2-Methoxy-benzohydrazide.

The title compound, C(8)H(10)N(2)O(2), crystallizes as two independent mol-ecules linked by N-H⋯N and N-H⋯O hydrogen bonds into a linear chain running along the a axis of the monoclinic unit cell. The intra- and inter-molecular hydrogen bonds are described as a two-ring R(2) (2)(10) motif. The six-membered R(1) (1)(6) rings formed by the intra-molecular inter-actions are almost planar (r.m.s. deviations 0.06 and 0.08 Å). In one mol-ecule, the aromatic and hydrogen-bonded rings are oriented at 4.8 (2)°, whereas in the other mol-ecule these rings are oriented at 6.1 (4)°.

Related literature

For related structures, see: Ashiq et al. (2009 ▶); Kallel et al. (1992 ▶); Saraogi et al. (2002 ▶). For the biological activity of hydrazides, see: Ara et al. (2007 ▶); El-Emam et al. (2004 ▶); Maqsood et al. (2006 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C8H10N2O2

M = 166.18

Monoclinic,

a = 7.6486 (5) Å

b = 10.7123 (7) Å

c = 20.4781 (13) Å

β = 95.563 (3)°

V = 1669.95 (19) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.22 × 0.19 × 0.11 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: none

15129 measured reflections

2938 independent reflections

1695 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.110

S = 1.02

2938 reflections

237 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.12 e Å−3

Δρmin = −0.16 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, global. DOI: 10.1107/S1600536809038227/ng2643sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038227/ng2643Isup2.hkl

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

C8H10N2O2	F(000) = 704
Mr = 166.18	Dx = 1.322 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2389 reflections
a = 7.6486 (5) Å	θ = 2.7–22.7°
b = 10.7123 (7) Å	µ = 0.10 mm−1
c = 20.4781 (13) Å	T = 296 K
β = 95.563 (3)°	Needle, colourless
V = 1669.95 (19) Å3	0.22 × 0.19 × 0.11 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	1695 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.045
graphite	θmax = 25.0°, θmin = 2.0°
ω scans	h = −9→9
15129 measured reflections	k = −12→12
2938 independent reflections	l = −24→24

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0442P)2 + 0.2288P] where P = (Fo2 + 2Fc2)/3
2938 reflections	(Δ/σ)max < 0.001
237 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.16 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
O1	0.1822 (2)	0.26307 (16)	0.04342 (10)	0.0827 (6)
O2	0.6697 (2)	0.39866 (15)	0.11303 (8)	0.0656 (5)
N2	0.4302 (3)	0.0831 (2)	0.06058 (12)	0.0615 (6)
N1	0.4586 (2)	0.21149 (17)	0.07266 (9)	0.0525 (5)
H1N	0.569 (3)	0.235 (2)	0.0811 (11)	0.063*
H21N	0.335 (3)	0.066 (2)	0.0792 (11)	0.063*
H22N	0.400 (3)	0.081 (2)	0.0191 (12)	0.063*
C1	0.3759 (3)	0.43070 (19)	0.07062 (10)	0.0437 (5)
C2	0.2404 (3)	0.5132 (2)	0.05221 (12)	0.0618 (7)
H2	0.1317	0.4815	0.0359	0.074*
C3	0.2614 (5)	0.6394 (3)	0.05727 (14)	0.0803 (9)
H3	0.1683	0.6925	0.0442	0.096*
C4	0.4197 (5)	0.6872 (3)	0.08160 (14)	0.0802 (9)
H4	0.4341	0.7732	0.0853	0.096*
C5	0.5589 (4)	0.6088 (2)	0.10075 (12)	0.0669 (7)
H5	0.6664	0.6419	0.1174	0.080*
C6	0.5379 (3)	0.4812 (2)	0.09505 (10)	0.0486 (6)
C7	0.3323 (3)	0.2961 (2)	0.06103 (10)	0.0462 (6)
C8	0.8411 (3)	0.4463 (3)	0.13126 (16)	0.0977 (10)
H8A	0.8430	0.4878	0.1729	0.147*
H8B	0.8720	0.5045	0.0986	0.147*
H8C	0.9239	0.3787	0.1346	0.147*
O3	1.10200 (18)	0.94743 (13)	0.10222 (7)	0.0552 (4)
O4	0.64141 (19)	0.94752 (16)	0.19111 (7)	0.0652 (5)
N3	0.8244 (2)	1.01543 (17)	0.09341 (9)	0.0471 (5)
H3N	0.720 (3)	1.012 (2)	0.1063 (10)	0.057*
N4	0.8484 (3)	1.1070 (2)	0.04533 (11)	0.0558 (5)
H41N	0.862 (3)	1.062 (2)	0.0055 (12)	0.067*
H42N	0.950 (3)	1.140 (2)	0.0583 (11)	0.067*
C9	0.9165 (3)	0.85915 (19)	0.17588 (10)	0.0406 (5)
C10	1.0450 (3)	0.7726 (2)	0.19540 (11)	0.0572 (6)
H10	1.1445	0.7682	0.1728	0.069*
C11	1.0305 (4)	0.6926 (2)	0.24713 (13)	0.0740 (8)
H11	1.1178	0.6341	0.2587	0.089*
C12	0.8864 (4)	0.7004 (3)	0.28123 (13)	0.0738 (8)
H12	0.8768	0.6476	0.3168	0.089*
C13	0.7564 (3)	0.7843 (2)	0.26394 (11)	0.0615 (7)
H13	0.6591	0.7886	0.2878	0.074*
C14	0.7681 (3)	0.8634 (2)	0.21101 (10)	0.0459 (5)
C15	0.9534 (3)	0.94351 (18)	0.12070 (10)	0.0400 (5)
C16	0.4932 (4)	0.9605 (4)	0.22740 (15)	0.1152 (13)
H16A	0.4315	0.8825	0.2275	0.173*
H16B	0.4164	1.0236	0.2075	0.173*
H16C	0.5316	0.9842	0.2717	0.173*

	U11	U22	U33	U12	U13	U23
O1	0.0401 (10)	0.0727 (12)	0.1326 (16)	−0.0064 (9)	−0.0057 (10)	0.0055 (11)
O2	0.0463 (10)	0.0639 (11)	0.0838 (12)	−0.0039 (8)	−0.0079 (8)	−0.0035 (9)
N2	0.0550 (13)	0.0518 (14)	0.0805 (15)	−0.0044 (10)	0.0207 (12)	−0.0025 (12)
N1	0.0415 (11)	0.0404 (12)	0.0756 (14)	−0.0010 (10)	0.0055 (10)	−0.0032 (10)
C1	0.0458 (13)	0.0462 (14)	0.0409 (12)	0.0049 (11)	0.0136 (10)	0.0060 (10)
C2	0.0587 (15)	0.0638 (18)	0.0644 (16)	0.0143 (13)	0.0142 (12)	0.0144 (13)
C3	0.100 (2)	0.061 (2)	0.083 (2)	0.0307 (18)	0.0275 (18)	0.0185 (16)
C4	0.123 (3)	0.0454 (17)	0.079 (2)	0.0049 (19)	0.045 (2)	0.0001 (15)
C5	0.086 (2)	0.0551 (17)	0.0623 (17)	−0.0126 (15)	0.0217 (14)	−0.0100 (13)
C6	0.0554 (14)	0.0487 (15)	0.0436 (13)	0.0014 (12)	0.0136 (11)	0.0008 (11)
C7	0.0389 (13)	0.0556 (15)	0.0452 (13)	0.0005 (12)	0.0104 (10)	0.0047 (11)
C8	0.0504 (16)	0.114 (3)	0.124 (3)	−0.0211 (16)	−0.0132 (16)	−0.007 (2)
O3	0.0440 (9)	0.0614 (10)	0.0626 (10)	0.0031 (7)	0.0167 (7)	0.0124 (8)
O4	0.0523 (10)	0.0894 (13)	0.0575 (10)	0.0187 (9)	0.0243 (8)	0.0182 (9)
N3	0.0421 (11)	0.0499 (12)	0.0506 (11)	0.0010 (9)	0.0107 (9)	0.0135 (9)
N4	0.0528 (12)	0.0576 (14)	0.0571 (13)	−0.0035 (10)	0.0063 (10)	0.0184 (11)
C9	0.0446 (12)	0.0366 (12)	0.0410 (12)	−0.0033 (10)	0.0069 (10)	−0.0014 (10)
C10	0.0569 (15)	0.0503 (15)	0.0657 (16)	0.0051 (12)	0.0131 (12)	0.0071 (13)
C11	0.081 (2)	0.0605 (17)	0.0807 (19)	0.0116 (14)	0.0108 (16)	0.0273 (15)
C12	0.089 (2)	0.0649 (18)	0.0679 (18)	−0.0072 (16)	0.0074 (16)	0.0266 (15)
C13	0.0641 (17)	0.0711 (18)	0.0512 (15)	−0.0101 (14)	0.0149 (12)	0.0114 (13)
C14	0.0463 (13)	0.0507 (14)	0.0406 (13)	−0.0027 (11)	0.0039 (10)	0.0005 (11)
C15	0.0416 (12)	0.0389 (12)	0.0401 (12)	−0.0015 (10)	0.0079 (10)	−0.0031 (10)
C16	0.078 (2)	0.184 (4)	0.093 (2)	0.051 (2)	0.0534 (18)	0.039 (2)

O1—C7	1.222 (2)	O3—C15	1.233 (2)
O2—C6	1.364 (3)	O4—C14	1.356 (2)
O2—C8	1.423 (3)	O4—C16	1.421 (3)
N2—N1	1.410 (3)	N3—C15	1.331 (3)
N2—H21N	0.88 (2)	N3—N4	1.414 (2)
N2—H22N	0.86 (2)	N3—H3N	0.87 (2)
N1—C7	1.329 (3)	N4—H41N	0.96 (2)
N1—H1N	0.88 (2)	N4—H42N	0.87 (2)
C1—C2	1.386 (3)	C9—C10	1.382 (3)
C1—C6	1.399 (3)	C9—C14	1.403 (3)
C1—C7	1.488 (3)	C9—C15	1.495 (3)
C2—C3	1.364 (4)	C10—C11	1.375 (3)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.364 (4)	C11—C12	1.363 (3)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.383 (4)	C12—C13	1.362 (3)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.380 (3)	C13—C14	1.385 (3)
C5—H5	0.9300	C13—H13	0.9300
C8—H8A	0.9600	C16—H16A	0.9600
C8—H8B	0.9600	C16—H16B	0.9600
C8—H8C	0.9600	C16—H16C	0.9600
C6—O2—C8	118.5 (2)	C14—O4—C16	119.39 (19)
N1—N2—H21N	104.3 (15)	C15—N3—N4	123.54 (18)
N1—N2—H22N	102.9 (16)	C15—N3—H3N	120.8 (14)
H21N—N2—H22N	105 (2)	N4—N3—H3N	115.5 (15)
C7—N1—N2	122.49 (19)	N3—N4—H41N	105.8 (14)
C7—N1—H1N	120.3 (15)	N3—N4—H42N	104.1 (15)
N2—N1—H1N	116.3 (15)	H41N—N4—H42N	107 (2)
C2—C1—C6	117.6 (2)	C10—C9—C14	117.5 (2)
C2—C1—C7	115.5 (2)	C10—C9—C15	116.33 (18)
C6—C1—C7	126.91 (19)	C14—C9—C15	126.12 (19)
C3—C2—C1	122.1 (3)	C11—C10—C9	122.2 (2)
C3—C2—H2	118.9	C11—C10—H10	118.9
C1—C2—H2	118.9	C9—C10—H10	118.9
C2—C3—C4	119.6 (3)	C12—C11—C10	119.1 (2)
C2—C3—H3	120.2	C12—C11—H11	120.4
C4—C3—H3	120.2	C10—C11—H11	120.4
C3—C4—C5	120.4 (3)	C13—C12—C11	120.9 (2)
C3—C4—H4	119.8	C13—C12—H12	119.6
C5—C4—H4	119.8	C11—C12—H12	119.6
C6—C5—C4	119.9 (3)	C12—C13—C14	120.4 (2)
C6—C5—H5	120.1	C12—C13—H13	119.8
C4—C5—H5	120.1	C14—C13—H13	119.8
O2—C6—C5	122.8 (2)	O4—C14—C13	122.9 (2)
O2—C6—C1	116.9 (2)	O4—C14—C9	117.24 (18)
C5—C6—C1	120.3 (2)	C13—C14—C9	119.9 (2)
O1—C7—N1	120.0 (2)	O3—C15—N3	121.28 (19)
O1—C7—C1	120.8 (2)	O3—C15—C9	119.98 (19)
N1—C7—C1	119.20 (19)	N3—C15—C9	118.72 (17)
O2—C8—H8A	109.5	O4—C16—H16A	109.5
O2—C8—H8B	109.5	O4—C16—H16B	109.5
H8A—C8—H8B	109.5	H16A—C16—H16B	109.5
O2—C8—H8C	109.5	O4—C16—H16C	109.5
H8A—C8—H8C	109.5	H16A—C16—H16C	109.5
H8B—C8—H8C	109.5	H16B—C16—H16C	109.5
C6—C1—C2—C3	0.1 (3)	C14—C9—C10—C11	0.0 (3)
C7—C1—C2—C3	−179.1 (2)	C15—C9—C10—C11	177.5 (2)
C1—C2—C3—C4	−0.5 (4)	C9—C10—C11—C12	−1.3 (4)
C2—C3—C4—C5	0.4 (4)	C10—C11—C12—C13	1.2 (4)
C3—C4—C5—C6	0.2 (4)	C11—C12—C13—C14	0.2 (4)
C8—O2—C6—C5	−7.4 (3)	C16—O4—C14—C13	3.1 (3)
C8—O2—C6—C1	173.2 (2)	C16—O4—C14—C9	−176.4 (2)
C4—C5—C6—O2	−180.0 (2)	C12—C13—C14—O4	179.1 (2)
C4—C5—C6—C1	−0.7 (3)	C12—C13—C14—C9	−1.5 (3)
C2—C1—C6—O2	179.89 (18)	C10—C9—C14—O4	−179.18 (19)
C7—C1—C6—O2	−1.1 (3)	C15—C9—C14—O4	3.7 (3)
C2—C1—C6—C5	0.5 (3)	C10—C9—C14—C13	1.3 (3)
C7—C1—C6—C5	179.5 (2)	C15—C9—C14—C13	−175.8 (2)
N2—N1—C7—O1	5.1 (3)	N4—N3—C15—O3	−4.7 (3)
N2—N1—C7—C1	−175.71 (19)	N4—N3—C15—C9	173.79 (19)
C2—C1—C7—O1	−6.0 (3)	C10—C9—C15—O3	−11.5 (3)
C6—C1—C7—O1	175.0 (2)	C14—C9—C15—O3	165.7 (2)
C2—C1—C7—N1	174.84 (19)	C10—C9—C15—N3	169.98 (19)
C6—C1—C7—N1	−4.2 (3)	C14—C9—C15—N3	−12.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21N···O3i	0.88 (2)	2.27 (2)	3.091 (3)	155 (2)
N3—H3N···N2ii	0.87 (2)	2.44 (2)	3.111 (3)	134.2 (18)
N4—H41N···O3iii	0.96 (2)	2.25 (3)	3.136 (3)	152.3 (19)
N4—H42N···O1iv	0.87 (2)	2.26 (2)	3.055 (3)	153 (2)
N1—H1N···O2	0.89 (2)	1.98 (2)	2.655 (2)	130.8 (17)
N3—H3N···O4	0.86 (2)	2.01 (2)	2.653 (2)	129.9 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H21N⋯O3i	0.88 (2)	2.27 (2)	3.091 (3)	155 (2)
N3—H3N⋯N2ii	0.87 (2)	2.44 (2)	3.111 (3)	134.2 (18)
N4—H41N⋯O3iii	0.96 (2)	2.25 (3)	3.136 (3)	152.3 (19)
N4—H42N⋯O1iv	0.87 (2)	2.26 (2)	3.055 (3)	153 (2)
N1—H1N⋯O2	0.89 (2)	1.98 (2)	2.655 (2)	130.8 (17)
N3—H3N⋯O4	0.86 (2)	2.01 (2)	2.653 (2)	129.9 (19)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .