3,5-Di-tert-butyl-N-[2-(methyl­sulfan­yl)phen­yl]salicylaldimine

The molecule of the title compound, C₂₂H₂₉NOS, is non-planar, with a dihedral angle of 32.06 (9)° between the two aromatic rings.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.147
• Data-to-parameter ratio = 20.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.59 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.28 Ratio

Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C30    -   C31     ..       5.58 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C30

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   2 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
   3 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: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

3,5-Di-tert-butyl-N-[2-(methylsulfanyl)phenyl]salicylaldimine

Crystal data

C22H29NOS	F(000) = 768
Mr = 355.52	Dx = 1.169 Mg m^−3
Monoclinic, P21/c	Melting point: 408-409 K K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 17.876 (3) Å	Cell parameters from 25 reflections
b = 8.990 (2) Å	θ = 6.7–12.1°
c = 12.6963 (12) Å	µ = 0.17 mm^−1
β = 98.161 (8)°	T = 173 K
V = 2019.7 (6) Å^3	Prism, yellow
Z = 4	0.48 × 0.37 × 0.37 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	θmax = 27.5°, θmin = 1.2°
Non–profiled ω/2θ scans	h = −23→22
4796 measured reflections	k = 0→11
4589 independent reflections	l = 0→16
3291 reflections with I > 2σ(I)	3 standard reflections every 120 min
Rint = 0.041	intensity decay: 4%

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.047	w = 1/[σ^2(Fo^2) + (0.0762P)^2 + 1.1485P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.147	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.41 e Å^−3
4589 reflections	Δρmin = −0.32 e Å^−3
230 parameters

Special details

Experimental. ¹H NMR (CDCl₃, 400 MHz): δ 13.51 (s, 1H, OH), 8.69 (s, 1H, N═CH), 7.51 (d, 1H, aromatic), 7.29 (m, 3H, aromatic), 7.21 (m, 2H, aromatic), 2.50 (s, 3H, SCH₃), 1.51 [s, 9H, C(CH₃)₃], 1.36 [s, 9H, C(CH₃)₃]. IR (Nujol, ν, cm^-1): 3577 (OH); 1612 (s, N═C). UV–vis [CH₂Cl₂: λ_max (ε)]: 368 nm (9570 M^-1 cm^-1), 273 nm (18000 M^-1 cm^-1). Analysis calculated (found) (%) for C₂₂H₂₉NOS: C 74.32 (74.37), H 8.22 (8.26), N 3.94 (4.10).

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
C1	−0.07395 (13)	−0.0093 (3)	0.1911 (2)	0.0438 (6)
H1A	−0.0963	−0.0817	0.2352	0.066*
H1B	−0.0859	−0.0376	0.116	0.066*
H1C	−0.0947	0.0897	0.2015	0.066*
C2	0.05535 (11)	0.1284 (2)	0.14188 (15)	0.0221 (4)
C3	0.00688 (12)	0.1960 (3)	0.06061 (17)	0.0291 (5)
H3	−0.045	0.1685	0.0487	0.035*
C4	0.03354 (13)	0.3034 (3)	−0.00327 (17)	0.0318 (5)
H4	−0.0002	0.3494	−0.0582	0.038*
C5	0.10838 (13)	0.3435 (3)	0.01238 (17)	0.0308 (5)
H5	0.1263	0.4166	−0.032	0.037*
C6	0.15783 (11)	0.2775 (2)	0.09276 (16)	0.0246 (4)
H6	0.2097	0.3048	0.1032	0.03*
C7	0.13141 (11)	0.1709 (2)	0.15835 (15)	0.0204 (4)
C10	0.23143 (11)	0.1679 (2)	0.30129 (15)	0.0209 (4)
H10	0.2425	0.2678	0.2847	0.025*
C11	0.27598 (11)	0.0964 (2)	0.39182 (15)	0.0198 (4)
C12	0.25793 (11)	−0.0476 (2)	0.42390 (15)	0.0203 (4)
C13	0.29698 (11)	−0.1093 (2)	0.51831 (16)	0.0220 (4)
C14	0.35433 (11)	−0.0249 (2)	0.57330 (15)	0.0220 (4)
H14	0.3815	−0.0662	0.6363	0.026*
C15	0.37539 (11)	0.1181 (2)	0.54254 (15)	0.0202 (4)
C16	0.33453 (10)	0.1768 (2)	0.45179 (15)	0.0207 (4)
H16	0.3463	0.2738	0.4293	0.025*
C20	0.27372 (12)	−0.2612 (2)	0.55858 (18)	0.0303 (5)
C21	0.32552 (14)	−0.3088 (3)	0.6600 (2)	0.0388 (6)
H21A	0.3092	−0.4058	0.6836	0.058*
H21B	0.3227	−0.2349	0.7161	0.058*
H21C	0.3777	−0.316	0.6451	0.058*
C22	0.27868 (16)	−0.3824 (3)	0.4742 (2)	0.0446 (7)
H22A	0.2637	−0.4784	0.5014	0.067*
H22B	0.3307	−0.3888	0.4586	0.067*
H22C	0.2448	−0.3572	0.4091	0.067*
C23	0.19312 (13)	−0.2499 (3)	0.5860 (2)	0.0430 (6)
H23A	0.1779	−0.3464	0.6119	0.064*
H23B	0.1585	−0.2217	0.5222	0.064*
H23C	0.1915	−0.1745	0.6413	0.064*
C30	0.43953 (11)	0.2017 (2)	0.61101 (16)	0.0247 (4)
C31	0.51127 (15)	0.1075 (3)	0.6268 (3)	0.0581 (9)
H31A	0.5008	0.0122	0.6592	0.087*
H31B	0.5509	0.1602	0.6735	0.087*
H31C	0.5281	0.0896	0.5577	0.087*
C32	0.4171 (2)	0.2316 (4)	0.7196 (3)	0.0710 (11)
H32A	0.4048	0.1373	0.7521	0.107*
H32B	0.3728	0.297	0.7122	0.107*
H32C	0.4591	0.2797	0.765	0.107*
C33	0.45904 (18)	0.3473 (3)	0.5608 (3)	0.0605 (9)
H33A	0.4737	0.3276	0.4906	0.091*
H33B	0.5011	0.395	0.6063	0.091*
H33C	0.4149	0.4131	0.5531	0.091*
N1	0.17763 (9)	0.10003 (18)	0.24318 (12)	0.0206 (3)
O1	0.20141 (9)	−0.12534 (16)	0.36808 (12)	0.0271 (3)
S1	0.02656 (3)	−0.00619 (6)	0.22854 (4)	0.02903 (16)
H1	0.1809 (19)	−0.084 (4)	0.316 (3)	0.065 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0290 (11)	0.0495 (16)	0.0532 (16)	−0.0074 (11)	0.0067 (11)	0.0160 (13)
C2	0.0281 (10)	0.0194 (9)	0.0182 (9)	0.0008 (8)	0.0014 (8)	0.0016 (7)
C3	0.0250 (10)	0.0327 (11)	0.0282 (11)	0.0005 (9)	−0.0015 (8)	0.0071 (9)
C4	0.0337 (11)	0.0342 (12)	0.0259 (10)	0.0058 (9)	−0.0015 (9)	0.0125 (9)
C5	0.0365 (12)	0.0307 (11)	0.0252 (10)	−0.0003 (9)	0.0040 (9)	0.0106 (9)
C6	0.0257 (10)	0.0255 (10)	0.0231 (10)	−0.0002 (8)	0.0050 (8)	0.0039 (8)
C7	0.0250 (9)	0.0192 (9)	0.0166 (9)	0.0028 (8)	0.0016 (7)	−0.0003 (7)
C10	0.0238 (9)	0.0201 (9)	0.0190 (9)	0.0015 (8)	0.0037 (7)	0.0034 (7)
C11	0.0209 (9)	0.0197 (9)	0.0188 (9)	0.0024 (7)	0.0026 (7)	0.0010 (7)
C12	0.0207 (9)	0.0187 (9)	0.0208 (9)	−0.0007 (7)	0.0001 (7)	−0.0009 (7)
C13	0.0211 (9)	0.0199 (9)	0.0244 (10)	0.0013 (7)	0.0010 (8)	0.0034 (8)
C14	0.0220 (9)	0.0236 (10)	0.0198 (9)	0.0015 (8)	0.0009 (7)	0.0036 (8)
C15	0.0198 (9)	0.0204 (9)	0.0208 (9)	0.0009 (7)	0.0038 (7)	−0.0010 (7)
C16	0.0219 (9)	0.0183 (9)	0.0222 (9)	−0.0006 (7)	0.0041 (7)	0.0009 (7)
C20	0.0304 (10)	0.0231 (10)	0.0342 (11)	−0.0055 (9)	−0.0071 (9)	0.0107 (9)
C21	0.0413 (13)	0.0319 (12)	0.0388 (13)	−0.0061 (10)	−0.0097 (11)	0.0151 (10)
C22	0.0565 (16)	0.0189 (11)	0.0519 (16)	0.0010 (10)	−0.0151 (13)	0.0038 (10)
C23	0.0340 (12)	0.0436 (15)	0.0487 (15)	−0.0122 (11)	−0.0032 (11)	0.0219 (12)
C30	0.0254 (10)	0.0246 (10)	0.0235 (10)	−0.0019 (8)	0.0012 (8)	−0.0028 (8)
C31	0.0339 (14)	0.0493 (17)	0.082 (2)	0.0003 (12)	−0.0245 (14)	−0.0208 (15)
C32	0.078 (2)	0.089 (3)	0.0509 (18)	−0.042 (2)	0.0263 (16)	−0.0395 (18)
C33	0.0596 (18)	0.0461 (17)	0.0657 (19)	−0.0294 (14)	−0.0263 (15)	0.0175 (14)
N1	0.0226 (8)	0.0216 (8)	0.0169 (8)	0.0039 (6)	0.0004 (6)	0.0008 (6)
O1	0.0306 (8)	0.0201 (7)	0.0266 (8)	−0.0037 (6)	−0.0096 (6)	0.0030 (6)
S1	0.0302 (3)	0.0291 (3)	0.0269 (3)	−0.0055 (2)	0.00072 (19)	0.0085 (2)

Geometric parameters (Å, º)

C1—S1	1.792 (2)	C15—C30	1.533 (3)
C1—H1A	0.98	C16—H16	0.95
C1—H1B	0.98	C20—C23	1.533 (3)
C1—H1C	0.98	C20—C21	1.536 (3)
C2—C3	1.390 (3)	C20—C22	1.539 (3)
C2—C7	1.399 (3)	C21—H21A	0.98
C2—S1	1.760 (2)	C21—H21B	0.98
C3—C4	1.388 (3)	C21—H21C	0.98
C3—H3	0.95	C22—H22A	0.98
C4—C5	1.373 (3)	C22—H22B	0.98
C4—H4	0.95	C22—H22C	0.98
C5—C6	1.385 (3)	C23—H23A	0.98
C5—H5	0.95	C23—H23B	0.98
C6—C7	1.395 (3)	C23—H23C	0.98
C6—H6	0.95	C30—C32	1.514 (3)
C7—N1	1.413 (2)	C30—C33	1.518 (3)
C10—N1	1.281 (2)	C30—C31	1.526 (3)
C10—C11	1.452 (3)	C31—H31A	0.98
C10—H10	0.95	C31—H31B	0.98
C11—C16	1.404 (3)	C31—H31C	0.98
C11—C12	1.409 (3)	C32—H32A	0.98
C12—O1	1.345 (2)	C32—H32B	0.98
C12—C13	1.412 (3)	C32—H32C	0.98
C13—C14	1.382 (3)	C33—H33A	0.98
C13—C20	1.536 (3)	C33—H33B	0.98
C14—C15	1.411 (3)	C33—H33C	0.98
C14—H14	0.95	O1—H1	0.80 (4)
C15—C16	1.379 (3)
S1—C1—H1A	109.5	C23—C20—C22	110.7 (2)
S1—C1—H1B	109.5	C13—C20—C22	110.65 (19)
H1A—C1—H1B	109.5	C21—C20—C22	107.37 (19)
S1—C1—H1C	109.5	C20—C21—H21A	109.5
H1A—C1—H1C	109.5	C20—C21—H21B	109.5
H1B—C1—H1C	109.5	H21A—C21—H21B	109.5
C3—C2—C7	118.79 (19)	C20—C21—H21C	109.5
C3—C2—S1	123.92 (16)	H21A—C21—H21C	109.5
C7—C2—S1	117.27 (14)	H21B—C21—H21C	109.5
C4—C3—C2	120.6 (2)	C20—C22—H22A	109.5
C4—C3—H3	119.7	C20—C22—H22B	109.5
C2—C3—H3	119.7	H22A—C22—H22B	109.5
C5—C4—C3	120.43 (19)	C20—C22—H22C	109.5
C5—C4—H4	119.8	H22A—C22—H22C	109.5
C3—C4—H4	119.8	H22B—C22—H22C	109.5
C4—C5—C6	120.1 (2)	C20—C23—H23A	109.5
C4—C5—H5	120	C20—C23—H23B	109.5
C6—C5—H5	120	H23A—C23—H23B	109.5
C5—C6—C7	119.95 (19)	C20—C23—H23C	109.5
C5—C6—H6	120	H23A—C23—H23C	109.5
C7—C6—H6	120	H23B—C23—H23C	109.5
C6—C7—C2	120.16 (17)	C32—C30—C33	109.6 (2)
C6—C7—N1	123.62 (17)	C32—C30—C31	107.8 (3)
C2—C7—N1	116.21 (17)	C33—C30—C31	107.1 (2)
N1—C10—C11	121.88 (18)	C32—C30—C15	109.26 (19)
N1—C10—H10	119.1	C33—C30—C15	112.47 (18)
C11—C10—H10	119.1	C31—C30—C15	110.45 (18)
C16—C11—C12	120.01 (17)	C30—C31—H31A	109.5
C16—C11—C10	118.97 (18)	C30—C31—H31B	109.5
C12—C11—C10	120.88 (17)	H31A—C31—H31B	109.5
O1—C12—C11	120.73 (17)	C30—C31—H31C	109.5
O1—C12—C13	119.16 (17)	H31A—C31—H31C	109.5
C11—C12—C13	120.04 (17)	H31B—C31—H31C	109.5
C14—C13—C12	117.06 (18)	C30—C32—H32A	109.5
C14—C13—C20	122.43 (17)	C30—C32—H32B	109.5
C12—C13—C20	120.48 (17)	H32A—C32—H32B	109.5
C13—C14—C15	124.65 (18)	C30—C32—H32C	109.5
C13—C14—H14	117.7	H32A—C32—H32C	109.5
C15—C14—H14	117.7	H32B—C32—H32C	109.5
C16—C15—C14	116.72 (17)	C30—C33—H33A	109.5
C16—C15—C30	123.45 (18)	C30—C33—H33B	109.5
C14—C15—C30	119.81 (17)	H33A—C33—H33B	109.5
C15—C16—C11	121.46 (18)	C30—C33—H33C	109.5
C15—C16—H16	119.3	H33A—C33—H33C	109.5
C11—C16—H16	119.3	H33B—C33—H33C	109.5
C23—C20—C13	108.94 (18)	C10—N1—C7	122.34 (17)
C23—C20—C21	107.6 (2)	C12—O1—H1	115 (3)
C13—C20—C21	111.54 (17)	C2—S1—C1	102.46 (11)
C7—C2—C3—C4	0.2 (3)	C13—C14—C15—C16	0.9 (3)
S1—C2—C3—C4	178.77 (18)	C13—C14—C15—C30	179.28 (19)
C2—C3—C4—C5	0.5 (4)	C14—C15—C16—C11	−1.4 (3)
C3—C4—C5—C6	−0.4 (4)	C30—C15—C16—C11	−179.69 (18)
C4—C5—C6—C7	−0.4 (3)	C12—C11—C16—C15	−0.1 (3)
C5—C6—C7—C2	1.2 (3)	C10—C11—C16—C15	175.70 (18)
C5—C6—C7—N1	−178.89 (19)	C14—C13—C20—C23	114.3 (2)
C3—C2—C7—C6	−1.1 (3)	C12—C13—C20—C23	−63.4 (3)
S1—C2—C7—C6	−179.72 (15)	C14—C13—C20—C21	−4.3 (3)
C3—C2—C7—N1	178.99 (18)	C12—C13—C20—C21	178.0 (2)
S1—C2—C7—N1	0.4 (2)	C14—C13—C20—C22	−123.8 (2)
N1—C10—C11—C16	179.55 (18)	C12—C13—C20—C22	58.5 (3)
N1—C10—C11—C12	−4.7 (3)	C16—C15—C30—C32	115.1 (3)
C16—C11—C12—O1	179.17 (18)	C14—C15—C30—C32	−63.1 (3)
C10—C11—C12—O1	3.5 (3)	C16—C15—C30—C33	−6.9 (3)
C16—C11—C12—C13	2.1 (3)	C14—C15—C30—C33	174.9 (2)
C10—C11—C12—C13	−173.58 (18)	C16—C15—C30—C31	−126.5 (2)
O1—C12—C13—C14	−179.62 (18)	C14—C15—C30—C31	55.3 (3)
C11—C12—C13—C14	−2.5 (3)	C11—C10—N1—C7	176.62 (17)
O1—C12—C13—C20	−1.8 (3)	C6—C7—N1—C10	35.9 (3)
C11—C12—C13—C20	175.29 (18)	C2—C7—N1—C10	−144.14 (19)
C12—C13—C14—C15	1.0 (3)	C3—C2—S1—C1	−5.6 (2)
C20—C13—C14—C15	−176.75 (19)	C7—C2—S1—C1	172.94 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.80 (4)	1.90 (4)	2.571 (2)	142 (3)