(1SR,3RS,3aSR,6aRS)-Methyl 5-methyl-4,6-dioxo-3-[2-(trifluoro-meth-yl)phen-yl]octa-hydro-pyrrolo-[3,4-c]pyrrole-1-carboxyl-ate.

In the title compound, C(16)H(15)F(3)N(2)O(4), the relative stereochemistry of the four stereogenic C atoms has been determined. The carb-oxy-methyl and 2-(trifluoro-meth-yl)-phenyl substituents of the pyrrolidine cycle have a cis mutual arrangement. The five-membered saturated aza-cycle adopts an envelope conformation with the N atom occupying the flap position. In the crystal, adjacent mol-ecules are combined in centrosymmetric dimers by two weak N-H⋯O hydrogen bonds.

Related literature

For general background to the chemistry affording bicyclic pyrrolo­[3,4-c]pyrrole-based scaffolds and structural determination, see: Kudryavtsev & Irkha (2005 ▶); Kudryavtsev (2008 ▶); Kudryavtsev & Zagulyaeva (2008 ▶); Kudryavtsev et al. (2011 ▶).

Experimental

Crystal data

C16H15F3N2O4

M = 356.30

Orthorhombic,

a = 11.6168 (4) Å

b = 12.7385 (5) Å

c = 21.2429 (8) Å

V = 3143.5 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.13 mm−1

T = 150 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.955, T max = 0.968

28987 measured reflections

4585 independent reflections

3698 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.115

S = 1.05

4585 reflections

286 parameters

All H-atom parameters refined

Δρmax = 0.41 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812051471/ff2094sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051471/ff2094Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812051471/ff2094Isup3.cml

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

C16H15F3N2O4	F(000) = 1472
Mr = 356.30	Dx = 1.506 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 7037 reflections
a = 11.6168 (4) Å	θ = 2.6–30.2°
b = 12.7385 (5) Å	µ = 0.13 mm−1
c = 21.2429 (8) Å	T = 150 K
V = 3143.5 (2) Å3	Block, colourless
Z = 8	0.35 × 0.30 × 0.25 mm

Bruker SMART APEXII diffractometer	4585 independent reflections
Radiation source: fine-focus sealed tube	3698 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω scans	θmax = 30.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −16→16
Tmin = 0.955, Tmax = 0.968	k = −17→16
28987 measured reflections	l = −29→29

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)] = 0.041	Hydrogen site location: difference Fourier map
wR(F2) = 0.115	All H-atom parameters refined
S = 1.05	w = 1/[σ2(Fo2) + (0.0599P)2 + 0.958P] where P = (Fo2 + 2Fc2)/3
4585 reflections	(Δ/σ)max = 0.001
286 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.36 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
N1	0.37232 (8)	0.96741 (8)	0.58121 (4)	0.01832 (19)
N2	0.43578 (9)	0.80090 (8)	0.70073 (5)	0.0223 (2)
O1	0.59707 (8)	0.90401 (9)	0.70207 (5)	0.0323 (2)
O2	0.25210 (8)	0.73656 (7)	0.69180 (4)	0.0293 (2)
O3	0.60527 (8)	1.01872 (8)	0.56746 (4)	0.0261 (2)
O4	0.59604 (7)	1.12962 (7)	0.64969 (4)	0.0265 (2)
F1	0.02339 (7)	0.95536 (7)	0.66222 (4)	0.0360 (2)
F2	0.01291 (10)	1.04045 (8)	0.57563 (5)	0.0519 (3)
F3	−0.11317 (8)	0.92265 (11)	0.59782 (7)	0.0708 (4)
C1	0.49344 (10)	0.89519 (10)	0.69792 (5)	0.0218 (2)
C2	0.40611 (10)	0.98226 (9)	0.68818 (5)	0.0187 (2)
C3	0.42693 (10)	1.03976 (9)	0.62520 (5)	0.0182 (2)
C4	0.25821 (9)	0.94880 (9)	0.60901 (5)	0.0180 (2)
C5	0.29053 (9)	0.92447 (9)	0.67894 (5)	0.0187 (2)
C6	0.31822 (10)	0.80982 (9)	0.69077 (5)	0.0206 (2)
C7	0.49500 (13)	0.70166 (11)	0.71063 (7)	0.0309 (3)
C8	0.55262 (10)	1.05870 (9)	0.60979 (5)	0.0197 (2)
C9	0.71865 (12)	1.14732 (14)	0.64520 (7)	0.0352 (3)
C10	−0.00083 (11)	0.94442 (12)	0.60086 (7)	0.0342 (3)
C11	0.19231 (9)	0.86470 (9)	0.57357 (5)	0.0182 (2)
C12	0.25319 (10)	0.78516 (10)	0.54317 (6)	0.0238 (2)
C13	0.19746 (11)	0.70890 (10)	0.50777 (6)	0.0246 (2)
C14	0.07863 (11)	0.70963 (10)	0.50236 (6)	0.0241 (2)
C15	0.01667 (11)	0.78587 (10)	0.53409 (6)	0.0265 (3)
C16	0.07221 (10)	0.86314 (10)	0.56912 (6)	0.0224 (2)
H4	0.2122 (13)	1.0153 (12)	0.6103 (7)	0.023 (4)*
H14	0.0394 (13)	0.6570 (12)	0.4770 (7)	0.024 (4)*
H5	0.2277 (12)	0.9465 (11)	0.7074 (7)	0.018 (3)*
H1	0.3693 (12)	0.9935 (12)	0.5427 (7)	0.021 (4)*
H3	0.3902 (13)	1.1102 (12)	0.6286 (7)	0.025 (4)*
H15	−0.0638 (14)	0.7870 (13)	0.5322 (8)	0.034 (4)*
H2	0.4071 (13)	1.0292 (13)	0.7231 (7)	0.028 (4)*
H12	0.3371 (15)	0.7847 (13)	0.5480 (8)	0.034 (4)*
H13	0.2416 (14)	0.6568 (13)	0.4868 (8)	0.032 (4)*
H73	0.5522 (17)	0.7131 (15)	0.7416 (10)	0.051 (5)*
H72	0.5263 (16)	0.6773 (15)	0.6724 (10)	0.048 (5)*
H93	0.7376 (17)	1.2026 (16)	0.6754 (9)	0.053 (5)*
H71	0.4386 (16)	0.6518 (15)	0.7264 (9)	0.043 (5)*
H92	0.7571 (18)	1.0823 (17)	0.6561 (9)	0.052 (6)*
H91	0.7395 (18)	1.1612 (16)	0.6019 (10)	0.057 (6)*

	U11	U22	U33	U12	U13	U23
N1	0.0192 (4)	0.0201 (5)	0.0156 (4)	−0.0034 (3)	−0.0001 (3)	−0.0012 (3)
N2	0.0226 (5)	0.0219 (5)	0.0223 (4)	−0.0002 (4)	−0.0016 (4)	0.0028 (4)
O1	0.0209 (4)	0.0408 (6)	0.0351 (5)	−0.0038 (4)	−0.0069 (4)	0.0116 (4)
O2	0.0306 (5)	0.0260 (5)	0.0313 (4)	−0.0092 (4)	−0.0024 (4)	0.0040 (4)
O3	0.0235 (4)	0.0328 (5)	0.0219 (4)	−0.0027 (4)	0.0024 (3)	−0.0044 (3)
O4	0.0226 (4)	0.0287 (5)	0.0282 (4)	−0.0085 (4)	0.0013 (3)	−0.0080 (4)
F1	0.0303 (4)	0.0427 (5)	0.0349 (4)	0.0047 (3)	0.0050 (3)	−0.0139 (4)
F2	0.0706 (7)	0.0358 (5)	0.0493 (6)	0.0292 (5)	−0.0191 (5)	−0.0091 (4)
F3	0.0184 (4)	0.0833 (8)	0.1107 (10)	0.0122 (5)	−0.0119 (5)	−0.0622 (8)
C1	0.0222 (5)	0.0272 (6)	0.0162 (5)	−0.0026 (4)	−0.0030 (4)	0.0019 (4)
C2	0.0199 (5)	0.0206 (5)	0.0157 (4)	−0.0035 (4)	0.0002 (4)	−0.0033 (4)
C3	0.0191 (5)	0.0176 (5)	0.0178 (4)	−0.0020 (4)	−0.0002 (4)	−0.0017 (4)
C4	0.0169 (5)	0.0184 (5)	0.0185 (5)	−0.0004 (4)	0.0001 (4)	−0.0024 (4)
C5	0.0172 (5)	0.0215 (5)	0.0174 (4)	−0.0020 (4)	0.0016 (4)	−0.0021 (4)
C6	0.0223 (5)	0.0235 (6)	0.0161 (5)	−0.0027 (4)	0.0010 (4)	0.0000 (4)
C7	0.0309 (7)	0.0268 (7)	0.0352 (7)	0.0057 (5)	−0.0003 (5)	0.0065 (5)
C8	0.0207 (5)	0.0195 (5)	0.0189 (5)	−0.0022 (4)	−0.0014 (4)	0.0009 (4)
C9	0.0232 (6)	0.0457 (9)	0.0367 (7)	−0.0127 (6)	0.0005 (5)	−0.0083 (6)
C10	0.0202 (6)	0.0376 (8)	0.0448 (8)	0.0082 (5)	−0.0101 (5)	−0.0172 (6)
C11	0.0182 (5)	0.0191 (5)	0.0174 (5)	−0.0019 (4)	−0.0003 (4)	−0.0009 (4)
C12	0.0186 (5)	0.0255 (6)	0.0274 (5)	−0.0036 (4)	0.0050 (4)	−0.0062 (4)
C13	0.0254 (6)	0.0226 (6)	0.0257 (5)	−0.0034 (5)	0.0065 (4)	−0.0061 (4)
C14	0.0262 (6)	0.0228 (6)	0.0231 (5)	−0.0045 (5)	−0.0024 (4)	−0.0039 (4)
C15	0.0198 (5)	0.0290 (6)	0.0307 (6)	0.0000 (5)	−0.0065 (5)	−0.0059 (5)
C16	0.0185 (5)	0.0234 (6)	0.0254 (5)	0.0036 (4)	−0.0044 (4)	−0.0048 (4)

N1—C3	1.4578 (14)	C4—C5	1.5633 (15)
N1—C4	1.4704 (14)	C4—H4	1.002 (15)
N1—H1	0.884 (15)	C5—C6	1.5164 (17)
N2—C1	1.3766 (16)	C5—H5	0.988 (14)
N2—C6	1.3866 (15)	C7—H73	0.95 (2)
N2—C7	1.4545 (16)	C7—H72	0.94 (2)
O1—C1	1.2124 (14)	C7—H71	0.972 (19)
O2—C6	1.2089 (15)	C9—H93	0.98 (2)
O3—C8	1.2008 (14)	C9—H92	0.97 (2)
O4—C8	1.3375 (14)	C9—H91	0.97 (2)
O4—C9	1.4451 (15)	C10—C16	1.4990 (17)
F1—C10	1.3406 (17)	C11—C12	1.3942 (16)
F2—C10	1.3452 (19)	C11—C16	1.3984 (15)
F3—C10	1.3357 (16)	C12—C13	1.3886 (16)
C1—C2	1.5173 (17)	C12—H12	0.980 (17)
C2—C5	1.5437 (15)	C13—C14	1.3852 (17)
C2—C3	1.5444 (15)	C13—H13	0.950 (17)
C2—H2	0.953 (16)	C14—C15	1.3842 (18)
C3—C8	1.5157 (16)	C14—H14	0.973 (15)
C3—H3	0.997 (16)	C15—C16	1.3923 (17)
C4—C11	1.5168 (15)	C15—H15	0.936 (17)
C3—N1—C4	103.70 (8)	N2—C7—H72	110.1 (12)
C3—N1—H1	112.0 (10)	H73—C7—H72	112.3 (16)
C4—N1—H1	113.3 (9)	N2—C7—H71	107.4 (11)
C1—N2—C6	113.64 (10)	H73—C7—H71	109.5 (16)
C1—N2—C7	122.31 (11)	H72—C7—H71	110.0 (16)
C6—N2—C7	124.00 (11)	O3—C8—O4	124.67 (11)
C8—O4—C9	115.80 (10)	O3—C8—C3	125.80 (10)
O1—C1—N2	124.12 (12)	O4—C8—C3	109.51 (9)
O1—C1—C2	127.31 (11)	O4—C9—H93	106.9 (12)
N2—C1—C2	108.57 (10)	O4—C9—H92	107.7 (12)
C1—C2—C5	104.50 (9)	H93—C9—H92	110.8 (17)
C1—C2—C3	111.11 (9)	O4—C9—H91	109.7 (12)
C5—C2—C3	104.61 (9)	H93—C9—H91	115.8 (17)
C1—C2—H2	110.2 (10)	H92—C9—H91	105.6 (17)
C5—C2—H2	114.1 (10)	F3—C10—F1	105.89 (13)
C3—C2—H2	112.0 (10)	F3—C10—F2	106.58 (12)
N1—C3—C8	112.42 (9)	F1—C10—F2	105.55 (11)
N1—C3—C2	100.80 (9)	F3—C10—C16	112.82 (11)
C8—C3—C2	114.43 (9)	F1—C10—C16	112.98 (11)
N1—C3—H3	115.4 (9)	F2—C10—C16	112.44 (13)
C8—C3—H3	106.6 (9)	C12—C11—C16	117.67 (10)
C2—C3—H3	107.3 (9)	C12—C11—C4	119.15 (10)
N1—C4—C11	111.69 (9)	C16—C11—C4	123.17 (10)
N1—C4—C5	101.36 (8)	C13—C12—C11	121.52 (11)
C11—C4—C5	116.93 (9)	C13—C12—H12	121.0 (10)
N1—C4—H4	110.8 (9)	C11—C12—H12	117.4 (10)
C11—C4—H4	109.9 (9)	C14—C13—C12	120.32 (11)
C5—C4—H4	105.7 (8)	C14—C13—H13	120.2 (10)
C6—C5—C2	104.70 (9)	C12—C13—H13	119.4 (10)
C6—C5—C4	113.54 (9)	C15—C14—C13	118.85 (11)
C2—C5—C4	103.61 (9)	C15—C14—H14	120.6 (9)
C6—C5—H5	109.2 (8)	C13—C14—H14	120.5 (9)
C2—C5—H5	115.4 (8)	C14—C15—C16	121.01 (11)
C4—C5—H5	110.4 (8)	C14—C15—H15	120.6 (10)
O2—C6—N2	124.03 (11)	C16—C15—H15	118.4 (10)
O2—C6—C5	127.72 (11)	C15—C16—C11	120.57 (11)
N2—C6—C5	108.25 (9)	C15—C16—C10	117.79 (11)
N2—C7—H73	107.4 (12)	C11—C16—C10	121.63 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.884 (15)	2.363 (15)	3.1738 (13)	152.5 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.884 (15)	2.363 (15)	3.1738 (13)	152.5 (13)

Symmetry code: (i) .