#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/47/7214761.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7214761
loop_
_publ_author_name
'Riisiö, Antti'
'Hänninen, Mikko M.'
'Sillanpää, Reijo'
_publ_section_title
;
 Alkyl and diether bridged
 N,N,N′,N′-tetra(2-hydroxybenzyl)diamines: effects of
 hydrogen bonding on structure and solubility
;
_journal_issue                   21
_journal_name_full               CrystEngComm
_journal_page_first              7258
_journal_paper_doi               10.1039/c2ce26027a
_journal_volume                  14
_journal_year                    2012
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C42 H56 N2 O6, C4 H10 O'
_chemical_formula_sum            'C46 H66 N2 O7'
_chemical_formula_weight         759.01
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2012-06-04T15:55:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 113.402(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.4087(12)
_cell_length_b                   12.1422(5)
_cell_length_c                   15.9143(7)
_cell_measurement_reflns_used    4866
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      26.733
_cell_measurement_theta_min      0.407
_cell_measurement_wavelength     0.71073
_cell_volume                     4506.0(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      223(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8379
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.49
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.41
_refine_diff_density_min         -0.29
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         4411
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1048
_refine_ls_R_factor_gt           0.0661
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1019P)²+2.5142P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1741
_refine_ls_wR_factor_ref         0.2044
_reflns_number_gt                2847
_reflns_number_total             4411
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c2ce26027a.txt
_cod_data_source_block           H4L3_3
_cod_original_cell_volume        4506.0(3)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7214761
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.31606(8) 0.59847(15) 0.34055(12) 0.0639(5) Uani 1 1 d .
H1 H 0.2846(13) 0.551(2) 0.3249(19) 0.077 Uiso 1 1 d .
O2 O 0.20876(8) 0.51548(15) 0.40910(12) 0.0682(5) Uani 1 1 d .
H2 H 0.2227(13) 0.459(3) 0.393(2) 0.082 Uiso 1 1 d .
O3 O 0 0.3639(4) 0.25 0.1322(14) Uani 1 2 d S
O18 O 0.25517(8) 0.30186(14) 0.39868(13) 0.0694(5) Uani 1 1 d .
N8 N 0.23858(9) 0.43832(16) 0.24536(13) 0.0580(5) Uani 1 1 d .
C1 C 0.33853(10) 0.58251(19) 0.27613(17) 0.0561(6) Uani 1 1 d .
C2 C 0.39426(11) 0.6190(2) 0.29545(18) 0.0646(7) Uani 1 1 d .
C3 C 0.41667(12) 0.6016(2) 0.2306(2) 0.0731(8) Uani 1 1 d .
H3 H 0.4537 0.6279 0.2425 0.088 Uiso 1 1 calc R
C4 C 0.38720(11) 0.5471(2) 0.14879(18) 0.0657(7) Uani 1 1 d .
C5 C 0.33157(11) 0.5134(2) 0.13062(17) 0.0602(6) Uani 1 1 d .
H5 H 0.3104 0.4772 0.0752 0.072 Uiso 1 1 calc R
C6 C 0.30651(10) 0.53204(19) 0.19269(16) 0.0549(6) Uani 1 1 d .
C7 C 0.24505(11) 0.5000(2) 0.17031(17) 0.0629(7) Uani 1 1 d .
H7A H 0.2214 0.5666 0.1578 0.076 Uiso 1 1 calc R
H7B H 0.2311 0.4547 0.1148 0.076 Uiso 1 1 calc R
C9 C 0.17701(11) 0.4259(2) 0.22663(19) 0.0679(7) Uani 1 1 d .
H9A H 0.1724 0.3658 0.2642 0.081 Uiso 1 1 calc R
H9B H 0.1561 0.4059 0.1622 0.081 Uiso 1 1 calc R
C10 C 0.15145(10) 0.5295(2) 0.24654(18) 0.0635(7) Uani 1 1 d .
C11 C 0.10936(12) 0.5880(3) 0.1768(2) 0.0836(9) Uani 1 1 d .
H11 H 0.0974 0.5627 0.1163 0.1 Uiso 1 1 calc R
C12 C 0.08439(14) 0.6827(3) 0.1937(3) 0.0953(11) Uani 1 1 d .
C13 C 0.10298(14) 0.7188(3) 0.2827(3) 0.0862(9) Uani 1 1 d .
H13 H 0.0869 0.7833 0.2951 0.103 Uiso 1 1 calc R
C14 C 0.14470(12) 0.6634(2) 0.3553(2) 0.0704(7) Uani 1 1 d .
C15 C 0.16849(10) 0.5685(2) 0.33569(18) 0.0599(6) Uani 1 1 d .
C16 C 0.26939(13) 0.3320(2) 0.2618(2) 0.0717(8) Uani 1 1 d .
H16A H 0.2983 0.3346 0.2356 0.086 Uiso 1 1 calc R
H16B H 0.2422 0.2731 0.231 0.086 Uiso 1 1 calc R
C17 C 0.29789(13) 0.3069(2) 0.3616(2) 0.0724(8) Uani 1 1 d .
H17A H 0.3181 0.2364 0.3708 0.087 Uiso 1 1 calc R
H17B H 0.3259 0.3645 0.3928 0.087 Uiso 1 1 calc R
C19 C 0.27448(12) 0.2498(2) 0.48558(18) 0.0645(7) Uani 1 1 d .
H19A H 0.3071 0.29 0.53 0.077 Uiso 1 1 calc R
H19B H 0.2866 0.1741 0.4814 0.077 Uiso 1 1 calc R
C20 C 0.42846(13) 0.6760(3) 0.3851(2) 0.0862(9) Uani 1 1 d .
H20A H 0.4455 0.6213 0.4326 0.129 Uiso 1 1 calc R
H20B H 0.4033 0.7234 0.4015 0.129 Uiso 1 1 calc R
H20C H 0.4585 0.7199 0.3786 0.129 Uiso 1 1 calc R
C21 C 0.41442(15) 0.5257(3) 0.0807(2) 0.0919(10) Uani 1 1 d .
H21A H 0.4243 0.5953 0.0608 0.138 Uiso 1 1 calc R
H21B H 0.3875 0.4864 0.0282 0.138 Uiso 1 1 calc R
H21C H 0.4488 0.4817 0.1097 0.138 Uiso 1 1 calc R
C22 C 0.03872(19) 0.7448(5) 0.1150(3) 0.152(2) Uani 1 1 d .
H22A H 0.054 0.7653 0.0703 0.228 Uiso 1 1 calc R
H22B H 0.0276 0.8106 0.1385 0.228 Uiso 1 1 calc R
H22C H 0.0055 0.6979 0.0863 0.228 Uiso 1 1 calc R
C23 C 0.16249(16) 0.7027(3) 0.4517(2) 0.0932(10) Uani 1 1 d .
H23A H 0.145 0.7737 0.4518 0.14 Uiso 1 1 calc R
H23B H 0.2039 0.7099 0.4799 0.14 Uiso 1 1 calc R
H23C H 0.1501 0.6501 0.486 0.14 Uiso 1 1 calc R
C24 C 0.0340(2) 0.4322(5) 0.3214(4) 0.159(2) Uani 1 1 d D
H24A H 0.0094 0.4728 0.345 0.19 Uiso 1 1 calc R
H24B H 0.0535 0.486 0.2978 0.19 Uiso 1 1 calc R
C25 C 0.0749(3) 0.3732(5) 0.3928(4) 0.176(2) Uani 1 1 d DU
H25A H 0.0561 0.3152 0.4126 0.263 Uiso 1 1 calc R
H25B H 0.0945 0.4225 0.4437 0.263 Uiso 1 1 calc R
H25C H 0.1025 0.341 0.3719 0.263 Uiso 1 1 calc R
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 0 '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 0.006 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 O1 H1 106.1(17) . .
C15 O2 H2 112(2) . .
C24 O3 C24 107.1(6) . 2
C19 O18 C17 113.4(2) . .
C7 N8 C16 111.44(19) . .
C7 N8 C9 109.76(19) . .
C16 N8 C9 113.0(2) . .
O1 C1 C6 121.0(2) . .
O1 C1 C2 118.5(2) . .
C6 C1 C2 120.4(2) . .
C3 C2 C1 118.1(2) . .
C3 C2 C20 121.5(2) . .
C1 C2 C20 120.4(2) . .
C2 C3 C4 123.2(2) . .
C2 C3 H3 118.4 . .
C4 C3 H3 118.4 . .
C3 C4 C5 117.6(2) . .
C3 C4 C21 121.5(3) . .
C5 C4 C21 121.0(3) . .
C4 C5 C6 121.3(2) . .
C4 C5 H5 119.3 . .
C6 C5 H5 119.3 . .
C5 C6 C1 119.3(2) . .
C5 C6 C7 120.9(2) . .
C1 C6 C7 119.8(2) . .
N8 C7 C6 112.2(2) . .
N8 C7 H7A 109.2 . .
C6 C7 H7A 109.2 . .
N8 C7 H7B 109.2 . .
C6 C7 H7B 109.2 . .
H7A C7 H7B 107.9 . .
N8 C9 C10 112.5(2) . .
N8 C9 H9A 109.1 . .
C10 C9 H9A 109.1 . .
N8 C9 H9B 109.1 . .
C10 C9 H9B 109.1 . .
H9A C9 H9B 107.8 . .
C15 C10 C11 117.9(3) . .
C15 C10 C9 120.9(2) . .
C11 C10 C9 121.2(3) . .
C12 C11 C10 122.3(3) . .
C12 C11 H11 118.9 . .
C10 C11 H11 118.9 . .
C13 C12 C11 117.7(3) . .
C13 C12 C22 121.8(4) . .
C11 C12 C22 120.5(4) . .
C12 C13 C14 122.6(3) . .
C12 C13 H13 118.7 . .
C14 C13 H13 118.7 . .
C13 C14 C15 117.9(3) . .
C13 C14 C23 121.2(3) . .
C15 C14 C23 120.9(3) . .
O2 C15 C10 122.3(2) . .
O2 C15 C14 116.2(2) . .
C10 C15 C14 121.5(2) . .
N8 C16 C17 111.4(2) . .
N8 C16 H16A 109.3 . .
C17 C16 H16A 109.3 . .
N8 C16 H16B 109.3 . .
C17 C16 H16B 109.3 . .
H16A C16 H16B 108 . .
O18 C17 C16 108.7(2) . .
O18 C17 H17A 109.9 . .
C16 C17 H17A 109.9 . .
O18 C17 H17B 109.9 . .
C16 C17 H17B 109.9 . .
H17A C17 H17B 108.3 . .
O18 C19 C19 106.9(3) . 7_556
O18 C19 H19A 110.3 . .
C19 C19 H19A 110.3 7_556 .
O18 C19 H19B 110.3 . .
C19 C19 H19B 110.3 7_556 .
H19A C19 H19B 108.6 . .
C2 C20 H20A 109.5 . .
C2 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C2 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C4 C21 H21A 109.5 . .
C4 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C4 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C12 C22 H22A 109.5 . .
C12 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C12 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C14 C23 H23A 109.5 . .
C14 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C14 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
O3 C24 C25 112.3(5) . .
O3 C24 H24A 109.2 . .
C25 C24 H24A 109.2 . .
O3 C24 H24B 109.2 . .
C25 C24 H24B 109.2 . .
H24A C24 H24B 107.9 . .
C24 C25 H25A 109.5 . .
C24 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C24 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.371(3) .
O1 H1 0.94(3) .
O2 C15 1.370(3) .
O2 H2 0.86(3) .
O3 C24 1.395(6) .
O3 C24 1.395(6) 2
O18 C19 1.419(3) .
O18 C17 1.428(3) .
N8 C7 1.473(3) .
N8 C16 1.478(3) .
N8 C9 1.479(3) .
C1 C6 1.394(3) .
C1 C2 1.397(3) .
C2 C3 1.379(4) .
C2 C20 1.511(4) .
C3 C4 1.385(4) .
C3 H3 0.94 .
C4 C5 1.387(4) .
C4 C21 1.521(4) .
C5 C6 1.390(3) .
C5 H5 0.94 .
C6 C7 1.508(3) .
C7 H7A 0.98 .
C7 H7B 0.98 .
C9 C10 1.506(4) .
C9 H9A 0.98 .
C9 H9B 0.98 .
C10 C15 1.392(4) .
C10 C11 1.392(4) .
C11 C12 1.390(5) .
C11 H11 0.94 .
C12 C13 1.375(5) .
C12 C22 1.525(5) .
C13 C14 1.392(4) .
C13 H13 0.94 .
C14 C15 1.393(4) .
C14 C23 1.495(4) .
C16 C17 1.493(4) .
C16 H16A 0.98 .
C16 H16B 0.98 .
C17 H17A 0.98 .
C17 H17B 0.98 .
C19 C19 1.487(5) 7_556
C19 H19A 0.98 .
C19 H19B 0.98 .
C20 H20A 0.97 .
C20 H20B 0.97 .
C20 H20C 0.97 .
C21 H21A 0.97 .
C21 H21B 0.97 .
C21 H21C 0.97 .
C22 H22A 0.97 .
C22 H22B 0.97 .
C22 H22C 0.97 .
C23 H23A 0.97 .
C23 H23B 0.97 .
C23 H23C 0.97 .
C24 C25 1.395(6) .
C24 H24A 0.98 .
C24 H24B 0.98 .
C25 H25A 0.97 .
C25 H25B 0.97 .
C25 H25C 0.97 .
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
O1 H1 N8 0.94(3) 1.91(3) 2.754(3) 148(2)
O2 H2 O18 0.86(3) 2.07(3) 2.881(3) 158(3)
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O1 C1 C2 C3 179.3(2) . .
C6 C1 C2 C3 -1.3(4) . .
O1 C1 C2 C20 -0.7(4) . .
C6 C1 C2 C20 178.6(3) . .
C1 C2 C3 C4 -1.8(4) . .
C20 C2 C3 C4 178.2(3) . .
C2 C3 C4 C5 2.9(4) . .
C2 C3 C4 C21 -177.6(3) . .
C3 C4 C5 C6 -0.9(4) . .
C21 C4 C5 C6 179.6(3) . .
C4 C5 C6 C1 -2.1(4) . .
C4 C5 C6 C7 177.0(2) . .
O1 C1 C6 C5 -177.5(2) . .
C2 C1 C6 C5 3.2(4) . .
O1 C1 C6 C7 3.4(3) . .
C2 C1 C6 C7 -175.9(2) . .
C16 N8 C7 C6 -63.8(3) . .
C9 N8 C7 C6 170.3(2) . .
C5 C6 C7 N8 131.8(2) . .
C1 C6 C7 N8 -49.1(3) . .
C7 N8 C9 C10 -77.6(3) . .
C16 N8 C9 C10 157.4(2) . .
N8 C9 C10 C15 -66.8(3) . .
N8 C9 C10 C11 114.4(3) . .
C15 C10 C11 C12 0.0(4) . .
C9 C10 C11 C12 178.8(3) . .
C10 C11 C12 C13 0.6(5) . .
C10 C11 C12 C22 179.5(3) . .
C11 C12 C13 C14 -0.9(5) . .
C22 C12 C13 C14 -179.8(3) . .
C12 C13 C14 C15 0.6(4) . .
C12 C13 C14 C23 -177.9(3) . .
C11 C10 C15 O2 178.7(2) . .
C9 C10 C15 O2 -0.1(3) . .
C11 C10 C15 C14 -0.4(4) . .
C9 C10 C15 C14 -179.2(2) . .
C13 C14 C15 O2 -179.1(2) . .
C23 C14 C15 O2 -0.6(4) . .
C13 C14 C15 C10 0.1(4) . .
C23 C14 C15 C10 178.5(2) . .
C7 N8 C16 C17 140.6(2) . .
C9 N8 C16 C17 -95.2(3) . .
C19 O18 C17 C16 163.8(2) . .
N8 C16 C17 O18 59.8(3) . .
C17 O18 C19 C19 -179.6(2) . 7_556
C24 O3 C24 C25 -172.7(6) 2 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139198231
