#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/50/2005057.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_2005057
loop_
_publ_author_name
'Elliot, D.'
'Price, C. L.'
'Martin, L. L.'
'Taylor, M. R.'
_publ_contact_author
;
   Dr Max R. Taylor
   Chemistry Department
   The Flinders University of South Australia
   GPO Box 2100
   Adelaide 5001
   Australia
;
_publ_section_title
;
 {2-[Bis(1-methyl-2-benzimidazolylmethyl)amino]-ethanol}chlorocopper(II)
 Chloride Hydrate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1421
_journal_page_last               1423
_journal_paper_doi               10.1107/S0108270196001205
_journal_volume                  52
_journal_year                    1996
_chemical_formula_iupac          '[Cu Cl (C20 H23 N5 O)] Cl , (H2 O)'
_chemical_formula_moiety         'C20 H23 Cl Cu N5 O 1+, Cl 1-, H2 O'
_chemical_formula_structural     '(Cu Cl (C20 H23 N5 O)) Cl (H2 O)'
_chemical_formula_sum            'C20 H25 Cl2 Cu N5 O2'
_chemical_formula_weight         501.90
_chemical_name_systematic
;N-2-hydroxyethyl-N,N-bis[1-methyl-2-benzimidazolylmethyl]aminechlorocopper(II)
 chloride hydrate
;
_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'
_audit_creation_method           from_xtal_archive_file_using_CIFIO
_cell_angle_alpha                90.00000
_cell_angle_beta                 99.46(2)
_cell_angle_gamma                90.00000
_cell_formula_units_Z            4
_cell_length_a                   8.336(2)
_cell_length_b                   15.044(4)
_cell_length_c                   17.454(6)
_cell_measurement_reflns_used    6
_cell_measurement_temperature    293
_cell_measurement_theta_max      22.16
_cell_measurement_theta_min      19.24
_cell_volume                     2159.1(11)
_computing_data_reduction
'Xtal DIFDAT ADDREF ABSORB SORTRF (Hall, Flack & Stewart, 1992)'
_computing_molecular_graphics    Xtal
_computing_publication_material  Xtal_CIFIO
_computing_structure_refinement  Xtal_CRYLSQ
_computing_structure_solution    Xtal
_diffrn_ambient_temperature      293
_diffrn_measurement_device       CAD4
_diffrn_measurement_method       'ω/2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_av_sigmaI/netI    .043
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6289
_diffrn_reflns_theta_max         30.0
_diffrn_reflns_theta_min         1.8
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         6
_exptl_absorpt_coefficient_mu    1.29
_exptl_absorpt_correction_T_max  .6869
_exptl_absorpt_correction_T_min  .6398
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            blue-green
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_meas      1.540(10)
_exptl_crystal_density_method
;
  flotation in 1,1,1-trichloroethane and 1,2-dibromoethane
;
_exptl_crystal_description       prism
_exptl_crystal_F_000             1035.77
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.27
_refine_diff_density_max         .667
_refine_diff_density_min         -.508
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.765
_refine_ls_goodness_of_fit_obs   1.798
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5902
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          .063
_refine_ls_R_factor_obs          .056
_refine_ls_shift/esd_max         .383
_refine_ls_shift/esd_mean        .102
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         .106
_refine_ls_wR_factor_obs         .104
_reflns_number_observed          5902
_reflns_number_total             6289
_reflns_observed_criterion       refl_observed_if_Fsqd_>0
_cod_data_source_file            sk1011.cif
_cod_data_source_block           david
_cod_original_cell_volume        2159.0(10)
_cod_original_sg_symbol_Hall     -P_2ybc
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2005057
_cod_database_fobs_code          2005057
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
-x,1/2+y,1/2-z
-x,-y,-z
+x,1/2-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_thermal_displace_type
Cu .54780(3) .62181(2) .45713(2) .03150(10) Uani
Cl(1) .76579(8) .54412(5) .43435(4) .0491(3) Uani
Cl(2) .95721(8) .82912(6) .49576(6) .0681(5) Uani
N(1) .3354(2) .68940(10) .47840(10) .0331(9) Uani
C(1) .3255(3) .6847(2) .5624(2) .0390(10) Uani
C(2) .4904(3) .6642(2) .60590(10) .0350(10) Uani
N(3) .6089(2) .63600(10) .57020(10) .0360(10) Uani
C(4) .7451(3) .6255(2) .62830(10) .0360(10) Uani
C(5) .9032(3) .5994(2) .6245(2) .0430(10) Uani
C(6) 1.0103(4) .5958(2) .6936(2) .0490(10) Uani
C(7) .9639(4) .6171(2) .7643(2) .051(2) Uani
C(8) .8073(4) .6434(2) .7686(2) .0460(10) Uani
C(9) .6997(3) .6475(2) .69930(10) .0380(10) Uani
N(10) .5368(3) .67190(10) .68290(10) .0370(10) Uani
C(11) .4369(4) .6963(2) .7407(2) .050(2) Uani
C(1') .1930(3) .6471(2) .4289(2) .0380(10) Uani
C(2') .2505(3) .6197(2) .35620(10) .0350(10) Uani
N(3') .4062(2) .59900(10) .35740(10) .0337(9) Uani
C(4') .4208(3) .5772(2) .28160(10) .0340(10) Uani
C(5') .5545(3) .5536(2) .2484(2) .0420(10) Uani
C(6') .5300(4) .5382(2) .1695(2) .049(2) Uani
C(7') .3773(4) .5474(2) .1242(2) .051(2) Uani
C(8') .2427(4) .5711(2) .1555(2) .0450(10) Uani
C(9') .2679(3) .5861(2) .23530(10) .0360(10) Uani
N(10') .1625(2) .61340(10) .28470(10) .0370(10) Uani
C(11') -.0112(3) .6315(3) .2605(2) .054(2) Uani
C(12) .3531(3) .7829(2) .4522(2) .0400(10) Uani
C(13) .5226(3) .8180(2) .4722(2) .0430(10) Uani
O(1) .6226(2) .76340(10) .43300(10) .0420(10) Uani
O(2) .1686(4) .9923(2) .4346(2) .070(2) Uani
H(5) .928(3) .582(2) .574(2) .040(7) Uiso
H(6) 1.114(4) .578(2) .689(2) .060(10) Uiso
H(7) 1.035(4) .608(2) .812(2) .050(10) Uiso
H(8) .774(4) .654(2) .815(2) .044(9) Uiso
H(111) .483(4) .739(3) .775(2) .090(10) Uiso
H(211) .413(4) .641(2) .773(2) .070(10) Uiso
H(311) .331(5) .721(2) .715(2) .080(10) Uiso
H(5') .667(3) .546(2) .281(2) .045(8) Uiso
H(6') .607(4) .521(2) .145(2) .060(10) Uiso
H(7') .362(3) .539(2) .068(2) .052(9) Uiso
H(8') .138(3) .580(2) .127(2) .051(8) Uiso
H(111') -.056(5) .640(3) .297(2) .090(10) Uiso
H(211') -.024(4) .679(3) .225(2) .090(10) Uiso
H(311') -.074(5) .580(3) .233(2) .110(10) Uiso
H(1) .252(3) .635(2) .573(2) .042(8) Uiso
H(21) .294(3) .739(2) .580(2) .043(8) Uiso
H(1') .102(4) .685(2) .420(2) .036(9) Uiso
H(21') .164(4) .587(2) .455(2) .054(9) Uiso
H(12) .322(3) .783(2) .400(2) .043(8) Uiso
H(212) .295(3) .810(2) .473(2) .038(9) Uiso
H(13) .527(4) .879(2) .454(2) .040(10) Uiso
H(213) .560(3) .822(2) .5320(10) .034(7) Uiso
H(1'') .718(4) .773(2) .451(2) .070(10) Uiso
H(20) .118(4) .972(3) .443(2) .010(10) Uiso
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu .263 1.266 Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1
Cl .132 .159 Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1
C .002 .002 Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1
N .004 .003 Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1
O .008 .006 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
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
10 0 0
0 16 0
0 0 16
-10 0 0
0 -16 0
0 0 -16
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
Cl(1) Cu N(1) 177.24(6) yes
Cl(1) Cu N(3) 98.63(6) yes
Cl(1) Cu N(3') 97.93(6) yes
Cl(1) Cu O(1) 101.52(5) yes
N(1) Cu N(3) 81.88(8) yes
N(1) Cu N(3') 80.91(8) yes
N(1) Cu O(1) 81.14(7) yes
N(3) Cu N(3') 157.81(9) yes
N(3) Cu O(1) 92.89(8) yes
N(3') Cu O(1) 98.18(7) yes
Cu N(1) C(1) 109.50(10) ?
Cu N(1) C(1') 107.5(2) ?
Cu N(1) C(12) 105.6(2) ?
C(1) N(1) C(1') 112.6(2) ?
C(1) N(1) C(12) 111.8(2) ?
C(1') N(1) C(12) 109.5(2) ?
N(1) C(1) C(2) 108.5(2) ?
N(1) C(1) H(1) 110(2) ?
N(1) C(1) H(21) 111(2) ?
C(2) C(1) H(1) 107(2) ?
C(2) C(1) H(21) 107(2) ?
H(1) C(1) H(21) 112(3) ?
C(1) C(2) N(3) 121.7(2) ?
C(1) C(2) N(10) 125.7(2) ?
N(3) C(2) N(10) 112.7(2) ?
Cu N(3) C(2) 114.70(10) ?
Cu N(3) C(4) 139.4(2) ?
C(2) N(3) C(4) 105.9(2) ?
N(3) C(4) C(5) 131.4(2) ?
N(3) C(4) C(9) 108.1(2) ?
C(5) C(4) C(9) 120.5(2) ?
C(4) C(5) C(6) 116.9(3) ?
C(4) C(5) H(5) 117.0(10) ?
C(6) C(5) H(5) 126.0(10) ?
C(5) C(6) C(7) 122.2(3) ?
C(5) C(6) H(6) 115(2) ?
C(7) C(6) H(6) 123(2) ?
C(6) C(7) C(8) 121.2(3) ?
C(6) C(7) H(7) 121(2) ?
C(8) C(7) H(7) 117(2) ?
C(7) C(8) C(9) 116.7(3) ?
C(7) C(8) H(8) 122(2) ?
C(9) C(8) H(8) 121(2) ?
C(4) C(9) C(8) 122.4(3) ?
C(4) C(9) N(10) 106.1(2) ?
C(8) C(9) N(10) 131.5(3) ?
C(2) N(10) C(9) 107.2(2) ?
C(2) N(10) C(11) 127.8(2) ?
C(9) N(10) C(11) 125.0(2) ?
N(10) C(11) H(111) 114(2) ?
N(10) C(11) H(211) 111(2) ?
N(10) C(11) H(311) 110(2) ?
H(111) C(11) H(211) 107(3) ?
H(111) C(11) H(311) 106(3) ?
H(211) C(11) H(311) 108(3) ?
N(1) C(1') C(2') 106.0(2) ?
N(1) C(1') H(1') 112(2) ?
N(1) C(1') H(21') 109(2) ?
C(2') C(1') H(1') 113(2) ?
C(2') C(1') H(21') 106(2) ?
H(1') C(1') H(21') 110(3) ?
C(1') C(2') N(3') 120.1(2) ?
C(1') C(2') N(10') 127.6(2) ?
N(3') C(2') N(10') 112.4(2) ?
Cu N(3') C(2') 114.5(2) ?
Cu N(3') C(4') 138.7(2) ?
C(2') N(3') C(4') 106.2(2) ?
N(3') C(4') C(5') 131.5(2) ?
N(3') C(4') C(9') 108.3(2) ?
C(5') C(4') C(9') 120.2(2) ?
C(4') C(5') C(6') 117.6(2) ?
C(4') C(5') H(5') 122(2) ?
C(6') C(5') H(5') 121(2) ?
C(5') C(6') C(7') 121.6(3) ?
C(5') C(6') H(6') 123(2) ?
C(7') C(6') H(6') 115(2) ?
C(6') C(7') C(8') 122.0(3) ?
C(6') C(7') H(7') 121(2) ?
C(8') C(7') H(7') 117(2) ?
C(7') C(8') C(9') 116.2(2) ?
C(7') C(8') H(8') 125(2) ?
C(9') C(8') H(8') 119(2) ?
C(4') C(9') C(8') 122.4(2) ?
C(4') C(9') N(10') 106.2(2) ?
C(8') C(9') N(10') 131.3(2) ?
C(2') N(10') C(9') 107.0(2) ?
C(2') N(10') C(11') 128.1(2) ?
C(9') N(10') C(11') 124.9(2) ?
N(10') C(11') H(111') 112(3) ?
N(10') C(11') H(211') 110(2) ?
N(10') C(11') H(311') 114(2) ?
H(111') C(11') H(211') 112(4) ?
H(111') C(11') H(311') 103(4) ?
H(211') C(11') H(311') 106(3) ?
N(1) C(12) C(13) 113.5(2) ?
N(1) C(12) H(12) 107(2) ?
N(1) C(12) H(212) 105(2) ?
C(13) C(12) H(12) 109(2) ?
C(13) C(12) H(212) 110(2) ?
H(12) C(12) H(212) 112(3) ?
C(12) C(13) O(1) 106.9(2) ?
C(12) C(13) H(13) 110(2) ?
C(12) C(13) H(213) 112.0(10) ?
O(1) C(13) H(13) 109(2) ?
O(1) C(13) H(213) 114.0(10) ?
H(13) C(13) H(213) 104(2) ?
Cu O(1) C(13) 104.5(2) ?
Cu O(1) H(1'') 111(2) ?
C(13) O(1) H(1'') 109(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cu Cl(1) 2.2510(10) yes
Cu N(1) 2.127(2) yes
Cu N(3) 1.967(2) yes
Cu N(3') 1.966(2) yes
Cu O(1) 2.278(2) yes
N(1) C(1) 1.484(3) ?
N(1) C(1') 1.491(3) ?
N(1) C(12) 1.494(4) ?
C(1) C(2) 1.490(3) ?
C(1) H(1) 1.00(3) ?
C(1) H(21) .92(3) ?
C(2) N(3) 1.322(3) ?
C(2) N(10) 1.340(3) ?
N(3) C(4) 1.400(3) ?
C(4) C(5) 1.387(4) ?
C(4) C(9) 1.395(4) ?
C(5) C(6) 1.380(4) ?
C(5) H(5) .97(3) ?
C(6) C(7) 1.389(5) ?
C(6) H(6) .92(3) ?
C(7) C(8) 1.378(4) ?
C(7) H(7) .95(3) ?
C(8) C(9) 1.383(4) ?
C(8) H(8) .91(3) ?
C(9) N(10) 1.391(3) ?
N(10) C(11) 1.457(4) ?
C(11) H(111) .92(4) ?
C(11) H(211) 1.04(3) ?
C(11) H(311) 1.00(4) ?
C(1') C(2') 1.486(4) ?
C(1') H(1') .94(3) ?
C(1') H(21') 1.06(3) ?
C(2') N(3') 1.331(3) ?
C(2') N(10') 1.343(3) ?
N(3') C(4') 1.388(3) ?
C(4') C(5') 1.384(4) ?
C(4') C(9') 1.398(3) ?
C(5') C(6') 1.379(4) ?
C(5') H(5') 1.02(3) ?
C(6') C(7') 1.390(4) ?
C(6') H(6') .87(3) ?
C(7') C(8') 1.374(4) ?
C(7') H(7') .98(3) ?
C(8') C(9') 1.392(4) ?
C(8') H(8') .94(3) ?
C(9') N(10') 1.390(3) ?
N(10') C(11') 1.466(3) ?
C(11') H(111') .79(4) ?
C(11') H(211') .93(4) ?
C(11') H(311') 1.01(4) ?
C(12) C(13) 1.494(4) ?
C(12) H(12) .91(3) ?
C(12) H(212) .77(3) ?
C(13) O(1) 1.422(4) ?
C(13) H(13) .97(3) ?
C(13) H(213) 1.03(3) ?
O(1) H(1'') .81(3) ?
O(2) H(20) .57(4) ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
O(2) Cl(2) 3.300(4)
O(2) C(12) 3.498(4)
O(2) C(13) 3.921(4)
O(2) C(6') 3.405(5)
O(2) C(8') 3.723(4)
O(2) Cl(2) 3.195(4)
O(2) O(2) 3.908(5)
O(2) C(7) 3.576(4)
O(2) C(7') 3.526(4)
O(2) C(8') 3.921(4)
Cu Cl(1) 2.2502(9)
Cu N(1) 2.127(2)
Cu C(1) 2.971(3)
Cu C(2) 2.791(3)
Cu N(3) 1.967(2)
Cu C(4) 3.164(2)
Cu C(1') 2.942(2)
Cu C(2') 2.795(2)
Cu N(3') 1.966(2)
Cu C(4') 3.145(2)
Cu C(12) 2.910(3)
Cu C(13) 2.973(3)
Cu O(1) 2.278(2)
O(1) Cu 2.278(2)
O(1) Cl(2) 2.992(2)
O(1) N(1) 2.867(3)
O(1) N(3) 3.084(3)
O(1) N(3') 3.214(3)
O(1) C(12) 2.343(3)
O(1) C(13) 1.422(4)
