#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/12/2231254.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_2231254
loop_
_publ_author_name
'Swaminathan, K.'
'Sethusankar, K.'
'Murugan, G.'
'Bakthadoss, M.'
_publ_section_title
;
 (E)-2-(2-Formylphenoxymethyl)-3-phenylprop-2-enenitrile
;
_journal_coeditor_code           PV2417
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2000
_journal_paper_doi               10.1107/S1600536811025670
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C17 H13 N O2'
_chemical_formula_moiety         'C17 H13 N O2'
_chemical_formula_sum            'C17 H13 N O2'
_chemical_formula_weight         263.28
_chemical_name_systematic
;
(E)-2-(2-Formylphenoxymethyl)-3-phenylprop-2-enenitrile
;
_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                68.283(2)
_cell_angle_beta                 73.432(2)
_cell_angle_gamma                79.804(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0157(4)
_cell_length_b                   9.2589(4)
_cell_length_c                   10.2348(5)
_cell_measurement_reflns_used    2628
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.97
_cell_measurement_theta_min      0.991
_cell_volume                     674.20(6)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       '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  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12600
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         2.64
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.174
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0367
_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)+(0.0528P)²+0.0828P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.1016
_reflns_number_gt                2162
_reflns_number_total             2628
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2417.cif
_cod_data_source_block           I
_cod_database_code               2231254
_cod_database_fobs_code          2231254
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C C1 0.26890(18) 0.64113(15) 0.64335(14) 0.0532(3) Uani d . 1 1
H H1 0.3008 0.6132 0.7305 0.064 Uiso calc R 1 1
C C2 0.2241(2) 0.79493(15) 0.57315(15) 0.0595(4) Uani d . 1 1
H H2 0.2270 0.8700 0.6125 0.071 Uiso calc R 1 1
C C3 0.17519(19) 0.83824(15) 0.44570(16) 0.0602(4) Uani d . 1 1
H H3 0.1450 0.9425 0.3981 0.072 Uiso calc R 1 1
C C4 0.1710(2) 0.72668(16) 0.38826(16) 0.0648(4) Uani d . 1 1
H H4 0.1372 0.7556 0.3017 0.078 Uiso calc R 1 1
C C5 0.21649(18) 0.57237(15) 0.45793(15) 0.0570(3) Uani d . 1 1
H H5 0.2129 0.4980 0.4180 0.068 Uiso calc R 1 1
C C6 0.26761(15) 0.52628(13) 0.58692(13) 0.0449(3) Uani d . 1 1
C C7 0.31669(16) 0.36612(13) 0.66887(13) 0.0468(3) Uani d . 1 1
H H7 0.3373 0.3542 0.7574 0.056 Uiso calc R 1 1
C C8 0.33774(15) 0.23310(13) 0.64123(13) 0.0462(3) Uani d . 1 1
C C9 0.31738(18) 0.22202(14) 0.51102(15) 0.0543(3) Uani d . 1 1
C C10 0.38224(15) 0.08068(13) 0.74939(14) 0.0486(3) Uani d . 1 1
H H10A 0.4728 0.0193 0.7021 0.058 Uiso calc R 1 1
H H10B 0.4233 0.0975 0.8227 0.058 Uiso calc R 1 1
C C11 0.23087(14) -0.14432(12) 0.91208(12) 0.0385(3) Uani d . 1 1
C C12 0.37770(16) -0.21887(14) 0.96098(14) 0.0496(3) Uani d . 1 1
H H12 0.4804 -0.1690 0.9277 0.059 Uiso calc R 1 1
C C13 0.37016(19) -0.36785(15) 1.05952(15) 0.0582(4) Uani d . 1 1
H H13 0.4686 -0.4175 1.0935 0.070 Uiso calc R 1 1
C C14 0.2212(2) -0.44558(15) 1.10927(14) 0.0586(4) Uani d . 1 1
H H14 0.2196 -0.5474 1.1741 0.070 Uiso calc R 1 1
C C15 0.07545(17) -0.37049(14) 1.06170(13) 0.0497(3) Uani d . 1 1
H H15 -0.0262 -0.4218 1.0954 0.060 Uiso calc R 1 1
C C16 0.07657(14) -0.21887(13) 0.96393(11) 0.0395(3) Uani d . 1 1
C C17 -0.08123(16) -0.14054(16) 0.91668(14) 0.0534(3) Uani d . 1 1
H H17 -0.0751 -0.0399 0.8497 0.064 Uiso calc R 1 1
N N1 0.3060(2) 0.20353(14) 0.40992(15) 0.0774(4) Uani d . 1 1
O O1 0.22458(10) 0.00245(9) 0.81342(9) 0.0484(2) Uani d . 1 1
O O2 -0.21885(12) -0.19734(13) 0.95850(12) 0.0737(3) Uani d . 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
C2 C1 C6 121.36(12)
C2 C1 H1 119.3
C6 C1 H1 119.3
C3 C2 C1 120.28(12)
C3 C2 H2 119.9
C1 C2 H2 119.9
C2 C3 C4 119.54(12)
C2 C3 H3 120.2
C4 C3 H3 120.2
C3 C4 C5 120.40(13)
C3 C4 H4 119.8
C5 C4 H4 119.8
C4 C5 C6 120.90(12)
C4 C5 H5 119.6
C6 C5 H5 119.6
C5 C6 C1 117.51(11)
C5 C6 C7 124.85(11)
C1 C6 C7 117.62(11)
C8 C7 C6 132.27(12)
C8 C7 H7 113.9
C6 C7 H7 113.9
C7 C8 C9 124.29(11)
C7 C8 C10 121.16(11)
C9 C8 C10 114.54(10)
N1 C9 C8 175.55(14)
O1 C10 C8 106.15(9)
O1 C10 H10A 110.5
C8 C10 H10A 110.5
O1 C10 H10B 110.5
C8 C10 H10B 110.5
H10A C10 H10B 108.7
O1 C11 C12 123.92(10)
O1 C11 C16 115.88(9)
C12 C11 C16 120.20(10)
C13 C12 C11 119.10(12)
C13 C12 H12 120.4
C11 C12 H12 120.4
C14 C13 C12 121.87(12)
C14 C13 H13 119.1
C12 C13 H13 119.1
C15 C14 C13 118.78(12)
C15 C14 H14 120.6
C13 C14 H14 120.6
C14 C15 C16 121.20(12)
C14 C15 H15 119.4
C16 C15 H15 119.4
C15 C16 C11 118.81(11)
C15 C16 C17 120.15(11)
C11 C16 C17 121.04(10)
O2 C17 C16 124.38(12)
O2 C17 H17 117.8
C16 C17 H17 117.8
C11 O1 C10 118.29(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3719(18)
C1 C6 1.3879(17)
C1 H1 0.9300
C2 C3 1.3656(19)
C2 H2 0.9300
C3 C4 1.3735(19)
C3 H3 0.9300
C4 C5 1.3758(18)
C4 H4 0.9300
C5 C6 1.3865(17)
C5 H5 0.9300
C6 C7 1.4555(17)
C7 C8 1.3351(16)
C7 H7 0.9300
C8 C9 1.4298(19)
C8 C10 1.4950(17)
C9 N1 1.1397(17)
C10 O1 1.4324(13)
C10 H10A 0.9700
C10 H10B 0.9700
C11 O1 1.3631(13)
C11 C12 1.3802(16)
C11 C16 1.3945(15)
C12 C13 1.3743(18)
C12 H12 0.9300
C13 C14 1.374(2)
C13 H13 0.9300
C14 C15 1.3684(19)
C14 H14 0.9300
C15 C16 1.3900(16)
C15 H15 0.9300
C16 C17 1.4575(17)
C17 O2 1.2026(15)
C17 H17 0.9300
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
C12 H12 O2 1_655 0.93 2.48 3.2675(17) 143
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
C6 C1 C2 C3 0.6(2)
C1 C2 C3 C4 0.1(2)
C2 C3 C4 C5 -0.3(2)
C3 C4 C5 C6 -0.1(2)
C4 C5 C6 C1 0.8(2)
C4 C5 C6 C7 179.50(13)
C2 C1 C6 C5 -1.04(19)
C2 C1 C6 C7 -179.87(11)
C5 C6 C7 C8 5.5(2)
C1 C6 C7 C8 -175.73(13)
C6 C7 C8 C9 1.5(2)
C6 C7 C8 C10 -177.29(12)
C7 C8 C10 O1 104.09(13)
C9 C8 C10 O1 -74.78(13)
O1 C11 C12 C13 -179.25(11)
C16 C11 C12 C13 0.92(18)
C11 C12 C13 C14 0.9(2)
C12 C13 C14 C15 -1.7(2)
C13 C14 C15 C16 0.54(19)
C14 C15 C16 C11 1.25(17)
C14 C15 C16 C17 -179.03(11)
O1 C11 C16 C15 178.18(10)
C12 C11 C16 C15 -1.98(16)
O1 C11 C16 C17 -1.54(16)
C12 C11 C16 C17 178.30(11)
C15 C16 C17 O2 1.27(19)
C11 C16 C17 O2 -179.01(12)
C12 C11 O1 C10 4.17(16)
C16 C11 O1 C10 -175.99(9)
C8 C10 O1 C11 176.89(9)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656870
