#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/82/2218209.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_2218209
loop_
_publ_author_name
'Wang, Yuan'
'Liu, Zheng'
'Gao, Jiong-Yang'
_publ_section_title
;(3,5-Dichlorosalicylaldehyde
 thiosemicarbazonato-κ³S,N¹,O)(N,N'-dimethylformamide-κO)copper(II)
 dimethylformamide solvate
;
_journal_coeditor_code           OM2219
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m633
_journal_page_last               m634
_journal_paper_doi               10.1107/S1600536808008982
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac
'[Cu (C8 H5 Cl2 N3 O S) (C3 H 7 N O)], C3 H7 N O'
_chemical_formula_moiety         'C11 H12 Cl2 Cu N4 O2 S, C3 H7 N O'
_chemical_formula_sum            'C14 H19 Cl2 Cu N5 O3 S'
_chemical_formula_weight         471.84
_chemical_name_systematic
;
(3,5-Dichlorosalicylaldehyde
thiosemicarbazonato-κ³S,O,N)(N,N'-
dimethylformamide-κO)copper(II) dimethylformamide 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                 94.263(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4979(10)
_cell_length_b                   9.8057(12)
_cell_length_c                   21.744(2)
_cell_measurement_reflns_used    3442
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.758
_cell_measurement_theta_min      2.28
_cell_volume                     2019.5(4)
_computing_cell_refinement       'SMART (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       'φ and ω'
_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  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9869
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    1.473
_exptl_absorpt_correction_T_max  0.7188
_exptl_absorpt_correction_T_min  0.5322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             964
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.497
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3558
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0364
_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)+(0.0377P)²+1.6178P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0982
_reflns_number_gt                2587
_reflns_number_total             3558
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om2219.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 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2218209
_cod_database_fobs_code          2218209
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_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 0.54152(4) 0.31930(4) 0.51062(2) 0.04237(15) Uani d . 1
Cl Cl1 0.29920(11) -0.05605(11) 0.41172(6) 0.0706(3) Uani d . 1
Cl Cl2 0.69572(16) -0.09500(13) 0.24825(6) 0.0928(4) Uani d . 1
N N1 0.7172(3) 0.3290(3) 0.46944(12) 0.0353(6) Uani d . 1
N N2 0.8232(3) 0.4197(3) 0.48940(14) 0.0433(7) Uani d . 1
N N3 0.8875(3) 0.5886(3) 0.55631(15) 0.0592(9) Uani d . 1
H H3A 0.9666 0.5938 0.5396 0.071 Uiso calc R 1
H H3B 0.8710 0.6418 0.5864 0.071 Uiso calc R 1
N N4 0.1645(3) 0.2314(4) 0.58339(19) 0.0736(11) Uani d . 1
N N5 0.3114(4) 0.6470(4) 0.24057(17) 0.0673(10) Uani d . 1
O O1 0.4724(2) 0.1664(2) 0.46316(13) 0.0515(6) Uani d . 1
O O2 0.3799(2) 0.3059(3) 0.56320(12) 0.0536(7) Uani d . 1
O O3 0.4168(4) 0.7162(4) 0.15577(16) 0.0890(10) Uani d . 1
S S1 0.63125(9) 0.49051(9) 0.57083(4) 0.0431(2) Uani d . 1
C C1 0.7899(3) 0.4974(3) 0.53551(15) 0.0386(8) Uani d . 1
C C2 0.7456(3) 0.2575(3) 0.42245(17) 0.0427(8) Uani d . 1
H H2 0.8309 0.2751 0.4055 0.051 Uiso calc R 1
C C3 0.6572(3) 0.1521(3) 0.39345(17) 0.0430(8) Uani d . 1
C C4 0.5275(4) 0.1113(3) 0.41651(18) 0.0440(9) Uani d . 1
C C5 0.4564(4) 0.0012(3) 0.38446(19) 0.0496(10) Uani d . 1
C C6 0.5066(5) -0.0603(4) 0.3345(2) 0.0604(11) Uani d . 1
H H6 0.4566 -0.1317 0.3150 0.072 Uiso calc R 1
C C7 0.6330(5) -0.0162(4) 0.31267(18) 0.0579(10) Uani d . 1
C C8 0.7069(4) 0.0878(4) 0.34189(18) 0.0517(10) Uani d . 1
H H8 0.7916 0.1163 0.3272 0.062 Uiso calc R 1
C C9 0.2784(4) 0.2276(4) 0.55256(19) 0.0568(10) Uani d . 1
H H9 0.2831 0.1632 0.5214 0.068 Uiso calc R 1
C C10 0.1465(5) 0.3332(6) 0.6303(3) 0.1007(19) Uani d . 1
H H10A 0.2270 0.3927 0.6334 0.151 Uiso calc R 1
H H10B 0.1377 0.2890 0.6692 0.151 Uiso calc R 1
H H10C 0.0629 0.3854 0.6195 0.151 Uiso calc R 1
C C11 0.0480(5) 0.1379(6) 0.5678(3) 0.118(2) Uani d . 1
H H11A -0.0330 0.1885 0.5517 0.178 Uiso calc R 1
H H11B 0.0252 0.0896 0.6042 0.178 Uiso calc R 1
H H11C 0.0750 0.0740 0.5374 0.178 Uiso calc R 1
C C12 0.3156(6) 0.7130(5) 0.1874(2) 0.0765(14) Uani d . 1
H H12 0.2351 0.7607 0.1731 0.092 Uiso calc R 1
C C13 0.4330(6) 0.5683(5) 0.2633(3) 0.1003(18) Uani d . 1
H H13A 0.4152 0.4732 0.2556 0.151 Uiso calc R 1
H H13B 0.4508 0.5831 0.3068 0.151 Uiso calc R 1
H H13C 0.5139 0.5963 0.2425 0.151 Uiso calc R 1
C C14 0.1882(5) 0.6465(6) 0.2757(2) 0.0926(16) Uani d . 1
H H14A 0.1149 0.7001 0.2547 0.139 Uiso calc R 1
H H14B 0.2121 0.6847 0.3158 0.139 Uiso calc R 1
H H14C 0.1557 0.5546 0.2800 0.139 Uiso calc R 1
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'
Cu Cu 0.3201 1.2651 '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'
Cl Cl 0.1484 0.1585 '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_publ_flag
O1 Cu1 N1 93.55(11) y
O1 Cu1 O2 90.55(11) y
N1 Cu1 O2 172.04(11) y
O1 Cu1 S1 176.26(8) y
N1 Cu1 S1 86.04(8) y
O2 Cu1 S1 89.43(8) y
C2 N1 N2 114.1(3) ?
C2 N1 Cu1 125.1(2) ?
N2 N1 Cu1 120.8(2) ?
C1 N2 N1 113.5(3) ?
C1 N3 H3A 120.0 ?
C1 N3 H3B 120.0 ?
H3A N3 H3B 120.0 ?
C9 N4 C10 121.6(4) ?
C9 N4 C11 120.2(5) ?
C10 N4 C11 118.0(4) ?
C12 N5 C14 122.7(4) ?
C12 N5 C13 118.8(4) ?
C14 N5 C13 118.4(4) ?
C4 O1 Cu1 127.5(2) y
C9 O2 Cu1 123.8(3) y
C1 S1 Cu1 94.29(11) y
N2 C1 N3 116.3(3) ?
N2 C1 S1 125.3(2) ?
N3 C1 S1 118.4(3) ?
N1 C2 C3 126.0(3) ?
N1 C2 H2 117.0 ?
C3 C2 H2 117.0 ?
C8 C3 C4 120.6(3) ?
C8 C3 C2 116.9(3) ?
C4 C3 C2 122.5(3) ?
O1 C4 C3 124.8(3) ?
O1 C4 C5 119.6(3) ?
C3 C4 C5 115.6(3) ?
C6 C5 C4 123.0(4) ?
C6 C5 Cl1 119.3(3) ?
C4 C5 Cl1 117.7(3) ?
C5 C6 C7 119.8(3) ?
C5 C6 H6 120.1 ?
C7 C6 H6 120.1 ?
C8 C7 C6 119.9(4) ?
C8 C7 Cl2 120.7(3) ?
C6 C7 Cl2 119.4(3) ?
C7 C8 C3 121.1(4) ?
C7 C8 H8 119.4 ?
C3 C8 H8 119.4 ?
O2 C9 N4 123.0(4) ?
O2 C9 H9 118.5 ?
N4 C9 H9 118.5 ?
N4 C10 H10A 109.5 ?
N4 C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
N4 C10 H10C 109.5 ?
H10A C10 H10C 109.5 ?
H10B C10 H10C 109.5 ?
N4 C11 H11A 109.5 ?
N4 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
N4 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
O3 C12 N5 125.3(5) ?
O3 C12 H12 117.3 ?
N5 C12 H12 117.3 ?
N5 C13 H13A 109.5 ?
N5 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
N5 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
N5 C14 H14A 109.5 ?
N5 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
N5 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O1 1.909(2) y
Cu1 N1 1.954(3) y
Cu1 O2 1.985(2) y
Cu1 S1 2.2567(10) y
Cl1 C5 1.740(4) ?
Cl2 C7 1.743(4) ?
N1 C2 1.284(4) ?
N1 N2 1.388(3) ?
N2 C1 1.316(4) ?
N3 C1 1.342(4) ?
N3 H3A 0.8600 ?
N3 H3B 0.8600 ?
N4 C9 1.315(5) ?
N4 C10 1.446(6) ?
N4 C11 1.458(6) ?
N5 C12 1.328(6) ?
N5 C14 1.444(6) ?
N5 C13 1.446(6) ?
O1 C4 1.294(4) ?
O2 C9 1.241(4) ?
O3 C12 1.223(6) ?
S1 C1 1.743(3) ?
C2 C3 1.447(4) ?
C2 H2 0.9300 ?
C3 C8 1.398(5) ?
C3 C4 1.421(5) ?
C4 C5 1.427(5) ?
C5 C6 1.359(6) ?
C6 C7 1.393(6) ?
C6 H6 0.9300 ?
C7 C8 1.367(5) ?
C8 H8 0.9300 ?
C9 H9 0.9300 ?
C10 H10A 0.9600 ?
C10 H10B 0.9600 ?
C10 H10C 0.9600 ?
C11 H11A 0.9600 ?
C11 H11B 0.9600 ?
C11 H11C 0.9600 ?
C12 H12 0.9300 ?
C13 H13A 0.9600 ?
C13 H13B 0.9600 ?
C13 H13C 0.9600 ?
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 0.9600 ?
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
N3 H3A N2 3_766 0.86 2.14 2.992(4) 170 y
N3 H3B O3 4_676 0.86 2.08 2.886(4) 157 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
O1 Cu1 N1 C2 7.1(3)
O2 Cu1 N1 C2 127.9(7)
S1 Cu1 N1 C2 -176.6(3)
O1 Cu1 N1 N2 -174.1(2)
O2 Cu1 N1 N2 -53.3(9)
S1 Cu1 N1 N2 2.2(2)
C2 N1 N2 C1 176.6(3)
Cu1 N1 N2 C1 -2.3(4)
N1 Cu1 O1 C4 -7.1(3)
O2 Cu1 O1 C4 179.7(3)
S1 Cu1 O1 C4 -90.6(13)
O1 Cu1 O2 C9 -7.4(3)
N1 Cu1 O2 C9 -128.4(7)
S1 Cu1 O2 C9 176.3(3)
O1 Cu1 S1 C1 82.5(12)
N1 Cu1 S1 C1 -1.24(14)
O2 Cu1 S1 C1 172.22(14)
N1 N2 C1 N3 -179.1(3)
N1 N2 C1 S1 0.9(4)
Cu1 S1 C1 N2 0.6(3)
Cu1 S1 C1 N3 -179.4(3)
N2 N1 C2 C3 177.6(3)
Cu1 N1 C2 C3 -3.5(5)
N1 C2 C3 C8 178.9(3)
N1 C2 C3 C4 -2.9(6)
Cu1 O1 C4 C3 3.3(5)
Cu1 O1 C4 C5 -176.6(2)
C8 C3 C4 O1 -178.8(3)
C2 C3 C4 O1 3.1(5)
C8 C3 C4 C5 1.2(5)
C2 C3 C4 C5 -176.9(3)
O1 C4 C5 C6 179.0(3)
C3 C4 C5 C6 -1.0(5)
O1 C4 C5 Cl1 -1.6(4)
C3 C4 C5 Cl1 178.5(3)
C4 C5 C6 C7 0.1(6)
Cl1 C5 C6 C7 -179.4(3)
C5 C6 C7 C8 0.7(6)
C5 C6 C7 Cl2 -179.5(3)
C6 C7 C8 C3 -0.5(6)
Cl2 C7 C8 C3 179.7(3)
C4 C3 C8 C7 -0.5(6)
C2 C3 C8 C7 177.7(3)
Cu1 O2 C9 N4 -171.5(3)
C10 N4 C9 O2 3.2(7)
C11 N4 C9 O2 179.0(4)
C14 N5 C12 O3 -179.7(5)
C13 N5 C12 O3 -1.9(8)
