3-Hy­droxy-2-[(4-hy­droxy­benz­yl)aza­nium­yl]propano­ate monohydrate

In the title hydrated zwitterion, C₁₀H₁₃NO₄·H₂O, the N—C—C—OH side chain shows a gauche conformation [torsion angle = −59.05 (18)°]. In the crystal, the components are linked by O—H...O, N—H...O and C—H...O hydrogen bonds to generate a three-dimensional supra­molecular network.

Key indicators

• Single-crystal synchrotron study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.097
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level A
DIFF019_ALERT_1_A  _diffrn_standards_number is missing
            Number of standards used in measurement.

Author Response: This is a synchrotron data

DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.

Author Response: This is a synchrotron data

DIFF022_ALERT_1_A  _diffrn_standards_decay_% is missing
            Percentage decrease in standards intensity.

Author Response: This is a synchrotron data

Alert level C
CRYSC01_ALERT_1_C No recognised colour has been given for crystal colour.
STRVA01_ALERT_4_C           Flack test results are meaningless.
           From the CIF: _refine_ls_abs_structure_Flack    0.200
           From the CIF: _refine_ls_abs_structure_Flack_su    1.200
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         12 Report

Alert level G
ABSMU01_ALERT_1_G  Calculation of _exptl_absorpt_correction_mu
                not performed for this radiation type.
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      1.200 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT791_ALERT_4_G The Model has Chirality at C2      (Chiral SPGR)          R Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         23 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          3 Note
PLAT916_ALERT_2_G Hooft y and Flack x Parameter values differ by .       0.11 Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Note

   3 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: mar165; cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL-2000 (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: pubCIF (Westrip, 2010).

3-Hydroxy-2-[(4-hydroxybenzyl)azaniumyl]propanoate monohydrate

Crystal data

C10H13NO4·H2O	Dx = 1.447 Mg m^−3
Mr = 229.23	Synchrotron radiation, λ = 0.7200 Å
Orthorhombic, P212121	Cell parameters from 5057 reflections
a = 5.5140 (11) Å	θ = 2.7–29.6°
b = 12.418 (3) Å	µ = 0.12 mm^−1
c = 15.372 (3) Å	T = 100 K
V = 1052.6 (4) Å^3	Block, light yelloe
Z = 4	0.30 × 0.20 × 0.20 mm
F(000) = 488

Data collection

Mar165 diffractometer	2624 reflections with I > 2σ(I)
Radiation source: synchrotron, 3W1A at BSRF	Rint = 0.025
oscillation mode scans	θmax = 29.3°, θmin = 2.7°
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	h = 0→7
Tmin = 0.965, Tmax = 0.977	k = −16→16
5039 measured reflections	l = −20→20
2721 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.036	w = 1/[σ^2(Fo^2) + (0.0569P)^2 + 0.2819P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.097	(Δ/σ)max < 0.001
S = 1.11	Δρmax = 0.19 e Å^−3
2721 reflections	Δρmin = −0.22 e Å^−3
164 parameters	Absolute structure: Refined as an inversion twin
0 restraints	Absolute structure parameter: 0.2 (12)
Primary atom site location: structure-invariant direct methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component inversion twin.

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

	x	y	z	Uiso*/Ueq
O1	−0.1740 (2)	0.64457 (10)	0.46536 (8)	0.0124 (3)
O2	−0.1669 (3)	0.49448 (10)	0.38500 (9)	0.0145 (3)
O3	0.2072 (3)	0.74505 (10)	0.34128 (9)	0.0153 (3)
H3	0.297 (6)	0.788 (2)	0.2981 (18)	0.023*
O4	0.6113 (3)	0.16978 (11)	0.65474 (10)	0.0157 (3)
H4	0.507 (5)	0.116 (2)	0.6406 (18)	0.024*
N1	0.3273 (3)	0.63321 (11)	0.49124 (9)	0.0087 (3)
H1A	0.282 (5)	0.7061 (19)	0.4913 (15)	0.010*
H1B	0.499 (5)	0.6282 (19)	0.4830 (16)	0.010*
C1	−0.0667 (3)	0.57215 (13)	0.42362 (11)	0.0094 (3)
C2	0.2125 (3)	0.57711 (13)	0.41594 (11)	0.0097 (3)
H2	0.276793	0.501896	0.413099	0.012*
C3	0.2880 (4)	0.63678 (14)	0.33320 (11)	0.0118 (3)
H3A	0.466456	0.634670	0.326401	0.014*
H3B	0.213318	0.602571	0.281565	0.014*
C4	0.2672 (3)	0.59029 (14)	0.58072 (11)	0.0113 (3)
H4A	0.338442	0.638592	0.625116	0.014*
H4B	0.088978	0.590776	0.588583	0.014*
C5	0.3605 (3)	0.47754 (14)	0.59503 (11)	0.0104 (3)
C6	0.2266 (4)	0.38722 (13)	0.56981 (11)	0.0120 (3)
H6	0.077310	0.396915	0.539990	0.014*
C7	0.3078 (4)	0.28317 (14)	0.58753 (11)	0.0132 (3)
H7	0.215956	0.222503	0.569270	0.016*
C8	0.5258 (3)	0.26924 (14)	0.63247 (11)	0.0122 (3)
C9	0.6632 (3)	0.35835 (15)	0.65700 (12)	0.0132 (3)
H9	0.812625	0.348687	0.686782	0.016*
C10	0.5809 (4)	0.46163 (13)	0.63769 (12)	0.0121 (3)
H10	0.676154	0.522158	0.653820	0.014*
O5	0.4627 (3)	0.88897 (11)	0.23976 (9)	0.0154 (3)
H5A	0.381 (5)	0.927 (2)	0.2039 (19)	0.023*
H5B	0.595 (6)	0.864 (2)	0.2161 (19)	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0082 (6)	0.0102 (5)	0.0188 (6)	0.0008 (5)	0.0009 (5)	−0.0022 (5)
O2	0.0108 (7)	0.0111 (6)	0.0216 (6)	−0.0021 (5)	−0.0026 (5)	−0.0048 (5)
O3	0.0190 (7)	0.0096 (5)	0.0173 (6)	0.0027 (5)	0.0047 (5)	0.0035 (5)
O4	0.0141 (7)	0.0085 (6)	0.0246 (7)	0.0025 (5)	−0.0049 (5)	−0.0007 (5)
N1	0.0074 (7)	0.0066 (6)	0.0122 (6)	−0.0005 (5)	0.0002 (5)	0.0003 (5)
C1	0.0101 (8)	0.0066 (6)	0.0117 (7)	−0.0001 (6)	0.0001 (6)	0.0003 (5)
C2	0.0092 (8)	0.0083 (6)	0.0117 (7)	0.0002 (6)	0.0001 (6)	−0.0008 (5)
C3	0.0105 (8)	0.0111 (7)	0.0137 (7)	0.0016 (6)	0.0014 (6)	0.0007 (6)
C4	0.0112 (9)	0.0114 (7)	0.0113 (7)	0.0008 (6)	0.0007 (6)	0.0003 (6)
C5	0.0098 (8)	0.0110 (7)	0.0106 (7)	−0.0003 (6)	0.0007 (6)	0.0011 (5)
C6	0.0108 (9)	0.0119 (7)	0.0134 (7)	−0.0016 (6)	−0.0012 (6)	0.0019 (6)
C7	0.0142 (9)	0.0106 (7)	0.0149 (7)	−0.0024 (6)	−0.0020 (7)	−0.0002 (6)
C8	0.0126 (9)	0.0112 (7)	0.0127 (7)	0.0009 (6)	0.0015 (6)	−0.0004 (6)
C9	0.0101 (8)	0.0139 (7)	0.0155 (7)	0.0001 (6)	−0.0022 (6)	−0.0001 (6)
C10	0.0106 (8)	0.0115 (7)	0.0141 (7)	−0.0031 (6)	−0.0014 (6)	−0.0006 (6)
O5	0.0146 (8)	0.0158 (6)	0.0157 (6)	0.0026 (5)	0.0016 (5)	0.0035 (5)

Geometric parameters (Å, º)

O1—C1	1.253 (2)	C4—C5	1.508 (2)
O2—C1	1.260 (2)	C4—H4A	0.9900
O3—C3	1.422 (2)	C4—H4B	0.9900
O3—H3	0.98 (3)	C5—C10	1.395 (3)
O4—C8	1.366 (2)	C5—C6	1.398 (2)
O4—H4	0.90 (3)	C6—C7	1.394 (2)
N1—C2	1.492 (2)	C6—H6	0.9500
N1—C4	1.512 (2)	C7—C8	1.397 (3)
N1—H1A	0.94 (2)	C7—H7	0.9500
N1—H1B	0.96 (3)	C8—C9	1.393 (2)
C1—C2	1.545 (3)	C9—C10	1.393 (2)
C2—C3	1.530 (2)	C9—H9	0.9500
C2—H2	1.0000	C10—H10	0.9500
C3—H3A	0.9900	O5—H5A	0.85 (3)
C3—H3B	0.9900	O5—H5B	0.87 (3)
C3—O3—H3	107.0 (16)	C5—C4—H4A	109.1
C8—O4—H4	112.6 (18)	N1—C4—H4A	109.1
C2—N1—C4	116.62 (14)	C5—C4—H4B	109.1
C2—N1—H1A	109.8 (15)	N1—C4—H4B	109.1
C4—N1—H1A	106.3 (15)	H4A—C4—H4B	107.8
C2—N1—H1B	106.7 (14)	C10—C5—C6	118.48 (16)
C4—N1—H1B	108.3 (15)	C10—C5—C4	119.83 (16)
H1A—N1—H1B	109 (2)	C6—C5—C4	121.64 (17)
O1—C1—O2	125.72 (17)	C7—C6—C5	121.34 (17)
O1—C1—C2	118.72 (15)	C7—C6—H6	119.3
O2—C1—C2	115.54 (15)	C5—C6—H6	119.3
N1—C2—C3	107.65 (14)	C6—C7—C8	119.17 (16)
N1—C2—C1	112.46 (14)	C6—C7—H7	120.4
C3—C2—C1	110.73 (14)	C8—C7—H7	120.4
N1—C2—H2	108.6	O4—C8—C9	117.56 (16)
C3—C2—H2	108.6	O4—C8—C7	122.21 (16)
C1—C2—H2	108.6	C9—C8—C7	120.23 (16)
O3—C3—C2	107.47 (13)	C10—C9—C8	119.76 (17)
O3—C3—H3A	110.2	C10—C9—H9	120.1
C2—C3—H3A	110.2	C8—C9—H9	120.1
O3—C3—H3B	110.2	C9—C10—C5	120.98 (16)
C2—C3—H3B	110.2	C9—C10—H10	119.5
H3A—C3—H3B	108.5	C5—C10—H10	119.5
C5—C4—N1	112.66 (14)	H5A—O5—H5B	112 (3)
C4—N1—C2—C3	177.31 (14)	C10—C5—C6—C7	0.9 (3)
C4—N1—C2—C1	55.06 (18)	C4—C5—C6—C7	−176.43 (16)
O1—C1—C2—N1	28.0 (2)	C5—C6—C7—C8	0.9 (3)
O2—C1—C2—N1	−153.20 (14)	C6—C7—C8—O4	177.55 (17)
O1—C1—C2—C3	−92.54 (18)	C6—C7—C8—C9	−1.8 (3)
O2—C1—C2—C3	86.31 (18)	O4—C8—C9—C10	−178.43 (17)
N1—C2—C3—O3	−59.05 (18)	C7—C8—C9—C10	0.9 (3)
C1—C2—C3—O3	64.27 (18)	C8—C9—C10—C5	0.9 (3)
C2—N1—C4—C5	65.0 (2)	C6—C5—C10—C9	−1.7 (3)
N1—C4—C5—C10	96.82 (19)	C4—C5—C10—C9	175.60 (17)
N1—C4—C5—C6	−85.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O5	0.98 (3)	1.79 (3)	2.759 (2)	166 (2)
O4—H4···O2^i	0.90 (3)	1.72 (3)	2.624 (2)	174 (3)
N1—H1A···O1^ii	0.94 (2)	1.98 (2)	2.8390 (19)	150 (2)
N1—H1B···O1^iii	0.96 (3)	1.84 (3)	2.782 (2)	170 (2)
C2—H2···O4^iv	1.00	2.54	3.300 (2)	132
C4—H4A···O3^ii	0.99	2.55	3.392 (2)	143
O5—H5A···O2^v	0.85 (3)	1.99 (3)	2.8380 (19)	172 (3)
O5—H5B···O4^vi	0.87 (3)	1.92 (3)	2.785 (2)	171 (3)

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