Mol­ecular structures of two copper com­plexes with the pharmaceuticals nor­flox­acin and tin­id­az­ole, when powder X-ray diffraction assists multi-domain single-crystal X-ray diffraction

Tobón Zapata, G.E.; Martínez Carmona, D.M.; Echeverría, G.A.; Piro, O.E.

doi:10.1107/S2052520622003766

Molecular structures of two copper complexes with the pharmaceuticals norfloxacin and tinidazole, when powder X-ray diffraction assists multi-domain single-crystal X-ray diffraction

G. E. Tobón Zapata, D. M. Martínez Carmona, G. A. Echeverría and O. E. Piro

The crystal structures of bis[1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-ium-4-yl)-1,4-dihydroquinoline-3-carboxylato]copper(II) sulfate heptahydrate, [Cu(C₁₆H₁₈FN₃O₃)₂]SO₄·7H₂O or [Cu(nor)₂]SO₄·7H₂O (nor is norfloxacin), and bis{1-[2-(ethylsulfonyl)ethyl]-2-methyl-5-nitroimide}dinitratocopper(II), [Cu(NO₃)₂(C₈H₁₃N₃O₄S)₂] or [Cu(NO₃)₂(tnz)₂] (tnz is tinidazole), were solved by X-ray diffraction. Both complexes crystallize in the space group P2₁/c, with Z = 4 (for nor) and Z = 2 (for ntz) molecules per unit cell. In [Cu(nor)₂]SO₄·7H₂O, the Cu^II ion is at the centre of a square-planar environment, trans coordinated to two independent norfloxacin molecules in the zwitterionic form acting as bidentate ligands through one of the carboxyl (cbx) and the carbonyl (cb) O atoms. The solid is further stabilized by an extensive network of N—H

O(sulfate), N—H

O(cbx), N—H

OW, OW—H

O(sulfate) and OW—H

OW hydrogen bonds. The [Cu(NO₃)₂(tnz)₂] complex is centrosymmetric, with the Cu^II ion in a square planar environment, coordinated to a tinidazole molecule acting as a monodentate ligand through its imidazole N atom and to one nitrate O atom. The vibrational FT–IR absorption spectra and thermal behaviour of the complexes were also studied and are briefly discussed based on the crystal structures.

Keywords: copper(II) complexes of norfloxacin and tinidazole; X-ray crystal structures; PXRD-assisted SCXRD; vibrational IR spectra; thermal decomposition.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520622003766/yv5004sup1.cif Contains datablocks global, I, II
	Portable Document Format (PDF) file https://doi.org/10.1107/S2052520622003766/yv5004sup2.pdf Supplementary material
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520622003766/yv5004Isup3.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520622003766/yv5004IIsup4.hkl Contains datablock II

CCDC references: 900244; 2082848

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011) for (I); CrysAlis PRO (Rigaku OD, 2015) for (II). Cell refinement: CrysAlis PRO (Agilent, 2011) for (I); CrysAlis PRO (Rigaku OD, 2015) for (II). Data reduction: CrysAlis PRO (Agilent, 2011) for (I); CrysAlis PRO (Rigaku OD, 2015) for (II). For both structures, program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b).

\ Bis[1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-ium-4-yl)-1,4-dihydroquinoline-3-\ carboxylato]copper(II) sulfate heptahydrate, (I) top

Crystal data top

[Cu(C₁₆H₁₈FN₃O₃)₂]SO₄·7H₂O	F(000) = 1928
M_r = 924.38	D_x = 1.586 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.5418 Å
a = 10.4613 (3) Å	Cell parameters from 3814 reflections
b = 31.2244 (8) Å	θ = 3.7–73.9°
c = 12.2241 (3) Å	µ = 2.13 mm⁻¹
β = 104.450 (3)°	T = 295 K
V = 3866.66 (18) Å³	Fragment, blue
Z = 4	0.43 × 0.18 × 0.03 mm

Data collection top

Agilent Xcalibur Eos Gemini diffractometer	7439 independent reflections
Radiation source: Enhance (Cu) X-ray Source	5339 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 16.0604 pixels mm^-1	θ_max = 71.0°, θ_min = 4.0°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −12→12
T_min = 0.689, T_max = 1.000	k = −38→37
15203 measured reflections	l = −14→10

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: mixed
wR(F²) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0647P)² + 1.3763P] where P = (F_o² + 2F_c²)/3
7439 reflections	(Δ/σ)_max = 0.001
571 parameters	Δρ_max = 0.53 e Å⁻³
19 restraints	Δρ_min = −0.39 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C11	−0.1186 (3)	0.08238 (9)	0.7887 (2)	0.0307 (6)
C12	−0.0212 (3)	0.08576 (9)	0.9016 (2)	0.0286 (6)
C13	0.0638 (3)	0.05221 (9)	0.9514 (2)	0.0262 (5)
C14	0.1427 (3)	0.05986 (9)	1.0657 (2)	0.0258 (5)
C15	0.2225 (3)	0.02711 (9)	1.1261 (2)	0.0283 (6)
H15	0.2228	0.0002	1.0938	0.034*
C16	0.2988 (3)	0.03479 (9)	1.2312 (2)	0.0285 (6)
C17	0.3084 (3)	0.07574 (9)	1.2835 (2)	0.0268 (6)
C18	0.2265 (3)	0.10767 (9)	1.2257 (2)	0.0273 (6)
H18	0.2276	0.1346	1.2582	0.033*
C19	0.1420 (3)	0.09988 (8)	1.1185 (2)	0.0254 (5)
C21	0.1295 (3)	−0.07446 (9)	0.7028 (2)	0.0301 (6)
C22	0.0315 (3)	−0.07892 (9)	0.5910 (2)	0.0277 (6)
C23	−0.0658 (3)	−0.04814 (8)	0.5456 (2)	0.0266 (5)
C24	−0.1452 (3)	−0.05645 (8)	0.4328 (2)	0.0247 (5)
C25	−0.2352 (3)	−0.02540 (9)	0.3761 (2)	0.0283 (6)
H25	−0.2424	0.0007	0.4108	0.034*
C26	−0.3115 (3)	−0.03356 (9)	0.2710 (2)	0.0285 (6)
C27	−0.3131 (3)	−0.07375 (9)	0.2164 (2)	0.0257 (5)
C28	−0.2217 (3)	−0.10386 (9)	0.2707 (2)	0.0261 (5)
H28	−0.2176	−0.1303	0.2366	0.031*
C29	−0.1354 (3)	−0.09525 (8)	0.3761 (2)	0.0249 (5)
C110	−0.0180 (3)	0.12398 (9)	0.9584 (2)	0.0300 (6)
H110	−0.0741	0.1457	0.9230	0.036*
C111	0.0559 (3)	0.17520 (9)	1.1114 (2)	0.0343 (7)
H11A	0.0129	0.1950	1.0524	0.041*
H11B	0.1456	0.1852	1.1418	0.041*
C112	−0.0161 (4)	0.17582 (12)	1.2042 (3)	0.0484 (8)
H11C	−0.0156	0.2044	1.2334	0.073*
H11D	−0.1056	0.1666	1.1744	0.073*
H11E	0.0271	0.1568	1.2638	0.073*
C113	0.5361 (3)	0.07588 (10)	1.3852 (2)	0.0363 (7)
H11F	0.5634	0.0998	1.3457	0.044*
H11G	0.5444	0.0499	1.3442	0.044*
C114	0.6244 (3)	0.07312 (10)	1.5033 (3)	0.0424 (8)
H11H	0.6005	0.0483	1.5418	0.051*
H11I	0.7155	0.0699	1.5000	0.051*
C115	0.4703 (3)	0.11908 (12)	1.5686 (2)	0.0424 (8)
H11J	0.4623	0.1455	1.6082	0.051*
H11K	0.4417	0.0956	1.6088	0.051*
C116	0.3832 (3)	0.12133 (10)	1.4490 (2)	0.0353 (7)
H11L	0.2918	0.1251	1.4511	0.042*
H11M	0.4088	0.1456	1.4098	0.042*
C210	0.0400 (3)	−0.11557 (9)	0.5300 (2)	0.0298 (6)
H210	0.1052	−0.1354	0.5615	0.036*
C211	−0.0272 (3)	−0.16725 (10)	0.3794 (3)	0.0427 (8)
H21A	0.0630	−0.1773	0.4056	0.051*
H21B	−0.0473	−0.1649	0.2977	0.051*
C212	−0.1185 (5)	−0.19914 (12)	0.4114 (4)	0.0717 (13)
H21C	−0.1083	−0.2264	0.3783	0.108*
H21D	−0.0978	−0.2019	0.4921	0.108*
H21E	−0.2081	−0.1895	0.3843	0.108*
C213	−0.5431 (3)	−0.07480 (10)	0.1142 (2)	0.0346 (7)
H21F	−0.5524	−0.0492	0.1564	0.042*
H21G	−0.5718	−0.0991	0.1514	0.042*
C214	−0.6282 (3)	−0.07104 (10)	−0.0055 (3)	0.0409 (7)
H21H	−0.7202	−0.0684	−0.0042	0.049*
H21I	−0.6036	−0.0456	−0.0409	0.049*
C215	−0.4697 (3)	−0.11622 (11)	−0.0697 (2)	0.0387 (7)
H21J	−0.4385	−0.0925	−0.1074	0.046*
H21K	−0.4607	−0.1423	−0.1102	0.046*
C216	−0.3870 (3)	−0.11949 (10)	0.0511 (2)	0.0311 (6)
H21L	−0.4147	−0.1441	0.0877	0.037*
H21M	−0.2948	−0.1232	0.0517	0.037*
N11	0.0601 (2)	0.13206 (7)	1.06092 (18)	0.0288 (5)
N12	0.3971 (2)	0.08169 (7)	1.38910 (18)	0.0286 (5)
N13	0.6096 (2)	0.11253 (8)	1.56612 (19)	0.0358 (6)
H13A	0.6373	0.1350	1.5334	0.043*
H13B	0.6595	0.1106	1.6365	0.043*
N21	−0.0394 (2)	−0.12446 (7)	0.42867 (19)	0.0290 (5)
N22	−0.4034 (2)	−0.08045 (8)	0.11240 (18)	0.0290 (5)
N23	−0.6101 (2)	−0.10945 (9)	−0.07104 (19)	0.0371 (6)
H23A	−0.6571	−0.1065	−0.1421	0.045*
H23B	−0.6403	−0.1324	−0.0421	0.045*
O1	0.6929 (3)	0.17969 (8)	1.4610 (2)	0.0543 (6)
O2	0.5560 (3)	0.24126 (10)	1.4655 (3)	0.0762 (9)
O1W	0.5280 (4)	0.19254 (11)	1.7676 (3)	0.0908 (11)
H1A	0.511 (6)	0.2167 (9)	1.796 (5)	0.136*
H1B	0.570 (6)	0.2003 (16)	1.718 (4)	0.136*
O3	0.6948 (3)	0.21358 (11)	1.6361 (2)	0.0746 (9)
O2W	0.9107 (3)	0.27358 (11)	1.3321 (2)	0.0649 (8)
H2A	0.874 (4)	0.2595 (14)	1.376 (3)	0.097*
H2B	0.852 (3)	0.2773 (16)	1.271 (2)	0.097*
O4	0.7907 (3)	0.24842 (8)	1.5053 (3)	0.0602 (7)
O3W	0.6432 (4)	0.19064 (11)	1.2156 (3)	0.0796 (9)
H3A	0.646 (6)	0.1887 (15)	1.2865 (15)	0.119*
H3B	0.666 (6)	0.2167 (7)	1.207 (4)	0.119*
O4W	−0.7155 (3)	−0.16850 (9)	0.0375 (3)	0.0687 (8)
H4A	−0.663 (4)	−0.1705 (14)	0.105 (2)	0.103*
H4B	−0.723 (5)	−0.1949 (6)	0.015 (3)	0.103*
O5W	1.1771 (3)	0.29173 (13)	1.3659 (3)	0.0805 (10)
H5A	1.223 (4)	0.2803 (17)	1.427 (3)	0.121*
H5B	1.101 (3)	0.2794 (17)	1.356 (4)	0.121*
O6W	1.3591 (3)	0.27839 (14)	1.5645 (3)	0.0838 (10)
H6A	1.410 (5)	0.2583 (14)	1.551 (4)	0.126*
H6B	1.358 (6)	0.2748 (18)	1.6341 (18)	0.126*
O7W	1.3296 (4)	0.27774 (14)	1.7932 (3)	0.0942 (11)
H7A	1.402 (4)	0.269 (2)	1.836 (5)	0.141*
O11	−0.1095 (2)	0.05163 (7)	0.72254 (15)	0.0362 (5)
O12	−0.2054 (2)	0.11010 (8)	0.76522 (18)	0.0538 (7)
O13	0.0771 (2)	0.01636 (6)	0.90494 (15)	0.0326 (4)
O21	0.1072 (2)	−0.04761 (7)	0.77461 (16)	0.0370 (5)
O22	0.2278 (2)	−0.09795 (7)	0.72096 (17)	0.0425 (5)
O23	−0.0864 (2)	−0.01374 (6)	0.59537 (15)	0.0321 (4)
F1	0.36983 (18)	0.00254 (5)	1.29009 (14)	0.0385 (4)
F2	−0.38851 (18)	−0.00192 (5)	0.21422 (14)	0.0395 (4)
Cu1	−0.00292 (4)	0.00158 (2)	0.74970 (3)	0.02858 (13)
S1	0.68249 (8)	0.22095 (3)	1.51666 (7)	0.04002 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C11	0.0306 (15)	0.0353 (15)	0.0206 (13)	0.0000 (12)	−0.0040 (11)	−0.0025 (11)
C12	0.0277 (14)	0.0358 (15)	0.0177 (12)	0.0000 (11)	−0.0031 (11)	−0.0031 (11)
C13	0.0256 (13)	0.0301 (14)	0.0216 (13)	−0.0031 (11)	0.0031 (11)	−0.0031 (10)
C14	0.0243 (13)	0.0287 (14)	0.0211 (13)	−0.0010 (11)	−0.0003 (11)	−0.0027 (10)
C15	0.0290 (14)	0.0274 (13)	0.0256 (13)	−0.0025 (11)	0.0011 (11)	−0.0052 (11)
C16	0.0276 (14)	0.0302 (14)	0.0245 (13)	0.0011 (11)	0.0001 (11)	0.0031 (11)
C17	0.0226 (13)	0.0347 (15)	0.0207 (12)	−0.0029 (11)	0.0012 (10)	−0.0011 (10)
C18	0.0280 (14)	0.0301 (14)	0.0208 (13)	−0.0014 (11)	0.0007 (11)	−0.0038 (10)
C19	0.0263 (13)	0.0265 (13)	0.0201 (12)	−0.0006 (11)	−0.0007 (11)	−0.0027 (10)
C21	0.0310 (15)	0.0344 (15)	0.0201 (13)	−0.0007 (12)	−0.0028 (11)	−0.0018 (11)
C22	0.0251 (13)	0.0348 (15)	0.0190 (12)	−0.0015 (11)	−0.0023 (11)	−0.0026 (10)
C23	0.0284 (14)	0.0269 (13)	0.0220 (13)	−0.0039 (11)	0.0018 (11)	−0.0018 (10)
C24	0.0253 (13)	0.0261 (13)	0.0192 (12)	−0.0021 (10)	−0.0010 (10)	−0.0014 (10)
C25	0.0301 (14)	0.0243 (13)	0.0262 (13)	−0.0008 (11)	−0.0009 (11)	−0.0030 (10)
C26	0.0278 (14)	0.0281 (14)	0.0245 (13)	0.0022 (11)	−0.0031 (11)	0.0026 (10)
C27	0.0263 (13)	0.0312 (14)	0.0173 (12)	−0.0033 (11)	0.0009 (10)	−0.0024 (10)
C28	0.0253 (13)	0.0286 (13)	0.0219 (13)	−0.0013 (11)	0.0014 (11)	−0.0035 (10)
C29	0.0240 (13)	0.0262 (13)	0.0223 (12)	−0.0016 (10)	0.0018 (10)	−0.0008 (10)
C110	0.0294 (14)	0.0344 (15)	0.0221 (13)	0.0055 (12)	−0.0014 (11)	−0.0006 (11)
C111	0.0449 (17)	0.0243 (14)	0.0284 (14)	0.0035 (12)	−0.0009 (13)	−0.0030 (11)
C112	0.052 (2)	0.051 (2)	0.0432 (18)	0.0104 (17)	0.0127 (16)	−0.0089 (16)
C113	0.0260 (15)	0.0462 (18)	0.0322 (15)	0.0034 (13)	−0.0011 (12)	−0.0084 (13)
C114	0.0333 (16)	0.0423 (18)	0.0405 (18)	0.0029 (14)	−0.0115 (14)	−0.0025 (14)
C115	0.0392 (17)	0.060 (2)	0.0234 (14)	−0.0047 (15)	−0.0001 (13)	−0.0104 (14)
C116	0.0277 (15)	0.0479 (18)	0.0255 (14)	0.0017 (13)	−0.0026 (12)	−0.0091 (12)
C210	0.0270 (14)	0.0345 (15)	0.0230 (13)	0.0032 (12)	−0.0026 (11)	−0.0002 (11)
C211	0.0436 (18)	0.0380 (17)	0.0359 (16)	0.0135 (14)	−0.0098 (14)	−0.0142 (13)
C212	0.106 (4)	0.0346 (19)	0.063 (3)	−0.011 (2)	0.000 (2)	−0.0078 (18)
C213	0.0272 (14)	0.0442 (17)	0.0275 (14)	0.0020 (12)	−0.0028 (12)	−0.0082 (12)
C214	0.0339 (16)	0.0427 (17)	0.0353 (16)	0.0030 (14)	−0.0114 (13)	−0.0013 (13)
C215	0.0355 (16)	0.057 (2)	0.0202 (13)	−0.0053 (15)	0.0004 (12)	−0.0085 (13)
C216	0.0266 (14)	0.0405 (16)	0.0230 (13)	0.0028 (12)	0.0000 (11)	−0.0068 (11)
N11	0.0301 (12)	0.0290 (12)	0.0228 (11)	0.0035 (10)	−0.0017 (9)	−0.0038 (9)
N12	0.0263 (12)	0.0359 (13)	0.0196 (11)	−0.0008 (10)	−0.0016 (9)	−0.0033 (9)
N13	0.0358 (14)	0.0422 (14)	0.0221 (11)	−0.0044 (11)	−0.0063 (10)	−0.0005 (10)
N21	0.0280 (12)	0.0291 (12)	0.0247 (11)	0.0046 (9)	−0.0034 (9)	−0.0062 (9)
N22	0.0252 (12)	0.0362 (13)	0.0215 (11)	0.0002 (10)	−0.0020 (9)	−0.0030 (9)
N23	0.0325 (13)	0.0487 (15)	0.0228 (11)	−0.0045 (11)	−0.0067 (10)	−0.0031 (10)
O1	0.0696 (17)	0.0405 (13)	0.0553 (15)	−0.0036 (12)	0.0203 (13)	−0.0039 (11)
O2	0.0478 (17)	0.086 (2)	0.084 (2)	0.0203 (15)	−0.0025 (16)	−0.0129 (17)
O1W	0.126 (3)	0.075 (2)	0.082 (2)	−0.018 (2)	0.044 (2)	−0.0095 (19)
O3	0.079 (2)	0.104 (3)	0.0427 (15)	−0.0062 (19)	0.0186 (15)	−0.0066 (15)
O2W	0.0515 (16)	0.086 (2)	0.0559 (17)	−0.0053 (16)	0.0116 (13)	−0.0046 (16)
O4	0.0579 (17)	0.0471 (15)	0.0740 (19)	−0.0094 (12)	0.0133 (15)	0.0034 (13)
O3W	0.101 (3)	0.072 (2)	0.0565 (17)	−0.014 (2)	0.0020 (18)	−0.0089 (15)
O4W	0.089 (2)	0.0488 (16)	0.077 (2)	−0.0145 (15)	0.0354 (18)	−0.0065 (14)
O5W	0.0542 (18)	0.125 (3)	0.0563 (18)	−0.0023 (19)	0.0035 (14)	0.0282 (19)
O6W	0.0558 (19)	0.125 (3)	0.065 (2)	0.0102 (19)	0.0035 (16)	0.011 (2)
O7W	0.084 (3)	0.120 (3)	0.064 (2)	−0.011 (2)	−0.0087 (18)	0.013 (2)
O11	0.0391 (12)	0.0396 (11)	0.0221 (10)	0.0052 (9)	−0.0072 (8)	−0.0060 (8)
O12	0.0508 (14)	0.0591 (15)	0.0348 (12)	0.0251 (12)	−0.0204 (11)	−0.0159 (11)
O13	0.0388 (11)	0.0306 (10)	0.0219 (9)	0.0032 (9)	−0.0049 (8)	−0.0044 (8)
O21	0.0397 (12)	0.0403 (11)	0.0231 (10)	0.0068 (9)	−0.0068 (9)	−0.0065 (8)
O22	0.0333 (11)	0.0538 (13)	0.0308 (11)	0.0128 (10)	−0.0102 (9)	−0.0095 (10)
O23	0.0359 (11)	0.0324 (10)	0.0213 (9)	0.0032 (8)	−0.0051 (8)	−0.0061 (8)
F1	0.0429 (10)	0.0312 (9)	0.0321 (9)	0.0044 (7)	−0.0081 (8)	0.0038 (7)
F2	0.0447 (10)	0.0316 (9)	0.0315 (9)	0.0083 (8)	−0.0104 (8)	0.0011 (7)
Cu1	0.0320 (2)	0.0301 (2)	0.0189 (2)	−0.00106 (17)	−0.00257 (17)	−0.00483 (15)
S1	0.0409 (4)	0.0387 (4)	0.0387 (4)	0.0018 (3)	0.0067 (3)	−0.0015 (3)

Geometric parameters (Å, º) top

C11—O12	1.235 (3)	C27—N22	1.397 (3)
C11—O11	1.274 (3)	C28—C29	1.402 (3)
C11—C12	1.501 (3)	C29—N21	1.390 (3)
C12—C110	1.377 (4)	C110—N11	1.338 (3)
C12—C13	1.410 (4)	C111—N11	1.486 (3)
C13—O13	1.278 (3)	C111—C112	1.511 (4)
C13—C14	1.454 (3)	C113—N12	1.478 (3)
C14—C15	1.407 (4)	C113—C114	1.509 (4)
C14—C19	1.407 (4)	C114—N13	1.479 (4)
C15—C16	1.355 (4)	C115—N13	1.479 (4)
C16—F1	1.348 (3)	C115—C116	1.518 (4)
C16—C17	1.422 (4)	C116—N12	1.464 (4)
C17—C18	1.387 (4)	C210—N21	1.337 (3)
C17—N12	1.401 (3)	C211—N21	1.484 (3)
C18—C19	1.407 (3)	C211—C212	1.498 (5)
C19—N11	1.392 (3)	C213—N22	1.478 (3)
C21—O22	1.237 (3)	C213—C214	1.515 (4)
C21—O21	1.277 (3)	C214—N23	1.481 (4)
C21—C22	1.497 (3)	C215—N23	1.481 (4)
C22—C210	1.381 (4)	C215—C216	1.517 (4)
C22—C23	1.409 (4)	C216—N22	1.463 (3)
C23—O23	1.279 (3)	O1—S1	1.474 (2)
C23—C24	1.445 (3)	O2—S1	1.460 (3)
C24—C25	1.407 (4)	O3—S1	1.452 (3)
C24—C29	1.412 (4)	O4—S1	1.454 (3)
C25—C26	1.357 (4)	O11—Cu1	1.900 (2)
C26—F2	1.352 (3)	O13—Cu1	1.9292 (18)
C26—C27	1.420 (4)	O21—Cu1	1.898 (2)
C27—C28	1.386 (4)	O23—Cu1	1.9311 (18)

O12—C11—O11	123.2 (3)	N21—C29—C24	117.9 (2)
O12—C11—C12	117.1 (3)	C28—C29—C24	120.4 (2)
O11—C11—C12	119.7 (2)	N11—C110—C12	124.6 (3)
C110—C12—C13	119.5 (2)	N11—C111—C112	113.3 (3)
C110—C12—C11	116.7 (2)	N12—C113—C114	110.4 (2)
C13—C12—C11	123.7 (2)	N13—C114—C113	109.3 (2)
O13—C13—C12	125.8 (2)	N13—C115—C116	110.2 (2)
O13—C13—C14	118.2 (2)	N12—C116—C115	109.4 (3)
C12—C13—C14	116.0 (2)	N21—C210—C22	124.3 (3)
C15—C14—C19	118.4 (2)	N21—C211—C212	111.5 (3)
C15—C14—C13	120.3 (2)	N22—C213—C214	109.9 (2)
C19—C14—C13	121.3 (2)	N23—C214—C213	109.7 (2)
C16—C15—C14	120.1 (3)	N23—C215—C216	110.1 (2)
F1—C16—C15	119.3 (3)	N22—C216—C215	109.4 (2)
F1—C16—C17	117.7 (2)	C110—N11—C19	119.5 (2)
C15—C16—C17	123.0 (3)	C110—N11—C111	119.0 (2)
C18—C17—N12	123.8 (2)	C19—N11—C111	121.5 (2)
C18—C17—C16	116.8 (2)	C17—N12—C116	116.6 (2)
N12—C17—C16	119.3 (2)	C17—N12—C113	112.6 (2)
C17—C18—C19	121.0 (2)	C116—N12—C113	109.9 (2)
N11—C19—C14	118.8 (2)	C114—N13—C115	110.9 (2)
N11—C19—C18	120.7 (2)	C210—N21—C29	120.2 (2)
C14—C19—C18	120.4 (2)	C210—N21—C211	117.8 (2)
O22—C21—O21	123.6 (2)	C29—N21—C211	121.9 (2)
O22—C21—C22	117.2 (2)	C27—N22—C216	116.9 (2)
O21—C21—C22	119.2 (3)	C27—N22—C213	114.5 (2)
C210—C22—C23	119.4 (2)	C216—N22—C213	110.4 (2)
C210—C22—C21	116.7 (2)	C214—N23—C215	111.7 (2)
C23—C22—C21	124.0 (2)	C11—O11—Cu1	129.99 (18)
O23—C23—C22	125.2 (2)	C13—O13—Cu1	125.30 (17)
O23—C23—C24	118.6 (2)	C21—O21—Cu1	128.97 (18)
C22—C23—C24	116.1 (2)	C23—O23—Cu1	125.71 (18)
C25—C24—C29	118.1 (2)	O21—Cu1—O11	178.25 (9)
C25—C24—C23	120.0 (2)	O21—Cu1—O13	86.49 (8)
C29—C24—C23	121.8 (2)	O11—Cu1—O13	93.83 (8)
C26—C25—C24	120.0 (3)	O21—Cu1—O23	93.71 (8)
F2—C26—C25	118.9 (2)	O11—Cu1—O23	86.01 (8)
F2—C26—C27	117.9 (2)	O13—Cu1—O23	178.69 (9)
C25—C26—C27	123.1 (2)	O3—S1—O4	108.29 (18)
C28—C27—N22	124.3 (2)	O3—S1—O2	110.1 (2)
C28—C27—C26	116.6 (2)	O4—S1—O2	110.29 (19)
N22—C27—C26	119.1 (2)	O3—S1—O1	109.10 (17)
C27—C28—C29	121.3 (2)	O4—S1—O1	108.80 (16)
N21—C29—C28	121.6 (2)	O2—S1—O1	110.21 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C110—H110···O4Wⁱ	0.93	2.47	3.126 (4)	127
C111—H11B···O7Wⁱⁱ	0.97	2.59	3.481 (5)	153
C113—H11F···O22ⁱⁱⁱ	0.97	2.52	3.140 (4)	122
C113—H11G···F1	0.97	2.31	2.935 (3)	121
C113—H11G···F2^iv	0.97	2.49	3.423 (3)	162
C114—H11H···F1^v	0.97	2.55	3.448 (4)	153
C115—H11J···O1W	0.97	2.40	3.288 (5)	152
C210—H210···O1ⁱⁱⁱ	0.93	2.60	3.417 (4)	147
C211—H21A···S1ⁱⁱⁱ	0.97	2.93	3.892 (3)	171
C211—H21B···O5W^vi	0.97	2.51	3.277 (4)	136
C213—H21F···F1^vii	0.97	2.57	3.502 (3)	161
C213—H21F···F2	0.97	2.24	2.882 (3)	123
C214—H21I···F2^viii	0.97	2.57	3.457 (4)	152
C215—H21K···O3W^ix	0.97	2.52	3.203 (4)	127
N13—H13A···O1	0.89	1.82	2.714 (4)	178
N13—H13A···S1	0.89	2.74	3.555 (3)	152
N13—H13B···O12^iv	0.89	1.83	2.706 (3)	166
N23—H23A···O22^vii	0.89	1.82	2.705 (3)	172
N23—H23B···O4W	0.89	1.80	2.666 (4)	165
O1W—H1A···O2^x	0.87 (1)	2.40 (4)	3.139 (5)	143 (5)
O1W—H1B···O3	0.87 (1)	1.88 (2)	2.732 (5)	167 (6)
O2W—H2A···O4	0.85 (1)	2.02 (2)	2.828 (4)	158 (5)
O2W—H2B···O3^xi	0.85 (1)	2.04 (1)	2.882 (4)	173 (4)
O3W—H3A···O1	0.86 (1)	2.09 (2)	2.934 (4)	168 (6)
O3W—H3A···S1	0.86 (1)	2.92 (2)	3.722 (3)	155 (4)
O3W—H3B···O3^xi	0.86 (1)	2.39 (2)	3.232 (5)	165 (5)
O4W—H4A···O1W^xii	0.87 (1)	1.95 (2)	2.785 (6)	160 (4)
O4W—H4B···O2^xiii	0.87 (1)	2.62 (4)	3.279 (5)	133 (4)
O4W—H4B···O4^xiii	0.87 (1)	1.90 (2)	2.723 (4)	158 (5)
O4W—H4B···S1^xiii	0.87 (1)	2.70 (2)	3.548 (3)	165 (4)
O5W—H5A···O6W	0.86 (1)	1.91 (2)	2.717 (4)	156 (5)
O5W—H5B···O2W	0.86 (1)	1.95 (2)	2.772 (4)	159 (6)
O6W—H6A···O2^xiv	0.86 (1)	2.13 (3)	2.880 (5)	146 (5)
O6W—H6B···O7W	0.86 (1)	2.04 (1)	2.889 (5)	167 (5)
O7W—H7A···O2^xv	0.86 (1)	1.98 (2)	2.812 (4)	164 (7)

Symmetry codes: (i) −x−1, −y, −z+1; (ii) x−1, −y+1/2, z−1/2; (iii) −x+1, −y, −z+2; (iv) x+1, y, z+1; (v) −x+1, −y, −z+3; (vi) −x+1, y−1/2, −z+3/2; (vii) x−1, y, z−1; (viii) −x−1, −y, −z; (ix) −x, −y, −z+1; (x) x, −y+1/2, z+1/2; (xi) x, −y+1/2, z−1/2; (xii) −x, −y, −z+2; (xiii) −x, y−1/2, −z+3/2; (xiv) x+1, y, z; (xv) x+1, −y+1/2, z+1/2.

Bis{1-[2-(ethylsulfonyl)ethyl]-2-methyl-5-nitroimide)dinitratocopper(II) (II) top

Crystal data top

[Cu(NO₃)₂(C₈H₁₃N₃O₄S)₂]	F(000) = 702
M_r = 682.11	D_x = 1.732 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.3063 (3) Å	Cell parameters from 1876 reflections
b = 10.8907 (5) Å	θ = 3.6–28.1°
c = 16.4396 (5) Å	µ = 1.08 mm⁻¹
β = 90.670 (3)°	T = 296 K
V = 1308.02 (9) Å³	Fragment, blue
Z = 2	0.26 × 0.18 × 0.04 mm

Data collection top

Xcalibur, Eos, Gemini diffractometer	2850 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	2257 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 16.0604 pixels mm^-1	θ_max = 28.8°, θ_min = 3.1°
Absorption correction: multi-scan CrysAlis PRO (Rigaku OD, 2015)	h = −9→9
T_min = 0.903, T_max = 1.000	k = −13→13
5901 measured reflections	l = −20→19

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0357P)² + 0.9317P] where P = (F_o² + 2F_c²)/3
2850 reflections	(Δ/σ)_max = 0.009
189 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.3168 (4)	0.6549 (3)	0.37000 (15)	0.0248 (6)
C2	0.3393 (4)	0.5418 (3)	0.26089 (15)	0.0260 (6)
C3	0.4058 (4)	0.4765 (3)	0.32474 (15)	0.0278 (7)
H3	0.4527	0.3972	0.3227	0.033*
C4	0.1939 (4)	0.7562 (3)	0.24456 (16)	0.0289 (7)
H4A	0.2267	0.7519	0.1876	0.035*
H4B	0.2395	0.8336	0.2660	0.035*
C5	−0.0135 (4)	0.7542 (3)	0.25107 (17)	0.0305 (7)
H5A	−0.0586	0.8357	0.2378	0.037*
H5B	−0.0436	0.7385	0.3074	0.037*
C6	−0.1054 (5)	0.6964 (3)	0.08866 (17)	0.0407 (8)
H6A	−0.1474	0.7805	0.0829	0.049*
H6B	0.0235	0.6938	0.0753	0.049*
C7	−0.2127 (6)	0.6140 (4)	0.0309 (2)	0.0638 (12)
H7A	−0.1628	0.5325	0.0327	0.096*
H7B	−0.2045	0.6456	−0.0235	0.096*
H7C	−0.3387	0.6119	0.0468	0.096*
C8	0.2742 (5)	0.7587 (3)	0.42395 (17)	0.0370 (8)
H8A	0.1507	0.7512	0.4426	0.055*
H8B	0.2874	0.8344	0.3946	0.055*
H8C	0.3569	0.7582	0.4698	0.055*
N1	0.3916 (3)	0.5482 (2)	0.39305 (12)	0.0249 (5)
N2	0.2837 (3)	0.6547 (2)	0.28858 (12)	0.0241 (5)
N3	0.3499 (3)	0.5053 (3)	0.17749 (14)	0.0355 (6)
N4	0.8211 (3)	0.5157 (3)	0.42758 (14)	0.0332 (6)
O1	0.3957 (4)	0.3990 (3)	0.16552 (14)	0.0587 (8)
O2	0.3176 (3)	0.5801 (3)	0.12362 (12)	0.0471 (6)
O3	−0.0547 (3)	0.5277 (2)	0.19919 (13)	0.0432 (6)
O4	−0.3248 (3)	0.6618 (3)	0.20998 (15)	0.0547 (7)
O5	0.7140 (3)	0.4248 (2)	0.43727 (13)	0.0422 (6)
O6	0.9632 (4)	0.5017 (3)	0.39217 (17)	0.0740 (10)
O7	0.7692 (4)	0.6141 (3)	0.45562 (17)	0.0659 (8)
S	−0.13532 (10)	0.64714 (8)	0.18994 (4)	0.03039 (19)
Cu	0.5000	0.5000	0.5000	0.02395 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0223 (13)	0.0300 (17)	0.0220 (12)	−0.0018 (12)	0.0000 (10)	−0.0007 (12)
C2	0.0230 (14)	0.0315 (17)	0.0234 (13)	−0.0012 (12)	−0.0025 (11)	−0.0033 (12)
C3	0.0247 (14)	0.0327 (19)	0.0261 (13)	0.0046 (12)	−0.0019 (11)	−0.0020 (12)
C4	0.0313 (15)	0.0277 (18)	0.0278 (14)	−0.0052 (12)	−0.0027 (11)	0.0079 (12)
C5	0.0317 (16)	0.0269 (17)	0.0325 (14)	0.0000 (12)	−0.0061 (12)	−0.0004 (12)
C6	0.053 (2)	0.035 (2)	0.0330 (15)	−0.0102 (16)	−0.0125 (14)	0.0099 (14)
C7	0.091 (3)	0.057 (3)	0.043 (2)	−0.023 (2)	−0.022 (2)	0.0028 (19)
C8	0.053 (2)	0.0307 (19)	0.0276 (14)	0.0035 (15)	−0.0007 (13)	−0.0047 (13)
N1	0.0228 (12)	0.0311 (14)	0.0208 (11)	0.0028 (10)	−0.0012 (9)	−0.0030 (10)
N2	0.0243 (12)	0.0268 (14)	0.0213 (10)	−0.0028 (10)	−0.0008 (9)	0.0017 (10)
N3	0.0325 (14)	0.050 (2)	0.0243 (12)	0.0023 (13)	−0.0030 (10)	−0.0063 (13)
N4	0.0275 (13)	0.0467 (19)	0.0255 (12)	−0.0008 (12)	−0.0016 (10)	0.0042 (12)
O1	0.088 (2)	0.0531 (19)	0.0348 (12)	0.0174 (15)	−0.0020 (12)	−0.0170 (12)
O2	0.0522 (15)	0.0635 (19)	0.0255 (11)	0.0033 (13)	−0.0033 (10)	0.0012 (11)
O3	0.0568 (15)	0.0257 (14)	0.0468 (13)	−0.0044 (11)	−0.0144 (11)	0.0070 (10)
O4	0.0302 (12)	0.069 (2)	0.0646 (15)	−0.0107 (12)	−0.0006 (11)	−0.0059 (14)
O5	0.0440 (14)	0.0408 (16)	0.0418 (12)	−0.0050 (11)	−0.0080 (10)	0.0079 (11)
O6	0.0371 (15)	0.116 (3)	0.0694 (18)	0.0052 (16)	0.0210 (13)	0.0283 (17)
O7	0.079 (2)	0.0490 (19)	0.0689 (17)	0.0136 (15)	−0.0264 (15)	−0.0263 (14)
S	0.0291 (4)	0.0275 (4)	0.0344 (4)	−0.0066 (3)	−0.0052 (3)	0.0061 (3)
Cu	0.0231 (3)	0.0290 (3)	0.0196 (2)	0.0030 (2)	−0.00049 (17)	−0.0005 (2)

Geometric parameters (Å, º) top

C1—N1	1.337 (4)	N1—Cu	1.990 (2)
C1—N2	1.357 (3)	N3—O2	1.223 (3)
C1—C8	1.472 (4)	N3—O1	1.222 (4)
C2—C3	1.353 (4)	N4—O6	1.205 (3)
C2—N2	1.375 (4)	N4—O7	1.229 (4)
C2—N3	1.430 (3)	N4—O5	1.273 (3)
C3—N1	1.373 (3)	O3—S	1.436 (2)
C4—N2	1.472 (4)	O4—S	1.436 (2)
C4—C5	1.520 (4)	O5—Cu	2.053 (2)
C5—S	1.773 (3)	Cu—N1ⁱ	1.990 (2)
C6—C7	1.518 (5)	Cu—O5ⁱ	2.053 (2)
C6—S	1.765 (3)

N1—C1—N2	110.2 (2)	O1—N3—C2	115.8 (3)
N1—C1—C8	125.8 (2)	O6—N4—O7	124.3 (3)
N2—C1—C8	124.0 (3)	O6—N4—O5	119.8 (3)
C3—C2—N2	108.5 (2)	O7—N4—O5	116.0 (3)
C3—C2—N3	125.1 (3)	N4—O5—Cu	103.06 (19)
N2—C2—N3	125.8 (3)	O4—S—O3	118.17 (16)
C2—C3—N1	107.8 (3)	O4—S—C6	108.24 (16)
N2—C4—C5	113.2 (2)	O3—S—C6	108.68 (16)
C4—C5—S	117.6 (2)	O4—S—C5	106.03 (15)
C7—C6—S	110.0 (2)	O3—S—C5	109.48 (14)
C1—N1—C3	107.3 (2)	C6—S—C5	105.53 (15)
C1—N1—Cu	129.56 (19)	N1ⁱ—Cu—N1	180.0
C3—N1—Cu	122.6 (2)	N1ⁱ—Cu—O5ⁱ	87.65 (9)
C1—N2—C2	106.1 (2)	N1—Cu—O5ⁱ	92.35 (9)
C1—N2—C4	123.9 (2)	N1ⁱ—Cu—O5	92.35 (9)
C2—N2—C4	129.9 (2)	N1—Cu—O5	87.65 (9)
O2—N3—O1	124.4 (3)	O5ⁱ—Cu—O5	180.0
O2—N3—C2	119.8 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O2	0.97	2.25	2.914 (4)	125
C4—H4B···O3ⁱⁱ	0.97	2.58	3.263 (4)	128
C5—H5A···O3ⁱⁱ	0.97	2.47	3.126 (4)	125
C6—H6A···O7ⁱⁱⁱ	0.97	2.46	3.136 (4)	127
C6—H6B···O2	0.97	2.60	3.383 (4)	138
C7—H7B···O7ⁱⁱⁱ	0.96	2.65	3.210 (5)	118
C8—H8B···O1^iv	0.96	2.62	3.224 (4)	121

Symmetry codes: (ii) −x, y+1/2, −z+1/2; (iii) x−1, −y+3/2, z−1/2; (iv) −x+1, y+1/2, −z+1/2.

Crystal data and structure refinement results for complexes [Cu(nor)₂]SO₄·7H₂O and [Cu(NO₃)₂(tnz)₂] top

Complex	[Cu(nor)₂]SO₄·7H₂O	[Cu(NO₃)₂(tnz)₂]
Chemical formula	C₃₂H₅₀CuF₂N₆O₁₇S	C₁₆H₂₆CuN₈O₁₄S₂
Formula weight	924.38	682.11
Temperature (K)	295 (2)	296 (2)
Wavelength (Å)	1.54184	0.71073
Crystal system	Monoclinic	Monoclinic
Space group	P2₁/c	P2₁/c
Unit-cell dimensions
a (Å)	10.4613 (3)	7.3063 (3)
b (Å)	31.2244 (8)	10.8907 (5)
c (Å)	12.2241 (3)	16.4396 (5)
β (°)	104.450 (3)	90.670 (3)
Volume (Å³)	3866.7 (2)	1308.02 (9)
Z	4	2
Density (calculated, Mg m^-3)	1.588	1.732
Absorption coeff. (mm^-1)	2.126	1.079
F(000)	1932	702
Crystal coloor	Blue	Blue
Crystal size (mm³)	0.43 × 0.17 × 0.03	0.255 × 0.179 × 0.042
θ range (°) for data collection	3.99–70.97	3.105–28.814
Index ranges	-12≤h≤12, -38≤k≤37, -14≤l≤10	-9≤h≤9, -13≤k≤13, -20≤l≤19
Reflections collected	15203	5901
Independent reflections	7439 (R_int = 0.0347)	2850 (R_int = 0.0350)
Obs. reflections [I > 2σ(I)]	5339	2257
Completeness (%)	99.8 (to θ = 70.97°)	99.9 (to θ = 25.242°)
Refinement method	Full-matrix least-squares on F²	Full-matrix least-squares on F²
Data/restraints/parameters	7439/19/571	2850/0/189
Goodness-of-fit on F²	1.005	1.058
Final R indices^a [I > 2σ(I)]	R1 = 0.0472, wR2 = 0.1220	R1 = 0.0431, wR2 = 0.0935
R indices (all data)	R1 = 0.0688, wR2 = 0.1421	R1 = 0.0605, wR2 = 0.1033
Largest diff. peak/hole (e Å^-3)	0.532/-0.387	0.496/-0.355

Note: (a) R1 = Σ//F_o/ – /F_c///Σ/F_o/, wR2 = [Σw(/F_o/² – /F_c/²)²/Σw(/F_o/²)²]^1/2

Powder diffraction data for [Cu(NO₃)₂(tnz)₂] top

Compound	[Cu(NO₃)₂(tnz)₂]
Molecular weight (g mol^-1)	682.11
Crystal system	Monoclinic
Space group	P2₁/c
a (Å)	7.3116 (4)
b (Å)	10.8923 (4)
c (Å)	16.4498 (5)
β (°)	90.660 (3)
V (Å³)	1310.0 (2)
Z	2
D_calc (mg cm^-3)	1.73

Bond distances (Å) and angles (°) around copper(II) in [Cu(nor)₂]SO₄·7H₂O top

Cu—O11	1.900 (2)	O21—Cu—O11	178.25 (9)
Cu—O13	1.929 (2)	O21—Cu—O13	86.49 (8)
Cu—O21	1.898 (2)	O11—Cu—O13	93.83 (8)
Cu—O23	1.931 (2)	O21—Cu—O23	93.71 (8)
		O11—Cu—O23	86.01 (8)
		O13—Cu—O23	178.69 (9)

Bond distances (Å) and angles (°) around copper(II) in centrosymmetric [Cu(NO₃)₂(tnz)₂] top

Cu—N1	1.990 (2)	Cu—O5	2.053 (2)
N1—Cu—O5	87.65 (9)

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Mol­ecular structures of two copper com­plexes with the pharmaceuticals nor­flox­acin and tin­id­az­ole, when powder X-ray diffraction assists multi-domain single-crystal X-ray diffraction

Supporting information

Molecular structures of two copper complexes with the pharmaceuticals norfloxacin and tinidazole, when powder X-ray diffraction assists multi-domain single-crystal X-ray diffraction