#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/23/7002397.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_7002397
loop_
_publ_author_name
'Bowmaker, Graham A.'
'Chaichit, Narongsak'
'Hanna, John V.'
'Pakawatchai, Chaveng'
'Skelton, Brian W.'
'White, Allan H.'
_publ_section_title
;
 Spectroscopy and structures of two complete families, one mononuclear,
 the other binuclear, of 1 : 2 CuX : dptu
 stoichiometry (X = Cl, Br, I; ‘dptu’ =
 N,N′-diphenylthiourea)
;
_journal_issue                   39
_journal_name_full               'Dalton Transactions'
_journal_page_first              8308
_journal_page_last               8316
_journal_paper_doi               10.1039/b909167j
_journal_year                    2009
_chemical_formula_moiety         'C26 H24 Br Cu N4 S2, H2 O'
_chemical_formula_sum            'C26 H26 Br Cu N4 O S2'
_chemical_formula_weight         618.08
_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_date             2007-11-14T07:52:14-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90.047(3)
_cell_angle_beta                 73.966(3)
_cell_angle_gamma                69.386(4)
_cell_formula_units_Z            2
_cell_length_a                   9.4378(5)
_cell_length_b                   12.1456(6)
_cell_length_c                   12.6684(4)
_cell_measurement_reflns_used    10681
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      37.5235
_cell_measurement_theta_min      3.3555
_cell_volume                     1298.51(11)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May 8 2007,13:10:02)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May 8 2007,13:10:02)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May 8 2007,13:10:02)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4738
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device_type
;
Oxford Diffraction Gemini diffractometer
;
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0622971087
_diffrn_orient_matrix_UB_12      0.0559677401
_diffrn_orient_matrix_UB_13      0.0094996982
_diffrn_orient_matrix_UB_21      0.0552954822
_diffrn_orient_matrix_UB_22      0.0282314241
_diffrn_orient_matrix_UB_23      -0.0043898359
_diffrn_orient_matrix_UB_31      0.0107442887
_diffrn_orient_matrix_UB_32      0.0001379742
_diffrn_orient_matrix_UB_33      -0.0575544179
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0831
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            27220
_diffrn_reflns_theta_full        36.5
_diffrn_reflns_theta_max         37.63
_diffrn_reflns_theta_min         3.37
_exptl_absorpt_coefficient_mu    2.568
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.62371
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May 8 2007,13:10:02)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.967
_refine_diff_density_min         -0.85
_refine_diff_density_rms         0.13
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         12945
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0336
_refine_ls_shift/su_max          0.044
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0453P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0737
_refine_ls_wR_factor_ref         0.0948
_reflns_number_gt                8308
_reflns_number_total             12945
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            b909167j.txt
_cod_data_source_block           gb0715
_cod_original_cell_volume        1298.51(10)
_cod_original_sg_symbol_Hall     -P_1
_cod_database_code               7002397
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 0.445832(9) 0.604967(7) 0.268191(6) 0.01384(2) Uani 1 1 d . . .
Br1 Br 0.334507(7) 0.812611(6) 0.307922(5) 0.01611(2) Uani 1 1 d . . .
S1 S 0.629153(18) 0.506188(14) 0.114691(12) 0.01381(4) Uani 1 1 d . . .
C1 C 0.64633(7) 0.59530(5) 0.01103(5) 0.01128(13) Uani 1 1 d . . .
N11 N 0.75998(6) 0.55270(5) -0.08593(4) 0.01414(13) Uani 1 1 d . . .
H11 H 0.7652 0.6006 -0.1378 0.017 Uiso 1 1 calc R . .
C111 C 0.87281(7) 0.43411(6) -0.10957(5) 0.01405(15) Uani 1 1 d . . .
C112 C 1.03266(7) 0.41543(6) -0.13193(5) 0.01549(15) Uani 1 1 d . . .
H112 H 1.0659 0.4807 -0.1321 0.019 Uiso 1 1 calc R . .
C113 C 1.14436(8) 0.29968(7) -0.15426(5) 0.01984(17) Uani 1 1 d . . .
H113 H 1.254 0.2863 -0.1706 0.024 Uiso 1 1 calc R . .
C114 C 1.09508(9) 0.20444(7) -0.15258(6) 0.02241(19) Uani 1 1 d . . .
H114 H 1.1704 0.1257 -0.1657 0.027 Uiso 1 1 calc R . .
C115 C 0.93438(9) 0.22508(6) -0.13158(5) 0.02037(17) Uani 1 1 d . . .
H115 H 0.9005 0.1601 -0.1313 0.024 Uiso 1 1 calc R . .
C116 C 0.82402(8) 0.33910(6) -0.11126(5) 0.01624(15) Uani 1 1 d . . .
H116 H 0.7149 0.3525 -0.0985 0.019 Uiso 1 1 calc R . .
N12 N 0.54821(6) 0.70842(5) 0.02489(4) 0.01333(13) Uani 1 1 d . . .
H12 H 0.4837 0.7381 0.0915 0.016 Uiso 1 1 calc R . .
C121 C 0.54096(7) 0.78491(5) -0.06173(5) 0.01385(14) Uani 1 1 d . . .
C122 C 0.45048(8) 0.78086(6) -0.12993(6) 0.01975(16) Uani 1 1 d . . .
H122 H 0.395 0.728 -0.1197 0.024 Uiso 1 1 calc R . .
C123 C 0.44146(9) 0.85523(7) -0.21415(6) 0.02410(18) Uani 1 1 d . . .
H123 H 0.3791 0.8537 -0.2611 0.029 Uiso 1 1 calc R . .
C124 C 0.52435(9) 0.93142(6) -0.22858(6) 0.02197(18) Uani 1 1 d . . .
H124 H 0.5183 0.9822 -0.2855 0.026 Uiso 1 1 calc R . .
C125 C 0.61584(9) 0.93383(6) -0.16035(6) 0.02437(18) Uani 1 1 d . . .
H125 H 0.6726 0.9858 -0.171 0.029 Uiso 1 1 calc R . .
C126 C 0.62456(8) 0.86027(6) -0.07636(6) 0.01862(16) Uani 1 1 d . . .
H126 H 0.6872 0.8617 -0.0295 0.022 Uiso 1 1 calc R . .
S2 S 0.387676(18) 0.475109(14) 0.379267(12) 0.01395(4) Uani 1 1 d . . .
C2 C 0.26080(7) 0.54768(5) 0.50575(5) 0.01173(13) Uani 1 1 d . . .
N21 N 0.18004(6) 0.49492(4) 0.57825(4) 0.01235(12) Uani 1 1 d . . .
H21 H 0.1073 0.5394 0.6371 0.015 Uiso 1 1 calc R . .
C211 C 0.20201(7) 0.37229(5) 0.56810(5) 0.01185(14) Uani 1 1 d . . .
C212 C 0.06838(7) 0.34231(6) 0.58800(5) 0.01581(15) Uani 1 1 d . . .
H212 H -0.0343 0.4025 0.6071 0.019 Uiso 1 1 calc R . .
C213 C 0.08595(8) 0.22382(6) 0.57972(5) 0.01812(16) Uani 1 1 d . . .
H213 H -0.005 0.203 0.5927 0.022 Uiso 1 1 calc R . .
C214 C 0.23621(9) 0.13549(6) 0.55256(6) 0.02164(18) Uani 1 1 d . . .
H214 H 0.2482 0.0546 0.5451 0.026 Uiso 1 1 calc R . .
C215 C 0.36857(8) 0.16642(6) 0.53638(6) 0.02238(19) Uani 1 1 d . . .
H215 H 0.471 0.1062 0.5193 0.027 Uiso 1 1 calc R . .
C216 C 0.35256(8) 0.28447(6) 0.54501(5) 0.01637(15) Uani 1 1 d . . .
H216 H 0.4431 0.3052 0.5353 0.02 Uiso 1 1 calc R . .
N22 N 0.23655(6) 0.66132(5) 0.52993(4) 0.01306(13) Uani 1 1 d . . .
H22 H 0.2744 0.696 0.4739 0.016 Uiso 1 1 calc R . .
C221 C 0.15908(7) 0.73482(5) 0.63220(5) 0.01332(14) Uani 1 1 d . . .
C222 C 0.09105(8) 0.85519(6) 0.62839(6) 0.01859(17) Uani 1 1 d . . .
H222 H 0.0919 0.8856 0.5592 0.022 Uiso 1 1 calc R . .
C223 C 0.02112(9) 0.93226(7) 0.72578(6) 0.02295(19) Uani 1 1 d . . .
H223 H -0.0244 1.0151 0.7232 0.028 Uiso 1 1 calc R . .
C224 C 0.01853(8) 0.88669(6) 0.82691(6) 0.02062(17) Uani 1 1 d . . .
H224 H -0.0308 0.9385 0.8936 0.025 Uiso 1 1 calc R . .
C225 C 0.08788(8) 0.76565(6) 0.83039(5) 0.01699(16) Uani 1 1 d . . .
H225 H 0.0857 0.7352 0.8996 0.02 Uiso 1 1 calc R . .
C226 C 0.16031(7) 0.68876(6) 0.73372(5) 0.01493(15) Uani 1 1 d . . .
H226 H 0.21 0.6062 0.7362 0.018 Uiso 1 1 calc R . .
O1 O 0.15604(6) 0.35548(4) 0.29842(4) 0.01791(12) Uani 1 1 d D . .
H1A H 0.2080(9) 0.3825(7) 0.3225(7) 0.020(2) Uiso 1 1 d D . .
H1B H 0.1650(13) 0.2922(9) 0.2964(9) 0.056(4) 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 0 '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 0.006 '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'
Br Br -0.2901 2.4595 '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
S1 Cu1 S2 108.433(7) . . ?
S1 Cu1 Br1 125.575(7) . . ?
S2 Cu1 Br1 125.986(6) . . ?
C1 S1 Cu1 111.905(19) . . ?
N12 C1 N11 118.74(5) . . ?
N12 C1 S1 120.92(4) . . ?
N11 C1 S1 120.34(4) . . ?
C1 N11 C111 123.71(5) . . ?
C1 N11 H11 118.1 . . ?
C111 N11 H11 118.1 . . ?
C116 C111 C112 120.44(6) . . ?
C116 C111 N11 120.66(6) . . ?
C112 C111 N11 118.90(7) . . ?
C111 C112 C113 119.50(7) . . ?
C111 C112 H112 120.3 . . ?
C113 C112 H112 120.2 . . ?
C114 C113 C112 120.05(7) . . ?
C114 C113 H113 120 . . ?
C112 C113 H113 120 . . ?
C113 C114 C115 119.56(6) . . ?
C113 C114 H114 120.2 . . ?
C115 C114 H114 120.2 . . ?
C116 C115 C114 120.60(8) . . ?
C116 C115 H115 119.7 . . ?
C114 C115 H115 119.7 . . ?
C115 C116 C111 119.81(7) . . ?
C115 C116 H116 120.1 . . ?
C111 C116 H116 120.1 . . ?
C1 N12 C121 124.47(5) . . ?
C1 N12 H12 117.8 . . ?
C121 N12 H12 117.8 . . ?
C122 C121 C126 121.10(6) . . ?
C122 C121 N12 118.78(7) . . ?
C126 C121 N12 120.12(7) . . ?
C121 C122 C123 119.46(8) . . ?
C121 C122 H122 120.3 . . ?
C123 C122 H122 120.3 . . ?
C124 C123 C122 119.57(8) . . ?
C124 C123 H123 120.2 . . ?
C122 C123 H123 120.2 . . ?
C125 C124 C123 120.42(7) . . ?
C125 C124 H124 119.8 . . ?
C123 C124 H124 119.8 . . ?
C124 C125 C126 120.11(8) . . ?
C124 C125 H125 119.9 . . ?
C126 C125 H125 119.9 . . ?
C121 C126 C125 119.33(7) . . ?
C121 C126 H126 120.3 . . ?
C125 C126 H126 120.3 . . ?
C2 S2 Cu1 109.94(2) . . ?
N22 C2 N21 119.08(5) . . ?
N22 C2 S2 119.16(5) . . ?
N21 C2 S2 121.67(5) . . ?
C2 N21 C211 125.49(4) . . ?
C2 N21 H21 117.3 . . ?
C211 N21 H21 117.3 . . ?
C212 C211 C216 120.52(6) . . ?
C212 C211 N21 118.29(5) . . ?
C216 C211 N21 121.10(6) . . ?
C213 C212 C211 119.59(5) . . ?
C213 C212 H212 120.2 . . ?
C211 C212 H212 120.2 . . ?
C212 C213 C214 120.30(7) . . ?
C212 C213 H213 119.8 . . ?
C214 C213 H213 119.8 . . ?
C215 C214 C213 119.58(7) . . ?
C215 C214 H214 120.2 . . ?
C213 C214 H214 120.2 . . ?
C216 C215 C214 120.66(6) . . ?
C216 C215 H215 119.7 . . ?
C214 C215 H215 119.7 . . ?
C215 C216 C211 119.25(7) . . ?
C215 C216 H216 120.4 . . ?
C211 C216 H216 120.4 . . ?
C2 N22 C221 130.00(5) . . ?
C2 N22 H22 115 . . ?
C221 N22 H22 115 . . ?
C222 C221 C226 120.51(6) . . ?
C222 C221 N22 117.65(6) . . ?
C226 C221 N22 121.70(5) . . ?
C221 C222 C223 120.21(6) . . ?
C221 C222 H222 119.9 . . ?
C223 C222 H222 119.9 . . ?
C224 C223 C222 119.49(7) . . ?
C224 C223 H223 120.3 . . ?
C222 C223 H223 120.3 . . ?
C225 C224 C223 120.14(6) . . ?
C225 C224 H224 119.9 . . ?
C223 C224 H224 119.9 . . ?
C226 C225 C224 120.65(6) . . ?
C226 C225 H225 119.7 . . ?
C224 C225 H225 119.7 . . ?
C225 C226 C221 118.97(6) . . ?
C225 C226 H226 120.5 . . ?
C221 C226 H226 120.5 . . ?
H1A O1 H1B 124.7(11) . . ?
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 S1 2.21139(19) . ?
Cu1 S2 2.2261(2) . ?
Cu1 Br1 2.35745(16) . ?
S1 C1 1.7120(6) . ?
C1 N12 1.3378(7) . ?
C1 N11 1.3443(7) . ?
N11 C111 1.4288(8) . ?
N11 H11 0.88 . ?
C111 C116 1.3869(11) . ?
C111 C112 1.3895(10) . ?
C112 C113 1.3996(9) . ?
C112 H112 0.95 . ?
C113 C114 1.3885(13) . ?
C113 H113 0.95 . ?
C114 C115 1.3939(11) . ?
C114 H114 0.95 . ?
C115 C116 1.3800(9) . ?
C115 H115 0.95 . ?
C116 H116 0.95 . ?
N12 C121 1.4388(8) . ?
N12 H12 0.88 . ?
C121 C122 1.3839(11) . ?
C121 C126 1.3867(11) . ?
C122 C123 1.3996(10) . ?
C122 H122 0.95 . ?
C123 C124 1.3903(13) . ?
C123 H123 0.95 . ?
C124 C125 1.3869(13) . ?
C124 H124 0.95 . ?
C125 C126 1.3911(10) . ?
C125 H125 0.95 . ?
C126 H126 0.95 . ?
S2 C2 1.7242(5) . ?
C2 N22 1.3377(9) . ?
C2 N21 1.3392(8) . ?
N21 C211 1.4302(8) . ?
N21 H21 0.88 . ?
C211 C212 1.3908(10) . ?
C211 C216 1.3946(8) . ?
C212 C213 1.3899(10) . ?
C212 H212 0.95 . ?
C213 C214 1.3925(9) . ?
C213 H213 0.95 . ?
C214 C215 1.3902(12) . ?
C214 H214 0.95 . ?
C215 C216 1.3888(10) . ?
C215 H215 0.95 . ?
C216 H216 0.95 . ?
N22 C221 1.4231(7) . ?
N22 H22 0.88 . ?
C221 C222 1.3813(9) . ?
C221 C226 1.4043(9) . ?
C222 C223 1.3955(9) . ?
C222 H222 0.95 . ?
C223 C224 1.3934(11) . ?
C223 H223 0.95 . ?
C224 C225 1.3893(10) . ?
C224 H224 0.95 . ?
C225 C226 1.3876(8) . ?
C225 H225 0.95 . ?
C226 H226 0.95 . ?
O1 H1A 0.799(10) . ?
O1 H1B 0.743(11) . ?
