L-Phenyl­alaninium 4-sulfonate

In the crystal structure of the title compound (H₂SPA), C₉H₁₁NO₅S, hydrogen-bonding inter­actions lead to the formation of a three-dimensional network

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.025
• wR factor = 0.067
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

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           27.48
           From the CIF: _reflns_number_total               2239
           Count of symmetry unique reflns         1281
           Completeness (_total/calc)            174.79%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       958
           Fraction of Friedel pairs measured     0.748
           Are heavy atom types Z>Si present        yes
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
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
   1 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   4 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: CrystalClear (Rigaku/MSC, 2004); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Siemens, 1994); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

4-sulfonato-L-phenylalaninium

Crystal data

C9H11NO5S	F(000) = 256
Mr = 245.25	Dx = 1.547 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1568 reflections
a = 5.6357 (16) Å	θ = 3.7–27.5°
b = 9.177 (3) Å	µ = 0.31 mm^−1
c = 10.308 (3) Å	T = 293 K
β = 98.950 (4)°	Prism, white
V = 526.6 (3) Å^3	0.30 × 0.15 × 0.08 mm
Z = 2

Data collection

Bruker CCD area-detector diffractometer	2239 independent reflections
Radiation source: fine-focus sealed tube	2195 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
φ and ω scans	θmax = 27.5°, θmin = 3.7°
Absorption correction: multi-scan CrystalClear (Rigaku/MSC, 2004)	h = −7→7
Tmin = 0.945, Tmax = 0.975	k = −11→11
4021 measured reflections	l = −13→12

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)] = 0.025	H-atom parameters constrained
wR(F^2) = 0.067	w = 1/[σ^2(Fo^2) + (0.0432P)^2 + 0.0703P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
2239 reflections	Δρmax = 0.30 e Å^−3
145 parameters	Δρmin = −0.28 e Å^−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.06 (6)

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
S1	0.82638 (6)	0.56005 (4)	0.83462 (3)	0.01299 (10)
O1	0.9343 (2)	0.42486 (13)	0.89558 (11)	0.0197 (3)
O2	0.9862 (2)	0.68305 (13)	0.85619 (11)	0.0179 (3)
O3	0.5917 (2)	0.58587 (13)	0.87428 (11)	0.0182 (3)
O4	0.5318 (2)	0.70033 (13)	0.15723 (11)	0.0196 (3)
O5	0.1481 (2)	0.64988 (14)	0.17362 (12)	0.0203 (3)
H5	0.1265	0.7359	0.1538	0.030*
N1	0.3880 (2)	0.39200 (15)	0.04440 (12)	0.0140 (3)
H1A	0.2424	0.4133	0.0019	0.021*
H1B	0.4072	0.2957	0.0476	0.021*
H1C	0.4986	0.4316	0.0024	0.021*
C1	0.7713 (3)	0.52412 (17)	0.66357 (15)	0.0141 (3)
C2	0.5808 (3)	0.4351 (2)	0.61243 (16)	0.0219 (4)
H2A	0.4763	0.3995	0.6664	0.026*
C3	0.5474 (3)	0.3995 (2)	0.47952 (17)	0.0234 (4)
H3A	0.4227	0.3374	0.4456	0.028*
C4	0.6983 (3)	0.45566 (18)	0.39635 (15)	0.0155 (3)
C5	0.8843 (3)	0.5474 (3)	0.44906 (15)	0.0228 (4)
H5A	0.9845	0.5870	0.3946	0.027*
C6	0.9232 (3)	0.5809 (2)	0.58298 (16)	0.0228 (4)
H6A	1.0503	0.6410	0.6177	0.027*
C7	0.6656 (3)	0.41358 (19)	0.25252 (14)	0.0157 (3)
H7A	0.6922	0.3097	0.2453	0.019*
H7B	0.7847	0.4638	0.2105	0.019*
C8	0.4148 (3)	0.45136 (18)	0.18091 (15)	0.0134 (3)
H8A	0.2935	0.4074	0.2273	0.016*
C9	0.3745 (3)	0.61499 (19)	0.17025 (15)	0.0136 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01714 (16)	0.01037 (18)	0.01138 (16)	−0.00135 (15)	0.00204 (11)	0.00000 (14)
O1	0.0268 (6)	0.0123 (6)	0.0170 (6)	−0.0001 (5)	−0.0057 (4)	0.0015 (5)
O2	0.0223 (6)	0.0138 (6)	0.0177 (6)	−0.0053 (5)	0.0033 (4)	−0.0019 (5)
O3	0.0194 (5)	0.0180 (7)	0.0184 (5)	−0.0015 (5)	0.0070 (4)	−0.0014 (5)
O4	0.0244 (6)	0.0138 (6)	0.0219 (6)	−0.0034 (5)	0.0073 (5)	0.0010 (5)
O5	0.0193 (6)	0.0130 (6)	0.0288 (7)	0.0040 (5)	0.0042 (5)	0.0038 (5)
N1	0.0181 (6)	0.0122 (7)	0.0117 (6)	−0.0005 (5)	0.0022 (5)	−0.0016 (5)
C1	0.0162 (7)	0.0146 (9)	0.0113 (6)	0.0016 (6)	0.0015 (5)	0.0000 (6)
C2	0.0232 (8)	0.0287 (10)	0.0137 (7)	−0.0088 (8)	0.0024 (6)	0.0030 (7)
C3	0.0257 (9)	0.0273 (10)	0.0157 (8)	−0.0111 (7)	−0.0020 (6)	0.0013 (7)
C4	0.0182 (7)	0.0142 (8)	0.0131 (7)	0.0052 (6)	−0.0008 (5)	−0.0005 (6)
C5	0.0220 (7)	0.0307 (10)	0.0169 (7)	−0.0060 (8)	0.0067 (5)	−0.0029 (8)
C6	0.0218 (7)	0.0284 (11)	0.0186 (7)	−0.0103 (8)	0.0044 (6)	−0.0050 (7)
C7	0.0170 (7)	0.0169 (8)	0.0131 (7)	0.0028 (6)	0.0016 (5)	−0.0007 (6)
C8	0.0170 (7)	0.0139 (8)	0.0098 (7)	0.0002 (6)	0.0034 (5)	−0.0019 (6)
C9	0.0172 (7)	0.0152 (8)	0.0084 (6)	0.0017 (6)	0.0023 (5)	0.0006 (6)

Geometric parameters (Å, º)

S1—O2	1.4397 (13)	C2—H2A	0.9300
S1—O3	1.4632 (12)	C3—C4	1.397 (2)
S1—O1	1.4782 (12)	C3—H3A	0.9300
S1—C1	1.7730 (16)	C4—C5	1.388 (2)
O4—C9	1.206 (2)	C4—C7	1.515 (2)
O5—C9	1.321 (2)	C5—C6	1.398 (2)
O5—H5	0.8200	C5—H5A	0.9300
N1—C8	1.4945 (19)	C6—H6A	0.9300
N1—H1A	0.8900	C7—C8	1.529 (2)
N1—H1B	0.8900	C7—H7A	0.9700
N1—H1C	0.8900	C7—H7B	0.9700
C1—C6	1.384 (2)	C8—C9	1.520 (3)
C1—C2	1.386 (2)	C8—H8A	0.9800
C2—C3	1.392 (2)
O2—S1—O3	113.64 (7)	C5—C4—C7	120.47 (15)
O2—S1—O1	112.72 (7)	C3—C4—C7	120.90 (15)
O3—S1—O1	110.31 (7)	C4—C5—C6	120.87 (15)
O2—S1—C1	107.93 (7)	C4—C5—H5A	119.6
O3—S1—C1	106.38 (7)	C6—C5—H5A	119.6
O1—S1—C1	105.27 (7)	C1—C6—C5	119.54 (16)
C9—O5—H5	109.5	C1—C6—H6A	120.2
C8—N1—H1A	109.5	C5—C6—H6A	120.2
C8—N1—H1B	109.5	C4—C7—C8	112.15 (13)
H1A—N1—H1B	109.5	C4—C7—H7A	109.2
C8—N1—H1C	109.5	C8—C7—H7A	109.2
H1A—N1—H1C	109.5	C4—C7—H7B	109.2
H1B—N1—H1C	109.5	C8—C7—H7B	109.2
C6—C1—C2	120.56 (15)	H7A—C7—H7B	107.9
C6—C1—S1	119.86 (12)	N1—C8—C9	107.45 (13)
C2—C1—S1	119.54 (12)	N1—C8—C7	108.79 (13)
C1—C2—C3	119.37 (15)	C9—C8—C7	112.05 (14)
C1—C2—H2A	120.3	N1—C8—H8A	109.5
C3—C2—H2A	120.3	C9—C8—H8A	109.5
C2—C3—C4	121.02 (16)	C7—C8—H8A	109.5
C2—C3—H3A	119.5	O4—C9—O5	125.12 (16)
C4—C3—H3A	119.5	O4—C9—C8	123.04 (16)
C5—C4—C3	118.59 (15)	O5—C9—C8	111.82 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O1^i	0.82	1.82	2.6438 (19)	177
N1—H1A···O1^ii	0.89	1.91	2.7861 (19)	169
N1—H1B···O3^iii	0.89	2.09	2.929 (2)	157
N1—H1C···O3^iv	0.89	2.06	2.8607 (18)	149

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