Bis(triethano­lamine-κ³N,O,O′)nickel(II) benzene-1,4-dicarboxyl­ate

The title compound, [Ni(C₆H₁₅NO₃)₂](C₈H₄O₄), consists of a [Ni(H₃tea)₂]²⁺ cation (H₃tea is triethano­lamine) and a benzene-1,4-dicarboxyl­ate (terephthalate) anion. The Ni^II atom lies on an inversion centre and exhibits a slightly distorted octa­hedral coordination geometry formed by two mol­ecules of H₃tea acting as N,O,O′-tridentate ligands; the anion is also centrosymmetric. All the OH groups of H₃tea are involved in an O—H...O hydrogen-bonding network with terephthalate O atoms, thus linking the mol­ecular units in chains and forming a two-dimensional infinite network.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.027
• wR factor = 0.066
• Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
            identifier.
            block
CRYSC01_ALERT_1_C No recognised colour has been given for crystal colour.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   O1      ..       5.67 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   O2      ..       5.41 su

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

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

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Computing details

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 2005); software used to prepare material for publication: SHELXL97.

Bis(triethanolamine-κ³N,O,O')nickel(II) benzene-1,4-dicarboxylate

Crystal data

[Ni(C6H15NO3)2](C8H4O4)	Z = 1
Mr = 521.20	F(000) = 276
Triclinic, P1	Dx = 1.591 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8910 (2) Å	Cell parameters from 7109 reflections
b = 8.6355 (2) Å	θ = 4.2–27.5°
c = 9.2002 (3) Å	µ = 0.95 mm^−1
α = 89.420 (1)°	T = 100 K
β = 72.741 (1)°	Pale blue, block
γ = 66.316 (1)°	0.26 × 0.22 × 0.06 mm
V = 543.99 (3) Å^3

Data collection

Nonius KappaCCD diffractometer	2463 independent reflections
Radiation source: fine-focus sealed tube	2294 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	Rint = 0.033
Detector resolution: 9 pixels mm^-1	θmax = 27.5°, θmin = 4.2°
φ scans and ω scans with κ offset	h = −10→10
Absorption correction: multi-scan (XPREP in SHELXTL; Sheldrick, 2005)	k = −11→11
Tmin = 0.790, Tmax = 0.945	l = −11→11
7109 measured reflections

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.066	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0156P)^2 + 0.3221P] where P = (Fo^2 + 2Fc^2)/3
2463 reflections	(Δ/σ)max < 0.001
152 parameters	Δρmax = 0.46 e Å^−3
0 restraints	Δρmin = −0.43 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	1.0000	0.0000	0.5000	0.00955 (9)
O1	1.23060 (14)	0.06356 (13)	0.39646 (12)	0.0127 (2)
H1O	1.3434	−0.0342	0.3595	0.019*
O3	0.57232 (16)	0.31113 (14)	0.18004 (13)	0.0191 (2)
H3O	0.5490	0.3373	0.0853	0.029*
O2	0.86055 (14)	0.22604 (13)	0.64946 (11)	0.0123 (2)
H2O	0.7533	0.2395	0.7299	0.018*
O4	0.55869 (15)	0.80116 (14)	0.28916 (12)	0.0170 (2)
O5	0.45989 (14)	0.70522 (14)	0.11922 (12)	0.0150 (2)
N1	0.87332 (17)	0.15466 (15)	0.34945 (13)	0.0108 (2)
C1	1.0432 (2)	0.14758 (19)	0.22015 (16)	0.0139 (3)
H1A	0.9977	0.2400	0.1576	0.017*
H1B	1.1012	0.0376	0.1539	0.017*
C2	1.1994 (2)	0.1658 (2)	0.27464 (17)	0.0146 (3)
H2A	1.3229	0.1289	0.1881	0.017*
H2B	1.1578	0.2868	0.3115	0.017*
C5	0.7607 (2)	0.07798 (19)	0.29418 (17)	0.0148 (3)
H5A	0.6379	0.1011	0.3783	0.018*
H5B	0.8373	−0.0471	0.2744	0.018*
C6	0.7086 (2)	0.1380 (2)	0.15125 (17)	0.0159 (3)
H6B	0.8284	0.1246	0.0677	0.019*
H6A	0.6522	0.0667	0.1174	0.019*
C3	0.7462 (2)	0.32920 (19)	0.43360 (17)	0.0139 (3)
H3A	0.6106	0.3401	0.4778	0.017*
H3B	0.7458	0.4141	0.3604	0.017*
C4	0.8147 (2)	0.36776 (19)	0.56201 (17)	0.0148 (3)
H4B	0.9318	0.3905	0.5175	0.018*
H4A	0.7108	0.4710	0.6303	0.018*
C7	0.9494 (2)	0.60460 (18)	0.13372 (17)	0.0124 (3)
H7	0.9152	0.6755	0.2255	0.015*
C8	0.8025 (2)	0.59932 (18)	0.08122 (16)	0.0118 (3)
C9	0.8544 (2)	0.49319 (19)	−0.05274 (17)	0.0126 (3)
H9	0.7557	0.4876	−0.0888	0.015*
C10	0.5910 (2)	0.71015 (18)	0.16966 (16)	0.0121 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.00725 (13)	0.00982 (14)	0.01034 (14)	−0.00249 (10)	−0.00258 (9)	0.00105 (9)
O1	0.0096 (4)	0.0129 (5)	0.0135 (5)	−0.0031 (4)	−0.0030 (4)	0.0022 (4)
O3	0.0168 (5)	0.0192 (6)	0.0168 (6)	−0.0016 (5)	−0.0076 (4)	0.0030 (4)
O2	0.0096 (5)	0.0128 (5)	0.0120 (5)	−0.0031 (4)	−0.0021 (4)	0.0014 (4)
O4	0.0106 (5)	0.0183 (5)	0.0175 (6)	−0.0027 (4)	−0.0028 (4)	−0.0037 (4)
O5	0.0095 (5)	0.0199 (6)	0.0135 (5)	−0.0041 (4)	−0.0036 (4)	0.0013 (4)
N1	0.0097 (5)	0.0111 (6)	0.0109 (6)	−0.0038 (5)	−0.0031 (4)	0.0001 (5)
C1	0.0125 (6)	0.0158 (7)	0.0112 (7)	−0.0048 (6)	−0.0026 (5)	0.0020 (5)
C2	0.0118 (6)	0.0166 (7)	0.0152 (7)	−0.0065 (6)	−0.0035 (6)	0.0052 (6)
C5	0.0156 (7)	0.0151 (7)	0.0178 (8)	−0.0075 (6)	−0.0094 (6)	0.0036 (6)
C6	0.0134 (7)	0.0169 (7)	0.0164 (7)	−0.0039 (6)	−0.0068 (6)	0.0007 (6)
C3	0.0123 (6)	0.0113 (7)	0.0146 (7)	−0.0017 (6)	−0.0042 (6)	0.0016 (6)
C4	0.0172 (7)	0.0110 (7)	0.0153 (7)	−0.0057 (6)	−0.0043 (6)	0.0013 (6)
C7	0.0125 (6)	0.0123 (7)	0.0115 (7)	−0.0047 (6)	−0.0032 (5)	0.0012 (5)
C8	0.0095 (6)	0.0107 (7)	0.0136 (7)	−0.0036 (5)	−0.0023 (5)	0.0037 (5)
C9	0.0110 (6)	0.0136 (7)	0.0146 (7)	−0.0054 (6)	−0.0055 (5)	0.0041 (5)
C10	0.0105 (6)	0.0120 (7)	0.0123 (7)	−0.0039 (6)	−0.0027 (5)	0.0045 (5)

Geometric parameters (Å, º)

Ni1—O1^i	2.0696 (10)	C2—H2A	0.9900
Ni1—O1	2.0696 (10)	C2—H2B	0.9900
Ni1—O2	2.0839 (10)	C5—C6	1.517 (2)
Ni1—O2^i	2.0840 (10)	C5—H5A	0.9900
Ni1—N1^i	2.1007 (12)	C5—H5B	0.9900
Ni1—N1	2.1008 (12)	C6—H6B	0.9900
O1—C2	1.4371 (17)	C6—H6A	0.9900
O1—H1O	0.9182	C3—C4	1.527 (2)
O3—C6	1.4177 (18)	C3—H3A	0.9900
O3—H3O	0.9500	C3—H3B	0.9900
O2—C4	1.4398 (17)	C4—H4B	0.9900
O2—H2O	0.9102	C4—H4A	0.9900
O4—C10	1.2576 (18)	C7—C9^ii	1.394 (2)
O5—C10	1.2682 (17)	C7—C8	1.398 (2)
N1—C1	1.4852 (18)	C7—H7	0.9500
N1—C3	1.4919 (18)	C8—C9	1.396 (2)
N1—C5	1.4949 (18)	C8—C10	1.5133 (19)
C1—C2	1.523 (2)	C9—C7^ii	1.394 (2)
C1—H1A	0.9900	C9—H9	0.9500
C1—H1B	0.9900
O1^i—Ni1—O1	180.0	C1—C2—H2B	109.7
O1^i—Ni1—O2	89.81 (4)	H2A—C2—H2B	108.2
O1—Ni1—O2	90.19 (4)	N1—C5—C6	117.01 (13)
O1^i—Ni1—O2^i	90.19 (4)	N1—C5—H5A	108.0
O1—Ni1—O2^i	89.81 (4)	C6—C5—H5A	108.0
O2—Ni1—O2^i	180.0	N1—C5—H5B	108.0
O1^i—Ni1—N1^i	83.35 (4)	C6—C5—H5B	108.0
O1—Ni1—N1^i	96.65 (4)	H5A—C5—H5B	107.3
O2—Ni1—N1^i	96.08 (4)	O3—C6—C5	110.87 (12)
O2^i—Ni1—N1^i	83.92 (4)	O3—C6—H6B	109.5
O1^i—Ni1—N1	96.65 (4)	C5—C6—H6B	109.5
O1—Ni1—N1	83.35 (4)	O3—C6—H6A	109.5
O2—Ni1—N1	83.92 (4)	C5—C6—H6A	109.5
O2^i—Ni1—N1	96.08 (4)	H6B—C6—H6A	108.1
N1^i—Ni1—N1	179.999 (1)	N1—C3—C4	112.19 (11)
C2—O1—Ni1	112.64 (8)	N1—C3—H3A	109.2
C2—O1—H1O	109.9	C4—C3—H3A	109.2
Ni1—O1—H1O	109.4	N1—C3—H3B	109.2
C6—O3—H3O	105.0	C4—C3—H3B	109.2
C4—O2—Ni1	108.91 (8)	H3A—C3—H3B	107.9
C4—O2—H2O	110.0	O2—C4—C3	110.37 (12)
Ni1—O2—H2O	118.0	O2—C4—H4B	109.6
C1—N1—C3	113.36 (12)	C3—C4—H4B	109.6
C1—N1—C5	110.06 (11)	O2—C4—H4A	109.6
C3—N1—C5	112.04 (11)	C3—C4—H4A	109.6
C1—N1—Ni1	104.02 (8)	H4B—C4—H4A	108.1
C3—N1—Ni1	108.07 (8)	C9^ii—C7—C8	120.63 (14)
C5—N1—Ni1	108.88 (9)	C9^ii—C7—H7	119.7
N1—C1—C2	112.44 (12)	C8—C7—H7	119.7
N1—C1—H1A	109.1	C9—C8—C7	119.21 (13)
C2—C1—H1A	109.1	C9—C8—C10	121.43 (13)
N1—C1—H1B	109.1	C7—C8—C10	119.36 (13)
C2—C1—H1B	109.1	C7^ii—C9—C8	120.15 (13)
H1A—C1—H1B	107.8	C7^ii—C9—H9	119.9
O1—C2—C1	110.01 (12)	C8—C9—H9	119.9
O1—C2—H2A	109.7	O4—C10—O5	124.73 (13)
C1—C2—H2A	109.7	O4—C10—C8	116.82 (13)
O1—C2—H2B	109.7	O5—C10—C8	118.45 (13)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O4^iii	0.92	1.66	2.5744 (14)	175
O3—H3O···O5^iv	0.95	1.95	2.8491 (15)	158
O2—H2O···O5^v	0.91	1.72	2.6272 (14)	172

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