In the title compound, C
4H
8N
3O
+·C
7H
5O
2−, the asymmetric unit comprises one creatininium cation and one benzoate anion. Intermolecular N—H
O hydrogen bonds link the cations and anions into ion pairs, which are further linked into zigzag chains by other N—H
O hydrogen bonds. The crystal packing also exhibits weak intermolecular C—H
O hydrogen bonds and dipole–dipole interactions.
Supporting information
CCDC reference: 642959
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.037
- wR factor = 0.102
- Data-to-parameter ratio = 12.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
C7 H5 O2
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
1 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
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.
1-Methyl-4-oxotetrahydro-2
H-imidazol-2-iminium benzoate
top
Crystal data top
C4H8N3O+·C7H5O2− | F(000) = 496 |
Mr = 235.24 | Dx = 1.356 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5569 reflections |
a = 8.5574 (5) Å | θ = 2.7–27.4° |
b = 6.2094 (4) Å | µ = 0.10 mm−1 |
c = 22.0169 (14) Å | T = 293 K |
β = 99.904 (1)° | Block, colourless |
V = 1152.46 (12) Å3 | 0.21 × 0.14 × 0.10 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 1849 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.020 |
Graphite monochromator | θmax = 25.0°, θmin = 1.9° |
ω scans | h = −10→10 |
10515 measured reflections | k = −7→7 |
2030 independent reflections | l = −26→26 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.102 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0576P)2 + 0.1908P] where P = (Fo2 + 2Fc2)/3 |
2030 reflections | (Δ/σ)max = 0.001 |
167 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C2 | 0.51063 (14) | 0.1130 (2) | 0.63994 (5) | 0.0433 (3) | |
C4 | 0.42380 (16) | 0.1822 (2) | 0.53974 (6) | 0.0505 (3) | |
C5 | 0.54536 (18) | 0.3498 (2) | 0.56494 (6) | 0.0553 (4) | |
H5A | 0.6361 | 0.3450 | 0.5439 | 0.066* | |
H5B | 0.5000 | 0.4933 | 0.5611 | 0.066* | |
C7 | 0.69483 (18) | 0.4153 (3) | 0.67350 (7) | 0.0599 (4) | |
H7A | 0.7196 | 0.3374 | 0.7116 | 0.090* | |
H7B | 0.6441 | 0.5487 | 0.6805 | 0.090* | |
H7C | 0.7908 | 0.4443 | 0.6579 | 0.090* | |
N1 | 0.58928 (13) | 0.28774 (18) | 0.62907 (5) | 0.0509 (3) | |
N3 | 0.41224 (13) | 0.0471 (2) | 0.58814 (5) | 0.0482 (3) | |
H3N | 0.5821 (19) | 0.056 (3) | 0.7266 (8) | 0.062 (4)* | |
N6 | 0.52016 (15) | 0.0086 (2) | 0.69217 (5) | 0.0523 (3) | |
H6N | 0.355 (2) | −0.081 (3) | 0.5874 (8) | 0.075 (5)* | |
H7N | 0.458 (2) | −0.112 (3) | 0.6923 (8) | 0.076 (5)* | |
O8 | 0.35158 (13) | 0.16664 (18) | 0.48779 (4) | 0.0654 (3) | |
C9 | 0.25012 (15) | −0.4131 (2) | 0.63998 (6) | 0.0478 (3) | |
C10 | 0.14474 (15) | −0.6085 (2) | 0.63640 (6) | 0.0463 (3) | |
C11 | 0.05767 (17) | −0.6708 (3) | 0.58000 (7) | 0.0599 (4) | |
H11 | 0.0628 | −0.5886 | 0.5451 | 0.072* | |
C12 | −0.03606 (19) | −0.8520 (3) | 0.57489 (8) | 0.0720 (5) | |
H12 | −0.0945 | −0.8908 | 0.5369 | 0.086* | |
C13 | −0.0431 (2) | −0.9751 (3) | 0.62593 (10) | 0.0781 (5) | |
H13 | −0.1057 | −1.0983 | 0.6226 | 0.094* | |
C14 | 0.0426 (2) | −0.9164 (3) | 0.68221 (9) | 0.0754 (5) | |
H14 | 0.0378 | −1.0005 | 0.7168 | 0.091* | |
C15 | 0.13566 (16) | −0.7331 (2) | 0.68759 (7) | 0.0567 (4) | |
H15 | 0.1924 | −0.6936 | 0.7259 | 0.068* | |
O1 | 0.32389 (12) | −0.35367 (16) | 0.69172 (4) | 0.0588 (3) | |
O2 | 0.26005 (14) | −0.32158 (18) | 0.58999 (4) | 0.0659 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C2 | 0.0443 (7) | 0.0487 (7) | 0.0360 (6) | 0.0058 (5) | 0.0043 (5) | −0.0024 (5) |
C4 | 0.0535 (7) | 0.0585 (8) | 0.0387 (7) | 0.0051 (6) | 0.0057 (6) | −0.0003 (6) |
C5 | 0.0629 (8) | 0.0591 (8) | 0.0427 (7) | −0.0007 (6) | 0.0056 (6) | 0.0053 (6) |
C7 | 0.0611 (8) | 0.0609 (9) | 0.0550 (8) | −0.0100 (7) | 0.0023 (6) | −0.0078 (7) |
N1 | 0.0560 (6) | 0.0538 (6) | 0.0402 (6) | −0.0051 (5) | 0.0007 (5) | −0.0002 (5) |
N3 | 0.0517 (6) | 0.0549 (7) | 0.0362 (6) | −0.0035 (5) | 0.0025 (4) | −0.0022 (5) |
N6 | 0.0601 (7) | 0.0568 (7) | 0.0367 (6) | −0.0046 (6) | −0.0009 (5) | 0.0001 (5) |
O8 | 0.0727 (7) | 0.0807 (7) | 0.0381 (5) | −0.0033 (5) | −0.0033 (5) | 0.0028 (5) |
C9 | 0.0481 (7) | 0.0514 (7) | 0.0414 (7) | 0.0041 (6) | 0.0011 (5) | 0.0000 (5) |
C10 | 0.0422 (6) | 0.0504 (7) | 0.0445 (7) | 0.0064 (5) | 0.0026 (5) | −0.0014 (5) |
C11 | 0.0567 (8) | 0.0709 (9) | 0.0493 (8) | −0.0020 (7) | 0.0010 (6) | −0.0060 (7) |
C12 | 0.0593 (9) | 0.0771 (11) | 0.0752 (11) | −0.0077 (8) | −0.0010 (8) | −0.0233 (9) |
C13 | 0.0617 (10) | 0.0581 (9) | 0.1103 (15) | −0.0082 (8) | 0.0030 (10) | −0.0067 (10) |
C14 | 0.0667 (10) | 0.0669 (10) | 0.0887 (12) | −0.0046 (8) | 0.0025 (9) | 0.0238 (9) |
C15 | 0.0514 (8) | 0.0609 (8) | 0.0542 (8) | 0.0017 (6) | −0.0012 (6) | 0.0075 (6) |
O1 | 0.0681 (6) | 0.0598 (6) | 0.0424 (5) | −0.0086 (5) | −0.0078 (4) | 0.0016 (4) |
O2 | 0.0830 (7) | 0.0695 (7) | 0.0422 (6) | −0.0186 (5) | 0.0022 (5) | 0.0042 (5) |
Geometric parameters (Å, º) top
C2—N6 | 1.3103 (16) | N6—H7N | 0.922 (19) |
C2—N1 | 1.3202 (17) | C9—O2 | 1.2545 (16) |
C2—N3 | 1.3590 (16) | C9—O1 | 1.2590 (15) |
C4—O8 | 1.2068 (16) | C9—C10 | 1.5058 (19) |
C4—N3 | 1.3732 (18) | C10—C15 | 1.3804 (19) |
C4—C5 | 1.508 (2) | C10—C11 | 1.3887 (19) |
C5—N1 | 1.4494 (17) | C11—C12 | 1.375 (2) |
C5—H5A | 0.9700 | C11—H11 | 0.9300 |
C5—H5B | 0.9700 | C12—C13 | 1.369 (3) |
C7—N1 | 1.4477 (17) | C12—H12 | 0.9300 |
C7—H7A | 0.9600 | C13—C14 | 1.376 (3) |
C7—H7B | 0.9600 | C13—H13 | 0.9300 |
C7—H7C | 0.9600 | C14—C15 | 1.383 (2) |
N3—H6N | 0.934 (19) | C14—H14 | 0.9300 |
N6—H3N | 0.896 (17) | C15—H15 | 0.9300 |
| | | |
N6—C2—N1 | 127.53 (12) | C2—N6—H3N | 121.3 (10) |
N6—C2—N3 | 121.57 (13) | C2—N6—H7N | 117.2 (11) |
N1—C2—N3 | 110.91 (11) | H3N—N6—H7N | 121.4 (15) |
O8—C4—N3 | 126.37 (13) | O2—C9—O1 | 124.20 (13) |
O8—C4—C5 | 127.77 (13) | O2—C9—C10 | 116.70 (11) |
N3—C4—C5 | 105.85 (11) | O1—C9—C10 | 119.09 (11) |
N1—C5—C4 | 102.83 (11) | C15—C10—C11 | 118.48 (14) |
N1—C5—H5A | 111.2 | C15—C10—C9 | 121.76 (12) |
C4—C5—H5A | 111.2 | C11—C10—C9 | 119.72 (12) |
N1—C5—H5B | 111.2 | C12—C11—C10 | 121.13 (15) |
C4—C5—H5B | 111.2 | C12—C11—H11 | 119.4 |
H5A—C5—H5B | 109.1 | C10—C11—H11 | 119.4 |
N1—C7—H7A | 109.5 | C13—C12—C11 | 119.80 (15) |
N1—C7—H7B | 109.5 | C13—C12—H12 | 120.1 |
H7A—C7—H7B | 109.5 | C11—C12—H12 | 120.1 |
N1—C7—H7C | 109.5 | C12—C13—C14 | 119.99 (16) |
H7A—C7—H7C | 109.5 | C12—C13—H13 | 120.0 |
H7B—C7—H7C | 109.5 | C14—C13—H13 | 120.0 |
C2—N1—C7 | 127.25 (11) | C13—C14—C15 | 120.32 (16) |
C2—N1—C5 | 109.89 (11) | C13—C14—H14 | 119.8 |
C7—N1—C5 | 122.69 (12) | C15—C14—H14 | 119.8 |
C2—N3—C4 | 110.52 (12) | C10—C15—C14 | 120.27 (14) |
C2—N3—H6N | 121.3 (10) | C10—C15—H15 | 119.9 |
C4—N3—H6N | 127.9 (10) | C14—C15—H15 | 119.9 |
| | | |
O8—C4—C5—N1 | 179.65 (14) | O2—C9—C10—C15 | 174.16 (13) |
N3—C4—C5—N1 | −0.95 (14) | O1—C9—C10—C15 | −4.74 (19) |
N6—C2—N1—C7 | −5.5 (2) | O2—C9—C10—C11 | −3.70 (19) |
N3—C2—N1—C7 | 174.57 (13) | O1—C9—C10—C11 | 177.40 (12) |
N6—C2—N1—C5 | 179.24 (13) | C15—C10—C11—C12 | 0.2 (2) |
N3—C2—N1—C5 | −0.64 (15) | C9—C10—C11—C12 | 178.10 (13) |
C4—C5—N1—C2 | 0.97 (15) | C10—C11—C12—C13 | −0.7 (2) |
C4—C5—N1—C7 | −174.51 (12) | C11—C12—C13—C14 | 0.5 (3) |
N6—C2—N3—C4 | −179.91 (12) | C12—C13—C14—C15 | 0.2 (3) |
N1—C2—N3—C4 | −0.02 (15) | C11—C10—C15—C14 | 0.5 (2) |
O8—C4—N3—C2 | −179.95 (13) | C9—C10—C15—C14 | −177.39 (13) |
C5—C4—N3—C2 | 0.64 (14) | C13—C14—C15—C10 | −0.7 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H6N···O2 | 0.934 (19) | 1.706 (19) | 2.6377 (16) | 176 (2) |
N6—H7N···O1 | 0.922 (19) | 1.88 (2) | 2.8062 (16) | 178 (2) |
N6—H3N···O1i | 0.896 (17) | 1.923 (17) | 2.8061 (15) | 168 (1) |
C5—H5B···O2ii | 0.97 | 2.53 | 3.300 (2) | 137 |
C7—H7A···O1i | 0.96 | 2.52 | 3.433 (2) | 159 |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x, y+1, z. |