7-Methyl-5-[(4-methyl­benzene)­sulfon­yl]-2H,5H-[1,3]dioxolo[4,5-f]indole: crystal structure and Hirshfeld analysis

The mol­ecule in the title compound has the shape of the letter L. In the crystal, weak 4-tolyl-C—H...π(C₆-ring of indole) and S—O...π(1,3-dioxole) contacts link the mol­ecules into a supra­molecular layer in the ab plane.

Key indicators

• Single-crystal X-ray study
• T = 290 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.125
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C13 Check
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........         G2 Check

Alert level G
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O1             105.7 Degree
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O2             106.1 Degree
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          9 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SIR2014 (Burla et al., 2015); program(s) used to refine structure: SHELXL2014/6 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: MarvinSketch (ChemAxon, 2010) and publCIF (Westrip, 2010).

7-Methyl-5-[(4-methylbenzene)sulfonyl]-2H,5H-[1,3]dioxolo[4,5-f]indole

Crystal data

C17H15NO4S	F(000) = 1376
Mr = 329.36	Dx = 1.407 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.2673 (13) Å	Cell parameters from 9928 reflections
b = 12.5337 (9) Å	θ = 2.2–26.4°
c = 17.6096 (15) Å	µ = 0.23 mm^−1
β = 112.628 (3)°	T = 290 K
V = 3110.3 (4) Å^3	Irregular, colourless
Z = 8	0.35 × 0.28 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer	2784 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.028
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	θmax = 26.4°, θmin = 2.2°
Tmin = 0.709, Tmax = 0.745	h = −19→19
27617 measured reflections	k = −15→15
3198 independent reflections	l = −22→21

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.125	w = 1/[σ^2(Fo^2) + (0.0609P)^2 + 2.5262P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
3198 reflections	Δρmax = 0.26 e Å^−3
210 parameters	Δρmin = −0.27 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.63451 (17)	−0.0477 (2)	0.44548 (14)	0.0694 (7)
H1B	0.5872	−0.0417	0.4695	0.083*
H1A	0.6615	−0.1188	0.4565	0.083*
C2	0.71138 (13)	0.08717 (16)	0.41601 (11)	0.0460 (4)
C3	0.77317 (13)	0.16699 (16)	0.41880 (11)	0.0471 (4)
H3	0.8199	0.1899	0.4679	0.057*
C4	0.76150 (11)	0.21227 (14)	0.34255 (11)	0.0398 (4)
C5	0.81363 (13)	0.29544 (15)	0.32141 (12)	0.0474 (4)
C6	0.77434 (14)	0.30697 (15)	0.23940 (13)	0.0511 (5)
H6	0.7939	0.3563	0.2097	0.061*
C7	0.68969 (11)	0.17599 (13)	0.26958 (10)	0.0363 (4)
C8	0.62689 (12)	0.09373 (14)	0.26740 (11)	0.0399 (4)
H8	0.5796	0.0698	0.2190	0.048*
C9	0.64139 (12)	0.05175 (14)	0.34288 (11)	0.0414 (4)
C10	0.54356 (13)	0.35424 (15)	0.12094 (11)	0.0450 (4)
C11	0.46506 (13)	0.33127 (17)	0.13887 (12)	0.0513 (5)
H11	0.4494	0.2610	0.1450	0.062*
C12	0.41023 (14)	0.41411 (19)	0.14760 (13)	0.0585 (5)
H12	0.3576	0.3989	0.1600	0.070*
C13	0.43162 (16)	0.51894 (19)	0.13835 (14)	0.0603 (5)
C14	0.51076 (19)	0.53963 (19)	0.12083 (19)	0.0789 (8)
H14	0.5265	0.6100	0.1149	0.095*
C15	0.56675 (18)	0.45869 (18)	0.11193 (18)	0.0695 (7)
H15	0.6197	0.4741	0.1000	0.083*
C16	0.89722 (17)	0.3540 (2)	0.38141 (17)	0.0742 (7)
H16A	0.9423	0.3037	0.4161	0.111*
H16B	0.8764	0.4002	0.4146	0.111*
H16C	0.9265	0.3958	0.3519	0.111*
C17	0.3709 (2)	0.6088 (2)	0.1472 (2)	0.0907 (9)
H17A	0.4101	0.6595	0.1865	0.136*
H17B	0.3241	0.5809	0.1658	0.136*
H17C	0.3400	0.6432	0.0949	0.136*
N	0.69912 (11)	0.23364 (12)	0.20445 (10)	0.0447 (4)
O1	0.59147 (10)	−0.03034 (12)	0.35900 (9)	0.0605 (4)
O2	0.70666 (11)	0.02948 (14)	0.48058 (9)	0.0708 (5)
O3	0.56284 (12)	0.15436 (12)	0.09072 (9)	0.0636 (4)
O4	0.66542 (13)	0.28779 (14)	0.06197 (10)	0.0718 (5)
S	0.61611 (4)	0.25106 (4)	0.11113 (3)	0.04973 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0734 (14)	0.0767 (15)	0.0543 (13)	−0.0216 (12)	0.0204 (11)	0.0117 (11)
C2	0.0420 (9)	0.0550 (11)	0.0375 (9)	−0.0013 (8)	0.0116 (7)	0.0063 (8)
C3	0.0406 (9)	0.0561 (11)	0.0371 (9)	−0.0072 (8)	0.0067 (7)	−0.0005 (8)
C4	0.0341 (8)	0.0407 (9)	0.0423 (9)	−0.0017 (7)	0.0121 (7)	−0.0019 (7)
C5	0.0416 (9)	0.0446 (10)	0.0557 (11)	−0.0046 (8)	0.0184 (8)	0.0015 (8)
C6	0.0528 (11)	0.0455 (10)	0.0605 (12)	−0.0022 (8)	0.0281 (9)	0.0077 (9)
C7	0.0373 (8)	0.0359 (8)	0.0357 (8)	0.0060 (6)	0.0140 (6)	0.0007 (7)
C8	0.0372 (8)	0.0404 (9)	0.0374 (9)	−0.0008 (7)	0.0092 (7)	−0.0037 (7)
C9	0.0365 (8)	0.0414 (9)	0.0447 (10)	−0.0024 (7)	0.0138 (7)	0.0015 (7)
C10	0.0489 (10)	0.0457 (10)	0.0380 (9)	0.0053 (8)	0.0139 (7)	0.0037 (7)
C11	0.0478 (10)	0.0528 (11)	0.0490 (11)	−0.0034 (8)	0.0141 (8)	0.0027 (9)
C12	0.0447 (10)	0.0735 (14)	0.0561 (12)	0.0056 (10)	0.0179 (9)	0.0034 (10)
C13	0.0582 (12)	0.0620 (13)	0.0538 (12)	0.0172 (10)	0.0141 (10)	0.0006 (10)
C14	0.0844 (17)	0.0455 (12)	0.114 (2)	0.0059 (11)	0.0467 (16)	0.0118 (13)
C15	0.0691 (14)	0.0508 (12)	0.104 (2)	0.0064 (10)	0.0505 (14)	0.0160 (12)
C16	0.0631 (13)	0.0690 (15)	0.0804 (17)	−0.0278 (12)	0.0166 (12)	−0.0014 (12)
C17	0.0891 (19)	0.0856 (19)	0.091 (2)	0.0387 (16)	0.0270 (16)	−0.0044 (16)
N	0.0482 (8)	0.0456 (8)	0.0419 (8)	0.0030 (7)	0.0191 (7)	0.0048 (6)
O1	0.0558 (8)	0.0645 (9)	0.0548 (9)	−0.0203 (7)	0.0143 (7)	0.0108 (7)
O2	0.0675 (9)	0.0912 (12)	0.0436 (8)	−0.0247 (9)	0.0102 (7)	0.0182 (8)
O3	0.0841 (10)	0.0512 (8)	0.0418 (8)	0.0043 (7)	0.0092 (7)	−0.0097 (6)
O4	0.0925 (12)	0.0847 (11)	0.0534 (9)	0.0253 (10)	0.0450 (9)	0.0168 (8)
S	0.0639 (3)	0.0513 (3)	0.0347 (3)	0.0115 (2)	0.0198 (2)	0.00229 (18)

Geometric parameters (Å, º)

C1—O2	1.417 (3)	C10—C11	1.382 (3)
C1—O1	1.424 (3)	C10—S	1.7539 (19)
C1—H1B	0.9700	C11—C12	1.379 (3)
C1—H1A	0.9700	C11—H11	0.9300
C2—C3	1.363 (3)	C12—C13	1.379 (3)
C2—O2	1.373 (2)	C12—H12	0.9300
C2—C9	1.392 (3)	C13—C14	1.382 (3)
C3—C4	1.404 (3)	C13—C17	1.503 (3)
C3—H3	0.9300	C14—C15	1.374 (3)
C4—C7	1.406 (2)	C14—H14	0.9300
C4—C5	1.445 (3)	C15—H15	0.9300
C5—C6	1.341 (3)	C16—H16A	0.9600
C5—C16	1.499 (3)	C16—H16B	0.9600
C6—N	1.414 (2)	C16—H16C	0.9600
C6—H6	0.9300	C17—H17A	0.9600
C7—C8	1.398 (2)	C17—H17B	0.9600
C7—N	1.409 (2)	C17—H17C	0.9600
C8—C9	1.366 (2)	N—S	1.6589 (16)
C8—H8	0.9300	O3—S	1.4264 (16)
C9—O1	1.374 (2)	O4—S	1.4245 (16)
C10—C15	1.381 (3)
O2—C1—O1	108.90 (17)	C13—C12—C11	121.5 (2)
O2—C1—H1B	109.9	C13—C12—H12	119.2
O1—C1—H1B	109.9	C11—C12—H12	119.2
O2—C1—H1A	109.9	C12—C13—C14	118.2 (2)
O1—C1—H1A	109.9	C12—C13—C17	121.2 (2)
H1B—C1—H1A	108.3	C14—C13—C17	120.6 (2)
C3—C2—O2	127.80 (17)	C15—C14—C13	121.5 (2)
C3—C2—C9	122.80 (17)	C15—C14—H14	119.2
O2—C2—C9	109.39 (16)	C13—C14—H14	119.2
C2—C3—C4	115.51 (16)	C14—C15—C10	119.2 (2)
C2—C3—H3	122.2	C14—C15—H15	120.4
C4—C3—H3	122.2	C10—C15—H15	120.4
C3—C4—C7	120.70 (16)	C5—C16—H16A	109.5
C3—C4—C5	131.16 (16)	C5—C16—H16B	109.5
C7—C4—C5	108.13 (16)	H16A—C16—H16B	109.5
C6—C5—C4	107.02 (16)	C5—C16—H16C	109.5
C6—C5—C16	127.80 (19)	H16A—C16—H16C	109.5
C4—C5—C16	125.17 (19)	H16B—C16—H16C	109.5
C5—C6—N	110.52 (17)	C13—C17—H17A	109.5
C5—C6—H6	124.7	C13—C17—H17B	109.5
N—C6—H6	124.7	H17A—C17—H17B	109.5
C8—C7—C4	123.30 (16)	C13—C17—H17C	109.5
C8—C7—N	129.75 (15)	H17A—C17—H17C	109.5
C4—C7—N	106.87 (15)	H17B—C17—H17C	109.5
C9—C8—C7	113.86 (15)	C7—N—C6	107.42 (15)
C9—C8—H8	123.1	C7—N—S	126.55 (13)
C7—C8—H8	123.1	C6—N—S	121.92 (13)
C8—C9—O1	126.47 (16)	C9—O1—C1	105.71 (15)
C8—C9—C2	123.82 (16)	C2—O2—C1	106.13 (16)
O1—C9—C2	109.70 (16)	O4—S—O3	120.32 (10)
C15—C10—C11	120.45 (19)	O4—S—N	105.29 (10)
C15—C10—S	119.21 (16)	O3—S—N	106.38 (8)
C11—C10—S	120.33 (15)	O4—S—C10	108.84 (9)
C12—C11—C10	119.1 (2)	O3—S—C10	109.32 (10)
C12—C11—H11	120.5	N—S—C10	105.67 (8)
C10—C11—H11	120.5
O2—C2—C3—C4	−179.98 (19)	C17—C13—C14—C15	−179.5 (3)
C9—C2—C3—C4	0.3 (3)	C13—C14—C15—C10	−0.2 (4)
C2—C3—C4—C7	0.4 (3)	C11—C10—C15—C14	−0.1 (4)
C2—C3—C4—C5	−178.72 (19)	S—C10—C15—C14	−179.0 (2)
C3—C4—C5—C6	178.8 (2)	C8—C7—N—C6	−178.99 (17)
C7—C4—C5—C6	−0.3 (2)	C4—C7—N—C6	−2.23 (18)
C3—C4—C5—C16	0.3 (3)	C8—C7—N—S	23.7 (3)
C7—C4—C5—C16	−178.9 (2)	C4—C7—N—S	−159.50 (13)
C4—C5—C6—N	−1.1 (2)	C5—C6—N—C7	2.1 (2)
C16—C5—C6—N	177.4 (2)	C5—C6—N—S	160.66 (14)
C3—C4—C7—C8	−0.6 (3)	C8—C9—O1—C1	178.0 (2)
C5—C4—C7—C8	178.63 (16)	C2—C9—O1—C1	−1.6 (2)
C3—C4—C7—N	−177.66 (16)	O2—C1—O1—C9	3.5 (3)
C5—C4—C7—N	1.60 (19)	C3—C2—O2—C1	−176.7 (2)
C4—C7—C8—C9	0.2 (2)	C9—C2—O2—C1	3.0 (2)
N—C7—C8—C9	176.48 (16)	O1—C1—O2—C2	−4.0 (3)
C7—C8—C9—O1	−179.05 (17)	C7—N—S—O4	−164.49 (15)
C7—C8—C9—C2	0.5 (3)	C6—N—S—O4	41.24 (17)
C3—C2—C9—C8	−0.8 (3)	C7—N—S—O3	−35.75 (17)
O2—C2—C9—C8	179.44 (18)	C6—N—S—O3	169.99 (15)
C3—C2—C9—O1	178.81 (18)	C7—N—S—C10	80.39 (16)
O2—C2—C9—O1	−0.9 (2)	C6—N—S—C10	−73.87 (16)
C15—C10—C11—C12	0.0 (3)	C15—C10—S—O4	−24.4 (2)
S—C10—C11—C12	178.91 (15)	C11—C10—S—O4	156.74 (16)
C10—C11—C12—C13	0.4 (3)	C15—C10—S—O3	−157.60 (19)
C11—C12—C13—C14	−0.7 (4)	C11—C10—S—O3	23.51 (18)
C11—C12—C13—C17	179.4 (2)	C15—C10—S—N	88.3 (2)
C12—C13—C14—C15	0.6 (4)	C11—C10—S—N	−90.61 (17)

Hydrogen-bond geometry (Å, º)

Cg1 and Cg2 are the centroids of the (O1,O2,C1,C2,C9) and (C2–C4,C7–C9) rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cg2^i	0.93	2.88	3.662 (2)	142
S—O3···Cg1^i	1.42 (1)	3.77 (1)	4.9921 (12)	144 (1)
S—O4···Cg1^ii	1.43 (1)	3.86 (1)	4.9243 (12)	132 (1)

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