2-[(1RS,3RS,3aRS,6aSR)-5-Benzyl-4,6-dioxo-3-phenyl­octa­hydro­pyrrolo­[3,4-c]pyrrol-1-yl]acetamide

Kudryavtsev, K.V.; Churakov, A.V.; Dogan, O.

doi:10.1107/S1600536811045181

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3186

https://doi.org/10.1107/S1600536811045181

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2-[(1RS,3RS,3aRS,6aSR)-5-Benzyl-4,6-dioxo-3-phenyloctahydropyrrolo[3,4-c]pyrrol-1-yl]acetamide

Konstantin V. Kudryavtsev,^a ^* Andrei V. Churakov ^b and Ozdemir Dogan ^c

^aDepartment of Chemistry, M.V. Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russian Federation, ^bInstitute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskii prosp. 31, Moscow 119991, Russian Federation, and ^cDepartment of Chemistry, Middle East Technical University, Ankara 06531, Turkey
^*Correspondence e-mail: kudr@org.chem.msu.ru

(Received 23 October 2011; accepted 27 October 2011; online 5 November 2011)

In the title compound, C₂₁H₂₁N₃O₃, 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 interactions 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_r = 363.41
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.035
wR(F²) = 0.108
S = 1.02
3561 reflections
329 parameters
All H-atom parameters refined
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.16 e Å⁻³

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) -x, -y+2, -z; (ii) -x+1, -y+2, -z; (iii) -x, -y+2, -z+1.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811045181/ff2039sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811045181/ff2039Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811045181/ff2039Isup3.cml

checkCIF report

Comment top

The adjacent molecules are combined into ribbons along a-axis by hydrogen bonds between neighbouring amide groups (Fig. 2). These ribbons are linked by T-shaped C—H···π interactions between phenyl substituents. Of interest, secondary amine hydrogen atom NH does not participate in hydrogen bonding.

Related literature top

For general background [to what?], see: Kudryavtsev & Irkha (2005); Kudryavtsev (2008, 2011).

Experimental top

1.134 g (10.69 mmol) of benzaldehyde, 1.410 g (10.68 mmol) of L-asparagine and 2.000 g (10.68 mmol) of N-benzylmaleimide were stirred at 140°C in 30 ml of DMF under an inert atmosphere during 4 h. After cooling to room temperature the reaction mixture was concentrated on rotary evaporator. The residue was chromatographed on silica gel 60 (particle size 0.040–0.063 mm) using CHCl₃—MeOH (40: 1) as eluent. 2-[(1RS,3RS,3aRS,6aSR)-5-Benzyl-4,6-dioxo-3- phenyloctahydropyrrolo[3,4-c]pyrrol-1-yl]acetamide. Yield 22%, colorless crystals, mp 148–149°C. ¹H NMR (DMSO-d₆, δ, J/Hz): 2.44 (dd, 1H, J = 15.0, 8.8); 2.58 (dd, 1H, J = 15.0, 3.5); 3.23 (dd, 1H, J = 8.8, 7.5); 3.42 (dt, 2H, J = 8.1, 3.5); 4.15 (d, 1H, J = 7.5); 4.57 (s, 2H); 6.93 (s, 1H); 7.25–7.31(m, 4H); 7.32–7.40 (m, 5H); 7.46 (br.s, 1H); 7.47–7.51 (m, 2H). Found (%): C, 69.34; H, 5.85; N, 11.78. C₂₁H₂₁N₃O₃. Calculated (%): C, 69.41; H, 5.82; N, 11.56. The crystals for X-ray analysis were obtained by slow evaporation of saturated chloroform solution at ambient tempreture.

Structure description top

For general background [to what?], see: Kudryavtsev & Irkha (2005); Kudryavtsev (2008, 2011).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing the numbering scheme adopted. Displacement ellipsoids are shown at the 50% probability level.
	Fig. 2. Hydrogen-bonded ribbons along a-axis in the structure of the title compound.

2-[(1RS,3RS,3aRS,6aSR)-5-Benzyl-4,6-dioxo-3- phenyloctahydropyrrolo[3,4-c]pyrrol-1-yl]acetamide top

Crystal data top

C₂₁H₂₁N₃O₃	Z = 2
M_r = 363.41	F(000) = 384
Triclinic, P1	D_x = 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

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.011
Radiation source: fine-focus sealed tube	θ_max = 25.5°, θ_min = 2.5°
Graphite monochromator	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 top

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(F_o²) + (0.0636P)² + 0.0755P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3561 reflections	Δρ_max = 0.23 e Å⁻³
329 parameters	Δρ_min = −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)

Crystal data top

C₂₁H₂₁N₃O₃	γ = 113.94 (4)°
M_r = 363.41	V = 958.1 (8) Å³
Triclinic, P1	Z = 2
a = 9.101 (5) Å	Mo Kα radiation
b = 9.270 (5) Å	µ = 0.09 mm⁻¹
c = 12.945 (5) Å	T = 293 K
α = 103.73 (4)°	0.50 × 0.40 × 0.30 mm
β = 92.30 (4)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.011
4399 measured reflections	2 standard reflections every 120 min
3561 independent reflections	intensity decay: none
2309 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.108	All H-atom parameters refined
S = 1.02	Δρ_max = 0.23 e Å⁻³
3561 reflections	Δρ_min = −0.16 e Å⁻³
329 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
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y+2, −z; (ii) −x+1, −y+2, −z; (iii) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁N₃O₃
M_r	363.41
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.101 (5), 9.270 (5), 12.945 (5)
α, β, γ (°)	103.73 (4), 92.30 (4), 113.94 (4)
V (Å³)	958.1 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.40 × 0.30

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4399, 3561, 2309
R_int	0.011
(sin θ/λ)_max (Å⁻¹)	0.605

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.108, 1.02
No. of reflections	3561
No. of parameters	329
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.16

Computer programs: CAD4 (Schagen et al., 1988), XCAD4 (Harms, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x, −y+2, −z; (ii) −x+1, −y+2, −z; (iii) −x, −y+2, −z+1.

Acknowledgements

This study was partially supported by the Russian Foundation for Basic Research (project Nos. 11–03-00630 − a and 11–03-91375-ST_a) and State Contract No. 11.519.11.2032.

References

Harms, K. (1997). XCAD4. University of Marburg, Germany. Google Scholar
Kudryavtsev, K. V. (2008). Russ. Chem. Bull. 57, 2364–2372. Web of Science CrossRef CAS Google Scholar
Kudryavtsev, K. V. (2011). Heterocycles, 83, 323–330. CAS Google Scholar
Kudryavtsev, K. V. & Irkha, V. V. (2005). Molecules, 10, 755–761. Web of Science CrossRef PubMed CAS Google Scholar
Schagen, J. D., Strauer, L., van Meurs, F. & Williams, G. (1988). CAD4. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

2-[(1RS,3RS,3aRS,6aSR)-5-Benzyl-4,6-dioxo-3-phenyl­octa­hydro­pyrrolo­[3,4-c]pyrrol-1-yl]acetamide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-[(1RS,3RS,3aRS,6aSR)-5-Benzyl-4,6-dioxo-3-phenyloctahydropyrrolo[3,4-c]pyrrol-1-yl]acetamide