Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801011941/ci6028sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801011941/ci6028Isup2.hkl |
CCDC reference: 170917
The title compound was crystallized by the slow evaporation of an aqueous solution of D-phenylglycine and sulfuric acid in a stoichiometric ratio of 2:1. Colourless needle-shaped transparent crystals were obtained.
The H atoms of the water molecule were located from difference Fourier maps and refined, while all the other H atoms were fixed by geometric constraints using HFIX. 91 Friedel pairs were used to determine the Flack parameter.
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.
2C8H10NO2+·SO42−·H2O | F(000) = 440 |
Mr = 418.42 | Dx = 1.427 Mg m−3 Dm = 1.429 Mg m−3 Dm measured by flotation |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71070 Å |
a = 12.3201 (12) Å | Cell parameters from 25 reflections |
b = 5.9377 (15) Å | θ = 8.3–13.6° |
c = 14.2908 (16) Å | µ = 0.22 mm−1 |
β = 111.369 (10)° | T = 293 K |
V = 973.5 (3) Å3 | Needles, colorless |
Z = 2 | 0.25 × 0.20 × 0.15 mm |
Enraf-Nonius sealed tube diffractometer | 1778 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.044 |
Graphite monochromator | θmax = 25.0°, θmin = 2.7° |
ω–2θ scans | h = −14→13 |
Absorption correction: ψ scan (North et.al.,1968) | k = 0→7 |
Tmin = 0.949, Tmax = 0.968 | l = 0→16 |
1968 measured reflections | 3 standard reflections every 60 min |
1877 independent reflections | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.133 | w = 1/[σ2(Fo2) + (0.1005P)2 + 0.3547P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
1877 reflections | Δρmax = 0.40 e Å−3 |
263 parameters | Δρmin = −0.38 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 91 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.05 (14) |
2C8H10NO2+·SO42−·H2O | V = 973.5 (3) Å3 |
Mr = 418.42 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 12.3201 (12) Å | µ = 0.22 mm−1 |
b = 5.9377 (15) Å | T = 293 K |
c = 14.2908 (16) Å | 0.25 × 0.20 × 0.15 mm |
β = 111.369 (10)° |
Enraf-Nonius sealed tube diffractometer | 1778 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et.al.,1968) | Rint = 0.044 |
Tmin = 0.949, Tmax = 0.968 | 3 standard reflections every 60 min |
1968 measured reflections | intensity decay: none |
1877 independent reflections |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.133 | Δρmax = 0.40 e Å−3 |
S = 1.07 | Δρmin = −0.38 e Å−3 |
1877 reflections | Absolute structure: Flack (1983), 91 Friedel pairs |
263 parameters | Absolute structure parameter: −0.05 (14) |
1 restraint |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.81961 (7) | 0.97758 (17) | 0.74803 (6) | 0.0317 (3) | |
O1A | 0.7916 (3) | 0.8243 (8) | 0.6634 (2) | 0.0597 (10) | |
O1B | 0.8547 (3) | 1.1969 (6) | 0.7224 (3) | 0.0544 (9) | |
O1C | 0.9136 (2) | 0.8889 (6) | 0.8370 (2) | 0.0426 (7) | |
O1D | 0.7121 (2) | 1.0069 (5) | 0.77330 (19) | 0.0384 (7) | |
O1 | 0.8619 (3) | 0.2951 (6) | −0.0271 (2) | 0.0485 (8) | |
O2 | 0.6907 (2) | 0.3879 (7) | −0.1440 (2) | 0.0506 (8) | |
H2 | 0.6968 | 0.2634 | −0.1665 | 0.076* | |
C11 | 0.7837 (3) | 0.4299 (8) | −0.0651 (3) | 0.0373 (10) | |
C12 | 0.7852 (3) | 0.6639 (8) | −0.0240 (3) | 0.0352 (9) | |
H12 | 0.7530 | 0.7681 | −0.0806 | 0.042* | |
N11 | 0.9091 (3) | 0.7255 (7) | 0.0319 (3) | 0.0414 (8) | |
H11A | 0.9127 | 0.8634 | 0.0573 | 0.062* | |
H11B | 0.9481 | 0.7222 | −0.0097 | 0.062* | |
H11C | 0.9408 | 0.6277 | 0.0816 | 0.062* | |
C13 | 0.7140 (3) | 0.6849 (8) | 0.0432 (3) | 0.0351 (9) | |
C14 | 0.6449 (4) | 0.8740 (9) | 0.0342 (4) | 0.0524 (11) | |
H14 | 0.6413 | 0.9842 | −0.0131 | 0.063* | |
C15 | 0.5812 (4) | 0.8982 (12) | 0.0960 (5) | 0.0706 (17) | |
H15 | 0.5338 | 1.0237 | 0.0893 | 0.085* | |
C16 | 0.5878 (4) | 0.7371 (13) | 0.1672 (4) | 0.0649 (17) | |
H16 | 0.5460 | 0.7551 | 0.2094 | 0.078* | |
C17 | 0.6557 (4) | 0.5509 (13) | 0.1756 (4) | 0.0649 (16) | |
H17 | 0.6592 | 0.4412 | 0.2231 | 0.078* | |
C18 | 0.7193 (4) | 0.5241 (10) | 0.1142 (3) | 0.0510 (13) | |
H18 | 0.7658 | 0.3972 | 0.1208 | 0.061* | |
OW1 | 0.0318 (3) | 0.5103 (7) | 0.8120 (3) | 0.0501 (8) | |
HW1 | −0.030 (6) | 0.419 (14) | 0.773 (5) | 0.08 (2)* | |
HW2 | −0.005 (6) | 0.612 (17) | 0.829 (5) | 0.09 (3)* | |
O3 | 0.5245 (3) | 0.6447 (6) | 0.4267 (2) | 0.0465 (8) | |
O4 | 0.4780 (2) | 0.3180 (7) | 0.3419 (2) | 0.0491 (8) | |
H4 | 0.4195 | 0.3858 | 0.3064 | 0.074* | |
C21 | 0.5420 (3) | 0.4508 (8) | 0.4145 (3) | 0.0347 (9) | |
C22 | 0.6484 (3) | 0.3243 (7) | 0.4858 (2) | 0.0296 (8) | |
H22 | 0.6266 | 0.1665 | 0.4887 | 0.036* | |
N21 | 0.6792 (2) | 0.4244 (6) | 0.5883 (2) | 0.0345 (8) | |
H21A | 0.6180 | 0.4159 | 0.6071 | 0.052* | |
H21B | 0.6993 | 0.5680 | 0.5869 | 0.052* | |
H21C | 0.7387 | 0.3488 | 0.6317 | 0.052* | |
C23 | 0.7482 (3) | 0.3319 (8) | 0.4479 (3) | 0.0331 (8) | |
C24 | 0.7621 (4) | 0.1522 (9) | 0.3928 (3) | 0.0461 (10) | |
H24 | 0.7136 | 0.0276 | 0.3834 | 0.055* | |
C25 | 0.8476 (4) | 0.1540 (11) | 0.3512 (4) | 0.0580 (13) | |
H25 | 0.8572 | 0.0310 | 0.3147 | 0.070* | |
C26 | 0.9190 (4) | 0.3433 (12) | 0.3648 (3) | 0.0563 (14) | |
H26 | 0.9758 | 0.3477 | 0.3362 | 0.068* | |
C27 | 0.9058 (4) | 0.5224 (11) | 0.4201 (3) | 0.0548 (14) | |
H27 | 0.9546 | 0.6467 | 0.4299 | 0.066* | |
C28 | 0.8195 (3) | 0.5195 (9) | 0.4617 (3) | 0.0439 (11) | |
H28 | 0.8099 | 0.6422 | 0.4984 | 0.053* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0309 (4) | 0.0326 (5) | 0.0258 (4) | 0.0008 (4) | 0.0034 (3) | −0.0018 (4) |
O1A | 0.0614 (19) | 0.072 (2) | 0.0495 (18) | −0.014 (2) | 0.0249 (16) | −0.026 (2) |
O1B | 0.0408 (15) | 0.050 (2) | 0.0562 (18) | −0.0052 (15) | −0.0017 (14) | 0.0155 (17) |
O1C | 0.0360 (13) | 0.0475 (17) | 0.0379 (14) | 0.0128 (14) | 0.0058 (11) | 0.0084 (14) |
O1D | 0.0274 (12) | 0.0449 (18) | 0.0343 (12) | −0.0043 (13) | 0.0010 (10) | −0.0141 (14) |
O1 | 0.0356 (14) | 0.052 (2) | 0.0464 (16) | 0.0065 (14) | 0.0012 (12) | −0.0110 (15) |
O2 | 0.0347 (14) | 0.057 (2) | 0.0454 (16) | 0.0087 (15) | −0.0024 (12) | −0.0173 (16) |
C11 | 0.0282 (17) | 0.054 (3) | 0.0301 (17) | 0.0003 (18) | 0.0110 (14) | −0.0067 (18) |
C12 | 0.0310 (18) | 0.043 (2) | 0.0291 (17) | −0.0008 (18) | 0.0086 (14) | 0.0014 (18) |
N11 | 0.0346 (17) | 0.044 (2) | 0.0471 (18) | −0.0116 (16) | 0.0167 (14) | −0.0114 (18) |
C13 | 0.0288 (17) | 0.041 (2) | 0.0327 (17) | 0.0006 (17) | 0.0082 (14) | −0.0034 (17) |
C14 | 0.048 (2) | 0.043 (3) | 0.068 (3) | 0.013 (2) | 0.024 (2) | 0.007 (3) |
C15 | 0.048 (3) | 0.074 (4) | 0.095 (4) | 0.023 (3) | 0.032 (3) | −0.006 (4) |
C16 | 0.044 (2) | 0.103 (5) | 0.053 (3) | 0.009 (3) | 0.024 (2) | −0.009 (3) |
C17 | 0.062 (3) | 0.090 (5) | 0.049 (2) | 0.018 (3) | 0.028 (2) | 0.017 (3) |
C18 | 0.051 (2) | 0.059 (4) | 0.047 (2) | 0.017 (2) | 0.024 (2) | 0.009 (2) |
OW1 | 0.0441 (16) | 0.052 (2) | 0.0509 (17) | 0.0055 (17) | 0.0132 (14) | 0.0097 (17) |
O3 | 0.0408 (15) | 0.0454 (19) | 0.0465 (16) | 0.0071 (15) | 0.0077 (12) | −0.0034 (15) |
O4 | 0.0352 (14) | 0.056 (2) | 0.0389 (15) | 0.0081 (15) | −0.0067 (12) | −0.0056 (15) |
C21 | 0.0265 (16) | 0.047 (3) | 0.0301 (17) | 0.0017 (18) | 0.0100 (14) | 0.0019 (18) |
C22 | 0.0255 (15) | 0.0303 (19) | 0.0283 (16) | −0.0032 (15) | 0.0042 (13) | −0.0027 (15) |
N21 | 0.0310 (14) | 0.040 (2) | 0.0289 (14) | 0.0008 (13) | 0.0071 (12) | 0.0003 (13) |
C23 | 0.0268 (16) | 0.040 (2) | 0.0265 (16) | 0.0061 (16) | 0.0025 (13) | 0.0036 (16) |
C24 | 0.047 (2) | 0.042 (2) | 0.049 (2) | 0.002 (2) | 0.0172 (19) | −0.004 (2) |
C25 | 0.058 (3) | 0.064 (3) | 0.060 (3) | 0.015 (3) | 0.031 (2) | −0.009 (3) |
C26 | 0.040 (2) | 0.088 (4) | 0.045 (2) | 0.010 (3) | 0.0211 (19) | 0.000 (3) |
C27 | 0.037 (2) | 0.074 (4) | 0.052 (2) | −0.012 (2) | 0.0149 (19) | −0.001 (3) |
C28 | 0.041 (2) | 0.050 (3) | 0.041 (2) | −0.003 (2) | 0.0144 (17) | −0.004 (2) |
S1—O1A | 1.451 (4) | C18—H18 | 0.9300 |
S1—O1B | 1.460 (4) | OW1—HW1 | 0.94 (8) |
S1—O1C | 1.470 (3) | OW1—HW2 | 0.84 (9) |
S1—O1D | 1.505 (3) | O3—C21 | 1.196 (6) |
O1—C11 | 1.218 (5) | O4—C21 | 1.312 (5) |
O2—C11 | 1.305 (5) | O4—H4 | 0.8200 |
O2—H2 | 0.8200 | C21—C22 | 1.533 (5) |
C11—C12 | 1.506 (6) | C22—N21 | 1.495 (5) |
C12—N11 | 1.488 (5) | C22—C23 | 1.514 (5) |
C12—C13 | 1.523 (5) | C22—H22 | 0.9800 |
C12—H12 | 0.9800 | N21—H21A | 0.8900 |
N11—H11A | 0.8900 | N21—H21B | 0.8900 |
N11—H11B | 0.8900 | N21—H21C | 0.8900 |
N11—H11C | 0.8900 | C23—C24 | 1.374 (6) |
C13—C18 | 1.376 (7) | C23—C28 | 1.388 (6) |
C13—C14 | 1.387 (7) | C24—C25 | 1.385 (6) |
C14—C15 | 1.386 (7) | C24—H24 | 0.9300 |
C14—H14 | 0.9300 | C25—C26 | 1.396 (9) |
C15—C16 | 1.377 (9) | C25—H25 | 0.9300 |
C15—H15 | 0.9300 | C26—C27 | 1.369 (8) |
C16—C17 | 1.366 (9) | C26—H26 | 0.9300 |
C16—H16 | 0.9300 | C27—C28 | 1.394 (6) |
C17—C18 | 1.383 (6) | C27—H27 | 0.9300 |
C17—H17 | 0.9300 | C28—H28 | 0.9300 |
O1A—S1—O1B | 110.6 (2) | C13—C18—H18 | 119.9 |
O1A—S1—O1C | 111.6 (2) | C17—C18—H18 | 119.9 |
O1B—S1—O1C | 108.95 (19) | HW1—OW1—HW2 | 100 (6) |
O1A—S1—O1D | 108.06 (17) | C21—O4—H4 | 109.5 |
O1B—S1—O1D | 108.89 (19) | O3—C21—O4 | 127.3 (4) |
O1C—S1—O1D | 108.60 (16) | O3—C21—C22 | 122.0 (4) |
C11—O2—H2 | 109.5 | O4—C21—C22 | 110.7 (4) |
O1—C11—O2 | 124.2 (4) | N21—C22—C23 | 112.9 (3) |
O1—C11—C12 | 122.4 (3) | N21—C22—C21 | 107.9 (3) |
O2—C11—C12 | 113.3 (4) | C23—C22—C21 | 110.9 (3) |
N11—C12—C11 | 107.5 (3) | N21—C22—H22 | 108.3 |
N11—C12—C13 | 110.8 (3) | C23—C22—H22 | 108.3 |
C11—C12—C13 | 113.2 (3) | C21—C22—H22 | 108.3 |
N11—C12—H12 | 108.4 | C22—N21—H21A | 109.5 |
C11—C12—H12 | 108.4 | C22—N21—H21B | 109.5 |
C13—C12—H12 | 108.4 | H21A—N21—H21B | 109.5 |
C12—N11—H11A | 109.5 | C22—N21—H21C | 109.5 |
C12—N11—H11B | 109.5 | H21A—N21—H21C | 109.5 |
H11A—N11—H11B | 109.5 | H21B—N21—H21C | 109.5 |
C12—N11—H11C | 109.5 | C24—C23—C28 | 120.0 (4) |
H11A—N11—H11C | 109.5 | C24—C23—C22 | 118.0 (4) |
H11B—N11—H11C | 109.5 | C28—C23—C22 | 121.9 (4) |
C18—C13—C14 | 119.5 (4) | C23—C24—C25 | 120.9 (5) |
C18—C13—C12 | 121.6 (4) | C23—C24—H24 | 119.6 |
C14—C13—C12 | 118.9 (4) | C25—C24—H24 | 119.6 |
C15—C14—C13 | 119.7 (5) | C24—C25—C26 | 119.0 (5) |
C15—C14—H14 | 120.1 | C24—C25—H25 | 120.5 |
C13—C14—H14 | 120.1 | C26—C25—H25 | 120.5 |
C16—C15—C14 | 120.3 (5) | C27—C26—C25 | 120.3 (4) |
C16—C15—H15 | 119.9 | C27—C26—H26 | 119.9 |
C14—C15—H15 | 119.9 | C25—C26—H26 | 119.9 |
C17—C16—C15 | 119.8 (4) | C26—C27—C28 | 120.4 (5) |
C17—C16—H16 | 120.1 | C26—C27—H27 | 119.8 |
C15—C16—H16 | 120.1 | C28—C27—H27 | 119.8 |
C16—C17—C18 | 120.5 (5) | C23—C28—C27 | 119.4 (4) |
C16—C17—H17 | 119.7 | C23—C28—H28 | 120.3 |
C18—C17—H17 | 119.7 | C27—C28—H28 | 120.3 |
C13—C18—C17 | 120.1 (5) | ||
O1—C11—C12—N11 | 25.0 (5) | O3—C21—C22—N21 | 30.7 (5) |
O2—C11—C12—N11 | −155.6 (3) | O4—C21—C22—N21 | −149.7 (3) |
O1—C11—C12—C13 | −97.7 (5) | O3—C21—C22—C23 | −93.4 (4) |
O2—C11—C12—C13 | 81.8 (4) | O4—C21—C22—C23 | 86.1 (4) |
N11—C12—C13—C18 | −77.3 (5) | N21—C22—C23—C24 | 142.7 (4) |
C11—C12—C13—C18 | 43.6 (5) | C21—C22—C23—C24 | −96.1 (4) |
N11—C12—C13—C14 | 100.9 (5) | N21—C22—C23—C28 | −41.6 (5) |
C11—C12—C13—C14 | −138.3 (4) | C21—C22—C23—C28 | 79.6 (4) |
C18—C13—C14—C15 | −0.6 (7) | C28—C23—C24—C25 | 0.6 (7) |
C12—C13—C14—C15 | −178.8 (5) | C22—C23—C24—C25 | 176.3 (4) |
C13—C14—C15—C16 | 1.0 (9) | C23—C24—C25—C26 | −0.8 (7) |
C14—C15—C16—C17 | −1.2 (9) | C24—C25—C26—C27 | 1.1 (8) |
C15—C16—C17—C18 | 0.9 (9) | C25—C26—C27—C28 | −1.2 (8) |
C14—C13—C18—C17 | 0.3 (7) | C24—C23—C28—C27 | −0.6 (6) |
C12—C13—C18—C17 | 178.4 (5) | C22—C23—C28—C27 | −176.2 (4) |
C16—C17—C18—C13 | −0.5 (8) | C26—C27—C28—C23 | 1.0 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1Di | 0.82 | 1.79 | 2.610 (5) | 174 |
O4—H4···O1Dii | 0.82 | 1.76 | 2.578 (4) | 175 |
N11—H11A···OW1iii | 0.89 | 1.95 | 2.680 (6) | 139 |
N11—H11B···O1iv | 0.89 | 2.25 | 2.877 (6) | 128 |
N11—H11B···O1Cv | 0.89 | 2.30 | 2.969 (5) | 132 |
N11—H11C···O1Cvi | 0.89 | 2.25 | 3.049 (5) | 149 |
N21—H21A···O3ii | 0.89 | 2.30 | 2.951 (5) | 130 |
N21—H21B···O1A | 0.89 | 1.97 | 2.761 (5) | 147 |
N21—H21C···O1Bvii | 0.89 | 1.78 | 2.674 (5) | 178 |
OW1—HW2···O1Cviii | 0.84 (9) | 1.95 (9) | 2.771 (5) | 164 (7) |
OW1—HW1···O1Bix | 0.94 (7) | 1.88 (8) | 2.798 (6) | 167 (7) |
Symmetry codes: (i) x, y−1, z−1; (ii) −x+1, y−1/2, −z+1; (iii) −x+1, y+1/2, −z+1; (iv) −x+2, y+1/2, −z; (v) x, y, z−1; (vi) −x+2, y−1/2, −z+1; (vii) x, y−1, z; (viii) x−1, y, z; (ix) x−1, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | 2C8H10NO2+·SO42−·H2O |
Mr | 418.42 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 293 |
a, b, c (Å) | 12.3201 (12), 5.9377 (15), 14.2908 (16) |
β (°) | 111.369 (10) |
V (Å3) | 973.5 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.25 × 0.20 × 0.15 |
Data collection | |
Diffractometer | Enraf-Nonius sealed tube diffractometer |
Absorption correction | ψ scan (North et.al.,1968) |
Tmin, Tmax | 0.949, 0.968 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1968, 1877, 1778 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.133, 1.07 |
No. of reflections | 1877 |
No. of parameters | 263 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.40, −0.38 |
Absolute structure | Flack (1983), 91 Friedel pairs |
Absolute structure parameter | −0.05 (14) |
Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 1999), SHELXL97.
S1—O1A | 1.451 (4) | O1—C11 | 1.218 (5) |
S1—O1B | 1.460 (4) | O2—C11 | 1.305 (5) |
S1—O1C | 1.470 (3) | O3—C21 | 1.196 (6) |
S1—O1D | 1.505 (3) | O4—C21 | 1.312 (5) |
O1—C11—C12—N11 | 25.0 (5) | O3—C21—C22—N21 | 30.7 (5) |
N11—C12—C13—C18 | −77.3 (5) | N21—C22—C23—C28 | −41.6 (5) |
C11—C12—C13—C18 | 43.6 (5) | C21—C22—C23—C28 | 79.6 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1Di | 0.82 | 1.79 | 2.610 (5) | 174 |
O4—H4···O1Dii | 0.82 | 1.76 | 2.578 (4) | 175 |
N11—H11A···OW1iii | 0.89 | 1.95 | 2.680 (6) | 139 |
N11—H11B···O1iv | 0.89 | 2.25 | 2.877 (6) | 128 |
N11—H11B···O1Cv | 0.89 | 2.30 | 2.969 (5) | 132 |
N11—H11C···O1Cvi | 0.89 | 2.25 | 3.049 (5) | 149 |
N21—H21A···O3ii | 0.89 | 2.30 | 2.951 (5) | 130 |
N21—H21B···O1A | 0.89 | 1.97 | 2.761 (5) | 147 |
N21—H21C···O1Bvii | 0.89 | 1.78 | 2.674 (5) | 178 |
OW1—HW2···O1Cviii | 0.84 (9) | 1.95 (9) | 2.771 (5) | 164 (7) |
OW1—HW1···O1Bix | 0.94 (7) | 1.88 (8) | 2.798 (6) | 167 (7) |
Symmetry codes: (i) x, y−1, z−1; (ii) −x+1, y−1/2, −z+1; (iii) −x+1, y+1/2, −z+1; (iv) −x+2, y+1/2, −z; (v) x, y, z−1; (vi) −x+2, y−1/2, −z+1; (vii) x, y−1, z; (viii) x−1, y, z; (ix) x−1, y−1, z. |
D-Phenylglycine is an important starting material in the production of semisynthetic penicillins and cephalosporins and its derivatives are used in the synthesis of antitumor drugs and other pharmacological applications (Satyam et al., 1996; Jayasinghe et al., 1994). The crystal structure of D-phenylglycine hydrochloride (Ravichandran et al., 1998) has been reported. In the present study, the phenylglycine with sulfuric acid was undertaken.
The asymmetric unit of the title compound, (I), consists of two crystallographically independent protonated phenylglycinium cations, a sulfate anion and a water molecule. In the phenylglycinium molecules, the O1—C11—C12—N11 and O3—C21—C22—N21 torsion angle of 25.0 (5) and 30.7 (5)°, respectively, show that the orientation of the carboxyl group is influenced by the phenyl substitution at the Cα atoms. In α-glycine (Marsh, 1958) and diglycine hydrochloride (Natarajan et al., 1992), the O1—C11—C12—N11 values are 19.1 and 0.3°, and 16.5°, respectively. The aggregation of hydrophillic zone is along (101) and the hydrophobic zone is along (202).
All the O atoms of the sulfate ion are involved in hydrogen bonding. One of the O atoms (O1D), as acceptor, links two crystallographically independent phenylglycinium molecules through strong hydrogen bonds [2.610 (5) and 2.578 (4) Å], resulting in an increased S1—O1D bond distance [1.505 (3) Å]. A bifurcated hydrogen bond is observed in a amino N atom and water molecule with sulfate O atoms (Jeffrey & Saenger, 1991). A zigzag (Z1) head-to-tail sequence is observed, since N11—H11B···O1(-x + 2, y + 1/2, -z) and N21—H21A···O3(-x + 1, y - 1/2, -z + 1) connects two 21-related amino acids (Vijayan, 1988).