#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/52/2225273.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_2225273
loop_
_publ_author_name
'Wang, Li'
'Sun, Yin-Xia'
'Tong, Jun-Feng'
_publ_section_title
;
 6,6'-Diethoxy-2,2'-[propane-1,3-diyldioxybis(nitrilomethylidyne)]diphenol
;
_journal_coeditor_code           HG2634
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o512
_journal_paper_doi               10.1107/S1600536810003430
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H26 N2 O6'
_chemical_formula_moiety         'C21 H26 N2 O6'
_chemical_formula_sum            'C21 H26 N2 O6'
_chemical_formula_weight         402.44
_chemical_name_systematic
;
6,6'-Diethoxy-2,2'-[propane-1,3-diyldioxybis(nitrilomethylidyne)]diphenol
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_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                   25.292(2)
_cell_length_b                   34.412(3)
_cell_length_c                   4.7176(5)
_cell_measurement_reflns_used    1648
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.296
_cell_measurement_theta_min      2.864
_cell_volume                     4106.0(7)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method       'phi and omega 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  0.0478
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            5348
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9839
_exptl_absorpt_correction_T_min  0.9581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle-like
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.140
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         1031
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0365
_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)+(0.0510P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0897
_reflns_number_gt                817
_reflns_number_total             1031
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            hg2634.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 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        4105.9(7)
_cod_database_code               2225273
_cod_database_fobs_code          2225273
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
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
N N1 0.23158(9) 0.17094(6) 0.6113(5) 0.0506(6) Uani d . 1 . .
O O1 0.21889(7) 0.20179(5) 0.4290(5) 0.0556(5) Uani d . 1 . .
O O2 0.28824(6) 0.11584(5) 0.8533(5) 0.0577(6) Uani d . 1 . .
H H2 0.2826 0.1334 0.7399 0.087 Uiso calc R 1 . .
O O3 0.29360(7) 0.05913(6) 1.2148(5) 0.0613(6) Uani d . 1 . .
C C1 0.26566(10) 0.21504(7) 0.2881(7) 0.0518(7) Uani d . 1 . .
H H1A 0.2796 0.1948 0.1660 0.062 Uiso calc R 1 . .
H H1B 0.2926 0.2220 0.4255 0.062 Uiso calc R 1 . .
C C2 0.2500 0.2500 0.1155(10) 0.0525(10) Uani d S 1 . .
H H2A 0.2794 0.2571 -0.0059 0.063 Uiso calc PR 0.50 . .
H H2B 0.2206 0.2429 -0.0059 0.063 Uiso calc PR 0.50 . .
C C3 0.19084(11) 0.15810(7) 0.7412(6) 0.0485(7) Uani d . 1 . .
H H3 0.1580 0.1692 0.7050 0.058 Uiso calc R 1 . .
C C4 0.19489(10) 0.12638(7) 0.9451(6) 0.0445(7) Uani d . 1 . .
C C5 0.24271(10) 0.10703(7) 0.9928(6) 0.0437(7) Uani d . 1 . .
C C6 0.24500(10) 0.07660(7) 1.1909(6) 0.0456(7) Uani d . 1 . .
C C7 0.20034(10) 0.06695(8) 1.3422(7) 0.0532(7) Uani d . 1 . .
H H7 0.2021 0.0474 1.4782 0.064 Uiso calc R 1 . .
C C8 0.15281(11) 0.08595(8) 1.2947(7) 0.0555(8) Uani d . 1 . .
H H8 0.1228 0.0788 1.3960 0.067 Uiso calc R 1 . .
C C9 0.15006(10) 0.11522(8) 1.0988(7) 0.0514(7) Uani d . 1 . .
H H9 0.1181 0.1278 1.0674 0.062 Uiso calc R 1 . .
C C10 0.29937(10) 0.02900(8) 1.4204(7) 0.0603(9) Uani d . 1 . .
H H10A 0.2739 0.0085 1.3867 0.072 Uiso calc R 1 . .
H H10B 0.2939 0.0392 1.6100 0.072 Uiso calc R 1 . .
C C11 0.35463(10) 0.01383(9) 1.3886(11) 0.0812(12) Uani d . 1 . .
H H11A 0.3609 0.0072 1.1938 0.122 Uiso calc R 1 . .
H H11B 0.3590 -0.0088 1.5048 0.122 Uiso calc R 1 . .
H H11C 0.3793 0.0335 1.4467 0.122 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'
O O 0.0106 0.0060 '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'
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
C3 N1 O1 . . 111.8(2) ?
N1 O1 C1 . . 109.68(18) ?
C5 O2 H2 . . 109.5 ?
C6 O3 C10 . . 117.7(2) ?
O1 C1 C2 . . 106.76(19) ?
O1 C1 H1A . . 110.4 ?
C2 C1 H1A . . 110.4 ?
O1 C1 H1B . . 110.4 ?
C2 C1 H1B . . 110.4 ?
H1A C1 H1B . . 108.6 ?
C1 C2 C1 14 . 114.5(4) ?
C1 C2 H2A 14 . 108.6 ?
C1 C2 H2A . . 108.6 ?
C1 C2 H2B 14 . 108.6 ?
C1 C2 H2B . . 108.6 ?
H2A C2 H2B . . 107.6 ?
N1 C3 C4 . . 121.2(2) ?
N1 C3 H3 . . 119.4 ?
C4 C3 H3 . . 119.4 ?
C5 C4 C9 . . 119.1(3) ?
C5 C4 C3 . . 121.5(2) ?
C9 C4 C3 . . 119.3(2) ?
O2 C5 C4 . . 123.2(2) ?
O2 C5 C6 . . 116.9(2) ?
C4 C5 C6 . . 119.8(2) ?
O3 C6 C7 . . 125.9(2) ?
O3 C6 C5 . . 114.7(2) ?
C7 C6 C5 . . 119.4(2) ?
C6 C7 C8 . . 120.9(3) ?
C6 C7 H7 . . 119.5 ?
C8 C7 H7 . . 119.5 ?
C9 C8 C7 . . 120.0(3) ?
C9 C8 H8 . . 120.0 ?
C7 C8 H8 . . 120.0 ?
C8 C9 C4 . . 120.7(2) ?
C8 C9 H9 . . 119.6 ?
C4 C9 H9 . . 119.6 ?
O3 C10 C11 . . 106.3(3) ?
O3 C10 H10A . . 110.5 ?
C11 C10 H10A . . 110.5 ?
O3 C10 H10B . . 110.5 ?
C11 C10 H10B . . 110.5 ?
H10A C10 H10B . . 108.7 ?
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
N1 C3 . 1.278(3) ?
N1 O1 . 1.403(3) ?
O1 C1 . 1.431(3) ?
O2 C5 . 1.361(3) ?
O2 H2 . 0.8200 ?
O3 C6 . 1.373(3) ?
O3 C10 . 1.427(3) ?
C1 C2 . 1.506(4) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 C1 14 1.506(4) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.459(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.399(3) ?
C4 C9 . 1.400(4) ?
C5 C6 . 1.405(4) ?
C6 C7 . 1.377(4) ?
C7 C8 . 1.387(4) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.369(4) ?
C8 H8 . 0.9300 ?
C9 H9 . 0.9300 ?
C10 C11 . 1.500(4) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 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 H2 N1 . 0.82 1.92 2.636(2) 145.0 y
C11 H11C O1 3_556 0.96 2.57 3.410(3) 146.0 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
C3 N1 O1 C1 . . . . -179.8(2) ?
N1 O1 C1 C2 . . . . -175.5(2) ?
O1 C1 C2 C1 . . . 14 67.48(19) ?
O1 N1 C3 C4 . . . . -179.0(2) ?
N1 C3 C4 C5 . . . . -4.3(4) ?
N1 C3 C4 C9 . . . . 175.1(3) ?
C9 C4 C5 O2 . . . . 179.9(3) ?
C3 C4 C5 O2 . . . . -0.7(4) ?
C9 C4 C5 C6 . . . . 0.6(4) ?
C3 C4 C5 C6 . . . . -180.0(2) ?
C10 O3 C6 C7 . . . . -2.1(4) ?
C10 O3 C6 C5 . . . . 177.5(2) ?
O2 C5 C6 O3 . . . . -0.9(3) ?
C4 C5 C6 O3 . . . . 178.4(2) ?
O2 C5 C6 C7 . . . . 178.7(2) ?
C4 C5 C6 C7 . . . . -1.9(4) ?
O3 C6 C7 C8 . . . . -178.2(3) ?
C5 C6 C7 C8 . . . . 2.2(4) ?
C6 C7 C8 C9 . . . . -1.2(4) ?
C7 C8 C9 C4 . . . . -0.1(4) ?
C5 C4 C9 C8 . . . . 0.4(4) ?
C3 C4 C9 C8 . . . . -179.0(3) ?
C6 O3 C10 C11 . . . . 176.8(3) ?
