[2-Oxido-1-naphthaldehyde (2-hydroxy­benzoyl)hydrazonato]pyridine­copper(II)

The approximately planar complex mol­ecule, [Cu(C₁₈H₁₂N₂O₃)(C₅H₅N)], contains one L²⁻ ligand (L²⁻ is the dianion of 2-hydr­oxy-1-naphthaldehyde 2-hydroxy­benzoyl­hydra­zone), one Cu atom and one pyridine mol­ecule. The Cu centre shows square-planar N₂O₂Cu coordination. The tridentate dianion has an intra­molecular N...H—O hydrogen bond. Each pair of adjacent mol­ecules is linked together by π–π stacking and Cu...N inter­actions, which lead to the existence of a dimer. Owing to C—H...O hydrogen bonds, these dimers are further assembled into a two-dimensional framework.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.045
• wR factor = 0.117
• Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT410_ALERT_2_C Short Intra H...H Contact  H1     ..  H10     ..       1.99 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H20    ..  O3      ..       2.81 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          3
            N3  -CU1 -N1  -C1   -135.30  0.70   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          6
            N3  -CU1 -N1  -N2     42.50  0.80   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         10
            N1  -CU1 -N3  -C23   130.30  0.70   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         13
            N1  -CU1 -N3  -C19   -47.80  0.80   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         16
            O2  -CU1 -O1  -C3    -25.90  1.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         18
            O1  -CU1 -O2  -C12    24.80  1.00   1.555   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

   1 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
   8 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); 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: SHELXTL.

[2-Oxido-1-naphthaldehyde (2-hydroxybenzoyl)hydrazonato]pyridinecopper(II)

Crystal data

[Cu(C18H12N2O3)(C5H5N)]	F(000) = 916
Mr = 446.94	Dx = 1.575 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.745 (2) Å	Cell parameters from 2185 reflections
b = 8.1666 (17) Å	θ = 2.4–22.8°
c = 20.380 (4) Å	µ = 1.19 mm^−1
β = 105.397 (3)°	T = 298 K
V = 1884.5 (7) Å^3	Block, dark-green
Z = 4	0.28 × 0.21 × 0.12 mm

Data collection

Siemens SMART CCD area-detector diffractometer	3369 independent reflections
Radiation source: fine-focus sealed tube	2557 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
φ and ω scans	θmax = 25.2°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→14
Tmin = 0.732, Tmax = 0.870	k = −9→9
9587 measured reflections	l = −23→24

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.117	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0671P)^2] where P = (Fo^2 + 2Fc^2)/3
3369 reflections	(Δ/σ)max = 0.001
271 parameters	Δρmax = 0.42 e Å^−3
0 restraints	Δρmin = −0.22 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	0.37035 (3)	0.35584 (5)	0.538908 (19)	0.04049 (17)
N1	0.4003 (2)	0.3662 (3)	0.45168 (13)	0.0359 (6)
N2	0.5022 (2)	0.2846 (3)	0.44709 (13)	0.0398 (6)
N3	0.3656 (2)	0.3512 (3)	0.63614 (14)	0.0429 (7)
O1	0.22946 (18)	0.4762 (3)	0.50983 (11)	0.0451 (6)
O2	0.51191 (18)	0.2262 (3)	0.55857 (11)	0.0430 (5)
O3	0.6526 (2)	0.1424 (3)	0.39276 (13)	0.0728 (9)
H3	0.5959	0.1997	0.3941	0.109*
C1	0.3401 (3)	0.4425 (4)	0.39870 (16)	0.0370 (7)
H1	0.3697	0.4427	0.3606	0.044*
C2	0.2323 (3)	0.5267 (4)	0.39339 (15)	0.0356 (7)
C3	0.1841 (3)	0.5376 (4)	0.44958 (17)	0.0399 (8)
C4	0.0754 (3)	0.6247 (4)	0.44113 (19)	0.0472 (9)
H4	0.0419	0.6322	0.4776	0.057*
C5	0.0208 (3)	0.6960 (4)	0.3817 (2)	0.0524 (9)
H5	−0.0497	0.7514	0.3783	0.063*
C6	0.0664 (3)	0.6897 (4)	0.32421 (18)	0.0449 (8)
C7	0.0093 (3)	0.7674 (4)	0.2627 (2)	0.0559 (9)
H7	−0.0603	0.8244	0.2600	0.067*
C8	0.0519 (3)	0.7621 (5)	0.20754 (19)	0.0563 (10)
H8	0.0122	0.8139	0.1673	0.068*
C9	0.1566 (3)	0.6772 (5)	0.2121 (2)	0.0564 (10)
H9	0.1867	0.6714	0.1743	0.068*
C10	0.2158 (3)	0.6022 (4)	0.27137 (17)	0.0472 (9)
H10	0.2863	0.5482	0.2731	0.057*
C11	0.1731 (3)	0.6042 (4)	0.32986 (17)	0.0389 (8)
C12	0.5519 (3)	0.2132 (4)	0.50576 (17)	0.0366 (7)
C13	0.6577 (3)	0.1120 (4)	0.51070 (17)	0.0376 (7)
C14	0.7017 (3)	0.0795 (5)	0.45528 (18)	0.0493 (9)
C15	0.8002 (3)	−0.0206 (5)	0.4634 (2)	0.0617 (11)
H15	0.8289	−0.0442	0.4261	0.074*
C16	0.8552 (3)	−0.0846 (5)	0.5255 (2)	0.0609 (11)
H16	0.9218	−0.1498	0.5304	0.073*
C17	0.8131 (3)	−0.0535 (4)	0.5806 (2)	0.0577 (10)
H17	0.8502	−0.0983	0.6228	0.069*
C18	0.7155 (3)	0.0445 (4)	0.57320 (17)	0.0449 (8)
H18	0.6875	0.0662	0.6109	0.054*
C19	0.4437 (4)	0.2628 (5)	0.68190 (19)	0.0681 (12)
H19	0.4973	0.1991	0.6668	0.082*
C20	0.4491 (4)	0.2606 (6)	0.7490 (2)	0.0763 (13)
H20	0.5062	0.1982	0.7790	0.092*
C21	0.3704 (4)	0.3502 (4)	0.77237 (19)	0.0602 (11)
H21	0.3730	0.3516	0.8184	0.072*
C22	0.2879 (4)	0.4379 (5)	0.72634 (19)	0.0633 (11)
H22	0.2311	0.4979	0.7402	0.076*
C23	0.2891 (3)	0.4370 (5)	0.65940 (18)	0.0535 (9)
H23	0.2333	0.4998	0.6287	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0381 (3)	0.0503 (3)	0.0345 (3)	0.00528 (18)	0.01215 (18)	−0.00078 (18)
N1	0.0336 (14)	0.0389 (15)	0.0346 (15)	0.0011 (12)	0.0081 (12)	−0.0045 (12)
N2	0.0336 (14)	0.0468 (16)	0.0402 (17)	0.0070 (13)	0.0121 (12)	−0.0024 (13)
N3	0.0428 (16)	0.0491 (17)	0.0378 (16)	0.0070 (13)	0.0125 (13)	0.0005 (13)
O1	0.0427 (13)	0.0544 (15)	0.0407 (14)	0.0080 (11)	0.0156 (11)	0.0001 (11)
O2	0.0407 (13)	0.0546 (14)	0.0354 (13)	0.0069 (11)	0.0130 (10)	0.0010 (11)
O3	0.0677 (18)	0.109 (2)	0.0475 (17)	0.0357 (16)	0.0260 (14)	0.0031 (15)
C1	0.0383 (18)	0.0421 (19)	0.0321 (18)	−0.0011 (15)	0.0120 (14)	−0.0037 (15)
C2	0.0339 (17)	0.0345 (17)	0.0365 (18)	−0.0026 (14)	0.0061 (14)	−0.0065 (14)
C3	0.0370 (18)	0.0385 (19)	0.044 (2)	−0.0013 (15)	0.0097 (15)	−0.0054 (15)
C4	0.042 (2)	0.049 (2)	0.054 (2)	0.0068 (16)	0.0196 (17)	−0.0035 (17)
C5	0.040 (2)	0.049 (2)	0.066 (3)	0.0110 (17)	0.0116 (18)	−0.0017 (19)
C6	0.043 (2)	0.0376 (19)	0.050 (2)	−0.0004 (15)	0.0059 (17)	−0.0030 (16)
C7	0.048 (2)	0.051 (2)	0.062 (3)	0.0077 (18)	0.0019 (19)	0.0046 (19)
C8	0.056 (2)	0.054 (2)	0.051 (2)	−0.0073 (19)	−0.0016 (19)	0.0113 (19)
C9	0.061 (2)	0.057 (2)	0.049 (2)	−0.010 (2)	0.0091 (19)	0.0021 (18)
C10	0.044 (2)	0.050 (2)	0.044 (2)	−0.0006 (16)	0.0060 (16)	−0.0008 (16)
C11	0.0373 (18)	0.0321 (17)	0.044 (2)	−0.0039 (14)	0.0042 (15)	−0.0044 (14)
C12	0.0356 (17)	0.0346 (18)	0.041 (2)	−0.0036 (14)	0.0127 (15)	−0.0052 (15)
C13	0.0345 (17)	0.0319 (17)	0.045 (2)	−0.0010 (14)	0.0091 (15)	−0.0035 (14)
C14	0.048 (2)	0.056 (2)	0.043 (2)	0.0082 (18)	0.0110 (17)	−0.0062 (17)
C15	0.056 (2)	0.067 (3)	0.068 (3)	0.014 (2)	0.026 (2)	−0.013 (2)
C16	0.046 (2)	0.051 (2)	0.084 (3)	0.0124 (18)	0.015 (2)	−0.007 (2)
C17	0.049 (2)	0.046 (2)	0.072 (3)	0.0087 (18)	0.008 (2)	0.009 (2)
C18	0.046 (2)	0.0392 (19)	0.050 (2)	0.0013 (16)	0.0134 (16)	0.0017 (16)
C19	0.075 (3)	0.090 (3)	0.043 (2)	0.039 (3)	0.022 (2)	0.006 (2)
C20	0.089 (3)	0.099 (3)	0.041 (2)	0.043 (3)	0.017 (2)	0.014 (2)
C21	0.083 (3)	0.061 (3)	0.041 (2)	0.016 (2)	0.025 (2)	0.0055 (19)
C22	0.080 (3)	0.069 (3)	0.051 (2)	0.028 (2)	0.035 (2)	0.006 (2)
C23	0.054 (2)	0.065 (2)	0.043 (2)	0.0187 (19)	0.0148 (17)	0.0063 (19)

Geometric parameters (Å, º)

Cu1—O1	1.880 (2)	C8—C9	1.394 (5)
Cu1—N1	1.904 (3)	C8—H8	0.9300
Cu1—O2	1.922 (2)	C9—C10	1.368 (5)
Cu1—N3	1.997 (3)	C9—H9	0.9300
N1—C1	1.284 (4)	C10—C11	1.411 (5)
N1—N2	1.395 (3)	C10—H10	0.9300
N2—C12	1.319 (4)	C12—C13	1.473 (4)
N3—C23	1.323 (4)	C13—C14	1.386 (5)
N3—C19	1.333 (5)	C13—C18	1.389 (4)
O1—C3	1.302 (4)	C14—C15	1.391 (5)
O2—C12	1.288 (3)	C15—C16	1.363 (5)
O3—C14	1.353 (4)	C15—H15	0.9300
O3—H3	0.8200	C16—C17	1.366 (5)
C1—C2	1.420 (4)	C16—H16	0.9300
C1—H1	0.9300	C17—C18	1.372 (4)
C2—C3	1.409 (4)	C17—H17	0.9300
C2—C11	1.443 (4)	C18—H18	0.9300
C3—C4	1.430 (4)	C19—C20	1.353 (5)
C4—C5	1.344 (5)	C19—H19	0.9300
C4—H4	0.9300	C20—C21	1.360 (5)
C5—C6	1.412 (5)	C20—H20	0.9300
C5—H5	0.9300	C21—C22	1.360 (5)
C6—C7	1.406 (5)	C21—H21	0.9300
C6—C11	1.413 (4)	C22—C23	1.368 (5)
C7—C8	1.346 (5)	C22—H22	0.9300
C7—H7	0.9300	C23—H23	0.9300
O1—Cu1—N1	92.75 (10)	C9—C10—C11	122.0 (3)
O1—Cu1—O2	173.84 (9)	C9—C10—H10	119.0
N1—Cu1—O2	81.66 (10)	C11—C10—H10	119.0
O1—Cu1—N3	93.94 (10)	C10—C11—C6	116.4 (3)
N1—Cu1—N3	171.13 (11)	C10—C11—C2	124.0 (3)
O2—Cu1—N3	91.89 (10)	C6—C11—C2	119.7 (3)
C1—N1—N2	117.8 (2)	O2—C12—N2	123.4 (3)
C1—N1—Cu1	127.6 (2)	O2—C12—C13	118.5 (3)
N2—N1—Cu1	114.59 (19)	N2—C12—C13	118.1 (3)
C12—N2—N1	109.3 (2)	C14—C13—C18	118.3 (3)
C23—N3—C19	116.3 (3)	C14—C13—C12	122.8 (3)
C23—N3—Cu1	123.1 (2)	C18—C13—C12	118.9 (3)
C19—N3—Cu1	120.6 (2)	O3—C14—C13	122.5 (3)
C3—O1—Cu1	127.19 (19)	O3—C14—C15	118.0 (3)
C12—O2—Cu1	111.0 (2)	C13—C14—C15	119.6 (3)
C14—O3—H3	109.5	C16—C15—C14	120.7 (3)
N1—C1—C2	125.4 (3)	C16—C15—H15	119.7
N1—C1—H1	117.3	C14—C15—H15	119.7
C2—C1—H1	117.3	C15—C16—C17	120.4 (4)
C3—C2—C1	120.8 (3)	C15—C16—H16	119.8
C3—C2—C11	120.0 (3)	C17—C16—H16	119.8
C1—C2—C11	119.2 (3)	C16—C17—C18	119.5 (4)
O1—C3—C2	126.1 (3)	C16—C17—H17	120.3
O1—C3—C4	115.7 (3)	C18—C17—H17	120.3
C2—C3—C4	118.1 (3)	C17—C18—C13	121.5 (3)
C5—C4—C3	121.4 (3)	C17—C18—H18	119.2
C5—C4—H4	119.3	C13—C18—H18	119.2
C3—C4—H4	119.3	N3—C19—C20	123.6 (3)
C4—C5—C6	122.4 (3)	N3—C19—H19	118.2
C4—C5—H5	118.8	C20—C19—H19	118.2
C6—C5—H5	118.8	C19—C20—C21	119.5 (4)
C7—C6—C5	121.8 (3)	C19—C20—H20	120.3
C7—C6—C11	119.9 (3)	C21—C20—H20	120.3
C5—C6—C11	118.3 (3)	C22—C21—C20	117.9 (4)
C8—C7—C6	122.4 (4)	C22—C21—H21	121.0
C8—C7—H7	118.8	C20—C21—H21	121.0
C6—C7—H7	118.8	C21—C22—C23	119.4 (3)
C7—C8—C9	118.5 (4)	C21—C22—H22	120.3
C7—C8—H8	120.8	C23—C22—H22	120.3
C9—C8—H8	120.8	N3—C23—C22	123.2 (3)
C10—C9—C8	121.0 (4)	N3—C23—H23	118.4
C10—C9—H9	119.5	C22—C23—H23	118.4
C8—C9—H9	119.5
O1—Cu1—N1—C1	3.6 (3)	C8—C9—C10—C11	1.2 (5)
O2—Cu1—N1—C1	−179.0 (3)	C9—C10—C11—C6	−0.7 (5)
N3—Cu1—N1—C1	−135.3 (7)	C9—C10—C11—C2	179.9 (3)
O1—Cu1—N1—N2	−178.60 (19)	C7—C6—C11—C10	−0.3 (5)
O2—Cu1—N1—N2	−1.20 (18)	C5—C6—C11—C10	−179.6 (3)
N3—Cu1—N1—N2	42.5 (8)	C7—C6—C11—C2	179.1 (3)
C1—N1—N2—C12	−179.7 (3)	C5—C6—C11—C2	−0.1 (5)
Cu1—N1—N2—C12	2.3 (3)	C3—C2—C11—C10	178.8 (3)
O1—Cu1—N3—C23	−8.6 (3)	C1—C2—C11—C10	0.1 (5)
N1—Cu1—N3—C23	130.3 (7)	C3—C2—C11—C6	−0.6 (4)
O2—Cu1—N3—C23	173.4 (3)	C1—C2—C11—C6	−179.4 (3)
O1—Cu1—N3—C19	173.3 (3)	Cu1—O2—C12—N2	1.7 (4)
N1—Cu1—N3—C19	−47.8 (8)	Cu1—O2—C12—C13	−177.6 (2)
O2—Cu1—N3—C19	−4.7 (3)	N1—N2—C12—O2	−2.7 (4)
N1—Cu1—O1—C3	−1.2 (3)	N1—N2—C12—C13	176.6 (2)
O2—Cu1—O1—C3	−25.9 (10)	O2—C12—C13—C14	174.5 (3)
N3—Cu1—O1—C3	173.0 (3)	N2—C12—C13—C14	−4.8 (5)
O1—Cu1—O2—C12	24.8 (10)	O2—C12—C13—C18	−4.7 (4)
N1—Cu1—O2—C12	−0.2 (2)	N2—C12—C13—C18	175.9 (3)
N3—Cu1—O2—C12	−174.1 (2)	C18—C13—C14—O3	−178.7 (3)
N2—N1—C1—C2	177.5 (3)	C12—C13—C14—O3	2.0 (5)
Cu1—N1—C1—C2	−4.8 (5)	C18—C13—C14—C15	1.0 (5)
N1—C1—C2—C3	2.5 (5)	C12—C13—C14—C15	−178.3 (3)
N1—C1—C2—C11	−178.7 (3)	O3—C14—C15—C16	178.5 (4)
Cu1—O1—C3—C2	−0.3 (5)	C13—C14—C15—C16	−1.2 (6)
Cu1—O1—C3—C4	−179.8 (2)	C14—C15—C16—C17	1.1 (6)
C1—C2—C3—O1	0.1 (5)	C15—C16—C17—C18	−0.8 (6)
C11—C2—C3—O1	−178.6 (3)	C16—C17—C18—C13	0.6 (5)
C1—C2—C3—C4	179.7 (3)	C14—C13—C18—C17	−0.7 (5)
C11—C2—C3—C4	1.0 (4)	C12—C13—C18—C17	178.6 (3)
O1—C3—C4—C5	178.9 (3)	C23—N3—C19—C20	−1.6 (6)
C2—C3—C4—C5	−0.7 (5)	Cu1—N3—C19—C20	176.6 (4)
C3—C4—C5—C6	0.0 (6)	N3—C19—C20—C21	1.1 (7)
C4—C5—C6—C7	−178.8 (3)	C19—C20—C21—C22	0.7 (7)
C4—C5—C6—C11	0.4 (5)	C20—C21—C22—C23	−2.0 (7)
C5—C6—C7—C8	−179.9 (3)	C19—N3—C23—C22	0.2 (6)
C11—C6—C7—C8	0.9 (5)	Cu1—N3—C23—C22	−178.0 (3)
C6—C7—C8—C9	−0.4 (6)	C21—C22—C23—N3	1.6 (6)
C7—C8—C9—C10	−0.7 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O3^i	0.93	2.81	3.347 (5)	118

Symmetry code: (i) x, −y+1/2, z+1/2.