Crystal structure of N,N-diisopropyl-4-methyl­benzene­sulfonamide

The synthesis and crystal structure of a diisopropyl-substituted p-tolunesulfonamide is discussed. This structure features C—H...O hydrogen bonds (both intra- and inter­molecular) and inter­molecular C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.042
• wR factor = 0.109
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

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Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.64 Report
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00564 Ang.
PLAT761_ALERT_1_C CIF Contains no X-H Bonds ......................     Please Check
PLAT762_ALERT_1_C CIF Contains no X-Y-H or H-Y-H Angles ..........     Please Check
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage         83 %

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          6 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          9 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   2 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009; Bourhis et al., 2015) and XP (Sheldrick, 2008); software used to prepare material for publication: CrystalMaker (Palmer, 2007).

N,N-Diisopropyl-4-methylbenzenesulfonamide

Crystal data

C13H21NO2S	F(000) = 552
Mr = 255.37	Dx = 1.242 Mg m^−3
Monoclinic, Pc	Cu Kα radiation, λ = 1.54178 Å
a = 12.87828 (18) Å	Cell parameters from 9971 reflections
b = 6.88418 (10) Å	θ = 3.6–72.1°
c = 16.2080 (2) Å	µ = 2.03 mm^−1
β = 108.1513 (8)°	T = 173 K
V = 1365.43 (3) Å^3	Block, colourless
Z = 4	0.18 × 0.16 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer	4746 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.034
Absorption correction: multi-scan (SADABS; Bruker, 2013)	θmax = 72.1°, θmin = 3.6°
Tmin = 0.640, Tmax = 0.754	h = −15→15
15150 measured reflections	k = −8→8
4924 independent reflections	l = −20→18

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.042	w = 1/[σ^2(Fo^2) + (0.0814P)^2 + 0.0782P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.109	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.63 e Å^−3
4924 reflections	Δρmin = −0.24 e Å^−3
317 parameters	Absolute structure: Flack x determined using 2083 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
2 restraints	Absolute structure parameter: 0.002 (14)
Primary atom site location: structure-invariant direct methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
S1	0.25085 (5)	0.34566 (10)	0.27005 (5)	0.0236 (2)
O1	0.1864 (2)	0.3511 (4)	0.32791 (17)	0.0323 (6)
O2	0.3339 (2)	0.4906 (3)	0.27789 (17)	0.0315 (5)
N1	0.3086 (2)	0.1339 (4)	0.27951 (19)	0.0249 (6)
C1	0.1606 (3)	0.3671 (5)	0.1623 (2)	0.0240 (7)
C2	0.0507 (3)	0.3170 (5)	0.1436 (2)	0.0274 (7)
H2	0.0228	0.2759	0.1885	0.033*
C3	−0.0170 (3)	0.3280 (5)	0.0586 (3)	0.0308 (7)
H3	−0.0918	0.2937	0.0456	0.037*
C4	0.0219 (3)	0.3880 (5)	−0.0081 (2)	0.0298 (7)
C5	0.1322 (3)	0.4381 (5)	0.0119 (2)	0.0303 (7)
H5	0.1603	0.4787	−0.0330	0.036*
C6	0.2006 (3)	0.4289 (5)	0.0968 (2)	0.0291 (7)
H6	0.2752	0.4652	0.1101	0.035*
C7	−0.0533 (3)	0.4041 (6)	−0.1000 (3)	0.0393 (9)
H7A	−0.1056	0.5097	−0.1038	0.059*
H7B	−0.0930	0.2816	−0.1171	0.059*
H7C	−0.0103	0.4315	−0.1390	0.059*
C8	0.2723 (3)	−0.0367 (5)	0.3194 (2)	0.0271 (7)
H8	0.3160	−0.1489	0.3092	0.033*
C9	0.3011 (3)	−0.0184 (6)	0.4176 (3)	0.0365 (8)
H9A	0.2604	0.0900	0.4318	0.055*
H9B	0.3797	0.0054	0.4428	0.055*
H9C	0.2818	−0.1391	0.4415	0.055*
C10	0.1530 (3)	−0.0920 (6)	0.2761 (3)	0.0357 (8)
H10A	0.1378	−0.0968	0.2130	0.054*
H10B	0.1056	0.0050	0.2905	0.054*
H10C	0.1389	−0.2198	0.2971	0.054*
C11	0.3851 (3)	0.0994 (5)	0.2283 (2)	0.0279 (7)
H11	0.3971	0.2268	0.2030	0.034*
C12	0.3388 (4)	−0.0400 (6)	0.1535 (3)	0.0396 (9)
H12A	0.2677	0.0079	0.1168	0.059*
H12B	0.3296	−0.1685	0.1763	0.059*
H12C	0.3890	−0.0495	0.1190	0.059*
C13	0.4957 (3)	0.0315 (7)	0.2889 (3)	0.0405 (9)
H13A	0.4871	−0.0953	0.3135	0.061*
H13B	0.5230	0.1260	0.3359	0.061*
H13C	0.5478	0.0203	0.2561	0.061*
S1A	0.68214 (5)	0.14554 (10)	0.62704 (5)	0.0245 (2)
O1A	0.7462 (2)	0.1368 (4)	0.71678 (18)	0.0341 (6)
O2A	0.5988 (2)	0.0023 (4)	0.59227 (18)	0.0321 (6)
N1A	0.6249 (2)	0.3582 (4)	0.60873 (19)	0.0245 (6)
C1A	0.7733 (3)	0.1253 (5)	0.5650 (2)	0.0244 (6)
C2A	0.8822 (3)	0.1807 (5)	0.6000 (2)	0.0273 (7)
H2A	0.9094	0.2242	0.6584	0.033*
C3A	0.9505 (3)	0.1721 (5)	0.5491 (3)	0.0298 (7)
H3A	1.0248	0.2099	0.5732	0.036*
C4A	0.9125 (3)	0.1091 (5)	0.4631 (2)	0.0295 (7)
C5A	0.8030 (3)	0.0539 (5)	0.4289 (2)	0.0300 (7)
H5A	0.7754	0.0116	0.3703	0.036*
C6A	0.7346 (3)	0.0606 (5)	0.4797 (2)	0.0275 (7)
H6A	0.6606	0.0207	0.4561	0.033*
C7A	0.9887 (3)	0.0957 (6)	0.4096 (3)	0.0395 (9)
H7AA	1.0400	−0.0115	0.4310	0.059*
H7AB	1.0293	0.2177	0.4142	0.059*
H7AC	0.9464	0.0723	0.3488	0.059*
C8A	0.6606 (3)	0.5254 (5)	0.6691 (2)	0.0284 (7)
H8A	0.6168	0.6393	0.6390	0.034*
C9A	0.6315 (4)	0.4982 (6)	0.7524 (3)	0.0400 (9)
H9AA	0.5536	0.4672	0.7381	0.060*
H9AB	0.6472	0.6181	0.7867	0.060*
H9AC	0.6749	0.3916	0.7863	0.060*
C10A	0.7800 (3)	0.5825 (6)	0.6868 (3)	0.0396 (9)
H10E	0.7948	0.7034	0.7204	0.059*
H10D	0.7948	0.6015	0.6316	0.059*
H10F	0.8273	0.4791	0.7199	0.059*
C11A	0.5500 (3)	0.3973 (5)	0.5205 (2)	0.0285 (7)
H11A	0.5371	0.2713	0.4882	0.034*
C12A	0.5984 (3)	0.5382 (6)	0.4700 (3)	0.0382 (8)
H12D	0.6099	0.6647	0.4992	0.057*
H12E	0.5480	0.5529	0.4110	0.057*
H12F	0.6684	0.4876	0.4674	0.057*
C13A	0.4399 (3)	0.4693 (6)	0.5249 (3)	0.0371 (8)
H13D	0.4116	0.3783	0.5592	0.056*
H13E	0.3883	0.4781	0.4660	0.056*
H13F	0.4489	0.5978	0.5522	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0291 (4)	0.0182 (4)	0.0235 (4)	0.0012 (3)	0.0081 (3)	−0.0022 (3)
O1	0.0406 (14)	0.0291 (14)	0.0286 (13)	0.0074 (10)	0.0126 (10)	−0.0021 (9)
O2	0.0357 (12)	0.0214 (11)	0.0341 (13)	−0.0035 (10)	0.0062 (10)	−0.0020 (9)
N1	0.0300 (15)	0.0225 (14)	0.0233 (15)	0.0042 (11)	0.0100 (12)	0.0020 (10)
C1	0.0288 (15)	0.0201 (15)	0.0230 (16)	0.0045 (12)	0.0080 (12)	0.0001 (11)
C2	0.0284 (15)	0.0218 (14)	0.0338 (17)	0.0031 (13)	0.0123 (13)	0.0005 (12)
C3	0.0286 (15)	0.0212 (15)	0.0400 (19)	0.0001 (12)	0.0070 (14)	−0.0023 (13)
C4	0.0387 (17)	0.0178 (14)	0.0301 (18)	0.0067 (14)	0.0067 (14)	−0.0014 (12)
C5	0.0381 (17)	0.0265 (17)	0.0280 (17)	0.0061 (14)	0.0130 (13)	0.0056 (13)
C6	0.0300 (15)	0.0265 (17)	0.0313 (18)	0.0021 (13)	0.0104 (13)	0.0052 (13)
C7	0.049 (2)	0.0281 (18)	0.0316 (19)	0.0017 (16)	−0.0012 (15)	−0.0011 (14)
C8	0.0343 (16)	0.0201 (15)	0.0298 (17)	0.0005 (13)	0.0140 (13)	0.0030 (13)
C9	0.047 (2)	0.0337 (19)	0.0285 (18)	−0.0011 (16)	0.0117 (15)	0.0063 (14)
C10	0.0382 (18)	0.0300 (17)	0.043 (2)	−0.0069 (15)	0.0182 (15)	−0.0011 (15)
C11	0.0323 (16)	0.0247 (15)	0.0301 (17)	0.0029 (13)	0.0144 (13)	0.0013 (13)
C12	0.052 (2)	0.040 (2)	0.0306 (19)	0.0053 (18)	0.0188 (16)	−0.0065 (15)
C13	0.0327 (17)	0.046 (2)	0.045 (2)	0.0097 (16)	0.0149 (16)	0.0061 (17)
S1A	0.0310 (4)	0.0190 (4)	0.0267 (4)	0.0036 (3)	0.0135 (3)	0.0040 (3)
O1A	0.0438 (15)	0.0305 (13)	0.0311 (14)	0.0098 (11)	0.0161 (11)	0.0078 (9)
O2A	0.0371 (12)	0.0230 (12)	0.0422 (15)	−0.0022 (10)	0.0211 (11)	0.0008 (10)
N1A	0.0289 (14)	0.0197 (13)	0.0256 (15)	0.0031 (10)	0.0096 (11)	−0.0003 (10)
C1A	0.0304 (16)	0.0191 (14)	0.0274 (17)	0.0070 (12)	0.0141 (13)	0.0023 (11)
C2A	0.0284 (15)	0.0231 (15)	0.0296 (17)	0.0022 (13)	0.0078 (13)	0.0000 (12)
C3A	0.0286 (15)	0.0214 (15)	0.0398 (19)	0.0018 (13)	0.0114 (13)	0.0035 (13)
C4A	0.0370 (17)	0.0182 (14)	0.0381 (19)	0.0080 (13)	0.0185 (15)	0.0069 (13)
C5A	0.0396 (17)	0.0248 (16)	0.0269 (17)	0.0072 (14)	0.0120 (13)	−0.0004 (12)
C6A	0.0274 (14)	0.0242 (16)	0.0300 (17)	0.0051 (13)	0.0075 (12)	−0.0001 (13)
C7A	0.047 (2)	0.0306 (18)	0.052 (2)	0.0040 (16)	0.0325 (18)	0.0047 (16)
C8A	0.0350 (16)	0.0237 (15)	0.0260 (16)	0.0044 (13)	0.0089 (13)	−0.0022 (12)
C9A	0.055 (2)	0.038 (2)	0.0320 (19)	0.0065 (18)	0.0203 (17)	−0.0040 (15)
C10A	0.042 (2)	0.038 (2)	0.035 (2)	−0.0047 (17)	0.0059 (15)	−0.0056 (16)
C11A	0.0335 (17)	0.0251 (16)	0.0254 (16)	0.0041 (14)	0.0070 (13)	−0.0006 (13)
C12A	0.051 (2)	0.039 (2)	0.0285 (18)	0.0049 (17)	0.0186 (16)	0.0072 (15)
C13A	0.0298 (16)	0.0352 (19)	0.045 (2)	0.0068 (15)	0.0091 (14)	0.0003 (16)

Geometric parameters (Å, º)

S1—O1	1.434 (3)	S1A—O1A	1.433 (3)
S1—O2	1.439 (3)	S1A—O2A	1.437 (3)
S1—N1	1.622 (3)	S1A—N1A	1.624 (3)
S1—C1	1.777 (3)	S1A—C1A	1.773 (4)
N1—C8	1.484 (4)	N1A—C8A	1.489 (4)
N1—C11	1.493 (4)	N1A—C11A	1.479 (4)
C1—C2	1.395 (5)	C1A—C2A	1.393 (5)
C1—C6	1.383 (5)	C1A—C6A	1.390 (5)
C2—H2	0.9500	C2A—H2A	0.9500
C2—C3	1.384 (5)	C2A—C3A	1.381 (5)
C3—H3	0.9500	C3A—H3A	0.9500
C3—C4	1.388 (6)	C3A—C4A	1.395 (5)
C4—C5	1.398 (5)	C4A—C5A	1.398 (5)
C4—C7	1.507 (5)	C4A—C7A	1.500 (5)
C5—H5	0.9500	C5A—H5A	0.9500
C5—C6	1.385 (5)	C5A—C6A	1.381 (5)
C6—H6	0.9500	C6A—H6A	0.9500
C7—H7A	0.9800	C7A—H7AA	0.9800
C7—H7B	0.9800	C7A—H7AB	0.9800
C7—H7C	0.9800	C7A—H7AC	0.9800
C8—H8	1.0000	C8A—H8A	1.0000
C8—C9	1.524 (5)	C8A—C9A	1.521 (5)
C8—C10	1.525 (5)	C8A—C10A	1.525 (5)
C9—H9A	0.9800	C9A—H9AA	0.9800
C9—H9B	0.9800	C9A—H9AB	0.9800
C9—H9C	0.9800	C9A—H9AC	0.9800
C10—H10A	0.9800	C10A—H10D	0.9800
C10—H10B	0.9800	C10A—H10E	0.9800
C10—H10C	0.9800	C10A—H10F	0.9800
C11—H11	1.0000	C11A—H11A	1.0000
C11—C12	1.516 (5)	C11A—C12A	1.522 (5)
C11—C13	1.529 (5)	C11A—C13A	1.525 (5)
C12—H12A	0.9800	C12A—H12D	0.9800
C12—H12B	0.9800	C12A—H12E	0.9800
C12—H12C	0.9800	C12A—H12F	0.9800
C13—H13A	0.9800	C13A—H13D	0.9800
C13—H13B	0.9800	C13A—H13E	0.9800
C13—H13C	0.9800	C13A—H13F	0.9800
O1—S1—O2	119.35 (16)	O1A—S1A—O2A	119.54 (16)
O1—S1—N1	107.65 (15)	O1A—S1A—N1A	107.96 (15)
O1—S1—C1	107.80 (16)	O1A—S1A—C1A	107.38 (17)
O2—S1—N1	107.99 (14)	O2A—S1A—N1A	107.79 (15)
O2—S1—C1	105.66 (16)	O2A—S1A—C1A	105.62 (16)
N1—S1—C1	107.92 (15)	N1A—S1A—C1A	108.09 (15)
C8—N1—S1	123.7 (2)	C8A—N1A—S1A	123.2 (2)
C8—N1—C11	117.9 (3)	C11A—N1A—S1A	117.6 (2)
C11—N1—S1	117.0 (2)	C11A—N1A—C8A	118.1 (3)
C2—C1—S1	120.1 (3)	C2A—C1A—S1A	120.6 (3)
C6—C1—S1	119.6 (3)	C6A—C1A—S1A	119.6 (3)
C6—C1—C2	120.3 (3)	C6A—C1A—C2A	119.8 (3)
C1—C2—H2	120.5	C1A—C2A—H2A	120.2
C3—C2—C1	119.0 (3)	C3A—C2A—C1A	119.6 (3)
C3—C2—H2	120.5	C3A—C2A—H2A	120.2
C2—C3—H3	119.2	C2A—C3A—H3A	119.3
C2—C3—C4	121.6 (3)	C2A—C3A—C4A	121.3 (3)
C4—C3—H3	119.2	C4A—C3A—H3A	119.3
C3—C4—C5	118.6 (3)	C3A—C4A—C5A	118.5 (3)
C3—C4—C7	121.0 (3)	C3A—C4A—C7A	120.5 (3)
C5—C4—C7	120.3 (3)	C5A—C4A—C7A	121.0 (3)
C4—C5—H5	119.8	C4A—C5A—H5A	119.8
C6—C5—C4	120.3 (3)	C6A—C5A—C4A	120.5 (3)
C6—C5—H5	119.8	C6A—C5A—H5A	119.8
C1—C6—C5	120.2 (3)	C1A—C6A—H6A	119.8
C1—C6—H6	119.9	C5A—C6A—C1A	120.4 (3)
C5—C6—H6	119.9	C5A—C6A—H6A	119.8
C4—C7—H7A	109.5	C4A—C7A—H7AA	109.5
C4—C7—H7B	109.5	C4A—C7A—H7AB	109.5
C4—C7—H7C	109.5	C4A—C7A—H7AC	109.5
H7A—C7—H7B	109.5	H7AA—C7A—H7AB	109.5
H7A—C7—H7C	109.5	H7AA—C7A—H7AC	109.5
H7B—C7—H7C	109.5	H7AB—C7A—H7AC	109.5
N1—C8—H8	105.7	N1A—C8A—H8A	105.8
N1—C8—C9	112.5 (3)	N1A—C8A—C9A	112.1 (3)
N1—C8—C10	114.0 (3)	N1A—C8A—C10A	114.2 (3)
C9—C8—H8	105.7	C9A—C8A—H8A	105.8
C9—C8—C10	112.5 (3)	C9A—C8A—C10A	112.2 (3)
C10—C8—H8	105.7	C10A—C8A—H8A	105.8
C8—C9—H9A	109.5	C8A—C9A—H9AA	109.5
C8—C9—H9B	109.5	C8A—C9A—H9AB	109.5
C8—C9—H9C	109.5	C8A—C9A—H9AC	109.5
H9A—C9—H9B	109.5	H9AA—C9A—H9AB	109.5
H9A—C9—H9C	109.5	H9AA—C9A—H9AC	109.5
H9B—C9—H9C	109.5	H9AB—C9A—H9AC	109.5
C8—C10—H10A	109.5	C8A—C10A—H10D	109.5
C8—C10—H10B	109.5	C8A—C10A—H10E	109.5
C8—C10—H10C	109.5	C8A—C10A—H10F	109.5
H10A—C10—H10B	109.5	H10D—C10A—H10E	109.5
H10A—C10—H10C	109.5	H10D—C10A—H10F	109.5
H10B—C10—H10C	109.5	H10E—C10A—H10F	109.5
N1—C11—H11	107.5	N1A—C11A—H11A	107.5
N1—C11—C12	112.5 (3)	N1A—C11A—C12A	112.5 (3)
N1—C11—C13	109.6 (3)	N1A—C11A—C13A	110.5 (3)
C12—C11—H11	107.5	C12A—C11A—H11A	107.5
C12—C11—C13	112.1 (3)	C12A—C11A—C13A	111.1 (3)
C13—C11—H11	107.5	C13A—C11A—H11A	107.5
C11—C12—H12A	109.5	C11A—C12A—H12D	109.5
C11—C12—H12B	109.5	C11A—C12A—H12E	109.5
C11—C12—H12C	109.5	C11A—C12A—H12F	109.5
H12A—C12—H12B	109.5	H12D—C12A—H12E	109.5
H12A—C12—H12C	109.5	H12D—C12A—H12F	109.5
H12B—C12—H12C	109.5	H12E—C12A—H12F	109.5
C11—C13—H13A	109.5	C11A—C13A—H13D	109.5
C11—C13—H13B	109.5	C11A—C13A—H13E	109.5
C11—C13—H13C	109.5	C11A—C13A—H13F	109.5
H13A—C13—H13B	109.5	H13D—C13A—H13E	109.5
H13A—C13—H13C	109.5	H13D—C13A—H13F	109.5
H13B—C13—H13C	109.5	H13E—C13A—H13F	109.5

Hydrogen-bond geometry (Å, º)

Cg1 and Cg2 are the centroids of the C1–C6 and C1A–C6A rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2^i	1.00	2.56	3.464 (4)	151
C9—H9A···O1	0.98	2.44	3.071 (5)	121
C10—H10B···O1	0.98	2.59	3.157 (5)	117
C9A—H9AC···O1A	0.98	2.41	3.039 (5)	121
C10A—H10F···O1A	0.98	2.57	3.157 (5)	118
C3—H3···Cg2^ii	0.95	2.95	3.515 (4)	120
C3A—H3A···Cg1^iii	0.95	2.96	3.548 (4)	121

Symmetry codes: (i) x, y−1, z; (ii) x−1, −y, z−1/2; (iii) x+1, −y+1, z+1/2.