#------------------------------------------------------------------------------
#$Date: 2025-08-19 14:52:15 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301804 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/52/2215202.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_2215202
loop_
_publ_author_name
'Ya-Mei Pei'
'Xiang-Gao Meng'
'Chun-Shan Zhou'
_publ_section_title
;N,N,N',N'-Tetrakis(benzimidazol-2-ylmethyl)ethane-1,2-diamine
 methanol tetrasolvate dihydrate
;
_journal_coeditor_code           LH2470
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3762
_journal_page_last               o3762
_journal_paper_doi               10.1107/S1600536807038111
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C34 H32 N10, 4C H4 O, 2H2 O'
_chemical_formula_moiety         'C34 H32 N10, 4(C H4 O), 2(H2 O)'
_chemical_formula_sum            'C38 H52 N10 O6'
_chemical_formula_weight         744.90
_chemical_name_systematic
;
N,N,N',N'-Tetrakis(benzimidazol-2-ylmethyl)\
ethane-1,2-diamine methanol tetrasolvate dihydrate
;
_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                100.5000(10)
_cell_angle_beta                 101.7630(10)
_cell_angle_gamma                99.4170(10)
_cell_formula_units_Z            1
_cell_length_a                   9.2349(6)
_cell_length_b                   10.4290(7)
_cell_length_c                   11.5344(8)
_cell_measurement_reflns_used    3273
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.86
_cell_measurement_theta_min      2.30
_cell_volume                     1045.83(12)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  PLATON
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '0.3° wide ω exposures'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine focus sealed Siemens Mo tube'
_diffrn_radiation_type           'Mo k\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0936
_diffrn_reflns_av_sigmaI/netI    0.0695
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10988
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_correction_T_min  0.9837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             398
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.258
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4083
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0586
_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)+(0.087P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1496
_refine_ls_wR_factor_ref         0.1627
_reflns_number_gt                2726
_reflns_number_total             4083
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2470.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               2215202
_cod_database_fobs_code          2215202
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
C C1 0.0644(2) 0.05926(17) 0.52781(15) 0.0480(4) Uani d . 1
H H1A 0.0399 0.1163 0.5943 0.058 Uiso calc R 1
H H1B 0.1549 0.0289 0.5604 0.058 Uiso calc R 1
C C2 0.1912(2) 0.0801(2) 0.36638(17) 0.0568(5) Uani d . 1
H H2A 0.1693 -0.0161 0.3554 0.068 Uiso calc R 1
H H2B 0.2955 0.1131 0.4118 0.068 Uiso calc R 1
C C3 0.1733(2) 0.11411(17) 0.24450(16) 0.0503(5) Uani d . 1
C C4 0.0658(2) 0.16310(17) 0.07461(16) 0.0545(5) Uani d . 1
C C5 -0.0262(3) 0.1985(2) -0.01979(18) 0.0683(6) Uani d . 1
H H5 -0.1238 0.2093 -0.0182 0.082 Uiso calc R 1
C C6 0.0359(4) 0.2169(2) -0.11684(19) 0.0812(7) Uani d . 1
H H6 -0.0208 0.2428 -0.1815 0.097 Uiso calc R 1
C C7 0.1793(4) 0.1977(3) -0.1200(2) 0.0887(8) Uani d . 1
H H7 0.2159 0.2091 -0.1876 0.106 Uiso calc R 1
C C8 0.2696(3) 0.1622(2) -0.0263(2) 0.0758(7) Uani d . 1
H H8 0.3660 0.1491 -0.0295 0.091 Uiso calc R 1
C C9 0.2119(2) 0.14626(18) 0.07405(17) 0.0567(5) Uani d . 1
C C10 0.1497(2) 0.27781(18) 0.49058(18) 0.0553(5) Uani d . 1
H H10A 0.1750 0.3237 0.4291 0.066 Uiso calc R 1
H H10B 0.2408 0.2903 0.5542 0.066 Uiso calc R 1
C C11 0.0337(2) 0.33503(17) 0.54216(17) 0.0504(5) Uani d . 1
C C12 -0.0839(2) 0.43572(17) 0.66124(17) 0.0550(5) Uani d . 1
C C13 -0.1279(3) 0.5076(2) 0.7564(2) 0.0724(6) Uani d . 1
H H13 -0.0576 0.5504 0.8287 0.087 Uiso calc R 1
C C14 -0.2771(3) 0.5143(2) 0.7419(2) 0.0815(7) Uani d . 1
H H14 -0.3078 0.5633 0.8048 0.098 Uiso calc R 1
C C15 -0.3834(3) 0.4495(2) 0.6349(3) 0.0812(7) Uani d . 1
H H15 -0.4841 0.4557 0.6277 0.097 Uiso calc R 1
C C16 -0.3428(3) 0.3760(2) 0.5389(2) 0.0719(6) Uani d . 1
H H16 -0.4138 0.3326 0.4671 0.086 Uiso calc R 1
C C17 -0.1918(2) 0.36981(18) 0.55440(18) 0.0552(5) Uani d . 1
C C18 0.4678(4) 0.8728(4) 0.2625(4) 0.1300(12) Uani d . 1
H H18A 0.5412 0.8183 0.2553 0.195 Uiso calc R 1
H H18B 0.3708 0.8250 0.2126 0.195 Uiso calc R 1
H H18C 0.4617 0.8944 0.3457 0.195 Uiso calc R 1
C C19 0.6472(5) 0.4394(4) 0.0909(4) 0.174(2) Uani d . 1
H H19A 0.6046 0.5171 0.1058 0.261 Uiso calc R 1
H H19B 0.5715 0.3674 0.0368 0.261 Uiso calc R 1
H H19C 0.7307 0.4586 0.0546 0.261 Uiso calc R 1
N N1 0.09316(17) 0.13561(13) 0.43655(12) 0.0474(4) Uani d . 1
N N2 0.27737(18) 0.11545(16) 0.18230(14) 0.0581(4) Uani d . 1
N N3 0.04414(19) 0.14113(15) 0.18572(13) 0.0521(4) Uani d D 1
H H3A -0.040(2) 0.151(2) 0.2111(18) 0.063 Uiso d D 1
N N4 0.05769(19) 0.41225(14) 0.65166(14) 0.0560(4) Uani d . 1
N N5 -0.11288(19) 0.30662(16) 0.48112(15) 0.0553(4) Uani d D 1
H H5A -0.143(2) 0.259(2) 0.4045(18) 0.066 Uiso d D 1
O O1 0.75915(17) 0.17048(18) 0.23664(15) 0.0740(5) Uani d D 1
H H1C 0.732(3) 0.238(3) 0.209(3) 0.111 Uiso d D 1
H H1D 0.682(3) 0.114(3) 0.236(3) 0.111 Uiso d D 1
O O2 0.6956(3) 0.4047(2) 0.1961(3) 0.1419(10) Uani d D 1
H H2C 0.771(4) 0.468(4) 0.242(4) 0.213 Uiso d D 1
O O3 0.5088(2) 0.9845(3) 0.2266(3) 0.1536(11) Uani d D 1
H H3B 0.444(5) 1.036(5) 0.228(5) 0.230 Uiso d D 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
_geom_angle_publ_flag
N1 C1 C1 . 2_556 110.60(17) no
N1 C1 H1A . . 109.5 no
C1 C1 H1A 2_556 . 109.5 no
N1 C1 H1B . . 109.5 no
C1 C1 H1B 2_556 . 109.5 no
H1A C1 H1B . . 108.1 no
N1 C2 C3 . . 113.09(14) no
N1 C2 H2A . . 109.0 no
C3 C2 H2A . . 109.0 no
N1 C2 H2B . . 109.0 no
C3 C2 H2B . . 109.0 no
H2A C2 H2B . . 107.8 no
N2 C3 N3 . . 113.39(16) no
N2 C3 C2 . . 124.18(17) no
N3 C3 C2 . . 122.37(15) no
C5 C4 C9 . . 122.96(18) no
C5 C4 N3 . . 131.8(2) no
C9 C4 N3 . . 105.17(17) no
C4 C5 C6 . . 116.0(2) no
C4 C5 H5 . . 122.0 no
C6 C5 H5 . . 122.0 no
C7 C6 C5 . . 121.8(2) no
C7 C6 H6 . . 119.1 no
C5 C6 H6 . . 119.1 no
C8 C7 C6 . . 121.9(2) no
C8 C7 H7 . . 119.1 no
C6 C7 H7 . . 119.1 no
C7 C8 C9 . . 117.8(2) no
C7 C8 H8 . . 121.1 no
C9 C8 H8 . . 121.1 no
N2 C9 C4 . . 109.66(15) no
N2 C9 C8 . . 130.7(2) no
C4 C9 C8 . . 119.6(2) no
N1 C10 C11 . . 110.23(15) no
N1 C10 H10A . . 109.6 no
C11 C10 H10A . . 109.6 no
N1 C10 H10B . . 109.6 no
C11 C10 H10B . . 109.6 no
H10A C10 H10B . . 108.1 no
N4 C11 N5 . . 112.63(17) no
N4 C11 C10 . . 125.50(18) no
N5 C11 C10 . . 121.80(17) no
C13 C12 N4 . . 130.5(2) no
C13 C12 C17 . . 119.8(2) no
N4 C12 C17 . . 109.68(16) no
C14 C13 C12 . . 118.6(2) no
C14 C13 H13 . . 120.7 no
C12 C13 H13 . . 120.7 no
C13 C14 C15 . . 121.3(2) no
C13 C14 H14 . . 119.4 no
C15 C14 H14 . . 119.4 no
C16 C15 C14 . . 121.4(2) no
C16 C15 H15 . . 119.3 no
C14 C15 H15 . . 119.3 no
C15 C16 C17 . . 117.0(2) no
C15 C16 H16 . . 121.5 no
C17 C16 H16 . . 121.5 no
N5 C17 C16 . . 132.83(19) no
N5 C17 C12 . . 105.11(17) no
C16 C17 C12 . . 122.06(19) no
O3 C18 H18A . . 109.5 no
O3 C18 H18B . . 109.5 no
H18A C18 H18B . . 109.5 no
O3 C18 H18C . . 109.5 no
H18A C18 H18C . . 109.5 no
H18B C18 H18C . . 109.5 no
O2 C19 H19A . . 109.5 no
O2 C19 H19B . . 109.5 no
H19A C19 H19B . . 109.5 no
O2 C19 H19C . . 109.5 no
H19A C19 H19C . . 109.5 no
H19B C19 H19C . . 109.5 no
C2 N1 C10 . . 112.26(14) no
C2 N1 C1 . . 111.51(13) no
C10 N1 C1 . . 111.94(13) no
C3 N2 C9 . . 105.00(16) no
C3 N3 C4 . . 106.77(15) no
C3 N3 H3A . . 129.9(13) no
C4 N3 H3A . . 123.2(13) no
C11 N4 C12 . . 104.79(16) no
C11 N5 C17 . . 107.78(16) no
C11 N5 H5A . . 121.4(13) no
C17 N5 H5A . . 130.7(13) no
H1C O1 H1D . . 110(2) no
C19 O2 H2C . . 109(3) no
C18 O3 H3B . . 114(4) no
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 N1 . 1.471(2) no
C1 C1 2_556 1.508(4) no
C1 H1A . 0.9700 no
C1 H1B . 0.9700 no
C2 N1 . 1.452(2) no
C2 C3 . 1.495(2) no
C2 H2A . 0.9700 no
C2 H2B . 0.9700 no
C3 N2 . 1.311(2) no
C3 N3 . 1.346(2) no
C4 C5 . 1.384(3) no
C4 C9 . 1.389(3) no
C4 N3 . 1.390(2) no
C5 C6 . 1.386(3) no
C5 H5 . 0.9300 no
C6 C7 . 1.378(4) no
C6 H6 . 0.9300 no
C7 C8 . 1.372(4) no
C7 H7 . 0.9300 no
C8 C9 . 1.394(3) no
C8 H8 . 0.9300 no
C9 N2 . 1.389(3) no
C10 N1 . 1.462(2) no
C10 C11 . 1.482(3) no
C10 H10A . 0.9700 no
C10 H10B . 0.9700 no
C11 N4 . 1.323(2) no
C11 N5 . 1.349(2) no
C12 C13 . 1.384(3) no
C12 N4 . 1.391(3) no
C12 C17 . 1.397(3) no
C13 C14 . 1.368(3) no
C13 H13 . 0.9300 no
C14 C15 . 1.389(4) no
C14 H14 . 0.9300 no
C15 C16 . 1.381(3) no
C15 H15 . 0.9300 no
C16 C17 . 1.383(3) no
C16 H16 . 0.9300 no
C17 N5 . 1.373(2) no
C18 O3 . 1.330(4) no
C18 H18A . 0.9600 no
C18 H18B . 0.9600 no
C18 H18C . 0.9600 no
C19 O2 . 1.340(4) no
C19 H19A . 0.9600 no
C19 H19B . 0.9600 no
C19 H19C . 0.9600 no
N3 H3A . 0.899(18) no
N5 H5A . 0.895(19) no
O1 H1C . 0.87(2) no
O1 H1D . 0.84(2) no
O2 H2C . 0.88(3) no
O3 H3B . 0.86(3) no
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 H1C O2 . 0.87(2) 1.85(2) 2.702(3) 164(3) yes
O3 H3B N2 1_565 0.86(3) 1.90(4) 2.731(2) 163(5) yes
N5 H5A O1 1_455 0.895(19) 1.94(2) 2.828(2) 169.5(19) yes
N3 H3A O1 1_455 0.899(18) 1.972(19) 2.862(2) 170.0(18) yes
O2 H2C N4 2_666 0.88(3) 1.89(3) 2.765(3) 173(5) yes
O1 H1D O3 1_545 0.84(2) 1.89(2) 2.731(3) 177(3) yes
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
_geom_torsion_publ_flag
N1 C2 C3 N2 . 156.56(17) no
N1 C2 C3 N3 . -26.3(3) no
C9 C4 C5 C6 . -0.1(3) no
N3 C4 C5 C6 . 177.65(19) no
C4 C5 C6 C7 . 1.5(3) no
C5 C6 C7 C8 . -1.4(4) no
C6 C7 C8 C9 . -0.3(4) no
C5 C4 C9 N2 . 177.98(17) no
N3 C4 C9 N2 . -0.3(2) no
C5 C4 C9 C8 . -1.5(3) no
N3 C4 C9 C8 . -179.79(18) no
C7 C8 C9 N2 . -177.7(2) no
C7 C8 C9 C4 . 1.7(3) no
N1 C10 C11 N4 . 132.12(17) no
N1 C10 C11 N5 . -44.6(2) no
N4 C12 C13 C14 . -179.68(19) no
C17 C12 C13 C14 . -1.4(3) no
C12 C13 C14 C15 . 0.8(3) no
C13 C14 C15 C16 . -0.2(4) no
C14 C15 C16 C17 . 0.1(3) no
C15 C16 C17 N5 . 179.17(19) no
C15 C16 C17 C12 . -0.7(3) no
C13 C12 C17 N5 . -178.53(16) no
N4 C12 C17 N5 . 0.09(19) no
C13 C12 C17 C16 . 1.4(3) no
N4 C12 C17 C16 . -179.99(17) no
C3 C2 N1 C10 . -77.3(2) no
C3 C2 N1 C1 . 156.14(16) no
C11 C10 N1 C2 . 169.89(14) no
C11 C10 N1 C1 . -63.81(19) no
C1 C1 N1 C2 2_556 -84.5(2) no
C1 C1 N1 C10 2_556 148.77(19) no
N3 C3 N2 C9 . 0.2(2) no
C2 C3 N2 C9 . 177.57(17) no
C4 C9 N2 C3 . 0.0(2) no
C8 C9 N2 C3 . 179.5(2) no
N2 C3 N3 C4 . -0.4(2) no
C2 C3 N3 C4 . -177.79(16) no
C5 C4 N3 C3 . -177.6(2) no
C9 C4 N3 C3 . 0.38(19) no
N5 C11 N4 C12 . -0.37(19) no
C10 C11 N4 C12 . -177.35(15) no
C13 C12 N4 C11 . 178.59(18) no
C17 C12 N4 C11 . 0.16(18) no
N4 C11 N5 C17 . 0.4(2) no
C10 C11 N5 C17 . 177.55(14) no
C16 C17 N5 C11 . 179.8(2) no
C12 C17 N5 C11 . -0.30(18) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168309295
