N-Hydro­xy­succin­imide

The molecule of the title compound, C₄H₅NO₃, is planar (mean deviation of non-H atoms 0.03 Å). The N-C bond lengths are significantly different [1.365 (2) and 1.392 (2) Å]. The C=O group associated with the shorter N-C bond accepts a classical intermolecular hydrogen bond from the hydroxy H atom.

Key indicators

• Single-crystal X-ray study
• T = 133 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.108
• Data-to-parameter ratio = 11.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.36
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           30.01
           From the CIF: _reflns_number_total                860
           Count of symmetry unique reflns          861
           Completeness (_total/calc)             99.88%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   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
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

C4H5NO3	Dx = 1.563 Mg m^−3
Mr = 115.09	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 3627 reflections
a = 5.4266 (8) Å	θ = 2.8–30.5°
b = 7.2419 (12) Å	µ = 0.14 mm^−1
c = 12.445 (2) Å	T = 133 K
V = 489.09 (13) Å^3	Irregular tablet, colourless
Z = 4	0.30 × 0.25 × 0.10 mm
F(000) = 240

Data collection

Bruker SMART 1000 CCD diffractometer	803 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.071
Graphite monochromator	θmax = 30.0°, θmin = 3.3°
Detector resolution: 8.192 pixels mm^-1	h = −7→7
ω scans	k = −10→10
5566 measured reflections	l = −17→17
860 independent reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0857P)^2 + 0.0226P] where P = (Fo^2 + 2Fc^2)/3
860 reflections	(Δ/σ)max < 0.001
77 parameters	Δρmax = 0.48 e Å^−3
0 restraints	Δρmin = −0.20 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. 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.

The anomalous dispersion effects were not significant and Friedel opposite reflections were therefore merged. The Flack parameter is meaningless in such cases.

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

	x	y	z	Uiso*/Ueq
C1	0.3418 (3)	0.45792 (19)	0.36706 (11)	0.0183 (3)
C2	0.4766 (3)	0.5929 (2)	0.29615 (11)	0.0210 (3)
H2A	0.3675	0.6966	0.2755	0.025*
H2B	0.5367	0.5314	0.2301	0.025*
C3	0.6938 (3)	0.6623 (2)	0.36469 (12)	0.0222 (3)
H3A	0.8527	0.6213	0.3337	0.027*
H3B	0.6934	0.7988	0.3689	0.027*
C4	0.6549 (3)	0.5788 (2)	0.47386 (13)	0.0210 (3)
N	0.4578 (2)	0.45687 (16)	0.46436 (10)	0.0189 (3)
O1	0.1590 (2)	0.36643 (15)	0.34513 (9)	0.0232 (3)
O2	0.7672 (3)	0.60296 (19)	0.55634 (10)	0.0321 (3)
O3	0.3621 (2)	0.36006 (16)	0.54995 (9)	0.0237 (3)
H0	0.494 (7)	0.282 (4)	0.575 (2)	0.063 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0211 (6)	0.0130 (6)	0.0208 (6)	0.0023 (5)	0.0012 (5)	−0.0006 (5)
C2	0.0271 (7)	0.0155 (6)	0.0203 (6)	−0.0023 (6)	0.0009 (6)	0.0007 (5)
C3	0.0209 (6)	0.0181 (6)	0.0277 (7)	−0.0007 (6)	0.0006 (6)	0.0036 (5)
C4	0.0208 (6)	0.0147 (6)	0.0274 (7)	0.0000 (6)	−0.0018 (6)	0.0018 (5)
N	0.0209 (6)	0.0149 (5)	0.0208 (6)	−0.0008 (5)	−0.0006 (5)	0.0037 (4)
O1	0.0240 (5)	0.0220 (5)	0.0236 (5)	−0.0038 (5)	−0.0010 (5)	0.0013 (4)
O2	0.0356 (7)	0.0299 (7)	0.0307 (6)	−0.0073 (5)	−0.0109 (6)	0.0037 (5)
O3	0.0254 (6)	0.0231 (6)	0.0227 (5)	0.0005 (5)	0.0017 (5)	0.0081 (4)

Geometric parameters (Å, º)

C1—O1	1.224 (2)	N—O3	1.3769 (16)
C1—N	1.365 (2)	C2—H2A	0.9900
C1—C2	1.507 (2)	C2—H2B	0.9900
C2—C3	1.539 (2)	C3—H3A	0.9900
C3—C4	1.502 (2)	C3—H3B	0.9900
C4—O2	1.207 (2)	O3—H0	0.97 (3)
C4—N	1.392 (2)
O1—C1—N	124.65 (13)	C1—C2—H2A	110.7
O1—C1—C2	127.90 (13)	C3—C2—H2A	110.7
N—C1—C2	107.44 (12)	C1—C2—H2B	110.7
C1—C2—C3	105.01 (13)	C3—C2—H2B	110.7
C4—C3—C2	105.20 (12)	H2A—C2—H2B	108.8
O2—C4—N	123.54 (14)	C4—C3—H3A	110.7
O2—C4—C3	129.80 (14)	C2—C3—H3A	110.7
N—C4—C3	106.65 (13)	C4—C3—H3B	110.7
C1—N—O3	121.03 (12)	C2—C3—H3B	110.7
C1—N—C4	115.22 (12)	H3A—C3—H3B	108.8
O3—N—C4	123.17 (12)	N—O3—H0	105.7 (18)
O1—C1—C2—C3	−178.69 (15)	O1—C1—N—C4	−176.73 (14)
N—C1—C2—C3	2.65 (16)	C2—C1—N—C4	1.98 (17)
C1—C2—C3—C4	−5.83 (16)	O2—C4—N—C1	175.34 (16)
C2—C3—C4—O2	−174.31 (18)	C3—C4—N—C1	−5.86 (17)
C2—C3—C4—N	6.99 (16)	O2—C4—N—O3	4.0 (2)
O1—C1—N—O3	−5.2 (2)	C3—C4—N—O3	−177.16 (12)
C2—C1—N—O3	173.48 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H0···O1^i	0.97 (3)	1.71 (3)	2.6442 (16)	161 (3)
C3—H3A···O1^ii	0.99	2.49	3.320 (2)	142
C2—H2B···O2^iii	0.99	2.60	3.585 (2)	174

Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) x+1, y, z; (iii) −x+3/2, −y+1, z−1/2.