N-(2-Hydroxy­lbenzo­yl)-N′-(picolino­yl)hydrazine

The title mol­ecule, C₁₃H₁₁N₃O₃, is non-planar. The dihedral angle between the pyridine and benzene rings is 80.5 (1)°. Inter­molecular O—H...O and N—H...O hydrogen bonds link the mol­ecules into columns along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.039
• wR factor = 0.105
• Data-to-parameter ratio = 9.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.50
           From the CIF: _reflns_number_total               1551
           Count of symmetry unique reflns         1578
           Completeness (_total/calc)             98.29%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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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, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.

N-(2-Hydroxylbenzoyl)-N'-(picolinoyl)hydrazine

Crystal data

C13H11N3O3	F(000) = 536
Mr = 257.25	Dx = 1.475 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1502 reflections
a = 4.6152 (7) Å	θ = 2.6–25.2°
b = 10.0698 (16) Å	µ = 0.11 mm^−1
c = 24.928 (4) Å	T = 291 K
V = 1158.5 (3) Å^3	Needle, colourless
Z = 4	0.46 × 0.15 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1260 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.039
Graphite monochromator	θmax = 27.5°, θmin = 2.6°
φ and ω scans	h = −5→5
6078 measured reflections	k = −12→13
1551 independent reflections	l = −32→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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0577P)^2 + 0.0547P] where P = (Fo^2 + 2Fc^2)/3
1551 reflections	(Δ/σ)max = 0.001
173 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.18 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
C1	−0.1367 (6)	0.7339 (2)	0.79610 (9)	0.0349 (6)
C2	−0.0511 (7)	0.8402 (3)	0.76493 (10)	0.0469 (7)
H2	0.0859	0.9004	0.7774	0.056*
C3	−0.1739 (8)	0.8551 (3)	0.71454 (10)	0.0510 (8)
H3	−0.1223	0.9264	0.6928	0.061*
C4	−0.3717 (8)	0.7637 (3)	0.69733 (11)	0.0494 (7)
H4	−0.4583	0.7720	0.6638	0.059*
C5	−0.4410 (7)	0.6584 (3)	0.73073 (10)	0.0505 (7)
H5	−0.5722	0.5953	0.7183	0.061*
C6	−0.0113 (6)	0.7173 (2)	0.85127 (9)	0.0348 (6)
C7	0.1699 (6)	0.5271 (2)	0.94281 (9)	0.0324 (5)
C8	0.2413 (6)	0.4974 (2)	1.00039 (9)	0.0312 (5)
C9	0.1157 (6)	0.5573 (2)	1.04466 (9)	0.0324 (5)
C10	0.1850 (6)	0.5137 (2)	1.09630 (10)	0.0396 (6)
H10	0.0969	0.5525	1.1260	0.048*
C11	0.3826 (7)	0.4139 (3)	1.10318 (10)	0.0435 (7)
H11	0.4290	0.3860	1.1377	0.052*
C12	0.5135 (6)	0.3541 (3)	1.06002 (11)	0.0438 (7)
H12	0.6465	0.2859	1.0652	0.053*
C13	0.4458 (6)	0.3964 (2)	1.00884 (10)	0.0381 (6)
H13	0.5371	0.3574	0.9796	0.046*
N1	−0.3295 (6)	0.6424 (2)	0.77979 (8)	0.0440 (6)
N2	−0.1551 (5)	0.6327 (2)	0.88283 (7)	0.0394 (5)
H2A	−0.3074	0.5932	0.8710	0.047*
N3	−0.0590 (5)	0.6086 (2)	0.93463 (8)	0.0390 (5)
H3A	−0.1446	0.6453	0.9615	0.047*
O1	0.2039 (5)	0.78049 (19)	0.86543 (7)	0.0461 (5)
O2	0.3055 (5)	0.47847 (18)	0.90543 (7)	0.0449 (5)
O3	−0.0736 (5)	0.66020 (18)	1.03827 (7)	0.0485 (5)
H3B	−0.1280	0.6861	1.0678	0.073*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0391 (14)	0.0417 (12)	0.0240 (10)	0.0042 (12)	0.0008 (11)	−0.0003 (10)
C2	0.0572 (18)	0.0472 (14)	0.0362 (14)	−0.0067 (15)	−0.0030 (14)	0.0065 (11)
C3	0.067 (2)	0.0501 (15)	0.0359 (14)	−0.0003 (16)	0.0008 (15)	0.0100 (12)
C4	0.0580 (19)	0.0631 (17)	0.0272 (13)	0.0075 (16)	−0.0078 (13)	0.0022 (12)
C5	0.0556 (19)	0.0618 (16)	0.0342 (14)	−0.0071 (16)	−0.0116 (14)	−0.0017 (12)
C6	0.0369 (15)	0.0390 (12)	0.0285 (12)	0.0033 (12)	0.0002 (11)	−0.0054 (10)
C7	0.0357 (14)	0.0357 (11)	0.0258 (11)	−0.0044 (11)	−0.0013 (11)	0.0015 (9)
C8	0.0324 (14)	0.0350 (11)	0.0264 (12)	−0.0029 (9)	−0.0003 (10)	−0.0014 (9)
C9	0.0319 (14)	0.0334 (11)	0.0318 (12)	0.0007 (10)	0.0009 (11)	0.0019 (9)
C10	0.0448 (16)	0.0466 (13)	0.0275 (12)	0.0025 (13)	0.0024 (13)	0.0004 (10)
C11	0.0481 (17)	0.0521 (15)	0.0305 (13)	0.0040 (14)	−0.0053 (13)	0.0069 (11)
C12	0.0421 (16)	0.0445 (13)	0.0448 (15)	0.0083 (13)	−0.0058 (13)	0.0048 (11)
C13	0.0385 (15)	0.0403 (12)	0.0354 (13)	0.0032 (12)	−0.0008 (12)	−0.0045 (11)
N1	0.0493 (14)	0.0509 (12)	0.0316 (11)	−0.0071 (12)	−0.0074 (11)	0.0014 (9)
N2	0.0383 (12)	0.0552 (12)	0.0248 (10)	−0.0060 (11)	−0.0072 (10)	0.0068 (9)
N3	0.0407 (13)	0.0550 (12)	0.0214 (9)	0.0064 (11)	−0.0025 (9)	0.0020 (9)
O1	0.0475 (12)	0.0557 (10)	0.0349 (9)	−0.0116 (10)	−0.0081 (9)	−0.0008 (8)
O2	0.0510 (12)	0.0560 (10)	0.0276 (9)	0.0061 (10)	0.0041 (9)	−0.0068 (8)
O3	0.0587 (13)	0.0568 (11)	0.0301 (9)	0.0190 (10)	0.0023 (10)	0.0011 (8)

Geometric parameters (Å, º)

C1—N1	1.344 (3)	C8—C9	1.385 (3)
C1—C2	1.380 (4)	C8—C13	1.403 (3)
C1—C6	1.501 (3)	C9—O3	1.365 (3)
C2—C3	1.386 (4)	C9—C10	1.397 (3)
C2—H2	0.93	C10—C11	1.368 (4)
C3—C4	1.366 (4)	C10—H10	0.93
C3—H3	0.93	C11—C12	1.373 (4)
C4—C5	1.386 (4)	C11—H11	0.93
C4—H4	0.93	C12—C13	1.381 (3)
C5—N1	1.337 (3)	C12—H12	0.93
C5—H5	0.93	C13—H13	0.93
C6—O1	1.231 (3)	N2—N3	1.387 (3)
C6—N2	1.336 (3)	N2—H2A	0.86
C7—O2	1.225 (3)	N3—H3A	0.86
C7—N3	1.354 (3)	O3—H3B	0.82
C7—C8	1.503 (3)
N1—C1—C2	123.4 (2)	O3—C9—C8	120.4 (2)
N1—C1—C6	117.1 (2)	O3—C9—C10	119.5 (2)
C2—C1—C6	119.4 (2)	C8—C9—C10	120.1 (2)
C1—C2—C3	118.5 (3)	C11—C10—C9	119.9 (2)
C1—C2—H2	120.7	C11—C10—H10	120.0
C3—C2—H2	120.7	C9—C10—H10	120.0
C4—C3—C2	119.0 (3)	C10—C11—C12	121.1 (2)
C4—C3—H3	120.5	C10—C11—H11	119.4
C2—C3—H3	120.5	C12—C11—H11	119.4
C3—C4—C5	118.8 (3)	C11—C12—C13	119.3 (2)
C3—C4—H4	120.6	C11—C12—H12	120.4
C5—C4—H4	120.6	C13—C12—H12	120.4
N1—C5—C4	123.6 (3)	C12—C13—C8	121.0 (2)
N1—C5—H5	118.2	C12—C13—H13	119.5
C4—C5—H5	118.2	C8—C13—H13	119.5
O1—C6—N2	124.1 (2)	C5—N1—C1	116.7 (2)
O1—C6—C1	121.1 (2)	C6—N2—N3	120.1 (2)
N2—C6—C1	114.8 (2)	C6—N2—H2A	120.0
O2—C7—N3	121.8 (2)	N3—N2—H2A	120.0
O2—C7—C8	122.3 (2)	C7—N3—N2	119.7 (2)
N3—C7—C8	115.8 (2)	C7—N3—H3A	120.1
C9—C8—C13	118.5 (2)	N2—N3—H3A	120.1
C9—C8—C7	125.6 (2)	C9—O3—H3B	109.5
C13—C8—C7	115.8 (2)
N1—C1—C2—C3	1.3 (4)	C7—C8—C9—C10	175.1 (2)
C6—C1—C2—C3	−178.7 (3)	O3—C9—C10—C11	−177.6 (2)
C1—C2—C3—C4	−0.8 (4)	C8—C9—C10—C11	1.6 (4)
C2—C3—C4—C5	−0.6 (5)	C9—C10—C11—C12	−0.6 (4)
C3—C4—C5—N1	1.6 (5)	C10—C11—C12—C13	0.5 (4)
N1—C1—C6—O1	166.1 (2)	C11—C12—C13—C8	−1.3 (4)
C2—C1—C6—O1	−13.9 (4)	C9—C8—C13—C12	2.3 (4)
N1—C1—C6—N2	−15.5 (3)	C7—C8—C13—C12	−175.5 (3)
C2—C1—C6—N2	164.5 (2)	C4—C5—N1—C1	−1.1 (4)
O2—C7—C8—C9	173.9 (2)	C2—C1—N1—C5	−0.3 (4)
N3—C7—C8—C9	−7.8 (4)	C6—C1—N1—C5	179.7 (3)
O2—C7—C8—C13	−8.5 (4)	O1—C6—N2—N3	−1.9 (4)
N3—C7—C8—C13	169.8 (2)	C1—C6—N2—N3	179.7 (2)
C13—C8—C9—O3	176.8 (2)	O2—C7—N3—N2	3.7 (3)
C7—C8—C9—O3	−5.7 (4)	C8—C7—N3—N2	−174.7 (2)
C13—C8—C9—C10	−2.4 (4)	C6—N2—N3—C7	−77.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2^i	0.86	2.29	2.988 (3)	138
N3—H3A···O3	0.86	1.95	2.636 (3)	136
O3—H3B···O1^ii	0.82	1.87	2.678 (3)	170

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