#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/22/2222260.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_2222260
loop_
_publ_author_name
'Tanak, Hasan'
'Bingöl Alpaslan, Yelda'
'Yavuz, Metin'
'Ağar, Erbil'
'Erşahin, Ferda'
'Büyükgüngör, Orhan'
_publ_section_title
;
 2-[(2,4-Dimethylphenyl)iminomethyl]-3,5-dimethoxyphenol
;
_journal_coeditor_code           CI2808
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1572
_journal_paper_doi               10.1107/S1600536809021278
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C17 H19 N O3'
_chemical_formula_moiety         'C17 H19 N O3'
_chemical_formula_sum            'C17 H19 N O3'
_chemical_formula_weight         285.33
_chemical_name_systematic
;
2-[(2,4-Dimethylphenyl)iminomethyl]-3,5-dimethoxyphenol
;
_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                 97.542(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.7070(2)
_cell_length_b                   11.283(5)
_cell_length_c                   28.216(5)
_cell_measurement_reflns_used    10962
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.15
_cell_measurement_theta_min      1.46
_cell_volume                     1485.6(7)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Stoe IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            13316
_diffrn_reflns_theta_full        25.63
_diffrn_reflns_theta_max         25.63
_diffrn_reflns_theta_min         1.46
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9939
_exptl_absorpt_correction_T_min  0.9771
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.670
_exptl_crystal_size_mid          0.313
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.092
_refine_diff_density_min         -0.144
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2797
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0599P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1106
_reflns_number_gt                1808
_reflns_number_total             2797
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2808.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222260
_cod_database_fobs_code          2222260
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 -0.1970(3) 0.07461(10) 0.06735(5) 0.0759(4) Uani d . 1 . .
H H1A -0.0686 0.0847 0.0896 0.114 Uiso calc PR 0.62(3) . .
O O2 -0.3588(3) 0.47471(10) 0.10480(4) 0.0735(4) Uani d . 1 . .
O O3 -0.9431(3) 0.29177(10) -0.02381(4) 0.0721(4) Uani d . 1 . .
N N1 0.1167(3) 0.18286(12) 0.13482(5) 0.0584(4) Uani d . 1 . .
H H1B 0.0796 0.1207 0.1175 0.070 Uiso calc PR 0.38(3) . .
C C1 -0.2694(3) 0.27691(13) 0.08638(6) 0.0534(4) Uani d . 1 . .
C C2 -0.3428(4) 0.17509(14) 0.05865(6) 0.0580(4) Uani d . 1 . .
C C3 -0.5703(4) 0.17634(14) 0.02150(6) 0.0610(5) Uani d . 1 . .
H H3 -0.6186 0.1085 0.0035 0.073 Uiso calc R 1 . .
C C4 -0.7208(3) 0.27934(14) 0.01202(6) 0.0569(4) Uani d . 1 . .
C C5 -0.6564(4) 0.38249(14) 0.03878(6) 0.0593(4) Uani d . 1 . .
H H5 -0.7616 0.4515 0.0317 0.071 Uiso calc R 1 . .
C C6 -0.4362(3) 0.38028(13) 0.07557(6) 0.0553(4) Uani d . 1 . .
C C7 -0.0392(3) 0.27603(14) 0.12467(6) 0.0565(4) Uani d . 1 . .
H H7 -0.0002 0.3443 0.1428 0.068 Uiso calc R 1 . .
C C8 0.3450(3) 0.17699(14) 0.17280(6) 0.0555(4) Uani d . 1 . .
C C9 0.4693(3) 0.06605(15) 0.18298(6) 0.0590(4) Uani d . 1 . .
C C10 0.6896(4) 0.05720(16) 0.22082(6) 0.0657(5) Uani d . 1 . .
H H10 0.7713 -0.0168 0.2279 0.079 Uiso calc R 1 . .
C C11 0.7925(4) 0.15256(17) 0.24829(6) 0.0655(5) Uani d . 1 . .
C C12 0.6723(4) 0.26180(17) 0.23629(7) 0.0694(5) Uani d . 1 . .
H H12 0.7412 0.3283 0.2536 0.083 Uiso calc R 1 . .
C C13 0.4512(4) 0.27460(16) 0.19910(6) 0.0661(5) Uani d . 1 . .
H H13 0.3736 0.3492 0.1918 0.079 Uiso calc R 1 . .
C C14 0.3707(4) -0.04062(15) 0.15315(7) 0.0758(6) Uani d . 1 . .
H H14A 0.4782 -0.1089 0.1653 0.114 Uiso calc R 1 . .
H H14B 0.4005 -0.0269 0.1206 0.114 Uiso calc R 1 . .
H H14C 0.1706 -0.0540 0.1546 0.114 Uiso calc R 1 . .
C C15 1.0290(4) 0.1388(2) 0.28958(7) 0.0865(6) Uani d . 1 . .
H H15A 0.9977 0.1930 0.3146 0.130 Uiso calc PR 0.50 . .
H H15B 1.2103 0.1555 0.2789 0.130 Uiso calc PR 0.50 . .
H H15C 1.0293 0.0590 0.3015 0.130 Uiso calc PR 0.50 . .
H H15D 1.1605 0.0787 0.2821 0.130 Uiso calc PR 0.50 . .
H H15E 0.9479 0.1162 0.3177 0.130 Uiso calc PR 0.50 . .
H H15F 1.1289 0.2127 0.2952 0.130 Uiso calc PR 0.50 . .
C C16 -0.5298(4) 0.57876(15) 0.09754(7) 0.0788(6) Uani d . 1 . .
H H16A -0.4572 0.6380 0.1204 0.118 Uiso calc R 1 . .
H H16B -0.7242 0.5602 0.1015 0.118 Uiso calc R 1 . .
H H16C -0.5232 0.6082 0.0658 0.118 Uiso calc R 1 . .
C C17 -1.0150(5) 0.19050(17) -0.05323(8) 0.0852(7) Uani d . 1 . .
H H17A -1.1735 0.2093 -0.0770 0.128 Uiso calc R 1 . .
H H17B -1.0670 0.1261 -0.0339 0.128 Uiso calc R 1 . .
H H17C -0.8529 0.1679 -0.0686 0.128 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 H1A . . 109.5 ?
C6 O2 C16 . . 117.08(12) ?
C4 O3 C17 . . 116.70(13) ?
C7 N1 C8 . . 123.93(15) ?
C7 N1 H1B . . 118.0 ?
C8 N1 H1B . . 118.0 ?
C2 C1 C6 . . 117.64(14) ?
C2 C1 C7 . . 121.47(14) ?
C6 C1 C7 . . 120.88(14) ?
O1 C2 C3 . . 118.22(14) ?
O1 C2 C1 . . 120.65(14) ?
C3 C2 C1 . . 121.13(14) ?
C4 C3 C2 . . 118.77(15) ?
C4 C3 H3 . . 120.6 ?
C2 C3 H3 . . 120.6 ?
O3 C4 C3 . . 124.01(14) ?
O3 C4 C5 . . 113.93(13) ?
C3 C4 C5 . . 122.06(14) ?
C6 C5 C4 . . 118.92(14) ?
C6 C5 H5 . . 120.5 ?
C4 C5 H5 . . 120.5 ?
O2 C6 C5 . . 124.00(14) ?
O2 C6 C1 . . 114.55(13) ?
C5 C6 C1 . . 121.46(15) ?
N1 C7 C1 . . 121.77(15) ?
N1 C7 H7 . . 119.1 ?
C1 C7 H7 . . 119.1 ?
C13 C8 C9 . . 119.42(15) ?
C13 C8 N1 . . 123.59(15) ?
C9 C8 N1 . . 116.99(14) ?
C10 C9 C8 . . 118.20(16) ?
C10 C9 C14 . . 121.02(15) ?
C8 C9 C14 . . 120.76(14) ?
C11 C10 C9 . . 123.23(17) ?
C11 C10 H10 . . 118.4 ?
C9 C10 H10 . . 118.4 ?
C10 C11 C12 . . 117.21(16) ?
C10 C11 C15 . . 121.56(18) ?
C12 C11 C15 . . 121.23(18) ?
C11 C12 C13 . . 121.49(17) ?
C11 C12 H12 . . 119.3 ?
C13 C12 H12 . . 119.3 ?
C8 C13 C12 . . 120.38(17) ?
C8 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
C9 C14 H14A . . 109.5 ?
C9 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C9 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C11 C15 H15A . . 109.5 ?
C11 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C11 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C11 C15 H15D . . 109.5 ?
H15A C15 H15D . . 141.1 ?
H15B C15 H15D . . 56.3 ?
H15C C15 H15D . . 56.3 ?
C11 C15 H15E . . 109.5 ?
H15A C15 H15E . . 56.3 ?
H15B C15 H15E . . 141.1 ?
H15C C15 H15E . . 56.3 ?
H15D C15 H15E . . 109.5 ?
C11 C15 H15F . . 109.5 ?
H15A C15 H15F . . 56.3 ?
H15B C15 H15F . . 56.3 ?
H15C C15 H15F . . 141.1 ?
H15D C15 H15F . . 109.5 ?
H15E C15 H15F . . 109.5 ?
O2 C16 H16A . . 109.5 ?
O2 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O2 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
O3 C17 H17A . . 109.5 ?
O3 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
O3 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
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 C2 . 1.3312(18) ?
O1 H1A . 0.82 ?
O2 C6 . 1.3673(19) ?
O2 C16 . 1.4229(19) ?
O3 C4 . 1.3634(18) ?
O3 C17 . 1.427(2) ?
N1 C7 . 1.293(2) ?
N1 C8 . 1.4159(19) ?
N1 H1B . 0.86 ?
C1 C2 . 1.407(2) ?
C1 C6 . 1.416(2) ?
C1 C7 . 1.426(2) ?
C2 C3 . 1.397(2) ?
C3 C4 . 1.369(2) ?
C3 H3 . 0.93 ?
C4 C5 . 1.399(2) ?
C5 C6 . 1.367(2) ?
C5 H5 . 0.93 ?
C7 H7 . 0.93 ?
C8 C13 . 1.384(2) ?
C8 C9 . 1.396(2) ?
C9 C10 . 1.391(2) ?
C9 C14 . 1.507(2) ?
C10 C11 . 1.376(3) ?
C10 H10 . 0.93 ?
C11 C12 . 1.380(3) ?
C11 C15 . 1.510(2) ?
C12 C13 . 1.385(2) ?
C12 H12 . 0.93 ?
C13 H13 . 0.93 ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 0.96 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
C15 H15D . 0.96 ?
C15 H15E . 0.96 ?
C15 H15F . 0.96 ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 0.96 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1A N1 0.82 1.820(10) 2.561(2) 149
N1 H1B O1 0.86 1.860(10) 2.561(2) 136.730(10)
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
C6 C1 C2 O1 . . . . -179.15(16) ?
C7 C1 C2 O1 . . . . -0.4(3) ?
C6 C1 C2 C3 . . . . 0.6(3) ?
C7 C1 C2 C3 . . . . 179.39(17) ?
O1 C2 C3 C4 . . . . -179.62(16) ?
C1 C2 C3 C4 . . . . 0.6(3) ?
C17 O3 C4 C3 . . . . -1.3(3) ?
C17 O3 C4 C5 . . . . 178.46(17) ?
C2 C3 C4 O3 . . . . 178.77(17) ?
C2 C3 C4 C5 . . . . -0.9(3) ?
O3 C4 C5 C6 . . . . -179.76(16) ?
C3 C4 C5 C6 . . . . 0.0(3) ?
C16 O2 C6 C5 . . . . 3.4(3) ?
C16 O2 C6 C1 . . . . -176.22(17) ?
C4 C5 C6 O2 . . . . -178.32(16) ?
C4 C5 C6 C1 . . . . 1.3(3) ?
C2 C1 C6 O2 . . . . 178.09(15) ?
C7 C1 C6 O2 . . . . -0.7(2) ?
C2 C1 C6 C5 . . . . -1.6(3) ?
C7 C1 C6 C5 . . . . 179.61(16) ?
C8 N1 C7 C1 . . . . -179.15(15) ?
C2 C1 C7 N1 . . . . 1.8(3) ?
C6 C1 C7 N1 . . . . -179.44(15) ?
C7 N1 C8 C13 . . . . -9.1(3) ?
C7 N1 C8 C9 . . . . 172.11(16) ?
C13 C8 C9 C10 . . . . 2.6(3) ?
N1 C8 C9 C10 . . . . -178.54(15) ?
C13 C8 C9 C14 . . . . -176.31(17) ?
N1 C8 C9 C14 . . . . 2.6(2) ?
C8 C9 C10 C11 . . . . -0.7(3) ?
C14 C9 C10 C11 . . . . 178.17(18) ?
C9 C10 C11 C12 . . . . -1.5(3) ?
C9 C10 C11 C15 . . . . 179.01(18) ?
C10 C11 C12 C13 . . . . 1.9(3) ?
C15 C11 C12 C13 . . . . -178.59(18) ?
C9 C8 C13 C12 . . . . -2.2(3) ?
N1 C8 C13 C12 . . . . 178.98(17) ?
C11 C12 C13 C8 . . . . -0.1(3) ?
