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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804021427/ac6116sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804021427/ac6116Isup2.hkl
Contains datablock I

CCDC reference: 252961

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

Computing details top

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) top
Crystal data top
C33H29NSZ = 2
Mr = 471.63F(000) = 500
Triclinic, P1Dx = 1.217 Mg m3
Hall symbol: -P 1Melting point: 409 K
a = 10.009 (2) ÅCu Kα radiation, λ = 1.5418 Å
b = 10.519 (3) ÅCell parameters from 25 reflections
c = 13.311 (1) Åθ = 12.0–18.4°
α = 106.822 (13)°µ = 1.26 mm1
β = 99.037 (13)°T = 293 K
γ = 100.245 (19)°Prismatic, colourless
V = 1287.3 (5) Å30.24 × 0.24 × 0.15 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.024
ω–2θ scansθmax = 73.9°, θmin = 5.2°
Absorption correction: ψ scan
(North et al., 1968)
h = 1212
Tmin = 0.716, Tmax = 0.827k = 1213
5442 measured reflectionsl = 160
5207 independent reflections3 standard reflections every 120 reflections
3437 reflections with I > 2σ(I) intensity decay: 1%
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.043 w = 1/[σ2(Fo2) + (0.0525P)2 + 0.217P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.122(Δ/σ)max < 0.001
S = 1.07Δρmax = 0.34 e Å3
5207 reflectionsΔρmin = 0.20 e Å3
345 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
S10.05767 (5)0.42981 (5)0.25809 (4)0.05087 (16)
N10.00227 (17)0.26189 (17)0.18844 (13)0.0496 (4)
C10.22993 (19)0.44546 (18)0.34880 (15)0.0399 (4)
C20.26318 (19)0.59537 (19)0.42044 (15)0.0410 (4)
C30.3031 (2)0.6345 (2)0.53182 (16)0.0447 (5)
H30.30480.56790.56490.042 (5)*
C40.3404 (2)0.7709 (2)0.59438 (17)0.0507 (5)
H40.36760.79520.66880.060 (6)*
C50.3375 (2)0.8709 (2)0.54715 (19)0.0567 (6)
H50.36240.96260.58930.053 (6)*
C60.2975 (2)0.8343 (2)0.43707 (19)0.0590 (6)
H60.29480.90150.40480.066 (7)*
C70.2613 (2)0.6987 (2)0.37440 (18)0.0505 (5)
H70.23510.67560.30.047 (6)*
C80.33973 (19)0.41776 (19)0.28167 (15)0.0412 (4)
C90.3234 (2)0.2907 (2)0.20559 (17)0.0533 (5)
H90.24420.22250.19470.048 (6)*
C100.4215 (2)0.2631 (3)0.14585 (19)0.0626 (6)
H100.40750.17740.09480.071 (7)*
C110.5398 (3)0.3616 (3)0.16129 (19)0.0653 (7)
H110.60540.34350.12020.068 (7)*
C120.5605 (2)0.4869 (3)0.2378 (2)0.0624 (6)
H120.64130.55350.24970.074 (7)*
C130.4614 (2)0.5148 (2)0.29760 (17)0.0500 (5)
H130.47680.60020.34940.052 (6)*
C140.21018 (19)0.34865 (18)0.41448 (15)0.0404 (4)
C150.0974 (2)0.3378 (2)0.46367 (17)0.0501 (5)
H150.03130.38760.4540.056 (6)*
C160.0820 (3)0.2544 (2)0.52653 (19)0.0609 (6)
H160.00550.24810.5580.077 (8)*
C170.1793 (3)0.1808 (2)0.54282 (19)0.0610 (6)
H170.16780.1230.58370.064 (7)*
C180.2934 (2)0.1936 (2)0.49816 (18)0.0533 (5)
H180.3610.14650.51080.065 (7)*
C190.3086 (2)0.27632 (18)0.43426 (16)0.0440 (5)
H190.38630.28330.40420.037 (5)*
C200.0075 (2)0.2198 (2)0.07144 (17)0.0540 (5)
H20A0.00260.12480.04730.065 (7)*
H20B0.07460.27340.05980.056 (6)*
C210.1225 (2)0.1886 (2)0.21632 (18)0.0538 (5)
H21A0.20730.19450.17310.055 (6)*
H21B0.12180.23310.29130.062 (6)*
C220.1348 (2)0.2351 (2)0.00215 (17)0.0537 (5)
C230.1528 (3)0.3613 (3)0.0002 (2)0.0681 (6)
H230.08670.43960.04440.080 (9)*
C240.2672 (3)0.3737 (4)0.0661 (2)0.0866 (9)
H240.27760.45970.06650.092 (9)*
C250.3650 (3)0.2594 (5)0.1312 (3)0.0960 (10)
H250.44230.26740.17570.107 (10)*
C260.3490 (3)0.1334 (4)0.1307 (3)0.0977 (10)
H260.41520.05540.17520.117 (11)*
C270.2346 (3)0.1220 (3)0.0643 (2)0.0759 (7)
H270.22480.03560.06450.081 (9)*
C280.1243 (2)0.0395 (2)0.19885 (17)0.0510 (5)
C290.2440 (3)0.0607 (3)0.1463 (2)0.0682 (7)
H290.32330.03620.1190.077 (8)*
C300.2490 (3)0.1966 (3)0.1333 (2)0.0807 (8)
H300.33080.26260.09710.087 (8)*
C310.1335 (3)0.2345 (3)0.1737 (2)0.0753 (7)
H310.13650.32580.16590.094 (9)*
C320.0142 (3)0.1363 (3)0.2256 (2)0.0724 (7)
H320.06510.16130.25230.097 (10)*
C330.0096 (2)0.0006 (3)0.2390 (2)0.0632 (6)
H330.07230.0650.27590.069 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0463 (3)0.0497 (3)0.0536 (3)0.0144 (2)0.0028 (2)0.0149 (2)
N10.0434 (9)0.0534 (10)0.0472 (10)0.0053 (8)0.0106 (8)0.0126 (8)
C10.0397 (10)0.0385 (10)0.0412 (10)0.0110 (8)0.0061 (8)0.0129 (8)
C20.0389 (10)0.0387 (10)0.0450 (11)0.0109 (8)0.0090 (8)0.0122 (8)
C30.0462 (11)0.0429 (11)0.0469 (11)0.0123 (9)0.0109 (9)0.0162 (9)
C40.0495 (12)0.0513 (12)0.0446 (12)0.0121 (9)0.0088 (9)0.0062 (10)
C50.0589 (13)0.0373 (11)0.0642 (15)0.0124 (10)0.0072 (11)0.0049 (10)
C60.0667 (14)0.0421 (12)0.0683 (15)0.0148 (10)0.0058 (12)0.0218 (11)
C70.0575 (12)0.0453 (12)0.0485 (12)0.0136 (9)0.0054 (10)0.0174 (10)
C80.0416 (10)0.0453 (11)0.0373 (10)0.0136 (8)0.0043 (8)0.0150 (9)
C90.0452 (12)0.0553 (13)0.0516 (12)0.0118 (10)0.0085 (10)0.0067 (10)
C100.0614 (14)0.0701 (16)0.0510 (13)0.0245 (12)0.0134 (11)0.0060 (12)
C110.0622 (15)0.0937 (19)0.0581 (14)0.0339 (14)0.0305 (12)0.0337 (14)
C120.0519 (13)0.0735 (16)0.0720 (16)0.0131 (12)0.0216 (12)0.0359 (14)
C130.0494 (12)0.0496 (12)0.0525 (12)0.0112 (9)0.0118 (10)0.0189 (10)
C140.0394 (10)0.0356 (10)0.0422 (10)0.0071 (8)0.0060 (8)0.0094 (8)
C150.0494 (11)0.0507 (12)0.0538 (12)0.0169 (10)0.0154 (10)0.0173 (10)
C160.0629 (14)0.0648 (15)0.0626 (14)0.0127 (11)0.0281 (12)0.0259 (12)
C170.0754 (16)0.0537 (13)0.0626 (14)0.0139 (12)0.0209 (12)0.0302 (12)
C180.0585 (13)0.0408 (11)0.0624 (14)0.0149 (10)0.0083 (11)0.0204 (10)
C190.0407 (10)0.0405 (11)0.0499 (12)0.0093 (8)0.0097 (9)0.0138 (9)
C200.0498 (12)0.0590 (14)0.0490 (12)0.0109 (10)0.0128 (10)0.0116 (10)
C210.0397 (11)0.0638 (14)0.0538 (13)0.0082 (10)0.0123 (10)0.0144 (11)
C220.0510 (12)0.0656 (14)0.0445 (12)0.0099 (11)0.0145 (10)0.0181 (11)
C230.0743 (16)0.0766 (17)0.0606 (15)0.0189 (14)0.0184 (13)0.0308 (14)
C240.098 (2)0.114 (3)0.081 (2)0.045 (2)0.0332 (18)0.0616 (19)
C250.0673 (19)0.159 (3)0.082 (2)0.025 (2)0.0131 (16)0.072 (2)
C260.0693 (19)0.127 (3)0.081 (2)0.0107 (19)0.0121 (16)0.046 (2)
C270.0680 (16)0.0794 (19)0.0680 (17)0.0003 (14)0.0032 (13)0.0258 (14)
C280.0463 (11)0.0571 (13)0.0444 (11)0.0029 (10)0.0098 (9)0.0143 (10)
C290.0521 (14)0.0737 (17)0.0674 (16)0.0010 (12)0.0016 (12)0.0217 (13)
C300.0751 (19)0.0650 (17)0.0789 (19)0.0164 (15)0.0067 (15)0.0138 (14)
C310.100 (2)0.0581 (16)0.0681 (17)0.0095 (15)0.0273 (16)0.0215 (13)
C320.0753 (17)0.0702 (17)0.0760 (18)0.0204 (14)0.0163 (14)0.0286 (14)
C330.0507 (13)0.0635 (15)0.0661 (15)0.0051 (11)0.0031 (11)0.0174 (12)
Geometric parameters (Å, º) top
S1—N11.6852 (18)C16—H160.93
S1—C11.8941 (19)C17—C181.371 (3)
N1—C211.469 (3)C17—H170.93
N1—C201.480 (3)C18—C191.388 (3)
C1—C141.529 (3)C18—H180.93
C1—C21.533 (3)C19—H190.93
C1—C81.537 (3)C20—C221.513 (3)
C2—C31.389 (3)C20—H20A0.97
C2—C71.396 (3)C20—H20B0.97
C3—C41.383 (3)C21—C281.514 (3)
C3—H30.93C21—H21A0.97
C4—C51.374 (3)C21—H21B0.97
C4—H40.93C22—C271.374 (3)
C5—C61.375 (3)C22—C231.378 (3)
C5—H50.93C23—C241.382 (4)
C6—C71.376 (3)C23—H230.93
C6—H60.93C24—C251.366 (5)
C7—H70.93C24—H240.93
C8—C131.386 (3)C25—C261.365 (5)
C8—C91.388 (3)C25—H250.93
C9—C101.376 (3)C26—C271.378 (4)
C9—H90.93C26—H260.93
C10—C111.372 (3)C27—H270.93
C10—H100.93C28—C331.375 (3)
C11—C121.370 (3)C28—C291.377 (3)
C11—H110.93C29—C301.380 (4)
C12—C131.385 (3)C29—H290.93
C12—H120.93C30—C311.370 (4)
C13—H130.93C30—H300.93
C14—C191.385 (3)C31—C321.363 (4)
C14—C151.395 (3)C31—H310.93
C15—C161.382 (3)C32—C331.379 (3)
C15—H150.93C32—H320.93
C16—C171.377 (3)C33—H330.93
N1—S1—C1105.61 (8)C18—C17—H17120.4
C21—N1—C20113.52 (16)C16—C17—H17120.4
C21—N1—S1116.97 (14)C17—C18—C19120.5 (2)
C20—N1—S1116.77 (14)C17—C18—H18119.7
C14—C1—C2111.42 (15)C19—C18—H18119.7
C14—C1—C8112.01 (14)C14—C19—C18121.19 (19)
C2—C1—C8111.58 (15)C14—C19—H19119.4
C14—C1—S1109.78 (12)C18—C19—H19119.4
C2—C1—S1101.39 (12)N1—C20—C22115.60 (17)
C8—C1—S1110.15 (12)N1—C20—H20A108.4
C3—C2—C7117.50 (18)C22—C20—H20A108.4
C3—C2—C1122.12 (16)N1—C20—H20B108.4
C7—C2—C1120.29 (17)C22—C20—H20B108.4
C4—C3—C2121.07 (19)H20A—C20—H20B107.4
C4—C3—H3119.5N1—C21—C28113.32 (17)
C2—C3—H3119.5N1—C21—H21A108.9
C5—C4—C3120.3 (2)C28—C21—H21A108.9
C5—C4—H4119.8N1—C21—H21B108.9
C3—C4—H4119.8C28—C21—H21B108.9
C4—C5—C6119.5 (2)H21A—C21—H21B107.7
C4—C5—H5120.2C27—C22—C23117.6 (2)
C6—C5—H5120.2C27—C22—C20120.6 (2)
C5—C6—C7120.4 (2)C23—C22—C20121.7 (2)
C5—C6—H6119.8C22—C23—C24121.2 (3)
C7—C6—H6119.8C22—C23—H23119.4
C6—C7—C2121.2 (2)C24—C23—H23119.4
C6—C7—H7119.4C25—C24—C23119.9 (3)
C2—C7—H7119.4C25—C24—H24120
C13—C8—C9117.18 (18)C23—C24—H24120
C13—C8—C1122.07 (17)C26—C25—C24119.8 (3)
C9—C8—C1120.67 (17)C26—C25—H25120.1
C10—C9—C8121.6 (2)C24—C25—H25120.1
C10—C9—H9119.2C25—C26—C27119.9 (3)
C8—C9—H9119.2C25—C26—H26120
C11—C10—C9120.3 (2)C27—C26—H26120
C11—C10—H10119.9C22—C27—C26121.5 (3)
C9—C10—H10119.9C22—C27—H27119.2
C12—C11—C10119.4 (2)C26—C27—H27119.2
C12—C11—H11120.3C33—C28—C29117.5 (2)
C10—C11—H11120.3C33—C28—C21121.66 (19)
C11—C12—C13120.2 (2)C29—C28—C21120.7 (2)
C11—C12—H12119.9C28—C29—C30121.5 (2)
C13—C12—H12119.9C28—C29—H29119.2
C12—C13—C8121.2 (2)C30—C29—H29119.2
C12—C13—H13119.4C31—C30—C29120.1 (2)
C8—C13—H13119.4C31—C30—H30120
C19—C14—C15117.32 (18)C29—C30—H30120
C19—C14—C1121.44 (17)C32—C31—C30119.0 (3)
C15—C14—C1121.07 (16)C32—C31—H31120.5
C16—C15—C14121.3 (2)C30—C31—H31120.5
C16—C15—H15119.4C31—C32—C33120.8 (3)
C14—C15—H15119.4C31—C32—H32119.6
C17—C16—C15120.3 (2)C33—C32—H32119.6
C17—C16—H16119.8C28—C33—C32121.0 (2)
C15—C16—H16119.8C28—C33—H33119.5
C18—C17—C16119.3 (2)C32—C33—H33119.5
C1—S1—N1—C21108.64 (16)C2—C1—C14—C1567.1 (2)
C1—S1—N1—C20112.05 (15)C8—C1—C14—C15167.08 (17)
N1—S1—C1—C1453.23 (14)S1—C1—C14—C1544.4 (2)
N1—S1—C1—C2171.16 (11)C19—C14—C15—C162.2 (3)
N1—S1—C1—C870.57 (14)C1—C14—C15—C16177.47 (19)
C14—C1—C2—C314.5 (2)C14—C15—C16—C170.6 (3)
C8—C1—C2—C3111.50 (19)C15—C16—C17—C181.6 (4)
S1—C1—C2—C3131.27 (16)C16—C17—C18—C192.1 (3)
C14—C1—C2—C7168.95 (17)C15—C14—C19—C181.7 (3)
C8—C1—C2—C765.0 (2)C1—C14—C19—C18176.91 (18)
S1—C1—C2—C752.2 (2)C17—C18—C19—C140.5 (3)
C7—C2—C3—C40.4 (3)C21—N1—C20—C2257.5 (2)
C1—C2—C3—C4176.18 (17)S1—N1—C20—C2283.2 (2)
C2—C3—C4—C50.6 (3)C20—N1—C21—C2869.8 (2)
C3—C4—C5—C60.2 (3)S1—N1—C21—C28149.62 (15)
C4—C5—C6—C70.4 (3)N1—C20—C22—C27109.1 (2)
C5—C6—C7—C20.5 (3)N1—C20—C22—C2373.2 (3)
C3—C2—C7—C60.1 (3)C27—C22—C23—C240.0 (4)
C1—C2—C7—C6176.76 (18)C20—C22—C23—C24177.8 (2)
C14—C1—C8—C13117.65 (19)C22—C23—C24—C250.1 (4)
C2—C1—C8—C138.1 (2)C23—C24—C25—C260.3 (4)
S1—C1—C8—C13119.86 (17)C24—C25—C26—C270.3 (5)
C14—C1—C8—C959.1 (2)C23—C22—C27—C260.0 (4)
C2—C1—C8—C9175.17 (17)C20—C22—C27—C26177.8 (2)
S1—C1—C8—C963.4 (2)C25—C26—C27—C220.1 (5)
C13—C8—C9—C102.1 (3)N1—C21—C28—C3350.1 (3)
C1—C8—C9—C10178.99 (19)N1—C21—C28—C29133.1 (2)
C8—C9—C10—C110.7 (3)C33—C28—C29—C300.6 (4)
C9—C10—C11—C121.0 (4)C21—C28—C29—C30177.5 (2)
C10—C11—C12—C131.3 (3)C28—C29—C30—C310.5 (4)
C11—C12—C13—C80.1 (3)C29—C30—C31—C320.6 (4)
C9—C8—C13—C121.8 (3)C30—C31—C32—C331.0 (4)
C1—C8—C13—C12178.64 (18)C29—C28—C33—C321.0 (4)
C2—C1—C14—C19107.92 (19)C21—C28—C33—C32177.8 (2)
C8—C1—C14—C1917.9 (2)C31—C32—C33—C281.2 (4)
S1—C1—C14—C19140.57 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···N10.932.573.185 (3)124
C15—H15···S10.932.813.148 (3)103
 

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