#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:58:52 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180366 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/35/7203560.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7203560
loop_
_publ_author_name
'Jones, Leigh F.'
'Camm, Kenneth D.'
'Kilner, Colin A.'
'Halcrow, Malcolm A.'
_publ_section_title
;
 Novel hydrogen bond network topologies in complexes of the ditopic
 ligand 5-amino-3-(pyrid-2-yl)-1H-pyrazole
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              719
_journal_paper_doi               10.1039/b609424d
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C18 H19 Cu N9, 2[Cl O4]'
_chemical_formula_sum            'C18 H19 Cl2 Cu N9 O8'
_chemical_formula_weight         623.86
_chemical_name_systematic
;
Bis[5-amino-3-(pyrid-2-yl)pyrazole][acetonitrile]copper(II)
diperchlorate (4)
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.4093(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.5384(7)
_cell_length_b                   8.2388(2)
_cell_length_c                   14.5781(6)
_cell_measurement_reflns_used    17974
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.67
_cell_volume                     2418.04(14)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEX (McArdle, 1995)'
_computing_publication_material  'local program'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Nonius KappaCCD area detector diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_av_sigmaI/netI    0.0482
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17974
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.67
_exptl_absorpt_coefficient_mu    1.190
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Using multiple and symmetry-related data measurements via the program SORTAV
See R.H. Blessing, Acta Cryst (1995), A51, 33-38
;
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1268
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.899
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2771
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0763P)²+2.9672P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1329
_reflns_number_gt                2122
_reflns_number_total             2771
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b609424d.txt
_cod_data_source_block           c:\datasets\leeds\lfj15c\lfj15c
_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 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7203560
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_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.57687(5) 0.2500 0.02537(18) Uani 1 2 d S . .
N2 N 0.07303(12) 0.5914(3) 0.36375(17) 0.0280(5) Uani 1 1 d . . .
C3 C 0.13683(15) 0.5506(3) 0.3693(2) 0.0330(7) Uani 1 1 d . . .
H3 H 0.1496 0.5017 0.3165 0.040 Uiso 1 1 calc R . .
C4 C 0.18474(16) 0.5766(4) 0.4486(2) 0.0393(7) Uani 1 1 d . . .
H4 H 0.2298 0.5485 0.4497 0.047 Uiso 1 1 calc R . .
C5 C 0.16639(17) 0.6442(4) 0.5264(2) 0.0423(8) Uani 1 1 d . . .
H5 H 0.1986 0.6627 0.5819 0.051 Uiso 1 1 calc R . .
C6 C 0.10069(16) 0.6845(4) 0.5225(2) 0.0384(7) Uani 1 1 d . . .
H6 H 0.0870 0.7312 0.5752 0.046 Uiso 1 1 calc R . .
C7 C 0.05515(15) 0.6561(3) 0.44081(19) 0.0306(6) Uani 1 1 d . . .
C8 C -0.01602(14) 0.6922(3) 0.42786(19) 0.0293(6) Uani 1 1 d . . .
N9 N -0.05206(12) 0.6572(3) 0.34385(16) 0.0294(5) Uani 1 1 d . . .
N10 N -0.11550(13) 0.7016(3) 0.34820(18) 0.0322(5) Uani 1 1 d D . .
H10 H -0.1476(16) 0.706(5) 0.301(2) 0.067(8) Uiso 1 1 d D . .
C11 C -0.11869(16) 0.7640(4) 0.4332(2) 0.0344(7) Uani 1 1 d . . .
C12 C -0.05454(16) 0.7594(4) 0.4862(2) 0.0371(7) Uani 1 1 d . . .
H12 H -0.0402 0.7948 0.5489 0.045 Uiso 1 1 calc R . .
N13 N -0.17624(15) 0.8206(4) 0.4526(2) 0.0466(7) Uani 1 1 d D . .
H13A H -0.2142(14) 0.796(5) 0.420(2) 0.067(8) Uiso 1 1 d D . .
H13B H -0.1771(18) 0.832(5) 0.5108(18) 0.067(8) Uiso 1 1 d D . .
N14 N 0.0000 0.3144(4) 0.2500 0.0334(8) Uani 1 2 d S . .
C15 C 0.0000 0.1783(5) 0.2500 0.0347(9) Uani 1 2 d S . .
C16 C 0.0000 0.0007(6) 0.2500 0.0673(17) Uani 1 2 d S . .
H16A H 0.0143 -0.0389 0.3142 0.101 Uiso 0.50 1 calc PR . .
H16B H 0.0306 -0.0389 0.2113 0.101 Uiso 0.50 1 calc PR . .
H16C H -0.0449 -0.0389 0.2245 0.101 Uiso 0.50 1 calc PR . .
Cl17 Cl -0.31025(4) 0.56798(9) 0.28178(5) 0.0350(2) Uani 1 1 d . . .
O18 O -0.24652(15) 0.5606(4) 0.2576(3) 0.0826(11) Uani 1 1 d . . .
O19 O -0.30922(18) 0.6949(4) 0.3499(2) 0.0769(9) Uani 1 1 d . . .
O20 O -0.36039(14) 0.5985(4) 0.2016(2) 0.0613(8) Uani 1 1 d . . .
O21 O -0.32417(18) 0.4199(4) 0.3228(2) 0.0802(11) Uani 1 1 d . . .
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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N2 173.16(13) 2 . ?
N2 Cu1 N9 80.16(10) . . ?
N2 Cu1 N9 97.56(10) . 2 ?
N9 Cu1 N9 141.52(14) . 2 ?
N2 Cu1 N14 93.42(6) . . ?
N9 Cu1 N14 109.24(7) . . ?
C3 N2 C7 118.0(3) . . ?
C3 N2 Cu1 126.6(2) . . ?
C7 N2 Cu1 115.25(19) . . ?
N2 C3 C4 122.6(3) . . ?
N2 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
C3 C4 C5 119.1(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 119.1(3) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C7 119.0(3) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
N2 C7 C6 122.1(3) . . ?
N2 C7 C8 113.5(2) . . ?
C6 C7 C8 124.4(3) . . ?
N9 C8 C12 111.7(3) . . ?
N9 C8 C7 115.7(2) . . ?
C12 C8 C7 132.6(3) . . ?
C8 N9 N10 105.1(2) . . ?
C8 N9 Cu1 115.10(19) . . ?
N10 N9 Cu1 139.54(19) . . ?
C11 N10 N9 111.3(2) . . ?
C11 N10 H10 124(3) . . ?
N9 N10 H10 124(3) . . ?
N13 C11 N10 121.6(3) . . ?
N13 C11 C12 131.7(3) . . ?
N10 C11 C12 106.6(3) . . ?
C8 C12 C11 105.3(3) . . ?
C8 C12 H12 127.4 . . ?
C11 C12 H12 127.4 . . ?
C11 N13 H13A 123(3) . . ?
C11 N13 H13B 116(3) . . ?
H13A N13 H13B 112(2) . . ?
C15 N14 Cu1 180.000(1) . . ?
N14 C15 C16 180.000(1) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O21 Cl17 O20 109.09(18) . . ?
O21 Cl17 O18 109.9(2) . . ?
O20 Cl17 O18 110.9(2) . . ?
O21 Cl17 O19 108.2(2) . . ?
O20 Cl17 O19 110.4(2) . . ?
O18 Cl17 O19 108.3(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 2.008(2) . ?
Cu1 N9 2.008(2) . ?
Cu1 N14 2.163(4) . ?
N2 C3 1.340(4) . ?
N2 C7 1.358(4) . ?
C3 C4 1.379(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.381(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.467(4) . ?
C8 N9 1.331(4) . ?
C8 C12 1.386(4) . ?
N9 N10 1.367(3) . ?
N10 C11 1.355(4) . ?
N10 H10 0.86(2) . ?
C11 N13 1.352(4) . ?
C11 C12 1.389(4) . ?
C12 H12 0.9500 . ?
N13 H13A 0.85(2) . ?
N13 H13B 0.86(2) . ?
N14 C15 1.121(5) . ?
C15 C16 1.463(6) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
Cl17 O21 1.412(3) . ?
Cl17 O20 1.419(3) . ?
Cl17 O18 1.423(3) . ?
Cl17 O19 1.439(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N10 H10 O18 0.86(2) 2.34(4) 2.988(4) 133(4) .
N13 H13A O19 0.85(2) 2.18(3) 3.026(5) 171(4) .
N13 H13B O19 0.86(2) 2.12(3) 2.956(4) 166(4) 7_466
