#------------------------------------------------------------------------------
#$Date: 2016-03-23 01:51:24 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179158 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/19/4311996.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_4311996
loop_
_publ_author_name
'Eric L. Klein'
'Masood A. Khan'
'Robert P. Houser'
_publ_section_title
;
 Synthesis, Characterization, and Reactivity of New Copper(II) Complexes
 of 2-Methylthio-N-(2-pyridylmethyl)acetamide
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              7272
_journal_page_last               7274
_journal_paper_doi               10.1021/ic049136e
_journal_volume                  43
_journal_year                    2004
_chemical_formula_sum            'C10 H15 Cl Cu N2 O2 S'
_chemical_formula_weight         326.29
_chemical_name_systematic
; 
 ? 
;
_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                78.0590(10)
_cell_angle_beta                 80.3540(10)
_cell_angle_gamma                84.5680(10)
_cell_formula_units_Z            2
_cell_length_a                   7.3002(3)
_cell_length_b                   8.2461(4)
_cell_length_c                   10.8430(5)
_cell_measurement_reflns_used    4921
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.4
_cell_measurement_theta_min      4.2
_cell_volume                     628.36(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0159
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7396
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.53
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.107
_exptl_absorpt_correction_T_max  0.4312
_exptl_absorpt_correction_T_min  0.3850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker(2001)SADABS,BrukerAXSInc.,Madison,WI
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             334
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.48
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.0378(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2694
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0199
_refine_ls_R_factor_gt           0.0197
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0235P)²+0.4754P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0506
_refine_ls_wR_factor_ref         0.0508
_reflns_number_gt                2673
_reflns_number_total             2694
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic049136esi20040701_033607_2.cif
_cod_data_source_block           '[Cu(LN2S)Cl(MeOH)]'
_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 
;
_cod_database_code               4311996
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.69706(2) 0.739051(18) -0.210060(14) 0.01129(5) Uani 1 1 d . . .
Cl1 Cl 0.60604(5) 1.00101(4) -0.29036(3) 0.01687(7) Uani 1 1 d . . .
S1 S 0.61887(4) 0.77472(4) 0.00060(3) 0.01309(7) Uani 1 1 d . . .
O1 O 1.01513(13) 0.77671(12) -0.24448(9) 0.0158(2) Uani 1 1 d D . .
O2 O 0.83493(14) 0.31235(12) 0.03049(9) 0.0168(2) Uani 1 1 d . . .
N1 N 0.70895(15) 0.64242(14) -0.36802(11) 0.0129(2) Uani 1 1 d . . .
N2 N 0.74466(16) 0.50899(14) -0.13331(11) 0.0125(2) Uani 1 1 d . . .
C1 C 0.67658(19) 0.72532(17) -0.48380(13) 0.0162(3) Uani 1 1 d . . .
H1A H 0.6373 0.8399 -0.4942 0.019 Uiso 1 1 calc R . .
C2 C 0.6986(2) 0.64911(19) -0.58784(13) 0.0183(3) Uani 1 1 d . . .
H2A H 0.6754 0.7102 -0.6687 0.022 Uiso 1 1 calc R . .
C3 C 0.7554(2) 0.48156(18) -0.57198(13) 0.0182(3) Uani 1 1 d . . .
H3A H 0.7727 0.4264 -0.6422 0.022 Uiso 1 1 calc R . .
C4 C 0.78651(19) 0.39590(17) -0.45261(13) 0.0159(3) Uani 1 1 d . . .
H4A H 0.8243 0.2810 -0.4396 0.019 Uiso 1 1 calc R . .
C5 C 0.76176(17) 0.48000(17) -0.35223(13) 0.0125(3) Uani 1 1 d . . .
C6 C 0.79290(19) 0.39353(16) -0.22009(12) 0.0137(3) Uani 1 1 d . . .
H6A H 0.7149 0.2969 -0.1910 0.016 Uiso 1 1 calc R . .
H6B H 0.9250 0.3527 -0.2211 0.016 Uiso 1 1 calc R . .
C7 C 0.77166(17) 0.45495(16) -0.01420(12) 0.0118(2) Uani 1 1 d . . .
C8 C 0.72138(19) 0.57753(17) 0.07530(13) 0.0137(3) Uani 1 1 d . . .
H8A H 0.8351 0.5976 0.1070 0.016 Uiso 1 1 calc R . .
H8B H 0.6325 0.5275 0.1498 0.016 Uiso 1 1 calc R . .
C9 C 0.7744(2) 0.92126(17) 0.02135(14) 0.0183(3) Uani 1 1 d . . .
H9A H 0.7438 0.9437 0.1080 0.027 Uiso 1 1 calc R . .
H9B H 0.7607 1.0249 -0.0406 0.027 Uiso 1 1 calc R . .
H9C H 0.9031 0.8747 0.0079 0.027 Uiso 1 1 calc R . .
C10 C 1.0950(2) 0.9241(2) -0.31769(15) 0.0235(3) Uani 1 1 d . . .
H10A H 1.2304 0.9125 -0.3203 0.035 Uiso 1 1 calc R . .
H10B H 1.0439 1.0189 -0.2785 0.035 Uiso 1 1 calc R . .
H10C H 1.0658 0.9424 -0.4047 0.035 Uiso 1 1 calc R . .
H1 H 1.0705(16) 0.743(2) -0.1750(8) 0.026(5) Uiso 1 1 d 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'
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'
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 N1 82.31(5) . . ?
N2 Cu1 Cl1 173.18(4) . . ?
N1 Cu1 Cl1 98.44(3) . . ?
N2 Cu1 O1 89.97(4) . . ?
N1 Cu1 O1 93.65(4) . . ?
Cl1 Cu1 O1 96.74(3) . . ?
N2 Cu1 S1 84.09(3) . . ?
N1 Cu1 S1 160.32(3) . . ?
Cl1 Cu1 S1 93.433(13) . . ?
O1 Cu1 S1 100.50(3) . . ?
C9 S1 C8 102.58(7) . . ?
C9 S1 Cu1 106.36(5) . . ?
C8 S1 Cu1 97.38(4) . . ?
C10 O1 Cu1 123.33(9) . . ?
C10 O1 H1 108.7(11) . . ?
Cu1 O1 H1 114.4(8) . . ?
C5 N1 C1 119.23(12) . . ?
C5 N1 Cu1 114.07(9) . . ?
C1 N1 Cu1 126.64(9) . . ?
C7 N2 C6 117.25(11) . . ?
C7 N2 Cu1 124.94(9) . . ?
C6 N2 Cu1 116.46(8) . . ?
N1 C1 C2 122.08(13) . . ?
N1 C1 H1A 119.0 . . ?
C2 C1 H1A 119.0 . . ?
C1 C2 C3 118.73(13) . . ?
C1 C2 H2A 120.6 . . ?
C3 C2 H2A 120.6 . . ?
C4 C3 C2 119.17(13) . . ?
C4 C3 H3A 120.4 . . ?
C2 C3 H3A 120.4 . . ?
C3 C4 C5 119.13(13) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
N1 C5 C4 121.64(12) . . ?
N1 C5 C6 116.75(12) . . ?
C4 C5 C6 121.61(12) . . ?
N2 C6 C5 109.43(11) . . ?
N2 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
N2 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
O2 C7 N2 125.44(12) . . ?
O2 C7 C8 117.94(11) . . ?
N2 C7 C8 116.62(11) . . ?
C7 C8 S1 113.26(9) . . ?
C7 C8 H8A 108.9 . . ?
S1 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
S1 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
S1 C9 H9A 109.5 . . ?
S1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
S1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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 N2 1.9316(11) . ?
Cu1 N1 2.0194(12) . ?
Cu1 Cl1 2.2382(4) . ?
Cu1 O1 2.3293(10) . ?
Cu1 S1 2.3322(4) . ?
S1 C9 1.8048(14) . ?
S1 C8 1.8133(14) . ?
O1 C10 1.4240(17) . ?
O1 H1 0.896(4) . ?
O2 C7 1.2519(16) . ?
N1 C5 1.3421(17) . ?
N1 C1 1.3464(17) . ?
N2 C7 1.3176(17) . ?
N2 C6 1.4533(17) . ?
C1 C2 1.381(2) . ?
C1 H1A 0.9500 . ?
C2 C3 1.388(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.384(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.3860(19) . ?
C4 H4A 0.9500 . ?
C5 C6 1.5063(18) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.5213(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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
O1 H1 O2 0.896(4) 1.774(4) 2.6674(14) 175.1(15) 2_765
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Cu1 S1 C9 120.42(6) . . . . ?
N1 Cu1 S1 C9 166.85(11) . . . . ?
Cl1 Cu1 S1 C9 -65.96(5) . . . . ?
O1 Cu1 S1 C9 31.55(6) . . . . ?
N2 Cu1 S1 C8 14.94(6) . . . . ?
N1 Cu1 S1 C8 61.36(11) . . . . ?
Cl1 Cu1 S1 C8 -171.44(5) . . . . ?
O1 Cu1 S1 C8 -73.93(5) . . . . ?
N2 Cu1 O1 C10 171.58(11) . . . . ?
N1 Cu1 O1 C10 89.29(11) . . . . ?
Cl1 Cu1 O1 C10 -9.66(11) . . . . ?
S1 Cu1 O1 C10 -104.44(10) . . . . ?
N2 Cu1 N1 C5 -6.95(9) . . . . ?
Cl1 Cu1 N1 C5 179.90(8) . . . . ?
O1 Cu1 N1 C5 82.53(9) . . . . ?
S1 Cu1 N1 C5 -53.60(15) . . . . ?
N2 Cu1 N1 C1 175.67(12) . . . . ?
Cl1 Cu1 N1 C1 2.52(11) . . . . ?
O1 Cu1 N1 C1 -94.85(11) . . . . ?
S1 Cu1 N1 C1 129.02(11) . . . . ?
N1 Cu1 N2 C7 175.65(11) . . . . ?
O1 Cu1 N2 C7 81.96(11) . . . . ?
S1 Cu1 N2 C7 -18.60(10) . . . . ?
N1 Cu1 N2 C6 9.34(9) . . . . ?
O1 Cu1 N2 C6 -84.35(9) . . . . ?
S1 Cu1 N2 C6 175.09(9) . . . . ?
C5 N1 C1 C2 -1.0(2) . . . . ?
Cu1 N1 C1 C2 176.28(10) . . . . ?
N1 C1 C2 C3 0.2(2) . . . . ?
C1 C2 C3 C4 0.6(2) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C1 N1 C5 C4 0.97(19) . . . . ?
Cu1 N1 C5 C4 -176.62(10) . . . . ?
C1 N1 C5 C6 -179.05(12) . . . . ?
Cu1 N1 C5 C6 3.36(14) . . . . ?
C3 C4 C5 N1 -0.2(2) . . . . ?
C3 C4 C5 C6 179.83(12) . . . . ?
C7 N2 C6 C5 -177.13(11) . . . . ?
Cu1 N2 C6 C5 -9.73(14) . . . . ?
N1 C5 C6 N2 3.83(16) . . . . ?
C4 C5 C6 N2 -176.19(12) . . . . ?
C6 N2 C7 O2 -0.19(19) . . . . ?
Cu1 N2 C7 O2 -166.41(10) . . . . ?
C6 N2 C7 C8 179.71(11) . . . . ?
Cu1 N2 C7 C8 13.49(16) . . . . ?
O2 C7 C8 S1 -176.58(10) . . . . ?
N2 C7 C8 S1 3.51(15) . . . . ?
C9 S1 C8 C7 -122.26(10) . . . . ?
Cu1 S1 C8 C7 -13.60(9) . . . . ?
