3-Bromo­methyl-1-phenyl­sulfonyl-1H-indole-2-carbonitrile

In the title mol­ecule, C₁₆H₁₁BrN₂O₂S, the phenyl ring and mean plane of the indole ring system make a dihedral angle of 82.9 (1)°. Inter­molecular C—H...O hydrogen bonds link the mol­ecules into linear chains extended along the a axis. The crystal packing is further stabilized by van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.044
• wR factor = 0.120
• Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low ....       0.90

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.55
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C2     -   C16    ...       1.42 Ang.

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

   3 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

3-Bromomethyl-1-phenylsulfonyl-1H-indole-2-carbonitrile

Crystal data

C16H11BrN2O2S	Z = 2
Mr = 375.24	F(000) = 376
Triclinic, P1	Dx = 1.608 Mg m^−3
a = 8.2689 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9841 (15) Å	Cell parameters from 6233 reflections
c = 11.805 (2) Å	θ = 1.5–27.4°
α = 77.722 (3)°	µ = 2.80 mm^−1
β = 86.703 (3)°	T = 293 K
γ = 64.795 (3)°	Block, yellow
V = 774.8 (2) Å^3	0.29 × 0.21 × 0.16 mm

Data collection

Bruker SMART APEX area-detector diffractometer	3157 independent reflections
Radiation source: fine-focus sealed tube	2493 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
ω scans	θmax = 27.4°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
Tmin = 0.499, Tmax = 0.639	k = −11→11
6233 measured reflections	l = −15→14

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0728P)^2 + 0.1871P] where P = (Fo^2 + 2Fc^2)/3
3157 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.67 e Å^−3
0 restraints	Δρmin = −0.19 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
Br1	0.46514 (5)	−0.39437 (5)	0.32151 (3)	0.07063 (18)
S1	−0.03439 (10)	0.34730 (10)	0.21489 (8)	0.0579 (2)
O1	−0.0758 (4)	0.4792 (3)	0.2753 (3)	0.0807 (8)
O2	−0.1675 (3)	0.3389 (4)	0.1494 (3)	0.0848 (9)
N1	0.0376 (3)	0.1694 (3)	0.3189 (2)	0.0521 (6)
C2	0.0683 (4)	0.0112 (4)	0.2983 (3)	0.0510 (7)
C3	0.1785 (4)	−0.1126 (4)	0.3828 (3)	0.0505 (7)
C4	0.2259 (4)	−0.0345 (4)	0.4611 (3)	0.0488 (7)
C5	0.1396 (4)	0.1397 (4)	0.4193 (3)	0.0472 (7)
C6	0.1575 (5)	0.2520 (5)	0.4777 (3)	0.0613 (9)
H6	0.1012	0.3677	0.4499	0.074*
C7	0.2625 (5)	0.1834 (5)	0.5786 (3)	0.0666 (10)
H7	0.2763	0.2552	0.6195	0.080*
C8	0.3475 (5)	0.0127 (6)	0.6209 (3)	0.0683 (10)
H8	0.4170	−0.0280	0.6893	0.082*
C9	0.3310 (4)	−0.0989 (5)	0.5632 (3)	0.0593 (8)
H9	0.3888	−0.2143	0.5918	0.071*
C10	0.1536 (4)	0.3225 (4)	0.1322 (3)	0.0471 (7)
C11	0.2769 (5)	0.3736 (5)	0.1644 (3)	0.0644 (9)
H11	0.2560	0.4281	0.2260	0.077*
C12	0.4302 (5)	0.3426 (6)	0.1038 (4)	0.0769 (11)
H12	0.5149	0.3752	0.1250	0.092*
C13	0.4595 (6)	0.2645 (6)	0.0129 (4)	0.0804 (12)
H13	0.5652	0.2418	−0.0266	0.097*
C14	0.3337 (6)	0.2189 (5)	−0.0208 (3)	0.0774 (11)
H14	0.3531	0.1689	−0.0847	0.093*
C15	0.1802 (5)	0.2464 (4)	0.0389 (3)	0.0616 (8)
H15	0.0956	0.2143	0.0168	0.074*
C16	−0.0129 (6)	−0.0121 (5)	0.2043 (3)	0.0686 (10)
N17	−0.0686 (7)	−0.0477 (6)	0.1346 (3)	0.1075 (14)
C18	0.2333 (5)	−0.2945 (4)	0.3918 (3)	0.0604 (8)
H18A	0.1441	−0.3108	0.3525	0.073*
H18B	0.2417	−0.3498	0.4727	0.073*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0615 (3)	0.0650 (3)	0.0908 (3)	−0.02375 (19)	0.02008 (19)	−0.0386 (2)
S1	0.0399 (4)	0.0499 (5)	0.0770 (6)	−0.0141 (3)	0.0017 (4)	−0.0098 (4)
O1	0.0724 (17)	0.0504 (14)	0.103 (2)	−0.0082 (12)	0.0171 (15)	−0.0236 (14)
O2	0.0439 (14)	0.093 (2)	0.110 (2)	−0.0285 (14)	−0.0186 (13)	0.0003 (17)
N1	0.0502 (14)	0.0501 (15)	0.0620 (15)	−0.0261 (12)	0.0082 (12)	−0.0153 (12)
C2	0.0520 (17)	0.0571 (19)	0.0577 (17)	−0.0328 (15)	0.0140 (14)	−0.0222 (15)
C3	0.0466 (16)	0.0501 (17)	0.0621 (18)	−0.0242 (14)	0.0186 (14)	−0.0226 (15)
C4	0.0424 (15)	0.0540 (18)	0.0570 (17)	−0.0242 (14)	0.0154 (13)	−0.0213 (14)
C5	0.0393 (15)	0.0523 (17)	0.0569 (17)	−0.0229 (13)	0.0157 (13)	−0.0215 (14)
C6	0.0547 (19)	0.060 (2)	0.083 (2)	−0.0309 (16)	0.0225 (17)	−0.0352 (18)
C7	0.064 (2)	0.085 (3)	0.075 (2)	−0.043 (2)	0.0140 (18)	−0.043 (2)
C8	0.058 (2)	0.098 (3)	0.060 (2)	−0.039 (2)	0.0064 (16)	−0.028 (2)
C9	0.0495 (18)	0.064 (2)	0.063 (2)	−0.0223 (16)	0.0095 (15)	−0.0143 (16)
C10	0.0427 (15)	0.0423 (15)	0.0538 (17)	−0.0181 (13)	−0.0044 (12)	−0.0032 (13)
C11	0.066 (2)	0.080 (2)	0.065 (2)	−0.046 (2)	0.0013 (17)	−0.0180 (18)
C12	0.063 (2)	0.103 (3)	0.077 (3)	−0.055 (2)	0.0003 (19)	−0.003 (2)
C13	0.066 (2)	0.086 (3)	0.076 (3)	−0.029 (2)	0.019 (2)	−0.002 (2)
C14	0.101 (3)	0.071 (2)	0.063 (2)	−0.039 (2)	0.020 (2)	−0.0191 (19)
C15	0.073 (2)	0.058 (2)	0.0601 (19)	−0.0350 (18)	−0.0023 (17)	−0.0092 (16)
C16	0.088 (3)	0.081 (3)	0.058 (2)	−0.054 (2)	0.0129 (18)	−0.0212 (18)
N17	0.154 (4)	0.141 (4)	0.074 (2)	−0.099 (4)	0.009 (2)	−0.040 (2)
C18	0.061 (2)	0.0510 (18)	0.078 (2)	−0.0289 (16)	0.0209 (17)	−0.0246 (16)

Geometric parameters (Å, º)

Br1—C18	1.959 (3)	C8—C9	1.380 (5)
S1—O2	1.417 (3)	C8—H8	0.9300
S1—O1	1.420 (3)	C9—H9	0.9300
S1—N1	1.690 (3)	C10—C15	1.376 (5)
S1—C10	1.744 (3)	C10—C11	1.382 (4)
N1—C2	1.405 (4)	C11—C12	1.370 (5)
N1—C5	1.406 (4)	C11—H11	0.9300
C2—C3	1.352 (5)	C12—C13	1.359 (6)
C2—C16	1.425 (5)	C12—H12	0.9300
C3—C4	1.433 (4)	C13—C14	1.374 (6)
C3—C18	1.480 (4)	C13—H13	0.9300
C4—C9	1.392 (5)	C14—C15	1.368 (6)
C4—C5	1.401 (4)	C14—H14	0.9300
C5—C6	1.396 (4)	C15—H15	0.9300
C6—C7	1.380 (5)	C16—N17	1.128 (5)
C6—H6	0.9300	C18—H18A	0.9700
C7—C8	1.375 (6)	C18—H18B	0.9700
C7—H7	0.9300
O2—S1—O1	121.29 (19)	C9—C8—H8	119.6
O2—S1—N1	104.86 (16)	C8—C9—C4	118.4 (3)
O1—S1—N1	105.02 (16)	C8—C9—H9	120.8
O2—S1—C10	109.85 (17)	C4—C9—H9	120.8
O1—S1—C10	110.64 (16)	C15—C10—C11	121.2 (3)
N1—S1—C10	103.37 (13)	C15—C10—S1	119.4 (2)
C2—N1—C5	106.8 (3)	C11—C10—S1	119.3 (3)
C2—N1—S1	123.6 (2)	C12—C11—C10	118.8 (3)
C5—N1—S1	125.2 (2)	C12—C11—H11	120.6
C3—C2—N1	110.2 (3)	C10—C11—H11	120.6
C3—C2—C16	125.8 (3)	C13—C12—C11	120.5 (4)
N1—C2—C16	123.9 (3)	C13—C12—H12	119.8
C2—C3—C4	107.6 (3)	C11—C12—H12	119.8
C2—C3—C18	125.0 (3)	C12—C13—C14	120.3 (4)
C4—C3—C18	127.4 (3)	C12—C13—H13	119.9
C9—C4—C5	120.1 (3)	C14—C13—H13	119.9
C9—C4—C3	132.7 (3)	C15—C14—C13	120.5 (4)
C5—C4—C3	107.2 (3)	C15—C14—H14	119.7
C6—C5—C4	121.3 (3)	C13—C14—H14	119.7
C6—C5—N1	130.6 (3)	C14—C15—C10	118.6 (3)
C4—C5—N1	108.1 (3)	C14—C15—H15	120.7
C7—C6—C5	116.9 (3)	C10—C15—H15	120.7
C7—C6—H6	121.6	N17—C16—C2	172.9 (5)
C5—C6—H6	121.6	C3—C18—Br1	110.1 (2)
C8—C7—C6	122.5 (3)	C3—C18—H18A	109.6
C8—C7—H7	118.8	Br1—C18—H18A	109.6
C6—C7—H7	118.8	C3—C18—H18B	109.6
C7—C8—C9	120.9 (3)	Br1—C18—H18B	109.6
C7—C8—H8	119.6	H18A—C18—H18B	108.1
O2—S1—N1—C2	41.7 (3)	S1—N1—C5—C4	−159.0 (2)
O1—S1—N1—C2	170.6 (2)	C4—C5—C6—C7	−0.5 (5)
C10—S1—N1—C2	−73.4 (3)	N1—C5—C6—C7	176.9 (3)
O2—S1—N1—C5	−165.0 (3)	C5—C6—C7—C8	0.3 (5)
O1—S1—N1—C5	−36.1 (3)	C6—C7—C8—C9	0.0 (6)
C10—S1—N1—C5	79.9 (3)	C7—C8—C9—C4	−0.1 (5)
C5—N1—C2—C3	2.0 (3)	C5—C4—C9—C8	−0.1 (4)
S1—N1—C2—C3	159.5 (2)	C3—C4—C9—C8	−178.6 (3)
C5—N1—C2—C16	179.4 (3)	O2—S1—C10—C15	−21.1 (3)
S1—N1—C2—C16	−23.2 (4)	O1—S1—C10—C15	−157.6 (3)
N1—C2—C3—C4	−1.2 (3)	N1—S1—C10—C15	90.4 (3)
C16—C2—C3—C4	−178.5 (3)	O2—S1—C10—C11	161.5 (3)
N1—C2—C3—C18	177.2 (3)	O1—S1—C10—C11	24.9 (3)
C16—C2—C3—C18	−0.1 (5)	N1—S1—C10—C11	−87.1 (3)
C2—C3—C4—C9	178.5 (3)	C15—C10—C11—C12	−2.0 (5)
C18—C3—C4—C9	0.1 (5)	S1—C10—C11—C12	175.4 (3)
C2—C3—C4—C5	−0.1 (3)	C10—C11—C12—C13	0.7 (6)
C18—C3—C4—C5	−178.5 (3)	C11—C12—C13—C14	1.4 (7)
C9—C4—C5—C6	0.4 (4)	C12—C13—C14—C15	−2.2 (7)
C3—C4—C5—C6	179.3 (3)	C13—C14—C15—C10	0.8 (6)
C9—C4—C5—N1	−177.5 (3)	C11—C10—C15—C14	1.3 (5)
C3—C4—C5—N1	1.3 (3)	S1—C10—C15—C14	−176.1 (3)
C2—N1—C5—C6	−179.7 (3)	C2—C3—C18—Br1	95.9 (3)
S1—N1—C5—C6	23.3 (4)	C4—C3—C18—Br1	−85.9 (3)
C2—N1—C5—C4	−2.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.93	2.37	2.949 (5)	120
C12—H12···O2^i	0.93	2.53	3.385 (6)	153

Symmetry code: (i) x+1, y, z.