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The title compound, C6H13N4+·ClO4, crystallizes in the space group P21/n. The structure can be solved in the orthorhombic space group Pnma, but analysis of the refinement parameters showed that the choice of the P21/n space group is the correct one. All interatomic distances can be considered as normal. Molecules are assembled by intermolecular N—H...O hydrogen bonds into a zigzag chain structure along the b axis. In the structure, weak intermolecular C—H...N hydrogen bonds create a two-dimensional net structure in the (011) plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804029320/rz6017sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804029320/rz6017Isup2.hkl
Contains datablock I

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804029320/rz6017sup3.cif
Contains datablock zal19

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804029320/rz6017IIsup4.hkl
Contains datablock II

CCDC reference: 259587

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](Cl-O) = 0.003 Å
  • R factor = 0.076
  • wR factor = 0.202
  • Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.94
Author Response: ... Because collected data were relatively weak, there is a large amount of reflections with small intensities, and a part of reflections was marked as unobserved and excluded from the data set by diffractometer data reduction software. This affect fraction of unique reflections observed (out to \q=25\%) which is equal to 94%.

Alert level B RINTA01_ALERT_3_B The value of Rint is greater than 0.15 Rint given 0.179 PLAT020_ALERT_3_B The value of Rint is greater than 0.10 ......... 0.18 PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors for Cl1
1 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 0 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrysAlis CCD (UNIL IC & KUMA 2000); cell refinement: CrysAlis RED (UNIL IC & KUMA 2000); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1990b) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

3,5,7-Triaza-1-azoniatricyclo[3.3.1.13,7]decane perchlorate top
Crystal data top
C6H13N4+·ClO4F(000) = 504
Mr = 240.65Dx = 1.642 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3276 reflections
a = 9.2662 (19) Åθ = 2–25°
b = 9.6794 (16) ŵ = 0.40 mm1
c = 10.854 (2) ÅT = 291 K
β = 90.061 (17)°Sphere, colourless
V = 973.5 (3) Å30.50 × 0.47 × 0.43 × 0.47 (radius) mm
Z = 4
Data collection top
Kuma KM-4-CCD
diffractometer
1736 independent reflections
Radiation source: fine-focus sealed tube1599 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.179
ω scansθmax = 25.1°, θmin = 2.8°
Absorption correction: numerical
(X-RED; Stoe & Cie, 1999)
h = 1111
Tmin = 0.821, Tmax = 0.850k = 1111
12433 measured reflectionsl = 1212
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.076Hydrogen site location: mixed
wR(F2) = 0.202H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.1322P)2 + 0.3022P]
where P = (Fo2 + 2Fc2)/3
1736 reflections(Δ/σ)max < 0.001
136 parametersΔρmax = 0.59 e Å3
0 restraintsΔρmin = 0.68 e Å3
Special details top

Experimental. Because collected data were relatively weak, there is a large amount of reflections with small intensities, and a part of reflections was marked as unobserved and excluded from the data set by diffractometer data reduction software. This affect fraction of unique reflections observed (out to θ=25°) which is equal to 94%.

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
Cl10.24004 (8)0.61931 (7)0.61710 (6)0.0431 (4)
O10.2487 (3)0.7385 (3)0.6952 (2)0.0644 (8)
O20.1307 (3)0.5289 (4)0.6579 (3)0.0890 (10)
O30.2063 (5)0.6622 (3)0.4965 (3)0.0990 (12)
O40.3716 (3)0.5467 (4)0.6174 (3)0.0946 (11)
N10.2581 (3)0.7500 (2)0.9662 (2)0.0420 (7)
H1N0.27130.81120.89580.063*
C10.3685 (4)0.6337 (4)0.9617 (3)0.0515 (8)
H1A0.35340.57800.88850.062*
H1B0.46520.67180.95840.062*
N20.3527 (3)0.5496 (3)1.0698 (3)0.0506 (7)
C20.2057 (4)0.4937 (3)1.0727 (3)0.0526 (8)
H2A0.18880.43980.99880.063*
H2B0.19590.43251.14300.063*
N30.0977 (3)0.6031 (3)1.0809 (2)0.0453 (7)
C30.1083 (3)0.6881 (3)0.9729 (3)0.0455 (7)
H3A0.03680.76120.97640.055*
H3B0.08980.63290.90000.055*
C40.3764 (4)0.6348 (4)1.1786 (3)0.0575 (10)
H4A0.47290.67361.17540.069*
H4B0.37020.57721.25160.069*
N40.2710 (3)0.7473 (3)1.1882 (2)0.0510 (7)
C50.1269 (4)0.6864 (4)1.1906 (3)0.0512 (8)
H5A0.05570.75961.19630.061*
H5B0.11760.62881.26330.061*
C60.2840 (4)0.8346 (3)1.0815 (3)0.0532 (8)
H6A0.37970.87511.07890.064*
H6B0.21400.90901.08610.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0598 (6)0.0312 (5)0.0383 (5)0.0021 (3)0.0010 (3)0.0021 (3)
O10.097 (2)0.0448 (15)0.0515 (14)0.0004 (13)0.0017 (12)0.0184 (11)
O20.093 (2)0.064 (2)0.110 (2)0.0278 (16)0.0292 (17)0.0005 (18)
O30.202 (4)0.0510 (17)0.0443 (16)0.002 (2)0.0210 (18)0.0035 (12)
O40.0665 (17)0.082 (2)0.135 (3)0.0206 (16)0.0148 (16)0.043 (2)
N10.0579 (15)0.0316 (13)0.0365 (13)0.0024 (11)0.0027 (11)0.0062 (10)
C10.0552 (18)0.0459 (19)0.053 (2)0.0129 (14)0.0076 (15)0.0073 (14)
N20.0552 (15)0.0416 (16)0.0551 (16)0.0123 (12)0.0024 (12)0.0102 (12)
C20.076 (2)0.0298 (16)0.0523 (18)0.0039 (15)0.0026 (16)0.0038 (14)
N30.0517 (15)0.0444 (16)0.0399 (14)0.0045 (11)0.0008 (11)0.0009 (11)
C30.0519 (17)0.0450 (18)0.0395 (16)0.0036 (14)0.0045 (12)0.0007 (13)
C40.0577 (19)0.060 (2)0.055 (2)0.0068 (16)0.0149 (16)0.0221 (16)
N40.0765 (19)0.0373 (15)0.0392 (14)0.0058 (12)0.0084 (12)0.0001 (11)
C50.0648 (19)0.054 (2)0.0352 (16)0.0065 (16)0.0052 (13)0.0017 (14)
C60.081 (2)0.0303 (16)0.0480 (17)0.0046 (15)0.0068 (15)0.0001 (13)
Geometric parameters (Å, º) top
Cl1—O41.407 (3)C2—H2B0.9700
Cl1—O31.408 (3)N3—C31.436 (4)
Cl1—O21.411 (3)N3—C51.463 (4)
Cl1—O11.434 (2)C3—H3A0.9700
N1—C31.514 (4)C3—H3B0.9700
N1—C61.515 (4)C4—N41.466 (5)
N1—C11.522 (4)C4—H4A0.9700
N1—H1N0.9748C4—H4B0.9700
C1—N21.436 (4)N4—C61.439 (4)
C1—H1A0.9700N4—C51.460 (4)
C1—H1B0.9700C5—H5A0.9700
N2—C41.456 (5)C5—H5B0.9700
N2—C21.466 (4)C6—H6A0.9700
C2—N31.459 (4)C6—H6B0.9700
C2—H2A0.9700
O4—Cl1—O3109.9 (2)C2—N3—C5108.9 (3)
O4—Cl1—O2108.2 (2)N3—C3—N1109.3 (2)
O3—Cl1—O2108.4 (2)N3—C3—H3A109.8
O4—Cl1—O1110.62 (18)N1—C3—H3A109.8
O3—Cl1—O1108.95 (18)N3—C3—H3B109.8
O2—Cl1—O1110.68 (18)N1—C3—H3B109.8
C3—N1—C6108.6 (2)H3A—C3—H3B108.3
C3—N1—C1109.0 (2)N2—C4—N4112.2 (3)
C6—N1—C1108.7 (3)N2—C4—H4A109.2
C3—N1—H1N113.2N4—C4—H4A109.2
C6—N1—H1N107.4N2—C4—H4B109.2
C1—N1—H1N109.8N4—C4—H4B109.2
N2—C1—N1108.9 (2)H4A—C4—H4B107.9
N2—C1—H1A109.9C6—N4—C5109.2 (3)
N1—C1—H1A109.9C6—N4—C4108.9 (3)
N2—C1—H1B109.9C5—N4—C4108.1 (3)
N1—C1—H1B109.9N4—C5—N3112.1 (2)
H1A—C1—H1B108.3N4—C5—H5A109.2
C1—N2—C4109.1 (3)N3—C5—H5A109.2
C1—N2—C2108.8 (2)N4—C5—H5B109.2
C4—N2—C2109.3 (2)N3—C5—H5B109.2
N3—C2—N2111.7 (3)H5A—C5—H5B107.9
N3—C2—H2A109.3N4—C6—N1109.5 (3)
N2—C2—H2A109.3N4—C6—H6A109.8
N3—C2—H2B109.3N1—C6—H6A109.8
N2—C2—H2B109.3N4—C6—H6B109.8
H2A—C2—H2B107.9N1—C6—H6B109.8
C3—N3—C2108.6 (2)H6A—C6—H6B108.2
C3—N3—C5109.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.972.373.189 (4)142
N1—H1N···O10.972.302.944 (4)123
C2—H2B···N4ii0.972.583.531 (4)166
Symmetry codes: (i) x+1/2, y+1/2, z+3/2; (ii) x+1/2, y1/2, z+5/2.
 

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