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The crystal structure of the title compound, C4H12N5+·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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680400652X/wn6232sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680400652X/wn6232Isup2.hkl
Contains datablock I

CCDC reference: 238810

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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

Computing details top

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.

(I) top
Crystal data top
C4H12N5+·BrF(000) = 424
Mr = 210.10Dx = 1.623 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2039 reflections
a = 8.2094 (18) Åθ = 2.7–26.8°
b = 14.203 (3) ŵ = 4.72 mm1
c = 8.1261 (18) ÅT = 298 K
β = 114.807 (3)°Block, white
V = 860.1 (3) Å30.70 × 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 tube1237 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.069
φ and ω scansθmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
h = 97
Tmin = 0.064, Tmax = 0.094k = 1616
4122 measured reflectionsl = 99
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075H-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 parametersΔρmax = 0.45 e Å3
0 restraintsΔρmin = 0.68 e Å3
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
Br10.84638 (4)0.01794 (2)0.22214 (4)0.03571 (15)
C10.1962 (5)0.2442 (3)0.2781 (4)0.0457 (9)
H1A0.10110.25660.31460.069*
H1B0.15590.19960.18040.069*
H1C0.23000.30170.23870.069*
C20.3496 (5)0.1043 (2)0.4597 (5)0.0452 (9)
H2A0.39580.07250.38410.068*
H2B0.22870.08400.42870.068*
H2C0.42290.08970.58450.068*
C30.4767 (4)0.2609 (2)0.5485 (4)0.0278 (7)
C40.7318 (4)0.1656 (2)0.6806 (4)0.0282 (7)
N10.3515 (3)0.20560 (18)0.4321 (3)0.0329 (6)
N20.4587 (3)0.35357 (19)0.5360 (3)0.0406 (7)
H2D0.36510.37820.45180.049*
H2E0.54050.38910.61210.049*
N30.6179 (3)0.22676 (18)0.6946 (3)0.0299 (6)
N40.7588 (4)0.1529 (2)0.5316 (3)0.0369 (7)
H4A0.69980.18590.43620.044*
H4B0.83520.11170.53070.044*
N50.8320 (4)0.1151 (2)0.8259 (3)0.0434 (8)
H5A0.82150.12290.92590.052*
H5B0.90740.07470.81980.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0333 (2)0.0362 (2)0.0356 (2)0.00294 (14)0.01255 (15)0.00019 (14)
C10.0334 (19)0.046 (2)0.046 (2)0.0047 (16)0.0048 (16)0.0008 (16)
C20.0380 (19)0.028 (2)0.066 (2)0.0049 (15)0.0183 (17)0.0021 (16)
C30.0281 (16)0.0259 (18)0.0324 (16)0.0012 (13)0.0157 (14)0.0012 (13)
C40.0277 (16)0.0277 (18)0.0280 (16)0.0034 (13)0.0105 (13)0.0015 (13)
N10.0271 (14)0.0298 (16)0.0369 (14)0.0001 (11)0.0087 (11)0.0004 (12)
N20.0329 (16)0.0294 (17)0.0461 (16)0.0002 (12)0.0032 (13)0.0006 (12)
N30.0317 (14)0.0298 (15)0.0268 (13)0.0055 (12)0.0107 (11)0.0015 (11)
N40.0401 (16)0.0423 (18)0.0304 (14)0.0115 (13)0.0169 (12)0.0044 (12)
N50.0472 (17)0.050 (2)0.0345 (15)0.0229 (14)0.0190 (13)0.0140 (13)
Geometric parameters (Å, º) top
C1—N11.467 (4)C3—N31.354 (4)
C1—H1A0.9600C4—N31.316 (4)
C1—H1B0.9600C4—N51.330 (4)
C1—H1C0.9600C4—N41.331 (4)
C2—N11.457 (4)N2—H2D0.8600
C2—H2A0.9600N2—H2E0.8600
C2—H2B0.9600N4—H4A0.8600
C2—H2C0.9600N4—H4B0.8600
C3—N21.324 (4)N5—H5A0.8600
C3—N11.324 (4)N5—H5B0.8600
N1—C1—H1A109.5N3—C4—N4124.3 (3)
N1—C1—H1B109.5N5—C4—N4117.2 (3)
H1A—C1—H1B109.5C3—N1—C2122.1 (3)
N1—C1—H1C109.5C3—N1—C1121.6 (3)
H1A—C1—H1C109.5C2—N1—C1116.0 (3)
H1B—C1—H1C109.5C3—N2—H2D120.0
N1—C2—H2A109.5C3—N2—H2E120.0
N1—C2—H2B109.5H2D—N2—H2E120.0
H2A—C2—H2B109.5C4—N3—C3122.6 (2)
N1—C2—H2C109.5C4—N4—H4A120.0
H2A—C2—H2C109.5C4—N4—H4B120.0
H2B—C2—H2C109.5H4A—N4—H4B120.0
N2—C3—N1120.5 (3)C4—N5—H5A120.0
N2—C3—N3116.8 (3)C4—N5—H5B120.0
N1—C3—N3122.4 (3)H5A—N5—H5B120.0
N3—C4—N5118.4 (3)
N2—C3—N1—C2168.7 (3)N5—C4—N3—C3160.4 (3)
N3—C3—N1—C24.5 (5)N4—C4—N3—C322.2 (5)
N2—C3—N1—C14.6 (5)N2—C3—N3—C4128.5 (3)
N3—C3—N1—C1177.8 (3)N1—C3—N3—C458.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5B···Br1i0.862.553.400 (3)169
N5—H5A···Br1ii0.862.773.460 (3)139
N4—H4B···Br1i0.863.143.867 (3)144
N4—H4B···Br10.862.873.469 (3)128
N4—H4A···N3iii0.862.183.017 (4)165
N2—H2E···Br1iv0.862.643.422 (3)152
N2—H2D···Br1v0.862.623.422 (3)155
Symmetry codes: (i) x+2, y, z+1; (ii) x, y, z+1; (iii) x, y+1/2, z1/2; (iv) x, y+1/2, z+1/2; (v) x+1, y+1/2, z+1/2.
 

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