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The crystal structure of the title compound, C3H10N+·ClO4, redetermined at 97 K, is isostructural with C3H10N+·BF4 [Gotoh, Ishikawa & Ishida (2005). Acta Cryst. E61, o4016–o4017]. Both the cation and the anion lie on a mirror plane and are connected by N—H...O and C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806007987/lh2014sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806007987/lh2014Isup2.hkl
Contains datablock I

CCDC reference: 605119

Key indicators

  • Single-crystal X-ray study
  • T = 93 K
  • Mean [sigma](l-O) = 0.002 Å
  • R factor = 0.024
  • wR factor = 0.062
  • Data-to-parameter ratio = 13.7

checkCIF/PLATON results

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Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.615 0.905 Tmin(prime) and Tmax expected: 0.796 0.905 RR(prime) = 0.773 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.77 PLAT480_ALERT_4_C Long H...A H-Bond Reported H4 .. O3 .. 2.61 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 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: PROCESS-AUTO (Rigaku/MSC and Rigaku Corporation, 2004); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

Trimethylammonium perchlorate top
Crystal data top
C3H10N+·ClO4F(000) = 168.00
Mr = 159.57Dx = 1.519 Mg m3
Monoclinic, P21/mMo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybCell parameters from 3847 reflections
a = 5.504 (4) Åθ = 3.6–29.0°
b = 8.605 (6) ŵ = 0.50 mm1
c = 7.580 (8) ÅT = 93 K
β = 103.67 (4)°Prism, colorless
V = 348.8 (5) Å30.45 × 0.35 × 0.20 mm
Z = 2
Data collection top
Rigaku R-AXIS RAPID II
diffractometer
941 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm-1Rint = 0.018
ω scansθmax = 29.0°, θmin = 3.6°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 77
Tmin = 0.615, Tmax = 0.905k = 1011
3864 measured reflectionsl = 1010
985 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.024 w = 1/[σ2(Fo2) + (0.0294P)2 + 0.1361P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.062(Δ/σ)max = 0.001
S = 1.13Δρmax = 0.22 e Å3
985 reflectionsΔρmin = 0.43 e Å3
72 parameters
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
Cl10.51787 (6)0.25000.29280 (4)0.01217 (11)
O10.78696 (19)0.25000.32837 (15)0.0193 (2)
O20.4473 (2)0.25000.46464 (16)0.0321 (3)
O30.42010 (18)0.11436 (11)0.19055 (13)0.0307 (2)
N10.9199 (2)0.25000.74375 (15)0.0121 (2)
C11.0694 (2)0.10697 (13)0.73561 (15)0.0198 (2)
C20.8146 (3)0.25000.9076 (2)0.0176 (3)
H10.793 (4)0.25000.646 (3)0.021 (5)*
H21.203 (3)0.105 (2)0.845 (2)0.029 (4)*
H31.130 (3)0.113 (2)0.633 (2)0.030 (4)*
H40.967 (3)0.020 (2)0.732 (2)0.025 (4)*
H50.713 (3)0.154 (2)0.9043 (19)0.026 (4)*
H60.959 (4)0.25001.021 (3)0.030 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.01190 (16)0.01346 (16)0.01050 (15)0.0000.00137 (10)0.000
O10.0108 (5)0.0278 (6)0.0187 (5)0.0000.0027 (4)0.000
O20.0209 (6)0.0637 (10)0.0138 (5)0.0000.0083 (4)0.000
O30.0277 (4)0.0222 (4)0.0374 (5)0.0062 (4)0.0018 (4)0.0129 (4)
N10.0127 (5)0.0130 (5)0.0100 (5)0.0000.0015 (4)0.000
C10.0247 (5)0.0150 (4)0.0225 (5)0.0051 (4)0.0112 (4)0.0007 (4)
C20.0193 (7)0.0185 (7)0.0178 (7)0.0000.0099 (5)0.000
Geometric parameters (Å, º) top
Cl1—O31.4337 (11)N1—H10.89 (2)
Cl1—O3i1.4337 (11)C1—H20.969 (17)
Cl1—O11.4414 (15)C1—H30.919 (17)
Cl1—O21.4446 (17)C1—H40.934 (16)
N1—C21.489 (2)C2—H50.995 (16)
N1—C1i1.4898 (15)C2—H61.02 (2)
N1—C11.4898 (14)
O1···N13.059 (4)O2···H12.07 (2)
O2···N12.940 (3)O2···H3v2.669 (17)
O1···H12.40 (2)O2···H3vi2.669 (17)
O1···H32.868 (16)O3···H2vii2.611 (15)
O1···H3i2.868 (16)O3···H2iii2.864 (17)
O1···H4ii2.781 (17)O3···H4viii2.610 (17)
O1···H4iii2.781 (17)O3···H5viii2.477 (17)
O1···H6iv2.71 (2)O3···H6vii2.81 (2)
O3—Cl1—O3i109.00 (10)C1—N1—H1107.4 (7)
O3—Cl1—O1109.81 (5)N1—C1—H2107.1 (10)
O3i—Cl1—O1109.81 (5)N1—C1—H3107.8 (11)
O3—Cl1—O2109.93 (6)H2—C1—H3112.0 (14)
O3i—Cl1—O2109.93 (6)N1—C1—H4109.1 (10)
O1—Cl1—O2108.34 (8)H2—C1—H4109.7 (14)
C2—N1—C1i111.23 (8)H3—C1—H4111.1 (14)
C2—N1—C1111.23 (8)N1—C2—H5107.8 (9)
C1i—N1—C1111.40 (13)N1—C2—H6108.8 (13)
C2—N1—H1107.9 (14)H5—C2—H6109.9 (11)
C1i—N1—H1107.4 (7)
Symmetry codes: (i) x, y+1/2, z; (ii) x+2, y+1/2, z+1; (iii) x+2, y, z+1; (iv) x, y, z1; (v) x1, y, z; (vi) x1, y+1/2, z; (vii) x1, y, z1; (viii) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.89 (2)2.40 (2)3.059 (4)131 (2)
N1—H1···O20.89 (2)2.07 (2)2.940 (3)166 (2)
C1—H4···O3viii0.934 (16)2.610 (17)3.451 (4)150.2 (13)
C2—H5···O3viii0.995 (17)2.477 (17)3.406 (4)155.2 (13)
Symmetry code: (viii) x+1, y, z+1.
 

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