Methyl 2-(4-methyl­phenyl­sulfonamido)-3-phenyl­propanoate

Yin, P.; Hu, M.-L.; Xiong, J.; Yan, X.-W.

doi:10.1107/S1600536807018600

Methyl 2-(4-methylphenylsulfonamido)-3-phenylpropanoate

P. Yin, M.-L. Hu, J. Xiong and X.-W. Yan

The title compound, C₁₇H₁₉NO₄S, has two independent molecules in the asymmetric unit linked by an N—H

O hydrogen bond. The principal difference between them lies in the relative orientations of the two aromatic rings. These are inclined at an angle of 3.70 (3)° in one molecule but at 58.41 (12)° in the other. N—H

O hydrogen bonds form zigzag chains down the a axis and these chains are further stabilized by weak C—H

O interactions, forming a network structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807018600/sj2288sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807018600/sj2288Isup2.hkl Contains datablock I

CCDC reference: 647702

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.007 Å
R factor = 0.078
wR factor = 0.172
Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.68 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.38 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C33
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT480_ALERT_4_C Long H...A H-Bond Reported H21    ..  O4      ..       2.68 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H30    ..  O1      ..       2.68 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9     ..  O8      ..       2.67 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.02
           From the CIF: _reflns_number_total               5844
           Count of symmetry unique reflns         3356
           Completeness (_total/calc)            174.14%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2488
           Fraction of Friedel pairs measured     0.741
           Are heavy atom types Z>Si present        yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C32    = .          S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   2 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
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The sulfonamide group is present in many bioactive compounds and has been used as protecting group (Yan et al., 2007; Patani & Lavoie, 1996). In an extension of research on sulfonamide derivatives, we report here the synthesis and structure of the title compound (1), Fig. 1.

The title compound, C₁₇H₈NO₄S, has two independent molecules in the asymmetric unit linked by an N—H···O hydrogen bond. The methyl-3-phenyl propanoate residue carries a 4-methylbenzenesulfonamide substituent in the 2-position. The principal difference between the two unique molecules lies in the relative orientations of the two aromatic rings. These are inclined at 3.70 (3)° in one molecule but 58.41 (12)° in the other. N—H···O hydrogen bonds form zigzag rows down the a axis and these rows are further stabilized by weak C—H···O interactions forming a network structure.

Related literature top

For general background, see Patani & Lavoie (1996) and Yan et al. (2007). For related structures, see Ziemer et al. (2001), Kazak et al. (2000), Creaser et al. (2001) and Yu (2006).

Experimental top

Aqueous NaOH (20 ml, 10%) was added dropwise to a mixture of 4-methylbenzene-1-sulfonyl chloride (10 mmol, 1.905 g) and methyl 2-amino-3-phenylpropanoate (12 mmol, 2.148 g) with constant stirring for 4 h. The solvent was then evaporated in a vacuum. After column chromatography on silica eluting with petroleum ether/ethyl acetate (5/1 v/v), the purified product was dissolved in ethanol and left for 10 d until single crystals formed.

Structure description top

For general background, see Patani & Lavoie (1996) and Yan et al. (2007). For related structures, see Ziemer et al. (2001), Kazak et al. (2000), Creaser et al. (2001) and Yu (2006).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. The asymmetric unit of (I) showing 30% probability displacement ellipsoids and the atomic numbering. The hydrogen bond linking the two unique molecules is shown as a dashed line.
	Fig. 2. The crystal packing of (I) viewed down the b axis. Hydrogen bonds are drawn as dashed lines.

Methyl 2-(4-methylphenylsulfonamido)-3-phenylpropanoate top

Crystal data top

C₁₇H₁₉NO₄S	F(000) = 1408
M_r = 333.39	D_x = 1.336 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3436 reflections
a = 7.5812 (4) Å	θ = 2.2–24.2°
b = 11.6107 (7) Å	µ = 0.22 mm⁻¹
c = 37.659 (2) Å	T = 298 K
V = 3314.8 (3) Å³	Block, colorless
Z = 8	0.29 × 0.24 × 0.09 mm

Data collection top

Bruker APEX area-detector diffractometer	5844 independent reflections
Radiation source: fine-focus sealed tube	5517 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
φ and ω scans	θ_max = 25.0°, θ_min = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −8→9
T_min = 0.938, T_max = 0.979	k = −13→13
17577 measured reflections	l = −44→39

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.078	H-atom parameters constrained
wR(F²) = 0.172	w = 1/[σ²(F_o²) + (0.0689P)² + 1.5711P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
5844 reflections	Δρ_max = 0.49 e Å⁻³
419 parameters	Δρ_min = −0.36 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 2489 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.03 (1)

Crystal data top

C₁₇H₁₉NO₄S	V = 3314.8 (3) Å³
M_r = 333.39	Z = 8
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.5812 (4) Å	µ = 0.22 mm⁻¹
b = 11.6107 (7) Å	T = 298 K
c = 37.659 (2) Å	0.29 × 0.24 × 0.09 mm

Data collection top

Bruker APEX area-detector diffractometer	5844 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	5517 reflections with I > 2σ(I)
T_min = 0.938, T_max = 0.979	R_int = 0.041
17577 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.078	H-atom parameters constrained
wR(F²) = 0.172	Δρ_max = 0.49 e Å⁻³
S = 1.05	Δρ_min = −0.36 e Å⁻³
5844 reflections	Absolute structure: Flack (1983), 2489 Friedel pairs
419 parameters	Absolute structure parameter: −0.03 (1)
0 restraints

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
S1	0.30565 (15)	0.41714 (9)	0.88519 (3)	0.0308 (3)
S2	0.78670 (15)	0.65352 (10)	0.87955 (3)	0.0332 (3)
O1	0.1703 (4)	0.3475 (3)	0.90049 (9)	0.0436 (8)
O2	0.2899 (5)	0.5393 (3)	0.88534 (10)	0.0485 (9)
O3	0.5169 (5)	0.1975 (3)	0.97873 (9)	0.0509 (10)
O4	0.5427 (7)	0.3860 (3)	0.97724 (10)	0.0735 (14)
O5	0.7735 (5)	0.5321 (3)	0.88491 (10)	0.0526 (10)
O6	0.6695 (4)	0.7071 (3)	0.85494 (9)	0.0485 (9)
O7	0.9814 (6)	0.5722 (3)	0.80681 (9)	0.0555 (10)
O8	1.0416 (8)	0.7242 (5)	0.77332 (11)	0.0972 (19)
N1	0.4871 (5)	0.3878 (3)	0.90489 (10)	0.0357 (9)
H1	0.5673	0.4402	0.9051	0.043*
N2	0.9852 (5)	0.6845 (3)	0.86746 (9)	0.0331 (9)
H2	1.0716	0.6608	0.8803	0.040*
C1	0.4465 (10)	0.2586 (7)	0.73480 (15)	0.077 (2)
H1A	0.4116	0.3152	0.7176	0.115*
H1B	0.3857	0.1876	0.7302	0.115*
H1C	0.5714	0.2462	0.7332	0.115*
C2	0.4004 (8)	0.3011 (5)	0.77176 (13)	0.0469 (13)
C3	0.4548 (8)	0.4083 (5)	0.78334 (14)	0.0509 (14)
H3	0.5141	0.4564	0.7676	0.061*
C4	0.4240 (7)	0.4458 (4)	0.81734 (14)	0.0427 (13)
H4	0.4633	0.5179	0.8247	0.051*
C5	0.3334 (6)	0.3744 (4)	0.84049 (12)	0.0324 (11)
C6	0.2739 (7)	0.2682 (4)	0.82948 (13)	0.0456 (13)
H6	0.2119	0.2205	0.8449	0.055*
C7	0.3082 (8)	0.2343 (5)	0.79527 (14)	0.0550 (15)
H7	0.2670	0.1630	0.7877	0.066*
C8	0.7147 (8)	0.0712 (5)	0.80804 (15)	0.0575 (15)
H8	0.7168	0.0360	0.7859	0.069*
C9	0.7900 (8)	0.1786 (5)	0.81268 (14)	0.0540 (14)
H9	0.8446	0.2154	0.7937	0.065*
C10	0.7839 (7)	0.2306 (4)	0.84540 (13)	0.0422 (12)
H10	0.8338	0.3032	0.8482	0.051*
C11	0.7059 (6)	0.1780 (4)	0.87402 (11)	0.0323 (10)
C12	0.6303 (7)	0.0701 (5)	0.86856 (14)	0.0463 (13)
H12	0.5740	0.0337	0.8874	0.056*
C13	0.6364 (8)	0.0164 (5)	0.83651 (16)	0.0551 (15)
H13	0.5881	−0.0567	0.8338	0.066*
C14	0.7054 (6)	0.2304 (4)	0.91055 (11)	0.0361 (11)
H14A	0.7918	0.2920	0.9112	0.043*
H14B	0.7425	0.1723	0.9275	0.043*
C15	0.5268 (6)	0.2789 (4)	0.92248 (11)	0.0285 (10)
H15	0.4343	0.2231	0.9166	0.034*
C16	0.5283 (6)	0.2975 (4)	0.96227 (13)	0.0358 (11)
C17	0.5214 (9)	0.1996 (6)	1.01749 (14)	0.0658 (17)
H17A	0.6413	0.1932	1.0254	0.099*
H17B	0.4539	0.1362	1.0266	0.099*
H17C	0.4720	0.2707	1.0259	0.099*
C18	0.6813 (9)	0.8776 (5)	1.02333 (15)	0.0652 (17)
H18A	0.5868	0.8395	1.0356	0.098*
H18B	0.6526	0.9575	1.0203	0.098*
H18C	0.7879	0.8708	1.0369	0.098*
C19	0.7072 (7)	0.8225 (4)	0.98741 (13)	0.0427 (12)
C20	0.6593 (6)	0.7100 (5)	0.98159 (13)	0.0460 (13)
H20	0.6089	0.6681	1.0000	0.055*
C21	0.6837 (7)	0.6577 (4)	0.94926 (12)	0.0414 (12)
H21	0.6495	0.5816	0.9459	0.050*
C22	0.7590 (5)	0.7186 (4)	0.92179 (12)	0.0314 (10)
C23	0.8106 (7)	0.8313 (4)	0.92689 (13)	0.0401 (12)
H23	0.8630	0.8725	0.9085	0.048*
C24	0.7836 (7)	0.8820 (4)	0.95953 (14)	0.0444 (12)
H24	0.8176	0.9582	0.9629	0.053*
C25	1.2226 (7)	1.0151 (5)	0.93353 (15)	0.0491 (14)
H25	1.2241	1.0585	0.9543	0.059*
C26	1.3082 (7)	0.9111 (5)	0.93215 (14)	0.0519 (14)
H26	1.3702	0.8849	0.9519	0.062*
C27	1.3029 (7)	0.8457 (4)	0.90196 (14)	0.0421 (12)
H27	1.3591	0.7745	0.9016	0.051*
C28	1.2150 (6)	0.8836 (4)	0.87189 (12)	0.0343 (11)
C29	1.1317 (6)	0.9901 (4)	0.87353 (14)	0.0404 (12)
H29	1.0729	1.0183	0.8537	0.049*
C30	1.1352 (7)	1.0544 (4)	0.90425 (16)	0.0457 (13)
H30	1.0777	1.1251	0.9051	0.055*
C31	1.2030 (7)	0.8098 (4)	0.83955 (13)	0.0439 (12)
H31A	1.2943	0.7513	0.8406	0.053*
H31B	1.2250	0.8569	0.8187	0.053*
C32	1.0244 (6)	0.7511 (4)	0.83555 (12)	0.0385 (12)
H32	0.9350	0.8118	0.8336	0.046*
C33	1.0183 (7)	0.6815 (5)	0.80167 (13)	0.0471 (14)
C34	0.9743 (10)	0.4971 (6)	0.77597 (17)	0.076 (2)
H34A	0.9096	0.5345	0.7573	0.113*
H34B	0.9165	0.4264	0.7822	0.113*
H34C	1.0919	0.4809	0.7680	0.113*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0306 (6)	0.0310 (6)	0.0309 (6)	0.0008 (5)	−0.0019 (5)	0.0014 (5)
S2	0.0268 (5)	0.0380 (6)	0.0347 (6)	−0.0098 (5)	0.0015 (5)	−0.0005 (5)
O1	0.0349 (18)	0.054 (2)	0.0419 (19)	0.0009 (17)	0.0030 (15)	0.0007 (16)
O2	0.053 (2)	0.0405 (19)	0.052 (2)	0.0063 (18)	−0.008 (2)	−0.0012 (16)
O3	0.077 (3)	0.041 (2)	0.0342 (19)	−0.008 (2)	0.0005 (18)	0.0058 (16)
O4	0.139 (4)	0.046 (2)	0.036 (2)	−0.004 (3)	−0.002 (2)	−0.0130 (18)
O5	0.053 (2)	0.041 (2)	0.064 (2)	−0.0175 (17)	0.018 (2)	−0.0087 (18)
O6	0.0319 (19)	0.074 (3)	0.0391 (19)	−0.0033 (19)	−0.0007 (15)	−0.0007 (18)
O7	0.073 (3)	0.050 (2)	0.043 (2)	0.001 (2)	0.005 (2)	−0.0105 (19)
O8	0.152 (5)	0.106 (4)	0.033 (2)	−0.051 (4)	0.012 (3)	−0.001 (2)
N1	0.035 (2)	0.036 (2)	0.035 (2)	−0.0139 (19)	−0.0022 (18)	0.0040 (17)
N2	0.029 (2)	0.037 (2)	0.034 (2)	−0.0010 (17)	−0.0003 (17)	0.0051 (17)
C1	0.088 (5)	0.102 (6)	0.040 (3)	0.008 (4)	0.004 (3)	−0.004 (4)
C2	0.053 (3)	0.056 (4)	0.032 (3)	0.012 (3)	−0.003 (2)	0.002 (3)
C3	0.055 (3)	0.058 (4)	0.040 (3)	−0.006 (3)	0.002 (3)	0.018 (3)
C4	0.048 (3)	0.036 (3)	0.044 (3)	−0.009 (2)	−0.007 (2)	0.011 (2)
C5	0.033 (2)	0.035 (2)	0.030 (2)	0.004 (2)	−0.003 (2)	0.0047 (19)
C6	0.056 (3)	0.045 (3)	0.036 (3)	−0.017 (3)	−0.004 (2)	0.002 (2)
C7	0.069 (4)	0.045 (3)	0.051 (3)	−0.018 (3)	−0.005 (3)	−0.008 (3)
C8	0.055 (3)	0.075 (4)	0.042 (3)	0.005 (3)	−0.002 (3)	−0.028 (3)
C9	0.056 (3)	0.070 (4)	0.037 (3)	0.001 (3)	0.012 (3)	0.000 (3)
C10	0.043 (3)	0.042 (3)	0.041 (3)	−0.001 (3)	0.000 (2)	0.000 (2)
C11	0.027 (2)	0.033 (2)	0.036 (2)	0.007 (2)	−0.001 (2)	0.0027 (19)
C12	0.043 (3)	0.053 (3)	0.043 (3)	0.000 (3)	0.007 (2)	0.004 (3)
C13	0.058 (4)	0.049 (3)	0.058 (4)	−0.005 (3)	0.005 (3)	−0.023 (3)
C14	0.030 (2)	0.044 (3)	0.035 (3)	−0.001 (2)	−0.002 (2)	0.002 (2)
C15	0.029 (2)	0.024 (2)	0.033 (2)	−0.0012 (19)	0.0010 (19)	−0.0007 (19)
C16	0.030 (3)	0.041 (3)	0.037 (3)	−0.002 (2)	−0.002 (2)	0.001 (2)
C17	0.082 (4)	0.079 (4)	0.036 (3)	0.001 (4)	0.011 (3)	0.013 (3)
C18	0.070 (4)	0.075 (4)	0.051 (4)	−0.003 (4)	0.014 (3)	−0.007 (3)
C19	0.033 (3)	0.054 (3)	0.041 (3)	0.004 (3)	0.000 (2)	−0.002 (2)
C20	0.039 (3)	0.059 (3)	0.040 (3)	−0.013 (3)	0.008 (2)	0.013 (3)
C21	0.042 (3)	0.041 (3)	0.042 (3)	−0.011 (3)	0.005 (2)	0.005 (2)
C22	0.022 (2)	0.035 (3)	0.037 (2)	0.0004 (18)	−0.0012 (18)	0.002 (2)
C23	0.044 (3)	0.036 (3)	0.041 (3)	−0.005 (2)	0.015 (2)	0.008 (2)
C24	0.047 (3)	0.034 (3)	0.052 (3)	−0.001 (3)	0.003 (3)	0.000 (2)
C25	0.040 (3)	0.049 (3)	0.059 (3)	−0.010 (3)	0.007 (3)	−0.016 (3)
C26	0.045 (3)	0.063 (4)	0.047 (3)	−0.018 (3)	−0.005 (3)	0.004 (3)
C27	0.033 (3)	0.037 (3)	0.056 (3)	−0.001 (3)	−0.002 (3)	0.006 (2)
C28	0.025 (2)	0.035 (2)	0.043 (3)	−0.011 (2)	0.006 (2)	0.009 (2)
C29	0.036 (3)	0.034 (3)	0.051 (3)	−0.003 (2)	−0.004 (2)	0.014 (2)
C30	0.037 (3)	0.028 (3)	0.071 (4)	0.001 (2)	0.008 (3)	−0.004 (3)
C31	0.040 (3)	0.042 (3)	0.050 (3)	−0.006 (3)	0.010 (3)	0.005 (2)
C32	0.038 (3)	0.041 (3)	0.037 (3)	−0.003 (2)	0.008 (2)	0.006 (2)
C33	0.043 (3)	0.070 (4)	0.029 (3)	−0.009 (3)	0.000 (2)	0.001 (3)
C34	0.090 (5)	0.073 (4)	0.064 (4)	0.002 (4)	0.002 (4)	−0.031 (4)

Geometric parameters (Å, º) top

S1—O2	1.423 (3)	C13—H13	0.9300
S1—O1	1.428 (4)	C14—C15	1.534 (6)
S1—N1	1.600 (4)	C14—H14A	0.9700
S1—C5	1.768 (5)	C14—H14B	0.9700
S2—O6	1.427 (4)	C15—C16	1.514 (6)
S2—O5	1.427 (4)	C15—H15	0.9800
S2—N2	1.613 (4)	C17—H17A	0.9600
S2—C22	1.774 (5)	C17—H17B	0.9600
O3—C16	1.318 (6)	C17—H17C	0.9600
O3—C17	1.460 (6)	C18—C19	1.509 (7)
O4—C16	1.178 (6)	C18—H18A	0.9600
O7—C33	1.313 (7)	C18—H18B	0.9600
O7—C34	1.453 (7)	C18—H18C	0.9600
O8—C33	1.190 (6)	C19—C20	1.374 (7)
N1—C15	1.459 (6)	C19—C24	1.384 (7)
N1—H1	0.8600	C20—C21	1.373 (7)
N2—C32	1.459 (6)	C20—H20	0.9300
N2—H2	0.8600	C21—C22	1.377 (6)
C1—C2	1.517 (8)	C21—H21	0.9300
C1—H1A	0.9600	C22—C23	1.378 (6)
C1—H1B	0.9600	C23—C24	1.378 (7)
C1—H1C	0.9600	C23—H23	0.9300
C2—C7	1.368 (8)	C24—H24	0.9300
C2—C3	1.382 (8)	C25—C30	1.365 (8)
C3—C4	1.373 (7)	C25—C26	1.371 (8)
C3—H3	0.9300	C25—H25	0.9300
C4—C5	1.385 (7)	C26—C27	1.368 (7)
C4—H4	0.9300	C26—H26	0.9300
C5—C6	1.377 (7)	C27—C28	1.386 (7)
C6—C7	1.372 (7)	C27—H27	0.9300
C6—H6	0.9300	C28—C29	1.390 (7)
C7—H7	0.9300	C28—C31	1.492 (7)
C8—C13	1.381 (8)	C29—C30	1.377 (7)
C8—C9	1.382 (8)	C29—H29	0.9300
C8—H8	0.9300	C30—H30	0.9300
C9—C10	1.373 (7)	C31—C32	1.523 (7)
C9—H9	0.9300	C31—H31A	0.9700
C10—C11	1.373 (6)	C31—H31B	0.9700
C10—H10	0.9300	C32—C33	1.511 (7)
C11—C12	1.393 (7)	C32—H32	0.9800
C11—C14	1.504 (6)	C34—H34A	0.9600
C12—C13	1.359 (7)	C34—H34B	0.9600
C12—H12	0.9300	C34—H34C	0.9600

O2—S1—O1	120.2 (2)	C14—C15—H15	108.8
O2—S1—N1	106.4 (2)	O4—C16—O3	123.3 (5)
O1—S1—N1	108.1 (2)	O4—C16—C15	126.8 (5)
O2—S1—C5	107.1 (2)	O3—C16—C15	109.8 (4)
O1—S1—C5	108.1 (2)	O3—C17—H17A	109.5
N1—S1—C5	106.2 (2)	O3—C17—H17B	109.5
O6—S2—O5	118.6 (2)	H17A—C17—H17B	109.5
O6—S2—N2	107.5 (2)	O3—C17—H17C	109.5
O5—S2—N2	109.0 (2)	H17A—C17—H17C	109.5
O6—S2—C22	108.9 (2)	H17B—C17—H17C	109.5
O5—S2—C22	106.6 (2)	C19—C18—H18A	109.5
N2—S2—C22	105.6 (2)	C19—C18—H18B	109.5
C16—O3—C17	117.0 (4)	H18A—C18—H18B	109.5
C33—O7—C34	118.0 (5)	C19—C18—H18C	109.5
C15—N1—S1	124.9 (3)	H18A—C18—H18C	109.5
C15—N1—H1	117.5	H18B—C18—H18C	109.5
S1—N1—H1	117.5	C20—C19—C24	117.7 (5)
C32—N2—S2	122.7 (3)	C20—C19—C18	120.8 (5)
C32—N2—H2	118.6	C24—C19—C18	121.5 (5)
S2—N2—H2	118.6	C21—C20—C19	121.7 (5)
C2—C1—H1A	109.5	C21—C20—H20	119.1
C2—C1—H1B	109.5	C19—C20—H20	119.1
H1A—C1—H1B	109.5	C20—C21—C22	119.7 (5)
C2—C1—H1C	109.5	C20—C21—H21	120.2
H1A—C1—H1C	109.5	C22—C21—H21	120.2
H1B—C1—H1C	109.5	C21—C22—C23	120.0 (4)
C7—C2—C3	117.3 (5)	C21—C22—S2	120.2 (4)
C7—C2—C1	121.8 (6)	C23—C22—S2	119.7 (4)
C3—C2—C1	120.9 (6)	C22—C23—C24	119.2 (4)
C4—C3—C2	122.0 (5)	C22—C23—H23	120.4
C4—C3—H3	119.0	C24—C23—H23	120.4
C2—C3—H3	119.0	C23—C24—C19	121.7 (5)
C3—C4—C5	118.7 (5)	C23—C24—H24	119.2
C3—C4—H4	120.6	C19—C24—H24	119.2
C5—C4—H4	120.6	C30—C25—C26	119.6 (5)
C6—C5—C4	120.6 (5)	C30—C25—H25	120.2
C6—C5—S1	119.9 (4)	C26—C25—H25	120.2
C4—C5—S1	119.4 (4)	C27—C26—C25	120.4 (5)
C7—C6—C5	118.5 (5)	C27—C26—H26	119.8
C7—C6—H6	120.7	C25—C26—H26	119.8
C5—C6—H6	120.7	C26—C27—C28	121.1 (5)
C2—C7—C6	122.8 (5)	C26—C27—H27	119.4
C2—C7—H7	118.6	C28—C27—H27	119.4
C6—C7—H7	118.6	C27—C28—C29	117.7 (5)
C13—C8—C9	119.7 (5)	C27—C28—C31	120.9 (4)
C13—C8—H8	120.2	C29—C28—C31	121.3 (4)
C9—C8—H8	120.2	C30—C29—C28	120.7 (5)
C10—C9—C8	119.8 (5)	C30—C29—H29	119.6
C10—C9—H9	120.1	C28—C29—H29	119.6
C8—C9—H9	120.1	C25—C30—C29	120.4 (5)
C11—C10—C9	121.5 (5)	C25—C30—H30	119.8
C11—C10—H10	119.2	C29—C30—H30	119.8
C9—C10—H10	119.2	C28—C31—C32	113.1 (4)
C10—C11—C12	117.5 (4)	C28—C31—H31A	109.0
C10—C11—C14	122.6 (4)	C32—C31—H31A	109.0
C12—C11—C14	119.9 (4)	C28—C31—H31B	109.0
C13—C12—C11	122.0 (5)	C32—C31—H31B	109.0
C13—C12—H12	119.0	H31A—C31—H31B	107.8
C11—C12—H12	119.0	N2—C32—C33	113.9 (4)
C12—C13—C8	119.5 (5)	N2—C32—C31	109.7 (4)
C12—C13—H13	120.2	C33—C32—C31	110.5 (4)
C8—C13—H13	120.2	N2—C32—H32	107.5
C11—C14—C15	114.7 (4)	C33—C32—H32	107.5
C11—C14—H14A	108.6	C31—C32—H32	107.5
C15—C14—H14A	108.6	O8—C33—O7	124.5 (5)
C11—C14—H14B	108.6	O8—C33—C32	122.0 (5)
C15—C14—H14B	108.6	O7—C33—C32	113.5 (4)
H14A—C14—H14B	107.6	O7—C34—H34A	109.5
N1—C15—C16	109.1 (4)	O7—C34—H34B	109.5
N1—C15—C14	111.5 (4)	H34A—C34—H34B	109.5
C16—C15—C14	109.6 (4)	O7—C34—H34C	109.5
N1—C15—H15	108.8	H34A—C34—H34C	109.5
C16—C15—H15	108.8	H34B—C34—H34C	109.5

O2—S1—N1—C15	155.8 (4)	C14—C15—C16—O4	103.6 (6)
O1—S1—N1—C15	25.5 (4)	N1—C15—C16—O3	163.4 (4)
C5—S1—N1—C15	−90.3 (4)	C14—C15—C16—O3	−74.2 (5)
O6—S2—N2—C32	−2.8 (4)	C24—C19—C20—C21	−0.7 (8)
O5—S2—N2—C32	126.9 (4)	C18—C19—C20—C21	−179.2 (5)
C22—S2—N2—C32	−118.9 (4)	C19—C20—C21—C22	0.4 (8)
C7—C2—C3—C4	2.2 (9)	C20—C21—C22—C23	0.4 (7)
C1—C2—C3—C4	−176.0 (6)	C20—C21—C22—S2	−178.5 (4)
C2—C3—C4—C5	−0.9 (8)	O6—S2—C22—C21	110.8 (4)
C3—C4—C5—C6	−0.6 (8)	O5—S2—C22—C21	−18.2 (4)
C3—C4—C5—S1	175.7 (4)	N2—S2—C22—C21	−134.0 (4)
O2—S1—C5—C6	−150.3 (4)	O6—S2—C22—C23	−68.1 (4)
O1—S1—C5—C6	−19.6 (5)	O5—S2—C22—C23	162.9 (4)
N1—S1—C5—C6	96.2 (4)	N2—S2—C22—C23	47.1 (4)
O2—S1—C5—C4	33.4 (4)	C21—C22—C23—C24	−0.8 (7)
O1—S1—C5—C4	164.1 (4)	S2—C22—C23—C24	178.1 (4)
N1—S1—C5—C4	−80.0 (4)	C22—C23—C24—C19	0.5 (8)
C4—C5—C6—C7	0.7 (8)	C20—C19—C24—C23	0.3 (8)
S1—C5—C6—C7	−175.6 (4)	C18—C19—C24—C23	178.7 (5)
C3—C2—C7—C6	−2.1 (9)	C30—C25—C26—C27	−1.5 (8)
C1—C2—C7—C6	176.1 (6)	C25—C26—C27—C28	1.5 (8)
C5—C6—C7—C2	0.7 (9)	C26—C27—C28—C29	−0.4 (7)
C13—C8—C9—C10	−1.0 (9)	C26—C27—C28—C31	−177.4 (4)
C8—C9—C10—C11	0.6 (8)	C27—C28—C29—C30	−0.8 (7)
C9—C10—C11—C12	−0.9 (7)	C31—C28—C29—C30	176.2 (4)
C9—C10—C11—C14	176.8 (5)	C26—C25—C30—C29	0.4 (8)
C10—C11—C12—C13	1.6 (8)	C28—C29—C30—C25	0.8 (8)
C14—C11—C12—C13	−176.2 (5)	C27—C28—C31—C32	102.0 (5)
C11—C12—C13—C8	−2.0 (9)	C29—C28—C31—C32	−74.9 (6)
C9—C8—C13—C12	1.7 (9)	S2—N2—C32—C33	−80.4 (5)
C10—C11—C14—C15	106.8 (5)	S2—N2—C32—C31	155.2 (3)
C12—C11—C14—C15	−75.4 (5)	C28—C31—C32—N2	−55.8 (5)
S1—N1—C15—C16	−108.6 (4)	C28—C31—C32—C33	177.8 (4)
S1—N1—C15—C14	130.1 (4)	C34—O7—C33—O8	2.2 (9)
C11—C14—C15—N1	−75.1 (5)	C34—O7—C33—C32	−179.3 (5)
C11—C14—C15—C16	164.0 (4)	N2—C32—C33—O8	177.5 (5)
C17—O3—C16—O4	0.5 (8)	C31—C32—C33—O8	−58.5 (7)
C17—O3—C16—C15	178.4 (4)	N2—C32—C33—O7	−1.0 (6)
N1—C15—C16—O4	−18.8 (7)	C31—C32—C33—O7	123.0 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5	0.86	2.04	2.844 (5)	155
N2—H2···O2ⁱ	0.86	2.18	2.938 (5)	146
C21—H21···O4	0.93	2.68	3.494 (6)	146
C30—H30···O1ⁱⁱ	0.93	2.68	3.416 (6)	137
C9—H9···O8ⁱⁱⁱ	0.93	2.67	3.521 (7)	153

Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z; (iii) −x+2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₉NO₄S
M_r	333.39
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	7.5812 (4), 11.6107 (7), 37.659 (2)
V (Å³)	3314.8 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.29 × 0.24 × 0.09

Data collection
Diffractometer	Bruker APEX area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.938, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	17577, 5844, 5517
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.078, 0.172, 1.05
No. of reflections	5844
No. of parameters	419
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.36
Absolute structure	Flack (1983), 2489 Friedel pairs
Absolute structure parameter	−0.03 (1)

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2002), SHELXL97.