Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804029320/rz6017sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804029320/rz6017Isup2.hkl | |
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804029320/rz6017sup3.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804029320/rz6017IIsup4.hkl |
CCDC reference: 259587
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (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
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.
C6H13N4+·ClO4− | F(000) = 504 |
Mr = 240.65 | Dx = 1.642 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3276 reflections |
a = 9.2662 (19) Å | θ = 2–25° |
b = 9.6794 (16) Å | µ = 0.40 mm−1 |
c = 10.854 (2) Å | T = 291 K |
β = 90.061 (17)° | Sphere, colourless |
V = 973.5 (3) Å3 | 0.50 × 0.47 × 0.43 × 0.47 (radius) mm |
Z = 4 |
Kuma KM-4-CCD diffractometer | 1736 independent reflections |
Radiation source: fine-focus sealed tube | 1599 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.179 |
ω scans | θmax = 25.1°, θmin = 2.8° |
Absorption correction: numerical (X-RED; Stoe & Cie, 1999) | h = −11→11 |
Tmin = 0.821, Tmax = 0.850 | k = −11→11 |
12433 measured reflections | l = −12→12 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: structure-invariant direct methods |
R[F2 > 2σ(F2)] = 0.076 | Hydrogen site location: mixed |
wR(F2) = 0.202 | H 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 parameters | Δρmax = 0.59 e Å−3 |
0 restraints | Δρmin = −0.68 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.24004 (8) | 0.61931 (7) | 0.61710 (6) | 0.0431 (4) | |
O1 | 0.2487 (3) | 0.7385 (3) | 0.6952 (2) | 0.0644 (8) | |
O2 | 0.1307 (3) | 0.5289 (4) | 0.6579 (3) | 0.0890 (10) | |
O3 | 0.2063 (5) | 0.6622 (3) | 0.4965 (3) | 0.0990 (12) | |
O4 | 0.3716 (3) | 0.5467 (4) | 0.6174 (3) | 0.0946 (11) | |
N1 | 0.2581 (3) | 0.7500 (2) | 0.9662 (2) | 0.0420 (7) | |
H1N | 0.2713 | 0.8112 | 0.8958 | 0.063* | |
C1 | 0.3685 (4) | 0.6337 (4) | 0.9617 (3) | 0.0515 (8) | |
H1A | 0.3534 | 0.5780 | 0.8885 | 0.062* | |
H1B | 0.4652 | 0.6718 | 0.9584 | 0.062* | |
N2 | 0.3527 (3) | 0.5496 (3) | 1.0698 (3) | 0.0506 (7) | |
C2 | 0.2057 (4) | 0.4937 (3) | 1.0727 (3) | 0.0526 (8) | |
H2A | 0.1888 | 0.4398 | 0.9988 | 0.063* | |
H2B | 0.1959 | 0.4325 | 1.1430 | 0.063* | |
N3 | 0.0977 (3) | 0.6031 (3) | 1.0809 (2) | 0.0453 (7) | |
C3 | 0.1083 (3) | 0.6881 (3) | 0.9729 (3) | 0.0455 (7) | |
H3A | 0.0368 | 0.7612 | 0.9764 | 0.055* | |
H3B | 0.0898 | 0.6329 | 0.9000 | 0.055* | |
C4 | 0.3764 (4) | 0.6348 (4) | 1.1786 (3) | 0.0575 (10) | |
H4A | 0.4729 | 0.6736 | 1.1754 | 0.069* | |
H4B | 0.3702 | 0.5772 | 1.2516 | 0.069* | |
N4 | 0.2710 (3) | 0.7473 (3) | 1.1882 (2) | 0.0510 (7) | |
C5 | 0.1269 (4) | 0.6864 (4) | 1.1906 (3) | 0.0512 (8) | |
H5A | 0.0557 | 0.7596 | 1.1963 | 0.061* | |
H5B | 0.1176 | 0.6288 | 1.2633 | 0.061* | |
C6 | 0.2840 (4) | 0.8346 (3) | 1.0815 (3) | 0.0532 (8) | |
H6A | 0.3797 | 0.8751 | 1.0789 | 0.064* | |
H6B | 0.2140 | 0.9090 | 1.0861 | 0.064* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0598 (6) | 0.0312 (5) | 0.0383 (5) | −0.0021 (3) | −0.0010 (3) | −0.0021 (3) |
O1 | 0.097 (2) | 0.0448 (15) | 0.0515 (14) | 0.0004 (13) | −0.0017 (12) | −0.0184 (11) |
O2 | 0.093 (2) | 0.064 (2) | 0.110 (2) | −0.0278 (16) | 0.0292 (17) | −0.0005 (18) |
O3 | 0.202 (4) | 0.0510 (17) | 0.0443 (16) | 0.002 (2) | −0.0210 (18) | 0.0035 (12) |
O4 | 0.0665 (17) | 0.082 (2) | 0.135 (3) | 0.0206 (16) | −0.0148 (16) | −0.043 (2) |
N1 | 0.0579 (15) | 0.0316 (13) | 0.0365 (13) | 0.0024 (11) | 0.0027 (11) | 0.0062 (10) |
C1 | 0.0552 (18) | 0.0459 (19) | 0.053 (2) | 0.0129 (14) | 0.0076 (15) | 0.0073 (14) |
N2 | 0.0552 (15) | 0.0416 (16) | 0.0551 (16) | 0.0123 (12) | 0.0024 (12) | 0.0102 (12) |
C2 | 0.076 (2) | 0.0298 (16) | 0.0523 (18) | −0.0039 (15) | 0.0026 (16) | 0.0038 (14) |
N3 | 0.0517 (15) | 0.0444 (16) | 0.0399 (14) | −0.0045 (11) | 0.0008 (11) | 0.0009 (11) |
C3 | 0.0519 (17) | 0.0450 (18) | 0.0395 (16) | 0.0036 (14) | −0.0045 (12) | −0.0007 (13) |
C4 | 0.0577 (19) | 0.060 (2) | 0.055 (2) | −0.0068 (16) | −0.0149 (16) | 0.0221 (16) |
N4 | 0.0765 (19) | 0.0373 (15) | 0.0392 (14) | −0.0058 (12) | −0.0084 (12) | −0.0001 (11) |
C5 | 0.0648 (19) | 0.054 (2) | 0.0352 (16) | 0.0065 (16) | 0.0052 (13) | 0.0017 (14) |
C6 | 0.081 (2) | 0.0303 (16) | 0.0480 (17) | −0.0046 (15) | −0.0068 (15) | −0.0001 (13) |
Cl1—O4 | 1.407 (3) | C2—H2B | 0.9700 |
Cl1—O3 | 1.408 (3) | N3—C3 | 1.436 (4) |
Cl1—O2 | 1.411 (3) | N3—C5 | 1.463 (4) |
Cl1—O1 | 1.434 (2) | C3—H3A | 0.9700 |
N1—C3 | 1.514 (4) | C3—H3B | 0.9700 |
N1—C6 | 1.515 (4) | C4—N4 | 1.466 (5) |
N1—C1 | 1.522 (4) | C4—H4A | 0.9700 |
N1—H1N | 0.9748 | C4—H4B | 0.9700 |
C1—N2 | 1.436 (4) | N4—C6 | 1.439 (4) |
C1—H1A | 0.9700 | N4—C5 | 1.460 (4) |
C1—H1B | 0.9700 | C5—H5A | 0.9700 |
N2—C4 | 1.456 (5) | C5—H5B | 0.9700 |
N2—C2 | 1.466 (4) | C6—H6A | 0.9700 |
C2—N3 | 1.459 (4) | C6—H6B | 0.9700 |
C2—H2A | 0.9700 | ||
O4—Cl1—O3 | 109.9 (2) | C2—N3—C5 | 108.9 (3) |
O4—Cl1—O2 | 108.2 (2) | N3—C3—N1 | 109.3 (2) |
O3—Cl1—O2 | 108.4 (2) | N3—C3—H3A | 109.8 |
O4—Cl1—O1 | 110.62 (18) | N1—C3—H3A | 109.8 |
O3—Cl1—O1 | 108.95 (18) | N3—C3—H3B | 109.8 |
O2—Cl1—O1 | 110.68 (18) | N1—C3—H3B | 109.8 |
C3—N1—C6 | 108.6 (2) | H3A—C3—H3B | 108.3 |
C3—N1—C1 | 109.0 (2) | N2—C4—N4 | 112.2 (3) |
C6—N1—C1 | 108.7 (3) | N2—C4—H4A | 109.2 |
C3—N1—H1N | 113.2 | N4—C4—H4A | 109.2 |
C6—N1—H1N | 107.4 | N2—C4—H4B | 109.2 |
C1—N1—H1N | 109.8 | N4—C4—H4B | 109.2 |
N2—C1—N1 | 108.9 (2) | H4A—C4—H4B | 107.9 |
N2—C1—H1A | 109.9 | C6—N4—C5 | 109.2 (3) |
N1—C1—H1A | 109.9 | C6—N4—C4 | 108.9 (3) |
N2—C1—H1B | 109.9 | C5—N4—C4 | 108.1 (3) |
N1—C1—H1B | 109.9 | N4—C5—N3 | 112.1 (2) |
H1A—C1—H1B | 108.3 | N4—C5—H5A | 109.2 |
C1—N2—C4 | 109.1 (3) | N3—C5—H5A | 109.2 |
C1—N2—C2 | 108.8 (2) | N4—C5—H5B | 109.2 |
C4—N2—C2 | 109.3 (2) | N3—C5—H5B | 109.2 |
N3—C2—N2 | 111.7 (3) | H5A—C5—H5B | 107.9 |
N3—C2—H2A | 109.3 | N4—C6—N1 | 109.5 (3) |
N2—C2—H2A | 109.3 | N4—C6—H6A | 109.8 |
N3—C2—H2B | 109.3 | N1—C6—H6A | 109.8 |
N2—C2—H2B | 109.3 | N4—C6—H6B | 109.8 |
H2A—C2—H2B | 107.9 | N1—C6—H6B | 109.8 |
C3—N3—C2 | 108.6 (2) | H6A—C6—H6B | 108.2 |
C3—N3—C5 | 109.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.97 | 2.37 | 3.189 (4) | 142 |
N1—H1N···O1 | 0.97 | 2.30 | 2.944 (4) | 123 |
C2—H2B···N4ii | 0.97 | 2.58 | 3.531 (4) | 166 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) −x+1/2, y−1/2, −z+5/2. |