(6R,7R)-3-Hydroxymethyl-7-(2-phenyl­acetamido)-3-cephem-4-carboxylic acid lactone

Zhou, X.-L.; Wang, H.; Wang, Y.; Shi, P.-J.

doi:10.1107/S1600536811043881

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3101

doi:10.1107/S1600536811043881

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(6R,7R)-3-Hydroxymethyl-7-(2-phenylacetamido)-3-cephem-4-carboxylic acid lactone

Xiao-Liang Zhou,^a ^* Hao Wang,^a Yan Wang ^a and Pei-Ji Shi ^a

^aInstitute of Radiation Medicine, Peking Union Medical College & Chinese Academy of Medical Sciences, Tianjin 300192, People's Republic of China
^*Correspondence e-mail: wobushibaojian@163.com

(Received 20 September 2011; accepted 22 October 2011; online 29 October 2011)

In the title compound {systematic name: N-[(4R,5R)-3,11-dioxo-10-oxa-6-thia-2-azatricyclo[6.3.0.0^2,5]undec-1(8)-en-4-yl]-2-phenylacetamide}, C₁₆H₁₄N₂O₄S, the four- and five-membered rings adopt planar conformations (with r.m.s. deviations of 0.0349 and 0.0108 Å respectively) while the six-membered ring adopts a half-chair, or envelope-like, conformation with the S atom in the flap position. In the crystal, molecules are linked by N—H⋯O hydrogen bonds.

Related literature

For standard bond lengths, see: Allen et al. (1987 ) and for ring puckering parameters, see: Cremer & Pople (1975 ). The title compound is an important synthetic intermediate for cephalosporins. For its synthesis, see: Yu et al. (2009 ).

Experimental

Crystal data

C₁₆H₁₄N₂O₄S
M_r = 330.35
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.1300 (13) Å
b = 9.7060 (14) Å
c = 16.701 (2) Å
V = 1480.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 113 K
0.26 × 0.24 × 0.22 mm

Data collection

Rigaku Saturn724 CCD diffractometer
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2009 ) T_min = 0.940, T_max = 0.949
21123 measured reflections
4249 independent reflections
3823 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.065
S = 1.02
4249 reflections
213 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.29 e Å⁻³
Absolute structure: Flack (1983 ), 1803 Friedel pairs
Flack parameter: −0.02 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯O4ⁱ	0.778 (15)	2.276 (15)	3.0506 (14)	173.5 (14)
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrystalClear-SM Expert (Rigaku, 2009); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2009); software used to prepare material for publication: CrystalStructure.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811043881/zj2026sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811043881/zj2026Isup2.hkl

checkCIF report

Comment top

The title compound is a lactone derivative of cephalosporin, which was fond originally as an impurity in the synthetic process, but now has become an useful intermediate, because the lactone ring enhances the stability of the molecule and adds new sites for structure reformation.There is one molecule in the asymmetric unit of the title compound. The absolute configuration has been determined by refinement of the Flack parameter (Flack, 1983) which converged to -0.02 (4). The ring A (N1—C1—C2—C3) and ring C (C4—C5—O3—C6—C7) adopt planer conformation with the r.m.s. deviation were 0.0349 and 0.0108 respectively, the ring B (S1—C3—N1—C4—C7—C8) displays half chair conformation with atom S1 in the flap position [the displacement from the C-atom mean plane is 0.3949 (6) Å], with the r.m.s. deviation was 0.2468 and with puckering parameters (Cremer and Pople, 1975) of Q (total puckering amplitude) = 0.6064 (10) Å, θ (azimuthal angle) = 127.68 (10)°, ϕ (phase angle) = 188.04 (15)°. The dihedral angle between ring A and ring B was 36.45 (7) °, and the dihedral angle between ring B and ring C was 10.34 (7) °. The spatial orientation of the phenyl ring can be described by the dihedral angle between the phenyl ring and the ring A [42.06 (6)]. The torsion angle of C4—N1—C3—S1 was -39.63 (13)°, and the torsion angle of N2—C2—C3—N1 was 120.16 (10)°. In the crystal, molecules are linked by N—H···O [N2—H1···O4=173.5 (14)°, N2···O4=3.0506 (14) Å] hydrogen bonds.

Related literature top

For standard bond lengths, see: Allen et al. (1987) and for ring puckering parameters, see: Cremer & Pople (1975). The title compound is an important synthetic intermediate for cephalosporins. For its synthesis, see: Yu et al. (2009).

Experimental top

The title compound was synthesized according to the literature method (Yu et al. (2009). Colorless Prism-shaped single crystals suitable for X-ray structure determination were recrystallized from acetone by the slow evaporation of the solvent at room temperature after several days.

Computing details top

Data collection: CrystalClear-SM Expert (Rigaku, 2009); cell refinement: CrystalClear-SM Expert (Rigaku, 2009); data reduction: CrystalClear-SM Expert (Rigaku, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2009); software used to prepare material for publication: CrystalStructure (Rigaku, 2009).

Figures top

	Fig. 1. Molecular structure of the title compound with the atomic numbering scheme and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The crystal packing of the title compound viewed along the a axis, hydrogen bonds are shown as dashed lines.

N-[(4R,5R)-3,11-Dioxo-10-oxa-6-thia-2- azatricyclo[6.3.0.0^2,5]undec-1(8)-en-4-yl]-2-phenylacetamide top

Crystal data top

C₁₆H₁₄N₂O₄S	F(000) = 688
M_r = 330.35	D_x = 1.483 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5950 reflections
a = 9.1300 (13) Å	θ = 1.2–29.9°
b = 9.7060 (14) Å	µ = 0.24 mm⁻¹
c = 16.701 (2) Å	T = 113 K
V = 1480.0 (3) Å³	Prism, colourless
Z = 4	0.26 × 0.24 × 0.22 mm

Data collection top

Rigaku Saturn724 CCD diffractometer	4249 independent reflections
Radiation source: rotating anode	3823 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.043
Detector resolution: 14.222 pixels mm^-1	θ_max = 30.0°, θ_min = 2.4°
ω scans	h = −12→12
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2009)	k = −13→13
T_min = 0.940, T_max = 0.949	l = −23→22
21123 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.027	w = 1/[σ²(F_o²) + (0.0358P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.065	(Δ/σ)_max = 0.001
S = 1.02	Δρ_max = 0.25 e Å⁻³
4249 reflections	Δρ_min = −0.29 e Å⁻³
213 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0067 (12)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1803 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.02 (4)

Crystal data top

C₁₆H₁₄N₂O₄S	V = 1480.0 (3) Å³
M_r = 330.35	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.1300 (13) Å	µ = 0.24 mm⁻¹
b = 9.7060 (14) Å	T = 113 K
c = 16.701 (2) Å	0.26 × 0.24 × 0.22 mm

Data collection top

Rigaku Saturn724 CCD diffractometer	4249 independent reflections
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2009)	3823 reflections with I > 2σ(I)
T_min = 0.940, T_max = 0.949	R_int = 0.043
21123 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.065	Δρ_max = 0.25 e Å⁻³
S = 1.02	Δρ_min = −0.29 e Å⁻³
4249 reflections	Absolute structure: Flack (1983), 1803 Friedel pairs
213 parameters	Absolute structure parameter: −0.02 (4)
0 restraints

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	U_iso*/U_eq
S1	0.67754 (3)	0.52846 (3)	0.117029 (18)	0.01734 (8)
O1	0.88288 (11)	0.84664 (9)	0.27380 (5)	0.0225 (2)
O2	1.16829 (11)	0.84019 (9)	0.14678 (5)	0.0244 (2)
O3	1.13554 (11)	0.75318 (9)	0.02326 (5)	0.0200 (2)
O4	0.49856 (10)	0.45642 (8)	0.28773 (5)	0.0208 (2)
N1	0.91224 (11)	0.64624 (10)	0.19268 (6)	0.0154 (2)
N2	0.58912 (12)	0.67140 (11)	0.27251 (6)	0.0160 (2)
C1	0.85344 (13)	0.73156 (12)	0.25163 (7)	0.0160 (2)
C2	0.73837 (13)	0.62194 (12)	0.27474 (7)	0.0157 (2)
H2	0.7621	0.5770	0.3270	0.019*
C3	0.79901 (12)	0.53771 (12)	0.20224 (7)	0.0145 (2)
H3	0.8404	0.4462	0.2180	0.017*
C4	0.97995 (13)	0.66890 (12)	0.11842 (7)	0.0148 (2)
C5	1.10260 (14)	0.76339 (12)	0.10264 (7)	0.0173 (3)
C6	1.03597 (15)	0.65749 (13)	−0.01579 (7)	0.0184 (3)
H6A	1.0906	0.5813	−0.0415	0.022*
H6B	0.9764	0.7051	−0.0569	0.022*
C7	0.94119 (14)	0.60460 (13)	0.05064 (7)	0.0160 (3)
C8	0.82046 (14)	0.50169 (12)	0.04180 (7)	0.0175 (2)
H8A	0.8610	0.4076	0.0475	0.021*
H8B	0.7772	0.5097	−0.0124	0.021*
C9	0.47668 (14)	0.58147 (13)	0.28174 (7)	0.0163 (2)
C10	0.32515 (14)	0.64414 (12)	0.28916 (7)	0.0176 (2)
H10A	0.2560	0.5957	0.2532	0.021*
H10B	0.3279	0.7425	0.2735	0.021*
C11	0.27483 (13)	0.63045 (12)	0.37592 (8)	0.0159 (2)
C12	0.35751 (14)	0.68729 (12)	0.43847 (8)	0.0182 (3)
H12	0.4433	0.7385	0.4263	0.022*
C13	0.31636 (15)	0.67012 (13)	0.51797 (7)	0.0206 (3)
H13	0.3739	0.7093	0.5595	0.025*
C14	0.19037 (15)	0.59516 (14)	0.53662 (8)	0.0243 (3)
H14	0.1618	0.5824	0.5908	0.029*
C15	0.10737 (15)	0.53953 (14)	0.47505 (8)	0.0257 (3)
H15	0.0213	0.4889	0.4875	0.031*
C16	0.14795 (13)	0.55650 (13)	0.39503 (8)	0.0207 (3)
H16	0.0895	0.5179	0.3536	0.025*
H1	0.5708 (16)	0.7467 (16)	0.2600 (8)	0.021 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01461 (14)	0.02029 (15)	0.01712 (13)	0.00003 (12)	−0.00149 (12)	−0.00324 (12)
O1	0.0267 (5)	0.0206 (4)	0.0201 (4)	−0.0045 (4)	0.0017 (4)	−0.0043 (4)
O2	0.0271 (5)	0.0249 (5)	0.0213 (4)	−0.0103 (5)	0.0002 (4)	−0.0028 (4)
O3	0.0252 (5)	0.0186 (4)	0.0162 (4)	−0.0050 (4)	0.0036 (4)	−0.0004 (4)
O4	0.0214 (4)	0.0130 (4)	0.0278 (5)	0.0011 (4)	0.0042 (4)	0.0025 (4)
N1	0.0166 (5)	0.0162 (5)	0.0135 (5)	−0.0044 (4)	0.0004 (4)	0.0002 (4)
N2	0.0170 (5)	0.0122 (5)	0.0188 (5)	0.0014 (4)	0.0027 (4)	0.0023 (4)
C1	0.0175 (6)	0.0184 (6)	0.0119 (5)	−0.0009 (5)	−0.0013 (4)	0.0007 (4)
C2	0.0165 (6)	0.0161 (5)	0.0145 (6)	−0.0006 (5)	0.0007 (5)	0.0013 (5)
C3	0.0152 (6)	0.0142 (5)	0.0143 (5)	−0.0020 (5)	−0.0003 (4)	0.0017 (4)
C4	0.0153 (5)	0.0144 (5)	0.0149 (5)	−0.0005 (5)	0.0004 (5)	0.0008 (5)
C5	0.0192 (6)	0.0153 (6)	0.0173 (6)	−0.0006 (5)	0.0015 (5)	0.0010 (5)
C6	0.0228 (6)	0.0166 (6)	0.0158 (6)	−0.0008 (5)	0.0021 (5)	−0.0015 (5)
C7	0.0170 (6)	0.0142 (6)	0.0168 (6)	0.0035 (5)	0.0005 (5)	0.0005 (5)
C8	0.0166 (5)	0.0193 (6)	0.0166 (5)	−0.0005 (5)	0.0009 (5)	−0.0047 (4)
C9	0.0191 (6)	0.0173 (6)	0.0126 (5)	0.0001 (5)	0.0018 (5)	0.0000 (5)
C10	0.0174 (6)	0.0165 (6)	0.0190 (6)	−0.0002 (5)	0.0013 (5)	0.0024 (5)
C11	0.0155 (6)	0.0134 (5)	0.0188 (6)	0.0040 (5)	0.0015 (5)	0.0009 (5)
C12	0.0178 (6)	0.0132 (5)	0.0237 (6)	0.0023 (5)	0.0014 (5)	−0.0005 (5)
C13	0.0231 (6)	0.0189 (6)	0.0198 (6)	0.0059 (6)	−0.0004 (5)	−0.0048 (5)
C14	0.0274 (7)	0.0247 (7)	0.0210 (6)	0.0045 (6)	0.0064 (6)	−0.0013 (5)
C15	0.0203 (6)	0.0286 (7)	0.0282 (7)	−0.0048 (6)	0.0104 (5)	−0.0030 (6)
C16	0.0152 (6)	0.0229 (6)	0.0238 (7)	−0.0007 (5)	0.0018 (5)	−0.0029 (5)

Geometric parameters (Å, º) top

S1—C3	1.8065 (12)	C6—H6A	0.9900
S1—C8	1.8300 (12)	C6—H6B	0.9900
O1—C1	1.2070 (14)	C7—C8	1.4949 (17)
O2—C5	1.2079 (15)	C8—H8A	0.9900
O3—C5	1.3630 (14)	C8—H8B	0.9900
O3—C6	1.4540 (15)	C9—C10	1.5164 (18)
O4—C9	1.2341 (14)	C10—C11	1.5258 (17)
N1—C1	1.3940 (15)	C10—H10A	0.9900
N1—C4	1.4030 (15)	C10—H10B	0.9900
N1—C3	1.4846 (15)	C11—C16	1.3997 (16)
N2—C9	1.3563 (16)	C11—C12	1.4019 (17)
N2—C2	1.4452 (16)	C12—C13	1.3900 (17)
N2—H1	0.778 (15)	C12—H12	0.9500
C1—C2	1.5443 (17)	C13—C14	1.3963 (19)
C2—C3	1.5623 (16)	C13—H13	0.9500
C2—H2	1.0000	C14—C15	1.3868 (19)
C3—H3	1.0000	C14—H14	0.9500
C4—C7	1.3401 (17)	C15—C16	1.3966 (17)
C4—C5	1.4713 (17)	C15—H15	0.9500
C6—C7	1.4978 (17)	C16—H16	0.9500

C3—S1—C8	96.33 (5)	C4—C7—C6	108.27 (11)
C5—O3—C6	110.17 (9)	C8—C7—C6	125.58 (10)
C1—N1—C4	134.50 (10)	C7—C8—S1	111.29 (8)
C1—N1—C3	94.44 (9)	C7—C8—H8A	109.4
C4—N1—C3	120.87 (9)	S1—C8—H8A	109.4
C9—N2—C2	119.79 (10)	C7—C8—H8B	109.4
C9—N2—H1	118.2 (11)	S1—C8—H8B	109.4
C2—N2—H1	121.4 (11)	H8A—C8—H8B	108.0
O1—C1—N1	132.89 (11)	O4—C9—N2	121.31 (12)
O1—C1—C2	135.44 (11)	O4—C9—C10	122.38 (11)
N1—C1—C2	91.67 (9)	N2—C9—C10	116.21 (11)
N2—C2—C1	113.96 (10)	C9—C10—C11	108.50 (10)
N2—C2—C3	119.21 (10)	C9—C10—H10A	110.0
C1—C2—C3	85.74 (9)	C11—C10—H10A	110.0
N2—C2—H2	111.8	C9—C10—H10B	110.0
C1—C2—H2	111.8	C11—C10—H10B	110.0
C3—C2—H2	111.8	H10A—C10—H10B	108.4
N1—C3—C2	87.64 (8)	C16—C11—C12	118.53 (12)
N1—C3—S1	112.21 (8)	C16—C11—C10	120.69 (11)
C2—C3—S1	114.77 (8)	C12—C11—C10	120.75 (11)
N1—C3—H3	113.3	C13—C12—C11	121.27 (12)
C2—C3—H3	113.3	C13—C12—H12	119.4
S1—C3—H3	113.3	C11—C12—H12	119.4
C7—C4—N1	123.87 (11)	C12—C13—C14	119.88 (12)
C7—C4—C5	109.87 (11)	C12—C13—H13	120.1
N1—C4—C5	126.25 (11)	C14—C13—H13	120.1
O2—C5—O3	121.94 (11)	C15—C14—C13	119.19 (12)
O2—C5—C4	130.79 (12)	C15—C14—H14	120.4
O3—C5—C4	107.27 (10)	C13—C14—H14	120.4
O3—C6—C7	104.35 (9)	C14—C15—C16	121.24 (12)
O3—C6—H6A	110.9	C14—C15—H15	119.4
C7—C6—H6A	110.9	C16—C15—H15	119.4
O3—C6—H6B	110.9	C15—C16—C11	119.88 (12)
C7—C6—H6B	110.9	C15—C16—H16	120.1
H6A—C6—H6B	108.9	C11—C16—H16	120.1
C4—C7—C8	126.11 (11)

C4—N1—C1—O1	−30.8 (2)	N1—C4—C5—O2	−1.1 (2)
C3—N1—C1—O1	−173.70 (14)	C7—C4—C5—O3	−0.01 (14)
C4—N1—C1—C2	148.54 (13)	N1—C4—C5—O3	179.44 (11)
C3—N1—C1—C2	5.61 (9)	C5—O3—C6—C7	−2.54 (13)
C9—N2—C2—C1	171.83 (10)	N1—C4—C7—C8	1.1 (2)
C9—N2—C2—C3	72.89 (15)	C5—C4—C7—C8	−179.45 (11)
O1—C1—C2—N2	53.78 (19)	N1—C4—C7—C6	178.94 (11)
N1—C1—C2—N2	−125.50 (10)	C5—C4—C7—C6	−1.59 (14)
O1—C1—C2—C3	173.95 (15)	O3—C6—C7—C4	2.50 (14)
N1—C1—C2—C3	−5.33 (9)	O3—C6—C7—C8	−179.63 (11)
C1—N1—C3—C2	−5.55 (9)	C4—C7—C8—S1	26.83 (16)
C4—N1—C3—C2	−155.48 (10)	C6—C7—C8—S1	−150.67 (10)
C1—N1—C3—S1	110.30 (9)	C3—S1—C8—C7	−49.31 (9)
C4—N1—C3—S1	−39.63 (13)	C2—N2—C9—O4	−4.00 (18)
N2—C2—C3—N1	120.16 (10)	C2—N2—C9—C10	172.50 (10)
C1—C2—C3—N1	5.01 (8)	O4—C9—C10—C11	69.25 (15)
N2—C2—C3—S1	6.73 (13)	N2—C9—C10—C11	−107.21 (12)
C1—C2—C3—S1	−108.42 (9)	C9—C10—C11—C16	−119.87 (12)
C8—S1—C3—N1	56.24 (9)	C9—C10—C11—C12	57.76 (14)
C8—S1—C3—C2	154.26 (9)	C16—C11—C12—C13	0.65 (17)
C1—N1—C4—C7	−130.03 (14)	C10—C11—C12—C13	−177.03 (11)
C3—N1—C4—C7	5.52 (18)	C11—C12—C13—C14	−0.08 (19)
C1—N1—C4—C5	50.6 (2)	C12—C13—C14—C15	−0.42 (19)
C3—N1—C4—C5	−173.86 (11)	C13—C14—C15—C16	0.3 (2)
C6—O3—C5—O2	−177.82 (12)	C14—C15—C16—C11	0.2 (2)
C6—O3—C5—C4	1.67 (13)	C12—C11—C16—C15	−0.72 (18)
C7—C4—C5—O2	179.42 (14)	C10—C11—C16—C15	176.96 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O4ⁱ	0.778 (15)	2.276 (15)	3.0506 (14)	173.5 (14)

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄N₂O₄S
M_r	330.35
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	113
a, b, c (Å)	9.1300 (13), 9.7060 (14), 16.701 (2)
V (Å³)	1480.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.26 × 0.24 × 0.22

Data collection
Diffractometer	Rigaku Saturn724 CCD diffractometer
Absorption correction	Multi-scan (CrystalClear-SM Expert; Rigaku, 2009)
T_min, T_max	0.940, 0.949
No. of measured, independent and observed [I > 2σ(I)] reflections	21123, 4249, 3823
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.065, 1.02
No. of reflections	4249
No. of parameters	213
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.29
Absolute structure	Flack (1983), 1803 Friedel pairs
Absolute structure parameter	−0.02 (4)

Computer programs: CrystalClear-SM Expert (Rigaku, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O4ⁱ	0.778 (15)	2.276 (15)	3.0506 (14)	173.5 (14)

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Acknowledgements

The authors acknowledge financial support from the Institute of Radiation Medicine, Chinese Academy of Medical Sciences (No. SF1002).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Cremer, D. & &Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Rigaku (2009). CrystalClear-SM Expert and CrystalStructure. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yu, K., Sun, N., Fang, S., Mo, W., Hu, B., Shen, Z. & Hu, X. (2009). Org. Process Res. Dev. 13, 815–819. Web of Science CrossRef CAS Google Scholar

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Volume 67| Part 11| November 2011| Page o3101

doi:10.1107/S1600536811043881

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

(6R,7R)-3-Hydroxymethyl-7-(2-phenyl­acetamido)-3-cephem-4-carboxylic acid lactone

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(6R,7R)-3-Hydroxymethyl-7-(2-phenylacetamido)-3-cephem-4-carboxylic acid lactone