1,5-Dihydr­oxy-1-(3-nitro­phen­yl)pentan-3-one

Inter­molecular O—H...O and weak C—H...O hydrogen bonding helps to stabilize the crystal structure of the title compound, C₁₁H₁₃NO₅.

Key indicators

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.027
• wR factor = 0.073
• Data-to-parameter ratio = 9.3

checkCIF/PLATON results

No syntax errors found



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           27.50
           From the CIF: _reflns_number_total               1513
           Count of symmetry unique reflns         1519
           Completeness (_total/calc)             99.61%
           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
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7     = .          R

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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.

1,5-Dihydroxy-1-(3-nitrophenyl)pentan-3-one

Crystal data

C11H13NO5	F(000) = 504
Mr = 239.22	Dx = 1.447 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 10500 reflections
a = 5.0521 (1) Å	θ = 3.2–27.5°
b = 6.9787 (2) Å	µ = 0.12 mm^−1
c = 31.1510 (6) Å	T = 153 K
V = 1098.29 (4) Å^3	Block, colourless
Z = 4	0.24 × 0.23 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	1467 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.016
Graphite monochromator	θmax = 27.5°, θmin = 3.2°
ω scans	h = −6→6
10797 measured reflections	k = −9→9
1513 independent reflections	l = −40→40

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.073	w = 1/[σ^2(Fo^2) + (0.0486P)^2 + 0.259P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.001
1513 reflections	Δρmax = 0.22 e Å^−3
163 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.025 (4)

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.

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

	x	y	z	Uiso*/Ueq
O1	0.0749 (2)	0.32593 (15)	0.59773 (3)	0.0264 (3)
O2	−0.1839 (2)	0.63151 (14)	0.55750 (3)	0.0207 (2)
O3	−0.1643 (2)	1.19917 (16)	0.51586 (4)	0.0257 (3)
O4	0.7515 (2)	−0.07638 (16)	0.64335 (4)	0.0299 (3)
O5	1.0051 (3)	−0.00873 (18)	0.69712 (4)	0.0377 (3)
N	0.8210 (3)	0.02925 (17)	0.67275 (4)	0.0217 (3)
C1	0.6788 (3)	0.21105 (19)	0.67907 (4)	0.0175 (3)
C2	0.7480 (3)	0.3272 (2)	0.71330 (4)	0.0209 (3)
H2	0.8851	0.2916	0.7326	0.025*
C3	0.6100 (3)	0.4974 (2)	0.71842 (4)	0.0236 (3)
H3	0.6523	0.5802	0.7416	0.028*
C4	0.4095 (3)	0.5479 (2)	0.68980 (4)	0.0215 (3)
H4	0.3155	0.6644	0.6939	0.026*
C5	0.3453 (3)	0.4293 (2)	0.65525 (4)	0.0171 (3)
C6	0.4812 (3)	0.25773 (19)	0.65000 (4)	0.0177 (3)
H6	0.4395	0.1740	0.6269	0.021*
C7	0.1310 (3)	0.48748 (19)	0.62371 (4)	0.0168 (3)
H7	−0.0321	0.5226	0.6401	0.020*
C8	0.2188 (3)	0.6603 (2)	0.59712 (4)	0.0185 (3)
H8A	0.2688	0.7658	0.6168	0.022*
H8B	0.3776	0.6250	0.5803	0.022*
C9	0.0063 (3)	0.73043 (19)	0.56688 (4)	0.0153 (3)
C10	0.0429 (3)	0.9272 (2)	0.54760 (4)	0.0179 (3)
H10A	0.1187	1.0138	0.5696	0.021*
H10B	0.1704	0.9189	0.5235	0.021*
C11	−0.2135 (3)	1.0106 (2)	0.53139 (5)	0.0227 (3)
H11A	−0.2853	0.9297	0.5080	0.027*
H11B	−0.3452	1.0148	0.5549	0.027*
H1O	−0.039 (5)	0.362 (3)	0.5779 (6)	0.035 (6)*
H3O	−0.318 (5)	1.243 (4)	0.5085 (8)	0.057 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0336 (6)	0.0156 (5)	0.0299 (5)	0.0023 (5)	−0.0159 (5)	−0.0030 (4)
O2	0.0177 (5)	0.0186 (4)	0.0258 (5)	−0.0026 (4)	−0.0038 (4)	0.0014 (4)
O3	0.0203 (5)	0.0200 (5)	0.0367 (5)	−0.0005 (5)	−0.0047 (5)	0.0122 (4)
O4	0.0342 (6)	0.0223 (5)	0.0332 (6)	0.0075 (5)	−0.0067 (5)	−0.0061 (4)
O5	0.0375 (6)	0.0338 (6)	0.0417 (6)	0.0152 (6)	−0.0186 (6)	−0.0009 (6)
N	0.0222 (6)	0.0194 (6)	0.0235 (5)	0.0028 (5)	−0.0015 (5)	0.0036 (5)
C1	0.0173 (6)	0.0171 (6)	0.0183 (5)	0.0010 (6)	0.0014 (5)	0.0037 (5)
C2	0.0217 (6)	0.0251 (7)	0.0159 (5)	0.0003 (6)	−0.0015 (5)	0.0036 (5)
C3	0.0281 (7)	0.0258 (7)	0.0170 (6)	0.0007 (7)	−0.0027 (6)	−0.0036 (6)
C4	0.0244 (7)	0.0196 (6)	0.0205 (6)	0.0035 (6)	0.0000 (5)	−0.0016 (5)
C5	0.0176 (6)	0.0171 (6)	0.0166 (5)	0.0006 (6)	−0.0003 (5)	0.0025 (5)
C6	0.0194 (6)	0.0168 (6)	0.0169 (5)	−0.0005 (6)	−0.0012 (5)	0.0011 (5)
C7	0.0162 (6)	0.0143 (6)	0.0198 (5)	0.0003 (5)	−0.0016 (5)	0.0002 (5)
C8	0.0148 (6)	0.0191 (6)	0.0217 (6)	−0.0007 (5)	−0.0032 (5)	0.0043 (5)
C9	0.0135 (6)	0.0161 (6)	0.0162 (5)	0.0015 (5)	0.0015 (5)	−0.0006 (5)
C10	0.0155 (6)	0.0153 (6)	0.0228 (6)	0.0002 (6)	−0.0013 (5)	0.0025 (5)
C11	0.0200 (7)	0.0180 (6)	0.0300 (6)	−0.0028 (6)	−0.0068 (6)	0.0080 (6)

Geometric parameters (Å, º)

O1—C7	1.4164 (16)	C4—H4	0.9500
O1—H1O	0.88 (2)	C5—C6	1.3900 (19)
O2—C9	1.2185 (17)	C5—C7	1.5172 (18)
O3—C11	1.4242 (17)	C6—H6	0.9500
O3—H3O	0.86 (3)	C7—C8	1.5289 (18)
O4—N	1.2268 (16)	C7—H7	1.0000
O5—N	1.2296 (16)	C8—C9	1.5097 (18)
N—C1	1.4711 (18)	C8—H8A	0.9900
C1—C2	1.3843 (19)	C8—H8B	0.9900
C1—C6	1.3869 (18)	C9—C10	1.5100 (18)
C2—C3	1.386 (2)	C10—C11	1.5073 (19)
C2—H2	0.9500	C10—H10A	0.9900
C3—C4	1.395 (2)	C10—H10B	0.9900
C3—H3	0.9500	C11—H11A	0.9900
C4—C5	1.3958 (19)	C11—H11B	0.9900
C7—O1—H1O	107.8 (14)	C5—C7—C8	110.78 (11)
C11—O3—H3O	105 (2)	O1—C7—H7	108.8
O4—N—O5	123.21 (13)	C5—C7—H7	108.8
O4—N—C1	118.59 (12)	C8—C7—H7	108.8
O5—N—C1	118.20 (12)	C9—C8—C7	112.79 (11)
C2—C1—C6	123.17 (13)	C9—C8—H8A	109.0
C2—C1—N	119.01 (12)	C7—C8—H8A	109.0
C6—C1—N	117.82 (12)	C9—C8—H8B	109.0
C1—C2—C3	117.60 (13)	C7—C8—H8B	109.0
C1—C2—H2	121.2	H8A—C8—H8B	107.8
C3—C2—H2	121.2	O2—C9—C8	121.78 (12)
C2—C3—C4	120.56 (13)	O2—C9—C10	121.08 (12)
C2—C3—H3	119.7	C8—C9—C10	117.11 (11)
C4—C3—H3	119.7	C11—C10—C9	112.27 (11)
C3—C4—C5	120.78 (14)	C11—C10—H10A	109.2
C3—C4—H4	119.6	C9—C10—H10A	109.1
C5—C4—H4	119.6	C11—C10—H10B	109.1
C6—C5—C4	119.11 (13)	C9—C10—H10B	109.2
C6—C5—C7	120.45 (12)	H10A—C10—H10B	107.9
C4—C5—C7	120.43 (12)	O3—C11—C10	108.71 (12)
C1—C6—C5	118.77 (12)	O3—C11—H11A	109.9
C1—C6—H6	120.6	C10—C11—H11A	109.9
C5—C6—H6	120.6	O3—C11—H11B	109.9
O1—C7—C5	107.45 (11)	C10—C11—H11B	109.9
O1—C7—C8	112.11 (11)	H11A—C11—H11B	108.3
O4—N—C1—C2	177.17 (13)	C7—C5—C6—C1	178.91 (12)
O5—N—C1—C2	−3.27 (19)	C6—C5—C7—O1	11.47 (17)
O4—N—C1—C6	−3.07 (19)	C4—C5—C7—O1	−168.85 (13)
O5—N—C1—C6	176.49 (13)	C6—C5—C7—C8	−111.30 (14)
C6—C1—C2—C3	0.4 (2)	C4—C5—C7—C8	68.38 (16)
N—C1—C2—C3	−179.88 (12)	O1—C7—C8—C9	63.08 (15)
C1—C2—C3—C4	−0.1 (2)	C5—C7—C8—C9	−176.89 (11)
C2—C3—C4—C5	−0.6 (2)	C7—C8—C9—O2	−16.94 (18)
C3—C4—C5—C6	1.0 (2)	C7—C8—C9—C10	164.78 (11)
C3—C4—C5—C7	−178.65 (13)	O2—C9—C10—C11	21.99 (17)
C2—C1—C6—C5	0.1 (2)	C8—C9—C10—C11	−159.71 (12)
N—C1—C6—C5	−179.68 (12)	C9—C10—C11—O3	176.99 (11)
C4—C5—C6—C1	−0.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2	0.88 (2)	2.12 (2)	2.7977 (15)	133.6 (19)
O1—H1O···O3^i	0.88 (2)	2.33 (2)	2.9577 (15)	128.5 (18)
O3—H3O···O3^ii	0.86 (3)	1.95 (3)	2.8036 (9)	169 (3)
C8—H8B···O2^iii	0.99	2.33	3.2664 (18)	158
C10—H10A···O1^iv	0.99	2.36	3.1949 (17)	142

Symmetry codes: (i) x, y−1, z; (ii) x−1/2, −y+5/2, −z+1; (iii) x+1, y, z; (iv) x, y+1, z.