#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/02/2210281.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_2210281
loop_
_publ_author_name
'Xiao-Yan Yang'
'Ying Li'
'Xiao-Lian He'
'Xue-Mei Li'
'Shu-Sheng Zhang'
_publ_section_title
;
 2-Methoxy-N-[3-(2-nitrophenyl)allylidene]aniline
;
_journal_coeditor_code           HK2093
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3643
_journal_page_last               o3644
_journal_paper_doi               10.1107/S1600536806029217
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C16 H14 N2 O3'
_chemical_formula_moiety         'C16 H14 N2 O3'
_chemical_formula_sum            'C16 H14 N2 O3'
_chemical_formula_weight         282.29
_chemical_name_systematic
;
2-Methoxy-N-[3-(2-nitrophenyl)allylidene]aniline
;
_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                90.00
_cell_angle_beta                 90.706(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.0515(16)
_cell_length_b                   5.0488(6)
_cell_length_c                   20.118(2)
_cell_measurement_reflns_used    2071
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      24.1
_cell_measurement_theta_min      2.5
_cell_volume                     1427.1(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Siemens, 1996)'
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Siemens SMART 1000 CCD area-detector'
_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  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7553
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         1.45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9899
_exptl_absorpt_correction_T_min  0.9631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2807
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0458
_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)+(0.0652P)²+0.1418P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1283
_reflns_number_gt                2042
_reflns_number_total             2807
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2093.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2210281
_cod_database_fobs_code          2210281
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
O O1 0.28620(10) -0.1918(4) 0.41565(9) 0.1187(7) Uani d . 1
O O2 0.38646(11) -0.4750(3) 0.45093(7) 0.0893(5) Uani d . 1
O O3 0.17541(8) 0.8439(2) 0.10452(6) 0.0639(4) Uani d . 1
N N1 0.36702(11) -0.2717(3) 0.42192(7) 0.0658(4) Uani d . 1
N N2 0.19187(9) 0.5246(3) 0.20933(6) 0.0546(4) Uani d . 1
C C1 0.44503(11) -0.1106(3) 0.39505(7) 0.0520(4) Uani d . 1
C C2 0.53250(13) -0.1336(4) 0.42679(8) 0.0637(5) Uani d . 1
H H2A 0.5411 -0.2553 0.4610 0.076 Uiso calc R 1
C C3 0.60640(13) 0.0241(4) 0.40736(9) 0.0692(5) Uani d . 1
H H3A 0.6654 0.0108 0.4286 0.083 Uiso calc R 1
C C4 0.59322(12) 0.2022(4) 0.35645(9) 0.0659(5) Uani d . 1
H H4A 0.6429 0.3118 0.3437 0.079 Uiso calc R 1
C C5 0.50627(11) 0.2180(4) 0.32436(8) 0.0578(4) Uani d . 1
H H5A 0.4991 0.3364 0.2892 0.069 Uiso calc R 1
C C6 0.42849(11) 0.0634(3) 0.34249(7) 0.0499(4) Uani d . 1
C C7 0.33900(11) 0.0828(3) 0.30426(7) 0.0538(4) Uani d . 1
H H7A 0.3013 -0.0683 0.3013 0.065 Uiso calc R 1
C C8 0.30795(11) 0.2982(3) 0.27380(7) 0.0543(4) Uani d . 1
H H8A 0.3436 0.4525 0.2783 0.065 Uiso calc R 1
C C9 0.22210(11) 0.3082(3) 0.23400(7) 0.0525(4) Uani d . 1
H H9A 0.1881 0.1530 0.2262 0.063 Uiso calc R 1
C C10 0.10516(10) 0.5228(3) 0.17227(7) 0.0476(4) Uani d . 1
C C11 0.02780(11) 0.3663(4) 0.18824(8) 0.0597(4) Uani d . 1
H H11A 0.0328 0.2493 0.2238 0.072 Uiso calc R 1
C C12 -0.05654(12) 0.3804(4) 0.15250(10) 0.0691(5) Uani d . 1
H H12A -0.1077 0.2731 0.1637 0.083 Uiso calc R 1
C C13 -0.06419(13) 0.5534(4) 0.10058(10) 0.0728(5) Uani d . 1
H H13A -0.1211 0.5650 0.0766 0.087 Uiso calc R 1
C C14 0.01176(12) 0.7110(4) 0.08334(9) 0.0647(5) Uani d . 1
H H14A 0.0059 0.8265 0.0475 0.078 Uiso calc R 1
C C15 0.09631(10) 0.6988(3) 0.11876(7) 0.0492(4) Uani d . 1
C C16 0.17010(14) 1.0206(4) 0.04932(9) 0.0711(5) Uani d . 1
H H16A 0.2298 1.1112 0.0449 0.107 Uiso calc R 1
H H16B 0.1204 1.1476 0.0564 0.107 Uiso calc R 1
H H16C 0.1566 0.9221 0.0095 0.107 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'
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_publ_flag
C15 O3 C16 117.68(12) yes
O2 N1 O1 122.60(17) yes
O2 N1 C1 118.74(15) yes
O1 N1 C1 118.64(14) yes
C9 N2 C10 118.67(14) yes
C2 C1 C6 122.88(16) ?
C2 C1 N1 116.43(14) yes
C6 C1 N1 120.62(14) ?
C3 C2 C1 119.48(16) ?
C3 C2 H2A 120.3 ?
C1 C2 H2A 120.3 ?
C2 C3 C4 119.84(16) ?
C2 C3 H3A 120.1 ?
C4 C3 H3A 120.1 ?
C3 C4 C5 119.88(17) ?
C3 C4 H4A 120.1 ?
C5 C4 H4A 120.1 ?
C4 C5 C6 122.57(15) ?
C4 C5 H5A 118.7 ?
C6 C5 H5A 118.7 ?
C1 C6 C5 115.31(14) ?
C1 C6 C7 124.99(15) ?
C5 C6 C7 119.62(13) ?
C8 C7 C6 125.02(15) ?
C8 C7 H7A 117.5 ?
C6 C7 H7A 117.5 ?
C7 C8 C9 123.84(16) yes
C7 C8 H8A 118.1 ?
C9 C8 H8A 118.1 ?
N2 C9 C8 121.38(15) yes
N2 C9 H9A 119.3 ?
C8 C9 H9A 119.3 ?
C11 C10 C15 118.55(14) ?
C11 C10 N2 123.54(14) ?
C15 C10 N2 117.83(13) ?
C12 C11 C10 121.41(16) ?
C12 C11 H11A 119.3 ?
C10 C11 H11A 119.3 ?
C13 C12 C11 119.39(16) ?
C13 C12 H12A 120.3 ?
C11 C12 H12A 120.3 ?
C12 C13 C14 120.52(16) ?
C12 C13 H13A 119.7 ?
C14 C13 H13A 119.7 ?
C13 C14 C15 120.58(16) ?
C13 C14 H14A 119.7 ?
C15 C14 H14A 119.7 ?
O3 C15 C14 124.50(14) ?
O3 C15 C10 115.93(12) ?
C14 C15 C10 119.56(14) ?
O3 C16 H16A 109.5 ?
O3 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
O3 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N1 1.2104(18) yes
O2 N1 1.2101(17) yes
O3 C15 1.3645(18) yes
O3 C16 1.4259(19) yes
N1 C1 1.473(2) yes
N2 C9 1.2709(19) yes
N2 C10 1.4206(18) yes
C1 C2 1.383(2) ?
C1 C6 1.392(2) ?
C2 C3 1.370(3) ?
C2 H2A 0.9300 ?
C3 C4 1.374(3) ?
C3 H3A 0.9300 ?
C4 C5 1.377(2) ?
C4 H4A 0.9300 ?
C5 C6 1.395(2) ?
C5 H5A 0.9300 ?
C6 C7 1.469(2) ?
C7 C8 1.320(2) yes
C7 H7A 0.9300 ?
C8 C9 1.441(2) yes
C8 H8A 0.9300 ?
C9 H9A 0.9300 ?
C10 C11 1.385(2) ?
C10 C15 1.400(2) ?
C11 C12 1.380(2) ?
C11 H11A 0.9300 ?
C12 C13 1.365(3) ?
C12 H12A 0.9300 ?
C13 C14 1.379(2) ?
C13 H13A 0.9300 ?
C14 C15 1.379(2) ?
C14 H14A 0.9300 ?
C16 H16A 0.9600 ?
C16 H16B 0.9600 ?
C16 H16C 0.9600 ?
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 H2A O2 3_646 0.93 2.45 3.344(2) 162 yes
C7 H7A O1 1_555 0.93 2.40 2.745(2) 102 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
O2 N1 C1 C2 -26.6(2)
O1 N1 C1 C2 151.44(18)
O2 N1 C1 C6 156.36(16)
O1 N1 C1 C6 -25.6(2)
C6 C1 C2 C3 1.5(3)
N1 C1 C2 C3 -175.46(15)
C1 C2 C3 C4 -0.4(3)
C2 C3 C4 C5 -1.2(3)
C3 C4 C5 C6 1.7(3)
C2 C1 C6 C5 -1.0(2)
N1 C1 C6 C5 175.85(14)
C2 C1 C6 C7 175.68(15)
N1 C1 C6 C7 -7.5(2)
C4 C5 C6 C1 -0.6(2)
C4 C5 C6 C7 -177.47(15)
C1 C6 C7 C8 152.43(17)
C5 C6 C7 C8 -31.0(2)
C6 C7 C8 C9 176.91(14)
C10 N2 C9 C8 -178.04(13)
C7 C8 C9 N2 175.23(16)
C9 N2 C10 C11 36.7(2)
C9 N2 C10 C15 -146.62(15)
C15 C10 C11 C12 0.3(2)
N2 C10 C11 C12 176.97(15)
C10 C11 C12 C13 -0.4(3)
C11 C12 C13 C14 0.7(3)
C12 C13 C14 C15 -0.8(3)
C16 O3 C15 C14 0.2(2)
C16 O3 C15 C10 178.44(14)
C13 C14 C15 O3 178.84(17)
C13 C14 C15 C10 0.6(3)
C11 C10 C15 O3 -178.74(14)
N2 C10 C15 O3 4.4(2)
C11 C10 C15 C14 -0.4(2)
N2 C10 C15 C14 -177.25(14)
