Ethyl phenyl­sulfonyl­acetate

The ethyl ­acetate portion of the mol­ecule of ethyl phenyl­sulfonyl­acetate, C₁₀H₁₂O₄S, is nearly planar, and it makes a dihedral angle of 44.3 (1)° with the plane of the aromatic ring.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.038
• wR factor = 0.098
• Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.25 Ratio
PLAT320_ALERT_2_C Check Hybridisation of  C9     in Main Residue .          ?
PLAT731_ALERT_1_C Bond    Calc     0.95(3), Rep   0.950(10) ......       3.00 su-Rat
              C3   -H3      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.95(3), Rep   0.950(10) ......       3.00 su-Rat
              C5   -H5      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.95(3), Rep   0.950(10) ......       3.00 su-Rat
              C10  -H103    1.555   1.555

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.50
           From the CIF: _reflns_number_total               2341
           Count of symmetry unique reflns         1398
           Completeness (_total/calc)            167.45%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       943
           Fraction of Friedel pairs measured     0.675
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   3 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-II (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Ethyl phenylsulfonylacetate

Crystal data

C10H12O4S	F(000) = 240
Mr = 228.26	Dx = 1.371 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2044 reflections
a = 8.8812 (3) Å	θ = 2.5–27.7°
b = 5.8066 (2) Å	µ = 0.28 mm^−1
c = 11.5280 (5) Å	T = 298 K
β = 111.583 (1)°	Block, colorless
V = 552.81 (4) Å^3	0.42 × 0.21 × 0.13 mm
Z = 2

Data collection

Bruker APEX area-detector diffractometer	2273 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.014
Graphite monochromator	θmax = 27.5°, θmin = 1.9°
φ and ω scans	h = −10→11
3436 measured reflections	k = −7→7
2341 independent reflections	l = −14→7

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	All H-atom parameters refined
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.0648P)^2 + 0.013P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
2341 reflections	Δρmax = 0.18 e Å^−3
184 parameters	Δρmin = −0.28 e Å^−3
13 restraints	Absolute structure: Flack (1983); 974 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.19 (8)

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

	x	y	z	Uiso*/Ueq
S1	1.05927 (5)	0.50000 (8)	0.29261 (4)	0.03713 (15)
O1	1.2033 (1)	0.4115 (4)	0.2808 (2)	0.0563 (5)
O2	1.0662 (2)	0.7175 (3)	0.3536 (2)	0.0542 (4)
O3	0.7236 (2)	0.1374 (4)	0.2874 (2)	0.0772 (7)
O4	0.7614 (2)	0.4816 (3)	0.3776 (1)	0.0429 (3)
C1	0.9054 (2)	0.5136 (4)	0.1429 (2)	0.0369 (4)
C2	0.7910 (3)	0.6879 (4)	0.1151 (2)	0.0470 (5)
C3	0.6698 (3)	0.6913 (5)	−0.0027 (3)	0.0619 (7)
C4	0.6635 (3)	0.5260 (6)	−0.0890 (2)	0.0614 (7)
C5	0.7773 (3)	0.3513 (6)	−0.0597 (2)	0.0586 (7)
C6	0.8999 (3)	0.3445 (4)	0.0566 (2)	0.0466 (5)
C7	0.9901 (3)	0.2853 (4)	0.3732 (2)	0.0409 (5)
C8	0.8099 (3)	0.2907 (4)	0.3413 (2)	0.0414 (5)
C9	0.5868 (3)	0.5080 (6)	0.3463 (3)	0.0556 (6)
C10	0.5595 (3)	0.7018 (6)	0.4182 (3)	0.0641 (7)
H2	0.799 (3)	0.799 (3)	0.176 (2)	0.04 (1)*
H3	0.593 (4)	0.813 (5)	−0.018 (3)	0.10 (1)*
H4	0.581 (2)	0.530 (6)	−0.170 (1)	0.07 (1)*
H5	0.771 (5)	0.229 (6)	−0.116 (3)	0.13 (2)*
H6	0.985 (2)	0.237 (4)	0.079 (2)	0.05 (1)*
H71	1.051 (3)	0.317 (5)	0.459 (1)	0.06 (1)*
H72	1.021 (3)	0.135 (3)	0.356 (2)	0.06 (1)*
H91	0.551 (5)	0.355 (3)	0.348 (3)	0.09 (1)*
H92	0.551 (3)	0.546 (5)	0.261 (1)	0.05 (1)*
H101	0.449 (2)	0.740 (6)	0.396 (3)	0.08 (1)*
H102	0.606 (3)	0.661 (6)	0.504 (1)	0.07 (1)*
H103	0.613 (4)	0.839 (4)	0.409 (3)	0.09 (1)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0320 (2)	0.0404 (3)	0.0363 (2)	−0.0046 (2)	0.0095 (2)	0.0000 (2)
O1	0.031 (1)	0.081 (1)	0.056 (1)	0.001 (1)	0.014 (1)	0.004 (1)
O2	0.066 (1)	0.045 (1)	0.045 (1)	−0.014 (1)	0.013 (1)	−0.006 (1)
O3	0.058 (1)	0.062 (1)	0.119 (2)	−0.023 (1)	0.040 (1)	−0.038 (1)
O4	0.033 (1)	0.045 (1)	0.048 (1)	−0.005 (1)	0.013 (1)	−0.005 (1)
C1	0.034 (1)	0.042 (1)	0.033 (1)	−0.001 (1)	0.010 (1)	0.002 (1)
C2	0.051 (1)	0.043 (1)	0.046 (1)	0.010 (1)	0.016 (1)	0.003 (1)
C3	0.055 (2)	0.066 (2)	0.057 (1)	0.020 (1)	0.011 (1)	0.011 (1)
C4	0.050 (1)	0.084 (2)	0.041 (1)	0.005 (2)	0.005 (1)	0.008 (2)
C5	0.054 (1)	0.074 (2)	0.044 (1)	−0.001 (1)	0.013 (1)	−0.016 (1)
C6	0.044 (1)	0.048 (1)	0.047 (1)	0.007 (1)	0.016 (1)	−0.007 (1)
C7	0.039 (1)	0.039 (1)	0.043 (1)	0.001 (1)	0.013 (1)	0.007 (1)
C8	0.043 (1)	0.040 (1)	0.042 (1)	−0.004 (1)	0.016 (1)	0.000 (1)
C9	0.034 (1)	0.070 (2)	0.062 (1)	−0.005 (1)	0.017 (1)	−0.017 (2)
C10	0.042 (1)	0.071 (2)	0.081 (2)	−0.005 (1)	0.024 (1)	−0.018 (2)

Geometric parameters (Å, º)

S1—O1	1.431 (2)	C9—C10	1.470 (4)
S1—O2	1.436 (2)	C2—H2	0.94 (1)
S1—C1	1.766 (2)	C3—H3	0.95 (1)
S1—C7	1.792 (2)	C4—H4	0.95 (1)
O3—C8	1.190 (3)	C5—H5	0.95 (1)
O4—C8	1.312 (3)	C6—H6	0.94 (1)
O4—C9	1.465 (2)	C7—H71	0.95 (1)
C1—C2	1.385 (3)	C7—H72	0.96 (1)
C1—C6	1.386 (3)	C9—H91	0.95 (1)
C2—C3	1.388 (4)	C9—H92	0.94 (1)
C3—C4	1.369 (4)	C10—H101	0.95 (1)
C4—C5	1.383 (4)	C10—H102	0.95 (1)
C5—C6	1.382 (3)	C10—H103	0.95 (1)
C7—C8	1.505 (3)
O1—S1—O2	118.9 (1)	C2—C3—H3	116 (2)
O1—S1—C1	108.7 (1)	C3—C4—H4	120 (2)
O2—S1—C1	108.5 (1)	C5—C4—H4	119 (2)
O1—S1—C7	106.7 (1)	C6—C5—H5	118 (3)
O2—S1—C7	108.6 (1)	C4—C5—H5	122 (3)
C1—S1—C7	104.4 (1)	C5—C6—H6	124 (2)
C8—O4—C9	116.8 (2)	C1—C6—H6	117 (2)
C2—C1—C6	121.5 (2)	C8—C7—H71	113 (2)
C2—C1—S1	119.8 (2)	S1—C7—H71	103 (2)
C6—C1—S1	118.7 (2)	C8—C7—H72	109 (2)
C1—C2—C3	118.4 (2)	S1—C7—H72	110 (2)
C2—C3—C4	120.7 (2)	H71—C7—H72	107 (2)
C3—C4—C5	120.4 (2)	O4—C9—H91	103 (2)
C4—C5—C6	120.2 (2)	C10—C9—H91	125 (2)
C5—C6—C1	118.9 (2)	O4—C9—H92	102 (2)
S1—C7—C8	113.3 (2)	C10—C9—H92	110 (2)
O3—C8—O4	125.1 (2)	H91—C9—H92	105 (3)
O3—C8—C7	122.3 (2)	C9—C10—H101	113 (2)
O4—C8—C7	112.6 (2)	C9—C10—H102	107 (2)
O4—C9—C10	108.7 (2)	H101—C10—H102	110 (3)
C1—C2—H2	119 (2)	C9—C10—H103	113 (2)
C3—C2—H2	123 (2)	H101—C10—H103	106 (3)
C4—C3—H3	123 (2)	H102—C10—H103	106 (3)
O1—S1—C1—C2	−146.6 (2)	C4—C5—C6—C1	0.7 (4)
O2—S1—C1—C2	−15.9 (2)	C2—C1—C6—C5	0.0 (4)
C7—S1—C1—C2	99.8 (2)	S1—C1—C6—C5	178.4 (2)
O1—S1—C1—C6	35.0 (2)	O1—S1—C7—C8	−152.2 (2)
O2—S1—C1—C6	165.7 (2)	O2—S1—C7—C8	78.4 (2)
C7—S1—C1—C6	−78.6 (2)	C1—S1—C7—C8	−37.2 (2)
C6—C1—C2—C3	−0.5 (4)	C9—O4—C8—O3	−1.4 (3)
S1—C1—C2—C3	−178.8 (2)	C9—O4—C8—C7	177.5 (2)
C1—C2—C3—C4	0.1 (4)	S1—C7—C8—O3	114.1 (2)
C2—C3—C4—C5	0.6 (4)	S1—C7—C8—O4	−64.9 (2)
C3—C4—C5—C6	−1.1 (4)	C8—O4—C9—C10	167.0 (2)