tert-Butyl N-[2-(N-isobutyl-4-meth­oxy­benzene­sulfonamido)­eth­yl]carbamate

Bai, X.-G.; Wang, J.-X.

doi:10.1107/S1600536814009143

organic compounds

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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Page o674

doi:10.1107/S1600536814009143

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tert-Butyl N-[2-(N-isobutyl-4-methoxybenzenesulfonamido)ethyl]carbamate

Xiao-Guang Bai ^a and Ju-Xian Wang ^a ^*

^aInstitute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, People's Republic of China
^*Correspondence e-mail: imbjxwang@gmail.com

(Received 15 April 2014; accepted 23 April 2014; online 17 May 2014)

The title compound, C₁₈H₃₀N₂O₅S, was synthesized by the reaction of tert-butyl 2-(isobutylamino)ethylcarbamate with p-methoxyphenylsulfonyl chloride. In the molecule, two intramolecular C—H⋯O hydrogen bonds are observed. In the crystal, molecules are linked by N—H⋯O hydrogen bonds involving the imino group N atom and the ester group O atom into chains running parallel to the b axis. The chains are further connected by C—H⋯O hydrogen bonds, forming layers parallel to the bc plane.

CCDC reference: 998938

Related literature

For potential HIV-1 protease inhibitors, see: Surleraux et al. (2005 ); Ghosh et al. (2006 , 2011 ); Guo et al. (2010 ). For the structure of the methoxy analogue, see: Chatziefthimiou et al. (2006 )

Experimental

Crystal data

C₁₈H₃₀N₂O₅S
M_r = 386.50
Monoclinic, P 2₁ /c
a = 19.2484 (5) Å
b = 5.29088 (12) Å
c = 20.1825 (6) Å
β = 92.497 (3)°
V = 2053.46 (9) Å³
Z = 4
Cu Kα radiation
μ = 1.65 mm⁻¹
T = 293 K
0.28 × 0.16 × 0.14 mm

Data collection

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ) T_min = 0.776, T_max = 1.000
11865 measured reflections
3658 independent reflections
3122 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.089
S = 1.05
3658 reflections
245 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O2	0.97	2.43	2.9106 (19)	110
C13—H13A⋯O3	0.97	2.48	3.107 (2)	122
C3—H3⋯O4ⁱ	0.93	2.59	3.402 (2)	147
N2—H2A⋯O4ⁱⁱ	0.82 (2)	2.38 (2)	3.190 (2)	171 (2)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x, y+1, z.

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC.

Supporting information

CCDC reference: 998938

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814009143/rz5120sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814009143/rz5120Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814009143/rz5120Isup3.cml

checkCIF report

Comment top

As a part of our ongoing project aimed at the development of potential HIV-1 protease inhibitors (Surleraux et al., 2005; Ghosh et al., 2006, 2011; Guo et al., 2010), we have synthesized the title compound and report its crystal structure herein.

The molecular structure of the title compound is illustrated in Fig. 1. Bond distances and angles are similar to those found in the methoxy analogue (Chatziefthimiou et al., 2006). The molecular conformation is stabilized by two intramolecular C—H···O hydrogen bonds (Table 1). In the crystal, the molecules are linked into chains by intermolecular N—H···O hydrogen bonds (Table 1) parallel to the b axis (Fig. 2), which are further connected to form layers parallel to the bc plane by C—H···O hydrogen bonds (Table 1).

Related literature top

For potential HIV-1 protease inhibitors, see: Surleraux et al. (2005); Ghosh et al. (2006, 2011); Guo et al. (2010). For the structure of the methoxy analogue, see: Chatziefthimiou et al. (2006)

Experimental top

To a solution of tert-butyl 2-(isobutylamino)ethylcarbamate (1.13 g, 5.2 mmol) and "N,N-diisopropylethylamine (1.34 g, 10.4 mmol) in dichloromethane (10 ml) was added dropwise a solution of p-methoxyphenylsulfonyl chloride (1.18 g, 5.7 mmol) in dichloromethane (3 ml) over a period of 10 min at room temperature. The reaction mixture was stirred for 5 h at the same temperature and concentrated under reduced pressure. tert-Butyl 2-(N-isobutyl-4-methoxyphenylsulfonamido)ethylcarbamate was obtained as a white solid by flash chromatography (40 g silica gel, petroleum ether/AcOEt, 1:10 v/v). The yield is 42%. Colourless block crystals suitable for X-ray diffraction were obtained in 3 day by slow evaporation of a petroleum ether/AcOEt (4:1 v/v) solution.

Computing details top

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: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Partial packing diagram of the title compound showing the formation of a molecular chain through N—H···O hydrogen bonds. Hydrogen atoms not involved in hydrogen bonding (dashed lines) are omitted.

tert-Butyl N-[2-(N-isobutyl-4-methoxybenzenesulfonamido)ethyl]carbamat top

Crystal data top

C₁₈H₃₀N₂O₅S	F(000) = 832
M_r = 386.50	D_x = 1.250 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 5271 reflections
a = 19.2484 (5) Å	θ = 4.4–67.1°
b = 5.29088 (12) Å	µ = 1.65 mm⁻¹
c = 20.1825 (6) Å	T = 293 K
β = 92.497 (3)°	Block, colorless
V = 2053.46 (9) Å³	0.28 × 0.16 × 0.14 mm
Z = 4

Data collection top

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer	3658 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	3122 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.031
Detector resolution: 10.4713 pixels mm^-1	θ_max = 67.2°, θ_min = 4.4°
ω scans	h = −21→22
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −4→6
T_min = 0.776, T_max = 1.000	l = −22→24
11865 measured reflections

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0429P)² + 0.3785P] where P = (F_o² + 2F_c²)/3
3658 reflections	(Δ/σ)_max = 0.001
245 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₈H₃₀N₂O₅S	V = 2053.46 (9) Å³
M_r = 386.50	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 19.2484 (5) Å	µ = 1.65 mm⁻¹
b = 5.29088 (12) Å	T = 293 K
c = 20.1825 (6) Å	0.28 × 0.16 × 0.14 mm
β = 92.497 (3)°

Data collection top

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer	3658 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	3122 reflections with I > 2σ(I)
T_min = 0.776, T_max = 1.000	R_int = 0.031
11865 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.17 e Å⁻³
3658 reflections	Δρ_min = −0.30 e Å⁻³
245 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
C1	0.85965 (7)	0.6201 (3)	0.54057 (7)	0.0368 (3)
C2	0.82937 (9)	0.6078 (3)	0.60169 (8)	0.0474 (4)
H2	0.7921	0.7121	0.6107	0.057*
C3	0.85494 (9)	0.4403 (4)	0.64878 (8)	0.0527 (4)
H3	0.8347	0.4314	0.6897	0.063*
C4	0.91066 (8)	0.2845 (3)	0.63579 (8)	0.0440 (4)
C5	0.94134 (8)	0.2961 (3)	0.57509 (8)	0.0435 (4)
H5	0.9788	0.1921	0.5662	0.052*
C6	0.91528 (8)	0.4657 (3)	0.52769 (7)	0.0403 (3)
H6	0.9356	0.4754	0.4868	0.048*
C7	0.98789 (12)	−0.0418 (4)	0.67445 (11)	0.0687 (6)
H7A	0.9749	−0.1530	0.6384	0.103*
H7B	0.9983	−0.1396	0.7137	0.103*
H7C	1.0282	0.0537	0.6634	0.103*
C8	0.70575 (8)	0.5843 (3)	0.45894 (8)	0.0420 (3)
H8A	0.6984	0.6863	0.4980	0.050*
H8B	0.7095	0.4093	0.4730	0.050*
C9	0.64333 (8)	0.6121 (3)	0.41093 (8)	0.0447 (4)
H9	0.6499	0.5001	0.3730	0.054*
C10	0.57790 (9)	0.5294 (4)	0.44490 (10)	0.0602 (5)
H10A	0.5853	0.3658	0.4645	0.090*
H10B	0.5397	0.5213	0.4128	0.090*
H10C	0.5675	0.6491	0.4788	0.090*
C11	0.63562 (11)	0.8797 (4)	0.38541 (12)	0.0743 (6)
H11A	0.6288	0.9921	0.4219	0.111*
H11B	0.5963	0.8894	0.3546	0.111*
H11C	0.6769	0.9276	0.3635	0.111*
C12	0.80312 (8)	0.4772 (3)	0.38535 (8)	0.0426 (3)
H12A	0.7712	0.3368	0.3783	0.051*
H12B	0.8454	0.4114	0.4069	0.051*
C13	0.82046 (9)	0.5869 (4)	0.31821 (8)	0.0517 (4)
H13A	0.8475	0.7399	0.3254	0.062*
H13B	0.8493	0.4669	0.2956	0.062*
C14	0.72163 (8)	0.4609 (3)	0.24696 (7)	0.0410 (3)
C15	0.62067 (9)	0.3966 (3)	0.17124 (8)	0.0459 (4)
C16	0.57907 (11)	0.2465 (4)	0.21953 (10)	0.0642 (5)
H16A	0.6083	0.1208	0.2407	0.096*
H16B	0.5408	0.1655	0.1961	0.096*
H16C	0.5617	0.3581	0.2525	0.096*
C17	0.65827 (11)	0.2296 (4)	0.12362 (9)	0.0646 (5)
H17A	0.6895	0.3305	0.0989	0.097*
H17B	0.6250	0.1496	0.0936	0.097*
H17C	0.6842	0.1028	0.1481	0.097*
C18	0.57448 (13)	0.5846 (4)	0.13381 (13)	0.0827 (7)
H18A	0.5534	0.6958	0.1647	0.124*
H18B	0.5388	0.4956	0.1086	0.124*
H18C	0.6019	0.6816	0.1044	0.124*
N1	0.77172 (6)	0.6617 (2)	0.42986 (6)	0.0371 (3)
N2	0.76011 (8)	0.6456 (3)	0.27567 (7)	0.0474 (3)
O1	0.93204 (7)	0.1260 (3)	0.68599 (6)	0.0611 (3)
O2	0.78598 (6)	1.0150 (2)	0.50924 (6)	0.0505 (3)
O3	0.88216 (6)	0.8952 (2)	0.43790 (5)	0.0462 (3)
O4	0.73211 (6)	0.2357 (2)	0.25588 (6)	0.0495 (3)
O5	0.67038 (6)	0.5608 (2)	0.20784 (6)	0.0511 (3)
S1	0.825787 (18)	0.82405 (6)	0.478139 (18)	0.03723 (12)
H2A	0.7503 (11)	0.793 (4)	0.2665 (10)	0.060 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0318 (7)	0.0407 (7)	0.0375 (7)	−0.0033 (6)	−0.0025 (6)	−0.0012 (6)
C2	0.0405 (8)	0.0577 (10)	0.0443 (8)	0.0031 (7)	0.0057 (7)	−0.0026 (7)
C3	0.0501 (10)	0.0697 (11)	0.0390 (8)	−0.0005 (8)	0.0101 (7)	0.0035 (8)
C4	0.0441 (8)	0.0474 (8)	0.0400 (8)	−0.0088 (7)	−0.0052 (6)	0.0062 (7)
C5	0.0372 (8)	0.0486 (9)	0.0442 (8)	0.0021 (7)	−0.0017 (6)	0.0011 (7)
C6	0.0345 (7)	0.0497 (8)	0.0366 (7)	0.0005 (6)	0.0007 (6)	0.0017 (6)
C7	0.0723 (13)	0.0631 (12)	0.0693 (12)	0.0052 (10)	−0.0139 (10)	0.0211 (10)
C8	0.0367 (8)	0.0466 (8)	0.0428 (8)	−0.0027 (7)	0.0007 (6)	0.0046 (7)
C9	0.0363 (8)	0.0500 (9)	0.0476 (8)	0.0010 (7)	−0.0013 (6)	0.0004 (7)
C10	0.0389 (9)	0.0742 (12)	0.0675 (11)	−0.0056 (9)	0.0011 (8)	0.0022 (10)
C11	0.0536 (11)	0.0713 (13)	0.0980 (16)	0.0155 (10)	0.0030 (11)	0.0339 (12)
C12	0.0400 (8)	0.0428 (8)	0.0444 (8)	0.0040 (7)	−0.0050 (6)	−0.0050 (7)
C13	0.0422 (9)	0.0688 (11)	0.0442 (8)	−0.0069 (8)	0.0024 (7)	−0.0105 (8)
C14	0.0461 (8)	0.0429 (8)	0.0342 (7)	−0.0037 (7)	0.0034 (6)	−0.0027 (6)
C15	0.0509 (9)	0.0383 (8)	0.0475 (8)	−0.0074 (7)	−0.0082 (7)	−0.0010 (7)
C16	0.0576 (11)	0.0712 (12)	0.0645 (11)	−0.0108 (10)	0.0085 (9)	0.0014 (10)
C17	0.0709 (13)	0.0721 (12)	0.0509 (10)	−0.0149 (10)	0.0038 (9)	−0.0163 (9)
C18	0.0884 (16)	0.0549 (11)	0.1003 (17)	−0.0064 (11)	−0.0478 (14)	0.0101 (11)
N1	0.0324 (6)	0.0399 (6)	0.0386 (6)	−0.0009 (5)	−0.0021 (5)	−0.0010 (5)
N2	0.0557 (8)	0.0455 (8)	0.0405 (7)	−0.0096 (7)	−0.0031 (6)	−0.0014 (6)
O1	0.0663 (8)	0.0678 (8)	0.0489 (7)	0.0010 (7)	−0.0025 (6)	0.0188 (6)
O2	0.0520 (7)	0.0400 (6)	0.0593 (7)	0.0084 (5)	−0.0007 (5)	−0.0097 (5)
O3	0.0422 (6)	0.0462 (6)	0.0502 (6)	−0.0078 (5)	0.0016 (5)	0.0059 (5)
O4	0.0555 (7)	0.0411 (6)	0.0512 (6)	0.0035 (5)	−0.0035 (5)	−0.0034 (5)
O5	0.0606 (7)	0.0367 (6)	0.0543 (6)	−0.0050 (5)	−0.0165 (5)	−0.0016 (5)
S1	0.03497 (19)	0.03481 (19)	0.0416 (2)	−0.00052 (14)	−0.00156 (14)	−0.00101 (14)

Geometric parameters (Å, º) top

C1—C6	1.381 (2)	C11—H11C	0.9600
C1—C2	1.389 (2)	C12—N1	1.474 (2)
C1—S1	1.7621 (15)	C12—C13	1.524 (2)
C2—C3	1.375 (2)	C12—H12A	0.9700
C2—H2	0.9300	C12—H12B	0.9700
C3—C4	1.387 (3)	C13—N2	1.448 (2)
C3—H3	0.9300	C13—H13A	0.9700
C4—O1	1.365 (2)	C13—H13B	0.9700
C4—C5	1.384 (2)	C14—O4	1.2205 (19)
C5—C6	1.389 (2)	C14—N2	1.342 (2)
C5—H5	0.9300	C14—O5	1.345 (2)
C6—H6	0.9300	C15—O5	1.4677 (19)
C7—O1	1.421 (3)	C15—C17	1.513 (3)
C7—H7A	0.9600	C15—C16	1.513 (3)
C7—H7B	0.9600	C15—C18	1.514 (3)
C7—H7C	0.9600	C16—H16A	0.9600
C8—N1	1.4797 (19)	C16—H16B	0.9600
C8—C9	1.518 (2)	C16—H16C	0.9600
C8—H8A	0.9700	C17—H17A	0.9600
C8—H8B	0.9700	C17—H17B	0.9600
C9—C11	1.512 (3)	C17—H17C	0.9600
C9—C10	1.524 (2)	C18—H18A	0.9600
C9—H9	0.9800	C18—H18B	0.9600
C10—H10A	0.9600	C18—H18C	0.9600
C10—H10B	0.9600	N1—S1	1.6378 (12)
C10—H10C	0.9600	N2—H2A	0.82 (2)
C11—H11A	0.9600	O2—S1	1.4294 (12)
C11—H11B	0.9600	O3—S1	1.4338 (12)

C6—C1—C2	119.91 (14)	N1—C12—H12B	108.8
C6—C1—S1	119.56 (11)	C13—C12—H12B	108.8
C2—C1—S1	120.50 (12)	H12A—C12—H12B	107.7
C3—C2—C1	119.52 (15)	N2—C13—C12	114.06 (14)
C3—C2—H2	120.2	N2—C13—H13A	108.7
C1—C2—H2	120.2	C12—C13—H13A	108.7
C2—C3—C4	120.60 (15)	N2—C13—H13B	108.7
C2—C3—H3	119.7	C12—C13—H13B	108.7
C4—C3—H3	119.7	H13A—C13—H13B	107.6
O1—C4—C5	123.89 (16)	O4—C14—N2	124.23 (15)
O1—C4—C3	115.82 (15)	O4—C14—O5	125.63 (14)
C5—C4—C3	120.29 (15)	N2—C14—O5	110.14 (14)
C4—C5—C6	118.87 (15)	O5—C15—C17	110.24 (14)
C4—C5—H5	120.6	O5—C15—C16	109.76 (14)
C6—C5—H5	120.6	C17—C15—C16	112.57 (16)
C1—C6—C5	120.81 (14)	O5—C15—C18	102.60 (13)
C1—C6—H6	119.6	C17—C15—C18	110.70 (17)
C5—C6—H6	119.6	C16—C15—C18	110.52 (18)
O1—C7—H7A	109.5	C15—C16—H16A	109.5
O1—C7—H7B	109.5	C15—C16—H16B	109.5
H7A—C7—H7B	109.5	H16A—C16—H16B	109.5
O1—C7—H7C	109.5	C15—C16—H16C	109.5
H7A—C7—H7C	109.5	H16A—C16—H16C	109.5
H7B—C7—H7C	109.5	H16B—C16—H16C	109.5
N1—C8—C9	112.90 (12)	C15—C17—H17A	109.5
N1—C8—H8A	109.0	C15—C17—H17B	109.5
C9—C8—H8A	109.0	H17A—C17—H17B	109.5
N1—C8—H8B	109.0	C15—C17—H17C	109.5
C9—C8—H8B	109.0	H17A—C17—H17C	109.5
H8A—C8—H8B	107.8	H17B—C17—H17C	109.5
C11—C9—C8	111.82 (15)	C15—C18—H18A	109.5
C11—C9—C10	110.57 (16)	C15—C18—H18B	109.5
C8—C9—C10	109.38 (13)	H18A—C18—H18B	109.5
C11—C9—H9	108.3	C15—C18—H18C	109.5
C8—C9—H9	108.3	H18A—C18—H18C	109.5
C10—C9—H9	108.3	H18B—C18—H18C	109.5
C9—C10—H10A	109.5	C12—N1—C8	116.13 (12)
C9—C10—H10B	109.5	C12—N1—S1	116.31 (10)
H10A—C10—H10B	109.5	C8—N1—S1	116.30 (10)
C9—C10—H10C	109.5	C14—N2—C13	120.87 (16)
H10A—C10—H10C	109.5	C14—N2—H2A	118.5 (15)
H10B—C10—H10C	109.5	C13—N2—H2A	120.5 (15)
C9—C11—H11A	109.5	C4—O1—C7	117.91 (14)
C9—C11—H11B	109.5	C14—O5—C15	120.56 (12)
H11A—C11—H11B	109.5	O2—S1—O3	119.77 (7)
C9—C11—H11C	109.5	O2—S1—N1	107.05 (7)
H11A—C11—H11C	109.5	O3—S1—N1	106.12 (7)
H11B—C11—H11C	109.5	O2—S1—C1	107.89 (7)
N1—C12—C13	113.64 (13)	O3—S1—C1	107.48 (7)
N1—C12—H12A	108.8	N1—S1—C1	108.05 (7)
C13—C12—H12A	108.8

C6—C1—C2—C3	−0.4 (2)	C5—C4—O1—C7	−1.8 (2)
S1—C1—C2—C3	177.48 (13)	C3—C4—O1—C7	178.47 (16)
C1—C2—C3—C4	0.1 (3)	O4—C14—O5—C15	0.1 (2)
C2—C3—C4—O1	179.80 (16)	N2—C14—O5—C15	−179.50 (14)
C2—C3—C4—C5	0.1 (3)	C17—C15—O5—C14	−61.01 (19)
O1—C4—C5—C6	−179.78 (15)	C16—C15—O5—C14	63.5 (2)
C3—C4—C5—C6	−0.1 (2)	C18—C15—O5—C14	−178.95 (17)
C2—C1—C6—C5	0.4 (2)	C12—N1—S1—O2	171.49 (10)
S1—C1—C6—C5	−177.50 (12)	C8—N1—S1—O2	−46.10 (12)
C4—C5—C6—C1	−0.1 (2)	C12—N1—S1—O3	42.49 (12)
N1—C8—C9—C11	−57.0 (2)	C8—N1—S1—O3	−175.09 (10)
N1—C8—C9—C10	−179.83 (14)	C12—N1—S1—C1	−72.54 (12)
N1—C12—C13—N2	−70.15 (18)	C8—N1—S1—C1	69.88 (12)
C13—C12—N1—C8	127.99 (14)	C6—C1—S1—O2	−161.35 (12)
C13—C12—N1—S1	−89.53 (14)	C2—C1—S1—O2	20.79 (15)
C9—C8—N1—C12	−78.70 (17)	C6—C1—S1—O3	−30.90 (14)
C9—C8—N1—S1	138.82 (12)	C2—C1—S1—O3	151.23 (13)
O4—C14—N2—C13	2.9 (2)	C6—C1—S1—N1	83.23 (13)
O5—C14—N2—C13	−177.48 (14)	C2—C1—S1—N1	−94.64 (13)
C12—C13—N2—C14	−72.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O2	0.97	2.43	2.9106 (19)	110
C13—H13A···O3	0.97	2.48	3.107 (2)	122
C3—H3···O4ⁱ	0.93	2.59	3.402 (2)	147
N2—H2A···O4ⁱⁱ	0.82 (2)	2.38 (2)	3.190 (2)	171 (2)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O2	0.97	2.43	2.9106 (19)	110
C13—H13A···O3	0.97	2.48	3.107 (2)	122
C3—H3···O4ⁱ	0.93	2.59	3.402 (2)	147
N2—H2A···O4ⁱⁱ	0.82 (2)	2.38 (2)	3.190 (2)	171 (2)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, y+1, z.

Acknowledgements

We are grateful for the financial support from the National Natural Science Foundation of China (No. 81302644).

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