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In the title compound, C9H11NO2·C7H6O2, the amino acid mol­ecule exists as a zwitterion and the carboxylic acid mol­ecule is in an unionized state. There is a strong O—H...O inter­molecular hydrogen bond between the phenyl­alanine and benzoic acid mol­ecules, and these mol­ecular pairs form hydrogen-bonded double layers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805031661/at6033sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805031661/at6033Isup2.hkl
Contains datablock I

CCDC reference: 289626

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.071
  • wR factor = 0.187
  • Data-to-parameter ratio = 7.1

checkCIF/PLATON results

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Alert level B PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.97 Deg.
Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.07 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
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 25.00 From the CIF: _reflns_number_total 1364 Count of symmetry unique reflns 1370 Completeness (_total/calc) 99.56% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: XCAD4 (Harms & Wocadlo, 1996); data reduction: XCAD4; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

L-Phenylalanine benzoic acid solvate top
Crystal data top
C9H11NO2·C7H6O2F(000) = 304
Mr = 287.31Dx = 1.331 Mg m3
Dm = 1.32 (2) Mg m3
Dm measured by flotation
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 25 reflections
a = 5.419 (2) Åθ = 9.6–14.1°
b = 7.438 (2) ŵ = 0.10 mm1
c = 17.814 (3) ÅT = 293 K
β = 92.94 (2)°Block, colourless
V = 717.1 (3) Å30.22 × 0.20 × 0.18 mm
Z = 2
Data collection top
Nonius MACH3
diffractometer
925 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
Graphite monochromatorθmax = 25.0°, θmin = 2.3°
ω–2θ scansh = 06
Absorption correction: ψ scan
(North et al., 1968)
k = 18
Tmin = 0.98, Tmax = 0.99l = 2121
1749 measured reflections2 standard reflections every 60 min
1364 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.071Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.187H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.1183P)2]
where P = (Fo2 + 2Fc2)/3
1364 reflections(Δ/σ)max < 0.001
193 parametersΔρmax = 0.50 e Å3
1 restraintΔρmin = 0.36 e Å3
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
O10.6823 (7)0.8790 (7)0.4908 (2)0.0445 (11)
O20.3197 (8)0.8994 (9)0.5437 (2)0.0537 (13)
O30.4874 (8)0.8877 (7)0.6784 (2)0.0473 (12)
H30.42770.88920.63520.071*
O40.1611 (10)0.7170 (8)0.6975 (2)0.0633 (15)
N10.1086 (8)1.0826 (7)0.4278 (3)0.0324 (12)
H1A0.04041.11820.38380.049*
H1B0.15631.17830.45480.049*
H1C0.00131.02010.45250.049*
C10.4567 (10)0.9131 (8)0.4900 (3)0.0337 (13)
C20.3279 (10)0.9668 (8)0.4149 (3)0.0306 (13)
H20.44431.03430.38530.037*
C30.2499 (13)0.7955 (8)0.3718 (3)0.0417 (15)
H3A0.38720.71170.37560.050*
H3B0.11450.74120.39730.050*
C40.1717 (10)0.8143 (7)0.2909 (3)0.0326 (13)
C50.3201 (10)0.9008 (9)0.2408 (3)0.0378 (14)
H50.46660.95410.25890.045*
C60.2560 (12)0.9095 (10)0.1651 (3)0.0451 (16)
H60.35930.96720.13260.054*
C70.0399 (12)0.8330 (9)0.1377 (4)0.0465 (17)
H70.00420.83870.08660.056*
C80.1127 (12)0.7472 (9)0.1862 (4)0.0482 (17)
H80.25860.69350.16790.058*
C90.0476 (12)0.7417 (9)0.2615 (4)0.0426 (15)
H90.15430.68740.29390.051*
C100.3386 (11)0.8041 (9)0.7214 (3)0.0374 (14)
C110.4033 (10)0.8198 (8)0.8028 (3)0.0319 (12)
C120.6119 (10)0.9067 (9)0.8312 (3)0.0394 (14)
H120.71850.96090.79870.047*
C130.6627 (13)0.9134 (11)0.9075 (4)0.0506 (17)
H130.80810.96710.92620.061*
C140.5020 (14)0.8419 (11)0.9563 (3)0.054 (2)
H140.53510.85031.00790.064*
C150.2917 (13)0.7578 (10)0.9282 (3)0.0496 (18)
H150.18170.70860.96100.060*
C160.2435 (12)0.7462 (9)0.8528 (3)0.0436 (16)
H160.10110.68790.83440.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.038 (2)0.032 (3)0.063 (3)0.003 (2)0.0050 (18)0.015 (2)
O20.061 (3)0.061 (3)0.039 (2)0.009 (3)0.0002 (19)0.010 (3)
O30.063 (3)0.042 (3)0.036 (2)0.011 (3)0.003 (2)0.005 (2)
O40.082 (4)0.057 (4)0.049 (3)0.032 (3)0.015 (2)0.001 (3)
N10.040 (3)0.019 (3)0.037 (3)0.004 (2)0.005 (2)0.003 (2)
C10.043 (3)0.018 (3)0.040 (3)0.003 (3)0.002 (2)0.001 (3)
C20.037 (3)0.015 (3)0.040 (3)0.001 (2)0.004 (2)0.003 (2)
C30.065 (4)0.011 (3)0.049 (3)0.003 (3)0.003 (3)0.003 (3)
C40.044 (3)0.015 (3)0.039 (3)0.003 (3)0.004 (2)0.009 (3)
C50.039 (3)0.028 (3)0.046 (3)0.007 (3)0.003 (2)0.005 (3)
C60.060 (4)0.035 (4)0.041 (3)0.006 (4)0.008 (3)0.003 (3)
C70.060 (4)0.030 (4)0.048 (4)0.010 (3)0.012 (3)0.009 (3)
C80.042 (4)0.028 (4)0.074 (5)0.003 (3)0.010 (3)0.012 (4)
C90.052 (4)0.021 (3)0.055 (4)0.003 (3)0.010 (3)0.001 (3)
C100.041 (3)0.026 (3)0.044 (3)0.004 (3)0.001 (3)0.001 (3)
C110.037 (3)0.016 (3)0.042 (3)0.002 (3)0.001 (2)0.000 (3)
C120.046 (3)0.027 (3)0.046 (3)0.007 (3)0.003 (3)0.001 (3)
C130.060 (4)0.041 (4)0.050 (4)0.000 (4)0.009 (3)0.008 (4)
C140.075 (4)0.054 (5)0.031 (3)0.011 (4)0.006 (3)0.003 (3)
C150.061 (4)0.045 (4)0.043 (4)0.002 (4)0.010 (3)0.005 (3)
C160.049 (4)0.027 (4)0.054 (4)0.002 (3)0.002 (3)0.006 (3)
Geometric parameters (Å, º) top
O1—C11.248 (7)C6—C71.369 (9)
O2—C11.245 (7)C6—H60.9300
O3—C101.298 (7)C7—C81.383 (10)
O3—H30.8200C7—H70.9300
O4—C101.218 (7)C8—C91.369 (9)
N1—C21.495 (7)C8—H80.9300
N1—H1A0.8900C9—H90.9300
N1—H1B0.8900C10—C111.479 (8)
N1—H1C0.8900C11—C121.376 (8)
C1—C21.530 (8)C11—C161.386 (8)
C2—C31.535 (8)C12—C131.374 (8)
C2—H20.9800C12—H120.9300
C3—C41.489 (9)C13—C141.369 (10)
C3—H3A0.9700C13—H130.9300
C3—H3B0.9700C14—C151.372 (10)
C4—C91.384 (8)C14—H140.9300
C4—C51.389 (8)C15—C161.358 (9)
C5—C61.377 (8)C15—H150.9300
C5—H50.9300C16—H160.9300
C10—O3—H3109.5C6—C7—C8119.8 (6)
C2—N1—H1A109.5C6—C7—H7120.1
C2—N1—H1B109.5C8—C7—H7120.1
H1A—N1—H1B109.5C9—C8—C7119.6 (6)
C2—N1—H1C109.5C9—C8—H8120.2
H1A—N1—H1C109.5C7—C8—H8120.2
H1B—N1—H1C109.5C8—C9—C4122.1 (6)
O2—C1—O1126.6 (5)C8—C9—H9118.9
O2—C1—C2115.5 (5)C4—C9—H9118.9
O1—C1—C2117.8 (5)O4—C10—O3123.5 (5)
N1—C2—C1110.2 (4)O4—C10—C11121.8 (6)
N1—C2—C3110.7 (5)O3—C10—C11114.7 (5)
C1—C2—C3108.8 (5)C12—C11—C16118.6 (5)
N1—C2—H2109.0C12—C11—C10123.1 (5)
C1—C2—H2109.0C16—C11—C10118.3 (5)
C3—C2—H2109.0C13—C12—C11120.0 (6)
C4—C3—C2117.6 (5)C13—C12—H12120.0
C4—C3—H3A107.9C11—C12—H12120.0
C2—C3—H3A107.9C14—C13—C12120.8 (7)
C4—C3—H3B107.9C14—C13—H13119.6
C2—C3—H3B107.9C12—C13—H13119.6
H3A—C3—H3B107.2C13—C14—C15119.3 (6)
C9—C4—C5116.9 (5)C13—C14—H14120.4
C9—C4—C3121.7 (5)C15—C14—H14120.4
C5—C4—C3121.4 (5)C16—C15—C14120.2 (6)
C6—C5—C4121.7 (6)C16—C15—H15119.9
C6—C5—H5119.1C14—C15—H15119.9
C4—C5—H5119.1C15—C16—C11121.0 (6)
C7—C6—C5119.8 (6)C15—C16—H16119.5
C7—C6—H6120.1C11—C16—H16119.5
C5—C6—H6120.1
O2—C1—C2—N130.5 (7)C5—C4—C9—C82.7 (9)
O1—C1—C2—N1153.1 (5)C3—C4—C9—C8175.2 (6)
O2—C1—C2—C391.2 (7)O4—C10—C11—C12175.4 (7)
O1—C1—C2—C385.3 (6)O3—C10—C11—C123.7 (9)
N1—C2—C3—C471.9 (7)O4—C10—C11—C165.8 (9)
C1—C2—C3—C4166.8 (5)O3—C10—C11—C16175.1 (6)
C2—C3—C4—C9129.4 (6)C16—C11—C12—C132.4 (10)
C2—C3—C4—C552.8 (8)C10—C11—C12—C13178.9 (6)
C9—C4—C5—C61.8 (9)C11—C12—C13—C143.1 (11)
C3—C4—C5—C6176.1 (6)C12—C13—C14—C152.0 (11)
C4—C5—C6—C70.6 (10)C13—C14—C15—C160.2 (11)
C5—C6—C7—C80.1 (10)C14—C15—C16—C110.6 (11)
C6—C7—C8—C90.9 (10)C12—C11—C16—C150.5 (10)
C7—C8—C9—C42.3 (10)C10—C11—C16—C15179.4 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O20.821.712.524 (5)176
N1—H1A···O4i0.891.922.790 (6)167
N1—H1B···O1ii0.891.962.842 (6)170
N1—H1C···O1iii0.892.153.026 (6)168
Symmetry codes: (i) x, y+1/2, z+1; (ii) x+1, y+1/2, z+1; (iii) x1, y, z.
 

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