Crystal structure of benzyl 3-oxo-2-oxa-5-aza­bicyclo­[2.2.1]heptane-5-carboxyl­ate

Krishnamurthy, S.; Jalli, V.; Vagvala, T.C.; Moriguchi, T.; Tsuge, A.

doi:10.1107/S2056989015010464

organic compounds

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ISSN: 2056-9890

Volume 71| Part 7| July 2015| Pages o447-o448

doi:10.1107/S2056989015010464

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Crystal structure of benzyl 3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate

Suvratha Krishnamurthy,^a ^* Venkataprasad Jalli,^a Tarun Chand Vagvala,^b Tetsuji Moriguchi ^a and Akihiko Tsuge ^a

^aDepartment of Applied Chemistry, Graduate School of Engineering, Kyushu Institute of Technology, 1-1 sensui-cho tobata-ku kitakyushu 804-8550, Japan, and ^bDepartment of Biological Functions and Systems Graduate School of Life Science and Systems Engineering, Kyushu Institute of Technology, 2-4 Hibikino, Wakamatsu-ku, Kitakyushu 808-0196, Japan
^*Correspondence e-mail: suvrathak@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 23 May 2015; accepted 1 June 2015; online 6 June 2015)

The title compound, C₁₃H₁₃NO₄ (also known as N-benzyloxycarbonyl-4-hydroxy-L-proline lactone), crystallizes with two molecules in the asymmetric unit. They have slightly different conformations: the fused ring systems almost overlap, but different C—O—C—C torsion angles for the central chains of −155.5 (2) and −178.6 (2)° lead to different twists for the terminal benzene ring. In the crystal, the molecules are linked by C—H⋯O interactions, generating a three-dimensional network. The absolute structure was established based on an unchanging chiral centre in the synthesis.

Keywords: crystal structure; 4-hydroxyproline; C—H⋯O interactions.

CCDC reference: 1402251

1. Related literature

For biological background, see: Dickens et al. (2008 ); Erdmann & Wennemers (2011 ); Krishnamurthy et al. (2014 ); Gómez-Vidal & Silverman (2001 ). For the synthesis, see: Lombardo et al. (2012 ).

2. Experimental

2.1. Crystal data

C₁₃H₁₃NO₄
M_r = 247.24
Monoclinic, P 2₁
a = 11.212 (2) Å
b = 8.8943 (16) Å
c = 12.258 (2) Å
β = 105.345 (2)°
V = 1178.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 90 K
0.40 × 0.35 × 0.30 mm

2.2. Data collection

Bruker APEX II KY CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.709, T_max = 0.969
11252 measured reflections
4157 independent reflections
4079 reflections with I > 2σ(I)
R_int = 0.035

2.3. Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.073
S = 1.06
4157 reflections
325 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O5ⁱ	0.98	2.42	3.3493 (18)	159
C2—H2A⋯O7ⁱⁱ	0.97	2.46	3.2116 (18)	134
C3—H3⋯O5ⁱⁱⁱ	0.98	2.37	3.2816 (18)	155
C4—H4B⋯O7ⁱⁱⁱ	0.97	2.39	3.3408 (18)	168
C15—H15A⋯O3^iv	0.97	2.44	3.1382 (19)	128
C16—H16⋯O1^v	0.98	2.49	3.2207 (18)	131
C26—H26⋯O6^vi	0.93	2.58	3.4584 (19)	157
Symmetry codes: (i) x-1, y-1, z; (ii) x-1, y, z; (iii) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (iv) x+1, y+1, z; (v) $[-x+1, y+{\script{1\over 2}}, -z]$ ; (vi) x, y-1, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 1402251

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015010464/hb7435sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015010464/hb7435Isup2.hkl

checkCIF report

Chemical context top

Four possible stereoisomers exists for 4-hydroxyproline. The (2S,4R)-isomer is mainly found in collagen and its presence in collagen is a very important factor for its triple helix stabilization (Erdmann & Wennemers, 2011). Moreover (2S,4S)- of 4-hydroxyproline isomer was found to have anticancer activity (Dickens et al. 2008)

For related derivatives and synthesis see (Krishnamurthy et al. 2014, Gomez-Vidal and Silverman, 2001)

Synthesis and crystallization top

(I) was prepared in exactly the same manner as described by (Lombardo et al. 2012). To a solution of Z-Hyp-OH (3.0 g, 11.3 mmol) and triphenylphosphine (3.5 g, 13.3 mmol) in dry THF (50 mL) at 0 °C, was added DEAD (40% in toluene, 5.7 mL, 12.4 mmol), under argon. The resulting solution was warmed to room temperature and stirred. After 12 h, the solvent was evaporated to give a crude residue which was purified directly by flash chromatography on silica gel (EtOAc:hexane, 40:60, v/v) to give I as a white solid ( 2 g, 72 %). (¹H NMR matched Lombardo et al. 2012)

Single crystals were obtained by vapour diffusion method at room temperature, i.e., pentane vapour was allowed to slowly diffuse into a EtOAc (0.3 ml) solution of I at room temperature. Single crystals were obtained after three days.

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 1.

Related literature top

For biological background, see: Dickens et al. (2008); Erdmann & Wennemers (2011); Krishnamurthy et al. (2014); Gómez-Vidal & Silverman (2001). For the synthesis, see: Lombardo et al. (2012).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. Molecular configuration for the title compound with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.
	Fig. 2. Crystal packing diagram of the title compound.
	Fig. 3. Synthetic scheme for the title compound (I)

(I) top

Crystal data top

C₁₃H₁₃NO₄	Z = 4
M_r = 247.24	F(000) = 520
Monoclinic, P2₁	D_x = 1.393 Mg m⁻³
a = 11.212 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.8943 (16) Å	µ = 0.10 mm⁻¹
c = 12.258 (2) Å	T = 90 K
β = 105.345 (2)°	Prism, colorless
V = 1178.8 (4) Å³	0.40 × 0.35 × 0.30 mm

Data collection top

Bruker APEX II KY CCD diffractometer	4157 independent reflections
Radiation source: fine-focus sealed tube	4079 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 8.333 pixels mm^-1	θ_max = 25.0°, θ_min = 1.7°
ϕandω–scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→10
T_min = 0.709, T_max = 0.969	l = −14→14
11252 measured reflections

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.073	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0404P)² + 0.1656P] where P = (F_o² + 2F_c²)/3
4157 reflections	(Δ/σ)_max < 0.001
325 parameters	Δρ_max = 0.19 e Å⁻³
1 restraint	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₃H₁₃NO₄	V = 1178.8 (4) Å³
M_r = 247.24	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 11.212 (2) Å	µ = 0.10 mm⁻¹
b = 8.8943 (16) Å	T = 90 K
c = 12.258 (2) Å	0.40 × 0.35 × 0.30 mm
β = 105.345 (2)°

Data collection top

Bruker APEX II KY CCD diffractometer	4157 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4079 reflections with I > 2σ(I)
T_min = 0.709, T_max = 0.969	R_int = 0.035
11252 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	1 restraint
wR(F²) = 0.073	H-atom parameters constrained
S = 1.06	Δρ_max = 0.19 e Å⁻³
4157 reflections	Δρ_min = −0.16 e Å⁻³
325 parameters

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
C1	0.03159 (12)	0.45789 (16)	0.37070 (12)	0.0215 (3)
H1	−0.0256	0.4019	0.31	0.026*
C2	−0.02168 (13)	0.52285 (17)	0.46339 (12)	0.0235 (3)
H2A	−0.0862	0.5968	0.4356	0.028*
H2B	−0.0493	0.4465	0.5077	0.028*
C3	0.10287 (13)	0.59254 (17)	0.52422 (12)	0.0229 (3)
H3	0.1023	0.6507	0.592	0.027*
C4	0.19041 (13)	0.45866 (17)	0.54550 (11)	0.0229 (3)
H4A	0.2754	0.4888	0.5535	0.027*
H4B	0.1852	0.4018	0.6116	0.027*
C5	0.09010 (12)	0.59924 (16)	0.33634 (11)	0.0210 (3)
C6	0.19212 (13)	0.25806 (16)	0.39927 (12)	0.0218 (3)
C7	0.35825 (16)	0.0823 (2)	0.44690 (14)	0.0356 (4)
H7A	0.4176	0.1195	0.4083	0.043*
H7B	0.3012	0.0154	0.3961	0.043*
C8	0.42360 (14)	0.00050 (16)	0.55255 (13)	0.0265 (3)
C9	0.35980 (13)	−0.10101 (17)	0.60196 (15)	0.0319 (4)
H9	0.2765	−0.1189	0.5683	0.038*
C10	0.41768 (15)	−0.17599 (18)	0.70017 (15)	0.0341 (4)
H10	0.3731	−0.2425	0.7328	0.041*
C11	0.54297 (15)	−0.15203 (18)	0.75052 (14)	0.0310 (3)
H11	0.5828	−0.2035	0.8161	0.037*
C12	0.60744 (13)	−0.05120 (18)	0.70219 (13)	0.0290 (3)
H12	0.6911	−0.0349	0.7354	0.035*
C13	0.54857 (13)	0.02589 (18)	0.60467 (13)	0.0281 (3)
H13	0.5926	0.095	0.5737	0.034*
C14	0.96660 (12)	0.95675 (15)	0.18254 (11)	0.0199 (3)
H14	0.9969	0.9291	0.2625	0.024*
C15	1.06237 (13)	0.96354 (17)	0.11437 (12)	0.0228 (3)
H15A	1.1262	1.0383	0.1421	0.027*
H15B	1.0989	0.8666	0.1065	0.027*
C16	0.96511 (13)	1.01286 (16)	0.00832 (12)	0.0230 (3)
H16	0.9969	1.0321	−0.0575	0.028*
C17	0.86734 (13)	0.88969 (16)	−0.00859 (11)	0.0227 (3)
H17A	0.7863	0.926	−0.0497	0.027*
H17B	0.8892	0.8029	−0.0472	0.027*
C18	0.90739 (12)	1.11153 (16)	0.15699 (11)	0.0200 (3)
C19	0.81590 (12)	0.74552 (15)	0.15094 (12)	0.0190 (3)
C20	0.66990 (14)	0.54756 (16)	0.09787 (12)	0.0257 (3)
H20A	0.6144	0.5876	0.1394	0.031*
H20B	0.7242	0.4745	0.145	0.031*
C21	0.59844 (12)	0.47712 (16)	−0.01037 (12)	0.0224 (3)
C22	0.47838 (13)	0.52208 (17)	−0.06415 (13)	0.0259 (3)
H22	0.4391	0.5936	−0.0305	0.031*
C23	0.41709 (13)	0.46052 (18)	−0.16784 (13)	0.0280 (3)
H23	0.3365	0.49	−0.2028	0.034*
C24	0.47492 (14)	0.35578 (17)	−0.21940 (13)	0.0293 (3)
H24	0.4339	0.3158	−0.2894	0.035*
C25	0.59509 (15)	0.31033 (18)	−0.16600 (14)	0.0310 (3)
H25	0.6349	0.2404	−0.2006	0.037*
C26	0.65512 (13)	0.36930 (17)	−0.06153 (13)	0.0262 (3)
H26	0.7344	0.3364	−0.0251	0.031*
N1	0.13918 (11)	0.37446 (13)	0.43984 (10)	0.0227 (3)
N2	0.87336 (11)	0.85642 (14)	0.11057 (9)	0.0213 (2)
O1	0.10735 (9)	0.63621 (12)	0.24784 (8)	0.0278 (2)
O2	0.13217 (9)	0.68041 (11)	0.43299 (8)	0.0233 (2)
O3	0.15344 (9)	0.20350 (13)	0.30604 (9)	0.0302 (2)
O4	0.29114 (9)	0.20752 (12)	0.47981 (8)	0.0267 (2)
O5	0.85762 (8)	1.19197 (12)	0.21078 (8)	0.0252 (2)
O6	0.91040 (9)	1.14515 (11)	0.04972 (8)	0.0232 (2)
O7	0.82890 (8)	0.71808 (11)	0.25057 (8)	0.0224 (2)
O8	0.74174 (9)	0.66846 (11)	0.06459 (8)	0.0244 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0192 (6)	0.0193 (7)	0.0234 (7)	0.0006 (6)	0.0013 (5)	−0.0015 (6)
C2	0.0206 (7)	0.0251 (7)	0.0246 (7)	0.0012 (6)	0.0055 (6)	0.0036 (6)
C3	0.0257 (7)	0.0239 (7)	0.0195 (7)	0.0011 (6)	0.0068 (6)	0.0003 (6)
C4	0.0246 (7)	0.0232 (7)	0.0200 (7)	0.0005 (6)	0.0043 (5)	0.0000 (6)
C5	0.0185 (6)	0.0229 (7)	0.0204 (7)	0.0071 (5)	0.0031 (5)	0.0010 (5)
C6	0.0188 (6)	0.0196 (7)	0.0268 (7)	−0.0004 (5)	0.0056 (5)	0.0016 (6)
C7	0.0374 (9)	0.0358 (8)	0.0343 (8)	0.0174 (7)	0.0109 (7)	−0.0006 (7)
C8	0.0245 (7)	0.0228 (8)	0.0325 (8)	0.0074 (6)	0.0081 (6)	−0.0035 (6)
C9	0.0171 (7)	0.0253 (8)	0.0502 (10)	−0.0003 (6)	0.0031 (6)	−0.0034 (7)
C10	0.0282 (8)	0.0255 (8)	0.0497 (10)	0.0006 (6)	0.0123 (7)	0.0060 (7)
C11	0.0278 (8)	0.0301 (8)	0.0329 (8)	0.0075 (6)	0.0042 (6)	0.0019 (6)
C12	0.0172 (7)	0.0322 (8)	0.0360 (8)	0.0036 (6)	0.0041 (6)	−0.0069 (7)
C13	0.0242 (7)	0.0253 (7)	0.0383 (9)	0.0007 (6)	0.0144 (7)	−0.0027 (7)
C14	0.0181 (6)	0.0208 (7)	0.0198 (6)	−0.0006 (5)	0.0032 (5)	−0.0009 (5)
C15	0.0201 (7)	0.0227 (7)	0.0262 (7)	0.0004 (6)	0.0073 (5)	−0.0026 (6)
C16	0.0262 (7)	0.0216 (7)	0.0239 (7)	0.0022 (6)	0.0111 (6)	−0.0007 (6)
C17	0.0253 (7)	0.0238 (7)	0.0183 (7)	−0.0008 (6)	0.0047 (5)	−0.0011 (6)
C18	0.0147 (6)	0.0220 (7)	0.0225 (7)	−0.0046 (5)	0.0034 (5)	−0.0025 (5)
C19	0.0149 (6)	0.0178 (7)	0.0238 (7)	0.0030 (5)	0.0043 (5)	−0.0001 (5)
C20	0.0267 (7)	0.0222 (8)	0.0284 (8)	−0.0069 (6)	0.0075 (6)	0.0006 (6)
C21	0.0213 (7)	0.0200 (7)	0.0266 (7)	−0.0057 (6)	0.0077 (5)	0.0017 (6)
C22	0.0224 (7)	0.0222 (7)	0.0345 (8)	0.0009 (6)	0.0103 (6)	0.0006 (6)
C23	0.0174 (7)	0.0278 (7)	0.0362 (8)	−0.0019 (6)	0.0028 (6)	0.0057 (7)
C24	0.0284 (8)	0.0271 (8)	0.0295 (8)	−0.0064 (6)	0.0026 (6)	−0.0028 (6)
C25	0.0298 (8)	0.0269 (8)	0.0376 (8)	0.0013 (6)	0.0112 (6)	−0.0057 (7)
C26	0.0178 (7)	0.0252 (7)	0.0350 (8)	0.0008 (6)	0.0061 (6)	0.0018 (6)
N1	0.0230 (6)	0.0191 (6)	0.0225 (6)	0.0033 (5)	0.0001 (5)	−0.0003 (5)
N2	0.0221 (6)	0.0216 (6)	0.0182 (6)	−0.0028 (5)	0.0016 (5)	−0.0011 (5)
O1	0.0283 (5)	0.0338 (6)	0.0224 (5)	0.0082 (5)	0.0086 (4)	0.0067 (4)
O2	0.0272 (5)	0.0203 (5)	0.0220 (5)	−0.0007 (4)	0.0058 (4)	0.0011 (4)
O3	0.0254 (5)	0.0293 (6)	0.0332 (6)	0.0024 (5)	0.0028 (4)	−0.0082 (5)
O4	0.0253 (5)	0.0249 (5)	0.0288 (5)	0.0079 (4)	0.0052 (4)	0.0010 (4)
O5	0.0210 (5)	0.0265 (5)	0.0280 (5)	−0.0002 (4)	0.0060 (4)	−0.0053 (4)
O6	0.0266 (5)	0.0192 (5)	0.0239 (5)	0.0018 (4)	0.0068 (4)	0.0018 (4)
O7	0.0207 (5)	0.0234 (5)	0.0226 (5)	0.0002 (4)	0.0049 (4)	0.0023 (4)
O8	0.0253 (5)	0.0230 (5)	0.0239 (5)	−0.0070 (4)	0.0048 (4)	−0.0011 (4)

Geometric parameters (Å, º) top

C1—N1	1.4776 (17)	C14—N2	1.4763 (17)
C1—C5	1.528 (2)	C14—C18	1.525 (2)
C1—C2	1.530 (2)	C14—C15	1.5263 (19)
C1—H1	0.98	C14—H14	0.98
C2—C3	1.530 (2)	C15—C16	1.524 (2)
C2—H2A	0.97	C15—H15A	0.97
C2—H2B	0.97	C15—H15B	0.97
C3—O2	1.4710 (17)	C16—O6	1.4775 (16)
C3—C4	1.521 (2)	C16—C17	1.525 (2)
C3—H3	0.98	C16—H16	0.98
C4—N1	1.4746 (18)	C17—N2	1.4742 (18)
C4—H4A	0.97	C17—H17A	0.97
C4—H4B	0.97	C17—H17B	0.97
C5—O1	1.1973 (18)	C18—O5	1.2053 (17)
C5—O2	1.3606 (17)	C18—O6	1.3576 (17)
C6—O3	1.2113 (18)	C19—O7	1.2158 (17)
C6—N1	1.3519 (19)	C19—N2	1.3423 (18)
C6—O4	1.3526 (17)	C19—O8	1.3475 (16)
C7—O4	1.4592 (18)	C20—O8	1.4648 (16)
C7—C8	1.497 (2)	C20—C21	1.494 (2)
C7—H7A	0.97	C20—H20A	0.97
C7—H7B	0.97	C20—H20B	0.97
C8—C9	1.387 (2)	C21—C26	1.388 (2)
C8—C13	1.396 (2)	C21—C22	1.392 (2)
C9—C10	1.379 (2)	C22—C23	1.388 (2)
C9—H9	0.93	C22—H22	0.93
C10—C11	1.393 (2)	C23—C24	1.380 (2)
C10—H10	0.93	C23—H23	0.93
C11—C12	1.380 (2)	C24—C25	1.393 (2)
C11—H11	0.93	C24—H24	0.93
C12—C13	1.385 (2)	C25—C26	1.383 (2)
C12—H12	0.93	C25—H25	0.93
C13—H13	0.93	C26—H26	0.93

N1—C1—C5	103.08 (11)	C15—C14—H14	116.7
N1—C1—C2	100.58 (11)	C16—C15—C14	91.73 (10)
C5—C1—C2	100.05 (11)	C16—C15—H15A	113.3
N1—C1—H1	116.8	C14—C15—H15A	113.3
C5—C1—H1	116.8	C16—C15—H15B	113.3
C2—C1—H1	116.8	C14—C15—H15B	113.3
C3—C2—C1	91.69 (11)	H15A—C15—H15B	110.7
C3—C2—H2A	113.3	O6—C16—C15	101.81 (10)
C1—C2—H2A	113.3	O6—C16—C17	105.66 (10)
C3—C2—H2B	113.3	C15—C16—C17	103.63 (11)
C1—C2—H2B	113.3	O6—C16—H16	114.8
H2A—C2—H2B	110.7	C15—C16—H16	114.8
O2—C3—C4	106.41 (11)	C17—C16—H16	114.8
O2—C3—C2	101.74 (11)	N2—C17—C16	99.60 (11)
C4—C3—C2	103.34 (12)	N2—C17—H17A	111.9
O2—C3—H3	114.6	C16—C17—H17A	111.9
C4—C3—H3	114.6	N2—C17—H17B	111.9
C2—C3—H3	114.6	C16—C17—H17B	111.9
N1—C4—C3	99.40 (11)	H17A—C17—H17B	109.6
N1—C4—H4A	111.9	O5—C18—O6	122.20 (13)
C3—C4—H4A	111.9	O5—C18—C14	131.54 (13)
N1—C4—H4B	111.9	O6—C18—C14	106.07 (11)
C3—C4—H4B	111.9	O7—C19—N2	125.19 (13)
H4A—C4—H4B	109.6	O7—C19—O8	124.89 (12)
O1—C5—O2	122.78 (14)	N2—C19—O8	109.92 (12)
O1—C5—C1	131.28 (13)	O8—C20—C21	105.41 (11)
O2—C5—C1	105.77 (11)	O8—C20—H20A	110.7
O3—C6—N1	124.85 (13)	C21—C20—H20A	110.7
O3—C6—O4	125.12 (13)	O8—C20—H20B	110.7
N1—C6—O4	109.97 (12)	C21—C20—H20B	110.7
O4—C7—C8	107.58 (12)	H20A—C20—H20B	108.8
O4—C7—H7A	110.2	C26—C21—C22	119.05 (13)
C8—C7—H7A	110.2	C26—C21—C20	119.26 (13)
O4—C7—H7B	110.2	C22—C21—C20	121.62 (13)
C8—C7—H7B	110.2	C23—C22—C21	120.20 (14)
H7A—C7—H7B	108.5	C23—C22—H22	119.9
C9—C8—C13	118.47 (14)	C21—C22—H22	119.9
C9—C8—C7	120.22 (14)	C24—C23—C22	120.46 (14)
C13—C8—C7	121.29 (14)	C24—C23—H23	119.8
C10—C9—C8	121.21 (14)	C22—C23—H23	119.8
C10—C9—H9	119.4	C23—C24—C25	119.60 (14)
C8—C9—H9	119.4	C23—C24—H24	120.2
C9—C10—C11	119.95 (15)	C25—C24—H24	120.2
C9—C10—H10	120.0	C26—C25—C24	119.89 (15)
C11—C10—H10	120.0	C26—C25—H25	120.1
C12—C11—C10	119.38 (15)	C24—C25—H25	120.1
C12—C11—H11	120.3	C25—C26—C21	120.76 (13)
C10—C11—H11	120.3	C25—C26—H26	119.6
C11—C12—C13	120.54 (14)	C21—C26—H26	119.6
C11—C12—H12	119.7	C6—N1—C4	127.24 (12)
C13—C12—H12	119.7	C6—N1—C1	123.02 (11)
C12—C13—C8	120.43 (14)	C4—N1—C1	108.53 (11)
C12—C13—H13	119.8	C19—N2—C17	127.75 (12)
C8—C13—H13	119.8	C19—N2—C14	123.84 (11)
N2—C14—C18	102.83 (10)	C17—N2—C14	108.07 (11)
N2—C14—C15	100.74 (11)	C5—O2—C3	106.52 (11)
C18—C14—C15	100.54 (11)	C6—O4—C7	115.82 (11)
N2—C14—H14	116.7	C18—O6—C16	106.04 (10)
C18—C14—H14	116.7	C19—O8—C20	115.16 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O5ⁱ	0.98	2.42	3.3493 (18)	159
C2—H2A···O7ⁱⁱ	0.97	2.46	3.2116 (18)	134
C3—H3···O5ⁱⁱⁱ	0.98	2.37	3.2816 (18)	155
C4—H4B···O7ⁱⁱⁱ	0.97	2.39	3.3408 (18)	168
C15—H15A···O3^iv	0.97	2.44	3.1382 (19)	128
C16—H16···O1^v	0.98	2.49	3.2207 (18)	131
C26—H26···O6^vi	0.93	2.58	3.4584 (19)	157

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O5ⁱ	0.98	2.42	3.3493 (18)	159
C2—H2A···O7ⁱⁱ	0.97	2.46	3.2116 (18)	134
C3—H3···O5ⁱⁱⁱ	0.98	2.37	3.2816 (18)	155
C4—H4B···O7ⁱⁱⁱ	0.97	2.39	3.3408 (18)	168
C15—H15A···O3^iv	0.97	2.44	3.1382 (19)	128
C16—H16···O1^v	0.98	2.49	3.2207 (18)	131
C26—H26···O6^vi	0.93	2.58	3.4584 (19)	157

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

Acknowledgements

We are grateful to the Center for Instrumental Analysis, Kyushu Institute of Technology (KITCIA), for the ¹H NMR and X-ray analysis.

References

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Volume 71| Part 7| July 2015| Pages o447-o448

doi:10.1107/S2056989015010464

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

Crystal structure of benzyl 3-oxo-2-oxa-5-aza­bi­cyclo­[2.2.1]heptane-5-carboxyl­ate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of benzyl 3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate