trans-Bis(dimethyl sulfoxide-κO)bis­(3-nitro­benzo­hydroxamato-κ²O,O′)zinc(II)

Single crystals of the title complex, [Zn(C₇H₅N₂O₄)₂(C₂H₆OS)₂] or [Zn(NBZH)₂(DMSO)₂], were isolated from a dimethyl sulfoxide (DMSO) solution containing [Zn(NBZH)₂]·2H₂O (NBZH = 3-nitro­benzo­hydroxamate anion). The asymmetric unit comprises of one O,O′-chelating NBZH anion, one O-bound DMSO ligand and one zinc(II) cation localized on an inversion centre. The three-dimensional crystal packing includes N—H...O and C—H...O hydrogen bonding, as well as O...H and H...H contacts identified by Hirshfeld isosurface analysis.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.032
• wR factor = 0.097
• Data-to-parameter ratio = 21.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...     Please Check
PLAT220_ALERT_2_C Non-Solvent  Resd 1  C   Ueq(max)/Ueq(min) Range        3.4 Ratio
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         S1 Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8A      ..O1       .       2.66 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          3 Report

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 Degree
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Zn1      --O1       .        6.2 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Zn1      --O5       .       14.4 s.u.
PLAT794_ALERT_5_G Tentative Bond Valency for Zn1       (II)      .       1.99 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          6 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 2006), Mercury (Macrae et al., 2006) and CrystalExplorer17 (Turner et al., 2017); software used to prepare material for publication: publCIF (Westrip, 2010).

trans-Bis(dimethyl sulfoxide-κO)bis(3-nitrobenzohydroxamato-κ²O,O')zinc(II)

Crystal data

[Zn(C7H5N2O4)2(C2H6OS)2]	Z = 1
Mr = 583.91	F(000) = 298
Triclinic, P1	Dx = 1.663 Mg m^−3
a = 6.4899 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.8961 (3) Å	Cell parameters from 9996 reflections
c = 11.4224 (4) Å	θ = 3.0–30.3°
α = 83.496 (1)°	µ = 1.30 mm^−1
β = 84.591 (1)°	T = 294 K
γ = 89.567 (1)°	Block, yellow
V = 578.98 (3) Å^3	0.20 × 0.15 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer	2961 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.032
Absorption correction: multi-scan (SADABS; Bruker, 2014)	θmax = 30.6°, θmin = 3.0°
Tmin = 0.786, Tmax = 0.880	h = −9→9
30874 measured reflections	k = −11→11
3558 independent reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: mixed
wR(F^2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	w = 1/[σ^2(Fo^2) + (0.0663P)^2 + 0.1979P] where P = (Fo^2 + 2Fc^2)/3
3558 reflections	(Δ/σ)max = 0.001
166 parameters	Δρmax = 0.65 e Å^−3
0 restraints	Δρmin = −0.53 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Zn1	0.500000	0.500000	1.000000	0.03291 (10)
S1	0.35743 (8)	0.88919 (6)	0.91043 (4)	0.04435 (13)
C1	0.8166 (2)	0.47473 (18)	0.82661 (13)	0.0259 (3)
O1	0.75668 (17)	0.64360 (15)	0.98049 (10)	0.0319 (2)
N1	0.88330 (19)	0.58558 (17)	0.89218 (12)	0.0281 (3)
H1	1.006 (3)	0.618 (3)	0.8898 (19)	0.037 (5)*
C3	0.8709 (2)	0.32583 (19)	0.64935 (13)	0.0288 (3)
H3	0.730590	0.299127	0.659747	0.035*
O2	0.63195 (17)	0.41942 (16)	0.84399 (10)	0.0350 (3)
O5	0.30496 (19)	0.70808 (15)	0.89650 (12)	0.0388 (3)
C6	1.2902 (3)	0.3979 (3)	0.61715 (16)	0.0396 (4)
H6	1.431200	0.421972	0.607033	0.048*
O4	1.0035 (3)	0.1408 (2)	0.38495 (13)	0.0596 (4)
C5	1.2036 (3)	0.3072 (2)	0.53664 (15)	0.0386 (4)
H5	1.283893	0.269754	0.472840	0.046*
O3	0.7091 (3)	0.1606 (2)	0.48421 (16)	0.0629 (4)
C4	0.9935 (3)	0.2746 (2)	0.55502 (14)	0.0317 (3)
C2	0.9584 (2)	0.41788 (18)	0.72915 (12)	0.0259 (3)
C8	0.1489 (5)	1.0145 (3)	0.8571 (3)	0.0721 (8)
H8A	0.165888	1.130499	0.872306	0.108*
H8B	0.020259	0.970410	0.896870	0.108*
H8C	0.148280	1.010210	0.773505	0.108*
N2	0.8946 (3)	0.18484 (19)	0.46896 (13)	0.0413 (3)
C7	1.1708 (2)	0.4532 (2)	0.71197 (15)	0.0331 (3)
H7	1.231884	0.514253	0.764663	0.040*
C9	0.5491 (5)	0.9574 (4)	0.7945 (3)	0.0868 (10)
H9A	0.507520	0.927737	0.720948	0.130*
H9B	0.677978	0.902758	0.809873	0.130*
H9C	0.565880	1.078767	0.789709	0.130*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.02448 (13)	0.04346 (16)	0.03212 (15)	−0.01039 (10)	0.00407 (9)	−0.01494 (11)
S1	0.0614 (3)	0.0350 (2)	0.0395 (2)	−0.01645 (19)	−0.0177 (2)	−0.00475 (17)
C1	0.0233 (6)	0.0292 (7)	0.0254 (6)	−0.0030 (5)	−0.0023 (5)	−0.0036 (5)
O1	0.0265 (5)	0.0382 (6)	0.0324 (5)	−0.0062 (4)	0.0034 (4)	−0.0145 (4)
N1	0.0212 (5)	0.0331 (6)	0.0303 (6)	−0.0053 (5)	0.0014 (4)	−0.0082 (5)
C3	0.0265 (6)	0.0305 (7)	0.0298 (7)	−0.0011 (5)	−0.0033 (5)	−0.0046 (5)
O2	0.0234 (5)	0.0491 (7)	0.0346 (6)	−0.0105 (4)	0.0028 (4)	−0.0179 (5)
O5	0.0351 (6)	0.0337 (6)	0.0491 (7)	−0.0088 (5)	−0.0093 (5)	−0.0071 (5)
C6	0.0250 (7)	0.0538 (10)	0.0398 (9)	0.0008 (7)	0.0016 (6)	−0.0084 (7)
O4	0.0774 (11)	0.0651 (10)	0.0399 (8)	0.0042 (8)	−0.0002 (7)	−0.0262 (7)
C5	0.0355 (8)	0.0470 (9)	0.0328 (8)	0.0067 (7)	0.0037 (6)	−0.0090 (7)
O3	0.0543 (9)	0.0770 (11)	0.0651 (10)	−0.0103 (8)	−0.0140 (7)	−0.0338 (8)
C4	0.0375 (8)	0.0303 (7)	0.0284 (7)	0.0026 (6)	−0.0055 (6)	−0.0057 (6)
C2	0.0244 (6)	0.0275 (6)	0.0258 (6)	0.0001 (5)	−0.0019 (5)	−0.0032 (5)
C8	0.102 (2)	0.0500 (13)	0.0705 (16)	0.0217 (13)	−0.0284 (15)	−0.0171 (12)
N2	0.0558 (9)	0.0359 (7)	0.0350 (7)	0.0027 (6)	−0.0089 (6)	−0.0124 (6)
C7	0.0250 (7)	0.0431 (8)	0.0323 (7)	−0.0027 (6)	−0.0028 (5)	−0.0092 (6)
C9	0.0757 (18)	0.090 (2)	0.086 (2)	−0.0402 (16)	−0.0005 (15)	0.0262 (17)

Geometric parameters (Å, º)

Zn1—O1^i	2.0029 (11)	C6—C7	1.381 (2)
Zn1—O1	2.0029 (11)	C6—C5	1.389 (3)
Zn1—O2^i	2.0675 (11)	C6—H6	0.9300
Zn1—O2	2.0675 (11)	O4—N2	1.219 (2)
Zn1—O5	2.3473 (12)	C5—C4	1.381 (3)
Zn1—O5^i	2.3474 (12)	C5—H5	0.9300
S1—O5	1.5019 (13)	O3—N2	1.214 (2)
S1—C9	1.769 (3)	C4—N2	1.471 (2)
S1—C8	1.783 (3)	C2—C7	1.400 (2)
C1—O2	1.2686 (17)	C8—H8A	0.9600
C1—N1	1.3153 (19)	C8—H8B	0.9600
C1—C2	1.484 (2)	C8—H8C	0.9600
O1—N1	1.3584 (16)	C7—H7	0.9300
N1—H1	0.84 (2)	C9—H9A	0.9600
C3—C4	1.375 (2)	C9—H9B	0.9600
C3—C2	1.391 (2)	C9—H9C	0.9600
C3—H3	0.9300
O1^i—Zn1—O1	180.0	C7—C6—C5	121.26 (15)
O1^i—Zn1—O2^i	81.79 (4)	C7—C6—H6	119.4
O1—Zn1—O2^i	98.20 (4)	C5—C6—H6	119.4
O1^i—Zn1—O2	98.21 (4)	C4—C5—C6	117.40 (15)
O1—Zn1—O2	81.80 (4)	C4—C5—H5	121.3
O2^i—Zn1—O2	180.0	C6—C5—H5	121.3
O1^i—Zn1—O5	86.04 (4)	C3—C4—C5	122.78 (16)
O1—Zn1—O5	93.96 (4)	C3—C4—N2	118.22 (15)
O2^i—Zn1—O5	88.40 (5)	C5—C4—N2	118.98 (15)
O2—Zn1—O5	91.60 (5)	C3—C2—C7	118.73 (14)
O1^i—Zn1—O5^i	93.96 (4)	C3—C2—C1	116.91 (13)
O1—Zn1—O5^i	86.04 (4)	C7—C2—C1	124.35 (13)
O2^i—Zn1—O5^i	91.60 (5)	S1—C8—H8A	109.5
O2—Zn1—O5^i	88.40 (5)	S1—C8—H8B	109.5
O5—Zn1—O5^i	180.00 (5)	H8A—C8—H8B	109.5
O5—S1—C9	106.83 (13)	S1—C8—H8C	109.5
O5—S1—C8	105.71 (11)	H8A—C8—H8C	109.5
C9—S1—C8	97.80 (16)	H8B—C8—H8C	109.5
O2—C1—N1	120.85 (13)	O3—N2—O4	123.43 (17)
O2—C1—C2	119.91 (13)	O3—N2—C4	118.52 (15)
N1—C1—C2	119.22 (12)	O4—N2—C4	118.04 (17)
N1—O1—Zn1	106.70 (8)	C6—C7—C2	120.31 (15)
C1—N1—O1	120.95 (12)	C6—C7—H7	119.8
C1—N1—H1	124.8 (15)	C2—C7—H7	119.8
O1—N1—H1	113.9 (15)	S1—C9—H9A	109.5
C4—C3—C2	119.51 (14)	S1—C9—H9B	109.5
C4—C3—H3	120.2	H9A—C9—H9B	109.5
C2—C3—H3	120.2	S1—C9—H9C	109.5
C1—O2—Zn1	107.94 (9)	H9A—C9—H9C	109.5
S1—O5—Zn1	115.22 (7)	H9B—C9—H9C	109.5
O2—C1—N1—O1	0.2 (2)	C4—C3—C2—C1	177.88 (13)
C2—C1—N1—O1	178.50 (12)	O2—C1—C2—C3	9.7 (2)
Zn1—O1—N1—C1	9.65 (16)	N1—C1—C2—C3	−168.60 (14)
N1—C1—O2—Zn1	−9.65 (17)	O2—C1—C2—C7	−171.33 (15)
C2—C1—O2—Zn1	172.04 (10)	N1—C1—C2—C7	10.3 (2)
C9—S1—O5—Zn1	91.19 (13)	C3—C4—N2—O3	0.5 (2)
C8—S1—O5—Zn1	−165.37 (12)	C5—C4—N2—O3	−178.16 (18)
C7—C6—C5—C4	0.1 (3)	C3—C4—N2—O4	179.45 (16)
C2—C3—C4—C5	1.5 (2)	C5—C4—N2—O4	0.8 (2)
C2—C3—C4—N2	−177.04 (13)	C5—C6—C7—C2	0.3 (3)
C6—C5—C4—C3	−1.0 (3)	C3—C2—C7—C6	0.3 (2)
C6—C5—C4—N2	177.56 (15)	C1—C2—C7—C6	−178.66 (15)
C4—C3—C2—C7	−1.1 (2)

Symmetry code: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8C···O4^ii	0.96	2.55	3.381 (3)	145
C8—H8A···O1^iii	0.96	2.66	3.533 (3)	150
N1—H1···O5^iv	0.84 (2)	2.08 (2)	2.916 (1)	175 (2)

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