2-[(1RS,3RS,3aRS,6aSR)-5-Benzyl-4,6-dioxo-3-phenyl-octa-hydro-pyrrolo-[3,4-c]pyrrol-1-yl]acetamide.

In the title compound, C(21)H(21)N(3)O(3), the relative stereochemistry of the four stereogenic C atoms has been determined. The dihedral angle between the phenyl rings is 77.63 (7)°. In the crystal, ribbons spread along the a axis are formed by N-H⋯O hydrogen bonds. C-H⋯π inter-actions also occur.

Related literature

For general background to chemistry affording polycyclic pyrrolidine-based scaffolds, see: Kudryavtsev & Irkha (2005 ▶); Kudryavtsev (2008 ▶, 2011 ▶).

Experimental

Crystal data

C21H21N3O3

M = 363.41

Triclinic,

a = 9.101 (5) Å

b = 9.270 (5) Å

c = 12.945 (5) Å

α = 103.73 (4)°

β = 92.30 (4)°

γ = 113.94 (4)°

V = 958.1 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.50 × 0.40 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

4399 measured reflections

3561 independent reflections

2309 reflections with I > 2σ(I)

R int = 0.011

2 standard reflections every 120 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.108

S = 1.02

3561 reflections

329 parameters

All H-atom parameters refined

Δρmax = 0.23 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CAD4 (Schagen et al., 1988 ▶); cell refinement: CAD4; data reduction: XCAD4 (Harms, 1997 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811045181/ff2039sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045181/ff2039Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811045181/ff2039Isup3.cml

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

C21H21N3O3	Z = 2
Mr = 363.41	F(000) = 384
Triclinic, P1	Dx = 1.260 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.101 (5) Å	Cell parameters from 25 reflections
b = 9.270 (5) Å	θ = 12–13°
c = 12.945 (5) Å	µ = 0.09 mm−1
α = 103.73 (4)°	T = 293 K
β = 92.30 (4)°	Block, colourless
γ = 113.94 (4)°	0.50 × 0.40 × 0.30 mm
V = 958.1 (8) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.011
Radiation source: fine-focus sealed tube	θmax = 25.5°, θmin = 2.5°
graphite	h = −10→10
ω scans	k = −11→11
4399 measured reflections	l = −2→15
3561 independent reflections	2 standard reflections every 120 min
2309 reflections with I > 2σ(I)	intensity decay: none

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	All H-atom parameters refined
wR(F2) = 0.108	w = 1/[σ2(Fo2) + (0.0636P)2 + 0.0755P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3561 reflections	Δρmax = 0.23 e Å−3
329 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.019 (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
N1	−0.24934 (15)	0.58343 (15)	0.22990 (10)	0.0479 (3)
N2	0.22129 (15)	0.92640 (17)	0.28729 (10)	0.0483 (3)
N3	0.32943 (19)	1.0559 (2)	−0.00733 (12)	0.0609 (4)
O1	−0.27577 (14)	0.69214 (15)	0.09260 (9)	0.0641 (3)
O2	−0.16268 (15)	0.53957 (17)	0.38310 (11)	0.0802 (4)
O3	0.36090 (17)	0.8890 (2)	0.08216 (11)	0.0822 (5)
C1	0.15214 (17)	0.83233 (18)	0.36351 (11)	0.0422 (3)
C2	−0.02806 (17)	0.80608 (18)	0.34669 (11)	0.0425 (3)
C3	−0.15032 (18)	0.6298 (2)	0.32723 (12)	0.0504 (4)
C4	−0.20472 (17)	0.70517 (18)	0.17794 (11)	0.0441 (3)
C5	−0.05359 (16)	0.84700 (18)	0.24194 (11)	0.0399 (3)
C6	0.10000 (17)	0.85783 (19)	0.19148 (11)	0.0419 (3)
C7	0.13948 (19)	0.9617 (2)	0.11336 (14)	0.0480 (4)
C8	0.28660 (18)	0.9660 (2)	0.06133 (12)	0.0504 (4)
C9	−0.3871 (2)	0.4207 (2)	0.18643 (16)	0.0583 (4)
C10	−0.54238 (19)	0.41544 (18)	0.22548 (13)	0.0510 (4)
C11	−0.6492 (2)	0.4469 (2)	0.16611 (15)	0.0647 (5)
C12	−0.7917 (3)	0.4421 (3)	0.2033 (2)	0.0843 (7)
C13	−0.8263 (3)	0.4063 (3)	0.2991 (2)	0.0888 (7)
C14	−0.7207 (3)	0.3752 (3)	0.3577 (2)	0.0867 (7)
C15	−0.5794 (3)	0.3789 (2)	0.32126 (16)	0.0691 (5)
C16	0.23862 (16)	0.91778 (18)	0.47794 (11)	0.0410 (3)
C17	0.34576 (19)	1.0818 (2)	0.50956 (13)	0.0510 (4)
C18	0.4222 (2)	1.1578 (2)	0.61503 (15)	0.0604 (4)
C19	0.3912 (2)	1.0709 (3)	0.69041 (14)	0.0607 (5)
C20	0.2857 (2)	0.9079 (3)	0.65957 (14)	0.0651 (5)
C21	0.2094 (2)	0.8303 (2)	0.55396 (13)	0.0559 (4)
H1	0.1496 (17)	0.7255 (19)	0.3441 (11)	0.043 (4)*
H6	0.0843 (17)	0.7458 (19)	0.1533 (11)	0.045 (4)*
H72	0.045 (2)	0.917 (2)	0.0574 (14)	0.060 (5)*
H5	−0.0619 (17)	0.9502 (18)	0.2500 (11)	0.041 (4)*
H22	−0.0542 (19)	0.874 (2)	0.4050 (13)	0.054 (4)*
H17	0.369 (2)	1.143 (2)	0.4586 (14)	0.062 (5)*
H71	0.158 (2)	1.071 (2)	0.1478 (14)	0.063 (5)*
H21	0.135 (2)	0.718 (2)	0.5356 (14)	0.068 (5)*
H92	−0.356 (2)	0.339 (2)	0.2133 (14)	0.070 (5)*
H18	0.497 (2)	1.268 (2)	0.6354 (15)	0.075 (6)*
H91	−0.397 (2)	0.400 (2)	0.1100 (16)	0.072 (6)*
H2	0.308 (2)	0.920 (2)	0.2746 (13)	0.060 (5)*
H19	0.450 (2)	1.126 (2)	0.7648 (17)	0.083 (6)*
H32	0.275 (2)	1.114 (2)	−0.0222 (15)	0.074 (6)*
H11	−0.622 (2)	0.479 (2)	0.1011 (16)	0.076 (6)*
H15	−0.502 (3)	0.348 (3)	0.3604 (17)	0.099 (7)*
H20	0.262 (2)	0.843 (2)	0.7129 (17)	0.085 (6)*
H31	0.423 (3)	1.069 (2)	−0.0340 (16)	0.082 (6)*
H14	−0.748 (3)	0.347 (3)	0.4305 (19)	0.111 (8)*
H12	−0.858 (3)	0.462 (3)	0.1610 (19)	0.103 (8)*
H13	−0.926 (3)	0.398 (3)	0.323 (2)	0.111 (8)*

	U11	U22	U33	U12	U13	U23
N1	0.0463 (7)	0.0459 (7)	0.0468 (7)	0.0128 (6)	0.0111 (6)	0.0166 (6)
N2	0.0359 (7)	0.0718 (9)	0.0450 (7)	0.0238 (6)	0.0155 (5)	0.0272 (6)
N3	0.0601 (9)	0.0864 (11)	0.0618 (9)	0.0404 (8)	0.0319 (7)	0.0461 (8)
O1	0.0597 (7)	0.0739 (8)	0.0508 (7)	0.0174 (6)	0.0008 (5)	0.0249 (6)
O2	0.0680 (8)	0.0850 (9)	0.0834 (9)	0.0099 (7)	0.0072 (7)	0.0579 (8)
O3	0.0839 (9)	0.1354 (12)	0.0919 (10)	0.0783 (9)	0.0596 (8)	0.0819 (9)
C1	0.0432 (8)	0.0473 (9)	0.0417 (8)	0.0220 (7)	0.0146 (6)	0.0164 (7)
C2	0.0403 (8)	0.0511 (8)	0.0374 (8)	0.0194 (7)	0.0138 (6)	0.0138 (7)
C3	0.0455 (8)	0.0585 (9)	0.0492 (9)	0.0169 (7)	0.0150 (7)	0.0268 (8)
C4	0.0425 (8)	0.0514 (8)	0.0413 (8)	0.0204 (7)	0.0123 (6)	0.0166 (7)
C5	0.0391 (7)	0.0436 (8)	0.0435 (8)	0.0205 (6)	0.0150 (6)	0.0172 (6)
C6	0.0415 (8)	0.0505 (9)	0.0424 (8)	0.0240 (7)	0.0171 (6)	0.0191 (7)
C7	0.0434 (9)	0.0611 (10)	0.0488 (9)	0.0246 (8)	0.0156 (7)	0.0261 (8)
C8	0.0497 (9)	0.0702 (10)	0.0435 (8)	0.0296 (8)	0.0173 (7)	0.0288 (8)
C9	0.0572 (10)	0.0448 (9)	0.0604 (11)	0.0109 (8)	0.0126 (8)	0.0115 (8)
C10	0.0520 (9)	0.0370 (8)	0.0525 (9)	0.0090 (7)	0.0098 (7)	0.0101 (7)
C11	0.0676 (11)	0.0618 (11)	0.0554 (10)	0.0225 (9)	0.0022 (9)	0.0105 (9)
C12	0.0716 (14)	0.0691 (13)	0.1083 (18)	0.0337 (11)	−0.0010 (13)	0.0137 (12)
C13	0.0777 (15)	0.0622 (12)	0.130 (2)	0.0300 (11)	0.0492 (15)	0.0267 (13)
C14	0.0970 (17)	0.0768 (14)	0.0990 (17)	0.0351 (13)	0.0525 (14)	0.0445 (13)
C15	0.0751 (12)	0.0611 (11)	0.0751 (13)	0.0222 (9)	0.0264 (10)	0.0363 (10)
C16	0.0377 (7)	0.0511 (8)	0.0428 (8)	0.0245 (6)	0.0125 (6)	0.0170 (6)
C17	0.0521 (9)	0.0527 (9)	0.0531 (9)	0.0243 (8)	0.0122 (7)	0.0192 (8)
C18	0.0535 (10)	0.0590 (11)	0.0627 (11)	0.0251 (9)	0.0055 (8)	0.0048 (9)
C19	0.0530 (10)	0.0871 (14)	0.0468 (9)	0.0407 (10)	0.0049 (8)	0.0080 (9)
C20	0.0699 (12)	0.0902 (14)	0.0494 (10)	0.0406 (11)	0.0139 (9)	0.0321 (10)
C21	0.0582 (10)	0.0600 (11)	0.0508 (9)	0.0211 (9)	0.0101 (8)	0.0250 (8)

N1—C4	1.379 (2)	C9—C10	1.506 (2)
N1—C3	1.386 (2)	C9—H92	1.030 (18)
N1—C9	1.473 (2)	C9—H91	0.955 (19)
N2—C6	1.452 (2)	C10—C11	1.377 (3)
N2—C1	1.4639 (19)	C10—C15	1.381 (2)
N2—H2	0.832 (18)	C11—C12	1.389 (3)
N3—C8	1.324 (2)	C11—H11	0.97 (2)
N3—H32	0.91 (2)	C12—C13	1.374 (4)
N3—H31	0.90 (2)	C12—H12	0.90 (2)
O1—C4	1.2120 (18)	C13—C14	1.361 (4)
O2—C3	1.2053 (19)	C13—H13	0.95 (3)
O3—C8	1.2281 (19)	C14—C15	1.378 (3)
C1—C16	1.511 (2)	C14—H14	1.05 (2)
C1—C2	1.555 (2)	C15—H15	1.01 (2)
C1—H1	0.953 (15)	C16—C17	1.378 (2)
C2—C3	1.509 (2)	C16—C21	1.386 (2)
C2—C5	1.525 (2)	C17—C18	1.384 (3)
C2—H22	0.966 (16)	C17—H17	0.943 (18)
C4—C5	1.494 (2)	C18—C19	1.375 (3)
C5—C6	1.543 (2)	C18—H18	0.93 (2)
C5—H5	0.972 (14)	C19—C20	1.368 (3)
C6—C7	1.513 (2)	C19—H19	0.99 (2)
C6—H6	0.987 (15)	C20—C21	1.386 (3)
C7—C8	1.513 (2)	C20—H20	1.00 (2)
C7—H72	0.978 (18)	C21—H21	0.944 (19)
C7—H71	0.944 (19)
C4—N1—C3	112.94 (13)	O3—C8—N3	122.40 (15)
C4—N1—C9	123.65 (14)	O3—C8—C7	121.10 (13)
C3—N1—C9	123.41 (14)	N3—C8—C7	116.50 (14)
C6—N2—C1	107.05 (12)	N1—C9—C10	112.20 (14)
C6—N2—H2	112.4 (12)	N1—C9—H92	106.3 (10)
C1—N2—H2	109.2 (12)	C10—C9—H92	109.0 (10)
C8—N3—H32	122.6 (12)	N1—C9—H91	105.6 (11)
C8—N3—H31	118.2 (12)	C10—C9—H91	111.2 (11)
H32—N3—H31	118.8 (17)	H92—C9—H91	112.5 (15)
N2—C1—C16	113.54 (13)	C11—C10—C15	119.19 (18)
N2—C1—C2	101.61 (11)	C11—C10—C9	120.46 (16)
C16—C1—C2	114.38 (12)	C15—C10—C9	120.35 (17)
N2—C1—H1	112.9 (9)	C10—C11—C12	119.8 (2)
C16—C1—H1	108.1 (8)	C10—C11—H11	120.2 (12)
C2—C1—H1	106.1 (9)	C12—C11—H11	119.9 (12)
C3—C2—C5	104.30 (13)	C13—C12—C11	120.3 (2)
C3—C2—C1	114.00 (13)	C13—C12—H12	123.5 (16)
C5—C2—C1	106.24 (11)	C11—C12—H12	116.2 (16)
C3—C2—H22	108.6 (9)	C14—C13—C12	119.9 (2)
C5—C2—H22	110.1 (9)	C14—C13—H13	120.0 (15)
C1—C2—H22	113.2 (9)	C12—C13—H13	120.1 (15)
O2—C3—N1	123.89 (15)	C13—C14—C15	120.3 (2)
O2—C3—C2	127.97 (15)	C13—C14—H14	119.8 (13)
N1—C3—C2	108.13 (13)	C15—C14—H14	119.9 (13)
O1—C4—N1	124.11 (15)	C14—C15—C10	120.5 (2)
O1—C4—C5	127.43 (14)	C14—C15—H15	122.1 (12)
N1—C4—C5	108.40 (13)	C10—C15—H15	117.3 (12)
C4—C5—C2	105.30 (12)	C17—C16—C21	118.60 (15)
C4—C5—C6	112.59 (12)	C17—C16—C1	121.77 (14)
C2—C5—C6	103.62 (11)	C21—C16—C1	119.62 (14)
C4—C5—H5	111.1 (8)	C16—C17—C18	120.74 (17)
C2—C5—H5	115.4 (8)	C16—C17—H17	119.8 (11)
C6—C5—H5	108.6 (8)	C18—C17—H17	119.4 (11)
N2—C6—C7	113.43 (13)	C19—C18—C17	120.39 (18)
N2—C6—C5	100.79 (11)	C19—C18—H18	119.3 (12)
C7—C6—C5	113.69 (12)	C17—C18—H18	120.3 (12)
N2—C6—H6	111.2 (8)	C20—C19—C18	119.24 (17)
C7—C6—H6	108.8 (8)	C20—C19—H19	121.2 (12)
C5—C6—H6	108.7 (8)	C18—C19—H19	119.5 (12)
C6—C7—C8	113.10 (13)	C19—C20—C21	120.81 (18)
C6—C7—H72	108.4 (9)	C19—C20—H20	120.4 (12)
C8—C7—H72	109.2 (10)	C21—C20—H20	118.8 (12)
C6—C7—H71	111.0 (10)	C20—C21—C16	120.22 (18)
C8—C7—H71	108.4 (11)	C20—C21—H21	118.8 (11)
H72—C7—H71	106.6 (14)	C16—C21—H21	121.0 (11)
C6—N2—C1—C16	−162.41 (12)	C4—C5—C6—C7	90.44 (16)
C6—N2—C1—C2	−39.10 (14)	C2—C5—C6—C7	−156.31 (13)
N2—C1—C2—C3	129.33 (13)	N2—C6—C7—C8	67.80 (18)
C16—C1—C2—C3	−107.94 (15)	C5—C6—C7—C8	−177.81 (13)
N2—C1—C2—C5	15.04 (14)	C6—C7—C8—O3	0.9 (2)
C16—C1—C2—C5	137.77 (13)	C6—C7—C8—N3	−179.38 (15)
C4—N1—C3—O2	−176.19 (15)	C4—N1—C9—C10	−92.44 (19)
C9—N1—C3—O2	3.4 (2)	C3—N1—C9—C10	87.97 (19)
C4—N1—C3—C2	2.69 (17)	N1—C9—C10—C11	92.8 (2)
C9—N1—C3—C2	−177.68 (13)	N1—C9—C10—C15	−87.3 (2)
C5—C2—C3—O2	171.11 (16)	C15—C10—C11—C12	0.2 (3)
C1—C2—C3—O2	55.7 (2)	C9—C10—C11—C12	−179.83 (16)
C5—C2—C3—N1	−7.71 (15)	C10—C11—C12—C13	0.1 (3)
C1—C2—C3—N1	−123.14 (13)	C11—C12—C13—C14	−0.1 (3)
C3—N1—C4—O1	−178.84 (14)	C12—C13—C14—C15	−0.2 (4)
C9—N1—C4—O1	1.5 (2)	C13—C14—C15—C10	0.5 (3)
C3—N1—C4—C5	3.74 (16)	C11—C10—C15—C14	−0.5 (3)
C9—N1—C4—C5	−175.89 (13)	C9—C10—C15—C14	179.51 (17)
O1—C4—C5—C2	174.29 (15)	N2—C1—C16—C17	13.95 (19)
N1—C4—C5—C2	−8.41 (15)	C2—C1—C16—C17	−102.06 (16)
O1—C4—C5—C6	−73.49 (19)	N2—C1—C16—C21	−166.52 (13)
N1—C4—C5—C6	103.82 (14)	C2—C1—C16—C21	77.47 (17)
C3—C2—C5—C4	9.55 (14)	C21—C16—C17—C18	−0.2 (2)
C1—C2—C5—C4	130.31 (12)	C1—C16—C17—C18	179.33 (13)
C3—C2—C5—C6	−108.87 (13)	C16—C17—C18—C19	−0.6 (2)
C1—C2—C5—C6	11.89 (14)	C17—C18—C19—C20	0.9 (3)
C1—N2—C6—C7	168.92 (12)	C18—C19—C20—C21	−0.4 (3)
C1—N2—C6—C5	47.03 (14)	C19—C20—C21—C16	−0.4 (3)
C4—C5—C6—N2	−147.85 (12)	C17—C16—C21—C20	0.7 (2)
C2—C5—C6—N2	−34.60 (14)	C1—C16—C21—C20	−178.86 (14)

Cg1 is the centroid of the C10–C15 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H32···O1i	0.91 (2)	2.194 (19)	3.003 (2)	147.3 (16)
N3—H31···O3ii	0.90 (2)	2.00 (2)	2.903 (2)	175.7 (18)
C18—H18···Cg1iii	0.93 (2)	2.71	3.627	166.5

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10–C15 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H32⋯O1i	0.91 (2)	2.194 (19)	3.003 (2)	147.3 (16)
N3—H31⋯O3ii	0.90 (2)	2.00 (2)	2.903 (2)	175.7 (18)
C18—H18⋯Cg1iii	0.93 (2)	2.71	3.627	166.5

Symmetry codes: (i) ; (ii) ; (iii) .