2-Nitro­propane-1,3-diol

The title mol­ecule, C₃H₇NO₄, adopts a nearly symmetric conformation. The crystal structure is stabilized by inter­molecular O—H...O hydrogen bonds, linking the mol­ecules to form a three-dimensional framework.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.034
• wR factor = 0.086
• Data-to-parameter ratio = 7.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.56
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1

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           26.23
           From the CIF: _reflns_number_total                597
           Count of symmetry unique reflns          597
           Completeness (_total/calc)            100.00%
           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

   1 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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

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

2-Nitropropane-1,3-diol

Crystal data

C3H7NO4	Dx = 1.445 Mg m^−3
Mr = 121.10	Melting point: 327.15 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1246 reflections
a = 10.331 (3) Å	θ = 3.8–23.1°
b = 6.322 (2) Å	µ = 0.14 mm^−1
c = 8.520 (3) Å	T = 294 K
V = 556.5 (3) Å^3	Prism, colorless
Z = 4	0.24 × 0.20 × 0.18 mm
F(000) = 256

Data collection

Bruker SMART CCD area-detector diffractometer	597 independent reflections
Radiation source: fine-focus sealed tube	505 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 26.2°, θmin = 3.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→12
Tmin = 0.968, Tmax = 0.976	k = −7→6
2868 measured reflections	l = −10→10

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0499P)^2 + 0.0466P] where P = (Fo^2 + 2Fc^2)/3
597 reflections	(Δ/σ)max < 0.001
79 parameters	Δρmax = 0.12 e Å^−3
1 restraint	Δρmin = −0.14 e Å^−3

Special details

Experimental. ¹H NMR (DMSO-d₆, δ, p.p.m.): 3.62 (t, 4H), 4.56 (q, 1H), 5.09 (t, 2H).

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.8876 (2)	0.7482 (4)	0.4725 (3)	0.0769 (7)
O2	0.7428 (2)	0.5568 (3)	0.5828 (4)	0.0803 (7)
O3	0.63039 (17)	1.0546 (3)	0.5997 (3)	0.0601 (6)
H3	0.582 (4)	1.007 (6)	0.672 (6)	0.090*
O4	0.99210 (18)	0.6747 (3)	0.8253 (3)	0.0610 (6)
H4	0.945 (4)	0.610 (6)	0.904 (6)	0.091*
N1	0.8136 (2)	0.7103 (3)	0.5793 (3)	0.0493 (6)
C1	0.7585 (3)	1.0710 (4)	0.6550 (4)	0.0460 (6)
H1A	0.7619	1.1742	0.7391	0.055*
H1B	0.8138	1.1207	0.5707	0.055*
C2	0.8090 (2)	0.8610 (4)	0.7146 (3)	0.0378 (5)
H2	0.7493	0.8060	0.7941	0.045*
C3	0.9433 (2)	0.8754 (4)	0.7846 (3)	0.0484 (6)
H3A	1.0010	0.9415	0.7094	0.058*
H3B	0.9405	0.9641	0.8775	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0849 (15)	0.0957 (17)	0.0500 (12)	−0.0133 (14)	0.0215 (13)	−0.0177 (12)
O2	0.0934 (15)	0.0493 (12)	0.0981 (19)	−0.0177 (12)	−0.0066 (16)	−0.0129 (13)
O3	0.0476 (11)	0.0719 (13)	0.0609 (13)	0.0000 (9)	−0.0076 (10)	0.0244 (12)
O4	0.0501 (11)	0.0806 (14)	0.0523 (12)	0.0221 (9)	0.0064 (9)	0.0175 (12)
N1	0.0517 (12)	0.0443 (12)	0.0521 (14)	−0.0015 (10)	−0.0046 (11)	−0.0032 (11)
C1	0.0456 (14)	0.0426 (12)	0.0499 (14)	−0.0003 (10)	−0.0005 (11)	0.0053 (11)
C2	0.0370 (11)	0.0410 (11)	0.0355 (11)	0.0001 (10)	0.0049 (10)	0.0006 (11)
C3	0.0416 (13)	0.0586 (14)	0.0449 (13)	0.0023 (12)	−0.0011 (12)	−0.0002 (12)

Geometric parameters (Å, º)

O1—N1	1.213 (3)	C1—C2	1.514 (3)
O2—N1	1.215 (3)	C1—H1A	0.9700
O3—C1	1.409 (3)	C1—H1B	0.9700
O3—H3	0.85 (5)	C2—C3	1.512 (3)
O4—C3	1.409 (3)	C2—H2	0.9800
O4—H4	0.92 (5)	C3—H3A	0.9700
N1—C2	1.496 (3)	C3—H3B	0.9700
C1—O3—H3	109 (3)	N1—C2—C1	108.1 (2)
C3—O4—H4	113 (2)	C3—C2—C1	113.3 (2)
O1—N1—O2	123.8 (3)	N1—C2—H2	109.0
O1—N1—C2	118.2 (2)	C3—C2—H2	109.0
O2—N1—C2	118.0 (2)	C1—C2—H2	109.0
O3—C1—C2	111.8 (2)	O4—C3—C2	111.8 (2)
O3—C1—H1A	109.3	O4—C3—H3A	109.3
C2—C1—H1A	109.3	C2—C3—H3A	109.3
O3—C1—H1B	109.3	O4—C3—H3B	109.3
C2—C1—H1B	109.3	C2—C3—H3B	109.3
H1A—C1—H1B	107.9	H3A—C3—H3B	107.9
N1—C2—C3	108.3 (2)
O1—N1—C2—C3	−58.1 (3)	O3—C1—C2—N1	63.8 (3)
O2—N1—C2—C3	121.9 (3)	O3—C1—C2—C3	−176.3 (2)
O1—N1—C2—C1	65.0 (3)	N1—C2—C3—O4	−54.6 (3)
O2—N1—C2—C1	−115.1 (3)	C1—C2—C3—O4	−174.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3^i	0.92 (5)	1.88 (5)	2.765 (3)	161 (4)
O3—H3···O4^ii	0.85 (5)	1.97 (5)	2.800 (3)	165 (4)

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