#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/12/2221243.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_2221243
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Kia, Reza'
'Kargar, Hadi'
'Jamshidvand, Arezoo'
_publ_section_title
;
 N,N'-Bis(2-hydroxy-3-ethoxybenzylidene)butane-1,4-diamine
;
_journal_coeditor_code           AT2734
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o706
_journal_paper_doi               10.1107/S1600536809007545
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C22 H28 N2 O4'
_chemical_formula_moiety         'C22 H28 N2 O4'
_chemical_formula_sum            'C22 H28 N2 O4'
_chemical_formula_weight         384.46
_chemical_name_systematic
;
N,N'-Bis(2-hydroxy-3-ethoxybenzylidene)butane-1,4-diamine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.779(2)
_cell_angle_beta                 99.908(2)
_cell_angle_gamma                101.239(2)
_cell_formula_units_Z            1
_cell_length_a                   6.8647(2)
_cell_length_b                   6.9052(2)
_cell_length_c                   10.8083(3)
_cell_measurement_reflns_used    2475
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.35
_cell_measurement_theta_min      2.45
_cell_volume                     493.23(3)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL  (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector diffractometer
;
_diffrn_measurement_method       'φ and ω scans'
_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  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0410
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8962
_diffrn_reflns_theta_full        30.40
_diffrn_reflns_theta_max         30.40
_diffrn_reflns_theta_min         1.92
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9938
_exptl_absorpt_correction_T_min  0.9610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             206
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.266
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2954
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0491
_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)+(0.0681P)²+0.0470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1308
_reflns_number_gt                2157
_reflns_number_total             2954
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2734.cif
_cod_data_source_block           I
_cod_original_cell_volume        493.23(2)
_cod_database_code               2221243
_cod_database_fobs_code          2221243
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.69496(13) 0.51130(12) 0.23213(9) 0.0191(2) Uani d . 1 . .
H H1 0.5792 0.4902 0.1870 0.029 Uiso calc R 1 . .
O O2 1.05734(12) 0.52787(12) 0.36073(8) 0.0178(2) Uani d . 1 . .
N N1 0.35928(15) 0.30726(15) 0.10848(10) 0.0181(2) Uani d . 1 . .
C C1 0.75200(17) 0.33702(16) 0.25124(11) 0.0149(2) Uani d . 1 . .
C C2 0.94642(17) 0.34181(16) 0.32117(11) 0.0157(2) Uani d . 1 . .
C C3 1.00920(18) 0.16571(17) 0.34438(12) 0.0177(2) Uani d . 1 . .
H H3A 1.1398 0.1690 0.3921 0.021 Uiso calc R 1 . .
C C4 0.88179(18) -0.01729(17) 0.29812(12) 0.0188(3) Uani d . 1 . .
H H4A 0.9259 -0.1372 0.3146 0.023 Uiso calc R 1 . .
C C5 0.69162(18) -0.02237(17) 0.22845(12) 0.0178(2) Uani d . 1 . .
H H5A 0.6058 -0.1462 0.1964 0.021 Uiso calc R 1 . .
C C6 0.62455(17) 0.15406(16) 0.20476(11) 0.0157(2) Uani d . 1 . .
C C7 0.42169(18) 0.14831(17) 0.13323(11) 0.0169(2) Uani d . 1 . .
H H7A 0.3346 0.0238 0.1046 0.020 Uiso calc R 1 . .
C C8 0.15522(17) 0.29668(17) 0.03663(12) 0.0185(3) Uani d . 1 . .
H H8A 0.0561 0.2041 0.0735 0.022 Uiso calc R 1 . .
H H8B 0.1478 0.2459 -0.0517 0.022 Uiso calc R 1 . .
C C9 0.10389(17) 0.50109(17) 0.03934(11) 0.0170(2) Uani d . 1 . .
H H9A 0.2076 0.5946 0.0065 0.020 Uiso calc R 1 . .
H H9B 0.1064 0.5488 0.1276 0.020 Uiso calc R 1 . .
C C10 1.26442(17) 0.54481(17) 0.42136(12) 0.0182(3) Uani d . 1 . .
H H10A 1.3370 0.4755 0.3676 0.022 Uiso calc R 1 . .
H H10B 1.2713 0.4857 0.5032 0.022 Uiso calc R 1 . .
C C11 1.35712(19) 0.76329(19) 0.44083(13) 0.0227(3) Uani d . 1 . .
H H11A 1.5003 0.7823 0.4795 0.034 Uiso calc R 1 . .
H H11B 1.2866 0.8291 0.4964 0.034 Uiso calc R 1 . .
H H11C 1.3448 0.8205 0.3593 0.034 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
C1 O1 H1 . . 109.5 ?
C2 O2 C10 . . 117.43(9) ?
C7 N1 C8 . . 120.11(11) ?
O1 C1 C6 . . 122.32(10) ?
O1 C1 C2 . . 118.03(10) ?
C6 C1 C2 . . 119.65(10) ?
O2 C2 C3 . . 125.83(11) ?
O2 C2 C1 . . 114.48(9) ?
C3 C2 C1 . . 119.70(11) ?
C2 C3 C4 . . 120.70(11) ?
C2 C3 H3A . . 119.7 ?
C4 C3 H3A . . 119.7 ?
C5 C4 C3 . . 119.72(11) ?
C5 C4 H4A . . 120.1 ?
C3 C4 H4A . . 120.1 ?
C4 C5 C6 . . 120.48(11) ?
C4 C5 H5A . . 119.8 ?
C6 C5 H5A . . 119.8 ?
C5 C6 C1 . . 119.75(10) ?
C5 C6 C7 . . 120.42(11) ?
C1 C6 C7 . . 119.83(10) ?
N1 C7 C6 . . 121.38(11) ?
N1 C7 H7A . . 119.3 ?
C6 C7 H7A . . 119.3 ?
N1 C8 C9 . . 109.97(10) ?
N1 C8 H8A . . 109.7 ?
C9 C8 H8A . . 109.7 ?
N1 C8 H8B . . 109.7 ?
C9 C8 H8B . . 109.7 ?
H8A C8 H8B . . 108.2 ?
C8 C9 C9 . 2_565 111.80(13) ?
C8 C9 H9A . . 109.3 ?
C9 C9 H9A 2_565 . 109.3 ?
C8 C9 H9B . . 109.3 ?
C9 C9 H9B 2_565 . 109.3 ?
H9A C9 H9B . . 107.9 ?
O2 C10 C11 . . 106.44(9) ?
O2 C10 H10A . . 110.4 ?
C11 C10 H10A . . 110.4 ?
O2 C10 H10B . . 110.4 ?
C11 C10 H10B . . 110.4 ?
H10A C10 H10B . . 108.6 ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 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 C1 . 1.3507(12) ?
O1 H1 . 0.8400 ?
O2 C2 . 1.3662(13) ?
O2 C10 . 1.4391(13) ?
N1 C7 . 1.2776(14) ?
N1 C8 . 1.4666(14) ?
C1 C6 . 1.4037(16) ?
C1 C2 . 1.4096(16) ?
C2 C3 . 1.3871(15) ?
C3 C4 . 1.4033(17) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.3833(16) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.4036(15) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.4641(15) ?
C7 H7A . 0.9500 ?
C8 C9 . 1.5201(15) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C9 2_565 1.527(2) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C11 . 1.5081(17) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
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 H1 N1 . 0.8400 1.8200 2.5638(14) 147.00 y
C5 H5A O1 1_545 0.9500 2.5900 3.2268(14) 125.00 y
C11 H11B Cg1 2_766 0.9800 2.9600 3.5403(15) 145.00 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
C10 O2 C2 C3 . . . . 6.39(17) ?
C10 O2 C2 C1 . . . . -173.76(10) ?
O1 C1 C2 O2 . . . . -0.84(16) ?
C6 C1 C2 O2 . . . . 179.55(10) ?
O1 C1 C2 C3 . . . . 179.02(10) ?
C6 C1 C2 C3 . . . . -0.60(17) ?
O2 C2 C3 C4 . . . . -179.65(11) ?
C1 C2 C3 C4 . . . . 0.51(18) ?
C2 C3 C4 C5 . . . . 0.10(18) ?
C3 C4 C5 C6 . . . . -0.61(18) ?
C4 C5 C6 C1 . . . . 0.51(18) ?
C4 C5 C6 C7 . . . . -178.73(11) ?
O1 C1 C6 C5 . . . . -179.51(11) ?
C2 C1 C6 C5 . . . . 0.09(17) ?
O1 C1 C6 C7 . . . . -0.25(17) ?
C2 C1 C6 C7 . . . . 179.35(10) ?
C8 N1 C7 C6 . . . . -179.99(10) ?
C5 C6 C7 N1 . . . . -178.57(11) ?
C1 C6 C7 N1 . . . . 2.18(18) ?
C7 N1 C8 C9 . . . . 170.13(11) ?
N1 C8 C9 C9 . . . 2_565 177.44(12) ?
C2 O2 C10 C11 . . . . 173.37(10) ?
