Bis{2′-[1-(2-hydroxy­phenyl)­ethyl­idene]­benzohydr­azido}bis­(pyridine-κN)­zinc(II)

In the centrosymmetric title compound, [Zn(C₁₅H₁₃N₂O₂)₂(C₅H₅N)₂], the Zn atom is chelated by the O and N atoms of two bidentate ligands. The coordination geometry of the central Zn atom is octahedral. The crystal packing is stabilized by intermolecular C—H...O interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.064
• wR factor = 0.145
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.25
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.31 Ratio
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         C3
PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ......         C8
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            O2  -ZN1 -O2  -C9      0.00 55.00   3.756   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         10
            N1  -ZN1 -N1  -C7    101.00100.00   3.756   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         15
            N1  -ZN1 -N1  -N2    -81.00100.00   3.756   1.555   1.555   3.756
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         18
            N3  -ZN1 -N3  -C16  -113.00100.00   3.756   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         23
            N3  -ZN1 -N3  -C20    72.00100.00   3.756   1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  10 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
   3 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
   7 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Bis{2'-[1-(2-hydroxyphenyl)ethylidene]benzohydrazido}bis(pyridine-κN)zinc(II)

Crystal data

[Zn(C15H13N2O2)2(C5H5N)2]	F(000) = 760
Mr = 730.12	Dx = 1.340 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.3531 (11) Å	Cell parameters from 2851 reflections
b = 15.0133 (16) Å	θ = 1.9–27.0°
c = 11.6892 (12) Å	µ = 0.73 mm^−1
β = 95.138 (2)°	T = 293 K
V = 1809.6 (3) Å^3	Block, light yellow
Z = 2	0.29 × 0.20 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3933 independent reflections
Radiation source: fine-focus sealed tube	3304 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 83.66 pixels mm^-1	θmax = 27.0°, θmin = 1.9°
ω scans	h = −13→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −19→15
Tmin = 0.817, Tmax = 0.892	l = −13→14
9919 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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.22	w = 1/[σ^2(Fo^2) + (0.0583P)^2 + 0.6177P] where P = (Fo^2 + 2Fc^2)/3
3933 reflections	(Δ/σ)max < 0.001
237 parameters	Δρmax = 0.54 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

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

	x	y	z	Uiso*/Ueq
Zn1	1.0000	0.0000	0.5000	0.03982 (17)
O1	0.6597 (3)	0.0240 (2)	0.1600 (3)	0.0745 (9)
O2	1.09075 (19)	0.11709 (13)	0.53913 (17)	0.0431 (5)
N1	0.9181 (2)	0.01801 (15)	0.3191 (2)	0.0394 (6)
N2	1.1629 (2)	0.05382 (16)	0.7123 (2)	0.0378 (5)
N3	0.8164 (2)	0.05780 (18)	0.5519 (2)	0.0464 (6)
C1	0.9485 (5)	0.1064 (3)	0.0358 (3)	0.0711 (11)
H1B	1.0345	0.1214	0.0567	0.085*
C2	0.9000 (7)	0.1148 (3)	−0.0769 (4)	0.1006 (18)
H2C	0.9537	0.1330	−0.1321	0.121*
C3	0.7728 (8)	0.0963 (3)	−0.1072 (4)	0.116 (2)
H3A	0.7389	0.1044	−0.1829	0.139*
C4	0.6946 (5)	0.0659 (3)	−0.0280 (4)	0.0914 (16)
H4A	0.6082	0.0528	−0.0503	0.110*
C5	0.7431 (4)	0.0542 (2)	0.0864 (3)	0.0612 (10)
C6	0.8713 (3)	0.0757 (2)	0.1197 (3)	0.0476 (7)
C7	0.9310 (3)	0.0764 (2)	0.2406 (3)	0.0431 (7)
C8	1.0184 (4)	0.1537 (3)	0.2727 (3)	0.0701 (11)
H8A	1.0519	0.1483	0.3517	0.105*
H8B	0.9703	0.2082	0.2622	0.105*
H8C	1.0890	0.1541	0.2248	0.105*
C9	1.1602 (2)	0.11658 (18)	0.6340 (2)	0.0351 (6)
C10	1.2486 (3)	0.19371 (18)	0.6594 (2)	0.0355 (6)
C11	1.3164 (3)	0.2050 (2)	0.7658 (3)	0.0520 (8)
H11A	1.3058	0.1648	0.8246	0.062*
C12	1.3999 (4)	0.2763 (3)	0.7844 (3)	0.0662 (10)
H12A	1.4455	0.2835	0.8560	0.079*
C13	1.4163 (4)	0.3361 (3)	0.6993 (3)	0.0686 (11)
H13A	1.4736	0.3835	0.7125	0.082*
C14	1.3482 (4)	0.3260 (2)	0.5947 (3)	0.0603 (9)
H14A	1.3587	0.3670	0.5366	0.072*
C15	1.2646 (3)	0.2560 (2)	0.5744 (3)	0.0446 (7)
H15A	1.2182	0.2502	0.5029	0.054*
C16	0.7190 (3)	0.0096 (2)	0.5837 (3)	0.0537 (8)
H16A	0.7301	−0.0517	0.5903	0.064*
C17	0.6031 (3)	0.0451 (3)	0.6074 (3)	0.0637 (10)
H17A	0.5377	0.0087	0.6307	0.076*
C18	0.5846 (4)	0.1341 (3)	0.5965 (4)	0.0733 (11)
H18A	0.5058	0.1596	0.6105	0.088*
C19	0.6836 (4)	0.1854 (3)	0.5647 (4)	0.0799 (12)
H19A	0.6740	0.2468	0.5577	0.096*
C20	0.7975 (4)	0.1450 (3)	0.5432 (3)	0.0661 (10)
H20A	0.8648	0.1804	0.5214	0.079*
H1O	0.695 (4)	−0.003 (2)	0.209 (3)	0.050 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0386 (3)	0.0384 (3)	0.0419 (3)	−0.0086 (2)	0.00053 (19)	0.0007 (2)
O1	0.0497 (16)	0.0660 (18)	0.103 (2)	0.0087 (13)	−0.0186 (16)	0.0156 (17)
O2	0.0464 (11)	0.0396 (11)	0.0419 (11)	−0.0096 (9)	−0.0028 (9)	0.0049 (9)
N1	0.0411 (13)	0.0351 (13)	0.0419 (13)	−0.0070 (10)	0.0031 (10)	0.0018 (10)
N2	0.0409 (13)	0.0352 (13)	0.0373 (13)	−0.0062 (10)	0.0034 (10)	0.0034 (10)
N3	0.0426 (14)	0.0476 (16)	0.0492 (15)	−0.0007 (11)	0.0050 (11)	0.0021 (12)
C1	0.109 (3)	0.056 (2)	0.049 (2)	−0.005 (2)	0.013 (2)	0.0079 (17)
C2	0.187 (6)	0.070 (3)	0.047 (2)	−0.009 (3)	0.020 (3)	0.007 (2)
C3	0.221 (7)	0.062 (3)	0.055 (3)	−0.007 (4)	−0.046 (4)	0.007 (2)
C4	0.131 (4)	0.047 (2)	0.084 (3)	0.000 (2)	−0.053 (3)	0.001 (2)
C5	0.080 (3)	0.0322 (18)	0.067 (2)	0.0053 (16)	−0.018 (2)	0.0017 (16)
C6	0.069 (2)	0.0324 (16)	0.0409 (16)	0.0022 (14)	0.0004 (15)	0.0012 (13)
C7	0.0459 (17)	0.0418 (17)	0.0415 (16)	−0.0038 (13)	0.0032 (13)	0.0037 (13)
C8	0.090 (3)	0.061 (2)	0.057 (2)	−0.034 (2)	−0.009 (2)	0.0169 (18)
C9	0.0333 (14)	0.0351 (15)	0.0378 (14)	−0.0003 (11)	0.0087 (11)	−0.0046 (12)
C10	0.0342 (14)	0.0344 (15)	0.0392 (15)	−0.0016 (11)	0.0098 (11)	−0.0074 (12)
C11	0.063 (2)	0.052 (2)	0.0409 (17)	−0.0147 (16)	0.0069 (15)	−0.0052 (15)
C12	0.074 (2)	0.069 (3)	0.054 (2)	−0.025 (2)	0.0009 (18)	−0.0192 (19)
C13	0.078 (3)	0.053 (2)	0.077 (3)	−0.0292 (19)	0.020 (2)	−0.021 (2)
C14	0.077 (2)	0.0441 (19)	0.062 (2)	−0.0160 (17)	0.0206 (19)	−0.0023 (17)
C15	0.0489 (17)	0.0389 (16)	0.0470 (17)	−0.0015 (13)	0.0090 (13)	−0.0023 (14)
C16	0.0522 (19)	0.052 (2)	0.058 (2)	−0.0044 (15)	0.0077 (16)	−0.0042 (16)
C17	0.048 (2)	0.078 (3)	0.066 (2)	−0.0047 (18)	0.0119 (17)	−0.003 (2)
C18	0.048 (2)	0.091 (3)	0.082 (3)	0.020 (2)	0.0090 (19)	−0.001 (2)
C19	0.070 (3)	0.061 (3)	0.110 (3)	0.021 (2)	0.012 (2)	0.010 (2)
C20	0.058 (2)	0.049 (2)	0.092 (3)	0.0042 (17)	0.013 (2)	0.013 (2)

Geometric parameters (Å, º)

Zn1—O2^i	2.0261 (19)	C7—C8	1.498 (4)
Zn1—O2	2.0261 (19)	C8—H8A	0.9600
Zn1—N3^i	2.222 (3)	C8—H8B	0.9600
Zn1—N3	2.222 (3)	C8—H8C	0.9600
Zn1—N1	2.223 (2)	C9—C10	1.489 (4)
Zn1—N1^i	2.223 (2)	C10—C11	1.383 (4)
O1—C5	1.351 (5)	C10—C15	1.385 (4)
O1—H1O	0.77 (4)	C11—C12	1.380 (5)
O2—C9	1.267 (3)	C11—H11A	0.9300
N1—C7	1.284 (4)	C12—C13	1.362 (5)
N1—N2^i	1.395 (3)	C12—H12A	0.9300
N2—C9	1.312 (4)	C13—C14	1.364 (5)
N2—N1^i	1.395 (3)	C13—H13A	0.9300
N3—C16	1.322 (4)	C14—C15	1.369 (4)
N3—C20	1.327 (4)	C14—H14A	0.9300
C1—C2	1.372 (6)	C15—H15A	0.9300
C1—C6	1.398 (5)	C16—C17	1.363 (5)
C1—H1B	0.9300	C16—H16A	0.9300
C2—C3	1.362 (8)	C17—C18	1.354 (6)
C2—H2C	0.9300	C17—H17A	0.9300
C3—C4	1.362 (8)	C18—C19	1.360 (6)
C3—H3A	0.9300	C18—H18A	0.9300
C4—C5	1.397 (5)	C19—C20	1.369 (5)
C4—H4A	0.9300	C19—H19A	0.9300
C5—C6	1.387 (5)	C20—H20A	0.9300
C6—C7	1.491 (4)
O2^i—Zn1—O2	180.00 (6)	C6—C7—C8	115.6 (3)
O2^i—Zn1—N3^i	89.44 (9)	C7—C8—H8A	109.5
O2—Zn1—N3^i	90.56 (9)	C7—C8—H8B	109.5
O2^i—Zn1—N3	90.56 (9)	H8A—C8—H8B	109.5
O2—Zn1—N3	89.44 (9)	C7—C8—H8C	109.5
N3^i—Zn1—N3	180.0	H8A—C8—H8C	109.5
O2^i—Zn1—N1	76.19 (8)	H8B—C8—H8C	109.5
O2—Zn1—N1	103.81 (8)	O2—C9—N2	126.2 (3)
N3^i—Zn1—N1	92.88 (9)	O2—C9—C10	117.4 (2)
N3—Zn1—N1	87.12 (9)	N2—C9—C10	116.4 (2)
O2^i—Zn1—N1^i	103.81 (8)	C11—C10—C15	118.6 (3)
O2—Zn1—N1^i	76.19 (8)	C11—C10—C9	121.9 (3)
N3^i—Zn1—N1^i	87.12 (9)	C15—C10—C9	119.6 (3)
N3—Zn1—N1^i	92.88 (9)	C12—C11—C10	119.9 (3)
N1—Zn1—N1^i	180.0	C12—C11—H11A	120.1
C5—O1—H1O	111 (3)	C10—C11—H11A	120.1
C9—O2—Zn1	114.07 (17)	C13—C12—C11	120.8 (3)
C7—N1—N2^i	116.0 (2)	C13—C12—H12A	119.6
C7—N1—Zn1	135.0 (2)	C11—C12—H12A	119.6
N2^i—N1—Zn1	108.97 (16)	C12—C13—C14	119.6 (3)
C9—N2—N1^i	113.4 (2)	C12—C13—H13A	120.2
C16—N3—C20	116.8 (3)	C14—C13—H13A	120.2
C16—N3—Zn1	123.8 (2)	C13—C14—C15	120.5 (3)
C20—N3—Zn1	119.3 (2)	C13—C14—H14A	119.7
C2—C1—C6	121.4 (4)	C15—C14—H14A	119.7
C2—C1—H1B	119.3	C14—C15—C10	120.6 (3)
C6—C1—H1B	119.3	C14—C15—H15A	119.7
C3—C2—C1	119.6 (5)	C10—C15—H15A	119.7
C3—C2—H2C	120.2	N3—C16—C17	123.4 (3)
C1—C2—H2C	120.2	N3—C16—H16A	118.3
C2—C3—C4	120.7 (4)	C17—C16—H16A	118.3
C2—C3—H3A	119.6	C18—C17—C16	119.1 (4)
C4—C3—H3A	119.6	C18—C17—H17A	120.5
C3—C4—C5	120.6 (5)	C16—C17—H17A	120.5
C3—C4—H4A	119.7	C17—C18—C19	118.7 (4)
C5—C4—H4A	119.7	C17—C18—H18A	120.6
O1—C5—C6	123.3 (3)	C19—C18—H18A	120.6
O1—C5—C4	117.1 (4)	C18—C19—C20	118.8 (4)
C6—C5—C4	119.5 (4)	C18—C19—H19A	120.6
C5—C6—C1	118.2 (3)	C20—C19—H19A	120.6
C5—C6—C7	124.9 (3)	N3—C20—C19	123.2 (4)
C1—C6—C7	116.6 (3)	N3—C20—H20A	118.4
N1—C7—C6	127.7 (3)	C19—C20—H20A	118.4
N1—C7—C8	116.7 (3)
O2^i—Zn1—O2—C9	0 (55)	C2—C1—C6—C5	−0.4 (6)
N3^i—Zn1—O2—C9	−77.37 (19)	C2—C1—C6—C7	−175.1 (4)
N3—Zn1—O2—C9	102.63 (19)	N2^i—N1—C7—C6	−1.0 (5)
N1—Zn1—O2—C9	−170.48 (18)	Zn1—N1—C7—C6	177.2 (2)
N1^i—Zn1—O2—C9	9.52 (18)	N2^i—N1—C7—C8	−179.6 (3)
O2^i—Zn1—N1—C7	−169.7 (3)	Zn1—N1—C7—C8	−1.5 (5)
O2—Zn1—N1—C7	10.3 (3)	C5—C6—C7—N1	44.0 (5)
N3^i—Zn1—N1—C7	−81.0 (3)	C1—C6—C7—N1	−141.6 (4)
N3—Zn1—N1—C7	99.0 (3)	C5—C6—C7—C8	−137.4 (4)
N1^i—Zn1—N1—C7	101 (100)	C1—C6—C7—C8	37.0 (4)
O2^i—Zn1—N1—N2^i	8.53 (16)	Zn1—O2—C9—N2	−10.1 (3)
O2—Zn1—N1—N2^i	−171.47 (16)	Zn1—O2—C9—C10	169.17 (17)
N3^i—Zn1—N1—N2^i	97.24 (18)	N1^i—N2—C9—O2	1.8 (4)
N3—Zn1—N1—N2^i	−82.76 (18)	N1^i—N2—C9—C10	−177.5 (2)
N1^i—Zn1—N1—N2^i	−81 (100)	O2—C9—C10—C11	171.9 (3)
O2^i—Zn1—N3—C16	22.6 (3)	N2—C9—C10—C11	−8.7 (4)
O2—Zn1—N3—C16	−157.4 (3)	O2—C9—C10—C15	−8.5 (4)
N3^i—Zn1—N3—C16	−113 (100)	N2—C9—C10—C15	170.9 (3)
N1—Zn1—N3—C16	98.8 (3)	C15—C10—C11—C12	−1.3 (5)
N1^i—Zn1—N3—C16	−81.2 (3)	C9—C10—C11—C12	178.3 (3)
O2^i—Zn1—N3—C20	−152.2 (3)	C10—C11—C12—C13	0.2 (6)
O2—Zn1—N3—C20	27.8 (3)	C11—C12—C13—C14	0.7 (6)
N3^i—Zn1—N3—C20	72 (100)	C12—C13—C14—C15	−0.6 (6)
N1—Zn1—N3—C20	−76.1 (3)	C13—C14—C15—C10	−0.6 (5)
N1^i—Zn1—N3—C20	103.9 (3)	C11—C10—C15—C14	1.5 (5)
C6—C1—C2—C3	2.6 (7)	C9—C10—C15—C14	−178.1 (3)
C1—C2—C3—C4	−2.8 (8)	C20—N3—C16—C17	−0.1 (5)
C2—C3—C4—C5	0.8 (8)	Zn1—N3—C16—C17	−175.0 (3)
C3—C4—C5—O1	179.9 (4)	N3—C16—C17—C18	1.0 (6)
C3—C4—C5—C6	1.4 (6)	C16—C17—C18—C19	−1.4 (6)
O1—C5—C6—C1	180.0 (3)	C17—C18—C19—C20	1.0 (7)
C4—C5—C6—C1	−1.6 (5)	C16—N3—C20—C19	−0.4 (6)
O1—C5—C6—C7	−5.7 (5)	Zn1—N3—C20—C19	174.8 (3)
C4—C5—C6—C7	172.7 (3)	C18—C19—C20—N3	0.0 (7)

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1	0.77 (4)	2.56 (4)	3.120 (4)	131 (3)
O1—H1O···N2^i	0.77 (4)	1.83 (4)	2.545 (4)	155 (3)
C8—H8A···O2	0.96	2.24	3.185 (4)	167
C20—H20A···O2	0.93	2.52	3.069 (5)	118
C13—H13A···O1^ii	0.93	2.50	3.344 (5)	152

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