#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/51/2215145.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_2215145
loop_
_publ_author_name
'Yan-Ping Zhang'
'Xiao Chen'
'Jun-Yan Shi'
'Li Xu'
'Wen-Kui Dong'
_publ_section_title
;
 5,5'-Bis(diethylamino)-2,2'-[ethylenedioxybis(nitrilomethylidyne)]diphenol
;
_journal_coeditor_code           HG2270
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3852
_journal_page_last               o3852
_journal_paper_doi               10.1107/S1600536807038597
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C24 H34 N4 O4'
_chemical_formula_moiety         'C24 H34 N4 O4'
_chemical_formula_sum            'C24 H34 N4 O4'
_chemical_formula_weight         442.55
_chemical_name_systematic
;
5,5'-Bis(diethylamino)-2,2'-[ethylenedioxybis(nitrilomethylidyne)]diphenol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 97.063(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.3705(10)
_cell_length_b                   18.386(2)
_cell_length_c                   8.9368(16)
_cell_measurement_reflns_used    1428
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.16
_cell_measurement_theta_min      2.216
_cell_volume                     1201.9(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 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  0.0424
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6175
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.22
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9671
_exptl_absorpt_correction_T_min  0.9544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.163
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2114
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0428
_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)+(0.0358P)²+0.4459P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.1231
_reflns_number_gt                1249
_reflns_number_total             2114
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2270.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2215145
_cod_database_fobs_code          2215145
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
N N1 0.7756(3) 0.48722(11) 0.1956(2) 0.0493(5) Uani d . 1
N N2 0.3985(2) 0.32076(11) 0.7116(2) 0.0521(6) Uani d . 1
O O1 0.7825(2) 0.52817(9) 0.06124(18) 0.0582(5) Uani d . 1
O O2 0.8711(2) 0.41916(11) 0.4589(2) 0.0755(6) Uani d . 1
H H2 0.8884 0.4424 0.3836 0.113 Uiso calc R 1
C C1 0.9679(3) 0.53421(13) 0.0339(3) 0.0526(7) Uani d . 1
H H1A 1.0441 0.5442 0.1280 0.063 Uiso calc R 1
H H1B 0.9800 0.5746 -0.0340 0.063 Uiso calc R 1
C C2 0.6097(3) 0.47704(12) 0.2187(2) 0.0432(6) Uani d . 1
H H2A 0.5166 0.4960 0.1500 0.052 Uiso calc R 1
C C3 0.5613(3) 0.43738(12) 0.3469(2) 0.0381(5) Uani d . 1
C C4 0.6890(3) 0.40947(13) 0.4609(3) 0.0449(6) Uani d . 1
C C5 0.6359(3) 0.37169(13) 0.5808(2) 0.0452(6) Uani d . 1
H H5 0.7245 0.3536 0.6544 0.054 Uiso calc R 1
C C6 0.4517(3) 0.35996(12) 0.5943(2) 0.0403(5) Uani d . 1
C C7 0.3223(3) 0.38893(12) 0.4812(2) 0.0439(6) Uani d . 1
H H7 0.1981 0.3825 0.4866 0.053 Uiso calc R 1
C C8 0.3788(3) 0.42628(12) 0.3639(2) 0.0433(6) Uani d . 1
H H8 0.2904 0.4454 0.2913 0.052 Uiso calc R 1
C C9 0.5293(3) 0.28426(14) 0.8212(3) 0.0605(7) Uani d . 1
H H9A 0.6319 0.2680 0.7716 0.073 Uiso calc R 1
H H9B 0.4719 0.2416 0.8585 0.073 Uiso calc R 1
C C10 0.5996(4) 0.33191(18) 0.9531(3) 0.0809(9) Uani d . 1
H H10A 0.6590 0.3738 0.9174 0.121 Uiso calc R 1
H H10B 0.6853 0.3050 1.0214 0.121 Uiso calc R 1
H H10C 0.4992 0.3473 1.0045 0.121 Uiso calc R 1
C C11 0.2080(3) 0.31521(14) 0.7367(3) 0.0580(7) Uani d . 1
H H11A 0.1447 0.3591 0.6995 0.070 Uiso calc R 1
H H11B 0.2016 0.3124 0.8443 0.070 Uiso calc R 1
C C12 0.1107(4) 0.25025(17) 0.6610(3) 0.0808(9) Uani d . 1
H H12A 0.0987 0.2565 0.5536 0.121 Uiso calc R 1
H H12B -0.0084 0.2459 0.6931 0.121 Uiso calc R 1
H H12C 0.1800 0.2070 0.6882 0.121 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
C2 N1 O1 . . 110.35(18)
C6 N2 C9 . . 122.09(19)
C6 N2 C11 . . 121.92(19)
C9 N2 C11 . . 116.0(2)
C1 O1 N1 . . 108.75(17)
C4 O2 H2 . . 109.5
O1 C1 C1 . 3_765 111.2(2)
O1 C1 H1A . . 109.4
C1 C1 H1A 3_765 . 109.4
O1 C1 H1B . . 109.4
C1 C1 H1B 3_765 . 109.4
H1A C1 H1B . . 108.0
N1 C2 C3 . . 122.5(2)
N1 C2 H2A . . 118.7
C3 C2 H2A . . 118.7
C8 C3 C4 . . 116.2(2)
C8 C3 C2 . . 120.0(2)
C4 C3 C2 . . 123.8(2)
O2 C4 C5 . . 117.0(2)
O2 C4 C3 . . 121.4(2)
C5 C4 C3 . . 121.6(2)
C4 C5 C6 . . 121.3(2)
C4 C5 H5 . . 119.3
C6 C5 H5 . . 119.3
N2 C6 C5 . . 121.4(2)
N2 C6 C7 . . 121.1(2)
C5 C6 C7 . . 117.4(2)
C8 C7 C6 . . 120.0(2)
C8 C7 H7 . . 120.0
C6 C7 H7 . . 120.0
C7 C8 C3 . . 123.5(2)
C7 C8 H8 . . 118.3
C3 C8 H8 . . 118.3
N2 C9 C10 . . 113.2(2)
N2 C9 H9A . . 108.9
C10 C9 H9A . . 108.9
N2 C9 H9B . . 108.9
C10 C9 H9B . . 108.9
H9A C9 H9B . . 107.7
C9 C10 H10A . . 109.5
C9 C10 H10B . . 109.5
H10A C10 H10B . . 109.5
C9 C10 H10C . . 109.5
H10A C10 H10C . . 109.5
H10B C10 H10C . . 109.5
N2 C11 C12 . . 113.7(2)
N2 C11 H11A . . 108.8
C12 C11 H11A . . 108.8
N2 C11 H11B . . 108.8
C12 C11 H11B . . 108.8
H11A C11 H11B . . 107.7
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
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C2 . 1.279(3)
N1 O1 . 1.424(2)
N2 C6 . 1.369(3)
N2 C9 . 1.452(3)
N2 C11 . 1.452(3)
O1 C1 . 1.422(2)
O2 C4 . 1.357(2)
O2 H2 . 0.8200
C1 C1 3_765 1.498(4)
C1 H1A . 0.9700
C1 H1B . 0.9700
C2 C3 . 1.439(3)
C2 H2A . 0.9300
C3 C8 . 1.387(3)
C3 C4 . 1.397(3)
C4 C5 . 1.373(3)
C5 C6 . 1.394(3)
C5 H5 . 0.9300
C6 C7 . 1.407(3)
C7 C8 . 1.361(3)
C7 H7 . 0.9300
C8 H8 . 0.9300
C9 C10 . 1.508(4)
C9 H9A . 0.9700
C9 H9B . 0.9700
C10 H10A . 0.9600
C10 H10B . 0.9600
C10 H10C . 0.9600
C11 C12 . 1.510(4)
C11 H11A . 0.9700
C11 H11B . 0.9700
C12 H12A . 0.9600
C12 H12B . 0.9600
C12 H12C . 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2 N1 0.820(10) 1.96(2) 2.68(2) 146.00(10) 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_4
_geom_torsion
C2 N1 O1 C1 . -176.15(19)
N1 O1 C1 C1 3_765 78.7(3)
O1 N1 C2 C3 . -179.86(19)
N1 C2 C3 C8 . -178.2(2)
N1 C2 C3 C4 . 3.2(3)
C8 C3 C4 O2 . -177.8(2)
C2 C3 C4 O2 . 0.9(3)
C8 C3 C4 C5 . 1.6(3)
C2 C3 C4 C5 . -179.7(2)
O2 C4 C5 C6 . 178.9(2)
C3 C4 C5 C6 . -0.4(4)
C9 N2 C6 C5 . -5.2(3)
C11 N2 C6 C5 . 172.8(2)
C9 N2 C6 C7 . 173.7(2)
C11 N2 C6 C7 . -8.3(3)
C4 C5 C6 N2 . 178.3(2)
C4 C5 C6 C7 . -0.6(3)
N2 C6 C7 C8 . -178.5(2)
C5 C6 C7 C8 . 0.4(3)
C6 C7 C8 C3 . 0.8(3)
C4 C3 C8 C7 . -1.8(3)
C2 C3 C8 C7 . 179.5(2)
C6 N2 C9 C10 . 88.5(3)
C11 N2 C9 C10 . -89.6(3)
C6 N2 C11 C12 . 91.9(3)
C9 N2 C11 C12 . -90.0(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139072944
