3-Hydr­oxy-4-methoxy­benzaldehyde (pyridine-2-carbon­yl)hydrazone

The molecule of the title compound, C₁₄H₁₃N₃O₃, is nearly planar. The crystal structure is stabilized mainly through inter­molecular O—H...O, N—H...O and C—H...O hydrogen bonds

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.039
• wR factor = 0.107
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

---

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.

3-Hydroxy-4-methoxybenzaldehyde (pyridine-2-carbonyl)hydrazone

Crystal data

C14H13N3O3	F(000) = 568
Mr = 271.27	Dx = 1.344 Mg m^−3
Monoclinic, P21/n	Melting point = 448–449 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.515 (3) Å	Cell parameters from 3286 reflections
b = 13.590 (5) Å	θ = 2.2–26.4°
c = 13.172 (5) Å	µ = 0.10 mm^−1
β = 94.689 (7)°	T = 294 K
V = 1340.6 (9) Å^3	Block, colourless
Z = 4	0.24 × 0.22 × 0.18 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer	2744 independent reflections
Radiation source: fine-focus sealed tube	2124 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 26.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −9→4
Tmin = 0.970, Tmax = 0.983	k = −16→16
7403 measured reflections	l = −15→16

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.107	w = 1/[σ^2(Fo^2) + (0.0447P)^2 + 0.4125P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
2744 reflections	Δρmax = 0.16 e Å^−3
191 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.072 (4)

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
O1	0.31713 (15)	1.06286 (9)	0.68041 (10)	0.0551 (4)
O2	0.47414 (15)	0.78899 (9)	0.23738 (9)	0.0482 (3)
H2B	0.538 (3)	0.8350 (18)	0.2689 (17)	0.082 (7)*
O3	0.24731 (13)	0.66584 (8)	0.14967 (8)	0.0384 (3)
N1	−0.07973 (19)	1.00590 (11)	0.79677 (11)	0.0475 (4)
N2	0.10376 (17)	0.94748 (10)	0.64619 (10)	0.0367 (3)
H2A	0.003 (3)	0.9225 (13)	0.6669 (14)	0.051 (5)*
N3	0.17186 (15)	0.91462 (9)	0.55741 (9)	0.0352 (3)
C1	−0.1743 (3)	1.03223 (15)	0.87351 (15)	0.0585 (5)
H1	−0.2858	1.0035	0.8778	0.070*
C2	−0.1165 (3)	1.09922 (14)	0.94631 (15)	0.0614 (5)
H2	−0.1871	1.1158	0.9985	0.074*
C3	0.0459 (3)	1.14087 (15)	0.94059 (16)	0.0683 (6)
H3	0.0893	1.1859	0.9897	0.082*
C4	0.1468 (3)	1.11626 (14)	0.86152 (15)	0.0575 (5)
H4	0.2582	1.1447	0.8560	0.069*
C5	0.0789 (2)	1.04868 (11)	0.79100 (12)	0.0369 (4)
C6	0.17962 (19)	1.02117 (11)	0.70115 (12)	0.0359 (4)
C7	0.07981 (19)	0.84611 (11)	0.51278 (11)	0.0367 (4)
H7	−0.0215	0.8241	0.5420	0.044*
C8	0.12566 (19)	0.80057 (11)	0.41827 (11)	0.0331 (3)
C9	0.0076 (2)	0.73285 (12)	0.37225 (13)	0.0437 (4)
H9	−0.0975	0.7184	0.4018	0.052*
C10	0.0438 (2)	0.68619 (12)	0.28264 (13)	0.0429 (4)
H10	−0.0373	0.6412	0.2524	0.051*
C11	0.19982 (18)	0.70629 (10)	0.23816 (11)	0.0319 (3)
C12	0.32237 (18)	0.77404 (10)	0.28470 (11)	0.0308 (3)
C13	0.28387 (18)	0.82065 (10)	0.37289 (11)	0.0311 (3)
H13	0.3641	0.8662	0.4029	0.037*
C14	0.1283 (2)	0.59517 (14)	0.10102 (14)	0.0552 (5)
H14A	0.1154	0.5406	0.1461	0.083*
H14B	0.1755	0.5724	0.0397	0.083*
H14C	0.0138	0.6251	0.0846	0.083*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0449 (7)	0.0583 (8)	0.0648 (8)	−0.0184 (6)	0.0215 (6)	−0.0214 (6)
O2	0.0385 (6)	0.0590 (8)	0.0502 (7)	−0.0175 (5)	0.0221 (5)	−0.0199 (6)
O3	0.0337 (5)	0.0446 (6)	0.0380 (6)	−0.0049 (4)	0.0101 (4)	−0.0142 (5)
N1	0.0424 (8)	0.0613 (9)	0.0403 (8)	−0.0032 (7)	0.0125 (6)	−0.0093 (7)
N2	0.0343 (7)	0.0435 (7)	0.0339 (7)	−0.0066 (6)	0.0131 (5)	−0.0083 (6)
N3	0.0327 (6)	0.0416 (7)	0.0327 (7)	−0.0015 (5)	0.0109 (5)	−0.0057 (5)
C1	0.0506 (10)	0.0775 (13)	0.0500 (11)	−0.0004 (9)	0.0208 (8)	−0.0077 (10)
C2	0.0832 (14)	0.0579 (11)	0.0472 (11)	0.0134 (10)	0.0299 (10)	−0.0056 (9)
C3	0.0985 (16)	0.0555 (12)	0.0539 (12)	−0.0130 (11)	0.0243 (11)	−0.0227 (10)
C4	0.0682 (12)	0.0543 (11)	0.0522 (11)	−0.0173 (9)	0.0174 (9)	−0.0179 (9)
C5	0.0420 (8)	0.0357 (8)	0.0337 (8)	0.0022 (6)	0.0063 (6)	−0.0019 (6)
C6	0.0330 (7)	0.0379 (8)	0.0373 (8)	−0.0011 (6)	0.0062 (6)	−0.0043 (6)
C7	0.0333 (8)	0.0420 (8)	0.0364 (8)	−0.0045 (6)	0.0129 (6)	−0.0030 (7)
C8	0.0338 (7)	0.0341 (8)	0.0325 (8)	−0.0010 (6)	0.0088 (6)	−0.0021 (6)
C9	0.0347 (8)	0.0529 (10)	0.0462 (10)	−0.0125 (7)	0.0190 (7)	−0.0093 (8)
C10	0.0361 (8)	0.0469 (9)	0.0470 (10)	−0.0134 (7)	0.0114 (7)	−0.0144 (7)
C11	0.0321 (7)	0.0323 (7)	0.0321 (8)	0.0011 (6)	0.0069 (6)	−0.0046 (6)
C12	0.0281 (7)	0.0316 (7)	0.0337 (8)	−0.0016 (6)	0.0094 (6)	−0.0003 (6)
C13	0.0313 (7)	0.0304 (7)	0.0320 (8)	−0.0041 (6)	0.0054 (6)	−0.0021 (6)
C14	0.0463 (10)	0.0661 (12)	0.0536 (11)	−0.0128 (8)	0.0079 (8)	−0.0299 (9)

Geometric parameters (Å, º)

O1—C6	1.2286 (18)	C4—C5	1.375 (2)
O2—C12	1.3589 (17)	C4—H4	0.9300
O2—H2B	0.87 (2)	C5—C6	1.503 (2)
O3—C11	1.3624 (17)	C7—C8	1.457 (2)
O3—C14	1.4281 (18)	C7—H7	0.9300
N1—C1	1.331 (2)	C8—C9	1.383 (2)
N1—C5	1.334 (2)	C8—C13	1.400 (2)
N2—C6	1.336 (2)	C9—C10	1.386 (2)
N2—N3	1.3881 (17)	C9—H9	0.9300
N2—H2A	0.892 (19)	C10—C11	1.380 (2)
N3—C7	1.2745 (19)	C10—H10	0.9300
C1—C2	1.367 (3)	C11—C12	1.407 (2)
C1—H1	0.9300	C12—C13	1.375 (2)
C2—C3	1.353 (3)	C13—H13	0.9300
C2—H2	0.9300	C14—H14A	0.9600
C3—C4	1.379 (3)	C14—H14B	0.9600
C3—H3	0.9300	C14—H14C	0.9600
C12—O2—H2B	109.6 (15)	N3—C7—H7	118.4
C11—O3—C14	117.19 (12)	C8—C7—H7	118.4
C1—N1—C5	117.46 (15)	C9—C8—C13	118.62 (14)
C6—N2—N3	121.83 (13)	C9—C8—C7	117.98 (13)
C6—N2—H2A	117.1 (12)	C13—C8—C7	123.39 (13)
N3—N2—H2A	121.0 (12)	C8—C9—C10	120.92 (14)
C7—N3—N2	113.58 (12)	C8—C9—H9	119.5
N1—C1—C2	123.55 (18)	C10—C9—H9	119.5
N1—C1—H1	118.2	C11—C10—C9	120.24 (14)
C2—C1—H1	118.2	C11—C10—H10	119.9
C3—C2—C1	118.43 (18)	C9—C10—H10	119.9
C3—C2—H2	120.8	O3—C11—C10	125.05 (13)
C1—C2—H2	120.8	O3—C11—C12	115.40 (12)
C2—C3—C4	119.67 (18)	C10—C11—C12	119.54 (13)
C2—C3—H3	120.2	O2—C12—C13	124.14 (13)
C4—C3—H3	120.2	O2—C12—C11	116.23 (13)
C5—C4—C3	118.40 (18)	C13—C12—C11	119.63 (12)
C5—C4—H4	120.8	C12—C13—C8	121.04 (13)
C3—C4—H4	120.8	C12—C13—H13	119.5
N1—C5—C4	122.48 (15)	C8—C13—H13	119.5
N1—C5—C6	116.51 (13)	O3—C14—H14A	109.5
C4—C5—C6	120.99 (15)	O3—C14—H14B	109.5
O1—C6—N2	123.68 (14)	H14A—C14—H14B	109.5
O1—C6—C5	123.18 (14)	O3—C14—H14C	109.5
N2—C6—C5	113.14 (13)	H14A—C14—H14C	109.5
N3—C7—C8	123.17 (13)	H14B—C14—H14C	109.5
C6—N2—N3—C7	−177.77 (14)	N3—C7—C8—C13	6.5 (2)
C5—N1—C1—C2	−0.8 (3)	C13—C8—C9—C10	−0.5 (2)
N1—C1—C2—C3	−0.3 (3)	C7—C8—C9—C10	−179.46 (16)
C1—C2—C3—C4	1.0 (3)	C8—C9—C10—C11	0.5 (3)
C2—C3—C4—C5	−0.7 (3)	C14—O3—C11—C10	−1.8 (2)
C1—N1—C5—C4	1.2 (3)	C14—O3—C11—C12	178.77 (14)
C1—N1—C5—C6	−177.36 (15)	C9—C10—C11—O3	−179.00 (15)
C3—C4—C5—N1	−0.5 (3)	C9—C10—C11—C12	0.4 (2)
C3—C4—C5—C6	178.01 (17)	O3—C11—C12—O2	−1.54 (19)
N3—N2—C6—O1	−2.8 (2)	C10—C11—C12—O2	179.04 (14)
N3—N2—C6—C5	176.80 (13)	O3—C11—C12—C13	178.30 (13)
N1—C5—C6—O1	171.67 (15)	C10—C11—C12—C13	−1.1 (2)
C4—C5—C6—O1	−6.9 (3)	O2—C12—C13—C8	−179.10 (14)
N1—C5—C6—N2	−7.9 (2)	C11—C12—C13—C8	1.1 (2)
C4—C5—C6—N2	173.52 (16)	C9—C8—C13—C12	−0.3 (2)
N2—N3—C7—C8	179.82 (13)	C7—C8—C13—C12	178.62 (14)
N3—C7—C8—C9	−174.56 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3^i	0.89 (2)	2.26 (2)	3.093 (2)	155 (2)
O2—H2B···O1^ii	0.87 (2)	1.85 (2)	2.722 (2)	173 (2)
C7—H7···O3^i	0.93	2.33	3.203 (2)	155
N2—H2A···N1	0.89 (2)	2.184 (19)	2.629 (2)	110.2 (14)

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