#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/55/2015566.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_2015566
loop_
_publ_author_name
'Dege, Necmi'
'İçbudak, Hasan'
'Adıyaman, Elif'
_publ_section_title
;
 Bis(acesulfamato-κ²O⁴,N)bis(3-methylpyridine)copper(II)
;
_journal_coeditor_code           GZ3026
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m401
_journal_page_last               m403
_journal_paper_doi               10.1107/S0108270106027880
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '[Cu (C4 H4  O4 N S)2 (C6 H7 N)2]'
_chemical_formula_moiety         'C20 H22 Cu N4 O8 S2'
_chemical_formula_sum            'C20 H22 Cu N4 O8 S2'
_chemical_formula_weight         574.08
_chemical_name_common
;
 Bis(acesulfamato-κ²O,N)bis(3-methylpyridine)copper(II)
;
_chemical_name_systematic
;
Bis[6-methyl-1,2,3-oxathiazin-4(3H)-one
2,2-dioxide(1-)-κ²N³,O⁴]bis(3-methylpyridine)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                 104.892(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.7385(6)
_cell_length_b                   9.1792(7)
_cell_length_c                   12.5005(8)
_cell_measurement_reflns_used    47042
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.94
_cell_measurement_theta_min      2.22
_cell_volume                     1190.80(14)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18687
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         2.79
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.146
_exptl_absorpt_correction_T_max  0.6989
_exptl_absorpt_correction_T_min  0.5805
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             590
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.916
_refine_diff_density_min         -1.292
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2736
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0475
_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)+(0.0452P)²+2.0095P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1189
_reflns_number_gt                2395
_reflns_number_total             2736
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gz3026.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2015566
_cod_database_fobs_code          2015566
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
Cu Cu1 0.5000 0.0000 0.5000 0.03805(16) Uani d S 1
S S1 0.15288(8) 0.04844(9) 0.31144(6) 0.0432(2) Uani d . 1
O O1 0.0570(2) 0.1674(3) 0.34204(19) 0.0511(6) Uani d . 1
O O2 0.0935(3) -0.0885(3) 0.3119(2) 0.0642(7) Uani d . 1
O O3 0.1724(3) 0.0980(4) 0.2098(2) 0.0774(9) Uani d . 1
O O4 0.37662(18) 0.0765(2) 0.58717(18) 0.03805(16) Uani d . 1
N N1 0.2811(2) 0.0612(3) 0.4071(2) 0.0430(6) Uani d . 1
N N2 0.5560(2) 0.2034(3) 0.4786(2) 0.0385(5) Uani d . 1
C C1 0.2744(3) 0.0914(3) 0.5103(3) 0.0399(6) Uani d . 1
C C2 0.1575(3) 0.1469(3) 0.5332(3) 0.0394(6) Uani d . 1
H H2 0.1524 0.1551 0.6061 0.047 Uiso calc R 1
C C3 0.0579(3) 0.1862(3) 0.4515(3) 0.0395(6) Uani d . 1
C C4 -0.0617(3) 0.2603(4) 0.4616(3) 0.0586(9) Uani d . 1
H H4A -0.1177 0.2758 0.3891 0.088 Uiso calc PR 0.50
H H4B -0.0400 0.3524 0.4980 0.088 Uiso calc PR 0.50
H H4C -0.1046 0.2006 0.5041 0.088 Uiso calc PR 0.50
H H4D -0.0572 0.2767 0.5383 0.088 Uiso calc PR 0.50
H H4E -0.1349 0.2001 0.4295 0.088 Uiso calc PR 0.50
H H4F -0.0703 0.3520 0.4234 0.088 Uiso calc PR 0.50
C C5 0.5287(3) 0.2654(4) 0.3786(3) 0.0479(7) Uani d . 1
H H5 0.4768 0.2156 0.3187 0.057 Uiso calc R 1
C C6 0.5752(4) 0.4008(4) 0.3619(3) 0.0566(9) Uani d . 1
H H6 0.5556 0.4417 0.2914 0.068 Uiso calc R 1
C C7 0.6512(3) 0.4752(4) 0.4506(3) 0.0519(8) Uani d . 1
H H7 0.6838 0.5665 0.4402 0.062 Uiso calc R 1
C C8 0.6788(3) 0.4142(3) 0.5548(3) 0.0436(7) Uani d . 1
C C9 0.6285(3) 0.2777(3) 0.5643(3) 0.0403(6) Uani d . 1
H H9 0.6460 0.2351 0.6341 0.048 Uiso calc R 1
C C10 0.7622(4) 0.4886(5) 0.6547(4) 0.0719(12) Uani d . 1
H H10A 0.7469 0.4466 0.7205 0.108 Uiso calc R 1
H H10B 0.7418 0.5906 0.6521 0.108 Uiso calc R 1
H H10C 0.8512 0.4762 0.6554 0.108 Uiso calc R 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
_geom_angle_publ_flag
N2 Cu1 N2 3_656 . 180.00(5) ?
N2 Cu1 O4 3_656 . 89.49(9) ?
N2 Cu1 O4 . . 90.51(9) ?
N2 Cu1 O4 3_656 3_656 90.51(9) ?
N2 Cu1 O4 . 3_656 89.49(9) ?
O4 Cu1 O4 . 3_656 180.00(9) ?
N2 Cu1 N1 3_656 3_656 90.42(9) ?
N2 Cu1 N1 . 3_656 89.58(9) ?
O4 Cu1 N1 . 3_656 120.64(8) ?
O4 Cu1 N1 3_656 3_656 59.36(8) ?
N2 Cu1 N1 3_656 . 89.58(9) ?
N2 Cu1 N1 . . 90.42(9) ?
O4 Cu1 N1 . . 59.36(8) y
O4 Cu1 N1 3_656 . 120.64(8) ?
N1 Cu1 N1 3_656 . 180.0 ?
O2 S1 O3 . . 117.5(2) ?
O2 S1 N1 . . 111.73(16) ?
O3 S1 N1 . . 110.76(19) ?
O2 S1 O1 . . 106.57(16) ?
O3 S1 O1 . . 104.25(16) ?
N1 S1 O1 . . 104.84(13) y
C3 O1 S1 . . 118.61(19) ?
C1 O4 Cu1 . . 100.79(19) ?
C1 N1 S1 . . 119.5(2) y
C1 N1 Cu1 . . 82.61(18) y
S1 N1 Cu1 . . 154.46(15) ?
C5 N2 C9 . . 118.4(3) ?
C5 N2 Cu1 . . 121.4(2) ?
C9 N2 Cu1 . . 120.1(2) ?
O4 C1 N1 . . 117.2(3) ?
O4 C1 C2 . . 121.0(3) ?
N1 C1 C2 . . 121.8(3) ?
C3 C2 C1 . . 120.9(3) ?
C3 C2 H2 . . 119.6 ?
C1 C2 H2 . . 119.6 ?
C2 C3 O1 . . 122.0(3) ?
C2 C3 C4 . . 127.1(3) ?
O1 C3 C4 . . 110.8(3) ?
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 ?
C3 C4 H4D . . 109.5 ?
H4A C4 H4D . . 141.1 ?
H4B C4 H4D . . 56.3 ?
H4C C4 H4D . . 56.3 ?
C3 C4 H4E . . 109.5 ?
H4A C4 H4E . . 56.3 ?
H4B C4 H4E . . 141.1 ?
H4C C4 H4E . . 56.3 ?
H4D C4 H4E . . 109.5 ?
C3 C4 H4F . . 109.5 ?
H4A C4 H4F . . 56.3 ?
H4B C4 H4F . . 56.3 ?
H4C C4 H4F . . 141.1 ?
H4D C4 H4F . . 109.5 ?
H4E C4 H4F . . 109.5 ?
N2 C5 C6 . . 121.7(3) ?
N2 C5 H5 . . 119.1 ?
C6 C5 H5 . . 119.1 ?
C5 C6 C7 . . 119.3(3) ?
C5 C6 H6 . . 120.4 ?
C7 C6 H6 . . 120.4 ?
C6 C7 C8 . . 119.9(3) ?
C6 C7 H7 . . 120.1 ?
C8 C7 H7 . . 120.1 ?
C7 C8 C9 . . 117.1(3) ?
C7 C8 C10 . . 122.6(3) ?
C9 C8 C10 . . 120.3(3) ?
N2 C9 C8 . . 123.6(3) ?
N2 C9 H9 . . 118.2 ?
C8 C9 H9 . . 118.2 ?
C8 C10 H10A . . 109.5 ?
C8 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C8 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 N2 3_656 2.001(2) ?
Cu1 N2 . 2.001(2) y
Cu1 O4 . 2.044(2) y
Cu1 O4 3_656 2.044(2) ?
Cu1 N1 3_656 2.405(3) ?
Cu1 N1 . 2.405(3) y
S1 O2 . 1.411(3) ?
S1 O3 . 1.415(3) ?
S1 N1 . 1.579(3) y
S1 O1 . 1.613(2) ?
O1 C3 . 1.377(4) ?
O4 C1 . 1.267(4) y
N1 C1 . 1.340(4) y
N2 C5 . 1.335(4) ?
N2 C9 . 1.338(4) ?
C1 C2 . 1.449(4) ?
C2 C3 . 1.325(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.487(4) ?
C4 H4A . 0.9600 ?
C4 H4B . 0.9600 ?
C4 H4C . 0.9600 ?
C4 H4D . 0.9600 ?
C4 H4E . 0.9600 ?
C4 H4F . 0.9600 ?
C5 C6 . 1.376(5) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.377(5) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.378(5) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.382(4) ?
C8 C10 . 1.501(5) ?
C9 H9 . 0.9300 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 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
C4 H4C O2 3_556 0.96 2.49 3.334(5) 146.1
C2 H2 O3 4_566 0.93 2.59 3.194(4) 122.9
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
O2 S1 O1 C3 . 80.3(3)
O3 S1 O1 C3 . -154.7(3)
N1 S1 O1 C3 . -38.3(3)
N2 Cu1 O4 C1 3_656 -88.37(18)
N2 Cu1 O4 C1 . 91.63(18)
N1 Cu1 O4 C1 3_656 -178.56(16)
N1 Cu1 O4 C1 . 1.44(16)
O2 S1 N1 C1 . -80.2(3)
O3 S1 N1 C1 . 146.8(3)
O1 S1 N1 C1 . 34.9(3)
O2 S1 N1 Cu1 . 66.9(4)
O3 S1 N1 Cu1 . -66.2(4)
O1 S1 N1 Cu1 . -178.1(3)
N2 Cu1 N1 C1 3_656 88.31(18)
N2 Cu1 N1 C1 . -91.69(18)
O4 Cu1 N1 C1 . -1.35(15)
O4 Cu1 N1 C1 3_656 178.65(15)
N2 Cu1 N1 S1 3_656 -63.2(4)
N2 Cu1 N1 S1 . 116.8(4)
O4 Cu1 N1 S1 . -152.8(4)
O4 Cu1 N1 S1 3_656 27.2(4)
O4 Cu1 N2 C5 . -112.9(2)
O4 Cu1 N2 C5 3_656 67.1(2)
N1 Cu1 N2 C5 3_656 126.5(2)
N1 Cu1 N2 C5 . -53.5(2)
O4 Cu1 N2 C9 . 70.9(2)
O4 Cu1 N2 C9 3_656 -109.1(2)
N1 Cu1 N2 C9 3_656 -49.7(2)
N1 Cu1 N2 C9 . 130.3(2)
Cu1 O4 C1 N1 . -2.5(3)
Cu1 O4 C1 C2 . -179.0(2)
S1 N1 C1 O4 . 168.4(2)
Cu1 N1 C1 O4 . 2.1(2)
S1 N1 C1 C2 . -15.1(4)
Cu1 N1 C1 C2 . 178.6(3)
O4 C1 C2 C3 . 168.2(3)
N1 C1 C2 C3 . -8.1(5)
C1 C2 C3 O1 . 4.4(5)
C1 C2 C3 C4 . -172.4(3)
S1 O1 C3 C2 . 21.4(4)
S1 O1 C3 C4 . -161.4(2)
C9 N2 C5 C6 . 1.4(5)
Cu1 N2 C5 C6 . -174.9(3)
N2 C5 C6 C7 . -0.5(6)
C5 C6 C7 C8 . -0.5(6)
C6 C7 C8 C9 . 0.6(5)
C6 C7 C8 C10 . 179.3(4)
C5 N2 C9 C8 . -1.2(4)
Cu1 N2 C9 C8 . 175.1(2)
C7 C8 C9 N2 . 0.2(5)
C10 C8 C9 N2 . -178.4(3)
