#------------------------------------------------------------------------------
#$Date: 2016-03-25 11:00:33 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179772 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/68/7006838.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_7006838
loop_
_publ_author_name
'Pask, Christopher M.'
'Camm, Kenneth D.'
'Bullen, Neil J.'
'Carr, Michael J.'
'Clegg, William'
'Kilner, Colin A.'
'Halcrow, Malcolm A.'
_publ_section_title
;
 Two complexes of copper(II) salts with
 5-amino-3-(pyrid-2-yl)-1H-pyrazole, the prototype for a new class of
 ditopic ligand.
;
_journal_issue                   5
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              662
_journal_page_last               664
_journal_paper_doi               10.1039/b514634h
_journal_year                    2006
_chemical_formula_moiety         'C16 H18 Cu N8 O, S O4, C H4 O, H2 O'
_chemical_formula_sum            'C17 H24 Cu N8 O7 S'
_chemical_formula_weight         548.04
_chemical_name_common
;
Bis(5-amino-3-(pyrid-2-yl)pyrazole)aquacopper(ii) sulfate
monohydrate mono-methanol solvate
;
_chemical_name_systematic
;
Bis[5-amino-3-(pyrid-2-yl)pyrazole]aquacopper(II) sulfate
monohydrate mono-methanol solvate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 102.705(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1984(11)
_cell_length_b                   12.8621(14)
_cell_length_c                   17.3027(19)
_cell_measurement_reflns_used    4267
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      21.29
_cell_measurement_theta_min      2.42
_cell_volume                     2214.1(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'fine-slice ω scans'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_source         'Daresbury SRS station 9.8'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6814
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_sigmaI/netI    0.0500
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13828
_diffrn_reflns_theta_full        22.24
_diffrn_reflns_theta_max         22.24
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    1.139
_exptl_absorpt_correction_T_max  1.162
_exptl_absorpt_correction_T_min  0.796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2002). SADABS v. 2.03. University of
G/ottingen, Germany.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1132
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         3183
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0347P)²+5.1877P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.1010
_reflns_number_gt                2280
_reflns_number_total             3183
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b514634h.txt
_cod_data_source_block           c:\shared\chris\crysta~1\cp180a\leeds105
_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      'P 21/n'
_cod_database_code               7006838
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.33430(6) 0.38234(4) 0.63310(3) 0.03278(19) Uani 1 1 d . . .
N2 N 0.2473(4) 0.4122(3) 0.7344(2) 0.0317(9) Uani 1 1 d . . .
C3 C 0.2850(5) 0.4781(4) 0.7945(3) 0.0370(12) Uani 1 1 d . . .
H3 H 0.3655 0.5166 0.7978 0.044 Uiso 1 1 calc R . .
C4 C 0.2121(5) 0.4931(4) 0.8522(3) 0.0435(13) Uani 1 1 d . . .
H4 H 0.2414 0.5414 0.8940 0.052 Uiso 1 1 calc R . .
C5 C 0.0963(5) 0.4364(4) 0.8477(3) 0.0425(13) Uani 1 1 d . . .
H5 H 0.0447 0.4452 0.8867 0.051 Uiso 1 1 calc R . .
C6 C 0.0555(5) 0.3674(4) 0.7869(3) 0.0366(12) Uani 1 1 d . . .
H6 H -0.0246 0.3281 0.7830 0.044 Uiso 1 1 calc R . .
C7 C 0.1334(5) 0.3559(3) 0.7314(3) 0.0292(11) Uani 1 1 d . . .
C8 C 0.1004(5) 0.2864(3) 0.6631(3) 0.0307(11) Uani 1 1 d . . .
N9 N 0.1808(4) 0.2890(3) 0.6125(2) 0.0311(9) Uani 1 1 d . . .
N10 N 0.1248(4) 0.2221(3) 0.5524(2) 0.0341(10) Uani 1 1 d . . .
H10 H 0.1582 0.2090 0.5106 0.041 Uiso 1 1 calc R . .
C11 C 0.0109(5) 0.1790(3) 0.5665(3) 0.0321(11) Uani 1 1 d . . .
C12 C -0.0064(5) 0.2172(3) 0.6383(3) 0.0344(12) Uani 1 1 d . . .
H12 H -0.0756 0.2002 0.6650 0.041 Uiso 1 1 calc R . .
N13 N -0.0653(4) 0.1124(3) 0.5149(2) 0.0433(11) Uani 1 1 d . . .
H13A H -0.0415 0.0959 0.4706 0.052 Uiso 1 1 calc R . .
H13B H -0.1387 0.0857 0.5256 0.052 Uiso 1 1 calc R . .
N14 N 0.2780(4) 0.4676(3) 0.5302(2) 0.0309(9) Uani 1 1 d . . .
C15 C 0.1802(5) 0.4485(4) 0.4672(3) 0.0381(12) Uani 1 1 d . . .
H15 H 0.1243 0.3898 0.4688 0.046 Uiso 1 1 calc R . .
C16 C 0.1552(5) 0.5086(4) 0.3998(3) 0.0431(13) Uani 1 1 d . . .
H16 H 0.0850 0.4913 0.3558 0.052 Uiso 1 1 calc R . .
C17 C 0.2352(5) 0.5947(4) 0.3983(3) 0.0437(13) Uani 1 1 d . . .
H17 H 0.2215 0.6375 0.3524 0.052 Uiso 1 1 calc R . .
C18 C 0.3350(5) 0.6182(4) 0.4635(3) 0.0373(12) Uani 1 1 d . . .
H18 H 0.3890 0.6784 0.4634 0.045 Uiso 1 1 calc R . .
C19 C 0.3562(5) 0.5541(3) 0.5288(3) 0.0301(11) Uani 1 1 d . . .
C20 C 0.4624(5) 0.5656(3) 0.5994(3) 0.0305(11) Uani 1 1 d . . .
N21 N 0.4735(4) 0.4878(3) 0.6516(2) 0.0353(10) Uani 1 1 d . . .
N22 N 0.5789(4) 0.5119(3) 0.7114(2) 0.0408(11) Uani 1 1 d . . .
H22 H 0.6073 0.4738 0.7540 0.049 Uiso 1 1 calc R . .
C23 C 0.6349(5) 0.6038(4) 0.6959(3) 0.0375(12) Uani 1 1 d . . .
C24 C 0.5622(5) 0.6394(4) 0.6250(3) 0.0364(12) Uani 1 1 d . . .
H24 H 0.5767 0.7017 0.5986 0.044 Uiso 1 1 calc R . .
N25 N 0.7423(4) 0.6437(3) 0.7475(3) 0.0486(12) Uani 1 1 d . . .
H25A H 0.7775 0.6099 0.7914 0.058 Uiso 1 1 calc R . .
H25B H 0.7769 0.7035 0.7372 0.058 Uiso 1 1 calc R . .
O26 O 0.4723(3) 0.2684(2) 0.6794(2) 0.0369(8) Uani 1 1 d D . .
H26A H 0.472(6) 0.247(4) 0.726(2) 0.068(10) Uiso 1 1 d D . .
H26B H 0.507(5) 0.225(3) 0.653(3) 0.068(10) Uiso 1 1 d D . .
S27 S 0.72157(12) 0.40198(9) 0.89105(7) 0.0338(3) Uani 1 1 d . . .
O28 O 0.7457(4) 0.3701(3) 0.8146(2) 0.0494(9) Uani 1 1 d . . .
O29 O 0.5771(3) 0.3924(3) 0.8899(2) 0.0451(9) Uani 1 1 d . . .
O30 O 0.7965(3) 0.3335(3) 0.95486(19) 0.0425(9) Uani 1 1 d . . .
O31 O 0.7627(3) 0.5095(2) 0.9090(2) 0.0516(10) Uani 1 1 d . . .
O32 O 1.0279(4) 0.3528(3) 1.0661(2) 0.0447(9) Uani 1 1 d D . .
H32A H 0.966(4) 0.366(4) 1.025(3) 0.068(10) Uiso 1 1 d D . .
H32B H 1.091(4) 0.396(4) 1.071(3) 0.068(10) Uiso 1 1 d D . .
O33 O 0.4630(4) 0.2082(3) 0.8281(2) 0.0441(9) Uani 1 1 d . . .
H33 H 0.5040 0.2597 0.8518 0.053 Uiso 1 1 calc R . .
C34 C 0.3547(5) 0.1816(4) 0.8630(3) 0.0498(14) Uani 1 1 d . . .
H34A H 0.3853 0.1314 0.9058 0.075 Uiso 1 1 calc R . .
H34B H 0.2823 0.1507 0.8229 0.075 Uiso 1 1 calc R . .
H34C H 0.3213 0.2443 0.8846 0.075 Uiso 1 1 calc R . .
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'
S S 0.1246 0.1234 '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
N21 Cu1 N9 173.76(16) . . ?
N21 Cu1 N14 79.94(16) . . ?
N9 Cu1 N14 96.30(15) . . ?
N21 Cu1 O26 91.18(15) . . ?
N9 Cu1 O26 94.91(14) . . ?
N14 Cu1 O26 138.46(14) . . ?
N21 Cu1 N2 99.08(15) . . ?
N9 Cu1 N2 78.54(15) . . ?
N14 Cu1 N2 121.22(14) . . ?
O26 Cu1 N2 100.19(13) . . ?
C3 N2 C7 117.8(4) . . ?
C3 N2 Cu1 130.2(3) . . ?
C7 N2 Cu1 111.9(3) . . ?
N2 C3 C4 123.0(5) . . ?
N2 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?
C5 C4 C3 118.4(5) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C6 C5 C4 120.0(5) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 118.6(5) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
N2 C7 C6 122.2(4) . . ?
N2 C7 C8 113.6(4) . . ?
C6 C7 C8 124.2(4) . . ?
N9 C8 C12 111.5(4) . . ?
N9 C8 C7 116.9(4) . . ?
C12 C8 C7 131.5(4) . . ?
C8 N9 N10 105.6(4) . . ?
C8 N9 Cu1 119.0(3) . . ?
N10 N9 Cu1 135.3(3) . . ?
C11 N10 N9 110.5(4) . . ?
C11 N10 H10 124.8 . . ?
N9 N10 H10 124.8 . . ?
N13 C11 N10 122.0(4) . . ?
N13 C11 C12 130.5(4) . . ?
N10 C11 C12 107.4(4) . . ?
C11 C12 C8 104.9(4) . . ?
C11 C12 H12 127.6 . . ?
C8 C12 H12 127.6 . . ?
C11 N13 H13A 120.0 . . ?
C11 N13 H13B 120.0 . . ?
H13A N13 H13B 120.0 . . ?
C15 N14 C19 118.1(4) . . ?
C15 N14 Cu1 128.8(3) . . ?
C19 N14 Cu1 113.2(3) . . ?
N14 C15 C16 123.9(5) . . ?
N14 C15 H15 118.1 . . ?
C16 C15 H15 118.1 . . ?
C15 C16 C17 117.9(5) . . ?
C15 C16 H16 121.1 . . ?
C17 C16 H16 121.1 . . ?
C18 C17 C16 119.6(5) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C19 C18 C17 119.7(5) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
N14 C19 C18 120.9(4) . . ?
N14 C19 C20 113.4(4) . . ?
C18 C19 C20 125.7(4) . . ?
N21 C20 C24 110.4(4) . . ?
N21 C20 C19 115.4(4) . . ?
C24 C20 C19 134.1(4) . . ?
C20 N21 N22 106.3(4) . . ?
C20 N21 Cu1 117.5(3) . . ?
N22 N21 Cu1 135.7(3) . . ?
N21 N22 C23 110.1(4) . . ?
N21 N22 H22 124.9 . . ?
C23 N22 H22 124.9 . . ?
N25 C23 C24 131.8(5) . . ?
N25 C23 N22 120.8(5) . . ?
C24 C23 N22 107.4(4) . . ?
C23 C24 C20 105.8(4) . . ?
C23 C24 H24 127.1 . . ?
C20 C24 H24 127.1 . . ?
C23 N25 H25B 120.0 . . ?
C23 N25 H25A 120.0 . . ?
H25B N25 H25A 120.0 . . ?
Cu1 O26 H26A 117(3) . . ?
Cu1 O26 H26B 126(3) . . ?
H26A O26 H26B 112(3) . . ?
O28 S27 O31 111.2(2) . . ?
O28 S27 O29 109.4(2) . . ?
O31 S27 O29 108.8(2) . . ?
O28 S27 O30 110.2(2) . . ?
O31 S27 O30 109.1(2) . . ?
O29 S27 O30 108.0(2) . . ?
H32A O32 H32B 112(3) . . ?
C34 O33 H33 109.5 . . ?
O33 C34 H34A 109.5 . . ?
O33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
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 N21 1.939(4) . ?
Cu1 N9 1.942(4) . ?
Cu1 N14 2.063(4) . ?
Cu1 O26 2.068(3) . ?
Cu1 N2 2.166(4) . ?
N2 C3 1.330(6) . ?
N2 C7 1.360(6) . ?
C3 C4 1.384(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.370(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.383(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.461(6) . ?
C8 N9 1.325(6) . ?
C8 C12 1.399(6) . ?
N9 N10 1.373(5) . ?
N10 C11 1.357(6) . ?
N10 H10 0.8800 . ?
C11 N13 1.352(6) . ?
C11 C12 1.382(6) . ?
C12 H12 0.9500 . ?
N13 H13A 0.8800 . ?
N13 H13B 0.8800 . ?
N14 C15 1.328(6) . ?
N14 C19 1.372(6) . ?
C15 C16 1.375(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.377(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.377(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.451(6) . ?
C20 N21 1.336(6) . ?
C20 C24 1.391(6) . ?
N21 N22 1.353(5) . ?
N22 C23 1.365(6) . ?
N22 H22 0.8800 . ?
C23 N25 1.353(6) . ?
C23 C24 1.365(7) . ?
C24 H24 0.9500 . ?
N25 H25B 0.8800 . ?
N25 H25A 0.8800 . ?
O26 H26A 0.85(3) . ?
O26 H26B 0.85(3) . ?
S27 O28 1.456(3) . ?
S27 O31 1.459(3) . ?
S27 O29 1.474(3) . ?
S27 O30 1.486(3) . ?
O32 H32A 0.86(3) . ?
O32 H32B 0.84(3) . ?
O33 C34 1.413(6) . ?
O33 H33 0.8400 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
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 O30 0.88 1.95 2.779(5) 155.5 4_565
N13 H13A O29 0.88 2.04 2.858(5) 153.6 4_565
N13 H13B O31 0.88 2.11 2.950(5) 158.6 2_546
N22 H22 O28 0.88 2.05 2.841(5) 148.4 .
N25 H25A O31 0.88 2.44 3.251(6) 153.0 .
N25 H25B O28 0.88 2.32 3.116(6) 151.2 2_656
O26 H26A O33 0.85(3) 1.86(3) 2.707(5) 175(5) .
O26 H26B O32 0.85(3) 1.85(3) 2.662(5) 158(5) 4_565
O32 H32A O30 0.86(3) 1.93(3) 2.708(5) 151(5) .
O32 H32B O31 0.84(3) 1.89(3) 2.735(5) 176(5) 3_767
O33 H33 O29 0.84 1.92 2.750(5) 169.0 .
