2-[2-(4-Methoxy­phen­yl)vin­yl]-3-[(2-maleimid­yl)acet­yl]-2,3-dihydro-1,3-benzothia­zole

The crystal packing of the title compound {systematic name: 3-[(2,3-dioxo-3-pyrrolin-1-yl)acet­yl]-2-[2-(4-methoxy­phen­yl)vin­yl]-2,3-dihydro-1,3-benzothia­zole}, C₂₈H₂₂N₂O₄S, is stabil­ized by inter­molecular C—H...O and C—H...S hydrogen bonds and by π–π stacking inter­actions occurring between a benzene ring and the pyrrole ring of centrosymmetrically related mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.102
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.03 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.28 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C5     -   C6      ..       5.53 su

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

(I)

Crystal data

C28H22N2O4S	F(000) = 1008
Mr = 482.54	Dx = 1.321 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2910 reflections
a = 9.970 (5) Å	θ = 2.2–21.9°
b = 10.191 (5) Å	µ = 0.17 mm^−1
c = 23.941 (11) Å	T = 273 K
β = 94.310 (7)°	Block, colourless
V = 2426 (2) Å^3	0.28 × 0.22 × 0.16 mm
Z = 4

Data collection

APEX II CCD area detector diffractometer	4258 independent reflections
Radiation source: fine-focus sealed tube	3012 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→10
Tmin = 0.952, Tmax = 0.973	k = −12→11
12808 measured reflections	l = −28→28

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.102	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0413P)^2 + 0.6152P] where P = (Fo^2 + 2Fc^2)/3
4258 reflections	(Δ/σ)max < 0.001
317 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.21 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
S1	0.47726 (6)	0.51328 (5)	0.08892 (2)	0.06071 (18)
O1	−0.04815 (19)	0.11811 (18)	−0.14953 (8)	0.0970 (6)
O2	0.48525 (19)	0.12135 (15)	0.20196 (7)	0.0830 (5)
O3	0.8038 (2)	0.01662 (18)	0.21663 (8)	0.1049 (7)
O4	0.4564 (2)	−0.16266 (18)	0.11186 (9)	0.0962 (6)
N1	0.47664 (15)	0.27929 (14)	0.13590 (6)	0.0415 (4)
N2	0.63509 (18)	−0.04743 (15)	0.15230 (7)	0.0549 (4)
C1	0.1723 (2)	0.0603 (2)	−0.02253 (9)	0.0592 (6)
H1	0.1947	−0.0057	0.0033	0.071*
C2	0.0798 (2)	0.0340 (2)	−0.06707 (9)	0.0645 (6)
H2	0.0422	−0.0493	−0.0714	0.077*
C28	−0.1074 (4)	−0.0070 (3)	−0.15874 (14)	0.1269 (13)
H29A	−0.0383	−0.0709	−0.1633	0.190*
H29B	−0.1676	−0.0046	−0.1920	0.190*
H29C	−0.1566	−0.0304	−0.1272	0.190*
C4	0.1032 (2)	0.2537 (2)	−0.09825 (10)	0.0678 (6)
H4	0.0805	0.3202	−0.1238	0.081*
C5	0.1955 (2)	0.2770 (2)	−0.05411 (9)	0.0598 (6)
H5	0.2345	0.3597	−0.0501	0.072*
C6	0.2320 (2)	0.1809 (2)	−0.01541 (8)	0.0504 (5)
C7	0.3290 (2)	0.2061 (2)	0.03326 (8)	0.0530 (5)
H7	0.3181	0.1594	0.0660	0.064*
C8	0.42845 (19)	0.2891 (2)	0.03347 (7)	0.0487 (5)
H8	0.4464	0.3233	−0.0012	0.058*
C9	0.51688 (19)	0.33594 (17)	0.08219 (7)	0.0420 (4)
C10	0.66753 (19)	0.33310 (17)	0.07491 (8)	0.0457 (5)
C11	0.7171 (2)	0.2987 (2)	0.02465 (9)	0.0589 (6)
H11	0.6587	0.2703	−0.0050	0.071*
C12	0.8543 (3)	0.3064 (3)	0.01840 (14)	0.0877 (9)
H12	0.8870	0.2843	−0.0157	0.105*
C13	0.9413 (3)	0.3460 (3)	0.0616 (2)	0.1043 (11)
H13	1.0330	0.3511	0.0571	0.125*
C14	0.8931 (3)	0.3781 (3)	0.11135 (16)	0.0920 (9)
H14	0.9527	0.4030	0.1412	0.110*
C15	0.7569 (2)	0.3745 (2)	0.11843 (10)	0.0654 (6)
H15	0.7253	0.3998	0.1524	0.078*
C16	0.3576 (2)	0.47935 (18)	0.13649 (8)	0.0486 (5)
C17	0.2615 (2)	0.5654 (2)	0.15317 (9)	0.0590 (5)
H17	0.2533	0.6489	0.1377	0.071*
C18	0.1779 (2)	0.5255 (2)	0.19318 (9)	0.0627 (6)
H18	0.1133	0.5826	0.2052	0.075*
C19	0.1901 (2)	0.4021 (3)	0.21515 (8)	0.0643 (6)
H19	0.1325	0.3762	0.2419	0.077*
C20	0.2860 (2)	0.3139 (2)	0.19868 (8)	0.0556 (5)
H20	0.2925	0.2301	0.2140	0.067*
C21	0.37187 (19)	0.35372 (17)	0.15892 (7)	0.0435 (4)
C22	0.5196 (2)	0.16048 (18)	0.15752 (8)	0.0507 (5)
C23	0.6122 (2)	0.07637 (19)	0.12467 (9)	0.0577 (5)
H23A	0.5716	0.0621	0.0871	0.069*
H23B	0.6972	0.1213	0.1219	0.069*
C24	0.7253 (3)	−0.0644 (2)	0.19840 (10)	0.0711 (7)
C25	0.7005 (3)	−0.1992 (2)	0.21900 (10)	0.0865 (9)
H25	0.7496	−0.2404	0.2486	0.104*
C26	0.5996 (3)	−0.2501 (2)	0.18928 (11)	0.0825 (8)
H26	0.5646	−0.3335	0.1942	0.099*
C27	0.5491 (3)	−0.1543 (2)	0.14641 (10)	0.0643 (6)
C3	0.0437 (2)	0.1318 (2)	−0.10499 (9)	0.0640 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0722 (4)	0.0390 (3)	0.0734 (4)	0.0045 (3)	0.0218 (3)	0.0143 (3)
O1	0.0944 (14)	0.0924 (13)	0.0966 (13)	−0.0170 (11)	−0.0435 (11)	0.0115 (10)
O2	0.1232 (15)	0.0665 (10)	0.0646 (10)	0.0271 (10)	0.0410 (10)	0.0300 (8)
O3	0.1215 (17)	0.0706 (12)	0.1156 (15)	−0.0017 (11)	−0.0367 (12)	−0.0219 (11)
O4	0.0954 (14)	0.0831 (13)	0.1070 (14)	−0.0198 (11)	−0.0139 (12)	−0.0003 (11)
N1	0.0526 (10)	0.0365 (8)	0.0363 (8)	−0.0007 (7)	0.0088 (7)	0.0040 (6)
N2	0.0735 (12)	0.0339 (9)	0.0569 (10)	0.0013 (8)	0.0027 (9)	0.0047 (7)
C1	0.0666 (15)	0.0544 (13)	0.0554 (13)	−0.0023 (11)	−0.0029 (11)	0.0071 (10)
C2	0.0678 (15)	0.0555 (13)	0.0687 (14)	−0.0148 (11)	−0.0041 (12)	−0.0014 (11)
C28	0.135 (3)	0.119 (3)	0.117 (2)	−0.060 (2)	−0.058 (2)	0.011 (2)
C4	0.0684 (15)	0.0605 (14)	0.0724 (15)	0.0007 (12)	−0.0083 (12)	0.0171 (12)
C5	0.0570 (14)	0.0518 (12)	0.0706 (14)	−0.0096 (10)	0.0039 (11)	0.0021 (11)
C6	0.0462 (12)	0.0539 (12)	0.0511 (12)	−0.0009 (9)	0.0033 (9)	0.0014 (10)
C7	0.0577 (13)	0.0540 (12)	0.0479 (12)	−0.0002 (10)	0.0091 (10)	0.0043 (9)
C8	0.0477 (12)	0.0611 (12)	0.0381 (10)	−0.0017 (10)	0.0084 (9)	0.0074 (9)
C9	0.0491 (11)	0.0379 (10)	0.0394 (10)	−0.0004 (8)	0.0061 (8)	0.0076 (8)
C10	0.0458 (11)	0.0360 (10)	0.0552 (12)	−0.0034 (8)	0.0025 (9)	0.0128 (9)
C11	0.0548 (14)	0.0572 (13)	0.0665 (14)	0.0039 (11)	0.0167 (11)	0.0129 (11)
C12	0.0691 (19)	0.0753 (17)	0.125 (2)	0.0117 (15)	0.0455 (18)	0.0233 (17)
C13	0.0487 (18)	0.0738 (19)	0.192 (4)	0.0009 (14)	0.019 (2)	0.031 (2)
C14	0.0562 (18)	0.0673 (17)	0.147 (3)	−0.0136 (14)	−0.0297 (18)	0.0204 (18)
C15	0.0633 (15)	0.0522 (12)	0.0779 (15)	−0.0096 (11)	−0.0130 (12)	0.0086 (11)
C16	0.0519 (12)	0.0440 (11)	0.0502 (11)	−0.0004 (9)	0.0047 (9)	−0.0028 (9)
C17	0.0605 (14)	0.0497 (12)	0.0663 (14)	0.0052 (11)	0.0015 (11)	−0.0108 (10)
C18	0.0535 (13)	0.0775 (16)	0.0565 (13)	0.0092 (12)	−0.0001 (11)	−0.0225 (12)
C19	0.0545 (14)	0.0938 (18)	0.0457 (12)	−0.0017 (13)	0.0108 (10)	−0.0062 (12)
C20	0.0587 (13)	0.0648 (13)	0.0438 (11)	−0.0039 (11)	0.0072 (10)	0.0035 (10)
C21	0.0499 (12)	0.0446 (11)	0.0358 (10)	−0.0027 (9)	0.0024 (8)	−0.0041 (8)
C22	0.0677 (14)	0.0397 (11)	0.0455 (11)	−0.0009 (9)	0.0094 (10)	0.0074 (9)
C23	0.0761 (15)	0.0391 (11)	0.0593 (13)	0.0072 (10)	0.0136 (11)	0.0122 (9)
C24	0.103 (2)	0.0439 (12)	0.0641 (15)	0.0086 (13)	−0.0070 (14)	−0.0095 (11)
C25	0.153 (3)	0.0476 (14)	0.0567 (14)	0.0227 (16)	−0.0066 (16)	0.0059 (11)
C26	0.140 (3)	0.0393 (12)	0.0700 (16)	−0.0032 (14)	0.0168 (17)	0.0043 (12)
C27	0.0863 (19)	0.0437 (12)	0.0640 (15)	−0.0036 (12)	0.0122 (13)	−0.0022 (11)
C3	0.0543 (14)	0.0732 (15)	0.0622 (14)	−0.0031 (12)	−0.0110 (11)	0.0022 (12)

Geometric parameters (Å, º)

S1—C16	1.745 (2)	C9—C10	1.525 (3)
S1—C9	1.859 (2)	C10—C11	1.380 (3)
O1—C3	1.360 (3)	C10—C15	1.385 (3)
O1—C28	1.416 (3)	C11—C12	1.390 (3)
O2—C22	1.210 (2)	C11—H11	0.9300
O3—C24	1.197 (3)	C12—C13	1.360 (4)
O4—C27	1.197 (3)	C12—H12	0.9300
N1—C22	1.373 (2)	C13—C14	1.358 (4)
N1—C21	1.434 (2)	C13—H13	0.9300
N1—C9	1.492 (2)	C14—C15	1.381 (4)
N2—C24	1.381 (3)	C14—H14	0.9300
N2—C27	1.386 (3)	C15—H15	0.9300
N2—C23	1.435 (2)	C16—C17	1.380 (3)
C1—C6	1.370 (3)	C16—C21	1.392 (3)
C1—C2	1.383 (3)	C17—C18	1.377 (3)
C1—H1	0.9300	C17—H17	0.9300
C2—C3	1.378 (3)	C18—C19	1.365 (3)
C2—H2	0.9300	C18—H18	0.9300
C28—H29A	0.9600	C19—C20	1.391 (3)
C28—H29B	0.9600	C19—H19	0.9300
C28—H29C	0.9600	C20—C21	1.388 (3)
C4—C5	1.369 (3)	C20—H20	0.9300
C4—C3	1.381 (3)	C22—C23	1.521 (3)
C4—H4	0.9300	C23—H23A	0.9700
C5—C6	1.378 (3)	C23—H23B	0.9700
C5—H5	0.9300	C24—C25	1.486 (3)
C6—C7	1.479 (3)	C25—C26	1.296 (4)
C7—C8	1.303 (3)	C25—H25	0.9300
C7—H7	0.9300	C26—C27	1.477 (3)
C8—C9	1.487 (3)	C26—H26	0.9300
C8—H8	0.9300
C16—S1—C9	91.38 (9)	C14—C13—H13	120.3
C3—O1—C28	117.6 (2)	C12—C13—H13	120.3
C22—N1—C21	122.52 (15)	C13—C14—C15	121.2 (3)
C22—N1—C9	124.73 (15)	C13—C14—H14	119.4
C21—N1—C9	112.17 (14)	C15—C14—H14	119.4
C24—N2—C27	110.08 (19)	C14—C15—C10	119.9 (3)
C24—N2—C23	123.37 (18)	C14—C15—H15	120.0
C27—N2—C23	124.61 (19)	C10—C15—H15	120.0
C6—C1—C2	121.9 (2)	C17—C16—C21	121.73 (19)
C6—C1—H1	119.1	C17—C16—S1	125.93 (16)
C2—C1—H1	119.1	C21—C16—S1	112.29 (14)
C3—C2—C1	119.6 (2)	C18—C17—C16	118.9 (2)
C3—C2—H2	120.2	C18—C17—H17	120.6
C1—C2—H2	120.2	C16—C17—H17	120.6
O1—C28—H29A	109.5	C19—C18—C17	119.9 (2)
O1—C28—H29B	109.5	C19—C18—H18	120.0
H29A—C28—H29B	109.5	C17—C18—H18	120.0
O1—C28—H29C	109.5	C18—C19—C20	121.9 (2)
H29A—C28—H29C	109.5	C18—C19—H19	119.0
H29B—C28—H29C	109.5	C20—C19—H19	119.0
C5—C4—C3	120.3 (2)	C21—C20—C19	118.6 (2)
C5—C4—H4	119.9	C21—C20—H20	120.7
C3—C4—H4	119.9	C19—C20—H20	120.7
C4—C5—C6	121.6 (2)	C20—C21—C16	118.91 (18)
C4—C5—H5	119.2	C20—C21—N1	127.85 (17)
C6—C5—H5	119.2	C16—C21—N1	113.24 (16)
C1—C6—C5	117.60 (19)	O2—C22—N1	121.41 (18)
C1—C6—C7	120.37 (18)	O2—C22—C23	119.47 (17)
C5—C6—C7	122.01 (19)	N1—C22—C23	119.11 (16)
C8—C7—C6	124.59 (19)	N2—C23—C22	109.80 (17)
C8—C7—H7	117.7	N2—C23—H23A	109.7
C6—C7—H7	117.7	C22—C23—H23A	109.7
C7—C8—C9	128.15 (18)	N2—C23—H23B	109.7
C7—C8—H8	115.9	C22—C23—H23B	109.7
C9—C8—H8	115.9	H23A—C23—H23B	108.2
C8—C9—N1	111.70 (15)	O3—C24—N2	125.0 (2)
C8—C9—C10	115.80 (15)	O3—C24—C25	129.5 (2)
N1—C9—C10	114.97 (14)	N2—C24—C25	105.4 (2)
C8—C9—S1	105.24 (13)	C26—C25—C24	109.2 (2)
N1—C9—S1	103.22 (11)	C26—C25—H25	125.4
C10—C9—S1	104.23 (12)	C24—C25—H25	125.4
C11—C10—C15	118.8 (2)	C25—C26—C27	109.1 (2)
C11—C10—C9	121.64 (18)	C25—C26—H26	125.5
C15—C10—C9	119.45 (19)	C27—C26—H26	125.5
C10—C11—C12	120.0 (2)	O4—C27—N2	124.5 (2)
C10—C11—H11	120.0	O4—C27—C26	129.7 (2)
C12—C11—H11	120.0	N2—C27—C26	105.8 (2)
C13—C12—C11	120.8 (3)	O1—C3—C2	124.7 (2)
C13—C12—H12	119.6	O1—C3—C4	116.2 (2)
C11—C12—H12	119.6	C2—C3—C4	119.0 (2)
C14—C13—C12	119.4 (3)
C6—C1—C2—C3	−1.4 (3)	C17—C18—C19—C20	0.5 (3)
C3—C4—C5—C6	0.1 (4)	C18—C19—C20—C21	0.3 (3)
C2—C1—C6—C5	0.7 (3)	C19—C20—C21—C16	−0.9 (3)
C2—C1—C6—C7	179.0 (2)	C19—C20—C21—N1	−179.64 (18)
C4—C5—C6—C1	−0.1 (3)	C17—C16—C21—C20	0.7 (3)
C4—C5—C6—C7	−178.4 (2)	S1—C16—C21—C20	178.20 (14)
C1—C6—C7—C8	150.6 (2)	C17—C16—C21—N1	179.61 (17)
C5—C6—C7—C8	−31.2 (3)	S1—C16—C21—N1	−2.9 (2)
C6—C7—C8—C9	169.52 (18)	C22—N1—C21—C20	−10.3 (3)
C7—C8—C9—N1	−2.1 (3)	C9—N1—C21—C20	161.29 (18)
C7—C8—C9—C10	132.0 (2)	C22—N1—C21—C16	170.83 (17)
C7—C8—C9—S1	−113.5 (2)	C9—N1—C21—C16	−17.5 (2)
C22—N1—C9—C8	86.4 (2)	C21—N1—C22—O2	−11.0 (3)
C21—N1—C9—C8	−85.05 (18)	C9—N1—C22—O2	178.48 (19)
C22—N1—C9—C10	−48.2 (2)	C21—N1—C22—C23	168.87 (17)
C21—N1—C9—C10	140.37 (15)	C9—N1—C22—C23	−1.7 (3)
C22—N1—C9—S1	−161.04 (15)	C24—N2—C23—C22	−79.4 (3)
C21—N1—C9—S1	27.54 (16)	C27—N2—C23—C22	83.2 (2)
C16—S1—C9—C8	92.84 (14)	O2—C22—C23—N2	4.8 (3)
C16—S1—C9—N1	−24.40 (13)	N1—C22—C23—N2	−175.05 (17)
C16—S1—C9—C10	−144.85 (13)	C27—N2—C24—O3	−173.2 (3)
C8—C9—C10—C11	4.8 (2)	C23—N2—C24—O3	−8.5 (4)
N1—C9—C10—C11	137.50 (18)	C27—N2—C24—C25	5.9 (3)
S1—C9—C10—C11	−110.27 (17)	C23—N2—C24—C25	170.7 (2)
C8—C9—C10—C15	−179.65 (17)	O3—C24—C25—C26	175.4 (3)
N1—C9—C10—C15	−47.0 (2)	N2—C24—C25—C26	−3.7 (3)
S1—C9—C10—C15	65.27 (18)	C24—C25—C26—C27	0.2 (3)
C15—C10—C11—C12	−0.2 (3)	C24—N2—C27—O4	175.8 (2)
C9—C10—C11—C12	175.32 (18)	C23—N2—C27—O4	11.2 (4)
C10—C11—C12—C13	0.9 (4)	C24—N2—C27—C26	−5.8 (2)
C11—C12—C13—C14	0.1 (4)	C23—N2—C27—C26	−170.36 (19)
C12—C13—C14—C15	−1.7 (4)	C25—C26—C27—O4	−178.3 (3)
C13—C14—C15—C10	2.3 (4)	C25—C26—C27—N2	3.4 (3)
C11—C10—C15—C14	−1.3 (3)	C28—O1—C3—C2	−2.4 (4)
C9—C10—C15—C14	−176.97 (19)	C28—O1—C3—C4	177.8 (3)
C9—S1—C16—C17	−165.92 (18)	C1—C2—C3—O1	−178.5 (2)
C9—S1—C16—C21	16.67 (15)	C1—C2—C3—C4	1.4 (4)
C21—C16—C17—C18	0.1 (3)	C5—C4—C3—O1	179.1 (2)
S1—C16—C17—C18	−177.03 (16)	C5—C4—C3—C2	−0.7 (4)
C16—C17—C18—C19	−0.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···N1	0.93	2.53	2.867 (3)	102
C20—H20···O2	0.93	2.26	2.789 (3)	116
C8—H8···S1^i	0.93	2.83	3.734 (2)	165
C18—H18···O2^ii	0.93	2.53	3.243 (3)	134

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1/2, y+1/2, −z+1/2.