{2-[(Benzo-yloxy)meth-yl]-1-oxo-3H-pyrrolizin-2-yl}methyl benzoate.

The title compound, C(23)H(19)NO(5), was prepared by esterification of 2,2-bis-(hy-droxy-meth-yl)-2,3-dihydro-1H-pyrrolizin-1-one with benzoyl chloride in pyridine·The pyrrolizine ring system is approximately planar with a maximum deviation of 0.008 (2) Å from the least-squares plane; the two phenyl rings are oriented at dihedral angles of 64.26 (11) and 70.75 (10)° with respect to the pyrrolizine ring system. Weak inter-molecular C-H⋯O hydrogen bonding occurs in the crystal structure.

Related literature

For general background to 2,3-dihydro­pyrrolizine derivatives and for the biological activity of related compounds, see: Skvortsov & Astakhova (1992 ▶); Albrecht et al. (2008 ▶); Morúaa et al. (2009 ▶). For side effects of non-steroidal anti-inflammatory drugs, see: Mishra et al. (2008 ▶). For the synthesis, see: Clemo & Ramage (1931 ▶). For the natural source of the compound, see: Meinwald & Meinwald (1965 ▶). For related structures, see: Ali et al. (2010a ▶,b ▶,c ▶).

Experimental

Crystal data

C23H19NO5

M = 389.39

Triclinic,

a = 8.0438 (8) Å

b = 11.9359 (13) Å

c = 12.0614 (13) Å

α = 64.417 (2)°

β = 72.670 (2)°

γ = 77.390 (2)°

V = 991.65 (18) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.42 × 0.20 × 0.14 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

13906 measured reflections

4932 independent reflections

3206 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.161

S = 1.01

4932 reflections

262 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶) and PLATON (Spek, 2009) ▶.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810051974/xu5119sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051974/xu5119Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H19NO5	Z = 2
Mr = 389.39	F(000) = 408
Triclinic, P1	Dx = 1.304 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0438 (8) Å	Cell parameters from 4932 reflections
b = 11.9359 (13) Å	θ = 1.9–28.3°
c = 12.0614 (13) Å	µ = 0.09 mm−1
α = 64.417 (2)°	T = 298 K
β = 72.670 (2)°	Block, colourless
γ = 77.390 (2)°	0.42 × 0.20 × 0.14 mm
V = 991.65 (18) Å3

Bruker SMART APEX CCD area-detector diffractometer	3206 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
graphite	θmax = 28.3°, θmin = 1.9°
Detector resolution: 83.66 pixels mm-1	h = −10→10
ω scans	k = −15→15
13906 measured reflections	l = −16→16
4932 independent reflections

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0698P)2 + 0.1946P] where P = (Fo2 + 2Fc2)/3
4932 reflections	(Δ/σ)max < 0.001
262 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.3231 (2)	0.62080 (14)	0.45737 (13)	0.0694 (4)
O2	0.55937 (16)	0.70317 (12)	0.43879 (11)	0.0533 (3)
O3	0.4749 (2)	0.66084 (19)	0.82292 (15)	0.0944 (6)
O4	0.7843 (2)	0.85334 (13)	0.61521 (14)	0.0689 (4)
O5	0.6833 (2)	1.05268 (15)	0.57098 (18)	0.0907 (6)
N1	0.8947 (2)	0.56213 (15)	0.69252 (13)	0.0537 (4)
C1	0.6217 (3)	0.8044 (2)	0.17996 (19)	0.0714 (6)
H1A	0.6835	0.8284	0.2187	0.086*
C2	0.6589 (4)	0.8481 (3)	0.0492 (2)	0.0926 (9)
H2A	0.7452	0.9019	0.0003	0.111*
C3	0.5692 (4)	0.8123 (3)	−0.0073 (2)	0.0869 (8)
H3A	0.5949	0.8415	−0.0950	0.104*
C4	0.4434 (4)	0.7349 (2)	0.0627 (2)	0.0818 (7)
H4A	0.3832	0.7105	0.0231	0.098*
C5	0.4036 (3)	0.6918 (2)	0.19253 (19)	0.0668 (6)
H5A	0.3154	0.6395	0.2404	0.080*
C6	0.4945 (2)	0.72617 (16)	0.25171 (16)	0.0479 (4)
C7	0.4475 (2)	0.67765 (16)	0.39199 (16)	0.0486 (4)
C8	0.5139 (3)	0.66392 (18)	0.57460 (16)	0.0559 (5)
H8A	0.5044	0.5748	0.6154	0.067*
H8B	0.4021	0.7070	0.6007	0.067*
C9	0.6569 (3)	0.69529 (17)	0.61193 (16)	0.0531 (5)
C10	0.6152 (3)	0.63955 (19)	0.75869 (17)	0.0575 (5)
C11	0.7683 (2)	0.56484 (17)	0.79665 (16)	0.0513 (4)
C12	0.8376 (3)	0.4943 (2)	0.90126 (19)	0.0686 (6)
H12A	0.7816	0.4800	0.9850	0.082*
C13	1.0058 (3)	0.4495 (3)	0.8577 (2)	0.0821 (7)
H13A	1.0838	0.3989	0.9075	0.098*
C14	1.0393 (3)	0.4921 (2)	0.7279 (2)	0.0730 (6)
H14A	1.1429	0.4753	0.6747	0.088*
C15	0.8401 (3)	0.63095 (18)	0.57321 (16)	0.0562 (5)
H15A	0.8340	0.5748	0.5360	0.067*
H15B	0.9201	0.6920	0.5134	0.067*
C16	0.6544 (3)	0.83585 (18)	0.5645 (2)	0.0647 (5)
H16A	0.6843	0.8735	0.4729	0.078*
H16B	0.5396	0.8729	0.5947	0.078*
C17	0.7803 (3)	0.96426 (18)	0.61761 (18)	0.0553 (5)
C18	0.9055 (2)	0.96183 (17)	0.68757 (17)	0.0520 (4)
C19	1.0125 (3)	0.8561 (2)	0.7402 (2)	0.0678 (6)
H19A	1.0122	0.7839	0.7288	0.081*
C20	1.1203 (3)	0.8573 (2)	0.8099 (3)	0.0820 (7)
H20A	1.1929	0.7858	0.8449	0.098*
C21	1.1210 (3)	0.9627 (3)	0.8276 (3)	0.0848 (7)
H21A	1.1931	0.9627	0.8753	0.102*
C22	1.0158 (3)	1.0683 (2)	0.7753 (3)	0.0856 (8)
H22A	1.0161	1.1400	0.7875	0.103*
C23	0.9094 (3)	1.0683 (2)	0.7047 (2)	0.0704 (6)
H23A	0.8395	1.1408	0.6681	0.084*

	U11	U22	U33	U12	U13	U23
O1	0.0775 (10)	0.0854 (10)	0.0497 (8)	−0.0319 (8)	−0.0126 (7)	−0.0209 (7)
O2	0.0670 (8)	0.0615 (8)	0.0392 (6)	−0.0112 (6)	−0.0191 (6)	−0.0204 (6)
O3	0.0874 (12)	0.1345 (16)	0.0621 (10)	0.0270 (11)	−0.0207 (9)	−0.0554 (10)
O4	0.0845 (10)	0.0583 (8)	0.0831 (10)	0.0067 (7)	−0.0485 (8)	−0.0329 (7)
O5	0.1067 (13)	0.0594 (9)	0.1268 (15)	0.0124 (9)	−0.0780 (12)	−0.0321 (9)
N1	0.0598 (9)	0.0614 (10)	0.0416 (8)	−0.0062 (7)	−0.0165 (7)	−0.0187 (7)
C1	0.0742 (14)	0.0969 (16)	0.0524 (11)	−0.0331 (12)	−0.0164 (10)	−0.0254 (11)
C2	0.0941 (18)	0.127 (2)	0.0526 (13)	−0.0546 (17)	−0.0050 (12)	−0.0194 (14)
C3	0.1055 (19)	0.118 (2)	0.0402 (11)	−0.0312 (16)	−0.0152 (12)	−0.0256 (12)
C4	0.1089 (19)	0.1024 (19)	0.0540 (12)	−0.0312 (15)	−0.0293 (13)	−0.0326 (12)
C5	0.0874 (15)	0.0748 (14)	0.0505 (11)	−0.0283 (11)	−0.0223 (10)	−0.0225 (10)
C6	0.0548 (10)	0.0505 (10)	0.0432 (9)	−0.0038 (8)	−0.0173 (8)	−0.0197 (8)
C7	0.0577 (11)	0.0498 (10)	0.0446 (9)	−0.0045 (8)	−0.0180 (8)	−0.0206 (8)
C8	0.0724 (12)	0.0609 (11)	0.0391 (9)	−0.0075 (9)	−0.0183 (9)	−0.0202 (8)
C9	0.0686 (12)	0.0568 (11)	0.0415 (9)	0.0010 (9)	−0.0231 (8)	−0.0232 (8)
C10	0.0684 (12)	0.0700 (13)	0.0429 (10)	0.0037 (10)	−0.0178 (9)	−0.0321 (9)
C11	0.0632 (11)	0.0585 (11)	0.0363 (9)	−0.0074 (9)	−0.0155 (8)	−0.0195 (8)
C12	0.0811 (15)	0.0813 (15)	0.0422 (10)	−0.0107 (12)	−0.0227 (10)	−0.0166 (10)
C13	0.0791 (16)	0.0966 (18)	0.0647 (14)	0.0073 (13)	−0.0366 (12)	−0.0211 (13)
C14	0.0586 (12)	0.0927 (17)	0.0661 (13)	0.0062 (11)	−0.0233 (10)	−0.0306 (12)
C15	0.0709 (12)	0.0633 (12)	0.0392 (9)	−0.0046 (9)	−0.0170 (9)	−0.0229 (8)
C16	0.0837 (14)	0.0601 (12)	0.0653 (12)	0.0008 (10)	−0.0422 (11)	−0.0260 (10)
C17	0.0616 (11)	0.0504 (11)	0.0547 (11)	−0.0034 (9)	−0.0213 (9)	−0.0176 (9)
C18	0.0478 (10)	0.0543 (11)	0.0521 (10)	−0.0074 (8)	−0.0132 (8)	−0.0171 (8)
C19	0.0672 (13)	0.0619 (13)	0.0826 (15)	0.0046 (10)	−0.0339 (11)	−0.0304 (11)
C20	0.0737 (15)	0.0752 (15)	0.1005 (19)	0.0050 (12)	−0.0476 (14)	−0.0259 (14)
C21	0.0734 (15)	0.0923 (18)	0.1029 (19)	−0.0155 (13)	−0.0445 (14)	−0.0326 (15)
C22	0.0815 (16)	0.0752 (16)	0.123 (2)	−0.0121 (12)	−0.0450 (16)	−0.0446 (15)
C23	0.0637 (13)	0.0565 (12)	0.0986 (17)	−0.0037 (9)	−0.0348 (12)	−0.0283 (12)

O1—C7	1.203 (2)	C9—C15	1.544 (3)
O2—C7	1.339 (2)	C9—C10	1.554 (2)
O2—C8	1.446 (2)	C10—C11	1.423 (3)
O3—C10	1.209 (2)	C11—C12	1.382 (2)
O4—C17	1.330 (2)	C12—C13	1.377 (3)
O4—C16	1.448 (2)	C12—H12A	0.9300
O5—C17	1.195 (2)	C13—C14	1.380 (3)
N1—C14	1.340 (2)	C13—H13A	0.9300
N1—C11	1.368 (2)	C14—H14A	0.9300
N1—C15	1.462 (2)	C15—H15A	0.9700
C1—C6	1.364 (3)	C15—H15B	0.9700
C1—C2	1.387 (3)	C16—H16A	0.9700
C1—H1A	0.9300	C16—H16B	0.9700
C2—C3	1.359 (3)	C17—C18	1.483 (3)
C2—H2A	0.9300	C18—C19	1.377 (3)
C3—C4	1.348 (3)	C18—C23	1.381 (3)
C3—H3A	0.9300	C19—C20	1.381 (3)
C4—C5	1.378 (3)	C19—H19A	0.9300
C4—H4A	0.9300	C20—C21	1.366 (4)
C5—C6	1.380 (2)	C20—H20A	0.9300
C5—H5A	0.9300	C21—C22	1.367 (3)
C6—C7	1.486 (2)	C21—H21A	0.9300
C8—C9	1.520 (3)	C22—C23	1.375 (3)
C8—H8A	0.9700	C22—H22A	0.9300
C8—H8B	0.9700	C23—H23A	0.9300
C9—C16	1.518 (3)
C7—O2—C8	114.90 (14)	C12—C11—C10	142.85 (19)
C17—O4—C16	118.43 (15)	C13—C12—C11	106.76 (19)
C14—N1—C11	109.83 (16)	C13—C12—H12A	126.6
C14—N1—C15	135.85 (17)	C11—C12—H12A	126.6
C11—N1—C15	114.29 (15)	C12—C13—C14	108.64 (19)
C6—C1—C2	120.1 (2)	C12—C13—H13A	125.7
C6—C1—H1A	120.0	C14—C13—H13A	125.7
C2—C1—H1A	120.0	N1—C14—C13	107.3 (2)
C3—C2—C1	119.9 (2)	N1—C14—H14A	126.4
C3—C2—H2A	120.0	C13—C14—H14A	126.4
C1—C2—H2A	120.0	N1—C15—C9	103.49 (14)
C4—C3—C2	120.5 (2)	N1—C15—H15A	111.1
C4—C3—H3A	119.7	C9—C15—H15A	111.1
C2—C3—H3A	119.7	N1—C15—H15B	111.1
C3—C4—C5	120.2 (2)	C9—C15—H15B	111.1
C3—C4—H4A	119.9	H15A—C15—H15B	109.0
C5—C4—H4A	119.9	O4—C16—C9	105.05 (14)
C4—C5—C6	120.1 (2)	O4—C16—H16A	110.7
C4—C5—H5A	119.9	C9—C16—H16A	110.7
C6—C5—H5A	119.9	O4—C16—H16B	110.7
C1—C6—C5	119.15 (17)	C9—C16—H16B	110.7
C1—C6—C7	122.40 (16)	H16A—C16—H16B	108.8
C5—C6—C7	118.44 (17)	O5—C17—O4	122.90 (18)
O1—C7—O2	123.14 (16)	O5—C17—C18	125.42 (18)
O1—C7—C6	124.05 (16)	O4—C17—C18	111.66 (16)
O2—C7—C6	112.81 (15)	C19—C18—C23	118.99 (19)
O2—C8—C9	108.01 (15)	C19—C18—C17	122.41 (18)
O2—C8—H8A	110.1	C23—C18—C17	118.54 (17)
C9—C8—H8A	110.1	C18—C19—C20	120.0 (2)
O2—C8—H8B	110.1	C18—C19—H19A	120.0
C9—C8—H8B	110.1	C20—C19—H19A	120.0
H8A—C8—H8B	108.4	C21—C20—C19	120.4 (2)
C16—C9—C8	110.34 (15)	C21—C20—H20A	119.8
C16—C9—C15	112.71 (17)	C19—C20—H20A	119.8
C8—C9—C15	113.55 (15)	C20—C21—C22	120.0 (2)
C16—C9—C10	108.49 (15)	C20—C21—H21A	120.0
C8—C9—C10	106.88 (16)	C22—C21—H21A	120.0
C15—C9—C10	104.41 (14)	C21—C22—C23	120.0 (2)
O3—C10—C11	129.35 (18)	C21—C22—H22A	120.0
O3—C10—C9	123.08 (18)	C23—C22—H22A	120.0
C11—C10—C9	107.57 (16)	C22—C23—C18	120.6 (2)
N1—C11—C12	107.50 (17)	C22—C23—H23A	119.7
N1—C11—C10	109.64 (15)	C18—C23—H23A	119.7
C6—C1—C2—C3	−0.4 (4)	C9—C10—C11—C12	175.6 (3)
C1—C2—C3—C4	0.3 (5)	N1—C11—C12—C13	−0.4 (2)
C2—C3—C4—C5	0.4 (4)	C10—C11—C12—C13	−179.3 (3)
C3—C4—C5—C6	−1.0 (4)	C11—C12—C13—C14	0.1 (3)
C2—C1—C6—C5	−0.2 (4)	C11—N1—C14—C13	−0.5 (3)
C2—C1—C6—C7	−179.2 (2)	C15—N1—C14—C13	−178.2 (2)
C4—C5—C6—C1	0.9 (3)	C12—C13—C14—N1	0.2 (3)
C4—C5—C6—C7	180.0 (2)	C14—N1—C15—C9	−176.2 (2)
C8—O2—C7—O1	−3.6 (3)	C11—N1—C15—C9	6.1 (2)
C8—O2—C7—C6	176.72 (14)	C16—C9—C15—N1	110.08 (16)
C1—C6—C7—O1	170.9 (2)	C8—C9—C15—N1	−123.51 (16)
C5—C6—C7—O1	−8.2 (3)	C10—C9—C15—N1	−7.47 (19)
C1—C6—C7—O2	−9.5 (3)	C17—O4—C16—C9	−162.70 (17)
C5—C6—C7—O2	171.47 (17)	C8—C9—C16—O4	175.02 (15)
C7—O2—C8—C9	177.88 (14)	C15—C9—C16—O4	−56.9 (2)
O2—C8—C9—C16	68.2 (2)	C10—C9—C16—O4	58.2 (2)
O2—C8—C9—C15	−59.5 (2)	C16—O4—C17—O5	−6.0 (3)
O2—C8—C9—C10	−174.06 (14)	C16—O4—C17—C18	172.28 (17)
C16—C9—C10—O3	65.9 (3)	O5—C17—C18—C19	179.3 (2)
C8—C9—C10—O3	−53.1 (3)	O4—C17—C18—C19	1.1 (3)
C15—C9—C10—O3	−173.7 (2)	O5—C17—C18—C23	2.0 (3)
C16—C9—C10—C11	−113.60 (18)	O4—C17—C18—C23	−176.29 (19)
C8—C9—C10—C11	127.42 (17)	C23—C18—C19—C20	0.6 (3)
C15—C9—C10—C11	6.8 (2)	C17—C18—C19—C20	−176.7 (2)
C14—N1—C11—C12	0.5 (2)	C18—C19—C20—C21	0.3 (4)
C15—N1—C11—C12	178.82 (17)	C19—C20—C21—C22	−0.6 (4)
C14—N1—C11—C10	179.85 (17)	C20—C21—C22—C23	−0.1 (4)
C15—N1—C11—C10	−1.9 (2)	C21—C22—C23—C18	1.1 (4)
O3—C10—C11—N1	177.2 (2)	C19—C18—C23—C22	−1.3 (3)
C9—C10—C11—N1	−3.3 (2)	C17—C18—C23—C22	176.1 (2)
O3—C10—C11—C12	−3.9 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O3i	0.93	2.59	3.299 (3)	133
C20—H20A···O3ii	0.93	2.44	3.269 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O3i	0.93	2.59	3.299 (3)	133
C20—H20A⋯O3ii	0.93	2.44	3.269 (3)	149

Symmetry codes: (i) ; (ii) .