#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/11/2221128.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_2221128
loop_
_publ_author_name
'Jia, Zhen'
_publ_section_title
;
 6,6'-Diethoxy-2,2'-[propane-1,2-diylbis(nitrilomethylidyne)]diphenol
;
_journal_coeditor_code           LH2762
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o646
_journal_paper_doi               10.1107/S1600536809003328
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C21 H26 N2 O4'
_chemical_formula_moiety         'C21 H26 N2 O4'
_chemical_formula_sum            'C21 H26 N2 O4'
_chemical_formula_weight         370.44
_chemical_name_systematic
;
6,6'-Diethoxy-2,2'-[propane-1,2-diylbis(nitrilomethylidyne)]diphenol
;
_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                113.845(5)
_cell_angle_beta                 109.628(6)
_cell_angle_gamma                108.812(5)
_cell_formula_units_Z            2
_cell_length_a                   9.140(3)
_cell_length_b                   11.451(4)
_cell_length_c                   13.013(5)
_cell_measurement_reflns_used    1361
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      23.859
_cell_measurement_theta_min      2.412
_cell_volume                     993.6(6)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_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      273(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0550
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4894
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9923
_exptl_absorpt_correction_T_min  0.9898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.261
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3451
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0658
_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)+(0.1202P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1679
_refine_ls_wR_factor_ref         0.1934
_reflns_number_gt                2325
_reflns_number_total             3451
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2762.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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        993.5(6)
_cod_database_code               2221128
_cod_database_fobs_code          2221128
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 0.2732(2) 0.85334(19) 0.31097(15) 0.0615(5) Uani d . 1 . .
H H1 0.2881 0.8851 0.3848 0.092 Uiso calc R 1 . .
O O2 0.1699(2) 0.75251(19) 0.06238(15) 0.0625(5) Uani d . 1 . .
O O3 0.1229(2) 0.44342(19) 0.38472(16) 0.0658(5) Uani d . 1 . .
H H3 0.1614 0.5336 0.4307 0.099 Uiso calc R 1 . .
O O4 0.0549(2) 0.16836(19) 0.25933(17) 0.0666(5) Uani d . 1 . .
N N1 0.1898(3) 0.8527(2) 0.4813(2) 0.0553(5) Uani d . 1 . .
N N2 0.3270(3) 0.7183(2) 0.60118(19) 0.0571(5) Uani d . 1 . .
C C1 -0.0337(3) 0.6987(3) 0.2479(2) 0.0521(6) Uani d . 1 . .
C C2 0.0950(3) 0.7499(2) 0.2166(2) 0.0477(6) Uani d . 1 . .
C C3 0.0365(3) 0.6931(3) 0.0830(2) 0.0514(6) Uani d . 1 . .
C C4 -0.1454(3) 0.5848(3) -0.0147(3) 0.0621(7) Uani d . 1 . .
H H4 -0.1842 0.5446 -0.1036 0.075 Uiso calc R 1 . .
C C5 -0.2713(4) 0.5348(3) 0.0171(3) 0.0717(8) Uani d . 1 . .
H H5 -0.3937 0.4618 -0.0504 0.086 Uiso calc R 1 . .
C C6 -0.2174(3) 0.5916(3) 0.1466(3) 0.0673(7) Uani d . 1 . .
H H6 -0.3033 0.5588 0.1674 0.081 Uiso calc R 1 . .
C C7 0.0251(4) 0.7553(3) 0.3859(3) 0.0554(6) Uani d . 1 . .
H H7 -0.0619 0.7182 0.4045 0.067 Uiso calc R 1 . .
C C8 0.1151(4) 0.6978(3) -0.0732(2) 0.0642(7) Uani d . 1 . .
H H8A 0.0269 0.7214 -0.1103 0.077 Uiso calc R 1 . .
H H8B 0.0583 0.5892 -0.1270 0.077 Uiso calc R 1 . .
C C9 0.2824(4) 0.7724(3) -0.0729(3) 0.0811(9) Uani d . 1 . .
H H9A 0.3376 0.8797 -0.0192 0.122 Uiso calc R 1 . .
H H9B 0.2492 0.7382 -0.1626 0.122 Uiso calc R 1 . .
H H9C 0.3681 0.7475 -0.0369 0.122 Uiso calc R 1 . .
C C10 0.3713(3) 0.5196(3) 0.5889(2) 0.0523(6) Uani d . 1 . .
C C11 0.2296(3) 0.4113(3) 0.4549(2) 0.0509(6) Uani d . 1 . .
C C12 0.1958(3) 0.2656(3) 0.3898(2) 0.0543(6) Uani d . 1 . .
C C13 0.3036(4) 0.2294(3) 0.4590(3) 0.0641(7) Uani d . 1 . .
H H13 0.2816 0.1324 0.4161 0.077 Uiso calc R 1 . .
C C14 0.4442(4) 0.3374(3) 0.5920(3) 0.0722(8) Uani d . 1 . .
H H14 0.5158 0.3124 0.6379 0.087 Uiso calc R 1 . .
C C15 0.4778(4) 0.4803(3) 0.6557(3) 0.0687(7) Uani d . 1 . .
H H15 0.5728 0.5520 0.7446 0.082 Uiso calc R 1 . .
C C16 0.4133(3) 0.6729(3) 0.6564(2) 0.0563(6) Uani d . 1 . .
H H16 0.5092 0.7418 0.7454 0.068 Uiso calc R 1 . .
C C17 0.0096(4) 0.0166(3) 0.1890(3) 0.0718(8) Uani d . 1 . .
H H17A -0.0139 -0.0273 0.2360 0.086 Uiso calc R 1 . .
H H17B 0.1100 0.0128 0.1810 0.086 Uiso calc R 1 . .
C C18 -0.1577(5) -0.0678(3) 0.0545(3) 0.0911(10) Uani d . 1 . .
H H18A -0.2550 -0.0608 0.0637 0.137 Uiso calc R 1 . .
H H18B -0.1943 -0.1717 0.0050 0.137 Uiso calc R 1 . .
H H18C -0.1316 -0.0253 0.0079 0.137 Uiso calc R 1 . .
C C19 0.3894(4) 0.8780(3) 0.6768(2) 0.0609(7) Uani d . 1 . .
H H19A 0.4958 0.9345 0.6779 0.073 Uiso calc R 1 . .
H H19B 0.4262 0.9145 0.7681 0.073 Uiso calc R 1 . .
C C20 0.2425(4) 0.9054(3) 0.6181(2) 0.0606(7) Uani d . 1 . .
H H20 0.1354 0.8498 0.6181 0.073 Uiso calc R 1 . .
C C21 0.3133(5) 1.0728(3) 0.6992(3) 0.0823(9) Uani d . 1 . .
H H21A 0.4190 1.1274 0.7001 0.123 Uiso calc R 1 . .
H H21B 0.3464 1.1076 0.7889 0.123 Uiso calc R 1 . .
H H21C 0.2192 1.0891 0.6599 0.123 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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 H1 . . 109.5 ?
C3 O2 C8 . . 116.92(19) ?
C11 O3 H3 . . 109.5 ?
C12 O4 C17 . . 118.2(2) ?
C7 N1 C20 . . 120.5(2) ?
C16 N2 C19 . . 118.7(2) ?
C6 C1 C2 . . 119.9(2) ?
C6 C1 C7 . . 120.0(2) ?
C2 C1 C7 . . 120.1(2) ?
O1 C2 C1 . . 122.0(2) ?
O1 C2 C3 . . 118.7(2) ?
C1 C2 C3 . . 119.4(2) ?
O2 C3 C4 . . 125.7(2) ?
O2 C3 C2 . . 115.3(2) ?
C4 C3 C2 . . 119.1(2) ?
C3 C4 C5 . . 121.1(2) ?
C3 C4 H4 . . 119.4 ?
C5 C4 H4 . . 119.4 ?
C6 C5 C4 . . 120.5(2) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C5 C6 C1 . . 120.0(3) ?
C5 C6 H6 . . 120.0 ?
C1 C6 H6 . . 120.0 ?
N1 C7 C1 . . 122.4(2) ?
N1 C7 H7 . . 118.8 ?
C1 C7 H7 . . 118.8 ?
O2 C8 C9 . . 107.9(2) ?
O2 C8 H8A . . 110.1 ?
C9 C8 H8A . . 110.1 ?
O2 C8 H8B . . 110.1 ?
C9 C8 H8B . . 110.1 ?
H8A C8 H8B . . 108.4 ?
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 ?
C15 C10 C11 . . 119.3(2) ?
C15 C10 C16 . . 119.9(2) ?
C11 C10 C16 . . 120.8(2) ?
O3 C11 C12 . . 118.1(2) ?
O3 C11 C10 . . 121.8(2) ?
C12 C11 C10 . . 120.0(2) ?
O4 C12 C13 . . 124.9(2) ?
O4 C12 C11 . . 115.6(2) ?
C13 C12 C11 . . 119.5(2) ?
C12 C13 C14 . . 120.2(3) ?
C12 C13 H13 . . 119.9 ?
C14 C13 H13 . . 119.9 ?
C15 C14 C13 . . 120.3(2) ?
C15 C14 H14 . . 119.9 ?
C13 C14 H14 . . 119.9 ?
C14 C15 C10 . . 120.7(3) ?
C14 C15 H15 . . 119.6 ?
C10 C15 H15 . . 119.6 ?
N2 C16 C10 . . 123.6(2) ?
N2 C16 H16 . . 118.2 ?
C10 C16 H16 . . 118.2 ?
O4 C17 C18 . . 107.3(2) ?
O4 C17 H17A . . 110.3 ?
C18 C17 H17A . . 110.3 ?
O4 C17 H17B . . 110.3 ?
C18 C17 H17B . . 110.3 ?
H17A C17 H17B . . 108.5 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
N2 C19 C20 . . 112.0(2) ?
N2 C19 H19A . . 109.2 ?
C20 C19 H19A . . 109.2 ?
N2 C19 H19B . . 109.2 ?
C20 C19 H19B . . 109.2 ?
H19A C19 H19B . . 107.9 ?
N1 C20 C19 . . 109.1(2) ?
N1 C20 C21 . . 109.2(2) ?
C19 C20 C21 . . 110.2(2) ?
N1 C20 H20 . . 109.5 ?
C19 C20 H20 . . 109.5 ?
C21 C20 H20 . . 109.5 ?
C20 C21 H21A . . 109.5 ?
C20 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C20 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 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 . 1.341(3) ?
O1 H1 . 0.8200 ?
O2 C3 . 1.361(3) ?
O2 C8 . 1.437(3) ?
O3 C11 . 1.351(3) ?
O3 H3 . 0.8200 ?
O4 C12 . 1.364(3) ?
O4 C17 . 1.423(3) ?
N1 C7 . 1.262(3) ?
N1 C20 . 1.461(3) ?
N2 C16 . 1.263(3) ?
N2 C19 . 1.461(3) ?
C1 C6 . 1.393(3) ?
C1 C2 . 1.401(3) ?
C1 C7 . 1.456(4) ?
C2 C3 . 1.404(3) ?
C3 C4 . 1.376(3) ?
C4 C5 . 1.382(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.362(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.490(4) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 C15 . 1.391(3) ?
C10 C11 . 1.397(3) ?
C10 C16 . 1.447(3) ?
C11 C12 . 1.394(3) ?
C12 C13 . 1.387(4) ?
C13 C14 . 1.388(4) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.366(4) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C17 C18 . 1.489(4) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C19 C20 . 1.503(4) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C20 C21 . 1.521(4) ?
C20 H20 . 0.9800 ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 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
O3 H3 N2 . 0.82 1.89 2.614(3) 146.7
O1 H1 N1 . 0.82 1.85 2.576(2) 146.2
