#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/98/2009831.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_2009831
loop_
_publ_author_name
'Atria, A.M.'
'Baggio, R.F.'
'Espinosa, N.'
'Garland, M.T.'
'Manzur, J.'
'Moreno, Y.'
'Spodine, E.'
_publ_section_title
;Dichloro- and
 dibromo[N-(2-pyridylmethylidene)-2-thienylmethylamine-N,N']copper(II)
 complexes, [CuCl₂(C₁₁H₁₀N₂S)] and [CuBr₂(C₁₁H₁₀N₂S)]
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1066
_journal_page_last               1069
_journal_paper_doi               10.1107/S0108270193012181
_journal_volume                  50
_journal_year                    1994
_chemical_formula_moiety         '[Cu Cl2  (C11 H11 N2 S)]'
_chemical_formula_sum            'C11 H11 Cl2 Cu N2 S'
_chemical_formula_weight         336.7
_chemical_name_systematic
;
Dichoro 2[N-(2-thienylmethyl)imino methyl]pyridine copper(II)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                79.210(10)
_cell_angle_beta                 75.270(10)
_cell_angle_gamma                67.920(10)
_cell_formula_units_Z            2
_cell_length_a                   8.1150(10)
_cell_length_b                   8.7720(10)
_cell_length_c                   10.2260(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      10
_cell_measurement_theta_min      5
_cell_volume                     648.96(14)
_computing_cell_refinement       P3/P4-PC
_computing_data_collection       'P3/P4-PC (Siemens, 1991)'
_computing_data_reduction        'XDISK in SHELXTL-Plus (Sheldrick,1991)'
_computing_molecular_graphics    'XP in SHELXTL-Plus'
_computing_publication_material  'XPUBL in SHELXTL-Plus'
_computing_structure_refinement  'XLS in SHELXTL-Plus'
_computing_structure_solution    'XS in SHELXTL-Plus'
_diffrn_ambient_temperature      293
_diffrn_measurement_device       'Siemens R3m'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0115
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2396
_diffrn_reflns_reduction_process 1707
_diffrn_reflns_theta_max         22.5
_diffrn_reflns_theta_min         1.5
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 48
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    2.231
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_description       needles
_exptl_crystal_F_000             338
_exptl_crystal_size_max          .50
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .10
_refine_diff_density_max         .28
_refine_diff_density_min         -.54
_refine_ls_goodness_of_fit_obs   1.02
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    22
_refine_ls_number_parameters     200
_refine_ls_number_reflns         1563
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          2.93
_refine_ls_R_factor_obs          0.027
_refine_ls_shift/esd_max         0.96
_refine_ls_shift/esd_mean        0.03
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(F) + 0.0022F²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         4.53
_refine_ls_wR_factor_obs         0.044
_reflns_number_observed          1563
_reflns_number_total             1707
_reflns_observed_criterion       F>4.0\s(F)
_cod_data_source_file            as1080.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(F) +
0.0022F^2^]' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w = 1/[\s^2^(F) + 0.0022F^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        649.0(2)
_cod_database_code               2009831
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_type_symbol
Cu .21200(10) .52010(10) .47150(10) .0340(10) Uani . . . . Cu
Cl(1) -.06270(10) .69390(10) .56230(10) .0410(10) Uani . . . . Cl
Cl(2) .23100(10) .68040(10) .27170(10) .0500(10) Uani . . . . Cl
N(1) .4590(3) .3494(3) .4119(2) .0340(10) Uani . . . . N
N(2) .2597(3) .3964(3) .6567(3) .0330(10) Uani . . . . N
C(1) .5543(4) .3261(4) .2858(3) .0470(10) Uani . . . . C
C(2) .7131(5) .1943(4) .2588(4) .055(2) Uani . . . . C
C(3) .7785(5) .0823(4) .3621(4) .056(2) Uani . . . . C
C(4) .6810(4) .1058(4) .4935(4) .0480(10) Uani . . . . C
C(5) .5232(4) .2395(4) .5150(3) .0360(10) Uani . . . . C
C(6) .4070(4) .2739(4) .6493(3) .0380(10) Uani . . . . C
C(7) .1324(4) .4351(3) .7896(3) .0400(10) Uani . . D . C
C(8) .1907(19) .3200(12) .9086(10) .037(5) Uani . . D A C
C(9) .276(3) .3317(17) 1.0043(15) .065(7) Uani . . D A C
C(10) .2975(17) .1945(10) 1.1075(9) .051(4) Uani . . D A C
C(11) .2172(17) .0914(10) 1.0930(8) .049(4) Uani . . D A C
S .1211(6) .1498(5) .9533(3) .0600(10) Uani . . D A S
C(8') .173(3) .3135(18) .9093(14) .039(8) Uani . . D B C
C(9') .135(3) .170(2) .9547(19) .068(13) Uani . . D B C
C(10') .232(3) .0718(15) 1.0582(18) .062(7) Uani . . D B C
C(11') .331(3) .1454(13) 1.0924(15) .048(6) Uani . . D B C
S' .3163(18) .3318(9) 1.0007(8) .059(2) Uani . . D B S
H(1) .5092 .4038 .2124 .080 Uiso calc ? . . H
H(2) .7787 .1812 .1668 .080 Uiso calc ? . . H
H(3) .8887 -.0105 .3443 .080 Uiso calc ? . . H
H(4) .7239 .0306 .5688 .080 Uiso calc ? . . H
H(6) .4424 .2055 .7295 .080 Uiso calc ? . . H
H(7A) .0155 .4387 .7819 .080 Uiso calc ? . . H
H(7B) .1198 .5433 .8066 .080 Uiso calc ? . . H
H(9) .3292 .4158 .9926 .080 Uiso calc ? . . H
H(10) .3605 .1787 1.1794 .080 Uiso calc ? . . H
H(11) .2210 -.0102 1.1493 .080 Uiso calc ? . . H
H(9') .0825 .1269 .9026 .080 Uiso calc ? . . H
H(10') .2057 -.0216 1.1122 .080 Uiso calc ? . . H
H(11') .3988 .1052 1.1638 .080 Uiso calc ? . . H
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.002 0.002 Int._Tables_Vol_C_Table_6.1.1.4_and_6.1.1.5_(1992)
H 0 0 Int._Tables_Vol_C_Table_6.1.1.4_and_6.1.1.5_(1992)
Cl .132 0.159 Int._Tables_Vol_C_Table_6.1.1.4_and_6.1.1.5_(1992)
Cu 0.263 1.266 Int._Tables_Vol_C_Table_6.1.1.4_and_6.1.1.5_(1992)
N 0.004 0.003 Int._Tables_Vol_C_Table_6.1.1.4_and_6.1.1.5_(1992)
S 0.110 0.124 Int._Tables_Vol_C_Table_6.1.1.4_and_6.1.1.5_(1992)
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Cl(1) Cu Cl(2) 2_566 . . 105.50(10) yes
Cl(1) Cu N(1) 2_566 . . 88.10(10) yes
Cl(2) Cu N(1) . . . 92.90(10) yes
Cl(1) Cu N(2) 2_566 . . 90.80(10) yes
Cl(2) Cu N(2) . . . 162.10(10) yes
N(1) Cu N(2) . . . 80.20(10) yes
Cl(1) Cu Cl(1) 2_566 . . 91.10(10) yes
Cl(2) Cu Cl(1) . . . 93.70(10) yes
N(1) Cu Cl(1) . . . 173.30(10) yes
N(2) Cu Cl(1) . . . 93.20(10) yes
Cu Cl(1) Cu . 2_566 2_566 88.90(10) yes
Cu N(1) C(1) . . . 128.0(2) yes
Cu N(1) C(5) . . . 113.6(2) yes
C(1) N(1) C(5) . . . 118.1(2) yes
Cu N(2) C(6) . . . 113.7(2) yes
Cu N(2) C(7) . . . 125.1(2) yes
C(6) N(2) C(7) . . . 121.1(2) yes
N(1) C(1) H(1) . . . 118.3(2) ?
N(1) C(1) C(2) . . . 121.8(3) yes
H(1) C(1) C(2) . . . 119.8(2) ?
C(1) C(2) H(2) . . . 119.8(2) ?
C(1) C(2) C(3) . . . 120.5(3) yes
H(2) C(2) C(3) . . . 119.7(2) ?
C(2) C(3) H(3) . . . 121.1(2) ?
C(2) C(3) C(4) . . . 118.2(3) yes
H(3) C(3) C(4) . . . 120.7(2) ?
C(3) C(4) H(4) . . . 120.5(2) ?
C(3) C(4) C(5) . . . 119.0(3) yes
H(4) C(4) C(5) . . . 120.5(2) ?
N(1) C(5) C(4) . . . 122.4(3) yes
N(1) C(5) C(6) . . . 114.0(2) yes
C(4) C(5) C(6) . . . 123.6(3) yes
N(2) C(6) C(5) . . . 118.4(3) yes
N(2) C(6) H(6) . . . 121.1(2) ?
C(5) C(6) H(6) . . . 120.5(2) ?
N(2) C(7) H(7A) . . . 108.1(2) ?
N(2) C(7) H(7B) . . . 108.5(2) ?
H(7A) C(7) H(7B) . . . 107.60(10) ?
N(2) C(7) C(8) . . . 115.1(4) yes
H(7A) C(7) C(8) . . . 110.3(6) ?
H(7B) C(7) C(8) . . . 107.0(5) ?
N(2) C(7) C(8') . . . 117.4(6) yes
H(7A) C(7) C(8') . . . 103.7(9) ?
H(7B) C(7) C(8') . . . 111.0(7) ?
C(7) C(8) C(9) . . . 131.2(12) no
C(7) C(8) S . . . 117.8(10) no
C(9) C(8) S . . . 110.5(9) no
C(8) C(9) H(9) . . . 121.2(8) ?
C(8) C(9) C(10) . . . 112.4(16) no
H(9) C(9) C(10) . . . 125.8(11) ?
C(9) C(10) H(10) . . . 123.8(11) ?
C(9) C(10) C(11) . . . 112.3(13) no
H(10) C(10) C(11) . . . 123.9(5) ?
C(10) C(11) H(11) . . . 124.9(5) ?
C(10) C(11) S . . . 112.8(7) no
H(11) C(11) S . . . 122.0(4) ?
C(8) S C(11) . . . 91.8(6) no
C(9') C(8') S' . . . 110.6(14) no
C(8') C(9') H(9') . . . 121.5(12) ?
C(8') C(9') C(10') . . . 112.(2) no
H(9') C(9') C(10') . . . 123.2(12) ?
C(9') C(10') H(10') . . . 123.2(14) ?
C(9') C(10') C(11') . . . 112.4(15) no
H(10') C(10') C(11') . . . 122.7(9) ?
C(10') C(11') H(11') . . . 126.1(8) ?
C(10') C(11') S' . . . 112.8(14) no
H(11') C(11') S' . . . 120.9(9) ?
C(8') S' C(11') . . . 91.8(11) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu Cl(1) . 2_566 2.6980(10) yes
Cu Cl(2) . . 2.2590(10) yes
Cu N(1) . . 2.023(2) yes
Cu N(2) . . 2.050(2) yes
Cu Cl(1) . . 2.2540(10) yes
N(1) C(1) . . 1.333(4) yes
N(1) C(5) . . 1.354(4) yes
N(2) C(6) . . 1.268(3) yes
N(2) C(7) . . 1.492(3) yes
C(1) H(1) . . 0.960 ?
C(1) C(2) . . 1.375(4) yes
C(2) H(2) . . 0.960 ?
C(2) C(3) . . 1.367(5) yes
C(3) H(3) . . 0.960 ?
C(3) C(4) . . 1.384(5) yes
C(4) H(4) . . 0.960 ?
C(4) C(5) . . 1.374(4) yes
C(5) C(6) . . 1.467(4) yes
C(6) H(6) . . 0.960 ?
C(7) H(7A) . . 0.960 ?
C(7) H(7B) . . 0.960 ?
C(7) C(8) . . 1.482(10) yes
C(8) C(9) . . 1.37(3) no
C(8) S . . 1.733(14) no
C(9) H(9) . . 0.960 ?
C(9) C(10) . . 1.433(15) no
C(10) H(10) . . 0.960 ?
C(10) C(11) . . 1.344(19) no
C(11) H(11) . . 0.960 ?
C(11) S . . 1.704(11) no
C(8') C(9') . . 1.38(3) no
C(8') S' . . 1.73(3) no
C(9') H(9') . . 0.960 ?
C(9') C(10') . . 1.43(3) no
C(10') H(10') . . 0.960 ?
C(10') C(11') . . 1.34(3) no
C(11') H(11') . . 0.960 ?
C(11') S' . . 1.704(14) no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
H(1) Cl(2) 2.662 . yes
H(4) Cl(1) 2.810 1_645 yes
H(7A) Cl(1) 2.869 . yes
H(7A) Cl(2) 2.782 2_566 yes
H(11) Cl(2) 2.749 1_546 yes
H(10') Cl(2) 2.777 1_546 yes
