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The crystal structure of the title compound, C
4H
12N
5+·Br
−, shows that the C—N bonds in this compound range in length from 1.316 (4) to 1.354 (4) Å. The dihedral angle between the two guanide planes is 68.5 (1)°. The crystal packing is stabilized by N—H
N and N—H
Br hydrogen bonds. The bromide anions are involved in six hydrogen bonds and are sandwiched between layers of
N,N-dimethylbiguanidium cations.
Supporting information
CCDC reference: 238810
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (N-C) = 0.004 Å
- R factor = 0.034
- wR factor = 0.075
- Data-to-parameter ratio = 16.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.70 mm
PLAT414_ALERT_2_C Short Intra D-H..H-X H1C .. H2D .. 1.95 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4B .. BR1 .. 3.14 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
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1999); software used to prepare material for publication: SHELXTL/PC.
Crystal data top
C4H12N5+·Br− | F(000) = 424 |
Mr = 210.10 | Dx = 1.623 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2039 reflections |
a = 8.2094 (18) Å | θ = 2.7–26.8° |
b = 14.203 (3) Å | µ = 4.72 mm−1 |
c = 8.1261 (18) Å | T = 298 K |
β = 114.807 (3)° | Block, white |
V = 860.1 (3) Å3 | 0.70 × 0.50 × 0.50 mm |
Z = 4 | |
Data collection top
Bruker SMART 1K CCD area-detector diffractometer | 1516 independent reflections |
Radiation source: fine-focus sealed tube | 1237 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.069 |
φ and ω scans | θmax = 25.0°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | h = −9→7 |
Tmin = 0.064, Tmax = 0.094 | k = −16→16 |
4122 measured reflections | l = −9→9 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.075 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0418P)2] where P = (Fo2 + 2Fc2)/3 |
1516 reflections | (Δ/σ)max = 0.001 |
93 parameters | Δρmax = 0.45 e Å−3 |
0 restraints | Δρmin = −0.68 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Br1 | 0.84638 (4) | 0.01794 (2) | 0.22214 (4) | 0.03571 (15) | |
C1 | 0.1962 (5) | 0.2442 (3) | 0.2781 (4) | 0.0457 (9) | |
H1A | 0.1011 | 0.2566 | 0.3146 | 0.069* | |
H1B | 0.1559 | 0.1996 | 0.1804 | 0.069* | |
H1C | 0.2300 | 0.3017 | 0.2387 | 0.069* | |
C2 | 0.3496 (5) | 0.1043 (2) | 0.4597 (5) | 0.0452 (9) | |
H2A | 0.3958 | 0.0725 | 0.3841 | 0.068* | |
H2B | 0.2287 | 0.0840 | 0.4287 | 0.068* | |
H2C | 0.4229 | 0.0897 | 0.5845 | 0.068* | |
C3 | 0.4767 (4) | 0.2609 (2) | 0.5485 (4) | 0.0278 (7) | |
C4 | 0.7318 (4) | 0.1656 (2) | 0.6806 (4) | 0.0282 (7) | |
N1 | 0.3515 (3) | 0.20560 (18) | 0.4321 (3) | 0.0329 (6) | |
N2 | 0.4587 (3) | 0.35357 (19) | 0.5360 (3) | 0.0406 (7) | |
H2D | 0.3651 | 0.3782 | 0.4518 | 0.049* | |
H2E | 0.5405 | 0.3891 | 0.6121 | 0.049* | |
N3 | 0.6179 (3) | 0.22676 (18) | 0.6946 (3) | 0.0299 (6) | |
N4 | 0.7588 (4) | 0.1529 (2) | 0.5316 (3) | 0.0369 (7) | |
H4A | 0.6998 | 0.1859 | 0.4362 | 0.044* | |
H4B | 0.8352 | 0.1117 | 0.5307 | 0.044* | |
N5 | 0.8320 (4) | 0.1151 (2) | 0.8259 (3) | 0.0434 (8) | |
H5A | 0.8215 | 0.1229 | 0.9259 | 0.052* | |
H5B | 0.9074 | 0.0747 | 0.8198 | 0.052* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0333 (2) | 0.0362 (2) | 0.0356 (2) | 0.00294 (14) | 0.01255 (15) | −0.00019 (14) |
C1 | 0.0334 (19) | 0.046 (2) | 0.046 (2) | 0.0047 (16) | 0.0048 (16) | −0.0008 (16) |
C2 | 0.0380 (19) | 0.028 (2) | 0.066 (2) | −0.0049 (15) | 0.0183 (17) | −0.0021 (16) |
C3 | 0.0281 (16) | 0.0259 (18) | 0.0324 (16) | 0.0012 (13) | 0.0157 (14) | −0.0012 (13) |
C4 | 0.0277 (16) | 0.0277 (18) | 0.0280 (16) | −0.0034 (13) | 0.0105 (13) | −0.0015 (13) |
N1 | 0.0271 (14) | 0.0298 (16) | 0.0369 (14) | −0.0001 (11) | 0.0087 (11) | −0.0004 (12) |
N2 | 0.0329 (16) | 0.0294 (17) | 0.0461 (16) | 0.0002 (12) | 0.0032 (13) | −0.0006 (12) |
N3 | 0.0317 (14) | 0.0298 (15) | 0.0268 (13) | 0.0055 (12) | 0.0107 (11) | −0.0015 (11) |
N4 | 0.0401 (16) | 0.0423 (18) | 0.0304 (14) | 0.0115 (13) | 0.0169 (12) | 0.0044 (12) |
N5 | 0.0472 (17) | 0.050 (2) | 0.0345 (15) | 0.0229 (14) | 0.0190 (13) | 0.0140 (13) |
Geometric parameters (Å, º) top
C1—N1 | 1.467 (4) | C3—N3 | 1.354 (4) |
C1—H1A | 0.9600 | C4—N3 | 1.316 (4) |
C1—H1B | 0.9600 | C4—N5 | 1.330 (4) |
C1—H1C | 0.9600 | C4—N4 | 1.331 (4) |
C2—N1 | 1.457 (4) | N2—H2D | 0.8600 |
C2—H2A | 0.9600 | N2—H2E | 0.8600 |
C2—H2B | 0.9600 | N4—H4A | 0.8600 |
C2—H2C | 0.9600 | N4—H4B | 0.8600 |
C3—N2 | 1.324 (4) | N5—H5A | 0.8600 |
C3—N1 | 1.324 (4) | N5—H5B | 0.8600 |
| | | |
N1—C1—H1A | 109.5 | N3—C4—N4 | 124.3 (3) |
N1—C1—H1B | 109.5 | N5—C4—N4 | 117.2 (3) |
H1A—C1—H1B | 109.5 | C3—N1—C2 | 122.1 (3) |
N1—C1—H1C | 109.5 | C3—N1—C1 | 121.6 (3) |
H1A—C1—H1C | 109.5 | C2—N1—C1 | 116.0 (3) |
H1B—C1—H1C | 109.5 | C3—N2—H2D | 120.0 |
N1—C2—H2A | 109.5 | C3—N2—H2E | 120.0 |
N1—C2—H2B | 109.5 | H2D—N2—H2E | 120.0 |
H2A—C2—H2B | 109.5 | C4—N3—C3 | 122.6 (2) |
N1—C2—H2C | 109.5 | C4—N4—H4A | 120.0 |
H2A—C2—H2C | 109.5 | C4—N4—H4B | 120.0 |
H2B—C2—H2C | 109.5 | H4A—N4—H4B | 120.0 |
N2—C3—N1 | 120.5 (3) | C4—N5—H5A | 120.0 |
N2—C3—N3 | 116.8 (3) | C4—N5—H5B | 120.0 |
N1—C3—N3 | 122.4 (3) | H5A—N5—H5B | 120.0 |
N3—C4—N5 | 118.4 (3) | | |
| | | |
N2—C3—N1—C2 | −168.7 (3) | N5—C4—N3—C3 | −160.4 (3) |
N3—C3—N1—C2 | 4.5 (5) | N4—C4—N3—C3 | 22.2 (5) |
N2—C3—N1—C1 | 4.6 (5) | N2—C3—N3—C4 | −128.5 (3) |
N3—C3—N1—C1 | 177.8 (3) | N1—C3—N3—C4 | 58.1 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5B···Br1i | 0.86 | 2.55 | 3.400 (3) | 169 |
N5—H5A···Br1ii | 0.86 | 2.77 | 3.460 (3) | 139 |
N4—H4B···Br1i | 0.86 | 3.14 | 3.867 (3) | 144 |
N4—H4B···Br1 | 0.86 | 2.87 | 3.469 (3) | 128 |
N4—H4A···N3iii | 0.86 | 2.18 | 3.017 (4) | 165 |
N2—H2E···Br1iv | 0.86 | 2.64 | 3.422 (3) | 152 |
N2—H2D···Br1v | 0.86 | 2.62 | 3.422 (3) | 155 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) x, y, z+1; (iii) x, −y+1/2, z−1/2; (iv) x, −y+1/2, z+1/2; (v) −x+1, y+1/2, −z+1/2. |
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