#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/39/2013948.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_2013948
loop_
_publ_author_name
'Bivián-Castro, Egla Y.'
'Bernès, Sylvain'
'Escalante, Jaime'
'Mendoza-Díaz, Guillermo'
_publ_section_title
;
 Chloro(histamine)(1,10-phenanthroline)copper(II) chloride monohydrate
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m205
_journal_page_last               m207
_journal_paper_doi               10.1107/S0108270104006560
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          '[Cu Cl (C5 H9 N3) (C12 H8 N2)] Cl , H2 O'
_chemical_formula_moiety         'C17 H17 Cl Cu N5 + , Cl - , H2 O'
_chemical_formula_sum            'C17 H19 Cl2 Cu N5 O'
_chemical_formula_weight         443.81
_chemical_name_systematic
;
chloro[2-(4-imidazolyl-\kN¹)ethylamine-\kN](1,10-phenanthroline-
κ²N,N')copper(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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.621(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.2744(14)
_cell_length_b                   12.6490(11)
_cell_length_c                   17.760(2)
_cell_measurement_reflns_used    83
_cell_measurement_temperature    296.0(10)
_cell_measurement_theta_max      12.84
_cell_measurement_theta_min      4.79
_cell_volume                     3816.4(6)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'SHELXTL and PLUTON (Spek, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXTL (Sheldrick, 1997a)'
_diffrn_ambient_temperature      296.0(10)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7754
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.01
_diffrn_standards_decay_%        1.9
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.441
_exptl_absorpt_correction_T_max  0.749
_exptl_absorpt_correction_T_min  0.611
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(XSCANS; Siemens, 1996)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1816
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.329
_refine_ls_extinction_coef       0.00084(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997b)'
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4402
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0327
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.041P)²+2.422P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0899
_reflns_number_gt                3424
_reflns_number_total             4402
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fa1052.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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 

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 

The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'geom + difmap' was changed to
'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_cell_volume        3816.3(6)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2013948
_cod_database_fobs_code          2013948
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_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cu1 0.244720(15) 0.46880(2) 0.627264(14) 0.04056(10) Uani d . 1 . . Cu
Cl1 0.14405(3) 0.54257(5) 0.66187(4) 0.05477(16) Uani d . 1 . . Cl
Cl2 0.10799(4) 0.17292(5) 0.50320(3) 0.05519(17) Uani d . 1 . . Cl
O1 0.10750(15) 0.2930(2) 0.66279(13) 0.0912(7) Uani d . 1 . . O
H1A 0.1247 0.3666 0.6668 0.137 Uiso d R 1 . . H
H1B 0.1029 0.2733 0.6100 0.137 Uiso d R 1 . . H
N1 0.31711(11) 0.45575(15) 0.74039(10) 0.0427(4) Uani d . 1 . . N
C2 0.32395(15) 0.52384(19) 0.79922(14) 0.0504(6) Uani d . 1 . . C
H2A 0.2885 0.5780 0.7959 0.060 Uiso calc R 1 . . H
N3 0.38847(13) 0.50415(18) 0.86363(12) 0.0548(5) Uani d . 1 . . N
H3A 0.4040 0.5388 0.9084 0.066 Uiso calc R 1 . . H
C4 0.42560(14) 0.4198(2) 0.84650(14) 0.0517(6) Uani d . 1 . . C
H4A 0.4723 0.3892 0.8807 0.062 Uiso calc R 1 . . H
C5 0.38164(12) 0.38857(18) 0.76982(12) 0.0414(5) Uani d . 1 . . C
C6 0.39192(13) 0.2982(2) 0.72057(14) 0.0513(6) Uani d . 1 . . C
H6A 0.4251 0.2451 0.7566 0.062 Uiso calc R 1 . . H
H6B 0.4186 0.3230 0.6857 0.062 Uiso calc R 1 . . H
C7 0.31428(14) 0.24783(18) 0.66878(14) 0.0500(5) Uani d . 1 . . C
H7A 0.3242 0.1807 0.6479 0.060 Uiso calc R 1 . . H
H7B 0.2832 0.2342 0.7017 0.060 Uiso calc R 1 . . H
N8 0.26978(11) 0.31793(15) 0.60039(11) 0.0438(4) Uani d . 1 . . N
H8A 0.2239 0.2859 0.5720 0.053 Uiso calc R 1 . . H
H8B 0.2972 0.3231 0.5676 0.053 Uiso calc R 1 . . H
N9 0.18285(11) 0.49783(16) 0.50863(11) 0.0447(4) Uani d . 1 . . N
C10 0.11063(14) 0.4623(2) 0.46528(15) 0.0557(6) Uani d . 1 . . C
H10A 0.0856 0.4181 0.4901 0.067 Uiso calc R 1 . . H
C11 0.07149(15) 0.4892(2) 0.38392(16) 0.0626(7) Uani d . 1 . . C
H11A 0.0215 0.4626 0.3552 0.075 Uiso calc R 1 . . H
C12 0.10727(16) 0.5546(2) 0.34717(15) 0.0596(7) Uani d . 1 . . C
H12A 0.0817 0.5728 0.2930 0.072 Uiso calc R 1 . . H
C13 0.18255(14) 0.5947(2) 0.39081(13) 0.0477(5) Uani d . 1 . . C
C14 0.22366(17) 0.6675(2) 0.35811(15) 0.0577(7) Uani d . 1 . . C
H14A 0.2002 0.6889 0.3044 0.069 Uiso calc R 1 . . H
C15 0.29501(17) 0.7051(2) 0.40328(16) 0.0584(7) Uani d . 1 . . C
H15A 0.3197 0.7530 0.3807 0.070 Uiso calc R 1 . . H
C16 0.33399(14) 0.67254(18) 0.48610(15) 0.0478(5) Uani d . 1 . . C
C17 0.40914(16) 0.7073(2) 0.53668(19) 0.0620(7) Uani d . 1 . . C
H17A 0.4374 0.7535 0.5169 0.074 Uiso calc R 1 . . H
C18 0.44040(16) 0.6730(2) 0.61482(19) 0.0628(7) Uani d . 1 . . C
H18A 0.4905 0.6944 0.6484 0.075 Uiso calc R 1 . . H
C19 0.39688(13) 0.6059(2) 0.64365(16) 0.0532(6) Uani d . 1 . . C
H19A 0.4186 0.5845 0.6975 0.064 Uiso calc R 1 . . H
N20 0.32584(10) 0.57059(16) 0.59859(11) 0.0428(4) Uani d . 1 . . N
C21 0.29507(12) 0.60318(17) 0.52024(13) 0.0402(5) Uani d . 1 . . C
C22 0.21826(13) 0.56329(18) 0.47211(13) 0.0403(5) Uani d . 1 . . C
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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
1 -3 0
4 0 0
1 3 0
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 Cu1 N9 171.01(8) y
N1 Cu1 N8 92.05(7) y
N9 Cu1 N8 90.77(8) y
N1 Cu1 N20 91.67(7) y
N9 Cu1 N20 79.35(7) y
N8 Cu1 N20 105.49(7) y
N1 Cu1 Cl1 93.63(6) y
N9 Cu1 Cl1 90.54(6) y
N8 Cu1 Cl1 133.99(6) y
N20 Cu1 Cl1 119.91(6) y
H1A O1 H1B 103.4 n
C2 N1 C5 106.30(19) n
C2 N1 Cu1 125.80(16) n
C5 N1 Cu1 126.48(15) n
N1 C2 N3 110.7(2) n
N1 C2 H2A 124.7 n
N3 C2 H2A 124.7 n
C2 N3 C4 108.2(2) n
C2 N3 H3A 125.9 n
C4 N3 H3A 125.9 n
N3 C4 C5 107.0(2) n
N3 C4 H4A 126.5 n
C5 C4 H4A 126.5 n
C4 C5 N1 107.8(2) n
C4 C5 C6 130.8(2) n
N1 C5 C6 121.35(18) n
C5 C6 C7 112.66(19) n
C5 C6 H6A 109.1 n
C7 C6 H6A 109.1 n
C5 C6 H6B 109.1 n
C7 C6 H6B 109.1 n
H6A C6 H6B 107.8 n
N8 C7 C6 110.72(19) n
N8 C7 H7A 109.5 n
C6 C7 H7A 109.5 n
N8 C7 H7B 109.5 n
C6 C7 H7B 109.5 n
H7A C7 H7B 108.1 n
C7 N8 Cu1 117.80(14) n
C7 N8 H8A 107.9 n
Cu1 N8 H8A 107.9 n
C7 N8 H8B 107.9 n
Cu1 N8 H8B 107.9 n
H8A N8 H8B 107.2 n
C10 N9 C22 118.31(19) n
C10 N9 Cu1 126.34(17) n
C22 N9 Cu1 115.29(14) n
N9 C10 C11 122.3(3) n
N9 C10 H10A 118.9 n
C11 C10 H10A 118.9 n
C12 C11 C10 119.4(2) n
C12 C11 H11A 120.3 n
C10 C11 H11A 120.3 n
C11 C12 C13 120.1(2) n
C11 C12 H12A 119.9 n
C13 C12 H12A 119.9 n
C12 C13 C22 117.1(2) n
C12 C13 C14 124.1(2) n
C22 C13 C14 118.8(2) n
C15 C14 C13 121.5(2) n
C15 C14 H14A 119.2 n
C13 C14 H14A 119.2 n
C14 C15 C16 121.1(2) n
C14 C15 H15A 119.5 n
C16 C15 H15A 119.5 n
C21 C16 C17 116.8(2) n
C21 C16 C15 118.9(2) n
C17 C16 C15 124.3(2) n
C18 C17 C16 119.7(2) n
C18 C17 H17A 120.1 n
C16 C17 H17A 120.1 n
C17 C18 C19 119.3(2) n
C17 C18 H18A 120.3 n
C19 C18 H18A 120.3 n
N20 C19 C18 123.5(2) n
N20 C19 H19A 118.3 n
C18 C19 H19A 118.3 n
C19 N20 C21 117.4(2) n
C19 N20 Cu1 131.47(16) n
C21 N20 Cu1 111.17(14) n
N20 C21 C16 123.3(2) n
N20 C21 C22 116.55(19) n
C16 C21 C22 120.1(2) n
N9 C22 C13 122.8(2) n
N9 C22 C21 117.61(18) n
C13 C22 C21 119.5(2) n
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 . 1.9634(18) y
Cu1 N9 . 2.0241(18) y
Cu1 N8 . 2.0593(19) y
Cu1 N20 . 2.1613(19) y
Cu1 Cl1 . 2.3380(7) y
O1 H1A . 0.9764 n
O1 H1B . 0.9433 n
N1 C2 . 1.324(3) n
N1 C5 . 1.390(3) n
C2 N3 . 1.329(3) n
C2 H2A . 0.9300 n
N3 C4 . 1.358(3) n
N3 H3A . 0.8600 n
C4 C5 . 1.360(3) n
C4 H4A . 0.9300 n
C5 C6 . 1.493(3) n
C6 C7 . 1.518(3) n
C6 H6A . 0.9700 n
C6 H6B . 0.9700 n
C7 N8 . 1.482(3) n
C7 H7A . 0.9700 n
C7 H7B . 0.9700 n
N8 H8A . 0.9000 n
N8 H8B . 0.9000 n
N9 C10 . 1.337(3) n
N9 C22 . 1.354(3) n
C10 C11 . 1.398(4) n
C10 H10A . 0.9300 n
C11 C12 . 1.362(4) n
C11 H11A . 0.9300 n
C12 C13 . 1.402(4) n
C12 H12A . 0.9300 n
C13 C22 . 1.405(3) n
C13 C14 . 1.439(4) n
C14 C15 . 1.341(4) n
C14 H14A . 0.9300 n
C15 C16 . 1.438(3) n
C15 H15A . 0.9300 n
C16 C21 . 1.400(3) n
C16 C17 . 1.406(4) n
C17 C18 . 1.362(4) n
C17 H17A . 0.9300 n
C18 C19 . 1.384(4) n
C18 H18A . 0.9300 n
C19 N20 . 1.326(3) n
C19 H19A . 0.9300 n
N20 C21 . 1.359(3) n
C21 C22 . 1.439(3) n
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 Cl1 1_555 0.98 2.26 3.228(3) 171 y
O1 H1B Cl2 1_555 0.94 2.31 3.218(2) 161 y
N3 H3A Cl2 4_556 0.86 2.38 3.169(2) 154 y
N8 H8A Cl2 1_555 0.90 2.47 3.3651(19) 171 y
N8 H8B Cl2 7_556 0.90 2.49 3.379(2) 170 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
_geom_torsion_publ_flag
N8 Cu1 N1 C2 -171.0(2) n
N20 Cu1 N1 C2 83.5(2) n
Cl1 Cu1 N1 C2 -36.6(2) n
N8 Cu1 N1 C5 24.53(19) n
N20 Cu1 N1 C5 -81.04(19) n
Cl1 Cu1 N1 C5 158.85(18) n
C5 N1 C2 N3 0.1(3) n
Cu1 N1 C2 N3 -166.98(16) n
N1 C2 N3 C4 0.0(3) n
C2 N3 C4 C5 -0.2(3) n
N3 C4 C5 N1 0.2(3) n
N3 C4 C5 C6 -177.3(2) n
C2 N1 C5 C4 -0.2(3) n
Cu1 N1 C5 C4 166.77(16) n
C2 N1 C5 C6 177.6(2) n
Cu1 N1 C5 C6 -15.4(3) n
C4 C5 C6 C7 142.3(3) n
N1 C5 C6 C7 -34.9(3) n
C5 C6 C7 N8 72.2(3) n
C6 C7 N8 Cu1 -56.5(2) n
N1 Cu1 N8 C7 11.83(17) n
N9 Cu1 N8 C7 -176.70(16) n
N20 Cu1 N8 C7 104.14(16) n
Cl1 Cu1 N8 C7 -85.21(17) n
N8 Cu1 N9 C10 75.9(2) n
N20 Cu1 N9 C10 -178.5(2) n
Cl1 Cu1 N9 C10 -58.1(2) n
N8 Cu1 N9 C22 -106.95(17) n
N20 Cu1 N9 C22 -1.34(16) n
Cl1 Cu1 N9 C22 119.04(16) n
C22 N9 C10 C11 0.9(4) n
Cu1 N9 C10 C11 178.0(2) n
N9 C10 C11 C12 -0.7(4) n
C10 C11 C12 C13 -0.2(4) n
C11 C12 C13 C22 0.7(4) n
C11 C12 C13 C14 -177.5(3) n
C12 C13 C14 C15 178.5(2) n
C22 C13 C14 C15 0.4(4) n
C13 C14 C15 C16 1.1(4) n
C14 C15 C16 C21 -2.1(4) n
C14 C15 C16 C17 179.0(2) n
C21 C16 C17 C18 0.1(4) n
C15 C16 C17 C18 178.9(2) n
C16 C17 C18 C19 -1.2(4) n
C17 C18 C19 N20 1.4(4) n
C18 C19 N20 C21 -0.3(4) n
C18 C19 N20 Cu1 -178.9(2) n
N1 Cu1 N20 C19 0.7(2) n
N9 Cu1 N20 C19 -179.7(2) n
N8 Cu1 N20 C19 -91.9(2) n
Cl1 Cu1 N20 C19 95.9(2) n
N1 Cu1 N20 C21 -177.99(15) n
N9 Cu1 N20 C21 1.59(15) n
N8 Cu1 N20 C21 89.42(15) n
Cl1 Cu1 N20 C21 -82.84(15) n
C19 N20 C21 C16 -1.0(3) n
Cu1 N20 C21 C16 177.89(17) n
C19 N20 C21 C22 179.5(2) n
Cu1 N20 C21 C22 -1.6(2) n
C17 C16 C21 N20 1.1(3) n
C15 C16 C21 N20 -177.8(2) n
C17 C16 C21 C22 -179.4(2) n
C15 C16 C21 C22 1.7(3) n
C10 N9 C22 C13 -0.4(3) n
Cu1 N9 C22 C13 -177.77(17) n
C10 N9 C22 C21 178.3(2) n
Cu1 N9 C22 C21 0.9(3) n
C12 C13 C22 N9 -0.5(3) n
C14 C13 C22 N9 177.9(2) n
C12 C13 C22 C21 -179.1(2) n
C14 C13 C22 C21 -0.8(3) n
N20 C21 C22 N9 0.6(3) n
C16 C21 C22 N9 -179.0(2) n
N20 C21 C22 C13 179.3(2) n
C16 C21 C22 C13 -0.2(3) n
