tert-Butyl 1,4-dioxo-3,6-di­phenyl-1,2,4,5-tetrahydro­pyrrolo­[3,4-c]­pyrrole-2-carboxyl­ate

The title compound, C₂₃H₂₀N₂O₄, is a soluble precursor (`latent pigment') of diketopyrrolo­pyrrole pigments. The tert-butoxy­carbonyl group is twisted by 78.5 (1)° with respect to the heterocyclic ring system. In the crystal structure, pairs of mol­ecules form centrosymmetric dimers through N—H...O intermolecular hydrogen bonds and are stacked in a herring-bone fashion along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 93 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.051
• wR factor = 0.141
• Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.96

Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C9     -   C10     ..       6.24 su

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: TEXSAN; molecular graphics: ORTEP-III (Burnett & Johnson, 1996); software used to prepare material for publication: TEXSAN.

tert-Butyl 1,4-dioxo-3,6-diphenyl-1,2,4,5-tetrahydropyrrolo[3,4-c]pyrrole-2-carboxylate

Crystal data

C23H20N2O4	F(000) = 816.0
Mr = 388.41	Dx = 1.363 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2yn	Cell parameters from 11787 reflections
a = 6.0502 (6) Å	θ = 3.5–68.1°
b = 16.524 (2) Å	µ = 0.77 mm^−1
c = 19.031 (2) Å	T = 93 K
β = 95.744 (7)°	Needle, orange
V = 1893.0 (4) Å^3	0.50 × 0.10 × 0.05 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID Imaging Plate diffractometer	2370 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.052
72 frames, Δ ω = 10° scans	θmax = 68.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −6→6
Tmin = 0.683, Tmax = 0.962	k = −19→19
17683 measured reflections	l = −22→22
3329 independent reflections

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.051	w = 1/[σ^2(Fo^2) + {0.05[Max(Fo^2,0) + 2Fc^2]/3}^2]
wR(F^2) = 0.141	(Δ/σ)max = 0.0003
S = 1.08	Δρmax = 0.28 e Å^−3
3329 reflections	Δρmin = −0.31 e Å^−3
265 parameters

Special details

Refinement. Refinement using reflections with F² > -10.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.6588 (3)	0.44808 (9)	0.43621 (8)	0.0304 (5)
O2	0.2487 (3)	0.63815 (10)	0.19288 (8)	0.0321 (5)
O3	0.5302 (3)	0.5064 (1)	0.09514 (9)	0.0362 (5)
O4	0.6918 (2)	0.62674 (9)	0.12789 (8)	0.0273 (4)
N1	0.3505 (3)	0.5308 (1)	0.41702 (10)	0.0266 (5)
N2	0.5512 (3)	0.5515 (1)	0.21071 (10)	0.0258 (5)
C1	0.5364 (4)	0.5121 (1)	0.3217 (1)	0.0250 (6)
C2	0.3569 (4)	0.5669 (1)	0.3048 (1)	0.0243 (6)
C3	0.3629 (4)	0.5932 (1)	0.2324 (1)	0.0264 (6)
C4	0.6549 (4)	0.5017 (1)	0.2640 (1)	0.0253 (6)
C5	0.5350 (4)	0.4904 (1)	0.3958 (1)	0.0257 (6)
C6	0.2423 (4)	0.5778 (1)	0.3632 (1)	0.0244 (6)
C7	0.0459 (4)	0.6246 (1)	0.3742 (1)	0.0262 (6)
C8	−0.0509 (4)	0.6215 (1)	0.4379 (1)	0.0283 (7)
C9	−0.2418 (4)	0.6649 (1)	0.4465 (1)	0.0299 (7)
C10	−0.3382 (4)	0.7128 (2)	0.3917 (1)	0.0345 (7)
C11	−0.2432 (4)	0.7169 (1)	0.3286 (1)	0.0325 (7)
C12	−0.0541 (4)	0.6726 (1)	0.3193 (1)	0.0294 (7)
C13	0.8493 (4)	0.4510 (1)	0.2559 (1)	0.0245 (6)
C14	0.9746 (4)	0.4548 (1)	0.1979 (1)	0.0310 (7)
C15	1.1575 (4)	0.4054 (2)	0.1940 (1)	0.0319 (7)
C16	1.2211 (4)	0.3512 (1)	0.2476 (1)	0.0343 (7)
C17	1.0993 (4)	0.3470 (1)	0.3057 (1)	0.0357 (7)
C18	0.9168 (4)	0.3965 (1)	0.3098 (1)	0.0325 (7)
C19	0.5905 (4)	0.5576 (1)	0.1373 (1)	0.0268 (6)
C20	0.7371 (4)	0.6527 (1)	0.0553 (1)	0.0287 (7)
C21	0.8436 (5)	0.7349 (2)	0.0702 (1)	0.0402 (8)
C22	0.8985 (4)	0.5941 (2)	0.0270 (1)	0.0328 (7)
C23	0.5206 (4)	0.6589 (2)	0.0090 (1)	0.0366 (7)
H1N	0.325 (4)	0.533 (1)	0.465 (1)	0.0319*
H8	0.0152	0.5892	0.4757	0.0340*
H9	−0.3071	0.6619	0.4897	0.0358*
H10	−0.4691	0.7428	0.3976	0.0413*
H11	−0.3082	0.7503	0.2914	0.0390*
H12	0.0082	0.6748	0.2754	0.0353*
H14	0.9334	0.4918	0.1607	0.0372*
H15	1.2402	0.4088	0.1543	0.0383*
H16	1.3465	0.3172	0.2447	0.0412*
H17	1.1417	0.3099	0.3428	0.0429*
H18	0.8361	0.3934	0.3500	0.0390*
H21A	0.9737	0.7287	0.1022	0.0483*
H21B	0.7418	0.7694	0.0906	0.0483*
H21C	0.8821	0.7579	0.0274	0.0483*
H22A	1.0338	0.5942	0.0570	0.0393*
H22B	0.8366	0.5412	0.0254	0.0393*
H22C	0.9266	0.6101	−0.0192	0.0393*
H23A	0.4483	0.6078	0.0069	0.0439*
H23B	0.5489	0.6749	−0.0372	0.0439*
H23C	0.4280	0.6980	0.0281	0.0439*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.036 (1)	0.0324 (9)	0.0225 (8)	0.0067 (8)	0.0020 (7)	0.0025 (7)
O2	0.0312 (10)	0.0379 (10)	0.0269 (9)	0.0024 (8)	0.0008 (7)	0.0046 (8)
O3	0.048 (1)	0.0341 (10)	0.0260 (9)	−0.0099 (8)	0.0027 (8)	−0.0044 (8)
O4	0.0349 (10)	0.0269 (8)	0.0210 (8)	−0.0040 (7)	0.0063 (7)	0.0009 (7)
N1	0.028 (1)	0.031 (1)	0.021 (1)	0.0023 (9)	0.0045 (9)	0.0001 (8)
N2	0.029 (1)	0.031 (1)	0.0181 (10)	0.0014 (9)	0.0042 (8)	0.0017 (8)
C1	0.028 (1)	0.029 (1)	0.019 (1)	−0.001 (1)	0.0022 (9)	0.0003 (9)
C2	0.024 (1)	0.028 (1)	0.021 (1)	0.000 (1)	0.0026 (9)	0.0021 (10)
C3	0.028 (1)	0.029 (1)	0.022 (1)	−0.000 (1)	0.0002 (10)	0.0008 (10)
C4	0.030 (1)	0.023 (1)	0.022 (1)	−0.003 (1)	−0.0001 (10)	−0.0017 (9)
C5	0.029 (1)	0.027 (1)	0.022 (1)	−0.002 (1)	0.0033 (10)	0.0010 (10)
C6	0.026 (1)	0.023 (1)	0.025 (1)	−0.0025 (10)	0.0007 (10)	−0.0000 (9)
C7	0.026 (1)	0.026 (1)	0.027 (1)	−0.004 (1)	0.0034 (10)	−0.0011 (10)
C8	0.031 (1)	0.028 (1)	0.026 (1)	−0.003 (1)	0.003 (1)	−0.0026 (10)
C9	0.029 (1)	0.034 (1)	0.027 (1)	−0.001 (1)	0.004 (1)	−0.006 (1)
C10	0.029 (1)	0.034 (1)	0.041 (1)	0.001 (1)	0.004 (1)	−0.009 (1)
C11	0.032 (1)	0.028 (1)	0.037 (1)	0.003 (1)	0.001 (1)	0.001 (1)
C12	0.030 (1)	0.029 (1)	0.029 (1)	−0.002 (1)	0.003 (1)	0.000 (1)
C13	0.026 (1)	0.024 (1)	0.023 (1)	−0.0035 (10)	0.0028 (9)	−0.0026 (10)
C14	0.031 (1)	0.033 (1)	0.028 (1)	−0.002 (1)	0.003 (1)	0.001 (1)
C15	0.031 (1)	0.036 (1)	0.030 (1)	−0.000 (1)	0.006 (1)	−0.005 (1)
C16	0.034 (1)	0.032 (1)	0.037 (1)	0.001 (1)	0.004 (1)	−0.006 (1)
C17	0.041 (2)	0.032 (1)	0.034 (1)	0.009 (1)	0.006 (1)	0.004 (1)
C18	0.036 (1)	0.035 (1)	0.028 (1)	0.003 (1)	0.009 (1)	−0.000 (1)
C19	0.030 (1)	0.029 (1)	0.022 (1)	−0.001 (1)	0.0036 (10)	0.003 (1)
C20	0.036 (1)	0.032 (1)	0.020 (1)	0.001 (1)	0.010 (1)	0.0026 (10)
C21	0.048 (2)	0.033 (1)	0.041 (2)	−0.005 (1)	0.012 (1)	0.003 (1)
C22	0.032 (2)	0.040 (1)	0.028 (1)	0.001 (1)	0.009 (1)	0.002 (1)
C23	0.042 (2)	0.038 (1)	0.029 (1)	0.008 (1)	0.005 (1)	0.007 (1)

Geometric parameters (Å, º)

O1—C5	1.236 (3)	C11—C12	1.385 (3)
O2—C3	1.221 (3)	C11—H11	0.950
O3—C19	1.196 (3)	C12—H12	0.950
O4—C19	1.317 (3)	C13—C14	1.403 (3)
O4—C20	1.498 (2)	C13—C18	1.394 (3)
N1—C5	1.395 (3)	C14—C15	1.383 (3)
N1—C6	1.395 (3)	C14—H14	0.950
N1—H1N	0.94 (2)	C15—C16	1.382 (3)
N2—C3	1.427 (3)	C15—H15	0.950
N2—C4	1.404 (3)	C16—C17	1.391 (3)
N2—C19	1.445 (3)	C16—H16	0.950
C1—C2	1.425 (3)	C17—C18	1.383 (3)
C1—C4	1.382 (3)	C17—H17	0.950
C1—C5	1.455 (3)	C18—H18	0.950
C2—C3	1.449 (3)	C20—C21	1.517 (3)
C2—C6	1.379 (3)	C20—C22	1.512 (3)
C4—C13	1.465 (3)	C20—C23	1.508 (3)
C6—C7	1.450 (3)	C21—H21A	0.950
C7—C8	1.400 (3)	C21—H21B	0.950
C7—C12	1.401 (3)	C21—H21C	0.950
C8—C9	1.382 (3)	C22—H22A	0.950
C8—H8	0.950	C22—H22B	0.950
C9—C10	1.390 (3)	C22—H22C	0.950
C9—H9	0.950	C23—H23A	0.950
C10—C11	1.384 (3)	C23—H23B	0.950
C10—H10	0.950	C23—H23C	0.950
O1···N1^i	2.821 (2)	H1N···H1N^i	2.64 (5)
C5···H1N^i	2.73 (2)
C19—O4—C20	120.3 (2)	C6—C7—C8	121.7 (2)
C5—N1—C6	112.6 (2)	C6—C7—C12	119.6 (2)
C5—N1—H1N	121 (1)	C8—C7—C12	118.7 (2)
C6—N1—H1N	125 (1)	C7—C8—C9	120.6 (2)
C3—N2—C4	112.7 (2)	C8—C9—C10	120.0 (2)
C3—N2—C19	117.4 (2)	C9—C10—C11	119.9 (2)
C4—N2—C19	129.4 (2)	C10—C11—C12	120.4 (2)
C2—C1—C4	110.1 (2)	C7—C12—C11	120.3 (2)
C2—C1—C5	107.3 (2)	C4—C13—C14	124.1 (2)
C4—C1—C5	142.5 (2)	C4—C13—C18	118.1 (2)
C1—C2—C3	108.3 (2)	C14—C13—C18	117.8 (2)
C1—C2—C6	109.5 (2)	C13—C14—C15	120.9 (2)
C3—C2—C6	142.2 (2)	C14—C15—C16	120.6 (2)
O2—C3—N2	122.3 (2)	C15—C16—C17	119.2 (2)
O2—C3—C2	134.5 (2)	C16—C17—C18	120.3 (2)
N2—C3—C2	103.1 (2)	C13—C18—C17	121.2 (2)
N2—C4—C1	105.7 (2)	O3—C19—O4	129.6 (2)
N2—C4—C13	124.4 (2)	O3—C19—N2	122.0 (2)
C1—C4—C13	129.9 (2)	O4—C19—N2	108.4 (2)
O1—C5—N1	122.9 (2)	O4—C20—C21	101.3 (2)
O1—C5—C1	132.9 (2)	O4—C20—C22	109.2 (2)
N1—C5—C1	104.2 (2)	O4—C20—C23	109.3 (2)
N1—C6—C2	106.4 (2)	C21—C20—C22	111.2 (2)
N1—C6—C7	121.5 (2)	C21—C20—C23	112.1 (2)
C2—C6—C7	132.1 (2)	C22—C20—C23	112.9 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.94 (2)	1.90 (2)	2.821 (2)	166 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.