#------------------------------------------------------------------------------
#$Date: 2018-08-09 15:09:44 +0200 (jue 09 de ago de 2018) $
#$Revision: 209504 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/24/7012416.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_7012416
loop_
_publ_author_name
'Caltagirone, Claudia'
'Bencini, Andrea'
'Demartin, Francesco'
'Devillanova, Francesco A.'
'Garau, Alessandra'
'Isaia, Francesco'
'Lippolis, Vito'
'Mariani, Palma'
'Papke, Ulrich'
'Tei, Lorenzo'
'Verani, Gaetano'
_publ_section_title
;
 Redox chemosensors: coordination chemistry towards CuII, ZnII, CdII,
 HgII, and PbII of 1-aza-4,10-dithia-7-oxacyclododecane ([12]aneNS2O)
 and its N-ferrocenylmethyl derivativeElectronic supplementary
 information (ESI) available: synthetic details including analytical
 and spectroscopic data for the isolated complexes. Ortep views of the
 coordination sphere around the metal centres in 1, 2 and 5. See
 http://www.rsc.org/suppdata/dt/b2/b210806m/
;
_journal_issue                   5
_journal_name_full               'Dalton Transactions'
_journal_page_first              901
_journal_paper_doi               10.1039/b210806m
_journal_year                    2003
_chemical_formula_analytical     'C8 H17 Cu N O S2 2+, 2 (NO3 1-)'
_chemical_formula_sum            'C8 H17 Cu N3 O7 S2'
_chemical_formula_weight         394.91
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 111.320(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.7630(10)
_cell_length_b                   14.9520(10)
_cell_length_c                   14.7470(10)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.9
_cell_measurement_theta_min      2.7
_cell_volume                     3032.4(4)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'SMART CCD diffractometer'
_diffrn_measurement_method       'omega scan'
_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  0.0280
_diffrn_reflns_av_sigmaI/netI    0.1217
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26392
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    1.750
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            Blue
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_description       prism
_exptl_crystal_F_000             1624
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.893
_refine_ls_goodness_of_fit_obs   1.078
_refine_ls_matrix_type           full
_refine_ls_number_parameters     440
_refine_ls_number_reflns         5339
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.910
_refine_ls_restrained_S_obs      1.100
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_obs          0.0356
_refine_ls_shift/esd_max         0.040
_refine_ls_shift/esd_mean        0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0421P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0888
_refine_ls_wR_factor_obs         0.0870
_reflns_number_observed          3655
_reflns_number_total             5339
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b210806m.txt
_cod_data_source_block           da144
_cod_depositor_comments
;
 Updating space group information.

 Antanas Vaitkus,
 2018-08-09

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0421P)^2^+0.0000P] 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^)+(0.0421P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      ' P21/c'
_cod_database_code               7012416
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'
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
CuA Cu 0.28545(3) 0.78290(3) 0.02627(3) 0.04466(13) Uani 1 d . .
CuB Cu 0.23749(3) 0.20772(3) 0.43556(3) 0.04368(13) Uani 1 d . .
S4A S 0.25695(8) 0.70786(7) -0.12126(8) 0.0634(3) Uani 1 d . .
S4B S 0.18811(9) 0.10557(8) 0.29699(7) 0.0699(3) Uani 1 d . .
S10A S 0.26786(9) 0.89545(7) 0.13525(8) 0.0686(3) Uani 1 d . .
S10B S 0.26213(8) 0.26030(8) 0.59380(8) 0.0686(3) Uani 1 d . .
O7A O 0.1357(2) 0.8584(2) -0.0768(2) 0.0671(8) Uani 1 d . .
O7B O 0.1394(2) 0.1021(2) 0.4818(2) 0.0571(7) Uani 1 d . .
O21 O 0.4160(2) 0.7363(2) 0.1517(2) 0.0679(8) Uani 1 d . .
O22 O 0.4618(2) 0.6607(2) 0.0526(2) 0.0795(9) Uani 1 d . .
O23 O 0.5031(2) 0.6183(2) 0.2022(2) 0.0973(11) Uani 1 d . .
O31A O 0.2092(6) 0.7158(5) 0.0840(6) 0.048(2) Uani 0.50 d PD .
O32A O 0.1963(10) 0.5829(11) 0.1371(11) 0.162(8) Uani 0.50 d PD .
O33A O 0.1523(8) 0.6101(6) -0.0069(7) 0.153(4) Uani 0.50 d PD .
O31B O 0.1896(10) 0.6982(9) 0.0622(10) 0.165(7) Uani 0.50 d PD .
O32B O 0.1506(7) 0.5905(7) 0.1190(9) 0.085(4) Uani 0.50 d PD .
O33B O 0.2734(5) 0.5878(4) 0.0779(6) 0.087(2) Uani 0.50 d PD .
O41 O 0.1138(2) 0.2703(2) 0.3672(2) 0.0840(10) Uani 1 d . .
O42 O 0.1782(3) 0.3975(3) 0.4027(4) 0.151(2) Uani 1 d . .
O43 O 0.0292(3) 0.3906(3) 0.3430(4) 0.147(2) Uani 1 d . .
O51 O 0.3155(2) 0.2820(2) 0.3513(2) 0.0658(8) Uani 1 d . .
O52 O 0.4182(2) 0.3296(2) 0.4889(2) 0.0664(8) Uani 1 d . .
O53 O 0.4105(2) 0.3930(2) 0.3567(2) 0.0811(9) Uani 1 d . .
N1A N 0.3659(2) 0.8702(2) -0.0139(2) 0.0449(7) Uani 1 d . .
N1B N 0.3560(2) 0.1317(2) 0.4942(2) 0.0461(7) Uani 1 d . .
N2 N 0.4604(2) 0.6704(2) 0.1355(2) 0.0560(8) Uani 1 d . .
N4 N 0.1019(3) 0.3526(3) 0.3698(3) 0.0838(13) Uani 1 d . .
N3 N 0.1948(3) 0.6316(3) 0.0826(3) 0.0705(11) Uani 1 d D .
N5 N 0.3815(2) 0.3358(2) 0.3991(2) 0.0516(8) Uani 1 d . .
C5A C 0.1431(3) 0.7582(4) -0.1995(3) 0.0801(14) Uani 1 d . .
H5AA H 0.1572(3) 0.8073(4) -0.2353(3) 0.052(11) Uiso 1 calc R .
H5AB H 0.1057(3) 0.7141(4) -0.2464(3) 0.108(18) Uiso 1 calc R .
C5B C 0.1126(3) 0.0270(3) 0.3327(3) 0.0787(14) Uani 1 d . .
H5BA H 0.0625(3) 0.0037(3) 0.2746(3) 0.112(17) Uiso 1 calc R .
H5BB H 0.1525(3) -0.0230(3) 0.3668(3) 0.089(16) Uiso 1 calc R .
C6A C 0.0827(3) 0.7927(4) -0.1437(4) 0.0843(15) Uani 1 d . .
H6AA H 0.0227(3) 0.8182(4) -0.1885(4) 0.094(15) Uiso 1 calc R .
H6AB H 0.0663(3) 0.7438(4) -0.1093(4) 0.084(15) Uiso 1 calc R .
C6B C 0.0657(3) 0.0688(3) 0.3966(3) 0.0723(12) Uani 1 d . .
H6BA H 0.0234(3) 0.1172(3) 0.3623(3) 0.076(14) Uiso 1 calc R .
H6BB H 0.0267(3) 0.0247(3) 0.4142(3) 0.074(13) Uiso 1 calc R .
C8A C 0.0887(3) 0.8898(4) -0.0154(4) 0.0859(15) Uani 1 d . .
H8AA H 0.0703(3) 0.8397(4) 0.0160(4) 0.095(17) Uiso 1 calc R .
H8AB H 0.0301(3) 0.9220(4) -0.0533(4) 0.109(17) Uiso 1 calc R .
C8B C 0.1029(3) 0.1464(4) 0.5462(3) 0.0767(13) Uani 1 d . .
H8BA H 0.0649(3) 0.1051(4) 0.5687(3) 0.117(18) Uiso 1 calc R .
H8BB H 0.0610(3) 0.1955(4) 0.5128(3) 0.104(19) Uiso 1 calc R .
C9A C 0.1556(4) 0.9501(3) 0.0595(4) 0.091(2) Uani 1 d . .
H9AA H 0.1224(4) 0.9724(3) 0.1008(4) 0.101(16) Uiso 1 calc R .
H9AB H 0.1714(4) 1.0009(3) 0.0272(4) 0.077(14) Uiso 1 calc R .
C9B C 0.1870(4) 0.1817(4) 0.6316(3) 0.086(2) Uani 1 d . .
H9BA H 0.2271(4) 0.1320(4) 0.6659(3) 0.100(20) Uiso 1 calc R .
H9BB H 0.1623(4) 0.2116(4) 0.6762(3) 0.097(16) Uiso 1 calc R .
C11A C 0.3610(4) 0.9658(3) 0.1199(3) 0.0762(13) Uani 1 d . .
H11A H 0.3511(4) 1.0270(3) 0.1362(3) 0.079(13) Uiso 1 calc R .
H11A' H 0.4242(4) 0.9465(3) 0.1645(3) 0.128(22) Uiso 1 calc R .
C11B C 0.3803(3) 0.2106(3) 0.6482(3) 0.0703(13) Uani 1 d . .
H11B H 0.4288(3) 0.2515(3) 0.6422(3) 0.090(15) Uiso 1 calc R .
H11B' H 0.3940(3) 0.2009(3) 0.7169(3) 0.060(11) Uiso 1 calc R .
C12A C 0.3598(3) 0.9628(2) 0.0176(3) 0.0623(11) Uani 1 d . .
H12A H 0.3004(3) 0.9902(2) -0.0261(3) 0.058(11) Uiso 1 calc R .
H12A' H 0.4143(3) 0.9970(2) 0.0140(3) 0.063(11) Uiso 1 calc R .
C12B C 0.3874(3) 0.1229(3) 0.6009(3) 0.0691(12) Uani 1 d . .
H12B H 0.4541(3) 0.1018(3) 0.6270(3) 0.084(14) Uiso 1 calc R .
H12B' H 0.3470(3) 0.0788(3) 0.6165(3) 0.054(11) Uiso 1 calc R .
C2A C 0.3500(3) 0.8672(3) -0.1195(2) 0.0577(10) Uani 1 d . .
H2AA H 0.4030(3) 0.8974(3) -0.1309(2) 0.057(11) Uiso 1 calc R .
H2AB H 0.2900(3) 0.8978(3) -0.1564(2) 0.059(11) Uiso 1 calc R .
C2B C 0.3469(3) 0.0433(3) 0.4477(3) 0.0735(13) Uani 1 d . .
H2BA H 0.3061(3) 0.0051(3) 0.4700(3) 0.063(12) Uiso 1 calc R .
H2BB H 0.4106(3) 0.0158(3) 0.4666(3) 0.104(16) Uiso 1 calc R .
C3A C 0.3447(3) 0.7719(3) -0.1526(3) 0.0656(12) Uani 1 d . .
H3AA H 0.4082(3) 0.7445(3) -0.1231(3) 0.049(10) Uiso 1 calc R .
H3AB H 0.3274(3) 0.7707(3) -0.2226(3) 0.081(13) Uiso 1 calc R .
C3B C 0.3039(3) 0.0507(3) 0.3399(3) 0.0795(14) Uani 1 d . .
H3BA H 0.2966(3) -0.0087(3) 0.3119(3) 0.082(13) Uiso 1 calc R .
H3BB H 0.3484(3) 0.0837(3) 0.3175(3) 0.082(14) Uiso 1 calc R .
HN1B H 0.4062(3) 0.1720(3) 0.4791(3) 0.052(10) Uiso 1 d R .
HN1A H 0.4257(3) 0.8530(3) 0.0217(3) 0.054(11) Uiso 1 d R .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 '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'
O O 0.0106 0.0060 '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'
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'
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
O31A CuA N1A 168.9(2) . . ?
O31A CuA O31B 11.2(5) . . ?
N1A CuA O31B 174.8(4) . . ?
O31A CuA O21 86.5(3) . . ?
N1A CuA O21 91.28(11) . . ?
O31B CuA O21 93.4(4) . . ?
O31A CuA S4A 103.0(2) . . ?
N1A CuA S4A 87.86(8) . . ?
O31B CuA S4A 92.0(4) . . ?
O21 CuA S4A 115.27(8) . . ?
O31A CuA S10A 81.2(2) . . ?
N1A CuA S10A 87.78(9) . . ?
O31B CuA S10A 90.4(4) . . ?
O21 CuA S10A 86.30(8) . . ?
S4A CuA S10A 158.08(4) . . ?
O41 CuB N1B 173.05(12) . . ?
O41 CuB O51 92.75(12) . . ?
N1B CuB O51 88.70(11) . . ?
O41 CuB S10B 97.37(10) . . ?
N1B CuB S10B 88.02(9) . . ?
O51 CuB S10B 116.84(7) . . ?
O41 CuB O7B 85.14(11) . . ?
N1B CuB O7B 91.49(10) . . ?
O51 CuB O7B 162.90(9) . . ?
S10B CuB O7B 80.25(7) . . ?
O41 CuB S4B 85.98(10) . . ?
N1B CuB S4B 87.39(9) . . ?
O51 CuB S4B 84.52(7) . . ?
S10B CuB S4B 158.03(4) . . ?
O7B CuB S4B 78.40(7) . . ?
C3A S4A C5A 101.7(2) . . ?
C3A S4A CuA 94.61(13) . . ?
C5A S4A CuA 101.7(2) . . ?
C3B S4B C5B 102.0(2) . . ?
C3B S4B CuB 91.96(14) . . ?
C5B S4B CuB 100.93(14) . . ?
C11A S10A C9A 103.1(3) . . ?
C11A S10A CuA 92.98(13) . . ?
C9A S10A CuA 101.5(2) . . ?
C11B S10B C9B 101.3(2) . . ?
C11B S10B CuB 94.54(13) . . ?
C9B S10B CuB 101.16(14) . . ?
C8A O7A C6A 113.9(4) . . ?
C8B O7B C6B 113.6(3) . . ?
C8B O7B CuB 107.4(2) . . ?
C6B O7B CuB 109.1(2) . . ?
N2 O21 CuA 116.1(2) . . ?
N3 O31A CuA 129.0(4) . . ?
O32B O32A N3 80.6(20) . . ?
O32B O32A O33B 126.2(24) . . ?
N3 O32A O33B 54.1(7) . . ?
N3 O33A O31B 39.3(5) . . ?
N3 O33A O33B 48.7(5) . . ?
O31B O33A O33B 72.0(7) . . ?
N3 O31B O33A 51.6(7) . . ?
N3 O31B CuA 131.8(12) . . ?
O33A O31B CuA 115.6(9) . . ?
O32A O32B N3 66.5(17) . . ?
N3 O33B O32A 40.1(5) . . ?
N3 O33B O33A 45.1(4) . . ?
O32A O33B O33A 71.2(6) . . ?
N4 O41 CuB 124.6(3) . . ?
N5 O51 CuB 116.7(2) . . ?
C12A N1A C2A 110.8(3) . . ?
C12A N1A CuA 114.2(2) . . ?
C2A N1A CuA 114.0(2) . . ?
C2B N1B C12B 110.9(3) . . ?
C2B N1B CuB 113.0(2) . . ?
C12B N1B CuB 113.5(2) . . ?
O23 N2 O22 121.7(4) . . ?
O23 N2 O21 119.7(4) . . ?
O22 N2 O21 118.5(3) . . ?
O43 N4 O41 127.0(4) . . ?
O43 N4 O42 117.7(4) . . ?
O41 N4 O42 115.2(4) . . ?
O31B N3 O32A 147.7(13) . . ?
O31B N3 O32B 130.5(11) . . ?
O32A N3 O32B 33.0(9) . . ?
O31B N3 O31A 18.1(9) . . ?
O32A N3 O31A 134.1(10) . . ?
O32B N3 O31A 129.4(7) . . ?
O31B N3 O33A 89.1(9) . . ?
O32A N3 O33A 118.0(11) . . ?
O32B N3 O33A 101.3(8) . . ?
O31A N3 O33A 106.2(6) . . ?
O31B N3 O33B 115.0(10) . . ?
O32A N3 O33B 85.8(8) . . ?
O32B N3 O33B 113.9(7) . . ?
O31A N3 O33B 109.6(5) . . ?
O33A N3 O33B 86.2(6) . . ?
O53 N5 O52 120.0(3) . . ?
O53 N5 O51 120.1(3) . . ?
O52 N5 O51 119.8(3) . . ?
C6A C5A S4A 112.9(3) . . ?
C6B C5B S4B 112.6(3) . . ?
O7A C6A C5A 109.4(4) . . ?
O7B C6B C5B 108.8(4) . . ?
O7A C8A C9A 109.2(4) . . ?
O7B C8B C9B 108.9(4) . . ?
C8A C9A S10A 113.2(3) . . ?
C8B C9B S10B 112.1(3) . . ?
C12A C11A S10A 112.1(3) . . ?
C12B C11B S10B 111.9(3) . . ?
N1A C12A C11A 111.4(3) . . ?
N1B C12B C11B 111.6(3) . . ?
N1A C2A C3A 109.9(3) . . ?
N1B C2B C3B 111.2(3) . . ?
C2A C3A S4A 112.3(3) . . ?
C2B C3B S4B 113.2(3) . . ?
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
CuA O31A 1.922(6) . ?
CuA N1A 1.995(3) . ?
CuA O31B 2.106(13) . ?
CuA O21 2.242(3) . ?
CuA S4A 2.3459(11) . ?
CuA S10A 2.4054(11) . ?
CuB O41 1.972(3) . ?
CuB N1B 2.000(3) . ?
CuB O51 2.268(3) . ?
CuB S10B 2.3620(11) . ?
CuB O7B 2.402(2) . ?
CuB S4B 2.4406(11) . ?
S4A C3A 1.801(4) . ?
S4A C5A 1.820(5) . ?
S4B C3B 1.791(5) . ?
S4B C5B 1.824(4) . ?
S10A C11A 1.810(5) . ?
S10A C9A 1.821(5) . ?
S10B C11B 1.794(4) . ?
S10B C9B 1.836(4) . ?
O7A C8A 1.407(5) . ?
O7A C6A 1.412(5) . ?
O7B C8B 1.417(5) . ?
O7B C6B 1.420(4) . ?
O21 N2 1.254(4) . ?
O22 N2 1.238(4) . ?
O23 N2 1.233(4) . ?
O31A N3 1.276(9) . ?
O32A O32B 0.64(2) . ?
O32A N3 1.077(14) . ?
O32A O33B 1.669(15) . ?
O33A N3 1.280(10) . ?
O33A O31B 1.633(14) . ?
O33A O33B 1.802(13) . ?
O31B N3 1.035(13) . ?
O32B N3 1.159(9) . ?
O33B N3 1.356(6) . ?
O41 N4 1.246(4) . ?
O42 N4 1.247(5) . ?
O43 N4 1.150(5) . ?
O51 N5 1.263(4) . ?
O52 N5 1.239(4) . ?
O53 N5 1.225(4) . ?
N1A C12A 1.473(4) . ?
N1A C2A 1.488(4) . ?
N1B C2B 1.473(5) . ?
N1B C12B 1.476(4) . ?
C5A C6A 1.506(6) . ?
C5B C6B 1.495(6) . ?
C8A C9A 1.488(7) . ?
C8B C9B 1.506(6) . ?
C11A C12A 1.504(5) . ?
C11B C12B 1.507(6) . ?
C2A C3A 1.498(5) . ?
C2B C3B 1.485(6) . ?
