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In the title compound, C8H12N3O+·Cl, all bond lengths and angles show normal values. The crystal packing is stabilized by inter­molecular N—H...Cl and N—H...O hydrogen bonds, which link the mol­ecules into infinite ribbons running along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806053219/cv2157sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806053219/cv2157Isup2.hkl
Contains datablock I

CCDC reference: 633668

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.039
  • wR factor = 0.101
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 Cl
Alert level G PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 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: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 1999); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

4-Methoxyphenylguanidinium chloride top
Crystal data top
C8H12N3O+·ClZ = 2
Mr = 201.66F(000) = 212
Triclinic, P1Dx = 1.373 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.605 (4) ÅCell parameters from 1274 reflections
b = 7.618 (5) Åθ = 2.8–27.9°
c = 10.497 (7) ŵ = 0.36 mm1
α = 70.778 (8)°T = 298 K
β = 78.696 (9)°Block, colourless
γ = 89.888 (9)°0.49 × 0.46 × 0.38 mm
V = 487.9 (5) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
1778 independent reflections
Radiation source: fine-focus sealed tube1519 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
φ and ω scansθmax = 25.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 77
Tmin = 0.845, Tmax = 0.877k = 97
2626 measured reflectionsl = 1212
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.101 w = 1/[σ2(Fo2) + (0.0468P)2 + 0.1401P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
1778 reflectionsΔρmax = 0.22 e Å3
119 parametersΔρmin = 0.23 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.072 (8)
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
Cl10.25894 (8)0.73591 (7)0.43247 (6)0.0461 (2)
O10.6974 (2)0.2980 (2)0.12850 (14)0.0450 (4)
N10.0093 (3)0.1347 (2)0.28900 (18)0.0459 (5)
H1A0.04700.01790.32440.055*
N20.0801 (3)0.4303 (3)0.2887 (2)0.0499 (5)
H2A0.15520.50280.32290.060*
H2B0.02150.47650.21990.060*
N30.2762 (3)0.1745 (3)0.44760 (19)0.0520 (5)
H3B0.35290.24490.48300.062*
H3C0.30050.05550.48100.062*
C10.6871 (4)0.2778 (4)0.2588 (2)0.0515 (6)
H1B0.82210.30560.31790.077*
H1C0.59250.36210.30140.077*
H1D0.64000.15210.24400.077*
C20.1546 (3)0.1783 (3)0.0517 (2)0.0432 (5)
H2C0.02720.14700.03700.052*
C30.3284 (3)0.2130 (3)0.0539 (2)0.0413 (5)
H3A0.31830.20350.13850.050*
C40.5164 (3)0.2619 (3)0.0318 (2)0.0355 (5)
C50.5299 (3)0.2785 (3)0.0941 (2)0.0408 (5)
H5A0.65610.31430.10800.049*
C60.3562 (3)0.2418 (3)0.1987 (2)0.0412 (5)
H6A0.36560.25240.28320.049*
C70.1686 (3)0.1896 (3)0.1780 (2)0.0375 (5)
C80.1205 (3)0.2492 (3)0.3416 (2)0.0384 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0403 (3)0.0459 (3)0.0508 (4)0.0011 (2)0.0037 (2)0.0220 (3)
O10.0404 (8)0.0537 (10)0.0408 (8)0.0022 (7)0.0010 (6)0.0212 (7)
N10.0450 (10)0.0357 (10)0.0507 (11)0.0023 (8)0.0096 (8)0.0175 (9)
N20.0535 (11)0.0413 (11)0.0552 (12)0.0091 (9)0.0020 (9)0.0218 (9)
N30.0423 (11)0.0597 (12)0.0534 (12)0.0024 (9)0.0053 (9)0.0270 (10)
C10.0540 (14)0.0590 (15)0.0414 (12)0.0019 (11)0.0025 (10)0.0237 (11)
C20.0348 (11)0.0488 (13)0.0524 (13)0.0010 (9)0.0075 (10)0.0263 (11)
C30.0423 (12)0.0470 (13)0.0394 (11)0.0048 (9)0.0079 (9)0.0212 (10)
C40.0372 (11)0.0302 (10)0.0379 (11)0.0042 (8)0.0034 (8)0.0122 (9)
C50.0379 (11)0.0443 (12)0.0426 (11)0.0001 (9)0.0087 (9)0.0177 (10)
C60.0482 (12)0.0420 (12)0.0364 (11)0.0020 (9)0.0074 (9)0.0181 (10)
C70.0388 (11)0.0309 (10)0.0399 (11)0.0026 (8)0.0009 (9)0.0130 (9)
C80.0357 (11)0.0448 (13)0.0386 (11)0.0043 (9)0.0076 (9)0.0194 (10)
Geometric parameters (Å, º) top
O1—C41.370 (2)C1—H1C0.9600
O1—C11.440 (3)C1—H1D0.9600
N1—C81.327 (3)C2—C71.377 (3)
N1—C71.434 (3)C2—C31.387 (3)
N1—H1A0.8600C2—H2C0.9300
N2—C81.312 (3)C3—C41.380 (3)
N2—H2A0.8600C3—H3A0.9300
N2—H2B0.8600C4—C51.388 (3)
N3—C81.325 (3)C5—C61.380 (3)
N3—H3B0.8600C5—H5A0.9300
N3—H3C0.8600C6—C71.381 (3)
C1—H1B0.9600C6—H6A0.9300
C4—O1—C1116.65 (16)C4—C3—C2119.24 (19)
C8—N1—C7125.47 (18)C4—C3—H3A120.4
C8—N1—H1A117.3C2—C3—H3A120.4
C7—N1—H1A117.3O1—C4—C3123.99 (18)
C8—N2—H2A120.0O1—C4—C5115.88 (18)
C8—N2—H2B120.0C3—C4—C5120.13 (18)
H2A—N2—H2B120.0C6—C5—C4120.04 (19)
C8—N3—H3B120.0C6—C5—H5A120.0
C8—N3—H3C120.0C4—C5—H5A120.0
H3B—N3—H3C120.0C5—C6—C7120.06 (19)
O1—C1—H1B109.5C5—C6—H6A120.0
O1—C1—H1C109.5C7—C6—H6A120.0
H1B—C1—H1C109.5C2—C7—C6119.73 (18)
O1—C1—H1D109.5C2—C7—N1119.29 (19)
H1B—C1—H1D109.5C6—C7—N1120.85 (19)
H1C—C1—H1D109.5N2—C8—N3121.23 (19)
C7—C2—C3120.77 (19)N2—C8—N1121.09 (19)
C7—C2—H2C119.6N3—C8—N1117.7 (2)
C3—C2—H2C119.6
C7—C2—C3—C40.9 (3)C3—C2—C7—C62.1 (3)
C1—O1—C4—C31.7 (3)C3—C2—C7—N1173.79 (19)
C1—O1—C4—C5178.77 (19)C5—C6—C7—C21.5 (3)
C2—C3—C4—O1179.57 (19)C5—C6—C7—N1174.34 (19)
C2—C3—C4—C50.9 (3)C8—N1—C7—C2109.6 (2)
O1—C4—C5—C6178.93 (18)C8—N1—C7—C674.6 (3)
C3—C4—C5—C61.5 (3)C7—N1—C8—N23.7 (3)
C4—C5—C6—C70.3 (3)C7—N1—C8—N3177.62 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···Cl10.862.443.270 (2)161
N1—H1A···Cl1i0.862.383.202 (2)161
N3—H3B···Cl1ii0.862.563.244 (3)137
N3—H3C···Cl1i0.862.653.397 (3)146
N2—H2B···O1iii0.862.363.093 (3)144
Symmetry codes: (i) x, y1, z; (ii) x1, y+1, z+1; (iii) x+1, y+1, z.
 

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