#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/04/2200471.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_2200471
loop_
_publ_author_name
'Daly, Robert I.'
'Hockless, David C. R.'
'Taylor, Max R.'
'Martin, Lisandra L.'
_publ_section_title
;{2-(4,7-Dimethyl-1,4,7-triazacyclonon-1-yl)-N-methyl-N-[(1-methylbenzimidazol-2-yl)methyl]ethylamine}copper(II)
 bis(perchlorate)
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m355
_journal_page_last               m356
_journal_paper_doi               10.1107/S1600536801011540
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          '[Cu (C20 H34 N6)](Cl O4)2'
_chemical_formula_moiety         'C20 H34 Cu N6 2+, 2Cl O4 1-'
_chemical_formula_sum            'C20 H34 Cl2 Cu N6 O8'
_chemical_formula_weight         620.98
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.978(2)
_cell_length_b                   16.518(2)
_cell_length_c                   23.950(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    213.2
_cell_measurement_theta_max      49.8
_cell_measurement_theta_min      48.6
_cell_volume                     5134.2(13)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1992)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1992-1997)'
_computing_molecular_graphics    'Xtal3.4 PIG ORTEP'
_computing_publication_material  'Xtal3.4 BONDLA CIFIO'
_computing_structure_refinement  'Xtal3.4 CRYLSQ (Hall et al., 1995)'
_computing_structure_solution    'PATTYy in DIRDIF92 (Beurskens et al., 1992)'
_diffrn_ambient_temperature      213.2
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Rigaku AFC-6R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4291
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        60.07
_diffrn_reflns_theta_max         60.07
_diffrn_reflns_theta_min         1.85
_diffrn_standards_decay_%        .54
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.637
_exptl_absorpt_correction_T_max  .483
_exptl_absorpt_correction_T_min  .382
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_meas      ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             2584.00
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .28
_exptl_crystal_size_min          .20
_refine_diff_density_max         1.195
_refine_diff_density_min         -.547
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.377
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         3263
_refine_ls_R_factor_gt           .054
_refine_ls_shift/su_max          .0003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'calc w=1/[σ²(Fo²)+(0.1Fo²)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .165
_reflns_number_gt                3263
_reflns_number_total             3823
_reflns_threshold_expression     Fsqd>1.5σ(Fsqd)
_cod_data_source_file            cv6040.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        5134.0(10)
_cod_original_formula_sum        'C20 H34 Cl2 Cu N6 O8 '
_cod_database_code               2200471
_cod_database_fobs_code          2200471
loop_
_symmetry_equiv_pos_as_xyz
'  +x,  +y,  +z'
'1/2+x,1/2-y,  -z'
'  -x,1/2+y,1/2-z'
'1/2-x,  -y,1/2+z'
'  -x,  -y,  -z'
'1/2-x,1/2+y,  +z'
'  +x,1/2-y,1/2+z'
'1/2+x,  +y,1/2-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_calc_attached_atom
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu .16186(4) -.00140(3) .12678(2) .0211(4) Uani ? ? 1.00000 ? ?
Cl1 -.35065(8) .04176(8) .11549(5) .0423(7) Uani ? ? 1.00000 ? ?
Cl2 -.41164(8) -.28659(6) -.27905(5) .0400(6) Uani ? ? 1.00000 ? ?
O11 -.4288(3) .0894(3) .14298(19) .075(3) Uani ? ? 1.00000 ? ?
O12 -.2791(4) .0166(3) .1562(2) .093(4) Uani ? ? 1.00000 ? ?
O13 -.2996(3) .0904(3) .07510(17) .075(3) Uani ? ? 1.00000 ? ?
O14 -.3983(3) -.0255(3) .0899(2) .084(3) Uani ? ? 1.00000 ? ?
O21 -.3395(4) -.2251(3) -.2759(2) .089(3) Uani ? ? 1.00000 ? ?
O22 -.3669(3) -.3631(2) -.26532(18) .069(3) Uani ? ? 1.00000 ? ?
O23 -.4516(5) -.2871(3) -.3334(2) .111(4) Uani ? ? 1.00000 ? ?
O24 -.4930(6) -.2724(4) -.2432(3) .157(6) Uani ? ? 1.00000 ? ?
N1 .2295(2) .07895(18) .17890(13) .0236(16) Uani ? ? 1.00000 ? ?
N2 .2440(3) .06738(18) .06230(13) .0264(17) Uani ? ? 1.00000 ? ?
N3 .3004(3) -.06548(19) .13277(14) .0257(17) Uani ? ? 1.00000 ? ?
N4 .0271(2) .0265(2) .16738(13) .0244(17) Uani ? ? 1.00000 ? ?
N5 .0712(2) -.0849(2) .09150(13) .0251(17) Uani ? ? 1.00000 ? ?
N6 -.0604(3) -.1683(2) .10945(15) .034(2) Uani ? ? 1.00000 ? ?
C1 .2911(3) .1401(2) .14838(17) .030(2) Uani ? ? 1.00000 ? ?
C2 .2521(3) .1478(2) .08901(17) .032(2) Uani ? ? 1.00000 ? ?
C3 .3473(3) .0299(3) .05528(18) .033(2) Uani ? ? 1.00000 ? ?
C4 .3502(3) -.0574(2) .07673(18) .030(2) Uani ? ? 1.00000 ? ?
C5 .3632(3) -.0265(3) .17784(18) .031(2) Uani ? ? 1.00000 ? ?
C6 .2951(3) .0253(3) .21475(16) .028(2) Uani ? ? 1.00000 ? ?
C7 .1896(4) .0746(3) .00866(18) .039(2) Uani ? ? 1.00000 ? ?
C8 .2860(4) -.1529(2) .1457(2) .038(2) Uani ? ? 1.00000 ? ?
C9 .1466(3) .1196(3) .21298(18) .030(2) Uani ? ? 1.00000 ? ?
C10 .0581(3) .0623(3) .22223(16) .030(2) Uani ? ? 1.00000 ? ?
C11 -.0309(3) -.0496(3) .17436(17) .031(2) Uani ? ? 1.00000 ? ?
C12 -.0075(3) -.1007(2) .12460(15) .026(2) Uani ? ? 1.00000 ? ?
C13 -.0110(3) -.1981(2) .06251(17) .031(2) Uani ? ? 1.00000 ? ?
C14 -.0341(4) -.2651(3) .0287(2) .044(3) Uani ? ? 1.00000 ? ?
C15 .0285(4) -.2757(3) -.0175(2) .046(3) Uani ? ? 1.00000 ? ?
C16 .1090(4) -.2229(3) -.0310(2) .040(3) Uani ? ? 1.00000 ? ?
C17 .1307(3) -.1568(3) .00347(17) .031(2) Uani ? ? 1.00000 ? ?
C18 .0696(3) -.1458(2) .05065(16) .026(2) Uani ? ? 1.00000 ? ?
C19 -.1509(4) -.2018(3) .1377(2) .048(3) Uani ? ? 1.00000 ? ?
C20 -.0322(4) .0844(3) .1331(2) .038(3) Uani ? ? 1.00000 ? ?
H1a .28600 .19090 .16680 .03700 Uiso ? ? 1.00000 ? ?
H1b .36160 .12340 .14800 .03700 Uiso ? ? 1.00000 ? ?
H2a .18650 .17290 .08940 .03900 Uiso ? ? 1.00000 ? ?
H2b .29900 .18030 .06820 .03900 Uiso ? ? 1.00000 ? ?
H3a .39650 .06090 .07510 .04100 Uiso ? ? 1.00000 ? ?
H3b .36420 .02960 .01660 .04100 Uiso ? ? 1.00000 ? ?
H4a .42010 -.07380 .07970 .03800 Uiso ? ? 1.00000 ? ?
H4b .31520 -.09110 .05100 .03800 Uiso ? ? 1.00000 ? ?
H5a .41500 .00660 .16110 .03700 Uiso ? ? 1.00000 ? ?
H5b .39570 -.06730 .19970 .03700 Uiso ? ? 1.00000 ? ?
H6a .33610 .05750 .23870 .03500 Uiso ? ? 1.00000 ? ?
H6b .25160 -.00890 .23670 .03500 Uiso ? ? 1.00000 ? ?
H7a .22630 .10980 -.01550 .04800 Uiso ? ? 1.00000 ? ?
H7b .18390 .02260 -.00840 .04800 Uiso ? ? 1.00000 ? ?
H7c .12200 .09570 .01460 .04800 Uiso ? ? 1.00000 ? ?
H8a .35050 -.17890 .14710 .04600 Uiso ? ? 1.00000 ? ?
H8b .24440 -.17690 .11730 .04600 Uiso ? ? 1.00000 ? ?
H8c .25180 -.15800 .18070 .04600 Uiso ? ? 1.00000 ? ?
H9a .17410 .13550 .24800 .03800 Uiso ? ? 1.00000 ? ?
H9b .12220 .16600 .19360 .03800 Uiso ? ? 1.00000 ? ?
H10a .07900 .02020 .24710 .03700 Uiso ? ? 1.00000 ? ?
H10b .00150 .09060 .23810 .03700 Uiso ? ? 1.00000 ? ?
H11a -.01100 -.07620 .20760 .03700 Uiso ? ? 1.00000 ? ?
H11b -.10330 -.03820 .17590 .03700 Uiso ? ? 1.00000 ? ?
H14 -.08820 -.30150 .03750 .05200 Uiso ? ? 1.00000 ? ?
H15 .01540 -.32020 -.04190 .05500 Uiso ? ? 1.00000 ? ?
H16 .14890 -.23160 -.06330 .04800 Uiso ? ? 1.00000 ? ?
H17 .18570 -.12060 -.00500 .03800 Uiso ? ? 1.00000 ? ?
H19a -.13300 -.21490 .17530 .06000 Uiso ? ? 1.00000 ? ?
H19b -.20440 -.16290 .13760 .06000 Uiso ? ? 1.00000 ? ?
H19c -.17250 -.24930 .11890 .06000 Uiso ? ? 1.00000 ? ?
H20a .00650 .13270 .12840 .04600 Uiso ? ? 1.00000 ? ?
H20b -.04620 .06120 .09750 .04600 Uiso ? ? 1.00000 ? ?
H20c -.09560 .09660 .15120 .04600 Uiso ? ? 1.00000 ? ?
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C .017029 .008972 'Int Tables Vol IV Tables 2.2B and 2.3.1'
H 0 0 'Int Tables Vol IV Tables 2.2B and 2.3.1'
Cl .348023 .702027 'Int Tables Vol IV Tables 2.2B and 2.3.1'
Cu -2.019 .588989 'Int Tables Vol IV Tables 2.2B and 2.3.1'
N .028992 .018005 'Int Tables Vol IV Tables 2.2B and 2.3.1'
O .046997 .031982 'Int Tables Vol IV Tables 2.2B and 2.3.1'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 1 1
0 4 0
0 0 8
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
N1 Cu N2 83.33(12) yes
N1 Cu N3 85.23(13) yes
N1 Cu N4 85.97(13) yes
N1 Cu N5 165.60(13) yes
N2 Cu N3 83.84(12) yes
N2 Cu N4 129.11(12) yes
N2 Cu N5 110.22(12) yes
N3 Cu N4 144.42(13) yes
N3 Cu N5 100.68(13) yes
N4 Cu N5 81.62(13) yes
O11 Cl1 O12 107.9(3) ?
O11 Cl1 O13 109.2(3) ?
O11 Cl1 O14 108.6(3) ?
O12 Cl1 O13 109.3(3) ?
O12 Cl1 O14 110.9(3) ?
O13 Cl1 O14 110.7(3) ?
O21 Cl2 O22 111.2(3) ?
O21 Cl2 O23 107.8(3) ?
O21 Cl2 O24 111.0(3) ?
O22 Cl2 O23 111.1(3) ?
O22 Cl2 O24 108.5(3) ?
O23 Cl2 O24 107.2(4) ?
Cu N1 C1 112.2(2) ?
Cu N1 C6 102.3(2) ?
Cu N1 C9 108.5(2) ?
C1 N1 C6 112.2(3) ?
C1 N1 C9 110.4(3) ?
C6 N1 C9 111.0(3) ?
Cu N2 C2 101.3(2) ?
Cu N2 C3 107.6(2) ?
Cu N2 C7 115.1(3) ?
C2 N2 C3 111.0(3) ?
C2 N2 C7 109.8(3) ?
C3 N2 C7 111.6(3) ?
Cu N3 C4 105.4(2) ?
Cu N3 C5 107.4(2) ?
Cu N3 C8 113.4(3) ?
C4 N3 C5 111.9(3) ?
C4 N3 C8 109.1(3) ?
C5 N3 C8 109.6(3) ?
Cu N4 C10 106.0(2) ?
Cu N4 C11 107.3(2) ?
Cu N4 C20 109.0(3) ?
C10 N4 C11 112.0(3) ?
C10 N4 C20 111.9(3) ?
C11 N4 C20 110.4(3) ?
Cu N5 C12 109.8(3) ?
Cu N5 C18 142.9(3) ?
C12 N5 C18 105.4(3) ?
C12 N6 C13 105.9(3) ?
C12 N6 C19 126.3(4) ?
C13 N6 C19 127.7(4) ?
N1 C1 C2 109.9(3) ?
N1 C1 H1a 109.6 ?
N1 C1 H1b 109.0 ?
C2 C1 H1a 109.7 ?
C2 C1 H1b 109.6 ?
H1a C1 H1b 109.0 ?
N2 C2 C1 110.7(3) ?
N2 C2 H2a 109.5 ?
N2 C2 H2b 109.0 ?
C1 C2 H2a 109.2 ?
C1 C2 H2b 109.0 ?
H2a C2 H2b 109.5 ?
N2 C3 C4 112.1(3) ?
N2 C3 H3a 109.1 ?
N2 C3 H3b 108.7 ?
C4 C3 H3a 108.9 ?
C4 C3 H3b 108.4 ?
H3a C3 H3b 109.6 ?
N3 C4 C3 112.0(3) ?
N3 C4 H4a 108.7 ?
N3 C4 H4b 109.0 ?
C3 C4 H4a 108.5 ?
C3 C4 H4b 108.9 ?
H4a C4 H4b 109.9 ?
N3 C5 C6 110.3(3) ?
N3 C5 H5a 109.1 ?
N3 C5 H5b 109.5 ?
C6 C5 H5a 109.3 ?
C6 C5 H5b 109.7 ?
H5a C5 H5b 108.9 ?
N1 C6 C5 109.3(3) ?
N1 C6 H6a 109.6 ?
N1 C6 H6b 109.2 ?
C5 C6 H6a 110.1 ?
C5 C6 H6b 109.3 ?
H6a C6 H6b 109.3 ?
N2 C7 H7a 110.0 ?
N2 C7 H7b 109.8 ?
N2 C7 H7c 109.9 ?
H7a C7 H7b 109.3 ?
H7a C7 H7c 109.2 ?
H7b C7 H7c 108.7 ?
N3 C8 H8a 109.8 ?
N3 C8 H8b 109.0 ?
N3 C8 H8c 109.2 ?
H8a C8 H8b 109.7 ?
H8a C8 H8c 110.0 ?
H8b C8 H8c 109.1 ?
N1 C9 C10 110.1(3) ?
N1 C9 H9a 109.5 ?
N1 C9 H9b 109.4 ?
C10 C9 H9a 109.4 ?
C10 C9 H9b 109.0 ?
H9a C9 H9b 109.5 ?
N4 C10 C9 108.9(3) ?
N4 C10 H10a 109.6 ?
N4 C10 H10b 109.8 ?
C9 C10 H10a 109.5 ?
C9 C10 H10b 109.9 ?
H10a C10 H10b 109.2 ?
N4 C11 C12 106.7(3) ?
N4 C11 H11a 110.6 ?
N4 C11 H11b 109.8 ?
C12 C11 H11a 110.7 ?
C12 C11 H11b 110.0 ?
H11a C11 H11b 109.1 ?
N5 C12 N6 113.2(3) ?
N5 C12 C11 121.7(4) ?
N6 C12 C11 125.1(4) ?
N6 C13 C14 130.5(4) ?
N6 C13 C18 107.1(3) ?
C14 C13 C18 122.3(4) ?
C13 C14 C15 115.8(4) ?
C13 C14 H14 122.0 ?
C15 C14 H14 122.2 ?
C14 C15 C16 123.0(4) ?
C14 C15 H15 118.9 ?
C16 C15 H15 118.1 ?
C15 C16 C17 120.1(4) ?
C15 C16 H16 120.4 ?
C17 C16 H16 119.5 ?
C16 C17 C18 117.8(4) ?
C16 C17 H17 121.0 ?
C18 C17 H17 121.2 ?
N5 C18 C13 108.3(3) ?
N5 C18 C17 130.6(4) ?
C13 C18 C17 121.0(4) ?
N6 C19 H19a 109.0 ?
N6 C19 H19b 109.3 ?
N6 C19 H19c 109.3 ?
H19a C19 H19b 109.6 ?
H19a C19 H19c 109.4 ?
H19b C19 H19c 110.1 ?
N4 C20 H20a 109.5 ?
N4 C20 H20b 109.7 ?
N4 C20 H20c 109.6 ?
H20a C20 H20b 109.4 ?
H20a C20 H20c 109.5 ?
H20b C20 H20c 109.2 ?
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
Cu N1 . . 2.022(3) yes
Cu N2 . . 2.194(3) yes
Cu N3 . . 2.091(3) yes
Cu N4 . . 2.053(3) yes
Cu N5 . . 2.000(3) yes
Cl1 O11 . . 1.443(5) ?
Cl1 O12 . . 1.409(5) ?
Cl1 O13 . . 1.421(4) ?
Cl1 O14 . . 1.411(5) ?
Cl2 O21 . . 1.383(5) ?
Cl2 O22 . . 1.428(4) ?
Cl2 O23 . . 1.401(6) ?
Cl2 O24 . . 1.381(8) ?
N1 C1 . . 1.481(5) ?
N1 C6 . . 1.499(5) ?
N1 C9 . . 1.508(5) ?
N2 C2 . . 1.479(5) ?
N2 C3 . . 1.486(5) ?
N2 C7 . . 1.470(6) ?
N3 C4 . . 1.496(5) ?
N3 C5 . . 1.498(5) ?
N3 C8 . . 1.488(5) ?
N4 C10 . . 1.496(5) ?
N4 C11 . . 1.475(5) ?
N4 C20 . . 1.477(6) ?
N5 C12 . . 1.319(5) ?
N5 C18 . . 1.403(5) ?
N6 C12 . . 1.359(5) ?
N6 C13 . . 1.384(5) ?
N6 C19 . . 1.464(6) ?
C1 C2 . . 1.515(6) ?
C1 H1a . . .951 ?
C1 H1b . . .955 ?
C2 H2a . . .946 ?
C2 H2b . . .952 ?
C3 C4 . . 1.532(6) ?
C3 H3a . . .946 ?
C3 H3b . . .952 ?
C4 H4a . . .950 ?
C4 H4b . . .946 ?
C5 C6 . . 1.515(6) ?
C5 H5a . . .955 ?
C5 H5b . . .952 ?
C6 H6a . . .946 ?
C6 H6b . . .956 ?
C7 H7a . . .948 ?
C7 H7b . . .954 ?
C7 H7c . . .955 ?
C8 H8a . . .942 ?
C8 H8b . . .955 ?
C8 H8c . . .952 ?
C9 C10 . . 1.504(6) ?
C9 H9a . . .949 ?
C9 H9b . . .950 ?
C10 H10a . . .955 ?
C10 H10b . . .950 ?
C11 C12 . . 1.492(6) ?
C11 H11a . . .946 ?
C11 H11b . . .958 ?
C13 C14 . . 1.404(6) ?
C13 C18 . . 1.386(6) ?
C14 C15 . . 1.383(7) ?
C14 H14 . . .948 ?
C15 C16 . . 1.399(7) ?
C15 H15 . . .955 ?
C16 C17 . . 1.398(6) ?
C16 H16 . . .942 ?
C17 C18 . . 1.392(6) ?
C17 H17 . . .952 ?
C19 H19a . . .955 ?
C19 H19b . . .946 ?
C19 H19c . . .947 ?
C20 H20a . . .949 ?
C20 H20b . . .952 ?
C20 H20c . . .951 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139064910
