(E)-6-(4-Chloro-phen-yl)-4-[(2-cyano-3-phenyl-all-yl)sulfan-yl]-2,2-difluoro-3-phenyl-1,3,2-oxaza-borinin-3-ium-2-uide.

In the title compound, C25H18BClF2N2OS, the characteristic B-N and B-O bond lengths are 1.571 (3) and 1.458 (3) Å, respectively. The phenyl rings form dihedral angles of 83.1 (1) and 64.6 (1)° with the chloro-phenyl ring. In the crystal, weak C-H⋯N, C-H⋯F, C-H⋯π and π-π inter-actions [centroid-centroid distances 3.877 (6) Å between the chloro-phenyl rings of neighbouring mol-ecules] held mol-ecules together, forming ladders along the b axis.

Related literature

For background to thio­acetanilides, see: Peruncheralathan et al. (2005 ▶); Li et al. (2010 ▶); Wu et al. (2009 ▶); Erten-Ela et al. (2008 ▶); Tokoro et al. (2010 ▶); Lu et al. (2002 ▶); Tsuboyama et al. (2003 ▶); Zhang et al. (2006 ▶). For the crystal structures of related compounds, see: Macedo et al. (2008 ▶).

Experimental

Crystal data

C25H18BClF2N2OS

M = 478.73

Monoclinic,

a = 9.6996 (19) Å

b = 16.290 (3) Å

c = 14.168 (3) Å

β = 98.71 (3)°

V = 2212.9 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 173 K

0.43 × 0.29 × 0.09 mm

Data collection

Rigaku MM007HF diffractometer with Saturn724+ CCD

Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku/MSC, 2008 ▶) T min = 0.685, T max = 1.000

15558 measured reflections

5081 independent reflections

4491 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.120

S = 1.18

5081 reflections

298 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrystalClear-SM Expert (Rigaku/MSC, 2008 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813007800/cv5394sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007800/cv5394Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C25H18BClF2N2OS	F(000) = 984
Mr = 478.73	Dx = 1.437 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7694 reflections
a = 9.6996 (19) Å	θ = 1.5–27.5°
b = 16.290 (3) Å	µ = 0.31 mm−1
c = 14.168 (3) Å	T = 173 K
β = 98.71 (3)°	Plate, colourless
V = 2212.9 (8) Å3	0.43 × 0.29 × 0.09 mm
Z = 4

Rigaku MM007HF diffractometer with Saturn724+ CCD	5081 independent reflections
Radiation source: Rotating Anode	4491 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.052
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 2.1°
ω scans at fixed χ = 45°	h = −12→12
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku/MSC, 2008)	k = −20→21
Tmin = 0.685, Tmax = 1.000	l = −18→18
15558 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 1.18	w = 1/[σ2(Fo2) + (0.0312P)2 + 1.2135P] where P = (Fo2 + 2Fc2)/3
5081 reflections	(Δ/σ)max = 0.001
298 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	1.18430 (6)	0.47712 (4)	1.29061 (4)	0.03843 (16)
S1	0.47463 (6)	0.63647 (4)	0.79190 (4)	0.03476 (16)
F1	0.61480 (16)	0.34159 (9)	0.78320 (10)	0.0494 (4)
F2	0.46844 (15)	0.35602 (9)	0.89236 (12)	0.0531 (4)
O1	0.69166 (16)	0.40858 (9)	0.92380 (11)	0.0328 (4)
N1	0.7666 (3)	0.74393 (18)	0.69117 (18)	0.0609 (7)
N2	0.51593 (17)	0.47557 (11)	0.80301 (12)	0.0262 (4)
C1	1.0468 (2)	0.47953 (14)	1.19668 (15)	0.0274 (5)
C2	1.0082 (2)	0.55340 (14)	1.15244 (16)	0.0304 (5)
H2	1.0558	0.6027	1.1730	0.036*
C3	0.8982 (2)	0.55382 (13)	1.07731 (16)	0.0292 (5)
H3	0.8696	0.6041	1.0465	0.035*
C4	0.8293 (2)	0.48155 (13)	1.04648 (15)	0.0250 (4)
C5	0.8714 (2)	0.40787 (13)	1.09205 (16)	0.0292 (5)
H5	0.8256	0.3582	1.0709	0.035*
C6	0.9795 (2)	0.40674 (14)	1.16804 (16)	0.0299 (5)
H6	1.0071	0.3568	1.2000	0.036*
C7	0.7153 (2)	0.48088 (13)	0.96488 (15)	0.0248 (4)
C8	0.6431 (2)	0.54917 (13)	0.93219 (15)	0.0275 (5)
H8	0.6567	0.5989	0.9674	0.033*
C9	0.5476 (2)	0.54684 (13)	0.84604 (15)	0.0261 (4)
C10	0.4192 (2)	0.47173 (13)	0.71416 (15)	0.0264 (4)
C11	0.4659 (2)	0.44916 (14)	0.63062 (15)	0.0299 (5)
H11	0.5618	0.4376	0.6303	0.036*
C12	0.3708 (2)	0.44347 (14)	0.54681 (16)	0.0332 (5)
H12	0.4020	0.4278	0.4890	0.040*
C13	0.2318 (2)	0.46038 (15)	0.54715 (17)	0.0353 (5)
H13	0.1674	0.4568	0.4897	0.042*
C14	0.1866 (2)	0.48238 (16)	0.63088 (17)	0.0371 (6)
H14	0.0907	0.4944	0.6309	0.044*
C15	0.2795 (2)	0.48729 (15)	0.71564 (17)	0.0351 (5)
H15	0.2475	0.5012	0.7737	0.042*
C16	0.5544 (2)	0.71958 (13)	0.86749 (16)	0.0305 (5)
H16A	0.4994	0.7701	0.8507	0.037*
H16B	0.5464	0.7061	0.9346	0.037*
C17	0.7407 (2)	0.74202 (16)	0.76730 (19)	0.0392 (6)
C18	0.7058 (2)	0.73849 (13)	0.86224 (16)	0.0290 (5)
C19	0.7974 (2)	0.75408 (13)	0.94089 (17)	0.0298 (5)
H19	0.7598	0.7497	0.9988	0.036*
C20	0.9453 (2)	0.77676 (13)	0.95341 (18)	0.0331 (5)
C21	1.0184 (3)	0.77306 (15)	1.04606 (19)	0.0399 (6)
H21	0.9705	0.7581	1.0972	0.048*
C22	1.1595 (3)	0.79076 (17)	1.0647 (2)	0.0497 (7)
H22	1.2079	0.7870	1.1281	0.060*
C23	1.2294 (3)	0.81371 (17)	0.9917 (3)	0.0549 (8)
H23	1.3263	0.8257	1.0045	0.066*
C24	1.1594 (3)	0.81935 (16)	0.8998 (2)	0.0525 (8)
H24	1.2083	0.8351	0.8494	0.063*
C25	1.0182 (3)	0.80214 (15)	0.8805 (2)	0.0412 (6)
H25	0.9703	0.8076	0.8172	0.049*
B1	0.5719 (3)	0.39255 (16)	0.85061 (19)	0.0319 (6)

	U11	U22	U33	U12	U13	U23
Cl1	0.0282 (3)	0.0561 (4)	0.0277 (3)	0.0032 (2)	−0.0063 (2)	−0.0049 (3)
S1	0.0339 (3)	0.0328 (3)	0.0334 (3)	0.0042 (2)	−0.0084 (2)	0.0026 (2)
F1	0.0668 (10)	0.0414 (8)	0.0339 (8)	0.0178 (7)	−0.0125 (7)	−0.0125 (6)
F2	0.0451 (9)	0.0497 (9)	0.0622 (11)	−0.0141 (7)	0.0003 (7)	0.0157 (8)
O1	0.0389 (9)	0.0252 (8)	0.0294 (9)	0.0015 (7)	−0.0102 (7)	−0.0042 (6)
N1	0.0547 (15)	0.090 (2)	0.0404 (15)	0.0242 (14)	0.0130 (11)	0.0166 (13)
N2	0.0249 (9)	0.0321 (10)	0.0201 (9)	−0.0005 (7)	−0.0013 (7)	−0.0020 (7)
C1	0.0232 (10)	0.0402 (12)	0.0181 (11)	0.0031 (9)	0.0005 (8)	−0.0029 (9)
C2	0.0307 (11)	0.0330 (12)	0.0266 (12)	−0.0051 (9)	0.0020 (9)	−0.0050 (9)
C3	0.0328 (11)	0.0278 (11)	0.0256 (12)	−0.0010 (9)	−0.0003 (9)	−0.0007 (9)
C4	0.0265 (10)	0.0281 (11)	0.0197 (11)	0.0020 (8)	0.0014 (8)	−0.0020 (8)
C5	0.0317 (11)	0.0278 (11)	0.0266 (12)	0.0011 (9)	−0.0004 (8)	−0.0011 (9)
C6	0.0325 (11)	0.0287 (11)	0.0265 (12)	0.0060 (9)	−0.0014 (9)	−0.0004 (9)
C7	0.0277 (10)	0.0263 (11)	0.0202 (11)	−0.0026 (8)	0.0029 (8)	−0.0011 (8)
C8	0.0294 (11)	0.0279 (11)	0.0229 (11)	0.0006 (9)	−0.0029 (8)	−0.0035 (8)
C9	0.0246 (10)	0.0308 (11)	0.0222 (11)	−0.0003 (8)	0.0011 (8)	−0.0006 (8)
C10	0.0266 (10)	0.0297 (11)	0.0214 (11)	−0.0042 (9)	−0.0011 (8)	0.0017 (8)
C11	0.0271 (11)	0.0366 (12)	0.0251 (12)	−0.0038 (9)	0.0014 (8)	−0.0026 (9)
C12	0.0390 (12)	0.0392 (13)	0.0210 (12)	−0.0095 (10)	0.0036 (9)	−0.0018 (9)
C13	0.0352 (12)	0.0430 (14)	0.0245 (12)	−0.0097 (10)	−0.0061 (9)	0.0050 (10)
C14	0.0254 (11)	0.0512 (15)	0.0326 (13)	−0.0026 (10)	−0.0020 (9)	0.0011 (11)
C15	0.0278 (11)	0.0507 (15)	0.0267 (13)	−0.0038 (10)	0.0035 (9)	−0.0049 (10)
C16	0.0297 (11)	0.0288 (11)	0.0317 (13)	0.0074 (9)	0.0002 (9)	0.0004 (9)
C17	0.0345 (12)	0.0473 (15)	0.0353 (15)	0.0106 (11)	0.0041 (10)	0.0065 (11)
C18	0.0318 (11)	0.0246 (10)	0.0311 (12)	0.0071 (9)	0.0066 (9)	0.0030 (9)
C19	0.0331 (11)	0.0248 (11)	0.0317 (13)	0.0024 (9)	0.0058 (9)	0.0010 (9)
C20	0.0330 (11)	0.0214 (10)	0.0449 (15)	0.0013 (9)	0.0061 (10)	0.0002 (10)
C21	0.0380 (13)	0.0353 (13)	0.0452 (16)	−0.0021 (10)	0.0029 (11)	−0.0054 (11)
C22	0.0386 (14)	0.0444 (15)	0.0616 (19)	−0.0029 (12)	−0.0067 (12)	−0.0058 (13)
C23	0.0334 (13)	0.0383 (15)	0.092 (3)	−0.0078 (12)	0.0072 (14)	−0.0011 (15)
C24	0.0411 (14)	0.0341 (14)	0.086 (2)	−0.0042 (12)	0.0215 (15)	0.0109 (14)
C25	0.0397 (13)	0.0314 (13)	0.0536 (17)	0.0016 (10)	0.0105 (11)	0.0096 (11)
B1	0.0342 (13)	0.0305 (13)	0.0284 (14)	−0.0032 (11)	−0.0040 (10)	−0.0041 (10)

Cl1—C1	1.736 (2)	C11—C12	1.392 (3)
S1—C9	1.748 (2)	C11—H11	0.9500
S1—C16	1.824 (2)	C12—C13	1.377 (3)
F1—B1	1.376 (3)	C12—H12	0.9500
F2—B1	1.375 (3)	C13—C14	1.373 (3)
O1—C7	1.318 (2)	C13—H13	0.9500
O1—B1	1.458 (3)	C14—C15	1.391 (3)
N1—C17	1.144 (3)	C14—H14	0.9500
N2—C9	1.326 (3)	C15—H15	0.9500
N2—C10	1.453 (3)	C16—C18	1.513 (3)
N2—B1	1.571 (3)	C16—H16A	0.9900
C1—C2	1.382 (3)	C16—H16B	0.9900
C1—C6	1.384 (3)	C17—C18	1.437 (3)
C2—C3	1.388 (3)	C18—C19	1.340 (3)
C2—H2	0.9500	C19—C20	1.466 (3)
C3—C4	1.391 (3)	C19—H19	0.9500
C3—H3	0.9500	C20—C21	1.396 (3)
C4—C5	1.394 (3)	C20—C25	1.400 (3)
C4—C7	1.474 (3)	C21—C22	1.384 (3)
C5—C6	1.385 (3)	C21—H21	0.9500
C5—H5	0.9500	C22—C23	1.372 (4)
C6—H6	0.9500	C22—H22	0.9500
C7—C8	1.358 (3)	C23—C24	1.377 (4)
C8—C9	1.417 (3)	C23—H23	0.9500
C8—H8	0.9500	C24—C25	1.384 (4)
C10—C11	1.380 (3)	C24—H24	0.9500
C10—C15	1.381 (3)	C25—H25	0.9500
C9—S1—C16	104.75 (10)	C13—C14—C15	120.7 (2)
C7—O1—B1	122.73 (17)	C13—C14—H14	119.6
C9—N2—C10	120.69 (18)	C15—C14—H14	119.6
C9—N2—B1	121.04 (17)	C10—C15—C14	119.0 (2)
C10—N2—B1	118.08 (17)	C10—C15—H15	120.5
C2—C1—C6	121.98 (19)	C14—C15—H15	120.5
C2—C1—Cl1	119.43 (17)	C18—C16—S1	116.79 (16)
C6—C1—Cl1	118.60 (17)	C18—C16—H16A	108.1
C1—C2—C3	118.4 (2)	S1—C16—H16A	108.1
C1—C2—H2	120.8	C18—C16—H16B	108.1
C3—C2—H2	120.8	S1—C16—H16B	108.1
C2—C3—C4	120.9 (2)	H16A—C16—H16B	107.3
C2—C3—H3	119.6	N1—C17—C18	178.8 (3)
C4—C3—H3	119.6	C19—C18—C17	123.4 (2)
C3—C4—C5	119.35 (19)	C19—C18—C16	121.6 (2)
C3—C4—C7	121.36 (19)	C17—C18—C16	115.0 (2)
C5—C4—C7	119.27 (19)	C18—C19—C20	131.4 (2)
C6—C5—C4	120.4 (2)	C18—C19—H19	114.3
C6—C5—H5	119.8	C20—C19—H19	114.3
C4—C5—H5	119.8	C21—C20—C25	117.7 (2)
C1—C6—C5	119.0 (2)	C21—C20—C19	116.8 (2)
C1—C6—H6	120.5	C25—C20—C19	125.4 (2)
C5—C6—H6	120.5	C22—C21—C20	121.2 (3)
O1—C7—C8	122.33 (19)	C22—C21—H21	119.4
O1—C7—C4	114.39 (18)	C20—C21—H21	119.4
C8—C7—C4	123.25 (19)	C23—C22—C21	120.0 (3)
C7—C8—C9	120.5 (2)	C23—C22—H22	120.0
C7—C8—H8	119.7	C21—C22—H22	120.0
C9—C8—H8	119.7	C22—C23—C24	120.1 (3)
N2—C9—C8	119.69 (19)	C22—C23—H23	119.9
N2—C9—S1	118.65 (15)	C24—C23—H23	119.9
C8—C9—S1	121.61 (16)	C23—C24—C25	120.3 (3)
C11—C10—C15	120.8 (2)	C23—C24—H24	119.9
C11—C10—N2	120.13 (19)	C25—C24—H24	119.9
C15—C10—N2	119.0 (2)	C24—C25—C20	120.7 (3)
C10—C11—C12	119.2 (2)	C24—C25—H25	119.7
C10—C11—H11	120.4	C20—C25—H25	119.7
C12—C11—H11	120.4	F2—B1—F1	110.8 (2)
C13—C12—C11	120.4 (2)	F2—B1—O1	109.0 (2)
C13—C12—H12	119.8	F1—B1—O1	108.0 (2)
C11—C12—H12	119.8	F2—B1—N2	109.24 (19)
C14—C13—C12	119.8 (2)	F1—B1—N2	110.0 (2)
C14—C13—H13	120.1	O1—B1—N2	109.71 (18)
C12—C13—H13	120.1
C6—C1—C2—C3	0.2 (3)	C10—C11—C12—C13	0.2 (3)
Cl1—C1—C2—C3	179.82 (17)	C11—C12—C13—C14	−0.5 (4)
C1—C2—C3—C4	−0.7 (3)	C12—C13—C14—C15	−0.4 (4)
C2—C3—C4—C5	0.2 (3)	C11—C10—C15—C14	−2.0 (4)
C2—C3—C4—C7	−178.1 (2)	N2—C10—C15—C14	−179.0 (2)
C3—C4—C5—C6	0.8 (3)	C13—C14—C15—C10	1.6 (4)
C7—C4—C5—C6	179.1 (2)	C9—S1—C16—C18	72.85 (18)
C2—C1—C6—C5	0.8 (3)	N1—C17—C18—C19	157 (14)
Cl1—C1—C6—C5	−178.86 (17)	N1—C17—C18—C16	−26 (14)
C4—C5—C6—C1	−1.3 (3)	S1—C16—C18—C19	−137.62 (19)
B1—O1—C7—C8	−10.5 (3)	S1—C16—C18—C17	45.1 (2)
B1—O1—C7—C4	171.5 (2)	C17—C18—C19—C20	−0.2 (4)
C3—C4—C7—O1	158.4 (2)	C16—C18—C19—C20	−177.3 (2)
C5—C4—C7—O1	−19.9 (3)	C18—C19—C20—C21	−167.7 (2)
C3—C4—C7—C8	−19.6 (3)	C18—C19—C20—C25	12.7 (4)
C5—C4—C7—C8	162.2 (2)	C25—C20—C21—C22	−2.5 (4)
O1—C7—C8—C9	−6.2 (3)	C19—C20—C21—C22	177.9 (2)
C4—C7—C8—C9	171.6 (2)	C20—C21—C22—C23	1.1 (4)
C10—N2—C9—C8	−179.45 (19)	C21—C22—C23—C24	0.1 (4)
B1—N2—C9—C8	5.6 (3)	C22—C23—C24—C25	0.2 (4)
C10—N2—C9—S1	−1.9 (3)	C23—C24—C25—C20	−1.7 (4)
B1—N2—C9—S1	−176.82 (16)	C21—C20—C25—C24	2.8 (4)
C7—C8—C9—N2	8.1 (3)	C19—C20—C25—C24	−177.7 (2)
C7—C8—C9—S1	−169.38 (17)	C7—O1—B1—F2	−97.9 (2)
C16—S1—C9—N2	−175.52 (17)	C7—O1—B1—F1	141.6 (2)
C16—S1—C9—C8	2.0 (2)	C7—O1—B1—N2	21.6 (3)
C9—N2—C10—C11	112.8 (2)	C9—N2—B1—F2	100.3 (2)
B1—N2—C10—C11	−72.1 (3)	C10—N2—B1—F2	−74.8 (3)
C9—N2—C10—C15	−70.1 (3)	C9—N2—B1—F1	−137.9 (2)
B1—N2—C10—C15	105.0 (2)	C10—N2—B1—F1	47.0 (3)
C15—C10—C11—C12	1.1 (3)	C9—N2—B1—O1	−19.2 (3)
N2—C10—C11—C12	178.1 (2)	C10—N2—B1—O1	165.75 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···F1i	0.99	2.35	3.184 (3)	141
C21—H21···N1ii	0.95	2.55	3.434 (4)	156
C15—H15···Cg1iii	0.95	2.52	3.394 (5)	153

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯F1i	0.99	2.35	3.184 (3)	141
C21—H21⋯N1ii	0.95	2.55	3.434 (4)	156
C15—H15⋯Cg1iii	0.95	2.52	3.394 (5)	153

Symmetry codes: (i) ; (ii) ; (iii) .