1-(p-Anisyl)-2-carboxy­ethanaminium p-toluene­sulfonate

The cation and anion in the title compound, C₁₀H₁₄NO₃⁺·C₇H₇O₃S⁻, (I), are linked by a short carboxyl­ic acid–sulfonate O...O hydrogen bond. Adjacent ion pairs are linked by hydrogen bonds involving the ammonium unit, giving rise to tightly held chains that run along the b axis of the monoclinic unit cell.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.058
• wR factor = 0.166
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.505     0.954
            Tmin' and Tmax expected:      0.937     0.958
            RR' =      0.542
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.54

Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.05 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.37 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.00 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.07 Ratio
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         S1
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C4
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Rat
              O5   -H5O     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.86(4), Rep   0.860(10) ......       4.00 su-Rat
              N1   -H1N     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Rat
              N1   -H2N     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Rat
              O5   -H5O     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Rat
              N1   -H2N     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(4), Rep   0.860(10) ......       4.00 su-Rat
              N1   -H1N     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.81(3), Rep   1.810(10) ......       3.00 su-Rat
              H5O  -O1      1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.91(3), Rep   1.900(10) ......       3.00 su-Rat
              H2N  -O2      1.555   3.656
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C10 H14 N O3

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

   9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4-PC (Kretschmar, 1994); cell refinement: CAD-4 VAX/PC Fortran System (Enraf-Nonius, 1988); data reduction: XCAD4 (Harms, 1997) in WinGX (Farrugia, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

1-(p-Anisyl)-2-carboxyethanaminium p-toluenesulfonate

Crystal data

C10H14NO3^+·C7H7O3S^−	F(000) = 776
Mr = 367.41	Dx = 1.354 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.095 (2) Å	θ = 8.3–11.3°
b = 6.448 (2) Å	µ = 0.21 mm^−1
c = 34.733 (3) Å	T = 298 K
β = 96.43 (2)°	Block, colorless
V = 1801.7 (6) Å^3	0.3 × 0.3 × 0.2 mm
Z = 4

Data collection

Enraf-Nonius CAD-4 diffractometer	2139 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Graphite monochromator	θmax = 25.0°, θmin = 1.2°
ω–2θ scans	h = −9→0
Absorption correction: empirical (using intensity measurements) via ψ scan (North et al., 1968)	k = −7→0
Tmin = 0.505, Tmax = 0.954	l = −41→41
3417 measured reflections	3 standard reflections every 60 min
3174 independent reflections	intensity decay: 1%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.166	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0861P)^2 + 0.6702P] where P = (Fo^2 + 2Fc^2)/3
3174 reflections	(Δ/σ)max = 0.001
244 parameters	Δρmax = 0.39 e Å^−3
4 restraints	Δρmin = −0.46 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.4027 (1)	0.6467 (1)	0.56572 (2)	0.0369 (3)
O1	0.2313 (3)	0.6055 (4)	0.5512 (1)	0.057 (1)
O2	0.5012 (4)	0.4649 (5)	0.5752 (1)	0.078 (1)
O3	0.4774 (3)	0.7855 (4)	0.5399 (1)	0.051 (1)
O4	0.1919 (4)	0.1081 (4)	0.5126 (1)	0.058 (1)
O5	0.1568 (3)	0.4138 (4)	0.4839 (1)	0.047 (1)
O6	0.0875 (4)	−0.4830 (5)	0.2940 (1)	0.076 (1)
N1	0.3390 (4)	−0.1556 (5)	0.4599 (1)	0.040 (1)
C1	0.3960 (4)	0.7801 (6)	0.6096 (1)	0.036 (1)
C2	0.3236 (5)	0.9740 (6)	0.6092 (1)	0.050 (1)
C3	0.3189 (6)	1.0797 (7)	0.6435 (1)	0.067 (1)
C4	0.3841 (6)	0.9951 (9)	0.6784 (1)	0.069 (1)
C5	0.4594 (7)	0.8041 (9)	0.6779 (1)	0.076 (2)
C6	0.4655 (5)	0.6961 (7)	0.6440 (1)	0.055 (1)
C7	0.3772 (9)	1.113 (1)	0.7160 (1)	0.123 (3)
C8	0.1639 (4)	0.2082 (6)	0.4836 (1)	0.036 (1)
C9	0.1325 (4)	0.1211 (5)	0.4438 (1)	0.037 (1)
C10	0.1643 (4)	−0.1111 (5)	0.4422 (1)	0.035 (1)
C12	0.1378 (4)	−0.2034 (5)	0.4022 (1)	0.035 (1)
C13	0.2127 (5)	−0.1250 (6)	0.3713 (1)	0.052 (1)
C14	0.1923 (5)	−0.2217 (7)	0.3358 (1)	0.057 (1)
C15	0.0964 (5)	−0.3989 (6)	0.3302 (1)	0.047 (1)
C16	0.0211 (5)	−0.4775 (6)	0.3605 (1)	0.050 (1)
C17	0.0426 (4)	−0.3797 (6)	0.3961 (1)	0.043 (1)
C18	−0.0057 (9)	−0.6675 (9)	0.2869 (1)	0.106 (2)
H5o	0.179 (6)	0.460 (7)	0.5068 (6)	0.08 (2)*
H1n	0.404 (5)	−0.061 (5)	0.453 (1)	0.07 (2)*
H2n	0.376 (5)	−0.264 (4)	0.450 (1)	0.06 (1)*
H3n	0.343 (4)	−0.169 (5)	0.4845 (3)	0.04 (1)*
H2	0.2783	1.0328	0.5859	0.060*
H3	0.2707	1.2107	0.6431	0.080*
H5	0.5073	0.7468	0.7010	0.091*
H6	0.5164	0.5668	0.6444	0.066*
H7a	0.2882	1.0590	0.7292	0.184*
H7b	0.3584	1.2571	0.7105	0.184*
H7c	0.4806	1.0959	0.7321	0.184*
H9a	0.2034	0.1915	0.4272	0.044*
H9b	0.0180	0.1485	0.4337	0.044*
H10	0.0880	−0.1801	0.4580	0.042*
H13	0.2774	−0.0057	0.3746	0.062*
H14	0.2435	−0.1674	0.3154	0.069*
H16	−0.0442	−0.5962	0.3571	0.060*
H17	−0.0086	−0.4344	0.4165	0.051*
H18a	0.0470	−0.7780	0.3023	0.160*
H18b	−0.0111	−0.7028	0.2600	0.160*
H18c	−0.1161	−0.6468	0.2938	0.160*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0395 (5)	0.0330 (5)	0.0388 (4)	0.0041 (4)	0.0074 (3)	−0.0040 (4)
O1	0.044 (2)	0.064 (2)	0.063 (2)	−0.016 (1)	0.012 (1)	−0.028 (1)
O2	0.115 (3)	0.055 (2)	0.066 (2)	0.052 (2)	0.014 (2)	0.001 (2)
O3	0.053 (2)	0.060 (2)	0.041 (1)	−0.011 (1)	0.012 (1)	−0.001 (1)
O4	0.100 (2)	0.034 (2)	0.040 (1)	0.006 (2)	0.009 (1)	0.000 (1)
O5	0.063 (2)	0.031 (2)	0.047 (1)	0.009 (1)	0.002 (1)	−0.008 (1)
O6	0.121 (3)	0.063 (2)	0.043 (2)	−0.014 (2)	0.002 (2)	−0.015 (1)
N1	0.051 (2)	0.032 (2)	0.035 (2)	0.009 (2)	−0.001 (1)	−0.002 (2)
C1	0.035 (2)	0.035 (2)	0.040 (2)	0.001 (2)	0.006 (1)	−0.001 (2)
C2	0.052 (2)	0.050 (3)	0.045 (2)	0.015 (2)	−0.003 (2)	−0.009 (2)
C3	0.073 (3)	0.060 (3)	0.065 (3)	0.016 (2)	0.003 (2)	−0.026 (2)
C4	0.087 (4)	0.075 (4)	0.045 (2)	−0.007 (3)	0.012 (2)	−0.021 (2)
C5	0.106 (4)	0.083 (4)	0.036 (2)	−0.004 (3)	−0.004 (2)	0.008 (2)
C6	0.077 (3)	0.044 (3)	0.043 (2)	0.003 (2)	−0.002 (2)	0.006 (2)
C7	0.183 (7)	0.128 (6)	0.060 (3)	−0.006 (5)	0.024 (4)	−0.043 (3)
C8	0.036 (2)	0.034 (2)	0.041 (2)	0.005 (2)	0.007 (1)	−0.003 (2)
C9	0.039 (2)	0.029 (2)	0.042 (2)	0.005 (2)	0.002 (1)	0.000 (1)
C10	0.038 (2)	0.029 (2)	0.039 (2)	−0.002 (2)	0.005 (1)	−0.002 (1)
C12	0.034 (2)	0.030 (2)	0.040 (2)	0.001 (2)	0.003 (1)	−0.001 (1)
C13	0.061 (3)	0.046 (3)	0.048 (2)	−0.020 (2)	0.011 (2)	−0.006 (2)
C14	0.075 (3)	0.058 (3)	0.040 (2)	−0.014 (2)	0.015 (2)	−0.003 (2)
C15	0.064 (3)	0.039 (2)	0.037 (2)	0.003 (2)	−0.002 (2)	−0.007 (2)
C16	0.063 (3)	0.037 (2)	0.048 (2)	−0.011 (2)	−0.006 (2)	−0.007 (2)
C17	0.051 (2)	0.032 (2)	0.045 (2)	−0.0046 (17)	0.00592)	0.004 (2)
C18	0.172 (6)	0.074 (4)	0.070 (3)	−0.040 (4)	0.002 (3)	−0.038 (3)

Geometric parameters (Å, º)

S1—O2	1.435 (3)	C15—C16	1.370 (5)
S1—O1	1.447 (3)	C16—C17	1.383 (5)
S1—O3	1.447 (3)	O5—H5o	0.85 (1)
S1—C1	1.756 (3)	N1—H1n	0.86 (1)
O4—C8	1.196 (4)	N1—H2n	0.85 (1)
O5—C8	1.327 (4)	N1—H3n	0.86 (1)
O6—C15	1.366 (4)	C2—H2	0.9300
O6—C18	1.415 (6)	C3—H3	0.9300
N1—C10	1.505 (4)	C5—H5	0.9300
C1—C6	1.374 (5)	C6—H6	0.9300
C1—C2	1.381 (5)	C7—H7a	0.9600
C2—C3	1.378 (5)	C7—H7b	0.9600
C3—C4	1.378 (6)	C7—H7c	0.9600
C4—C5	1.375 (7)	C9—H9a	0.9700
C4—C7	1.518 (6)	C9—H9b	0.9700
C5—C6	1.373 (6)	C10—H10	0.9800
C8—C9	1.489 (4)	C13—H13	0.9300
C9—C10	1.522 (5)	C14—H14	0.9300
C10—C12	1.503 (4)	C16—H16	0.9300
C12—C17	1.376 (5)	C17—H17	0.9300
C12—C13	1.387 (5)	C18—H18a	0.9600
C13—C14	1.374 (5)	C18—H18b	0.9600
C14—C15	1.383 (6)	C18—H18c	0.9600
O1—S1—O2	114.7 (2)	H1n—N1—H3n	113 (4)
O1—S1—O3	110.4 (2)	H2n—N1—H3n	111 (4)
O2—S1—O3	112.8 (2)	C3—C2—H2	120.3
O1—S1—C1	105.8 (2)	C1—C2—H2	120.3
O2—S1—C1	105.7 (2)	C2—C3—H3	119.3
O3—S1—C1	106.9 (2)	C4—C3—H3	119.3
C15—O6—C18	117.7 (4)	C6—C5—H5	119.2
C2—C1—C6	119.9 (3)	C4—C5—H5	119.2
C6—C1—S1	120.8 (3)	C5—C6—H6	120.2
C2—C1—S1	119.3 (3)	C1—C6—H6	120.2
C1—C2—C3	119.4 (4)	C4—C7—H7a	109.5
C2—C3—C4	121.3 (4)	C4—C7—H7b	109.5
C3—C4—C5	118.1 (4)	H7a—C7—H7b	109.5
C3—C4—C7	120.8 (5)	C4—C7—H7c	109.5
C5—C4—C7	121.1 (5)	H7a—C7—H7c	109.5
C4—C5—C6	121.6 (4)	H7b—C7—H7c	109.5
C1—C6—C5	119.7 (4)	C8—C9—H9a	109.0
O4—C8—O5	122.5 (3)	C10—C9—H9a	109.0
O4—C8—C9	125.1 (3)	C8—C9—H9b	109.0
O5—C8—C9	112.4 (3)	C10—C9—H9b	109.0
C8—C9—C10	113.1 (3)	H9a—C9—H9b	107.8
C12—C10—N1	109.4 (3)	C12—C10—H10	107.8
C12—C10—C9	114.6 (3)	N1—C10—H10	107.8
N1—C10—C9	109.1 (3)	C9—C10—H10	107.8
C10—C12—C13	122.8 (3)	C14—C13—H13	119.7
C10—C12—C17	119.3 (3)	C12—C13—H13	119.7
C13—C12—C17	117.9 (3)	C13—C14—H14	119.6
C12—C13—C14	120.6 (4)	C15—C14—H14	119.6
C13—C14—C15	120.7 (3)	C15—C16—H16	120.2
O6—C15—C16	125.4 (4)	C17—C16—H16	120.2
O6—C15—C14	115.4 (3)	C12—C17—H17	119.1
C14—C15—C16	119.2 (3)	C16—C17—H17	119.1
C15—C16—C17	119.7 (4)	O6—C18—H18a	109.5
C12—C17—C16	121.8 (3)	O6—C18—H18b	109.5
C8—O5—H5o	110 (3)	H18a—C18—H18b	109.5
C10—N1—H1n	109 (3)	O6—C18—H18c	109.5
C10—N1—H2n	110 (3)	H18a—C18—H18c	109.5
H1n—N1—H2n	102 (4)	H18b—C18—H18c	109.5
C10—N1—H3n	111 (2)
O2—S1—C1—C6	−5.0 (4)	C8—C9—C10—C12	−178.6 (3)
O1—S1—C1—C6	117.0 (3)	C8—C9—C10—N1	−55.5 (4)
O3—S1—C1—C6	−125.4 (3)	N1—C10—C12—C17	106.1 (4)
O2—S1—C1—C2	173.4 (3)	C9—C10—C12—C17	−131.1 (3)
O1—S1—C1—C2	−64.6 (3)	N1—C10—C12—C13	−70.4 (4)
O3—S1—C1—C2	53.0 (3)	C9—C10—C12—C13	52.5 (5)
C6—C1—C2—C3	−1.3 (6)	C17—C12—C13—C14	−0.2 (6)
S1—C1—C2—C3	−179.7 (3)	C10—C12—C13—C14	176.3 (4)
C1—C2—C3—C4	−0.5 (7)	C12—C13—C14—C15	0.1 (7)
C2—C3—C4—C5	2.1 (7)	C18—O6—C15—C16	−0.6 (7)
C2—C3—C4—C7	−179.6 (5)	C18—O6—C15—C14	178.5 (5)
C3—C4—C5—C6	−2.1 (8)	C13—C14—C15—O6	−178.9 (4)
C7—C4—C5—C6	179.7 (5)	C13—C14—C15—C16	0.2 (6)
C4—C5—C6—C1	0.4 (7)	O6—C15—C16—C17	178.7 (4)
C2—C1—C6—C5	1.3 (6)	C14—C15—C16—C17	−0.3 (6)
S1—C1—C6—C5	179.7 (3)	C13—C12—C17—C16	0.0 (5)
O4—C8—C9—C10	−8.6 (5)	C10—C12—C17—C16	−176.6 (3)
O5—C8—C9—C10	171.8 (3)	C15—C16—C17—C12	0.3 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5o···O1	0.85 (1)	1.81 (1)	2.653 (3)	169 (5)
N1—H2n···O2^i	0.85 (1)	1.90 (1)	2.736 (4)	167 (4)
N1—H1n···O3^ii	0.86 (1)	2.02 (2)	2.811 (5)	152 (4)
N1—H3n···O3^iii	0.86 (1)	2.12 (2)	2.903 (4)	152 (3)

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