Nitrato[1-(2-pyridylmethyl­imino­methyl)naphthalen-2-olato]zinc(II)

In the title mononuclear zinc(II) compound, [Zn(C₁₇H₁₃N₂O)(NO₃)], the Zn atom is four-coordinate, bonded to two N atoms and one O atom from the Schiff base ligand, and to one O atom from the nitrate anion. The four atoms around the Zn atom adopt an approximately square-planar configuration.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• R factor = 0.039
• wR factor = 0.114
• Data-to-parameter ratio = 14.2

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.

Nitrato[1-(2-pyridylmethyliminomethyl)naphthalen-2-olato]zinc(II)

Crystal data

[Zn(C17H13N2O)(NO3)]	F(000) = 792
Mr = 388.67	Dx = 1.664 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2887 reflections
a = 15.105 (2) Å	θ = 2.7–25.7°
b = 7.398 (2) Å	µ = 1.61 mm^−1
c = 15.056 (2) Å	T = 273 K
β = 112.72 (1)°	Block, yellow
V = 1551.9 (5) Å^3	0.22 × 0.21 × 0.17 mm
Z = 4

Data collection

Bruker APEX CCD area-detector diffractometer	3202 independent reflections
Radiation source: fine-focus sealed tube	2705 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 26.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→11
Tmin = 0.711, Tmax = 0.764	k = −9→9
8760 measured reflections	l = −18→18

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.114	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0647P)^2 + 0.5874P] where P = (Fo^2 + 2Fc^2)/3
3202 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.46 e Å^−3
0 restraints	Δρmin = −0.24 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
Zn1	0.26929 (2)	0.44524 (5)	0.47721 (2)	0.04086 (15)
O1	0.36943 (14)	0.3759 (3)	0.59242 (13)	0.0495 (5)
O2	0.19581 (15)	0.5317 (3)	0.55575 (15)	0.0507 (5)
O3	0.14963 (17)	0.2571 (3)	0.51785 (16)	0.0596 (6)
O4	0.1011 (2)	0.4079 (4)	0.6132 (2)	0.0800 (8)
N1	0.33846 (15)	0.3748 (3)	0.39988 (14)	0.0315 (5)
N2	0.17005 (16)	0.5215 (3)	0.35232 (16)	0.0371 (5)
N3	0.14739 (18)	0.3970 (4)	0.56281 (17)	0.0481 (6)
C1	0.48375 (18)	0.2704 (3)	0.52849 (16)	0.0319 (5)
C2	0.45092 (19)	0.3045 (4)	0.60261 (18)	0.0383 (6)
C3	0.5119 (2)	0.2538 (5)	0.6985 (2)	0.0544 (8)
H3	0.4906	0.2730	0.7480	0.065*
C4	0.5991 (2)	0.1793 (5)	0.7196 (2)	0.0521 (8)
H4	0.6361	0.1480	0.7830	0.063*
C5	0.6356 (2)	0.1476 (4)	0.64753 (19)	0.0383 (6)
C6	0.7284 (2)	0.0741 (4)	0.6706 (2)	0.0488 (8)
H6	0.7663	0.0478	0.7345	0.059*
C7	0.7630 (2)	0.0413 (4)	0.6019 (3)	0.0539 (8)
H7	0.8235	−0.0097	0.6179	0.065*
C8	0.7072 (2)	0.0849 (5)	0.5068 (2)	0.0522 (8)
H8	0.7308	0.0626	0.4592	0.063*
C9	0.6180 (2)	0.1600 (4)	0.4820 (2)	0.0443 (7)
H9	0.5828	0.1895	0.4179	0.053*
C10	0.57819 (18)	0.1938 (3)	0.55101 (17)	0.0335 (5)
C11	0.42373 (18)	0.3081 (3)	0.43067 (17)	0.0319 (5)
H11	0.4488	0.2819	0.3846	0.038*
C12	0.28716 (19)	0.3984 (4)	0.29580 (17)	0.0371 (6)
H12A	0.2757	0.2814	0.2643	0.044*
H12B	0.3258	0.4697	0.2703	0.044*
C13	0.19294 (19)	0.4924 (4)	0.27606 (18)	0.0353 (6)
C14	0.1336 (2)	0.5469 (4)	0.1849 (2)	0.0504 (8)
H14	0.1505	0.5260	0.1326	0.060*
C15	0.0487 (2)	0.6330 (5)	0.1727 (2)	0.0583 (8)
H15	0.0080	0.6721	0.1120	0.070*
C16	0.0248 (2)	0.6605 (4)	0.2505 (2)	0.0556 (8)
H16	−0.0327	0.7164	0.2433	0.067*
C17	0.0869 (2)	0.6045 (4)	0.3387 (2)	0.0476 (7)
H17	0.0710	0.6246	0.3917	0.057*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0370 (2)	0.0534 (3)	0.0348 (2)	−0.00132 (14)	0.01669 (15)	−0.00535 (13)
O1	0.0422 (11)	0.0805 (15)	0.0278 (9)	0.0060 (11)	0.0156 (8)	−0.0035 (10)
O2	0.0469 (12)	0.0630 (14)	0.0502 (12)	−0.0059 (11)	0.0278 (10)	−0.0129 (10)
O3	0.0596 (14)	0.0671 (15)	0.0539 (13)	−0.0101 (12)	0.0238 (11)	−0.0090 (11)
O4	0.0709 (18)	0.117 (2)	0.0768 (18)	−0.0091 (16)	0.0556 (16)	−0.0078 (16)
N1	0.0319 (11)	0.0366 (11)	0.0252 (10)	−0.0023 (9)	0.0103 (8)	−0.0023 (8)
N2	0.0316 (12)	0.0379 (12)	0.0395 (12)	−0.0019 (9)	0.0113 (10)	−0.0020 (9)
N3	0.0356 (13)	0.0752 (18)	0.0350 (12)	0.0001 (13)	0.0153 (10)	−0.0015 (12)
C1	0.0347 (13)	0.0323 (13)	0.0279 (11)	−0.0062 (11)	0.0111 (10)	−0.0014 (9)
C2	0.0369 (14)	0.0479 (15)	0.0287 (12)	−0.0072 (12)	0.0109 (11)	−0.0025 (11)
C3	0.0538 (19)	0.083 (2)	0.0265 (13)	−0.0055 (17)	0.0161 (13)	0.0031 (14)
C4	0.0517 (18)	0.064 (2)	0.0303 (14)	−0.0008 (15)	0.0041 (13)	0.0107 (13)
C5	0.0402 (15)	0.0315 (13)	0.0356 (13)	−0.0056 (11)	0.0060 (11)	0.0020 (11)
C6	0.0438 (17)	0.0370 (15)	0.0499 (17)	0.0009 (13)	0.0006 (14)	0.0065 (12)
C7	0.0357 (16)	0.0432 (17)	0.073 (2)	0.0040 (13)	0.0106 (16)	−0.0011 (15)
C8	0.0441 (17)	0.0563 (19)	0.0574 (19)	0.0039 (14)	0.0210 (15)	−0.0046 (14)
C9	0.0388 (15)	0.0543 (17)	0.0394 (14)	0.0031 (13)	0.0148 (12)	−0.0001 (13)
C10	0.0339 (13)	0.0303 (12)	0.0328 (12)	−0.0056 (10)	0.0088 (11)	−0.0012 (10)
C11	0.0342 (13)	0.0362 (13)	0.0277 (12)	−0.0034 (11)	0.0144 (10)	−0.0036 (10)
C12	0.0375 (14)	0.0462 (15)	0.0250 (12)	0.0021 (12)	0.0093 (10)	0.0010 (11)
C13	0.0351 (14)	0.0332 (13)	0.0349 (13)	−0.0025 (11)	0.0106 (11)	0.0016 (11)
C14	0.0451 (18)	0.063 (2)	0.0369 (15)	0.0027 (14)	0.0091 (13)	0.0053 (13)
C15	0.0474 (19)	0.062 (2)	0.0519 (18)	0.0071 (16)	0.0042 (15)	0.0124 (16)
C16	0.0379 (16)	0.0510 (18)	0.071 (2)	0.0058 (14)	0.0140 (15)	0.0004 (16)
C17	0.0374 (15)	0.0506 (17)	0.0556 (18)	0.0027 (13)	0.0188 (14)	−0.0032 (14)

Geometric parameters (Å, º)

Zn1—O1	1.880 (2)	C5—C10	1.417 (4)
Zn1—N1	1.913 (2)	C6—C7	1.349 (5)
Zn1—N2	1.981 (2)	C6—H6	0.9300
Zn1—O2	2.013 (2)	C7—C8	1.390 (5)
O1—C2	1.293 (3)	C7—H7	0.9300
O2—N3	1.264 (3)	C8—C9	1.369 (4)
O3—N3	1.244 (3)	C8—H8	0.9300
O4—N3	1.217 (3)	C9—C10	1.410 (4)
N1—C11	1.287 (3)	C9—H9	0.9300
N1—C12	1.466 (3)	C11—H11	0.9300
N2—C13	1.338 (3)	C12—C13	1.507 (4)
N2—C17	1.341 (4)	C12—H12A	0.9700
C1—C2	1.408 (3)	C12—H12B	0.9700
C1—C11	1.427 (3)	C13—C14	1.378 (4)
C1—C10	1.448 (4)	C14—C15	1.378 (5)
C2—C3	1.431 (4)	C14—H14	0.9300
C3—C4	1.348 (5)	C15—C16	1.367 (5)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.415 (4)	C16—C17	1.361 (4)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.416 (4)	C17—H17	0.9300
O1—Zn1—N1	93.06 (9)	C6—C7—H7	120.4
O1—Zn1—N2	176.32 (9)	C8—C7—H7	120.4
N1—Zn1—N2	83.73 (9)	C9—C8—C7	121.1 (3)
O1—Zn1—O2	88.53 (9)	C9—C8—H8	119.4
N1—Zn1—O2	177.16 (9)	C7—C8—H8	119.4
N2—Zn1—O2	94.60 (10)	C8—C9—C10	121.7 (3)
C2—O1—Zn1	127.65 (16)	C8—C9—H9	119.1
N3—O2—Zn1	105.48 (17)	C10—C9—H9	119.1
C11—N1—C12	118.2 (2)	C9—C10—C5	116.5 (2)
C11—N1—Zn1	126.24 (17)	C9—C10—C1	124.0 (2)
C12—N1—Zn1	115.53 (16)	C5—C10—C1	119.5 (2)
C13—N2—C17	118.6 (2)	N1—C11—C1	126.5 (2)
C13—N2—Zn1	114.64 (18)	N1—C11—H11	116.7
C17—N2—Zn1	126.6 (2)	C1—C11—H11	116.7
O4—N3—O3	122.5 (3)	N1—C12—C13	109.6 (2)
O4—N3—O2	119.4 (3)	N1—C12—H12A	109.8
O3—N3—O2	118.1 (2)	C13—C12—H12A	109.8
C2—C1—C11	120.3 (2)	N1—C12—H12B	109.8
C2—C1—C10	120.1 (2)	C13—C12—H12B	109.8
C11—C1—C10	119.6 (2)	H12A—C12—H12B	108.2
O1—C2—C1	126.1 (2)	N2—C13—C14	121.5 (3)
O1—C2—C3	116.0 (2)	N2—C13—C12	116.3 (2)
C1—C2—C3	117.8 (3)	C14—C13—C12	122.2 (3)
C4—C3—C2	122.3 (3)	C13—C14—C15	118.8 (3)
C4—C3—H3	118.8	C13—C14—H14	120.6
C2—C3—H3	118.8	C15—C14—H14	120.6
C3—C4—C5	121.5 (3)	C16—C15—C14	119.6 (3)
C3—C4—H4	119.3	C16—C15—H15	120.2
C5—C4—H4	119.3	C14—C15—H15	120.2
C4—C5—C6	121.2 (3)	C17—C16—C15	118.7 (3)
C4—C5—C10	118.8 (3)	C17—C16—H16	120.7
C6—C5—C10	120.0 (3)	C15—C16—H16	120.7
C7—C6—C5	121.4 (3)	N2—C17—C16	122.7 (3)
C7—C6—H6	119.3	N2—C17—H17	118.6
C5—C6—H6	119.3	C16—C17—H17	118.6
C6—C7—C8	119.2 (3)