(3S,5R,6S)-Di­phenyl­methyl 1-oxo-6-bromo­penicillanate

Soundararajan, K.; Sethuraman, V.; Thanigaimani, K.

doi:10.1107/S2414314620001431

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 5| Part 2| February 2020| x200143

https://doi.org/10.1107/S2414314620001431

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access

(3S,5R,6S)-Diphenylmethyl 1-oxo-6-bromopenicillanate

Krishnan Soundararajan,^a Velusamy Sethuraman ^a ^* and Kaliyaperumal Thanigaimani ^b

^aDepartment of Chemistry, Periyar Maniammai Institute of Science and Technology, Vallam-613 403, Thanjavur, Tamil Nadu, India, and ^bDepartment of Chemistry, Government Arts College, Tiruchirappalli- 620 022, Tamil Nadu, India
^*Correspondence e-mail: xrdsethu@gmail.com

Edited by H. Ishida, Okayama University, Japan (Received 6 January 2020; accepted 1 February 2020; online 11 February 2020)

In the title compound, C₂₁H₂₀BrNO₄S, a key intermediate in the synthesis of the widely used β-lactamase inhibitor tazobactam, the five-membered thiazolidine ring adopts an envelope conformation and the four-membered azetidine ring is in a distorted planar conformation. The crystal structure features C—H⋯O hydrogen bonds and a weak C—H⋯π interaction.

Keywords: crystal structure; 6-bromopenicillanate; β-lactamase inhibitor; hydrogen bond.

CCDC reference: 1981292

Structure description

The title compound (Fig. 1) is a key intermediate for the synthesis of tazobactam, a widely used β-lactamase inhibitor (Bai et al., 2001 ). The five-membered thiazolidine ring (N1/C3/C2/S1/C5) adopts an envelope conformation, with an r.m.s deviation of 0.318 Å and a maximum deviation of 0.305 (1) Å for atom S1. The four-membered azetidine ring (N1/C5–C7) is in a distorted planar conformation, with an r.m.s deviation of 0.052 Å. The dihedral angle between the mean planes of these rings is 49.7 (2)°. The two phenyl rings of the diphenylmethyl group are inclined at an angle of 79.0 (2)°.

Figure 1
The molecular structure of the title compound with atom labels and 50% probability displacement ellipsoids.

In the crystal (Fig. 2), the molecules self-assemble via C21—H21⋯O2 and C22—H22⋯O1 hydrogen bonds (Table 1), forming a three-dimensional network. Weak C—H⋯π interactions involving the C18–C23 ring also occur.

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C18–C23 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21⋯O2ⁱ	0.93	2.54	3.465 (5)	171
C22—H22⋯O1ⁱⁱ	0.93	2.55	3.375 (5)	148
C14—H14⋯Cgⁱⁱⁱ	0.93	2.68	3.533 (5)	153
Symmetry codes: (i) $[-y+1, x+1, z+{\script{1\over 4}}]$ ; (ii) $[-x+1, -y+1, z+{\script{1\over 2}}]$ ; (iii) $[y-1, -x+1, z-{\script{1\over 4}}]$ .

Figure 2
A partial packing diagram for the title compound. Dashed lines indicate the C—H⋯O hydrogen bonds.

Synthesis and crystallization

The title compound, which was a gift sample from Orchid Pharmaceutical Ltd, India, prepared according to the procedure of Xu et al. (2005 ), was dissolved in acetonitrile. It was heated over a water bath for few minutes and the resultant solution was allowed to cool. After a week, transparent yellow block-shaped crystals separated out.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₁H₂₀BrNO₄S
M_r	462.35
Crystal system, space group	Tetragonal, P4₁
Temperature (K)	293
a, c (Å)	11.076 (2), 16.478 (3)
V (Å³)	2021.4 (7)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	2.16
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004 )
T_min, T_max	0.563, 0.672
No. of measured, independent and observed [I > 2σ(I)] reflections	20917, 4005, 2553
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.083, 0.89
No. of reflections	4005
No. of parameters	255
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.27
Absolute structure	Flack (1983 )
Absolute structure parameter	0.016 (8)
Computer programs: APEX2 and SAINT (Bruker, 2004), SIR92 (Altomare et al., 1993 ), SHELXL2014 (Sheldrick, 2015 ) and ORTEP-3 for Windows (Farrugia, 2012 ).

Structural data

CCDC reference: 1981292

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314620001431/is4040sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620001431/is4040Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

(3S,5R,6S)-Diphenylmethyl 1-oxo-6-bromopenicillanate top

Crystal data top

C₂₁H₂₀BrNO₄S	D_x = 1.519 Mg m⁻³
M_r = 462.35	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₁	Cell parameters from 5313 reflections
Hall symbol: P 4w	θ = 2.2–20.7°
a = 11.076 (2) Å	µ = 2.16 mm⁻¹
c = 16.478 (3) Å	T = 293 K
V = 2021.4 (7) Å³	Block, yellow
Z = 4	0.30 × 0.25 × 0.20 mm
F(000) = 944

Data collection top

Bruker Kappa APEXII CCD diffractometer	4005 independent reflections
Radiation source: fine-focus sealed tube	2553 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.072
ω and φ scan	θ_max = 26.1°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −13→13
T_min = 0.563, T_max = 0.672	k = −13→13
20917 measured reflections	l = −20→20

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)] = 0.033	H-atom parameters constrained
wR(F²) = 0.083	w = 1/[σ²(F_o²) + (0.0349P)²] where P = (F_o² + 2F_c²)/3
S = 0.89	(Δ/σ)_max < 0.001
4005 reflections	Δρ_max = 0.20 e Å⁻³
255 parameters	Δρ_min = −0.27 e Å⁻³
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.016 (8)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	U_iso*/U_eq
Br1	0.00718 (4)	−0.08038 (4)	0.19956 (3)	0.07083 (18)
S1	0.35274 (8)	0.13083 (9)	0.18370 (7)	0.0532 (3)
O1	0.3126 (3)	0.1885 (3)	0.10598 (17)	0.0729 (9)
O2	−0.0067 (3)	0.2442 (3)	0.16015 (19)	0.0668 (9)
O3	0.1395 (2)	0.3262 (2)	0.39477 (18)	0.0509 (7)
O4	0.2319 (2)	0.4801 (2)	0.33087 (14)	0.0433 (7)
N1	0.1482 (2)	0.1911 (2)	0.24983 (18)	0.0340 (7)
C2	0.3557 (3)	0.2540 (3)	0.2593 (3)	0.0478 (11)
C3	0.2217 (3)	0.2991 (3)	0.2603 (2)	0.0355 (9)
H3	0.2088	0.3525	0.2137	0.043*
C5	0.2117 (3)	0.0786 (3)	0.2304 (2)	0.0393 (10)
H5	0.2207	0.0213	0.2753	0.047*
C6	0.1117 (3)	0.0491 (3)	0.1688 (2)	0.0433 (10)
H6	0.1423	0.0410	0.1132	0.052*
C7	0.0661 (3)	0.1762 (3)	0.1875 (3)	0.0429 (9)
C8	0.3934 (4)	0.1997 (4)	0.3415 (3)	0.0725 (15)
H8A	0.4010	0.2630	0.3809	0.109*
H8B	0.4695	0.1591	0.3357	0.109*
H8C	0.3333	0.1431	0.3591	0.109*
C9	0.4420 (4)	0.3490 (4)	0.2290 (4)	0.090 (2)
H9A	0.4384	0.4183	0.2640	0.135*
H9B	0.4200	0.3722	0.1749	0.135*
H9C	0.5226	0.3172	0.2290	0.135*
C10	0.1903 (3)	0.3669 (3)	0.3367 (2)	0.0385 (9)
C11	0.2093 (3)	0.5603 (3)	0.4013 (2)	0.0392 (9)
H11	0.2150	0.5123	0.4511	0.047*
C12	0.0850 (3)	0.6124 (3)	0.3960 (3)	0.0385 (9)
C13	0.0227 (4)	0.6223 (4)	0.3241 (3)	0.0489 (11)
H13	0.0566	0.5940	0.2761	0.059*
C14	−0.0922 (4)	0.6754 (4)	0.3235 (3)	0.0641 (13)
H14	−0.1342	0.6831	0.2749	0.077*
C15	−0.1417 (4)	0.7151 (4)	0.3933 (4)	0.0660 (13)
H15	−0.2187	0.7483	0.3925	0.079*
C16	−0.0808 (4)	0.7075 (4)	0.4651 (3)	0.0628 (13)
H16	−0.1156	0.7363	0.5127	0.075*
C17	0.0334 (4)	0.6563 (3)	0.4664 (3)	0.0508 (11)
H17	0.0756	0.6515	0.5150	0.061*
C18	0.3106 (3)	0.6508 (3)	0.4006 (2)	0.0370 (9)
C19	0.3129 (4)	0.7455 (4)	0.3469 (3)	0.0479 (11)
H19	0.2509	0.7545	0.3094	0.057*
C20	0.4071 (4)	0.8277 (4)	0.3484 (3)	0.0542 (12)
H20	0.4083	0.8914	0.3116	0.065*
C21	0.4986 (4)	0.8154 (4)	0.4038 (3)	0.0568 (12)
H21	0.5617	0.8708	0.4047	0.068*
C22	0.4969 (3)	0.7212 (4)	0.4581 (3)	0.0597 (12)
H22	0.5587	0.7129	0.4959	0.072*
C23	0.4040 (3)	0.6394 (3)	0.4562 (3)	0.0486 (10)
H23	0.4036	0.5755	0.4928	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0570 (3)	0.0518 (3)	0.1037 (4)	−0.0182 (2)	0.0112 (3)	−0.0148 (3)
S1	0.0352 (5)	0.0467 (6)	0.0777 (9)	−0.0011 (4)	0.0143 (6)	−0.0181 (6)
O1	0.075 (2)	0.090 (2)	0.054 (2)	−0.0136 (18)	0.0229 (18)	−0.0001 (18)
O2	0.0562 (19)	0.0591 (19)	0.085 (2)	0.0144 (16)	−0.0230 (16)	0.0023 (17)
O3	0.0619 (18)	0.0393 (16)	0.0516 (17)	−0.0119 (13)	0.0178 (16)	−0.0062 (14)
O4	0.0485 (15)	0.0305 (14)	0.0509 (17)	−0.0064 (12)	0.0093 (13)	−0.0076 (12)
N1	0.0290 (16)	0.0246 (16)	0.0486 (19)	0.0025 (12)	0.0027 (15)	−0.0078 (14)
C2	0.030 (2)	0.043 (2)	0.070 (3)	−0.0048 (19)	0.012 (2)	−0.015 (2)
C3	0.035 (2)	0.0265 (19)	0.046 (2)	−0.0021 (16)	0.0077 (18)	−0.0008 (17)
C5	0.039 (2)	0.032 (2)	0.047 (3)	0.0025 (17)	0.0037 (18)	−0.0097 (17)
C6	0.043 (2)	0.038 (2)	0.049 (3)	−0.0055 (17)	0.0026 (19)	−0.0081 (19)
C7	0.042 (2)	0.034 (2)	0.053 (3)	−0.0004 (17)	−0.001 (2)	−0.002 (2)
C8	0.052 (3)	0.083 (4)	0.082 (4)	0.016 (2)	−0.023 (3)	−0.030 (3)
C9	0.058 (3)	0.061 (3)	0.151 (6)	−0.027 (3)	0.045 (3)	−0.033 (3)
C10	0.033 (2)	0.030 (2)	0.053 (3)	−0.0017 (17)	0.002 (2)	−0.009 (2)
C11	0.048 (2)	0.032 (2)	0.038 (2)	−0.0027 (17)	0.0054 (19)	−0.0052 (18)
C12	0.039 (2)	0.030 (2)	0.046 (2)	−0.0059 (16)	0.000 (2)	−0.0033 (18)
C13	0.044 (2)	0.047 (2)	0.056 (3)	−0.0034 (19)	0.000 (2)	−0.011 (2)
C14	0.046 (3)	0.063 (3)	0.083 (4)	−0.006 (2)	−0.015 (3)	−0.010 (3)
C15	0.047 (3)	0.044 (3)	0.107 (4)	0.001 (2)	−0.001 (3)	−0.007 (3)
C16	0.061 (3)	0.049 (3)	0.079 (4)	0.010 (2)	0.020 (3)	−0.010 (3)
C17	0.061 (3)	0.042 (2)	0.049 (3)	0.007 (2)	0.005 (2)	−0.007 (2)
C18	0.033 (2)	0.032 (2)	0.046 (2)	0.0010 (16)	−0.0013 (18)	−0.0067 (19)
C19	0.040 (2)	0.048 (3)	0.057 (3)	−0.0060 (19)	−0.006 (2)	0.002 (2)
C20	0.051 (3)	0.045 (2)	0.066 (3)	−0.008 (2)	0.008 (2)	−0.002 (2)
C21	0.039 (2)	0.056 (3)	0.075 (3)	−0.003 (2)	0.003 (2)	−0.021 (3)
C22	0.042 (2)	0.053 (3)	0.085 (3)	0.004 (2)	−0.019 (2)	−0.009 (3)
C23	0.043 (2)	0.037 (2)	0.065 (3)	0.0060 (17)	−0.011 (2)	0.001 (2)

Geometric parameters (Å, º) top

Br1—C6	1.912 (4)	C11—C12	1.495 (5)
S1—O1	1.499 (3)	C11—C18	1.505 (5)
S1—C5	1.835 (4)	C11—H11	0.9800
S1—C2	1.847 (4)	C12—C13	1.375 (6)
O2—C7	1.191 (4)	C12—C17	1.382 (5)
O3—C10	1.199 (4)	C13—C14	1.401 (6)
O4—C10	1.338 (4)	C13—H13	0.9300
O4—C11	1.484 (4)	C14—C15	1.348 (7)
N1—C7	1.382 (5)	C14—H14	0.9300
N1—C3	1.458 (4)	C15—C16	1.364 (6)
N1—C5	1.466 (4)	C15—H15	0.9300
C2—C9	1.506 (6)	C16—C17	1.386 (6)
C2—C8	1.540 (6)	C16—H16	0.9300
C2—C3	1.567 (5)	C17—H17	0.9300
C3—C10	1.505 (5)	C18—C19	1.372 (5)
C3—H3	0.9800	C18—C23	1.388 (5)
C5—C6	1.537 (5)	C19—C20	1.385 (6)
C5—H5	0.9800	C19—H19	0.9300
C6—C7	1.528 (5)	C20—C21	1.371 (6)
C6—H6	0.9800	C20—H20	0.9300
C8—H8A	0.9600	C21—C22	1.374 (6)
C8—H8B	0.9600	C21—H21	0.9300
C8—H8C	0.9600	C22—C23	1.371 (5)
C9—H9A	0.9600	C22—H22	0.9300
C9—H9B	0.9600	C23—H23	0.9300
C9—H9C	0.9600

O1—S1—C5	103.90 (17)	O3—C10—O4	124.8 (3)
O1—S1—C2	105.5 (2)	O3—C10—C3	126.0 (3)
C5—S1—C2	88.00 (16)	O4—C10—C3	109.1 (3)
C10—O4—C11	116.5 (3)	O4—C11—C12	109.9 (3)
C7—N1—C3	123.6 (3)	O4—C11—C18	105.5 (3)
C7—N1—C5	93.0 (3)	C12—C11—C18	115.4 (3)
C3—N1—C5	117.1 (3)	O4—C11—H11	108.6
C9—C2—C8	113.1 (4)	C12—C11—H11	108.6
C9—C2—C3	112.4 (3)	C18—C11—H11	108.6
C8—C2—C3	111.8 (3)	C13—C12—C17	119.2 (4)
C9—C2—S1	107.7 (3)	C13—C12—C11	122.9 (4)
C8—C2—S1	108.0 (3)	C17—C12—C11	117.9 (4)
C3—C2—S1	103.1 (3)	C12—C13—C14	119.7 (4)
N1—C3—C10	112.3 (3)	C12—C13—H13	120.1
N1—C3—C2	105.4 (3)	C14—C13—H13	120.1
C10—C3—C2	112.8 (3)	C15—C14—C13	120.0 (4)
N1—C3—H3	108.7	C15—C14—H14	120.0
C10—C3—H3	108.7	C13—C14—H14	120.0
C2—C3—H3	108.7	C14—C15—C16	121.3 (4)
N1—C5—C6	88.8 (3)	C14—C15—H15	119.4
N1—C5—S1	103.4 (2)	C16—C15—H15	119.4
C6—C5—S1	113.8 (3)	C15—C16—C17	119.3 (4)
N1—C5—H5	115.7	C15—C16—H16	120.4
C6—C5—H5	115.7	C17—C16—H16	120.4
S1—C5—H5	115.7	C12—C17—C16	120.6 (4)
C7—C6—C5	84.8 (3)	C12—C17—H17	119.7
C7—C6—Br1	115.9 (3)	C16—C17—H17	119.7
C5—C6—Br1	114.8 (3)	C19—C18—C23	118.8 (4)
C7—C6—H6	112.8	C19—C18—C11	121.8 (3)
C5—C6—H6	112.8	C23—C18—C11	119.4 (3)
Br1—C6—H6	112.8	C18—C19—C20	120.4 (4)
O2—C7—N1	130.6 (3)	C18—C19—H19	119.8
O2—C7—C6	136.9 (4)	C20—C19—H19	119.8
N1—C7—C6	92.4 (3)	C21—C20—C19	120.2 (4)
C2—C8—H8A	109.5	C21—C20—H20	119.9
C2—C8—H8B	109.5	C19—C20—H20	119.9
H8A—C8—H8B	109.5	C20—C21—C22	119.9 (4)
C2—C8—H8C	109.5	C20—C21—H21	120.0
H8A—C8—H8C	109.5	C22—C21—H21	120.0
H8B—C8—H8C	109.5	C23—C22—C21	119.8 (4)
C2—C9—H9A	109.5	C23—C22—H22	120.1
C2—C9—H9B	109.5	C21—C22—H22	120.1
H9A—C9—H9B	109.5	C22—C23—C18	120.9 (4)
C2—C9—H9C	109.5	C22—C23—H23	119.5
H9A—C9—H9C	109.5	C18—C23—H23	119.5
H9B—C9—H9C	109.5

O1—S1—C2—C9	−58.9 (3)	C5—C6—C7—N1	−7.5 (3)
C5—S1—C2—C9	−162.8 (3)	Br1—C6—C7—N1	107.6 (3)
O1—S1—C2—C8	178.6 (3)	C11—O4—C10—O3	−1.9 (5)
C5—S1—C2—C8	74.7 (3)	C11—O4—C10—C3	−179.8 (3)
O1—S1—C2—C3	60.1 (3)	N1—C3—C10—O3	20.8 (5)
C5—S1—C2—C3	−43.8 (3)	C2—C3—C10—O3	−98.2 (4)
C7—N1—C3—C10	114.4 (4)	N1—C3—C10—O4	−161.3 (3)
C5—N1—C3—C10	−131.4 (3)	C2—C3—C10—O4	79.7 (4)
C7—N1—C3—C2	−122.4 (4)	C10—O4—C11—C12	−82.9 (4)
C5—N1—C3—C2	−8.2 (4)	C10—O4—C11—C18	152.0 (3)
C9—C2—C3—N1	152.1 (4)	O4—C11—C12—C13	−23.0 (5)
C8—C2—C3—N1	−79.5 (4)	C18—C11—C12—C13	96.2 (4)
S1—C2—C3—N1	36.3 (3)	O4—C11—C12—C17	159.5 (3)
C9—C2—C3—C10	−85.0 (4)	C18—C11—C12—C17	−81.4 (4)
C8—C2—C3—C10	43.4 (4)	C17—C12—C13—C14	−0.7 (6)
S1—C2—C3—C10	159.2 (3)	C11—C12—C13—C14	−178.2 (4)
C7—N1—C5—C6	−7.8 (3)	C12—C13—C14—C15	−0.8 (6)
C3—N1—C5—C6	−138.3 (3)	C13—C14—C15—C16	1.6 (7)
C7—N1—C5—S1	106.4 (2)	C14—C15—C16—C17	−0.9 (7)
C3—N1—C5—S1	−24.1 (4)	C13—C12—C17—C16	1.3 (6)
O1—S1—C5—N1	−66.7 (3)	C11—C12—C17—C16	179.0 (4)
C2—S1—C5—N1	38.7 (3)	C15—C16—C17—C12	−0.6 (6)
O1—S1—C5—C6	28.0 (3)	O4—C11—C18—C19	76.6 (4)
C2—S1—C5—C6	133.5 (3)	C12—C11—C18—C19	−45.0 (5)
N1—C5—C6—C7	7.1 (3)	O4—C11—C18—C23	−104.1 (4)
S1—C5—C6—C7	−97.1 (3)	C12—C11—C18—C23	134.3 (4)
N1—C5—C6—Br1	−109.1 (3)	C23—C18—C19—C20	0.2 (6)
S1—C5—C6—Br1	146.69 (19)	C11—C18—C19—C20	179.5 (4)
C3—N1—C7—O2	−43.8 (6)	C18—C19—C20—C21	−0.4 (6)
C5—N1—C7—O2	−169.4 (5)	C19—C20—C21—C22	0.1 (6)
C3—N1—C7—C6	133.5 (3)	C20—C21—C22—C23	0.3 (6)
C5—N1—C7—C6	7.9 (3)	C21—C22—C23—C18	−0.5 (6)
C5—C6—C7—O2	169.5 (5)	C19—C18—C23—C22	0.2 (6)
Br1—C6—C7—O2	−75.4 (6)	C11—C18—C23—C22	−179.1 (4)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C18–C23 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O2ⁱ	0.93	2.54	3.465 (5)	171
C22—H22···O1ⁱⁱ	0.93	2.55	3.375 (5)	148
C14—H14···Cgⁱⁱⁱ	0.93	2.68	3.533 (5)	153

Symmetry codes: (i) −y+1, x+1, z+1/4; (ii) −x+1, −y+1, z+1/2; (iii) y−1, −x+1, z−1/4.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
Bai, G. Y., Chen, L. G., Li, Y. & Cao, L. (2001). Jingxi Huagong, 18, 634–637. CAS Google Scholar
Bruker (2004). APEX2, SADABS, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Xu, W. L., Li, Y. Z., Zhang, Q. S. & Zhu, H. S. (2005). Synthesis, pp. 442–446. Web of Science CrossRef Google Scholar

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Volume 5| Part 2| February 2020| x200143

https://doi.org/10.1107/S2414314620001431

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(3S,5R,6S)-Di­phenyl­methyl 1-oxo-6-bromo­penicillanate

Structure description

Synthesis and crystallization

Refinement

Structural data

References

organic compounds

(3S,5R,6S)-Diphenylmethyl 1-oxo-6-bromopenicillanate