Bis{2′-[1-(2-hydroxy-5-chloro­phenyl)­ethyl­idene]­benzohydr­azido-κ²O,N^2′}bis­(pyridine-κN)­zinc(II)

The title compound, [Zn(C₁₅H₁₃ClN₂O₂)₂(C₅H₅N)₂], is a centrosymmetric monomer with octahedral geometry about the Zn atom. The mol­ecule is stabilized by intermolecular C—H...O and C—H...Cl interactions, so forming a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.054
• wR factor = 0.134
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ......         C9
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  N2      ..       3.27 Ang.
PLAT706_ALERT_1_C H...A   Calc     1.74(4), Rep     1.69(4), Dev..       1.25 Sigma
              H2D  -N2      1.555   3.656
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            O1  -ZN1 -O1  -C7   -121.00100.00   3.656   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          8
            N1  -ZN1 -N1  -C8    -59.00 35.00   3.656   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         13
            N1  -ZN1 -N1  -N2    117.00 35.00   3.656   1.555   1.555   3.656
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         20
            N3  -ZN1 -N3  -C16   101.00100.00   3.656   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         25
            N3  -ZN1 -N3  -C20   -79.00100.00   3.656   1.555   1.555   1.555

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   6 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: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Bis{2'-[1-(2-hydroxy-5-chlorophenyl)ethylidine]benzohydrazido- κ²O,N^2'}bis(pyridine-κN)zinc(II)

Crystal data

[Zn(C15H13ClN2O2)2(C5H5N)2]	F(000) = 824
Mr = 799.00	Dx = 1.384 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2652 reflections
a = 10.2453 (17) Å	θ = 2.0–26.5°
b = 15.388 (3) Å	µ = 0.83 mm^−1
c = 12.359 (2) Å	T = 273 K
β = 100.189 (3)°	Plate, light yellow
V = 1917.8 (5) Å^3	0.48 × 0.46 × 0.09 mm
Z = 2

Data collection

Bruker SMART APEX area-detector diffractometer	3939 independent reflections
Radiation source: fine-focus sealed tube	3205 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 83.66 pixels mm^-1	θmax = 26.5°, θmin = 2.0°
ω scan	h = −9→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→19
Tmin = 0.692, Tmax = 0.929	l = −15→14
8429 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0641P)^2 + 0.6133P] where P = (Fo^2 + 2Fc^2)/3
3939 reflections	(Δ/σ)max < 0.001
245 parameters	Δρmax = 0.54 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

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

	x	y	z	Uiso*/Ueq
Zn1	0.5000	0.0000	0.5000	0.04693 (17)
Cl1	0.46583 (15)	0.13135 (8)	−0.15097 (8)	0.1098 (4)
O1	0.59737 (19)	0.11333 (12)	0.53713 (14)	0.0503 (5)
O2	0.1376 (2)	0.02337 (17)	0.1666 (2)	0.0711 (7)
H2D	0.182 (4)	−0.006 (2)	0.216 (3)	0.071 (11)*
N1	0.4076 (2)	0.01629 (13)	0.32608 (17)	0.0428 (5)
N2	0.6782 (2)	0.05290 (13)	0.70600 (16)	0.0417 (5)
N3	0.3186 (2)	0.06151 (16)	0.54533 (18)	0.0533 (6)
C1	0.8255 (3)	0.2050 (2)	0.7659 (3)	0.0653 (8)
H1B	0.8202	0.1642	0.8205	0.078*
C2	0.9034 (4)	0.2774 (3)	0.7900 (3)	0.0906 (12)
H2C	0.9512	0.2851	0.8606	0.109*
C3	0.9110 (5)	0.3381 (3)	0.7112 (4)	0.0957 (14)
H3A	0.9643	0.3869	0.7278	0.115*
C4	0.8405 (4)	0.3269 (2)	0.6086 (4)	0.0865 (12)
H4A	0.8453	0.3686	0.5549	0.104*
C5	0.7624 (3)	0.25536 (19)	0.5827 (3)	0.0601 (8)
H5A	0.7139	0.2489	0.5121	0.072*
C6	0.7553 (3)	0.19244 (17)	0.6613 (2)	0.0442 (6)
C7	0.6709 (2)	0.11446 (16)	0.63095 (19)	0.0387 (5)
C8	0.4212 (3)	0.07092 (17)	0.2494 (2)	0.0464 (6)
C9	0.5179 (4)	0.1437 (2)	0.2796 (3)	0.0807 (12)
H9A	0.5573	0.1391	0.3558	0.121*
H9B	0.4724	0.1983	0.2669	0.121*
H9C	0.5859	0.1405	0.2353	0.121*
C10	0.3518 (3)	0.06968 (17)	0.1325 (2)	0.0456 (6)
C11	0.4255 (3)	0.09555 (18)	0.0531 (2)	0.0551 (7)
H11A	0.5155	0.1074	0.0741	0.066*
C12	0.3672 (4)	0.1038 (2)	−0.0552 (3)	0.0676 (9)
C13	0.2346 (5)	0.0890 (2)	−0.0877 (3)	0.0781 (11)
H13A	0.1950	0.0969	−0.1608	0.094*
C14	0.1610 (4)	0.0626 (2)	−0.0125 (3)	0.0746 (10)
H14A	0.0709	0.0521	−0.0351	0.090*
C15	0.2173 (3)	0.05092 (18)	0.0978 (2)	0.0543 (7)
C16	0.2223 (4)	0.0164 (2)	0.5770 (3)	0.0647 (8)
H16A	0.2295	−0.0438	0.5806	0.078*
C17	0.1109 (4)	0.0552 (3)	0.6052 (3)	0.0775 (10)
H17A	0.0452	0.0216	0.6277	0.093*
C18	0.0996 (4)	0.1427 (3)	0.5993 (3)	0.0835 (11)
H18A	0.0253	0.1703	0.6169	0.100*
C19	0.1976 (4)	0.1893 (3)	0.5675 (4)	0.0904 (12)
H19A	0.1922	0.2496	0.5638	0.108*
C20	0.3044 (4)	0.1475 (2)	0.5409 (3)	0.0744 (9)
H20A	0.3708	0.1805	0.5185	0.089*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0543 (3)	0.0434 (3)	0.0407 (2)	−0.0127 (2)	0.00203 (18)	−0.00083 (17)
Cl1	0.1753 (12)	0.1024 (8)	0.0643 (6)	0.0160 (8)	0.0558 (7)	0.0238 (5)
O1	0.0604 (12)	0.0428 (10)	0.0441 (10)	−0.0118 (9)	−0.0003 (8)	0.0033 (8)
O2	0.0457 (12)	0.0806 (16)	0.0842 (16)	0.0065 (12)	0.0036 (11)	0.0239 (13)
N1	0.0485 (13)	0.0389 (12)	0.0408 (11)	−0.0097 (9)	0.0070 (9)	−0.0009 (8)
N2	0.0441 (12)	0.0394 (12)	0.0411 (11)	−0.0081 (9)	0.0060 (9)	−0.0010 (9)
N3	0.0543 (14)	0.0540 (15)	0.0503 (13)	−0.0025 (12)	0.0060 (10)	0.0002 (11)
C1	0.070 (2)	0.067 (2)	0.0582 (18)	−0.0218 (17)	0.0097 (15)	−0.0114 (15)
C2	0.097 (3)	0.092 (3)	0.081 (3)	−0.046 (2)	0.008 (2)	−0.030 (2)
C3	0.108 (3)	0.067 (2)	0.119 (4)	−0.050 (2)	0.040 (3)	−0.035 (2)
C4	0.115 (3)	0.050 (2)	0.102 (3)	−0.029 (2)	0.039 (2)	−0.0021 (19)
C5	0.072 (2)	0.0425 (16)	0.0681 (19)	−0.0109 (15)	0.0196 (15)	0.0003 (13)
C6	0.0409 (14)	0.0398 (14)	0.0543 (15)	−0.0051 (11)	0.0154 (11)	−0.0096 (11)
C7	0.0379 (13)	0.0393 (13)	0.0404 (13)	−0.0029 (11)	0.0112 (10)	−0.0046 (10)
C8	0.0531 (16)	0.0400 (14)	0.0453 (14)	−0.0067 (12)	0.0061 (11)	0.0010 (11)
C9	0.115 (3)	0.067 (2)	0.0531 (18)	−0.045 (2)	−0.0035 (18)	0.0125 (15)
C10	0.0572 (17)	0.0348 (13)	0.0437 (13)	0.0036 (12)	0.0056 (11)	0.0009 (10)
C11	0.069 (2)	0.0471 (16)	0.0497 (15)	0.0024 (14)	0.0120 (13)	0.0073 (12)
C12	0.110 (3)	0.0480 (18)	0.0475 (16)	0.0085 (18)	0.0225 (17)	0.0052 (13)
C13	0.121 (3)	0.058 (2)	0.0454 (17)	−0.001 (2)	−0.0142 (19)	0.0036 (14)
C14	0.080 (2)	0.060 (2)	0.071 (2)	−0.0042 (18)	−0.0204 (18)	0.0099 (16)
C15	0.0610 (19)	0.0385 (15)	0.0592 (17)	0.0053 (13)	−0.0003 (14)	0.0030 (12)
C16	0.068 (2)	0.064 (2)	0.0631 (19)	−0.0033 (17)	0.0135 (16)	−0.0014 (15)
C17	0.063 (2)	0.098 (3)	0.074 (2)	−0.006 (2)	0.0179 (17)	0.000 (2)
C18	0.065 (2)	0.098 (3)	0.085 (3)	0.025 (2)	0.0094 (19)	0.000 (2)
C19	0.083 (3)	0.071 (3)	0.117 (3)	0.021 (2)	0.017 (2)	0.010 (2)
C20	0.069 (2)	0.060 (2)	0.094 (3)	0.0052 (18)	0.0126 (18)	0.0135 (18)

Geometric parameters (Å, º)

Zn1—O1^i	2.022 (2)	C5—H5A	0.9300
Zn1—O1	2.022 (2)	C6—C7	1.488 (3)
Zn1—N1	2.206 (2)	C8—C10	1.493 (4)
Zn1—N1^i	2.206 (2)	C8—C9	1.499 (4)
Zn1—N3	2.243 (3)	C9—H9A	0.9600
Zn1—N3^i	2.243 (3)	C9—H9B	0.9600
Cl1—C12	1.737 (4)	C9—H9C	0.9600
O1—C7	1.263 (3)	C10—C11	1.398 (4)
O2—C15	1.348 (5)	C10—C15	1.399 (4)
O2—H2D	0.87 (4)	C11—C12	1.372 (4)
N1—C8	1.291 (4)	C11—H11A	0.9300
N1—N2^i	1.393 (3)	C12—C13	1.366 (5)
N2—C7	1.321 (4)	C13—C14	1.359 (5)
N2—N1^i	1.393 (3)	C13—H13A	0.9300
N3—C16	1.324 (5)	C14—C15	1.395 (4)
N3—C20	1.331 (5)	C14—H14A	0.9300
C1—C2	1.372 (5)	C16—C17	1.385 (5)
C1—C6	1.378 (4)	C16—H16A	0.9300
C1—H1B	0.9300	C17—C18	1.353 (6)
C2—C3	1.361 (6)	C17—H17A	0.9300
C2—H2C	0.9300	C18—C19	1.348 (6)
C3—C4	1.356 (6)	C18—H18A	0.9300
C3—H3A	0.9300	C19—C20	1.359 (5)
C4—C5	1.366 (5)	C19—H19A	0.9300
C4—H4A	0.9300	C20—H20A	0.9300
C5—C6	1.383 (4)
O1^i—Zn1—O1	180.00 (13)	N2—C7—C6	116.3 (2)
O1^i—Zn1—N1	76.53 (8)	N1—C8—C10	127.3 (2)
O1—Zn1—N1	103.47 (8)	N1—C8—C9	117.1 (2)
O1^i—Zn1—N1^i	103.47 (8)	C10—C8—C9	115.6 (2)
O1—Zn1—N1^i	76.53 (8)	C8—C9—H9A	109.5
N1—Zn1—N1^i	180.0	C8—C9—H9B	109.5
O1^i—Zn1—N3	91.33 (10)	H9A—C9—H9B	109.5
O1—Zn1—N3	88.67 (10)	C8—C9—H9C	109.5
N1—Zn1—N3	87.98 (10)	H9A—C9—H9C	109.5
N1^i—Zn1—N3	92.02 (10)	H9B—C9—H9C	109.5
O1^i—Zn1—N3^i	88.67 (10)	C11—C10—C15	118.0 (3)
O1—Zn1—N3^i	91.33 (10)	C11—C10—C8	116.8 (3)
N1—Zn1—N3^i	92.02 (10)	C15—C10—C8	125.0 (2)
N1^i—Zn1—N3^i	87.98 (10)	C12—C11—C10	121.0 (3)
N3—Zn1—N3^i	180.0	C12—C11—H11A	119.5
C7—O1—Zn1	114.18 (16)	C10—C11—H11A	119.5
C15—O2—H2D	109 (3)	C13—C12—C11	120.7 (3)
C8—N1—N2^i	115.6 (2)	C13—C12—Cl1	120.5 (3)
C8—N1—Zn1	134.88 (18)	C11—C12—Cl1	118.8 (3)
N2^i—N1—Zn1	109.34 (14)	C14—C13—C12	119.4 (3)
C7—N2—N1^i	113.2 (2)	C14—C13—H13A	120.3
C16—N3—C20	116.8 (3)	C12—C13—H13A	120.3
C16—N3—Zn1	123.2 (2)	C13—C14—C15	121.6 (3)
C20—N3—Zn1	119.9 (2)	C13—C14—H14A	119.2
C2—C1—C6	120.3 (3)	C15—C14—H14A	119.2
C2—C1—H1B	119.9	O2—C15—C14	117.7 (3)
C6—C1—H1B	119.9	O2—C15—C10	123.1 (3)
C3—C2—C1	120.5 (4)	C14—C15—C10	119.2 (3)
C3—C2—H2C	119.8	N3—C16—C17	122.7 (3)
C1—C2—H2C	119.8	N3—C16—H16A	118.7
C4—C3—C2	119.6 (3)	C17—C16—H16A	118.7
C4—C3—H3A	120.2	C18—C17—C16	118.8 (4)
C2—C3—H3A	120.2	C18—C17—H17A	120.6
C3—C4—C5	121.0 (4)	C16—C17—H17A	120.6
C3—C4—H4A	119.5	C19—C18—C17	119.0 (4)
C5—C4—H4A	119.5	C19—C18—H18A	120.5
C4—C5—C6	120.1 (3)	C17—C18—H18A	120.5
C4—C5—H5A	119.9	C18—C19—C20	119.4 (4)
C6—C5—H5A	119.9	C18—C19—H19A	120.3
C1—C6—C5	118.5 (3)	C20—C19—H19A	120.3
C1—C6—C7	122.3 (3)	N3—C20—C19	123.3 (4)
C5—C6—C7	119.2 (2)	N3—C20—H20A	118.4
O1—C7—N2	125.8 (2)	C19—C20—H20A	118.4
O1—C7—C6	117.9 (2)
O1^i—Zn1—O1—C7	−121 (100)	N1^i—N2—C7—O1	−1.5 (4)
N1^i—Zn1—O1—C7	7.65 (17)	N1^i—N2—C7—C6	177.3 (2)
N1—Zn1—O1—C7	−172.35 (17)	C1—C6—C7—O1	171.5 (3)
N3—Zn1—O1—C7	100.11 (18)	C5—C6—C7—O1	−7.6 (4)
N3^i—Zn1—O1—C7	−79.89 (18)	C1—C6—C7—N2	−7.4 (4)
O1^i—Zn1—N1—C8	−167.1 (3)	C5—C6—C7—N2	173.6 (2)
O1—Zn1—N1—C8	12.9 (3)	N2^i—N1—C8—C10	2.4 (4)
N1^i—Zn1—N1—C8	−59 (35)	Zn1—N1—C8—C10	177.5 (2)
N3—Zn1—N1—C8	101.0 (3)	N2^i—N1—C8—C9	−177.0 (3)
N3^i—Zn1—N1—C8	−79.0 (3)	Zn1—N1—C8—C9	−2.0 (4)
O1^i—Zn1—N1—N2^i	8.19 (15)	N1—C8—C10—C11	−143.1 (3)
O1—Zn1—N1—N2^i	−171.81 (15)	C9—C8—C10—C11	36.3 (4)
N1^i—Zn1—N1—N2^i	117 (35)	N1—C8—C10—C15	41.8 (4)
N3—Zn1—N1—N2^i	−83.69 (16)	C9—C8—C10—C15	−138.7 (3)
N3^i—Zn1—N1—N2^i	96.31 (16)	C15—C10—C11—C12	1.1 (4)
O1^i—Zn1—N3—C16	24.2 (2)	C8—C10—C11—C12	−174.3 (3)
O1—Zn1—N3—C16	−155.8 (2)	C10—C11—C12—C13	1.7 (5)
N1^i—Zn1—N3—C16	−79.4 (2)	C10—C11—C12—Cl1	−177.1 (2)
N1—Zn1—N3—C16	100.6 (2)	C11—C12—C13—C14	−2.6 (5)
N3^i—Zn1—N3—C16	101 (100)	Cl1—C12—C13—C14	176.2 (3)
O1^i—Zn1—N3—C20	−155.8 (2)	C12—C13—C14—C15	0.6 (5)
O1—Zn1—N3—C20	24.2 (2)	C13—C14—C15—O2	−179.0 (3)
N1^i—Zn1—N3—C20	100.6 (2)	C13—C14—C15—C10	2.2 (5)
N1—Zn1—N3—C20	−79.4 (2)	C11—C10—C15—O2	178.3 (3)
N3^i—Zn1—N3—C20	−79 (100)	C8—C10—C15—O2	−6.7 (4)
C6—C1—C2—C3	0.7 (6)	C11—C10—C15—C14	−3.0 (4)
C1—C2—C3—C4	0.4 (7)	C8—C10—C15—C14	172.0 (3)
C2—C3—C4—C5	−0.4 (7)	C20—N3—C16—C17	−0.2 (5)
C3—C4—C5—C6	−0.7 (6)	Zn1—N3—C16—C17	179.8 (2)
C2—C1—C6—C5	−1.7 (5)	N3—C16—C17—C18	0.5 (6)
C2—C1—C6—C7	179.2 (3)	C16—C17—C18—C19	−0.8 (6)
C4—C5—C6—C1	1.7 (5)	C17—C18—C19—C20	0.8 (6)
C4—C5—C6—C7	−179.2 (3)	C16—N3—C20—C19	0.3 (5)
Zn1—O1—C7—N2	−6.4 (3)	Zn1—N3—C20—C19	−179.7 (3)
Zn1—O1—C7—C6	174.85 (16)	C18—C19—C20—N3	−0.6 (6)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2D···N1	0.87 (5)	2.45 (4)	3.101 (4)	132 (4)
C9—H9A···O1	0.96	2.24	3.177 (4)	165
C20—H20A···O1	0.93	2.51	3.053 (5)	117
O2—H2D···N2^i	0.87 (5)	1.69 (4)	2.522 (4)	160 (4)
C3—H3A···O2^ii	0.93	2.47	3.272 (6)	144
C9—H9B···Cl1^iii	0.96	2.82	3.629 (5)	143

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