N-[2-(Pyridin-2-yl)ethyl]-derivatives of methane-, benzene- and toluenesulfonamide: prospective ligands for metal coordination

The mol­ecular and supra­molecular structures are reported of N-[2-(pyridin-2-yl)ethyl]methane­sulfonamide, C₈H₁₂N₂O₂S, (I), N-[2-(pyridin-2-yl)ethyl]benzene­sulfonamide, C₁₃H₁₄N₂O₂S, (II), and N-[2-(pyridin-2-yl)ethyl]toluene­sulfonamide, C₁₄H₁₆N₂O₂S, (III). Although (II) and (III) are almost structurally identical, the N(amide)-C(ethyl)-C(ethyl)-C(pyridinyl) torsion angles for (I) and (II) are more closely comparable, with magnitudes of 175.37 (15)° for (I) and 169.04 (19)° for (II). This angle decreases dramatically with an additional methyl group in the para position of the sulfonamide substituent, resulting in a value of 62.9 (2)° for (III). In each of the three compounds there is an N-H...N hydrogen bond between the sulfon­amide of one mol­ecule and the pyridine N atom of a neighbor. Compound (I) forms hydrogen-bonded dimers, (II) uses its hydrogen bonding to connect supra­molecular layers, and the hydrogen bonding of (III) connects linear chains to form layers. For arene-substituted (II) and (III), the different conformations afforded by the variable dihedral angles promote inter­molecular [pi]-[pi] stacking in the benzene-substituted structure (II), but distorted intra­molecular T-shaped [pi]-stacking in the toluene-substituted structure (III), with a centroid-to-centroid distance of 4.9296 (10) Å.

Computing details

For all compounds, data collection: Instrument Service (Bruker, 2010); cell refinement: APEX2 (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalMaker (Palmer, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

(I) N-[2-(pyridin-2-yl)ethyl]methanesulfonamide

Crystal data

C8H12N2O2S	F(000) = 424
Mr = 200.27	Dx = 1.398 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.9122 (16) Å	Cell parameters from 128 reflections
b = 5.0428 (7) Å	θ = 4.3–29.0°
c = 17.279 (3) Å	µ = 0.31 mm^−1
β = 93.284 (2)°	T = 100 K
V = 949.3 (2) Å^3	Needle, colourless
Z = 4	0.51 × 0.10 × 0.09 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	2277 independent reflections
Radiation source: fine-focus sealed tube	1765 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
Detector resolution: 8.3333 pixels mm^-1	θmax = 28.6°, θmin = 1.9°
ω and φ scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −6→6
Tmin = 0.822, Tmax = 1.00	l = −22→23
10388 measured 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0475P)^2 + 0.4601P] where P = (Fo^2 + 2Fc^2)/3
2277 reflections	(Δ/σ)max = 0.001
122 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.38 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 (isotroπc) 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	0.65785 (4)	0.90289 (9)	0.34718 (2)	0.01895 (14)
O1	0.76528 (11)	1.0283 (3)	0.38274 (7)	0.0266 (3)
O2	0.56856 (12)	1.0654 (2)	0.30516 (7)	0.0233 (3)
C8	0.70704 (17)	0.6598 (4)	0.28261 (11)	0.0246 (4)
H8A	0.6357	0.5627	0.2602	0.037*
H8B	0.7628	0.5361	0.3106	0.037*
H8C	0.75	0.7455	0.241	0.037*
N1	0.59124 (14)	0.7524 (3)	0.41476 (9)	0.0211 (3)
H1	0.6386 (19)	0.690 (4)	0.4470 (13)	0.025*
C1	0.47383 (15)	0.6144 (4)	0.39803 (10)	0.0199 (4)
H1A	0.4756	0.4409	0.4249	0.024*
H1B	0.4624	0.5812	0.3416	0.024*
C2	0.36621 (16)	0.7782 (4)	0.42458 (11)	0.0228 (4)
H2A	0.381	0.8241	0.48	0.027*
H2B	0.3604	0.9455	0.3946	0.027*
C3	0.24739 (16)	0.6291 (4)	0.41358 (10)	0.0209 (4)
C4	0.16047 (17)	0.6880 (4)	0.35419 (11)	0.0279 (4)
H4	0.1748	0.8274	0.3188	0.033*
C5	0.05307 (18)	0.5430 (4)	0.34681 (12)	0.0311 (5)
H5	−0.0073	0.5826	0.3067	0.037*
C6	0.03450 (17)	0.3408 (4)	0.39810 (12)	0.0293 (5)
H6	−0.0387	0.2386	0.3945	0.035*
C7	0.12578 (17)	0.2904 (4)	0.45532 (11)	0.0269 (4)
H7	0.1137	0.1497	0.4906	0.032*
N2	0.23014 (14)	0.4298 (3)	0.46339 (9)	0.0228 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0177 (2)	0.0207 (2)	0.0183 (2)	−0.00267 (17)	0.00072 (16)	−0.00007 (17)
O1	0.0213 (7)	0.0323 (8)	0.0258 (7)	−0.0099 (6)	−0.0021 (5)	0.0012 (6)
O2	0.0235 (7)	0.0231 (7)	0.0231 (6)	0.0017 (5)	−0.0009 (5)	0.0019 (5)
C8	0.0224 (9)	0.0264 (10)	0.0255 (9)	0.0003 (8)	0.0066 (7)	−0.0007 (8)
N1	0.0165 (7)	0.0306 (9)	0.0159 (7)	−0.0043 (7)	−0.0015 (6)	0.0028 (6)
C1	0.0180 (8)	0.0240 (9)	0.0179 (8)	−0.0048 (7)	0.0012 (7)	−0.0018 (7)
C2	0.0197 (9)	0.0234 (9)	0.0254 (9)	−0.0025 (8)	0.0009 (7)	−0.0024 (8)
C3	0.0199 (9)	0.0229 (9)	0.0204 (8)	0.0005 (7)	0.0049 (7)	−0.0028 (7)
C4	0.0234 (10)	0.0302 (11)	0.0301 (10)	−0.0016 (8)	0.0019 (8)	0.0067 (8)
C5	0.0209 (10)	0.0408 (12)	0.0309 (10)	−0.0006 (9)	−0.0043 (8)	0.0054 (9)
C6	0.0184 (9)	0.0360 (11)	0.0335 (11)	−0.0076 (8)	0.0003 (8)	0.0002 (9)
C7	0.0246 (10)	0.0299 (11)	0.0263 (10)	−0.0058 (8)	0.0028 (8)	0.0031 (8)
N2	0.0202 (8)	0.0266 (9)	0.0217 (7)	−0.0017 (6)	0.0014 (6)	−0.0002 (6)

Geometric parameters (Å, º)

S1—O2	1.4377 (13)	C2—H2A	0.99
S1—O1	1.4384 (13)	C2—H2B	0.99
S1—N1	1.6016 (16)	C3—N2	1.343 (2)
S1—C8	1.7618 (19)	C3—C4	1.389 (3)
C8—H8A	0.98	C4—C5	1.381 (3)
C8—H8B	0.98	C4—H4	0.95
C8—H8C	0.98	C5—C6	1.373 (3)
N1—C1	1.472 (2)	C5—H5	0.95
N1—H1	0.80 (2)	C6—C7	1.386 (3)
C1—C2	1.528 (2)	C6—H6	0.95
C1—H1A	0.99	C7—N2	1.339 (2)
C1—H1B	0.99	C7—H7	0.95
C2—C3	1.502 (2)
O2—S1—O1	118.52 (8)	C3—C2—H2A	109.4
O2—S1—N1	108.39 (8)	C1—C2—H2A	109.4
O1—S1—N1	106.83 (8)	C3—C2—H2B	109.4
O2—S1—C8	107.39 (8)	C1—C2—H2B	109.4
O1—S1—C8	107.81 (9)	H2A—C2—H2B	108.0
N1—S1—C8	107.43 (9)	N2—C3—C4	121.23 (17)
S1—C8—H8A	109.5	N2—C3—C2	116.45 (16)
S1—C8—H8B	109.5	C4—C3—C2	122.30 (17)
H8A—C8—H8B	109.5	C5—C4—C3	119.66 (18)
S1—C8—H8C	109.5	C5—C4—H4	120.2
H8A—C8—H8C	109.5	C3—C4—H4	120.2
H8B—C8—H8C	109.5	C6—C5—C4	119.29 (18)
C1—N1—S1	120.46 (12)	C6—C5—H5	120.4
C1—N1—H1	118.2 (16)	C4—C5—H5	120.4
S1—N1—H1	112.9 (16)	C5—C6—C7	118.02 (18)
N1—C1—C2	111.16 (15)	C5—C6—H6	121.0
N1—C1—H1A	109.4	C7—C6—H6	121.0
C2—C1—H1A	109.4	N2—C7—C6	123.39 (18)
N1—C1—H1B	109.4	N2—C7—H7	118.3
C2—C1—H1B	109.4	C6—C7—H7	118.3
H1A—C1—H1B	108.0	C7—N2—C3	118.40 (16)
C3—C2—C1	111.36 (15)
O2—S1—N1—C1	48.03 (16)	C2—C3—C4—C5	179.71 (18)
O1—S1—N1—C1	176.81 (14)	C3—C4—C5—C6	−0.5 (3)
C8—S1—N1—C1	−67.72 (16)	C4—C5—C6—C7	−0.3 (3)
S1—N1—C1—C2	−102.11 (16)	C5—C6—C7—N2	0.6 (3)
N1—C1—C2—C3	−175.37 (15)	C6—C7—N2—C3	0.1 (3)
C1—C2—C3—N2	73.6 (2)	C4—C3—N2—C7	−1.0 (3)
C1—C2—C3—C4	−105.0 (2)	C2—C3—N2—C7	−179.55 (16)
N2—C3—C4—C5	1.3 (3)

(II) N-[2-(pyridin-2-yl)ethyl]benzenesulfonamide

Crystal data

C13H14N2O2S	F(000) = 552
Mr = 262.32	Dx = 1.376 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.4920 (7) Å	Cell parameters from 2969 reflections
b = 9.4328 (11) Å	θ = 2.3–26.2°
c = 24.569 (3) Å	µ = 0.25 mm^−1
β = 95.651 (2)°	T = 100 K
V = 1266.6 (3) Å^3	Needle, colourless
Z = 4	0.19 × 0.04 × 0.03 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	2768 independent reflections
Radiation source: fine-focus sealed tube	1800 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.094
Detector resolution: 8.3333 pixels mm^-1	θmax = 27.1°, θmin = 1.7°
ω and φ scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
Tmin = 0.94, Tmax = 0.99	l = −31→31
13893 measured 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0297P)^2] where P = (Fo^2 + 2Fc^2)/3
2768 reflections	(Δ/σ)max = 0.015
166 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.35 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	0.50738 (10)	0.87372 (6)	0.61471 (2)	0.01712 (16)
O1	0.6283 (3)	0.75088 (17)	0.59572 (6)	0.0232 (4)
O2	0.6496 (3)	0.99878 (16)	0.62970 (6)	0.0213 (4)
N1	0.2960 (3)	0.9214 (2)	0.56934 (8)	0.0183 (5)
H1	0.234 (4)	1.010 (2)	0.5719 (9)	0.022*
N2	−0.1253 (3)	0.78632 (19)	0.42114 (8)	0.0185 (5)
C12	0.1863 (4)	0.7532 (3)	0.77132 (10)	0.0246 (6)
H12	0.1241	0.7304	0.8041	0.03*
C11	0.0760 (4)	0.8584 (3)	0.73809 (10)	0.0239 (6)
H11	−0.0601	0.906	0.7486	0.029*
C10	0.1676 (4)	0.8928 (2)	0.68938 (9)	0.0197 (5)
H10	0.0933	0.963	0.667	0.024*
C9	0.3716 (4)	0.8216 (2)	0.67419 (9)	0.0151 (5)
C1	0.1505 (4)	0.8198 (2)	0.53482 (9)	0.0204 (5)
H1A	−0.0172	0.8529	0.5289	0.024*
H1B	0.1501	0.729	0.5534	0.024*
C2	0.2532 (4)	0.8009 (3)	0.47973 (9)	0.0228 (6)
H2A	0.2838	0.8935	0.4646	0.027*
H2B	0.4083	0.7512	0.4853	0.027*
C3	0.0831 (4)	0.7195 (3)	0.43932 (9)	0.0192 (5)
C7	−0.2838 (4)	0.7173 (2)	0.38525 (9)	0.0213 (6)
H7	−0.4289	0.7625	0.3726	0.026*
C6	−0.2417 (4)	0.5828 (2)	0.36626 (10)	0.0228 (6)
H6	−0.3555	0.5388	0.3413	0.027*
C14	0.4830 (4)	0.7161 (2)	0.70737 (9)	0.0190 (5)
H14	0.6199	0.6691	0.697	0.023*
C13	0.3895 (4)	0.6816 (3)	0.75580 (10)	0.0234 (6)
H13	0.4624	0.6104	0.778	0.028*
C5	−0.0267 (4)	0.5144 (2)	0.38516 (10)	0.0232 (6)
H5	0.007	0.4237	0.3731	0.028*
C4	0.1360 (4)	0.5836 (3)	0.42218 (9)	0.0220 (6)
H4	0.281	0.5396	0.4357	0.026*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0160 (3)	0.0196 (3)	0.0158 (3)	0.0019 (3)	0.0019 (2)	0.0009 (3)
O1	0.0268 (9)	0.0233 (9)	0.0205 (9)	0.0102 (8)	0.0069 (7)	0.0017 (8)
O2	0.0182 (9)	0.0243 (9)	0.0208 (9)	−0.0032 (7)	−0.0005 (7)	0.0028 (8)
N1	0.0200 (11)	0.0156 (11)	0.0180 (11)	0.0033 (9)	−0.0043 (9)	−0.0016 (9)
N2	0.0182 (11)	0.0188 (11)	0.0184 (11)	0.0004 (9)	0.0016 (8)	−0.0021 (8)
C12	0.0278 (14)	0.0300 (15)	0.0171 (14)	−0.0074 (12)	0.0072 (11)	0.0014 (12)
C11	0.0187 (13)	0.0299 (15)	0.0237 (14)	0.0014 (12)	0.0055 (10)	−0.0031 (12)
C10	0.0155 (12)	0.0221 (14)	0.0210 (13)	0.0018 (10)	−0.0010 (10)	−0.0002 (11)
C9	0.0146 (12)	0.0167 (12)	0.0136 (13)	−0.0024 (9)	−0.0004 (9)	−0.0022 (10)
C1	0.0205 (13)	0.0230 (13)	0.0177 (13)	−0.0010 (10)	0.0019 (10)	0.0021 (11)
C2	0.0175 (13)	0.0304 (15)	0.0207 (14)	0.0002 (11)	0.0023 (10)	−0.0028 (11)
C3	0.0169 (12)	0.0266 (15)	0.0148 (13)	−0.0005 (11)	0.0045 (10)	0.0022 (11)
C7	0.0194 (13)	0.0246 (15)	0.0194 (14)	0.0004 (11)	−0.0004 (10)	0.0009 (11)
C6	0.0251 (14)	0.0212 (14)	0.0223 (14)	−0.0056 (11)	0.0034 (11)	−0.0049 (11)
C14	0.0168 (12)	0.0192 (13)	0.0208 (14)	0.0017 (10)	0.0007 (10)	−0.0014 (10)
C13	0.0297 (14)	0.0201 (13)	0.0196 (14)	0.0005 (11)	−0.0016 (11)	0.0027 (11)
C5	0.0293 (14)	0.0147 (12)	0.0276 (14)	−0.0002 (11)	0.0119 (11)	−0.0021 (12)
C4	0.0228 (13)	0.0248 (14)	0.0189 (14)	0.0064 (11)	0.0046 (11)	0.0043 (11)

Geometric parameters (Å, º)

S1—O1	1.4363 (16)	C1—H1A	0.97
S1—O2	1.4426 (16)	C1—H1B	0.97
S1—N1	1.5931 (19)	C2—C3	1.505 (3)
S1—C9	1.774 (2)	C2—H2A	0.97
N1—C1	1.464 (3)	C2—H2B	0.97
N1—H1	0.90 (2)	C3—C4	1.389 (3)
N2—C3	1.343 (3)	C7—C6	1.379 (3)
N2—C7	1.345 (3)	C7—H7	0.93
C12—C11	1.386 (3)	C6—C5	1.385 (3)
C12—C13	1.390 (3)	C6—H6	0.93
C12—H12	0.93	C14—C13	1.381 (3)
C11—C10	1.382 (3)	C14—H14	0.93
C11—H11	0.93	C13—H13	0.93
C10—C9	1.388 (3)	C5—C4	1.375 (3)
C10—H10	0.93	C5—H5	0.93
C9—C14	1.389 (3)	C4—H4	0.93
C1—C2	1.527 (3)
O1—S1—O2	119.11 (10)	C3—C2—C1	112.65 (19)
O1—S1—N1	109.21 (10)	C3—C2—H2A	109.1
O2—S1—N1	106.65 (10)	C1—C2—H2A	109.1
O1—S1—C9	106.83 (10)	C3—C2—H2B	109.1
O2—S1—C9	106.11 (10)	C1—C2—H2B	109.1
N1—S1—C9	108.55 (11)	H2A—C2—H2B	107.8
C1—N1—S1	122.59 (16)	N2—C3—C4	121.9 (2)
C1—N1—H1	117.2 (14)	N2—C3—C2	115.7 (2)
S1—N1—H1	117.7 (14)	C4—C3—C2	122.4 (2)
C3—N2—C7	117.8 (2)	N2—C7—C6	123.2 (2)
C11—C12—C13	120.2 (2)	N2—C7—H7	118.4
C11—C12—H12	119.9	C6—C7—H7	118.4
C13—C12—H12	119.9	C7—C6—C5	118.7 (2)
C10—C11—C12	120.2 (2)	C7—C6—H6	120.6
C10—C11—H11	119.9	C5—C6—H6	120.6
C12—C11—H11	119.9	C13—C14—C9	119.7 (2)
C11—C10—C9	119.5 (2)	C13—C14—H14	120.2
C11—C10—H10	120.3	C9—C14—H14	120.2
C9—C10—H10	120.3	C14—C13—C12	119.9 (2)
C10—C9—C14	120.6 (2)	C14—C13—H13	120.0
C10—C9—S1	120.21 (18)	C12—C13—H13	120.0
C14—C9—S1	119.02 (17)	C4—C5—C6	118.5 (2)
N1—C1—C2	111.22 (19)	C4—C5—H5	120.7
N1—C1—H1A	109.4	C6—C5—H5	120.7
C2—C1—H1A	109.4	C5—C4—C3	119.8 (2)
N1—C1—H1B	109.4	C5—C4—H4	120.1
C2—C1—H1B	109.4	C3—C4—H4	120.1
H1A—C1—H1B	108.0
O1—S1—N1—C1	35.2 (2)	C7—N2—C3—C4	−0.2 (3)
O2—S1—N1—C1	165.09 (17)	C7—N2—C3—C2	−179.5 (2)
C9—S1—N1—C1	−81.0 (2)	C1—C2—C3—N2	68.6 (3)
C13—C12—C11—C10	−0.1 (4)	C1—C2—C3—C4	−110.8 (2)
C12—C11—C10—C9	−0.3 (3)	C3—N2—C7—C6	−0.3 (3)
C11—C10—C9—C14	0.3 (3)	N2—C7—C6—C5	0.4 (4)
C11—C10—C9—S1	−174.83 (17)	C10—C9—C14—C13	0.2 (3)
O1—S1—C9—C10	−153.95 (17)	S1—C9—C14—C13	175.36 (17)
O2—S1—C9—C10	78.00 (19)	C9—C14—C13—C12	−0.6 (3)
N1—S1—C9—C10	−36.3 (2)	C11—C12—C13—C14	0.5 (4)
O1—S1—C9—C14	30.9 (2)	C7—C6—C5—C4	0.1 (3)
O2—S1—C9—C14	−97.18 (19)	C6—C5—C4—C3	−0.6 (3)
N1—S1—C9—C14	148.52 (18)	N2—C3—C4—C5	0.6 (3)
S1—N1—C1—C2	−96.2 (2)	C2—C3—C4—C5	180.0 (2)
N1—C1—C2—C3	−169.04 (19)

(III) N-[2-(pyridin-2-yl)ethyl]toluenesulfonamide

Crystal data

C14H16N2O2S	Dx = 1.341 Mg m^−3
Mr = 276.35	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 129 reflections
a = 7.6869 (5) Å	θ = 3.2–24.8°
b = 15.7109 (10) Å	µ = 0.24 mm^−1
c = 22.6742 (14) Å	T = 100 K
V = 2738.3 (3) Å^3	Block, colourless
Z = 8	0.25 × 0.24 × 0.23 mm
F(000) = 1168

Data collection

Bruker APEXII CCD area-detector diffractometer	3221 independent reflections
Radiation source: fine-focus sealed tube	2429 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.103
Detector resolution: 8.3333 pixels mm^-1	θmax = 27.8°, θmin = 1.8°
ω and φ scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −20→20
Tmin = 0.90, Tmax = 0.95	l = −29→29
29603 measured 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0511P)^2 + 0.5958P] where P = (Fo^2 + 2Fc^2)/3
3221 reflections	(Δ/σ)max = 0.001
176 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.50 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 (isotroπc) 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	0.77568 (6)	0.65729 (3)	0.129057 (19)	0.02024 (14)
O1	0.59894 (16)	0.64405 (8)	0.14735 (6)	0.0296 (3)
O2	0.86748 (17)	0.59037 (8)	0.09914 (6)	0.0294 (3)
N1	0.88519 (19)	0.68080 (9)	0.18739 (6)	0.0198 (3)
H1	0.844 (2)	0.7242 (13)	0.2061 (8)	0.024*
N2	1.2340 (2)	0.82332 (9)	0.24113 (7)	0.0255 (4)
C21	0.7678 (3)	0.97221 (12)	−0.02566 (8)	0.0303 (4)
H21A	0.682	0.9649	−0.0572	0.045*
H21B	0.8833	0.9808	−0.043	0.045*
H21C	0.7366	1.0219	−0.0018	0.045*
C18	0.7699 (2)	0.89408 (11)	0.01265 (8)	0.0227 (4)
C17	0.6633 (2)	0.88763 (11)	0.06214 (8)	0.0220 (4)
H17	0.5901	0.934	0.0724	0.026*
C16	0.6621 (2)	0.81476 (11)	0.09668 (8)	0.0211 (4)
H16	0.587	0.8109	0.1298	0.025*
C15	0.7716 (2)	0.74731 (11)	0.08245 (7)	0.0185 (4)
C1	1.0717 (2)	0.66184 (11)	0.19239 (8)	0.0234 (4)
H1A	1.0924	0.6039	0.1767	0.028*
H1B	1.1031	0.6612	0.2347	0.028*
C2	1.1935 (2)	0.72375 (11)	0.16050 (8)	0.0257 (4)
H2A	1.3145	0.7028	0.1641	0.031*
H2B	1.1633	0.7246	0.1181	0.031*
C3	1.1844 (2)	0.81310 (11)	0.18431 (8)	0.0222 (4)
C7	1.2255 (3)	0.90199 (12)	0.26408 (8)	0.0287 (4)
H7	1.2602	0.9095	0.304	0.034*
C6	1.1694 (3)	0.97251 (12)	0.23331 (8)	0.0283 (4)
H6	1.1651	1.0269	0.2515	0.034*
C19	0.8759 (2)	0.82484 (12)	−0.00155 (8)	0.0254 (4)
H19	0.9477	0.8277	−0.0356	0.031*
C20	0.8785 (2)	0.75196 (12)	0.03298 (7)	0.0244 (4)
H20	0.9525	0.7057	0.023	0.029*
C5	1.1196 (3)	0.96181 (12)	0.17525 (9)	0.0295 (4)
H5	1.0806	1.009	0.1527	0.035*
C4	1.1271 (2)	0.88171 (12)	0.15046 (8)	0.0255 (4)
H4	1.0934	0.8733	0.1106	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0211 (2)	0.0157 (2)	0.0240 (2)	−0.00021 (16)	−0.00187 (17)	−0.00098 (16)
O1	0.0222 (7)	0.0263 (7)	0.0402 (8)	−0.0049 (5)	−0.0022 (6)	0.0079 (6)
O2	0.0386 (8)	0.0201 (7)	0.0296 (7)	0.0074 (6)	−0.0042 (6)	−0.0059 (5)
N1	0.0221 (8)	0.0178 (7)	0.0196 (7)	0.0014 (6)	0.0001 (6)	−0.0024 (6)
N2	0.0246 (8)	0.0241 (8)	0.0278 (8)	−0.0037 (6)	−0.0055 (6)	0.0055 (6)
C21	0.0365 (11)	0.0303 (11)	0.0240 (9)	−0.0016 (8)	−0.0038 (8)	0.0075 (8)
C18	0.0243 (9)	0.0241 (9)	0.0199 (9)	−0.0050 (7)	−0.0051 (7)	0.0005 (7)
C17	0.0233 (9)	0.0184 (9)	0.0242 (9)	0.0021 (7)	−0.0025 (7)	−0.0024 (7)
C16	0.0219 (9)	0.0210 (9)	0.0205 (9)	−0.0004 (7)	0.0001 (7)	−0.0028 (7)
C15	0.0194 (9)	0.0171 (8)	0.0189 (8)	−0.0003 (7)	−0.0041 (7)	−0.0017 (7)
C1	0.0223 (9)	0.0186 (9)	0.0294 (10)	0.0022 (7)	−0.0047 (7)	0.0004 (7)
C2	0.0197 (9)	0.0254 (10)	0.0320 (10)	0.0025 (7)	0.0020 (7)	−0.0004 (8)
C3	0.0180 (9)	0.0226 (9)	0.0261 (9)	−0.0027 (7)	0.0018 (7)	0.0029 (7)
C7	0.0316 (11)	0.0296 (10)	0.0248 (10)	−0.0115 (8)	−0.0037 (8)	0.0028 (8)
C6	0.0308 (11)	0.0210 (9)	0.0332 (11)	−0.0049 (8)	0.0056 (8)	−0.0017 (8)
C19	0.0247 (10)	0.0324 (10)	0.0192 (9)	0.0001 (8)	0.0013 (7)	−0.0001 (8)
C20	0.0241 (9)	0.0273 (10)	0.0219 (9)	0.0060 (7)	−0.0004 (7)	−0.0041 (7)
C5	0.0305 (11)	0.0246 (10)	0.0333 (11)	0.0021 (8)	0.0016 (8)	0.0101 (8)
C4	0.0273 (10)	0.0288 (10)	0.0203 (9)	0.0006 (8)	−0.0009 (7)	0.0036 (8)

Geometric parameters (Å, º)

S1—O1	1.4357 (13)	C15—C20	1.393 (2)
S1—O2	1.4365 (13)	C1—C2	1.531 (2)
S1—N1	1.6107 (15)	C1—H1A	0.99
S1—C15	1.7658 (17)	C1—H1B	0.99
N1—C1	1.469 (2)	C2—C3	1.506 (2)
N1—H1	0.86 (2)	C2—H2A	0.99
N2—C7	1.343 (2)	C2—H2B	0.99
N2—C3	1.353 (2)	C3—C4	1.394 (2)
C21—C18	1.504 (2)	C7—C6	1.379 (3)
C21—H21A	0.98	C7—H7	0.95
C21—H21B	0.98	C6—C5	1.381 (3)
C21—H21C	0.98	C6—H6	0.95
C18—C17	1.393 (2)	C19—C20	1.387 (3)
C18—C19	1.397 (3)	C19—H19	0.95
C17—C16	1.387 (2)	C20—H20	0.95
C17—H17	0.95	C5—C4	1.379 (3)
C16—C15	1.391 (2)	C5—H5	0.95
C16—H16	0.95	C4—H4	0.95
O1—S1—O2	119.68 (8)	N1—C1—H1B	108.4
O1—S1—N1	106.89 (8)	C2—C1—H1B	108.4
O2—S1—N1	107.39 (8)	H1A—C1—H1B	107.4
O1—S1—C15	105.79 (8)	C3—C2—C1	113.22 (15)
O2—S1—C15	108.20 (8)	C3—C2—H2A	108.9
N1—S1—C15	108.49 (8)	C1—C2—H2A	108.9
C1—N1—S1	121.81 (12)	C3—C2—H2B	108.9
C1—N1—H1	118.7 (13)	C1—C2—H2B	108.9
S1—N1—H1	113.2 (13)	H2A—C2—H2B	107.7
C7—N2—C3	117.67 (15)	N2—C3—C4	121.42 (17)
C18—C21—H21A	109.5	N2—C3—C2	116.02 (15)
C18—C21—H21B	109.5	C4—C3—C2	122.56 (16)
H21A—C21—H21B	109.5	N2—C7—C6	123.99 (17)
C18—C21—H21C	109.5	N2—C7—H7	118.0
H21A—C21—H21C	109.5	C6—C7—H7	118.0
H21B—C21—H21C	109.5	C7—C6—C5	118.11 (17)
C17—C18—C19	118.17 (16)	C7—C6—H6	120.9
C17—C18—C21	121.21 (16)	C5—C6—H6	120.9
C19—C18—C21	120.60 (17)	C20—C19—C18	121.41 (16)
C16—C17—C18	121.25 (16)	C20—C19—H19	119.3
C16—C17—H17	119.4	C18—C19—H19	119.3
C18—C17—H17	119.4	C19—C20—C15	119.29 (16)
C17—C16—C15	119.59 (16)	C19—C20—H20	120.4
C17—C16—H16	120.2	C15—C20—H20	120.4
C15—C16—H16	120.2	C4—C5—C6	119.20 (17)
C16—C15—C20	120.26 (16)	C4—C5—H5	120.4
C16—C15—S1	118.83 (13)	C6—C5—H5	120.4
C20—C15—S1	120.89 (13)	C5—C4—C3	119.61 (17)
N1—C1—C2	115.57 (14)	C5—C4—H4	120.2
N1—C1—H1A	108.4	C3—C4—H4	120.2
C2—C1—H1A	108.4
O1—S1—N1—C1	152.14 (13)	C7—N2—C3—C4	0.3 (3)
O2—S1—N1—C1	22.54 (15)	C7—N2—C3—C2	−179.19 (15)
C15—S1—N1—C1	−94.19 (14)	C1—C2—C3—N2	63.0 (2)
C19—C18—C17—C16	0.2 (3)	C1—C2—C3—C4	−116.49 (19)
C21—C18—C17—C16	178.39 (16)	C3—N2—C7—C6	0.0 (3)
C18—C17—C16—C15	1.2 (3)	N2—C7—C6—C5	−0.3 (3)
C17—C16—C15—C20	−1.6 (3)	C17—C18—C19—C20	−1.2 (3)
C17—C16—C15—S1	176.94 (13)	C21—C18—C19—C20	−179.44 (16)
O1—S1—C15—C16	38.47 (16)	C18—C19—C20—C15	0.8 (3)
O2—S1—C15—C16	167.86 (13)	C16—C15—C20—C19	0.6 (3)
N1—S1—C15—C16	−75.92 (15)	S1—C15—C20—C19	−177.91 (13)
O1—S1—C15—C20	−142.98 (14)	C7—C6—C5—C4	0.2 (3)
O2—S1—C15—C20	−13.58 (16)	C6—C5—C4—C3	0.1 (3)
N1—S1—C15—C20	102.63 (15)	N2—C3—C4—C5	−0.4 (3)
S1—N1—C1—C2	78.71 (18)	C2—C3—C4—C5	179.09 (16)
N1—C1—C2—C3	62.9 (2)