4,4'-Bis(dimethyl-amino)benzhydryl phenyl sulfone.

In the title compound, C(23)H(26)N(2)O(2)S, the sulfur-bound phenyl group is aligned approximately parallel to one of the two rings of the benzhydryl group, making a dihedral angle of 1.15 (9)°. The other forms a dihedral angle of 59.20 (9)° with the phenyl group bound to the S atom. In the crystal, mol-ecules are linked into strands along [100] by weak C-H⋯O contacts. Weak C-H⋯π inter-actions are also observed.

Related literature

For the history of the sulfone anion, see: Hinsberg (1897 ▶, 1917 ▶); Meek & Fowler (1968 ▶); Kobayashi & Toriyabe (1985 ▶); Veenstra & Zwanenburg (1975 ▶); Weber et al. (1985 ▶); Mayr et al. (2001 ▶, 2008 ▶). For a related structure, see: Li & Su (2005 ▶). For the graph-set analysis of hydrogen-bond networks, see: Bernstein et al. (1995 ▶); Etter et al. (1990 ▶).

Experimental

Crystal data

C23H26N2O2S

M = 394.53

Monoclinic,

a = 5.9835 (2) Å

b = 16.6036 (5) Å

c = 20.8340 (6) Å

β = 98.150 (2)°

V = 2048.90 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 200 K

0.31 × 0.13 × 0.09 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

13918 measured reflections

4468 independent reflections

3142 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.112

S = 1.03

4468 reflections

257 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.33 e Å−3

Data collection: COLLECT (Hooft, 2004 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680904642X/ng2679sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904642X/ng2679Isup2.hkl

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

C23H26N2O2S	F(000) = 840
Mr = 394.53	Dx = 1.279 (1) Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7329 reflections
a = 5.9835 (2) Å	θ = 3.1–27.1°
b = 16.6036 (5) Å	µ = 0.18 mm−1
c = 20.8340 (6) Å	T = 200 K
β = 98.150 (2)°	Rod, colourless
V = 2048.90 (11) Å3	0.31 × 0.13 × 0.09 mm
Z = 4

Nonius KappaCCD diffractometer	3142 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.050
MONTEL, graded multilayered X-ray optics	θmax = 27.1°, θmin = 3.4°
Detector resolution: 9 pixels mm-1	h = −7→7
CCD; rotation images; thick slices, phi/ω–scan	k = −21→20
13918 measured reflections	l = −25→26
4468 independent 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.043P)2 + 0.5546P] where P = (Fo2 + 2Fc2)/3
4468 reflections	(Δ/σ)max < 0.001
257 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.33 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 > 2σ(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
S1	0.74058 (8)	0.09486 (3)	0.15422 (2)	0.03368 (15)
O1	0.9739 (2)	0.11658 (8)	0.15443 (7)	0.0452 (4)
O2	0.6163 (2)	0.06134 (8)	0.09615 (6)	0.0460 (4)
N1	0.3991 (3)	0.38915 (10)	−0.04522 (8)	0.0481 (4)
N2	0.9032 (3)	0.34009 (9)	0.41719 (7)	0.0396 (4)
C1	0.5830 (3)	0.18149 (10)	0.17654 (8)	0.0291 (4)
H1	0.4310	0.1605	0.1829	0.035*
C2	0.5424 (3)	0.23697 (10)	0.11785 (8)	0.0284 (4)
C3	0.3353 (3)	0.23509 (11)	0.07836 (9)	0.0337 (4)
H3	0.2231	0.1985	0.0883	0.040*
C4	0.2872 (3)	0.28472 (11)	0.02511 (9)	0.0362 (4)
H4	0.1426	0.2820	−0.0004	0.043*
C5	0.4470 (3)	0.33879 (10)	0.00799 (9)	0.0334 (4)
C6	0.6582 (3)	0.33989 (11)	0.04706 (9)	0.0369 (4)
H6	0.7721	0.3755	0.0367	0.044*
C7	0.7035 (3)	0.28988 (10)	0.10057 (9)	0.0343 (4)
H7	0.8482	0.2918	0.1260	0.041*
C8	0.1893 (4)	0.38272 (16)	−0.08687 (12)	0.0651 (7)
H8A	0.1666	0.3269	−0.1017	0.098*
H8B	0.1908	0.4182	−0.1244	0.098*
H8C	0.0661	0.3986	−0.0631	0.098*
C9	0.5726 (4)	0.43670 (14)	−0.06787 (11)	0.0557 (6)
H9A	0.6485	0.4694	−0.0321	0.084*
H9B	0.5049	0.4721	−0.1030	0.084*
H9C	0.6828	0.4011	−0.0840	0.084*
C10	0.6815 (3)	0.21879 (10)	0.24073 (8)	0.0288 (4)
C11	0.8948 (3)	0.25420 (11)	0.25295 (9)	0.0326 (4)
H11	0.9933	0.2505	0.2211	0.039*
C12	0.9664 (3)	0.29446 (11)	0.31010 (8)	0.0334 (4)
H12	1.1117	0.3187	0.3162	0.040*
C13	0.8299 (3)	0.30059 (10)	0.35951 (8)	0.0322 (4)
C14	0.6190 (3)	0.26226 (11)	0.34831 (8)	0.0345 (4)
H14	0.5230	0.2633	0.3809	0.041*
C15	0.5488 (3)	0.22278 (10)	0.29024 (9)	0.0325 (4)
H15	0.4048	0.1976	0.2841	0.039*
C16	1.0909 (4)	0.39582 (15)	0.42066 (11)	0.0586 (6)
H16A	1.2192	0.3692	0.4051	0.088*
H16B	1.1346	0.4130	0.4657	0.088*
H16C	1.0459	0.4429	0.3936	0.088*
C17	0.7429 (4)	0.35926 (14)	0.46134 (10)	0.0514 (6)
H17A	0.6346	0.3993	0.4412	0.077*
H17B	0.8241	0.3811	0.5018	0.077*
H17C	0.6621	0.3103	0.4708	0.077*
C18	0.7267 (3)	0.02533 (10)	0.21776 (8)	0.0290 (4)
C19	0.9132 (3)	0.01217 (11)	0.26374 (9)	0.0366 (4)
H19	1.0483	0.0418	0.2624	0.044*
C20	0.9012 (4)	−0.04461 (11)	0.31178 (10)	0.0425 (5)
H20	1.0293	−0.0545	0.3433	0.051*
C21	0.7036 (4)	−0.08691 (11)	0.31415 (9)	0.0412 (5)
H21	0.6956	−0.1252	0.3476	0.049*
C22	0.5181 (4)	−0.07361 (11)	0.26796 (10)	0.0423 (5)
H22	0.3828	−0.1030	0.2696	0.051*
C23	0.5285 (3)	−0.01744 (11)	0.21925 (9)	0.0373 (4)
H23	0.4013	−0.0084	0.1873	0.045*

	U11	U22	U33	U12	U13	U23
S1	0.0452 (3)	0.0261 (2)	0.0328 (3)	0.00373 (19)	0.0159 (2)	0.00259 (18)
O1	0.0450 (8)	0.0352 (7)	0.0617 (9)	0.0052 (6)	0.0296 (7)	0.0088 (6)
O2	0.0762 (10)	0.0358 (7)	0.0268 (7)	0.0050 (7)	0.0096 (7)	−0.0029 (6)
N1	0.0550 (11)	0.0468 (10)	0.0399 (10)	0.0014 (8)	−0.0024 (8)	0.0149 (8)
N2	0.0448 (10)	0.0429 (9)	0.0320 (9)	−0.0050 (8)	0.0083 (7)	−0.0045 (7)
C1	0.0330 (10)	0.0264 (9)	0.0297 (9)	0.0013 (7)	0.0107 (8)	0.0004 (7)
C2	0.0333 (10)	0.0247 (9)	0.0285 (9)	0.0011 (7)	0.0090 (8)	−0.0016 (7)
C3	0.0326 (10)	0.0307 (9)	0.0382 (10)	−0.0040 (8)	0.0062 (8)	−0.0015 (8)
C4	0.0320 (10)	0.0399 (10)	0.0351 (10)	0.0014 (8)	−0.0008 (8)	−0.0011 (8)
C5	0.0414 (11)	0.0282 (9)	0.0306 (10)	0.0062 (8)	0.0048 (8)	0.0001 (7)
C6	0.0386 (11)	0.0327 (10)	0.0389 (11)	−0.0048 (8)	0.0041 (9)	0.0064 (8)
C7	0.0336 (10)	0.0334 (10)	0.0347 (10)	−0.0016 (8)	0.0008 (8)	0.0045 (8)
C8	0.0605 (15)	0.0772 (17)	0.0527 (15)	0.0080 (13)	−0.0092 (12)	0.0214 (13)
C9	0.0688 (15)	0.0517 (13)	0.0464 (13)	0.0004 (12)	0.0075 (11)	0.0193 (11)
C10	0.0334 (10)	0.0250 (9)	0.0287 (9)	0.0031 (7)	0.0070 (8)	0.0033 (7)
C11	0.0316 (10)	0.0373 (10)	0.0304 (10)	0.0046 (8)	0.0094 (8)	0.0036 (8)
C12	0.0297 (9)	0.0379 (10)	0.0327 (10)	−0.0022 (8)	0.0041 (8)	0.0037 (8)
C13	0.0385 (10)	0.0307 (9)	0.0275 (9)	0.0025 (8)	0.0051 (8)	0.0050 (7)
C14	0.0387 (11)	0.0372 (10)	0.0303 (10)	−0.0012 (8)	0.0144 (8)	0.0005 (8)
C15	0.0346 (10)	0.0291 (9)	0.0358 (10)	−0.0029 (8)	0.0116 (8)	0.0012 (8)
C16	0.0574 (14)	0.0714 (16)	0.0481 (13)	−0.0245 (12)	0.0108 (11)	−0.0139 (12)
C17	0.0615 (14)	0.0580 (13)	0.0373 (12)	−0.0138 (11)	0.0163 (10)	−0.0125 (10)
C18	0.0384 (10)	0.0210 (8)	0.0287 (9)	0.0003 (7)	0.0085 (8)	−0.0014 (7)
C19	0.0377 (10)	0.0316 (10)	0.0407 (11)	−0.0037 (8)	0.0063 (9)	−0.0001 (8)
C20	0.0516 (13)	0.0361 (10)	0.0377 (11)	0.0027 (9)	−0.0006 (9)	0.0041 (8)
C21	0.0629 (14)	0.0270 (10)	0.0361 (11)	−0.0007 (9)	0.0149 (10)	0.0048 (8)
C22	0.0505 (12)	0.0308 (10)	0.0483 (12)	−0.0095 (9)	0.0165 (10)	0.0007 (9)
C23	0.0394 (11)	0.0322 (10)	0.0401 (11)	−0.0030 (8)	0.0052 (9)	0.0009 (8)

S1—O2	1.4391 (13)	C9—H9C	0.9800
S1—O1	1.4413 (14)	C10—C15	1.390 (2)
S1—C18	1.7672 (17)	C10—C11	1.396 (2)
S1—C1	1.8163 (17)	C11—C12	1.380 (2)
N1—C5	1.386 (2)	C11—H11	0.9500
N1—C8	1.425 (3)	C12—C13	1.405 (3)
N1—C9	1.436 (3)	C12—H12	0.9500
N2—C13	1.385 (2)	C13—C14	1.403 (3)
N2—C16	1.449 (3)	C14—C15	1.388 (2)
N2—C17	1.455 (3)	C14—H14	0.9500
C1—C10	1.515 (2)	C15—H15	0.9500
C1—C2	1.523 (2)	C16—H16A	0.9800
C1—H1	1.0000	C16—H16B	0.9800
C2—C3	1.387 (2)	C16—H16C	0.9800
C2—C7	1.389 (2)	C17—H17A	0.9800
C3—C4	1.379 (3)	C17—H17B	0.9800
C3—H3	0.9500	C17—H17C	0.9800
C4—C5	1.394 (3)	C18—C19	1.381 (2)
C4—H4	0.9500	C18—C23	1.386 (2)
C5—C6	1.403 (3)	C19—C20	1.384 (3)
C6—C7	1.386 (2)	C19—H19	0.9500
C6—H6	0.9500	C20—C21	1.382 (3)
C7—H7	0.9500	C20—H20	0.9500
C8—H8A	0.9800	C21—C22	1.380 (3)
C8—H8B	0.9800	C21—H21	0.9500
C8—H8C	0.9800	C22—C23	1.386 (3)
C9—H9A	0.9800	C22—H22	0.9500
C9—H9B	0.9800	C23—H23	0.9500
O2—S1—O1	118.94 (9)	C15—C10—C11	116.64 (16)
O2—S1—C18	107.68 (8)	C15—C10—C1	118.88 (15)
O1—S1—C18	108.04 (8)	C11—C10—C1	124.38 (15)
O2—S1—C1	107.24 (8)	C12—C11—C10	121.71 (17)
O1—S1—C1	109.81 (8)	C12—C11—H11	119.1
C18—S1—C1	104.14 (8)	C10—C11—H11	119.1
C5—N1—C8	120.42 (18)	C11—C12—C13	121.72 (17)
C5—N1—C9	121.15 (17)	C11—C12—H12	119.1
C8—N1—C9	117.16 (17)	C13—C12—H12	119.1
C13—N2—C16	119.58 (16)	N2—C13—C14	121.74 (16)
C13—N2—C17	119.74 (16)	N2—C13—C12	121.64 (17)
C16—N2—C17	113.86 (16)	C14—C13—C12	116.59 (16)
C10—C1—C2	117.33 (14)	C15—C14—C13	120.88 (16)
C10—C1—S1	113.48 (12)	C15—C14—H14	119.6
C2—C1—S1	107.63 (11)	C13—C14—H14	119.6
C10—C1—H1	105.8	C14—C15—C10	122.38 (17)
C2—C1—H1	105.8	C14—C15—H15	118.8
S1—C1—H1	105.8	C10—C15—H15	118.8
C3—C2—C7	117.06 (16)	N2—C16—H16A	109.5
C3—C2—C1	119.33 (15)	N2—C16—H16B	109.5
C7—C2—C1	123.61 (15)	H16A—C16—H16B	109.5
C4—C3—C2	122.04 (17)	N2—C16—H16C	109.5
C4—C3—H3	119.0	H16A—C16—H16C	109.5
C2—C3—H3	119.0	H16B—C16—H16C	109.5
C3—C4—C5	121.21 (16)	N2—C17—H17A	109.5
C3—C4—H4	119.4	N2—C17—H17B	109.5
C5—C4—H4	119.4	H17A—C17—H17B	109.5
N1—C5—C4	121.43 (17)	N2—C17—H17C	109.5
N1—C5—C6	121.57 (17)	H17A—C17—H17C	109.5
C4—C5—C6	116.99 (16)	H17B—C17—H17C	109.5
C7—C6—C5	121.09 (17)	C19—C18—C23	120.87 (16)
C7—C6—H6	119.5	C19—C18—S1	120.24 (14)
C5—C6—H6	119.5	C23—C18—S1	118.85 (13)
C6—C7—C2	121.59 (17)	C18—C19—C20	119.31 (18)
C6—C7—H7	119.2	C18—C19—H19	120.3
C2—C7—H7	119.2	C20—C19—H19	120.3
N1—C8—H8A	109.5	C21—C20—C19	120.29 (18)
N1—C8—H8B	109.5	C21—C20—H20	119.9
H8A—C8—H8B	109.5	C19—C20—H20	119.9
N1—C8—H8C	109.5	C22—C21—C20	120.09 (18)
H8A—C8—H8C	109.5	C22—C21—H21	120.0
H8B—C8—H8C	109.5	C20—C21—H21	120.0
N1—C9—H9A	109.5	C21—C22—C23	120.20 (18)
N1—C9—H9B	109.5	C21—C22—H22	119.9
H9A—C9—H9B	109.5	C23—C22—H22	119.9
N1—C9—H9C	109.5	C22—C23—C18	119.23 (17)
H9A—C9—H9C	109.5	C22—C23—H23	120.4
H9B—C9—H9C	109.5	C18—C23—H23	120.4
O2—S1—C1—C10	174.47 (12)	C15—C10—C11—C12	−3.0 (3)
O1—S1—C1—C10	−54.96 (14)	C1—C10—C11—C12	173.26 (16)
C18—S1—C1—C10	60.52 (14)	C10—C11—C12—C13	1.2 (3)
O2—S1—C1—C2	−53.97 (13)	C16—N2—C13—C14	−163.95 (19)
O1—S1—C1—C2	76.60 (13)	C17—N2—C13—C14	−14.6 (3)
C18—S1—C1—C2	−167.92 (11)	C16—N2—C13—C12	18.3 (3)
C10—C1—C2—C3	−131.26 (17)	C17—N2—C13—C12	167.64 (18)
S1—C1—C2—C3	99.33 (16)	C11—C12—C13—N2	179.12 (16)
C10—C1—C2—C7	49.4 (2)	C11—C12—C13—C14	1.3 (3)
S1—C1—C2—C7	−80.00 (19)	N2—C13—C14—C15	−179.82 (16)
C7—C2—C3—C4	−1.6 (3)	C12—C13—C14—C15	−2.0 (3)
C1—C2—C3—C4	179.00 (16)	C13—C14—C15—C10	0.2 (3)
C2—C3—C4—C5	0.8 (3)	C11—C10—C15—C14	2.3 (3)
C8—N1—C5—C4	−4.7 (3)	C1—C10—C15—C14	−174.19 (16)
C9—N1—C5—C4	−171.44 (19)	O2—S1—C18—C19	140.96 (15)
C8—N1—C5—C6	175.4 (2)	O1—S1—C18—C19	11.31 (17)
C9—N1—C5—C6	8.6 (3)	C1—S1—C18—C19	−105.40 (15)
C3—C4—C5—N1	−179.57 (17)	O2—S1—C18—C23	−36.90 (16)
C3—C4—C5—C6	0.4 (3)	O1—S1—C18—C23	−166.54 (14)
N1—C5—C6—C7	179.29 (17)	C1—S1—C18—C23	76.74 (15)
C4—C5—C6—C7	−0.7 (3)	C23—C18—C19—C20	0.1 (3)
C5—C6—C7—C2	−0.2 (3)	S1—C18—C19—C20	−177.73 (14)
C3—C2—C7—C6	1.3 (3)	C18—C19—C20—C21	−0.8 (3)
C1—C2—C7—C6	−179.32 (16)	C19—C20—C21—C22	1.0 (3)
C2—C1—C10—C15	112.91 (18)	C20—C21—C22—C23	−0.4 (3)
S1—C1—C10—C15	−120.48 (15)	C21—C22—C23—C18	−0.3 (3)
C2—C1—C10—C11	−63.2 (2)	C19—C18—C23—C22	0.5 (3)
S1—C1—C10—C11	63.4 (2)	S1—C18—C23—C22	178.34 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1i	0.95	2.56	3.469 (2)	160
C17—H17C···Cg1ii	0.98	2.80	3.673 (2)	148
C21—H21···Cg1iii	0.95	2.74	3.633 (2)	158
C22—H22···Cg2iii	0.95	2.78	3.435 (2)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1i	0.95	2.56	3.469 (2)	160
C17—H17C⋯Cg1ii	0.98	2.80	3.673 (2)	148
C21—H21⋯Cg1iii	0.95	2.74	3.633 (2)	158
C22—H22⋯Cg2iii	0.95	2.78	3.435 (2)	127

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the C2–C7and C10–C15 rings, respectively.