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In the structure of the title compound, C9H13ClN4O, the guanidinium group is nearly coplanar with the 2-methoxy­phenyl ring, C=N having E geometry. The chloride ions are involved in inter­molecular hydrogen bonds with the H atoms of the amino­guanidinium ion.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806055383/hg2162sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806055383/hg2162Isup2.hkl
Contains datablock I

CCDC reference: 636679

Key indicators

  • Single-crystal X-ray study
  • T = 90 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.119
  • Data-to-parameter ratio = 18.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 Cl
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO–SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1995); software used to prepare material for publication: SHELX97-2 (Sheldrick, 1997) and local procedures.

(E)-1-[(2-Methoxyphenyl)methyleneamino]guanidinium chloride top
Crystal data top
C9H13N4O+·ClF(000) = 480
Mr = 228.68Dx = 1.377 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2659 reflections
a = 6.9550 (1) Åθ = 1.0–27.5°
b = 10.9089 (2) ŵ = 0.33 mm1
c = 14.5481 (3) ÅT = 90 K
β = 92.034 (1)°Plate, colourless
V = 1103.09 (3) Å30.30 × 0.20 × 0.07 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
2526 independent reflections
Radiation source: fine-focus sealed tube1837 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 18 pixels mm-1θmax = 27.5°, θmin = 2.3°
ω scans at fixed χ = 55°h = 99
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)
k = 1414
Tmin = 0.908, Tmax = 0.978l = 1818
4915 measured reflections
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.061P)2 + 0.3498P]
where P = (Fo2 + 2Fc2)/3
2526 reflections(Δ/σ)max < 0.001
137 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.34 e Å3
Special details top

Experimental. 1H NMR (DMSO-d6, p.p.m.): δ 3.85 (d, 3H), 7.00 (t, 1H), 7.10 (d, 1H), 7.43 (t, 1H), 7.79 (s, 4H), 8.09 (d, 1H), 8.45 (d, 1H), 12.18 (s, 1H). 13C NMR (DMSO-d6, p.p.m.): δ 55.71, 111.68, 120.44, 121.12, 126.16, 131.97, 141.76, 155.16, 157.54.

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
C10.3303 (3)0.17882 (18)0.53833 (13)0.0171 (4)
C20.3961 (3)0.23492 (19)0.61959 (13)0.0200 (4)
H20.42150.32050.62080.024*
C30.4241 (3)0.16532 (19)0.69852 (14)0.0219 (5)
H30.46800.20360.75400.026*
C40.3888 (3)0.0400 (2)0.69726 (14)0.0229 (5)
H40.41050.00750.75140.027*
C50.3219 (3)0.01508 (19)0.61704 (13)0.0197 (4)
H50.29620.10060.61660.024*
C60.2911 (3)0.05264 (18)0.53640 (13)0.0161 (4)
C70.2257 (3)0.00548 (18)0.45042 (13)0.0164 (4)
H70.21730.04140.39540.020*
C80.0772 (3)0.28227 (18)0.35589 (13)0.0170 (4)
C90.3575 (3)0.36550 (18)0.45291 (15)0.0240 (5)
H9A0.29540.41280.50090.036*
H9B0.32080.39940.39240.036*
H9C0.49750.37010.46240.036*
N10.1797 (2)0.11865 (15)0.44857 (11)0.0177 (4)
N20.1244 (2)0.16398 (15)0.36304 (11)0.0171 (4)
H2A0.12040.11600.31440.020*
N30.0325 (2)0.32762 (15)0.27298 (11)0.0209 (4)
H3A0.00240.40560.26670.025*
H3B0.03290.27960.22440.025*
N40.0772 (2)0.35331 (15)0.42969 (11)0.0205 (4)
H4A0.04740.43140.42420.025*
H4B0.10710.32240.48420.025*
O10.2971 (2)0.24004 (12)0.45732 (9)0.0215 (3)
Cl10.14083 (7)0.58955 (4)0.34831 (3)0.02149 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0149 (9)0.0200 (11)0.0167 (10)0.0008 (8)0.0027 (8)0.0005 (8)
C20.0204 (10)0.0185 (10)0.0212 (11)0.0005 (8)0.0029 (8)0.0035 (9)
C30.0200 (10)0.0270 (11)0.0187 (11)0.0017 (9)0.0003 (8)0.0070 (9)
C40.0245 (11)0.0272 (11)0.0168 (10)0.0003 (9)0.0004 (8)0.0020 (9)
C50.0196 (10)0.0196 (10)0.0201 (10)0.0009 (8)0.0031 (8)0.0003 (8)
C60.0129 (9)0.0179 (10)0.0178 (10)0.0009 (8)0.0024 (8)0.0026 (8)
C70.0139 (9)0.0198 (10)0.0156 (10)0.0014 (8)0.0014 (8)0.0014 (8)
C80.0151 (9)0.0166 (10)0.0195 (10)0.0014 (8)0.0020 (8)0.0017 (8)
C90.0308 (12)0.0157 (10)0.0256 (12)0.0026 (9)0.0041 (9)0.0026 (9)
N10.0173 (8)0.0199 (9)0.0158 (9)0.0008 (7)0.0001 (7)0.0039 (7)
N20.0220 (9)0.0148 (8)0.0144 (8)0.0001 (7)0.0001 (7)0.0006 (7)
N30.0318 (10)0.0144 (8)0.0165 (9)0.0016 (7)0.0001 (7)0.0009 (7)
N40.0307 (10)0.0147 (8)0.0160 (8)0.0022 (7)0.0002 (7)0.0006 (7)
O10.0300 (8)0.0156 (7)0.0189 (7)0.0014 (6)0.0006 (6)0.0010 (6)
Cl10.0284 (3)0.0192 (3)0.0169 (3)0.0026 (2)0.0001 (2)0.0017 (2)
Geometric parameters (Å, º) top
C1—O11.367 (2)C8—N41.324 (2)
C1—C21.394 (3)C8—N31.330 (2)
C1—C61.403 (3)C8—N21.335 (2)
C2—C31.385 (3)C9—O11.434 (2)
C2—H20.9500C9—H9A0.9800
C3—C41.389 (3)C9—H9B0.9800
C3—H30.9500C9—H9C0.9800
C4—C51.379 (3)N1—N21.381 (2)
C4—H40.9500N2—H2A0.8800
C5—C61.396 (3)N3—H3A0.8800
C5—H50.9500N3—H3B0.8800
C6—C71.461 (3)N4—H4A0.8800
C7—N11.275 (2)N4—H4B0.8800
C7—H70.9500
O1—C1—C2123.84 (18)N4—C8—N3120.72 (18)
O1—C1—C6115.80 (17)N4—C8—N2120.64 (18)
C2—C1—C6120.35 (18)N3—C8—N2118.63 (17)
C3—C2—C1119.67 (19)O1—C9—H9A109.5
C3—C2—H2120.2O1—C9—H9B109.5
C1—C2—H2120.2H9A—C9—H9B109.5
C2—C3—C4120.60 (18)O1—C9—H9C109.5
C2—C3—H3119.7H9A—C9—H9C109.5
C4—C3—H3119.7H9B—C9—H9C109.5
C5—C4—C3119.64 (19)C7—N1—N2115.29 (16)
C5—C4—H4120.2C8—N2—N1118.44 (16)
C3—C4—H4120.2C8—N2—H2A120.8
C4—C5—C6121.16 (19)N1—N2—H2A120.8
C4—C5—H5119.4C8—N3—H3A120.0
C6—C5—H5119.4C8—N3—H3B120.0
C5—C6—C1118.57 (18)H3A—N3—H3B120.0
C5—C6—C7121.58 (18)C8—N4—H4A120.0
C1—C6—C7119.82 (17)C8—N4—H4B120.0
N1—C7—C6120.57 (17)H4A—N4—H4B120.0
N1—C7—H7119.7C1—O1—C9117.65 (16)
C6—C7—H7119.7
O1—C1—C2—C3179.52 (17)C2—C1—C6—C7178.85 (17)
C6—C1—C2—C30.5 (3)C5—C6—C7—N15.8 (3)
C1—C2—C3—C40.5 (3)C1—C6—C7—N1176.25 (18)
C2—C3—C4—C51.1 (3)C6—C7—N1—N2178.53 (15)
C3—C4—C5—C60.8 (3)N4—C8—N2—N12.3 (3)
C4—C5—C6—C10.2 (3)N3—C8—N2—N1176.95 (15)
C4—C5—C6—C7178.17 (17)C7—N1—N2—C8178.96 (17)
O1—C1—C6—C5179.93 (16)C2—C1—O1—C98.5 (3)
C2—C1—C6—C50.8 (3)C6—C1—O1—C9172.39 (17)
O1—C1—C6—C72.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···Cl1i0.882.393.1861 (17)150
N3—H3A···Cl10.882.553.3035 (17)144
N3—H3B···Cl1i0.882.463.2435 (17)149
N4—H4A···Cl10.882.413.1964 (18)149
N4—H4B···Cl1ii0.882.623.3035 (17)135
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y1, z+1.
 

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