#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2223386.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_2223386
loop_
_publ_author_name
'Asiri, Abdullah Mohamed'
'Akkurt, Mehmet'
'Khan, Islam Ullah'
'Arshad, Muhammad N.'
'Khan, Salman A.'
_publ_section_title
;
 (2<i>Z</i>)-2-(4-Methylphenyl)-3-(2-naphthyl)prop-2-enenitrile
;
_journal_coeditor_code           HB5070
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2409
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H15 N'
_chemical_formula_moiety         'C20 H15 N'
_chemical_formula_sum            'C20 H15 N'
_chemical_formula_weight         269.33
_chemical_name_systematic
;
(2<i>Z</i>)-2-(4-Methylphenyl)-3-(2-naphthyl)prop-2-enenitrile
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3194(11)
_cell_length_b                   16.4796(16)
_cell_length_c                   7.2596(7)
_cell_measurement_reflns_used    1202
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.22
_cell_measurement_theta_min      3.31
_cell_volume                     1473.8(2)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0915
_diffrn_reflns_av_sigmaI/netI    0.1160
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16248
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.24
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.206
_refine_ls_abs_structure_Flack   none
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3659
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.950
_refine_ls_R_factor_all          0.1849
_refine_ls_R_factor_gt           0.0583
_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/[\s^2^(Fo^2^)+(0.0732P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1743
_reflns_number_gt                1549
_reflns_number_total             3659
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    hb5070.cif
_[local]_cod_data_source_block   I
_cod_database_code               2223386
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,1/2+z
3 1/2-x,y,1/2+z
4 1/2+x,-y,z
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0474(19) 0.072(3) 0.107(4) -0.0020(18) 0.000(2) -0.009(2)
C1 0.0332(17) 0.047(2) 0.036(2) 0.0056(17) 0.0002(16) -0.0009(19)
C2 0.0332(17) 0.048(2) 0.034(2) 0.0018(16) -0.0001(16) -0.0039(18)
C3 0.0353(17) 0.048(2) 0.028(2) 0.0005(16) -0.0054(16) -0.0042(17)
C4 0.0437(19) 0.047(2) 0.047(3) -0.0043(18) -0.001(2) 0.000(2)
C5 0.058(2) 0.044(2) 0.051(3) -0.005(2) -0.006(2) -0.004(2)
C6 0.056(2) 0.045(2) 0.060(3) 0.006(2) -0.005(2) -0.011(2)
C7 0.042(2) 0.054(3) 0.047(3) 0.0066(19) -0.0003(18) -0.007(2)
C8 0.0392(19) 0.044(2) 0.029(2) 0.0072(17) -0.0026(16) -0.0033(18)
C9 0.0374(19) 0.058(2) 0.039(3) 0.0041(19) 0.0064(18) 0.001(2)
C10 0.0418(19) 0.046(2) 0.040(2) -0.0020(17) 0.0063(17) 0.0063(19)
C11 0.0363(17) 0.046(2) 0.045(2) 0.0053(17) 0.0031(17) -0.0007(19)
C12 0.0411(18) 0.041(2) 0.044(2) -0.0011(17) -0.0014(19) 0.0056(19)
C13 0.0407(19) 0.036(2) 0.050(3) -0.0034(16) -0.0008(18) 0.0054(18)
C14 0.049(2) 0.047(2) 0.067(3) 0.002(2) -0.007(2) -0.006(2)
C15 0.076(3) 0.047(3) 0.067(3) 0.002(2) -0.007(3) -0.005(2)
C16 0.063(3) 0.041(2) 0.061(3) 0.007(2) 0.014(2) 0.008(2)
C17 0.051(2) 0.053(3) 0.082(4) 0.005(2) -0.010(2) 0.000(3)
C18 0.054(2) 0.044(2) 0.065(3) 0.0016(19) -0.010(2) -0.008(2)
C19 0.102(3) 0.058(3) 0.092(4) 0.024(3) 0.017(3) -0.006(3)
C20 0.047(2) 0.051(2) 0.053(3) 0.001(2) 0.005(2) 0.002(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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
N N1 0.2102(3) 0.2374(2) 0.2270(6) 0.0755(18) Uani . . 1.000
C C1 0.4123(2) 0.4123(2) 0.3160(5) 0.0387(11) Uani . . 1.000
C C2 0.4702(2) 0.4813(2) 0.2783(5) 0.0384(11) Uani . . 1.000
C C3 0.4291(3) 0.5598(2) 0.3140(5) 0.0371(11) Uani . . 1.000
C C4 0.4872(3) 0.6316(2) 0.2717(5) 0.0459(14) Uani . . 1.000
C C5 0.4449(3) 0.7059(2) 0.3090(5) 0.0510(14) Uani . . 1.000
C C6 0.3431(3) 0.7129(2) 0.3916(6) 0.0537(14) Uani . . 1.000
C C7 0.2845(3) 0.6454(2) 0.4337(5) 0.0477(16) Uani . . 1.000
C C8 0.3250(3) 0.5669(2) 0.3945(5) 0.0374(11) Uani . . 1.000
C C9 0.2669(3) 0.4948(2) 0.4371(5) 0.0448(14) Uani . . 1.000
C C10 0.3079(3) 0.4205(2) 0.3993(6) 0.0426(11) Uani . . 1.000
C C11 0.4613(2) 0.3337(2) 0.2763(5) 0.0424(11) Uani . . 1.000
C C12 0.4168(2) 0.2602(2) 0.2486(5) 0.0420(11) Uani . . 1.000
C C13 0.4813(3) 0.1865(2) 0.2136(5) 0.0422(14) Uani . . 1.000
C C14 0.4457(3) 0.1283(2) 0.0903(6) 0.0543(14) Uani . . 1.000
C C15 0.5086(3) 0.0608(2) 0.0502(7) 0.0633(17) Uani . . 1.000
C C16 0.6068(3) 0.0487(2) 0.1335(6) 0.0550(16) Uani . . 1.000
C C17 0.6417(3) 0.1063(2) 0.2582(7) 0.0620(18) Uani . . 1.000
C C18 0.5807(3) 0.1741(2) 0.2980(6) 0.0543(14) Uani . . 1.000
C C19 0.6730(4) -0.0271(2) 0.0951(8) 0.0840(19) Uani . . 1.000
C C20 0.3006(3) 0.2492(2) 0.2411(7) 0.0503(14) Uani . . 1.000
H H2 0.53910 0.47630 0.22730 0.0460 Uiso calc R 1.000
H H4 0.55540 0.62770 0.21750 0.0550 Uiso calc R 1.000
H H5 0.48410 0.75230 0.27940 0.0610 Uiso calc R 1.000
H H6 0.31510 0.76400 0.41800 0.0640 Uiso calc R 1.000
H H7 0.21680 0.65090 0.48910 0.0570 Uiso calc R 1.000
H H9 0.19910 0.49870 0.49250 0.0540 Uiso calc R 1.000
H H10 0.26780 0.37440 0.42780 0.0510 Uiso calc R 1.000
H H11 0.53670 0.33460 0.26870 0.0510 Uiso calc R 1.000
H H14 0.37860 0.13450 0.03350 0.0650 Uiso calc R 1.000
H H15 0.48350 0.02310 -0.03500 0.0750 Uiso calc R 1.000
H H17 0.70810 0.09910 0.31690 0.0750 Uiso calc R 1.000
H H18 0.60650 0.21190 0.38240 0.0650 Uiso calc R 1.000
H H19A 0.64500 -0.07140 0.16670 0.1260 Uiso calc R 1.000
H H19B 0.74750 -0.01760 0.12780 0.1260 Uiso calc R 1.000
H H19C 0.66850 -0.04030 -0.03350 0.1260 Uiso calc R 1.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0061 0.0033 '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'
C C 0.0033 0.0016 '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 C1 C10 118.4(3) no
C2 C1 C11 118.8(2) no
C10 C1 C11 122.7(3) no
C1 C2 C3 122.5(3) no
C2 C3 C4 123.0(3) no
C2 C3 C8 118.5(3) no
C4 C3 C8 118.6(3) no
C3 C4 C5 121.1(3) no
C4 C5 C6 120.4(3) no
C5 C6 C7 120.4(3) no
C6 C7 C8 121.0(3) no
C3 C8 C7 118.6(3) no
C3 C8 C9 118.5(3) no
C7 C8 C9 122.9(3) no
C8 C9 C10 121.6(3) no
C1 C10 C9 120.5(3) no
C1 C11 C12 131.4(2) no
C11 C12 C13 123.3(3) no
C11 C12 C20 121.5(3) no
C13 C12 C20 115.1(3) no
C12 C13 C14 120.8(3) no
C12 C13 C18 121.5(3) no
C14 C13 C18 117.7(3) no
C13 C14 C15 121.0(4) no
C14 C15 C16 121.2(4) no
C15 C16 C17 117.7(3) no
C15 C16 C19 121.0(4) no
C17 C16 C19 121.3(4) no
C16 C17 C18 121.7(4) no
C13 C18 C17 120.6(4) no
N1 C20 C12 176.0(5) no
C1 C2 H2 119.00 no
C3 C2 H2 119.00 no
C3 C4 H4 119.00 no
C5 C4 H4 120.00 no
C4 C5 H5 120.00 no
C6 C5 H5 120.00 no
C5 C6 H6 120.00 no
C7 C6 H6 120.00 no
C6 C7 H7 120.00 no
C8 C7 H7 119.00 no
C8 C9 H9 119.00 no
C10 C9 H9 119.00 no
C1 C10 H10 120.00 no
C9 C10 H10 120.00 no
C1 C11 H11 114.00 no
C12 C11 H11 114.00 no
C13 C14 H14 120.00 no
C15 C14 H14 119.00 no
C14 C15 H15 119.00 no
C16 C15 H15 119.00 no
C16 C17 H17 119.00 no
C18 C17 H17 119.00 no
C13 C18 H18 120.00 no
C17 C18 H18 120.00 no
C16 C19 H19A 109.00 no
C16 C19 H19B 110.00 no
C16 C19 H19C 110.00 no
H19A C19 H19B 109.00 no
H19A C19 H19C 109.00 no
H19B C19 H19C 109.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C20 1.135(5) no
C1 C2 1.370(4) no
C1 C10 1.428(5) no
C1 C11 1.458(5) no
C2 C3 1.413(5) no
C3 C4 1.417(5) no
C3 C8 1.414(5) no
C4 C5 1.358(5) no
C5 C6 1.395(5) no
C6 C7 1.361(5) no
C7 C8 1.415(5) no
C8 C9 1.421(5) no
C9 C10 1.353(5) no
C11 C12 1.345(5) no
C12 C13 1.474(5) no
C12 C20 1.444(4) no
C13 C14 1.383(5) no
C13 C18 1.384(5) no
C14 C15 1.387(5) no
C15 C16 1.367(6) no
C16 C17 1.380(6) no
C16 C19 1.518(5) no
C17 C18 1.377(5) no
C2 H2 0.9300 no
C4 H4 0.9300 no
C5 H5 0.9300 no
C6 H6 0.9300 no
C7 H7 0.9300 no
C9 H9 0.9300 no
C10 H10 0.9300 no
C11 H11 0.9300 no
C14 H14 0.9300 no
C15 H15 0.9300 no
C17 H17 0.9300 no
C18 H18 0.9300 no
C19 H19A 0.9600 no
C19 H19B 0.9600 no
C19 H19C 0.9600 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
N1 H10 2.7800 . no
N1 H4 2.9300 4_465 no
N1 H5 2.8200 4_465 no
N1 H19A 2.8800 4_455 no
C5 C13 3.549(5) 2_665 no
C6 C13 3.591(5) 2_665 no
C10 C20 3.049(5) . no
C13 C5 3.549(5) 2_664 no
C13 C6 3.591(5) 2_664 no
C20 C10 3.049(5) . no
C1 H9 3.0700 3_554 no
C1 H4 3.0100 2_665 no
C2 H9 2.9600 3_554 no
C3 H9 2.9900 3_554 no
C3 H2 3.0800 2_665 no
C8 H2 3.0200 2_665 no
C10 H4 2.9700 2_665 no
C11 H18 2.8000 . no
C12 H10 2.9300 . no
C14 H19B 3.0600 4_455 no
C16 H15 2.9000 2_655 no
C17 H15 3.0300 2_655 no
C18 H11 2.7100 . no
C20 H10 2.5000 . no
C20 H14 2.6000 . no
H2 H4 2.5000 . no
H2 H11 2.3500 . no
H2 C3 3.0800 2_664 no
H2 C8 3.0200 2_664 no
H4 H2 2.5000 . no
H4 C1 3.0100 2_664 no
H4 C10 2.9700 2_664 no
H4 N1 2.9300 4_565 no
H5 N1 2.8200 4_565 no
H7 H9 2.5200 . no
H9 H7 2.5200 . no
H9 C1 3.0700 3_555 no
H9 C2 2.9600 3_555 no
H9 C3 2.9900 3_555 no
H10 N1 2.7800 . no
H10 C12 2.9300 . no
H10 C20 2.5000 . no
H11 C18 2.7100 . no
H11 H2 2.3500 . no
H11 H18 2.3500 . no
H14 C20 2.6000 . no
H15 H19C 2.5100 . no
H15 C16 2.9000 2_654 no
H15 C17 3.0300 2_654 no
H17 H19B 2.4100 . no
H18 C11 2.8000 . no
H18 H11 2.3500 . no
H19A N1 2.8800 4_555 no
H19B H17 2.4100 . no
H19B C14 3.0600 4_555 no
H19C H15 2.5100 . no
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
C2 H2 Cg1 2_664 0.93 2.98 3.682(4) 134 yes
C7 H7 Cg2 3_555 0.93 2.93 3.695(4) 140 yes
C9 H9 Cg1 3_555 0.93 2.78 3.473(4) 133 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
C10 C1 C2 C3 -1.8(5) no
C11 C1 C2 C3 -179.5(3) no
C2 C1 C10 C9 1.0(6) no
C11 C1 C10 C9 178.5(4) no
C2 C1 C11 C12 -158.4(4) no
C10 C1 C11 C12 24.1(6) no
C1 C2 C3 C4 -178.5(3) no
C1 C2 C3 C8 1.1(5) no
C2 C3 C4 C5 -179.7(4) no
C8 C3 C4 C5 0.7(5) no
C2 C3 C8 C7 178.8(3) no
C2 C3 C8 C9 0.5(5) no
C4 C3 C8 C7 -1.6(5) no
C4 C3 C8 C9 -179.9(3) no
C3 C4 C5 C6 0.5(6) no
C4 C5 C6 C7 -0.8(6) no
C5 C6 C7 C8 -0.2(6) no
C6 C7 C8 C3 1.4(6) no
C6 C7 C8 C9 179.6(4) no
C3 C8 C9 C10 -1.3(6) no
C7 C8 C9 C10 -179.5(4) no
C8 C9 C10 C1 0.5(6) no
C1 C11 C12 C13 -178.6(4) no
C1 C11 C12 C20 4.9(7) no
C11 C12 C13 C14 -142.5(4) no
C11 C12 C13 C18 35.5(6) no
C20 C12 C13 C14 34.2(5) no
C20 C12 C13 C18 -147.8(4) no
C12 C13 C14 C15 176.8(4) no
C18 C13 C14 C15 -1.3(6) no
C12 C13 C18 C17 -177.5(4) no
C14 C13 C18 C17 0.6(6) no
C13 C14 C15 C16 1.2(6) no
C14 C15 C16 C17 -0.4(6) no
C14 C15 C16 C19 177.4(4) no
C15 C16 C17 C18 -0.3(6) no
C19 C16 C17 C18 -178.1(4) no
C16 C17 C18 C13 0.2(6) no