In the crystal structure of the title compound [systematic name: 3-amino-1,3-diazaspiro[4.5]decane-2,4-dione–phenylboronic acid (1/1)], C
8H
13N
3O
2·C
6H
7BO
2, molecules are held together by O—H
O, N—H
O and C—H
O hydrogen bonds and by an N—H
π interaction.
Supporting information
CCDC reference: 621377
Key indicators
- Single-crystal X-ray study
- T = 290 K
- Mean (C-C) = 0.004 Å
- R factor = 0.062
- wR factor = 0.168
- Data-to-parameter ratio = 22.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor N24 - HN4B ... ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 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: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Bruno et al., 2002); software used to prepare material for publication: WinGX (Farrugia, 1999).
3-Amino-1,3-diazaspiro[4.5]decane-2,4-dione–phenylboronic acid (1/1)
top
Crystal data top
C8H13N3O2·C6H7BO2 | Z = 2 |
Mr = 305.14 | F(000) = 324 |
Triclinic, P1 | Dx = 1.293 Mg m−3 |
Hall symbol: -P 1 | Melting point: not measured K |
a = 6.043 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.0940 (11) Å | Cell parameters from 22 reflections |
c = 12.3011 (12) Å | θ = 18.1–19.6° |
α = 62.514 (7)° | µ = 0.09 mm−1 |
β = 89.291 (9)° | T = 290 K |
γ = 80.182 (8)° | Prism, colorless |
V = 783.59 (17) Å3 | 0.35 × 0.26 × 0.26 mm |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.027 |
Radiation source: fine-focus sealed tube | θmax = 30.0°, θmin = 1.9° |
Graphite monochromator | h = 0→8 |
ω/2θ scans | k = −16→16 |
4971 measured reflections | l = −17→17 |
4568 independent reflections | 3 standard reflections every 120 min |
2434 reflections with I > 2σ(I) | intensity decay: 1% |
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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.168 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0593P)2 + 0.1895P] where P = (Fo2 + 2Fc2)/3 |
4568 reflections | (Δ/σ)max < 0.001 |
201 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.24 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. |
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 | |
C1 | 0.5923 (4) | 0.59886 (19) | 0.12456 (19) | 0.0392 (5) | |
C2 | 0.4760 (4) | 0.7207 (2) | 0.0476 (2) | 0.0464 (5) | |
H2 | 0.3374 | 0.7309 | 0.0088 | 0.056* | |
C3 | 0.5621 (4) | 0.8268 (2) | 0.0276 (2) | 0.0523 (6) | |
H3 | 0.4815 | 0.9074 | −0.0239 | 0.063* | |
C4 | 0.7686 (5) | 0.8126 (2) | 0.0845 (2) | 0.0551 (6) | |
H4 | 0.8266 | 0.8836 | 0.0723 | 0.066* | |
C5 | 0.8872 (4) | 0.6935 (2) | 0.1589 (2) | 0.0532 (6) | |
H5 | 1.0274 | 0.6838 | 0.1959 | 0.064* | |
C6 | 0.8003 (4) | 0.5877 (2) | 0.1794 (2) | 0.0448 (5) | |
H6 | 0.8823 | 0.5075 | 0.2309 | 0.054* | |
C22 | 0.2968 (4) | 0.09706 (19) | 0.33703 (19) | 0.0375 (5) | |
C24 | 0.0523 (4) | 0.05222 (19) | 0.22799 (19) | 0.0403 (5) | |
C25 | 0.1604 (3) | −0.07237 (18) | 0.33602 (18) | 0.0361 (4) | |
C26 | 0.3089 (5) | −0.1561 (2) | 0.2908 (2) | 0.0530 (6) | |
H6A | 0.2206 | −0.1669 | 0.2322 | 0.064* | |
H6B | 0.4314 | −0.1149 | 0.2491 | 0.064* | |
C27 | 0.4047 (5) | −0.2853 (2) | 0.3969 (3) | 0.0720 (8) | |
H7A | 0.5067 | −0.2752 | 0.4505 | 0.086* | |
H7B | 0.4901 | −0.3380 | 0.3649 | 0.086* | |
C28 | 0.2197 (6) | −0.3508 (2) | 0.4704 (3) | 0.0736 (9) | |
H8A | 0.1270 | −0.3691 | 0.4192 | 0.088* | |
H8B | 0.2870 | −0.4307 | 0.5399 | 0.088* | |
C29 | 0.0737 (5) | −0.2687 (2) | 0.5164 (2) | 0.0604 (7) | |
H9A | 0.1626 | −0.2589 | 0.5755 | 0.072* | |
H9B | −0.0489 | −0.3101 | 0.5579 | 0.072* | |
C210 | −0.0221 (4) | −0.1388 (2) | 0.4115 (2) | 0.0484 (6) | |
H10A | −0.1053 | −0.0867 | 0.4447 | 0.058* | |
H10B | −0.1266 | −0.1481 | 0.3583 | 0.058* | |
B | 0.4904 (4) | 0.4796 (2) | 0.1493 (2) | 0.0424 (6) | |
N21 | 0.2961 (3) | −0.02711 (16) | 0.39923 (16) | 0.0431 (4) | |
H21 | 0.3685 | −0.0758 | 0.4697 | 0.052* | |
N23 | 0.1428 (3) | 0.14600 (15) | 0.23466 (15) | 0.0384 (4) | |
N24 | 0.0879 (3) | 0.27618 (15) | 0.15091 (17) | 0.0442 (4) | |
HN4A | −0.0675 | 0.3032 | 0.1593 | 0.053* | |
HN4B | 0.0894 | 0.2831 | 0.0712 | 0.053* | |
O1 | 0.6159 (3) | 0.36252 (15) | 0.22137 (17) | 0.0617 (5) | |
H1O | 0.5342 | 0.3094 | 0.2445 | 0.093* | |
O2 | 0.2825 (3) | 0.49715 (15) | 0.0979 (2) | 0.0631 (5) | |
H2O | 0.2446 | 0.4283 | 0.1211 | 0.095* | |
O22 | 0.4060 (3) | 0.15951 (14) | 0.36219 (14) | 0.0480 (4) | |
O24 | −0.0848 (3) | 0.06779 (15) | 0.15003 (16) | 0.0629 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0414 (12) | 0.0396 (11) | 0.0407 (11) | −0.0116 (9) | 0.0046 (9) | −0.0207 (9) |
C2 | 0.0462 (13) | 0.0423 (12) | 0.0516 (13) | −0.0075 (10) | −0.0020 (11) | −0.0227 (11) |
C3 | 0.0589 (15) | 0.0379 (12) | 0.0617 (15) | −0.0089 (11) | 0.0040 (12) | −0.0245 (11) |
C4 | 0.0690 (17) | 0.0468 (13) | 0.0649 (16) | −0.0263 (12) | 0.0148 (14) | −0.0340 (13) |
C5 | 0.0497 (14) | 0.0598 (15) | 0.0599 (15) | −0.0203 (12) | 0.0010 (12) | −0.0327 (13) |
C6 | 0.0451 (13) | 0.0419 (12) | 0.0429 (12) | −0.0092 (10) | −0.0011 (10) | −0.0157 (10) |
C22 | 0.0406 (11) | 0.0371 (10) | 0.0361 (10) | −0.0102 (9) | 0.0001 (9) | −0.0169 (9) |
C24 | 0.0443 (12) | 0.0350 (10) | 0.0385 (11) | −0.0089 (9) | −0.0043 (10) | −0.0138 (9) |
C25 | 0.0404 (11) | 0.0331 (10) | 0.0341 (10) | −0.0095 (8) | −0.0029 (9) | −0.0140 (8) |
C26 | 0.0660 (16) | 0.0432 (12) | 0.0508 (13) | −0.0084 (11) | 0.0101 (12) | −0.0235 (11) |
C27 | 0.083 (2) | 0.0445 (14) | 0.0757 (19) | 0.0112 (14) | 0.0067 (17) | −0.0251 (14) |
C28 | 0.106 (2) | 0.0349 (13) | 0.0613 (17) | −0.0096 (14) | −0.0069 (17) | −0.0077 (12) |
C29 | 0.0682 (17) | 0.0492 (14) | 0.0463 (13) | −0.0184 (13) | 0.0009 (13) | −0.0051 (11) |
C210 | 0.0443 (13) | 0.0452 (12) | 0.0490 (13) | −0.0120 (10) | 0.0015 (11) | −0.0152 (11) |
B | 0.0435 (14) | 0.0401 (13) | 0.0450 (13) | −0.0110 (11) | 0.0051 (11) | −0.0200 (11) |
N21 | 0.0532 (11) | 0.0339 (9) | 0.0375 (9) | −0.0093 (8) | −0.0115 (8) | −0.0120 (8) |
N23 | 0.0446 (10) | 0.0291 (8) | 0.0376 (9) | −0.0080 (7) | −0.0052 (8) | −0.0118 (7) |
N24 | 0.0500 (11) | 0.0308 (9) | 0.0439 (10) | −0.0072 (8) | −0.0057 (9) | −0.0107 (8) |
O1 | 0.0636 (11) | 0.0427 (9) | 0.0645 (11) | −0.0214 (8) | −0.0100 (9) | −0.0088 (8) |
O2 | 0.0442 (10) | 0.0450 (9) | 0.1020 (15) | −0.0106 (8) | −0.0051 (10) | −0.0347 (10) |
O22 | 0.0573 (10) | 0.0424 (8) | 0.0440 (9) | −0.0195 (7) | −0.0071 (7) | −0.0163 (7) |
O24 | 0.0760 (12) | 0.0463 (9) | 0.0535 (10) | −0.0172 (8) | −0.0292 (9) | −0.0099 (8) |
Geometric parameters (Å, º) top
C1—C6 | 1.390 (3) | C26—H6A | 0.9700 |
C1—C2 | 1.392 (3) | C26—H6B | 0.9700 |
C1—B | 1.564 (3) | C27—C28 | 1.520 (4) |
C2—C3 | 1.382 (3) | C27—H7A | 0.9700 |
C2—H2 | 0.9300 | C27—H7B | 0.9700 |
C3—C4 | 1.384 (4) | C28—C29 | 1.514 (4) |
C3—H3 | 0.9300 | C28—H8A | 0.9700 |
C4—C5 | 1.368 (3) | C28—H8B | 0.9700 |
C4—H4 | 0.9300 | C29—C210 | 1.518 (3) |
C5—C6 | 1.380 (3) | C29—H9A | 0.9700 |
C5—H5 | 0.9300 | C29—H9B | 0.9700 |
C6—H6 | 0.9300 | C210—H10A | 0.9700 |
C22—O22 | 1.222 (2) | C210—H10B | 0.9700 |
C22—N21 | 1.335 (3) | B—O2 | 1.352 (3) |
C22—N23 | 1.398 (3) | B—O1 | 1.363 (3) |
C24—O24 | 1.201 (2) | N21—H21 | 0.8600 |
C24—N23 | 1.375 (3) | N23—N24 | 1.408 (2) |
C24—C25 | 1.517 (3) | N24—HN4A | 0.9611 |
C25—N21 | 1.462 (2) | N24—HN4B | 0.9445 |
C25—C210 | 1.521 (3) | O1—H1O | 0.8200 |
C25—C26 | 1.529 (3) | O2—H2O | 0.8200 |
C26—C27 | 1.519 (3) | | |
| | | |
C6—C1—C2 | 117.46 (19) | C26—C27—H7A | 109.3 |
C6—C1—B | 121.54 (19) | C28—C27—H7A | 109.3 |
C2—C1—B | 121.00 (19) | C26—C27—H7B | 109.3 |
C3—C2—C1 | 121.4 (2) | C28—C27—H7B | 109.3 |
C3—C2—H2 | 119.3 | H7A—C27—H7B | 108.0 |
C1—C2—H2 | 119.3 | C29—C28—C27 | 111.2 (2) |
C2—C3—C4 | 119.7 (2) | C29—C28—H8A | 109.4 |
C2—C3—H3 | 120.1 | C27—C28—H8A | 109.4 |
C4—C3—H3 | 120.1 | C29—C28—H8B | 109.4 |
C5—C4—C3 | 119.7 (2) | C27—C28—H8B | 109.4 |
C5—C4—H4 | 120.2 | H8A—C28—H8B | 108.0 |
C3—C4—H4 | 120.2 | C28—C29—C210 | 111.3 (2) |
C4—C5—C6 | 120.5 (2) | C28—C29—H9A | 109.4 |
C4—C5—H5 | 119.8 | C210—C29—H9A | 109.4 |
C6—C5—H5 | 119.8 | C28—C29—H9B | 109.4 |
C5—C6—C1 | 121.2 (2) | C210—C29—H9B | 109.4 |
C5—C6—H6 | 119.4 | H9A—C29—H9B | 108.0 |
C1—C6—H6 | 119.4 | C29—C210—C25 | 112.29 (19) |
O22—C22—N21 | 128.3 (2) | C29—C210—H10A | 109.1 |
O22—C22—N23 | 124.95 (19) | C25—C210—H10A | 109.1 |
N21—C22—N23 | 106.73 (17) | C29—C210—H10B | 109.1 |
O24—C24—N23 | 125.69 (19) | C25—C210—H10B | 109.1 |
O24—C24—C25 | 127.33 (19) | H10A—C210—H10B | 107.9 |
N23—C24—C25 | 106.97 (17) | O2—B—O1 | 122.9 (2) |
N21—C25—C24 | 100.63 (15) | O2—B—C1 | 118.6 (2) |
N21—C25—C210 | 113.68 (18) | O1—B—C1 | 118.4 (2) |
C24—C25—C210 | 109.49 (17) | C22—N21—C25 | 113.51 (17) |
N21—C25—C26 | 111.25 (18) | C22—N21—H21 | 123.2 |
C24—C25—C26 | 110.32 (18) | C25—N21—H21 | 123.2 |
C210—C25—C26 | 111.01 (18) | C24—N23—C22 | 111.74 (16) |
C27—C26—C25 | 111.2 (2) | C24—N23—N24 | 125.17 (16) |
C27—C26—H6A | 109.4 | C22—N23—N24 | 123.09 (16) |
C25—C26—H6A | 109.4 | N23—N24—HN4A | 106.3 |
C27—C26—H6B | 109.4 | N23—N24—HN4B | 107.0 |
C25—C26—H6B | 109.4 | HN4A—N24—HN4B | 104.5 |
H6A—C26—H6B | 108.0 | B—O1—H1O | 109.5 |
C26—C27—C28 | 111.6 (2) | B—O2—H2O | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O22 | 0.82 | 2.00 | 2.778 (2) | 158 |
O2—H2O···N24 | 0.82 | 2.09 | 2.897 (2) | 167 |
N24—HN4A···O1i | 0.96 | 2.18 | 3.120 (3) | 165 |
N21—H21···O22ii | 0.86 | 2.20 | 3.037 (2) | 166 |
C2—H2···O24iii | 0.93 | 2.55 | 3.222 (3) | 130 |
N24—HN4B···Cg1iv | 0.94 | 2.51 | 3.346 (3) | 147 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y, −z+1; (iii) −x, −y+1, −z; (iv) −x+1, −y+1, −z. |