#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/30/2233095.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_2233095
loop_
_publ_author_name
'Dege, Necmi'
'Demirtaş, Güneş'
'Içbudak, Hasan'
_publ_section_title
;
 trans-Bis(ethylenediamine-κ²N,N')bis(6-methyl-2,2,4-trioxo-3,4-dihydro-1,2λ⁶,3-oxathiazin-3-ido-κN)copper(II)
;
_journal_coeditor_code           BT5731
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m47
_journal_page_last               m48
_journal_paper_doi               10.1107/S1600536811051658
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Cu (C4 H4 N O4 S)2 (C2 H8 N2)2]'
_chemical_formula_moiety         'C12 H24 Cu N6 O8 S2'
_chemical_formula_sum            'C12 H24 Cu N6 O8 S2'
_chemical_formula_weight         508.03
_chemical_name_systematic
;
trans-Bis(ethylenediamine-κ²N,N')bis(6-methyl-2,2,4-
trioxo-3,4-dihydro-1,2λ⁶,3-oxathiazin-3-ido-κN)copper(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 93.017(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.9853(3)
_cell_length_b                   17.5355(6)
_cell_length_c                   8.4092(4)
_cell_measurement_reflns_used    28030
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.01
_cell_measurement_theta_min      2.32
_cell_volume                     1028.62(7)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997)and Mercury (Macrae et al., 2006)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution
'WinGX (Farrugia, 1997) and SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'w-scan rotation'
_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  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0155
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14620
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    1.317
_exptl_absorpt_correction_T_max  0.6779
_exptl_absorpt_correction_T_min  0.4383
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             526
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.252
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0244
_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)+(0.0309P)²+0.3289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0637
_refine_ls_wR_factor_ref         0.0649
_reflns_number_gt                1865
_reflns_number_total             2023
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5731.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2233095
_cod_database_fobs_code          2233095
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_symmetry_multiplicity
C C1 0.1200(3) 0.55390(12) 0.7619(2) 0.0473(4) Uani d . 1 1
C C2 0.0228(3) 0.59733(13) 0.8823(2) 0.0526(5) Uani d . 1 1
H H2 -0.0916 0.5781 0.9177 0.063 Uiso calc R 1 1
C C3 0.0877(3) 0.66195(12) 0.9434(2) 0.0483(4) Uani d . 1 1
C C4 -0.0106(3) 0.71462(15) 1.0516(3) 0.0697(6) Uani d . 1 1
H H4A -0.1428 0.7001 1.0557 0.105 Uiso calc R 1 1
H H4B -0.0027 0.7659 1.0123 0.105 Uiso calc R 1 1
H H4C 0.0502 0.7118 1.1565 0.105 Uiso calc R 1 1
C C5 0.5868(3) 0.36713(11) 0.6731(2) 0.0508(5) Uani d . 1 1
H H5A 0.6284 0.3403 0.7697 0.061 Uiso calc R 1 1
H H5B 0.6471 0.3438 0.5839 0.061 Uiso calc R 1 1
C C6 0.3715(3) 0.36387(11) 0.6486(3) 0.0539(5) Uani d . 1 1
H H6A 0.3310 0.3119 0.6257 0.065 Uiso calc R 1 1
H H6B 0.3123 0.3805 0.7444 0.065 Uiso calc R 1 1
Cu Cu1 0.5000 0.5000 0.5000 0.03988(11) Uani d S 1 2
N N1 0.2955(2) 0.57689(9) 0.71898(19) 0.0463(4) Uani d . 1 1
N N2 0.6387(2) 0.44831(9) 0.6856(2) 0.0435(3) Uani d . 1 1
N N3 0.3116(2) 0.41394(9) 0.51456(19) 0.0404(3) Uani d . 1 1
O O1 0.5067(2) 0.59346(10) 0.96415(19) 0.0653(4) Uani d . 1 1
O O2 0.5347(2) 0.68003(9) 0.7441(2) 0.0699(5) Uani d . 1 1
O O3 0.26382(19) 0.69080(8) 0.90616(17) 0.0539(3) Uani d . 1 1
O O4 0.0388(2) 0.49923(9) 0.6937(2) 0.0673(4) Uani d . 1 1
S S1 0.41531(6) 0.63171(3) 0.83179(6) 0.04469(13) Uani d . 1 1
H H2A 0.755(3) 0.4555(13) 0.691(3) 0.054(6) Uiso d . 1 1
H H2B 0.602(3) 0.4650(14) 0.776(3) 0.055(6) Uiso d . 1 1
H H3A 0.307(3) 0.3881(13) 0.429(3) 0.053(6) Uiso d . 1 1
H H3B 0.207(3) 0.4339(13) 0.526(3) 0.056(6) Uiso d . 1 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'
Cu Cu 0.3201 1.2651 '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'
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_3
_geom_angle
O4 C1 N1 . . 120.27(17)
O4 C1 C2 . . 120.39(17)
N1 C1 C2 . . 119.23(17)
C3 C2 C1 . . 123.79(18)
C3 C2 H2 . . 118.1
C1 C2 H2 . . 118.1
C2 C3 O3 . . 121.33(17)
C2 C3 C4 . . 127.8(2)
O3 C3 C4 . . 110.88(19)
C3 C4 H4A . . 109.5
C3 C4 H4B . . 109.5
H4A C4 H4B . . 109.5
C3 C4 H4C . . 109.5
H4A C4 H4C . . 109.5
H4B C4 H4C . . 109.5
N2 C5 C6 . . 106.65(15)
N2 C5 H5A . . 110.4
C6 C5 H5A . . 110.4
N2 C5 H5B . . 110.4
C6 C5 H5B . . 110.4
H5A C5 H5B . . 108.6
N3 C6 C5 . . 108.84(15)
N3 C6 H6A . . 109.9
C5 C6 H6A . . 109.9
N3 C6 H6B . . 109.9
C5 C6 H6B . . 109.9
H6A C6 H6B . . 108.3
N1 Cu1 N2 . . 86.97(6)
N1 Cu1 N3 . . 87.84(5)
N2 Cu1 N2 . 3_666 180.0
N2 Cu1 N3 . . 84.51(7)
N2 Cu1 N3 3_666 . 95.49(7)
N2 Cu1 N3 . 3_666 95.49(7)
N2 Cu1 N3 3_666 3_666 84.51(7)
N3 Cu1 N3 . 3_666 180.00(6)
C1 N1 S1 . . 118.93(13)
C5 N2 Cu1 . . 105.92(12)
C5 N2 H2A . . 113.1(16)
Cu1 N2 H2A . . 114.0(16)
C5 N2 H2B . . 107.8(16)
Cu1 N2 H2B . . 112.0(15)
H2A N2 H2B . . 104(2)
C6 N3 Cu1 . . 109.52(11)
C6 N3 H3A . . 109.1(15)
Cu1 N3 H3A . . 110.4(15)
C6 N3 H3B . . 112.7(16)
Cu1 N3 H3B . . 106.0(16)
H3A N3 H3B . . 109(2)
C3 O3 S1 . . 117.28(12)
O1 S1 O2 . . 115.84(11)
O1 S1 N1 . . 112.91(10)
O2 S1 N1 . . 111.20(9)
O1 S1 O3 . . 105.87(9)
O2 S1 O3 . . 103.33(8)
N1 S1 O3 . . 106.64(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O4 . 1.239(2) ?
C1 N1 . 1.357(2) ?
C1 C2 . 1.462(3) ?
C2 C3 . 1.315(3) ?
C2 H2 . 0.9300 ?
C3 O3 . 1.381(2) ?
C3 C4 . 1.489(3) ?
C4 H4A . 0.9600 ?
C4 H4B . 0.9600 ?
C4 H4C . 0.9600 ?
C5 N2 . 1.471(2) ?
C5 C6 . 1.509(3) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 N3 . 1.472(2) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
Cu1 N1 . 2.7434(15) y
Cu1 N1 3_666 2.7434(15) ?
Cu1 N2 . 2.0090(16) y
Cu1 N2 3_666 2.0090(16) ?
Cu1 N3 . 2.0101(14) y
Cu1 N3 3_666 2.0102(14) ?
N1 S1 . 1.5624(15) ?
N2 H2A . 0.82(2) ?
N2 H2B . 0.87(2) ?
N3 H3A . 0.85(2) ?
N3 H3B . 0.82(2) ?
O1 S1 . 1.4218(16) ?
O2 S1 . 1.4220(15) ?
O3 S1 . 1.6292(13) ?
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
N3 H3B O4 . 0.82(2) 2.20(2) 2.905(2) 143(2)
N2 H2A O4 1_655 0.82(2) 2.13(2) 2.931(2) 167(2)
N2 H2B O1 3_667 0.87(2) 2.57(2) 3.250(2) 137(2)
N3 H3A O2 3_666 0.85(2) 2.23(2) 2.974(2) 147(2)
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_site_symmetry_1
_geom_torsion
O4 C1 C2 C3 . -170.1(2)
N1 C1 C2 C3 . 6.0(3)
C1 C2 C3 O3 . -5.2(3)
C1 C2 C3 C4 . 172.3(2)
N2 C5 C6 N3 . 52.2(2)
O4 C1 N1 S1 . -165.20(17)
C2 C1 N1 S1 . 18.7(3)
C6 C5 N2 Cu1 . -49.01(18)
N3 Cu1 N2 C5 . 26.67(13)
N3 Cu1 N2 C5 3_666 -153.33(13)
C5 C6 N3 Cu1 . -29.1(2)
N2 Cu1 N3 C6 . 1.51(14)
N2 Cu1 N3 C6 3_666 -178.49(14)
C2 C3 O3 S1 . -18.8(2)
C4 C3 O3 S1 . 163.28(15)
C1 N1 S1 O1 . 78.40(17)
C1 N1 S1 O2 . -149.42(16)
C1 N1 S1 O3 . -37.46(18)
C3 O3 S1 O1 . -82.80(15)
C3 O3 S1 O2 . 154.99(15)
C3 O3 S1 N1 . 37.68(16)
