Diethyl 2,2′-[(5-dimethyl­amino-1-naphth­yl)sulfonyl­imino]diacetate

Zhang, Y.; Qu, Y.; Liu, T.

doi:10.1107/S1600536809041476

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2752

https://doi.org/10.1107/S1600536809041476

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Diethyl 2,2′-[(5-dimethylamino-1-naphthyl)sulfonylimino]diacetate

Yong Zhang,^a ^* Yuan Qu ^a and Ting Liu ^a

^aSchool of Chemical and Materials Engineering, Huangshi Institute of Technology, Huangshi 435003, People's Republic of China
^*Correspondence e-mail: zy0340907@yahoo.com.cn

(Received 23 September 2009; accepted 11 October 2009; online 17 October 2009)

In the title compound, C₂₀H₂₆N₂O₆S, the N atom of the dimethylamino group is displaced by 0.113 (2) Å from the plane of the naphthalene ring system. The two ethoxy groups adopt zigzag conformations. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds link the molecules, forming a three-dimensional network. Both ethyl groups are disordered over two sites with the ratios of refined occupancies being 0.857 (16):0.143 (16) and 0.517 (14):0.483 (14).

Related literature

For applications of ligands containing the 5-(dimethylamino) naphthalene-1-sulfonyl (dansyl) group, see: Corradini et al. (1997 ); Christoforou et al. (2006 ); Zhang et al. (2009 ).

Experimental

Crystal data

C₂₀H₂₆N₂O₆S
M_r = 422.49
Monoclinic, P 2₁ /c
a = 13.1266 (9) Å
b = 8.4592 (5) Å
c = 19.3206 (12) Å
β = 93.530 (1)°
V = 2141.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.970, T_max = 0.981
16359 measured reflections
4201 independent reflections
3705 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.145
S = 1.05
4201 reflections
306 parameters
12 restraints
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1	0.93	2.36	3.006 (3)	126
C13—H13A⋯O2ⁱ	0.97	2.36	3.272 (3)	157
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809041476/lh2912sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809041476/lh2912Isup2.hkl

checkCIF report

Comment top

Dansyl (5-(dimethylamino)naphthalene-1-sulfonyl) derivatives are of considerable interest because of their good fluorescent properties. Many fluorescent ligands bearing dansyl group have been reported in recent years (e.g. Corradini et al., 1997; Christoforou et al., 2006; Zhang et al., 2009). We are interested in preparing fluorescent ligands that are expected to bind to hydrophobic sites in proteins or membranes. With this in mind, the title compound, (I), was prepared and we report herein the crystal stucture.

In the molecular structure (Fig. 1), the N atom of the dimethylamino group is displaced by 0.113 (2) Å from the plane of the naphthalene ring system. The two ethoxycarbonyl groups adopt coiled conformations with C14—O4—C15—C16 and C18—O6—C119—C20 torsion angles of 90.1 (10)° and 159.6 (9)°, respectively. All bond lengths and bond angles are as expected. In the crystal structure (Fig.2) weak intermolecular C—H···O hydrogen bonds lead to the formation of a three-dimension network.

Related literature top

For applications of ligands containing the 5-(dimethylamino) naphthalene-1-sulfonyl (dansyl) group, see: Corradini et al. (1997); Christoforou et al. (2006); Zhang et al. (2009).

Experimental top

Diethyl iminodiacetate(0.38 g, 2 mmol) was added to a stirred solution of dansyl chloride(0.27 g, 1 mmol) in dry acetonitrile(40 ml). The reaction mixture was allowed to stir for 12 hr at 353 K. The progress of the reaction was monitored by TLC, untill the completion of reaction. The solvent was evaporated and the residue was purified by column chromatography (hexane-ethyl acetate,1:5 v/v) to afford the title compound as a yellow solid. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.

Structure description top

For applications of ligands containing the 5-(dimethylamino) naphthalene-1-sulfonyl (dansyl) group, see: Corradini et al. (1997); Christoforou et al. (2006); Zhang et al. (2009).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level. The disorder is not shown.
	Fig. 2. Part of the crystal structure of (I) showing weak hydrogen bonds as dashed lines.

Diethyl 2,2'-[(5-dimethylamino-1-naphthyl)sulfonylimino]diacetate top

Crystal data top

C₂₀H₂₆N₂O₆S	F(000) = 896
M_r = 422.49	D_x = 1.311 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7099 reflections
a = 13.1266 (9) Å	θ = 2.4–27.8°
b = 8.4592 (5) Å	µ = 0.19 mm⁻¹
c = 19.3206 (12) Å	T = 298 K
β = 93.530 (1)°	Block, yellow
V = 2141.3 (2) Å³	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	4201 independent reflections
Radiation source: fine-focus sealed tube	3705 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
φ and ω scans	θ_max = 26.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→16
T_min = 0.970, T_max = 0.981	k = −10→10
16359 measured reflections	l = −23→23

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0753P)² + 0.7093P] where P = (F_o² + 2F_c²)/3
4201 reflections	(Δ/σ)_max < 0.001
306 parameters	Δρ_max = 0.35 e Å⁻³
12 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₀H₂₆N₂O₆S	V = 2141.3 (2) Å³
M_r = 422.49	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.1266 (9) Å	µ = 0.19 mm⁻¹
b = 8.4592 (5) Å	T = 298 K
c = 19.3206 (12) Å	0.20 × 0.20 × 0.20 mm
β = 93.530 (1)°

Data collection top

Bruker SMART CCD diffractometer	4201 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3705 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.981	R_int = 0.040
16359 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	12 restraints
wR(F²) = 0.145	H-atom parameters constrained
S = 1.05	Δρ_max = 0.35 e Å⁻³
4201 reflections	Δρ_min = −0.27 e Å⁻³
306 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.95264 (17)	0.5912 (3)	0.37909 (11)	0.0578 (5)
C2	1.02352 (18)	0.4871 (3)	0.35796 (14)	0.0715 (7)
H2	1.0911	0.4969	0.3750	0.086*
C3	0.99669 (18)	0.3659 (3)	0.31122 (15)	0.0737 (7)
H3	1.0466	0.2959	0.2981	0.088*
C4	0.89929 (16)	0.3482 (3)	0.28453 (13)	0.0622 (6)
H4	0.8836	0.2689	0.2523	0.075*
C5	0.82149 (15)	0.4499 (2)	0.30558 (10)	0.0466 (4)
C6	0.71621 (15)	0.4373 (2)	0.28232 (10)	0.0446 (4)
C7	0.64297 (16)	0.5326 (2)	0.30780 (11)	0.0522 (5)
H7	0.5752	0.5227	0.2912	0.063*
C8	0.67007 (17)	0.6443 (3)	0.35867 (12)	0.0588 (5)
H8	0.6200	0.7065	0.3771	0.071*
C9	0.76932 (17)	0.6628 (3)	0.38138 (12)	0.0575 (5)
H9	0.7861	0.7382	0.4153	0.069*
C10	0.84776 (15)	0.5708 (2)	0.35492 (10)	0.0490 (5)
C11	0.9684 (3)	0.8725 (4)	0.39713 (18)	0.0941 (10)
H11A	1.0269	0.8936	0.3712	0.141*
H11B	0.9651	0.9487	0.4337	0.141*
H11C	0.9076	0.8794	0.3669	0.141*
C12	1.0732 (2)	0.6972 (5)	0.46859 (16)	0.0957 (10)
H12A	1.0791	0.5906	0.4854	0.144*
H12B	1.0742	0.7688	0.5072	0.144*
H12C	1.1293	0.7203	0.4406	0.144*
C13	0.59995 (17)	0.1130 (3)	0.32052 (11)	0.0548 (5)
H13A	0.5668	0.0108	0.3159	0.066*
H13B	0.5478	0.1937	0.3136	0.066*
C14	0.64919 (19)	0.1283 (3)	0.39272 (12)	0.0588 (5)
C15	0.6061 (8)	0.1733 (7)	0.5102 (2)	0.0874 (19)	0.857 (16)
H15A	0.6740	0.1337	0.5230	0.105*	0.857 (16)
H15B	0.5583	0.1241	0.5399	0.105*	0.857 (16)
C16	0.6032 (10)	0.3472 (8)	0.5176 (3)	0.149 (4)	0.857 (16)
H16A	0.6565	0.3935	0.4925	0.223*	0.857 (16)
H16B	0.6128	0.3748	0.5658	0.223*	0.857 (16)
H16C	0.5383	0.3861	0.4994	0.223*	0.857 (16)
C17	0.73411 (17)	−0.0060 (3)	0.24933 (12)	0.0552 (5)
H17A	0.7484	−0.0699	0.2905	0.066*
H17B	0.7988	0.0315	0.2339	0.066*
C18	0.68302 (16)	−0.1075 (2)	0.19336 (11)	0.0520 (5)
C19	0.7087 (7)	−0.2942 (12)	0.1072 (5)	0.073 (3)	0.517 (14)
H19A	0.6722	−0.2204	0.0762	0.088*	0.517 (14)
H19B	0.6624	−0.3784	0.1185	0.088*	0.517 (14)
C20	0.8001 (6)	−0.3609 (15)	0.0734 (5)	0.100 (3)	0.517 (14)
H20A	0.8432	−0.2759	0.0600	0.150*	0.517 (14)
H20B	0.7776	−0.4207	0.0331	0.150*	0.517 (14)
H20C	0.8378	−0.4285	0.1057	0.150*	0.517 (14)
C15'	0.626 (2)	0.223 (5)	0.4978 (12)	0.069 (9)	0.143 (16)
H15C	0.6659	0.3117	0.4825	0.083*	0.143 (16)
H15D	0.6711	0.1531	0.5253	0.083*	0.143 (16)
C16'	0.539 (3)	0.281 (6)	0.5403 (16)	0.122 (14)	0.143 (16)
H16D	0.5088	0.3735	0.5189	0.182*	0.143 (16)
H16E	0.5652	0.3060	0.5864	0.182*	0.143 (16)
H16F	0.4883	0.1993	0.5421	0.182*	0.143 (16)
C19'	0.7221 (11)	−0.3420 (9)	0.1268 (4)	0.069 (3)	0.483 (14)
H19C	0.6507	−0.3697	0.1290	0.083*	0.483 (14)
H19D	0.7638	−0.4342	0.1382	0.083*	0.483 (14)
C20'	0.7438 (12)	−0.2768 (12)	0.0564 (4)	0.101 (4)	0.483 (14)
H20D	0.7039	−0.1831	0.0474	0.152*	0.483 (14)
H20E	0.7263	−0.3544	0.0215	0.152*	0.483 (14)
H20F	0.8150	−0.2515	0.0556	0.152*	0.483 (14)
N1	0.97658 (16)	0.7153 (3)	0.42652 (11)	0.0706 (6)
N2	0.67264 (13)	0.1287 (2)	0.26716 (9)	0.0524 (4)
O1	0.74296 (13)	0.2660 (2)	0.16995 (8)	0.0631 (4)
O2	0.56924 (12)	0.3303 (2)	0.20057 (8)	0.0635 (4)
O3	0.73809 (15)	0.1308 (3)	0.40732 (10)	0.0988 (7)
O4	0.57813 (15)	0.1376 (3)	0.43757 (9)	0.0934 (7)
O5	0.59653 (12)	−0.0973 (2)	0.17180 (10)	0.0751 (5)
O6	0.74949 (13)	−0.2111 (2)	0.17216 (11)	0.0783 (6)
S1	0.67202 (4)	0.28980 (6)	0.22222 (3)	0.04759 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0469 (12)	0.0728 (14)	0.0531 (12)	−0.0099 (10)	−0.0019 (9)	0.0004 (10)
C2	0.0377 (12)	0.0952 (19)	0.0807 (17)	−0.0057 (12)	−0.0047 (11)	−0.0049 (14)
C3	0.0409 (12)	0.0834 (18)	0.0969 (19)	0.0088 (12)	0.0039 (12)	−0.0136 (15)
C4	0.0439 (12)	0.0645 (13)	0.0783 (15)	0.0032 (10)	0.0028 (10)	−0.0126 (12)
C5	0.0390 (10)	0.0492 (10)	0.0516 (11)	−0.0017 (8)	0.0024 (8)	0.0026 (9)
C6	0.0416 (10)	0.0439 (10)	0.0479 (10)	−0.0013 (8)	−0.0012 (8)	0.0002 (8)
C7	0.0409 (11)	0.0525 (11)	0.0625 (12)	0.0024 (9)	−0.0020 (9)	−0.0013 (10)
C8	0.0492 (12)	0.0585 (12)	0.0691 (14)	0.0070 (10)	0.0073 (10)	−0.0115 (11)
C9	0.0574 (13)	0.0585 (12)	0.0567 (12)	−0.0042 (10)	0.0027 (10)	−0.0115 (10)
C10	0.0433 (11)	0.0553 (11)	0.0481 (11)	−0.0033 (9)	−0.0003 (8)	0.0032 (9)
C11	0.094 (2)	0.086 (2)	0.100 (2)	−0.0227 (17)	−0.0109 (18)	−0.0207 (18)
C12	0.0681 (18)	0.139 (3)	0.0770 (18)	−0.0235 (18)	−0.0197 (14)	−0.0136 (18)
C13	0.0504 (12)	0.0551 (12)	0.0586 (12)	−0.0068 (9)	0.0010 (9)	−0.0018 (10)
C14	0.0591 (14)	0.0581 (13)	0.0587 (13)	0.0007 (11)	0.0002 (11)	−0.0021 (10)
C15	0.106 (4)	0.108 (4)	0.048 (2)	0.013 (3)	0.008 (2)	0.010 (2)
C16	0.252 (12)	0.115 (4)	0.075 (3)	0.068 (5)	−0.026 (4)	−0.014 (3)
C17	0.0509 (12)	0.0492 (11)	0.0642 (13)	0.0078 (9)	−0.0064 (10)	−0.0050 (9)
C18	0.0450 (12)	0.0507 (11)	0.0612 (12)	−0.0067 (9)	0.0104 (9)	−0.0046 (9)
C19	0.070 (4)	0.055 (5)	0.093 (7)	0.002 (4)	−0.003 (5)	−0.027 (5)
C20	0.091 (5)	0.108 (7)	0.103 (5)	0.003 (4)	0.019 (4)	−0.038 (5)
C15'	0.078 (16)	0.09 (2)	0.044 (12)	0.002 (13)	0.007 (11)	0.002 (13)
C16'	0.11 (3)	0.13 (3)	0.12 (2)	0.04 (2)	−0.006 (19)	0.01 (2)
C19'	0.092 (7)	0.044 (4)	0.074 (4)	−0.011 (4)	0.018 (4)	−0.005 (3)
C20'	0.153 (11)	0.085 (6)	0.067 (4)	−0.032 (6)	0.025 (5)	−0.010 (4)
N1	0.0575 (12)	0.0899 (16)	0.0630 (12)	−0.0152 (11)	−0.0086 (9)	−0.0105 (11)
N2	0.0545 (10)	0.0458 (9)	0.0570 (10)	0.0032 (8)	0.0041 (8)	−0.0042 (8)
O1	0.0666 (10)	0.0730 (10)	0.0499 (8)	0.0011 (8)	0.0046 (7)	−0.0043 (7)
O2	0.0521 (9)	0.0667 (9)	0.0688 (10)	0.0086 (7)	−0.0194 (7)	−0.0052 (8)
O3	0.0622 (12)	0.161 (2)	0.0711 (12)	0.0146 (13)	−0.0128 (9)	−0.0102 (13)
O4	0.0767 (13)	0.1434 (19)	0.0607 (11)	−0.0036 (13)	0.0095 (9)	−0.0127 (12)
O5	0.0455 (9)	0.0878 (12)	0.0910 (12)	−0.0035 (8)	−0.0051 (8)	−0.0257 (10)
O6	0.0566 (10)	0.0703 (11)	0.1090 (14)	−0.0017 (8)	0.0126 (9)	−0.0396 (10)
S1	0.0445 (3)	0.0501 (3)	0.0474 (3)	0.0023 (2)	−0.0045 (2)	−0.0020 (2)

Geometric parameters (Å, º) top

C1—C2	1.362 (4)	C15—H15A	0.9700
C1—N1	1.416 (3)	C15—H15B	0.9700
C1—C10	1.437 (3)	C16—H16A	0.9600
C2—C3	1.397 (4)	C16—H16B	0.9600
C2—H2	0.9300	C16—H16C	0.9600
C3—C4	1.357 (3)	C17—N2	1.450 (3)
C3—H3	0.9300	C17—C18	1.506 (3)
C4—C5	1.414 (3)	C17—H17A	0.9700
C4—H4	0.9300	C17—H17B	0.9700
C5—C10	1.426 (3)	C18—O5	1.188 (3)
C5—C6	1.431 (3)	C18—O6	1.319 (3)
C6—C7	1.369 (3)	C19—O6	1.509 (7)
C6—S1	1.777 (2)	C19—C20	1.510 (8)
C7—C8	1.394 (3)	C19—H19A	0.9700
C7—H7	0.9300	C19—H19B	0.9700
C8—C9	1.358 (3)	C20—H20A	0.9600
C8—H8	0.9300	C20—H20B	0.9600
C9—C10	1.412 (3)	C20—H20C	0.9600
C9—H9	0.9300	C15'—O4	1.477 (10)
C11—N1	1.447 (4)	C15'—C16'	1.529 (10)
C11—H11A	0.9600	C15'—H15C	0.9700
C11—H11B	0.9600	C15'—H15D	0.9700
C11—H11C	0.9600	C16'—H16D	0.9600
C12—N1	1.472 (3)	C16'—H16E	0.9600
C12—H12A	0.9600	C16'—H16F	0.9600
C12—H12B	0.9600	C19'—O6	1.444 (8)
C12—H12C	0.9600	C19'—C20'	1.511 (8)
C13—N2	1.453 (3)	C19'—H19C	0.9700
C13—C14	1.506 (3)	C19'—H19D	0.9700
C13—H13A	0.9700	C20'—H20D	0.9600
C13—H13B	0.9700	C20'—H20E	0.9600
C14—O3	1.184 (3)	C20'—H20F	0.9600
C14—O4	1.314 (3)	N2—S1	1.6160 (18)
C15—O4	1.460 (5)	O1—S1	1.4295 (17)
C15—C16	1.478 (7)	O2—S1	1.4292 (15)

C2—C1—N1	123.0 (2)	H15A—C15—H15B	108.6
C2—C1—C10	118.9 (2)	N2—C17—C18	112.89 (18)
N1—C1—C10	118.0 (2)	N2—C17—H17A	109.0
C1—C2—C3	121.2 (2)	C18—C17—H17A	109.0
C1—C2—H2	119.4	N2—C17—H17B	109.0
C3—C2—H2	119.4	C18—C17—H17B	109.0
C4—C3—C2	121.4 (2)	H17A—C17—H17B	107.8
C4—C3—H3	119.3	O5—C18—O6	125.1 (2)
C2—C3—H3	119.3	O5—C18—C17	125.7 (2)
C3—C4—C5	120.2 (2)	O6—C18—C17	109.14 (19)
C3—C4—H4	119.9	O6—C19—C20	106.4 (6)
C5—C4—H4	119.9	O6—C19—H19A	110.4
C4—C5—C10	118.66 (19)	C20—C19—H19A	110.4
C4—C5—C6	124.39 (19)	O6—C19—H19B	110.4
C10—C5—C6	116.92 (18)	C20—C19—H19B	110.4
C7—C6—C5	121.96 (18)	H19A—C19—H19B	108.6
C7—C6—S1	116.10 (15)	O4—C15'—C16'	106.3 (13)
C5—C6—S1	121.85 (15)	O4—C15'—H15C	110.5
C6—C7—C8	119.89 (19)	C16'—C15'—H15C	110.5
C6—C7—H7	120.1	O4—C15'—H15D	110.5
C8—C7—H7	120.1	C16'—C15'—H15D	110.5
C9—C8—C7	120.3 (2)	H15C—C15'—H15D	108.7
C9—C8—H8	119.9	C15'—C16'—H16D	109.5
C7—C8—H8	119.9	C15'—C16'—H16E	109.5
C8—C9—C10	121.7 (2)	H16D—C16'—H16E	109.5
C8—C9—H9	119.1	C15'—C16'—H16F	109.5
C10—C9—H9	119.1	H16D—C16'—H16F	109.5
C9—C10—C5	119.07 (18)	H16E—C16'—H16F	109.5
C9—C10—C1	121.5 (2)	O6—C19'—C20'	102.3 (6)
C5—C10—C1	119.39 (19)	O6—C19'—H19C	111.3
N1—C11—H11A	109.5	C20'—C19'—H19C	111.3
N1—C11—H11B	109.5	O6—C19'—H19D	111.3
H11A—C11—H11B	109.5	C20'—C19'—H19D	111.3
N1—C11—H11C	109.5	H19C—C19'—H19D	109.2
H11A—C11—H11C	109.5	C19'—C20'—H20D	109.5
H11B—C11—H11C	109.5	C19'—C20'—H20E	109.5
N1—C12—H12A	109.5	H20D—C20'—H20E	109.5
N1—C12—H12B	109.5	C19'—C20'—H20F	109.5
H12A—C12—H12B	109.5	H20D—C20'—H20F	109.5
N1—C12—H12C	109.5	H20E—C20'—H20F	109.5
H12A—C12—H12C	109.5	C1—N1—C11	114.8 (2)
H12B—C12—H12C	109.5	C1—N1—C12	115.4 (2)
N2—C13—C14	112.71 (18)	C11—N1—C12	110.7 (2)
N2—C13—H13A	109.0	C17—N2—C13	119.76 (18)
C14—C13—H13A	109.0	C17—N2—S1	121.31 (15)
N2—C13—H13B	109.0	C13—N2—S1	118.44 (14)
C14—C13—H13B	109.0	C14—O4—C15	120.0 (4)
H13A—C13—H13B	107.8	C14—O4—C15'	105.2 (9)
O3—C14—O4	124.8 (2)	C18—O6—C19'	123.6 (6)
O3—C14—C13	125.6 (2)	C18—O6—C19	111.1 (4)
O4—C14—C13	109.5 (2)	O2—S1—O1	118.12 (10)
O4—C15—C16	107.0 (4)	O2—S1—N2	109.44 (10)
O4—C15—H15A	110.3	O1—S1—N2	106.18 (9)
C16—C15—H15A	110.3	O2—S1—C6	106.70 (9)
O4—C15—H15B	110.3	O1—S1—C6	111.09 (10)
C16—C15—H15B	110.3	N2—S1—C6	104.51 (9)

N1—C1—C2—C3	179.8 (2)	C18—C17—N2—C13	88.7 (2)
C10—C1—C2—C3	2.7 (4)	C18—C17—N2—S1	−83.1 (2)
C1—C2—C3—C4	0.7 (4)	C14—C13—N2—C17	81.6 (2)
C2—C3—C4—C5	−2.2 (4)	C14—C13—N2—S1	−106.41 (19)
C3—C4—C5—C10	0.2 (4)	O3—C14—O4—C15	8.1 (5)
C3—C4—C5—C6	−177.7 (2)	C13—C14—O4—C15	−172.2 (3)
C4—C5—C6—C7	175.7 (2)	O3—C14—O4—C15'	26 (2)
C10—C5—C6—C7	−2.3 (3)	C13—C14—O4—C15'	−155 (2)
C4—C5—C6—S1	−0.8 (3)	C16—C15—O4—C14	90.1 (10)
C10—C5—C6—S1	−178.75 (15)	C16—C15—O4—C15'	39 (4)
C5—C6—C7—C8	−1.0 (3)	C16'—C15'—O4—C14	163 (3)
S1—C6—C7—C8	175.69 (17)	C16'—C15'—O4—C15	−62 (3)
C6—C7—C8—C9	2.2 (3)	O5—C18—O6—C19'	−9.6 (5)
C7—C8—C9—C10	−0.2 (4)	C17—C18—O6—C19'	170.0 (4)
C8—C9—C10—C5	−3.2 (3)	O5—C18—O6—C19	11.4 (6)
C8—C9—C10—C1	179.9 (2)	C17—C18—O6—C19	−169.0 (6)
C4—C5—C10—C9	−173.8 (2)	C20'—C19'—O6—C18	95.9 (12)
C6—C5—C10—C9	4.3 (3)	C20'—C19'—O6—C19	34.6 (15)
C4—C5—C10—C1	3.2 (3)	C20—C19—O6—C18	159.6 (9)
C6—C5—C10—C1	−178.75 (18)	C20—C19—O6—C19'	−72.0 (19)
C2—C1—C10—C9	172.3 (2)	C17—N2—S1—O2	126.11 (17)
N1—C1—C10—C9	−4.9 (3)	C13—N2—S1—O2	−45.80 (18)
C2—C1—C10—C5	−4.6 (3)	C17—N2—S1—O1	−2.41 (19)
N1—C1—C10—C5	178.17 (19)	C13—N2—S1—O1	−174.32 (15)
N2—C13—C14—O3	−10.0 (4)	C17—N2—S1—C6	−119.93 (17)
N2—C13—C14—O4	170.3 (2)	C13—N2—S1—C6	68.16 (17)
N2—C17—C18—O5	−10.7 (3)	C7—C6—S1—O2	14.37 (19)
N2—C17—C18—O6	169.75 (19)	C5—C6—S1—O2	−168.98 (16)
C2—C1—N1—C11	111.9 (3)	C7—C6—S1—O1	144.39 (16)
C10—C1—N1—C11	−71.0 (3)	C5—C6—S1—O1	−38.95 (19)
C2—C1—N1—C12	−18.7 (4)	C7—C6—S1—N2	−101.51 (17)
C10—C1—N1—C12	158.4 (2)	C5—C6—S1—N2	75.14 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1	0.93	2.36	3.006 (3)	126
C13—H13A···O2ⁱ	0.97	2.36	3.272 (3)	157

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₆N₂O₆S
M_r	422.49
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	13.1266 (9), 8.4592 (5), 19.3206 (12)
β (°)	93.530 (1)
V (Å³)	2141.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.970, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	16359, 4201, 3705
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.145, 1.05
No. of reflections	4201
No. of parameters	306
No. of restraints	12
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.27

Computer programs: SMART (Bruker, 2007), SAINT-Plus (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Selected torsion angles (º) top

C16—C15—O4—C14

90.1 (10)

C20—C19—O6—C18

159.6 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1	0.93	2.36	3.006 (3)	126.1
C13—H13A···O2ⁱ	0.97	2.36	3.272 (3)	157.3

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

References

Bruker (2007). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Christoforou, A. M., Marzilli, P. A. & Marzilli, L. G. (2006). Inorg. Chem. 45, 6771–6781. Web of Science CrossRef PubMed CAS Google Scholar
Corradini, R., Dossena, A., Galaverna, G., Marchelli, R., Panagia, A. & Sarto, G. (1997). J. Org. Chem. 62, 6283–6289. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, S., Zhao, B., Su, Z., Xia, X. & Zhang, Y. (2009). Acta Cryst. E65, o1452. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 65| Part 11| November 2009| Page o2752

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