#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/64/2016465.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_2016465
loop_
_publ_author_name
'Sabino, Jose R.'
'Cunha, Silvio'
'Souza, Aparecido R.'
'Quintino, Michelle P.'
_publ_section_title
;catena-Poly[[[1-benzoyl-2-(2-hydroxyethyl)-3-(2-pyridyl)guanidine]chloridocopper(II)]
 chloride 0.61-hydrate]
;
_journal_coeditor_code           SU3009
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m94
_journal_page_last               m96
_journal_paper_doi               10.1107/S0108270107067042
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Cu Cl (C15 H16 N4 O2)] Cl, 0.61H2 O'
_chemical_formula_moiety         'C15 H16 Cl Cu N4 O2 +, Cl -, 0.61(H2 O)'
_chemical_formula_sum            'C15 H17.22 Cl2 Cu N4 O2.61'
_chemical_formula_weight         429.75
_chemical_name_systematic
;
catena-Poly[[[N-benzoyl-N'-(2-hydroxyethyl)-\
N''-(2-pyridyl)guanidine]chloridocopper(II)] chloride monohydrate]
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 118.116(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.022(3)
_cell_length_b                   9.1140(10)
_cell_length_c                   17.005(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      35
_cell_measurement_theta_min      11
_cell_volume                     3693.8(9)
_computing_cell_refinement       'CAD4-PC (Enraf--Nonius, 1993)'
_computing_data_collection       'CAD4-PC (Enraf--Nonius, 1993)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
'Ortep-3 for Windows (Farrugia, 1997) and Platon (Spek, 2003)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7066
_diffrn_reflns_theta_full        67.89
_diffrn_reflns_theta_max         67.89
_diffrn_reflns_theta_min         3.71
_diffrn_standards_decay_%        6
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    4.504
_exptl_absorpt_correction_T_max  0.72
_exptl_absorpt_correction_T_min  0.5935
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'Spek, 2003'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1753
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.69
_refine_ls_extinction_coef       0.00266(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3318
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0946P)²+2.8853P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1384
_reflns_number_gt                2952
_reflns_number_total             3318
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su3009.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Gaussian' changed to 'gaussian'
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:

'_exptl_absorpt_correction_type' value 'Gaussian' changed to
'gaussian' 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_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2016465
_cod_database_fobs_code          2016465
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_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
Cu Cu1 0.330209(16) 0.59634(4) 0.27069(3) 0.0415(2) Uani d . 1
Cl Cl1 0.39689(4) 0.75791(9) 0.34806(6) 0.0662(3) Uani d . 1
Cl Cl2 0.18137(3) 0.52524(7) -0.09190(5) 0.0488(2) Uani d . 1
O O1 0.21733(8) 0.0859(2) 0.13948(13) 0.0440(5) Uani d . 1
O O2 0.27914(9) 0.7655(2) 0.20078(14) 0.0506(5) Uani d . 1
H H2C 0.2913 0.8386 0.1875 0.076 Uiso calc R 1
N N1 0.26795(9) 0.4830(2) 0.18277(15) 0.0376(5) Uani d . 1
N N2 0.31713(9) 0.2699(2) 0.19314(15) 0.0391(5) Uani d . 1
H H2 0.3181 0.1966 0.1621 0.047 Uiso calc R 1
N N3 0.22681(9) 0.2957(2) 0.07591(14) 0.0389(5) Uani d . 1
H H3 0.2145 0.3454 0.0273 0.047 Uiso calc R 1
N N4 0.37349(9) 0.4121(2) 0.32230(16) 0.0416(5) Uani d . 1
C C1 0.27086(10) 0.3553(3) 0.15410(16) 0.0350(5) Uani d . 1
C C2 0.21557(11) 0.5666(3) 0.1469(2) 0.0438(6) Uani d . 1
H H2A 0.2023 0.5735 0.1907 0.053 Uiso calc R 1
H H2B 0.1869 0.5193 0.0939 0.053 Uiso calc R 1
C C3 0.22848(12) 0.7173(3) 0.1245(2) 0.0476(7) Uani d . 1
H H3A 0.2339 0.713 0.072 0.057 Uiso calc R 1
H H3B 0.1979 0.7843 0.1127 0.057 Uiso calc R 1
C C6 0.20262(10) 0.1628(3) 0.07350(17) 0.0370(5) Uani d . 1
C C11 0.36338(10) 0.2851(3) 0.27723(18) 0.0394(6) Uani d . 1
C C12 0.39783(13) 0.1627(3) 0.3116(2) 0.0550(8) Uani d . 1
H H12 0.3904 0.077 0.2782 0.066 Uiso calc R 1
C C13 0.44289(15) 0.1706(4) 0.3954(3) 0.0765(12) Uani d . 1
H H13 0.4668 0.0908 0.4196 0.092 Uiso calc R 1
C C14 0.45213(15) 0.3004(4) 0.4436(3) 0.0776(12) Uani d . 1
H H14 0.482 0.3076 0.5009 0.093 Uiso calc R 1
C C15 0.41731(14) 0.4165(4) 0.4062(2) 0.0580(8) Uani d . 1
H H15 0.4237 0.5022 0.4393 0.07 Uiso calc R 1
C C21 0.15740(11) 0.1169(3) -0.01567(18) 0.0390(6) Uani d . 1
C C22 0.16135(13) -0.0202(3) -0.0464(2) 0.0483(7) Uani d . 1
H H22 0.192 -0.0799 -0.0124 0.058 Uiso calc R 1
C C23 0.11976(14) -0.0692(4) -0.1280(2) 0.0567(8) Uani d . 1
H H23 0.1225 -0.1613 -0.149 0.058(10) Uiso calc R 1
C C24 0.07412(13) 0.0193(5) -0.1780(2) 0.0652(9) Uani d . 1
H H24 0.0463 -0.0129 -0.233 0.078 Uiso calc R 1
C C25 0.06964(13) 0.1548(5) -0.1466(2) 0.0666(9) Uani d . 1
H H25 0.0384 0.2129 -0.1801 0.08 Uiso calc R 1
C C26 0.11144(12) 0.2061(4) -0.0652(2) 0.0530(7) Uani d . 1
H H26 0.1086 0.2985 -0.0444 0.064 Uiso calc R 1
O O11 0.0407(10) 0.508(2) -0.181(3) 0.124(10) Uani d PU 0.18
O O12 0.0136(10) 0.604(2) -0.221(3) 0.124(14) Uani d PU 0.18
O O13 0.0455(9) 0.564(3) -0.1229(18) 0.129(7) Uani d PU 0.25
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-4 4 -2
-3 2 2
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 Cu1 N4 . 90.38(9) y
N1 Cu1 O2 . 81.39(8) y
N4 Cu1 O2 . 171.16(9) y
N1 Cu1 Cl1 . 168.15(7) y
N4 Cu1 Cl1 . 98.85(7) y
O2 Cu1 Cl1 . 88.92(7) y
N1 Cu1 O1 4 86.55(8) y
N4 Cu1 O1 4 93.70(9) y
O2 Cu1 O1 4 89.03(8) y
Cl1 Cu1 O1 4 100.17(5) y
C6 O1 Cu1 4_545 121.24(17) ?
C3 O2 Cu1 . 112.91(15) ?
C3 O2 H2C . 109.5 ?
Cu1 O2 H2C . 121.8 ?
C1 N1 C2 . 122.4(2) ?
C1 N1 Cu1 . 126.29(17) ?
C2 N1 Cu1 . 111.16(17) ?
C1 N2 C11 . 128.4(2) ?
C1 N2 H2 . 115.8 ?
C11 N2 H2 . 115.8 ?
C6 N3 C1 . 123.3(2) ?
C6 N3 H3 . 118.4 ?
C1 N3 H3 . 118.4 ?
C11 N4 C15 . 117.8(2) ?
C11 N4 Cu1 . 123.65(18) ?
C15 N4 Cu1 . 118.5(2) ?
N1 C1 N2 . 123.1(2) ?
N1 C1 N3 . 122.3(2) ?
N2 C1 N3 . 114.5(2) ?
N1 C2 C3 . 106.6(2) ?
N1 C2 H2A . 110.4 ?
C3 C2 H2A . 110.4 ?
N1 C2 H2B . 110.4 ?
C3 C2 H2B . 110.4 ?
H2A C2 H2B . 108.6 ?
O2 C3 C2 . 106.5(2) ?
O2 C3 H3A . 110.4 ?
C2 C3 H3A . 110.4 ?
O2 C3 H3B . 110.4 ?
C2 C3 H3B . 110.4 ?
H3A C3 H3B . 108.6 ?
O1 C6 N3 . 122.5(2) ?
O1 C6 C21 . 122.0(2) ?
N3 C6 C21 . 115.5(2) ?
N4 C11 C12 . 122.3(2) ?
N4 C11 N2 . 121.0(2) ?
C12 C11 N2 . 116.7(2) ?
C13 C12 C11 . 118.9(3) ?
C13 C12 H12 . 120.5 ?
C11 C12 H12 . 120.5 ?
C12 C13 C14 . 118.7(3) ?
C12 C13 H13 . 120.6 ?
C14 C13 H13 . 120.6 ?
C15 C14 C13 . 119.6(3) ?
C15 C14 H14 . 120.2 ?
C13 C14 H14 . 120.2 ?
C14 C15 N4 . 122.5(3) ?
C14 C15 H15 . 118.7 ?
N4 C15 H15 . 118.7 ?
C22 C21 C26 . 120.5(3) ?
C22 C21 C6 . 117.9(2) ?
C26 C21 C6 . 121.5(3) ?
C21 C22 C23 . 120.1(3) ?
C21 C22 H22 . 120 ?
C23 C22 H22 . 120 ?
C24 C23 C22 . 119.8(3) ?
C24 C23 H23 . 120.1 ?
C22 C23 H23 . 120.1 ?
C25 C24 C23 . 120.2(3) ?
C25 C24 H24 . 119.9 ?
C23 C24 H24 . 119.9 ?
C24 C25 C26 . 120.7(3) ?
C24 C25 H25 . 119.7 ?
C26 C25 H25 . 119.7 ?
C21 C26 C25 . 118.8(3) ?
C21 C26 H26 . 120.6 ?
C25 C26 H26 . 120.6 ?
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
Cu1 N1 . 1.940(2) y
Cu1 N4 . 1.997(2) y
Cu1 O2 . 2.037(2) y
Cu1 Cl1 . 2.2162(8) y
Cu1 O1 4 2.417(2) y
O1 C6 . 1.220(3) y
O1 Cu1 4_545 2.417(2) ?
O2 C3 . 1.441(4) ?
O2 H2C . 0.82 ?
N1 C1 . 1.278(3) y
N1 C2 . 1.464(3) ?
N2 C1 . 1.352(3) y
N2 C11 . 1.394(3) ?
N2 H2 . 0.86 ?
N3 C6 . 1.367(3) ?
N3 C1 . 1.410(3) y
N3 H3 . 0.86 ?
N4 C11 . 1.343(3) ?
N4 C15 . 1.359(4) ?
C2 C3 . 1.509(4) ?
C2 H2A . 0.97 ?
C2 H2B . 0.97 ?
C3 H3A . 0.97 ?
C3 H3B . 0.97 ?
C6 C21 . 1.490(3) ?
C11 C12 . 1.393(4) ?
C12 C13 . 1.373(5) ?
C12 H12 . 0.93 ?
C13 C14 . 1.393(6) ?
C13 H13 . 0.93 ?
C14 C15 . 1.358(5) y
C14 H14 . 0.93 ?
C15 H15 . 0.93 ?
C21 C22 . 1.378(4) ?
C21 C26 . 1.388(4) ?
C22 C23 . 1.384(4) ?
C22 H22 . 0.93 ?
C23 C24 . 1.381(5) ?
C23 H23 . 0.93 ?
C24 C25 . 1.372(6) ?
C24 H24 . 0.93 ?
C25 C26 . 1.391(4) ?
C25 H25 . 0.93 ?
C26 H26 . 0.93 ?
O12 O12 2_554 0.90(6) ?
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
O2 H2C Cl2 7_565 0.82 2.42 3.173(2) 152.9 y
N2 H2 Cl2 7 0.86 2.35 3.204(2) 171.5 y
N3 H3 Cl2 . 0.86 2.43 3.275(2) 169.1 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 Cu1 O2 C3 . -3.42(19)
Cl1 Cu1 O2 C3 . 169.73(19)
O1 Cu1 O2 C3 4 -90.08(19)
N4 Cu1 N1 C1 . -25.1(2)
O2 Cu1 N1 C1 . 151.7(2)
Cl1 Cu1 N1 C1 . 116.2(3)
O1 Cu1 N1 C1 4 -118.8(2)
N4 Cu1 N1 C2 . 158.8(2)
O2 Cu1 N1 C2 . -24.43(18)
Cl1 Cu1 N1 C2 . -59.9(4)
O1 Cu1 N1 C2 4 65.12(19)
N1 Cu1 N4 C11 . 22.0(2)
Cl1 Cu1 N4 C11 . -150.5(2)
O1 Cu1 N4 C11 4 108.6(2)
N1 Cu1 N4 C15 . -161.1(3)
Cl1 Cu1 N4 C15 . 26.3(3)
O1 Cu1 N4 C15 4 -74.6(2)
C2 N1 C1 N2 . -172.2(3)
Cu1 N1 C1 N2 . 12.1(4)
C2 N1 C1 N3 . 11.4(4)
Cu1 N1 C1 N3 . -164.32(18)
C11 N2 C1 N1 . 14.9(4)
C11 N2 C1 N3 . -168.4(2)
C6 N3 C1 N1 . -125.5(3)
C6 N3 C1 N2 . 57.8(3)
C1 N1 C2 C3 . -129.6(3)
Cu1 N1 C2 C3 . 46.7(3)
Cu1 O2 C3 C2 . 28.9(3)
N1 C2 C3 O2 . -47.6(3)
Cu1 O1 C6 N3 4_545 94.5(3)
Cu1 O1 C6 C21 4_545 -86.4(3)
C1 N3 C6 O1 . 0.4(4)
C1 N3 C6 C21 . -178.8(2)
C15 N4 C11 C12 . -3.6(4)
Cu1 N4 C11 C12 . 173.2(2)
C15 N4 C11 N2 . 176.0(3)
Cu1 N4 C11 N2 . -7.2(4)
C1 N2 C11 N4 . -16.8(4)
C1 N2 C11 C12 . 162.8(3)
N4 C11 C12 C13 . 1.8(5)
N2 C11 C12 C13 . -177.9(3)
C11 C12 C13 C14 . 0.8(6)
C12 C13 C14 C15 . -1.3(7)
C13 C14 C15 N4 . -0.7(7)
C11 N4 C15 C14 . 3.1(5)
Cu1 N4 C15 C14 . -173.9(3)
O1 C6 C21 C22 . -51.2(4)
N3 C6 C21 C22 . 128.0(3)
O1 C6 C21 C26 . 126.4(3)
N3 C6 C21 C26 . -54.4(4)
C26 C21 C22 C23 . 1.0(5)
C6 C21 C22 C23 . 178.6(3)
C21 C22 C23 C24 . -0.5(5)
C22 C23 C24 C25 . -0.7(5)
C23 C24 C25 C26 . 1.4(6)
C22 C21 C26 C25 . -0.3(5)
C6 C21 C26 C25 . -177.8(3)
C24 C25 C26 C21 . -0.9(6)
