#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007179.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_2007179
loop_
_publ_author_name
'Warda, S. A.'
_publ_section_title
;
 An Exact Quasi-Ferrodistortive Ordering in
 (<i>N</i>,<i>N</i>'-Di-<i>n</i>-butylthiourea-<i>S</i>)(<i>N</i>-salicylideneglycinato-<i>O</i>,<i>N</i>,<i>O</i>')copper(II)
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              460
_journal_page_last               462
_journal_volume                  54
_journal_year                    1998
_chemical_formula_iupac          '[Cu(C9 H7 NO3)(C9 H20 N2 S)]'
_chemical_formula_sum            'C18 H27 Cu N3 O3 S'
_chemical_formula_weight         429.03
_chemical_name_systematic
;
 N,N'-dibutylthiourea-(N-salicylideneglycinato)copper(II)
;
_space_group_IT_number           78
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4cw'
_symmetry_space_group_name_H-M   'P 43'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1747(16)
_cell_length_b                   12.1747(16)
_cell_length_c                   13.791(2)
_cell_measurement_reflns_used    5000
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.97
_cell_measurement_theta_min      2.23
_cell_volume                     2044.1(5)
_computing_cell_refinement       'CELL (Stoe, 1997a)'
_computing_data_collection       'EXPOSE (Stoe, 1997b)'
_computing_data_reduction        'INTEGRATE (Stoe, 1997c)'
_computing_molecular_graphics    'XP in SHELXTL (Siemens, 1996b)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 70
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       'Image plate, Stoe IPDS'
_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  0.0576
_diffrn_reflns_av_sigmaI/netI    0.0511
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16171
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         2.23
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    1.192
_exptl_absorpt_correction_T_max  0.875
_exptl_absorpt_correction_T_min  0.425
_exptl_absorpt_correction_type   'Integration (XPREP; Siemens, 1996a)'
_exptl_crystal_colour            Violet
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             900
_exptl_crystal_size_max          0.87
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.276
_refine_ls_abs_structure_details
'Flack (1983) parameter = 0.000(13); 1799 Friedel pairs'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    H_atoms:_see_below
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3788
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          '< 0.001'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w=1/[\s^2^(Fo^2^)+(0.0362P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_ref         0.0803
_reflns_number_gt                2729
_reflns_number_total             3788
_reflns_threshold_expression     >2\s(I)
_[local]_cod_data_source_file    jz1262.cif
_[local]_cod_data_source_block   I
_cod_original_cell_volume        2044.2(5)
_cod_database_code               2007179
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'
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_type_symbol
Cu 0.87075(4) 0.08498(4) 0.00084(4) 0.05763(14) Uani d . 1 Cu
S 0.82208(8) 0.26332(8) -0.02520(9) 0.0653(3) Uani d . 1 S
O1 1.0250(2) 0.0949(2) 0.0017(3) 0.0660(7) Uani d . 1 O
N1 0.8718(2) -0.0728(2) -0.0070(3) 0.0559(8) Uani d . 1 N
C1 1.0974(3) 0.0143(3) -0.0064(3) 0.0569(9) Uani d . 1 C
O2 0.7199(2) 0.0645(2) 0.0423(2) 0.0728(9) Uani d . 1 O
N2 1.0327(3) 0.3166(2) -0.0232(3) 0.0680(10) Uani d D 1 N
H21 1.042(3) 0.2466(16) -0.004(4) 0.082 Uiso d D 1 H
C2 1.2089(3) 0.0407(3) -0.0154(3) 0.0650(12) Uani d . 1 C
H2 1.2181 0.1325 -0.0319 0.078 Uiso d R 1 H
N3 0.9157(3) 0.4493(2) -0.0802(3) 0.0658(9) Uani d D 1 N
H31 0.970(3) 0.494(3) -0.100(3) 0.079 Uiso d D 1 H
O3 0.5956(3) -0.0655(2) 0.0750(3) 0.0924(11) Uani d . 1 O
C3 1.2889(4) -0.0380(4) -0.0229(4) 0.0773(15) Uani d . 1 C
H3 1.3775 -0.0227 -0.0402 0.093 Uiso d R 1 H
C4 1.2595(4) -0.1491(4) -0.0204(4) 0.0850(15) Uani d . 1 C
H4 1.3187 -0.2045 -0.0177 0.102 Uiso d R 1 H
C5 1.1525(3) -0.1785(3) -0.0113(4) 0.0707(12) Uani d . 1 C
H5 1.1137 -0.2752 -0.0068 0.085 Uiso d R 1 H
C6 1.0683(3) -0.0981(3) -0.0070(3) 0.0576(10) Uani d . 1 C
C7 0.9570(3) -0.1364(3) -0.0051(3) 0.0583(9) Uani d . 1 C
H7 0.9418 -0.2311 0.0001 0.070 Uiso d R 1 H
C8 0.7620(3) -0.1189(3) -0.0026(4) 0.0624(10) Uani d . 1 C
H8A 0.7650 -0.1797 0.0374 0.075 Uiso d R 1 H
H8B 0.7304 -0.1481 -0.0765 0.075 Uiso d R 1 H
C9 0.6849(3) -0.0360(3) 0.0428(3) 0.0664(12) Uani d . 1 C
C10 0.9328(3) 0.3491(3) -0.0450(3) 0.0587(10) Uani d . 1 C
C11 1.1314(3) 0.3835(4) -0.0302(4) 0.0762(15) Uani d . 1 C
H11A 1.1257 0.4311 -0.0864 0.091 Uiso calc R 1 H
H11B 1.1945 0.3361 -0.0394 0.091 Uiso calc R 1 H
C12 1.1482(5) 0.4517(5) 0.0580(5) 0.115(2) Uani d . 1 C
H12A 1.1441 0.4056 0.1153 0.138 Uiso calc R 1 H
H12B 1.0906 0.5065 0.0624 0.138 Uiso calc R 1 H
C13 1.2601(6) 0.5086(6) 0.0543(6) 0.145(3) Uani d . 1 C
H13A 1.3157 0.4546 0.0379 0.174 Uiso calc R 1 H
H13B 1.2591 0.5632 0.0031 0.174 Uiso calc R 1 H
C14 1.2894(7) 0.5595(9) 0.1408(7) 0.197(5) Uani d . 1 C
H14A 1.3599 0.5938 0.1335 0.295 Uiso calc R 1 H
H14B 1.2930 0.5057 0.1916 0.295 Uiso calc R 1 H
H14C 1.2356 0.6141 0.1570 0.295 Uiso calc R 1 H
C15 0.8091(3) 0.4930(3) -0.1078(3) 0.0688(12) Uani d . 1 C
H15A 0.7643 0.4337 -0.1333 0.083 Uiso calc R 1 H
H15B 0.8192 0.5464 -0.1593 0.083 Uiso calc R 1 H
C16 0.7491(3) 0.5466(3) -0.0252(4) 0.0788(15) Uani d . 1 C
H16A 0.7929 0.6067 0.0002 0.095 Uiso calc R 1 H
H16B 0.7384 0.4937 0.0265 0.095 Uiso calc R 1 H
C17 0.6388(4) 0.5899(5) -0.0582(6) 0.119(2) Uani d . 1 C
H17A 0.6512 0.6458 -0.1072 0.143 Uiso calc R 1 H
H17B 0.5988 0.5303 -0.0887 0.143 Uiso calc R 1 H
C18 0.5687(5) 0.6378(5) 0.0196(7) 0.152(3) Uani d . 1 C
H18A 0.5003 0.6620 -0.0078 0.228 Uiso calc R 1 H
H18B 0.6058 0.6991 0.0486 0.228 Uiso calc R 1 H
H18C 0.5546 0.5830 0.0682 0.228 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cu 0.0571(3) 0.0518(3) 0.0640(3) 0.0036(2) 0.0087(3) 0.0027(2)
S 0.0571(5) 0.0505(5) 0.0884(10) 0.0029(4) 0.0076(5) 0.0076(5)
O1 0.0615(15) 0.0525(13) 0.084(2) 0.0113(12) 0.0036(18) 0.0038(16)
N1 0.0610(17) 0.0579(17) 0.049(2) 0.0010(14) 0.0088(17) -0.0008(17)
C1 0.062(2) 0.067(2) 0.042(3) 0.0071(17) 0.0000(19) 0.007(2)
O2 0.0657(17) 0.0522(16) 0.101(3) 0.0041(13) 0.0180(15) -0.0013(14)
N2 0.0566(18) 0.0513(17) 0.096(3) -0.0021(14) -0.0050(18) 0.0023(19)
C2 0.053(2) 0.080(3) 0.062(3) 0.0104(17) 0.000(2) 0.008(2)
N3 0.0563(18) 0.0515(18) 0.090(3) -0.0003(14) 0.0024(18) 0.0071(17)
O3 0.0697(19) 0.0637(18) 0.144(3) -0.0044(14) 0.041(2) -0.0066(18)
C3 0.065(3) 0.094(3) 0.073(4) 0.021(2) 0.002(2) 0.001(3)
C4 0.074(3) 0.091(3) 0.090(4) 0.029(2) -0.002(3) -0.009(3)
C5 0.073(3) 0.068(2) 0.071(3) 0.0237(18) 0.006(2) 0.001(2)
C6 0.066(2) 0.056(2) 0.051(3) 0.0107(18) 0.008(2) 0.000(2)
C7 0.074(2) 0.059(2) 0.041(3) 0.0070(17) 0.013(2) -0.001(2)
C8 0.066(2) 0.0519(19) 0.069(3) -0.0006(16) 0.015(2) 0.000(2)
C9 0.062(2) 0.055(2) 0.082(4) 0.0042(19) 0.015(2) -0.001(2)
C10 0.061(2) 0.049(2) 0.066(3) 0.0002(16) 0.0049(19) 0.0000(17)
C11 0.055(2) 0.069(3) 0.105(5) -0.0057(18) -0.011(2) 0.002(2)
C12 0.115(5) 0.113(4) 0.116(5) -0.048(4) -0.012(4) -0.001(4)
C13 0.154(7) 0.138(6) 0.142(7) -0.075(5) -0.011(5) -0.012(5)
C14 0.151(7) 0.312(14) 0.127(8) -0.090(8) 0.018(6) -0.069(8)
C15 0.058(2) 0.063(2) 0.085(4) 0.0020(18) -0.004(2) 0.011(2)
C16 0.061(2) 0.060(2) 0.115(5) 0.0031(18) 0.005(2) 0.010(2)
C17 0.071(3) 0.091(4) 0.195(7) 0.020(3) 0.012(4) 0.016(4)
C18 0.088(4) 0.100(4) 0.268(10) 0.014(3) 0.066(5) 0.017(6)
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_publ_flag
O1 Cu N1 93.34(12) yes
O1 Cu O2 162.05(15) yes
N1 Cu O2 83.92(12) yes
O1 Cu S 101.49(8) yes
N1 Cu S 160.74(11) yes
O2 Cu S 85.57(8) yes
C10 S Cu 113.44(13) ?
C1 O1 Cu 128.0(2) ?
C7 N1 C8 120.5(3) ?
C7 N1 Cu 126.9(3) ?
C8 N1 Cu 112.2(2) ?
O1 C1 C2 118.8(4) ?
O1 C1 C6 123.5(3) ?
C2 C1 C6 117.7(3) ?
C9 O2 Cu 115.7(2) ?
C10 N2 C11 125.5(3) ?
C10 N2 H21 118(3) ?
C11 N2 H21 117(3) ?
C3 C2 C1 122.4(4) ?
C3 C2 H2 126.7 ?
C1 C2 H2 109.6 ?
C10 N3 C15 124.9(3) ?
C10 N3 H31 124(3) ?
C15 N3 H31 111(3) ?
C2 C3 C4 119.5(4) ?
C2 C3 H3 125.7 ?
C4 C3 H3 114.3 ?
C5 C4 C3 120.2(4) ?
C5 C4 H4 121.2 ?
C3 C4 H4 118.3 ?
C4 C5 C6 121.1(4) ?
C4 C5 H5 127.3 ?
C6 C5 H5 111.6 ?
C1 C6 C5 119.1(4) ?
C1 C6 C7 123.5(3) ?
C5 C6 C7 117.4(3) ?
N1 C7 C6 124.3(3) ?
N1 C7 H7 117.6 ?
C6 C7 H7 118.1 ?
N1 C8 C9 109.3(3) ?
N1 C8 H8A 107.3 ?
C9 C8 H8A 108.2 ?
N1 C8 H8B 113.1 ?
C9 C8 H8B 111.5 ?
H8A C8 H8B 107.2 ?
O3 C9 O2 124.7(4) ?
O3 C9 C8 120.2(3) ?
O2 C9 C8 115.1(3) ?
N2 C10 N3 120.3(3) ?
N2 C10 S 120.3(3) ?
N3 C10 S 119.4(3) ?
N2 C11 C12 111.8(4) ?
N2 C11 H11A 109.3 ?
C12 C11 H11A 109.3 ?
N2 C11 H11B 109.3 ?
C12 C11 H11B 109.3 ?
H11A C11 H11B 107.9 ?
C11 C12 C13 110.4(6) ?
C11 C12 H12A 109.6 ?
C13 C12 H12A 109.6 ?
C11 C12 H12B 109.6 ?
C13 C12 H12B 109.6 ?
H12A C12 H12B 108.1 ?
C14 C13 C12 113.7(8) ?
C14 C13 H13A 108.8 ?
C12 C13 H13A 108.8 ?
C14 C13 H13B 108.8 ?
C12 C13 H13B 108.8 ?
H13A C13 H13B 107.7 ?
C13 C14 H14A 109.5 ?
C13 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
C13 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
N3 C15 C16 113.2(4) ?
N3 C15 H15A 108.9 ?
C16 C15 H15A 108.9 ?
N3 C15 H15B 108.9 ?
C16 C15 H15B 108.9 ?
H15A C15 H15B 107.8 ?
C15 C16 C17 110.7(5) ?
C15 C16 H16A 109.5 ?
C17 C16 H16A 109.5 ?
C15 C16 H16B 109.5 ?
C17 C16 H16B 109.5 ?
H16A C16 H16B 108.1 ?
C18 C17 C16 115.3(7) ?
C18 C17 H17A 108.4 ?
C16 C17 H17A 108.4 ?
C18 C17 H17B 108.4 ?
C16 C17 H17B 108.4 ?
H17A C17 H17B 107.5 ?
C17 C18 H18A 109.5 ?
C17 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
C17 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cu O1 1.882(2) yes
Cu N1 1.924(3) yes
Cu O2 1.940(3) yes
Cu S 2.2791(11) yes
S C10 1.727(4) ?
O1 C1 1.324(4) ?
N1 C7 1.295(5) ?
N1 C8 1.451(5) ?
C1 C2 1.401(5) ?
C1 C6 1.413(5) ?
O2 C9 1.295(5) ?
N2 C10 1.314(5) ?
N2 C11 1.455(5) ?
N2 H21 0.898(10) ?
C2 C3 1.370(6) ?
C2 H2 1.1462 ?
N3 C10 1.329(5) ?
N3 C15 1.454(5) ?
N3 H31 0.900(10) ?
O3 C9 1.228(5) ?
C3 C4 1.400(7) ?
C3 H3 1.1199 ?
C4 C5 1.357(6) ?
C4 H4 0.9870 ?
C5 C6 1.419(5) ?
C5 H5 1.2692 ?
C6 C7 1.432(5) ?
C7 H7 1.1701 ?
C8 C9 1.514(5) ?
C8 H8A 0.9230 ?
C8 H8B 1.1467 ?
C11 C12 1.488(8) ?
C11 H11A 0.9700 ?
C11 H11B 0.9700 ?
C12 C13 1.530(7) ?
C12 H12A 0.9700 ?
C12 H12B 0.9700 ?
C13 C14 1.390(11) ?
C13 H13A 0.9700 ?
C13 H13B 0.9700 ?
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 0.9600 ?
C15 C16 1.503(6) ?
C15 H15A 0.9700 ?
C15 H15B 0.9700 ?
C16 C17 1.513(7) ?
C16 H16A 0.9700 ?
C16 H16B 0.9700 ?
C17 C18 1.491(10) ?
C17 H17A 0.9700 ?
C17 H17B 0.9700 ?
C18 H18A 0.9600 ?
C18 H18B 0.9600 ?
C18 H18C 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
N2 H21 O1 1_555 0.90 1.85 2.722(4) 160 yes
N3 H31 O3 3_654 0.90 1.99 2.865(4) 165 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
O1 Cu S C10 4.6(2)
N1 Cu S C10 -135.0(4)
O2 Cu S C10 167.9(2)
N1 Cu O1 C1 3.3(5)
O2 Cu O1 C1 83.9(6)
S Cu O1 C1 -164.3(4)
O1 Cu N1 C7 3.7(4)
O2 Cu N1 C7 -158.5(4)
S Cu N1 C7 144.2(3)
O1 Cu N1 C8 175.9(3)
O2 Cu N1 C8 13.7(3)
S Cu N1 C8 -43.6(5)
Cu O1 C1 C2 172.6(3)
Cu O1 C1 C6 -7.2(7)
O1 Cu O2 C9 -85.0(5)
N1 Cu O2 C9 -2.9(3)
S Cu O2 C9 160.9(3)
O1 C1 C2 C3 179.2(5)
C6 C1 C2 C3 -1.0(7)
C1 C2 C3 C4 -0.9(8)
C2 C3 C4 C5 0.4(8)
C3 C4 C5 C6 1.9(8)
O1 C1 C6 C5 -176.9(4)
C2 C1 C6 C5 3.3(7)
O1 C1 C6 C7 4.1(7)
C2 C1 C6 C7 -175.6(4)
C4 C5 C6 C1 -3.8(8)
C4 C5 C6 C7 175.2(5)
C8 N1 C7 C6 -178.6(4)
Cu N1 C7 C6 -7.0(7)
C1 C6 C7 N1 3.2(8)
C5 C6 C7 N1 -175.8(5)
C7 N1 C8 C9 152.2(4)
Cu N1 C8 C9 -20.6(5)
Cu O2 C9 O3 173.0(4)
Cu O2 C9 C8 -8.4(5)
N1 C8 C9 O3 -162.4(5)
N1 C8 C9 O2 19.0(6)
C11 N2 C10 N3 2.6(7)
C11 N2 C10 S -175.6(4)
C15 N3 C10 N2 179.2(4)
C15 N3 C10 S -2.6(6)
Cu S C10 N2 -15.3(4)
Cu S C10 N3 166.5(3)
C10 N2 C11 C12 84.8(6)
N2 C11 C12 C13 172.1(6)
C11 C12 C13 C14 -170.2(8)
C10 N3 C15 C16 88.0(5)
N3 C15 C16 C17 -179.7(4)
C15 C16 C17 C18 175.8(4)