[Bis­(triazol-1-yl)acetato]nickel(II) monohydrate

The title complex, [Ni(C₆H₃N₆O₂)₂]·H₂O, contains an Ni^II ion on a twofold axis bound to two tridentate chelating bis­(triazol-1-yl)acetate anions and one uncoordinated water mol­ecule. In the complex, weak inter­molecular C—H...O hydrogen bonds inter­connect units to form a three-dimensional net with one-dimensional channels along the c-axis direction occupied by disordered water mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.008 Å
• H-atom completeness 84%
• Disorder in solvent or counterion
• R factor = 0.050
• wR factor = 0.160
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.00 Ratio
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         N6

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.89
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT076_ALERT_1_C Occupancy       0.50 less than 1.0 for Sp.pos  .         O3
PLAT076_ALERT_1_C Occupancy       0.50 less than 1.0 for Sp.pos  .        O3'
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    N     Ueq(max)/Ueq(min) ...       2.78 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         N3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Ni1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C5
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5     ..  O1      ..       2.65 Ang.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      38.00 A   3 
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          4
            N4  -NI1 -O1  -C4   -135.60  1.20   5.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          6
            N1  -NI1 -N1  -C1    -84.50  0.50   5.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         11
            N1  -NI1 -N1  -N2     83.70  0.40   5.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         23
            O1  -NI1 -N4  -C6    139.00  1.20   5.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         28
            O1  -NI1 -N4  -N5    -51.00  1.50   5.555   1.555   1.555   1.555
PLAT747_ALERT_1_C D...A   Calc    3.288(8), Rep     3.29000 ......    Missing su
              C1   -O2      1.555   6.655
PLAT747_ALERT_1_C D...A   Calc    3.231(7), Rep     3.23000 ......    Missing su
              C2   -O2      1.555   3.665
PLAT747_ALERT_1_C D...A   Calc    3.353(7), Rep     3.35000 ......    Missing su
              C3   -O1      1.555   3.665
PLAT747_ALERT_1_C D...A   Calc    3.307(9), Rep     3.31000 ......    Missing su
              C5   -O1      1.555   3.665
PLAT747_ALERT_1_C D...A   Calc    3.480(9), Rep     3.48000 ......    Missing su
              C5   -O1      1.555   6.665

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C12 H12 N12 Ni1 O5
            Atom count from the _atom_site data:  C12 H10 N12 Ni1 O5
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.893
            Tmax scaled      0.893 Tmin scaled      0.768
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    3
           From the CIF: _chemical_formula_sum  C12 H12 N12 Ni O5
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         36.00     36.00    0.00
           H         36.00     30.00    6.00
           N         36.00     36.00    0.00
           Ni         3.00      3.00    0.00
           O         15.00     15.00    0.00
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.02
           From the CIF: _reflns_number_total               1928
           Count of symmetry unique reflns         1107
           Completeness (_total/calc)            174.16%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       821
           Fraction of Friedel pairs measured     0.742
           Are heavy atom types Z>Si present        yes
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
  26 ALERT level C = Check and explain
   7 ALERT level G = General alerts; check

  14 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 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
  10 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 2005); cell refinement: SMART; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2005); software used to prepare material for publication: SHELXTL.

bis[bis(triazol-1-yl)acetato]nickel(II) monohydrate

Crystal data

[Ni(C6H3N6O2)2]·H2O	Dx = 1.417 Mg m^−3
Mr = 463.05	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P3221	Cell parameters from 3213 reflections
a = 12.406 (3) Å	θ = 2.5–24.3°
c = 12.211 (7) Å	µ = 0.94 mm^−1
V = 1627.5 (11) Å^3	T = 293 K
Z = 3	Block, green
F(000) = 708	0.20 × 0.14 × 0.12 mm

Data collection

Bruker APEX-II CCD area-detector diffractometer	1928 independent reflections
Radiation source: fine-focus sealed tube	1792 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.860, Tmax = 1.000	k = −14→9
8800 measured reflections	l = −14→14

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.160	w = 1/[σ^2(Fo^2) + (0.1281P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
1928 reflections	Δρmax = 1.05 e Å^−3
147 parameters	Δρmin = −0.52 e Å^−3
12 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (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	Occ. (<1)
Ni1	0.38247 (6)	0.0000	0.1667	0.0309 (3)
O1	0.5732 (4)	0.1363 (4)	0.1964 (3)	0.0553 (11)
O2	0.7078 (3)	0.2987 (4)	0.2972 (4)	0.0575 (10)
N1	0.3692 (4)	−0.0298 (3)	0.3278 (3)	0.0410 (10)
N2	0.4299 (4)	0.0693 (3)	0.3962 (3)	0.0404 (9)
N3	0.3599 (6)	−0.0960 (5)	0.4990 (5)	0.0726 (16)
N4	0.3531 (5)	0.1565 (5)	0.2000 (4)	0.0595 (13)
N5	0.4092 (4)	0.2206 (4)	0.2930 (3)	0.0443 (10)
N6	0.2965 (7)	0.2988 (8)	0.2347 (7)	0.112 (3)
C1	0.3274 (5)	−0.1291 (5)	0.3911 (4)	0.0464 (12)
H1	0.2821	−0.2107	0.3662	0.037 (13)*
C2	0.4278 (6)	0.0335 (5)	0.5001 (4)	0.0523 (14)
H2	0.4643	0.0847	0.5605	0.045 (14)*
C3	0.4953 (4)	0.1964 (4)	0.3509 (4)	0.0355 (10)
H3	0.5307	0.2556	0.4117	0.026 (10)*
C4	0.6040 (5)	0.2130 (4)	0.2747 (4)	0.0393 (11)
C5	0.3780 (6)	0.3072 (6)	0.3151 (6)	0.0602 (15)
H5	0.4060	0.3624	0.3738	0.12 (3)*
C6	0.2866 (8)	0.2028 (8)	0.1654 (7)	0.082 (2)
H6	0.2380	0.1763	0.1024	0.13 (3)*
O3	0.0000	0.086 (3)	0.3333	0.186 (10)	0.50
O3'	0.0000	−0.022 (2)	0.3333	0.162 (9)	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0364 (4)	0.0301 (4)	0.0241 (4)	0.0151 (2)	−0.00220 (16)	−0.0044 (3)
O1	0.071 (3)	0.048 (2)	0.040 (2)	0.0235 (19)	0.0151 (18)	−0.0096 (16)
O2	0.038 (2)	0.061 (2)	0.066 (3)	0.0190 (19)	0.0044 (17)	−0.0105 (19)
N1	0.044 (2)	0.0336 (19)	0.036 (2)	0.0125 (18)	0.0025 (16)	−0.0034 (15)
N2	0.045 (2)	0.0354 (19)	0.031 (2)	0.0130 (18)	0.0057 (17)	−0.0019 (16)
N3	0.079 (4)	0.059 (3)	0.062 (3)	0.021 (3)	0.006 (3)	0.013 (3)
N4	0.059 (3)	0.064 (3)	0.044 (2)	0.022 (2)	−0.018 (2)	−0.012 (2)
N5	0.048 (2)	0.038 (2)	0.042 (2)	0.0173 (19)	−0.0028 (19)	−0.0058 (17)
N6	0.089 (5)	0.106 (6)	0.136 (7)	0.045 (5)	−0.025 (5)	0.019 (6)
C1	0.049 (3)	0.038 (3)	0.043 (3)	0.016 (2)	0.006 (2)	0.002 (2)
C2	0.061 (3)	0.055 (3)	0.028 (3)	0.019 (3)	0.001 (2)	−0.001 (2)
C3	0.039 (2)	0.032 (2)	0.030 (2)	0.014 (2)	−0.0021 (19)	−0.0043 (18)
C4	0.047 (3)	0.035 (2)	0.036 (2)	0.021 (2)	0.005 (2)	0.0042 (19)
C5	0.053 (3)	0.048 (3)	0.082 (4)	0.027 (3)	−0.014 (3)	−0.012 (3)
C6	0.076 (5)	0.083 (5)	0.079 (5)	0.033 (4)	−0.035 (4)	−0.003 (4)
O3	0.164 (12)	0.192 (13)	0.194 (13)	0.082 (6)	0.054 (9)	0.027 (4)
O3'	0.172 (11)	0.154 (11)	0.165 (12)	0.086 (6)	0.021 (8)	0.010 (4)

Geometric parameters (Å, º)

Ni1—N1	1.993 (4)	N3—C2	1.392 (8)
Ni1—N1^i	1.993 (4)	N4—C6	1.289 (9)
Ni1—O1	2.142 (5)	N4—N5	1.362 (6)
Ni1—O1^i	2.142 (4)	N5—C5	1.338 (8)
Ni1—N4^i	2.185 (6)	N5—C3	1.433 (7)
Ni1—N4	2.185 (6)	N6—C5	1.376 (9)
O1—C4	1.266 (6)	N6—C6	1.416 (12)
O2—C4	1.223 (6)	C1—H1	0.9300
N1—C1	1.322 (6)	C2—H2	0.9300
N1—N2	1.361 (6)	C3—C4	1.565 (7)
N2—C2	1.340 (6)	C3—H3	0.9800
N2—C3	1.474 (6)	C5—H5	0.9300
N3—C1	1.379 (8)	C6—H6	0.9300
N1—Ni1—N1^i	178.9 (3)	C5—N5—N4	111.7 (5)
N1—Ni1—O1	86.31 (15)	C5—N5—C3	127.8 (4)
N1^i—Ni1—O1	92.89 (15)	N4—N5—C3	120.4 (4)
N1—Ni1—O1^i	92.89 (15)	C5—N6—C6	104.0 (8)
N1^i—Ni1—O1^i	86.31 (15)	N1—C1—N3	111.2 (4)
O1—Ni1—O1^i	89.5 (2)	N1—C1—H1	124.4
N1—Ni1—N4^i	93.79 (18)	N3—C1—H1	124.4
N1^i—Ni1—N4^i	86.90 (18)	N2—C2—N3	105.9 (5)
O1—Ni1—N4^i	172.44 (18)	N2—C2—H2	127.1
O1^i—Ni1—N4^i	82.90 (17)	N3—C2—H2	127.1
N1—Ni1—N4	86.90 (18)	N5—C3—N2	109.9 (4)
N1^i—Ni1—N4	93.79 (18)	N5—C3—C4	111.3 (4)
O1—Ni1—N4	82.90 (17)	N2—C3—C4	109.9 (4)
O1^i—Ni1—N4	172.44 (18)	N5—C3—H3	108.6
N4^i—Ni1—N4	104.7 (3)	N2—C3—H3	108.6
C4—O1—Ni1	121.4 (3)	C4—C3—H3	108.6
C1—N1—N2	105.3 (4)	O2—C4—O1	127.9 (5)
C1—N1—Ni1	135.1 (3)	O2—C4—C3	116.3 (4)
N2—N1—Ni1	118.8 (3)	O1—C4—C3	115.7 (4)
C2—N2—N1	111.8 (4)	N5—C5—N6	106.9 (7)
C2—N2—C3	128.2 (4)	N5—C5—H5	126.5
N1—N2—C3	119.7 (4)	N6—C5—H5	126.5
C1—N3—C2	105.7 (5)	N4—C6—N6	111.9 (6)
C6—N4—N5	105.5 (6)	N4—C6—H6	124.0
C6—N4—Ni1	139.7 (5)	N6—C6—H6	124.0
N5—N4—Ni1	114.3 (3)
N1—Ni1—O1—C4	−44.6 (4)	Ni1—N4—N5—C5	−173.7 (4)
N1^i—Ni1—O1—C4	136.2 (4)	C6—N4—N5—C3	−177.2 (6)
O1^i—Ni1—O1—C4	−137.5 (5)	Ni1—N4—N5—C3	9.5 (6)
N4^i—Ni1—O1—C4	−135.6 (12)	N2—N1—C1—N3	0.1 (6)
N4—Ni1—O1—C4	42.8 (4)	Ni1—N1—C1—N3	169.4 (4)
N1^i—Ni1—N1—C1	−84.5 (5)	C2—N3—C1—N1	−0.8 (7)
O1—Ni1—N1—C1	−129.2 (5)	N1—N2—C2—N3	−1.2 (7)
O1^i—Ni1—N1—C1	−39.9 (6)	C3—N2—C2—N3	−176.2 (5)
N4^i—Ni1—N1—C1	43.2 (6)	C1—N3—C2—N2	1.2 (7)
N4—Ni1—N1—C1	147.7 (5)	C5—N5—C3—N2	118.0 (6)
N1^i—Ni1—N1—N2	83.7 (4)	N4—N5—C3—N2	−65.9 (6)
O1—Ni1—N1—N2	39.0 (4)	C5—N5—C3—C4	−120.0 (6)
O1^i—Ni1—N1—N2	128.3 (4)	N4—N5—C3—C4	56.1 (6)
N4^i—Ni1—N1—N2	−148.6 (4)	C2—N2—C3—N5	−125.9 (5)
N4—Ni1—N1—N2	−44.1 (4)	N1—N2—C3—N5	59.4 (5)
C1—N1—N2—C2	0.7 (6)	C2—N2—C3—C4	111.2 (6)
Ni1—N1—N2—C2	−170.7 (4)	N1—N2—C3—C4	−63.5 (5)
C1—N1—N2—C3	176.2 (4)	Ni1—O1—C4—O2	−176.0 (4)
Ni1—N1—N2—C3	4.9 (6)	Ni1—O1—C4—C3	3.2 (6)
N1—Ni1—N4—C6	−132.4 (9)	N5—C3—C4—O2	114.0 (5)
N1^i—Ni1—N4—C6	48.5 (9)	N2—C3—C4—O2	−124.1 (5)
O1—Ni1—N4—C6	140.9 (9)	N5—C3—C4—O1	−65.4 (5)
O1^i—Ni1—N4—C6	139.0 (12)	N2—C3—C4—O1	56.6 (6)
N4^i—Ni1—N4—C6	−39.3 (8)	N4—N5—C5—N6	0.9 (7)
N1—Ni1—N4—N5	37.5 (4)	C3—N5—C5—N6	177.4 (5)
N1^i—Ni1—N4—N5	−141.6 (4)	C6—N6—C5—N5	−1.0 (8)
O1—Ni1—N4—N5	−49.1 (4)	N5—N4—C6—N6	−0.2 (9)
O1^i—Ni1—N4—N5	−51.0 (15)	Ni1—N4—C6—N6	170.3 (6)
N4^i—Ni1—N4—N5	130.6 (5)	C5—N6—C6—N4	0.7 (9)
C6—N4—N5—C5	−0.5 (8)

Symmetry code: (i) x−y, −y, −z+1/3.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2^ii	0.93	2.53	3.29	139
C2—H2···O2^iii	0.93	2.41	3.23	148
C3—H3···O1^iii	0.98	2.43	3.35	157
C5—H5···O1^iii	0.93	2.55	3.31	139
C5—H5···O1^iv	0.93	2.65	3.48	148

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