3-(4-tert-Butyl-2,6-dimethyl-3,5-dinitro­benzo­yl)-1,1-bis­(methyl­sulfan­yl)prop-2-en-1-one

The bond lengths and mol­ecular conformation of the title compound, C₁₇H₂₂N₂O₅S₂, can be correlated with electronic conjugation and steric effects.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.044
• wR factor = 0.115
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.767     1.000
            Tmin(prime) and Tmax expected:      0.928     0.953
            RR(prime) =      0.787
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.79
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.95
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.60 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2     -   C10     ..       5.35 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXTL.

3-(4-tert-Butyl-2,6-dimethyl-3,5-dinitrobenzoyl)- 1,1-bis(methylsulfanyl)prop-2-en-1-one

Crystal data

C17H22N2O5S2	Z = 2
Mr = 398.49	F(000) = 420
Triclinic, P1	Dx = 1.362 Mg m^−3
Hall symbol: -P 1	Melting point: 495 K
a = 8.657 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.193 (3) Å	Cell parameters from 1415 reflections
c = 12.561 (3) Å	θ = 2.5–25.1°
α = 67.272 (4)°	µ = 0.30 mm^−1
β = 71.840 (4)°	T = 294 K
γ = 82.758 (4)°	Prism, yellow
V = 971.5 (4) Å^3	0.24 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD diffractometer	3403 independent reflections
Radiation source: fine-focus sealed tube	2092 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −10→10
Tmin = 0.767, Tmax = 1.000	k = −12→12
4980 measured reflections	l = −14→8

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.05P)^2] where P = (Fo^2 + 2Fc^2)/3
3403 reflections	(Δ/σ)max = 0.003
242 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

Experimental. ¹³C NMR (CDCl₃): δ 187.5, 171.5, 150.3, 143.7, 131.3, 128.1, 111.4,37.3, 30.4, 17.5, 15.2, 15.1; ESI-MS: m/z 39 (M⁺ + 1)

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.

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

	x	y	z	Uiso*/Ueq
S1	0.42451 (10)	−0.02599 (8)	0.86759 (7)	0.0613 (3)
S2	0.29293 (10)	0.26659 (9)	0.80284 (8)	0.0658 (3)
O1	0.9484 (3)	0.1499 (2)	0.16461 (19)	0.0700 (7)
O2	0.8535 (3)	0.3633 (3)	0.1425 (2)	0.0800 (7)
O3	1.3217 (2)	0.2775 (2)	0.47569 (19)	0.0621 (6)
O4	1.2055 (3)	0.4832 (2)	0.41792 (18)	0.0620 (6)
O5	0.7083 (3)	−0.0312 (2)	0.69054 (18)	0.0733 (7)
N1	0.9173 (3)	0.2533 (3)	0.1943 (2)	0.0520 (6)
N2	1.2156 (3)	0.3558 (3)	0.43670 (19)	0.0449 (6)
C1	0.8387 (3)	0.1647 (2)	0.5194 (2)	0.0364 (6)
C2	0.8272 (3)	0.1724 (3)	0.4089 (2)	0.0374 (6)
C3	0.6837 (3)	0.1090 (3)	0.4027 (3)	0.0593 (8)
H3A	0.7094	0.0133	0.4061	0.089*
H3B	0.6589	0.1648	0.3286	0.089*
H3C	0.5914	0.1085	0.4694	0.089*
C4	0.9504 (3)	0.2432 (3)	0.3064 (2)	0.0349 (6)
C5	1.0865 (3)	0.3069 (2)	0.3025 (2)	0.0328 (6)
C6	1.2170 (3)	0.3914 (3)	0.1851 (2)	0.0422 (7)
C7	1.2390 (4)	0.3383 (3)	0.0811 (2)	0.0544 (8)
H7A	1.2509	0.2367	0.1103	0.082*
H7B	1.3344	0.3806	0.0171	0.082*
H7C	1.1455	0.3648	0.0515	0.082*
C8	1.3890 (4)	0.3768 (3)	0.2018 (3)	0.0622 (9)
H8A	1.3958	0.4348	0.2449	0.093*
H8B	1.4686	0.4074	0.1243	0.093*
H8C	1.4092	0.2793	0.2466	0.093*
C9	1.1640 (5)	0.5485 (3)	0.1449 (3)	0.0714 (10)
H9A	1.0616	0.5571	0.1280	0.107*
H9B	1.2444	0.6033	0.0735	0.107*
H9C	1.1531	0.5831	0.2079	0.107*
C10	1.0870 (3)	0.2911 (2)	0.4184 (2)	0.0336 (6)
C11	0.9705 (3)	0.2215 (2)	0.5263 (2)	0.0356 (6)
C12	0.9845 (4)	0.2086 (3)	0.6476 (2)	0.0528 (8)
H12A	0.8789	0.1921	0.7053	0.079*
H12B	1.0280	0.2950	0.6397	0.079*
H12C	1.0555	0.1306	0.6742	0.079*
C13	0.7030 (3)	0.0957 (3)	0.6328 (2)	0.0445 (7)
C14	0.5749 (3)	0.1891 (3)	0.6660 (2)	0.0465 (7)
H14	0.5807	0.2842	0.6150	0.056*
C15	0.4470 (3)	0.1490 (3)	0.7657 (2)	0.0435 (7)
C16	0.2412 (4)	−0.0253 (4)	0.9862 (3)	0.0854 (12)
H16A	0.2552	0.0364	1.0239	0.128*
H16B	0.2195	−0.1201	1.0449	0.128*
H16C	0.1517	0.0081	0.9525	0.128*
C17	0.3467 (4)	0.4321 (3)	0.6794 (3)	0.0688 (10)
H17A	0.4523	0.4602	0.6724	0.103*
H17B	0.2681	0.5035	0.6930	0.103*
H17C	0.3487	0.4215	0.6062	0.103*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0576 (5)	0.0609 (5)	0.0469 (5)	−0.0097 (4)	0.0108 (4)	−0.0176 (4)
S2	0.0527 (5)	0.0823 (6)	0.0607 (5)	0.0150 (4)	−0.0004 (4)	−0.0416 (5)
O1	0.0841 (17)	0.0793 (16)	0.0631 (15)	−0.0126 (13)	−0.0153 (12)	−0.0445 (13)
O2	0.0874 (18)	0.1008 (18)	0.0529 (14)	0.0290 (15)	−0.0422 (13)	−0.0213 (13)
O3	0.0491 (13)	0.0713 (15)	0.0718 (15)	0.0061 (11)	−0.0297 (12)	−0.0248 (12)
O4	0.0747 (16)	0.0480 (13)	0.0695 (14)	−0.0076 (11)	−0.0192 (12)	−0.0271 (11)
O5	0.0670 (15)	0.0417 (13)	0.0638 (14)	0.0065 (11)	0.0174 (11)	0.0002 (11)
N1	0.0505 (16)	0.0689 (18)	0.0379 (14)	0.0001 (13)	−0.0135 (12)	−0.0207 (14)
N2	0.0481 (16)	0.0492 (15)	0.0365 (13)	−0.0055 (12)	−0.0070 (11)	−0.0172 (11)
C1	0.0322 (15)	0.0314 (14)	0.0366 (15)	0.0048 (12)	−0.0025 (12)	−0.0102 (12)
C2	0.0332 (15)	0.0372 (15)	0.0393 (16)	0.0040 (12)	−0.0079 (12)	−0.0147 (12)
C3	0.0423 (19)	0.069 (2)	0.064 (2)	−0.0086 (15)	−0.0103 (15)	−0.0234 (17)
C4	0.0392 (16)	0.0376 (15)	0.0289 (14)	0.0083 (12)	−0.0121 (12)	−0.0142 (12)
C5	0.0361 (15)	0.0319 (14)	0.0278 (13)	0.0057 (12)	−0.0066 (11)	−0.0118 (11)
C6	0.0483 (17)	0.0416 (16)	0.0296 (14)	−0.0055 (13)	−0.0020 (12)	−0.0112 (12)
C7	0.059 (2)	0.0612 (19)	0.0353 (16)	−0.0100 (15)	0.0030 (14)	−0.0203 (14)
C8	0.050 (2)	0.082 (2)	0.0451 (18)	−0.0241 (17)	0.0079 (15)	−0.0234 (17)
C9	0.114 (3)	0.0418 (18)	0.0413 (18)	−0.0016 (18)	−0.0077 (18)	−0.0086 (15)
C10	0.0313 (14)	0.0322 (14)	0.0372 (15)	0.0016 (11)	−0.0082 (12)	−0.0143 (12)
C11	0.0404 (16)	0.0342 (14)	0.0272 (14)	0.0036 (12)	−0.0049 (12)	−0.0108 (11)
C12	0.062 (2)	0.0599 (19)	0.0336 (16)	−0.0015 (15)	−0.0097 (14)	−0.0166 (14)
C13	0.0430 (17)	0.0407 (17)	0.0363 (15)	0.0002 (13)	−0.0021 (13)	−0.0076 (13)
C14	0.0440 (17)	0.0432 (16)	0.0394 (16)	0.0047 (13)	−0.0012 (13)	−0.0116 (13)
C15	0.0364 (16)	0.0577 (18)	0.0417 (16)	−0.0001 (13)	−0.0079 (13)	−0.0266 (14)
C16	0.075 (3)	0.091 (3)	0.065 (2)	−0.025 (2)	0.0308 (19)	−0.034 (2)
C17	0.064 (2)	0.065 (2)	0.088 (3)	0.0202 (17)	−0.0213 (19)	−0.045 (2)

Geometric parameters (Å, º)

C15—S1	1.740 (3)	C6—C8	1.549 (4)
C15—S2	1.753 (3)	C7—H7A	0.9600
S1—C16	1.808 (3)	C7—H7B	0.9600
S2—C17	1.788 (3)	C7—H7C	0.9600
O1—N1	1.221 (3)	C8—H8A	0.9600
O2—N1	1.221 (3)	C8—H8B	0.9600
O3—N2	1.230 (3)	C8—H8C	0.9600
O4—N2	1.224 (3)	C9—H9A	0.9600
O5—C13	1.218 (3)	C9—H9B	0.9600
N1—C4	1.486 (3)	C9—H9C	0.9600
N2—C10	1.479 (3)	C10—C11	1.394 (3)
C1—C11	1.383 (4)	C11—C12	1.519 (3)
C1—C2	1.393 (3)	C12—H12A	0.9600
C1—C13	1.515 (4)	C12—H12B	0.9600
C2—C4	1.392 (3)	C12—H12C	0.9600
C2—C3	1.506 (4)	C13—C14	1.436 (3)
C3—H3A	0.9600	C14—C15	1.348 (4)
C3—H3B	0.9600	C14—H14	0.9300
C3—H3C	0.9600	C16—H16A	0.9600
C4—C5	1.395 (3)	C16—H16B	0.9600
C5—C10	1.403 (3)	C16—H16C	0.9600
C5—C6	1.555 (3)	C17—H17A	0.9600
C6—C9	1.538 (4)	C17—H17B	0.9600
C6—C7	1.548 (3)	C17—H17C	0.9600
C15—S1—C16	104.98 (15)	H8A—C8—H8C	109.5
C15—S2—C17	104.07 (14)	H8B—C8—H8C	109.5
O2—N1—O1	125.4 (3)	C6—C9—H9A	109.5
O2—N1—C4	116.4 (2)	C6—C9—H9B	109.5
O1—N1—C4	118.1 (2)	H9A—C9—H9B	109.5
O4—N2—O3	123.7 (2)	C6—C9—H9C	109.5
O4—N2—C10	117.9 (2)	H9A—C9—H9C	109.5
O3—N2—C10	118.3 (2)	H9B—C9—H9C	109.5
C11—C1—C2	120.9 (2)	C11—C10—C5	126.5 (2)
C11—C1—C13	119.7 (2)	C11—C10—N2	112.3 (2)
C2—C1—C13	119.4 (2)	C5—C10—N2	121.1 (2)
C4—C2—C1	117.4 (2)	C1—C11—C10	117.4 (2)
C4—C2—C3	122.2 (2)	C1—C11—C12	120.5 (2)
C1—C2—C3	120.4 (2)	C10—C11—C12	122.1 (2)
C2—C3—H3A	109.5	C11—C12—H12A	109.5
C2—C3—H3B	109.5	C11—C12—H12B	109.5
H3A—C3—H3B	109.5	H12A—C12—H12B	109.5
C2—C3—H3C	109.5	C11—C12—H12C	109.5
H3A—C3—H3C	109.5	H12A—C12—H12C	109.5
H3B—C3—H3C	109.5	H12B—C12—H12C	109.5
C2—C4—C5	126.5 (2)	O5—C13—C14	124.1 (3)
C2—C4—N1	112.0 (2)	O5—C13—C1	120.0 (2)
C5—C4—N1	121.4 (2)	C14—C13—C1	115.9 (2)
C4—C5—C10	111.3 (2)	C15—C14—C13	124.7 (3)
C4—C5—C6	124.8 (2)	C15—C14—H14	117.6
C10—C5—C6	123.9 (2)	C13—C14—H14	117.6
C9—C6—C7	108.9 (2)	C14—C15—S1	121.5 (2)
C9—C6—C8	110.2 (2)	C14—C15—S2	123.3 (2)
C7—C6—C8	103.9 (2)	S1—C15—S2	115.22 (15)
C9—C6—C5	107.9 (2)	S1—C16—H16A	109.5
C7—C6—C5	113.1 (2)	S1—C16—H16B	109.5
C8—C6—C5	112.7 (2)	H16A—C16—H16B	109.5
C6—C7—H7A	109.5	S1—C16—H16C	109.5
C6—C7—H7B	109.5	H16A—C16—H16C	109.5
H7A—C7—H7B	109.5	H16B—C16—H16C	109.5
C6—C7—H7C	109.5	S2—C17—H17A	109.5
H7A—C7—H7C	109.5	S2—C17—H17B	109.5
H7B—C7—H7C	109.5	H17A—C17—H17B	109.5
C6—C8—H8A	109.5	S2—C17—H17C	109.5
C6—C8—H8B	109.5	H17A—C17—H17C	109.5
H8A—C8—H8B	109.5	H17B—C17—H17C	109.5
C6—C8—H8C	109.5
C11—C1—C2—C4	−2.0 (3)	C6—C5—C10—N2	0.1 (3)
C13—C1—C2—C4	176.8 (2)	O4—N2—C10—C11	−99.3 (3)
C11—C1—C2—C3	179.5 (2)	O3—N2—C10—C11	77.0 (3)
C13—C1—C2—C3	−1.8 (3)	O4—N2—C10—C5	78.4 (3)
C1—C2—C4—C5	0.5 (4)	O3—N2—C10—C5	−105.3 (3)
C3—C2—C4—C5	179.1 (2)	C2—C1—C11—C10	2.4 (3)
C1—C2—C4—N1	−175.7 (2)	C13—C1—C11—C10	−176.3 (2)
C3—C2—C4—N1	2.8 (3)	C2—C1—C11—C12	−178.1 (2)
O2—N1—C4—C2	95.7 (3)	C13—C1—C11—C12	3.1 (3)
O1—N1—C4—C2	−80.9 (3)	C5—C10—C11—C1	−1.6 (4)
O2—N1—C4—C5	−80.7 (3)	N2—C10—C11—C1	176.0 (2)
O1—N1—C4—C5	102.7 (3)	C5—C10—C11—C12	179.0 (2)
C2—C4—C5—C10	0.3 (3)	N2—C10—C11—C12	−3.4 (3)
N1—C4—C5—C10	176.2 (2)	C11—C1—C13—O5	−91.0 (3)
C2—C4—C5—C6	−176.9 (2)	C2—C1—C13—O5	90.3 (3)
N1—C4—C5—C6	−1.0 (4)	C11—C1—C13—C14	88.1 (3)
C4—C5—C6—C9	90.5 (3)	C2—C1—C13—C14	−90.7 (3)
C10—C5—C6—C9	−86.4 (3)	O5—C13—C14—C15	1.4 (5)
C4—C5—C6—C7	−30.0 (3)	C1—C13—C14—C15	−177.6 (3)
C10—C5—C6—C7	153.1 (2)	C13—C14—C15—S1	0.3 (4)
C4—C5—C6—C8	−147.6 (2)	C13—C14—C15—S2	−180.0 (2)
C10—C5—C6—C8	35.6 (3)	C16—S1—C15—C14	178.3 (2)
C4—C5—C10—C11	0.2 (3)	C16—S1—C15—S2	−1.5 (2)
C6—C5—C10—C11	177.4 (2)	C17—S2—C15—C14	2.5 (3)
C4—C5—C10—N2	−177.2 (2)	C17—S2—C15—S1	−177.68 (15)