4-Nitro­phenyl 4-toluene­sulfonate: supramolecular aggregation through weak C—H...O, C—H...π and van der Waals interactions

In the crystal structure of the title compound, C₁₃H₁₁NO₅S, the dihedral angle between the mean planes of the 4-tolyl and 4-nitro­phenyl rings is 82.52 (4)°. There are weak C—H...O interactions, which generate rings of graph-set motifs S(5), S(6), (5), (6) and (9). The supramolecular aggregation is completed by the presence of C—H...π and van der Waals interactions.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.037
• wR factor = 0.091
• Data-to-parameter ratio = 35.0

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.93

Author Response: The slightly low completeness at theta max = 37 deg is a result of collecting data to such an exceptionally high scattering angle,but it does not present a problem, since the data/parameter ratio is also extremely high, at theta>30

Alert level B
PLAT480_ALERT_4_B Long H...A H-Bond Reported H7B    ..  O2      ..       3.00 Ang.

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         47 Perc.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6     ..  O2      ..       2.97 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6     ..  O3      ..       2.87 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3     ..  O2      ..       2.64 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6     ..  O1      ..       2.86 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5     ..  O1      ..       2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6     ..  O4      ..       2.69 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13    ..  O5      ..       2.90 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2     ..  CG      ..       3.07 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C7     ..  O2      ..       3.89 Ang.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C6     ..  O2      ..      92.00 Deg.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C6     ..  O3      ..      95.00 Deg.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C10    ..  O5      ..      98.00 Deg.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C12    ..  O4      ..      98.00 Deg.

   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  14 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
   2 ALERT type 3 Indicator that the structure quality may be low
  14 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; 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.

4-Nitrophenyl 4-toluenesulfonate

Crystal data

C13H11NO5S	F(000) = 608
Mr = 293.29	Dx = 1.519 Mg m^−3
Monoclinic, P21/c	Melting point = 368–369 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.3450 (4) Å	Cell parameters from 7340 reflections
b = 8.0160 (4) Å	θ = 2.5–37.0°
c = 12.3780 (7) Å	µ = 0.27 mm^−1
β = 104.391 (3)°	T = 150 K
V = 1282.57 (10) Å^3	Prism, colorless
Z = 4	0.37 × 0.27 × 0.10 mm

Data collection

Nonius KappaCCD (with Oxford Cryosystems Cryostream cooler) diffractometer	6437 independent reflections
Radiation source: fine-focus sealed tube	3045 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
ω scans with κ offsets	θmax = 37.1°, θmin = 2.8°
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	h = −22→22
Tmin = 0.887, Tmax = 0.973	k = −13→13
10707 measured reflections	l = −19→20

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.092	H-atom parameters constrained
S = 0.88	w = 1/[σ^2(Fo^2) + (0.0337P)^2] where P = (Fo^2 + 2Fc^2)/3
6437 reflections	(Δ/σ)max = 0.001
184 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.52 e Å^−3

Special details

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	0.75945 (2)	0.17905 (4)	0.23933 (2)	0.02194 (7)
O1	0.77600 (6)	0.05565 (10)	0.32526 (6)	0.02801 (19)
O2	0.73660 (6)	0.34616 (10)	0.26385 (6)	0.02787 (19)
O3	0.66279 (6)	0.12985 (10)	0.14016 (6)	0.02253 (17)
O4	0.59890 (7)	−0.60198 (10)	−0.04324 (7)	0.0333 (2)
O5	0.53415 (7)	−0.46018 (11)	−0.19332 (6)	0.0352 (2)
N1	0.57873 (7)	−0.46928 (12)	−0.09395 (7)	0.0241 (2)
C1	0.86393 (8)	0.17603 (13)	0.17674 (8)	0.0204 (2)
C2	0.95129 (9)	0.08355 (15)	0.22504 (9)	0.0270 (3)
H2	0.9532	0.0177	0.2874	0.0346 (13)*
C3	1.03629 (9)	0.09078 (15)	0.17870 (9)	0.0315 (3)
H3	1.0957	0.0307	0.2114	0.0346 (13)*
C4	1.03351 (9)	0.18646 (15)	0.08428 (9)	0.0265 (2)
C5	0.94383 (9)	0.27559 (16)	0.03685 (9)	0.0282 (3)
H5	0.9409	0.3389	−0.0268	0.0346 (13)*
C6	0.85901 (9)	0.27227 (15)	0.08211 (9)	0.0257 (2)
H6	0.7998	0.3332	0.0499	0.0346 (13)*
C7	1.12573 (10)	0.19353 (18)	0.03422 (11)	0.0389 (3)
H7A	1.1033	0.1756	−0.0448	0.096 (4)*
H7B	1.1744	0.1085	0.0672	0.096 (4)*
H7C	1.1581	0.3010	0.0485	0.096 (4)*
C8	0.65328 (8)	−0.02578 (13)	0.08513 (8)	0.0195 (2)
C9	0.61525 (9)	−0.01708 (14)	−0.02953 (8)	0.0221 (2)
H9	0.6060	0.0855	−0.0658	0.0346 (13)*
C10	0.59132 (8)	−0.16410 (13)	−0.08905 (8)	0.0210 (2)
H10	0.5641	−0.1623	−0.1659	0.0346 (13)*
C11	0.60875 (8)	−0.31398 (13)	−0.03178 (8)	0.0204 (2)
C12	0.64936 (9)	−0.32318 (14)	0.08232 (8)	0.0238 (2)
H12	0.6613	−0.4260	0.1181	0.0346 (13)*
C13	0.67188 (9)	−0.17601 (14)	0.14228 (8)	0.0240 (2)
H13	0.6989	−0.1780	0.2191	0.0346 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.02256 (13)	0.02290 (14)	0.02041 (12)	−0.00249 (12)	0.00547 (10)	−0.00321 (11)
O1	0.0315 (5)	0.0316 (5)	0.0201 (4)	−0.0053 (4)	0.0048 (3)	0.0027 (3)
O2	0.0297 (4)	0.0245 (4)	0.0312 (4)	−0.0021 (4)	0.0109 (3)	−0.0093 (3)
O3	0.0206 (4)	0.0210 (4)	0.0244 (4)	−0.0007 (3)	0.0024 (3)	−0.0035 (3)
O4	0.0404 (5)	0.0192 (4)	0.0409 (4)	−0.0026 (4)	0.0109 (4)	−0.0016 (4)
O5	0.0405 (5)	0.0349 (5)	0.0274 (4)	−0.0059 (4)	0.0029 (4)	−0.0090 (4)
N1	0.0225 (5)	0.0227 (5)	0.0286 (5)	−0.0021 (4)	0.0089 (4)	−0.0034 (4)
C1	0.0205 (5)	0.0201 (5)	0.0205 (5)	−0.0012 (5)	0.0047 (4)	−0.0025 (4)
C2	0.0277 (6)	0.0265 (6)	0.0261 (5)	0.0039 (5)	0.0054 (5)	0.0015 (5)
C3	0.0247 (6)	0.0303 (7)	0.0379 (6)	0.0083 (5)	0.0045 (5)	−0.0014 (5)
C4	0.0231 (6)	0.0278 (6)	0.0300 (6)	−0.0037 (5)	0.0092 (5)	−0.0103 (5)
C5	0.0261 (6)	0.0357 (7)	0.0230 (5)	−0.0027 (5)	0.0065 (5)	0.0008 (5)
C6	0.0209 (5)	0.0298 (6)	0.0241 (5)	0.0025 (5)	0.0016 (4)	0.0031 (4)
C7	0.0274 (6)	0.0471 (9)	0.0468 (8)	−0.0064 (6)	0.0178 (6)	−0.0139 (6)
C8	0.0173 (5)	0.0183 (5)	0.0230 (5)	−0.0014 (4)	0.0049 (4)	−0.0021 (4)
C9	0.0232 (5)	0.0204 (5)	0.0226 (5)	0.0012 (5)	0.0056 (4)	0.0024 (4)
C10	0.0212 (5)	0.0223 (6)	0.0186 (5)	0.0015 (5)	0.0036 (4)	0.0003 (4)
C11	0.0183 (5)	0.0197 (5)	0.0239 (5)	−0.0019 (5)	0.0065 (4)	−0.0028 (4)
C12	0.0275 (6)	0.0195 (5)	0.0241 (5)	0.0005 (5)	0.0062 (4)	0.0034 (4)
C13	0.0273 (6)	0.0237 (6)	0.0200 (5)	−0.0013 (5)	0.0039 (4)	0.0008 (4)

Geometric parameters (Å, º)

S1—O2	1.4232 (8)	C5—C6	1.3825 (15)
S1—O1	1.4288 (8)	C5—H5	0.9300
S1—O3	1.5935 (8)	C6—H6	0.9300
S1—C1	1.7556 (11)	C7—H7A	0.9600
O3—C8	1.4119 (12)	C7—H7B	0.9600
O4—N1	1.2304 (12)	C7—H7C	0.9600
O5—N1	1.2282 (11)	C8—C9	1.3852 (14)
N1—C11	1.4660 (13)	C8—C13	1.3874 (15)
C1—C2	1.3855 (15)	C9—C10	1.3844 (15)
C1—C6	1.3904 (15)	C9—H9	0.9300
C2—C3	1.3937 (16)	C10—C11	1.3850 (15)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.3907 (16)	C11—C12	1.3832 (14)
C3—H3	0.9300	C12—C13	1.3864 (15)
C4—C5	1.3922 (16)	C12—H12	0.9300
C4—C7	1.5102 (15)	C13—H13	0.9300
O2—S1—O1	119.64 (5)	C5—C6—H6	120.7
O2—S1—O3	102.82 (5)	C1—C6—H6	120.7
O1—S1—O3	110.36 (4)	C4—C7—H7A	109.5
O2—S1—C1	110.05 (5)	C4—C7—H7B	109.5
O1—S1—C1	109.03 (5)	H7A—C7—H7B	109.5
O3—S1—C1	103.66 (4)	C4—C7—H7C	109.5
C8—O3—S1	123.29 (7)	H7A—C7—H7C	109.5
O5—N1—O4	123.53 (10)	H7B—C7—H7C	109.5
O5—N1—C11	118.45 (9)	C9—C8—C13	122.66 (10)
O4—N1—C11	118.02 (9)	C9—C8—O3	114.58 (9)
C2—C1—C6	121.26 (10)	C13—C8—O3	122.53 (9)
C2—C1—S1	119.50 (8)	C10—C9—C8	118.67 (10)
C6—C1—S1	119.19 (9)	C10—C9—H9	120.7
C1—C2—C3	118.93 (10)	C8—C9—H9	120.7
C1—C2—H2	120.5	C9—C10—C11	118.61 (9)
C3—C2—H2	120.5	C9—C10—H10	120.7
C4—C3—C2	120.96 (11)	C11—C10—H10	120.7
C4—C3—H3	119.5	C12—C11—C10	122.83 (10)
C2—C3—H3	119.5	C12—C11—N1	118.51 (10)
C3—C4—C5	118.56 (10)	C10—C11—N1	118.61 (9)
C3—C4—C7	120.75 (11)	C11—C12—C13	118.62 (10)
C5—C4—C7	120.69 (11)	C11—C12—H12	120.7
C6—C5—C4	121.59 (11)	C13—C12—H12	120.7
C6—C5—H5	119.2	C12—C13—C8	118.56 (9)
C4—C5—H5	119.2	C12—C13—H13	120.7
C5—C6—C1	118.69 (11)	C8—C13—H13	120.7
O2—S1—O3—C8	177.66 (7)	S1—C1—C6—C5	176.74 (9)
O1—S1—O3—C8	−53.62 (9)	S1—O3—C8—C9	−138.45 (8)
C1—S1—O3—C8	63.01 (8)	S1—O3—C8—C13	46.95 (13)
O2—S1—C1—C2	122.94 (9)	C13—C8—C9—C10	2.38 (17)
O1—S1—C1—C2	−10.12 (11)	O3—C8—C9—C10	−172.20 (10)
O3—S1—C1—C2	−127.67 (9)	C8—C9—C10—C11	−1.53 (16)
O2—S1—C1—C6	−54.38 (10)	C9—C10—C11—C12	−0.21 (17)
O1—S1—C1—C6	172.55 (8)	C9—C10—C11—N1	177.06 (10)
O3—S1—C1—C6	55.00 (10)	O5—N1—C11—C12	173.51 (10)
C6—C1—C2—C3	1.39 (17)	O4—N1—C11—C12	−5.89 (15)
S1—C1—C2—C3	−175.88 (8)	O5—N1—C11—C10	−3.88 (15)
C1—C2—C3—C4	−1.18 (18)	O4—N1—C11—C10	176.72 (10)
C2—C3—C4—C5	0.13 (18)	C10—C11—C12—C13	1.18 (17)
C2—C3—C4—C7	−179.84 (11)	N1—C11—C12—C13	−176.09 (9)
C3—C4—C5—C6	0.76 (18)	C11—C12—C13—C8	−0.38 (16)
C7—C4—C5—C6	−179.27 (11)	C9—C8—C13—C12	−1.41 (16)
C4—C5—C6—C1	−0.56 (18)	O3—C8—C13—C12	172.75 (10)
C2—C1—C6—C5	−0.54 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.93	2.54	2.9161 (14)	105
C6—H6···O2	0.93	2.97	3.1474 (13)	92
C6—H6···O3	0.93	2.87	3.1002 (14)	95
C10—H10···O5	0.93	2.43	2.7187 (14)	98
C12—H12···O4	0.93	2.42	2.7098 (14)	98
C13—H13···O1	0.93	2.37	2.9907 (13)	124
C3—H3···O2^i	0.93	2.64	3.5305 (15)	162
C7—H7B···O2^i	0.96	3.00	3.8851 (17)	155
C6—H6···O1^ii	0.93	2.86	3.3893 (13)	117
C5—H5···O1^ii	0.93	2.63	3.2848 (14)	128
C6—H6···O4^iii	0.93	2.69	3.5770 (15)	159
C9—H9···O4^iii	0.93	2.53	3.3362 (14)	146
C7—H7C···O1^iv	0.96	2.59	3.4696 (16)	153
C10—H10···O5^v	0.93	2.50	3.2389 (13)	137
C12—H12···O2^vi	0.93	2.59	3.4828 (13)	161
C13—H13···O5^vii	0.93	2.90	3.2512 (14)	104
C2—H2···Cg^viii	0.93	3.07	3.772	134

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