#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/18/2231834.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_2231834
loop_
_publ_author_name
'Ghaemi, Akbar'
'Rayati, Saeed'
'Elahi, Ehsan'
'Ng, Seik Weng'
'Tiekink, Edward R. T.'
_publ_section_title
;
 2-{(1E)-1-[(3-{(E)-[1-(2-Hydroxy-4-methoxyphenyl)ethylidene]amino}-2,2-dimethylpropyl)imino]ethyl}-5-methoxyphenol
;
_journal_coeditor_code           BT5648
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2760
_journal_paper_doi               10.1107/S1600536811038815
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C23 H30 N2 O4'
_chemical_formula_moiety         'C23 H30 N2 O4'
_chemical_formula_sum            'C23 H30 N2 O4'
_chemical_formula_weight         398.49
_chemical_name_systematic
;
2-{(1E)-1-[(3-{(E)-[1-(2-Hydroxy-4-
methoxyphenyl)ethylidene]amino}-2,2-dimethylpropyl)imino]ethyl}-5-methoxyphenol
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m 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            4
_cell_length_a                   10.0764(7)
_cell_length_b                   36.069(2)
_cell_length_c                   5.8322(4)
_cell_measurement_reflns_used    2488
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.4928
_cell_measurement_theta_min      2.2540
_cell_volume                     2119.7(2)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2010)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2010)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2010)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type
'Agilent SuperNova Dual diffractometer with Atlas detector'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            6816
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         3.39
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.79318
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2010)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.179
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2419
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0545
_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)+(0.0642P)²+0.9075P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1474
_refine_ls_wR_factor_ref         0.1551
_reflns_number_gt                1952
_reflns_number_total             2419
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5648.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      ' P n m a '
_cod_database_code               2231834
_cod_database_fobs_code          2231834
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, 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_symmetry_multiplicity
O O1 0.30246(15) 0.64954(4) 0.1933(2) 0.0531(4) Uani d D 1 1
H H1 0.354(3) 0.6654(8) 0.256(6) 0.122(13) Uiso d D 1 1
O O2 0.13785(15) 0.53184(4) 0.4322(3) 0.0574(4) Uani d . 1 1
N N1 0.46777(15) 0.68176(4) 0.4452(3) 0.0419(4) Uani d . 1 1
C C1 0.39243(16) 0.62163(5) 0.5332(3) 0.0352(4) Uani d . 1 1
C C2 0.30646(17) 0.62129(5) 0.3409(3) 0.0372(4) Uani d . 1 1
C C3 0.22205(18) 0.59119(5) 0.3013(3) 0.0409(4) Uani d . 1 1
H H3 0.1682 0.5908 0.1719 0.049 Uiso calc R 1 1
C C4 0.21869(18) 0.56202(5) 0.4543(3) 0.0422(4) Uani d . 1 1
C C5 0.3005(2) 0.56209(5) 0.6471(3) 0.0477(5) Uani d . 1 1
H H5 0.2975 0.5425 0.7506 0.057 Uiso calc R 1 1
C C6 0.38514(19) 0.59118(5) 0.6829(3) 0.0436(4) Uani d . 1 1
H H6 0.4399 0.5908 0.8112 0.052 Uiso calc R 1 1
C C7 0.0463(2) 0.53147(6) 0.2451(5) 0.0660(6) Uani d . 1 1
H H7A -0.0043 0.5089 0.2490 0.099 Uiso calc R 1 1
H H7B 0.0942 0.5329 0.1031 0.099 Uiso calc R 1 1
H H7C -0.0125 0.5523 0.2576 0.099 Uiso calc R 1 1
C C8 0.47861(17) 0.65354(5) 0.5787(3) 0.0360(4) Uani d . 1 1
C C9 0.5749(2) 0.65215(6) 0.7746(4) 0.0538(5) Uani d . 1 1
H H9A 0.6438 0.6701 0.7504 0.081 Uiso calc R 1 1
H H9B 0.6134 0.6278 0.7836 0.081 Uiso calc R 1 1
H H9C 0.5293 0.6576 0.9151 0.081 Uiso calc R 1 1
C C10 0.54167(19) 0.71600(5) 0.4786(4) 0.0460(5) Uani d . 1 1
H H10A 0.6219 0.7153 0.3869 0.055 Uiso calc R 1 1
H H10B 0.5674 0.7181 0.6384 0.055 Uiso calc R 1 1
C C11 0.4589(2) 0.7500 0.4108(4) 0.0342(5) Uani d S 1 2
C C12 0.4327(3) 0.7500 0.1527(4) 0.0441(6) Uani d S 1 2
H H12A 0.5157 0.7500 0.0719 0.066 Uiso calc SR 1 2
H H12B 0.3830 0.7717 0.1121 0.066 Uiso calc PR 0.50 1
H H12C 0.3830 0.7283 0.1121 0.066 Uiso calc PR 0.50 1
C C13 0.3269(3) 0.7500 0.5407(5) 0.0493(7) Uani d S 1 2
H H13A 0.3437 0.7500 0.7027 0.074 Uiso calc SR 1 2
H H13B 0.2770 0.7283 0.5005 0.074 Uiso calc PR 0.50 1
H H13C 0.2770 0.7717 0.5005 0.074 Uiso calc PR 0.50 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_3
_geom_angle
C2 O1 H1 . 103(3)
C4 O2 C7 . 117.70(16)
C8 N1 C10 . 123.15(15)
C6 C1 C2 . 116.94(16)
C6 C1 C8 . 122.15(16)
C2 C1 C8 . 120.81(15)
O1 C2 C3 . 117.90(15)
O1 C2 C1 . 121.50(16)
C3 C2 C1 . 120.60(16)
C4 C3 C2 . 120.01(17)
C4 C3 H3 . 120.0
C2 C3 H3 . 120.0
O2 C4 C3 . 124.15(17)
O2 C4 C5 . 115.47(16)
C3 C4 C5 . 120.38(17)
C6 C5 C4 . 119.53(17)
C6 C5 H5 . 120.2
C4 C5 H5 . 120.2
C5 C6 C1 . 122.50(17)
C5 C6 H6 . 118.8
C1 C6 H6 . 118.8
O2 C7 H7A . 109.5
O2 C7 H7B . 109.5
H7A C7 H7B . 109.5
O2 C7 H7C . 109.5
H7A C7 H7C . 109.5
H7B C7 H7C . 109.5
N1 C8 C1 . 117.46(15)
N1 C8 C9 . 122.87(16)
C1 C8 C9 . 119.67(15)
C8 C9 H9A . 109.5
C8 C9 H9B . 109.5
H9A C9 H9B . 109.5
C8 C9 H9C . 109.5
H9A C9 H9C . 109.5
H9B C9 H9C . 109.5
N1 C10 C11 . 111.42(14)
N1 C10 H10A . 109.3
C11 C10 H10A . 109.3
N1 C10 H10B . 109.3
C11 C10 H10B . 109.3
H10A C10 H10B . 108.0
C12 C11 C13 . 109.7(2)
C12 C11 C10 . 110.34(14)
C13 C11 C10 . 110.17(14)
C12 C11 C10 7_575 110.34(14)
C13 C11 C10 7_575 110.17(14)
C10 C11 C10 7_575 106.04(19)
C11 C12 H12A . 109.5
C11 C12 H12B . 109.5
H12A C12 H12B . 109.5
C11 C12 H12C . 109.5
H12A C12 H12C . 109.5
H12B C12 H12C . 109.5
C11 C13 H13A . 109.5
C11 C13 H13B . 109.5
H13A C13 H13B . 109.5
C11 C13 H13C . 109.5
H13A C13 H13C . 109.5
H13B C13 H13C . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C2 . 1.334(2)
O1 H1 . 0.857(10)
O2 C4 . 1.366(2)
O2 C7 . 1.429(3)
N1 C8 . 1.286(2)
N1 C10 . 1.455(2)
C1 C6 . 1.405(2)
C1 C2 . 1.417(2)
C1 C8 . 1.466(2)
C2 C3 . 1.399(2)
C3 C4 . 1.380(3)
C3 H3 . 0.9300
C4 C5 . 1.394(3)
C5 C6 . 1.369(3)
C5 H5 . 0.9300
C6 H6 . 0.9300
C7 H7A . 0.9600
C7 H7B . 0.9600
C7 H7C . 0.9600
C8 C9 . 1.500(2)
C9 H9A . 0.9600
C9 H9B . 0.9600
C9 H9C . 0.9600
C10 C11 . 1.535(2)
C10 H10A . 0.9700
C10 H10B . 0.9700
C11 C12 . 1.528(3)
C11 C13 . 1.531(3)
C11 C10 7_575 1.535(2)
C12 H12A . 0.9600
C12 H12B . 0.9600
C12 H12C . 0.9600
C13 H13A . 0.9600
C13 H13B . 0.9600
C13 H13C . 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
O1 H1 N1 . 0.857(10) 1.695(17) 2.507(2) 157(4)
C7 H7c Cg1 6_455 0.96 2.75 3.547(2) 141
C9 H9b Cg1 6_556 0.96 2.66 3.456(2) 140
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_4
_geom_torsion
C6 C1 C2 O1 . 177.56(17)
C8 C1 C2 O1 . 1.1(3)
C6 C1 C2 C3 . -2.0(2)
C8 C1 C2 C3 . -178.41(16)
O1 C2 C3 C4 . -177.35(17)
C1 C2 C3 C4 . 2.2(3)
C7 O2 C4 C3 . -3.4(3)
C7 O2 C4 C5 . 176.26(19)
C2 C3 C4 O2 . 178.73(17)
C2 C3 C4 C5 . -0.9(3)
O2 C4 C5 C6 . 179.79(17)
C3 C4 C5 C6 . -0.5(3)
C4 C5 C6 C1 . 0.7(3)
C2 C1 C6 C5 . 0.5(3)
C8 C1 C6 C5 . 176.91(17)
C10 N1 C8 C1 . 176.40(16)
C10 N1 C8 C9 . -3.9(3)
C6 C1 C8 N1 . -172.62(17)
C2 C1 C8 N1 . 3.6(2)
C6 C1 C8 C9 . 7.7(3)
C2 C1 C8 C9 . -176.04(16)
C8 N1 C10 C11 . -144.49(18)
N1 C10 C11 C12 . -66.5(2)
N1 C10 C11 C13 . 54.8(2)
N1 C10 C11 C10 7_575 173.97(11)
