4-(2,6-Dichloro­phen­yl)-1,4-dihydroxy­butan-2-one

Mol­ecules of the title compound, C₁₀H₁₀Cl₂O₃, are linked by O—H...O hydrogen bonds into a sheet motif.

Key indicators

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.019
• wR factor = 0.055
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.35 Ratio

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               2205
           Count of symmetry unique reflns         1295
           Completeness (_total/calc)            170.27%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       910
           Fraction of Friedel pairs measured     0.703
           Are heavy atom types Z>Si present        yes
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
   1 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
   1 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, 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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2006).

4-(2,6-Dichlorophenyl)-1,4-dihydroxybutan-2-one

Crystal data

C10H10Cl2O3	F(000) = 256
Mr = 249.08	Dx = 1.566 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5260 reflections
a = 7.7674 (2) Å	θ = 3.1–27.5°
b = 8.7852 (2) Å	µ = 0.60 mm^−1
c = 8.3555 (3) Å	T = 153 K
β = 112.093 (1)°	Block, colorless
V = 528.30 (3) Å^3	0.45 × 0.42 × 0.36 mm
Z = 2

Data collection

Rigaku R-AXIS RAPID diffractometer	2205 independent reflections
Radiation source: Rotating Anode	2189 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.775, Tmax = 0.814	k = −10→11
5238 measured reflections	l = −10→10

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.019	w = 1/[σ^2(Fo^2) + (0.0395P)^2 + 0.0574P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.055	(Δ/σ)max = 0.001
S = 1.08	Δρmax = 0.30 e Å^−3
2205 reflections	Δρmin = −0.20 e Å^−3
145 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
3 restraints	Extinction coefficient: 0.145 (8)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 913 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.01 (4)

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

	x	y	z	Uiso*/Ueq
Cl1	0.80048 (5)	0.50000 (4)	0.38022 (4)	0.02470 (10)
Cl2	0.72164 (5)	1.11567 (3)	0.29746 (4)	0.02452 (10)
O1	0.67825 (12)	0.69652 (12)	0.05151 (11)	0.0192 (2)
H1O	0.5689 (18)	0.733 (3)	0.020 (3)	0.041 (6)*
O2	1.00631 (15)	0.93997 (14)	0.00308 (15)	0.0292 (2)
O3	1.34429 (14)	0.85526 (12)	0.00719 (13)	0.0234 (2)
H3O	1.305 (4)	0.9459 (15)	−0.010 (3)	0.057 (8)*
C1	0.75376 (17)	0.67988 (16)	0.44054 (15)	0.0178 (2)
C2	0.71627 (19)	0.6883 (2)	0.59083 (16)	0.0241 (3)
H2	0.7186	0.5990	0.6557	0.029*
C3	0.67562 (19)	0.8280 (2)	0.64475 (17)	0.0260 (3)
H3	0.6483	0.8348	0.7462	0.031*
C4	0.67490 (18)	0.95718 (18)	0.55081 (17)	0.0223 (3)
H4	0.6466	1.0533	0.5870	0.027*
C5	0.71581 (16)	0.94612 (15)	0.40294 (16)	0.0159 (2)
C6	0.75446 (17)	0.80738 (16)	0.34087 (16)	0.0135 (2)
C7	0.79676 (15)	0.80051 (15)	0.17700 (14)	0.0142 (2)
H7	0.7761	0.9044	0.1242	0.017*
C8	0.99777 (15)	0.75544 (15)	0.21321 (14)	0.0152 (2)
H8A	1.0745	0.7793	0.3351	0.018*
H8B	1.0036	0.6441	0.1976	0.018*
C9	1.07935 (15)	0.83537 (15)	0.09777 (14)	0.0153 (2)
C10	1.26894 (18)	0.77870 (17)	0.11409 (18)	0.0235 (3)
H10A	1.3553	0.7898	0.2358	0.028*
H10B	1.2599	0.6689	0.0855	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.03241 (17)	0.01355 (16)	0.02874 (16)	0.00171 (12)	0.01219 (12)	0.00397 (12)
Cl2	0.02904 (17)	0.01303 (16)	0.03068 (17)	0.00219 (13)	0.01031 (13)	0.00024 (12)
O1	0.0136 (4)	0.0254 (5)	0.0169 (4)	0.0004 (4)	0.0036 (3)	−0.0050 (4)
O2	0.0261 (5)	0.0296 (6)	0.0387 (5)	0.0081 (4)	0.0198 (4)	0.0168 (4)
O3	0.0213 (4)	0.0231 (5)	0.0333 (5)	0.0040 (4)	0.0189 (4)	0.0081 (4)
C1	0.0162 (5)	0.0185 (6)	0.0182 (5)	−0.0012 (5)	0.0059 (4)	0.0004 (5)
C2	0.0246 (6)	0.0301 (8)	0.0187 (5)	−0.0062 (6)	0.0095 (5)	0.0046 (5)
C3	0.0238 (6)	0.0388 (9)	0.0189 (5)	−0.0051 (6)	0.0118 (5)	−0.0049 (6)
C4	0.0189 (6)	0.0269 (7)	0.0221 (6)	−0.0010 (5)	0.0089 (5)	−0.0102 (5)
C5	0.0125 (5)	0.0150 (6)	0.0196 (5)	−0.0013 (4)	0.0054 (4)	−0.0018 (4)
C6	0.0109 (4)	0.0148 (6)	0.0150 (5)	−0.0004 (4)	0.0051 (3)	−0.0004 (4)
C7	0.0132 (5)	0.0156 (6)	0.0143 (5)	0.0013 (5)	0.0057 (4)	0.0002 (4)
C8	0.0127 (5)	0.0174 (6)	0.0163 (5)	0.0010 (5)	0.0066 (4)	0.0014 (4)
C9	0.0132 (5)	0.0156 (6)	0.0177 (5)	−0.0026 (5)	0.0066 (4)	−0.0015 (4)
C10	0.0176 (6)	0.0272 (8)	0.0309 (6)	0.0037 (6)	0.0149 (5)	0.0083 (6)

Geometric parameters (Å, º)

Cl1—C1	1.7380 (15)	C4—C5	1.3901 (18)
Cl2—C5	1.7400 (14)	C4—H4	0.9500
O1—C7	1.4336 (15)	C5—C6	1.4006 (18)
O1—H1O	0.852 (10)	C6—C7	1.5247 (16)
O2—C9	1.2061 (17)	C7—C8	1.5266 (16)
O3—C10	1.4093 (15)	C7—H7	1.0000
O3—H3O	0.846 (10)	C8—C9	1.5115 (16)
C1—C2	1.3937 (17)	C8—H8A	0.9900
C1—C6	1.3970 (19)	C8—H8B	0.9900
C2—C3	1.384 (2)	C9—C10	1.5113 (17)
C2—H2	0.9500	C10—H10A	0.9900
C3—C4	1.379 (2)	C10—H10B	0.9900
C3—H3	0.9500
C7—O1—H1O	106.0 (16)	O1—C7—C8	107.89 (10)
C10—O3—H3O	110.3 (19)	C6—C7—C8	112.46 (10)
C2—C1—C6	122.92 (13)	O1—C7—H7	107.9
C2—C1—Cl1	116.54 (11)	C6—C7—H7	107.9
C6—C1—Cl1	120.54 (9)	C8—C7—H7	107.9
C3—C2—C1	119.41 (13)	C9—C8—C7	113.33 (10)
C3—C2—H2	120.3	C9—C8—H8A	108.9
C1—C2—H2	120.3	C7—C8—H8A	108.9
C4—C3—C2	119.81 (11)	C9—C8—H8B	108.9
C4—C3—H3	120.1	C7—C8—H8B	108.9
C2—C3—H3	120.1	H8A—C8—H8B	107.7
C3—C4—C5	119.67 (13)	O2—C9—C10	120.81 (11)
C3—C4—H4	120.2	O2—C9—C8	124.47 (11)
C5—C4—H4	120.2	C10—C9—C8	114.68 (11)
C4—C5—C6	122.85 (13)	O3—C10—C9	114.11 (11)
C4—C5—Cl2	116.65 (10)	O3—C10—H10A	108.7
C6—C5—Cl2	120.49 (10)	C9—C10—H10A	108.7
C1—C6—C5	115.32 (11)	O3—C10—H10B	108.7
C1—C6—C7	123.64 (12)	C9—C10—H10B	108.7
C5—C6—C7	121.03 (12)	H10A—C10—H10B	107.6
O1—C7—C6	112.71 (10)
C6—C1—C2—C3	0.7 (2)	C4—C5—C6—C7	179.39 (11)
Cl1—C1—C2—C3	−179.18 (10)	Cl2—C5—C6—C7	−1.85 (16)
C1—C2—C3—C4	−0.8 (2)	C1—C6—C7—O1	55.57 (16)
C2—C3—C4—C5	−0.3 (2)	C5—C6—C7—O1	−125.43 (12)
C3—C4—C5—C6	1.50 (19)	C1—C6—C7—C8	−66.67 (16)
C3—C4—C5—Cl2	−177.30 (10)	C5—C6—C7—C8	112.34 (13)
C2—C1—C6—C5	0.40 (19)	O1—C7—C8—C9	91.02 (12)
Cl1—C1—C6—C5	−179.68 (9)	C6—C7—C8—C9	−144.06 (11)
C2—C1—C6—C7	179.46 (12)	C7—C8—C9—O2	10.09 (18)
Cl1—C1—C6—C7	−0.63 (17)	C7—C8—C9—C10	−172.46 (11)
C4—C5—C6—C1	−1.53 (18)	O2—C9—C10—O3	−1.79 (19)
Cl2—C5—C6—C1	177.23 (9)	C8—C9—C10—O3	−179.34 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O3^i	0.85 (1)	2.02 (1)	2.844 (1)	164 (2)
O3—H3O···O1^ii	0.85 (1)	2.24 (2)	3.032 (2)	156 (2)

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