Synthesis, crystal structure and Hirshfeld surface analysis of di­aqua­bis­(o-phenyl­enedi­amine-κ²N,N′)nickel(II) naphthalene-1,5-di­sulfonate

In the title salt, [Ni(C₆H₈N₂)₂(H₂O)₂]·(C₁₀H₆O₆S₂), the Ni^II atom exhibits a slightly tetra­gonally distorted {O₂N₄} octa­hedral coordination environment, with two pairs of equatorial Ni—N bonds and a pair of longer axial Ni—O bonds.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 563 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.097
• Data-to-parameter ratio = 12.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT031_ALERT_4_C Refined Extinction Parameter Within Range of ...      3.000 Sigma
PLAT975_ALERT_2_C Check Calcd Resid. Dens.  0.83Ang From O3      .       0.44 eA-3

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          9 Note
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          2 Note
PLAT794_ALERT_5_G Tentative Bond Valency for Ni1       (II)      .       1.95 Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          6 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         16 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Info

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

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

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Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2023); cell refinement: CrysAlis PRO (Rigaku OD, 2023); data reduction: CrysAlis PRO (Rigaku OD, 2023); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

Diaquabis(o-phenylenediamine-κ²N,N')nickel(II) naphthalene-1,5-disulfonate

Crystal data

[Ni(C6H8N2)2(H2O)2](C10H6O6S2)	F(000) = 620
Mr = 597.30	Dx = 1.611 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 12.7613 (3) Å	Cell parameters from 6737 reflections
b = 7.7054 (1) Å	θ = 4.1–71.0°
c = 13.4641 (3) Å	µ = 3.22 mm^−1
β = 111.554 (2)°	T = 563 K
V = 1231.36 (5) Å^3	Block, light green
Z = 2	0.22 × 0.18 × 0.14 mm

Data collection

XtaLAB Synergy, Single source at home/near, HyPix3000 diffractometer	2380 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	2152 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.038
Detector resolution: 10.0000 pixels mm^-1	θmax = 71.3°, θmin = 4.1°
ω scans	h = −15→15
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2023)	k = −9→9
Tmin = 0.573, Tmax = 1.000	l = −14→16
11384 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.036	w = 1/[σ^2(Fo^2) + (0.048P)^2 + 0.8302P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.097	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.50 e Å^−3
2380 reflections	Δρmin = −0.49 e Å^−3
194 parameters	Extinction correction: SHELXL (Sheldrick, 2015a), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
6 restraints	Extinction coefficient: 0.0006 (2)
Primary atom site location: iterative

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
Ni1	1.000000	0.500000	0.500000	0.02713 (17)
S1	0.69836 (5)	0.87424 (8)	0.39745 (4)	0.03779 (18)
O1W	0.83329 (14)	0.4677 (2)	0.38469 (14)	0.0412 (4)
O1	0.73435 (15)	0.7254 (2)	0.46852 (14)	0.0488 (5)
N1	0.99045 (16)	0.2387 (2)	0.53808 (16)	0.0330 (4)
O3	0.62288 (17)	0.8217 (3)	0.29283 (14)	0.0574 (5)
N2	0.93181 (15)	0.5408 (2)	0.61643 (14)	0.0298 (4)
O2	0.79217 (17)	0.9758 (3)	0.39332 (19)	0.0636 (6)
C11	0.47191 (16)	1.0579 (3)	0.52339 (16)	0.0276 (4)
C6	0.91414 (17)	0.3765 (3)	0.66003 (16)	0.0297 (4)
C1	0.94563 (18)	0.2253 (3)	0.62287 (17)	0.0319 (5)
C7	0.62041 (18)	1.0098 (3)	0.45202 (17)	0.0313 (5)
C10	0.50918 (19)	1.2316 (3)	0.54324 (18)	0.0350 (5)
H10	0.473811	1.306841	0.575033	0.042*
C5	0.86718 (19)	0.3671 (3)	0.73833 (18)	0.0381 (5)
H5	0.846130	0.468202	0.763862	0.046*
C8	0.65220 (18)	1.1796 (3)	0.47028 (19)	0.0385 (5)
H8	0.711068	1.221455	0.451995	0.046*
C9	0.5960 (2)	1.2909 (3)	0.5166 (2)	0.0405 (5)
H9	0.618250	1.406318	0.529312	0.049*
C2	0.9316 (2)	0.0661 (3)	0.6643 (2)	0.0446 (6)
H2	0.953980	−0.035050	0.639981	0.054*
C4	0.8518 (2)	0.2078 (4)	0.7781 (2)	0.0474 (6)
H4	0.819333	0.201834	0.829604	0.057*
C3	0.8845 (2)	0.0572 (4)	0.7417 (2)	0.0510 (6)
H3	0.874888	−0.049782	0.769179	0.061*
H2A	0.8674 (14)	0.596 (3)	0.585 (2)	0.049 (8)*
H2B	0.9775 (17)	0.607 (3)	0.6689 (15)	0.038 (7)*
H1A	0.946 (2)	0.188 (4)	0.4786 (15)	0.062 (9)*
H1B	1.0556 (14)	0.182 (3)	0.561 (2)	0.052 (8)*
H1WA	0.822 (3)	0.447 (5)	0.3199 (11)	0.072 (11)*
H1WB	0.787 (2)	0.546 (4)	0.386 (3)	0.085 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0287 (3)	0.0260 (3)	0.0306 (3)	0.00340 (18)	0.0155 (2)	0.00141 (19)
S1	0.0365 (3)	0.0456 (3)	0.0367 (3)	0.0168 (2)	0.0198 (2)	0.0050 (2)
O1W	0.0343 (9)	0.0495 (10)	0.0395 (9)	0.0062 (7)	0.0133 (7)	−0.0073 (8)
O1	0.0481 (10)	0.0549 (11)	0.0464 (10)	0.0299 (8)	0.0208 (8)	0.0131 (8)
N1	0.0353 (10)	0.0280 (9)	0.0418 (11)	0.0046 (8)	0.0212 (9)	0.0015 (8)
O3	0.0633 (12)	0.0736 (14)	0.0348 (9)	0.0262 (10)	0.0175 (9)	−0.0035 (9)
N2	0.0291 (9)	0.0302 (9)	0.0316 (9)	0.0041 (7)	0.0131 (8)	−0.0002 (7)
O2	0.0550 (12)	0.0644 (13)	0.0938 (17)	0.0090 (10)	0.0538 (12)	0.0030 (11)
C11	0.0259 (9)	0.0302 (10)	0.0258 (9)	0.0070 (8)	0.0085 (8)	0.0004 (8)
C6	0.0246 (10)	0.0356 (11)	0.0280 (10)	0.0001 (8)	0.0088 (8)	0.0024 (8)
C1	0.0294 (10)	0.0331 (11)	0.0347 (11)	0.0014 (8)	0.0135 (9)	0.0040 (9)
C7	0.0279 (10)	0.0368 (11)	0.0300 (10)	0.0089 (8)	0.0117 (9)	0.0014 (8)
C10	0.0348 (11)	0.0331 (11)	0.0374 (11)	0.0067 (9)	0.0137 (9)	−0.0044 (9)
C5	0.0349 (11)	0.0492 (14)	0.0331 (11)	−0.0016 (10)	0.0158 (9)	−0.0019 (10)
C8	0.0286 (11)	0.0411 (12)	0.0475 (13)	0.0015 (9)	0.0160 (10)	0.0034 (10)
C9	0.0386 (12)	0.0301 (11)	0.0516 (14)	−0.0005 (9)	0.0153 (11)	−0.0049 (10)
C2	0.0493 (14)	0.0354 (12)	0.0517 (15)	0.0012 (11)	0.0217 (12)	0.0085 (11)
C4	0.0461 (14)	0.0645 (17)	0.0366 (12)	−0.0081 (12)	0.0209 (11)	0.0059 (12)
C3	0.0573 (16)	0.0501 (15)	0.0487 (15)	−0.0050 (13)	0.0231 (13)	0.0153 (12)

Geometric parameters (Å, º)

Ni1—O1W^i	2.1381 (17)	C11—C7^ii	1.434 (3)
Ni1—O1W	2.1381 (17)	C11—C10	1.413 (3)
Ni1—N1	2.0924 (18)	C6—C1	1.385 (3)
Ni1—N1^i	2.0924 (18)	C6—C5	1.393 (3)
Ni1—N2^i	2.0776 (17)	C1—C2	1.386 (3)
Ni1—N2	2.0775 (17)	C7—C8	1.365 (3)
S1—O1	1.4558 (18)	C10—H10	0.9300
S1—O3	1.4419 (19)	C10—C9	1.363 (3)
S1—O2	1.448 (2)	C5—H5	0.9300
S1—C7	1.777 (2)	C5—C4	1.382 (4)
O1W—H1WA	0.846 (10)	C8—H8	0.9300
O1W—H1WB	0.850 (10)	C8—C9	1.403 (3)
N1—C1	1.456 (3)	C9—H9	0.9300
N1—H1A	0.886 (10)	C2—H2	0.9300
N1—H1B	0.889 (10)	C2—C3	1.383 (4)
N2—C6	1.447 (3)	C4—H4	0.9300
N2—H2A	0.882 (10)	C4—C3	1.383 (4)
N2—H2B	0.891 (10)	C3—H3	0.9300
C11—C11^ii	1.427 (4)
O1W—Ni1—O1W^i	180.0	H2A—N2—H2B	109 (3)
N1^i—Ni1—O1W^i	86.20 (8)	C11^ii—C11—C7^ii	117.6 (2)
N1^i—Ni1—O1W	93.80 (8)	C10—C11—C11^ii	119.1 (2)
N1—Ni1—O1W^i	93.80 (8)	C10—C11—C7^ii	123.28 (19)
N1—Ni1—O1W	86.20 (8)	C1—C6—N2	118.72 (18)
N1—Ni1—N1^i	180.0	C1—C6—C5	119.5 (2)
N2^i—Ni1—O1W	90.88 (7)	C5—C6—N2	121.8 (2)
N2^i—Ni1—O1W^i	89.12 (7)	C6—C1—N1	118.23 (19)
N2—Ni1—O1W	89.12 (7)	C6—C1—C2	120.1 (2)
N2—Ni1—O1W^i	90.88 (7)	C2—C1—N1	121.6 (2)
N2^i—Ni1—N1^i	83.26 (7)	C11^ii—C7—S1	120.95 (16)
N2—Ni1—N1^i	96.74 (7)	C8—C7—S1	117.60 (17)
N2—Ni1—N1	83.26 (7)	C8—C7—C11^ii	121.45 (19)
N2^i—Ni1—N1	96.74 (7)	C11—C10—H10	119.4
N2—Ni1—N2^i	180.00 (10)	C9—C10—C11	121.2 (2)
O1—S1—C7	106.30 (10)	C9—C10—H10	119.4
O3—S1—O1	110.91 (13)	C6—C5—H5	119.9
O3—S1—O2	112.29 (13)	C4—C5—C6	120.1 (2)
O3—S1—C7	107.13 (10)	C4—C5—H5	119.9
O2—S1—O1	112.67 (12)	C7—C8—H8	120.0
O2—S1—C7	107.12 (11)	C7—C8—C9	120.0 (2)
Ni1—O1W—H1WA	121 (2)	C9—C8—H8	120.0
Ni1—O1W—H1WB	115 (3)	C10—C9—C8	120.7 (2)
H1WA—O1W—H1WB	107 (3)	C10—C9—H9	119.7
Ni1—N1—H1A	106 (2)	C8—C9—H9	119.7
Ni1—N1—H1B	115 (2)	C1—C2—H2	119.9
C1—N1—Ni1	109.60 (13)	C3—C2—C1	120.2 (2)
C1—N1—H1A	112 (2)	C3—C2—H2	119.9
C1—N1—H1B	106.1 (19)	C5—C4—H4	119.9
H1A—N1—H1B	108 (3)	C5—C4—C3	120.2 (2)
Ni1—N2—H2A	107.0 (18)	C3—C4—H4	119.9
Ni1—N2—H2B	110.6 (16)	C2—C3—H3	120.1
C6—N2—Ni1	110.14 (13)	C4—C3—C2	119.8 (2)
C6—N2—H2A	110.8 (19)	C4—C3—H3	120.1
C6—N2—H2B	109.3 (17)
Ni1—N1—C1—C6	2.3 (2)	O2—S1—C7—C8	5.8 (2)
Ni1—N1—C1—C2	−179.29 (18)	C11^ii—C11—C10—C9	1.3 (4)
Ni1—N2—C6—C1	1.6 (2)	C11^ii—C7—C8—C9	1.7 (3)
Ni1—N2—C6—C5	−178.80 (17)	C11—C10—C9—C8	−1.1 (4)
S1—C7—C8—C9	−177.84 (18)	C6—C1—C2—C3	1.0 (4)
O1—S1—C7—C11^ii	−53.0 (2)	C6—C5—C4—C3	1.0 (4)
O1—S1—C7—C8	126.48 (19)	C1—C6—C5—C4	−0.3 (3)
N1—C1—C2—C3	−177.3 (2)	C1—C2—C3—C4	−0.3 (4)
O3—S1—C7—C11^ii	65.6 (2)	C7^ii—C11—C10—C9	−178.7 (2)
O3—S1—C7—C8	−114.9 (2)	C7—C8—C9—C10	−0.4 (4)
N2—C6—C1—N1	−2.7 (3)	C5—C6—C1—N1	177.67 (19)
N2—C6—C1—C2	178.9 (2)	C5—C6—C1—C2	−0.8 (3)
N2—C6—C5—C4	−179.9 (2)	C5—C4—C3—C2	−0.7 (4)
O2—S1—C7—C11^ii	−173.73 (18)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2^iii	0.89 (1)	2.48 (2)	3.268 (3)	148 (3)
N1—H1B···O2^i	0.89 (1)	2.18 (1)	3.066 (3)	175 (3)
N2—H2A···O1	0.88 (1)	2.10 (1)	2.941 (2)	160 (3)
N2—H2B···O3^iv	0.89 (1)	2.06 (1)	2.908 (3)	158 (2)
O1W—H1WA···O3^v	0.85 (1)	2.12 (2)	2.876 (3)	148 (3)
O1W—H1WB···O1	0.85 (1)	2.04 (2)	2.803 (2)	150 (3)

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