3-Methoxy-benzohydrazide.

The title compound, C(8)H(10)N(2)O(2), crystallizes with two independent mol-ecules in an asymmetric unit. The structure is stabilized by nine inter-molecular N-H⋯N, N-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For related structures, see: Ashiq, Jamal et al. (2008 ▶, 2009a ▶,b ▶); Jamal et al. (2008 ▶, 2009 ▶); Kallel et al. (1992 ▶); Saraogi et al. (2002 ▶). For the biological activity of hydrazides, see: Ara et al. (2007 ▶); Ashiq, Ara et al. (2008 ▶).

Experimental

Crystal data

C8H10N2O2

M = 166.18

Monoclinic,

a = 13.1288 (8) Å

b = 7.5417 (4) Å

c = 17.0734 (10) Å

β = 92.857 (3)°

V = 1688.40 (17) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.39 × 0.15 × 0.11 mm

Data collection

Bruker KAPPA APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.979, T max = 0.990

18386 measured reflections

4200 independent reflections

1708 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.126

S = 0.95

4200 reflections

237 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536809036526/pv2207sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036526/pv2207Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C8H10N2O2	F(000) = 704
Mr = 166.18	Dx = 1.308 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2161 reflections
a = 13.1288 (8) Å	θ = 3.3–20.5°
b = 7.5417 (4) Å	µ = 0.10 mm−1
c = 17.0734 (10) Å	T = 296 K
β = 92.857 (3)°	Needle, colourless
V = 1688.40 (17) Å3	0.39 × 0.15 × 0.11 mm
Z = 8

Bruker KAPPA APEXII CCD diffractometer	4200 independent reflections
Radiation source: fine-focus sealed tube	1708 reflections with I > 2σ(I)
graphite	Rint = 0.066
ω scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −17→17
Tmin = 0.979, Tmax = 0.990	k = −9→10
18386 measured reflections	l = −22→22

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ2(Fo2) + (0.0499P)2] where P = (Fo2 + 2Fc2)/3
4200 reflections	(Δ/σ)max < 0.001
237 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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.

	x	y	z	Uiso*/Ueq
O11	0.43146 (11)	0.04300 (19)	1.07269 (9)	0.0607 (5)
O12	0.08143 (12)	0.4522 (2)	0.92286 (10)	0.0767 (5)
N11	0.45156 (14)	0.3134 (2)	1.02178 (10)	0.0459 (5)
H11N	0.4261 (15)	0.422 (3)	1.0077 (12)	0.055*
N12	0.55933 (15)	0.3117 (2)	1.02887 (13)	0.0525 (5)
H12N	0.5835 (16)	0.216 (3)	0.9985 (12)	0.063*
H13N	0.5782 (17)	0.271 (3)	1.0737 (13)	0.063*
C11	0.28175 (15)	0.1986 (2)	1.03161 (12)	0.0406 (5)
C12	0.23758 (16)	0.3243 (3)	0.98111 (12)	0.0470 (6)
H12	0.2785	0.4009	0.9538	0.056*
C13	0.13289 (18)	0.3352 (3)	0.97163 (13)	0.0532 (6)
C14	0.07247 (18)	0.2229 (3)	1.01231 (15)	0.0646 (7)
H14	0.0018	0.2306	1.0059	0.078*
C15	0.11629 (19)	0.0994 (3)	1.06246 (15)	0.0676 (7)
H15	0.0751	0.0245	1.0904	0.081*
C16	0.22077 (18)	0.0856 (3)	1.07168 (13)	0.0545 (6)
H16	0.2500	0.0001	1.1049	0.065*
C17	0.39396 (16)	0.1793 (3)	1.04354 (12)	0.0415 (5)
C18	0.1395 (2)	0.5781 (4)	0.88291 (17)	0.0981 (11)
H18A	0.1783	0.6490	0.9204	0.147*
H18B	0.0946	0.6531	0.8516	0.147*
H18C	0.1850	0.5177	0.8496	0.147*
O21	0.72052 (11)	0.73719 (17)	0.21668 (8)	0.0534 (4)
O22	0.27188 (11)	0.6456 (2)	0.17438 (10)	0.0692 (5)
N21	0.61560 (13)	0.9272 (2)	0.15351 (11)	0.0471 (5)
H21N	0.5565 (16)	0.954 (3)	0.1308 (12)	0.057*
N22	0.69253 (15)	1.0512 (3)	0.13927 (12)	0.0531 (6)
H23N	0.7151 (16)	1.092 (3)	0.1850 (13)	0.064*
H22N	0.7419 (17)	0.994 (3)	0.1205 (14)	0.064*
C21	0.54632 (15)	0.6517 (2)	0.20011 (11)	0.0372 (5)
C22	0.44617 (16)	0.7004 (3)	0.18400 (12)	0.0442 (5)
H22	0.4313	0.8147	0.1665	0.053*
C23	0.36779 (16)	0.5814 (3)	0.19354 (12)	0.0460 (5)
C24	0.38825 (17)	0.4133 (3)	0.21999 (13)	0.0553 (6)
H24	0.3357	0.3330	0.2268	0.066*
C25	0.48845 (19)	0.3654 (3)	0.23633 (14)	0.0640 (7)
H25	0.5030	0.2514	0.2543	0.077*
C26	0.56714 (17)	0.4813 (3)	0.22674 (13)	0.0523 (6)
H26	0.6341	0.4459	0.2380	0.063*
C27	0.63403 (16)	0.7742 (3)	0.19120 (11)	0.0382 (5)
C28	0.18800 (17)	0.5274 (3)	0.17719 (16)	0.0711 (8)
H28A	0.2005	0.4247	0.1459	0.107*
H28B	0.1272	0.5858	0.1571	0.107*
H28C	0.1796	0.4919	0.2305	0.107*

	U11	U22	U33	U12	U13	U23
O11	0.0571 (10)	0.0390 (9)	0.0842 (12)	−0.0005 (8)	−0.0140 (8)	0.0216 (8)
O12	0.0586 (11)	0.0935 (13)	0.0778 (13)	0.0257 (10)	−0.0005 (9)	0.0264 (10)
N11	0.0468 (12)	0.0323 (10)	0.0577 (12)	0.0019 (9)	−0.0059 (9)	0.0088 (9)
N12	0.0491 (13)	0.0412 (11)	0.0660 (15)	0.0008 (9)	−0.0087 (10)	0.0088 (10)
C11	0.0475 (13)	0.0319 (11)	0.0418 (13)	0.0002 (10)	−0.0044 (10)	0.0006 (10)
C12	0.0478 (15)	0.0476 (13)	0.0459 (14)	0.0062 (11)	0.0042 (11)	0.0032 (11)
C13	0.0547 (16)	0.0549 (15)	0.0498 (15)	0.0110 (13)	−0.0008 (12)	0.0053 (12)
C14	0.0481 (15)	0.0648 (17)	0.0801 (19)	−0.0026 (13)	−0.0052 (14)	0.0020 (14)
C15	0.0629 (18)	0.0576 (17)	0.082 (2)	−0.0121 (13)	0.0019 (14)	0.0150 (14)
C16	0.0579 (16)	0.0431 (13)	0.0615 (16)	−0.0066 (12)	−0.0072 (12)	0.0119 (11)
C17	0.0529 (14)	0.0315 (12)	0.0396 (13)	−0.0005 (11)	−0.0035 (10)	0.0026 (10)
C18	0.091 (2)	0.115 (3)	0.091 (2)	0.0472 (19)	0.0296 (18)	0.0613 (19)
O21	0.0428 (9)	0.0515 (10)	0.0644 (11)	0.0025 (7)	−0.0106 (8)	0.0114 (7)
O22	0.0410 (10)	0.0611 (11)	0.1053 (14)	0.0010 (8)	0.0027 (9)	0.0147 (9)
N21	0.0419 (11)	0.0390 (11)	0.0589 (13)	−0.0055 (9)	−0.0130 (9)	0.0077 (9)
N22	0.0564 (14)	0.0431 (12)	0.0585 (14)	−0.0114 (10)	−0.0096 (11)	0.0018 (10)
C21	0.0444 (13)	0.0347 (12)	0.0323 (12)	0.0042 (10)	−0.0003 (9)	−0.0027 (9)
C22	0.0490 (14)	0.0359 (12)	0.0479 (14)	0.0050 (11)	0.0030 (11)	0.0044 (10)
C23	0.0449 (14)	0.0453 (13)	0.0481 (14)	0.0048 (11)	0.0042 (11)	−0.0009 (10)
C24	0.0577 (17)	0.0415 (14)	0.0666 (16)	−0.0048 (11)	0.0038 (13)	0.0016 (12)
C25	0.0660 (18)	0.0361 (13)	0.089 (2)	0.0054 (13)	−0.0042 (14)	0.0130 (12)
C26	0.0491 (14)	0.0396 (13)	0.0670 (16)	0.0040 (11)	−0.0073 (12)	0.0050 (11)
C27	0.0451 (14)	0.0350 (12)	0.0339 (12)	0.0035 (10)	−0.0039 (10)	−0.0040 (9)
C28	0.0483 (16)	0.0705 (18)	0.095 (2)	−0.0070 (13)	0.0064 (14)	−0.0227 (15)

O11—C17	1.234 (2)	O21—C27	1.228 (2)
O12—C13	1.368 (3)	O22—C23	1.373 (2)
O12—C18	1.415 (3)	O22—C28	1.419 (2)
N11—C17	1.327 (2)	N21—C27	1.337 (2)
N11—N12	1.414 (2)	N21—N22	1.407 (2)
N11—H11N	0.91 (2)	N21—H21N	0.87 (2)
N12—H12N	0.95 (2)	N22—H23N	0.88 (2)
N12—H13N	0.85 (2)	N22—H22N	0.85 (2)
C11—C16	1.374 (3)	C21—C22	1.380 (3)
C11—C12	1.389 (3)	C21—C26	1.385 (3)
C11—C17	1.484 (3)	C21—C27	1.490 (3)
C12—C13	1.378 (3)	C22—C23	1.381 (3)
C12—H12	0.9300	C22—H22	0.9300
C13—C14	1.372 (3)	C23—C24	1.368 (3)
C14—C15	1.372 (3)	C24—C25	1.379 (3)
C14—H14	0.9300	C24—H24	0.9300
C15—C16	1.377 (3)	C25—C26	1.369 (3)
C15—H15	0.9300	C25—H25	0.9300
C16—H16	0.9300	C26—H26	0.9300
C18—H18A	0.9600	C28—H28A	0.9600
C18—H18B	0.9600	C28—H28B	0.9600
C18—H18C	0.9600	C28—H28C	0.9600
C13—O12—C18	117.70 (18)	C23—O22—C28	118.35 (18)
C17—N11—N12	123.42 (17)	C27—N21—N22	122.87 (18)
C17—N11—H11N	123.5 (13)	C27—N21—H21N	123.3 (13)
N12—N11—H11N	112.5 (13)	N22—N21—H21N	113.5 (13)
N11—N12—H12N	108.7 (13)	N21—N22—H23N	107.0 (15)
N11—N12—H13N	109.0 (15)	N21—N22—H22N	107.2 (15)
H12N—N12—H13N	97.3 (19)	H23N—N22—H22N	106 (2)
C16—C11—C12	119.8 (2)	C22—C21—C26	118.87 (19)
C16—C11—C17	118.03 (18)	C22—C21—C27	123.24 (18)
C12—C11—C17	122.19 (19)	C26—C21—C27	117.88 (18)
C13—C12—C11	119.8 (2)	C21—C22—C23	120.78 (19)
C13—C12—H12	120.1	C21—C22—H22	119.6
C11—C12—H12	120.1	C23—C22—H22	119.6
O12—C13—C14	115.2 (2)	C24—C23—O22	124.6 (2)
O12—C13—C12	124.7 (2)	C24—C23—C22	120.4 (2)
C14—C13—C12	120.1 (2)	O22—C23—C22	115.02 (19)
C15—C14—C13	120.0 (2)	C23—C24—C25	118.6 (2)
C15—C14—H14	120.0	C23—C24—H24	120.7
C13—C14—H14	120.0	C25—C24—H24	120.7
C14—C15—C16	120.5 (2)	C26—C25—C24	121.8 (2)
C14—C15—H15	119.8	C26—C25—H25	119.1
C16—C15—H15	119.8	C24—C25—H25	119.1
C11—C16—C15	119.9 (2)	C25—C26—C21	119.6 (2)
C11—C16—H16	120.1	C25—C26—H26	120.2
C15—C16—H16	120.1	C21—C26—H26	120.2
O11—C17—N11	121.8 (2)	O21—C27—N21	120.57 (19)
O11—C17—C11	120.67 (18)	O21—C27—C21	121.92 (18)
N11—C17—C11	117.55 (17)	N21—C27—C21	117.51 (18)
O12—C18—H18A	109.5	O22—C28—H28A	109.5
O12—C18—H18B	109.5	O22—C28—H28B	109.5
H18A—C18—H18B	109.5	H28A—C28—H28B	109.5
O12—C18—H18C	109.5	O22—C28—H28C	109.5
H18A—C18—H18C	109.5	H28A—C28—H28C	109.5
H18B—C18—H18C	109.5	H28B—C28—H28C	109.5
C16—C11—C12—C13	0.1 (3)	C26—C21—C22—C23	−0.5 (3)
C17—C11—C12—C13	179.32 (18)	C27—C21—C22—C23	−179.80 (18)
C18—O12—C13—C14	176.3 (2)	C28—O22—C23—C24	−4.2 (3)
C18—O12—C13—C12	−4.0 (3)	C28—O22—C23—C22	175.51 (19)
C11—C12—C13—O12	−179.2 (2)	C21—C22—C23—C24	0.7 (3)
C11—C12—C13—C14	0.4 (3)	C21—C22—C23—O22	−179.05 (17)
O12—C13—C14—C15	179.5 (2)	O22—C23—C24—C25	179.3 (2)
C12—C13—C14—C15	−0.1 (4)	C22—C23—C24—C25	−0.4 (3)
C13—C14—C15—C16	−0.8 (4)	C23—C24—C25—C26	0.0 (3)
C12—C11—C16—C15	−1.0 (3)	C24—C25—C26—C21	0.1 (4)
C17—C11—C16—C15	179.8 (2)	C22—C21—C26—C25	0.1 (3)
C14—C15—C16—C11	1.3 (4)	C27—C21—C26—C25	179.42 (19)
N12—N11—C17—O11	0.9 (3)	N22—N21—C27—O21	1.5 (3)
N12—N11—C17—C11	−179.15 (17)	N22—N21—C27—C21	−178.00 (18)
C16—C11—C17—O11	16.9 (3)	C22—C21—C27—O21	168.96 (19)
C12—C11—C17—O11	−162.3 (2)	C26—C21—C27—O21	−10.3 (3)
C16—C11—C17—N11	−163.0 (2)	C22—C21—C27—N21	−11.6 (3)
C12—C11—C17—N11	17.8 (3)	C26—C21—C27—N21	169.15 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11N···N12i	0.91 (2)	2.12 (2)	2.958 (2)	153.3 (18)
N11—H11N···N11i	0.91 (2)	2.63 (2)	3.191 (2)	120.9 (13)
N12—H12N···O11ii	0.95 (2)	2.30 (2)	3.193 (2)	155.2 (18)
N12—H13N···N22iii	0.85 (2)	2.47 (2)	3.185 (3)	142.6 (19)
N21—H21N···O11iv	0.87 (2)	1.99 (2)	2.860 (2)	172 (2)
N22—H23N···O21v	0.88 (2)	2.14 (2)	3.007 (2)	168 (2)
C18—H18C···O21vi	0.96	2.58	3.498 (3)	160
C22—H22···O11iv	0.93	2.35	3.208 (3)	153
C26—H26···O21vii	0.93	2.56	3.439 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H11N⋯N12i	0.91 (2)	2.12 (2)	2.958 (2)	153.3 (18)
N11—H11N⋯N11i	0.91 (2)	2.63 (2)	3.191 (2)	120.9 (13)
N12—H12N⋯O11ii	0.95 (2)	2.30 (2)	3.193 (2)	155.2 (18)
N12—H13N⋯N22iii	0.85 (2)	2.47 (2)	3.185 (3)	142.6 (19)
N21—H21N⋯O11iv	0.87 (2)	1.99 (2)	2.860 (2)	172 (2)
N22—H23N⋯O21v	0.88 (2)	2.14 (2)	3.007 (2)	168 (2)
C18—H18C⋯O21vi	0.96	2.58	3.498 (3)	160
C22—H22⋯O11iv	0.93	2.35	3.208 (3)	153
C26—H26⋯O21vii	0.93	2.56	3.439 (3)	157

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .