Ethyl 2-[(Z)-2-(2-nitro­phen­yl)hydrazinyl­idene]propano­ate

In the mol­ecule of the title compound, C₁₁H₁₃N₃O₄, all non-H atoms are nearly coplanar with the largest deviation from the mean plane being 0.152 (2) Å. A strong intra­molecular N—H...O hydrogen bond closes a six-membered ring. In the crystal, mol­ecules are linked by π–π inter­actions [inter­centroid distance = 3.724 (2) Å], forming stacks parallel to the c axis.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.049
• wR factor = 0.146
• Data-to-parameter ratio = 21.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -3.318 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....         C8 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           5 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus (Bruker, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Ethyl 2-[(Z)-2-(2-nitrophenyl)hydrazinylidene]propanoate

Crystal data

C11H13N3O4	F(000) = 528
Mr = 251.24	Dx = 1.344 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.8614 (4) Å	Cell parameters from 3487 reflections
b = 15.8834 (6) Å	θ = 2.2–29.6°
c = 6.7495 (2) Å	µ = 0.10 mm^−1
β = 102.411 (2)°	T = 296 K
V = 1241.89 (7) Å^3	Plate, yellow
Z = 4	0.42 × 0.33 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer	1892 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.058
φ and ω scans	θmax = 29.6°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2015)	h = −16→16
Tmin = 0.452, Tmax = 0.746	k = −22→22
37344 measured reflections	l = −9→6
3487 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.049	w = 1/[σ^2(Fo^2) + (0.0566P)^2 + 0.2115P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.146	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.22 e Å^−3
3487 reflections	Δρmin = −0.22 e Å^−3
164 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0117 (17)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.65861 (13)	0.28676 (10)	0.4729 (2)	0.0471 (4)
C2	0.75897 (14)	0.23883 (12)	0.5128 (3)	0.0589 (4)
H2	0.8304	0.2655	0.5410	0.071*
C3	0.75360 (16)	0.15360 (12)	0.5110 (3)	0.0653 (5)
H3	0.8209	0.1217	0.5383	0.078*
C4	0.64643 (16)	0.11452 (11)	0.4679 (3)	0.0637 (5)
H4	0.6425	0.0560	0.4661	0.076*
C5	0.54619 (14)	0.16054 (10)	0.4280 (3)	0.0534 (4)
H5	0.4755	0.1328	0.3993	0.064*
C6	0.54875 (12)	0.24845 (9)	0.4298 (2)	0.0438 (3)
C7	0.25524 (13)	0.30082 (10)	0.3148 (2)	0.0480 (4)
C8	0.25598 (16)	0.39424 (11)	0.3224 (4)	0.0789 (6)
H8A	0.1780	0.4147	0.2918	0.118*
H8B	0.2938	0.4126	0.4557	0.118*
H8C	0.2966	0.4158	0.2246	0.118*
C9	0.14199 (13)	0.25757 (11)	0.2633 (2)	0.0516 (4)
C10	0.04194 (14)	0.12833 (12)	0.2233 (3)	0.0683 (5)
H10A	0.0062	0.1356	0.0809	0.082*
H10B	−0.0109	0.1488	0.3039	0.082*
C11	0.06936 (18)	0.03794 (13)	0.2684 (4)	0.0847 (6)
H11A	−0.0005	0.0054	0.2371	0.127*
H11B	0.1216	0.0185	0.1876	0.127*
H11C	0.1046	0.0316	0.4095	0.127*
N1	0.67284 (12)	0.37725 (9)	0.4780 (2)	0.0566 (4)
N2	0.44815 (10)	0.29405 (8)	0.3914 (2)	0.0483 (3)
H2N	0.4542	0.3492	0.3880	0.058*
N3	0.34528 (10)	0.25358 (8)	0.34835 (19)	0.0453 (3)
O1	0.58726 (11)	0.42318 (7)	0.4422 (2)	0.0711 (4)
O2	0.77058 (11)	0.40635 (9)	0.5191 (2)	0.0821 (4)
O3	0.05164 (10)	0.29500 (8)	0.2177 (2)	0.0730 (4)
O4	0.15006 (9)	0.17423 (7)	0.27317 (19)	0.0618 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0443 (8)	0.0505 (9)	0.0472 (9)	−0.0012 (7)	0.0111 (7)	−0.0009 (7)
C2	0.0433 (8)	0.0718 (12)	0.0616 (11)	0.0028 (8)	0.0112 (7)	0.0023 (9)
C3	0.0551 (10)	0.0688 (12)	0.0737 (12)	0.0187 (9)	0.0177 (9)	0.0083 (9)
C4	0.0738 (12)	0.0490 (9)	0.0716 (12)	0.0105 (9)	0.0229 (9)	0.0052 (9)
C5	0.0533 (9)	0.0480 (9)	0.0602 (10)	−0.0013 (7)	0.0153 (8)	−0.0002 (8)
C6	0.0433 (8)	0.0473 (8)	0.0415 (8)	0.0013 (6)	0.0106 (6)	0.0004 (6)
C7	0.0435 (8)	0.0507 (9)	0.0489 (9)	0.0016 (6)	0.0081 (7)	−0.0014 (7)
C8	0.0584 (11)	0.0524 (10)	0.1209 (18)	0.0058 (9)	0.0080 (11)	−0.0006 (11)
C9	0.0435 (8)	0.0579 (10)	0.0530 (10)	0.0030 (7)	0.0095 (7)	−0.0016 (8)
C10	0.0437 (9)	0.0739 (12)	0.0857 (14)	−0.0127 (8)	0.0106 (9)	−0.0092 (10)
C11	0.0770 (13)	0.0692 (13)	0.1053 (18)	−0.0216 (11)	0.0139 (12)	−0.0040 (12)
N1	0.0490 (8)	0.0564 (8)	0.0653 (9)	−0.0086 (6)	0.0142 (7)	−0.0056 (7)
N2	0.0406 (7)	0.0434 (7)	0.0601 (8)	−0.0015 (5)	0.0089 (6)	−0.0003 (6)
N3	0.0397 (6)	0.0499 (7)	0.0461 (7)	−0.0037 (5)	0.0089 (5)	−0.0017 (6)
O1	0.0567 (7)	0.0492 (7)	0.1059 (10)	−0.0022 (6)	0.0143 (7)	−0.0023 (7)
O2	0.0521 (7)	0.0716 (9)	0.1210 (12)	−0.0189 (6)	0.0154 (7)	−0.0065 (8)
O3	0.0443 (7)	0.0746 (9)	0.0952 (10)	0.0100 (6)	0.0041 (6)	0.0009 (7)
O4	0.0386 (6)	0.0560 (7)	0.0885 (9)	−0.0046 (5)	0.0084 (5)	−0.0047 (6)

Geometric parameters (Å, º)

C1—C2	1.390 (2)	C8—H8B	0.9600
C1—C6	1.411 (2)	C8—H8C	0.9600
C1—N1	1.447 (2)	C9—O3	1.2062 (18)
C2—C3	1.355 (3)	C9—O4	1.328 (2)
C2—H2	0.9300	C10—O4	1.4505 (19)
C3—C4	1.388 (3)	C10—C11	1.489 (3)
C3—H3	0.9300	C10—H10A	0.9700
C4—C5	1.372 (2)	C10—H10B	0.9700
C4—H4	0.9300	C11—H11A	0.9600
C5—C6	1.397 (2)	C11—H11B	0.9600
C5—H5	0.9300	C11—H11C	0.9600
C6—N2	1.3722 (18)	N1—O2	1.2233 (17)
C7—N3	1.2849 (18)	N1—O1	1.2311 (17)
C7—C9	1.482 (2)	N2—N3	1.3542 (16)
C7—C8	1.485 (2)	N2—H2N	0.8796
C8—H8A	0.9600
C2—C1—C6	121.23 (15)	H8A—C8—H8C	109.5
C2—C1—N1	116.67 (14)	H8B—C8—H8C	109.5
C6—C1—N1	122.10 (13)	O3—C9—O4	123.69 (15)
C3—C2—C1	120.59 (16)	O3—C9—C7	122.84 (16)
C3—C2—H2	119.7	O4—C9—C7	113.48 (13)
C1—C2—H2	119.7	O4—C10—C11	107.09 (15)
C2—C3—C4	119.19 (16)	O4—C10—H10A	110.3
C2—C3—H3	120.4	C11—C10—H10A	110.3
C4—C3—H3	120.4	O4—C10—H10B	110.3
C5—C4—C3	121.25 (16)	C11—C10—H10B	110.3
C5—C4—H4	119.4	H10A—C10—H10B	108.6
C3—C4—H4	119.4	C10—C11—H11A	109.5
C4—C5—C6	120.96 (16)	C10—C11—H11B	109.5
C4—C5—H5	119.5	H11A—C11—H11B	109.5
C6—C5—H5	119.5	C10—C11—H11C	109.5
N2—C6—C5	120.64 (14)	H11A—C11—H11C	109.5
N2—C6—C1	122.58 (14)	H11B—C11—H11C	109.5
C5—C6—C1	116.78 (14)	O2—N1—O1	121.46 (15)
N3—C7—C9	116.60 (14)	O2—N1—C1	118.74 (14)
N3—C7—C8	125.38 (15)	O1—N1—C1	119.80 (13)
C9—C7—C8	118.01 (14)	N3—N2—C6	119.79 (13)
C7—C8—H8A	109.5	N3—N2—H2N	122.8
C7—C8—H8B	109.5	C6—N2—H2N	117.2
H8A—C8—H8B	109.5	C7—N3—N2	115.92 (13)
C7—C8—H8C	109.5	C9—O4—C10	116.03 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1	0.88	1.94	2.6085 (17)	132