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A combination of O—H...O [dav(H...O) = 1.73 Å; θav(O—H...O) = 156°; dav(O...O) = 2.609 (3) Å] and N—H...O [dav(H...O) = 1.85 Å; θav(N—H...O) = 169°; dav(N...O) = 2.740 (2) Å] hydrogen bonds defines a layered structure for the title compound, (C5H12N)[H2AsO4].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803021457/ng6000sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803021457/ng6000Isup2.hkl
Contains datablock I

CCDC reference: 226635

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.018
  • wR factor = 0.042
  • Data-to-parameter ratio = 31.6

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.171 0.259 Tmin and Tmax expected: 0.141 0.259 RR = 1.217 Please check that your absorption correction is appropriate. PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.22
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 32.51 From the CIF: _reflns_number_total 3187 Count of symmetry unique reflns 1760 Completeness (_total/calc) 181.08% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1427 Fraction of Friedel pairs measured 0.811 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 2 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: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97; molecular graphics: ORTEP-3 (Farrugia, 1997) and ATOMS (Shape Software, 1999); software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
(C5H12N)[H2AsO4]F(000) = 232
Mr = 227.09Dx = 1.676 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 4144 reflections
a = 8.6593 (4) Åθ = 2.5–32.5°
b = 6.3233 (3) ŵ = 3.75 mm1
c = 8.9090 (4) ÅT = 293 K
β = 112.676 (1)°Chunk, colourless
V = 450.11 (4) Å30.56 × 0.53 × 0.36 mm
Z = 2
Data collection top
Bruker SMART1000 CCD
diffractometer
3187 independent reflections
Radiation source: fine-focus sealed tube2936 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
ω scansθmax = 32.5°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
h = 1213
Tmin = 0.171, Tmax = 0.259k = 99
5328 measured reflectionsl = 1113
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0246P)2]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.018(Δ/σ)max = 0.002
wR(F2) = 0.042Δρmax = 0.27 e Å3
S = 1.00Δρmin = 0.29 e Å3
3187 reflectionsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
101 parametersExtinction coefficient: 0.0311 (18)
1 restraintAbsolute structure: Flack (1983), 1504 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.063 (8)
Hydrogen site location: inferred from neighbouring sites
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
As10.813891 (12)0.47057 (2)0.937213 (14)0.02762 (4)
O10.64813 (15)0.3917 (2)0.96880 (16)0.0449 (3)
O20.99181 (11)0.4763 (4)1.10049 (11)0.03654 (19)
O30.76336 (14)0.71511 (19)0.85000 (16)0.0398 (3)
H10.85200.78740.86710.048*
O40.84122 (17)0.3272 (2)0.78576 (14)0.0450 (3)
H20.87040.18480.83750.054*
N10.35695 (16)0.6115 (2)0.80147 (17)0.0345 (3)
H30.35200.72440.86090.041*
H40.45490.54530.85480.041*
C10.3511 (2)0.6845 (3)0.6411 (2)0.0433 (4)
H50.44430.77880.65650.052*
H60.24810.76190.58490.052*
C20.3600 (2)0.4968 (5)0.5401 (2)0.0497 (6)
H70.46810.42880.59140.060*
H80.34970.54520.43340.060*
C30.2232 (3)0.3378 (4)0.5215 (3)0.0573 (5)
H90.23890.21380.46490.069*
H100.11530.39910.45670.069*
C40.2256 (3)0.2733 (4)0.6869 (3)0.0566 (5)
H110.13110.18150.67200.068*
H120.32730.19470.74580.068*
C50.2173 (2)0.4653 (6)0.7853 (2)0.0473 (3)
H130.11120.53720.73160.057*
H140.22510.42130.89230.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
As10.02546 (5)0.02915 (6)0.02792 (6)0.00088 (10)0.00993 (4)0.00347 (10)
O10.0347 (5)0.0522 (7)0.0521 (7)0.0012 (5)0.0215 (5)0.0214 (6)
O20.0335 (4)0.0355 (4)0.0321 (4)0.0063 (8)0.0033 (3)0.0007 (8)
O30.0297 (5)0.0330 (5)0.0492 (7)0.0015 (4)0.0068 (5)0.0137 (5)
O40.0518 (7)0.0494 (7)0.0288 (6)0.0095 (6)0.0103 (5)0.0031 (5)
N10.0345 (6)0.0377 (7)0.0338 (7)0.0035 (5)0.0159 (5)0.0040 (5)
C10.0469 (9)0.0412 (9)0.0436 (9)0.0043 (7)0.0193 (8)0.0103 (7)
C20.0622 (9)0.0603 (17)0.0317 (7)0.0107 (11)0.0238 (6)0.0086 (10)
C30.0698 (13)0.0603 (13)0.0365 (9)0.0028 (11)0.0146 (9)0.0110 (9)
C40.0741 (14)0.0454 (11)0.0514 (12)0.0161 (10)0.0254 (10)0.0065 (9)
C50.0468 (7)0.0585 (9)0.0437 (7)0.0108 (16)0.0252 (6)0.0019 (16)
Geometric parameters (Å, º) top
As1—O11.6431 (11)C1—H60.9700
As1—O21.6622 (8)C2—C31.513 (4)
As1—O31.7100 (11)C2—H70.9700
As1—O41.7161 (13)C2—H80.9700
O3—H10.8546C3—C41.522 (3)
O4—H20.9988C3—H90.9700
N1—C11.484 (2)C3—H100.9700
N1—C51.484 (3)C4—C51.516 (4)
N1—H30.9000C4—H110.9700
N1—H40.9000C4—H120.9700
C1—C21.509 (3)C5—H130.9700
C1—H50.9700C5—H140.9700
O1—As1—O2115.65 (6)C3—C2—H7109.3
O1—As1—O3105.37 (6)C1—C2—H8109.3
O2—As1—O3111.49 (9)C3—C2—H8109.3
O1—As1—O4111.63 (8)H7—C2—H8107.9
O2—As1—O4109.72 (7)C2—C3—C4110.73 (16)
O3—As1—O4102.08 (7)C2—C3—H9109.5
As1—O3—H1110.3C4—C3—H9109.5
As1—O4—H2101.6C2—C3—H10109.5
C1—N1—C5112.09 (14)C4—C3—H10109.5
C1—N1—H3109.2H9—C3—H10108.1
C5—N1—H3109.2C5—C4—C3111.06 (18)
C1—N1—H4109.2C5—C4—H11109.4
C5—N1—H4109.2C3—C4—H11109.4
H3—N1—H4107.9C5—C4—H12109.4
N1—C1—C2109.80 (16)C3—C4—H12109.4
N1—C1—H5109.7H11—C4—H12108.0
C2—C1—H5109.7N1—C5—C4109.65 (14)
N1—C1—H6109.7N1—C5—H13109.7
C2—C1—H6109.7C4—C5—H13109.7
H5—C1—H6108.2N1—C5—H14109.7
C1—C2—C3111.75 (16)C4—C5—H14109.7
C1—C2—H7109.3H13—C5—H14108.2
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H1···O2i0.851.742.588 (2)169
O4—H2···O2ii1.001.722.629 (3)149
N1—H3···O1iii0.901.852.720 (2)162
N1—H4···O10.901.862.759 (2)176
Symmetry codes: (i) x+2, y+1/2, z+2; (ii) x+2, y1/2, z+2; (iii) x+1, y+1/2, z+2.
 

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