1-(2-Hydroxy­phen­yl)ethanone benzoyl­hydrazone

In the title compound, the planes of the phen­yl and 2-(1-imino­eth­yl)phenol fragments form dihedral angles of 28.18 (11) and 28.51 (11)°, respectively, with the central –N—C(=O)– fragment. The mol­ecule is stabilized by inter­molecular N—H...O hydrogen bonds, which form a one-dimensional chain parallel to the a axis.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.059
• wR factor = 0.138
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C9

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   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

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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; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

1-(2-Hydroxyphenyl)ethanone benzoylhydrazone

Crystal data

C15H14N2O2	F(000) = 536
Mr = 254.28	Dx = 1.313 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1000 reflections
a = 4.9110 (18) Å	θ = 1.9–26.5°
b = 12.466 (4) Å	µ = 0.09 mm^−1
c = 21.018 (7) Å	T = 273 K
β = 91.299 (6)°	Block, colourless
V = 1286.4 (8) Å^3	0.43 × 0.22 × 0.19 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2662 independent reflections
Radiation source: fine-focus sealed tube	2342 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 83.66 pixels mm^-1	θmax = 26.5°, θmin = 1.9°
ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −15→15
Tmin = 0.964, Tmax = 0.985	l = −26→26
13472 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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.24	w = 1/[σ^2(Fo^2) + (0.0477P)^2 + 0.3287P] where P = (Fo^2 + 2Fc^2)/3
2662 reflections	(Δ/σ)max < 0.001
180 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.13 e Å^−3

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

	x	y	z	Uiso*/Ueq
O1	0.9051 (2)	0.41693 (12)	0.09318 (6)	0.0566 (4)
O2	0.8316 (3)	0.58248 (15)	0.24038 (8)	0.0767 (5)
N2	0.5453 (3)	0.43929 (12)	0.18429 (7)	0.0449 (4)
C8	0.4119 (3)	0.41479 (14)	0.23414 (8)	0.0427 (4)
C1	0.3696 (4)	0.27159 (17)	0.01252 (10)	0.0556 (5)
H1A	0.2834	0.2461	0.0485	0.067*
C2	0.2892 (5)	0.2355 (2)	−0.04705 (12)	0.0724 (7)
H2B	0.1504	0.1851	−0.0510	0.087*
C3	0.4119 (5)	0.2734 (2)	−0.10033 (11)	0.0699 (7)
H3A	0.3532	0.2504	−0.1404	0.084*
C4	0.6225 (5)	0.34559 (19)	−0.09430 (10)	0.0668 (6)
H4A	0.7082	0.3705	−0.1305	0.080*
C5	0.7075 (4)	0.38133 (16)	−0.03517 (9)	0.0533 (5)
H5A	0.8516	0.4295	−0.0315	0.064*
C6	0.5786 (3)	0.34572 (14)	0.01886 (8)	0.0427 (4)
C7	0.6706 (3)	0.38736 (14)	0.08213 (8)	0.0413 (4)
N1	0.4798 (3)	0.38807 (13)	0.12740 (7)	0.0446 (4)
C9	0.1998 (4)	0.32860 (17)	0.23603 (9)	0.0579 (5)
H9A	0.1776	0.2972	0.1945	0.087*
H9B	0.0299	0.3590	0.2488	0.087*
H9C	0.2559	0.2743	0.2660	0.087*
C10	0.4859 (3)	0.47663 (14)	0.29214 (9)	0.0455 (4)
C11	0.3536 (4)	0.45880 (18)	0.34919 (9)	0.0571 (5)
H11A	0.2178	0.4069	0.3503	0.068*
C12	0.4164 (5)	0.5151 (2)	0.40372 (10)	0.0668 (6)
H12A	0.3242	0.5012	0.4410	0.080*
C13	0.6163 (5)	0.59189 (18)	0.40280 (11)	0.0668 (6)
H13A	0.6612	0.6299	0.4396	0.080*
C14	0.7491 (5)	0.61253 (19)	0.34784 (11)	0.0680 (6)
H14A	0.8832	0.6652	0.3477	0.082*
C15	0.6884 (4)	0.55656 (16)	0.29208 (10)	0.0538 (5)
H2A	0.776 (6)	0.544 (2)	0.2113 (13)	0.088 (9)*
H1B	0.317 (4)	0.3845 (15)	0.1154 (9)	0.050 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0333 (7)	0.0790 (10)	0.0575 (8)	−0.0093 (6)	−0.0003 (5)	−0.0005 (7)
O2	0.0799 (11)	0.0846 (12)	0.0657 (10)	−0.0390 (9)	0.0026 (9)	−0.0064 (9)
N2	0.0378 (8)	0.0541 (9)	0.0428 (8)	−0.0048 (6)	−0.0018 (6)	−0.0006 (7)
C8	0.0364 (9)	0.0474 (10)	0.0442 (10)	0.0012 (7)	−0.0034 (7)	0.0032 (8)
C1	0.0506 (11)	0.0613 (12)	0.0550 (12)	−0.0084 (9)	0.0041 (9)	−0.0086 (9)
C2	0.0608 (13)	0.0805 (16)	0.0758 (16)	−0.0066 (12)	−0.0035 (12)	−0.0275 (13)
C3	0.0740 (15)	0.0801 (16)	0.0551 (13)	0.0199 (13)	−0.0106 (11)	−0.0205 (11)
C4	0.0847 (16)	0.0695 (14)	0.0467 (12)	0.0168 (12)	0.0090 (11)	0.0031 (10)
C5	0.0572 (11)	0.0526 (11)	0.0504 (11)	−0.0001 (9)	0.0060 (9)	0.0048 (9)
C6	0.0367 (9)	0.0452 (10)	0.0461 (10)	0.0061 (7)	0.0000 (7)	0.0015 (8)
C7	0.0341 (9)	0.0438 (9)	0.0460 (10)	−0.0009 (7)	0.0003 (7)	0.0069 (7)
N1	0.0322 (8)	0.0584 (10)	0.0432 (8)	−0.0062 (7)	−0.0030 (6)	−0.0006 (7)
C9	0.0590 (12)	0.0650 (13)	0.0498 (11)	−0.0169 (10)	0.0042 (9)	0.0003 (9)
C10	0.0416 (9)	0.0475 (10)	0.0472 (10)	0.0046 (8)	−0.0054 (7)	0.0017 (8)
C11	0.0576 (12)	0.0633 (12)	0.0503 (12)	−0.0006 (10)	0.0011 (9)	0.0003 (9)
C12	0.0746 (15)	0.0777 (15)	0.0481 (12)	0.0114 (12)	0.0010 (10)	−0.0062 (11)
C13	0.0745 (15)	0.0651 (14)	0.0602 (14)	0.0135 (12)	−0.0128 (11)	−0.0184 (11)
C14	0.0694 (14)	0.0604 (13)	0.0734 (15)	−0.0062 (11)	−0.0124 (12)	−0.0118 (11)
C15	0.0534 (11)	0.0545 (11)	0.0532 (12)	−0.0018 (9)	−0.0055 (9)	−0.0015 (9)

Geometric parameters (Å, º)

O1—C7	1.227 (2)	C5—H5A	0.9300
O2—C15	1.347 (3)	C6—C7	1.488 (2)
O2—H2A	0.82 (3)	C7—N1	1.350 (2)
N2—C8	1.285 (2)	N1—H1B	0.83 (2)
N2—N1	1.387 (2)	C9—H9A	0.9600
C8—C10	1.481 (3)	C9—H9B	0.9600
C8—C9	1.497 (3)	C9—H9C	0.9600
C1—C2	1.380 (3)	C10—C11	1.394 (3)
C1—C6	1.385 (3)	C10—C15	1.408 (3)
C1—H1A	0.9300	C11—C12	1.373 (3)
C2—C3	1.368 (3)	C11—H11A	0.9300
C2—H2B	0.9300	C12—C13	1.372 (3)
C3—C4	1.375 (3)	C12—H12A	0.9300
C3—H3A	0.9300	C13—C14	1.364 (3)
C4—C5	1.376 (3)	C13—H13A	0.9300
C4—H4A	0.9300	C14—C15	1.390 (3)
C5—C6	1.385 (3)	C14—H14A	0.9300
C15—O2—H2A	107.0 (19)	C7—N1—H1B	117.6 (14)
C8—N2—N1	118.75 (15)	N2—N1—H1B	119.1 (14)
N2—C8—C10	115.29 (16)	C8—C9—H9A	109.5
N2—C8—C9	124.04 (17)	C8—C9—H9B	109.5
C10—C8—C9	120.65 (16)	H9A—C9—H9B	109.5
C2—C1—C6	120.1 (2)	C8—C9—H9C	109.5
C2—C1—H1A	120.0	H9A—C9—H9C	109.5
C6—C1—H1A	120.0	H9B—C9—H9C	109.5
C3—C2—C1	120.6 (2)	C11—C10—C15	117.17 (18)
C3—C2—H2B	119.7	C11—C10—C8	120.95 (17)
C1—C2—H2B	119.7	C15—C10—C8	121.87 (17)
C2—C3—C4	119.7 (2)	C12—C11—C10	122.4 (2)
C2—C3—H3A	120.2	C12—C11—H11A	118.8
C4—C3—H3A	120.2	C10—C11—H11A	118.8
C3—C4—C5	120.5 (2)	C13—C12—C11	119.5 (2)
C3—C4—H4A	119.8	C13—C12—H12A	120.3
C5—C4—H4A	119.8	C11—C12—H12A	120.3
C4—C5—C6	120.1 (2)	C14—C13—C12	120.0 (2)
C4—C5—H5A	119.9	C14—C13—H13A	120.0
C6—C5—H5A	119.9	C12—C13—H13A	120.0
C1—C6—C5	119.08 (18)	C13—C14—C15	121.5 (2)
C1—C6—C7	121.86 (17)	C13—C14—H14A	119.3
C5—C6—C7	119.06 (16)	C15—C14—H14A	119.3
O1—C7—N1	121.88 (16)	O2—C15—C14	116.99 (19)
O1—C7—C6	122.60 (16)	O2—C15—C10	123.52 (18)
N1—C7—C6	115.51 (15)	C14—C15—C10	119.5 (2)
C7—N1—N2	117.36 (14)
N1—N2—C8—C10	−177.34 (14)	C8—N2—N1—C7	−158.92 (16)
N1—N2—C8—C9	4.1 (3)	N2—C8—C10—C11	179.10 (17)
C6—C1—C2—C3	−0.8 (3)	C9—C8—C10—C11	−2.3 (3)
C1—C2—C3—C4	1.9 (4)	N2—C8—C10—C15	0.1 (2)
C2—C3—C4—C5	−1.1 (3)	C9—C8—C10—C15	178.66 (18)
C3—C4—C5—C6	−0.8 (3)	C15—C10—C11—C12	−0.6 (3)
C2—C1—C6—C5	−1.1 (3)	C8—C10—C11—C12	−179.69 (19)
C2—C1—C6—C7	179.56 (19)	C10—C11—C12—C13	0.0 (3)
C4—C5—C6—C1	1.9 (3)	C11—C12—C13—C14	0.6 (3)
C4—C5—C6—C7	−178.73 (17)	C12—C13—C14—C15	−0.5 (3)
C1—C6—C7—O1	150.85 (18)	C13—C14—C15—O2	−179.7 (2)
C5—C6—C7—O1	−28.5 (3)	C13—C14—C15—C10	−0.1 (3)
C1—C6—C7—N1	−27.6 (2)	C11—C10—C15—O2	−179.74 (19)
C5—C6—C7—N1	153.06 (17)	C8—C10—C15—O2	−0.7 (3)
O1—C7—N1—N2	10.0 (3)	C11—C10—C15—C14	0.7 (3)
C6—C7—N1—N2	−171.54 (14)	C8—C10—C15—C14	179.72 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N2	0.82 (3)	1.81 (3)	2.545 (2)	148 (3)
C9—H9A···N1	0.96	2.36	2.792 (3)	107
N1—H1B···O1^i	0.83 (2)	2.10 (2)	2.919 (2)	165.2 (18)

Symmetry code: (i) x−1, y, z.