catena-Poly[[[(3,5-dimethyl-1H-pyrazole-κN²) copper(II)]-μ-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl­amino]acetato] nitrate monohydrate]

In the title complex, {[Cu(C₈H₁₂N₃O₂)(C₅H₈N)]NO₃·H₂O}_n, the Cu atom is coordinated by two [(3,5-dimethyl-1H-pyrazol-1-yl)methyl­amino]acetate anions and one 3,5-dimethyl-1H-pyrazole ligand. There is one nitrate anion and one water mol­ecule in the asymmetric unit. The crystal packing is stabilized by N—H...O and O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.036
• wR factor = 0.098
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT731_ALERT_1_B Bond    Calc     0.84(5), Rep   0.840(10) ......       5.00 su-Rat
              O4   -H4B     1.555   1.555
PLAT731_ALERT_1_B Bond    Calc     0.84(5), Rep   0.845(10) ......       5.00 su-Rat
              O4   -H4A     1.555   1.555
PLAT735_ALERT_1_B D-H     Calc     0.84(5), Rep   0.840(10) ......       5.00 su-Rat
              O4   -H4B     1.555   1.555
PLAT735_ALERT_1_B D-H     Calc     0.84(5), Rep   0.845(10) ......       5.00 su-Rat
              O4   -H4A     1.555   1.555

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.03 Ratio
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N3
PLAT736_ALERT_1_C H...A   Calc     2.14(5), Rep     2.13(2) ......       2.50 su-Rat
              H4A  -O33     1.555   7.666

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C13 H22 Cu1 N6 O6
            Atom count from _chemical_formula_moiety:C13 H22 Cu1 N5 O6

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

   7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.

catena-Poly[[[(3,5-dimethyl-1H-pyrazole-κN²)copper(II)]-µ-[(3,5-dimethyl- 1H-pyrazol-1-yl)methylamino]acetato] nitrate monohydrate]

Crystal data

[Cu(C8H12N3O2)(C5H8N)]NO3·H2O	F(000) = 1752
Mr = 421.91	Dx = 1.583 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 18154 reflections
a = 24.440 (2) Å	θ = 1.9–25.2°
b = 6.9711 (6) Å	µ = 1.28 mm^−1
c = 23.924 (2) Å	T = 173 K
β = 119.728 (6)°	Block, blue
V = 3539.6 (6) Å^3	0.29 × 0.24 × 0.16 mm
Z = 8

Data collection

Stoe IPDS-II two-circle diffractometer	3228 independent reflections
Radiation source: fine-focus sealed tube	2695 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.067
ω scans	θmax = 25.4°, θmin = 2.0°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −29→29
Tmin = 0.708, Tmax = 0.822	k = −8→8
18327 measured reflections	l = −28→27

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ^2(Fo^2) + (0.0737P)^2] where P = (Fo^2 + 2Fc^2)/3
3228 reflections	(Δ/σ)max = 0.002
245 parameters	Δρmax = 0.73 e Å^−3
3 restraints	Δρmin = −0.55 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
Cu1	0.659219 (14)	0.47135 (4)	0.712618 (14)	0.02637 (13)
O1	0.73194 (8)	0.6460 (3)	0.74072 (9)	0.0322 (4)
C1	0.76192 (12)	0.6337 (3)	0.71052 (12)	0.0290 (5)
O2	0.80718 (9)	0.7379 (3)	0.71995 (9)	0.0344 (4)
C2	0.74264 (13)	0.4776 (4)	0.65984 (14)	0.0322 (6)
H2A	0.7358	0.5350	0.6190	0.039*
H2B	0.7771	0.3825	0.6740	0.039*
N1	0.68442 (9)	0.3795 (3)	0.64866 (10)	0.0277 (4)
H1	0.6921	0.2483	0.6542	0.033*
N11	0.63133 (10)	0.6031 (3)	0.76742 (10)	0.0298 (4)
N12	0.64844 (11)	0.5498 (3)	0.82821 (11)	0.0356 (5)
H12	0.6678	0.4417	0.8462	0.043*
C13	0.63203 (15)	0.6838 (5)	0.85773 (15)	0.0436 (7)
C14	0.60224 (15)	0.8257 (4)	0.81387 (16)	0.0441 (7)
H14	0.5847	0.9395	0.8203	0.053*
C15	0.60229 (12)	0.7730 (4)	0.75801 (14)	0.0351 (6)
C16	0.6477 (2)	0.6641 (6)	0.92630 (17)	0.0666 (11)
H16A	0.6183	0.5743	0.9290	0.100*
H16B	0.6444	0.7896	0.9428	0.100*
H16C	0.6908	0.6154	0.9521	0.100*
C17	0.57856 (17)	0.8778 (4)	0.69652 (16)	0.0503 (8)
H17A	0.6006	0.8326	0.6742	0.075*
H17B	0.5861	1.0155	0.7052	0.075*
H17C	0.5332	0.8548	0.6695	0.075*
N21	0.57296 (9)	0.3964 (3)	0.64057 (10)	0.0273 (4)
C22	0.63098 (12)	0.4138 (4)	0.58382 (12)	0.0295 (5)
H22A	0.6287	0.5510	0.5722	0.035*
H22B	0.6354	0.3364	0.5516	0.035*
N22	0.57478 (10)	0.3571 (3)	0.58605 (10)	0.0265 (4)
C23	0.51994 (12)	0.2829 (3)	0.54001 (12)	0.0269 (5)
C24	0.48095 (12)	0.2730 (3)	0.56607 (13)	0.0293 (5)
H24	0.4388	0.2273	0.5455	0.035*
C25	0.51576 (12)	0.3437 (3)	0.62891 (12)	0.0280 (5)
C26	0.50973 (13)	0.2249 (3)	0.47556 (12)	0.0319 (6)
H26A	0.5136	0.3377	0.4533	0.048*
H26B	0.4675	0.1696	0.4501	0.048*
H26C	0.5414	0.1294	0.4809	0.048*
C27	0.49705 (13)	0.3593 (4)	0.67926 (14)	0.0371 (6)
H27A	0.5282	0.2933	0.7184	0.056*
H27B	0.4556	0.2999	0.6636	0.056*
H27C	0.4950	0.4948	0.6889	0.056*
N3	0.67808 (11)	0.9400 (3)	0.56584 (12)	0.0381 (5)
O31	0.71262 (14)	1.0761 (4)	0.57190 (16)	0.0707 (8)
O32	0.64591 (15)	0.9492 (4)	0.59254 (15)	0.0689 (7)
O33	0.67594 (13)	0.7960 (3)	0.53391 (13)	0.0591 (6)
O4	0.6896 (2)	0.7831 (6)	0.42067 (18)	0.0914 (10)
H4B	0.686 (3)	0.824 (8)	0.4515 (19)	0.110*
H4A	0.7268 (12)	0.741 (8)	0.437 (3)	0.110*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.02357 (19)	0.03404 (18)	0.02255 (19)	0.00034 (11)	0.01223 (14)	−0.00438 (11)
O1	0.0308 (10)	0.0395 (9)	0.0303 (10)	−0.0071 (7)	0.0182 (8)	−0.0084 (7)
C1	0.0276 (13)	0.0327 (12)	0.0255 (12)	0.0015 (10)	0.0124 (11)	0.0003 (9)
O2	0.0346 (10)	0.0404 (9)	0.0333 (10)	−0.0093 (8)	0.0207 (9)	−0.0086 (8)
C2	0.0269 (14)	0.0420 (13)	0.0309 (14)	−0.0043 (10)	0.0168 (12)	−0.0067 (11)
N1	0.0257 (11)	0.0334 (10)	0.0249 (11)	−0.0004 (8)	0.0134 (9)	−0.0037 (8)
N11	0.0282 (11)	0.0381 (11)	0.0243 (11)	−0.0005 (9)	0.0140 (9)	−0.0035 (8)
N12	0.0362 (13)	0.0451 (12)	0.0263 (12)	−0.0039 (9)	0.0161 (10)	−0.0042 (9)
C13	0.0421 (17)	0.0612 (18)	0.0382 (16)	−0.0172 (14)	0.0280 (14)	−0.0197 (14)
C14	0.0451 (17)	0.0477 (16)	0.0500 (19)	−0.0042 (13)	0.0314 (15)	−0.0172 (13)
C15	0.0287 (14)	0.0377 (13)	0.0386 (15)	−0.0025 (10)	0.0166 (12)	−0.0096 (11)
C16	0.078 (3)	0.095 (3)	0.041 (2)	−0.017 (2)	0.040 (2)	−0.0177 (18)
C17	0.057 (2)	0.0417 (15)	0.0466 (18)	0.0078 (14)	0.0218 (16)	−0.0008 (13)
N21	0.0275 (11)	0.0328 (10)	0.0229 (10)	0.0017 (8)	0.0135 (9)	−0.0008 (8)
C22	0.0267 (13)	0.0378 (12)	0.0240 (12)	−0.0017 (10)	0.0126 (11)	−0.0007 (10)
N22	0.0260 (11)	0.0314 (10)	0.0211 (10)	−0.0007 (8)	0.0109 (9)	−0.0025 (8)
C23	0.0269 (13)	0.0233 (11)	0.0255 (13)	0.0010 (9)	0.0092 (10)	−0.0006 (9)
C24	0.0266 (13)	0.0286 (11)	0.0301 (13)	−0.0003 (9)	0.0119 (11)	0.0001 (9)
C25	0.0264 (13)	0.0281 (11)	0.0293 (13)	0.0025 (9)	0.0138 (11)	0.0016 (9)
C26	0.0366 (14)	0.0304 (12)	0.0265 (13)	−0.0024 (10)	0.0139 (12)	−0.0038 (10)
C27	0.0341 (14)	0.0449 (14)	0.0387 (16)	0.0003 (11)	0.0229 (13)	−0.0018 (11)
N3	0.0318 (13)	0.0400 (12)	0.0371 (13)	−0.0015 (10)	0.0130 (11)	0.0037 (10)
O31	0.0701 (18)	0.0522 (14)	0.107 (2)	−0.0135 (13)	0.0569 (18)	−0.0149 (14)
O32	0.0774 (19)	0.0740 (17)	0.081 (2)	−0.0066 (13)	0.0594 (17)	−0.0044 (14)
O33	0.0696 (17)	0.0529 (13)	0.0595 (15)	−0.0113 (11)	0.0356 (13)	−0.0126 (11)
O4	0.113 (3)	0.101 (2)	0.072 (2)	0.003 (2)	0.054 (2)	−0.0029 (18)

Geometric parameters (Å, º)

Cu1—O1	1.9767 (17)	C17—H17A	0.9800
Cu1—N11	1.978 (2)	C17—H17B	0.9800
Cu1—N1	2.016 (2)	C17—H17C	0.9800
Cu1—N21	2.021 (2)	N21—C25	1.334 (3)
Cu1—O2^i	2.1476 (18)	N21—N22	1.355 (3)
O1—C1	1.261 (3)	C22—N22	1.455 (3)
C1—O2	1.247 (3)	C22—H22A	0.9900
C1—C2	1.520 (4)	C22—H22B	0.9900
O2—Cu1^ii	2.1477 (18)	N22—C23	1.347 (3)
C2—N1	1.479 (3)	C23—C24	1.375 (4)
C2—H2A	0.9900	C23—C26	1.491 (4)
C2—H2B	0.9900	C24—C25	1.399 (4)
N1—C22	1.470 (3)	C24—H24	0.9500
N1—H1	0.9300	C25—C27	1.489 (4)
N11—C15	1.341 (3)	C26—H26A	0.9800
N11—N12	1.351 (3)	C26—H26B	0.9800
N12—C13	1.346 (4)	C26—H26C	0.9800
N12—H12	0.8800	C27—H27A	0.9800
C13—C14	1.361 (5)	C27—H27B	0.9800
C13—C16	1.494 (5)	C27—H27C	0.9800
C14—C15	1.386 (4)	N3—O31	1.230 (3)
C14—H14	0.9500	N3—O32	1.236 (4)
C15—C17	1.479 (4)	N3—O33	1.247 (3)
C16—H16A	0.9800	O4—H4B	0.840 (10)
C16—H16B	0.9800	O4—H4A	0.845 (10)
C16—H16C	0.9800
O1—Cu1—N11	92.06 (8)	H16A—C16—H16C	109.5
O1—Cu1—N1	83.81 (8)	H16B—C16—H16C	109.5
N11—Cu1—N1	170.30 (9)	C15—C17—H17A	109.5
O1—Cu1—N21	146.20 (8)	C15—C17—H17B	109.5
N11—Cu1—N21	97.40 (9)	H17A—C17—H17B	109.5
N1—Cu1—N21	81.53 (8)	C15—C17—H17C	109.5
O1—Cu1—O2^i	105.47 (8)	H17A—C17—H17C	109.5
N11—Cu1—O2^i	89.03 (8)	H17B—C17—H17C	109.5
N1—Cu1—O2^i	100.52 (8)	C25—N21—N22	105.90 (19)
N21—Cu1—O2^i	107.06 (8)	C25—N21—Cu1	142.30 (18)
C1—O1—Cu1	116.31 (16)	N22—N21—Cu1	110.79 (15)
O2—C1—O1	124.9 (2)	N22—C22—N1	106.1 (2)
O2—C1—C2	117.2 (2)	N22—C22—H22A	110.5
O1—C1—C2	117.8 (2)	N1—C22—H22A	110.5
C1—O2—Cu1^ii	123.48 (16)	N22—C22—H22B	110.5
N1—C2—C1	111.4 (2)	N1—C22—H22B	110.5
N1—C2—H2A	109.3	H22A—C22—H22B	108.7
C1—C2—H2A	109.3	C23—N22—N21	111.7 (2)
N1—C2—H2B	109.3	C23—N22—C22	130.5 (2)
C1—C2—H2B	109.3	N21—N22—C22	117.54 (19)
H2A—C2—H2B	108.0	N22—C23—C24	106.3 (2)
C22—N1—C2	112.8 (2)	N22—C23—C26	122.6 (2)
C22—N1—Cu1	107.67 (15)	C24—C23—C26	131.1 (2)
C2—N1—Cu1	110.17 (15)	C23—C24—C25	106.3 (2)
C22—N1—H1	108.7	C23—C24—H24	126.9
C2—N1—H1	108.7	C25—C24—H24	126.9
Cu1—N1—H1	108.7	N21—C25—C24	109.7 (2)
C15—N11—N12	106.2 (2)	N21—C25—C27	121.4 (2)
C15—N11—Cu1	128.77 (19)	C24—C25—C27	128.9 (2)
N12—N11—Cu1	124.15 (17)	C23—C26—H26A	109.5
C13—N12—N11	111.1 (2)	C23—C26—H26B	109.5
C13—N12—H12	124.4	H26A—C26—H26B	109.5
N11—N12—H12	124.4	C23—C26—H26C	109.5
N12—C13—C14	106.5 (3)	H26A—C26—H26C	109.5
N12—C13—C16	122.1 (3)	H26B—C26—H26C	109.5
C14—C13—C16	131.4 (3)	C25—C27—H27A	109.5
C13—C14—C15	107.1 (3)	C25—C27—H27B	109.5
C13—C14—H14	126.4	H27A—C27—H27B	109.5
C15—C14—H14	126.4	C25—C27—H27C	109.5
N11—C15—C14	109.0 (3)	H27A—C27—H27C	109.5
N11—C15—C17	121.1 (2)	H27B—C27—H27C	109.5
C14—C15—C17	129.8 (3)	O31—N3—O32	118.3 (3)
C13—C16—H16A	109.5	O31—N3—O33	120.7 (3)
C13—C16—H16B	109.5	O32—N3—O33	120.9 (3)
H16A—C16—H16B	109.5	H4B—O4—H4A	107 (5)
C13—C16—H16C	109.5
N11—Cu1—O1—C1	−170.69 (18)	N12—N11—C15—C17	178.3 (3)
N1—Cu1—O1—C1	0.52 (18)	Cu1—N11—C15—C17	8.7 (4)
N21—Cu1—O1—C1	−64.1 (2)	C13—C14—C15—N11	0.0 (3)
O2^i—Cu1—O1—C1	99.75 (18)	C13—C14—C15—C17	−177.2 (3)
Cu1—O1—C1—O2	176.8 (2)	O1—Cu1—N21—C25	−138.7 (3)
Cu1—O1—C1—C2	−4.7 (3)	N11—Cu1—N21—C25	−33.7 (3)
O1—C1—O2—Cu1^ii	−3.1 (4)	N1—Cu1—N21—C25	156.1 (3)
C2—C1—O2—Cu1^ii	178.38 (17)	O2^i—Cu1—N21—C25	57.6 (3)
O2—C1—C2—N1	−173.8 (2)	O1—Cu1—N21—N22	55.3 (2)
O1—C1—C2—N1	7.6 (3)	N11—Cu1—N21—N22	160.30 (15)
C1—C2—N1—C22	113.8 (2)	N1—Cu1—N21—N22	−9.97 (15)
C1—C2—N1—Cu1	−6.6 (3)	O2^i—Cu1—N21—N22	−108.45 (15)
O1—Cu1—N1—C22	−119.76 (16)	C2—N1—C22—N22	−164.26 (19)
N21—Cu1—N1—C22	29.70 (15)	Cu1—N1—C22—N22	−42.5 (2)
O2^i—Cu1—N1—C22	135.60 (15)	C25—N21—N22—C23	0.7 (3)
O1—Cu1—N1—C2	3.63 (17)	Cu1—N21—N22—C23	171.89 (15)
N21—Cu1—N1—C2	153.08 (18)	C25—N21—N22—C22	175.7 (2)
O2^i—Cu1—N1—C2	−101.01 (17)	Cu1—N21—N22—C22	−13.1 (2)
O1—Cu1—N11—C15	75.3 (2)	N1—C22—N22—C23	−148.6 (2)
N21—Cu1—N11—C15	−72.2 (2)	N1—C22—N22—N21	37.5 (3)
O2^i—Cu1—N11—C15	−179.2 (2)	N21—N22—C23—C24	−0.3 (3)
O1—Cu1—N11—N12	−92.6 (2)	C22—N22—C23—C24	−174.4 (2)
N21—Cu1—N11—N12	120.0 (2)	N21—N22—C23—C26	−179.3 (2)
O2^i—Cu1—N11—N12	12.9 (2)	C22—N22—C23—C26	6.6 (4)
C15—N11—N12—C13	−1.2 (3)	N22—C23—C24—C25	−0.2 (3)
Cu1—N11—N12—C13	168.93 (18)	C26—C23—C24—C25	178.6 (2)
N11—N12—C13—C14	1.3 (3)	N22—N21—C25—C24	−0.9 (3)
N11—N12—C13—C16	−177.6 (3)	Cu1—N21—C25—C24	−167.3 (2)
N12—C13—C14—C15	−0.8 (3)	N22—N21—C25—C27	177.8 (2)
C16—C13—C14—C15	177.9 (3)	Cu1—N21—C25—C27	11.4 (4)
N12—N11—C15—C14	0.7 (3)	C23—C24—C25—N21	0.7 (3)
Cu1—N11—C15—C14	−168.85 (19)	C23—C24—C25—C27	−177.8 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N12—H12···O4^iii	0.88	2.23	3.014 (5)	148
O4—H4B···O33	0.84 (1)	2.11 (3)	2.891 (4)	155 (5)
O4—H4A···O33^iv	0.85 (1)	2.13 (2)	2.957 (5)	165 (6)
N1—H1···O1^i	0.93	2.38	2.910 (3)	116
N1—H1···O31^v	0.93	2.56	3.095 (3)	117
N1—H1···O32^v	0.93	2.48	3.230 (4)	138

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