(DL-Methio­ninato-κ²N,O)(2,2′,2′′-triamino­triethyl­amine-κ⁴N,N′,N′′,N′′′)nickel(II) perchlorate dihydrate

In the title compound, [Ni(C₅H₁₀NO₂S)(C₆H₁₈N₄)]ClO₄·2H₂O, the Ni^II atom is in a slightly distorted octa­hedral coordination environment. Inter­molecular hydrogen bonds link the cationic complexes into an extended two-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.068
• wR factor = 0.190
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT360_ALERT_2_B Short  C(sp3)-C(sp3) Bond  C8     -   C9     ...       1.33 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D       H2E    ..  H5D     ..       1.42 Ang.

Alert level C
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      2.419
            Test value =      2.100
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.39
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       2.42 e/A   
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C8
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl1
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker 1997); cell refinement: SAINT (Bruker, 1997; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

(dL-Methioninato-κ²N,O)(2,2',2''-triaminotriethylamine- κ⁴N,N',N'',N''')nickel(II) perchlorate dihydrate

Crystal data

[Ni(C5H10NO2S)(C6H18N4)]ClO4·2H2O	F(000) = 2064
Mr = 488.64	Dx = 1.553 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9526 reflections
a = 11.2597 (13) Å	θ = 1.8–26.1°
b = 18.703 (2) Å	µ = 1.20 mm^−1
c = 19.849 (2) Å	T = 293 K
V = 4180.1 (8) Å^3	Block, purple
Z = 8	0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3670 independent reflections
Radiation source: fine-focus sealed tube	3199 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→12
Tmin = 0.810, Tmax = 0.879	k = −21→22
21117 measured reflections	l = −23→23

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.190	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0889P)^2 + 16.6077P] where P = (Fo^2 + 2Fc^2)/3
3670 reflections	(Δ/σ)max = 0.010
244 parameters	Δρmax = 2.42 e Å^−3
7 restraints	Δρmin = −1.01 e Å^−3

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ni1	0.78024 (5)	0.49718 (3)	0.66268 (3)	0.0351 (3)
Cl1	0.75902 (14)	0.60682 (9)	0.41225 (8)	0.0589 (4)
S1	1.03070 (19)	0.68906 (10)	0.85873 (12)	0.0785 (6)
O1	0.6450 (3)	0.51068 (18)	0.73569 (19)	0.0412 (8)
O2	0.5817 (3)	0.5851 (2)	0.8150 (2)	0.0571 (11)
O3	0.7966 (12)	0.6001 (5)	0.4767 (4)	0.186 (5)
O4	0.8602 (7)	0.6163 (5)	0.3729 (5)	0.150 (3)
O5	0.7033 (6)	0.5410 (4)	0.3936 (4)	0.114 (2)
O6	0.6872 (8)	0.6638 (5)	0.4035 (7)	0.203 (6)
O1W	0.9385 (9)	0.1981 (5)	0.9027 (5)	0.176 (5)
H1E	0.9059	0.2436	0.8931	0.264*
H1F	0.9379	0.1666	0.8694	0.264*
O2W	0.8244 (7)	0.7064 (4)	0.5788 (3)	0.120 (2)
H2E	0.8237	0.6783	0.6106	0.180*
H2F	0.8233	0.6880	0.5412	0.180*
N1	0.6425 (4)	0.5209 (3)	0.5912 (2)	0.0476 (11)
H1C	0.5848	0.5466	0.6113	0.057*
H1D	0.6724	0.5472	0.5572	0.057*
N2	0.8856 (4)	0.4461 (2)	0.7376 (2)	0.0440 (10)
H2C	0.9609	0.4620	0.7354	0.053*
H2D	0.8567	0.4558	0.7788	0.053*
N3	0.9124 (4)	0.4899 (3)	0.5880 (2)	0.0515 (12)
H3C	0.9203	0.5322	0.5669	0.062*
H3D	0.9825	0.4785	0.6069	0.062*
N4	0.7428 (4)	0.3924 (2)	0.6328 (2)	0.0363 (9)
N5	0.8171 (4)	0.5997 (2)	0.6941 (3)	0.0484 (11)
H5C	0.8962	0.6054	0.6975	0.058*
H5D	0.7899	0.6310	0.6633	0.058*
C1	0.5921 (5)	0.4536 (3)	0.5642 (3)	0.0510 (14)
H1A	0.6280	0.4428	0.5209	0.061*
H1B	0.5072	0.4590	0.5576	0.061*
C2	0.6158 (5)	0.3933 (3)	0.6129 (3)	0.0460 (13)
H2A	0.5667	0.3993	0.6527	0.055*
H2B	0.5951	0.3481	0.5921	0.055*
C3	0.8824 (5)	0.3676 (3)	0.7250 (3)	0.0515 (14)
H3A	0.8924	0.3420	0.7672	0.062*
H3B	0.9468	0.3541	0.6951	0.062*
C4	0.7641 (5)	0.3478 (3)	0.6933 (3)	0.0452 (12)
H4A	0.7646	0.2977	0.6808	0.054*
H4B	0.7007	0.3552	0.7256	0.054*
C5	0.8775 (6)	0.4350 (4)	0.5400 (3)	0.0582 (16)
H5A	0.9465	0.4193	0.5148	0.070*
H5B	0.8205	0.4547	0.5083	0.070*
C6	0.8223 (5)	0.3712 (3)	0.5764 (3)	0.0489 (13)
H6A	0.7773	0.3431	0.5443	0.059*
H6B	0.8854	0.3412	0.5940	0.059*
C7	0.6539 (4)	0.5661 (3)	0.7713 (3)	0.0431 (12)
C8	0.7617 (6)	0.6146 (4)	0.7595 (4)	0.074 (2)
H8A	0.7257	0.6618	0.7528	0.089*
C9	0.8368 (8)	0.6256 (5)	0.8101 (4)	0.084 (2)
H9A	0.8931	0.5864	0.8119	0.101*
H9B	0.7929	0.6260	0.8522	0.101*
C10	0.9089 (6)	0.7004 (5)	0.8026 (4)	0.077 (2)
H10A	0.8600	0.7407	0.8158	0.093*
H10B	0.9361	0.7075	0.7567	0.093*
C11	0.9662 (8)	0.7045 (5)	0.9383 (4)	0.088 (2)
H11A	1.0256	0.6995	0.9727	0.133*
H11B	0.9039	0.6703	0.9459	0.133*
H11C	0.9338	0.7519	0.9397	0.133*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0275 (4)	0.0325 (4)	0.0454 (4)	−0.0025 (2)	0.0027 (3)	0.0001 (2)
Cl1	0.0495 (8)	0.0694 (10)	0.0580 (9)	0.0002 (7)	0.0018 (7)	0.0094 (7)
S1	0.0688 (12)	0.0580 (10)	0.1087 (15)	0.0142 (9)	0.0242 (11)	0.0153 (10)
O1	0.0299 (18)	0.0400 (19)	0.054 (2)	−0.0093 (14)	0.0057 (16)	−0.0058 (16)
O2	0.035 (2)	0.064 (3)	0.072 (3)	−0.0074 (19)	0.014 (2)	−0.019 (2)
O3	0.302 (15)	0.163 (8)	0.092 (5)	−0.066 (9)	−0.060 (7)	0.040 (5)
O4	0.111 (6)	0.130 (6)	0.208 (9)	−0.016 (5)	0.077 (6)	0.004 (6)
O5	0.097 (5)	0.099 (5)	0.146 (6)	−0.032 (4)	0.006 (4)	−0.021 (4)
O6	0.123 (7)	0.116 (7)	0.370 (17)	0.052 (6)	−0.025 (9)	0.030 (8)
O1W	0.180 (9)	0.142 (7)	0.206 (10)	0.056 (6)	−0.088 (8)	−0.090 (7)
O2W	0.156 (7)	0.109 (5)	0.094 (5)	0.001 (5)	0.007 (5)	−0.001 (4)
N1	0.045 (3)	0.044 (2)	0.054 (3)	0.008 (2)	−0.003 (2)	0.005 (2)
N2	0.033 (2)	0.045 (2)	0.054 (3)	−0.0025 (19)	−0.006 (2)	−0.001 (2)
N3	0.044 (3)	0.051 (3)	0.059 (3)	−0.006 (2)	0.015 (2)	0.003 (2)
N4	0.035 (2)	0.034 (2)	0.041 (2)	−0.0008 (17)	0.0023 (18)	0.0011 (17)
N5	0.037 (2)	0.041 (2)	0.067 (3)	−0.0112 (19)	0.010 (2)	−0.007 (2)
C1	0.041 (3)	0.057 (3)	0.054 (3)	0.001 (3)	−0.012 (3)	0.001 (3)
C2	0.034 (3)	0.047 (3)	0.057 (3)	−0.008 (2)	−0.001 (2)	−0.004 (3)
C3	0.052 (3)	0.046 (3)	0.057 (3)	0.009 (3)	−0.009 (3)	0.006 (3)
C4	0.049 (3)	0.035 (3)	0.052 (3)	0.000 (2)	−0.001 (3)	0.005 (2)
C5	0.055 (4)	0.064 (4)	0.056 (3)	−0.002 (3)	0.024 (3)	0.001 (3)
C6	0.049 (3)	0.044 (3)	0.054 (3)	0.006 (2)	0.008 (3)	−0.008 (2)
C7	0.029 (2)	0.046 (3)	0.054 (3)	−0.006 (2)	0.004 (2)	−0.002 (2)
C8	0.060 (4)	0.072 (4)	0.091 (5)	−0.039 (4)	0.032 (4)	−0.041 (4)
C9	0.082 (6)	0.090 (6)	0.080 (5)	−0.029 (5)	0.003 (4)	−0.003 (4)
C10	0.060 (4)	0.102 (6)	0.070 (4)	−0.039 (4)	0.014 (4)	−0.036 (4)
C11	0.090 (6)	0.094 (6)	0.081 (5)	−0.006 (5)	0.004 (5)	0.012 (5)

Geometric parameters (Å, º)

Ni1—N5	2.058 (4)	N5—C8	1.467 (8)
Ni1—N4	2.090 (4)	N5—H5C	0.9000
Ni1—N3	2.104 (5)	N5—H5D	0.9000
Ni1—O1	2.117 (4)	C1—C2	1.510 (8)
Ni1—N2	2.129 (4)	C1—H1A	0.9700
Ni1—N1	2.149 (5)	C1—H1B	0.9700
Cl1—O6	1.350 (7)	C2—H2A	0.9700
Cl1—O3	1.354 (8)	C2—H2B	0.9700
Cl1—O4	1.392 (7)	C3—C4	1.519 (8)
Cl1—O5	1.431 (7)	C3—H3A	0.9700
S1—C11	1.763 (9)	C3—H3B	0.9700
S1—C10	1.780 (8)	C4—H4A	0.9700
O1—C7	1.258 (6)	C4—H4B	0.9700
O2—C7	1.240 (6)	C5—C6	1.527 (8)
O1W—H1E	0.9465	C5—H5A	0.9700
O1W—H1F	0.8863	C5—H5B	0.9700
O2W—H2E	0.8223	C6—H6A	0.9700
O2W—H2F	0.8223	C6—H6B	0.9700
N1—C1	1.481 (8)	C7—C8	1.534 (8)
N1—H1C	0.9000	C8—C9	1.328 (11)
N1—H1D	0.9000	C8—H8A	0.9800
N2—C3	1.489 (7)	C9—C10	1.624 (10)
N2—H2C	0.9000	C9—H9A	0.9700
N2—H2D	0.9000	C9—H9B	0.9700
N3—C5	1.456 (8)	C10—H10A	0.9700
N3—H3C	0.9000	C10—H10B	0.9700
N3—H3D	0.9000	C11—H11A	0.9600
N4—C4	1.483 (7)	C11—H11B	0.9600
N4—C2	1.483 (7)	C11—H11C	0.9600
N4—C6	1.487 (7)
N5—Ni1—N4	178.86 (18)	C2—C1—H1B	109.7
N5—Ni1—N3	97.52 (19)	H1A—C1—H1B	108.2
N4—Ni1—N3	83.24 (18)	N4—C2—C1	110.4 (4)
N5—Ni1—O1	80.00 (16)	N4—C2—H2A	109.6
N4—Ni1—O1	99.27 (15)	C1—C2—H2A	109.6
N3—Ni1—O1	176.57 (17)	N4—C2—H2B	109.6
N5—Ni1—N2	95.42 (19)	C1—C2—H2B	109.6
N4—Ni1—N2	83.67 (17)	H2A—C2—H2B	108.1
N3—Ni1—N2	94.0 (2)	N2—C3—C4	109.3 (4)
O1—Ni1—N2	88.65 (16)	N2—C3—H3A	109.8
N5—Ni1—N1	98.8 (2)	C4—C3—H3A	109.8
N4—Ni1—N1	81.99 (18)	N2—C3—H3B	109.8
N3—Ni1—N1	93.3 (2)	C4—C3—H3B	109.8
O1—Ni1—N1	84.74 (17)	H3A—C3—H3B	108.3
N2—Ni1—N1	163.02 (18)	N4—C4—C3	109.9 (4)
O6—Cl1—O3	112.5 (8)	N4—C4—H4A	109.7
O6—Cl1—O4	108.5 (7)	C3—C4—H4A	109.7
O3—Cl1—O4	106.7 (7)	N4—C4—H4B	109.7
O6—Cl1—O5	112.5 (6)	C3—C4—H4B	109.7
O3—Cl1—O5	107.6 (5)	H4A—C4—H4B	108.2
O4—Cl1—O5	108.8 (5)	N3—C5—C6	110.6 (5)
C11—S1—C10	102.9 (4)	N3—C5—H5A	109.5
C7—O1—Ni1	115.2 (3)	C6—C5—H5A	109.5
H1E—O1W—H1F	116.3	N3—C5—H5B	109.5
H2E—O2W—H2F	115.5	C6—C5—H5B	109.5
C1—N1—Ni1	109.8 (3)	H5A—C5—H5B	108.1
C1—N1—H1C	109.7	N4—C6—C5	113.1 (4)
Ni1—N1—H1C	109.7	N4—C6—H6A	109.0
C1—N1—H1D	109.7	C5—C6—H6A	109.0
Ni1—N1—H1D	109.7	N4—C6—H6B	109.0
H1C—N1—H1D	108.2	C5—C6—H6B	109.0
C3—N2—Ni1	108.2 (3)	H6A—C6—H6B	107.8
C3—N2—H2C	110.1	O2—C7—O1	125.3 (5)
Ni1—N2—H2C	110.1	O2—C7—C8	117.1 (5)
C3—N2—H2D	110.1	O1—C7—C8	117.7 (5)
Ni1—N2—H2D	110.1	C9—C8—N5	115.4 (7)
H2C—N2—H2D	108.4	C9—C8—C7	118.8 (7)
C5—N3—Ni1	108.4 (3)	N5—C8—C7	111.0 (5)
C5—N3—H3C	110.0	C9—C8—H8A	103.1
Ni1—N3—H3C	110.0	N5—C8—H8A	103.1
C5—N3—H3D	110.0	C7—C8—H8A	103.1
Ni1—N3—H3D	110.0	C8—C9—C10	112.5 (7)
H3C—N3—H3D	108.4	C8—C9—H9A	109.1
C4—N4—C2	112.2 (4)	C10—C9—H9A	109.1
C4—N4—C6	111.2 (4)	C8—C9—H9B	109.1
C2—N4—C6	112.6 (4)	C10—C9—H9B	109.1
C4—N4—Ni1	105.4 (3)	H9A—C9—H9B	107.8
C2—N4—Ni1	105.0 (3)	C9—C10—S1	103.0 (6)
C6—N4—Ni1	110.0 (3)	C9—C10—H10A	111.2
C8—N5—Ni1	111.1 (4)	S1—C10—H10A	111.2
C8—N5—H5C	109.4	C9—C10—H10B	111.2
Ni1—N5—H5C	109.4	S1—C10—H10B	111.2
C8—N5—H5D	109.4	H10A—C10—H10B	109.1
Ni1—N5—H5D	109.4	S1—C11—H11A	109.5
H5C—N5—H5D	108.0	S1—C11—H11B	109.5
N1—C1—C2	109.6 (5)	H11A—C11—H11B	109.5
N1—C1—H1A	109.7	S1—C11—H11C	109.5
C2—C1—H1A	109.7	H11A—C11—H11C	109.5
N1—C1—H1B	109.7	H11B—C11—H11C	109.5
N5—Ni1—O1—C7	−9.3 (4)	O1—Ni1—N5—C8	18.5 (5)
N4—Ni1—O1—C7	169.8 (4)	N2—Ni1—N5—C8	−69.2 (5)
N2—Ni1—O1—C7	86.4 (4)	N1—Ni1—N5—C8	101.5 (5)
N1—Ni1—O1—C7	−109.2 (4)	Ni1—N1—C1—C2	22.4 (6)
N5—Ni1—N1—C1	−175.4 (4)	C4—N4—C2—C1	164.7 (5)
N4—Ni1—N1—C1	3.7 (4)	C6—N4—C2—C1	−69.0 (6)
N3—Ni1—N1—C1	86.4 (4)	Ni1—N4—C2—C1	50.7 (5)
O1—Ni1—N1—C1	−96.4 (4)	N1—C1—C2—N4	−49.6 (6)
N2—Ni1—N1—C1	−28.9 (8)	Ni1—N2—C3—C4	−30.5 (5)
N5—Ni1—N2—C3	−176.7 (4)	C2—N4—C4—C3	−161.2 (4)
N4—Ni1—N2—C3	4.0 (4)	C6—N4—C4—C3	71.7 (6)
N3—Ni1—N2—C3	−78.7 (4)	Ni1—N4—C4—C3	−47.4 (5)
O1—Ni1—N2—C3	103.5 (4)	N2—C3—C4—N4	53.5 (6)
N1—Ni1—N2—C3	36.5 (8)	Ni1—N3—C5—C6	−39.9 (6)
N5—Ni1—N3—C5	−157.5 (4)	C4—N4—C6—C5	−135.9 (5)
N4—Ni1—N3—C5	23.4 (4)	C2—N4—C6—C5	97.2 (6)
N2—Ni1—N3—C5	106.5 (4)	Ni1—N4—C6—C5	−19.6 (6)
N1—Ni1—N3—C5	−58.2 (4)	N3—C5—C6—N4	40.3 (7)
N3—Ni1—N4—C4	118.1 (3)	Ni1—O1—C7—O2	177.2 (5)
O1—Ni1—N4—C4	−64.2 (3)	Ni1—O1—C7—C8	−2.2 (7)
N2—Ni1—N4—C4	23.4 (3)	Ni1—N5—C8—C9	114.4 (6)
N1—Ni1—N4—C4	−147.5 (3)	Ni1—N5—C8—C7	−24.4 (8)
N3—Ni1—N4—C2	−123.3 (3)	O2—C7—C8—C9	61.2 (10)
O1—Ni1—N4—C2	54.4 (3)	O1—C7—C8—C9	−119.2 (8)
N2—Ni1—N4—C2	142.0 (3)	O2—C7—C8—N5	−161.5 (6)
N1—Ni1—N4—C2	−28.9 (3)	O1—C7—C8—N5	18.0 (9)
N3—Ni1—N4—C6	−1.8 (4)	N5—C8—C9—C10	69.4 (10)
O1—Ni1—N4—C6	175.8 (3)	C7—C8—C9—C10	−155.2 (6)
N2—Ni1—N4—C6	−96.6 (4)	C8—C9—C10—S1	−162.5 (7)
N1—Ni1—N4—C6	92.5 (4)	C11—S1—C10—C9	−78.0 (6)
N3—Ni1—N5—C8	−163.9 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···S1^i	0.90	2.80	3.530 (5)	139
O1W—H1E···O6^ii	0.95	2.03	2.945 (8)	161
N2—H2D···O5^ii	0.90	2.38	3.263 (9)	169
O1W—H1F···O2^iii	0.89	1.88	2.748 (8)	166
N2—H2C···O1^iv	0.90	2.34	3.205 (5)	163
N3—H3D···O4^v	0.90	2.54	3.334 (11)	148
C1—H1B···O5^vi	0.97	2.56	3.431 (9)	149
N1—H1D···O3	0.90	2.34	3.219 (11)	165
O2W—H2E···N5	0.82	2.22	3.038 (9)	178
O2W—H2F···O3	0.82	2.11	2.857 (12)	152
N3—H3C···O3	0.90	2.60	3.289 (11)	134
N5—H5D···O2W	0.90	2.23	3.038 (9)	150

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