3-Iodo-L-tyrosine hemihydrate

The crystal structure of the title compound [systematic name: (S)-2-ammonio-3-(3-iodo-4-hydroxy­phenyl)propanoate hemihydrate], C₉H₁₀INO₃·0.5H₂O, is stabilized by ionic inter­actions and a hydrogen-bond network. The hydrogen bonds, involving a water mol­ecule located on a twofold axis, form bridged layers of 3-iodo-L-tyrosine mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 109 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.021
• wR factor = 0.055
• Data-to-parameter ratio = 34.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.42
PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) .        100 Ang.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          4

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           35.00
           From the CIF: _reflns_number_total               4677
           Count of symmetry unique reflns         2543
           Completeness (_total/calc)            183.92%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2134
           Fraction of Friedel pairs measured     0.839
           Are heavy atom types Z>Si present        yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8     = .          S

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

   5 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
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: HKL-2000 (Otwinowski & Minor, 1997); cell refinement: HKL-2000; data reduction: HKL-2000; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990) and HKL-3000SM (Minor et al., 2006); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) and HKL-3000SM; molecular graphics: HKL-3000SM, Mercury (Macrae et al., 2006), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: HKL-3000SM.

(S)-2-Ammonio-3-(3-iodo-4-hydroxyphenyl)propanoate hemihydrate

Crystal data

C9H10INO3·0.5H2O	F(000) = 612
Mr = 316.09	Dx = 1.962 Mg m^−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71074 Å
Hall symbol: C 2y	Cell parameters from 24658 reflections
a = 18.789 (1) Å	θ = 3.0–35.0°
b = 5.908 (1) Å	µ = 2.98 mm^−1
c = 9.624 (1) Å	T = 109 K
β = 91.04 (1)°	Needle, colourless
V = 1068.1 (2) Å^3	0.48 × 0.04 × 0.04 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	4677 independent reflections
Radiation source: fine-focus sealed tube	4517 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
Detector resolution: 10 pixels mm^-1	θmax = 35.0°, θmin = 3.0°
ω scans with χ offset	h = −29→30
Absorption correction: multi-scan (Otwinowski et al., 2003)	k = −9→9
Tmin = 0.87, Tmax = 0.89	l = −15→15
24658 measured reflections

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)] = 0.021	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.055	w = 1/[σ^2(Fo^2) + (0.0308P)^2 + 1.2436P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.005
4677 reflections	Δρmax = 2.30 e Å^−3
135 parameters	Δρmin = −0.67 e Å^−3
2 restraints	Absolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (2)

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
I1	0.912940 (5)	0.88360 (3)	0.272044 (10)	0.01920 (3)
O2	0.77418 (8)	0.6732 (3)	0.87281 (16)	0.0183 (2)
C8	0.87786 (10)	0.4413 (3)	0.89134 (19)	0.0141 (3)
H10	0.9082	0.4396	0.9753	0.017*
C5	0.80394 (11)	0.3056 (3)	0.4448 (2)	0.0176 (3)
H6	0.7685	0.2060	0.4150	0.021*
N1	0.82220 (9)	0.2622 (3)	0.90435 (18)	0.0168 (3)
H2	0.8430	0.1272	0.9108	0.025*
H3	0.7935	0.2653	0.8298	0.025*
H4	0.7970	0.2876	0.9802	0.025*
C7	0.92455 (9)	0.3961 (7)	0.76484 (16)	0.0161 (3)
H8	0.9655	0.4959	0.7699	0.019*
H9	0.9420	0.2418	0.7702	0.019*
O3	0.88093 (8)	0.8427 (2)	0.87598 (16)	0.0198 (3)
C9	0.84153 (10)	0.6723 (3)	0.88003 (18)	0.0141 (3)
O1	0.79476 (8)	0.5149 (3)	0.22969 (15)	0.0191 (3)
H1	0.7657	0.4143	0.2135	0.029*
C4	0.82377 (10)	0.4850 (3)	0.35974 (19)	0.0157 (3)
C3	0.87537 (10)	0.6371 (3)	0.40881 (19)	0.0152 (3)
C2	0.90569 (10)	0.6125 (3)	0.54102 (19)	0.0155 (3)
H5	0.9384	0.7189	0.5737	0.019*
C6	0.83689 (11)	0.2752 (3)	0.5738 (2)	0.0174 (3)
H7	0.8251	0.1499	0.6271	0.021*
C1	0.88742 (10)	0.4292 (3)	0.62526 (19)	0.0152 (3)
O4	1.0000	1.0592 (4)	0.0000	0.0248 (4)
H11	1.035 (2)	0.967 (7)	0.050 (4)	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.02064 (5)	0.01818 (5)	0.01879 (5)	−0.00081 (6)	0.00088 (3)	0.00528 (5)
O2	0.0168 (6)	0.0176 (6)	0.0205 (6)	0.0014 (5)	0.0003 (5)	0.0020 (5)
C8	0.0164 (7)	0.0118 (6)	0.0140 (7)	−0.0001 (5)	−0.0018 (5)	0.0004 (5)
C5	0.0197 (8)	0.0165 (6)	0.0165 (8)	−0.0042 (6)	0.0004 (6)	−0.0017 (6)
N1	0.0208 (7)	0.0117 (5)	0.0180 (7)	−0.0010 (5)	0.0026 (5)	0.0008 (5)
C7	0.0165 (6)	0.0170 (9)	0.0148 (6)	0.0015 (10)	0.0001 (4)	0.0017 (8)
O3	0.0217 (6)	0.0120 (7)	0.0257 (7)	−0.0014 (4)	−0.0021 (5)	−0.0005 (4)
C9	0.0184 (7)	0.0121 (6)	0.0116 (6)	0.0008 (5)	−0.0016 (5)	0.0000 (5)
O1	0.0221 (6)	0.0201 (6)	0.0150 (6)	−0.0021 (5)	−0.0040 (5)	−0.0008 (5)
C4	0.0173 (7)	0.0161 (7)	0.0137 (7)	−0.0001 (5)	0.0004 (6)	−0.0017 (5)
C3	0.0159 (7)	0.0140 (6)	0.0158 (7)	−0.0003 (5)	0.0008 (6)	0.0001 (5)
C2	0.0167 (7)	0.0154 (7)	0.0144 (7)	−0.0012 (5)	−0.0006 (6)	0.0000 (5)
C6	0.0218 (8)	0.0152 (7)	0.0152 (7)	−0.0033 (6)	0.0013 (6)	0.0000 (5)
C1	0.0162 (7)	0.0146 (8)	0.0150 (7)	0.0005 (5)	0.0021 (5)	−0.0004 (5)
O4	0.0254 (10)	0.0221 (9)	0.0267 (11)	0.000	−0.0036 (8)	0.000

Geometric parameters (Å, º)

I1—C3	2.094 (2)	C7—H8	0.9700
O2—C9	1.266 (2)	C7—H9	0.9700
C8—N1	1.495 (2)	O3—C9	1.250 (2)
C8—C9	1.529 (2)	O1—C4	1.368 (2)
C8—C7	1.537 (3)	O1—H1	0.8200
C8—H10	0.9800	C4—C3	1.398 (3)
C5—C6	1.389 (3)	C3—C2	1.392 (3)
C5—C4	1.394 (3)	C2—C1	1.399 (3)
C5—H6	0.9300	C2—H5	0.9300
N1—H2	0.8900	C6—C1	1.399 (3)
N1—H3	0.8900	C6—H7	0.9300
N1—H4	0.8900	O4—H11	0.98 (3)
C7—C1	1.515 (2)
N1—C8—C9	109.01 (15)	H8—C7—H9	107.5
N1—C8—C7	110.71 (17)	O3—C9—O2	125.93 (17)
C9—C8—C7	111.06 (18)	O3—C9—C8	117.18 (16)
N1—C8—H10	108.7	O2—C9—C8	116.87 (16)
C9—C8—H10	108.7	C4—O1—H1	109.5
C7—C8—H10	108.7	O1—C4—C5	121.96 (17)
C6—C5—C4	120.25 (17)	O1—C4—C3	119.23 (17)
C6—C5—H6	119.9	C5—C4—C3	118.80 (17)
C4—C5—H6	119.9	C2—C3—C4	120.74 (17)
C8—N1—H2	109.5	C2—C3—I1	120.68 (13)
C8—N1—H3	109.5	C4—C3—I1	118.32 (13)
H2—N1—H3	109.5	C3—C2—C1	120.67 (17)
C8—N1—H4	109.5	C3—C2—H5	119.7
H2—N1—H4	109.5	C1—C2—H5	119.7
H3—N1—H4	109.5	C5—C6—C1	121.38 (17)
C1—C7—C8	114.82 (16)	C5—C6—H7	119.3
C1—C7—H8	108.6	C1—C6—H7	119.3
C8—C7—H8	108.6	C2—C1—C6	118.05 (17)
C1—C7—H9	108.6	C2—C1—C7	119.99 (19)
C8—C7—H9	108.6	C6—C1—C7	121.90 (19)
N1—C8—C7—C1	69.7 (3)	C5—C4—C3—I1	173.21 (14)
C9—C8—C7—C1	−51.5 (3)	C4—C3—C2—C1	2.8 (3)
N1—C8—C9—O3	176.23 (16)	I1—C3—C2—C1	−171.26 (14)
C7—C8—C9—O3	−61.5 (2)	C4—C5—C6—C1	3.7 (3)
N1—C8—C9—O2	−5.1 (2)	C3—C2—C1—C6	−1.3 (3)
C7—C8—C9—O2	117.09 (19)	C3—C2—C1—C7	175.87 (19)
C6—C5—C4—O1	177.17 (18)	C5—C6—C1—C2	−1.9 (3)
C6—C5—C4—C3	−2.2 (3)	C5—C6—C1—C7	−179.1 (2)
O1—C4—C3—C2	179.61 (18)	C8—C7—C1—C2	109.7 (2)
C5—C4—C3—C2	−1.0 (3)	C8—C7—C1—C6	−73.3 (3)
O1—C4—C3—I1	−6.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2···O3^i	0.89	1.86	2.729 (2)	165
N1—H3···O1^ii	0.89	2.29	2.920 (2)	128
N1—H4···O2^iii	0.89	2.08	2.880 (2)	150
O1—H1···O2^ii	0.82	1.80	2.585 (2)	158
O4—H11···O3^iv	0.98 (3)	1.87 (3)	2.823 (2)	165 (4)

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