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In the title compound, 2 C6H5NHC(NH2)2+·CO32-·H2O, the phenyl­guanidinium cations and carbonate anions are arranged to form planes parallel to bc. The water mol­ecules are located between these planes. A three-dimensional network of hydrogen bonds is observed in the crystal and H atoms of the guanidinium cations and water mol­ecules are involved. The phenyl­guanidinium cations show a conformation different from that observed in other guanidyl derivatives.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680102178X/na6122sup1.cif
Contains datablocks LRSA0267, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680102178X/na6122Isup2.hkl
Contains datablock I

CCDC reference: 180776

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.041
  • wR factor = 0.126
  • Data-to-parameter ratio = 18.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_420 Alert C D-H Without Acceptor N12 - H12B ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); data reduction: DATARED (Vasilev, unpublished); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976).

Bis phenylguanidinium carbonate monohydrate top
Crystal data top
2C7H10N3+·CO32·H2OF(000) = 744
Mr = 350.39Dx = 1.330 Mg m3
Monoclinic, P21/cMelting point: 417-419K with decomposition K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 15.527 (3) ÅCell parameters from 22 reflections
b = 10.648 (5) Åθ = 17.9–19.9°
c = 13.081 (5) ŵ = 0.10 mm1
β = 125.98 (2)°T = 293 K
V = 1750.1 (11) Å3Prismatic, colorless
Z = 40.21 × 0.19 × 0.19 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.033
Radiation source: fine-focus sealed tubeθmax = 28.0°, θmin = 1.6°
Graphite monochromatorh = 2016
ω–2θ scansk = 1414
8538 measured reflectionsl = 017
4209 independent reflections3 standard reflections every 500 reflections
2691 reflections with I > 2σ(I) intensity decay: 0.8
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)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.126 w = 1/[σ2(Fo2) + (0.0611P)2 + 0.1716P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.013
4209 reflectionsΔρmax = 0.17 e Å3
232 parametersΔρmin = 0.21 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: none
Special details top

Experimental. Omega scan angle= 0.90 + 0.35*tanθ (degrees), hor. width of the var. aperture APT= 1.40 + 0.00*tanθ (mm), required final sigma(I)/I = 0.050, distance from center of goniometer to the aperture disk = 173 mm, vert. height ot the manually insertable slit in front of the detector = 3.0 mm.

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
O10.16191 (9)0.51546 (10)0.36802 (11)0.0442 (3)
O20.10619 (10)0.60160 (10)0.47455 (12)0.0491 (3)
O30.14447 (10)0.72283 (10)0.36863 (12)0.0484 (3)
OW0.00985 (12)0.90127 (14)0.36233 (14)0.0545 (3)
HW10.0422 (18)0.843 (2)0.350 (2)0.072 (7)*
HW20.036 (2)0.930 (2)0.288 (2)0.078 (8)*
C0.13729 (12)0.61349 (14)0.40376 (14)0.0367 (3)
N110.16829 (12)0.71604 (13)0.17014 (14)0.0475 (4)
H11A0.13800.76880.10860.057*
H11B0.15290.71580.22340.057*
N120.26185 (11)0.63616 (13)0.10054 (13)0.0462 (3)
H12A0.23160.68880.03890.055*
H12B0.30760.58350.10900.055*
N130.28304 (11)0.55444 (13)0.27824 (13)0.0454 (3)
H130.25680.54740.32040.054*
C10.23782 (12)0.63615 (14)0.18260 (14)0.0373 (3)
C110.37191 (14)0.47852 (17)0.31423 (15)0.0468 (4)
C120.36770 (19)0.35040 (19)0.3270 (2)0.0645 (5)
H120.30610.31300.30910.077*
C130.4563 (2)0.2786 (3)0.3667 (3)0.0908 (9)
H13A0.45430.19230.37610.109*
C140.5470 (2)0.3325 (3)0.3923 (3)0.0956 (10)
H140.60600.28290.41880.115*
C150.55098 (11)0.45918 (18)0.37890 (14)0.0815 (7)
H150.61230.49570.39520.098*
C160.46401 (11)0.53270 (18)0.34120 (14)0.0608 (5)
H160.46730.61920.33390.073*
N210.09399 (12)0.14365 (13)0.51848 (15)0.0507 (4)
H21A0.05580.13260.54570.061*
H21B0.12030.08000.50530.061*
N220.07274 (12)0.35735 (13)0.51638 (15)0.0518 (4)
H22A0.03440.34790.54360.062*
H22B0.08530.43140.50190.062*
N230.17285 (12)0.27767 (13)0.45696 (15)0.0486 (4)
H230.18150.35350.44180.058*
C20.11218 (13)0.25852 (15)0.49693 (15)0.0412 (4)
C210.22410 (13)0.17881 (15)0.43814 (16)0.0429 (4)
C220.33062 (15)0.15534 (19)0.52751 (19)0.0556 (5)
H220.36970.20410.60030.067*
C230.37939 (18)0.0579 (2)0.5081 (3)0.0720 (7)
H23A0.45120.04090.56850.086*
C240.3223 (2)0.0126 (2)0.4008 (3)0.0776 (7)
H240.35520.07750.38820.093*
C250.2171 (2)0.0116 (2)0.3121 (2)0.0737 (6)
H250.17850.03660.23890.088*
C260.16773 (17)0.10721 (18)0.33021 (19)0.0578 (5)
H260.09590.12340.26920.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0604 (7)0.0319 (5)0.0582 (7)0.0003 (5)0.0449 (6)0.0025 (5)
O20.0715 (8)0.0372 (6)0.0646 (8)0.0045 (5)0.0545 (7)0.0053 (5)
O30.0716 (8)0.0331 (6)0.0599 (7)0.0019 (5)0.0494 (7)0.0011 (5)
OW0.0649 (9)0.0538 (8)0.0551 (8)0.0138 (7)0.0410 (8)0.0085 (6)
C0.0389 (8)0.0342 (8)0.0415 (8)0.0024 (6)0.0261 (7)0.0043 (6)
N110.0570 (8)0.0448 (8)0.0504 (8)0.0123 (6)0.0369 (7)0.0097 (6)
N120.0520 (8)0.0484 (8)0.0487 (8)0.0105 (6)0.0354 (7)0.0116 (6)
N130.0501 (8)0.0501 (8)0.0489 (8)0.0119 (6)0.0363 (7)0.0134 (6)
C10.0376 (8)0.0362 (8)0.0401 (8)0.0018 (6)0.0240 (7)0.0006 (6)
C110.0496 (9)0.0556 (10)0.0415 (9)0.0138 (8)0.0303 (8)0.0117 (8)
C120.0810 (14)0.0568 (12)0.0762 (14)0.0202 (10)0.0576 (13)0.0224 (10)
C130.120 (2)0.0763 (16)0.1015 (19)0.0528 (16)0.0791 (18)0.0411 (14)
C140.0878 (19)0.124 (2)0.0896 (18)0.0631 (18)0.0606 (16)0.0404 (17)
C150.0495 (12)0.123 (2)0.0703 (14)0.0221 (13)0.0343 (11)0.0163 (15)
C160.0511 (11)0.0747 (13)0.0558 (11)0.0072 (10)0.0311 (9)0.0071 (10)
N210.0649 (9)0.0384 (7)0.0699 (10)0.0030 (7)0.0515 (9)0.0068 (7)
N220.0665 (9)0.0387 (7)0.0742 (10)0.0037 (7)0.0548 (9)0.0038 (7)
N230.0641 (9)0.0336 (7)0.0687 (10)0.0033 (6)0.0505 (8)0.0063 (6)
C20.0452 (8)0.0393 (8)0.0436 (9)0.0019 (7)0.0285 (8)0.0012 (7)
C210.0520 (9)0.0372 (8)0.0540 (10)0.0035 (7)0.0393 (9)0.0069 (7)
C220.0536 (10)0.0614 (12)0.0600 (11)0.0012 (9)0.0379 (10)0.0066 (9)
C230.0612 (13)0.0782 (15)0.0963 (17)0.0241 (11)0.0572 (13)0.0334 (14)
C240.113 (2)0.0557 (13)0.108 (2)0.0252 (13)0.0897 (19)0.0171 (13)
C250.1070 (19)0.0502 (12)0.0780 (15)0.0077 (12)0.0623 (15)0.0041 (11)
C260.0655 (12)0.0500 (11)0.0574 (11)0.0040 (9)0.0359 (10)0.0020 (9)
Geometric parameters (Å, º) top
O1—C1.2900 (18)C15—H150.9300
O2—C1.2775 (18)C16—H160.9300
O3—C1.2804 (18)N21—C21.322 (2)
OW—HW10.87 (2)N21—H21A0.8600
OW—HW20.86 (3)N21—H21B0.8600
N11—C11.307 (2)N22—C21.315 (2)
N11—H11A0.8600N22—H22A0.8600
N11—H11B0.8600N22—H22B0.8600
N12—C11.328 (2)N23—C21.335 (2)
N12—H12A0.8600N23—C211.426 (2)
N12—H12B0.8600N23—H230.8600
N13—C11.335 (2)C21—C261.374 (3)
N13—C111.420 (2)C21—C221.376 (3)
N13—H130.8600C22—C231.393 (3)
C11—C121.381 (3)C22—H220.9300
C11—C161.382 (2)C23—C241.363 (4)
C12—C131.381 (3)C23—H23A0.9300
C12—H120.9300C24—C251.362 (3)
C13—C141.368 (4)C24—H240.9300
C13—H13A0.9300C25—C261.376 (3)
C14—C151.366 (4)C25—H250.9300
C14—H140.9300C26—H260.9300
C15—C161.377 (3)
HW1—OW—HW2103 (2)C15—C16—H16119.9
O2—C—O3120.00 (13)C11—C16—H16119.9
O2—C—O1120.07 (13)C2—N21—H21A120.0
O3—C—O1119.93 (13)C2—N21—H21B120.0
C1—N11—H11A120.0H21A—N21—H21B120.0
C1—N11—H11B120.0C2—N22—H22A120.0
H11A—N11—H11B120.0C2—N22—H22B120.0
C1—N12—H12A120.0H22A—N22—H22B120.0
C1—N12—H12B120.0C2—N23—C21123.29 (14)
H12A—N12—H12B120.0C2—N23—H23118.4
C1—N13—C11123.74 (13)C21—N23—H23118.4
C1—N13—H13118.1N22—C2—N21121.11 (14)
C11—N13—H13118.1N22—C2—N23118.01 (15)
N11—C1—N12120.19 (14)N21—C2—N23120.88 (15)
N11—C1—N13118.82 (14)C26—C21—C22119.63 (17)
N12—C1—N13120.98 (14)C26—C21—N23120.26 (16)
C12—C11—C16119.80 (17)C22—C21—N23120.12 (16)
C12—C11—N13119.80 (17)C21—C22—C23119.4 (2)
C16—C11—N13120.35 (16)C21—C22—H22120.3
C11—C12—C13119.0 (2)C23—C22—H22120.3
C11—C12—H12120.5C24—C23—C22120.2 (2)
C13—C12—H12120.5C24—C23—H23A119.9
C14—C13—C12120.9 (2)C22—C23—H23A119.9
C14—C13—H13A119.5C25—C24—C23120.2 (2)
C12—C13—H13A119.5C25—C24—H24119.9
C15—C14—C13120.1 (2)C23—C24—H24119.9
C15—C14—H14120.0C24—C25—C26120.3 (2)
C13—C14—H14120.0C24—C25—H25119.9
C14—C15—C16119.89 (13)C26—C25—H25119.9
C14—C15—H15120.1C21—C26—C25120.3 (2)
C16—C15—H15120.1C21—C26—H26119.9
C15—C16—C11120.26 (10)C25—C26—H26119.9
C1—N13—C11—C1654.4 (2)C2—N23—C21—C2679.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
OW—HW1···O30.87 (2)1.94 (3)2.7899 (19)165 (2)
OW—HW2···O1i0.86 (3)2.03 (3)2.868 (2)166 (2)
N21—H21A···OWii0.862.012.866 (2)170
N21—H21B···OWiii0.862.513.067 (2)123
N22—H22A···O2ii0.862.122.8830 (19)147
N22—H22B···O20.861.912.769 (2)175
N23—H23···O10.861.912.750 (2)164
N11—H11A···O2iv0.862.052.889 (2)164
N11—H11B···O30.861.982.831 (2)170
N12—H12A···O3iv0.862.032.878 (2)167
N13—H13···O10.861.942.7721 (17)163
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+1, z+1; (iii) x, y1, z; (iv) x, y+3/2, z1/2.
 

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