#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/37/2203745.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_2203745
loop_
_publ_author_name
'Qin, Shi-Dong'
'Feng, Si-Si'
'Zhang, Hong-Mei'
'Yang, Pin'
'Zhu, Miao-Li'
_publ_section_title
;N,N,N',N'-Tetrakis[(1H-benzimidazol-2-yl)methyl]ethane-1,2-diamine
 glycol disolvate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1121
_journal_page_last               o1122
_journal_paper_doi               10.1107/S1600536804012826
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C34 H32 N10 , 2C2 H6 O2'
_chemical_formula_moiety         'C34 H32 N10 , 2C2 H6 O2'
_chemical_formula_sum            'C38 H44 N10 O4'
_chemical_formula_weight         704.83
_chemical_name_systematic
;
N,N,N',N'-Tetrakis[(1H-benzimidazol-2-yl)methyl]ethane-1,2-diamine
glycol disolvate
;
_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           SHELXL97
_cell_angle_alpha                85.764(3)
_cell_angle_beta                 76.748(3)
_cell_angle_gamma                66.394(3)
_cell_formula_units_Z            1
_cell_length_a                   9.2367(15)
_cell_length_b                   9.7383(16)
_cell_length_c                   11.5791(19)
_cell_measurement_reflns_used    1058
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.58
_cell_measurement_theta_min      2.28
_cell_volume                     928.8(3)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1999)'
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 25.00
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_device_type  'Bruker SMART 1K 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  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4360
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.81
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9899
_exptl_absorpt_correction_T_min  0.9725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             374
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.278
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2992
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0689
_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)+(0.1469P)²+0.1154P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1977
_refine_ls_wR_factor_ref         0.2498
_reflns_number_gt                2074
_reflns_number_total             2992
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6318.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_database_code               2203745
_cod_database_fobs_code          2203745
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
C1 0.2053(4) 0.4922(4) 0.2594(3) 0.0535(9) Uani d . 1 C
C2 0.1950(4) 0.3802(4) 0.4297(3) 0.0540(9) Uani d . 1 C
C3 0.1825(5) 0.2893(5) 0.5258(4) 0.0717(11) Uani d . 1 C
H3 0.1458 0.2136 0.5239 0.086 Uiso calc R 1 H
C4 0.2272(6) 0.3164(6) 0.6243(4) 0.0889(14) Uani d . 1 C
H4 0.2198 0.2574 0.6905 0.107 Uiso calc R 1 H
C5 0.2817(6) 0.4262(6) 0.6289(4) 0.0883(14) Uani d . 1 C
H5 0.3105 0.4399 0.6977 0.106 Uiso calc R 1 H
C6 0.2951(5) 0.5171(5) 0.5346(4) 0.0797(13) Uani d . 1 C
H6 0.3308 0.5931 0.5383 0.096 Uiso calc R 1 H
C7 0.2529(4) 0.4906(4) 0.4331(3) 0.0577(9) Uani d . 1 C
C8 0.1841(5) 0.5368(4) 0.1367(3) 0.0632(10) Uani d . 1 C
H8A 0.0836 0.6242 0.1408 0.076 Uiso calc R 1 H
H8B 0.2719 0.5648 0.0956 0.076 Uiso calc R 1 H
C9 0.0889(4) 0.4788(4) -0.0245(3) 0.0534(9) Uani d . 1 C
H9A 0.1266 0.4044 -0.0877 0.064 Uiso calc R 1 H
H9B 0.1071 0.5663 -0.0577 0.064 Uiso calc R 1 H
C10 0.3460(4) 0.3086(4) 0.0211(3) 0.0577(9) Uani d . 1 C
H10A 0.4031 0.2744 0.0852 0.069 Uiso calc R 1 H
H10B 0.4039 0.3565 -0.0367 0.069 Uiso calc R 1 H
C11 0.3434(4) 0.1777(4) -0.0358(3) 0.0513(8) Uani d . 1 C
C12 0.2863(4) -0.0055(4) -0.0750(3) 0.0575(9) Uani d . 1 C
C13 0.2256(5) -0.1141(5) -0.0743(4) 0.0800(12) Uani d . 1 C
H13 0.1491 -0.1238 -0.0099 0.096 Uiso calc R 1 H
C14 0.2829(5) -0.2078(5) -0.1726(5) 0.0874(14) Uani d . 1 C
H14 0.2450 -0.2828 -0.1742 0.105 Uiso calc R 1 H
C15 0.3960(5) -0.1928(5) -0.2698(4) 0.0762(12) Uani d . 1 C
H15 0.4304 -0.2566 -0.3354 0.091 Uiso calc R 1 H
C16 0.4574(4) -0.0870(4) -0.2707(3) 0.0655(10) Uani d . 1 C
H16 0.5344 -0.0780 -0.3351 0.079 Uiso calc R 1 H
C17 0.4003(4) 0.0072(4) -0.1715(3) 0.0535(9) Uani d . 1 C
N1 0.1662(3) 0.3836(3) 0.3178(2) 0.0552(8) Uani d . 1 N
H1 0.1299 0.3268 0.2906 0.066 Uiso calc R 1 H
N2 0.2592(3) 0.5606(3) 0.3225(3) 0.0625(8) Uani d . 1 N
N3 0.4350(3) 0.1236(3) -0.1438(2) 0.0544(8) Uani d . 1 N
H3A 0.5028 0.1561 -0.1876 0.065 Uiso calc R 1 H
N4 0.2519(3) 0.1040(3) 0.0094(3) 0.0616(8) Uani d . 1 N
N5 0.1809(3) 0.4180(3) 0.0683(2) 0.0507(7) Uani d . 1 N
C18 0.0603(6) 1.0397(6) 0.3095(5) 0.0934(14) Uani d . 1 C
H18A 0.0165 0.9998 0.2581 0.112 Uiso calc R 1 H
H18B -0.0272 1.0907 0.3759 0.112 Uiso calc R 1 H
C19 0.1834(7) 0.9153(6) 0.3547(5) 0.1043(17) Uani d . 1 C
H19A 0.2354 0.9549 0.3995 0.125 Uiso calc R 1 H
H19B 0.1313 0.8595 0.4088 0.125 Uiso calc R 1 H
O1 0.1136(5) 1.1449(4) 0.2466(3) 0.1031(11) Uani d . 1 O
H1A 0.1554 1.1155 0.1776 0.155 Uiso calc R 1 H
O2 0.3022(4) 0.8170(3) 0.2660(3) 0.0987(11) Uani d . 1 O
H2 0.2943 0.7357 0.2713 0.148 Uiso calc R 1 H
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
N2 C1 N1 . . 113.6(3)
N2 C1 C8 . . 122.6(3)
N1 C1 C8 . . 123.8(3)
N1 C2 C3 . . 132.8(3)
N1 C2 C7 . . 106.1(3)
C3 C2 C7 . . 121.1(3)
C4 C3 C2 . . 116.6(4)
C4 C3 H3 . . 121.7
C2 C3 H3 . . 121.7
C5 C4 C3 . . 122.7(4)
C5 C4 H4 . . 118.7
C3 C4 H4 . . 118.7
C4 C5 C6 . . 121.5(4)
C4 C5 H5 . . 119.2
C6 C5 H5 . . 119.2
C5 C6 C7 . . 117.0(4)
C5 C6 H6 . . 121.5
C7 C6 H6 . . 121.5
C2 C7 C6 . . 121.1(4)
C2 C7 N2 . . 108.8(3)
C6 C7 N2 . . 130.1(4)
N5 C8 C1 . . 113.2(3)
N5 C8 H8A . . 108.9
C1 C8 H8A . . 108.9
N5 C8 H8B . . 108.9
C1 C8 H8B . . 108.9
H8A C8 H8B . . 107.8
N5 C9 C9 . 2_565 111.0(3)
N5 C9 H9A . . 109.4
C9 C9 H9A 2_565 . 109.4
N5 C9 H9B . . 109.4
C9 C9 H9B 2_565 . 109.4
H9A C9 H9B . . 108.0
N5 C10 C11 . . 111.1(3)
N5 C10 H10A . . 109.4
C11 C10 H10A . . 109.4
N5 C10 H10B . . 109.4
C11 C10 H10B . . 109.4
H10A C10 H10B . . 108.0
N4 C11 N3 . . 112.1(3)
N4 C11 C10 . . 125.6(3)
N3 C11 C10 . . 122.3(3)
C13 C12 C17 . . 120.5(3)
C13 C12 N4 . . 130.6(4)
C17 C12 N4 . . 108.9(3)
C14 C13 C12 . . 117.4(4)
C14 C13 H13 . . 121.3
C12 C13 H13 . . 121.3
C13 C14 C15 . . 121.5(4)
C13 C14 H14 . . 119.2
C15 C14 H14 . . 119.2
C16 C15 C14 . . 121.4(4)
C16 C15 H15 . . 119.3
C14 C15 H15 . . 119.3
C15 C16 C17 . . 117.1(4)
C15 C16 H16 . . 121.4
C17 C16 H16 . . 121.4
N3 C17 C12 . . 105.8(3)
N3 C17 C16 . . 132.2(3)
C12 C17 C16 . . 122.0(3)
C1 N1 C2 . . 106.9(3)
C1 N1 H1 . . 126.5
C2 N1 H1 . . 126.5
C1 N2 C7 . . 104.5(3)
C11 N3 C17 . . 107.6(3)
C11 N3 H3A . . 126.2
C17 N3 H3A . . 126.2
C11 N4 C12 . . 105.6(3)
C8 N5 C9 . . 111.8(3)
C8 N5 C10 . . 110.8(3)
C9 N5 C10 . . 112.5(3)
O1 C18 C19 . . 115.1(4)
O1 C18 H18A . . 108.5
C19 C18 H18A . . 108.5
O1 C18 H18B . . 108.5
C19 C18 H18B . . 108.5
H18A C18 H18B . . 107.5
O2 C19 C18 . . 113.8(5)
O2 C19 H19A . . 108.8
C18 C19 H19A . . 108.8
O2 C19 H19B . . 108.8
C18 C19 H19B . . 108.8
H19A C19 H19B . . 107.7
C18 O1 H1A . . 109.5
C19 O2 H2 . . 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
C1 N2 . 1.315(4) y
C1 N1 . 1.339(4) y
C1 C8 . 1.488(5) y
C2 N1 . 1.377(4) y
C2 C3 . 1.384(5) y
C2 C7 . 1.385(5) y
C3 C4 . 1.374(6) y
C3 H3 . 0.9300 ?
C4 C5 . 1.361(7) y
C4 H4 . 0.9300 ?
C5 C6 . 1.369(7) y
C5 H5 . 0.9300 ?
C6 C7 . 1.392(5) y
C6 H6 . 0.9300 ?
C7 N2 . 1.406(5) y
C8 N5 . 1.463(4) y
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 N5 . 1.466(4) y
C9 C9 2_565 1.500(6) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 N5 . 1.470(4) y
C10 C11 . 1.489(5) y
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 N4 . 1.316(4) y
C11 N3 . 1.347(4) y
C12 C13 . 1.380(5) y
C12 C17 . 1.385(5) y
C12 N4 . 1.390(4) y
C13 C14 . 1.379(6) y
C13 H13 . 0.9300 ?
C14 C15 . 1.392(6) y
C14 H14 . 0.9300 ?
C15 C16 . 1.359(5) y
C15 H15 . 0.9300 ?
C16 C17 . 1.389(5) y
C16 H16 . 0.9300 ?
C17 N3 . 1.372(4) y
N1 H1 . 0.8600 ?
N3 H3A . 0.8600 ?
C18 O1 . 1.397(5) ?
C18 C19 . 1.452(7) ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C19 O2 . 1.401(5) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
O1 H1A . 0.8200 ?
O2 H2 . 0.8200 ?
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
O1 H1A N4 1_565 0.82 1.94 2.734(4) 164 y
O2 H2 N2 . 0.82 1.89 2.693(4) 166 y
N3 H3A O2 2_665 0.86 1.93 2.767(4) 164 y
N1 H1 O1 1_545 0.86 1.95 2.774(4) 160 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
N1 C2 C3 C4 . 178.0(4)
C7 C2 C3 C4 . 1.2(5)
C2 C3 C4 C5 . -0.2(6)
C3 C4 C5 C6 . 0.1(7)
C4 C5 C6 C7 . -1.0(6)
N1 C2 C7 C6 . -179.8(3)
C3 C2 C7 C6 . -2.2(5)
N1 C2 C7 N2 . -0.1(3)
C3 C2 C7 N2 . 177.4(3)
C5 C6 C7 C2 . 2.0(6)
C5 C6 C7 N2 . -177.5(4)
N2 C1 C8 N5 . 159.0(3)
N1 C1 C8 N5 . -23.6(5)
N5 C10 C11 N4 . -46.1(5)
N5 C10 C11 N3 . 132.1(3)
C17 C12 C13 C14 . 0.0(6)
N4 C12 C13 C14 . 179.6(4)
C12 C13 C14 C15 . -0.7(7)
C13 C14 C15 C16 . 1.4(7)
C14 C15 C16 C17 . -1.1(6)
C13 C12 C17 N3 . -179.7(3)
N4 C12 C17 N3 . 0.6(4)
C13 C12 C17 C16 . 0.2(5)
N4 C12 C17 C16 . -179.4(3)
C15 C16 C17 N3 . -179.8(3)
C15 C16 C17 C12 . 0.3(5)
N2 C1 N1 C2 . 0.6(4)
C8 C1 N1 C2 . -177.0(3)
C3 C2 N1 C1 . -177.4(4)
C7 C2 N1 C1 . -0.3(3)
N1 C1 N2 C7 . -0.7(4)
C8 C1 N2 C7 . 177.0(3)
C2 C7 N2 C1 . 0.5(4)
C6 C7 N2 C1 . -179.9(4)
N4 C11 N3 C17 . 0.4(4)
C10 C11 N3 C17 . -178.1(3)
C12 C17 N3 C11 . -0.6(3)
C16 C17 N3 C11 . 179.5(4)
N3 C11 N4 C12 . 0.0(4)
C10 C11 N4 C12 . 178.4(3)
C13 C12 N4 C11 . 180.0(4)
C17 C12 N4 C11 . -0.4(4)
C1 C8 N5 C9 . 153.4(3)
C1 C8 N5 C10 . -80.2(4)
C9 C9 N5 C8 2_565 -84.1(4)
C9 C9 N5 C10 2_565 150.5(4)
C11 C10 N5 C8 . 173.0(3)
C11 C10 N5 C9 . -61.0(4)
O1 C18 C19 O2 . -69.1(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139066730
