Methyl [(4-nitro­phen­yl)hydrazono]acetate

Xu, J.

doi:10.1107/S1600536806044552

Methyl [(4-nitrophenyl)hydrazono]acetate

The asymmetric unit of the title compound, C₉H₉N₃O₄, consists of two independent but similar molecules which are located on mirror planes. The molecules pack along the b axis with an interplanar distance of b/2. Intramolecular N—H

O hydrogen bonds help to stablize the molecular structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806044552/dn2081sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806044552/dn2081Isup2.hkl Contains datablock I

CCDC reference: 627495

checkCIF report

Key indicators

Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.005 Å
R factor = 0.060
wR factor = 0.063
Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     -   N1      ..       5.33 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     -   C6      ..       5.35 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O8     -   C17     ..       5.57 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C10    -   C11     ..       5.65 su
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Methyl [(4-nitrophenyl)hydrazono]acetate top

Crystal data top

C₉H₉N₃O₄	F(000) = 464
M_r = 223.19	D_x = 1.342 Mg m⁻³
Monoclinic, P2/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2y	Cell parameters from 926 reflections
a = 6.164 (12) Å	θ = 2.9–22.7°
b = 6.402 (12) Å	µ = 0.11 mm⁻¹
c = 28.10 (5) Å	T = 291 K
β = 95.03 (3)°	Block, brown
V = 1105 (4) Å³	0.28 × 0.26 × 0.16 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	2266 independent reflections
Radiation source: sealed tube	1182 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
φ and ω scans	θ_max = 25.5°, θ_min = 0.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −7→7
T_min = 0.97, T_max = 0.98	k = −7→7
8214 measured reflections	l = −23→34

Refinement top

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.063	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0176P)²] where P = (F_o² + 2F_c²)/3
2266 reflections	(Δ/σ)_max < 0.001
195 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.6584 (5)	0.0000	0.23454 (11)	0.0595 (8)
C2	0.8154 (5)	0.0000	0.20097 (11)	0.0653 (9)
H2	0.9632	0.0000	0.2110	0.078*
C3	0.7448 (4)	0.0000	0.15247 (10)	0.0551 (7)
H3	0.8481	0.0000	0.1303	0.066*
C4	0.5301 (5)	0.0000	0.13652 (11)	0.0563 (8)
C5	0.3824 (5)	0.0000	0.16896 (10)	0.0605 (8)
H5	0.2357	0.0000	0.1579	0.073*
C6	0.4351 (5)	0.0000	0.21763 (11)	0.0581 (8)
H6	0.3272	0.0000	0.2388	0.070*
C7	0.6402 (5)	0.0000	0.36304 (13)	0.0738 (9)
H7	0.5380	0.0000	0.3855	0.089*
C8	0.8696 (5)	0.0000	0.37753 (12)	0.0617 (8)
C9	0.7994 (5)	0.0000	0.45966 (11)	0.0661 (8)
H9A	0.8733	−0.0249	0.4906	0.099*	0.50
H9B	0.6937	−0.1081	0.4524	0.099*	0.50
H9C	0.7273	0.1330	0.4595	0.099*	0.50
C10	0.7956 (5)	0.5000	0.27508 (13)	0.0643 (8)
C11	0.6380 (5)	0.5000	0.30544 (11)	0.0603 (8)
H11	0.4923	0.5000	0.2936	0.072*
C12	0.6945 (4)	0.5000	0.35495 (10)	0.0598 (8)
H12	0.5872	0.5000	0.3762	0.072*
C13	0.9132 (5)	0.5000	0.37152 (11)	0.0584 (8)
C14	1.0704 (4)	0.5000	0.33891 (10)	0.0544 (7)
H14	1.2174	0.5000	0.3498	0.065*
C15	1.0110 (5)	0.5000	0.29224 (11)	0.0623 (8)
H15	1.1177	0.5000	0.2708	0.075*
C16	0.8234 (4)	0.5000	0.14799 (10)	0.0471 (6)
H16	0.9311	0.5000	0.1268	0.057*
C17	0.5866 (4)	0.5000	0.12808 (12)	0.0573 (7)
C18	0.6680 (4)	0.5000	0.04677 (10)	0.0602 (8)
H18A	0.7652	0.3831	0.0513	0.090*	0.50
H18B	0.7506	0.6273	0.0484	0.090*	0.50
H18C	0.5872	0.4896	0.0161	0.090*	0.50
N1	0.4597 (4)	0.0000	0.08531 (9)	0.0597 (6)
N2	0.7204 (4)	0.0000	0.28354 (9)	0.0612 (7)
H2A	0.8562	0.0000	0.2936	0.073*
N3	0.5751 (4)	0.0000	0.31357 (10)	0.0674 (7)
N4	0.9746 (4)	0.5000	0.42269 (9)	0.0517 (6)
N5	0.7341 (4)	0.5000	0.22412 (10)	0.0631 (7)
H5A	0.5989	0.5000	0.2136	0.076*
N6	0.8827 (4)	0.5000	0.19483 (9)	0.0600 (6)
O1	0.2737 (3)	0.0000	0.07177 (6)	0.0591 (5)
O2	0.5977 (3)	0.0000	0.05447 (8)	0.0684 (6)
O3	1.0128 (3)	0.0000	0.35034 (7)	0.0501 (5)
O4	0.9481 (3)	0.0000	0.42590 (8)	0.0650 (6)
O5	1.1650 (3)	0.5000	0.44053 (6)	0.0538 (5)
O6	0.8339 (3)	0.5000	0.45314 (6)	0.0508 (5)
O7	0.4506 (3)	0.5000	0.15693 (7)	0.0679 (6)
O8	0.5284 (3)	0.5000	0.08137 (6)	0.0536 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0558 (17)	0.0639 (19)	0.059 (2)	0.000	0.0056 (16)	0.000
C2	0.0622 (19)	0.070 (2)	0.065 (2)	0.000	0.0123 (17)	0.000
C3	0.0636 (19)	0.0464 (16)	0.0559 (19)	0.000	0.0090 (15)	0.000
C4	0.0598 (19)	0.0511 (17)	0.060 (2)	0.000	0.0155 (16)	0.000
C5	0.0697 (19)	0.0546 (17)	0.057 (2)	0.000	0.0073 (17)	0.000
C6	0.0684 (19)	0.0477 (18)	0.0593 (19)	0.000	0.0111 (15)	0.000
C7	0.064 (2)	0.079 (2)	0.082 (3)	0.000	0.0253 (19)	0.000
C8	0.0599 (18)	0.0530 (17)	0.075 (2)	0.000	0.0191 (17)	0.000
C9	0.0654 (18)	0.0629 (18)	0.073 (2)	0.000	0.0221 (16)	0.000
C10	0.0584 (19)	0.066 (2)	0.072 (2)	0.000	0.0246 (18)	0.000
C11	0.0625 (18)	0.0572 (18)	0.062 (2)	0.000	0.0084 (16)	0.000
C12	0.0563 (18)	0.0703 (19)	0.0575 (18)	0.000	0.0317 (15)	0.000
C13	0.0558 (17)	0.0652 (19)	0.0564 (19)	0.000	0.0178 (15)	0.000
C14	0.0423 (14)	0.0646 (19)	0.0568 (19)	0.000	0.0082 (14)	0.000
C15	0.0654 (19)	0.067 (2)	0.057 (2)	0.000	0.0192 (16)	0.000
C16	0.0468 (15)	0.0405 (14)	0.0539 (17)	0.000	0.0030 (13)	0.000
C17	0.0485 (16)	0.0664 (19)	0.0582 (19)	0.000	0.0110 (15)	0.000
C18	0.0612 (16)	0.0637 (19)	0.0562 (19)	0.000	0.0082 (15)	0.000
N1	0.0594 (16)	0.0634 (16)	0.0584 (16)	0.000	0.0168 (14)	0.000
N2	0.0576 (15)	0.0695 (19)	0.0562 (17)	0.000	0.0032 (13)	0.000
N3	0.0673 (16)	0.0623 (16)	0.076 (2)	0.000	0.0258 (16)	0.000
N4	0.0560 (14)	0.0449 (13)	0.0563 (15)	0.000	0.0171 (13)	0.000
N5	0.0617 (15)	0.0609 (17)	0.0691 (18)	0.000	0.0189 (14)	0.000
N6	0.0691 (15)	0.0536 (15)	0.0581 (16)	0.000	0.0104 (14)	0.000
O1	0.0557 (11)	0.0599 (13)	0.0650 (13)	0.000	0.0239 (10)	0.000
O2	0.0656 (12)	0.0687 (14)	0.0729 (15)	0.000	0.0170 (12)	0.000
O3	0.0437 (9)	0.0541 (11)	0.0529 (12)	0.000	0.0063 (9)	0.000
O4	0.0701 (13)	0.0622 (13)	0.0665 (14)	0.000	0.0275 (11)	0.000
O5	0.0630 (12)	0.0460 (11)	0.0525 (12)	0.000	0.0051 (9)	0.000
O6	0.0411 (9)	0.0562 (11)	0.0561 (12)	0.000	0.0100 (9)	0.000
O7	0.0732 (13)	0.0683 (14)	0.0655 (13)	0.000	0.0249 (11)	0.000
O8	0.0610 (11)	0.0539 (11)	0.0463 (12)	0.000	0.0082 (9)	0.000

Geometric parameters (Å, º) top

C1—N2	1.396 (4)	C11—H11	0.9300
C1—C2	1.410 (4)	C12—C13	1.387 (5)
C1—C6	1.416 (5)	C12—H12	0.9300
C2—C3	1.394 (5)	C13—C14	1.391 (4)
C2—H2	0.9300	C13—N4	1.454 (4)
C3—C4	1.359 (4)	C14—C15	1.330 (4)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.344 (4)	C15—H15	0.9300
C4—N1	1.466 (5)	C16—N6	1.335 (4)
C5—C6	1.377 (5)	C16—C17	1.517 (4)
C5—H5	0.9300	C16—H16	0.9300
C6—H6	0.9300	C17—O7	1.216 (3)
C7—N3	1.413 (5)	C17—O8	1.330 (4)
C7—C8	1.436 (5)	C18—O8	1.354 (3)
C7—H7	0.9300	C18—H18A	0.9600
C8—O3	1.217 (3)	C18—H18B	0.9600
C8—O4	1.402 (4)	C18—H18C	0.9600
C9—O4	1.376 (4)	N1—O1	1.176 (3)
C9—H9A	0.9600	N1—O2	1.266 (3)
C9—H9B	0.9600	N2—N3	1.283 (3)
C9—H9C	0.9600	N2—H2A	0.8600
C10—C11	1.348 (4)	N4—O5	1.235 (3)
C10—C15	1.372 (5)	N4—O6	1.271 (3)
C10—N5	1.449 (5)	N5—N6	1.284 (3)
C11—C12	1.404 (5)	N5—H5A	0.8600

N2—C1—C2	121.0 (3)	C11—C12—H12	120.6
N2—C1—C6	120.3 (2)	C12—C13—C14	119.4 (3)
C2—C1—C6	118.7 (3)	C12—C13—N4	119.5 (3)
C3—C2—C1	118.7 (3)	C14—C13—N4	121.0 (3)
C3—C2—H2	120.6	C15—C14—C13	120.1 (3)
C1—C2—H2	120.6	C15—C14—H14	119.9
C4—C3—C2	122.3 (3)	C13—C14—H14	119.9
C4—C3—H3	118.9	C14—C15—C10	121.4 (3)
C2—C3—H3	118.9	C14—C15—H15	119.3
C5—C4—C3	118.3 (3)	C10—C15—H15	119.3
C5—C4—N1	120.4 (3)	N6—C16—C17	122.4 (2)
C3—C4—N1	121.3 (3)	N6—C16—H16	118.8
C4—C5—C6	124.0 (3)	C17—C16—H16	118.8
C4—C5—H5	118.0	O7—C17—O8	121.1 (3)
C6—C5—H5	118.0	O7—C17—C16	116.8 (3)
C5—C6—C1	118.1 (3)	O8—C17—C16	122.1 (2)
C5—C6—H6	120.9	O8—C18—H18A	109.5
C1—C6—H6	120.9	O8—C18—H18B	109.5
N3—C7—C8	117.8 (3)	H18A—C18—H18B	109.5
N3—C7—H7	121.1	O8—C18—H18C	109.5
C8—C7—H7	121.1	H18A—C18—H18C	109.5
O3—C8—O4	113.6 (3)	H18B—C18—H18C	109.5
O3—C8—C7	124.9 (3)	O1—N1—O2	118.2 (3)
O4—C8—C7	121.5 (2)	O1—N1—C4	120.9 (2)
O4—C9—H9A	109.5	O2—N1—C4	120.9 (3)
O4—C9—H9B	109.5	N3—N2—C1	120.1 (3)
H9A—C9—H9B	109.5	N3—N2—H2A	119.9
O4—C9—H9C	109.5	C1—N2—H2A	119.9
H9A—C9—H9C	109.5	N2—N3—C7	119.5 (3)
H9B—C9—H9C	109.5	O5—N4—O6	114.0 (3)
C11—C10—C15	120.4 (4)	O5—N4—C13	123.8 (2)
C11—C10—N5	119.0 (3)	O6—N4—C13	122.1 (3)
C15—C10—N5	120.6 (3)	N6—N5—C10	119.6 (3)
C10—C11—C12	119.8 (3)	N6—N5—H5A	120.2
C10—C11—H11	120.1	C10—N5—H5A	120.2
C12—C11—H11	120.1	N5—N6—C16	118.9 (3)
C13—C12—C11	118.8 (3)	C9—O4—C8	118.3 (3)
C13—C12—H12	120.6	C17—O8—C18	125.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3	0.86	1.79	2.486 (5)	137
N5—H5A···O7	0.86	1.76	2.458 (5)	136

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Methyl [(4-nitro­phen­yl)hydrazono]acetate

Supporting information

Key indicators

checkCIF/PLATON results

Methyl [(4-nitrophenyl)hydrazono]acetate