

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015010221/fk2088sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2056989015010221/fk2088Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015010221/fk2088Isup3.cml |
CCDC reference: 1403377
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.053
- wR factor = 0.141
- Data-to-parameter ratio = 17.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) Range 3.4 Ratio PLAT241_ALERT_2_C High Ueq as Compared to Neighbors for ..... C16 Check PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 22 Report
Alert level G PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ... 2 Report PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 7 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 3 ALERT level C = Check. Ensure it is not caused by an omission or oversight 2 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Aziridines are interesting and versatile building blocks in synthetic chemistry due to their high ring strain. By regioselective ring opening reactions, countless nitrogen-containing compounds are accessible (Stamm, 1999; Schneider, 2009). For example, the aziridine ring can be opened by triethylamine (Golz & Strohmann, 2015). In some cases, the three-membered aziridine ring is further activated by electron-withdrawing groups (Hu, 2004) to increase its reactivity.
The title compound, C17H27NO2S, is a representative of the class of activated aziridines, as it contains a triisopropylbenzene substituted sulfonyl ester attached to the nitrogen atom. In the aromatic ring, the bulky substituents lead to a distortion of its geometry. This is expressed by the increased bond lengths and out-of-plane bent substituents around the benzene ring. At the ipso-carbon, the bonds C10–C11 and C10–C6 are slightly elongated to 1.410 (3) Å. In contrast, the other bonds of the aromatic ring exhibit usual lengths [C4–C15 1.374 (3) Å, C5–C61.380 (3) Å, C11–C15 1.388 (3) Å, C4–C5 1.389 (3) Å]. The sulfonyl group as well as the adjacent isopropyl groups bend out of the aromatic plane. This is caused by steric repulsion between the isopropyl groups and the sulfonyl oxygen atoms. The sulfur atom deviates from the mean aromatic ring plane by 0.393 (4) Å. The carbon atoms C7 and C12 show distances of -0.125 (4) Å and -0.154 (4) Å, respectively (see Table 5). A similar distortion can also be observed at the isopropyl group in para position to the sulfonyl moiety. Here, C1 has a distance to the aromatic ring plane of 0.111 (5) Å, thus being distorted in the same direction as the sulfur atom. This is caused by steric repulsion between the C1 isopropyl group and the adjacent isopropyl groups in ortho position in respect of the sulfonyl moiety.
Crystal data, data collection and structure refinement details are summarized in Table 1.
Hydrogen atoms were located from difference Fourier maps, refined at idealized positions riding on the carbon atoms with isotropic displacement parameters Uiso(H) = 1.2Ueq(C) or 1.5Ueq(–CH3) and aromatic C–H = 0.95 Å, primary C–H = 0.98 Å, secondary C–H = 0.99 Å, tertiary C–H = 1.00 Å. All CH3 hydrogen atoms were allowed to rotate but not to tip. Aziridine protons could be located from difference Fourier maps, but were refined as idealized CH2 groups.
Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
![]() | Fig. 1. Molecular structure of the title compound with anisotropic displacement ellipsoids drawn at 50% probability level. |
C17H27NO2S | F(000) = 672 |
Mr = 309.45 | Dx = 1.160 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 6.2679 (8) Å | Cell parameters from 2277 reflections |
b = 17.5289 (18) Å | θ = 3.3–29.2° |
c = 16.3890 (13) Å | µ = 0.19 mm−1 |
β = 100.331 (10)° | T = 173 K |
V = 1771.5 (3) Å3 | Plate, colourless |
Z = 4 | 0.33 × 0.25 × 0.01 mm |
Agilent Xcalibur Sapphire3 diffractometer | 3449 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2479 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
Detector resolution: 16.0560 pixels mm-1 | θmax = 26.0°, θmin = 2.5° |
ω scans | h = −7→7 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | k = −15→21 |
Tmin = 0.782, Tmax = 1.000 | l = −20→20 |
9521 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.053 | H-atom parameters constrained |
wR(F2) = 0.141 | w = 1/[σ2(Fo2) + (0.0473P)2 + 0.8936P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
3449 reflections | Δρmax = 0.33 e Å−3 |
196 parameters | Δρmin = −0.58 e Å−3 |
C17H27NO2S | V = 1771.5 (3) Å3 |
Mr = 309.45 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 6.2679 (8) Å | µ = 0.19 mm−1 |
b = 17.5289 (18) Å | T = 173 K |
c = 16.3890 (13) Å | 0.33 × 0.25 × 0.01 mm |
β = 100.331 (10)° |
Agilent Xcalibur Sapphire3 diffractometer | 3449 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | 2479 reflections with I > 2σ(I) |
Tmin = 0.782, Tmax = 1.000 | Rint = 0.049 |
9521 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.141 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.33 e Å−3 |
3449 reflections | Δρmin = −0.58 e Å−3 |
196 parameters |
Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.71473 (10) | 0.20619 (4) | 0.37952 (4) | 0.0245 (2) | |
C10 | 0.7527 (4) | 0.26810 (13) | 0.29748 (14) | 0.0205 (5) | |
C15 | 0.8227 (4) | 0.28863 (14) | 0.16069 (15) | 0.0272 (6) | |
H15 | 0.8229 | 0.2705 | 0.1061 | 0.033* | |
C6 | 0.8105 (4) | 0.34434 (14) | 0.31802 (14) | 0.0246 (6) | |
C5 | 0.8842 (4) | 0.38836 (15) | 0.25903 (15) | 0.0297 (6) | |
H5 | 0.9273 | 0.4394 | 0.2726 | 0.036* | |
C11 | 0.7462 (4) | 0.24050 (14) | 0.21624 (15) | 0.0243 (6) | |
C4 | 0.8981 (4) | 0.36110 (15) | 0.18058 (15) | 0.0279 (6) | |
O1 | 0.7219 (3) | 0.12858 (10) | 0.35547 (11) | 0.0370 (5) | |
O2 | 0.8625 (3) | 0.22687 (11) | 0.45315 (10) | 0.0360 (5) | |
N1 | 0.4729 (4) | 0.23217 (13) | 0.39562 (14) | 0.0345 (6) | |
C17 | 0.3491 (5) | 0.17365 (19) | 0.4317 (2) | 0.0500 (9) | |
H17A | 0.4185 | 0.1234 | 0.4451 | 0.060* | |
H17B | 0.2536 | 0.1908 | 0.4702 | 0.060* | |
C16 | 0.2886 (6) | 0.1945 (3) | 0.3447 (2) | 0.0701 (12) | |
H16A | 0.1543 | 0.2246 | 0.3280 | 0.084* | |
H16B | 0.3190 | 0.1572 | 0.3029 | 0.084* | |
C12 | 0.6577 (5) | 0.16388 (14) | 0.18281 (15) | 0.0312 (6) | |
H12 | 0.5872 | 0.1391 | 0.2261 | 0.037* | |
C7 | 0.7975 (4) | 0.38301 (14) | 0.40041 (15) | 0.0290 (6) | |
H7 | 0.7291 | 0.3463 | 0.4347 | 0.035* | |
C1 | 0.9900 (5) | 0.41027 (15) | 0.11913 (15) | 0.0331 (7) | |
H1 | 0.9766 | 0.3811 | 0.0660 | 0.040* | |
C13 | 0.4860 (6) | 0.17400 (18) | 0.10515 (18) | 0.0489 (9) | |
H13A | 0.3751 | 0.2099 | 0.1166 | 0.073* | |
H13B | 0.4184 | 0.1246 | 0.0887 | 0.073* | |
H13C | 0.5539 | 0.1940 | 0.0602 | 0.073* | |
C3 | 0.8614 (5) | 0.48402 (17) | 0.10107 (18) | 0.0457 (8) | |
H3A | 0.7095 | 0.4719 | 0.0787 | 0.068* | |
H3B | 0.9223 | 0.5142 | 0.0605 | 0.068* | |
H3C | 0.8695 | 0.5133 | 0.1525 | 0.068* | |
C14 | 0.8399 (5) | 0.11176 (17) | 0.1661 (2) | 0.0471 (8) | |
H14A | 0.9167 | 0.1361 | 0.1259 | 0.071* | |
H14B | 0.7787 | 0.0631 | 0.1436 | 0.071* | |
H14C | 0.9415 | 0.1026 | 0.2180 | 0.071* | |
C2 | 1.2285 (5) | 0.42692 (19) | 0.1493 (2) | 0.0496 (9) | |
H2A | 1.2459 | 0.4567 | 0.2006 | 0.074* | |
H2B | 1.2856 | 0.4560 | 0.1068 | 0.074* | |
H2C | 1.3083 | 0.3788 | 0.1597 | 0.074* | |
C8 | 1.0244 (5) | 0.40142 (17) | 0.44750 (16) | 0.0407 (8) | |
H8A | 1.1099 | 0.3544 | 0.4564 | 0.061* | |
H8B | 1.0137 | 0.4243 | 0.5012 | 0.061* | |
H8C | 1.0951 | 0.4374 | 0.4151 | 0.061* | |
C9 | 0.6542 (6) | 0.45350 (17) | 0.38647 (18) | 0.0476 (8) | |
H9A | 0.7228 | 0.4919 | 0.3562 | 0.071* | |
H9B | 0.6351 | 0.4744 | 0.4401 | 0.071* | |
H9C | 0.5125 | 0.4396 | 0.3541 | 0.071* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0289 (4) | 0.0256 (4) | 0.0205 (3) | 0.0015 (3) | 0.0085 (3) | 0.0032 (3) |
C10 | 0.0213 (13) | 0.0238 (13) | 0.0168 (11) | 0.0008 (10) | 0.0048 (10) | 0.0025 (10) |
C15 | 0.0372 (16) | 0.0275 (14) | 0.0178 (12) | −0.0032 (12) | 0.0077 (11) | −0.0036 (10) |
C6 | 0.0284 (14) | 0.0279 (14) | 0.0174 (12) | −0.0012 (11) | 0.0039 (11) | −0.0011 (10) |
C5 | 0.0401 (17) | 0.0269 (14) | 0.0228 (13) | −0.0082 (12) | 0.0077 (12) | −0.0035 (11) |
C11 | 0.0283 (14) | 0.0233 (13) | 0.0212 (12) | 0.0003 (11) | 0.0043 (11) | −0.0005 (10) |
C4 | 0.0358 (16) | 0.0297 (15) | 0.0190 (12) | −0.0034 (12) | 0.0068 (11) | 0.0003 (11) |
O1 | 0.0590 (14) | 0.0250 (10) | 0.0292 (10) | 0.0063 (9) | 0.0137 (10) | 0.0051 (8) |
O2 | 0.0431 (13) | 0.0460 (12) | 0.0184 (9) | −0.0037 (9) | 0.0036 (9) | 0.0068 (8) |
N1 | 0.0286 (13) | 0.0448 (14) | 0.0326 (12) | −0.0001 (11) | 0.0128 (11) | 0.0007 (11) |
C17 | 0.0423 (19) | 0.053 (2) | 0.063 (2) | −0.0197 (15) | 0.0294 (17) | −0.0063 (17) |
C16 | 0.0294 (19) | 0.123 (4) | 0.059 (2) | −0.014 (2) | 0.0122 (17) | −0.030 (2) |
C12 | 0.0473 (18) | 0.0251 (14) | 0.0221 (13) | −0.0042 (12) | 0.0088 (12) | −0.0015 (11) |
C7 | 0.0442 (17) | 0.0251 (14) | 0.0197 (12) | −0.0084 (12) | 0.0115 (12) | −0.0048 (11) |
C1 | 0.0504 (18) | 0.0296 (15) | 0.0224 (13) | −0.0063 (13) | 0.0152 (13) | −0.0008 (11) |
C13 | 0.060 (2) | 0.0442 (19) | 0.0360 (16) | −0.0173 (16) | −0.0084 (16) | −0.0013 (14) |
C3 | 0.060 (2) | 0.0423 (19) | 0.0371 (16) | −0.0001 (16) | 0.0160 (16) | 0.0155 (14) |
C14 | 0.059 (2) | 0.0336 (17) | 0.0517 (19) | −0.0011 (15) | 0.0181 (17) | −0.0145 (15) |
C2 | 0.047 (2) | 0.055 (2) | 0.0497 (19) | −0.0071 (16) | 0.0182 (16) | 0.0124 (16) |
C8 | 0.056 (2) | 0.0432 (18) | 0.0215 (13) | −0.0145 (15) | 0.0028 (14) | −0.0060 (13) |
C9 | 0.070 (2) | 0.0402 (18) | 0.0353 (16) | 0.0090 (16) | 0.0172 (16) | −0.0109 (14) |
S1—C10 | 1.777 (2) | C7—H7 | 1.0000 |
S1—O1 | 1.4193 (19) | C7—C8 | 1.526 (4) |
S1—O2 | 1.4300 (19) | C7—C9 | 1.520 (4) |
S1—N1 | 1.649 (2) | C1—H1 | 1.0000 |
C10—C6 | 1.410 (3) | C1—C3 | 1.524 (4) |
C10—C11 | 1.410 (3) | C1—C2 | 1.517 (4) |
C15—H15 | 0.9500 | C13—H13A | 0.9800 |
C15—C11 | 1.388 (3) | C13—H13B | 0.9800 |
C15—C4 | 1.374 (4) | C13—H13C | 0.9800 |
C6—C5 | 1.380 (3) | C3—H3A | 0.9800 |
C6—C7 | 1.526 (3) | C3—H3B | 0.9800 |
C5—H5 | 0.9500 | C3—H3C | 0.9800 |
C5—C4 | 1.389 (3) | C14—H14A | 0.9800 |
C11—C12 | 1.518 (4) | C14—H14B | 0.9800 |
C4—C1 | 1.516 (3) | C14—H14C | 0.9800 |
N1—C17 | 1.473 (3) | C2—H2A | 0.9800 |
N1—C16 | 1.456 (4) | C2—H2B | 0.9800 |
C17—H17A | 0.9900 | C2—H2C | 0.9800 |
C17—H17B | 0.9900 | C8—H8A | 0.9800 |
C17—C16 | 1.455 (5) | C8—H8B | 0.9800 |
C16—H16A | 0.9900 | C8—H8C | 0.9800 |
C16—H16B | 0.9900 | C9—H9A | 0.9800 |
C12—H12 | 1.0000 | C9—H9B | 0.9800 |
C12—C13 | 1.523 (4) | C9—H9C | 0.9800 |
C12—C14 | 1.526 (4) | ||
O1—S1—C10 | 111.10 (11) | C8—C7—H7 | 107.9 |
O1—S1—O2 | 115.43 (12) | C9—C7—C6 | 110.6 (2) |
O1—S1—N1 | 112.65 (12) | C9—C7—H7 | 107.9 |
O2—S1—C10 | 109.23 (11) | C9—C7—C8 | 112.1 (2) |
O2—S1—N1 | 105.67 (12) | C4—C1—H1 | 107.8 |
N1—S1—C10 | 101.77 (11) | C4—C1—C3 | 111.1 (2) |
C6—C10—S1 | 117.51 (17) | C4—C1—C2 | 111.3 (2) |
C6—C10—C11 | 120.9 (2) | C3—C1—H1 | 107.8 |
C11—C10—S1 | 121.32 (19) | C2—C1—H1 | 107.8 |
C11—C15—H15 | 118.3 | C2—C1—C3 | 110.9 (2) |
C4—C15—H15 | 118.3 | C12—C13—H13A | 109.5 |
C4—C15—C11 | 123.4 (2) | C12—C13—H13B | 109.5 |
C10—C6—C7 | 125.5 (2) | C12—C13—H13C | 109.5 |
C5—C6—C10 | 117.8 (2) | H13A—C13—H13B | 109.5 |
C5—C6—C7 | 116.7 (2) | H13A—C13—H13C | 109.5 |
C6—C5—H5 | 118.6 | H13B—C13—H13C | 109.5 |
C6—C5—C4 | 122.7 (2) | C1—C3—H3A | 109.5 |
C4—C5—H5 | 118.6 | C1—C3—H3B | 109.5 |
C10—C11—C12 | 126.2 (2) | C1—C3—H3C | 109.5 |
C15—C11—C10 | 117.1 (2) | H3A—C3—H3B | 109.5 |
C15—C11—C12 | 116.6 (2) | H3A—C3—H3C | 109.5 |
C15—C4—C5 | 117.5 (2) | H3B—C3—H3C | 109.5 |
C15—C4—C1 | 121.6 (2) | C12—C14—H14A | 109.5 |
C5—C4—C1 | 120.9 (2) | C12—C14—H14B | 109.5 |
C17—N1—S1 | 116.0 (2) | C12—C14—H14C | 109.5 |
C16—N1—S1 | 116.1 (2) | H14A—C14—H14B | 109.5 |
C16—N1—C17 | 59.5 (2) | H14A—C14—H14C | 109.5 |
N1—C17—H17A | 117.8 | H14B—C14—H14C | 109.5 |
N1—C17—H17B | 117.8 | C1—C2—H2A | 109.5 |
H17A—C17—H17B | 114.9 | C1—C2—H2B | 109.5 |
C16—C17—N1 | 59.7 (2) | C1—C2—H2C | 109.5 |
C16—C17—H17A | 117.8 | H2A—C2—H2B | 109.5 |
C16—C17—H17B | 117.8 | H2A—C2—H2C | 109.5 |
N1—C16—H16A | 117.7 | H2B—C2—H2C | 109.5 |
N1—C16—H16B | 117.7 | C7—C8—H8A | 109.5 |
C17—C16—N1 | 60.8 (2) | C7—C8—H8B | 109.5 |
C17—C16—H16A | 117.7 | C7—C8—H8C | 109.5 |
C17—C16—H16B | 117.7 | H8A—C8—H8B | 109.5 |
H16A—C16—H16B | 114.8 | H8A—C8—H8C | 109.5 |
C11—C12—H12 | 107.9 | H8B—C8—H8C | 109.5 |
C11—C12—C13 | 110.9 (2) | C7—C9—H9A | 109.5 |
C11—C12—C14 | 111.0 (2) | C7—C9—H9B | 109.5 |
C13—C12—H12 | 107.9 | C7—C9—H9C | 109.5 |
C13—C12—C14 | 111.1 (2) | H9A—C9—H9B | 109.5 |
C14—C12—H12 | 107.9 | H9A—C9—H9C | 109.5 |
C6—C7—H7 | 107.9 | H9B—C9—H9C | 109.5 |
C8—C7—C6 | 110.4 (2) | ||
S1—C10—C6—C5 | 166.7 (2) | C5—C6—C7—C8 | −67.6 (3) |
S1—C10—C6—C7 | −13.6 (3) | C5—C6—C7—C9 | 57.1 (3) |
S1—C10—C11—C15 | −166.5 (2) | C5—C4—C1—C3 | −58.7 (4) |
S1—C10—C11—C12 | 15.3 (4) | C5—C4—C1—C2 | 65.4 (3) |
S1—N1—C17—C16 | −106.4 (3) | C11—C10—C6—C5 | −7.3 (4) |
S1—N1—C16—C17 | 106.1 (2) | C11—C10—C6—C7 | 172.4 (3) |
C10—S1—N1—C17 | 154.1 (2) | C11—C15—C4—C5 | −3.9 (4) |
C10—S1—N1—C16 | 87.0 (2) | C11—C15—C4—C1 | 177.0 (3) |
C10—C6—C5—C4 | 1.6 (4) | C4—C15—C11—C10 | −1.5 (4) |
C10—C6—C7—C8 | 112.8 (3) | C4—C15—C11—C12 | 176.8 (2) |
C10—C6—C7—C9 | −122.6 (3) | O1—S1—C10—C6 | −162.51 (19) |
C10—C11—C12—C13 | 125.2 (3) | O1—S1—C10—C11 | 11.4 (3) |
C10—C11—C12—C14 | −110.8 (3) | O1—S1—N1—C17 | 35.1 (2) |
C15—C11—C12—C13 | −52.9 (3) | O1—S1—N1—C16 | −32.0 (3) |
C15—C11—C12—C14 | 71.0 (3) | O2—S1—C10—C6 | −34.0 (2) |
C15—C4—C1—C3 | 120.4 (3) | O2—S1—C10—C11 | 139.9 (2) |
C15—C4—C1—C2 | −115.5 (3) | O2—S1—N1—C17 | −91.8 (2) |
C6—C10—C11—C15 | 7.2 (4) | O2—S1—N1—C16 | −158.9 (2) |
C6—C10—C11—C12 | −170.9 (2) | N1—S1—C10—C6 | 77.4 (2) |
C6—C5—C4—C15 | 3.8 (4) | N1—S1—C10—C11 | −108.7 (2) |
C6—C5—C4—C1 | −177.1 (3) | C7—C6—C5—C4 | −178.1 (3) |
Experimental details
Crystal data | |
Chemical formula | C17H27NO2S |
Mr | 309.45 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 173 |
a, b, c (Å) | 6.2679 (8), 17.5289 (18), 16.3890 (13) |
β (°) | 100.331 (10) |
V (Å3) | 1771.5 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.19 |
Crystal size (mm) | 0.33 × 0.25 × 0.01 |
Data collection | |
Diffractometer | Agilent Xcalibur Sapphire3 diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2013) |
Tmin, Tmax | 0.782, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9521, 3449, 2479 |
Rint | 0.049 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.141, 1.07 |
No. of reflections | 3449 |
No. of parameters | 196 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.33, −0.58 |
Computer programs: CrysAlis PRO (Agilent, 2013), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), OLEX2 (Dolomanov et al., 2009).
Atom | Deviation |
C4 | 0.033 (2) |
C5 | -0.013 (2) |
C6 | -0.026 (2) |
C10 | 0.046 (2) |
C11 | -0.026 (2) |
C15 | -0.014 (2) |
S1* | 0.393 (4) |
C1* | 0.111 (5) |
C7* | -0.125 (4) |
C12* | -0.154 (4) |
Note: (*) not used in the least-squares-plane calculation. |