#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/14/2201402.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_2201402
loop_
_publ_author_name
'Daniel E. Lynch'
_publ_section_title
;trans-Bis(2-amino-5-methyl-1,3,4-thiadiazole-κN)bis(3,5-dicarboxybenzoato-κO)copper(II)
 dihydrate
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m577
_journal_page_last               m579
_journal_paper_doi               10.1107/S1600536802017166
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          '[Cu (C9 H5 O6)2 (C3 H5 N3 S)2], 2H2 O'
_chemical_formula_moiety         'C24 H20 Cu N6 O12 S2, 2H2 O'
_chemical_formula_sum            'C24 H24 Cu N6 O14 S2'
_chemical_formula_weight         748.15
_chemical_name_systematic
;
trans-Bis(2-amino-5-methyl-1,3,4-thiadiazole-N)-bis(benzene-1-carboxylato-O-
3,5-dicarboxylic acid)copper(II) dihydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                112.096(4)
_cell_angle_beta                 90.354(3)
_cell_angle_gamma                110.549(2)
_cell_formula_units_Z            1
_cell_length_a                   8.4671(4)
_cell_length_b                   8.7971(5)
_cell_length_c                   11.6748(6)
_cell_measurement_reflns_used    3147
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     744.84(7)
_computing_cell_refinement       'DENZO and COLLECT'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction        'DENZO and COLLECT'
_computing_molecular_graphics
'PLUTON94 (Spek, 1994) and PLATON97 (Spek, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.929
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker--Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0888
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5879
_diffrn_reflns_theta_full        27.66
_diffrn_reflns_theta_max         27.66
_diffrn_reflns_theta_min         2.95
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.954
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             383
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.777
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3222
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
' w= 1/[σ²(Fo²)+(0.0527P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1332
_reflns_number_gt                2353
_reflns_number_total             3222
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6165.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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_database_code               2201402
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_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 0.5000 1.0000 0.0000 0.02718(19) Uani d S 1 . . Cu
S1 0.95661(11) 0.93680(13) -0.16985(7) 0.0426(3) Uani d . 1 . . S
C2 0.8217(4) 1.0443(5) -0.1072(3) 0.0317(7) Uani d . 1 . . C
N21 0.8478(4) 1.2071(4) -0.0965(3) 0.0461(8) Uani d . 1 . . N
H21 0.7768 1.2575 -0.0623 0.058 Uiso calc R 1 . . H
H22 0.9361 1.2648 -0.1236 0.058 Uiso calc R 1 . . H
N3 0.6935(3) 0.9478(4) -0.0695(2) 0.0312(6) Uani d . 1 . . N
N4 0.6936(3) 0.7828(4) -0.0904(2) 0.0351(7) Uani d . 1 . . N
C5 0.8209(5) 0.7576(5) -0.1432(3) 0.0408(8) Uani d . 1 . . C
C51 0.8503(6) 0.5897(5) -0.1788(4) 0.0580(11) Uani d . 1 . . C
H51 0.7761 0.5164 -0.1396 0.073 Uiso calc R 1 . . H
H52 0.9701 0.6172 -0.1502 0.073 Uiso calc R 1 . . H
H53 0.8243 0.5248 -0.2700 0.073 Uiso calc R 1 . . H
C6 0.7035(4) 1.0653(4) 0.3472(3) 0.0266(7) Uani d . 1 . . C
C61 0.6509(4) 1.0877(4) 0.2331(3) 0.0288(7) Uani d . 1 . . C
O60 0.7089(3) 1.2359(3) 0.2274(2) 0.0434(6) Uani d . 1 . . O
O61 0.5489(3) 0.9501(3) 0.14446(17) 0.0300(5) Uani d . 1 . . O
C7 0.8391(4) 1.1988(4) 0.4366(3) 0.0296(7) Uani d . 1 . . C
H7 0.8969 1.3059 0.4265 0.034(9) Uiso calc R 1 . . H
C8 0.8928(4) 1.1793(4) 0.5419(3) 0.0271(7) Uani d . 1 . . C
C81 1.0397(4) 1.3247(4) 0.6381(3) 0.0302(7) Uani d . 1 . . C
O80 1.0775(3) 1.3241(3) 0.73832(19) 0.0380(6) Uani d . 1 . . O
O81 1.1214(3) 1.4525(3) 0.6035(2) 0.0451(6) Uani d D 1 . . O
H81 1.188(4) 1.548(3) 0.660(3) 0.056 Uiso d D 1 . . H
C9 0.8069(4) 1.0239(4) 0.5564(3) 0.0298(7) Uani d . 1 . . C
H9 0.8402 1.0104 0.6287 0.031(8) Uiso calc R 1 . . H
C10 0.6725(4) 0.8876(4) 0.4664(3) 0.0310(7) Uani d . 1 . . C
C101 0.5886(4) 0.7196(5) 0.4814(3) 0.0376(8) Uani d . 1 . . C
O100 0.4900(4) 0.5854(3) 0.3908(2) 0.0609(8) Uani d . 1 . . O
O101 0.6232(4) 0.7200(3) 0.5871(2) 0.0583(8) Uani d D 1 . . O
H101 0.600(5) 0.624(3) 0.593(4) 0.073 Uiso d D 1 . . H
C11 0.6221(4) 0.9080(4) 0.3608(3) 0.0287(7) Uani d . 1 . . C
H11 0.5315 0.8135 0.2981 0.020(7) Uiso calc R 1 . . H
O1W 0.6564(4) 0.4168(4) 0.0375(3) 0.0636(8) Uani d D 1 . . O
H1W 0.700(6) 0.495(5) 0.109(3) 0.092(18) Uiso d D 1 . . H
H2W 0.550(3) 0.389(10) 0.043(6) 0.15(3) Uiso d D 1 . . H
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N3 Cu1 N3 . 2_675 180.0 ?
N3 Cu1 O61 . 2_675 89.60(9) ?
N3 Cu1 O61 2_675 2_675 90.40(9) ?
N3 Cu1 O61 . . 90.40(9) yes
N3 Cu1 O61 2_675 . 89.60(9) ?
O61 Cu1 O61 2_675 . 180.0 ?
C2 S1 C5 . . 87.53(16) ?
N3 C2 N21 . . 124.4(3) ?
N3 C2 S1 . . 112.3(3) ?
N21 C2 S1 . . 123.3(3) ?
C2 N21 H21 . . 120.0 ?
C2 N21 H22 . . 120.0 ?
H21 N21 H22 . . 120.0 ?
C2 N3 N4 . . 113.8(3) ?
C2 N3 Cu1 . . 129.2(2) ?
N4 N3 Cu1 . . 116.9(2) ?
C5 N4 N3 . . 112.1(3) ?
N4 C5 C51 . . 123.4(4) ?
N4 C5 S1 . . 114.3(3) ?
C51 C5 S1 . . 122.3(3) ?
C5 C51 H51 . . 109.5 ?
C5 C51 H52 . . 109.5 ?
H51 C51 H52 . . 109.5 ?
C5 C51 H53 . . 109.5 ?
H51 C51 H53 . . 109.5 ?
H52 C51 H53 . . 109.5 ?
C7 C6 C11 . . 119.2(3) ?
C7 C6 C61 . . 120.2(3) ?
C11 C6 C61 . . 120.5(3) ?
O60 C61 O61 . . 122.6(3) ?
O60 C61 C6 . . 120.7(3) ?
O61 C61 C6 . . 116.8(3) ?
C61 O61 Cu1 . . 111.69(19) ?
C6 C7 C8 . . 121.2(3) ?
C6 C7 H7 . . 119.4 ?
C8 C7 H7 . . 119.4 ?
C9 C8 C7 . . 118.9(3) ?
C9 C8 C81 . . 120.4(3) ?
C7 C8 C81 . . 120.7(3) ?
O80 C81 O81 . . 123.8(3) ?
O80 C81 C8 . . 123.2(3) ?
O81 C81 C8 . . 113.0(3) ?
C81 O81 H81 . . 117(3) ?
C8 C9 C10 . . 120.6(3) ?
C8 C9 H9 . . 119.7 ?
C10 C9 H9 . . 119.7 ?
C9 C10 C11 . . 119.8(3) ?
C9 C10 C101 . . 119.3(3) ?
C11 C10 C101 . . 120.8(3) ?
O100 C101 O101 . . 123.5(3) ?
O100 C101 C10 . . 119.6(3) ?
O101 C101 C10 . . 116.9(3) ?
C101 O101 H101 . . 119(3) ?
C6 C11 C10 . . 120.2(3) ?
C6 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
H1W O1W H2W . . 101(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 N3 . 1.953(3) yes
Cu1 N3 2_675 1.953(3) ?
Cu1 O61 2_675 1.971(2) ?
Cu1 O61 . 1.971(2) yes
S1 C2 . 1.727(3) ?
S1 C5 . 1.734(4) ?
C2 N3 . 1.317(4) ?
C2 N21 . 1.326(4) ?
N21 H21 . 0.88 ?
N21 H22 . 0.88 ?
N3 N4 . 1.379(4) ?
N4 C5 . 1.290(4) ?
C5 C51 . 1.488(5) ?
C51 H51 . 0.98 ?
C51 H52 . 0.98 ?
C51 H53 . 0.98 ?
C6 C7 . 1.380(4) ?
C6 C11 . 1.383(4) ?
C6 C61 . 1.504(4) ?
C61 O60 . 1.250(4) ?
C61 O61 . 1.262(4) ?
C7 C8 . 1.398(4) ?
C7 H7 . 0.95 ?
C8 C9 . 1.379(4) ?
C8 C81 . 1.493(4) ?
C81 O80 . 1.214(3) ?
C81 O81 . 1.306(4) ?
O81 H81 . 0.839(19) ?
C9 C10 . 1.384(4) ?
C9 H9 . 0.95 ?
C10 C11 . 1.396(4) ?
C10 C101 . 1.476(4) ?
C101 O100 . 1.252(4) ?
C101 O101 . 1.266(4) ?
O101 H101 . 0.831(19) ?
C11 H11 . 0.95 ?
O1W H1W . 0.83(2) ?
O1W H2W . 0.86(2) ?
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
N21 H21 O1W 1_565 0.88 2.04 2.904(5) 168 yes
N21 H22 O80 1_554 0.88 2.13 2.949(3) 155 yes
O81 H81 O60 2_786 0.84(2) 1.75(2) 2.570(3) 167(4) yes
O101 H101 O100 2_666 0.83(2) 1.81(2) 2.631(3) 169(4) yes
O1W H1W O80 2_776 0.83(2) 2.23(3) 2.993(4) 152(5) yes
O1W H2W N4 2_665 0.86(2) 2.30(4) 3.071(4) 150(6) yes
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
C5 S1 C2 N3 . 1.5(2)
C5 S1 C2 N21 . -179.8(3)
N21 C2 N3 N4 . -179.9(3)
S1 C2 N3 N4 . -1.2(3)
N21 C2 N3 Cu1 . 4.6(5)
S1 C2 N3 Cu1 . -176.71(14)
O61 Cu1 N3 C2 2_675 52.2(3)
O61 Cu1 N3 C2 . -127.8(3)
O61 Cu1 N3 N4 2_675 -123.2(2)
O61 Cu1 N3 N4 . 56.8(2)
C2 N3 N4 C5 . 0.0(4)
Cu1 N3 N4 C5 . 176.1(2)
N3 N4 C5 C51 . -178.7(3)
N3 N4 C5 S1 . 1.2(3)
C2 S1 C5 N4 . -1.5(2)
C2 S1 C5 C51 . 178.4(3)
C7 C6 C61 O60 . -12.0(4)
C11 C6 C61 O60 . 171.0(3)
C7 C6 C61 O61 . 167.0(3)
C11 C6 C61 O61 . -10.0(4)
O60 C61 O61 Cu1 . 1.2(4)
C6 C61 O61 Cu1 . -177.77(19)
N3 Cu1 O61 C61 . 89.7(2)
N3 Cu1 O61 C61 2_675 -90.3(2)
C11 C6 C7 C8 . -1.4(5)
C61 C6 C7 C8 . -178.5(3)
C6 C7 C8 C9 . -0.6(5)
C6 C7 C8 C81 . 180.0(3)
C9 C8 C81 O80 . -9.1(5)
C7 C8 C81 O80 . 170.2(3)
C9 C8 C81 O81 . 171.6(3)
C7 C8 C81 O81 . -9.0(4)
C7 C8 C9 C10 . 1.7(5)
C81 C8 C9 C10 . -178.9(3)
C8 C9 C10 C11 . -0.8(5)
C8 C9 C10 C101 . 177.0(3)
C9 C10 C101 O100 . -166.7(3)
C11 C10 C101 O100 . 11.0(5)
C9 C10 C101 O101 . 12.6(5)
C11 C10 C101 O101 . -169.7(3)
C7 C6 C11 C10 . 2.4(5)
C61 C6 C11 C10 . 179.4(3)
C9 C10 C11 C6 . -1.4(5)
C101 C10 C11 C6 . -179.0(3)
