Methyl 4-(3-nitro­benzene­sulfonyl­oxy)­benzoate

In the title mol­ecule, C₁₄H₁₁NO₇S, (I), there are weak C—H...O interactions which generate rings of motifs S(5), S(6), R¹₂(5) and R²₂(7). The supramolecular aggregation is completed by the presence of C—H...π and π–π interactions.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.036
• wR factor = 0.082
• Data-to-parameter ratio = 13.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

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

methyl 4-(3-nitrobenzenesulfonyloxy)benzoate

Crystal data

C14H11NO7S	F(000) = 696
Mr = 337.30	Dx = 1.578 Mg m^−3
Monoclinic, P21/c	Melting point = 374–375 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.125 (2) Å	Cell parameters from 928 reflections
b = 9.643 (2) Å	θ = 3.2–27.1°
c = 13.236 (3) Å	µ = 0.27 mm^−1
β = 90.257 (5)°	T = 120 K
V = 1419.9 (5) Å^3	Block, colourless
Z = 4	0.22 × 0.13 × 0.12 mm

Data collection

Bruker Proteum M diffractometer	2405 reflections with I > 2σ(I)
Radiation source: Bede microsource	Rint = 0.030
Graphite monochromator	θmax = 27.2°, θmin = 2.6°
Detector resolution: 8 pixels mm^-1	h = −13→14
ω scans	k = −12→9
9472 measured reflections	l = −16→15
3150 independent reflections

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)] = 0.036	Hydrogen site location: difference Fourier map
wR(F^2) = 0.082	Only H-atom coordinates refined
S = 0.95	w = 1/[σ^2(Fo^2) + (0.0439P)^2] where P = (Fo^2 + 2Fc^2)/3
3150 reflections	(Δ/σ)max < 0.001
241 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.39 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	0.26690 (4)	0.22089 (4)	−0.11608 (3)	0.01885 (12)
N1	0.45801 (15)	−0.00838 (18)	0.19664 (12)	0.0308 (4)
O1	0.53362 (12)	−0.00646 (17)	0.26416 (11)	0.0429 (4)
O2	0.37751 (14)	−0.09446 (15)	0.18929 (11)	0.0413 (4)
O3	0.22731 (11)	0.08619 (12)	−0.14288 (9)	0.0264 (3)
O4	0.29915 (11)	0.31888 (13)	−0.19137 (9)	0.0268 (3)
O5	0.15803 (9)	0.27944 (11)	−0.05147 (8)	0.0177 (3)
O6	0.10506 (13)	0.80063 (13)	0.23260 (10)	0.0333 (3)
O7	0.10570 (10)	0.90605 (11)	0.08157 (9)	0.0199 (3)
C1	0.46454 (15)	0.10074 (18)	0.11890 (13)	0.0232 (4)
C2	0.55868 (16)	0.1936 (2)	0.12132 (15)	0.0297 (5)
H2	0.6183 (18)	0.1882 (19)	0.1710 (16)	0.036*
C3	0.56406 (17)	0.2951 (2)	0.04769 (16)	0.0327 (5)
H3	0.6274 (18)	0.362 (2)	0.0479 (16)	0.039*
C4	0.47614 (16)	0.3041 (2)	−0.02634 (15)	0.0257 (4)
H4	0.4790 (17)	0.369 (2)	−0.0746 (16)	0.031*
C5	0.38284 (14)	0.20873 (18)	−0.02590 (13)	0.0195 (4)
C6	0.37584 (15)	0.10512 (18)	0.04601 (13)	0.0198 (4)
H6	0.3137 (17)	0.0418 (19)	0.0449 (14)	0.024*
C7	0.16383 (13)	0.41398 (16)	−0.00777 (12)	0.0158 (3)
C8	0.18674 (15)	0.42244 (18)	0.09460 (13)	0.0191 (4)
H8	0.2077 (15)	0.3430 (19)	0.1308 (14)	0.023*
C9	0.17491 (15)	0.54982 (18)	0.14107 (13)	0.0192 (4)
H9	0.1850 (15)	0.5553 (18)	0.2122 (15)	0.023*
C10	0.14204 (14)	0.66597 (17)	0.08523 (12)	0.0169 (3)
C11	0.12576 (14)	0.65505 (18)	−0.01888 (13)	0.0167 (3)
H11	0.1068 (15)	0.7333 (18)	−0.0570 (14)	0.020*
C12	0.13569 (14)	0.52781 (17)	−0.06627 (13)	0.0164 (3)
H12	0.1223 (15)	0.5181 (18)	−0.1343 (14)	0.020*
C13	0.11711 (15)	0.79580 (17)	0.14221 (13)	0.0205 (4)
C14	0.07278 (18)	1.03346 (19)	0.13207 (15)	0.0248 (4)
H14A	0.1358 (17)	1.0643 (19)	0.1784 (15)	0.030*
H14B	0.0625 (17)	1.1011 (19)	0.0802 (16)	0.030*
H14C	−0.0028 (18)	1.0212 (19)	0.1657 (15)	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0209 (2)	0.0209 (2)	0.0148 (2)	0.00241 (17)	0.00100 (16)	−0.00222 (17)
N1	0.0340 (9)	0.0385 (10)	0.0198 (8)	0.0190 (8)	0.0000 (7)	−0.0011 (7)
O1	0.0337 (7)	0.0690 (11)	0.0259 (8)	0.0200 (7)	−0.0049 (6)	0.0063 (7)
O2	0.0547 (9)	0.0349 (9)	0.0343 (9)	0.0013 (7)	−0.0063 (7)	0.0079 (7)
O3	0.0326 (7)	0.0236 (7)	0.0228 (7)	0.0017 (5)	−0.0034 (5)	−0.0075 (5)
O4	0.0282 (7)	0.0322 (7)	0.0200 (7)	0.0026 (6)	0.0051 (5)	0.0048 (5)
O5	0.0175 (6)	0.0165 (6)	0.0192 (6)	−0.0004 (5)	0.0017 (5)	−0.0025 (5)
O6	0.0627 (9)	0.0220 (7)	0.0151 (7)	0.0012 (6)	0.0033 (6)	−0.0019 (5)
O7	0.0275 (6)	0.0147 (6)	0.0174 (6)	0.0004 (5)	0.0011 (5)	−0.0002 (5)
C1	0.0243 (9)	0.0274 (10)	0.0178 (9)	0.0121 (8)	0.0024 (7)	−0.0044 (7)
C2	0.0213 (9)	0.0406 (12)	0.0271 (11)	0.0106 (8)	−0.0044 (8)	−0.0088 (9)
C3	0.0212 (9)	0.0365 (12)	0.0404 (12)	−0.0028 (9)	0.0004 (9)	−0.0069 (9)
C4	0.0226 (9)	0.0266 (11)	0.0279 (11)	0.0008 (8)	0.0035 (8)	0.0006 (8)
C5	0.0173 (8)	0.0223 (9)	0.0188 (9)	0.0044 (7)	0.0017 (7)	−0.0048 (7)
C6	0.0205 (8)	0.0204 (9)	0.0184 (9)	0.0045 (7)	0.0030 (7)	−0.0040 (7)
C7	0.0138 (8)	0.0159 (8)	0.0177 (9)	−0.0014 (6)	0.0017 (6)	−0.0026 (6)
C8	0.0208 (8)	0.0188 (9)	0.0178 (9)	0.0017 (7)	−0.0021 (7)	0.0039 (7)
C9	0.0217 (8)	0.0223 (9)	0.0137 (9)	−0.0012 (7)	−0.0012 (7)	0.0008 (7)
C10	0.0156 (8)	0.0191 (9)	0.0159 (9)	−0.0020 (7)	0.0009 (6)	−0.0003 (7)
C11	0.0164 (8)	0.0181 (9)	0.0156 (9)	0.0004 (7)	−0.0001 (6)	0.0034 (7)
C12	0.0146 (8)	0.0221 (9)	0.0126 (8)	−0.0007 (7)	0.0006 (6)	−0.0001 (7)
C13	0.0236 (9)	0.0192 (9)	0.0188 (9)	−0.0030 (7)	0.0000 (7)	−0.0002 (7)
C14	0.0320 (10)	0.0161 (9)	0.0263 (11)	−0.0002 (8)	0.0022 (9)	−0.0011 (8)

Geometric parameters (Å, º)

S1—O3	1.4163 (12)	C4—H4	0.89 (2)
S1—O4	1.4206 (13)	C5—C6	1.382 (2)
S1—O5	1.5894 (12)	C6—H6	0.922 (18)
S1—C5	1.7573 (17)	C7—C12	1.378 (2)
N1—O2	1.225 (2)	C7—C8	1.380 (2)
N1—O1	1.225 (2)	C8—C9	1.380 (2)
N1—C1	1.474 (2)	C8—H8	0.932 (18)
O5—C7	1.4219 (19)	C9—C10	1.390 (2)
O6—C13	1.205 (2)	C9—H9	0.949 (19)
O7—C13	1.338 (2)	C10—C11	1.393 (2)
O7—C14	1.447 (2)	C10—C13	1.488 (2)
C1—C6	1.378 (2)	C11—C12	1.383 (2)
C1—C2	1.378 (3)	C11—H11	0.932 (18)
C2—C3	1.382 (3)	C12—H12	0.917 (18)
C2—H2	0.93 (2)	C14—H14A	0.98 (2)
C3—C4	1.384 (3)	C14—H14B	0.95 (2)
C3—H3	0.95 (2)	C14—H14C	0.96 (2)
C4—C5	1.387 (2)
O3—S1—O4	120.90 (8)	C5—C6—H6	120.8 (12)
O3—S1—O5	102.93 (7)	C12—C7—C8	123.01 (15)
O4—S1—O5	109.67 (7)	C12—C7—O5	119.23 (14)
O3—S1—C5	109.59 (8)	C8—C7—O5	117.47 (14)
O4—S1—C5	109.51 (8)	C7—C8—C9	118.20 (16)
O5—S1—C5	102.53 (7)	C7—C8—H8	120.1 (12)
O2—N1—O1	124.60 (17)	C9—C8—H8	121.7 (12)
O2—N1—C1	117.83 (16)	C8—C9—C10	120.37 (16)
O1—N1—C1	117.57 (17)	C8—C9—H9	118.7 (11)
C7—O5—S1	120.64 (9)	C10—C9—H9	120.8 (11)
C13—O7—C14	114.92 (14)	C9—C10—C11	119.85 (16)
C6—C1—C2	122.55 (18)	C9—C10—C13	117.24 (15)
C6—C1—N1	118.26 (17)	C11—C10—C13	122.76 (15)
C2—C1—N1	119.19 (16)	C12—C11—C10	120.36 (16)
C1—C2—C3	118.62 (18)	C12—C11—H11	119.4 (11)
C1—C2—H2	121.2 (12)	C10—C11—H11	120.2 (11)
C3—C2—H2	120.2 (12)	C7—C12—C11	118.06 (16)
C2—C3—C4	120.72 (19)	C7—C12—H12	120.4 (11)
C2—C3—H3	120.6 (13)	C11—C12—H12	121.5 (11)
C4—C3—H3	118.6 (13)	O6—C13—O7	123.65 (16)
C3—C4—C5	118.81 (18)	O6—C13—C10	123.86 (16)
C3—C4—H4	121.6 (13)	O7—C13—C10	112.46 (14)
C5—C4—H4	119.6 (13)	O7—C14—H14A	111.5 (11)
C6—C5—C4	121.78 (17)	O7—C14—H14B	106.1 (12)
C6—C5—S1	118.20 (13)	H14A—C14—H14B	109.1 (16)
C4—C5—S1	119.99 (14)	O7—C14—H14C	109.5 (11)
C1—C6—C5	117.52 (17)	H14A—C14—H14C	112.0 (16)
C1—C6—H6	121.7 (12)	H14B—C14—H14C	108.4 (16)
O3—S1—O5—C7	178.58 (11)	C4—C5—C6—C1	0.9 (2)
O4—S1—O5—C7	−51.51 (13)	S1—C5—C6—C1	−177.16 (12)
C5—S1—O5—C7	64.78 (13)	S1—O5—C7—C12	82.62 (16)
O2—N1—C1—C6	3.9 (2)	S1—O5—C7—C8	−103.36 (15)
O1—N1—C1—C6	−176.06 (15)	C12—C7—C8—C9	3.3 (2)
O2—N1—C1—C2	−175.77 (16)	O5—C7—C8—C9	−170.44 (14)
O1—N1—C1—C2	4.3 (2)	C7—C8—C9—C10	−0.7 (2)
C6—C1—C2—C3	0.0 (3)	C8—C9—C10—C11	−2.7 (2)
N1—C1—C2—C3	179.71 (16)	C8—C9—C10—C13	173.00 (15)
C1—C2—C3—C4	0.6 (3)	C9—C10—C11—C12	3.5 (2)
C2—C3—C4—C5	−0.5 (3)	C13—C10—C11—C12	−171.87 (15)
C3—C4—C5—C6	−0.3 (3)	C8—C7—C12—C11	−2.5 (2)
C3—C4—C5—S1	177.75 (14)	O5—C7—C12—C11	171.19 (13)
O3—S1—C5—C6	−36.51 (15)	C10—C11—C12—C7	−1.0 (2)
O4—S1—C5—C6	−171.30 (13)	C14—O7—C13—O6	−2.3 (2)
O5—S1—C5—C6	72.30 (14)	C14—O7—C13—C10	175.73 (14)
O3—S1—C5—C4	145.38 (14)	C9—C10—C13—O6	−12.3 (3)
O4—S1—C5—C4	10.59 (16)	C11—C10—C13—O6	163.26 (17)
O5—S1—C5—C4	−105.81 (14)	C9—C10—C13—O7	169.75 (14)
C2—C1—C6—C5	−0.8 (3)	C11—C10—C13—O7	−14.7 (2)
N1—C1—C6—C5	179.54 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.93 (2)	2.438 (19)	2.717 (3)	97.2 (13)
C4—H4···O4	0.886 (19)	2.571 (18)	2.938 (2)	105.8 (13)
C6—H6···O2	0.920 (18)	2.422 (18)	2.702 (2)	97.6 (13)
C6—H6···O3	0.920 (18)	2.696 (18)	2.996 (2)	100.0 (13)
C9—H9···O6	0.946 (18)	2.543 (17)	2.816 (2)	96.8 (11)
C11—H11···O7	0.928 (16)	2.479 (16)	2.771 (2)	98.4 (11)
C12—H12···O4	0.915 (18)	2.855 (16)	3.184 (2)	102.7 (12)
C2—H2···O2^i	0.93 (2)	2.796 (19)	3.309 (3)	115.7 (14)
C4—H4···O1^ii	0.886 (19)	2.596 (19)	3.454 (3)	163.2 (15)
C6—H6···O7^iii	0.920 (18)	2.707 (19)	3.599 (2)	163.5 (15)
C9—H9···O3^iv	0.946 (18)	2.401 (18)	3.198 (2)	141.6 (13)
C8—H8···O4^iv	0.932 (18)	2.998 (18)	3.870 (2)	156.4 (14)
C12—H12···O6^v	0.915 (18)	2.489 (18)	3.152 (2)	129.6 (13)
C11—H11···O6^v	0.928 (16)	2.805 (16)	3.324 (2)	116.5 (11)
C14—H14A···O4^vi	0.98 (2)	2.74 (2)	3.712 (2)	173.3 (15)
C14—H14B···O5^vii	0.953 (19)	2.67 (2)	3.528 (2)	149.7 (15)
C14—H14B···O7^viii	0.953 (19)	2.839 (19)	3.497 (2)	127.1 (13)
C14—H14C···O3^ix	0.96 (2)	2.721 (19)	3.536 (2)	143.2 (15)
C3—H3···Cg2^x	0.95 (2)	2.85	3.70	149

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