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
CCDC reference: 180776
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
Data collection: CAD-4 Software (Enraf-Nonius, 1989); data reduction: DATARED (Vasilev, unpublished); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII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−·H2O | F(000) = 744 |
Mr = 350.39 | Dx = 1.330 Mg m−3 |
Monoclinic, P21/c | Melting point: 417-419K with decomposition K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 15.527 (3) Å | Cell parameters from 22 reflections |
b = 10.648 (5) Å | θ = 17.9–19.9° |
c = 13.081 (5) Å | µ = 0.10 mm−1 |
β = 125.98 (2)° | T = 293 K |
V = 1750.1 (11) Å3 | Prismatic, colorless |
Z = 4 | 0.21 × 0.19 × 0.19 mm |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.033 |
Radiation source: fine-focus sealed tube | θmax = 28.0°, θmin = 1.6° |
Graphite monochromator | h = −20→16 |
ω–2θ scans | k = −14→14 |
8538 measured reflections | l = 0→17 |
4209 independent reflections | 3 standard reflections every 500 reflections |
2691 reflections with I > 2σ(I) | intensity decay: 0.8 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H 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 reflections | Δρmax = 0.17 e Å−3 |
232 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
O1 | 0.16191 (9) | 0.51546 (10) | 0.36802 (11) | 0.0442 (3) | |
O2 | 0.10619 (10) | 0.60160 (10) | 0.47455 (12) | 0.0491 (3) | |
O3 | 0.14447 (10) | 0.72283 (10) | 0.36863 (12) | 0.0484 (3) | |
OW | 0.00985 (12) | 0.90127 (14) | 0.36233 (14) | 0.0545 (3) | |
HW1 | 0.0422 (18) | 0.843 (2) | 0.350 (2) | 0.072 (7)* | |
HW2 | −0.036 (2) | 0.930 (2) | 0.288 (2) | 0.078 (8)* | |
C | 0.13729 (12) | 0.61349 (14) | 0.40376 (14) | 0.0367 (3) | |
N11 | 0.16829 (12) | 0.71604 (13) | 0.17014 (14) | 0.0475 (4) | |
H11A | 0.1380 | 0.7688 | 0.1086 | 0.057* | |
H11B | 0.1529 | 0.7158 | 0.2234 | 0.057* | |
N12 | 0.26185 (11) | 0.63616 (13) | 0.10054 (13) | 0.0462 (3) | |
H12A | 0.2316 | 0.6888 | 0.0389 | 0.055* | |
H12B | 0.3076 | 0.5835 | 0.1090 | 0.055* | |
N13 | 0.28304 (11) | 0.55444 (13) | 0.27824 (13) | 0.0454 (3) | |
H13 | 0.2568 | 0.5474 | 0.3204 | 0.054* | |
C1 | 0.23782 (12) | 0.63615 (14) | 0.18260 (14) | 0.0373 (3) | |
C11 | 0.37191 (14) | 0.47852 (17) | 0.31423 (15) | 0.0468 (4) | |
C12 | 0.36770 (19) | 0.35040 (19) | 0.3270 (2) | 0.0645 (5) | |
H12 | 0.3061 | 0.3130 | 0.3091 | 0.077* | |
C13 | 0.4563 (2) | 0.2786 (3) | 0.3667 (3) | 0.0908 (9) | |
H13A | 0.4543 | 0.1923 | 0.3761 | 0.109* | |
C14 | 0.5470 (2) | 0.3325 (3) | 0.3923 (3) | 0.0956 (10) | |
H14 | 0.6060 | 0.2829 | 0.4188 | 0.115* | |
C15 | 0.55098 (11) | 0.45918 (18) | 0.37890 (14) | 0.0815 (7) | |
H15 | 0.6123 | 0.4957 | 0.3952 | 0.098* | |
C16 | 0.46401 (11) | 0.53270 (18) | 0.34120 (14) | 0.0608 (5) | |
H16 | 0.4673 | 0.6192 | 0.3339 | 0.073* | |
N21 | 0.09399 (12) | 0.14365 (13) | 0.51848 (15) | 0.0507 (4) | |
H21A | 0.0558 | 0.1326 | 0.5457 | 0.061* | |
H21B | 0.1203 | 0.0800 | 0.5053 | 0.061* | |
N22 | 0.07274 (12) | 0.35735 (13) | 0.51638 (15) | 0.0518 (4) | |
H22A | 0.0344 | 0.3479 | 0.5436 | 0.062* | |
H22B | 0.0853 | 0.4314 | 0.5019 | 0.062* | |
N23 | 0.17285 (12) | 0.27767 (13) | 0.45696 (15) | 0.0486 (4) | |
H23 | 0.1815 | 0.3535 | 0.4418 | 0.058* | |
C2 | 0.11218 (13) | 0.25852 (15) | 0.49693 (15) | 0.0412 (4) | |
C21 | 0.22410 (13) | 0.17881 (15) | 0.43814 (16) | 0.0429 (4) | |
C22 | 0.33062 (15) | 0.15534 (19) | 0.52751 (19) | 0.0556 (5) | |
H22 | 0.3697 | 0.2041 | 0.6003 | 0.067* | |
C23 | 0.37939 (18) | 0.0579 (2) | 0.5081 (3) | 0.0720 (7) | |
H23A | 0.4512 | 0.0409 | 0.5685 | 0.086* | |
C24 | 0.3223 (2) | −0.0126 (2) | 0.4008 (3) | 0.0776 (7) | |
H24 | 0.3552 | −0.0775 | 0.3882 | 0.093* | |
C25 | 0.2171 (2) | 0.0116 (2) | 0.3121 (2) | 0.0737 (6) | |
H25 | 0.1785 | −0.0366 | 0.2389 | 0.088* | |
C26 | 0.16773 (17) | 0.10721 (18) | 0.33021 (19) | 0.0578 (5) | |
H26 | 0.0959 | 0.1234 | 0.2692 | 0.069* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0604 (7) | 0.0319 (5) | 0.0582 (7) | −0.0003 (5) | 0.0449 (6) | −0.0025 (5) |
O2 | 0.0715 (8) | 0.0372 (6) | 0.0646 (8) | −0.0045 (5) | 0.0545 (7) | −0.0053 (5) |
O3 | 0.0716 (8) | 0.0331 (6) | 0.0599 (7) | 0.0019 (5) | 0.0494 (7) | 0.0011 (5) |
OW | 0.0649 (9) | 0.0538 (8) | 0.0551 (8) | 0.0138 (7) | 0.0410 (8) | 0.0085 (6) |
C | 0.0389 (8) | 0.0342 (8) | 0.0415 (8) | −0.0024 (6) | 0.0261 (7) | −0.0043 (6) |
N11 | 0.0570 (8) | 0.0448 (8) | 0.0504 (8) | 0.0123 (6) | 0.0369 (7) | 0.0097 (6) |
N12 | 0.0520 (8) | 0.0484 (8) | 0.0487 (8) | 0.0105 (6) | 0.0354 (7) | 0.0116 (6) |
N13 | 0.0501 (8) | 0.0501 (8) | 0.0489 (8) | 0.0119 (6) | 0.0363 (7) | 0.0134 (6) |
C1 | 0.0376 (8) | 0.0362 (8) | 0.0401 (8) | −0.0018 (6) | 0.0240 (7) | 0.0006 (6) |
C11 | 0.0496 (9) | 0.0556 (10) | 0.0415 (9) | 0.0138 (8) | 0.0303 (8) | 0.0117 (8) |
C12 | 0.0810 (14) | 0.0568 (12) | 0.0762 (14) | 0.0202 (10) | 0.0576 (13) | 0.0224 (10) |
C13 | 0.120 (2) | 0.0763 (16) | 0.1015 (19) | 0.0528 (16) | 0.0791 (18) | 0.0411 (14) |
C14 | 0.0878 (19) | 0.124 (2) | 0.0896 (18) | 0.0631 (18) | 0.0606 (16) | 0.0404 (17) |
C15 | 0.0495 (12) | 0.123 (2) | 0.0703 (14) | 0.0221 (13) | 0.0343 (11) | 0.0163 (15) |
C16 | 0.0511 (11) | 0.0747 (13) | 0.0558 (11) | 0.0072 (10) | 0.0311 (9) | 0.0071 (10) |
N21 | 0.0649 (9) | 0.0384 (7) | 0.0699 (10) | 0.0030 (7) | 0.0515 (9) | 0.0068 (7) |
N22 | 0.0665 (9) | 0.0387 (7) | 0.0742 (10) | −0.0037 (7) | 0.0548 (9) | −0.0038 (7) |
N23 | 0.0641 (9) | 0.0336 (7) | 0.0687 (10) | 0.0033 (6) | 0.0505 (8) | 0.0063 (6) |
C2 | 0.0452 (8) | 0.0393 (8) | 0.0436 (9) | −0.0019 (7) | 0.0285 (8) | 0.0012 (7) |
C21 | 0.0520 (9) | 0.0372 (8) | 0.0540 (10) | 0.0035 (7) | 0.0393 (9) | 0.0069 (7) |
C22 | 0.0536 (10) | 0.0614 (12) | 0.0600 (11) | −0.0012 (9) | 0.0379 (10) | 0.0066 (9) |
C23 | 0.0612 (13) | 0.0782 (15) | 0.0963 (17) | 0.0241 (11) | 0.0572 (13) | 0.0334 (14) |
C24 | 0.113 (2) | 0.0557 (13) | 0.108 (2) | 0.0252 (13) | 0.0897 (19) | 0.0171 (13) |
C25 | 0.1070 (19) | 0.0502 (12) | 0.0780 (15) | 0.0077 (12) | 0.0623 (15) | −0.0041 (11) |
C26 | 0.0655 (12) | 0.0500 (11) | 0.0574 (11) | 0.0040 (9) | 0.0359 (10) | 0.0020 (9) |
Geometric parameters (Å, º) top
O1—C | 1.2900 (18) | C15—H15 | 0.9300 |
O2—C | 1.2775 (18) | C16—H16 | 0.9300 |
O3—C | 1.2804 (18) | N21—C2 | 1.322 (2) |
OW—HW1 | 0.87 (2) | N21—H21A | 0.8600 |
OW—HW2 | 0.86 (3) | N21—H21B | 0.8600 |
N11—C1 | 1.307 (2) | N22—C2 | 1.315 (2) |
N11—H11A | 0.8600 | N22—H22A | 0.8600 |
N11—H11B | 0.8600 | N22—H22B | 0.8600 |
N12—C1 | 1.328 (2) | N23—C2 | 1.335 (2) |
N12—H12A | 0.8600 | N23—C21 | 1.426 (2) |
N12—H12B | 0.8600 | N23—H23 | 0.8600 |
N13—C1 | 1.335 (2) | C21—C26 | 1.374 (3) |
N13—C11 | 1.420 (2) | C21—C22 | 1.376 (3) |
N13—H13 | 0.8600 | C22—C23 | 1.393 (3) |
C11—C12 | 1.381 (3) | C22—H22 | 0.9300 |
C11—C16 | 1.382 (2) | C23—C24 | 1.363 (4) |
C12—C13 | 1.381 (3) | C23—H23A | 0.9300 |
C12—H12 | 0.9300 | C24—C25 | 1.362 (3) |
C13—C14 | 1.368 (4) | C24—H24 | 0.9300 |
C13—H13A | 0.9300 | C25—C26 | 1.376 (3) |
C14—C15 | 1.366 (4) | C25—H25 | 0.9300 |
C14—H14 | 0.9300 | C26—H26 | 0.9300 |
C15—C16 | 1.377 (3) | | |
| | | |
HW1—OW—HW2 | 103 (2) | C15—C16—H16 | 119.9 |
O2—C—O3 | 120.00 (13) | C11—C16—H16 | 119.9 |
O2—C—O1 | 120.07 (13) | C2—N21—H21A | 120.0 |
O3—C—O1 | 119.93 (13) | C2—N21—H21B | 120.0 |
C1—N11—H11A | 120.0 | H21A—N21—H21B | 120.0 |
C1—N11—H11B | 120.0 | C2—N22—H22A | 120.0 |
H11A—N11—H11B | 120.0 | C2—N22—H22B | 120.0 |
C1—N12—H12A | 120.0 | H22A—N22—H22B | 120.0 |
C1—N12—H12B | 120.0 | C2—N23—C21 | 123.29 (14) |
H12A—N12—H12B | 120.0 | C2—N23—H23 | 118.4 |
C1—N13—C11 | 123.74 (13) | C21—N23—H23 | 118.4 |
C1—N13—H13 | 118.1 | N22—C2—N21 | 121.11 (14) |
C11—N13—H13 | 118.1 | N22—C2—N23 | 118.01 (15) |
N11—C1—N12 | 120.19 (14) | N21—C2—N23 | 120.88 (15) |
N11—C1—N13 | 118.82 (14) | C26—C21—C22 | 119.63 (17) |
N12—C1—N13 | 120.98 (14) | C26—C21—N23 | 120.26 (16) |
C12—C11—C16 | 119.80 (17) | C22—C21—N23 | 120.12 (16) |
C12—C11—N13 | 119.80 (17) | C21—C22—C23 | 119.4 (2) |
C16—C11—N13 | 120.35 (16) | C21—C22—H22 | 120.3 |
C11—C12—C13 | 119.0 (2) | C23—C22—H22 | 120.3 |
C11—C12—H12 | 120.5 | C24—C23—C22 | 120.2 (2) |
C13—C12—H12 | 120.5 | C24—C23—H23A | 119.9 |
C14—C13—C12 | 120.9 (2) | C22—C23—H23A | 119.9 |
C14—C13—H13A | 119.5 | C25—C24—C23 | 120.2 (2) |
C12—C13—H13A | 119.5 | C25—C24—H24 | 119.9 |
C15—C14—C13 | 120.1 (2) | C23—C24—H24 | 119.9 |
C15—C14—H14 | 120.0 | C24—C25—C26 | 120.3 (2) |
C13—C14—H14 | 120.0 | C24—C25—H25 | 119.9 |
C14—C15—C16 | 119.89 (13) | C26—C25—H25 | 119.9 |
C14—C15—H15 | 120.1 | C21—C26—C25 | 120.3 (2) |
C16—C15—H15 | 120.1 | C21—C26—H26 | 119.9 |
C15—C16—C11 | 120.26 (10) | C25—C26—H26 | 119.9 |
| | | |
C1—N13—C11—C16 | 54.4 (2) | C2—N23—C21—C26 | 79.7 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
OW—HW1···O3 | 0.87 (2) | 1.94 (3) | 2.7899 (19) | 165 (2) |
OW—HW2···O1i | 0.86 (3) | 2.03 (3) | 2.868 (2) | 166 (2) |
N21—H21A···OWii | 0.86 | 2.01 | 2.866 (2) | 170 |
N21—H21B···OWiii | 0.86 | 2.51 | 3.067 (2) | 123 |
N22—H22A···O2ii | 0.86 | 2.12 | 2.8830 (19) | 147 |
N22—H22B···O2 | 0.86 | 1.91 | 2.769 (2) | 175 |
N23—H23···O1 | 0.86 | 1.91 | 2.750 (2) | 164 |
N11—H11A···O2iv | 0.86 | 2.05 | 2.889 (2) | 164 |
N11—H11B···O3 | 0.86 | 1.98 | 2.831 (2) | 170 |
N12—H12A···O3iv | 0.86 | 2.03 | 2.878 (2) | 167 |
N13—H13···O1 | 0.86 | 1.94 | 2.7721 (17) | 163 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x, −y+1, −z+1; (iii) x, y−1, z; (iv) x, −y+3/2, z−1/2. |