Aqua­{2,2′-[propane-1,3-diylbis(nitrilo­methyl­idyne)]diphenolato}zinc(II)

In the title compound, [Zn(C₁₇H₁₆N₂O₂)(H₂O)], the Zn^II atom has a distorted penta­coordinate square-pyramidal geometry. A mirror plane passes through the Zn^II atom, the central C atom of the propyl group and the O atom of the coordinated water mol­ecule. The two planar Schiff base groups make a dihedral angle of 39.49 (6)°. The crystal packing is stabilized by weak inter­molecular inter­actions via the coordinated water mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.018
• wR factor = 0.054
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

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Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8B    ..  O2      ..       2.63 Ang.

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

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

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Computing details

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2005) and CRYSTALS (Betteridge et al., 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

Aqua{2,2'-[propane-1,3-diylbis(nitrilomethylidyne)]diphenolato}zinc(II)

Crystal data

[Zn(C17H16N2O2)(H2O)]	F(000) = 752.00
Mr = 363.72	Dx = 1.536 Mg m^−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -p 2ac 2n	Cell parameters from 13198 reflections
a = 8.731 (7) Å	θ = 3.4–27.5°
b = 24.06 (2) Å	µ = 1.58 mm^−1
c = 7.488 (7) Å	T = 296 K
V = 1573 (2) Å^3	Platelet, colorless
Z = 4	0.20 × 0.20 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	1579 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.016
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −11→11
Tmin = 0.668, Tmax = 0.854	k = −31→31
15638 measured reflections	l = −9→9
1845 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.018	w = 1/[σ^2(Fo^2) + (0.0353P)^2 + 0.1946P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.054	(Δ/σ)max = 0.001
S = 1.10	Δρmax = 0.37 e Å^−3
1845 reflections	Δρmin = −0.25 e Å^−3
113 parameters

Special details

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Zn1	0.51100 (2)	0.2500	0.92419 (2)	0.01307 (8)
O1	0.67870 (9)	0.19252 (3)	0.8935 (1)	0.0201 (2)
O2	0.4222 (1)	0.2500	0.6762 (1)	0.0165 (2)
N1	0.3793 (1)	0.18579 (4)	1.0398 (1)	0.0185 (2)
C1	0.6923 (1)	0.14085 (4)	0.9488 (1)	0.0171 (2)
C2	0.8300 (1)	0.11175 (5)	0.9147 (1)	0.0222 (2)
C3	0.8504 (1)	0.05768 (5)	0.9720 (2)	0.0273 (3)
C4	0.7360 (2)	0.03003 (5)	1.0666 (2)	0.0300 (3)
C5	0.6004 (1)	0.05720 (5)	1.0991 (2)	0.0257 (3)
C7	0.4252 (1)	0.13625 (5)	1.0761 (1)	0.0200 (2)
C6	0.5755 (1)	0.11254 (5)	1.0419 (1)	0.0184 (2)
C8	0.2153 (1)	0.19674 (6)	1.0708 (2)	0.0236 (3)
C9	0.1861 (2)	0.2500	1.1745 (2)	0.0263 (4)
H2	0.9084	0.1294	0.8524	0.027*
H3	0.9418	0.0395	0.9472	0.033*
H4	0.7511	−0.0061	1.1069	0.036*
H5	0.5229	0.0388	1.1604	0.031*
H7	0.3541	0.1130	1.1305	0.024*
H8a	0.1715	0.1658	1.1361	0.028*
H8b	0.1634	0.1991	0.9565	0.028*
H9a	0.0805	0.2500	1.2147	0.032*
H9b	0.2508	0.2500	1.2798	0.032*
H2w	0.3592	0.2223	0.6564	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0098 (1)	0.0167 (1)	0.0127 (1)	0.0000	0.00057 (6)	0.0000
O1	0.0152 (4)	0.0171 (4)	0.0281 (4)	0.0024 (3)	0.0050 (3)	0.0076 (3)
O2	0.0123 (5)	0.0204 (5)	0.0168 (6)	0.0000	−0.0026 (4)	0.0000
N1	0.0133 (4)	0.0272 (5)	0.0149 (5)	−0.0037 (4)	−0.0001 (3)	0.0037 (4)
C1	0.0190 (5)	0.0158 (5)	0.0164 (5)	−0.0004 (4)	−0.0034 (4)	0.0000 (4)
C2	0.0223 (6)	0.0201 (6)	0.0242 (6)	0.0017 (5)	0.0013 (4)	0.0024 (4)
C3	0.0308 (6)	0.0198 (6)	0.0314 (7)	0.0078 (5)	−0.0015 (5)	0.0000 (5)
C4	0.0403 (8)	0.0151 (6)	0.0346 (7)	0.0004 (6)	−0.0038 (6)	0.0043 (5)
C5	0.0310 (6)	0.0189 (6)	0.0272 (7)	−0.0074 (5)	−0.0021 (5)	0.0043 (5)
C7	0.0177 (5)	0.0252 (6)	0.0173 (6)	−0.0083 (5)	−0.0014 (4)	0.0039 (4)
C6	0.0205 (5)	0.0177 (5)	0.0171 (5)	−0.0032 (5)	−0.0038 (4)	0.0008 (4)
C8	0.0127 (5)	0.0358 (7)	0.0223 (6)	−0.0051 (5)	0.0018 (4)	0.0080 (5)
C9	0.0138 (7)	0.051 (1)	0.0146 (8)	0.0000	0.0042 (6)	0.0000

Geometric parameters (Å, º)

Zn1—O1	2.027 (2)	C3—C4	1.393 (2)
Zn1—O1^i	2.027 (2)	C3—H3	0.9300
Zn1—O2	2.012 (1)	C4—C5	1.374 (2)
Zn1—N1	2.112 (2)	C4—H4	0.9301
Zn1—N1^i	2.112 (2)	C5—C6	1.416 (2)
O1—C1	1.316 (1)	C5—H5	0.9300
O2—H2w	0.8773	C7—C6	1.454 (2)
O2—H2w^i	0.8773	C7—H7	0.9300
N1—C7	1.287 (2)	C8—C9	1.520 (2)
N1—C8	1.474 (1)	C8—H8a	0.9700
C1—C2	1.415 (2)	C8—H8b	0.9700
C1—C6	1.410 (2)	C9—C8^i	1.520 (2)
C2—C3	1.382 (2)	C9—H9a	0.9700
C2—H2	0.9300	C9—H9b	0.9700
Zn1···C1	3.072 (3)	C2···H4^vii	3.5036
Zn1···C1^i	3.072 (3)	C2···H2w^iii	2.7247
Zn1···C7	3.058 (3)	C3···C5	2.381 (2)
Zn1···C7^i	3.058 (3)	C3···C6	2.788 (2)
Zn1···C6	3.469 (3)	C3···H2	2.0087
Zn1···C6^i	3.469 (3)	C3···H4	2.0316
Zn1···C8	3.085 (3)	C3···H4^vii	3.1308
Zn1···C8^i	3.085 (3)	C3···H5	3.2200
Zn1···C9	3.400 (2)	C3···H5^vii	3.4722
Zn1···H8b	3.2819	C4···C6	2.437 (2)
Zn1···H8b^i	3.2819	C4···H2	3.2483
Zn1···H8b^ii	3.3761	C4···H3	2.0202
Zn1···H8b^iii	3.3761	C4···H4^vii	3.4920
Zn1···H9b	3.5005	C4···H5	1.9993
Zn1···H2w	2.4945	C5···C7	2.447 (2)
Zn1···H2w^i	2.4945	C5···H3	3.2194
Zn1···H2w^ii	3.1699	C5···H3^viii	3.5128
Zn1···H2w^iii	3.1699	C5···H4	2.0141
O1···O1^i	2.766 (3)	C5···H7	2.5453
O1···O2	3.094 (3)	C7···C8	2.341 (2)
O1···O2^ii	2.590 (3)	C7···C9	3.520 (2)
O1···N1	2.839 (3)	C7···H2^iv	3.2163
O1···C2	2.355 (3)	C7···H5	2.5751
O1···C7	2.933 (3)	C7···H8a	2.3689
O1···C6	2.398 (3)	C7···H8b	2.8827
O1···C8^iii	3.493 (3)	C7···H9b	3.4840
O1···H2	2.5348	C6···H2	3.2594
O1···H2^iv	3.3573	C6···H2^iv	3.3178
O1···H8b^iii	2.6287	C6···H4	3.2774
O1···H2w	3.3835	C6···H5	2.0375
O1···H2w^ii	2.6124	C6···H7	2.0434
O1···H2w^iii	1.7706	C8···O1^iv	3.493 (4)
O2···O1^i	3.094 (3)	C8···O2^v	3.407 (2)
O2···O1^v	2.589 (3)	C8···N1^i	3.177 (2)
O2···O1^iv	2.589 (3)	C8···C8^i	2.563 (2)
O2···N1	3.153 (3)	C8···H2^ix	3.5331
O2···N1^i	3.153 (3)	C8···H7	2.3945
O2···C1^v	3.435 (3)	C8···H8a^i	3.3665
O2···C1^iv	3.435 (3)	C8···H8b^i	2.6882
O2···C2^v	3.489 (3)	C8···H9a	2.0467
O2···C2^iv	3.489 (3)	C8···H9b	2.0467
O2···C8^ii	3.407 (2)	C8···H2w	3.4034
O2···C8^iii	3.407 (2)	C8···H2w^iv	3.5971
O2···C9^ii	3.494 (2)	C9···O2^v	3.494 (2)
O2···H2^v	2.9135	C9···N1^i	2.500 (2)
O2···H2^iv	2.9135	C9···C7^i	3.520 (2)
O2···H8b	3.3183	C9···H8a	2.0515
O2···H8b^i	3.3183	C9···H8a^i	2.0515
O2···H8b^ii	2.6316	C9···H8b	2.0515
O2···H8b^iii	2.6316	C9···H8b^i	2.0515
O2···H9a^ii	3.2373	H2···O1^iii	3.3573
O2···H9b^vi	3.3243	H2···O2^ii	2.9135
N1···N1^i	3.090 (3)	H2···N1^iii	3.2455
N1···C1	3.017 (3)	H2···C1^iii	3.3627
N1···C6	2.458 (3)	H2···C7^iii	3.2163
N1···C8^i	3.177 (2)	H2···C6^iii	3.3178
N1···C9	2.500 (2)	H2···C8^x	3.5331
N1···H2^iv	3.2455	H3···C5^vii	3.5128
N1···H7	1.8923	H4···C2^viii	3.5036
N1···H8a	2.0108	H4···C3^viii	3.1308
N1···H8b	2.0108	H4···C4^viii	3.4920
N1···H8b^i	3.4090	H5···C3^viii	3.4722
N1···H9a	3.3029	H8a···C8^i	3.3665
N1···H9b	2.6224	H8b···Zn1^v	3.3761
N1···H2w	3.0072	H8b···O1^iv	2.6287
C1···O2^ii	3.435 (3)	H8b···O2^v	2.6316
C1···C3	2.437 (2)	H8b···N1^i	3.4090
C1···C4	2.835 (2)	H8b···C1^iv	3.3520
C1···C5	2.442 (2)	H8b···C8^i	2.6882
C1···C7	2.521 (2)	H9a···O2^v	3.2373
C1···H2	2.0391	H9a···N1^i	3.3029
C1···H2^iv	3.3627	H9a···C8^i	2.0467
C1···H3	3.2713	H9b···O2^xi	3.3243
C1···H5	3.2759	H9b···N1^i	2.6224
C1···H7	3.3190	H9b···C7^i	3.4840
C1···H8b^iii	3.3520	H9b···C8^i	2.0467
C1···H2w^iii	2.5662	H2w···Zn1^v	3.1699
C2···O2^ii	3.489 (3)	H2w···O1^v	2.6124
C2···C4	2.416 (2)	H2w···O1^iv	1.7706
C2···C5	2.766 (2)	H2w···C1^iv	2.5662
C2···C6	2.418 (2)	H2w···C2^iv	2.7247
C2···H3	2.0097	H2w···C8^iii	3.5971
C2···H4	3.2544
O1—Zn1—O1^i	86.05 (3)	C4—C3—H3	119.4824
O1—Zn1—O2	100.00 (3)	H3—C3—C2	119.4788
O1—Zn1—N1	86.59 (3)	C5—C4—C3	118.7 (1)
O1—Zn1—N1^i	159.89 (4)	C5—C4—H4	120.6474
O1^i—Zn1—O2	100.00 (3)	H4—C4—C3	120.6440
O1^i—Zn1—N1	159.89 (4)	C6—C5—C4	121.7 (1)
O1^i—Zn1—N1^i	86.59 (3)	C6—C5—H5	119.1280
O2—Zn1—N1	99.70 (3)	H5—C5—C4	119.1292
O2—Zn1—N1^i	99.70 (3)	C6—C7—N1	127.4 (1)
N1—Zn1—N1^i	94.06 (4)	C6—C7—H7	116.2955
C1—O1—Zn1	132.37 (7)	H7—C7—N1	116.2959
H2w—O2—Zn1	113.4404	C9—C8—N1	113.2 (1)
H2w—O2—H2w^i	98.9425	C9—C8—H8b	108.9331
H2w^i—O2—Zn1	113.4404	C9—C8—H8a	108.9352
C7—N1—Zn1	126.51 (8)	H8a—C8—N1	108.9460
C7—N1—C8	115.8 (1)	H8a—C8—H8b	107.7539
C8—N1—Zn1	117.56 (8)	H8b—C8—N1	108.9401
C2—C1—C6	117.7 (1)	C8^i—C9—C8	114.9 (1)
C2—C1—O1	119.1 (1)	C8^i—C9—H9b	108.5336
C6—C1—O1	123.2 (1)	C8^i—C9—H9a	108.5314
C3—C2—C1	121.3 (1)	H9a—C9—C8	108.5314
C3—C2—H2	119.3723	H9a—C9—H9b	107.5317
H2—C2—C1	119.3624	H9b—C9—C8	108.5336
C4—C3—C2	121.0 (1)
O2—Zn1—O1—C1	−106.63 (8)	C1—C2—C3—C4	−0.4 (2)
O1—Zn1—O2—H2w	80.2	C2—C3—C4—C5	1.3 (2)
O1—Zn1—N1—C7	6.15 (8)	C3—C4—C5—C6	−1.1 (2)
Zn1—O1—C1—C2	−176.12 (8)	C4—C5—C6—C1	0.0 (2)
Zn1—N1—C7—C6	−1.9 (2)	C4—C5—C6—C7	177.2 (1)
Zn1—N1—C8—C9	−52.29 (13)	N1—C7—C6—C1	−4.8 (2)
O1—C1—C2—C3	179.2 (1)	N1—C7—C6—C5	178.1 (1)
O1—C1—C6—C5	−179.0 (1)	N1—C8—C9—H9a	−166.4
O1—C1—C6—C7	4.0 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2w···O1^iv	0.88	1.77	2.590 (3)	154
C8—H8b···O2^v	0.97	2.63	3.407 (2)	137

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