5,6,7-Tri­methoxy-2,3-di­hydro-1H,8H-benzo­[a]­pyrrolo­[3,4-c]­carbazole-1,3-dione di­methyl sulfoxide solvate

The crystal structure of the title compound, C₂₁H₁₆N₂O₅·C₂H₆OS, was determined to investigate the electrocyclic reactivity of 3,4-di­aryl-1H-pyrrole-2,5-diones (3,4-bisarylmal­eimides) to the yield corresponding carbazole derivatives.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.076
• wR factor = 0.187
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          6

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius 1989); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELX97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

5,6,7-Trimethoxy-2,3-dihydro-1H,8H-benzo[a]pyrrolo[3,4-c]carbazole-1,3-dione dimethyl sulfoxide solvate

Crystal data

C21H16N2O5·C2H6OS	F(000) = 952
Mr = 454.50	Dx = 1.441 Mg m^−3
Monoclinic, P21/c	Melting point: 272 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54178 Å
a = 7.994 (2) Å	Cell parameters from 25 reflections
b = 20.040 (4) Å	θ = 30–44°
c = 13.644 (4) Å	µ = 1.76 mm^−1
β = 106.586 (12)°	T = 295 K
V = 2094.8 (9) Å^3	Needle, yellow
Z = 4	0.24 × 0.06 × 0.04 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	2943 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.062
Graphite monochromator	θmax = 74.0°, θmin = 4.0°
θ/2ω scans	h = −9→0
Absorption correction: psi-scan (CORINC; Dräger & Gattow, 1971)	k = 0→24
Tmin = 0.783, Tmax = 0.932	l = −16→17
4534 measured reflections	3 standard reflections every 60 min
4228 independent reflections	intensity decay: 5%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.187	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0644P)^2 + 1.9378P] where P = (Fo^2 + 2Fc^2)/3
4228 reflections	(Δ/σ)max < 0.001
298 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.7962 (4)	0.51606 (18)	0.3833 (3)	0.0311 (8)
C1A	0.8386 (4)	0.52185 (18)	0.2874 (3)	0.0330 (8)
C2	0.8208 (5)	0.4797 (2)	0.2033 (3)	0.0417 (9)
H2	0.7697	0.4378	0.2011	0.050*
C3	0.8809 (6)	0.5018 (2)	0.1238 (3)	0.0498 (10)
H3	0.8715	0.4741	0.0678	0.060*
C4	0.9549 (6)	0.5645 (2)	0.1252 (3)	0.0500 (11)
H4	0.9930	0.5780	0.0699	0.060*
C5	0.9731 (5)	0.6068 (2)	0.2065 (3)	0.0458 (10)
H5	1.0241	0.6486	0.2078	0.055*
C5A	0.9127 (5)	0.58497 (19)	0.2869 (3)	0.0375 (8)
N6	0.9150 (4)	0.61706 (17)	0.3766 (2)	0.0368 (7)
H6	0.954 (2)	0.6524 (19)	0.3967 (11)	0.039 (12)*
C7	0.8459 (4)	0.57645 (17)	0.4360 (3)	0.0318 (8)
C8	0.7298 (4)	0.46665 (18)	0.4343 (3)	0.0311 (8)
C9	0.6783 (5)	0.39624 (19)	0.4048 (3)	0.0361 (8)
N10	0.6322 (4)	0.36876 (17)	0.4856 (3)	0.0419 (8)
H10	0.6202 (8)	0.326 (3)	0.4940 (6)	0.072 (16)*
C11	0.6463 (5)	0.41469 (19)	0.5643 (3)	0.0361 (8)
C12	0.7110 (4)	0.47758 (18)	0.5301 (3)	0.0331 (8)
C13	0.7554 (4)	0.53893 (18)	0.5834 (3)	0.0308 (8)
C14	0.8275 (4)	0.58967 (17)	0.5343 (3)	0.0304 (7)
C15	0.8802 (4)	0.65043 (18)	0.5883 (3)	0.0340 (8)
C16	0.8666 (5)	0.65931 (18)	0.6853 (3)	0.0367 (8)
C17	0.7865 (5)	0.6089 (2)	0.7305 (3)	0.0372 (8)
C18	0.7331 (4)	0.55044 (19)	0.6801 (3)	0.0348 (8)
H18	0.6813	0.5179	0.7104	0.042*
O19	0.6745 (4)	0.36796 (14)	0.3257 (2)	0.0470 (7)
O20	0.6124 (4)	0.40231 (15)	0.6433 (2)	0.0497 (7)
O21	0.9541 (3)	0.69891 (13)	0.5426 (2)	0.0440 (7)
C22	0.8477 (7)	0.7568 (2)	0.5112 (4)	0.0611 (13)
H22A	0.7408	0.7443	0.4616	0.092*
H22B	0.9088	0.7885	0.4815	0.092*
H22C	0.8221	0.7764	0.5695	0.092*
O23	0.9225 (3)	0.71775 (13)	0.7376 (2)	0.0447 (7)
C24	1.0928 (5)	0.7125 (2)	0.8090 (3)	0.0554 (12)
H24A	1.0922	0.6782	0.8580	0.083*
H24B	1.1240	0.7543	0.8437	0.083*
H24C	1.1763	0.7014	0.7730	0.083*
O25	0.7720 (4)	0.62545 (15)	0.8243 (2)	0.0495 (7)
C26	0.6739 (6)	0.5813 (3)	0.8681 (3)	0.0555 (12)
H26A	0.5638	0.5719	0.8190	0.083*
H26B	0.6542	0.6016	0.9275	0.083*
H26C	0.7375	0.5404	0.8874	0.083*
S1	0.62426 (15)	0.19399 (6)	0.38603 (10)	0.0582 (4)
O2L	0.5746 (5)	0.22835 (17)	0.4712 (3)	0.0696 (10)
C3L	0.5485 (8)	0.1110 (3)	0.3870 (4)	0.0769 (16)
H3L1	0.6110	0.0897	0.4497	0.115*
H3L2	0.5672	0.0870	0.3302	0.115*
H3L3	0.4261	0.1115	0.3815	0.115*
C4L	0.4746 (7)	0.2194 (3)	0.2697 (4)	0.0652 (14)
H4L1	0.3576	0.2120	0.2728	0.098*
H4L2	0.4942	0.1940	0.2143	0.098*
H4L3	0.4908	0.2660	0.2587	0.098*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0253 (16)	0.037 (2)	0.0319 (18)	0.0048 (14)	0.0095 (14)	0.0027 (15)
C1A	0.0268 (16)	0.039 (2)	0.0338 (19)	0.0073 (15)	0.0093 (14)	0.0041 (16)
C2	0.039 (2)	0.050 (2)	0.038 (2)	0.0072 (18)	0.0135 (16)	−0.0049 (18)
C3	0.052 (2)	0.063 (3)	0.038 (2)	0.009 (2)	0.0179 (19)	−0.007 (2)
C4	0.047 (2)	0.071 (3)	0.038 (2)	0.002 (2)	0.0213 (18)	0.006 (2)
C5	0.046 (2)	0.049 (2)	0.046 (2)	−0.0020 (19)	0.0201 (19)	0.007 (2)
C5A	0.0353 (19)	0.041 (2)	0.037 (2)	0.0063 (16)	0.0109 (16)	0.0030 (16)
N6	0.0408 (17)	0.0330 (17)	0.0391 (18)	−0.0024 (14)	0.0155 (14)	0.0000 (14)
C7	0.0290 (17)	0.0328 (19)	0.0340 (19)	0.0022 (14)	0.0097 (14)	0.0033 (15)
C8	0.0238 (16)	0.0348 (19)	0.0331 (18)	0.0043 (14)	0.0055 (14)	−0.0013 (15)
C9	0.0349 (19)	0.0332 (19)	0.039 (2)	0.0032 (15)	0.0093 (15)	0.0003 (17)
N10	0.0471 (19)	0.0326 (18)	0.048 (2)	−0.0044 (14)	0.0169 (15)	0.0005 (15)
C11	0.0336 (18)	0.036 (2)	0.037 (2)	−0.0025 (15)	0.0079 (15)	0.0016 (16)
C12	0.0290 (17)	0.0338 (19)	0.036 (2)	0.0026 (14)	0.0093 (14)	0.0033 (15)
C13	0.0247 (16)	0.0353 (19)	0.0312 (18)	0.0045 (14)	0.0060 (13)	0.0013 (15)
C14	0.0284 (16)	0.0306 (18)	0.0323 (18)	0.0014 (14)	0.0090 (14)	0.0021 (15)
C15	0.0296 (18)	0.0346 (19)	0.038 (2)	0.0015 (14)	0.0099 (15)	0.0040 (16)
C16	0.038 (2)	0.0321 (19)	0.039 (2)	0.0042 (15)	0.0096 (16)	−0.0034 (16)
C17	0.0359 (19)	0.047 (2)	0.0288 (18)	0.0026 (17)	0.0096 (15)	−0.0047 (16)
C18	0.0301 (18)	0.041 (2)	0.0332 (19)	−0.0005 (15)	0.0086 (15)	0.0031 (16)
O19	0.0523 (17)	0.0445 (16)	0.0475 (17)	−0.0027 (13)	0.0195 (13)	−0.0121 (14)
O20	0.0630 (19)	0.0484 (17)	0.0411 (16)	−0.0128 (14)	0.0204 (14)	0.0030 (14)
O21	0.0465 (15)	0.0358 (15)	0.0534 (17)	−0.0058 (12)	0.0201 (13)	0.0007 (13)
C22	0.081 (3)	0.040 (2)	0.061 (3)	0.006 (2)	0.017 (3)	0.013 (2)
O23	0.0451 (15)	0.0390 (15)	0.0473 (16)	0.0017 (12)	0.0089 (13)	−0.0093 (13)
C24	0.043 (2)	0.056 (3)	0.060 (3)	0.000 (2)	0.004 (2)	−0.018 (2)
O25	0.0596 (18)	0.0523 (18)	0.0409 (16)	−0.0060 (14)	0.0211 (14)	−0.0066 (13)
C26	0.059 (3)	0.075 (3)	0.036 (2)	−0.010 (2)	0.020 (2)	−0.003 (2)
S1	0.0432 (6)	0.0558 (7)	0.0736 (8)	−0.0053 (5)	0.0133 (5)	−0.0108 (6)
O2L	0.088 (3)	0.057 (2)	0.064 (2)	−0.0114 (19)	0.0214 (19)	−0.0147 (17)
C3L	0.092 (4)	0.050 (3)	0.083 (4)	0.006 (3)	0.016 (3)	−0.007 (3)
C4L	0.075 (3)	0.057 (3)	0.063 (3)	0.008 (3)	0.018 (3)	−0.006 (2)

Geometric parameters (Å, º)

C1—C8	1.399 (5)	C15—C16	1.371 (5)
C1—C7	1.406 (5)	C15—O21	1.375 (4)
C1—C1A	1.447 (5)	C16—O23	1.378 (4)
C1A—C5A	1.398 (5)	C16—C17	1.427 (5)
C1A—C2	1.400 (5)	C17—O25	1.358 (4)
C2—C3	1.380 (6)	C17—C18	1.364 (5)
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.385 (6)	O21—C22	1.429 (5)
C3—H3	0.9300	C22—H22A	0.9600
C4—C5	1.372 (6)	C22—H22B	0.9600
C4—H4	0.9300	C22—H22C	0.9600
C5—C5A	1.390 (5)	O23—C24	1.434 (5)
C5—H5	0.9300	C24—H24A	0.9600
C5A—N6	1.378 (5)	C24—H24B	0.9600
N6—C7	1.371 (4)	C24—H24C	0.9600
N6—H6	0.7902	O25—C26	1.423 (5)
C7—C14	1.416 (5)	C26—H26A	0.9600
C8—C12	1.375 (5)	C26—H26B	0.9600
C8—C9	1.493 (5)	C26—H26C	0.9600
C9—O19	1.211 (4)	S1—O2L	1.499 (3)
C9—N10	1.374 (5)	S1—C4L	1.768 (5)
N10—C11	1.394 (5)	S1—C3L	1.770 (5)
N10—H10	0.8698	C3L—H3L1	0.9600
C11—O20	1.209 (4)	C3L—H3L2	0.9600
C11—C12	1.487 (5)	C3L—H3L3	0.9600
C12—C13	1.421 (5)	C4L—H4L1	0.9600
C13—C18	1.400 (5)	C4L—H4L2	0.9600
C13—C14	1.427 (5)	C4L—H4L3	0.9600
C14—C15	1.423 (5)
C8—C1—C7	116.5 (3)	C16—C15—O21	120.6 (3)
C8—C1—C1A	136.6 (3)	C16—C15—C14	121.1 (3)
C7—C1—C1A	106.8 (3)	O21—C15—C14	118.2 (3)
C5A—C1A—C2	119.1 (3)	C15—C16—O23	120.4 (3)
C5A—C1A—C1	106.6 (3)	C15—C16—C17	119.6 (3)
C2—C1A—C1	134.3 (4)	O23—C16—C17	119.8 (3)
C3—C2—C1A	118.3 (4)	O25—C17—C18	125.9 (4)
C3—C2—H2	120.9	O25—C17—C16	113.8 (3)
C1A—C2—H2	120.9	C18—C17—C16	120.3 (3)
C2—C3—C4	121.6 (4)	C17—C18—C13	120.7 (3)
C2—C3—H3	119.2	C17—C18—H18	119.6
C4—C3—H3	119.2	C13—C18—H18	119.6
C5—C4—C3	121.2 (4)	C15—O21—C22	114.4 (3)
C5—C4—H4	119.4	O21—C22—H22A	109.5
C3—C4—H4	119.4	O21—C22—H22B	109.5
C4—C5—C5A	117.6 (4)	H22A—C22—H22B	109.5
C4—C5—H5	121.2	O21—C22—H22C	109.5
C5A—C5—H5	121.2	H22A—C22—H22C	109.5
N6—C5A—C5	129.4 (4)	H22B—C22—H22C	109.5
N6—C5A—C1A	108.4 (3)	C16—O23—C24	113.2 (3)
C5—C5A—C1A	122.1 (4)	O23—C24—H24A	109.5
C7—N6—C5A	110.0 (3)	O23—C24—H24B	109.5
C7—N6—H6	120.7	H24A—C24—H24B	109.5
C5A—N6—H6	129.1	O23—C24—H24C	109.5
N6—C7—C1	108.2 (3)	H24A—C24—H24C	109.5
N6—C7—C14	128.1 (3)	H24B—C24—H24C	109.5
C1—C7—C14	123.7 (3)	C17—O25—C26	116.7 (3)
C12—C8—C1	121.3 (3)	O25—C26—H26A	109.5
C12—C8—C9	108.1 (3)	O25—C26—H26B	109.5
C1—C8—C9	130.5 (3)	H26A—C26—H26B	109.5
O19—C9—N10	125.7 (4)	O25—C26—H26C	109.5
O19—C9—C8	128.1 (4)	H26A—C26—H26C	109.5
N10—C9—C8	106.2 (3)	H26B—C26—H26C	109.5
C9—N10—C11	111.9 (3)	O2L—S1—C4L	107.6 (2)
C9—N10—H10	124.3	O2L—S1—C3L	105.0 (2)
C11—N10—H10	122.3	C4L—S1—C3L	97.6 (3)
O20—C11—N10	124.1 (4)	S1—C3L—H3L1	109.5
O20—C11—C12	129.8 (4)	S1—C3L—H3L2	109.5
N10—C11—C12	106.1 (3)	H3L1—C3L—H3L2	109.5
C8—C12—C13	123.0 (3)	S1—C3L—H3L3	109.5
C8—C12—C11	107.8 (3)	H3L1—C3L—H3L3	109.5
C13—C12—C11	129.2 (3)	H3L2—C3L—H3L3	109.5
C18—C13—C12	123.0 (3)	S1—C4L—H4L1	109.5
C18—C13—C14	120.1 (3)	S1—C4L—H4L2	109.5
C12—C13—C14	116.9 (3)	H4L1—C4L—H4L2	109.5
C7—C14—C15	123.7 (3)	S1—C4L—H4L3	109.5
C7—C14—C13	118.5 (3)	H4L1—C4L—H4L3	109.5
C15—C14—C13	117.9 (3)	H4L2—C4L—H4L3	109.5
C8—C1—C1A—C5A	−176.0 (4)	O20—C11—C12—C8	180.0 (4)
C7—C1—C1A—C5A	0.4 (4)	N10—C11—C12—C8	0.7 (4)
C8—C1—C1A—C2	4.0 (7)	O20—C11—C12—C13	2.4 (6)
C7—C1—C1A—C2	−179.7 (4)	N10—C11—C12—C13	−176.8 (3)
C5A—C1A—C2—C3	1.4 (5)	C8—C12—C13—C18	178.8 (3)
C1—C1A—C2—C3	−178.6 (4)	C11—C12—C13—C18	−4.0 (6)
C1A—C2—C3—C4	−1.0 (6)	C8—C12—C13—C14	−2.0 (5)
C2—C3—C4—C5	0.7 (7)	C11—C12—C13—C14	175.2 (3)
C3—C4—C5—C5A	−0.8 (6)	N6—C7—C14—C15	0.3 (6)
C4—C5—C5A—N6	179.9 (4)	C1—C7—C14—C15	179.0 (3)
C4—C5—C5A—C1A	1.2 (6)	N6—C7—C14—C13	−178.4 (3)
C2—C1A—C5A—N6	179.5 (3)	C1—C7—C14—C13	0.4 (5)
C1—C1A—C5A—N6	−0.5 (4)	C18—C13—C14—C7	−179.2 (3)
C2—C1A—C5A—C5	−1.5 (5)	C12—C13—C14—C7	1.5 (5)
C1—C1A—C5A—C5	178.4 (3)	C18—C13—C14—C15	2.0 (5)
C5—C5A—N6—C7	−178.3 (4)	C12—C13—C14—C15	−177.2 (3)
C1A—C5A—N6—C7	0.5 (4)	C7—C14—C15—C16	−176.9 (3)
C5A—N6—C7—C1	−0.3 (4)	C13—C14—C15—C16	1.7 (5)
C5A—N6—C7—C14	178.6 (3)	C7—C14—C15—O21	−0.4 (5)
C8—C1—C7—N6	177.1 (3)	C13—C14—C15—O21	178.3 (3)
C1A—C1—C7—N6	−0.1 (4)	O21—C15—C16—O23	1.7 (5)
C8—C1—C7—C14	−1.9 (5)	C14—C15—C16—O23	178.3 (3)
C1A—C1—C7—C14	−179.0 (3)	O21—C15—C16—C17	178.8 (3)
C7—C1—C8—C12	1.4 (5)	C14—C15—C16—C17	−4.7 (5)
C1A—C1—C8—C12	177.5 (4)	C15—C16—C17—O25	−176.3 (3)
C7—C1—C8—C9	−174.8 (3)	O23—C16—C17—O25	0.8 (5)
C1A—C1—C8—C9	1.3 (7)	C15—C16—C17—C18	3.9 (5)
C12—C8—C9—O19	178.8 (4)	O23—C16—C17—C18	−179.0 (3)
C1—C8—C9—O19	−4.6 (6)	O25—C17—C18—C13	−179.9 (3)
C12—C8—C9—N10	−0.4 (4)	C16—C17—C18—C13	−0.2 (5)
C1—C8—C9—N10	176.2 (3)	C12—C13—C18—C17	176.4 (3)
O19—C9—N10—C11	−178.3 (4)	C14—C13—C18—C17	−2.8 (5)
C8—C9—N10—C11	0.9 (4)	C16—C15—O21—C22	−72.9 (5)
C9—N10—C11—O20	179.7 (4)	C14—C15—O21—C22	110.5 (4)
C9—N10—C11—C12	−1.0 (4)	C15—C16—O23—C24	−99.1 (4)
C1—C8—C12—C13	0.5 (5)	C17—C16—O23—C24	83.8 (4)
C9—C8—C12—C13	177.5 (3)	C18—C17—O25—C26	−8.0 (6)
C1—C8—C12—C11	−177.2 (3)	C16—C17—O25—C26	172.3 (3)
C9—C8—C12—C11	−0.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···O21	0.79	2.20	2.741 (4)	126
N10—H10···O2L	0.87	2.00	2.849 (5)	164