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The hydrogensulfate anions of the title compound, C19H18N3+·HSO4-, form centrosymmetric hydrogen-bonded dimers. In the cation, the dihedral angles between the phenyl rings and the plane defined by the central guanidinium fragment are in the range 41.46 (6)-67.11 (5)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807014870/bt2317sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014870/bt2317Isup2.hkl
Contains datablock I

CCDC reference: 646755

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.035
  • wR factor = 0.103
  • Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K 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 0 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

N,N',N''-Triphenylguanidinium hydrogensulfate top
Crystal data top
C19H18N3+·HO4SF(000) = 808
Mr = 385.43Dx = 1.371 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8651 reflections
a = 12.2053 (5) Åθ = 2.5–27.2°
b = 9.4116 (4) ŵ = 0.20 mm1
c = 20.2984 (7) ÅT = 293 K
β = 126.7654 (15)°Plate, colourless
V = 1867.91 (13) Å30.39 × 0.22 × 0.12 mm
Z = 4
Data collection top
Bruker APEX2 CCD area-detector
diffractometer
4441 independent reflections
Radiation source: fine-focus sealed tube3434 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
φ and ω scansθmax = 27.9°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1516
Tmin = 0.910, Tmax = 0.976k = 1112
61192 measured reflectionsl = 2626
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0502P)2 + 0.494P]
where P = (Fo2 + 2Fc2)/3
4441 reflections(Δ/σ)max = 0.001
247 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.35 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
S10.40643 (4)0.32447 (4)0.44312 (2)0.04036 (11)
O10.30557 (11)0.44971 (12)0.41993 (7)0.0524 (3)
H10.353 (2)0.521 (2)0.4332 (13)0.079*
O20.51583 (11)0.33711 (11)0.53086 (6)0.0493 (3)
O30.32583 (12)0.19813 (12)0.42472 (7)0.0560 (3)
O40.45571 (13)0.34035 (11)0.39431 (7)0.0561 (3)
N10.59982 (12)0.01805 (14)0.44267 (7)0.0455 (3)
H1A0.60860.08260.47550.055*
N20.42903 (12)0.15318 (13)0.33702 (7)0.0441 (3)
H20.48350.22480.35850.053*
N30.44520 (12)0.09134 (12)0.31858 (7)0.0427 (3)
H3A0.46080.16890.34530.051*
C10.48911 (14)0.02650 (15)0.36404 (8)0.0396 (3)
C20.70439 (14)0.08710 (16)0.47730 (8)0.0424 (3)
C30.75284 (17)0.13919 (19)0.43523 (10)0.0543 (4)
H30.71620.10710.38250.065*
C40.85620 (18)0.2392 (2)0.47262 (12)0.0658 (5)
H40.88840.27570.44450.079*
C50.91200 (18)0.2853 (2)0.55133 (13)0.0690 (5)
H50.98110.35330.57600.083*
C60.86560 (18)0.2310 (2)0.59321 (11)0.0653 (5)
H60.90420.26120.64660.078*
C70.76181 (16)0.13154 (19)0.55643 (9)0.0532 (4)
H70.73070.09460.58500.064*
C80.28827 (14)0.18799 (16)0.27793 (8)0.0426 (3)
C90.25959 (18)0.33018 (18)0.25691 (10)0.0553 (4)
H90.33050.39530.27780.066*
C100.1248 (2)0.3751 (2)0.20465 (12)0.0713 (5)
H100.10540.47070.19080.086*
C110.02014 (19)0.2795 (3)0.17329 (11)0.0743 (6)
H110.07020.30980.13780.089*
C120.04883 (18)0.1390 (2)0.19427 (12)0.0702 (5)
H120.02270.07460.17280.084*
C130.18306 (16)0.09073 (19)0.24714 (10)0.0552 (4)
H130.20170.00480.26150.066*
C140.37676 (13)0.10838 (14)0.23290 (8)0.0375 (3)
C150.39207 (15)0.01328 (16)0.18697 (9)0.0456 (3)
H150.44410.06860.21110.055*
C160.32888 (17)0.04176 (19)0.10467 (9)0.0539 (4)
H160.33840.02180.07330.065*
C170.25215 (17)0.1630 (2)0.06859 (10)0.0565 (4)
H170.21020.18120.01320.068*
C180.23800 (16)0.25663 (19)0.11466 (10)0.0558 (4)
H180.18610.33850.09030.067*
C190.29994 (15)0.23082 (16)0.19699 (9)0.0470 (3)
H190.29010.29500.22800.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0472 (2)0.03614 (19)0.03978 (19)0.00068 (14)0.02711 (17)0.00020 (13)
O10.0449 (6)0.0487 (6)0.0552 (6)0.0059 (5)0.0254 (5)0.0062 (5)
O20.0514 (6)0.0448 (6)0.0410 (5)0.0043 (5)0.0219 (5)0.0048 (4)
O30.0623 (7)0.0472 (6)0.0552 (6)0.0119 (5)0.0333 (6)0.0005 (5)
O40.0812 (8)0.0467 (6)0.0629 (7)0.0105 (5)0.0551 (7)0.0099 (5)
N10.0460 (6)0.0500 (7)0.0333 (6)0.0020 (5)0.0198 (5)0.0050 (5)
N20.0372 (6)0.0413 (7)0.0410 (6)0.0046 (5)0.0166 (5)0.0071 (5)
N30.0521 (7)0.0374 (6)0.0336 (6)0.0041 (5)0.0229 (5)0.0002 (5)
C10.0406 (7)0.0441 (7)0.0344 (7)0.0039 (6)0.0226 (6)0.0022 (6)
C20.0390 (7)0.0448 (8)0.0378 (7)0.0049 (6)0.0198 (6)0.0013 (6)
C30.0573 (9)0.0587 (10)0.0515 (9)0.0023 (8)0.0349 (8)0.0029 (7)
C40.0612 (10)0.0650 (11)0.0814 (13)0.0039 (9)0.0482 (10)0.0025 (10)
C50.0503 (9)0.0611 (11)0.0794 (13)0.0070 (8)0.0302 (10)0.0131 (10)
C60.0555 (10)0.0708 (12)0.0517 (9)0.0035 (9)0.0224 (8)0.0155 (9)
C70.0500 (9)0.0627 (10)0.0419 (8)0.0031 (7)0.0248 (7)0.0022 (7)
C80.0388 (7)0.0536 (8)0.0330 (7)0.0007 (6)0.0202 (6)0.0060 (6)
C90.0499 (9)0.0590 (10)0.0506 (9)0.0032 (7)0.0267 (8)0.0061 (7)
C100.0596 (11)0.0783 (13)0.0611 (11)0.0212 (10)0.0282 (9)0.0153 (10)
C110.0447 (9)0.1082 (17)0.0522 (10)0.0150 (11)0.0195 (8)0.0057 (11)
C120.0426 (9)0.0966 (15)0.0647 (11)0.0140 (10)0.0285 (8)0.0304 (11)
C130.0469 (8)0.0613 (10)0.0571 (9)0.0081 (7)0.0310 (8)0.0168 (8)
C140.0365 (6)0.0404 (7)0.0336 (6)0.0024 (6)0.0200 (6)0.0016 (5)
C150.0493 (8)0.0467 (8)0.0425 (8)0.0035 (6)0.0284 (7)0.0013 (6)
C160.0574 (9)0.0676 (10)0.0435 (8)0.0082 (8)0.0339 (8)0.0075 (7)
C170.0488 (9)0.0793 (12)0.0359 (8)0.0069 (8)0.0223 (7)0.0075 (8)
C180.0480 (8)0.0602 (10)0.0505 (9)0.0068 (7)0.0248 (7)0.0189 (8)
C190.0486 (8)0.0436 (8)0.0470 (8)0.0041 (6)0.0277 (7)0.0048 (6)
Geometric parameters (Å, º) top
S1—O41.4420 (11)C7—H70.9300
S1—O31.4427 (11)C8—C91.384 (2)
S1—O21.4568 (11)C8—C131.384 (2)
S1—O11.5596 (11)C9—C101.386 (2)
O1—H10.82 (2)C9—H90.9300
N1—C11.3408 (17)C10—C111.369 (3)
N1—C21.4243 (19)C10—H100.9300
N1—H1A0.8600C11—C121.369 (3)
N2—C11.3336 (18)C11—H110.9300
N2—C81.4251 (18)C12—C131.392 (2)
N2—H20.8600C12—H120.9300
N3—C11.3329 (18)C13—H130.9300
N3—C141.4174 (16)C14—C151.383 (2)
N3—H3A0.8600C14—C191.386 (2)
C2—C71.378 (2)C15—C161.384 (2)
C2—C31.387 (2)C15—H150.9300
C3—C41.381 (2)C16—C171.376 (2)
C3—H30.9300C16—H160.9300
C4—C51.379 (3)C17—C181.369 (3)
C4—H40.9300C17—H170.9300
C5—C61.372 (3)C18—C191.382 (2)
C5—H50.9300C18—H180.9300
C6—C71.381 (3)C19—H190.9300
C6—H60.9300
O4—S1—O3114.07 (7)C9—C8—C13120.33 (15)
O4—S1—O2112.18 (7)C9—C8—N2115.89 (13)
O3—S1—O2111.58 (6)C13—C8—N2123.58 (14)
O4—S1—O1107.02 (7)C8—C9—C10119.72 (17)
O3—S1—O1104.60 (7)C8—C9—H9120.1
O2—S1—O1106.71 (6)C10—C9—H9120.1
S1—O1—H1104.5 (15)C11—C10—C9120.4 (2)
C1—N1—C2126.55 (12)C11—C10—H10119.8
C1—N1—H1A116.7C9—C10—H10119.8
C2—N1—H1A116.7C10—C11—C12119.77 (18)
C1—N2—C8129.86 (12)C10—C11—H11120.1
C1—N2—H2115.1C12—C11—H11120.1
C8—N2—H2115.1C11—C12—C13121.26 (18)
C1—N3—C14129.87 (12)C11—C12—H12119.4
C1—N3—H3A115.1C13—C12—H12119.4
C14—N3—H3A115.1C8—C13—C12118.55 (18)
N3—C1—N2124.39 (12)C8—C13—H13120.7
N3—C1—N1118.41 (13)C12—C13—H13120.7
N2—C1—N1117.19 (12)C15—C14—C19120.35 (13)
C7—C2—C3120.24 (15)C15—C14—N3122.38 (12)
C7—C2—N1117.80 (13)C19—C14—N3117.12 (12)
C3—C2—N1121.88 (13)C14—C15—C16119.06 (14)
C4—C3—C2119.24 (16)C14—C15—H15120.5
C4—C3—H3120.4C16—C15—H15120.5
C2—C3—H3120.4C17—C16—C15120.87 (15)
C5—C4—C3120.43 (17)C17—C16—H16119.6
C5—C4—H4119.8C15—C16—H16119.6
C3—C4—H4119.8C18—C17—C16119.61 (14)
C6—C5—C4119.98 (18)C18—C17—H17120.2
C6—C5—H5120.0C16—C17—H17120.2
C4—C5—H5120.0C17—C18—C19120.75 (15)
C5—C6—C7120.22 (17)C17—C18—H18119.6
C5—C6—H6119.9C19—C18—H18119.6
C7—C6—H6119.9C18—C19—C14119.36 (15)
C2—C7—C6119.86 (16)C18—C19—H19120.3
C2—C7—H7120.1C14—C19—H19120.3
C6—C7—H7120.1
C14—N3—C1—N231.4 (2)C13—C8—C9—C100.1 (2)
C14—N3—C1—N1149.68 (14)N2—C8—C9—C10175.14 (15)
C8—N2—C1—N332.2 (2)C8—C9—C10—C110.5 (3)
C8—N2—C1—N1146.74 (14)C9—C10—C11—C120.6 (3)
C2—N1—C1—N323.2 (2)C10—C11—C12—C130.1 (3)
C2—N1—C1—N2157.84 (14)C9—C8—C13—C120.6 (2)
C1—N1—C2—C7144.01 (15)N2—C8—C13—C12175.26 (15)
C1—N1—C2—C339.1 (2)C11—C12—C13—C80.6 (3)
C7—C2—C3—C42.0 (2)C1—N3—C14—C1527.4 (2)
N1—C2—C3—C4178.80 (15)C1—N3—C14—C19157.03 (14)
C2—C3—C4—C50.9 (3)C19—C14—C15—C160.4 (2)
C3—C4—C5—C60.5 (3)N3—C14—C15—C16175.90 (13)
C4—C5—C6—C70.9 (3)C14—C15—C16—C170.2 (2)
C3—C2—C7—C61.7 (2)C15—C16—C17—C180.0 (2)
N1—C2—C7—C6178.59 (15)C16—C17—C18—C190.0 (2)
C5—C6—C7—C20.2 (3)C17—C18—C19—C140.2 (2)
C1—N2—C8—C9173.67 (15)C15—C14—C19—C180.4 (2)
C1—N2—C8—C1311.5 (2)N3—C14—C19—C18176.10 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.82 (2)1.86 (2)2.6774 (16)170 (2)
N1—H1A···O3ii0.862.002.8314 (16)164
N2—H2···O2ii0.862.482.9123 (15)112
N3—H3A···O40.861.922.7633 (15)168
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z+1.
 

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