Hyung Jin'
_publ_section_title
;
 2-(1-Propyl-2,6-distyryl-1,4-dihydropyridin-4-ylidene)malononitrile
;
_journal_coeditor_code           NG2689
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3131
_journal_paper_doi               10.1107/S1600536809048892
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C27 H23 N3'
_chemical_formula_moiety         'C27 H23 N3'
_chemical_formula_sum            'C27 H23 N3'
_chemical_formula_weight         389.48
_chemical_name_systematic
;
2-(1-Propyl-2,6-distyryl-1,4-dihydropyridin-4-ylidene)malononitrile
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 99.790(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.586(2)
_cell_length_b                   17.827(2)
_cell_length_c                   7.4543(9)
_cell_measurement_reflns_used    690
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.06
_cell_measurement_theta_min      2.49
_cell_volume                     2172.0(4)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART 1000 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  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12600
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         2.28
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.630085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stick
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4433
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1335
_refine_ls_R_factor_gt           0.0610
_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)+(0.0808P)²+0.1288P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1534
_refine_ls_wR_factor_ref         0.2013
_reflns_number_gt                2084
_reflns_number_total             4433
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ng2689.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2171.9(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224377
_cod_database_fobs_code          2224377
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
N N1 0.35774(14) 0.08906(10) 0.2536(3) 0.0713(6) Uani d . 1 . .
N N2 0.3616(3) 0.42152(17) 0.2101(5) 0.1696(17) Uani d . 1 . .
N N3 0.1110(3) 0.3314(2) 0.1271(6) 0.186(2) Uani d . 1 . .
C C1 0.4116(2) 0.14869(13) 0.2691(3) 0.0772(8) Uani d . 1 . .
C C2 0.3815(2) 0.21977(15) 0.2438(4) 0.0889(9) Uani d . 1 . .
H H2 0.4182 0.2596 0.2518 0.107 Uiso calc R 1 . .
C C3 0.2971(3) 0.23522(16) 0.2060(4) 0.0938(10) Uani d . 1 . .
C C4 0.2452(2) 0.17187(15) 0.1836(4) 0.0900(9) Uani d . 1 . .
H H4 0.1889 0.1791 0.1539 0.108 Uiso calc R 1 . .
C C5 0.27456(19) 0.10081(14) 0.2040(4) 0.0780(7) Uani d . 1 . .
C C6 0.49940(19) 0.13383(15) 0.3018(4) 0.0803(8) Uani d . 1 . .
H H6 0.5171 0.0897 0.2545 0.096 Uiso calc R 1 . .
C C7 0.5559(2) 0.17842(14) 0.3937(4) 0.0843(8) Uani d . 1 . .
H H7 0.5369 0.2203 0.4483 0.101 Uiso calc R 1 . .
C C8 0.6446(2) 0.16912(15) 0.4189(4) 0.0828(8) Uani d . 1 . .
C C9 0.6811(2) 0.10774(16) 0.3513(4) 0.0902(9) Uani d . 1 . .
H H9 0.6487 0.0697 0.2918 0.108 Uiso calc R 1 . .
C C10 0.7643(3) 0.1027(2) 0.3714(5) 0.1122(11) Uani d . 1 . .
H H10 0.7879 0.0614 0.3243 0.135 Uiso calc R 1 . .
C C11 0.8137(2) 0.1581(2) 0.4608(5) 0.1264(13) Uani d . 1 . .
H H11 0.8703 0.1547 0.4722 0.152 Uiso calc R 1 . .
C C12 0.7787(3) 0.2177(2) 0.5321(5) 0.1301(14) Uani d . 1 . .
H H12 0.8116 0.2549 0.5942 0.156 Uiso calc R 1 . .
C C13 0.6951(2) 0.22324(18) 0.5128(4) 0.1046(11) Uani d . 1 . .
H H13 0.6720 0.2639 0.5635 0.125 Uiso calc R 1 . .
C C14 0.2655(3) 0.30813(17) 0.1869(4) 0.1153(13) Uani d . 1 . .
C C15 0.3178(3) 0.3705(2) 0.2000(5) 0.1326(16) Uani d . 1 . .
C C16 0.1804(4) 0.3210(2) 0.1529(6) 0.143(2) Uani d . 1 . .
C C17 0.22033(18) 0.03589(15) 0.1665(4) 0.0869(8) Uani d . 1 . .
H H17 0.2284 -0.0049 0.2451 0.104 Uiso calc R 1 . .
C C18 0.1602(2) 0.03298(17) 0.0248(5) 0.0929(9) Uani d . 1 . .
H H18 0.1523 0.0759 -0.0471 0.111 Uiso calc R 1 . .
C C19 0.1048(2) -0.0295(2) -0.0320(6) 0.1017(10) Uani d . 1 . .
C C20 0.0541(2) -0.0257(2) -0.1978(6) 0.1274(13) Uani d . 1 . .
H H20 0.0540 0.0172 -0.2686 0.153 Uiso calc R 1 . .
C C21 0.0036(3) -0.0844(3) -0.2604(8) 0.166(2) Uani d . 1 . .
H H21 -0.0296 -0.0811 -0.3740 0.199 Uiso calc R 1 . .
C C22 0.0015(3) -0.1471(3) -0.1589(12) 0.167(3) Uani d . 1 . .
H H22 -0.0327 -0.1867 -0.2026 0.200 Uiso calc R 1 . .
C C23 0.0501(3) -0.1516(3) 0.0085(10) 0.171(2) Uani d . 1 . .
H H23 0.0485 -0.1942 0.0800 0.206 Uiso calc R 1 . .
C C24 0.1018(2) -0.0927(2) 0.0712(7) 0.1312(13) Uani d . 1 . .
H H24 0.1348 -0.0960 0.1849 0.157 Uiso calc R 1 . .
C C25 0.38929(15) 0.01206(12) 0.2886(3) 0.0690(7) Uani d . 1 . .
H H25A 0.3520 -0.0159 0.3506 0.083 Uiso calc R 1 . .
H H25B 0.4418 0.0142 0.3687 0.083 Uiso calc R 1 . .
C C26 0.39921(16) -0.02907(13) 0.1163(3) 0.0744(7) Uani d . 1 . .
H H26A 0.3472 -0.0299 0.0341 0.089 Uiso calc R 1 . .
H H26B 0.4382 -0.0024 0.0565 0.089 Uiso calc R 1 . .
C C27 0.4281(3) -0.10736(17) 0.1544(5) 0.1335(14) Uani d . 1 . .
H H27A 0.4785 -0.1069 0.2395 0.200 Uiso calc R 1 . .
H H27B 0.4368 -0.1307 0.0432 0.200 Uiso calc R 1 . .
H H27C 0.3876 -0.1350 0.2049 0.200 Uiso calc R 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
C1 N1 C5 . . 120.5(2) ?
C1 N1 C25 . . 119.7(2) ?
C5 N1 C25 . . 119.7(2) ?
C2 C1 N1 . . 119.1(3) ?
C2 C1 C6 . . 121.6(3) ?
N1 C1 C6 . . 119.2(2) ?
C1 C2 C3 . . 122.6(3) ?
C1 C2 H2 . . 118.7 ?
C3 C2 H2 . . 118.7 ?
C14 C3 C2 . . 123.0(4) ?
C14 C3 C4 . . 121.4(4) ?
C2 C3 C4 . . 115.6(3) ?
C5 C4 C3 . . 122.2(3) ?
C5 C4 H4 . . 118.9 ?
C3 C4 H4 . . 118.9 ?
C4 C5 N1 . . 119.7(3) ?
C4 C5 C17 . . 121.3(3) ?
N1 C5 C17 . . 119.0(2) ?
C7 C6 C1 . . 125.1(3) ?
C7 C6 H6 . . 117.5 ?
C1 C6 H6 . . 117.5 ?
C6 C7 C8 . . 127.3(3) ?
C6 C7 H7 . . 116.4 ?
C8 C7 H7 . . 116.4 ?
C9 C8 C13 . . 118.0(3) ?
C9 C8 C7 . . 122.4(3) ?
C13 C8 C7 . . 119.6(3) ?
C10 C9 C8 . . 120.5(3) ?
C10 C9 H9 . . 119.7 ?
C8 C9 H9 . . 119.7 ?
C9 C10 C11 . . 120.8(4) ?
C9 C10 H10 . . 119.6 ?
C11 C10 H10 . . 119.6 ?
C12 C11 C10 . . 119.3(4) ?
C12 C11 H11 . . 120.3 ?
C10 C11 H11 . . 120.3 ?
C11 C12 C13 . . 120.3(3) ?
C11 C12 H12 . . 119.9 ?
C13 C12 H12 . . 119.9 ?
C12 C13 C8 . . 121.0(3) ?
C12 C13 H13 . . 119.5 ?
C8 C13 H13 . . 119.5 ?
C3 C14 C15 . . 120.9(4) ?
C3 C14 C16 . . 121.0(4) ?
C15 C14 C16 . . 118.1(3) ?
N2 C15 C14 . . 179.2(5) ?
N3 C16 C14 . . 179.3(5) ?
C18 C17 C5 . . 122.6(3) ?
C18 C17 H17 . . 118.7 ?
C5 C17 H17 . . 118.7 ?
C17 C18 C19 . . 127.8(3) ?
C17 C18 H18 . . 116.1 ?
C19 C18 H18 . . 116.1 ?
C24 C19 C20 . . 118.1(4) ?
C24 C19 C18 . . 123.1(4) ?
C20 C19 C18 . . 118.8(4) ?
C21 C20 C19 . . 120.9(5) ?
C21 C20 H20 . . 119.5 ?
C19 C20 H20 . . 119.5 ?
C22 C21 C20 . . 120.7(6) ?
C22 C21 H21 . . 119.6 ?
C20 C21 H21 . . 119.6 ?
C21 C22 C23 . . 119.5(5) ?
C21 C22 H22 . . 120.2 ?
C23 C22 H22 . . 120.2 ?
C22 C23 C24 . . 119.8(6) ?
C22 C23 H23 . . 120.1 ?
C24 C23 H23 . . 120.1 ?
C19 C24 C23 . . 120.9(5) ?
C19 C24 H24 . . 119.5 ?
C23 C24 H24 . . 119.5 ?
N1 C25 C26 . . 112.79(19) ?
N1 C25 H25A . . 109.0 ?
C26 C25 H25A . . 109.0 ?
N1 C25 H25B . . 109.0 ?
C26 C25 H25B . . 109.0 ?
H25A C25 H25B . . 107.8 ?
C27 C26 C25 . . 111.8(2) ?
C27 C26 H26A . . 109.3 ?
C25 C26 H26A . . 109.3 ?
C27 C26 H26B . . 109.3 ?
C25 C26 H26B . . 109.3 ?
H26A C26 H26B . . 107.9 ?
C26 C27 H27A . . 109.5 ?
C26 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C26 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
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 C1 . 1.381(3) ?
N1 C5 . 1.382(3) ?
N1 C25 . 1.476(3) ?
N2 C15 . 1.160(5) ?
N3 C16 . 1.148(6) ?
C1 C2 . 1.363(4) ?
C1 C6 . 1.459(4) ?
C2 C3 . 1.408(4) ?
C2 H2 . 0.9300 ?
C3 C14 . 1.399(4) ?
C3 C4 . 1.413(4) ?
C4 C5 . 1.357(3) ?
C4 H4 . 0.9300 ?
C5 C17 . 1.463(4) ?
C6 C7 . 1.327(4) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.461(4) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.386(4) ?
C8 C13 . 1.387(4) ?
C9 C10 . 1.364(4) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.380(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.362(5) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.373(5) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 C15 . 1.402(6) ?
C14 C16 . 1.411(6) ?
C17 C18 . 1.324(4) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.460(4) ?
C18 H18 . 0.9300 ?
C19 C24 . 1.369(5) ?
C19 C20 . 1.373(5) ?
C20 C21 . 1.372(5) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.353(7) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.367(8) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.386(6) ?
C23 H23 . 0.9300 ?
C24 H24 . 0.9300 ?
C25 C26 . 1.512(3) ?
C25 H25A . 0.9700 ?
C25 H25B . 0.9700 ?
C26 C27 . 1.487(3) ?
C26 H26A . 0.9700 ?
C26 H26B . 0.9700 ?
C27 H27A . 0.9600 ?
C27 H27B . 0.9600 ?
C27 H27C . 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 N1 C1 C2 . . . . 3.2(3) ?
C25 N1 C1 C2 . . . . -177.3(2) ?
C5 N1 C1 C6 . . . . -173.3(2) ?
C25 N1 C1 C6 . . . . 6.2(3) ?
N1 C1 C2 C3 . . . . 1.4(4) ?
C6 C1 C2 C3 . . . . 177.8(2) ?
C1 C2 C3 C14 . . . . 177.4(3) ?
C1 C2 C3 C4 . . . . -4.1(4) ?
C14 C3 C4 C5 . . . . -179.1(3) ?
C2 C3 C4 C5 . . . . 2.4(4) ?
C3 C4 C5 N1 . . . . 2.0(4) ?
C3 C4 C5 C17 . . . . -175.2(3) ?
C1 N1 C5 C4 . . . . -4.9(4) ?
C25 N1 C5 C4 . . . . 175.7(2) ?
C1 N1 C5 C17 . . . . 172.3(2) ?
C25 N1 C5 C17 . . . . -7.1(3) ?
C2 C1 C6 C7 . . . . 34.3(4) ?
N1 C1 C6 C7 . . . . -149.3(2) ?
C1 C6 C7 C8 . . . . -175.1(2) ?
C6 C7 C8 C9 . . . . -2.6(4) ?
C6 C7 C8 C13 . . . . 177.1(3) ?
C13 C8 C9 C10 . . . . -2.4(4) ?
C7 C8 C9 C10 . . . . 177.3(3) ?
C8 C9 C10 C11 . . . . 0.6(5) ?
C9 C10 C11 C12 . . . . 1.1(6) ?
C10 C11 C12 C13 . . . . -1.0(6) ?
C11 C12 C13 C8 . . . . -0.8(5) ?
C9 C8 C13 C12 . . . . 2.5(4) ?
C7 C8 C13 C12 . . . . -177.2(3) ?
C2 C3 C14 C15 . . . . 1.7(4) ?
C4 C3 C14 C15 . . . . -176.7(3) ?
C2 C3 C14 C16 . . . . -178.6(3) ?
C4 C3 C14 C16 . . . . 3.0(4) ?
C4 C5 C17 C18 . . . . 41.4(4) ?
N1 C5 C17 C18 . . . . -135.8(3) ?
C5 C17 C18 C19 . . . . 176.8(3) ?
C17 C18 C19 C24 . . . . 8.4(5) ?
C17 C18 C19 C20 . . . . -170.6(3) ?
C24 C19 C20 C21 . . . . -1.8(5) ?
C18 C19 C20 C21 . . . . 177.2(3) ?
C19 C20 C21 C22 . . . . 1.1(7) ?
C20 C21 C22 C23 . . . . 0.4(8) ?
C21 C22 C23 C24 . . . . -1.0(8) ?
C20 C19 C24 C23 . . . . 1.2(5) ?
C18 C19 C24 C23 . . . . -177.8(3) ?
C22 C23 C24 C19 . . . . 0.2(7) ?
C1 N1 C25 C26 . . . . -96.4(3) ?
C5 N1 C25 C26 . . . . 83.0(3) ?
N1 C25 C26 C27 . . . . -177.9(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655957
