Molecular structure of two copper complexes with pharmaceuticals norfloxacin and tinidazole, when powder X-ray diffraction assists multi-domains single-crystal X-ray diffraction. Addendum

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

doi:10.1107/S205252062201157X

addenda and errata

STRUCTURAL SCIENCE
CRYSTAL ENGINEERING
MATERIALS

ISSN: 2052-5206

Volume 79| Part 1| February 2023| Page 98

https://doi.org/10.1107/S205252062201157X

Molecular structure of two copper complexes with pharmaceuticals norfloxacin and tinidazole, when powder X-ray diffraction assists multi-domains single-crystal X-ray diffraction. Addendum

Gloria Elena Tobón Zapata,^a Dina Marcela Martínez Cardona,^a Gustavo Alberto Echeverría ^b and Oscar Enrique Piro ^b ^*

^aDepartamento de Farmacia, Facultad de Ciencias Farmacéuticas y Alimentarias, Universidad de Antioquía, AA 1226, Colombia, and ^bPhysics, Universidad Nacional de La Plata, C.C. 67, La Plata, Buenos Aires 1900, Argentina
^*Correspondence e-mail: piro@fisica.unlp.edu.ar

Edited by K. E. Knope, Georgetown University, USA (Received 3 November 2022; accepted 1 December 2022; online 21 January 2023)

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

CCDC reference: 2082848

Supporting information

CCDC reference: 2082848

Link https://doi.org/10.1107/S2052520622003766
Corrigendum

Cu(tnz)2(NO3)2. DOI: https://doi.org/10.1107/S205252062201157X/yv5008sup1.cif

Cu(tnz)2(NO3)2. DOI: https://doi.org/10.1107/S205252062201157X/yv5008Isup2.hkl

Computing details top

Data collection: CrysAlis PRO 1.171.38.41 (Rigaku OD, 2015); cell refinement: CrysAlis PRO 1.171.38.41 (Rigaku OD, 2015); data reduction: CrysAlis PRO 1.171.38.41 (Rigaku OD, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2014); molecular graphics: ORTEP for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2014/7 (Sheldrick, 2014).

bis[1-(2-(ethylsulfonyl) ethyl)-2-methyl-5-nitroimidazole] dinitrate copper(II) top

Crystal data top

C₁₆H₂₆CuN₈O₁₄S₂	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 CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	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

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
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.

Funding information

The following funding is acknowledged: Consejo Nacional de Investigaciones Científicas y Técnicas (grant No. PIP 0651); Universidad Nacional de La Plata (grant No. X857).

References

Castro-Ramírez, R., Ortiz-Pastrana, N., Caballero, A. B., Zimmerman, M. T., Stadelman, B. S., Gaertner, A. A. E., Brumaghim, J. L., Korrodi-Gregório, L., Pérez-Tomás, R., Gamez, P. & Barba-Behrens, N. (2018). Dalton Trans. 47, 7551–7560. PubMed Google Scholar
Tobón Zapata, G. E., Martínez Carmona, D. M., Echeverría, G. A. & Piro, O. E. (2022). Acta Cryst. B78, 490–498. CSD CrossRef IUCr Journals Google Scholar

This article is published by the International Union of Crystallography. Prior permission is not required to reproduce short quotations, tables and figures from this article, provided the original authors and source are cited. For more information, click here.

STRUCTURAL SCIENCE
CRYSTAL ENGINEERING
MATERIALS

ISSN: 2052-5206

Volume 79| Part 1| February 2023| Page 98

https://doi.org/10.1107/S205252062201157X

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

addenda and errata\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Molecular structure of two copper complexes with pharmaceuticals norfloxacin and tinidazole, when powder X-ray diffraction assists multi-domains single-crystal X-ray diffraction. Addendum

Supporting information

Funding information

References

addenda and errata