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The two independent ammonium cations of the title compound, NH4+.C7H5O4−.H2O, lie on twofold rotation axes. The ammonium cations, 2,4-dihydroxy­benzoate anions and water mol­ecules are linked into a three-dimensional structure via O—H...O and N—H...O hydrogen bonds and π–π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806044357/ob2090sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806044357/ob2090Isup2.hkl
Contains datablock I

CCDC reference: 630200

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.038
  • wR factor = 0.104
  • Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H4 .. O1 .. 2.66 Ang. PLAT731_ALERT_1_C Bond Calc 0.90(2), Rep 0.900(9) ...... 2.22 su-Ra N1 -H12 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.84(2), Rep 0.843(9) ...... 2.22 su-Ra O5 -H51 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.84(2), Rep 0.843(9) ...... 2.22 su-Ra O5 -H51 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.90(2), Rep 0.900(9) ...... 2.22 su-Ra N1 -H12 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 6 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Ammonium 2,4-dihydroxybenzoate monohydrate top
Crystal data top
H4N+·C7H5O4·H2OF(000) = 800
Mr = 189.17Dx = 1.451 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2644 reflections
a = 15.5715 (17) Åθ = 2.6–27.5°
b = 15.9806 (18) ŵ = 0.12 mm1
c = 7.3688 (8) ÅT = 298 K
β = 109.186 (2)°Block, red
V = 1731.8 (3) Å30.36 × 0.30 × 0.20 mm
Z = 8
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
1700 independent reflections
Radiation source: fine-focus sealed tube1492 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ω scansθmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 1914
Tmin = 0.957, Tmax = 0.976k = 1919
5274 measured reflectionsl = 99
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0555P)2 + 0.6723P]
where P = (Fo2 + 2Fc2)/3
1700 reflections(Δ/σ)max = 0.004
147 parametersΔρmax = 0.23 e Å3
21 restraintsΔρmin = 0.21 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
N10.00000.39586 (12)0.25000.0458 (5)
N20.50000.50424 (10)0.75000.0302 (4)
O10.10655 (6)0.10451 (6)0.07786 (15)0.0349 (3)
O20.23926 (7)0.04204 (6)0.12533 (16)0.0379 (3)
O30.09890 (7)0.25587 (6)0.17187 (18)0.0431 (3)
H3A0.08010.20870.13580.062 (6)*
O40.37340 (7)0.40841 (6)0.41785 (17)0.0418 (3)
H40.33690.44660.40700.079 (7)*
O50.12264 (8)0.50241 (8)0.52376 (19)0.0490 (3)
C10.23983 (9)0.18649 (8)0.20037 (18)0.0271 (3)
C20.19060 (9)0.25713 (8)0.22174 (19)0.0283 (3)
C30.23498 (9)0.33110 (8)0.2961 (2)0.0315 (3)
H30.20160.37710.31220.038*
C40.32796 (9)0.33672 (8)0.34595 (19)0.0299 (3)
C50.37859 (9)0.26806 (9)0.3227 (2)0.0339 (3)
H50.44140.27190.35470.041*
C60.33418 (9)0.19466 (8)0.2519 (2)0.0311 (3)
H60.36810.14880.23760.037*
C70.19290 (9)0.10648 (8)0.12962 (19)0.0286 (3)
H110.0384 (11)0.4312 (10)0.337 (2)0.058 (4)*
H120.0341 (13)0.3613 (11)0.206 (3)0.067 (4)*
H210.5351 (10)0.5375 (9)0.845 (2)0.045 (4)*
H220.4634 (10)0.4721 (10)0.793 (3)0.047 (5)*
H510.1598 (12)0.5206 (14)0.472 (3)0.084 (8)*
H520.1557 (12)0.4798 (13)0.627 (2)0.075 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0326 (11)0.0364 (11)0.0673 (14)0.0000.0147 (10)0.000
N20.0287 (9)0.0303 (9)0.0295 (9)0.0000.0067 (7)0.000
O10.0290 (5)0.0289 (5)0.0433 (6)0.0062 (4)0.0071 (4)0.0042 (4)
O20.0369 (6)0.0238 (5)0.0519 (7)0.0002 (4)0.0131 (5)0.0040 (4)
O30.0238 (5)0.0306 (6)0.0697 (8)0.0020 (4)0.0083 (5)0.0107 (5)
O40.0324 (6)0.0265 (5)0.0592 (7)0.0063 (4)0.0052 (5)0.0077 (5)
O50.0431 (7)0.0520 (7)0.0480 (7)0.0073 (5)0.0099 (6)0.0027 (5)
C10.0290 (7)0.0232 (7)0.0277 (7)0.0018 (5)0.0074 (5)0.0002 (5)
C20.0246 (7)0.0269 (7)0.0310 (7)0.0000 (5)0.0059 (5)0.0009 (5)
C30.0304 (7)0.0238 (7)0.0381 (8)0.0026 (5)0.0083 (6)0.0019 (5)
C40.0311 (7)0.0236 (6)0.0313 (7)0.0047 (5)0.0050 (6)0.0005 (5)
C50.0238 (7)0.0325 (7)0.0428 (8)0.0022 (6)0.0077 (6)0.0004 (6)
C60.0291 (7)0.0253 (7)0.0388 (8)0.0027 (5)0.0108 (6)0.0002 (5)
C70.0318 (7)0.0249 (7)0.0284 (7)0.0018 (5)0.0092 (6)0.0016 (5)
Geometric parameters (Å, º) top
N1—H110.914 (9)O5—H520.847 (9)
N1—H120.900 (9)C1—C61.3975 (19)
N2—H210.906 (9)C1—C21.4021 (18)
N2—H220.901 (9)C1—C71.4800 (18)
O1—C71.2717 (16)C2—C31.3878 (19)
O2—C71.2640 (17)C3—C41.3747 (19)
O3—C21.3527 (17)C3—H30.9300
O3—H3A0.8200C4—C51.394 (2)
O4—C41.3593 (16)C5—C61.3746 (19)
O4—H40.8200C5—H50.9300
O5—H510.843 (9)C6—H60.9300
H11—N1—H12107.8 (18)C2—C3—H3119.8
H21—N2—H22110.5 (17)O4—C4—C3121.80 (12)
C2—O3—H3A109.5O4—C4—C5117.93 (13)
C4—O4—H4109.5C3—C4—C5120.27 (12)
H51—O5—H52104.5 (13)C6—C5—C4118.95 (13)
C6—C1—C2117.32 (12)C6—C5—H5120.5
C6—C1—C7121.98 (12)C4—C5—H5120.5
C2—C1—C7120.68 (12)C5—C6—C1122.39 (12)
O3—C2—C3117.65 (12)C5—C6—H6118.8
O3—C2—C1121.66 (11)C1—C6—H6118.8
C3—C2—C1120.69 (13)O2—C7—O1121.91 (12)
C4—C3—C2120.35 (12)O2—C7—C1119.52 (12)
C4—C3—H3119.8O1—C7—C1118.56 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O10.821.802.5298 (13)147
O4—H4···O1i0.822.663.1483 (15)119
O4—H4···O2i0.821.902.7151 (15)174
O5—H51···O2i0.84 (1)1.96 (1)2.7902 (16)168 (2)
O5—H52···O2ii0.85 (1)2.04 (1)2.8567 (16)161 (2)
N1—H11···O50.91 (1)1.93 (1)2.8432 (17)178 (2)
N1—H12···O30.90 (1)2.02 (1)2.8792 (18)159 (2)
N2—H21···O1iii0.91 (1)2.02 (1)2.9193 (13)173 (2)
N2—H22···O1ii0.90 (1)2.07 (1)2.9606 (14)173 (2)
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x+1/2, y+1/2, z+1; (iii) x+1/2, y+1/2, z+1.
 

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