1'-Methyl-4'-tolyl-1H-indole-3-spiro-2'-pyrrolidine-3'-spiro-5''-(thia­zolo­[3,2-b][1,2,4]­triazole)-2,6''(3H,5''H)-dione

The title compound, C₂₂H₁₉N₅O₂S, was synthesized by an intermolecular [3 + 2]-cyclo­addition of the azomethine yl­ide derived from isatin and sarcosine by a de­carboxyl­ative route and 5-(4-methyl­benzyl­idene)­thia­zolo­[3,2-b][1,2,4]­triazol-6-one. In the mol­ecule, the two spiro junctions link a planar 2-ox­indole ring, a pyrrolidine ring in an envelope conformation and a thia­zolo­[3,2-b][1,2,4]­triazol-6-one system.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.066
• wR factor = 0.156
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.824     0.990
            Tmin' and Tmax expected:      0.959     0.989
            RR' =      0.858
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.86
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.17
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.77 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); 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.

1'-Methyl-4'-tolyl-1H-indole-3-spiro-2'-pyrrolidine-3'-spiro-5''- (thiazolo[3,2-b][1,2,4]triazole)-2,6''(3H,5''H)-dione

Crystal data

C22H19N5O2S	F(000) = 872
Mr = 417.48	Dx = 1.363 Mg m^−3
Monoclinic, P21/c	Melting point = 480–481 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 19.153 (6) Å	Cell parameters from 1005 reflections
b = 6.2858 (19) Å	θ = 2.6–24.4°
c = 16.968 (5) Å	µ = 0.19 mm^−1
β = 95.218 (5)°	T = 293 K
V = 2034.3 (11) Å^3	Block, colorless
Z = 4	0.22 × 0.08 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3582 independent reflections
Radiation source: fine-focus sealed tube	2218 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.064
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −16→22
Tmin = 0.824, Tmax = 0.990	k = −7→4
9314 measured reflections	l = −20→19

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.066	w = 1/[σ^2(Fo^2) + (0.084P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.156	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.75 e Å^−3
3582 reflections	Δρmin = −0.24 e Å^−3
273 parameters

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	0.25837 (5)	0.39822 (15)	0.31535 (6)	0.0433 (3)
O1	0.34057 (13)	−0.1422 (4)	0.38400 (16)	0.0480 (7)
O2	0.17105 (14)	0.4916 (4)	0.45820 (18)	0.0508 (8)
N1	0.36878 (15)	0.1629 (5)	0.32126 (18)	0.0389 (8)
N2	0.43507 (17)	0.1312 (6)	0.2977 (2)	0.0522 (9)
N3	0.38667 (19)	0.4456 (6)	0.2499 (2)	0.0546 (10)
N4	0.23113 (14)	0.0515 (4)	0.50634 (17)	0.0316 (7)
N5	0.27943 (16)	0.5807 (5)	0.51822 (18)	0.0416 (8)
H5	0.2709	0.7103	0.5305	0.050*
C1	0.26123 (17)	0.1603 (5)	0.3803 (2)	0.0311 (8)
C2	0.32639 (18)	0.0324 (6)	0.3633 (2)	0.0343 (9)
C3	0.4420 (2)	0.3024 (8)	0.2562 (3)	0.0589 (12)
H3	0.4826	0.3280	0.2316	0.071*
C4	0.34224 (19)	0.3502 (6)	0.2926 (2)	0.0394 (9)
C5	0.19504 (17)	0.0122 (6)	0.3706 (2)	0.0368 (9)
H5A	0.2123	−0.1321	0.3624	0.044*
C6	0.16745 (18)	0.0141 (6)	0.4527 (2)	0.0386 (9)
H6A	0.1335	0.1272	0.4568	0.046*
H6B	0.1459	−0.1208	0.4640	0.046*
C7	0.26784 (17)	0.2269 (5)	0.4706 (2)	0.0310 (8)
C8	0.2315 (2)	0.4492 (5)	0.4807 (2)	0.0359 (9)
C9	0.34451 (19)	0.4816 (6)	0.5347 (2)	0.0372 (9)
C10	0.4049 (2)	0.5661 (6)	0.5739 (2)	0.0528 (11)
H10	0.4063	0.7053	0.5925	0.063*
C11	0.4629 (2)	0.4348 (7)	0.5842 (3)	0.0550 (12)
H11	0.5048	0.4893	0.6081	0.066*
C12	0.4603 (2)	0.2274 (7)	0.5604 (2)	0.0509 (11)
H12	0.5000	0.1422	0.5690	0.061*
C13	0.39885 (19)	0.1425 (6)	0.5232 (2)	0.0394 (9)
H13	0.3968	0.0004	0.5080	0.047*
C14	0.34094 (18)	0.2725 (5)	0.5094 (2)	0.0320 (8)
C15	0.14260 (18)	0.0602 (5)	0.3008 (2)	0.0364 (9)
C16	0.1402 (2)	−0.0693 (7)	0.2338 (3)	0.0526 (11)
H16	0.1683	−0.1901	0.2344	0.063*
C17	0.0969 (2)	−0.0214 (8)	0.1666 (3)	0.0593 (12)
H17	0.0964	−0.1104	0.1228	0.071*
C18	0.0547 (2)	0.1555 (8)	0.1634 (3)	0.0556 (12)
C19	0.0564 (2)	0.2809 (8)	0.2298 (3)	0.0615 (13)
H19	0.0279	0.4008	0.2292	0.074*
C20	0.09934 (19)	0.2340 (6)	0.2977 (3)	0.0512 (11)
H20	0.0988	0.3218	0.3417	0.061*
C21	0.0080 (3)	0.2128 (10)	0.0891 (3)	0.0854 (17)
H21A	−0.0366	0.1432	0.0902	0.128*
H21B	0.0298	0.1672	0.0433	0.128*
H21C	0.0011	0.3640	0.0870	0.128*
C22	0.2183 (2)	0.0854 (6)	0.5891 (2)	0.0502 (11)
H22A	0.2621	0.1069	0.6203	0.075*
H22B	0.1951	−0.0371	0.6084	0.075*
H22C	0.1891	0.2085	0.5931	0.075*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0486 (6)	0.0324 (5)	0.0487 (6)	0.0035 (5)	0.0032 (5)	0.0094 (5)
O1	0.0469 (17)	0.0347 (16)	0.0632 (19)	0.0081 (13)	0.0099 (13)	−0.0022 (13)
O2	0.0420 (17)	0.0333 (15)	0.076 (2)	0.0096 (13)	0.0004 (14)	−0.0040 (14)
N1	0.0360 (19)	0.0418 (19)	0.0401 (19)	0.0000 (15)	0.0107 (14)	−0.0013 (15)
N2	0.043 (2)	0.058 (2)	0.058 (2)	−0.0022 (18)	0.0191 (17)	−0.0108 (19)
N3	0.068 (2)	0.052 (2)	0.046 (2)	−0.021 (2)	0.0153 (18)	0.0000 (17)
N4	0.0344 (17)	0.0262 (15)	0.0348 (18)	−0.0002 (13)	0.0069 (13)	0.0020 (13)
N5	0.055 (2)	0.0204 (15)	0.049 (2)	0.0034 (15)	0.0017 (16)	−0.0064 (14)
C1	0.035 (2)	0.0234 (17)	0.035 (2)	−0.0003 (16)	0.0018 (15)	0.0039 (15)
C2	0.042 (2)	0.027 (2)	0.034 (2)	0.0111 (17)	0.0021 (16)	−0.0033 (16)
C3	0.050 (3)	0.072 (3)	0.058 (3)	−0.015 (3)	0.023 (2)	−0.017 (3)
C4	0.046 (2)	0.034 (2)	0.037 (2)	−0.0062 (18)	−0.0012 (18)	−0.0048 (17)
C5	0.035 (2)	0.0235 (18)	0.052 (3)	−0.0007 (16)	0.0027 (18)	−0.0045 (17)
C6	0.032 (2)	0.0283 (19)	0.056 (3)	0.0001 (16)	0.0075 (18)	0.0016 (18)
C7	0.030 (2)	0.0211 (17)	0.042 (2)	0.0033 (15)	0.0042 (16)	0.0007 (15)
C8	0.041 (2)	0.0247 (19)	0.043 (2)	0.0053 (18)	0.0066 (17)	0.0011 (16)
C9	0.043 (2)	0.0295 (19)	0.039 (2)	−0.0019 (18)	0.0015 (17)	0.0047 (17)
C10	0.068 (3)	0.036 (2)	0.051 (3)	−0.013 (2)	−0.013 (2)	−0.0014 (19)
C11	0.052 (3)	0.059 (3)	0.050 (3)	−0.014 (2)	−0.016 (2)	0.004 (2)
C12	0.041 (3)	0.065 (3)	0.045 (3)	0.008 (2)	−0.0055 (19)	0.004 (2)
C13	0.041 (2)	0.035 (2)	0.041 (2)	0.0054 (18)	0.0014 (17)	−0.0007 (17)
C14	0.034 (2)	0.031 (2)	0.031 (2)	−0.0013 (17)	0.0049 (15)	0.0018 (15)
C15	0.031 (2)	0.0282 (19)	0.049 (2)	−0.0016 (16)	−0.0035 (17)	−0.0010 (17)
C16	0.048 (2)	0.045 (2)	0.064 (3)	0.008 (2)	−0.001 (2)	−0.009 (2)
C17	0.058 (3)	0.072 (3)	0.046 (3)	0.006 (3)	−0.005 (2)	−0.013 (2)
C18	0.039 (2)	0.074 (3)	0.054 (3)	−0.006 (2)	0.000 (2)	0.003 (2)
C19	0.043 (3)	0.060 (3)	0.079 (4)	0.014 (2)	−0.005 (2)	0.002 (3)
C20	0.041 (2)	0.047 (3)	0.063 (3)	0.007 (2)	−0.006 (2)	−0.012 (2)
C21	0.068 (3)	0.117 (5)	0.067 (4)	0.009 (3)	−0.018 (3)	0.006 (3)
C22	0.058 (3)	0.045 (2)	0.051 (3)	0.001 (2)	0.017 (2)	0.001 (2)

Geometric parameters (Å, º)

S1—C4	1.713 (4)	C9—C14	1.383 (5)
S1—C1	1.856 (3)	C9—C10	1.385 (5)
O1—C2	1.177 (4)	C10—C11	1.382 (6)
O2—C8	1.215 (4)	C10—H10	0.9300
N1—C4	1.355 (5)	C11—C12	1.365 (6)
N1—N2	1.380 (4)	C11—H11	0.9300
N1—C2	1.395 (5)	C12—C13	1.391 (5)
N2—C3	1.299 (6)	C12—H12	0.9300
N3—C4	1.311 (5)	C13—C14	1.380 (5)
N3—C3	1.387 (5)	C13—H13	0.9300
N4—C22	1.464 (5)	C15—C20	1.369 (5)
N4—C7	1.468 (4)	C15—C16	1.397 (5)
N4—C6	1.473 (4)	C16—C17	1.380 (6)
N5—C8	1.351 (4)	C16—H16	0.9300
N5—C9	1.399 (4)	C17—C18	1.374 (6)
N5—H5	0.8600	C17—H17	0.9300
C1—C2	1.534 (5)	C18—C19	1.373 (6)
C1—C5	1.569 (5)	C18—C21	1.521 (6)
C1—C7	1.582 (5)	C19—C20	1.384 (6)
C3—H3	0.9300	C19—H19	0.9300
C5—C15	1.511 (5)	C20—H20	0.9300
C5—C6	1.534 (5)	C21—H21A	0.9600
C5—H5A	0.9800	C21—H21B	0.9600
C6—H6A	0.9700	C21—H21C	0.9600
C6—H6B	0.9700	C22—H22A	0.9600
C7—C14	1.519 (5)	C22—H22B	0.9600
C7—C8	1.577 (5)	C22—H22C	0.9600
C4—S1—C1	90.81 (17)	C14—C9—C10	121.9 (4)
C4—N1—N2	110.3 (3)	C14—C9—N5	110.0 (3)
C4—N1—C2	118.5 (3)	C10—C9—N5	128.0 (4)
N2—N1—C2	131.1 (3)	C11—C10—C9	117.3 (4)
C3—N2—N1	100.3 (3)	C11—C10—H10	121.4
C4—N3—C3	100.9 (3)	C9—C10—H10	121.4
C22—N4—C7	114.6 (3)	C12—C11—C10	121.7 (4)
C22—N4—C6	114.5 (3)	C12—C11—H11	119.1
C7—N4—C6	105.4 (3)	C10—C11—H11	119.1
C8—N5—C9	112.2 (3)	C11—C12—C13	120.5 (4)
C8—N5—H5	123.9	C11—C12—H12	119.8
C9—N5—H5	123.9	C13—C12—H12	119.8
C2—C1—C5	109.4 (3)	C14—C13—C12	119.0 (4)
C2—C1—C7	109.1 (3)	C14—C13—H13	120.5
C5—C1—C7	104.6 (3)	C12—C13—H13	120.5
C2—C1—S1	106.9 (2)	C13—C14—C9	119.6 (3)
C5—C1—S1	115.8 (2)	C13—C14—C7	131.0 (3)
C7—C1—S1	110.9 (2)	C9—C14—C7	109.4 (3)
O1—C2—N1	124.9 (3)	C20—C15—C16	117.3 (4)
O1—C2—C1	127.0 (3)	C20—C15—C5	123.1 (3)
N1—C2—C1	108.0 (3)	C16—C15—C5	119.5 (3)
N2—C3—N3	117.7 (4)	C17—C16—C15	121.2 (4)
N2—C3—H3	121.1	C17—C16—H16	119.4
N3—C3—H3	121.1	C15—C16—H16	119.4
N3—C4—N1	110.8 (3)	C18—C17—C16	121.1 (4)
N3—C4—S1	135.5 (3)	C18—C17—H17	119.4
N1—C4—S1	113.6 (3)	C16—C17—H17	119.4
C15—C5—C6	116.7 (3)	C19—C18—C17	117.5 (4)
C15—C5—C1	115.9 (3)	C19—C18—C21	120.9 (4)
C6—C5—C1	104.0 (3)	C17—C18—C21	121.6 (4)
C15—C5—H5A	106.5	C18—C19—C20	121.9 (4)
C6—C5—H5A	106.5	C18—C19—H19	119.0
C1—C5—H5A	106.5	C20—C19—H19	119.0
N4—C6—C5	103.2 (3)	C15—C20—C19	120.9 (4)
N4—C6—H6A	111.1	C15—C20—H20	119.5
C5—C6—H6A	111.1	C19—C20—H20	119.5
N4—C6—H6B	111.1	C18—C21—H21A	109.5
C5—C6—H6B	111.1	C18—C21—H21B	109.5
H6A—C6—H6B	109.1	H21A—C21—H21B	109.5
N4—C7—C14	114.9 (3)	C18—C21—H21C	109.5
N4—C7—C8	112.8 (3)	H21A—C21—H21C	109.5
C14—C7—C8	100.6 (3)	H21B—C21—H21C	109.5
N4—C7—C1	101.7 (3)	N4—C22—H22A	109.5
C14—C7—C1	117.3 (3)	N4—C22—H22B	109.5
C8—C7—C1	110.0 (3)	H22A—C22—H22B	109.5
O2—C8—N5	126.9 (3)	N4—C22—H22C	109.5
O2—C8—C7	125.3 (3)	H22A—C22—H22C	109.5
N5—C8—C7	107.8 (3)	H22B—C22—H22C	109.5
C4—N1—N2—C3	−0.6 (4)	S1—C1—C7—C14	−84.3 (3)
C2—N1—N2—C3	175.1 (4)	C2—C1—C7—C8	147.3 (3)
C4—S1—C1—C2	−12.3 (2)	C5—C1—C7—C8	−95.7 (3)
C4—S1—C1—C5	−134.5 (3)	S1—C1—C7—C8	29.8 (3)
C4—S1—C1—C7	106.5 (2)	C9—N5—C8—O2	−179.1 (4)
C4—N1—C2—O1	171.9 (4)	C9—N5—C8—C7	0.9 (4)
N2—N1—C2—O1	−3.5 (6)	N4—C7—C8—O2	−57.1 (5)
C4—N1—C2—C1	−10.8 (4)	C14—C7—C8—O2	180.0 (4)
N2—N1—C2—C1	173.8 (3)	C1—C7—C8—O2	55.6 (5)
C5—C1—C2—O1	−42.0 (5)	N4—C7—C8—N5	122.9 (3)
C7—C1—C2—O1	71.8 (4)	C14—C7—C8—N5	0.0 (4)
S1—C1—C2—O1	−168.2 (3)	C1—C7—C8—N5	−124.4 (3)
C5—C1—C2—N1	140.7 (3)	C8—N5—C9—C14	−1.5 (4)
C7—C1—C2—N1	−105.4 (3)	C8—N5—C9—C10	−178.4 (4)
S1—C1—C2—N1	14.6 (3)	C14—C9—C10—C11	2.4 (6)
N1—N2—C3—N3	0.1 (5)	N5—C9—C10—C11	179.0 (4)
C4—N3—C3—N2	0.4 (5)	C9—C10—C11—C12	−3.0 (6)
C3—N3—C4—N1	−0.8 (4)	C10—C11—C12—C13	1.2 (7)
C3—N3—C4—S1	−176.2 (3)	C11—C12—C13—C14	1.4 (6)
N2—N1—C4—N3	0.9 (4)	C12—C13—C14—C9	−2.0 (5)
C2—N1—C4—N3	−175.4 (3)	C12—C13—C14—C7	179.9 (4)
N2—N1—C4—S1	177.4 (2)	C10—C9—C14—C13	0.1 (6)
C2—N1—C4—S1	1.1 (4)	N5—C9—C14—C13	−177.1 (3)
C1—S1—C4—N3	−177.6 (4)	C10—C9—C14—C7	178.6 (3)
C1—S1—C4—N1	7.1 (3)	N5—C9—C14—C7	1.4 (4)
C2—C1—C5—C15	−111.1 (3)	N4—C7—C14—C13	55.9 (5)
C7—C1—C5—C15	132.2 (3)	C8—C7—C14—C13	177.4 (4)
S1—C1—C5—C15	9.8 (4)	C1—C7—C14—C13	−63.4 (5)
C2—C1—C5—C6	119.4 (3)	N4—C7—C14—C9	−122.3 (3)
C7—C1—C5—C6	2.6 (3)	C8—C7—C14—C9	−0.9 (4)
S1—C1—C5—C6	−119.8 (3)	C1—C7—C14—C9	118.3 (3)
C22—N4—C6—C5	173.2 (3)	C6—C5—C15—C20	50.7 (5)
C7—N4—C6—C5	46.4 (3)	C1—C5—C15—C20	−72.4 (5)
C15—C5—C6—N4	−157.5 (3)	C6—C5—C15—C16	−133.4 (4)
C1—C5—C6—N4	−28.5 (3)	C1—C5—C15—C16	103.5 (4)
C22—N4—C7—C14	61.9 (4)	C20—C15—C16—C17	1.2 (6)
C6—N4—C7—C14	−171.3 (3)	C5—C15—C16—C17	−174.9 (4)
C22—N4—C7—C8	−52.7 (4)	C15—C16—C17—C18	0.0 (7)
C6—N4—C7—C8	74.1 (3)	C16—C17—C18—C19	−0.9 (7)
C22—N4—C7—C1	−170.4 (3)	C16—C17—C18—C21	178.6 (4)
C6—N4—C7—C1	−43.6 (3)	C17—C18—C19—C20	0.6 (7)
C2—C1—C7—N4	−92.9 (3)	C21—C18—C19—C20	−178.9 (4)
C5—C1—C7—N4	24.1 (3)	C16—C15—C20—C19	−1.5 (6)
S1—C1—C7—N4	149.6 (2)	C5—C15—C20—C19	174.5 (4)
C2—C1—C7—C14	33.2 (4)	C18—C19—C20—C15	0.7 (7)
C5—C1—C7—C14	150.2 (3)