N,N-Di­benzyl­tri­phenyl­methanesulfen­amide

The title compound, C₃₃H₂₉NS, is the result of the condensation reaction of (C₆H₅)₃CSCl and HN(CH₂C₆H₅)₂. In its crystalline state, the C-S-N plane forms a dihedral angle of 88.5 (1)% with the C-N-C plane, in good agreement with the value of 90.0° for the torsional fundamental state of the mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.043
• wR factor = 0.122
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.16 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   0 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 EXPRESS (Enraf-Nonius 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCDA4 (Harms, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

C33H29NS	Z = 2
Mr = 471.63	F(000) = 500
Triclinic, P1	Dx = 1.217 Mg m^−3
Hall symbol: -P 1	Melting point: 409 K
a = 10.009 (2) Å	Cu Kα radiation, λ = 1.5418 Å
b = 10.519 (3) Å	Cell parameters from 25 reflections
c = 13.311 (1) Å	θ = 12.0–18.4°
α = 106.822 (13)°	µ = 1.26 mm^−1
β = 99.037 (13)°	T = 293 K
γ = 100.245 (19)°	Prismatic, colourless
V = 1287.3 (5) Å^3	0.24 × 0.24 × 0.15 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.024
ω–2θ scans	θmax = 73.9°, θmin = 5.2°
Absorption correction: ψ scan (North et al., 1968)	h = −12→12
Tmin = 0.716, Tmax = 0.827	k = −12→13
5442 measured reflections	l = −16→0
5207 independent reflections	3 standard reflections every 120 reflections
3437 reflections with I > 2σ(I)	intensity decay: 1%

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.043	w = 1/[σ^2(Fo^2) + (0.0525P)^2 + 0.217P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.122	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.34 e Å^−3
5207 reflections	Δρmin = −0.20 e Å^−3
345 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.

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

	x	y	z	Uiso*/Ueq
S1	0.05767 (5)	0.42981 (5)	0.25809 (4)	0.05087 (16)
N1	−0.00227 (17)	0.26189 (17)	0.18844 (13)	0.0496 (4)
C1	0.22993 (19)	0.44546 (18)	0.34880 (15)	0.0399 (4)
C2	0.26318 (19)	0.59537 (19)	0.42044 (15)	0.0410 (4)
C3	0.3031 (2)	0.6345 (2)	0.53182 (16)	0.0447 (5)
H3	0.3048	0.5679	0.5649	0.042 (5)*
C4	0.3404 (2)	0.7709 (2)	0.59438 (17)	0.0507 (5)
H4	0.3676	0.7952	0.6688	0.060 (6)*
C5	0.3375 (2)	0.8709 (2)	0.54715 (19)	0.0567 (6)
H5	0.3624	0.9626	0.5893	0.053 (6)*
C6	0.2975 (2)	0.8343 (2)	0.43707 (19)	0.0590 (6)
H6	0.2948	0.9015	0.4048	0.066 (7)*
C7	0.2613 (2)	0.6987 (2)	0.37440 (18)	0.0505 (5)
H7	0.2351	0.6756	0.3	0.047 (6)*
C8	0.33973 (19)	0.41776 (19)	0.28167 (15)	0.0412 (4)
C9	0.3234 (2)	0.2907 (2)	0.20559 (17)	0.0533 (5)
H9	0.2442	0.2225	0.1947	0.048 (6)*
C10	0.4215 (2)	0.2631 (3)	0.14585 (19)	0.0626 (6)
H10	0.4075	0.1774	0.0948	0.071 (7)*
C11	0.5398 (3)	0.3616 (3)	0.16129 (19)	0.0653 (7)
H11	0.6054	0.3435	0.1202	0.068 (7)*
C12	0.5605 (2)	0.4869 (3)	0.2378 (2)	0.0624 (6)
H12	0.6413	0.5535	0.2497	0.074 (7)*
C13	0.4614 (2)	0.5148 (2)	0.29760 (17)	0.0500 (5)
H13	0.4768	0.6002	0.3494	0.052 (6)*
C14	0.21018 (19)	0.34865 (18)	0.41448 (15)	0.0404 (4)
C15	0.0974 (2)	0.3378 (2)	0.46367 (17)	0.0501 (5)
H15	0.0313	0.3876	0.454	0.056 (6)*
C16	0.0820 (3)	0.2544 (2)	0.52653 (19)	0.0609 (6)
H16	0.0055	0.2481	0.558	0.077 (8)*
C17	0.1793 (3)	0.1808 (2)	0.54282 (19)	0.0610 (6)
H17	0.1678	0.123	0.5837	0.064 (7)*
C18	0.2934 (2)	0.1936 (2)	0.49816 (18)	0.0533 (5)
H18	0.361	0.1465	0.5108	0.065 (7)*
C19	0.3086 (2)	0.27632 (18)	0.43426 (16)	0.0440 (5)
H19	0.3863	0.2833	0.4042	0.037 (5)*
C20	−0.0075 (2)	0.2198 (2)	0.07144 (17)	0.0540 (5)
H20A	−0.0026	0.1248	0.0473	0.065 (7)*
H20B	0.0746	0.2734	0.0598	0.056 (6)*
C21	−0.1225 (2)	0.1886 (2)	0.21632 (18)	0.0538 (5)
H21A	−0.2073	0.1945	0.1731	0.055 (6)*
H21B	−0.1218	0.2331	0.2913	0.062 (6)*
C22	−0.1348 (2)	0.2351 (2)	0.00215 (17)	0.0537 (5)
C23	−0.1528 (3)	0.3613 (3)	0.0002 (2)	0.0681 (6)
H23	−0.0867	0.4396	0.0444	0.080 (9)*
C24	−0.2672 (3)	0.3737 (4)	−0.0661 (2)	0.0866 (9)
H24	−0.2776	0.4597	−0.0665	0.092 (9)*
C25	−0.3650 (3)	0.2594 (5)	−0.1312 (3)	0.0960 (10)
H25	−0.4423	0.2674	−0.1757	0.107 (10)*
C26	−0.3490 (3)	0.1334 (4)	−0.1307 (3)	0.0977 (10)
H26	−0.4152	0.0554	−0.1752	0.117 (11)*
C27	−0.2346 (3)	0.1220 (3)	−0.0643 (2)	0.0759 (7)
H27	−0.2248	0.0356	−0.0645	0.081 (9)*
C28	−0.1243 (2)	0.0395 (2)	0.19885 (17)	0.0510 (5)
C29	−0.2440 (3)	−0.0607 (3)	0.1463 (2)	0.0682 (7)
H29	−0.3233	−0.0362	0.119	0.077 (8)*
C30	−0.2490 (3)	−0.1966 (3)	0.1333 (2)	0.0807 (8)
H30	−0.3308	−0.2626	0.0971	0.087 (8)*
C31	−0.1335 (3)	−0.2345 (3)	0.1737 (2)	0.0753 (7)
H31	−0.1365	−0.3258	0.1659	0.094 (9)*
C32	−0.0142 (3)	−0.1363 (3)	0.2256 (2)	0.0724 (7)
H32	0.0651	−0.1613	0.2523	0.097 (10)*
C33	−0.0096 (2)	−0.0006 (3)	0.2390 (2)	0.0632 (6)
H33	0.0723	0.065	0.2759	0.069 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0463 (3)	0.0497 (3)	0.0536 (3)	0.0144 (2)	0.0028 (2)	0.0149 (2)
N1	0.0434 (9)	0.0534 (10)	0.0472 (10)	0.0053 (8)	0.0106 (8)	0.0126 (8)
C1	0.0397 (10)	0.0385 (10)	0.0412 (10)	0.0110 (8)	0.0061 (8)	0.0129 (8)
C2	0.0389 (10)	0.0387 (10)	0.0450 (11)	0.0109 (8)	0.0090 (8)	0.0122 (8)
C3	0.0462 (11)	0.0429 (11)	0.0469 (11)	0.0123 (9)	0.0109 (9)	0.0162 (9)
C4	0.0495 (12)	0.0513 (12)	0.0446 (12)	0.0121 (9)	0.0088 (9)	0.0062 (10)
C5	0.0589 (13)	0.0373 (11)	0.0642 (15)	0.0124 (10)	0.0072 (11)	0.0049 (10)
C6	0.0667 (14)	0.0421 (12)	0.0683 (15)	0.0148 (10)	0.0058 (12)	0.0218 (11)
C7	0.0575 (12)	0.0453 (12)	0.0485 (12)	0.0136 (9)	0.0054 (10)	0.0174 (10)
C8	0.0416 (10)	0.0453 (11)	0.0373 (10)	0.0136 (8)	0.0043 (8)	0.0150 (9)
C9	0.0452 (12)	0.0553 (13)	0.0516 (12)	0.0118 (10)	0.0085 (10)	0.0067 (10)
C10	0.0614 (14)	0.0701 (16)	0.0510 (13)	0.0245 (12)	0.0134 (11)	0.0060 (12)
C11	0.0622 (15)	0.0937 (19)	0.0581 (14)	0.0339 (14)	0.0305 (12)	0.0337 (14)
C12	0.0519 (13)	0.0735 (16)	0.0720 (16)	0.0131 (12)	0.0216 (12)	0.0359 (14)
C13	0.0494 (12)	0.0496 (12)	0.0525 (12)	0.0112 (9)	0.0118 (10)	0.0189 (10)
C14	0.0394 (10)	0.0356 (10)	0.0422 (10)	0.0071 (8)	0.0060 (8)	0.0094 (8)
C15	0.0494 (11)	0.0507 (12)	0.0538 (12)	0.0169 (10)	0.0154 (10)	0.0173 (10)
C16	0.0629 (14)	0.0648 (15)	0.0626 (14)	0.0127 (11)	0.0281 (12)	0.0259 (12)
C17	0.0754 (16)	0.0537 (13)	0.0626 (14)	0.0139 (12)	0.0209 (12)	0.0302 (12)
C18	0.0585 (13)	0.0408 (11)	0.0624 (14)	0.0149 (10)	0.0083 (11)	0.0204 (10)
C19	0.0407 (10)	0.0405 (11)	0.0499 (12)	0.0093 (8)	0.0097 (9)	0.0138 (9)
C20	0.0498 (12)	0.0590 (14)	0.0490 (12)	0.0109 (10)	0.0128 (10)	0.0116 (10)
C21	0.0397 (11)	0.0638 (14)	0.0538 (13)	0.0082 (10)	0.0123 (10)	0.0144 (11)
C22	0.0510 (12)	0.0656 (14)	0.0445 (12)	0.0099 (11)	0.0145 (10)	0.0181 (11)
C23	0.0743 (16)	0.0766 (17)	0.0606 (15)	0.0189 (14)	0.0184 (13)	0.0308 (14)
C24	0.098 (2)	0.114 (3)	0.081 (2)	0.045 (2)	0.0332 (18)	0.0616 (19)
C25	0.0673 (19)	0.159 (3)	0.082 (2)	0.025 (2)	0.0131 (16)	0.072 (2)
C26	0.0693 (19)	0.127 (3)	0.081 (2)	−0.0107 (19)	−0.0121 (16)	0.046 (2)
C27	0.0680 (16)	0.0794 (19)	0.0680 (17)	0.0003 (14)	−0.0032 (13)	0.0258 (14)
C28	0.0463 (11)	0.0571 (13)	0.0444 (11)	0.0029 (10)	0.0098 (9)	0.0143 (10)
C29	0.0521 (14)	0.0737 (17)	0.0674 (16)	−0.0010 (12)	0.0016 (12)	0.0217 (13)
C30	0.0751 (19)	0.0650 (17)	0.0789 (19)	−0.0164 (15)	0.0067 (15)	0.0138 (14)
C31	0.100 (2)	0.0581 (16)	0.0681 (17)	0.0095 (15)	0.0273 (16)	0.0215 (13)
C32	0.0753 (17)	0.0702 (17)	0.0760 (18)	0.0204 (14)	0.0163 (14)	0.0286 (14)
C33	0.0507 (13)	0.0635 (15)	0.0661 (15)	0.0051 (11)	0.0031 (11)	0.0174 (12)

Geometric parameters (Å, º)

S1—N1	1.6852 (18)	C16—H16	0.93
S1—C1	1.8941 (19)	C17—C18	1.371 (3)
N1—C21	1.469 (3)	C17—H17	0.93
N1—C20	1.480 (3)	C18—C19	1.388 (3)
C1—C14	1.529 (3)	C18—H18	0.93
C1—C2	1.533 (3)	C19—H19	0.93
C1—C8	1.537 (3)	C20—C22	1.513 (3)
C2—C3	1.389 (3)	C20—H20A	0.97
C2—C7	1.396 (3)	C20—H20B	0.97
C3—C4	1.383 (3)	C21—C28	1.514 (3)
C3—H3	0.93	C21—H21A	0.97
C4—C5	1.374 (3)	C21—H21B	0.97
C4—H4	0.93	C22—C27	1.374 (3)
C5—C6	1.375 (3)	C22—C23	1.378 (3)
C5—H5	0.93	C23—C24	1.382 (4)
C6—C7	1.376 (3)	C23—H23	0.93
C6—H6	0.93	C24—C25	1.366 (5)
C7—H7	0.93	C24—H24	0.93
C8—C13	1.386 (3)	C25—C26	1.365 (5)
C8—C9	1.388 (3)	C25—H25	0.93
C9—C10	1.376 (3)	C26—C27	1.378 (4)
C9—H9	0.93	C26—H26	0.93
C10—C11	1.372 (3)	C27—H27	0.93
C10—H10	0.93	C28—C33	1.375 (3)
C11—C12	1.370 (3)	C28—C29	1.377 (3)
C11—H11	0.93	C29—C30	1.380 (4)
C12—C13	1.385 (3)	C29—H29	0.93
C12—H12	0.93	C30—C31	1.370 (4)
C13—H13	0.93	C30—H30	0.93
C14—C19	1.385 (3)	C31—C32	1.363 (4)
C14—C15	1.395 (3)	C31—H31	0.93
C15—C16	1.382 (3)	C32—C33	1.379 (3)
C15—H15	0.93	C32—H32	0.93
C16—C17	1.377 (3)	C33—H33	0.93
N1—S1—C1	105.61 (8)	C18—C17—H17	120.4
C21—N1—C20	113.52 (16)	C16—C17—H17	120.4
C21—N1—S1	116.97 (14)	C17—C18—C19	120.5 (2)
C20—N1—S1	116.77 (14)	C17—C18—H18	119.7
C14—C1—C2	111.42 (15)	C19—C18—H18	119.7
C14—C1—C8	112.01 (14)	C14—C19—C18	121.19 (19)
C2—C1—C8	111.58 (15)	C14—C19—H19	119.4
C14—C1—S1	109.78 (12)	C18—C19—H19	119.4
C2—C1—S1	101.39 (12)	N1—C20—C22	115.60 (17)
C8—C1—S1	110.15 (12)	N1—C20—H20A	108.4
C3—C2—C7	117.50 (18)	C22—C20—H20A	108.4
C3—C2—C1	122.12 (16)	N1—C20—H20B	108.4
C7—C2—C1	120.29 (17)	C22—C20—H20B	108.4
C4—C3—C2	121.07 (19)	H20A—C20—H20B	107.4
C4—C3—H3	119.5	N1—C21—C28	113.32 (17)
C2—C3—H3	119.5	N1—C21—H21A	108.9
C5—C4—C3	120.3 (2)	C28—C21—H21A	108.9
C5—C4—H4	119.8	N1—C21—H21B	108.9
C3—C4—H4	119.8	C28—C21—H21B	108.9
C4—C5—C6	119.5 (2)	H21A—C21—H21B	107.7
C4—C5—H5	120.2	C27—C22—C23	117.6 (2)
C6—C5—H5	120.2	C27—C22—C20	120.6 (2)
C5—C6—C7	120.4 (2)	C23—C22—C20	121.7 (2)
C5—C6—H6	119.8	C22—C23—C24	121.2 (3)
C7—C6—H6	119.8	C22—C23—H23	119.4
C6—C7—C2	121.2 (2)	C24—C23—H23	119.4
C6—C7—H7	119.4	C25—C24—C23	119.9 (3)
C2—C7—H7	119.4	C25—C24—H24	120
C13—C8—C9	117.18 (18)	C23—C24—H24	120
C13—C8—C1	122.07 (17)	C26—C25—C24	119.8 (3)
C9—C8—C1	120.67 (17)	C26—C25—H25	120.1
C10—C9—C8	121.6 (2)	C24—C25—H25	120.1
C10—C9—H9	119.2	C25—C26—C27	119.9 (3)
C8—C9—H9	119.2	C25—C26—H26	120
C11—C10—C9	120.3 (2)	C27—C26—H26	120
C11—C10—H10	119.9	C22—C27—C26	121.5 (3)
C9—C10—H10	119.9	C22—C27—H27	119.2
C12—C11—C10	119.4 (2)	C26—C27—H27	119.2
C12—C11—H11	120.3	C33—C28—C29	117.5 (2)
C10—C11—H11	120.3	C33—C28—C21	121.66 (19)
C11—C12—C13	120.2 (2)	C29—C28—C21	120.7 (2)
C11—C12—H12	119.9	C28—C29—C30	121.5 (2)
C13—C12—H12	119.9	C28—C29—H29	119.2
C12—C13—C8	121.2 (2)	C30—C29—H29	119.2
C12—C13—H13	119.4	C31—C30—C29	120.1 (2)
C8—C13—H13	119.4	C31—C30—H30	120
C19—C14—C15	117.32 (18)	C29—C30—H30	120
C19—C14—C1	121.44 (17)	C32—C31—C30	119.0 (3)
C15—C14—C1	121.07 (16)	C32—C31—H31	120.5
C16—C15—C14	121.3 (2)	C30—C31—H31	120.5
C16—C15—H15	119.4	C31—C32—C33	120.8 (3)
C14—C15—H15	119.4	C31—C32—H32	119.6
C17—C16—C15	120.3 (2)	C33—C32—H32	119.6
C17—C16—H16	119.8	C28—C33—C32	121.0 (2)
C15—C16—H16	119.8	C28—C33—H33	119.5
C18—C17—C16	119.3 (2)	C32—C33—H33	119.5
C1—S1—N1—C21	108.64 (16)	C2—C1—C14—C15	67.1 (2)
C1—S1—N1—C20	−112.05 (15)	C8—C1—C14—C15	−167.08 (17)
N1—S1—C1—C14	−53.23 (14)	S1—C1—C14—C15	−44.4 (2)
N1—S1—C1—C2	−171.16 (11)	C19—C14—C15—C16	−2.2 (3)
N1—S1—C1—C8	70.57 (14)	C1—C14—C15—C16	−177.47 (19)
C14—C1—C2—C3	14.5 (2)	C14—C15—C16—C17	0.6 (3)
C8—C1—C2—C3	−111.50 (19)	C15—C16—C17—C18	1.6 (4)
S1—C1—C2—C3	131.27 (16)	C16—C17—C18—C19	−2.1 (3)
C14—C1—C2—C7	−168.95 (17)	C15—C14—C19—C18	1.7 (3)
C8—C1—C2—C7	65.0 (2)	C1—C14—C19—C18	176.91 (18)
S1—C1—C2—C7	−52.2 (2)	C17—C18—C19—C14	0.5 (3)
C7—C2—C3—C4	−0.4 (3)	C21—N1—C20—C22	57.5 (2)
C1—C2—C3—C4	176.18 (17)	S1—N1—C20—C22	−83.2 (2)
C2—C3—C4—C5	0.6 (3)	C20—N1—C21—C28	69.8 (2)
C3—C4—C5—C6	−0.2 (3)	S1—N1—C21—C28	−149.62 (15)
C4—C5—C6—C7	−0.4 (3)	N1—C20—C22—C27	−109.1 (2)
C5—C6—C7—C2	0.5 (3)	N1—C20—C22—C23	73.2 (3)
C3—C2—C7—C6	−0.1 (3)	C27—C22—C23—C24	0.0 (4)
C1—C2—C7—C6	−176.76 (18)	C20—C22—C23—C24	177.8 (2)
C14—C1—C8—C13	−117.65 (19)	C22—C23—C24—C25	0.1 (4)
C2—C1—C8—C13	8.1 (2)	C23—C24—C25—C26	−0.3 (4)
S1—C1—C8—C13	119.86 (17)	C24—C25—C26—C27	0.3 (5)
C14—C1—C8—C9	59.1 (2)	C23—C22—C27—C26	0.0 (4)
C2—C1—C8—C9	−175.17 (17)	C20—C22—C27—C26	−177.8 (2)
S1—C1—C8—C9	−63.4 (2)	C25—C26—C27—C22	−0.1 (5)
C13—C8—C9—C10	−2.1 (3)	N1—C21—C28—C33	50.1 (3)
C1—C8—C9—C10	−178.99 (19)	N1—C21—C28—C29	−133.1 (2)
C8—C9—C10—C11	0.7 (3)	C33—C28—C29—C30	−0.6 (4)
C9—C10—C11—C12	1.0 (4)	C21—C28—C29—C30	−177.5 (2)
C10—C11—C12—C13	−1.3 (3)	C28—C29—C30—C31	0.5 (4)
C11—C12—C13—C8	−0.1 (3)	C29—C30—C31—C32	−0.6 (4)
C9—C8—C13—C12	1.8 (3)	C30—C31—C32—C33	1.0 (4)
C1—C8—C13—C12	178.64 (18)	C29—C28—C33—C32	1.0 (4)
C2—C1—C14—C19	−107.92 (19)	C21—C28—C33—C32	177.8 (2)
C8—C1—C14—C19	17.9 (2)	C31—C32—C33—C28	−1.2 (4)
S1—C1—C14—C19	140.57 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···N1	0.93	2.57	3.185 (3)	124
C15—H15···S1	0.93	2.81	3.148 (3)	103