#------------------------------------------------------------------------------
#$Date: 2015-05-13 23:33:03 +0300 (Wed, 13 May 2015) $
#$Revision: 136425 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/99/2019951.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_2019951
loop_
_publ_author_name
'Chantrapromma, Suchada'
'Kaewmanee, Narissara'
'Boonnak, Nawong'
'Chantrapromma, Kan'
'Ghabbour, Hazem A.'
'Fun, Hoong-Kun'
_publ_section_title
;
 Crystal structure of (E)-2-hydroxy-4′-methoxyazastilbene
;
_journal_coeditor_code           SU5124
_journal_issue                   6
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_page_first              571
_journal_paper_doi               10.1107/S2056989015008348
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C14 H13 N O2'
_chemical_formula_moiety         'C14 H13 N O2'
_chemical_formula_sum            'C14 H13 N O2'
_chemical_formula_weight         227.25
_chemical_melting_point_gt       388
_chemical_melting_point_lt       390
_chemical_name_common
;
(E)-2-Hydroxy-4'-methoxyazastilbene
;
_chemical_name_systematic
;
(E)-2-[(4-Methoxybenzylidene)amino]phenol
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 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                 101.3120(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.0357(3)
_cell_length_b                   5.5554(2)
_cell_length_c                   12.8733(5)
_cell_measurement_reflns_used    3449
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.54
_cell_measurement_theta_min      2.58
_cell_volume                     563.52(4)
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF
(Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0116
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26314
_diffrn_reflns_theta_full        30.54
_diffrn_reflns_theta_max         30.54
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9636
_exptl_absorpt_correction_T_min  0.9526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.41
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.278
_refine_ls_extinction_coef       0.054(8)
_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   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         3449
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0366
_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)+(0.0786P)²+0.0298P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.0996
_reflns_number_gt                3414
_reflns_number_total             3449
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su5124sup1.cif
_cod_data_source_block           I
_cod_database_code               2019951
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, 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_symmetry_multiplicity
O O1 0.29289(8) 0.08802(12) 0.07528(5) 0.01815(14) Uani d . 1 1
O O2 0.92146(10) 0.70962(12) 0.58775(6) 0.02323(15) Uani d . 1 1
H H1O2 0.859(2) 0.653(3) 0.5407(15) 0.028(3) Uiso d . 1 1
N N1 0.72131(9) 0.33548(14) 0.53665(5) 0.01630(16) Uani d . 1 1
C C1 0.54115(10) 0.13926(16) 0.38967(6) 0.01455(16) Uani d . 1 1
C C2 0.55623(10) 0.31817(15) 0.31478(7) 0.01598(16) Uani d . 1 1
H H2A 0.6239 0.4524 0.3353 0.019 Uiso calc R 1 1
C C3 0.47132(10) 0.29620(15) 0.21094(7) 0.01586(16) Uani d . 1 1
H H3A 0.4826 0.4149 0.1618 0.019 Uiso calc R 1 1
C C4 0.36790(10) 0.09459(15) 0.17945(6) 0.01416(16) Uani d . 1 1
C C5 0.35026(11) -0.08418(16) 0.25290(6) 0.01607(17) Uani d . 1 1
H H5A 0.2812 -0.2171 0.2326 0.019 Uiso calc R 1 1
C C6 0.43785(11) -0.05985(16) 0.35704(6) 0.01649(16) Uani d . 1 1
H H6A 0.4273 -0.1791 0.4061 0.020 Uiso calc R 1 1
C C7 0.63122(10) 0.15284(17) 0.49969(6) 0.01611(17) Uani d . 1 1
H H7A 0.6229 0.0242 0.5446 0.019 Uiso calc R 1 1
C C8 0.81013(9) 0.34278(15) 0.64262(6) 0.01427(16) Uani d . 1 1
C C9 0.91560(10) 0.54613(15) 0.66557(6) 0.01633(16) Uani d . 1 1
C C10 1.01507(11) 0.57944(17) 0.76609(7) 0.01860(17) Uani d . 1 1
H H10A 1.0854 0.7133 0.7803 0.022 Uiso calc R 1 1
C C11 1.00837(11) 0.41075(16) 0.84506(7) 0.01799(17) Uani d . 1 1
H H11A 1.0752 0.4309 0.9122 0.022 Uiso calc R 1 1
C C12 0.90092(10) 0.21016(17) 0.82364(6) 0.01711(16) Uani d . 1 1
H H12A 0.8951 0.0994 0.8770 0.021 Uiso calc R 1 1
C C13 0.80332(10) 0.17641(15) 0.72308(6) 0.01595(16) Uani d . 1 1
H H13A 0.7331 0.0424 0.7092 0.019 Uiso calc R 1 1
C C14 0.19195(12) -0.11830(17) 0.03898(7) 0.02058(18) Uani d . 1 1
H H14A 0.1551 -0.1096 -0.0365 0.031 Uiso calc R 1 1
H H14B 0.0948 -0.1225 0.0720 0.031 Uiso calc R 1 1
H H14C 0.2582 -0.2615 0.0570 0.031 Uiso calc R 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
C4 O1 C14 117.25(7)
C9 O2 H1O2 101.3(12)
C7 N1 C8 121.55(7)
C6 C1 C2 118.64(7)
C6 C1 C7 118.99(7)
C2 C1 C7 122.36(7)
C3 C2 C1 120.54(7)
C3 C2 H2A 119.7
C1 C2 H2A 119.7
C2 C3 C4 120.07(8)
C2 C3 H3A 120.0
C4 C3 H3A 120.0
O1 C4 C5 124.37(7)
O1 C4 C3 115.38(7)
C5 C4 C3 120.24(7)
C6 C5 C4 118.88(7)
C6 C5 H5A 120.6
C4 C5 H5A 120.6
C5 C6 C1 121.63(8)
C5 C6 H6A 119.2
C1 C6 H6A 119.2
N1 C7 C1 122.48(7)
N1 C7 H7A 118.8
C1 C7 H7A 118.8
C13 C8 C9 118.98(7)
C13 C8 N1 127.73(7)
C9 C8 N1 113.29(7)
O2 C9 C10 119.93(8)
O2 C9 C8 119.18(7)
C10 C9 C8 120.88(7)
C11 C10 C9 119.45(8)
C11 C10 H10A 120.3
C9 C10 H10A 120.3
C10 C11 C12 120.11(8)
C10 C11 H11A 119.9
C12 C11 H11A 119.9
C13 C12 C11 120.24(8)
C13 C12 H12A 119.9
C11 C12 H12A 119.9
C12 C13 C8 120.31(8)
C12 C13 H13A 119.8
C8 C13 H13A 119.8
O1 C14 H14A 109.5
O1 C14 H14B 109.5
H14A C14 H14B 109.5
O1 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.3586(9)
O1 C14 1.4287(10)
O2 C9 1.3599(11)
O2 H1O2 0.772(19)
N1 C7 1.2825(10)
N1 C8 1.4107(10)
C1 C6 1.3972(11)
C1 C2 1.4065(11)
C1 C7 1.4605(10)
C2 C3 1.3818(11)
C2 H2A 0.9300
C3 C4 1.4062(11)
C3 H3A 0.9300
C4 C5 1.3975(11)
C5 C6 1.3932(11)
C5 H5A 0.9300
C6 H6A 0.9300
C7 H7A 0.9300
C8 C13 1.3973(11)
C8 C9 1.4084(11)
C9 C10 1.3935(11)
C10 C11 1.3915(13)
C10 H10A 0.9300
C11 C12 1.4035(12)
C11 H11A 0.9300
C12 C13 1.3884(11)
C12 H12A 0.9300
C13 H13A 0.9300
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 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
O2 H1O2 N1 1_555 0.774(18) 2.078(17) 2.6315(11) 128.7(17) y
C14 H14B O2 2_464 0.96 2.71 3.2876(12) 119 y
C2 H2A Cg2 2_564 0.93 2.93 3.5662(9) 127 y
C13 H13A Cg1 2_555 0.93 2.76 3.4671(9) 134 y
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 -0.41(12)
C7 C1 C2 C3 178.77(7)
C1 C2 C3 C4 0.40(12)
C14 O1 C4 C5 -1.14(12)
C14 O1 C4 C3 177.64(7)
C2 C3 C4 O1 -178.73(7)
C2 C3 C4 C5 0.10(12)
O1 C4 C5 C6 178.14(7)
C3 C4 C5 C6 -0.58(12)
C4 C5 C6 C1 0.57(13)
C2 C1 C6 C5 -0.09(13)
C7 C1 C6 C5 -179.29(7)
C8 N1 C7 C1 -178.67(8)
C6 C1 C7 N1 -176.38(8)
C2 C1 C7 N1 4.45(12)
C7 N1 C8 C13 -6.46(13)
C7 N1 C8 C9 173.81(7)
C13 C8 C9 O2 -179.42(8)
N1 C8 C9 O2 0.34(11)
C13 C8 C9 C10 1.49(12)
N1 C8 C9 C10 -178.75(7)
O2 C9 C10 C11 -179.85(8)
C8 C9 C10 C11 -0.77(13)
C9 C10 C11 C12 -0.61(14)
C10 C11 C12 C13 1.27(13)
C11 C12 C13 C8 -0.54(13)
C9 C8 C13 C12 -0.82(12)
N1 C8 C13 C12 179.45(7)

_cod_database_fobs_code 2019951
