#------------------------------------------------------------------------------
#$Date: 2016-03-23 14:44:38 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179304 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/01/4320110.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_4320110
loop_
_publ_author_name
'Larry R. Falvello'
'Julio Gomez'
'Isabel Pascual'
'Milagros Tomás'
'Esteban P. Urriolabeitia'
'Arthur J. Schultz'
_publ_contact_author_address
; Department of Inorganic Chemistry
  University of Zaragoza
  Plaza San Francisco s/n
  E-50009 Zaragoza
  Spain
;
_publ_contact_author_fax         34()976761187
_publ_contact_author_name        'Larry R. Falvello'
_publ_contact_author_phone       34()976761179
_publ_section_title
;
 Saccharinate as a Versatile Polyfunctional Ligand. Four Distinct
 Coordination Modes, Misdirected Valence, and a Dominant Aggregate
 Structure from a Single Reaction System
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4455
_journal_page_last               4463
_journal_paper_doi               10.1021/ic010300x
_journal_volume                  40
_journal_year                    2001
_chemical_formula_sum            'C14 H22 Cu N6 O7 S2'
_chemical_formula_weight         514.04
_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
_cell_angle_alpha                98.05(3)
_cell_angle_beta                 92.39(3)
_cell_angle_gamma                99.08(3)
_cell_formula_units_Z            2
_cell_length_a                   7.0450(10)
_cell_length_b                   10.578(2)
_cell_length_c                   13.967(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    566(2)
_cell_measurement_theta_max      15.1
_cell_measurement_theta_min      12.5
_cell_volume                     1015.5(3)
_computing_molecular_graphics    'SHELXTL Rel. 5.05/VMS (Siemens, 1996)'
_computing_publication_material  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      566(2)
_diffrn_measurement_device       'Stoe AED-2'
_diffrn_measurement_method       'omega-2theta 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  0.0157
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3902
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    1.332
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_correction_T_min  0.869
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            dark_blue
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_description       'regular block'
_exptl_crystal_F_000             530
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.045
_refine_ls_goodness_of_fit_obs   1.079
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         3418
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_restrained_S_obs      1.079
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_obs          0.0296
_refine_ls_shift/esd_max         -0.092
_refine_ls_shift/esd_mean        0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0314P)²+0.4258P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0716
_refine_ls_wR_factor_obs         0.0668
_reflns_number_observed          3028
_reflns_number_total             3583
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic010300x_5.cif
_cod_data_source_block           cpd7XRay
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Psi-scan'
changed to 'psi-scan' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0314P)^2^+0.4258P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0314P)^2^+0.4258P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               4320110
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Cu1 Cu 0.25901(4) 0.49254(3) 0.21736(2) 0.01949(10) Uani 1 d . .
N3 N 0.4530(4) 0.3843(3) 0.2555(2) 0.0272(5) Uani 1 d . .
H31 H 0.4919(48) 0.3450(31) 0.2049(25) 0.038(10) Uiso 1 d . .
H32 H 0.4029(56) 0.3213(37) 0.2916(28) 0.057(11) Uiso 1 d . .
H33 H 0.5469(54) 0.4218(34) 0.2874(26) 0.042(11) Uiso 1 d . .
N4 N 0.4438(4) 0.5560(3) 0.1201(2) 0.0265(5) Uani 1 d . .
H41 H 0.4991(54) 0.4953(37) 0.0946(27) 0.052(11) Uiso 1 d . .
H42 H 0.4000(52) 0.5864(33) 0.0692(26) 0.047(10) Uiso 1 d . .
H43 H 0.5350(57) 0.6123(37) 0.1465(28) 0.054(12) Uiso 1 d . .
N5 N 0.0985(4) 0.4445(3) 0.3287(2) 0.0300(6) Uani 1 d . .
H51 H -0.0103(63) 0.4528(37) 0.3233(28) 0.056(13) Uiso 1 d . .
H52 H 0.1401(56) 0.4881(37) 0.3796(29) 0.053(12) Uiso 1 d . .
H53 H 0.1098(66) 0.3612(46) 0.3380(32) 0.085(15) Uiso 1 d . .
N6 N 0.0878(4) 0.6210(3) 0.1869(2) 0.0281(5) Uani 1 d . .
H61 H 0.1595(52) 0.6980(36) 0.1785(24) 0.048(10) Uiso 1 d . .
H62 H 0.0128(51) 0.6378(31) 0.2270(26) 0.037(10) Uiso 1 d . .
H63 H 0.0343(61) 0.5985(39) 0.1332(31) 0.065(14) Uiso 1 d . .
S1 S -0.13734(9) 0.29157(6) 0.09197(5) 0.01984(15) Uani 1 d . .
O2 O -0.2199(3) 0.2378(2) 0.17308(14) 0.0328(5) Uani 1 d . .
O3 O -0.2136(3) 0.4041(2) 0.06881(14) 0.0301(5) Uani 1 d . .
N1 N 0.0944(3) 0.3231(2) 0.1051(2) 0.0210(5) Uani 1 d . .
C1 C 0.1777(4) 0.2523(2) 0.0346(2) 0.0201(5) Uani 1 d . .
O1 O 0.3524(3) 0.2613(2) 0.02780(14) 0.0292(4) Uani 1 d . .
C2 C 0.0315(4) 0.1620(2) -0.0345(2) 0.0189(5) Uani 1 d . .
C3 C 0.0635(4) 0.0758(3) -0.1138(2) 0.0265(6) Uani 1 d . .
H3 H 0.1878(49) 0.0685(30) -0.1272(23) 0.041(9) Uiso 1 d . .
C4 C -0.0943(5) 0.0013(3) -0.1682(2) 0.0319(7) Uani 1 d . .
H4 H -0.0687(48) -0.0623(32) -0.2192(24) 0.046(10) Uiso 1 d . .
C5 C -0.2798(5) 0.0132(3) -0.1438(2) 0.0323(7) Uani 1 d . .
H5 H -0.3737(47) -0.0371(30) -0.1784(23) 0.036(9) Uiso 1 d . .
C6 C -0.3153(4) 0.0997(3) -0.0646(2) 0.0265(6) Uani 1 d . .
H6 H -0.4394(42) 0.1101(26) -0.0458(20) 0.022(7) Uiso 1 d . .
C7 C -0.1552(4) 0.1732(2) -0.0115(2) 0.0192(5) Uani 1 d . .
S2 S 0.62609(10) 0.74757(6) 0.36812(5) 0.0265(2) Uani 1 d . .
O5 O 0.4307(3) 0.7174(2) 0.32655(15) 0.0379(5) Uani 1 d . .
O6 O 0.7630(3) 0.6951(2) 0.3060(2) 0.0410(5) Uani 1 d . .
N2 N 0.6429(3) 0.7054(2) 0.4741(2) 0.0279(5) Uani 1 d . .
C8 C 0.7059(4) 0.8096(2) 0.5433(2) 0.0219(6) Uani 1 d . .
O4 O 0.7352(3) 0.8033(2) 0.62986(14) 0.0326(5) Uani 1 d . .
C9 C 0.7345(4) 0.9349(2) 0.5031(2) 0.0188(5) Uani 1 d . .
C10 C 0.7930(4) 1.0588(3) 0.5525(2) 0.0241(6) Uani 1 d . .
H10 H 0.8155(41) 1.0716(26) 0.6227(21) 0.027(8) Uiso 1 d . .
C11 C 0.8100(4) 1.1609(3) 0.4994(2) 0.0297(6) Uani 1 d . .
H11 H 0.8474(42) 1.2493(29) 0.5350(21) 0.031(8) Uiso 1 d . .
C12 C 0.7686(4) 1.1399(3) 0.3997(2) 0.0327(7) Uani 1 d . .
H12 H 0.7726(42) 1.2085(29) 0.3667(21) 0.028(8) Uiso 1 d . .
C13 C 0.7105(4) 1.0162(3) 0.3505(2) 0.0296(6) Uani 1 d . .
H13 H 0.6900(45) 1.0017(29) 0.2848(23) 0.037(9) Uiso 1 d . .
C14 C 0.6954(4) 0.9159(2) 0.4039(2) 0.0215(5) Uani 1 d . .
O7 O 0.7199(4) 0.4461(2) 0.4610(2) 0.0428(6) Uani 1 d . .
H71 H 0.6917(55) 0.5220(40) 0.4633(27) 0.057(12) Uiso 1 d . .
H72 H 0.6099(81) 0.3938(50) 0.4838(38) 0.111(19) Uiso 1 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'
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
N3 Cu1 N4 87.79(11) . . ?
N3 Cu1 N6 172.82(12) . . ?
N4 Cu1 N6 89.72(12) . . ?
N3 Cu1 N5 90.08(12) . . ?
N4 Cu1 N5 172.34(12) . . ?
N6 Cu1 N5 91.51(12) . . ?
N3 Cu1 N1 92.38(10) . . ?
N4 Cu1 N1 93.23(10) . . ?
N6 Cu1 N1 94.49(10) . . ?
N5 Cu1 N1 94.22(10) . . ?
N3 Cu1 O5 96.28(10) . . ?
N4 Cu1 O5 81.89(10) . . ?
N6 Cu1 O5 76.69(10) . . ?
N5 Cu1 O5 91.03(10) . . ?
N1 Cu1 O5 169.87(7) . . ?
Cu1 N3 H31 109.3(22) . . ?
Cu1 N3 H32 113.3(24) . . ?
H31 N3 H32 106.5(31) . . ?
Cu1 N3 H33 116.7(25) . . ?
H31 N3 H33 106.5(33) . . ?
H32 N3 H33 103.8(33) . . ?
Cu1 N4 H41 110.5(25) . . ?
Cu1 N4 H42 119.9(23) . . ?
H41 N4 H42 102.8(31) . . ?
Cu1 N4 H43 112.1(26) . . ?
H41 N4 H43 103.8(35) . . ?
H42 N4 H43 106.1(33) . . ?
Cu1 N5 H51 115.2(29) . . ?
Cu1 N5 H52 111.8(27) . . ?
H51 N5 H52 105.2(37) . . ?
Cu1 N5 H53 108.9(28) . . ?
H51 N5 H53 111.2(40) . . ?
H52 N5 H53 103.9(37) . . ?
Cu1 N6 H61 111.1(22) . . ?
Cu1 N6 H62 115.7(24) . . ?
H61 N6 H62 106.5(31) . . ?
Cu1 N6 H63 110.2(29) . . ?
H61 N6 H63 100.3(35) . . ?
H62 N6 H63 111.8(37) . . ?
O2 S1 O3 114.51(12) . . ?
O2 S1 N1 111.87(12) . . ?
O3 S1 N1 110.20(11) . . ?
O2 S1 C7 111.33(12) . . ?
O3 S1 C7 110.33(12) . . ?
N1 S1 C7 97.30(12) . . ?
C1 N1 S1 111.9(2) . . ?
C1 N1 Cu1 124.9(2) . . ?
S1 N1 Cu1 122.62(11) . . ?
O1 C1 N1 124.1(2) . . ?
O1 C1 C2 123.6(2) . . ?
N1 C1 C2 112.3(2) . . ?
C3 C2 C7 120.0(2) . . ?
C3 C2 C1 128.2(2) . . ?
C7 C2 C1 111.8(2) . . ?
C2 C3 C4 118.5(3) . . ?
C2 C3 H3 118.8(20) . . ?
C4 C3 H3 122.6(20) . . ?
C5 C4 C3 120.7(3) . . ?
C5 C4 H4 122.2(21) . . ?
C3 C4 H4 116.9(21) . . ?
C4 C5 C6 121.7(3) . . ?
C4 C5 H5 117.6(21) . . ?
C6 C5 H5 120.6(21) . . ?
C7 C6 C5 116.4(3) . . ?
C7 C6 H6 119.6(17) . . ?
C5 C6 H6 124.0(17) . . ?
C6 C7 C2 122.6(2) . . ?
C6 C7 S1 130.7(2) . . ?
C2 C7 S1 106.7(2) . . ?
O5 S2 O6 113.44(13) . . ?
O5 S2 N2 111.58(13) . . ?
O6 S2 N2 111.11(13) . . ?
O5 S2 C14 111.01(13) . . ?
O6 S2 C14 111.23(13) . . ?
N2 S2 C14 97.41(12) . . ?
S2 O5 Cu1 126.97(12) . . ?
C8 N2 S2 111.4(2) . . ?
O4 C8 N2 124.4(2) . . ?
O4 C8 C9 122.9(2) . . ?
N2 C8 C9 112.7(2) . . ?
C14 C9 C10 120.1(2) . . ?
C14 C9 C8 111.7(2) . . ?
C10 C9 C8 128.2(2) . . ?
C9 C10 C11 117.9(3) . . ?
C9 C10 H10 119.4(16) . . ?
C11 C10 H10 122.6(16) . . ?
C10 C11 C12 121.2(3) . . ?
C10 C11 H11 117.8(17) . . ?
C12 C11 H11 121.0(17) . . ?
C13 C12 C11 120.9(3) . . ?
C13 C12 H12 119.2(18) . . ?
C11 C12 H12 119.9(18) . . ?
C14 C13 C12 117.4(3) . . ?
C14 C13 H13 121.4(20) . . ?
C12 C13 H13 121.1(20) . . ?
C13 C14 C9 122.6(3) . . ?
C13 C14 S2 130.7(2) . . ?
C9 C14 S2 106.6(2) . . ?
H71 O7 H72 106.1(38) . . ?
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 N3 2.017(2) . ?
Cu1 N4 2.030(3) . ?
Cu1 N6 2.030(3) . ?
Cu1 N5 2.035(3) . ?
Cu1 N1 2.328(2) . ?
Cu1 O5 2.715(2) . ?
N3 H31 0.85(3) . ?
N3 H32 0.93(4) . ?
N3 H33 0.80(4) . ?
N4 H41 0.85(4) . ?
N4 H42 0.88(4) . ?
N4 H43 0.84(4) . ?
N5 H51 0.79(4) . ?
N5 H52 0.81(4) . ?
N5 H53 0.92(5) . ?
N6 H61 0.91(4) . ?
N6 H62 0.81(4) . ?
N6 H63 0.81(4) . ?
S1 O2 1.441(2) . ?
S1 O3 1.451(2) . ?
S1 N1 1.611(2) . ?
S1 C7 1.760(3) . ?
N1 C1 1.363(3) . ?
C1 O1 1.228(3) . ?
C1 C2 1.501(4) . ?
C2 C3 1.382(4) . ?
C2 C7 1.387(4) . ?
C3 C4 1.386(4) . ?
C3 H3 0.92(3) . ?
C4 C5 1.385(4) . ?
C4 H4 0.95(3) . ?
C5 C6 1.392(4) . ?
C5 H5 0.86(3) . ?
C6 C7 1.385(4) . ?
C6 H6 0.94(3) . ?
S2 O5 1.441(2) . ?
S2 O6 1.448(2) . ?
S2 N2 1.609(2) . ?
S2 C14 1.764(3) . ?
N2 C8 1.363(3) . ?
C8 O4 1.231(3) . ?
C8 C9 1.498(3) . ?
C9 C14 1.382(4) . ?
C9 C10 1.385(4) . ?
C10 C11 1.386(4) . ?
C10 H10 0.97(3) . ?
C11 C12 1.391(4) . ?
C11 H11 0.99(3) . ?
C12 C13 1.381(4) . ?
C12 H12 0.91(3) . ?
C13 C14 1.374(4) . ?
C13 H13 0.91(3) . ?
O7 H71 0.85(4) . ?
O7 H72 0.97(6) . ?
