#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/54/2225454.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_2225454
loop_
_publ_author_name
'Eltayeb, Naser Eltaher'
'Teoh, Siang Guan'
'Chantrapromma, Suchada'
'Fun, Hoong-Kun'
_publ_section_title
;
 (E)-4-Allyl-2-[(2-hydroxyphenyl)iminiomethyl]-6-methoxyphenolate
;
_journal_coeditor_code           CI5052
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o934
_journal_page_last               o935
_journal_paper_doi               10.1107/S160053681000838X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H17 N O3'
_chemical_formula_moiety         'C17 H17 N O3'
_chemical_formula_sum            'C17 H17 N O3'
_chemical_formula_weight         283.32
_chemical_name_systematic
;
(E)-4-Allyl-2-[(2-hydroxyphenyl)iminiomethyl]-6-methoxyphenolate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.719(3)
_cell_length_b                   9.1302(16)
_cell_length_c                   20.597(4)
_cell_measurement_reflns_used    4056
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.15
_cell_measurement_theta_min      1.98
_cell_volume                     2768.0(9)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX DUO CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_av_sigmaI/netI    0.0636
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16563
_diffrn_reflns_theta_full        30.15
_diffrn_reflns_theta_max         30.15
_diffrn_reflns_theta_min         1.98
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9982
_exptl_absorpt_correction_T_min  0.9550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.290
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4056
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0522
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0776P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1233
_refine_ls_wR_factor_ref         0.1413
_reflns_number_gt                2744
_reflns_number_total             4056
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5052.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 
;
_cod_database_code               2225454
_cod_database_fobs_code          2225454
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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_disorder_assembly
_atom_site_disorder_group
O O1 0.01450(7) 0.45448(12) 0.30069(5) 0.0161(2) Uani d . 1 . .
H H1O1 -0.0369 0.3930 0.3044 0.024 Uiso d R 1 . .
O O2 0.12030(7) 0.76365(12) 0.20618(6) 0.0180(3) Uani d . 1 . .
O O3 0.15126(7) 0.93837(13) 0.10464(5) 0.0197(3) Uani d . 1 . .
N N1 0.18381(8) 0.56151(14) 0.28699(6) 0.0135(3) Uani d . 1 . .
C C1 0.07946(9) 0.39626(16) 0.33947(7) 0.0135(3) Uani d . 1 . .
C C2 0.06178(10) 0.28421(18) 0.38347(8) 0.0167(3) Uani d . 1 . .
C C3 0.13112(11) 0.22677(18) 0.42119(8) 0.0186(3) Uani d . 1 . .
C C4 0.21898(11) 0.28105(18) 0.41570(8) 0.0177(3) Uani d . 1 . .
C C5 0.23708(10) 0.39363(17) 0.37262(8) 0.0153(3) Uani d . 1 . .
C C6 0.16809(10) 0.45100(16) 0.33395(7) 0.0136(3) Uani d . 1 . .
C C7 0.26375(10) 0.60410(17) 0.26593(7) 0.0145(3) Uani d . 1 . .
C C8 0.27799(9) 0.71113(16) 0.21797(7) 0.0133(3) Uani d . 1 . .
C C9 0.36954(10) 0.74371(17) 0.20005(8) 0.0150(3) Uani d . 1 . .
C C10 0.38828(10) 0.84469(17) 0.15316(8) 0.0166(3) Uani d . 1 . .
C C11 0.31474(11) 0.91227(17) 0.12006(8) 0.0166(3) Uani d . 1 . .
C C12 0.22584(10) 0.88183(16) 0.13544(8) 0.0147(3) Uani d . 1 . .
C C13 0.20324(10) 0.78420(16) 0.18785(7) 0.0139(3) Uani d . 1 . .
C C14 0.16825(13) 1.03310(19) 0.05078(9) 0.0221(4) Uani d . 1 . .
C C15 0.48556(11) 0.8797(2) 0.13422(9) 0.0207(4) Uani d . 1 . .
C C16 0.52342(10) 0.77196(19) 0.08627(8) 0.0188(3) Uani d . 1 . .
C C17 0.55487(11) 0.8048(2) 0.02828(9) 0.0244(4) Uani d . 1 . .
H H2 0.0021(12) 0.247(2) 0.3859(8) 0.015(4) Uiso d . 1 . .
H H3 0.1195(13) 0.144(2) 0.4528(9) 0.025(5) Uiso d . 1 . .
H H4 0.2678(14) 0.238(2) 0.4435(10) 0.031(5) Uiso d . 1 . .
H H5 0.2969(13) 0.435(2) 0.3707(9) 0.023(5) Uiso d . 1 . .
H H7 0.3152(12) 0.5554(19) 0.2862(8) 0.015(4) Uiso d . 1 . .
H H9 0.4179(13) 0.6900(19) 0.2254(8) 0.019(5) Uiso d . 1 . .
H H11 0.3273(13) 0.983(2) 0.0852(9) 0.024(5) Uiso d . 1 . .
H H14A 0.1109(14) 1.062(2) 0.0335(10) 0.030(5) Uiso d . 1 . .
H H14B 0.2011(14) 1.124(2) 0.0651(10) 0.034(6) Uiso d . 1 . .
H H14C 0.2072(13) 0.985(2) 0.0176(9) 0.025(5) Uiso d . 1 . .
H H15A 0.5199(14) 0.882(2) 0.1754(10) 0.032(6) Uiso d . 1 . .
H H15C 0.4901(12) 0.982(2) 0.1163(9) 0.015(4) Uiso d . 1 . .
H H16 0.5258(13) 0.672(2) 0.1013(9) 0.029(5) Uiso d . 1 . .
H H17A 0.5552(14) 0.909(2) 0.0120(10) 0.033(5) Uiso d . 1 . .
H H17B 0.5755(15) 0.729(2) -0.0016(10) 0.038(6) Uiso d . 1 . .
H H1N1 0.1343(15) 0.611(2) 0.2647(10) 0.035(6) Uiso d . 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 H1O1 . . 106.5 ?
C12 O3 C14 . . 116.60(12) ?
C7 N1 C6 . . 125.65(13) ?
C7 N1 H1N1 . . 112.1(13) ?
C6 N1 H1N1 . . 122.2(13) ?
O1 C1 C2 . . 122.72(13) ?
O1 C1 C6 . . 117.99(13) ?
C2 C1 C6 . . 119.29(13) ?
C3 C2 C1 . . 120.38(14) ?
C3 C2 H2 . . 121.2(11) ?
C1 C2 H2 . . 118.4(11) ?
C2 C3 C4 . . 120.32(15) ?
C2 C3 H3 . . 121.3(11) ?
C4 C3 H3 . . 118.4(11) ?
C5 C4 C3 . . 119.76(14) ?
C5 C4 H4 . . 121.5(12) ?
C3 C4 H4 . . 118.7(12) ?
C4 C5 C6 . . 120.37(14) ?
C4 C5 H5 . . 119.9(12) ?
C6 C5 H5 . . 119.7(12) ?
C5 C6 C1 . . 119.88(14) ?
C5 C6 N1 . . 122.62(13) ?
C1 C6 N1 . . 117.48(13) ?
N1 C7 C8 . . 124.88(14) ?
N1 C7 H7 . . 114.9(10) ?
C8 C7 H7 . . 120.2(10) ?
C7 C8 C13 . . 121.01(13) ?
C7 C8 C9 . . 117.85(13) ?
C13 C8 C9 . . 121.15(14) ?
C10 C9 C8 . . 120.97(14) ?
C10 C9 H9 . . 123.5(10) ?
C8 C9 H9 . . 115.5(10) ?
C9 C10 C11 . . 118.66(14) ?
C9 C10 C15 . . 121.01(14) ?
C11 C10 C15 . . 120.27(15) ?
C12 C11 C10 . . 121.80(15) ?
C12 C11 H11 . . 118.7(12) ?
C10 C11 H11 . . 119.5(12) ?
O3 C12 C11 . . 125.46(14) ?
O3 C12 C13 . . 113.32(13) ?
C11 C12 C13 . . 121.22(14) ?
O2 C13 C8 . . 122.23(14) ?
O2 C13 C12 . . 121.86(13) ?
C8 C13 C12 . . 115.91(13) ?
O3 C14 H14A . . 107.5(12) ?
O3 C14 H14B . . 110.9(12) ?
H14A C14 H14B . . 108.0(17) ?
O3 C14 H14C . . 111.6(11) ?
H14A C14 H14C . . 111.9(16) ?
H14B C14 H14C . . 106.9(16) ?
C16 C15 C10 . . 112.41(13) ?
C16 C15 H15A . . 113.0(12) ?
C10 C15 H15A . . 105.5(12) ?
C16 C15 H15C . . 109.9(10) ?
C10 C15 H15C . . 110.7(10) ?
H15A C15 H15C . . 105.0(16) ?
C17 C16 C15 . . 125.35(17) ?
C17 C16 H16 . . 119.6(12) ?
C15 C16 H16 . . 115.0(12) ?
C16 C17 H17A . . 121.2(12) ?
C16 C17 H17B . . 121.3(12) ?
H17A C17 H17B . . 117.4(17) ?
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
O1 C1 . 1.3546(17) ?
O1 H1O1 . 0.9454 ?
O2 C13 . 1.2915(17) ?
O3 C12 . 1.3691(18) ?
O3 C14 . 1.429(2) ?
N1 C7 . 1.3129(19) ?
N1 C6 . 1.4168(19) ?
N1 H1N1 . 0.97(2) ?
C1 C2 . 1.391(2) ?
C1 C6 . 1.4015(19) ?
C2 C3 . 1.386(2) ?
C2 H2 . 0.944(18) ?
C3 C4 . 1.390(2) ?
C3 H3 . 1.010(19) ?
C4 C5 . 1.384(2) ?
C4 H4 . 1.00(2) ?
C5 C6 . 1.393(2) ?
C5 H5 . 0.960(19) ?
C7 C8 . 1.405(2) ?
C7 H7 . 0.972(18) ?
C8 C13 . 1.428(2) ?
C8 C9 . 1.4285(19) ?
C9 C10 . 1.363(2) ?
C9 H9 . 1.010(18) ?
C10 C11 . 1.420(2) ?
C10 C15 . 1.518(2) ?
C11 C12 . 1.375(2) ?
C11 H11 . 0.982(19) ?
C12 C13 . 1.439(2) ?
C14 H14A . 0.95(2) ?
C14 H14B . 1.01(2) ?
C14 H14C . 0.99(2) ?
C15 C16 . 1.501(2) ?
C15 H15A . 0.99(2) ?
C15 H15C . 1.003(19) ?
C16 C17 . 1.316(2) ?
C16 H16 . 0.96(2) ?
C17 H17A . 1.01(2) ?
C17 H17B . 0.98(2) ?
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
O1 H1O1 O2 3_545 0.95 1.72 2.6443(16) 166 y
O1 H1O1 O3 3_545 0.95 2.55 3.1268(16) 119 y
N1 H1N1 O2 1_555 0.97(2) 1.85(2) 2.6553(18) 138(2) y
C14 H14B Cg1 8_665 1.01(2) 2.75(2) 3.569(2) 139(2) 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . 178.84(14) ?
C6 C1 C2 C3 . . . . -0.3(2) ?
C1 C2 C3 C4 . . . . 0.3(2) ?
C2 C3 C4 C5 . . . . 0.4(2) ?
C3 C4 C5 C6 . . . . -1.1(2) ?
C4 C5 C6 C1 . . . . 1.1(2) ?
C4 C5 C6 N1 . . . . -177.01(14) ?
O1 C1 C6 C5 . . . . -179.60(14) ?
C2 C1 C6 C5 . . . . -0.4(2) ?
O1 C1 C6 N1 . . . . -1.4(2) ?
C2 C1 C6 N1 . . . . 177.85(13) ?
C7 N1 C6 C5 . . . . 12.8(2) ?
C7 N1 C6 C1 . . . . -165.40(14) ?
C6 N1 C7 C8 . . . . 178.13(14) ?
N1 C7 C8 C13 . . . . 0.3(2) ?
N1 C7 C8 C9 . . . . -179.33(14) ?
C7 C8 C9 C10 . . . . 178.97(14) ?
C13 C8 C9 C10 . . . . -0.6(2) ?
C8 C9 C10 C11 . . . . -3.0(2) ?
C8 C9 C10 C15 . . . . 179.82(14) ?
C9 C10 C11 C12 . . . . 2.0(2) ?
C15 C10 C11 C12 . . . . 179.24(15) ?
C14 O3 C12 C11 . . . . 2.1(2) ?
C14 O3 C12 C13 . . . . -178.25(13) ?
C10 C11 C12 O3 . . . . -177.77(14) ?
C10 C11 C12 C13 . . . . 2.6(2) ?
C7 C8 C13 O2 . . . . 5.1(2) ?
C9 C8 C13 O2 . . . . -175.35(14) ?
C7 C8 C13 C12 . . . . -174.61(14) ?
C9 C8 C13 C12 . . . . 5.0(2) ?
O3 C12 C13 O2 . . . . -5.3(2) ?
C11 C12 C13 O2 . . . . 174.39(14) ?
O3 C12 C13 C8 . . . . 174.40(12) ?
C11 C12 C13 C8 . . . . -5.9(2) ?
C9 C10 C15 C16 . . . . 82.87(19) ?
C11 C10 C15 C16 . . . . -94.28(18) ?
C10 C15 C16 C17 . . . . 121.37(18) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656042
