2-Ammonio-3-phenyl­propanoic acid–mono­hydrogen sulfate–2-ammonio-3-phenyl­propanoate (1/1/1)

Sun, Y.-X.; You, Z.-L.

doi:10.1107/S1600536804018434

2-Ammonio-3-phenylpropanoic acid-monohydrogen sulfate-2-ammonio-3-phenylpropanoate (1/1/1)

The title compound, C₉H₁₂NO₂⁺·HSO₄^-·C₉H₁₁NO₂, consists of a neutral 2-ammonio-3-phenylpropanoate zwitterionic molecule, a 2-ammonio-3-phenylpropanoic acid cation, and a hydrogen sulfate anion. All the O and N atoms in the compound contribute to hydrogen bonds, leading to the formation of sheets parallel to the ab plane.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804018434/su6127sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804018434/su6127Isup2.hkl Contains datablock I

CCDC reference: 248858

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.011 Å
R factor = 0.075
wR factor = 0.163
Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         11
PLAT430_ALERT_2_B Short Inter D...A Contact  O7     ..  O8      ..       2.76 Ang.

Alert level C
CELLV02_ALERT_1_C  The supplied cell volume s.u. differs from that
            calculated from the cell parameter s.u.'s by > 2
            Calculated cell volume su =       6.90
            Cell volume su given      =       4.00
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.39 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.31 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.35 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.23 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1     -   C9      ..       5.71 su
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for        C10

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           26.00
           From the CIF: _reflns_number_total               3478
           Count of symmetry unique reflns         2218
           Completeness (_total/calc)            156.81%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1260
           Fraction of Friedel pairs measured     0.568
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

2-Ammonio-3-phenylpropanoic acid–monohydrogen sulfate–2-ammonio-3-phenylpropanoate (1/1/1) top

Crystal data top

C₉H₁₂NO₂⁺·HSO₄⁻·C₉H₁₁NO₂	F(000) = 452
M_r = 428.45	D_x = 1.412 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 13.439 (3) Å	Cell parameters from 512 reflections
b = 4.878 (3) Å	θ = 2.7–16.4°
c = 15.483 (3) Å	µ = 0.21 mm⁻¹
β = 97.05 (3)°	T = 293 K
V = 1007.4 (4) Å³	Block, colorless
Z = 2	0.27 × 0.20 × 0.18 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3478 independent reflections
Radiation source: fine-focus sealed tube	2086 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.074
ω scans	θ_max = 26.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→16
T_min = 0.946, T_max = 0.963	k = −5→5
5540 measured reflections	l = −17→19

Refinement top

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)] = 0.075	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.163	w = 1/[σ²(F_o²) + (0.0559P)²] where P = (F_o² + 2F_c²)/3
S = 0.95	(Δ/σ)_max < 0.001
3478 reflections	Δρ_max = 0.31 e Å⁻³
268 parameters	Δρ_min = −0.39 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 1260 Friedel pairs [CHECK]
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.15 (19)

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

	x	y	z	U_iso*/U_eq
S1	0.27011 (10)	0.5458 (4)	0.45100 (10)	0.0339 (4)
O1	1.0188 (3)	−0.1526 (9)	0.3637 (3)	0.0312 (11)
H1	1.0762	−0.1875	0.3852	0.047*
O2	1.0394 (3)	0.2232 (10)	0.4475 (3)	0.0461 (13)
O3	0.3978 (2)	1.0705 (10)	0.5850 (3)	0.0373 (11)
O4	0.3241 (3)	0.9620 (11)	0.7018 (3)	0.0450 (14)
O5	0.3753 (2)	0.6202 (9)	0.4369 (2)	0.0320 (11)
O6	0.2655 (3)	0.4295 (10)	0.5452 (2)	0.0331 (11)
O7	0.1957 (2)	0.7826 (10)	0.4402 (2)	0.0329 (11)
O8	0.2327 (3)	0.3076 (10)	0.3856 (2)	0.0371 (12)
C7	0.9085 (4)	0.2769 (15)	0.2492 (4)	0.0345 (16)
H7A	0.8620	0.4251	0.2324	0.041*
H7B	0.9759	0.3474	0.2483	0.041*
N1	0.8619 (3)	0.4276 (11)	0.3908 (3)	0.0327 (13)
H1A	0.8502	0.3747	0.4436	0.049*
H1B	0.8059	0.4954	0.3621	0.049*
H1C	0.9093	0.5561	0.3956	0.049*
C16	0.5368 (4)	0.7803 (15)	0.7527 (4)	0.0388 (17)
H16A	0.5847	0.9083	0.7335	0.047*
H16B	0.4995	0.8773	0.7930	0.047*
N2	0.5165 (3)	0.6421 (11)	0.5962 (3)	0.0299 (13)
H2A	0.4727	0.6453	0.5482	0.045*
H2B	0.5456	0.4782	0.6017	0.045*
H2C	0.5630	0.7702	0.5926	0.045*
C1	0.8908 (4)	0.0509 (16)	0.1836 (3)	0.0360 (15)
C2	0.7954 (5)	−0.0559 (17)	0.1596 (4)	0.053 (2)
H2	0.7419	0.0100	0.1864	0.063*
C3	0.7786 (7)	−0.255 (2)	0.0978 (5)	0.068 (3)
H3	0.7141	−0.3232	0.0833	0.081*
C4	0.8538 (8)	−0.353 (2)	0.0579 (5)	0.081 (3)
H4	0.8413	−0.4889	0.0157	0.097*
C5	0.9503 (8)	−0.2547 (19)	0.0790 (5)	0.076 (3)
H5	1.0028	−0.3246	0.0517	0.092*
C6	0.9679 (5)	−0.0484 (17)	0.1417 (4)	0.052 (2)
H6A	1.0322	0.0222	0.1553	0.062*
C8	0.8961 (4)	0.1874 (13)	0.3424 (3)	0.0240 (14)
H8A	0.8457	0.0417	0.3404	0.029*
C9	0.9921 (4)	0.0884 (16)	0.3916 (4)	0.0315 (17)
C10	0.5940 (4)	0.5522 (17)	0.8014 (4)	0.0368 (15)
C11	0.5590 (7)	0.441 (2)	0.8735 (5)	0.073 (3)
H11	0.4986	0.5006	0.8904	0.088*
C12	0.6164 (8)	0.231 (2)	0.9227 (5)	0.081 (3)
H12	0.5942	0.1529	0.9716	0.097*
C13	0.7030 (8)	0.154 (2)	0.8954 (6)	0.092 (4)
H13	0.7409	0.0205	0.9274	0.110*
C14	0.7387 (6)	0.258 (2)	0.8240 (6)	0.074 (3)
H14	0.7976	0.1927	0.8054	0.089*
C15	0.6835 (5)	0.4642 (17)	0.7801 (5)	0.056 (2)
H15	0.7090	0.5475	0.7335	0.067*
C17	0.4634 (4)	0.6968 (14)	0.6734 (3)	0.0282 (15)
H17	0.4275	0.5309	0.6874	0.034*
C18	0.3876 (4)	0.9292 (15)	0.6518 (4)	0.0312 (16)
H6	0.308 (4)	0.306 (12)	0.556 (4)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0259 (7)	0.0337 (11)	0.0422 (9)	0.0037 (9)	0.0047 (6)	−0.0011 (9)
O1	0.023 (2)	0.025 (3)	0.043 (3)	0.007 (2)	−0.0055 (18)	−0.007 (2)
O2	0.034 (2)	0.029 (3)	0.070 (3)	−0.004 (2)	−0.013 (2)	−0.005 (3)
O3	0.032 (2)	0.027 (3)	0.053 (3)	0.010 (2)	0.0064 (19)	0.004 (3)
O4	0.027 (2)	0.066 (4)	0.042 (3)	0.007 (2)	0.0041 (18)	−0.007 (3)
O5	0.0196 (19)	0.030 (3)	0.048 (2)	0.003 (2)	0.0103 (17)	0.000 (2)
O6	0.032 (2)	0.040 (3)	0.029 (2)	0.014 (2)	0.0068 (18)	0.007 (2)
O7	0.020 (2)	0.029 (3)	0.050 (3)	0.014 (2)	0.0036 (18)	0.000 (2)
O8	0.042 (2)	0.033 (3)	0.036 (2)	−0.010 (2)	0.0034 (19)	−0.008 (2)
C7	0.041 (3)	0.027 (4)	0.038 (4)	0.005 (3)	0.012 (3)	0.009 (3)
N1	0.026 (3)	0.031 (4)	0.041 (3)	0.000 (3)	0.001 (2)	0.000 (3)
C16	0.043 (4)	0.026 (5)	0.044 (4)	0.008 (4)	−0.007 (3)	−0.010 (3)
N2	0.021 (2)	0.025 (4)	0.043 (3)	0.003 (2)	0.001 (2)	0.000 (2)
C1	0.055 (4)	0.028 (4)	0.024 (3)	0.005 (4)	0.005 (3)	0.007 (3)
C2	0.062 (5)	0.043 (6)	0.049 (4)	0.010 (4)	−0.008 (3)	−0.003 (4)
C3	0.088 (6)	0.050 (7)	0.056 (5)	−0.007 (6)	−0.026 (5)	0.012 (5)
C4	0.144 (9)	0.055 (7)	0.038 (5)	−0.004 (7)	−0.011 (6)	0.002 (4)
C5	0.147 (9)	0.040 (6)	0.053 (5)	0.016 (6)	0.056 (6)	0.004 (5)
C6	0.075 (5)	0.042 (6)	0.042 (4)	0.007 (4)	0.021 (4)	0.006 (4)
C8	0.022 (3)	0.016 (4)	0.033 (3)	−0.002 (3)	0.001 (2)	−0.004 (3)
C9	0.021 (3)	0.036 (5)	0.038 (4)	−0.007 (3)	0.006 (3)	0.015 (4)
C10	0.044 (3)	0.028 (4)	0.037 (3)	0.000 (4)	−0.004 (3)	−0.001 (4)
C11	0.107 (6)	0.064 (7)	0.048 (5)	−0.007 (6)	0.006 (4)	0.000 (5)
C12	0.145 (9)	0.055 (8)	0.039 (5)	−0.018 (7)	−0.002 (6)	0.009 (5)
C13	0.136 (9)	0.057 (8)	0.065 (7)	0.006 (7)	−0.058 (6)	0.004 (6)
C14	0.061 (5)	0.052 (7)	0.100 (7)	0.006 (5)	−0.025 (5)	−0.002 (6)
C15	0.051 (4)	0.043 (6)	0.070 (5)	−0.001 (4)	−0.011 (4)	0.009 (4)
C17	0.027 (3)	0.023 (4)	0.033 (3)	0.000 (3)	0.002 (3)	0.005 (3)
C18	0.025 (3)	0.026 (4)	0.041 (4)	−0.002 (3)	−0.006 (3)	−0.008 (3)

Geometric parameters (Å, º) top

S1—O5	1.501 (3)	C1—C6	1.377 (8)
S1—O7	1.523 (4)	C1—C2	1.391 (9)
S1—O6	1.574 (4)	C2—C3	1.363 (11)
S1—O8	1.582 (4)	C2—H2	0.9300
O1—C9	1.317 (8)	C3—C4	1.337 (10)
O1—H1	0.8200	C3—H3	0.9300
O2—C9	1.205 (7)	C4—C5	1.384 (12)
O3—C18	1.264 (7)	C4—H4	0.9300
O4—C18	1.231 (6)	C5—C6	1.399 (11)
O6—H6	0.83 (6)	C5—H5	0.9300
C7—C1	1.498 (9)	C6—H6A	0.9300
C7—C8	1.536 (7)	C8—C9	1.495 (7)
C7—H7A	0.9700	C8—H8A	0.9800
C7—H7B	0.9700	C10—C15	1.355 (8)
N1—C8	1.493 (7)	C10—C11	1.375 (9)
N1—H1A	0.8900	C11—C12	1.441 (12)
N1—H1B	0.8900	C11—H11	0.9300
N1—H1C	0.8900	C12—C13	1.341 (12)
C16—C10	1.501 (9)	C12—H12	0.9300
C16—C17	1.533 (7)	C13—C14	1.357 (11)
C16—H16A	0.9700	C13—H13	0.9300
C16—H16B	0.9700	C14—C15	1.380 (11)
N2—C17	1.489 (6)	C14—H14	0.9300
N2—H2A	0.8900	C15—H15	0.9300
N2—H2B	0.8900	C17—C18	1.533 (9)
N2—H2C	0.8900	C17—H17	0.9800

O5—S1—O7	114.7 (2)	C5—C4—H4	119.8
O5—S1—O6	111.5 (2)	C4—C5—C6	119.2 (8)
O7—S1—O6	105.9 (2)	C4—C5—H5	120.4
O5—S1—O8	108.4 (2)	C6—C5—H5	120.4
O7—S1—O8	109.5 (2)	C1—C6—C5	120.5 (8)
O6—S1—O8	106.4 (3)	C1—C6—H6A	119.8
C9—O1—H1	109.5	C5—C6—H6A	119.8
S1—O6—H6	110 (5)	N1—C8—C9	107.3 (5)
C1—C7—C8	113.6 (6)	N1—C8—C7	108.9 (5)
C1—C7—H7A	108.8	C9—C8—C7	112.6 (4)
C8—C7—H7A	108.8	N1—C8—H8A	109.4
C1—C7—H7B	108.8	C9—C8—H8A	109.4
C8—C7—H7B	108.8	C7—C8—H8A	109.4
H7A—C7—H7B	107.7	O2—C9—O1	125.5 (6)
C8—N1—H1A	109.5	O2—C9—C8	122.4 (7)
C8—N1—H1B	109.5	O1—C9—C8	112.0 (6)
H1A—N1—H1B	109.5	C15—C10—C11	118.3 (7)
C8—N1—H1C	109.5	C15—C10—C16	121.9 (6)
H1A—N1—H1C	109.5	C11—C10—C16	119.7 (7)
H1B—N1—H1C	109.5	C10—C11—C12	119.7 (8)
C10—C16—C17	116.4 (6)	C10—C11—H11	120.1
C10—C16—H16A	108.2	C12—C11—H11	120.1
C17—C16—H16A	108.2	C13—C12—C11	117.6 (8)
C10—C16—H16B	108.2	C13—C12—H12	121.2
C17—C16—H16B	108.2	C11—C12—H12	121.2
H16A—C16—H16B	107.3	C12—C13—C14	124.0 (9)
C17—N2—H2A	109.5	C12—C13—H13	118.0
C17—N2—H2B	109.5	C14—C13—H13	118.0
H2A—N2—H2B	109.5	C13—C14—C15	116.8 (9)
C17—N2—H2C	109.5	C13—C14—H14	121.6
H2A—N2—H2C	109.5	C15—C14—H14	121.6
H2B—N2—H2C	109.5	C10—C15—C14	123.5 (8)
C6—C1—C2	117.7 (7)	C10—C15—H15	118.2
C6—C1—C7	120.8 (6)	C14—C15—H15	118.2
C2—C1—C7	121.5 (6)	N2—C17—C16	111.5 (4)
C3—C2—C1	121.5 (7)	N2—C17—C18	109.2 (5)
C3—C2—H2	119.2	C16—C17—C18	108.9 (5)
C1—C2—H2	119.2	N2—C17—H17	109.1
C4—C3—C2	120.7 (8)	C16—C17—H17	109.1
C4—C3—H3	119.6	C18—C17—H17	109.1
C2—C3—H3	119.6	O4—C18—O3	126.7 (6)
C3—C4—C5	120.4 (9)	O4—C18—C17	116.9 (6)
C3—C4—H4	119.8	O3—C18—C17	116.4 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O3ⁱ	0.83 (6)	1.69 (6)	2.519 (5)	176 (8)
N2—H2C···O5ⁱⁱ	0.89	1.98	2.828 (6)	160
N2—H2B···O5ⁱⁱⁱ	0.89	2.17	3.007 (6)	157
N2—H2A···O5	0.89	2.04	2.923 (6)	175
N1—H1C···O2^iv	0.89	2.57	3.047 (6)	114
N1—H1C···O1^v	0.89	2.15	3.005 (6)	162
N1—H1B···O4ⁱⁱⁱ	0.89	1.91	2.730 (6)	153
N1—H1A···O7ⁱⁱⁱ	0.89	2.02	2.905 (6)	172
O1—H1···O7^vi	0.82	1.73	2.543 (5)	171

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

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2-Ammonio-3-phenyl­propanoic acid-mono­hydrogen sulfate-2-ammonio-3-phenyl­propanoate (1/1/1)

Supporting information

Key indicators

checkCIF/PLATON results

2-Ammonio-3-phenylpropanoic acid-monohydrogen sulfate-2-ammonio-3-phenylpropanoate (1/1/1)