2,4-Di­nitro­phenyl 4-toluene­sulfonate: molecular aggregation through weak C—H...O interactions

The title mol­ecule, C₁₃H₁₀N₂O₇S, is stabilized by weak intermolecular C—H...O interactions. The dihedral angle between the mean planes of the 4-tolyl and 2,4-di­nitro­phenyl rings is 19.26 (3)°. Both O atoms of the 4-nitro group form a `fork-like' intermolecular hydrogen-bonding motif with the C—H groups of the aromatic rings. In addition, one of the O atoms of the 2-nitro group and one of the O atoms of the sulfonyl group are also involved in weak intermolecular hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.030
• wR factor = 0.087
• Data-to-parameter ratio = 12.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: SMART-NT (Bruker, 1998); cell refinement: SMART-NT; data reduction: SAINT-NT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXTL.

2,4-dinitrophenyl 4-toluenesulfonate

Crystal data

C13H10N2O7S	Dx = 1.634 Mg m^−3
Mr = 338.29	Melting point = 119–121 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8997 reflections
a = 13.3935 (7) Å	θ = 2.5–27.5°
b = 13.4828 (8) Å	µ = 0.28 mm^−1
c = 15.2291 (8) Å	T = 100 K
V = 2750.1 (3) Å^3	Plate, colorless
Z = 8	0.40 × 0.30 × 0.07 mm
F(000) = 1392

Data collection

Bruker SMART CCD area-detector diffractometer	3170 independent reflections
Radiation source: fine-focus sealed tube	2867 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 27.6°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1995)	h = −17→17
Tmin = 0.897, Tmax = 0.981	k = −17→17
31334 measured reflections	l = −19→19

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.087	All H-atom parameters refined
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0531P)^2 + 1.1269P] where P = (Fo^2 + 2Fc^2)/3
3170 reflections	(Δ/σ)max = 0.001
248 parameters	Δρmax = 0.55 e Å^−3
0 restraints	Δρmin = −0.29 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
S	0.45137 (2)	0.18709 (2)	0.592919 (19)	0.01305 (10)
O1	0.50212 (7)	0.17897 (7)	0.67450 (6)	0.0204 (2)
O2	0.45800 (7)	0.27661 (7)	0.54357 (6)	0.0190 (2)
O3	0.49147 (6)	0.09791 (6)	0.53102 (6)	0.01485 (19)
O4	0.65747 (7)	0.01324 (7)	0.60320 (6)	0.0195 (2)
O5	0.77963 (7)	0.11669 (9)	0.58437 (6)	0.0272 (2)
O6	0.84702 (7)	0.15067 (8)	0.26858 (7)	0.0246 (2)
O7	0.72232 (9)	0.17391 (9)	0.18095 (6)	0.0309 (3)
N1	0.70164 (8)	0.07684 (8)	0.56151 (7)	0.0152 (2)
N2	0.75767 (9)	0.15729 (8)	0.25340 (7)	0.0195 (2)
C1	0.02328 (11)	0.05642 (13)	0.62561 (11)	0.0250 (3)
C2	0.12992 (9)	0.09011 (9)	0.61783 (8)	0.0160 (3)
C3	0.19217 (10)	0.09016 (9)	0.69109 (8)	0.0158 (2)
C4	0.29185 (9)	0.11779 (9)	0.68452 (8)	0.0144 (2)
C5	0.32771 (9)	0.14782 (9)	0.60331 (8)	0.0126 (2)
C6	0.26692 (9)	0.15075 (9)	0.52920 (8)	0.0140 (2)
C7	0.16838 (9)	0.12091 (10)	0.53703 (8)	0.0154 (2)
C8	0.55817 (9)	0.11742 (9)	0.46365 (8)	0.0129 (2)
C9	0.66054 (9)	0.10640 (9)	0.47624 (7)	0.0126 (2)
C10	0.72717 (9)	0.12149 (9)	0.40843 (8)	0.0139 (2)
C11	0.68829 (10)	0.14494 (9)	0.32733 (8)	0.0150 (2)
C12	0.58680 (10)	0.15706 (9)	0.31256 (8)	0.0174 (3)
C13	0.52172 (10)	0.14405 (10)	0.38202 (8)	0.0165 (3)
H1A	−0.020 (2)	0.085 (2)	0.5896 (17)	0.069 (8)*
H1B	0.0017 (18)	0.0535 (18)	0.6819 (16)	0.058 (7)*
H1C	0.0208 (16)	−0.0149 (18)	0.6092 (14)	0.050 (6)*
H3	0.1657 (13)	0.0692 (13)	0.7475 (12)	0.028 (4)*
H4	0.3366 (13)	0.1161 (13)	0.7335 (12)	0.026 (4)*
H6	0.2916 (12)	0.1708 (11)	0.4750 (11)	0.017 (4)*
H7	0.1265 (12)	0.1225 (12)	0.4864 (11)	0.020 (4)*
H10	0.7939 (13)	0.1146 (12)	0.4191 (11)	0.021 (4)*
H12	0.5649 (12)	0.1761 (12)	0.2570 (12)	0.020 (4)*
H13	0.4521 (12)	0.1510 (12)	0.3718 (10)	0.017 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.01094 (16)	0.01450 (17)	0.01372 (16)	−0.00064 (10)	0.00048 (10)	−0.00202 (10)
O1	0.0157 (4)	0.0275 (5)	0.0179 (5)	−0.0011 (4)	−0.0040 (4)	−0.0048 (4)
O2	0.0168 (4)	0.0154 (5)	0.0249 (5)	−0.0005 (3)	0.0047 (4)	0.0004 (4)
O3	0.0144 (4)	0.0139 (4)	0.0163 (4)	−0.0007 (3)	0.0055 (3)	−0.0008 (3)
O4	0.0256 (5)	0.0196 (5)	0.0135 (4)	0.0004 (4)	0.0011 (3)	0.0034 (3)
O5	0.0181 (5)	0.0433 (6)	0.0201 (5)	−0.0064 (4)	−0.0072 (4)	0.0017 (4)
O6	0.0219 (5)	0.0283 (5)	0.0236 (5)	−0.0045 (4)	0.0104 (4)	−0.0039 (4)
O7	0.0414 (6)	0.0391 (6)	0.0123 (5)	0.0063 (5)	0.0068 (4)	0.0045 (4)
N1	0.0142 (5)	0.0198 (5)	0.0116 (5)	0.0027 (4)	−0.0002 (4)	−0.0014 (4)
N2	0.0278 (6)	0.0154 (5)	0.0154 (5)	−0.0016 (4)	0.0076 (4)	−0.0018 (4)
C1	0.0160 (6)	0.0333 (8)	0.0257 (7)	−0.0049 (6)	0.0021 (6)	−0.0002 (6)
C2	0.0140 (6)	0.0150 (6)	0.0190 (6)	0.0013 (4)	0.0019 (5)	−0.0020 (5)
C3	0.0180 (6)	0.0166 (6)	0.0128 (5)	0.0005 (5)	0.0043 (4)	0.0000 (4)
C4	0.0159 (6)	0.0151 (6)	0.0121 (6)	0.0018 (4)	−0.0013 (4)	−0.0006 (4)
C5	0.0103 (5)	0.0127 (6)	0.0147 (5)	0.0001 (4)	0.0012 (4)	−0.0017 (4)
C6	0.0160 (6)	0.0145 (6)	0.0115 (5)	0.0015 (4)	0.0018 (4)	−0.0004 (4)
C7	0.0143 (6)	0.0171 (6)	0.0147 (6)	0.0018 (5)	−0.0025 (4)	−0.0017 (4)
C8	0.0135 (6)	0.0124 (5)	0.0128 (5)	−0.0014 (4)	0.0023 (4)	−0.0010 (4)
C9	0.0148 (6)	0.0118 (5)	0.0112 (5)	−0.0001 (4)	−0.0015 (4)	−0.0008 (4)
C10	0.0125 (6)	0.0131 (6)	0.0160 (6)	−0.0007 (4)	0.0016 (4)	−0.0023 (4)
C11	0.0192 (6)	0.0130 (6)	0.0130 (5)	−0.0014 (4)	0.0050 (5)	−0.0010 (4)
C12	0.0221 (7)	0.0168 (6)	0.0132 (6)	0.0006 (5)	−0.0032 (5)	0.0013 (4)
C13	0.0144 (6)	0.0172 (6)	0.0179 (6)	0.0004 (5)	−0.0027 (5)	0.0005 (5)

Geometric parameters (Å, º)

S—O1	1.4204 (10)	C3—C4	1.3897 (18)
S—O2	1.4246 (10)	C3—H3	0.972 (18)
S—O3	1.6195 (9)	C4—C5	1.3871 (17)
S—C5	1.7460 (12)	C4—H4	0.958 (18)
O3—C8	1.3855 (14)	C5—C6	1.3922 (17)
O4—N1	1.2201 (14)	C6—C7	1.3848 (18)
O5—N1	1.2251 (15)	C6—H6	0.929 (16)
O6—N2	1.2220 (16)	C7—H7	0.954 (16)
O7—N2	1.2214 (16)	C8—C13	1.3830 (17)
N1—C9	1.4656 (15)	C8—C9	1.3924 (16)
N2—C11	1.4693 (16)	C9—C10	1.3800 (17)
C1—C2	1.5035 (18)	C10—C11	1.3771 (17)
C1—H1A	0.88 (3)	C10—H10	0.913 (17)
C1—H1B	0.90 (2)	C11—C12	1.3875 (19)
C1—H1C	0.99 (2)	C12—C13	1.3819 (18)
C2—C3	1.3927 (18)	C12—H12	0.932 (18)
C2—C7	1.3972 (17)	C13—H13	0.950 (16)
O1—S—O2	119.79 (6)	C4—C5—C6	121.91 (11)
O1—S—O3	107.05 (5)	C4—C5—S	119.85 (9)
O2—S—O3	107.54 (5)	C6—C5—S	118.21 (9)
O1—S—C5	110.57 (6)	C7—C6—C5	118.64 (11)
O2—S—C5	111.34 (6)	C7—C6—H6	120.0 (10)
O3—S—C5	98.17 (5)	C5—C6—H6	121.3 (10)
C8—O3—S	120.25 (8)	C6—C7—C2	120.90 (11)
O4—N1—O5	125.01 (11)	C6—C7—H7	119.0 (10)
O4—N1—C9	118.04 (10)	C2—C7—H7	120.1 (10)
O5—N1—C9	116.92 (10)	C13—C8—O3	119.17 (11)
O7—N2—O6	124.33 (12)	C13—C8—C9	119.94 (11)
O7—N2—C11	117.89 (12)	O3—C8—C9	120.84 (11)
O6—N2—C11	117.78 (11)	C10—C9—C8	121.20 (11)
C2—C1—H1A	115.9 (17)	C10—C9—N1	117.40 (10)
C2—C1—H1B	113.0 (16)	C8—C9—N1	121.39 (10)
H1A—C1—H1B	114 (2)	C11—C10—C9	117.42 (11)
C2—C1—H1C	107.7 (13)	C11—C10—H10	123.6 (10)
H1A—C1—H1C	104 (2)	C9—C10—H10	119.0 (10)
H1B—C1—H1C	100.7 (19)	C10—C11—C12	122.88 (11)
C3—C2—C7	118.99 (11)	C10—C11—N2	118.31 (11)
C3—C2—C1	120.38 (12)	C12—C11—N2	118.81 (11)
C7—C2—C1	120.63 (12)	C13—C12—C11	118.61 (11)
C4—C3—C2	121.17 (11)	C13—C12—H12	122.2 (10)
C4—C3—H3	119.5 (10)	C11—C12—H12	119.2 (10)
C2—C3—H3	119.3 (11)	C12—C13—C8	119.90 (12)
C5—C4—C3	118.36 (11)	C12—C13—H13	118.8 (10)
C5—C4—H4	119.0 (10)	C8—C13—H13	121.3 (10)
C3—C4—H4	122.7 (10)
O1—S—O3—C8	−104.44 (9)	C13—C8—C9—C10	−0.07 (19)
O2—S—O3—C8	25.49 (10)	O3—C8—C9—C10	177.14 (11)
C5—S—O3—C8	141.02 (9)	C13—C8—C9—N1	−179.09 (11)
C7—C2—C3—C4	−1.65 (19)	O3—C8—C9—N1	−1.88 (18)
C1—C2—C3—C4	177.76 (13)	O4—N1—C9—C10	−138.89 (12)
C2—C3—C4—C5	1.54 (19)	O5—N1—C9—C10	39.39 (16)
C3—C4—C5—C6	−0.07 (19)	O4—N1—C9—C8	40.17 (16)
C3—C4—C5—S	177.87 (9)	O5—N1—C9—C8	−141.55 (12)
O1—S—C5—C4	2.05 (12)	C8—C9—C10—C11	−1.89 (18)
O2—S—C5—C4	−133.69 (10)	N1—C9—C10—C11	177.17 (11)
O3—S—C5—C4	113.79 (10)	C9—C10—C11—C12	2.29 (19)
O1—S—C5—C6	−179.93 (9)	C9—C10—C11—N2	−177.53 (11)
O2—S—C5—C6	44.32 (11)	O7—N2—C11—C10	176.94 (12)
O3—S—C5—C6	−68.20 (10)	O6—N2—C11—C10	−3.36 (17)
C4—C5—C6—C7	−1.25 (18)	O7—N2—C11—C12	−2.88 (17)
S—C5—C6—C7	−179.22 (9)	O6—N2—C11—C12	176.82 (11)
C5—C6—C7—C2	1.14 (19)	C10—C11—C12—C13	−0.68 (19)
C3—C2—C7—C6	0.28 (19)	N2—C11—C12—C13	179.14 (11)
C1—C2—C7—C6	−179.13 (12)	C11—C12—C13—C8	−1.38 (19)
S—O3—C8—C13	−87.56 (13)	O3—C8—C13—C12	−175.52 (11)
S—O3—C8—C9	95.21 (12)	C9—C8—C13—C12	1.74 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O4^i	0.950 (16)	2.683 (16)	3.2107 (16)	115.7 (12)
C13—H13···O6^ii	0.950 (16)	2.560 (16)	3.2777 (16)	132.5 (12)
C12—H12···O1^iii	0.932 (18)	2.470 (17)	3.2549 (16)	141.9 (13)
C10—H10···O2^iv	0.913 (17)	2.703 (17)	3.4612 (15)	141.1 (14)
C6—H6···O7^ii	0.929 (16)	2.551 (16)	3.2706 (16)	134.6 (12)
C6—H6···O4^i	0.929 (16)	2.835 (15)	3.1592 (15)	101.8 (11)
C7—H7···O2^v	0.954 (16)	2.674 (16)	3.3698 (15)	130.2 (12)
C7—H7···O7^ii	0.954 (16)	2.937 (16)	3.4716 (16)	116.7 (11)
C3—H3···O4^vi	0.971 (18)	2.398 (18)	3.3325 (15)	161.2 (14)
C3—H3···O1^vi	0.971 (18)	2.899 (18)	3.4789 (15)	119.3 (12)
C3—H3···O6^i	0.971 (18)	2.979 (17)	3.3460 (16)	103.8 (11)
C4—H4···O5^vi	0.958 (18)	2.876 (17)	3.5234 (15)	125.8 (13)
C1—H1A···O2^v	0.88 (3)	2.77 (3)	3.531 (2)	145 (2)
C1—H1B···O1^vi	0.90 (2)	2.77 (2)	3.4752 (19)	136 (2)
C1—H1A···O5^vii	0.88 (3)	2.72 (3)	3.4211 (18)	137 (2)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1/2, y, −z+1/2; (iii) x, −y+1/2, z−1/2; (iv) x+1/2, −y+1/2, −z+1; (v) x−1/2, −y+1/2, −z+1; (vi) x−1/2, y, −z+3/2; (vii) x−1, y, z.