2-(3-Carboxy­methyl-4-nitro­phenyl)­propionic acid

The mol­ecules of the title di­carboxyl­ic acid, C₁₁H₁₁NO₆, are linked by two pairs of hydrogen bonds into a linear chain structure; the nitro group distorts the bond dimensions of the aromatic ring.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• R factor = 0.067
• wR factor = 0.195
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.695     0.971
            Tmin' and Tmax expected:      0.951     0.971
            RR' =      0.731
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.73

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.76
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.11 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.49 Ratio
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         C1
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

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

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Computing details

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

2-(3-Carboxymethyl-4-nitrophenyl)propionic acid

Crystal data

C11H11NO6	Z = 2
Mr = 253.21	F(000) = 264
Triclinic, P1	Dx = 1.431 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.468 (3) Å	Cell parameters from 5376 reflections
b = 8.550 (4) Å	θ = 3.4–27.5°
c = 9.525 (5) Å	µ = 0.12 mm^−1
α = 104.03 (3)°	T = 298 K
β = 91.42 (5)°	Block, yellow
γ = 94.33 (3)°	0.42 × 0.31 × 0.25 mm
V = 587.8 (5) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	2347 independent reflections
Radiation source: fine-focus sealed tube	1680 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ω scans	θmax = 26.2°, θmin = 3.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→8
Tmin = 0.695, Tmax = 0.971	k = −10→10
4881 measured reflections	l = −11→11

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.195	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0907P)^2 + 0.3164P] where P = (Fo^2 + 2Fc^2)/3
2347 reflections	(Δ/σ)max = 0.001
165 parameters	Δρmax = 0.47 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

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

	x	y	z	Uiso*/Ueq
O1	0.4588 (4)	0.4130 (3)	0.1499 (3)	0.0902 (8)
O2	0.3557 (4)	0.6209 (4)	0.0865 (3)	0.0972 (9)
O3	0.2473 (3)	1.0300 (3)	1.0159 (2)	0.0753 (7)
O4	0.0479 (3)	0.9282 (3)	0.8338 (2)	0.0616 (6)
O5	0.2541 (4)	1.2355 (3)	0.7748 (3)	0.0822 (7)
O6	0.2836 (4)	1.3122 (3)	0.5784 (3)	0.0932 (9)
N1	0.2679 (3)	1.2065 (3)	0.6446 (3)	0.0606 (7)
C1	0.3613 (5)	0.5298 (4)	0.1690 (4)	0.0659 (8)
C2	0.2467 (6)	0.5504 (4)	0.3002 (4)	0.083 (1)
C3	0.0632 (7)	0.4799 (6)	0.2553 (7)	0.152 (3)
C4	0.2538 (4)	0.7245 (4)	0.3901 (3)	0.0586 (7)
C5	0.3031 (4)	0.7601 (4)	0.5363 (3)	0.0599 (8)
C6	0.3085 (3)	0.9154 (4)	0.6263 (3)	0.0520 (7)
C7	0.2650 (3)	1.0369 (3)	0.5608 (3)	0.0486 (6)
C8	0.2152 (4)	1.0061 (4)	0.4162 (3)	0.0540 (7)
C9	0.2078 (4)	0.8511 (4)	0.3313 (3)	0.0586 (7)
C10	0.3613 (4)	0.9412 (4)	0.7848 (3)	0.0639 (8)
C11	0.2028 (4)	0.9659 (4)	0.8797 (3)	0.0531 (7)
H1	0.5092	0.4048	0.0733	0.108*
H3	0.1561	1.0469	1.0615	0.113*
H2	0.2961	0.4867	0.3624	0.100*
H3a	−0.0064	0.4846	0.3394	0.227*
H3b	0.0663	0.3692	0.2027	0.227*
H3c	0.0094	0.5396	0.1944	0.227*
H5	0.3341	0.6762	0.5762	0.072*
H8	0.1865	1.0903	0.3759	0.065*
H9	0.1719	0.8303	0.2339	0.070*
H10a	0.4194	0.8480	0.7988	0.077*
H10b	0.4475	1.0350	0.8139	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.125 (2)	0.078 (2)	0.074 (2)	0.037 (2)	0.045 (2)	0.017 (1)
O2	0.125 (2)	0.096 (2)	0.082 (2)	0.051 (2)	0.049 (1)	0.026 (2)
O3	0.054 (1)	0.124 (2)	0.042 (1)	0.006 (1)	−0.003 (1)	0.010 (1)
O4	0.053 (1)	0.085 (2)	0.042 (1)	0.001 (1)	0.003 (1)	0.007 (1)
O5	0.103 (2)	0.074 (2)	0.058 (1)	−0.001 (1)	0.005 (1)	−0.005 (1)
O6	0.129 (2)	0.061 (1)	0.092 (2)	0.015 (2)	0.026 (2)	0.019 (1)
N1	0.056 (1)	0.061 (2)	0.061 (2)	0.005 (1)	0.006 (1)	0.006 (1)
C1	0.080 (2)	0.053 (2)	0.060 (2)	0.003 (2)	0.017 (2)	0.004 (1)
C2	0.105 (3)	0.059 (2)	0.082 (2)	0.006 (2)	0.047 (2)	0.008 (2)
C3	0.123 (4)	0.082 (3)	0.211 (6)	−0.031 (3)	0.088 (4)	−0.034 (3)
C4	0.064 (2)	0.056 (2)	0.056 (2)	0.009 (1)	0.028 (1)	0.011 (1)
C5	0.060 (2)	0.066 (2)	0.061 (2)	0.02 (1)	0.025 (1)	0.023 (1)
C6	0.039 (1)	0.071 (2)	0.048 (1)	0.015 (1)	0.012 (1)	0.015 (1)
C7	0.039 (1)	0.055 (2)	0.049 (2)	0.008 (1)	0.009 (1)	0.006 (1)
C8	0.055 (2)	0.060 (2)	0.050 (2)	0.011 (1)	0.008 (1)	0.016 (1)
C9	0.059 (2)	0.071 (2)	0.042 (1)	0.005 (1)	0.009 (1)	0.005 (1)
C10	0.052 (2)	0.091 (2)	0.054 (2)	0.021 (2)	0.004 (1)	0.022 (2)
C11	0.052 (2)	0.065 (2)	0.044 (2)	0.011 (1)	−0.001 (1)	0.014 (1)

Geometric parameters (Å, º)

O1—C1	1.260 (4)	C7—C8	1.374 (4)
O2—C1	1.235 (4)	C8—C9	1.371 (4)
O3—C11	1.304 (3)	C10—C11	1.503 (4)
O4—C11	1.218 (3)	O1—H1	0.82
O5—N1	1.213 (3)	O3—H3	0.82
O6—N1	1.222 (3)	C2—H2	0.98
N1—C7	1.475 (4)	C3—H3a	0.96
C1—C2	1.514 (5)	C3—H3b	0.96
C2—C3	1.465 (7)	C3—H3c	0.96
C2—C4	1.523 (4)	C5—H5	0.93
C4—C5	1.385 (4)	C8—H8	0.93
C4—C9	1.395 (4)	C9—H9	0.93
C5—C6	1.392 (4)	C10—H10a	0.97
C6—C7	1.389 (4)	C10—H10b	0.97
C6—C10	1.510 (4)
O5—N1—O6	122.9 (3)	O4—C11—C10	123.2 (2)
O5—N1—C7	119.3 (3)	C1—O1—H1	109.5
O6—N1—C7	117.8 (3)	C11—O3—H3	109.5
O1—C1—O2	123.2 (3)	C3—C2—H2	106.8
O1—C1—C2	115.3 (3)	C1—C2—H2	106.8
O2—C1—C2	121.4 (3)	C4—C2—H2	106.8
C1—C2—C3	109.6 (4)	C2—C3—H3a	109.5
C1—C2—C4	113.3 (3)	C2—C3—H3b	109.5
C3—C2—C4	113.0 (3)	H3a—C3—H3b	109.5
C2—C4—C5	119.8 (3)	C2—C3—H3c	109.5
C2—C4—C9	122.2 (3)	H3a—C3—H3c	109.5
C5—C4—C9	118.0 (3)	H3b—C3—H3c	109.5
C4—C5—C6	123.1 (3)	C4—C5—H5	118.4
C5—C6—C7	116.2 (3)	C6—C5—H5	118.4
C5—C6—C10	119.1 (3)	C9—C8—H8	120.0
C7—C6—C10	124.7 (3)	C7—C8—H8	120.0
C6—C7—C8	122.3 (3)	C8—C9—H9	119.8
C6—C7—N1	121.2 (2)	C4—C9—H9	119.8
C8—C7—N1	116.5 (2)	C6—C10—H10a	109.1
C7—C8—C9	120.0 (3)	C11—C10—H10b	109.1
C4—C9—C8	120.4 (3)	C6—C10—H10b	109.1
O3—C11—C10	113.5 (2)	C11—C10—H10a	109.1
C6—C10—C11	112.5 (2)	H10a—C10—H10b	107.8
O3—C11—O4	123.3 (3)
O2—C1—C2—C3	79.8 (5)	C10—C6—C7—N1	0.2 (4)
O1—C1—C2—C3	−99.2 (5)	O5—N1—C7—C8	156.8 (3)
O2—C1—C2—C4	−47.4 (5)	O6—N1—C7—C8	−22.8 (4)
O1—C1—C2—C4	133.6 (4)	O5—N1—C7—C6	−22.4 (4)
C3—C2—C4—C5	110.0 (5)	O6—N1—C7—C6	157.9 (3)
C1—C2—C4—C5	−124.5 (4)	C6—C7—C8—C9	−0.3 (4)
C3—C2—C4—C9	−68.4 (5)	N1—C7—C8—C9	−179.5 (2)
C1—C2—C4—C9	57.1 (5)	C7—C8—C9—C4	−1.2 (4)
C9—C4—C5—C6	0.1 (4)	C5—C4—C9—C8	1.3 (4)
C2—C4—C5—C6	−178.4 (3)	C2—C4—C9—C8	179.7 (3)
C4—C5—C6—C7	−1.4 (4)	C7—C6—C10—C11	75.9 (4)
C4—C5—C6—C10	179.1 (3)	C5—C6—C10—C11	−104.6 (3)
C5—C6—C7—C8	1.5 (4)	C6—C10—C11—O4	17.8 (4)
C10—C6—C7—C8	−179.0 (3)	C6—C10—C11—O3	−162.7 (3)
C5—C6—C7—N1	−179.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.82	1.82	2.641 (4)	173
O3—H3···O4^ii	0.82	1.84	2.658 (3)	176

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+2, −z+2.