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In the title compound, C16H14N2O4S, the phenyl and quinoxaline 1,4-dioxide planes are approximately perpendicular, with a dihedral angle of 85.8 (2)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806001498/is6179sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806001498/is6179Isup2.hkl
Contains datablock I

CCDC reference: 298476

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.041
  • wR factor = 0.110
  • Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.94 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 - C5 .. 5.33 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for S1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

3-Ethylsulfonyl-2-phenylquinoxaline 1,4-dioxide top
Crystal data top
C16H14N2O4SF(000) = 688.00
Mr = 330.36Dx = 1.439 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ynCell parameters from 11903 reflections
a = 10.261 (5) Åθ = 3.1–27.5°
b = 8.573 (4) ŵ = 0.23 mm1
c = 17.898 (7) ÅT = 298 K
β = 104.415 (16)°Prism, brown
V = 1524.9 (11) Å30.55 × 0.45 × 0.32 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2423 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.026
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1313
Tmin = 0.859, Tmax = 0.928k = 118
14375 measured reflectionsl = 2323
3489 independent reflections
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.041 w = 1/[0.0009Fo2 + σ(Fo2)]/(4Fo2)
wR(F2) = 0.110(Δ/σ)max < 0.001
S = 1.01Δρmax = 0.29 e Å3
3489 reflectionsΔρmin = 0.29 e Å3
208 parameters
Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.08023 (4)0.19162 (6)0.42985 (3)0.04754 (13)
O10.35568 (12)0.11824 (18)0.48645 (8)0.0703 (4)
O20.30342 (12)0.64992 (17)0.32673 (8)0.0627 (4)
O30.09843 (18)0.1957 (2)0.51137 (8)0.0879 (5)
O40.03938 (12)0.25699 (18)0.38319 (10)0.0757 (4)
N10.34184 (12)0.24132 (17)0.44507 (8)0.0416 (3)
N20.31393 (12)0.51750 (16)0.36088 (6)0.0400 (3)
C10.21908 (14)0.29783 (19)0.40913 (9)0.0371 (4)
C20.45582 (14)0.31950 (19)0.43611 (9)0.0385 (4)
C30.58354 (16)0.2576 (2)0.46994 (10)0.0501 (5)
C40.69373 (17)0.3366 (2)0.46096 (11)0.0558 (5)
C50.68065 (17)0.4767 (2)0.42123 (11)0.0590 (5)
C60.55744 (17)0.5396 (2)0.38884 (10)0.0522 (5)
C70.44206 (14)0.4588 (2)0.39541 (9)0.0387 (4)
C80.20351 (13)0.43429 (19)0.36421 (9)0.0353 (3)
C90.07384 (14)0.4953 (2)0.31598 (9)0.0388 (4)
C100.00435 (17)0.5978 (2)0.34510 (11)0.0490 (5)
C110.12180 (19)0.6559 (2)0.29735 (13)0.0658 (6)
C120.1596 (2)0.6093 (3)0.22128 (14)0.0768 (7)
C130.0827 (2)0.5067 (3)0.19256 (12)0.0759 (7)
C140.0355 (2)0.4495 (2)0.23933 (10)0.0574 (5)
C150.0957 (2)0.0008 (2)0.39816 (11)0.0547 (5)
C160.0978 (3)0.0065 (3)0.31464 (14)0.1039 (10)
H30.59270.16480.49770.059*
H40.77900.29590.48190.066*
H50.75750.52900.41630.072*
H60.54990.63460.36310.063*
H100.02150.62780.39660.059*
H110.17460.72610.31640.080*
H120.23830.64840.18920.088*
H130.11040.47460.14140.086*
H140.08890.38110.21970.067*
H1520.17800.04660.42910.067*
H1510.02070.06270.40560.066*
H1610.16940.05840.30670.134*
H1620.01350.03090.28360.135*
H1630.11190.11190.30030.134*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0412 (2)0.0462 (2)0.0612 (2)0.01251 (19)0.02392 (19)0.0006 (2)
O10.0555 (8)0.0600 (9)0.0869 (9)0.0054 (6)0.0017 (7)0.0378 (7)
O20.0558 (7)0.0502 (8)0.0829 (9)0.0055 (6)0.0187 (6)0.0231 (6)
O30.1120 (13)0.0997 (13)0.0681 (9)0.0516 (10)0.0529 (9)0.0179 (8)
O40.0338 (6)0.0595 (9)0.1352 (13)0.0053 (6)0.0238 (7)0.0170 (8)
N10.0345 (6)0.0400 (7)0.0487 (7)0.0040 (5)0.0072 (5)0.0088 (6)
N20.0353 (6)0.0372 (7)0.0487 (7)0.0038 (5)0.0128 (5)0.0068 (5)
C10.0298 (7)0.0382 (8)0.0445 (8)0.0052 (6)0.0118 (6)0.0015 (6)
C20.0311 (7)0.0421 (9)0.0427 (8)0.0011 (6)0.0098 (6)0.0016 (7)
C30.0358 (8)0.0528 (11)0.0582 (10)0.0064 (7)0.0053 (7)0.0014 (8)
C40.0304 (8)0.0747 (14)0.0609 (10)0.0047 (8)0.0088 (7)0.0066 (10)
C50.0311 (8)0.0871 (15)0.0613 (10)0.0152 (9)0.0163 (7)0.0065 (10)
C60.0404 (9)0.0621 (12)0.0563 (9)0.0135 (8)0.0164 (7)0.0068 (8)
C70.0301 (7)0.0464 (9)0.0407 (8)0.0045 (6)0.0109 (6)0.0001 (7)
C80.0296 (7)0.0365 (8)0.0408 (7)0.0014 (6)0.0105 (6)0.0020 (6)
C90.0307 (7)0.0371 (8)0.0474 (8)0.0016 (6)0.0075 (6)0.0026 (6)
C100.0419 (9)0.0446 (10)0.0614 (10)0.0032 (7)0.0143 (7)0.0028 (8)
C110.0434 (10)0.0554 (13)0.1007 (17)0.0132 (9)0.0218 (10)0.0183 (11)
C120.0425 (10)0.0860 (17)0.0898 (16)0.0092 (11)0.0068 (10)0.0337 (13)
C130.0655 (14)0.0947 (18)0.0548 (11)0.0033 (13)0.0089 (10)0.0084 (11)
C140.0522 (10)0.0668 (13)0.0498 (10)0.0064 (9)0.0063 (8)0.0037 (9)
C150.0557 (10)0.0408 (10)0.0688 (11)0.0117 (8)0.0178 (8)0.0059 (8)
C160.171 (3)0.0669 (17)0.0979 (17)0.0329 (18)0.0795 (19)0.0203 (14)
Geometric parameters (Å, º) top
S1—O31.4245 (15)C10—C111.385 (2)
S1—O41.4169 (13)C11—C121.379 (3)
S1—C11.8054 (17)C12—C131.364 (3)
S1—C151.764 (2)C13—C141.381 (2)
O1—N11.277 (2)C15—C161.501 (3)
O2—N21.2811 (19)C3—H30.930
N1—C11.3534 (19)C4—H40.930
N1—C21.391 (2)C5—H50.930
N2—C71.3997 (19)C6—H60.930
N2—C81.353 (2)C10—H100.930
C1—C81.406 (2)C11—H110.930
C2—C31.404 (2)C12—H120.930
C2—C71.388 (2)C13—H130.930
C3—C41.361 (2)C14—H140.930
C4—C51.385 (3)C15—H1520.970
C5—C61.364 (2)C15—H1510.970
C6—C71.401 (2)C16—H1610.960
C8—C91.4890 (19)C16—H1620.960
C9—C101.377 (2)C16—H1630.960
C9—C141.387 (2)
O1···O1i3.5217 (19)C16···O2xii3.598 (3)
O1···C3i3.337 (2)C16···O2xi3.241 (3)
O2···C14ii3.421 (2)C16···N2xi3.485 (3)
O2···C16iii3.598 (3)S1···H4vi3.557
O2···C16ii3.241 (3)S1···H151v3.534
O3···C10iv3.450 (2)O1···H3i2.485
O3···C15v3.314 (2)O1···H13xiii2.822
O4···C4vi3.435 (2)O2···H14ii2.509
O4···C12vii3.430 (2)O2···H161ii2.594
N1···C5viii3.449 (2)O2···H162ii3.212
N1···C6viii3.450 (2)O2···H163iii2.791
N2···C3viii3.522 (2)O3···H5viii2.912
N2···C4viii3.444 (2)O3···H10iv2.743
N2···C16ii3.485 (3)O3···H11iv3.059
C1···C5viii3.530 (2)O3···H151v2.431
C2···C6viii3.392 (2)O4···H4vi2.889
C2···C7viii3.497 (2)O4···H12vii2.505
C3···O1i3.337 (2)N2···H161ii3.066
C3···N2viii3.522 (2)C3···H13xi3.195
C3···C7viii3.479 (2)C3···H152i3.213
C4···O4ix3.435 (2)C4···H12xi3.262
C4···N2viii3.444 (2)C4···H152i3.240
C5···N1viii3.449 (2)C6···H162ii2.990
C5···C1viii3.530 (2)C10···H5vi3.081
C6···N1viii3.450 (2)C10···H151iii3.094
C6···C2viii3.392 (2)C10···H163iii2.957
C7···C2viii3.497 (2)C11···H5vi2.926
C7···C3viii3.479 (2)C11···H151iii3.210
C10···O3iv3.450 (2)C11···H163iii3.108
C12···O4x3.430 (2)C14···H6xi3.258
C14···O2xi3.421 (2)C15···H10xii3.272
C15···O3v3.314 (2)
O3—S1—O4117.87 (11)C11—C12—C13120.81 (19)
O3—S1—C1106.80 (9)C12—C13—C14120.22 (19)
O3—S1—C15110.66 (10)C9—C14—C13119.31 (19)
O4—S1—C1106.95 (8)S1—C15—C16112.05 (16)
O4—S1—C15108.31 (9)C2—C3—H3120.9
C1—S1—C15105.48 (9)C4—C3—H3120.8
O1—N1—C1121.84 (14)C3—C4—H4119.5
O1—N1—C2119.32 (12)C5—C4—H4119.6
C1—N1—C2118.84 (14)C4—C5—H5119.4
O2—N2—C7119.17 (13)C6—C5—H5119.1
O2—N2—C8121.09 (12)C5—C6—H6120.7
C7—N2—C8119.73 (13)C7—C6—H6120.5
S1—C1—N1114.24 (12)C9—C10—H10120.2
S1—C1—C8123.64 (11)C11—C10—H10120.1
N1—C1—C8121.97 (14)C10—C11—H11120.2
N1—C2—C3119.30 (15)C12—C11—H11120.3
N1—C2—C7119.77 (13)C11—C12—H12119.6
C3—C2—C7120.92 (15)C13—C12—H12119.6
C2—C3—C4118.34 (17)C12—C13—H13119.9
C3—C4—C5120.98 (16)C14—C13—H13119.9
C4—C5—C6121.46 (18)C9—C14—H14120.3
C5—C6—C7118.83 (18)C13—C14—H14120.4
N2—C7—C2120.19 (14)S1—C15—H152109.3
N2—C7—C6120.37 (15)S1—C15—H151109.3
C2—C7—C6119.44 (14)C16—C15—H152109.1
N2—C8—C1119.13 (12)C16—C15—H151109.1
N2—C8—C9115.25 (13)H152—C15—H151107.9
C1—C8—C9125.57 (13)C15—C16—H161109.3
C8—C9—C10121.70 (14)C15—C16—H162109.4
C8—C9—C14117.84 (15)C15—C16—H163109.8
C10—C9—C14120.43 (15)H161—C16—H162109.5
C9—C10—C11119.70 (17)H161—C16—H163109.5
C10—C11—C12119.5 (2)H162—C16—H163109.5
O3—S1—C1—N157.74 (15)S1—C1—C8—C911.7 (2)
O3—S1—C1—C8117.86 (15)N1—C1—C8—N24.5 (2)
O3—S1—C15—C16171.41 (18)N1—C1—C8—C9172.99 (15)
O4—S1—C1—N1175.21 (13)N1—C2—C3—C4179.50 (16)
O4—S1—C1—C89.19 (17)N1—C2—C7—N22.5 (2)
O4—S1—C15—C1658.0 (2)N1—C2—C7—C6177.86 (15)
C1—S1—C15—C1656.25 (19)C3—C2—C7—N2178.87 (15)
C15—S1—C1—N160.04 (14)C3—C2—C7—C60.8 (2)
C15—S1—C1—C8124.36 (14)C7—C2—C3—C40.9 (2)
O1—N1—C1—S13.6 (2)C2—C3—C4—C51.7 (2)
O1—N1—C1—C8179.29 (15)C3—C4—C5—C60.9 (3)
O1—N1—C2—C32.8 (2)C4—C5—C6—C70.8 (3)
O1—N1—C2—C7175.84 (15)C5—C6—C7—N2178.06 (16)
C1—N1—C2—C3176.83 (15)C5—C6—C7—C21.6 (2)
C1—N1—C2—C74.5 (2)N2—C8—C9—C1092.2 (2)
C2—N1—C1—S1176.77 (12)N2—C8—C9—C1485.8 (2)
C2—N1—C1—C81.1 (2)C1—C8—C9—C1090.2 (2)
O2—N2—C7—C2176.69 (15)C1—C8—C9—C1491.8 (2)
O2—N2—C7—C63.7 (2)C8—C9—C10—C11177.66 (17)
O2—N2—C8—C1173.30 (15)C8—C9—C14—C13178.55 (19)
O2—N2—C8—C99.0 (2)C10—C9—C14—C130.5 (3)
C7—N2—C8—C16.5 (2)C14—C9—C10—C110.3 (2)
C7—N2—C8—C9171.25 (14)C9—C10—C11—C120.5 (3)
C8—N2—C7—C23.1 (2)C10—C11—C12—C130.1 (2)
C8—N2—C7—C6176.52 (15)C11—C12—C13—C140.9 (4)
S1—C1—C8—N2170.77 (12)C12—C13—C14—C91.1 (3)
Symmetry codes: (i) x+1, y, z+1; (ii) x+1/2, y+1/2, z+1/2; (iii) x, y+1, z; (iv) x, y+1, z+1; (v) x, y, z+1; (vi) x1, y, z; (vii) x1/2, y1/2, z+1/2; (viii) x+1, y+1, z+1; (ix) x+1, y, z; (x) x1/2, y+1/2, z+1/2; (xi) x+1/2, y1/2, z+1/2; (xii) x, y1, z; (xiii) x+1/2, y+1/2, z+1/2.
 

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