Crystal structure of a new mol­ecular salt: 4-amino­benzenaminium 5-carb­oxy­penta­noate

The asymmetric unit of the title mol­ecular salt, consists of half a 4-amino­benzenaminium cation and a half a 5-carb­oxy­penta­noate anion. Each ion lies about an inversion centre, the other half being generated by inversion symmetry. In the crystal, charge-assisted O—H...O, N—H...O and N—H...N hydrogen bonds together lead to the formation of a three-dimensional supra­molecular framework.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.001 Å
• R factor = 0.034
• wR factor = 0.092
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level B
PLAT920_ALERT_1_B Theta(Max)  in CIF and FCF Differ by ...........       2.78 Degree
PLAT922_ALERT_1_B wR2 in the CIF and FCF Differ by ...............    -0.0063 Check
PLAT927_ALERT_1_B Reported and Calculated  wR2 Differ by .........    -0.0105 Check
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          2 Check

Alert level C
PLAT222_ALERT_3_C Non-Solv.  Resd 1  H   Uiso(max)/Uiso(min) Range        5.3 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for   N1       --C1        .        6.7 s.u.
PLAT303_ALERT_2_C Full Occupancy Atom H2O       with # Connections       2.00 Check
PLAT751_ALERT_4_C Bond    Calc     1.22000, Rep   1.2197(6) ......  Senseless s.u.
              O2       -H2O             1.555   1.555 ........     #    3 Check
PLAT752_ALERT_4_C Angle   Calc      113.00, Rep   113.50(6) ......  Senseless s.u.
              C6      -O2      -H2O        1.555  1.555  1.555     #    1 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          8 Note
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          1 Check
PLAT921_ALERT_1_C R1  in the CIF and FCF Differ by ...............     0.0017 Check
PLAT923_ALERT_1_C S    Values in the CIF and FCF Differ by .......     -0.110 Check
PLAT928_ALERT_1_C Reported and Calculated    S value   Differ by .     -0.161 Check
PLAT939_ALERT_3_C Large Value of Not (SHELXL) Weight Optimized S .      12.23 Check

Alert level G
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension          1 Info
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT013_ALERT_1_G N.O.K.   _shelx_hkl_checksum Found in CIF ......     Please Check
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT300_ALERT_4_G Atom Site Occupancy of H1NC       Constrained at        0.5 Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          3 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          2 Note
PLAT953_ALERT_1_G Reported (CIF) and Actual (FCF) Hmax Differ by .          1 Units
PLAT954_ALERT_1_G Reported (CIF) and Actual (FCF) Kmax Differ by .          1 Units
PLAT955_ALERT_1_G Reported (CIF) and Actual (FCF) Lmax Differ by .          1 Units
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          5 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   4 ALERT level B = A potentially serious problem, consider carefully
  11 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  11 ALERT level G = General information/check it is not something unexpected

  11 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
   4 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

---

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2016/6 (Sheldrick, 2015), OLEX2 (Dolomanov et al., 2009), PLATON (Spek, 2009) and publCIF (Westrip (2010).

4-Aminoanilinium 5-carboxypentanoate

Crystal data

C6H9N2^+·C6H9O4^−	Z = 1
Mr = 254.28	F(000) = 136
Triclinic, P1	Dx = 1.378 Mg m^−3
a = 5.2918 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.1666 (4) Å	Cell parameters from 5347 reflections
c = 8.4205 (7) Å	θ = 5.2–29.2°
α = 92.069 (6)°	µ = 0.10 mm^−1
β = 104.165 (6)°	T = 100 K
γ = 97.172 (5)°	Block, purple
V = 306.47 (4) Å^3	0.42 × 0.38 × 0.32 mm

Data collection

Rigaku Oxford Diffraction XtaLAB Pro: Kappa dual offset/far diffractometer	1416 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	1341 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
ω scans	θmax = 29.1°, θmin = 5.0°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −5→7
Tmin = 0.924, Tmax = 1.000	k = −9→8
3776 measured reflections	l = −11→10

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.092	w = 1/[σ^2(Fo^2) + (0.0483P)^2 + 0.0998P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
1416 reflections	Δρmax = 0.39 e Å^−3
96 parameters	Δρmin = −0.22 e Å^−3
0 restraints	Extinction correction: (SHELXL-2016/6; Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.15 (2)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.88613 (16)	0.51078 (11)	0.73311 (10)	0.0284 (2)
O2	0.62365 (13)	0.36690 (9)	0.50333 (8)	0.0159 (2)
H2O	0.500000	0.500000	0.500000	0.079 (10)*
C4	0.90322 (17)	0.07097 (12)	0.49487 (11)	0.0140 (2)
H4A	0.867169	0.119848	0.384244	0.017*
H4B	0.735161	0.007357	0.511087	0.017*
C5	1.01023 (17)	0.23441 (12)	0.62353 (11)	0.0127 (2)
H5A	1.048177	0.183438	0.733310	0.015*
H5B	1.178973	0.295883	0.606644	0.015*
C6	0.82994 (17)	0.38253 (12)	0.62270 (11)	0.0122 (2)
N1	0.43897 (17)	0.62290 (12)	0.87167 (10)	0.0177 (2)
H1NA	0.268 (3)	0.582 (2)	0.8186 (19)	0.033 (4)*
H1NB	0.538 (3)	0.608 (2)	0.800 (2)	0.036 (4)*
H1NC	0.470 (5)	0.534 (3)	0.953 (3)	0.013 (6)*	0.5
C1	0.47080 (18)	0.81542 (13)	0.93517 (11)	0.0147 (2)
C2	0.65701 (19)	0.95024 (15)	0.89941 (12)	0.0180 (2)
H2	0.764255	0.916272	0.830590	0.022*
C3	0.68658 (19)	1.13477 (14)	0.96421 (12)	0.0179 (2)
H3	0.814280	1.227114	0.939883	0.021*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0309 (4)	0.0199 (4)	0.0270 (4)	0.0138 (3)	−0.0099 (3)	−0.0120 (3)
O2	0.0149 (4)	0.0149 (3)	0.0169 (4)	0.0069 (3)	0.0000 (3)	−0.0023 (3)
C4	0.0124 (4)	0.0124 (4)	0.0173 (5)	0.0051 (3)	0.0023 (3)	−0.0011 (3)
C5	0.0108 (4)	0.0119 (4)	0.0154 (4)	0.0034 (3)	0.0027 (3)	0.0006 (3)
C6	0.0131 (4)	0.0101 (4)	0.0144 (4)	0.0023 (3)	0.0049 (3)	0.0015 (3)
N1	0.0164 (4)	0.0225 (4)	0.0144 (4)	0.0030 (3)	0.0040 (3)	0.0012 (3)
C1	0.0137 (4)	0.0187 (5)	0.0107 (4)	0.0033 (3)	0.0009 (3)	0.0006 (3)
C2	0.0160 (4)	0.0246 (5)	0.0154 (4)	0.0041 (4)	0.0070 (3)	0.0008 (4)
C3	0.0149 (4)	0.0223 (5)	0.0172 (5)	0.0003 (4)	0.0064 (4)	0.0023 (4)

Geometric parameters (Å, º)

O1—C6	1.2379 (12)	N1—C1	1.4361 (13)
O2—C6	1.2802 (11)	N1—H1NA	0.914 (17)
O2—H2O	1.2197 (6)	N1—H1NB	0.906 (17)
C4—C5	1.5195 (12)	N1—H1NC	0.95 (2)
C4—C4^i	1.5213 (16)	C1—C2	1.3870 (14)
C4—H4A	0.9900	C1—C3^ii	1.3916 (13)
C4—H4B	0.9900	C2—C3	1.3876 (14)
C5—C6	1.5123 (12)	C2—H2	0.9500
C5—H5A	0.9900	C3—H3	0.9500
C5—H5B	0.9900
C6—O2—H2O	113.50 (6)	C1—N1—H1NA	111.1 (9)
C5—C4—C4^i	111.39 (9)	C1—N1—H1NB	111.9 (10)
C5—C4—H4A	109.3	H1NA—N1—H1NB	107.8 (14)
C4^i—C4—H4A	109.3	C1—N1—H1NC	114.7 (15)
C5—C4—H4B	109.3	H1NA—N1—H1NC	101.0 (18)
C4^i—C4—H4B	109.3	H1NB—N1—H1NC	109.6 (18)
H4A—C4—H4B	108.0	C2—C1—C3^ii	120.02 (9)
C6—C5—C4	115.04 (8)	C2—C1—N1	121.06 (8)
C6—C5—H5A	108.5	C3^ii—C1—N1	118.91 (9)
C4—C5—H5A	108.5	C1—C2—C3	119.97 (9)
C6—C5—H5B	108.5	C1—C2—H2	120.0
C4—C5—H5B	108.5	C3—C2—H2	120.0
H5A—C5—H5B	107.5	C2—C3—C1^ii	120.01 (9)
O1—C6—O2	123.47 (8)	C2—C3—H3	120.0
O1—C6—C5	120.06 (8)	C1^ii—C3—H3	120.0
O2—C6—C5	116.47 (8)
C4^i—C4—C5—C6	−179.82 (9)	C3^ii—C1—C2—C3	0.09 (16)
C4—C5—C6—O1	172.41 (9)	N1—C1—C2—C3	−179.06 (9)
C4—C5—C6—O2	−8.04 (12)	C1—C2—C3—C1^ii	−0.10 (16)

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y+2, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O2^iii	1.22	1.22	2.439 (1)	180
O2—H2O···O1^iii	1.22	2.45	3.178 (1)	116
N1—H1NA···O1^iv	0.91 (2)	1.97 (2)	2.871 (1)	171 (1)
N1—H1NB···O1	0.90 (2)	2.24 (2)	3.060 (1)	152 (1)
N1—H1NB···O2^iii	0.90 (2)	2.51 (2)	3.098 (1)	123 (1)
N1—H1NC···N1^v	0.95 (2)	1.89 (2)	2.840 (1)	174 (2)

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