2-(2-Methoxy­phenyl­hydrazono)-3-oxobutanoic acid

The crystal structure of the title compound, C₁₁H₁₂N₂O₄, contains two crystallographically independent mol­ecules in the asymmetric unit. The mol­ecules exist in the stereo­isomeric Z form, with the NH group forming an intramolecular N—H...O hydrogen bond with the carbonyl O atom of the carboxyl group. It is also confirmed that the compound exists in the hydra­zone form and not the azo form.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.046
• wR factor = 0.122
• Data-to-parameter ratio = 12.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

2-(2-Methoxyphenylhydrazono)-3-oxo-butanoic acid

Crystal data

C11H12N2O4	Z = 4
Mr = 236.23	F(000) = 496
Triclinic, P1	Dx = 1.388 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.105 (3) Å	Cell parameters from 25 reflections
b = 11.065 (2) Å	θ = 8.4–11.0°
c = 14.163 (4) Å	µ = 0.11 mm^−1
α = 111.17 (3)°	T = 293 K
β = 95.85 (4)°	Elongated needle, clear light yellow
γ = 102.97 (3)°	0.33 × 0.25 × 0.05 mm
V = 1130.6 (6) Å^3

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.042
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.0°
Graphite monochromator	h = 0→9
ω–2θ scans	k = −13→12
4142 measured reflections	l = −16→16
3962 independent reflections	3 standard reflections every 50 reflections
2114 reflections with I > 2σ(I)	intensity decay: 0.0%

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H-atom parameters constrained
S = 0.88	w = 1/[σ^2(Fo^2) + (0.0719P)^2] where P = (Fo^2 + 2Fc^2)/3
3962 reflections	(Δ/σ)max < 0.001
309 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.13 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.

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

	x	y	z	Uiso*/Ueq
O1	0.37034 (19)	−0.00055 (15)	0.66001 (12)	0.0661 (4)
O2	0.2691 (2)	0.20041 (17)	0.50280 (13)	0.0758 (5)
O3	0.1358 (2)	0.31415 (18)	0.43816 (13)	0.0833 (5)
H3O	0.0449	0.3350	0.4395	0.125*
O4	−0.1577 (2)	0.33469 (17)	0.48138 (13)	0.0758 (5)
N1	0.1271 (2)	0.11462 (15)	0.63415 (12)	0.0490 (4)
H1N	0.2136	0.1201	0.6039	0.059*
N2	−0.0001 (2)	0.16030 (16)	0.61250 (12)	0.0479 (4)
C1	0.1218 (3)	0.05626 (19)	0.70745 (15)	0.0491 (5)
C2	0.2501 (3)	−0.0054 (2)	0.72026 (16)	0.0517 (5)
C3	0.2467 (3)	−0.0654 (2)	0.79047 (18)	0.0628 (6)
H3	0.3314	−0.1069	0.7996	0.075*
C4	0.1183 (3)	−0.0639 (2)	0.84700 (19)	0.0699 (7)
H4	0.1157	−0.1055	0.8935	0.084*
C5	−0.0066 (3)	−0.0010 (2)	0.83513 (18)	0.0677 (7)
H5	−0.0924	0.0002	0.8740	0.081*
C6	−0.0046 (3)	0.0596 (2)	0.76637 (17)	0.0583 (6)
H6	−0.0880	0.1029	0.7592	0.070*
C7	0.0015 (2)	0.22091 (19)	0.54830 (15)	0.0468 (5)
C8	0.1456 (3)	0.2438 (2)	0.49468 (17)	0.0597 (6)
C9	−0.1499 (3)	0.2692 (2)	0.53534 (16)	0.0559 (6)
C10	−0.2947 (3)	0.2370 (3)	0.58675 (19)	0.0746 (7)
H10A	−0.3868	0.2703	0.5675	0.112*
H10B	−0.2548	0.2791	0.6604	0.112*
H10C	−0.3359	0.1409	0.5656	0.112*
C11	0.5090 (3)	−0.0582 (2)	0.6730 (2)	0.0762 (7)
H11A	0.5842	−0.0484	0.6265	0.114*
H11B	0.4621	−0.1523	0.6583	0.114*
H11C	0.5730	−0.0124	0.7429	0.114*
O1'	0.5158 (2)	0.51711 (17)	0.28300 (13)	0.0788 (5)
O2'	0.3233 (2)	0.7098 (2)	0.14893 (15)	0.0945 (6)
O3'	0.2915 (3)	0.8208 (2)	0.05051 (15)	0.1104 (7)
H3'O	0.3392	0.8399	0.0074	0.166*
O4'	0.5048 (3)	0.83538 (18)	−0.06765 (14)	0.0980 (6)
N1'	0.5984 (2)	0.62061 (16)	0.14815 (13)	0.0570 (5)
H1'N	0.5093	0.6293	0.1752	0.068*
N2'	0.6277 (2)	0.66395 (16)	0.07590 (13)	0.0533 (5)
C1'	0.7133 (3)	0.5592 (2)	0.18197 (16)	0.0559 (6)
C2'	0.6687 (3)	0.5049 (2)	0.25389 (18)	0.0633 (6)
C3'	0.7770 (4)	0.4421 (2)	0.2874 (2)	0.0787 (8)
H3'	0.7486	0.4044	0.3346	0.094*
C4'	0.9271 (4)	0.4353 (3)	0.2509 (2)	0.0881 (9)
H4'	0.9992	0.3925	0.2735	0.106*
C5'	0.9715 (4)	0.4907 (3)	0.1818 (2)	0.0857 (8)
H5'	1.0739	0.4863	0.1583	0.103*
C6'	0.8645 (3)	0.5531 (2)	0.14681 (19)	0.0704 (7)
H6'	0.8944	0.5908	0.0998	0.085*
C7'	0.5276 (3)	0.7248 (2)	0.04380 (16)	0.0561 (6)
C8'	0.3735 (3)	0.7500 (3)	0.0852 (2)	0.0740 (7)
C9'	0.5841 (3)	0.7712 (2)	−0.03530 (17)	0.0669 (7)
C10'	0.7367 (4)	0.7383 (3)	−0.0766 (2)	0.0846 (8)
H10D	0.7515	0.7683	−0.1317	0.127*
H10E	0.7194	0.6425	−0.1023	0.127*
H10F	0.8380	0.7830	−0.0225	0.127*
C11'	0.4609 (4)	0.4578 (3)	0.3535 (2)	0.1015 (10)
H11D	0.3524	0.4730	0.3680	0.152*
H11E	0.5460	0.4982	0.4166	0.152*
H11F	0.4476	0.3624	0.3231	0.152*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0603 (9)	0.0762 (11)	0.0852 (11)	0.0387 (8)	0.0227 (8)	0.0448 (9)
O2	0.0603 (10)	0.1012 (13)	0.0879 (12)	0.0366 (10)	0.0281 (9)	0.0505 (11)
O3	0.0780 (12)	0.1078 (14)	0.0968 (13)	0.0299 (10)	0.0299 (10)	0.0720 (12)
O4	0.0805 (11)	0.0900 (12)	0.0879 (12)	0.0397 (9)	0.0154 (9)	0.0614 (11)
N1	0.0462 (10)	0.0523 (10)	0.0587 (11)	0.0233 (8)	0.0120 (8)	0.0274 (9)
N2	0.0494 (10)	0.0480 (10)	0.0522 (10)	0.0220 (8)	0.0089 (8)	0.0219 (9)
C1	0.0519 (12)	0.0428 (12)	0.0538 (13)	0.0147 (10)	0.0016 (10)	0.0221 (11)
C2	0.0503 (12)	0.0485 (12)	0.0589 (14)	0.0194 (10)	0.0066 (11)	0.0221 (11)
C3	0.0675 (15)	0.0599 (14)	0.0718 (16)	0.0300 (12)	0.0062 (12)	0.0332 (13)
C4	0.0815 (18)	0.0740 (17)	0.0719 (16)	0.0293 (14)	0.0131 (14)	0.0452 (14)
C5	0.0687 (15)	0.0807 (17)	0.0756 (16)	0.0330 (13)	0.0234 (13)	0.0462 (15)
C6	0.0560 (13)	0.0642 (14)	0.0659 (15)	0.0286 (11)	0.0109 (11)	0.0318 (13)
C7	0.0501 (12)	0.0459 (12)	0.0478 (12)	0.0167 (10)	0.0079 (10)	0.0208 (11)
C8	0.0555 (14)	0.0643 (15)	0.0622 (15)	0.0165 (12)	0.0093 (11)	0.0291 (13)
C9	0.0586 (13)	0.0608 (14)	0.0552 (13)	0.0251 (11)	0.0065 (11)	0.0270 (12)
C10	0.0594 (14)	0.108 (2)	0.0856 (18)	0.0463 (14)	0.0231 (13)	0.0558 (16)
C11	0.0611 (15)	0.0851 (18)	0.099 (2)	0.0422 (13)	0.0178 (13)	0.0417 (16)
O1'	0.0853 (12)	0.0904 (13)	0.0804 (12)	0.0193 (10)	0.0200 (10)	0.0583 (11)
O2'	0.0907 (13)	0.1254 (16)	0.0956 (14)	0.0535 (12)	0.0373 (11)	0.0571 (13)
O3'	0.1262 (17)	0.1416 (18)	0.1036 (15)	0.0908 (15)	0.0272 (13)	0.0614 (14)
O4'	0.1442 (18)	0.0932 (14)	0.0799 (13)	0.0532 (13)	0.0088 (11)	0.0526 (12)
N1'	0.0687 (12)	0.0561 (11)	0.0580 (11)	0.0226 (9)	0.0142 (9)	0.0327 (10)
N2'	0.0682 (12)	0.0469 (10)	0.0491 (10)	0.0175 (9)	0.0108 (9)	0.0233 (9)
C1'	0.0712 (15)	0.0439 (12)	0.0525 (13)	0.0176 (11)	0.0025 (11)	0.0208 (11)
C2'	0.0771 (17)	0.0495 (13)	0.0593 (14)	0.0088 (12)	−0.0045 (13)	0.0272 (12)
C3'	0.096 (2)	0.0599 (16)	0.0784 (18)	0.0115 (15)	−0.0118 (16)	0.0392 (14)
C4'	0.099 (2)	0.0660 (17)	0.100 (2)	0.0333 (16)	−0.0077 (18)	0.0356 (17)
C5'	0.0867 (19)	0.0826 (19)	0.098 (2)	0.0444 (16)	0.0153 (16)	0.0363 (18)
C6'	0.0832 (18)	0.0652 (16)	0.0755 (17)	0.0321 (14)	0.0191 (14)	0.0347 (14)
C7'	0.0708 (15)	0.0524 (13)	0.0510 (13)	0.0250 (12)	0.0091 (11)	0.0234 (11)
C8'	0.0887 (19)	0.0788 (18)	0.0644 (16)	0.0383 (15)	0.0117 (15)	0.0319 (15)
C9'	0.0996 (19)	0.0524 (14)	0.0513 (14)	0.0221 (13)	0.0033 (13)	0.0265 (12)
C10'	0.103 (2)	0.092 (2)	0.0699 (17)	0.0239 (17)	0.0310 (16)	0.0444 (16)
C11'	0.113 (2)	0.118 (2)	0.093 (2)	0.0158 (19)	0.0294 (18)	0.072 (2)

Geometric parameters (Å, º)

O1—C2	1.364 (3)	O1'—C2'	1.365 (3)
O1—C11	1.438 (2)	O1'—C11'	1.435 (3)
O2—C8	1.216 (3)	O2'—C8'	1.209 (3)
O3—C8	1.311 (3)	O3'—C8'	1.319 (3)
O3—H3O	0.82	O3'—H3'O	0.82
O4—C9	1.234 (2)	O4'—C9'	1.228 (3)
N1—N2	1.302 (2)	N1'—N2'	1.299 (2)
N1—C1	1.406 (2)	N1'—C1'	1.409 (3)
N1—H1N	0.86	N1'—H1'N	0.86
N2—C7	1.310 (2)	N2'—C7'	1.308 (3)
C1—C6	1.384 (3)	C1'—C6'	1.375 (3)
C1—C2	1.396 (3)	C1'—C2'	1.396 (3)
C2—C3	1.380 (3)	C2'—C3'	1.380 (3)
C3—C4	1.376 (3)	C3'—C4'	1.376 (4)
C3—H3	0.93	C3'—H3'	0.93
C4—C5	1.380 (3)	C4'—C5'	1.367 (4)
C4—H4	0.93	C4'—H4'	0.93
C5—C6	1.366 (3)	C5'—C6'	1.379 (3)
C5—H5	0.93	C5'—H5'	0.93
C6—H6	0.93	C6'—H6'	0.93
C7—C9	1.465 (3)	C7'—C9'	1.464 (3)
C7—C8	1.481 (3)	C7'—C8'	1.473 (3)
C9—C10	1.486 (3)	C9'—C10'	1.483 (4)
C10—H10A	0.96	C10'—H10D	0.96
C10—H10B	0.96	C10'—H10E	0.96
C10—H10C	0.96	C10'—H10F	0.96
C11—H11A	0.96	C11'—H11D	0.96
C11—H11B	0.96	C11'—H11E	0.96
C11—H11C	0.96	C11'—H11F	0.96
C2—O1—C11	117.62 (17)	C2'—O1'—C11'	117.3 (2)
C8—O3—H3O	109.5	C8'—O3'—H3'O	109.5
N2—N1—C1	119.37 (17)	N2'—N1'—C1'	119.73 (19)
N2—N1—H1N	120.3	N2'—N1'—H1'N	120.1
C1—N1—H1N	120.3	C1'—N1'—H1'N	120.1
N1—N2—C7	121.97 (17)	N1'—N2'—C7'	122.04 (19)
C6—C1—C2	120.14 (19)	C6'—C1'—C2'	120.6 (2)
C6—C1—N1	122.01 (18)	C6'—C1'—N1'	122.0 (2)
C2—C1—N1	117.85 (19)	C2'—C1'—N1'	117.4 (2)
O1—C2—C3	125.39 (18)	O1'—C2'—C3'	125.8 (2)
O1—C2—C1	115.42 (18)	O1'—C2'—C1'	115.3 (2)
C3—C2—C1	119.2 (2)	C3'—C2'—C1'	118.9 (3)
C4—C3—C2	120.1 (2)	C4'—C3'—C2'	120.0 (3)
C4—C3—H3	120.0	C4'—C3'—H3'	120.0
C2—C3—H3	120.0	C2'—C3'—H3'	120.0
C3—C4—C5	120.4 (2)	C5'—C4'—C3'	120.8 (2)
C3—C4—H4	119.8	C5'—C4'—H4'	119.6
C5—C4—H4	119.8	C3'—C4'—H4'	119.6
C6—C5—C4	120.2 (2)	C4'—C5'—C6'	120.1 (3)
C6—C5—H5	119.9	C4'—C5'—H5'	120.0
C4—C5—H5	119.9	C6'—C5'—H5'	120.0
C5—C6—C1	119.9 (2)	C1'—C6'—C5'	119.6 (2)
C5—C6—H6	120.0	C1'—C6'—H6'	120.2
C1—C6—H6	120.0	C5'—C6'—H6'	120.2
N2—C7—C9	114.61 (18)	N2'—C7'—C9'	114.5 (2)
N2—C7—C8	123.68 (18)	N2'—C7'—C8'	123.7 (2)
C9—C7—C8	121.68 (18)	C9'—C7'—C8'	121.8 (2)
O2—C8—O3	120.9 (2)	O2'—C8'—O3'	120.5 (3)
O2—C8—C7	121.9 (2)	O2'—C8'—C7'	122.5 (2)
O3—C8—C7	117.2 (2)	O3'—C8'—C7'	117.0 (2)
O4—C9—C7	120.2 (2)	O4'—C9'—C7'	120.2 (2)
O4—C9—C10	120.52 (19)	O4'—C9'—C10'	120.5 (2)
C7—C9—C10	119.24 (18)	C7'—C9'—C10'	119.2 (2)
C9—C10—H10A	109.5	C9'—C10'—H10D	109.5
C9—C10—H10B	109.5	C9'—C10'—H10E	109.5
H10A—C10—H10B	109.5	H10D—C10'—H10E	109.5
C9—C10—H10C	109.5	C9'—C10'—H10F	109.5
H10A—C10—H10C	109.5	H10D—C10'—H10F	109.5
H10B—C10—H10C	109.5	H10E—C10'—H10F	109.5
O1—C11—H11A	109.5	O1'—C11'—H11D	109.5
O1—C11—H11B	109.5	O1'—C11'—H11E	109.5
H11A—C11—H11B	109.5	H11D—C11'—H11E	109.5
O1—C11—H11C	109.5	O1'—C11'—H11F	109.5
H11A—C11—H11C	109.5	H11D—C11'—H11F	109.5
H11B—C11—H11C	109.5	H11E—C11'—H11F	109.5
C1—N1—N2—C7	176.95 (17)	C1'—N1'—N2'—C7'	−178.14 (19)
N2—N1—C1—C6	−7.6 (3)	N2'—N1'—C1'—C6'	5.4 (3)
N2—N1—C1—C2	172.86 (17)	N2'—N1'—C1'—C2'	−175.06 (19)
C11—O1—C2—C3	−2.4 (3)	C11'—O1'—C2'—C3'	−1.0 (3)
C11—O1—C2—C1	177.75 (19)	C11'—O1'—C2'—C1'	177.5 (2)
C6—C1—C2—O1	−178.67 (19)	C6'—C1'—C2'—O1'	179.9 (2)
N1—C1—C2—O1	0.9 (3)	N1'—C1'—C2'—O1'	0.4 (3)
C6—C1—C2—C3	1.5 (3)	C6'—C1'—C2'—C3'	−1.5 (3)
N1—C1—C2—C3	−179.01 (19)	N1'—C1'—C2'—C3'	179.0 (2)
O1—C2—C3—C4	−180.0 (2)	O1'—C2'—C3'—C4'	179.2 (2)
C1—C2—C3—C4	−0.1 (3)	C1'—C2'—C3'—C4'	0.8 (4)
C2—C3—C4—C5	−0.9 (4)	C2'—C3'—C4'—C5'	0.3 (4)
C3—C4—C5—C6	0.5 (4)	C3'—C4'—C5'—C6'	−0.7 (4)
C4—C5—C6—C1	0.9 (4)	C2'—C1'—C6'—C5'	1.1 (3)
C2—C1—C6—C5	−1.8 (3)	N1'—C1'—C6'—C5'	−179.4 (2)
N1—C1—C6—C5	178.6 (2)	C4'—C5'—C6'—C1'	0.0 (4)
N1—N2—C7—C9	−178.31 (17)	N1'—N2'—C7'—C9'	177.82 (18)
N1—N2—C7—C8	−0.1 (3)	N1'—N2'—C7'—C8'	−0.2 (3)
N2—C7—C8—O2	4.2 (3)	N2'—C7'—C8'—O2'	−3.7 (4)
C9—C7—C8—O2	−177.8 (2)	C9'—C7'—C8'—O2'	178.4 (3)
N2—C7—C8—O3	−175.3 (2)	N2'—C7'—C8'—O3'	175.4 (2)
C9—C7—C8—O3	2.7 (3)	C9'—C7'—C8'—O3'	−2.4 (3)
N2—C7—C9—O4	175.8 (2)	N2'—C7'—C9'—O4'	−176.5 (2)
C8—C7—C9—O4	−2.4 (3)	C8'—C7'—C9'—O4'	1.5 (4)
N2—C7—C9—C10	−5.0 (3)	N2'—C7'—C9'—C10'	4.2 (3)
C8—C7—C9—C10	176.8 (2)	C8'—C7'—C9'—C10'	−177.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2	0.86	1.98	2.628 (2)	132
O3—H3O···O4	0.82	1.80	2.554 (2)	152
N1′—H1′N···O2′	0.86	1.98	2.633 (3)	132
O3′—H3′O···O4′	0.82	1.79	2.544 (3)	152