The crystal structure of the title compound (CAS: 4052–54-4), C
16H
18N
2O
5S, contains O—H
O and N—H
O hydrogen bonds. The four-membered ring is folded and the five-membered ring has an envelope conformation.
Supporting information
CCDC reference: 618305
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.006 Å
- R factor = 0.038
- wR factor = 0.082
- Data-to-parameter ratio = 12.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.12 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.13 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C4
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C6
PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C1 -C6 1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
PLAT432_ALERT_2_C Short Inter X...Y Contact S1 .. C8 .. 3.29 Ang.
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 25.47
From the CIF: _reflns_number_total 2703
Count of symmetry unique reflns 1587
Completeness (_total/calc) 170.32%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1116
Fraction of Friedel pairs measured 0.703
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
1-oxo-6-(2-phenylacetylamino)-1-penicillanic acid
top
Crystal data top
C16H18N2O5S | Dx = 1.368 Mg m−3 |
Mr = 350.38 | Mo Kα radiation, λ = 0.71073 Å |
Trigonal, P32 | Cell parameters from 1894 reflections |
a = 11.6285 (12) Å | θ = 2.8–21.2° |
c = 10.894 (2) Å | µ = 0.22 mm−1 |
V = 1275.7 (3) Å3 | T = 294 K |
Z = 3 | Block, colourless |
F(000) = 552 | 0.22 × 0.16 × 0.12 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2703 independent reflections |
Radiation source: fine-focus sealed tube | 1994 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
φ and ω scans | θmax = 25.5°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −14→12 |
Tmin = 0.943, Tmax = 0.974 | k = −11→14 |
6825 measured reflections | l = −8→13 |
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)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.082 | w = 1/[σ2(Fo2) + (0.0359P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.003 |
2703 reflections | Δρmax = 0.18 e Å−3 |
220 parameters | Δρmin = −0.16 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 1116 Freidel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.04 (8) |
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 | |
S1 | 0.61963 (8) | 0.71239 (8) | 0.25230 (7) | 0.0447 (2) | |
O1 | 0.1857 (2) | 0.3406 (2) | 0.3183 (2) | 0.0550 (7) | |
O2 | 0.4973 (2) | 0.6873 (2) | 0.5998 (2) | 0.0530 (6) | |
O3 | 0.5680 (2) | 0.7951 (2) | 0.3076 (2) | 0.0511 (6) | |
O4 | 0.8383 (2) | 0.6094 (3) | 0.5536 (3) | 0.0617 (7) | |
O5 | 0.9639 (2) | 0.8287 (2) | 0.5425 (3) | 0.0786 (10) | |
H5 | 1.0149 | 0.8171 | 0.5859 | 0.118* | |
N1 | 0.3236 (2) | 0.5574 (2) | 0.3515 (2) | 0.0400 (7) | |
H1 | 0.3383 | 0.6373 | 0.3439 | 0.048* | |
N2 | 0.6173 (2) | 0.6234 (2) | 0.4688 (2) | 0.0377 (6) | |
C1 | −0.0945 (4) | 0.4248 (4) | 0.3437 (4) | 0.0613 (10) | |
H1A | −0.0511 | 0.5038 | 0.3877 | 0.074* | |
C2 | −0.2271 (5) | 0.3398 (6) | 0.3644 (5) | 0.0908 (16) | |
H2 | −0.2730 | 0.3609 | 0.4216 | 0.109* | |
C3 | −0.2907 (5) | 0.2239 (7) | 0.2999 (8) | 0.119 (2) | |
H3 | −0.3810 | 0.1658 | 0.3116 | 0.142* | |
C4 | −0.2213 (6) | 0.1943 (5) | 0.2190 (8) | 0.120 (2) | |
H4 | −0.2642 | 0.1135 | 0.1778 | 0.144* | |
C5 | −0.0892 (4) | 0.2801 (4) | 0.1957 (5) | 0.0866 (14) | |
H5A | −0.0445 | 0.2592 | 0.1370 | 0.104* | |
C6 | −0.0243 (3) | 0.3963 (3) | 0.2598 (3) | 0.0471 (9) | |
C7 | 0.1212 (3) | 0.4926 (4) | 0.2383 (3) | 0.0549 (10) | |
H7A | 0.1393 | 0.4970 | 0.1510 | 0.066* | |
H7B | 0.1412 | 0.5803 | 0.2648 | 0.066* | |
C8 | 0.2113 (3) | 0.4554 (3) | 0.3048 (3) | 0.0385 (8) | |
C9 | 0.4179 (3) | 0.5340 (3) | 0.4132 (3) | 0.0388 (8) | |
H9 | 0.3735 | 0.4426 | 0.4440 | 0.047* | |
C10 | 0.5522 (3) | 0.5668 (3) | 0.3520 (3) | 0.0386 (8) | |
H10 | 0.5589 | 0.4910 | 0.3217 | 0.046* | |
C11 | 0.5074 (3) | 0.6279 (3) | 0.5138 (3) | 0.0396 (8) | |
C12 | 0.7512 (3) | 0.7378 (3) | 0.4626 (3) | 0.0392 (7) | |
H12 | 0.7507 | 0.8130 | 0.5027 | 0.047* | |
C13 | 0.8534 (3) | 0.7144 (4) | 0.5260 (3) | 0.0446 (8) | |
C14 | 0.7842 (3) | 0.7723 (3) | 0.3235 (3) | 0.0458 (8) | |
C15 | 0.8652 (4) | 0.9207 (4) | 0.3011 (4) | 0.0718 (12) | |
H15A | 0.9520 | 0.9549 | 0.3361 | 0.108* | |
H15B | 0.8217 | 0.9635 | 0.3386 | 0.108* | |
H15C | 0.8730 | 0.9377 | 0.2144 | 0.108* | |
C16 | 0.8453 (3) | 0.6975 (4) | 0.2632 (4) | 0.0612 (10) | |
H16A | 0.8420 | 0.7042 | 0.1756 | 0.092* | |
H16B | 0.7965 | 0.6057 | 0.2869 | 0.092* | |
H16C | 0.9360 | 0.7352 | 0.2889 | 0.092* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0469 (5) | 0.0523 (5) | 0.0350 (4) | 0.0250 (5) | −0.0026 (4) | 0.0060 (4) |
O1 | 0.0548 (15) | 0.0416 (14) | 0.0703 (18) | 0.0253 (12) | −0.0005 (13) | −0.0168 (12) |
O2 | 0.0510 (14) | 0.0750 (16) | 0.0383 (15) | 0.0354 (13) | 0.0005 (11) | −0.0030 (13) |
O3 | 0.0521 (14) | 0.0490 (13) | 0.0605 (16) | 0.0317 (12) | −0.0049 (11) | 0.0078 (12) |
O4 | 0.0548 (16) | 0.0560 (16) | 0.078 (2) | 0.0307 (13) | −0.0184 (13) | 0.0052 (13) |
O5 | 0.0534 (16) | 0.0490 (16) | 0.135 (3) | 0.0265 (14) | −0.0441 (17) | −0.0151 (15) |
N1 | 0.0350 (15) | 0.0381 (15) | 0.0475 (18) | 0.0186 (13) | −0.0077 (13) | 0.0012 (12) |
N2 | 0.0360 (14) | 0.0446 (16) | 0.0361 (15) | 0.0228 (13) | −0.0043 (12) | 0.0020 (12) |
C1 | 0.060 (3) | 0.070 (3) | 0.060 (3) | 0.037 (2) | −0.007 (2) | 0.004 (2) |
C2 | 0.063 (3) | 0.127 (5) | 0.096 (4) | 0.058 (3) | 0.015 (3) | 0.040 (3) |
C3 | 0.049 (3) | 0.116 (5) | 0.164 (7) | 0.021 (3) | −0.009 (4) | 0.052 (5) |
C4 | 0.066 (4) | 0.075 (3) | 0.185 (7) | 0.010 (3) | −0.062 (4) | −0.032 (4) |
C5 | 0.063 (3) | 0.091 (3) | 0.090 (3) | 0.027 (3) | −0.034 (2) | −0.042 (3) |
C6 | 0.0394 (19) | 0.052 (2) | 0.046 (2) | 0.0203 (17) | −0.0138 (17) | 0.0018 (18) |
C7 | 0.0450 (19) | 0.062 (2) | 0.047 (2) | 0.0190 (18) | −0.0099 (16) | 0.0089 (18) |
C8 | 0.0387 (19) | 0.048 (2) | 0.0274 (18) | 0.0207 (17) | 0.0033 (15) | −0.0062 (15) |
C9 | 0.0353 (17) | 0.0349 (18) | 0.046 (2) | 0.0173 (15) | −0.0011 (15) | 0.0069 (15) |
C10 | 0.0394 (18) | 0.0365 (18) | 0.043 (2) | 0.0211 (15) | −0.0001 (14) | −0.0009 (14) |
C11 | 0.0367 (19) | 0.050 (2) | 0.0343 (19) | 0.0232 (16) | 0.0050 (15) | 0.0121 (16) |
C12 | 0.0356 (18) | 0.0380 (18) | 0.047 (2) | 0.0209 (15) | −0.0081 (15) | −0.0051 (15) |
C13 | 0.045 (2) | 0.050 (2) | 0.046 (2) | 0.0289 (19) | −0.0107 (16) | −0.0092 (18) |
C14 | 0.0395 (19) | 0.049 (2) | 0.046 (2) | 0.0196 (17) | 0.0027 (16) | 0.0055 (16) |
C15 | 0.054 (2) | 0.059 (2) | 0.086 (3) | 0.016 (2) | 0.001 (2) | 0.016 (2) |
C16 | 0.049 (2) | 0.086 (3) | 0.054 (2) | 0.038 (2) | 0.0113 (19) | 0.001 (2) |
Geometric parameters (Å, º) top
S1—O3 | 1.492 (2) | C4—H4 | 0.9300 |
S1—C10 | 1.826 (3) | C5—C6 | 1.365 (5) |
S1—C14 | 1.849 (3) | C5—H5A | 0.9300 |
O1—C8 | 1.223 (4) | C6—C7 | 1.509 (4) |
O2—C11 | 1.203 (4) | C7—C8 | 1.504 (4) |
O4—C13 | 1.182 (4) | C7—H7A | 0.9700 |
O5—C13 | 1.320 (4) | C7—H7B | 0.9700 |
O5—H5 | 0.8200 | C9—C11 | 1.530 (5) |
N1—C8 | 1.349 (4) | C9—C10 | 1.561 (4) |
N1—C9 | 1.424 (4) | C9—H9 | 0.9800 |
N1—H1 | 0.8600 | C10—H10 | 0.9800 |
N2—C11 | 1.394 (4) | C12—C13 | 1.512 (4) |
N2—C10 | 1.458 (4) | C12—C14 | 1.565 (5) |
N2—C12 | 1.459 (4) | C12—H12 | 0.9800 |
C1—C2 | 1.371 (5) | C14—C15 | 1.517 (5) |
C1—C6 | 1.372 (5) | C14—C16 | 1.520 (5) |
C1—H1A | 0.9300 | C15—H15A | 0.9600 |
C2—C3 | 1.364 (9) | C15—H15B | 0.9600 |
C2—H2 | 0.9300 | C15—H15C | 0.9600 |
C3—C4 | 1.352 (8) | C16—H16A | 0.9600 |
C3—H3 | 0.9300 | C16—H16B | 0.9600 |
C4—C5 | 1.373 (7) | C16—H16C | 0.9600 |
| | | |
O3—S1—C10 | 103.47 (13) | N1—C9—H9 | 109.3 |
O3—S1—C14 | 105.21 (15) | C11—C9—H9 | 109.3 |
C10—S1—C14 | 89.03 (14) | C10—C9—H9 | 109.3 |
C13—O5—H5 | 109.5 | N2—C10—C9 | 88.1 (2) |
C8—N1—C9 | 120.6 (3) | N2—C10—S1 | 102.44 (19) |
C8—N1—H1 | 119.7 | C9—C10—S1 | 113.2 (2) |
C9—N1—H1 | 119.7 | N2—C10—H10 | 116.3 |
C11—N2—C10 | 92.6 (2) | C9—C10—H10 | 116.3 |
C11—N2—C12 | 124.2 (2) | S1—C10—H10 | 116.3 |
C10—N2—C12 | 116.6 (2) | O2—C11—N2 | 130.5 (3) |
C2—C1—C6 | 121.7 (4) | O2—C11—C9 | 137.8 (3) |
C2—C1—H1A | 119.1 | N2—C11—C9 | 91.8 (3) |
C6—C1—H1A | 119.1 | N2—C12—C13 | 113.0 (3) |
C3—C2—C1 | 119.1 (5) | N2—C12—C14 | 106.9 (2) |
C3—C2—H2 | 120.4 | C13—C12—C14 | 112.0 (3) |
C1—C2—H2 | 120.4 | N2—C12—H12 | 108.2 |
C4—C3—C2 | 119.3 (5) | C13—C12—H12 | 108.2 |
C4—C3—H3 | 120.3 | C14—C12—H12 | 108.2 |
C2—C3—H3 | 120.3 | O4—C13—O5 | 124.9 (3) |
C3—C4—C5 | 122.0 (5) | O4—C13—C12 | 125.3 (3) |
C3—C4—H4 | 119.0 | O5—C13—C12 | 109.8 (3) |
C5—C4—H4 | 119.0 | C15—C14—C16 | 112.3 (3) |
C6—C5—C4 | 119.2 (5) | C15—C14—C12 | 112.4 (3) |
C6—C5—H5A | 120.4 | C16—C14—C12 | 113.4 (3) |
C4—C5—H5A | 120.4 | C15—C14—S1 | 107.3 (2) |
C5—C6—C1 | 118.6 (3) | C16—C14—S1 | 107.2 (2) |
C5—C6—C7 | 121.0 (4) | C12—C14—S1 | 103.58 (19) |
C1—C6—C7 | 120.4 (4) | C14—C15—H15A | 109.5 |
C8—C7—C6 | 113.3 (3) | C14—C15—H15B | 109.5 |
C8—C7—H7A | 108.9 | H15A—C15—H15B | 109.5 |
C6—C7—H7A | 108.9 | C14—C15—H15C | 109.5 |
C8—C7—H7B | 108.9 | H15A—C15—H15C | 109.5 |
C6—C7—H7B | 108.9 | H15B—C15—H15C | 109.5 |
H7A—C7—H7B | 107.7 | C14—C16—H16A | 109.5 |
O1—C8—N1 | 121.0 (3) | C14—C16—H16B | 109.5 |
O1—C8—C7 | 123.2 (3) | H16A—C16—H16B | 109.5 |
N1—C8—C7 | 115.8 (3) | C14—C16—H16C | 109.5 |
N1—C9—C11 | 121.1 (3) | H16A—C16—H16C | 109.5 |
N1—C9—C10 | 121.6 (3) | H16B—C16—H16C | 109.5 |
C11—C9—C10 | 83.7 (2) | | |
| | | |
C6—C1—C2—C3 | 0.0 (7) | C10—N2—C11—O2 | −164.2 (4) |
C1—C2—C3—C4 | 1.2 (8) | C12—N2—C11—O2 | −39.3 (5) |
C2—C3—C4—C5 | −2.7 (9) | C10—N2—C11—C9 | 15.4 (2) |
C3—C4—C5—C6 | 2.8 (9) | C12—N2—C11—C9 | 140.3 (3) |
C4—C5—C6—C1 | −1.5 (6) | N1—C9—C11—O2 | 41.8 (5) |
C4—C5—C6—C7 | 179.3 (4) | C10—C9—C11—O2 | 165.1 (4) |
C2—C1—C6—C5 | 0.1 (6) | N1—C9—C11—N2 | −137.7 (3) |
C2—C1—C6—C7 | 179.4 (3) | C10—C9—C11—N2 | −14.4 (2) |
C5—C6—C7—C8 | −81.1 (4) | C11—N2—C12—C13 | 125.7 (3) |
C1—C6—C7—C8 | 99.7 (4) | C10—N2—C12—C13 | −120.6 (3) |
C9—N1—C8—O1 | 2.7 (4) | C11—N2—C12—C14 | −110.6 (3) |
C9—N1—C8—C7 | −178.2 (3) | C10—N2—C12—C14 | 3.1 (3) |
C6—C7—C8—O1 | 36.7 (5) | N2—C12—C13—O4 | 16.7 (5) |
C6—C7—C8—N1 | −142.3 (3) | C14—C12—C13—O4 | −104.1 (4) |
C8—N1—C9—C11 | −151.6 (3) | N2—C12—C13—O5 | −165.3 (3) |
C8—N1—C9—C10 | 105.6 (3) | C14—C12—C13—O5 | 73.8 (3) |
C11—N2—C10—C9 | −15.0 (2) | N2—C12—C14—C15 | 143.0 (3) |
C12—N2—C10—C9 | −145.8 (2) | C13—C12—C14—C15 | −92.7 (3) |
C11—N2—C10—S1 | 98.3 (2) | N2—C12—C14—C16 | −88.3 (3) |
C12—N2—C10—S1 | −32.4 (3) | C13—C12—C14—C16 | 36.1 (4) |
N1—C9—C10—N2 | 136.6 (3) | N2—C12—C14—S1 | 27.5 (3) |
C11—C9—C10—N2 | 13.8 (2) | C13—C12—C14—S1 | 151.9 (2) |
N1—C9—C10—S1 | 33.9 (4) | O3—S1—C14—C15 | −55.2 (3) |
C11—C9—C10—S1 | −89.0 (2) | C10—S1—C14—C15 | −158.9 (3) |
O3—S1—C10—N2 | −64.5 (2) | O3—S1—C14—C16 | −176.1 (2) |
C14—S1—C10—N2 | 40.9 (2) | C10—S1—C14—C16 | 80.2 (2) |
O3—S1—C10—C9 | 28.8 (2) | O3—S1—C14—C12 | 63.8 (2) |
C14—S1—C10—C9 | 134.2 (2) | C10—S1—C14—C12 | −39.9 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···O1i | 0.82 | 1.79 | 2.597 (3) | 166 |
N1—H1···O2ii | 0.86 | 2.33 | 3.142 (3) | 157 |
N1—H1···O3 | 0.86 | 2.40 | 2.844 (3) | 113 |
Symmetry codes: (i) −x+y+1, −x+1, z+1/3; (ii) −y+1, x−y+1, z−1/3. |