Crystal structure of 4-methyl-N-propyl­benzene­sulfonamide

The title compound comprises two mol­ecules in the asymmetric unit. Inter­molecular C—H...O and N—H...O hydrogen bonds lead to a three-dimensional network structure.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.031
• wR factor = 0.083
• Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.443
           From the CIF: _refine_ls_abs_structure_Flack_su    0.019
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00456 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8AA     ..O2       .       2.61 Ang.

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 ..........          7 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
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

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); software used to prepare material for publication: CrystalMaker (Palmer, 2007).

4-Methyl-N-propylbenzenesulfonamide

Crystal data

C10H15NO2S	F(000) = 912
Mr = 213.29	Dx = 1.278 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 15.9353 (9) Å	Cell parameters from 9996 reflections
b = 10.3526 (6) Å	θ = 2.4–26.4°
c = 14.8486 (9) Å	µ = 0.27 mm^−1
β = 115.1347 (6)°	T = 173 K
V = 2217.7 (2) Å^3	Block, colourless
Z = 8	0.45 × 0.40 × 0.39 mm

Data collection

Bruker APEXII CCD diffractometer	4422 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.028
Absorption correction: multi-scan (SADABS; Bruker, 2013)	θmax = 26.4°, θmin = 2.4°
Tmin = 0.684, Tmax = 0.745	h = −19→19
18931 measured reflections	k = −12→12
4554 independent reflections	l = −18→18

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.031	w = 1/[σ^2(Fo^2) + (0.0503P)^2 + 0.9882P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.083	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.27 e Å^−3
4554 reflections	Δρmin = −0.20 e Å^−3
265 parameters	Absolute structure: Flack x determined using 2140 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
2 restraints	Absolute structure parameter: 0.443 (19)
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
S1A	0.40337 (4)	0.32398 (6)	0.21849 (4)	0.02809 (16)
S1	0.61545 (4)	0.30322 (7)	0.77858 (4)	0.03083 (17)
O2A	0.33689 (14)	0.2460 (2)	0.14206 (15)	0.0368 (5)
C1A	0.48935 (19)	0.2218 (3)	0.3034 (2)	0.0266 (5)
C5	0.3803 (2)	0.1709 (3)	0.5601 (3)	0.0388 (7)
H5	0.3189	0.2015	0.5231	0.047*
C3A	0.6417 (2)	0.1911 (3)	0.4327 (2)	0.0325 (6)
H3A	0.7009	0.2249	0.4749	0.039*
C1	0.5341 (2)	0.2024 (3)	0.6871 (2)	0.0300 (6)
C6	0.4440 (2)	0.2486 (3)	0.6334 (2)	0.0366 (7)
H6	0.4267	0.3316	0.6470	0.044*
C4	0.4047 (2)	0.0488 (3)	0.5397 (2)	0.0347 (6)
C2A	0.5763 (2)	0.2713 (3)	0.3643 (2)	0.0324 (6)
H2A	0.5905	0.3593	0.3590	0.039*
N1	0.62264 (18)	0.4342 (2)	0.72284 (18)	0.0328 (5)
O2	0.58027 (16)	0.3406 (2)	0.84936 (15)	0.0400 (5)
C4A	0.6225 (2)	0.0614 (3)	0.4409 (2)	0.0319 (6)
O1A	0.45006 (14)	0.4257 (2)	0.19202 (16)	0.0362 (5)
C2	0.5590 (2)	0.0820 (3)	0.6681 (2)	0.0370 (7)
H2	0.6204	0.0514	0.7050	0.044*
C3	0.4942 (2)	0.0052 (3)	0.5949 (2)	0.0418 (7)
H3	0.5115	−0.0784	0.5825	0.050*
N1A	0.34797 (17)	0.3914 (2)	0.27586 (19)	0.0332 (5)
C5A	0.5348 (2)	0.0145 (3)	0.3788 (2)	0.0350 (6)
H5A	0.5204	−0.0736	0.3837	0.042*
C8	0.6443 (2)	0.4213 (3)	0.6357 (2)	0.0399 (7)
H8A	0.5885	0.3916	0.5774	0.048*
H8B	0.6936	0.3558	0.6499	0.048*
C9A	0.3349 (2)	0.5714 (3)	0.3760 (2)	0.0421 (7)
H9AA	0.2776	0.5292	0.3720	0.051*
H9AB	0.3659	0.6119	0.4425	0.051*
C6A	0.4685 (2)	0.0937 (3)	0.3105 (2)	0.0338 (6)
H6A	0.4090	0.0604	0.2688	0.041*
O1	0.70368 (15)	0.2382 (2)	0.81488 (17)	0.0411 (5)
C7	0.3343 (3)	−0.0346 (3)	0.4595 (3)	0.0480 (8)
H7A	0.3372	−0.0177	0.3960	0.072*
H7B	0.2720	−0.0144	0.4535	0.072*
H7C	0.3480	−0.1259	0.4772	0.072*
C7A	0.6943 (2)	−0.0253 (3)	0.5154 (2)	0.0420 (7)
H7AA	0.7558	0.0133	0.5359	0.063*
H7AB	0.6928	−0.1099	0.4851	0.063*
H7AC	0.6810	−0.0358	0.5737	0.063*
C8A	0.3984 (2)	0.4693 (3)	0.3654 (2)	0.0377 (6)
H8AA	0.4523	0.5114	0.3608	0.045*
H8AB	0.4219	0.4127	0.4248	0.045*
C10	0.6052 (3)	0.6546 (4)	0.5879 (3)	0.0575 (10)
H10D	0.5466	0.6260	0.5343	0.086*
H10E	0.6273	0.7319	0.5666	0.086*
H10F	0.5953	0.6747	0.6472	0.086*
C9	0.6761 (3)	0.5489 (4)	0.6120 (3)	0.0535 (9)
H9A	0.7334	0.5760	0.6696	0.064*
H9B	0.6916	0.5370	0.5546	0.064*
C10A	0.3090 (3)	0.6751 (4)	0.2977 (3)	0.0613 (11)
H10A	0.2820	0.6352	0.2316	0.092*
H10B	0.3645	0.7240	0.3061	0.092*
H10C	0.2636	0.7335	0.3044	0.092*
H1A	0.307 (2)	0.343 (3)	0.277 (2)	0.034 (9)*
H1	0.576 (2)	0.481 (3)	0.713 (2)	0.030 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0225 (3)	0.0303 (3)	0.0288 (3)	−0.0027 (3)	0.0082 (3)	0.0011 (3)
S1	0.0278 (3)	0.0362 (3)	0.0270 (3)	0.0067 (3)	0.0102 (3)	−0.0013 (3)
O2A	0.0286 (10)	0.0384 (11)	0.0336 (10)	−0.0029 (9)	0.0039 (9)	−0.0020 (9)
C1A	0.0250 (13)	0.0287 (13)	0.0257 (13)	−0.0013 (10)	0.0104 (11)	0.0008 (11)
C5	0.0275 (15)	0.0389 (17)	0.0436 (18)	0.0017 (12)	0.0088 (14)	−0.0004 (13)
C3A	0.0274 (14)	0.0338 (16)	0.0327 (15)	−0.0037 (11)	0.0094 (13)	−0.0031 (11)
C1	0.0281 (14)	0.0353 (14)	0.0289 (14)	0.0030 (11)	0.0143 (12)	0.0011 (11)
C6	0.0304 (14)	0.0304 (15)	0.0451 (17)	0.0054 (12)	0.0124 (14)	−0.0022 (12)
C4	0.0403 (16)	0.0338 (15)	0.0327 (14)	−0.0044 (12)	0.0180 (13)	−0.0004 (12)
C2A	0.0275 (14)	0.0305 (14)	0.0362 (15)	−0.0043 (11)	0.0106 (12)	0.0009 (11)
N1	0.0309 (12)	0.0334 (12)	0.0349 (12)	0.0048 (10)	0.0147 (10)	−0.0028 (10)
O2	0.0442 (12)	0.0468 (12)	0.0318 (10)	0.0060 (10)	0.0188 (9)	−0.0014 (9)
C4A	0.0348 (15)	0.0362 (15)	0.0263 (13)	0.0020 (12)	0.0143 (12)	0.0023 (11)
O1A	0.0305 (10)	0.0367 (11)	0.0405 (11)	−0.0013 (8)	0.0141 (9)	0.0073 (9)
C2	0.0347 (15)	0.0360 (15)	0.0392 (16)	0.0100 (12)	0.0147 (13)	0.0005 (13)
C3	0.0485 (19)	0.0360 (16)	0.0412 (17)	0.0063 (14)	0.0193 (15)	−0.0034 (13)
N1A	0.0244 (11)	0.0343 (13)	0.0404 (13)	−0.0051 (10)	0.0133 (10)	−0.0042 (10)
C5A	0.0417 (17)	0.0272 (14)	0.0353 (14)	−0.0046 (12)	0.0156 (13)	0.0016 (11)
C8	0.0415 (16)	0.0430 (16)	0.0420 (16)	0.0048 (14)	0.0243 (14)	−0.0015 (14)
C9A	0.0377 (16)	0.0497 (19)	0.0421 (17)	−0.0032 (14)	0.0199 (14)	−0.0107 (14)
C6A	0.0323 (14)	0.0337 (14)	0.0323 (14)	−0.0075 (12)	0.0105 (12)	−0.0024 (11)
O1	0.0334 (11)	0.0448 (13)	0.0379 (11)	0.0111 (9)	0.0083 (9)	0.0001 (9)
C7	0.051 (2)	0.0457 (18)	0.0440 (18)	−0.0119 (15)	0.0171 (16)	−0.0088 (15)
C7A	0.0437 (18)	0.0407 (17)	0.0381 (16)	0.0047 (13)	0.0139 (14)	0.0081 (13)
C8A	0.0321 (15)	0.0457 (16)	0.0323 (14)	−0.0014 (13)	0.0109 (12)	−0.0053 (13)
C10	0.079 (3)	0.0418 (19)	0.060 (2)	−0.0037 (19)	0.038 (2)	0.0091 (16)
C9	0.053 (2)	0.058 (2)	0.062 (2)	−0.0094 (17)	0.0365 (19)	−0.0031 (18)
C10A	0.082 (3)	0.042 (2)	0.051 (2)	0.0113 (19)	0.021 (2)	−0.0126 (16)

Geometric parameters (Å, º)

S1A—O2A	1.428 (2)	N1A—C8A	1.469 (4)
S1A—C1A	1.766 (3)	N1A—H1A	0.82 (3)
S1A—O1A	1.437 (2)	C5A—H5A	0.9500
S1A—N1A	1.622 (3)	C5A—C6A	1.381 (4)
S1—C1	1.766 (3)	C8—H8A	0.9900
S1—N1	1.618 (3)	C8—H8B	0.9900
S1—O2	1.438 (2)	C8—C9	1.509 (5)
S1—O1	1.441 (2)	C9A—H9AA	0.9900
C1A—C2A	1.392 (4)	C9A—H9AB	0.9900
C1A—C6A	1.382 (4)	C9A—C8A	1.518 (4)
C5—H5	0.9500	C9A—C10A	1.505 (6)
C5—C6	1.387 (5)	C6A—H6A	0.9500
C5—C4	1.393 (4)	C7—H7A	0.9800
C3A—H3A	0.9500	C7—H7B	0.9800
C3A—C2A	1.381 (4)	C7—H7C	0.9800
C3A—C4A	1.394 (4)	C7A—H7AA	0.9800
C1—C6	1.397 (4)	C7A—H7AB	0.9800
C1—C2	1.374 (4)	C7A—H7AC	0.9800
C6—H6	0.9500	C8A—H8AA	0.9900
C4—C3	1.385 (5)	C8A—H8AB	0.9900
C4—C7	1.512 (4)	C10—H10D	0.9800
C2A—H2A	0.9500	C10—H10E	0.9800
N1—C8	1.481 (4)	C10—H10F	0.9800
N1—H1	0.85 (3)	C10—C9	1.503 (6)
C4A—C5A	1.394 (4)	C9—H9A	0.9900
C4A—C7A	1.505 (4)	C9—H9B	0.9900
C2—H2	0.9500	C10A—H10A	0.9800
C2—C3	1.389 (5)	C10A—H10B	0.9800
C3—H3	0.9500	C10A—H10C	0.9800
O2A—S1A—C1A	108.49 (13)	N1—C8—H8A	109.5
O2A—S1A—O1A	119.48 (13)	N1—C8—H8B	109.5
O2A—S1A—N1A	105.96 (13)	N1—C8—C9	110.6 (3)
O1A—S1A—C1A	107.43 (13)	H8A—C8—H8B	108.1
O1A—S1A—N1A	106.77 (13)	C9—C8—H8A	109.5
N1A—S1A—C1A	108.27 (13)	C9—C8—H8B	109.5
N1—S1—C1	106.86 (13)	H9AA—C9A—H9AB	107.8
O2—S1—C1	109.52 (13)	C8A—C9A—H9AA	109.0
O2—S1—N1	106.43 (13)	C8A—C9A—H9AB	109.0
O2—S1—O1	118.26 (13)	C10A—C9A—H9AA	109.0
O1—S1—C1	107.03 (13)	C10A—C9A—H9AB	109.0
O1—S1—N1	108.23 (14)	C10A—C9A—C8A	113.1 (3)
C2A—C1A—S1A	120.0 (2)	C1A—C6A—H6A	120.3
C6A—C1A—S1A	119.4 (2)	C5A—C6A—C1A	119.5 (3)
C6A—C1A—C2A	120.6 (3)	C5A—C6A—H6A	120.3
C6—C5—H5	119.4	C4—C7—H7A	109.5
C6—C5—C4	121.2 (3)	C4—C7—H7B	109.5
C4—C5—H5	119.4	C4—C7—H7C	109.5
C2A—C3A—H3A	119.4	H7A—C7—H7B	109.5
C2A—C3A—C4A	121.2 (3)	H7A—C7—H7C	109.5
C4A—C3A—H3A	119.4	H7B—C7—H7C	109.5
C6—C1—S1	118.5 (2)	C4A—C7A—H7AA	109.5
C2—C1—S1	120.8 (2)	C4A—C7A—H7AB	109.5
C2—C1—C6	120.7 (3)	C4A—C7A—H7AC	109.5
C5—C6—C1	118.8 (3)	H7AA—C7A—H7AB	109.5
C5—C6—H6	120.6	H7AA—C7A—H7AC	109.5
C1—C6—H6	120.6	H7AB—C7A—H7AC	109.5
C5—C4—C7	120.5 (3)	N1A—C8A—C9A	110.1 (2)
C3—C4—C5	118.7 (3)	N1A—C8A—H8AA	109.6
C3—C4—C7	120.8 (3)	N1A—C8A—H8AB	109.6
C1A—C2A—H2A	120.4	C9A—C8A—H8AA	109.6
C3A—C2A—C1A	119.2 (3)	C9A—C8A—H8AB	109.6
C3A—C2A—H2A	120.4	H8AA—C8A—H8AB	108.2
S1—N1—H1	108 (2)	H10D—C10—H10E	109.5
C8—N1—S1	117.7 (2)	H10D—C10—H10F	109.5
C8—N1—H1	115 (2)	H10E—C10—H10F	109.5
C3A—C4A—C5A	118.3 (3)	C9—C10—H10D	109.5
C3A—C4A—C7A	120.8 (3)	C9—C10—H10E	109.5
C5A—C4A—C7A	120.9 (3)	C9—C10—H10F	109.5
C1—C2—H2	120.1	C8—C9—H9A	108.9
C1—C2—C3	119.7 (3)	C8—C9—H9B	108.9
C3—C2—H2	120.1	C10—C9—C8	113.5 (3)
C4—C3—C2	120.9 (3)	C10—C9—H9A	108.9
C4—C3—H3	119.5	C10—C9—H9B	108.9
C2—C3—H3	119.5	H9A—C9—H9B	107.7
S1A—N1A—H1A	111 (2)	C9A—C10A—H10A	109.5
C8A—N1A—S1A	120.07 (19)	C9A—C10A—H10B	109.5
C8A—N1A—H1A	117 (2)	C9A—C10A—H10C	109.5
C4A—C5A—H5A	119.4	H10A—C10A—H10B	109.5
C6A—C5A—C4A	121.2 (3)	H10A—C10A—H10C	109.5
C6A—C5A—H5A	119.4	H10B—C10A—H10C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3A—H3A···O2A^i	0.95	2.53	3.399 (4)	153
C6—H6···O1A^ii	0.95	2.59	3.474 (4)	156
C8—H8B···O2A^i	0.99	2.56	3.489 (4)	156
C8A—H8AA···O2^iii	0.99	2.61	3.594 (4)	170
N1A—H1A···O1^iv	0.82 (3)	2.14 (3)	2.925 (3)	161 (3)
N1—H1···O1A^ii	0.85 (3)	2.13 (4)	2.968 (3)	172 (3)

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