#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/29/2222996.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_2222996
loop_
_publ_author_name
'Fejfarová, Karla'
'Dehno Khalaji, Aliakbar'
'Dušek, Michal'
_publ_section_title
;
 N,N'-Bis(2,3-dimethoxybenzylidene)propane-1,3-diamine
;
_journal_coeditor_code           BT5030
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2288
_journal_paper_doi               10.1107/S1600536809031651
_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         370.4
_chemical_name_systematic
;
N,N'-Bis(2,3-dimethoxybenzylidene)propane-1,3-diamine
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3079(3)
_cell_length_b                   9.2915(2)
_cell_length_c                   13.8059(3)
_cell_measurement_reflns_used    24214
_cell_measurement_temperature    120
_cell_measurement_theta_max      62.3336
_cell_measurement_theta_min      3.1975
_cell_volume                     1963.66(7)
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material
'JANA2006 (Petříček et al.,  2007)'
_computing_structure_refinement
'JANA2006 (Petříček et al.,  2007)'
_computing_structure_solution    'SIR2002 (Burla et al.,  2003)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 20.7567
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device       'four-cycle diffractometer'
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer with an Atlas (Gemini ultra Cu)
detector
;
_diffrn_measurement_method       'Rotation method data acquisition using ω'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0027
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26538
_diffrn_reflns_reduction_process
;
Integration of the CCD images was done by program Crysalis RED
(Oxford diffraction, 2009). The same program was used for indexing of the
crystal shape and absorption correction.
;
_diffrn_reflns_theta_full        62.43
_diffrn_reflns_theta_max         62.43
_diffrn_reflns_theta_min         5.57
_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_T_max  0.871
_exptl_absorpt_correction_T_min  0.628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis Pro; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.2527
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular shape'
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.5143
_exptl_crystal_size_mid          0.3111
_exptl_crystal_size_min          0.2022
_refine_diff_density_max         0.10
_refine_diff_density_min         -0.09
_refine_ls_extinction_coef       28E2(10)
_refine_ls_extinction_method
'B--C type 1 Lorentzian isotropic (Becker & Coppens, 1974)'
_refine_ls_goodness_of_fit_ref   1.97
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_constraints    105
_refine_ls_number_parameters     244
_refine_ls_number_reflns         1623
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0248
_refine_ls_shift/su_max          0.0378
_refine_ls_shift/su_mean         0.0083
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/[σ²(I)+0.0016I²]
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0767
_reflns_number_gt                1616
_reflns_number_total             1623
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            bt5030.cif
_cod_data_source_block           I
_cod_database_code               2222996
_cod_database_fobs_code          2222996
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,z+1/2
3 x+1/2,-y+1/2,z
4 -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_disorder_assembly
_atom_site_disorder_group
O O1 0.26797(8) 0.00499(13) 0.18586(12) 0.0306(4) Uani d . 1 . .
O O2 0.18047(7) -0.18392(11) 0.07546(13) 0.0282(3) Uani d . 1 . .
O O3 0.46602(7) 0.01788(12) 0.27381(11) 0.0315(4) Uani d . 1 . .
O O4 0.57090(7) -0.12117(13) 0.40069(13) 0.0348(4) Uani d . 1 . .
N N1 0.22853(8) 0.43567(14) 0.17846(14) 0.0279(4) Uani d . 1 . .
N N2 0.46937(8) 0.45543(14) 0.24531(14) 0.0281(4) Uani d . 1 . .
C C1 0.18698(9) 0.20195(17) 0.11887(15) 0.0239(4) Uani d . 1 . .
C C2 0.20316(10) 0.05443(16) 0.12523(15) 0.0239(4) Uani d . 1 . .
C C3 0.16066(9) -0.04171(17) 0.06289(16) 0.0246(4) Uani d . 1 . .
C C4 0.10498(10) 0.01093(17) -0.00881(15) 0.0274(5) Uani d . 1 . .
C C5 0.09133(10) 0.15967(17) -0.01601(15) 0.0292(5) Uani d . 1 . .
C C6 0.13056(11) 0.25368(17) 0.04693(16) 0.0272(5) Uani d . 1 . .
C C7 0.23004(10) 0.30040(17) 0.18825(14) 0.0246(4) Uani d . 1 . .
C C8 0.27152(10) 0.52016(17) 0.25365(14) 0.0263(5) Uani d . 1 . .
C C9 0.34446(10) 0.61189(16) 0.21099(14) 0.0262(5) Uani d . 1 . .
C C10 0.41895(11) 0.52360(17) 0.16833(15) 0.0277(5) Uani d . 1 . .
C C11 0.47382(10) 0.31972(17) 0.24671(15) 0.0253(5) Uani d . 1 . .
C C12 0.52555(9) 0.24424(17) 0.32177(14) 0.0244(4) Uani d . 1 . .
C C13 0.52359(10) 0.09464(17) 0.32989(15) 0.0249(4) Uani d . 1 . .
C C14 0.57636(10) 0.02498(19) 0.39893(16) 0.0275(5) Uani d . 1 . .
C C15 0.62910(10) 0.10661(19) 0.46004(15) 0.0301(5) Uani d . 1 . .
C C16 0.62956(11) 0.25595(19) 0.45242(15) 0.0303(5) Uani d . 1 . .
C C17 0.57829(10) 0.32443(18) 0.38485(15) 0.0272(5) Uani d . 1 . .
C C18 0.23861(13) -0.0640(2) 0.27226(15) 0.0402(6) Uani d . 1 . .
C C19 0.14018(12) -0.28468(19) 0.01141(16) 0.0327(5) Uani d . 1 . .
C C20 0.50416(12) -0.0730(2) 0.20153(18) 0.0396(6) Uani d . 1 . .
C C21 0.62707(12) -0.1948(2) 0.46665(17) 0.0400(6) Uani d . 1 . .
H H4 0.076366 -0.053919 -0.052675 0.0329 Uiso d . 1 . .
H H5 0.053814 0.196398 -0.065946 0.035 Uiso d . 1 . .
H H6 0.119366 0.355051 0.041722 0.0327 Uiso d . 1 . .
H H7 0.260269 0.26004 0.242784 0.0295 Uiso d . 1 . .
H H8a 0.295303 0.456715 0.301782 0.0315 Uiso d . 1 . .
H H8b 0.229431 0.581308 0.284681 0.0315 Uiso d . 1 . .
H H9a 0.32086 0.674064 0.162003 0.0314 Uiso d . 1 . .
H H9b 0.366972 0.675138 0.259983 0.0314 Uiso d . 1 . .
H H10a 0.395548 0.450955 0.126235 0.0333 Uiso d . 1 . .
H H10b 0.456428 0.58522 0.131065 0.0333 Uiso d . 1 . .
H H11 0.443276 0.264808 0.198515 0.0303 Uiso d . 1 . .
H H15 0.66515 0.059858 0.507446 0.0361 Uiso d . 1 . .
H H16 0.666035 0.31172 0.494737 0.0364 Uiso d . 1 . .
H H17 0.5786 0.427575 0.380869 0.0327 Uiso d . 1 . .
H H18a 0.288071 -0.09841 0.308189 0.0482 Uiso d . 1 . .
H H18b 0.206536 0.003592 0.311013 0.0482 Uiso d . 1 . .
H H18c 0.201483 -0.14353 0.255709 0.0482 Uiso d . 1 . .
H H19a 0.156576 -0.380645 0.029678 0.0393 Uiso d . 1 . .
H H19b 0.077848 -0.274903 0.015211 0.0393 Uiso d . 1 . .
H H19c 0.159047 -0.266242 -0.053739 0.0393 Uiso d . 1 . .
H H20a 0.4592 -0.108672 0.159426 0.0475 Uiso d . 1 . .
H H20b 0.545747 -0.018776 0.164399 0.0475 Uiso d . 1 . .
H H20c 0.533122 -0.15241 0.23229 0.0475 Uiso d . 1 . .
H H21a 0.615974 -0.296407 0.463211 0.0479 Uiso d . 1 . .
H H21b 0.686855 -0.176274 0.449786 0.0479 Uiso d . 1 . .
H H21c 0.616154 -0.16141 0.531323 0.0479 Uiso d . 1 . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.018 0.009 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
H 0.000 0.000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
N 0.031 0.018 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
O 0.049 0.032 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 C18 . . . 115.54(13) ?
C3 O2 C19 . . . 117.35(15) ?
C13 O3 C20 . . . 115.95(13) ?
C14 O4 C21 . . . 116.94(15) ?
C7 N1 C8 . . . 116.79(16) ?
C10 N2 C11 . . . 118.25(16) ?
C2 C1 C6 . . . 119.40(16) ?
C2 C1 C7 . . . 119.17(16) ?
C6 C1 C7 . . . 121.43(14) ?
O1 C2 C1 . . . 119.59(15) ?
O1 C2 C3 . . . 119.70(13) ?
C1 C2 C3 . . . 120.35(16) ?
O2 C3 C2 . . . 115.82(16) ?
O2 C3 C4 . . . 124.38(16) ?
C2 C3 C4 . . . 119.75(14) ?
C3 C4 C5 . . . 119.16(16) ?
C3 C4 H4 . . . 120.42 ?
C5 C4 H4 . . . 120.4205 ?
C4 C5 C6 . . . 121.22(17) ?
C4 C5 H5 . . . 119.3896 ?
C6 C5 H5 . . . 119.3903 ?
C1 C6 C5 . . . 120.05(15) ?
C1 C6 H6 . . . 119.9753 ?
C5 C6 H6 . . . 119.9765 ?
N1 C7 C1 . . . 122.50(17) ?
N1 C7 H7 . . . 118.7511 ?
C1 C7 H7 . . . 118.7506 ?
N1 C8 C9 . . . 110.91(16) ?
N1 C8 H8a . . . 109.4708 ?
N1 C8 H8b . . . 109.4707 ?
C9 C8 H8a . . . 109.4715 ?
C9 C8 H8b . . . 109.4712 ?
H8a C8 H8b . . . 107.9975 ?
C8 C9 C10 . . . 113.38(13) ?
C8 C9 H9a . . . 109.4711 ?
C8 C9 H9b . . . 109.471 ?
C10 C9 H9a . . . 109.4708 ?
C10 C9 H9b . . . 109.4724 ?
H9a C9 H9b . . . 105.2553 ?
N2 C10 C9 . . . 110.39(16) ?
N2 C10 H10a . . . 109.4708 ?
N2 C10 H10b . . . 109.4703 ?
C9 C10 H10a . . . 109.472 ?
C9 C10 H10b . . . 109.4717 ?
H10a C10 H10b . . . 108.5415 ?
N2 C11 C12 . . . 120.82(17) ?
N2 C11 H11 . . . 119.5897 ?
C12 C11 H11 . . . 119.5889 ?
C11 C12 C13 . . . 121.11(15) ?
C11 C12 C17 . . . 119.41(14) ?
C13 C12 C17 . . . 119.48(16) ?
O3 C13 C12 . . . 119.09(15) ?
O3 C13 C14 . . . 120.77(15) ?
C12 C13 C14 . . . 120.03(16) ?
O4 C14 C13 . . . 115.84(16) ?
O4 C14 C15 . . . 124.64(17) ?
C13 C14 C15 . . . 119.52(16) ?
C14 C15 C16 . . . 120.02(17) ?
C14 C15 H15 . . . 119.9905 ?
C16 C15 H15 . . . 119.9904 ?
C15 C16 C17 . . . 120.65(17) ?
C15 C16 H16 . . . 119.6771 ?
C17 C16 H16 . . . 119.6769 ?
C12 C17 C16 . . . 120.28(15) ?
C12 C17 H17 . . . 119.8593 ?
C16 C17 H17 . . . 119.8611 ?
O1 C18 H18a . . . 109.4709 ?
O1 C18 H18b . . . 109.4711 ?
O1 C18 H18c . . . 109.4709 ?
H18a C18 H18b . . . 109.4714 ?
H18a C18 H18c . . . 109.4717 ?
H18b C18 H18c . . . 109.4712 ?
O2 C19 H19a . . . 109.4712 ?
O2 C19 H19b . . . 109.4713 ?
O2 C19 H19c . . . 109.4707 ?
H19a C19 H19b . . . 109.4714 ?
H19a C19 H19c . . . 109.4716 ?
H19b C19 H19c . . . 109.4711 ?
O3 C20 H20a . . . 109.4712 ?
O3 C20 H20b . . . 109.4716 ?
O3 C20 H20c . . . 109.4718 ?
H20a C20 H20b . . . 109.471 ?
H20a C20 H20c . . . 109.4707 ?
H20b C20 H20c . . . 109.4711 ?
O4 C21 H21a . . . 109.4718 ?
O4 C21 H21b . . . 109.4707 ?
O4 C21 H21c . . . 109.4713 ?
H21a C21 H21b . . . 109.4709 ?
H21a C21 H21c . . . 109.4715 ?
H21b C21 H21c . . . 109.4711 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 . . 1.377(2) .
O1 C18 . . 1.427(2) .
O2 C3 . . 1.3668(18) .
O2 C19 . . 1.428(2) .
O3 C13 . . 1.373(2) .
O3 C20 . . 1.432(3) .
O4 C14 . . 1.361(2) .
O4 C21 . . 1.427(3) .
N1 C7 . . 1.264(2) .
N1 C8 . . 1.458(2) .
N2 C10 . . 1.458(2) .
N2 C11 . . 1.263(2) .
C1 C2 . . 1.396(2) .
C1 C6 . . 1.401(3) .
C1 C7 . . 1.479(2) .
C2 C3 . . 1.401(2) .
C3 C4 . . 1.395(3) .
C4 C5 . . 1.401(2) .
C4 H4 . . 0.96 ?
C5 C6 . . 1.371(3) .
C5 H5 . . 0.96 ?
C6 H6 . . 0.96 ?
C7 H7 . . 0.96 ?
C8 C9 . . 1.523(2) .
C8 H8a . . 0.96 ?
C8 H8b . . 0.96 ?
C9 C10 . . 1.523(2) .
C9 H9a . . 0.96 ?
C9 H9b . . 0.96 ?
C10 H10a . . 0.96 ?
C10 H10b . . 0.96 ?
C11 C12 . . 1.481(3) .
C11 H11 . . 0.96 ?
C12 C13 . . 1.395(2) .
C12 C17 . . 1.402(2) .
C13 C14 . . 1.407(3) .
C14 C15 . . 1.392(3) .
C15 C16 . . 1.392(2) .
C15 H15 . . 0.96 ?
C16 C17 . . 1.375(3) .
C16 H16 . . 0.96 ?
C17 H17 . . 0.96 ?
C18 H18a . . 0.96 ?
C18 H18b . . 0.96 ?
C18 H18c . . 0.96 ?
C19 H19a . . 0.96 ?
C19 H19b . . 0.96 ?
C19 H19c . . 0.96 ?
C20 H20a . . 0.96 ?
C20 H20b . . 0.96 ?
C20 H20c . . 0.96 ?
C21 H21a . . 0.96 ?
C21 H21b . . 0.96 ?
C21 H21c . . 0.96 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_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
C5 H5 O4 . . 4_554 0.96 2.59 3.411(2) 143 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 226132
