Crystal structures of three β-halolactic acids: hydrogen bonding resulting in differing Z′

The crystal structures of three β-halolactic acids have been determined, namely, β-chloro­lactic acid (systematic name: 3-chloro-2-hy­droxy­propanoic acid, C₃H₅ClO₃) (I), β-bromo­lactic acid (systematic name: 3-bromo-2-hy­droxy­propanoic acid, C₃H₅BrO₃) (II), and β-iodo­lactic acid (systematic name: 2-hydroxy-3-iodo­propanoic acid, C₃H₅IO₃) (III). The number of mol­ecules in the asymmetric unit of each crystal structure (Z′) was found to be two for I and II, and one for III, making I and II isostructural and III unique. The difference between the mol­ecules in the asymmetric units of I and II is due to the direction of the hydrogen bond of the alcohol group to a neighboring mol­ecule. Mol­ecular packing shows that each structure has alternating layers of inter­molecular hydrogen bonding and halogen–halogen inter­actions. Hirshfeld surfaces and two-dimensional fingerprint plots were analyzed to further explore the inter­molecular inter­actions of these structures. In I and II, energy minimization is achieved by lowering of the symmetry to adopt two independent mol­ecular conformations in the asymmetric unit.

Computing details

For all structures, data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009), Mercury (Macrae et al., 2020) and CrystalExplorer (Spackman et al., 2021).

3-Chloro-2-hydroxypropanoic acid (21165)

Crystal data

C3H5ClO3	F(000) = 512
Mr = 124.52	Dx = 1.651 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.8897 (7) Å	Cell parameters from 4811 reflections
b = 10.6951 (8) Å	θ = 3.0–26.0°
c = 9.0496 (6) Å	µ = 0.65 mm^−1
β = 108.059 (2)°	T = 153 K
V = 1002.05 (12) Å^3	Plate, colourless
Z = 8	0.22 × 0.21 × 0.08 mm

Data collection

Bruker Venture D8 diffractometer	1644 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.129
Absorption correction: multi-scan (SADABS2016; Bruker, 2016)	θmax = 27.5°, θmin = 2.7°
Tmin = 0.682, Tmax = 0.746	h = −14→13
34621 measured reflections	k = −13→13
2294 independent reflections	l = −11→11

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.086	w = 1/[σ^2(Fo^2) + (0.0371P)^2 + 0.3727P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.001
2294 reflections	Δρmax = 0.28 e Å^−3
143 parameters	Δρmin = −0.32 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.

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

	x	y	z	Uiso*/Ueq
Cl1A	0.90026 (6)	0.16529 (6)	0.46073 (7)	0.03398 (17)
O1A	0.61723 (15)	0.10079 (14)	0.27482 (16)	0.0223 (3)
H1A	0.630 (2)	0.044 (2)	0.224 (3)	0.023 (7)*
O2A	0.65712 (17)	0.16424 (16)	0.66921 (17)	0.0304 (4)
H2A	0.637 (3)	0.227 (3)	0.708 (3)	0.046 (8)*
O3A	0.58743 (14)	0.28048 (13)	0.45347 (16)	0.0216 (3)
C1A	0.8043 (2)	0.0385 (2)	0.4917 (3)	0.0234 (5)
H1AA	0.819542	−0.036310	0.435266	0.028*
H1AB	0.830323	0.018025	0.603828	0.028*
C2A	0.6621 (2)	0.07151 (19)	0.4356 (2)	0.0194 (4)
H2AA	0.611759	−0.001565	0.454756	0.023*
C3A	0.63140 (19)	0.18414 (19)	0.5191 (2)	0.0181 (4)
Cl1B	0.07951 (5)	0.39421 (6)	0.36033 (7)	0.03451 (17)
O1B	0.36771 (15)	0.41250 (15)	0.42619 (17)	0.0227 (4)
H1B	0.438 (3)	0.379 (3)	0.457 (3)	0.044 (8)*
O2B	0.28656 (18)	0.33943 (17)	0.76908 (19)	0.0352 (4)
H2B	0.296 (3)	0.273 (3)	0.818 (3)	0.041 (8)*
O3B	0.35042 (16)	0.21788 (14)	0.60475 (17)	0.0289 (4)
C1B	0.1898 (2)	0.4971 (2)	0.4920 (2)	0.0233 (5)
H1BA	0.196511	0.576028	0.437887	0.028*
H1BB	0.156841	0.517323	0.579555	0.028*
C2B	0.3218 (2)	0.4379 (2)	0.5540 (2)	0.0191 (4)
H2BA	0.381583	0.498914	0.624543	0.023*
C3B	0.3211 (2)	0.3181 (2)	0.6435 (2)	0.0211 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1A	0.0262 (3)	0.0290 (3)	0.0477 (4)	−0.0023 (2)	0.0129 (3)	0.0052 (3)
O1A	0.0316 (9)	0.0193 (8)	0.0174 (8)	0.0009 (7)	0.0095 (7)	−0.0043 (7)
O2A	0.0516 (11)	0.0238 (9)	0.0182 (8)	0.0109 (8)	0.0144 (8)	−0.0003 (7)
O3A	0.0300 (8)	0.0169 (8)	0.0207 (8)	0.0032 (6)	0.0117 (6)	0.0016 (6)
C1A	0.0255 (11)	0.0189 (11)	0.0283 (12)	0.0028 (9)	0.0119 (10)	0.0021 (9)
C2A	0.0260 (11)	0.0171 (11)	0.0169 (10)	−0.0001 (9)	0.0095 (9)	0.0003 (8)
C3A	0.0196 (10)	0.0187 (12)	0.0176 (10)	−0.0014 (8)	0.0082 (9)	0.0007 (8)
Cl1B	0.0243 (3)	0.0377 (4)	0.0383 (3)	−0.0027 (3)	0.0049 (3)	−0.0039 (3)
O1B	0.0245 (8)	0.0270 (9)	0.0205 (8)	0.0054 (7)	0.0126 (7)	0.0036 (6)
O2B	0.0592 (12)	0.0280 (10)	0.0288 (9)	0.0098 (9)	0.0287 (9)	0.0090 (8)
O3B	0.0426 (10)	0.0180 (8)	0.0309 (9)	−0.0001 (7)	0.0182 (8)	−0.0014 (7)
C1B	0.0273 (11)	0.0198 (11)	0.0252 (11)	0.0024 (9)	0.0119 (9)	0.0001 (9)
C2B	0.0229 (11)	0.0186 (11)	0.0176 (10)	−0.0015 (8)	0.0091 (9)	−0.0009 (8)
C3B	0.0235 (11)	0.0227 (12)	0.0175 (11)	−0.0018 (9)	0.0071 (9)	0.0001 (9)

Geometric parameters (Å, º)

Cl1A—C1A	1.786 (2)	Cl1B—C1B	1.785 (2)
O1A—H1A	0.80 (2)	O1B—H1B	0.81 (3)
O1A—C2A	1.418 (2)	O1B—C2B	1.421 (2)
O2A—H2A	0.82 (3)	O2B—H2B	0.83 (3)
O2A—C3A	1.316 (2)	O2B—C3B	1.323 (2)
O3A—C3A	1.211 (2)	O3B—C3B	1.201 (2)
C1A—H1AA	0.9900	C1B—H1BA	0.9900
C1A—H1AB	0.9900	C1B—H1BB	0.9900
C1A—C2A	1.515 (3)	C1B—C2B	1.510 (3)
C2A—H2AA	1.0000	C2B—H2BA	1.0000
C2A—C3A	1.513 (3)	C2B—C3B	1.517 (3)
C2A—O1A—H1A	110.4 (16)	C2B—O1B—H1B	109.4 (19)
C3A—O2A—H2A	108 (2)	C3B—O2B—H2B	107.1 (18)
Cl1A—C1A—H1AA	109.5	Cl1B—C1B—H1BA	109.5
Cl1A—C1A—H1AB	109.5	Cl1B—C1B—H1BB	109.5
H1AA—C1A—H1AB	108.0	H1BA—C1B—H1BB	108.1
C2A—C1A—Cl1A	110.94 (15)	C2B—C1B—Cl1B	110.83 (15)
C2A—C1A—H1AA	109.5	C2B—C1B—H1BA	109.5
C2A—C1A—H1AB	109.5	C2B—C1B—H1BB	109.5
O1A—C2A—C1A	112.72 (16)	O1B—C2B—C1B	108.19 (16)
O1A—C2A—H2AA	108.5	O1B—C2B—H2BA	108.7
O1A—C2A—C3A	106.11 (16)	O1B—C2B—C3B	109.50 (17)
C1A—C2A—H2AA	108.5	C1B—C2B—H2BA	108.7
C3A—C2A—C1A	112.29 (17)	C1B—C2B—C3B	113.03 (17)
C3A—C2A—H2AA	108.5	C3B—C2B—H2BA	108.7
O2A—C3A—C2A	112.18 (18)	O2B—C3B—C2B	111.23 (18)
O3A—C3A—O2A	124.67 (19)	O3B—C3B—O2B	125.2 (2)
O3A—C3A—C2A	123.16 (18)	O3B—C3B—C2B	123.54 (18)
Cl1A—C1A—C2A—O1A	59.7 (2)	Cl1B—C1B—C2B—O1B	60.43 (19)
Cl1A—C1A—C2A—C3A	−60.1 (2)	Cl1B—C1B—C2B—C3B	−61.0 (2)
O1A—C2A—C3A—O2A	173.88 (17)	O1B—C2B—C3B—O2B	176.07 (17)
O1A—C2A—C3A—O3A	−5.6 (3)	O1B—C2B—C3B—O3B	−2.9 (3)
C1A—C2A—C3A—O2A	−62.5 (2)	C1B—C2B—C3B—O2B	−63.2 (2)
C1A—C2A—C3A—O3A	117.9 (2)	C1B—C2B—C3B—O3B	117.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O1B^i	0.80 (2)	1.96 (2)	2.752 (2)	170 (2)
O2A—H2A···O1A^ii	0.82 (3)	1.97 (3)	2.770 (2)	166 (3)
O2A—H2A···O3A^ii	0.82 (3)	2.45 (3)	2.959 (2)	121 (2)
C1A—H1AA···O3B^iii	0.99	2.63	3.195 (3)	116
C2A—H2AA···O3B^iii	1.00	2.44	3.114 (3)	124
O1B—H1B···O3A	0.81 (3)	1.95 (3)	2.723 (2)	159 (3)
O2B—H2B···O1B^ii	0.83 (3)	2.24 (3)	3.047 (2)	164 (2)
O2B—H2B···O3B^ii	0.83 (3)	2.47 (3)	2.963 (2)	119 (2)
C1B—H1BB···Cl1B^iv	0.99	2.95	3.764 (2)	141
C2B—H2BA···O3A^v	1.00	2.52	3.177 (3)	123

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

3-Bromo-2-hydroxypropanoic acid (mo_21189_0ma_a)

Crystal data

C3H5BrO3	F(000) = 656
Mr = 168.98	Dx = 2.096 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.3076 (4) Å	Cell parameters from 9452 reflections
b = 10.8912 (3) Å	θ = 2.7–27.3°
c = 9.0769 (3) Å	µ = 7.57 mm^−1
β = 106.673 (1)°	T = 301 K
V = 1070.85 (6) Å^3	Plate, colourless
Z = 8	0.4 × 0.15 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer	2079 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.048
Absorption correction: multi-scan (SADABS2016; Bruker, 2016)	θmax = 27.5°, θmin = 1.9°
Tmin = 0.488, Tmax = 0.746	h = −14→14
25050 measured reflections	k = −14→14
2469 independent reflections	l = −11→11

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.118	w = 1/[σ^2(Fo^2) + (0.0662P)^2 + 1.5353P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
2469 reflections	Δρmax = 1.28 e Å^−3
134 parameters	Δρmin = −0.95 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.

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

	x	y	z	Uiso*/Ueq
Br1A	0.10364 (4)	0.16899 (4)	0.54355 (6)	0.05749 (18)
Br1B	0.91376 (4)	0.39586 (5)	0.64075 (6)	0.05988 (18)
O3A	0.4161 (2)	0.2773 (2)	0.5508 (3)	0.0343 (5)
O1B	0.6270 (3)	0.4133 (2)	0.5699 (3)	0.0371 (5)
H1B	0.566391	0.368331	0.543845	0.048 (13)*
O1A	0.3836 (3)	0.1011 (2)	0.7284 (3)	0.0379 (6)
H1A	0.370903	0.042310	0.778162	0.057*
O3B	0.6459 (3)	0.2210 (2)	0.3935 (3)	0.0501 (7)
O2A	0.3537 (3)	0.1622 (3)	0.3393 (3)	0.0505 (8)
H2A	0.373757	0.222673	0.298229	0.076*
O2B	0.7047 (4)	0.3401 (3)	0.2277 (4)	0.0635 (10)
H2B	0.719 (7)	0.276 (7)	0.203 (8)	0.095*
C3A	0.3753 (3)	0.1828 (3)	0.4872 (4)	0.0292 (6)
C2A	0.3451 (3)	0.0719 (3)	0.5701 (4)	0.0302 (7)
H2AA	0.394352	0.002381	0.552467	0.036*
C2B	0.6706 (3)	0.4373 (3)	0.4414 (4)	0.0297 (6)
H2BA	0.613365	0.494429	0.373053	0.036*
C3B	0.6728 (4)	0.3190 (3)	0.3542 (4)	0.0342 (7)
C1B	0.7950 (3)	0.4981 (3)	0.4962 (4)	0.0387 (8)
H1BA	0.786612	0.575553	0.545101	0.046*
H1BB	0.825070	0.515574	0.408563	0.046*
C1A	0.2097 (4)	0.0372 (3)	0.5129 (4)	0.0396 (8)
H1AA	0.195341	−0.035446	0.567198	0.048*
H1AB	0.188908	0.017427	0.404309	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1A	0.0435 (3)	0.0478 (3)	0.0813 (4)	0.00380 (17)	0.0181 (2)	−0.0083 (2)
Br1B	0.0396 (3)	0.0708 (3)	0.0643 (3)	0.00844 (19)	0.0070 (2)	0.0066 (2)
O3A	0.0491 (14)	0.0264 (11)	0.0308 (12)	−0.0073 (10)	0.0168 (11)	−0.0023 (9)
O1B	0.0428 (14)	0.0438 (13)	0.0303 (12)	−0.0075 (11)	0.0193 (11)	−0.0090 (10)
O1A	0.0561 (16)	0.0347 (12)	0.0237 (11)	−0.0012 (11)	0.0124 (11)	0.0070 (9)
O3B	0.080 (2)	0.0268 (12)	0.0506 (16)	−0.0011 (13)	0.0293 (15)	−0.0004 (11)
O2A	0.090 (2)	0.0420 (14)	0.0235 (12)	−0.0201 (14)	0.0221 (13)	−0.0021 (10)
O2B	0.113 (3)	0.0477 (17)	0.0479 (17)	−0.0128 (18)	0.0520 (19)	−0.0116 (14)
C3A	0.0372 (17)	0.0264 (14)	0.0257 (15)	0.0002 (12)	0.0119 (13)	0.0006 (11)
C2A	0.0456 (19)	0.0215 (13)	0.0273 (15)	0.0022 (12)	0.0168 (14)	0.0021 (11)
C2B	0.0388 (17)	0.0260 (14)	0.0265 (15)	0.0015 (12)	0.0129 (13)	0.0006 (11)
C3B	0.0460 (19)	0.0312 (16)	0.0277 (16)	0.0028 (14)	0.0144 (14)	−0.0017 (12)
C1B	0.043 (2)	0.0343 (17)	0.0424 (19)	−0.0029 (15)	0.0177 (16)	0.0026 (14)
C1A	0.053 (2)	0.0252 (15)	0.044 (2)	−0.0047 (14)	0.0181 (17)	−0.0063 (13)

Geometric parameters (Å, º)

Br1A—C1A	1.941 (4)	O2B—C3B	1.319 (4)
Br1B—C1B	1.938 (4)	C3A—C2A	1.512 (4)
O3A—C3A	1.206 (4)	C2A—H2AA	0.9800
O1B—H1B	0.8200	C2A—C1A	1.517 (5)
O1B—C2B	1.415 (4)	C2B—H2BA	0.9800
O1A—H1A	0.8200	C2B—C3B	1.517 (4)
O1A—C2A	1.413 (4)	C2B—C1B	1.504 (5)
O3B—C3B	1.192 (4)	C1B—H1BA	0.9700
O2A—H2A	0.8200	C1B—H1BB	0.9700
O2A—C3A	1.313 (4)	C1A—H1AA	0.9700
O2B—H2B	0.76 (8)	C1A—H1AB	0.9700
C2B—O1B—H1B	109.5	C1B—C2B—H2BA	108.4
C2A—O1A—H1A	109.5	C1B—C2B—C3B	113.2 (3)
C3A—O2A—H2A	109.5	O3B—C3B—O2B	125.0 (3)
C3B—O2B—H2B	103 (6)	O3B—C3B—C2B	124.1 (3)
O3A—C3A—O2A	124.7 (3)	O2B—C3B—C2B	110.8 (3)
O3A—C3A—C2A	123.6 (3)	Br1B—C1B—H1BA	109.3
O2A—C3A—C2A	111.7 (3)	Br1B—C1B—H1BB	109.3
O1A—C2A—C3A	106.2 (3)	C2B—C1B—Br1B	111.8 (2)
O1A—C2A—H2AA	108.4	C2B—C1B—H1BA	109.3
O1A—C2A—C1A	113.0 (3)	C2B—C1B—H1BB	109.3
C3A—C2A—H2AA	108.4	H1BA—C1B—H1BB	107.9
C3A—C2A—C1A	112.2 (3)	Br1A—C1A—H1AA	109.3
C1A—C2A—H2AA	108.4	Br1A—C1A—H1AB	109.3
O1B—C2B—H2BA	108.4	C2A—C1A—Br1A	111.8 (2)
O1B—C2B—C3B	109.6 (3)	C2A—C1A—H1AA	109.3
O1B—C2B—C1B	108.8 (3)	C2A—C1A—H1AB	109.3
C3B—C2B—H2BA	108.4	H1AA—C1A—H1AB	107.9
O3A—C3A—C2A—O1A	−4.6 (5)	O2A—C3A—C2A—O1A	174.3 (3)
O3A—C3A—C2A—C1A	119.3 (4)	O2A—C3A—C2A—C1A	−61.8 (4)
O1B—C2B—C3B—O3B	−2.7 (5)	C3A—C2A—C1A—Br1A	−60.5 (3)
O1B—C2B—C3B—O2B	175.5 (3)	C3B—C2B—C1B—Br1B	−62.6 (3)
O1B—C2B—C1B—Br1B	59.5 (3)	C1B—C2B—C3B—O3B	119.0 (4)
O1A—C2A—C1A—Br1A	59.5 (3)	C1B—C2B—C3B—O2B	−62.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O1B^i	0.82	1.96	2.771 (3)	168
O2A—H2A···O3A^ii	0.82	2.43	2.974 (3)	125
O2A—H2A···O1A^ii	0.82	2.03	2.823 (4)	161
O2B—H2B···Br1B^ii	0.76 (8)	3.07 (8)	3.726 (4)	146 (7)
O2B—H2B···O1B^ii	0.76 (8)	2.47 (8)	3.118 (4)	145 (7)
O2B—H2B···O3B^ii	0.76 (8)	2.70 (7)	2.988 (4)	105 (6)
C2A—H2AA···O3B^iii	0.98	2.55	3.206 (4)	124
C2B—H2BA···O3A^iv	0.98	2.63	3.265 (4)	123
C1A—H1AA···O3B^iii	0.97	2.66	3.240 (5)	119

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

2-Hydroxy-3-iodopropanoic acid (21166)

Crystal data

C3H5IO3	F(000) = 400
Mr = 215.97	Dx = 2.504 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.4762 (8) Å	Cell parameters from 6362 reflections
b = 5.4370 (4) Å	θ = 3.6–27.0°
c = 9.1941 (7) Å	µ = 5.49 mm^−1
β = 92.848 (3)°	T = 153 K
V = 572.97 (7) Å^3	Plate, colourless
Z = 4	0.27 × 0.16 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer	1102 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.056
Absorption correction: multi-scan (SADABS2016; Bruker, 2016)	θmax = 27.5°, θmin = 3.6°
Tmin = 0.556, Tmax = 0.746	h = −14→14
16586 measured reflections	k = −6→7
1308 independent reflections	l = −11→11

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.025	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.057	w = 1/[σ^2(Fo^2) + (0.0197P)^2 + 1.2602P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
1308 reflections	Δρmax = 0.59 e Å^−3
69 parameters	Δρmin = −0.66 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.

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

	x	y	z	Uiso*/Ueq
I1	0.10060 (2)	0.11577 (5)	0.18694 (3)	0.03582 (11)
O1	0.3689 (2)	−0.0419 (5)	0.2883 (3)	0.0280 (6)
H1	0.435419	−0.096878	0.312553	0.042*
O2	0.3384 (3)	0.0992 (5)	−0.0900 (3)	0.0337 (7)
H2	0.349 (5)	0.211 (12)	−0.130 (7)	0.07 (2)*
O3	0.4187 (2)	0.3096 (5)	0.0974 (3)	0.0314 (6)
C1	0.2156 (3)	−0.1709 (7)	0.1191 (4)	0.0303 (8)
H1A	0.202299	−0.321458	0.176539	0.036*
H1B	0.197462	−0.209631	0.015196	0.036*
C2	0.3422 (3)	−0.0953 (6)	0.1394 (4)	0.0246 (7)
H2A	0.392167	−0.235737	0.109911	0.030*
C3	0.3704 (3)	0.1277 (6)	0.0481 (4)	0.0213 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.02602 (14)	0.03541 (17)	0.04660 (17)	−0.00509 (11)	0.00755 (10)	−0.00537 (12)
O1	0.0384 (14)	0.0265 (14)	0.0186 (12)	0.0055 (11)	−0.0021 (10)	0.0007 (10)
O2	0.0570 (19)	0.0251 (15)	0.0187 (13)	−0.0030 (13)	0.0000 (12)	0.0011 (12)
O3	0.0349 (14)	0.0280 (14)	0.0307 (14)	−0.0105 (11)	−0.0036 (11)	0.0033 (11)
C1	0.034 (2)	0.025 (2)	0.033 (2)	−0.0055 (15)	0.0048 (16)	−0.0041 (15)
C2	0.0328 (19)	0.0201 (18)	0.0209 (17)	0.0033 (14)	0.0017 (14)	−0.0009 (14)
C3	0.0208 (15)	0.0234 (18)	0.0199 (16)	0.0058 (14)	0.0027 (12)	−0.0015 (14)

Geometric parameters (Å, º)

I1—C1	2.154 (4)	C1—H1A	0.9900
O1—H1	0.8400	C1—H1B	0.9900
O1—C2	1.418 (4)	C1—C2	1.513 (5)
O2—H2	0.72 (6)	C2—H2A	1.0000
O2—C3	1.313 (4)	C2—C3	1.519 (5)
O3—C3	1.211 (4)
C2—O1—H1	109.5	O1—C2—H2A	108.6
C3—O2—H2	110 (5)	O1—C2—C3	109.2 (3)
I1—C1—H1A	109.3	C1—C2—H2A	108.6
I1—C1—H1B	109.3	C1—C2—C3	112.2 (3)
H1A—C1—H1B	108.0	C3—C2—H2A	108.6
C2—C1—I1	111.5 (2)	O2—C3—C2	112.6 (3)
C2—C1—H1A	109.3	O3—C3—O2	124.0 (3)
C2—C1—H1B	109.3	O3—C3—C2	123.4 (3)
O1—C2—C1	109.5 (3)
I1—C1—C2—O1	59.5 (3)	O1—C2—C3—O3	6.6 (5)
I1—C1—C2—C3	−61.9 (3)	C1—C2—C3—O2	−52.8 (4)
O1—C2—C3—O2	−174.4 (3)	C1—C2—C3—O3	128.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1^i	0.72 (6)	1.97 (6)	2.684 (4)	172 (7)
O2—H2···O3^i	0.72 (6)	2.68 (6)	3.101 (4)	120 (6)

Symmetry code: (i) x, −y+1/2, z−1/2.