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

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031291/sj2096sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031291/sj2096Isup2.hkl
Contains datablock I

CCDC reference: 621487

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

Computing details top

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 top
Crystal data top
C9H11NO5SF(000) = 256
Mr = 245.25Dx = 1.547 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1568 reflections
a = 5.6357 (16) Åθ = 3.7–27.5°
b = 9.177 (3) ŵ = 0.31 mm1
c = 10.308 (3) ÅT = 293 K
β = 98.950 (4)°Prism, white
V = 526.6 (3) Å30.30 × 0.15 × 0.08 mm
Z = 2
Data collection top
Bruker CCD area-detector
diffractometer
2239 independent reflections
Radiation source: fine-focus sealed tube2195 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
φ and ω scansθmax = 27.5°, θmin = 3.7°
Absorption correction: multi-scan
CrystalClear (Rigaku/MSC, 2004)
h = 77
Tmin = 0.945, Tmax = 0.975k = 1111
4021 measured reflectionsl = 1312
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025H-atom parameters constrained
wR(F2) = 0.067 w = 1/[σ2(Fo2) + (0.0432P)2 + 0.0703P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
2239 reflectionsΔρmax = 0.30 e Å3
145 parametersΔρmin = 0.28 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.06 (6)
Special details top

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 (Å2) top
xyzUiso*/Ueq
S10.82638 (6)0.56005 (4)0.83462 (3)0.01299 (10)
O10.9343 (2)0.42486 (13)0.89558 (11)0.0197 (3)
O20.9862 (2)0.68305 (13)0.85619 (11)0.0179 (3)
O30.5917 (2)0.58587 (13)0.87428 (11)0.0182 (3)
O40.5318 (2)0.70033 (13)0.15723 (11)0.0196 (3)
O50.1481 (2)0.64988 (14)0.17362 (12)0.0203 (3)
H50.12650.73590.15380.030*
N10.3880 (2)0.39200 (15)0.04440 (12)0.0140 (3)
H1A0.24240.41330.00190.021*
H1B0.40720.29570.04760.021*
H1C0.49860.43160.00240.021*
C10.7713 (3)0.52412 (17)0.66357 (15)0.0141 (3)
C20.5808 (3)0.4351 (2)0.61243 (16)0.0219 (4)
H2A0.47630.39950.66640.026*
C30.5474 (3)0.3995 (2)0.47952 (17)0.0234 (4)
H3A0.42270.33740.44560.028*
C40.6983 (3)0.45566 (18)0.39635 (15)0.0155 (3)
C50.8843 (3)0.5474 (3)0.44906 (15)0.0228 (4)
H5A0.98450.58700.39460.027*
C60.9232 (3)0.5809 (2)0.58298 (16)0.0228 (4)
H6A1.05030.64100.61770.027*
C70.6656 (3)0.41358 (19)0.25252 (14)0.0157 (3)
H7A0.69220.30970.24530.019*
H7B0.78470.46380.21050.019*
C80.4148 (3)0.45136 (18)0.18091 (15)0.0134 (3)
H8A0.29350.40740.22730.016*
C90.3745 (3)0.61499 (19)0.17025 (15)0.0136 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01714 (16)0.01037 (18)0.01138 (16)0.00135 (15)0.00204 (11)0.00000 (14)
O10.0268 (6)0.0123 (6)0.0170 (6)0.0001 (5)0.0057 (4)0.0015 (5)
O20.0223 (6)0.0138 (6)0.0177 (6)0.0053 (5)0.0033 (4)0.0019 (5)
O30.0194 (5)0.0180 (7)0.0184 (5)0.0015 (5)0.0070 (4)0.0014 (5)
O40.0244 (6)0.0138 (6)0.0219 (6)0.0034 (5)0.0073 (5)0.0010 (5)
O50.0193 (6)0.0130 (6)0.0288 (7)0.0040 (5)0.0042 (5)0.0038 (5)
N10.0181 (6)0.0122 (7)0.0117 (6)0.0005 (5)0.0022 (5)0.0016 (5)
C10.0162 (7)0.0146 (9)0.0113 (6)0.0016 (6)0.0015 (5)0.0000 (6)
C20.0232 (8)0.0287 (10)0.0137 (7)0.0088 (8)0.0024 (6)0.0030 (7)
C30.0257 (9)0.0273 (10)0.0157 (8)0.0111 (7)0.0020 (6)0.0013 (7)
C40.0182 (7)0.0142 (8)0.0131 (7)0.0052 (6)0.0008 (5)0.0005 (6)
C50.0220 (7)0.0307 (10)0.0169 (7)0.0060 (8)0.0067 (5)0.0029 (8)
C60.0218 (7)0.0284 (11)0.0186 (7)0.0103 (8)0.0044 (6)0.0050 (7)
C70.0170 (7)0.0169 (8)0.0131 (7)0.0028 (6)0.0016 (5)0.0007 (6)
C80.0170 (7)0.0139 (8)0.0098 (7)0.0002 (6)0.0034 (5)0.0019 (6)
C90.0172 (7)0.0152 (8)0.0084 (6)0.0017 (6)0.0023 (5)0.0006 (6)
Geometric parameters (Å, º) top
S1—O21.4397 (13)C2—H2A0.9300
S1—O31.4632 (12)C3—C41.397 (2)
S1—O11.4782 (12)C3—H3A0.9300
S1—C11.7730 (16)C4—C51.388 (2)
O4—C91.206 (2)C4—C71.515 (2)
O5—C91.321 (2)C5—C61.398 (2)
O5—H50.8200C5—H5A0.9300
N1—C81.4945 (19)C6—H6A0.9300
N1—H1A0.8900C7—C81.529 (2)
N1—H1B0.8900C7—H7A0.9700
N1—H1C0.8900C7—H7B0.9700
C1—C61.384 (2)C8—C91.520 (3)
C1—C21.386 (2)C8—H8A0.9800
C2—C31.392 (2)
O2—S1—O3113.64 (7)C5—C4—C7120.47 (15)
O2—S1—O1112.72 (7)C3—C4—C7120.90 (15)
O3—S1—O1110.31 (7)C4—C5—C6120.87 (15)
O2—S1—C1107.93 (7)C4—C5—H5A119.6
O3—S1—C1106.38 (7)C6—C5—H5A119.6
O1—S1—C1105.27 (7)C1—C6—C5119.54 (16)
C9—O5—H5109.5C1—C6—H6A120.2
C8—N1—H1A109.5C5—C6—H6A120.2
C8—N1—H1B109.5C4—C7—C8112.15 (13)
H1A—N1—H1B109.5C4—C7—H7A109.2
C8—N1—H1C109.5C8—C7—H7A109.2
H1A—N1—H1C109.5C4—C7—H7B109.2
H1B—N1—H1C109.5C8—C7—H7B109.2
C6—C1—C2120.56 (15)H7A—C7—H7B107.9
C6—C1—S1119.86 (12)N1—C8—C9107.45 (13)
C2—C1—S1119.54 (12)N1—C8—C7108.79 (13)
C1—C2—C3119.37 (15)C9—C8—C7112.05 (14)
C1—C2—H2A120.3N1—C8—H8A109.5
C3—C2—H2A120.3C9—C8—H8A109.5
C2—C3—C4121.02 (16)C7—C8—H8A109.5
C2—C3—H3A119.5O4—C9—O5125.12 (16)
C4—C3—H3A119.5O4—C9—C8123.04 (16)
C5—C4—C3118.59 (15)O5—C9—C8111.82 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O1i0.821.822.6438 (19)177
N1—H1A···O1ii0.891.912.7861 (19)169
N1—H1B···O3iii0.892.092.929 (2)157
N1—H1C···O3iv0.892.062.8607 (18)149
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x1, y, z1; (iii) x+1, y1/2, z+1; (iv) x, y, z1.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds