N-[(3RS)-3-(4-Chloro­phen­yl)heptano­yl]bornane-10,2-sultam

Cao, X.-F.; Yin, J.; Yu, G.-A.; Liu, S.-H.

doi:10.1107/S1600536805041176

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N-[(3RS)-3-(4-Chlorophenyl)heptanoyl]bornane-10,2-sultam

X.-F. Cao, J. Yin, G.-A. Yu and S.-H. Liu

In the title compound, C₂₃H₃₂ClNO₃S, molecules are linked via C—H

N/O interactions, forming two-dimensional sheets parallel to the (100) plane.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805041176/ob6600sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805041176/ob6600Isup2.hkl Contains datablock I

CCDC reference: 296626

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.005 Å
R factor = 0.051
wR factor = 0.120
Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C21
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

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           26.00
           From the CIF: _reflns_number_total               4179
           Count of symmetry unique reflns         2417
           Completeness (_total/calc)            172.90%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1762
           Fraction of Friedel pairs measured     0.729
           Are heavy atom types Z>Si present        yes

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The readily available enantiomers of bornane-10,2-sultam serve as efficient, versatile and practical chiral auxiliaries (Oppolzer, 1990), and we have focused our attention on this matter. In this paper, we present the X-ray crystallographic analysis of the title compound, (I).

In (I), the six-membered ring of sultam exhibits a boat form (Fig. 1). The C9/C4/C5/C6 and C6/C7/C8/C9 planes form a dihedral angle of 111.1 (1)°. The C3/C6/C9 plane forms almost equal dihedral angles with the above planes [124.1 (1) and 124.7 (1)°, respectively]. The molecules are linked via C—H···N/O interactions (Table 2) along the b and c axes, forming two-dimensional sheets parallel to the (100) plane (Fig. 2).

Experimental top

Compound (I) was synthesized from (-)-sultam and cinnamic chloride (Huang et al., 1999). Crystals suitable for X-ray data collection were obtained by slow evaporation of a methylene chloride solution at 292 K.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); 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, 2001); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. View of the molecule of (I), showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The molecular packing of (I), viewed along the b axis. Dashed lines indicate C—H···O/N interactions. H atoms not involved in these interactions have been omitted for clarity.

N-[(3RS)-3-(4-Chlorophenyl)heptoyl]bornane-10,2-sultam top

Crystal data top

C₂₃H₃₂ClNO₃S	F(000) = 468
M_r = 438.01	D_x = 1.261 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1773 reflections
a = 9.2278 (13) Å	θ = 2.2–21.7°
b = 9.6269 (14) Å	µ = 0.28 mm⁻¹
c = 13.1720 (19) Å	T = 292 K
β = 99.736 (2)°	Block, colorless
V = 1153.3 (3) Å³	0.30 × 0.20 × 0.10 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	3478 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.025
Graphite monochromator	θ_max = 26.0°, θ_min = 2.2°
ϕ and ω scans	h = −11→10
6334 measured reflections	k = −11→11
4179 independent reflections	l = −16→13

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)] = 0.051	H-atom parameters constrained
wR(F²) = 0.120	w = 1/[σ²(F_o²) + (0.0545P)² + 0.074P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
4179 reflections	Δρ_max = 0.18 e Å⁻³
265 parameters	Δρ_min = −0.19 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1762 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.08 (8)

Crystal data top

C₂₃H₃₂ClNO₃S	V = 1153.3 (3) Å³
M_r = 438.01	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.2278 (13) Å	µ = 0.28 mm⁻¹
b = 9.6269 (14) Å	T = 292 K
c = 13.1720 (19) Å	0.30 × 0.20 × 0.10 mm
β = 99.736 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3478 reflections with I > 2σ(I)
6334 measured reflections	R_int = 0.025
4179 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.120	Δρ_max = 0.18 e Å⁻³
S = 1.04	Δρ_min = −0.19 e Å⁻³
4179 reflections	Absolute structure: Flack (1983), 1762 Friedel pairs
265 parameters	Absolute structure parameter: 0.08 (8)
1 restraint

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	0.2483 (4)	0.8851 (5)	0.0375 (3)	0.0788 (12)
H1A	0.2050	0.9158	0.0949	0.118*
H1B	0.1726	0.8714	−0.0212	0.118*
H1C	0.3164	0.9539	0.0217	0.118*
C2	0.3824 (4)	0.6945 (7)	−0.0335 (3)	0.0951 (14)
H2A	0.4484	0.7611	−0.0552	0.143*
H2B	0.2990	0.6822	−0.0872	0.143*
H2C	0.4323	0.6074	−0.0194	0.143*
C3	0.3301 (4)	0.7475 (4)	0.0650 (3)	0.0581 (9)
C4	0.3622 (4)	0.5208 (4)	0.1407 (4)	0.0715 (11)
H4A	0.3679	0.4652	0.0801	0.086*
H4B	0.3414	0.4608	0.1956	0.086*
C5	0.5053 (4)	0.6058 (5)	0.1746 (3)	0.0761 (12)
H5A	0.5461	0.5885	0.2463	0.091*
H5B	0.5786	0.5837	0.1323	0.091*
C6	0.4530 (4)	0.7564 (4)	0.1583 (3)	0.0623 (10)
H6	0.5314	0.8216	0.1493	0.075*
C7	0.3695 (3)	0.7968 (4)	0.2446 (3)	0.0601 (9)
H7A	0.3412	0.8940	0.2403	0.072*
H7B	0.4271	0.7784	0.3119	0.072*
C8	0.2342 (3)	0.7008 (4)	0.2223 (2)	0.0471 (7)
H8	0.2419	0.6279	0.2748	0.056*
C9	0.2476 (3)	0.6359 (3)	0.1173 (3)	0.0485 (8)
C10	0.0958 (3)	0.5911 (4)	0.0643 (3)	0.0604 (9)
H10A	0.0810	0.4931	0.0761	0.073*
H10B	0.0850	0.6068	−0.0094	0.073*
C11	0.0484 (3)	0.8367 (4)	0.2951 (2)	0.0489 (8)
C12	−0.1083 (3)	0.8888 (4)	0.2821 (3)	0.0598 (9)
H12A	−0.1742	0.8097	0.2767	0.072*
H12B	−0.1302	0.9406	0.2181	0.072*
C13	−0.1377 (4)	0.9815 (4)	0.3704 (2)	0.0540 (8)
H13	−0.0594	1.0514	0.3814	0.065*
C14	−0.2833 (4)	1.0598 (5)	0.3379 (3)	0.0710 (11)
H14A	−0.2864	1.0957	0.2687	0.085*
H14B	−0.3640	0.9947	0.3358	0.085*
C15	−0.3062 (5)	1.1798 (6)	0.4090 (3)	0.0774 (11)
H15A	−0.3306	1.1418	0.4722	0.093*
H15B	−0.2143	1.2300	0.4267	0.093*
C16	−0.4202 (6)	1.2771 (6)	0.3662 (4)	0.0999 (16)
H16A	−0.5125	1.2271	0.3503	0.120*
H16B	−0.3972	1.3127	0.3019	0.120*
C17	−0.4410 (6)	1.3972 (5)	0.4337 (3)	0.0923 (14)
H17A	−0.4494	1.3641	0.5012	0.138*
H17B	−0.5290	1.4464	0.4050	0.138*
H17C	−0.3581	1.4585	0.4383	0.138*
C18	−0.1329 (3)	0.9057 (4)	0.4709 (3)	0.0501 (8)
C19	−0.0511 (4)	0.9582 (4)	0.5612 (3)	0.0644 (10)
H19	0.0021	1.0397	0.5586	0.077*
C20	−0.0473 (5)	0.8922 (5)	0.6545 (3)	0.0742 (11)
H20	0.0091	0.9284	0.7138	0.089*
C21	−0.1260 (5)	0.7740 (5)	0.6594 (3)	0.0683 (11)
C22	−0.2047 (4)	0.7178 (4)	0.5726 (3)	0.0692 (11)
H22	−0.2558	0.6351	0.5760	0.083*
C23	−0.2083 (4)	0.7845 (4)	0.4794 (3)	0.0624 (9)
H23	−0.2635	0.7461	0.4205	0.075*
Cl1	−0.12319 (16)	0.69322 (17)	0.77858 (8)	0.1100 (5)
N1	0.0880 (2)	0.7672 (3)	0.21134 (18)	0.0446 (6)
O1	−0.1025 (3)	0.7958 (3)	0.04964 (18)	0.0694 (7)
O2	−0.1295 (2)	0.6051 (3)	0.1631 (2)	0.0637 (7)
O3	0.1381 (2)	0.8544 (3)	0.37085 (17)	0.0699 (7)
S1	−0.03484 (7)	0.69304 (9)	0.11799 (5)	0.04449 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.075 (2)	0.081 (3)	0.083 (3)	−0.006 (2)	0.022 (2)	0.032 (2)
C2	0.083 (3)	0.143 (4)	0.067 (2)	0.000 (4)	0.034 (2)	−0.004 (4)
C3	0.0535 (19)	0.075 (3)	0.0492 (18)	−0.0005 (17)	0.0175 (15)	0.0043 (16)
C4	0.060 (2)	0.057 (2)	0.100 (3)	0.0092 (19)	0.020 (2)	−0.002 (2)
C5	0.047 (2)	0.100 (3)	0.082 (3)	0.019 (2)	0.0126 (19)	0.004 (3)
C6	0.0403 (18)	0.078 (3)	0.070 (2)	−0.0116 (18)	0.0147 (16)	−0.002 (2)
C7	0.0434 (17)	0.075 (3)	0.061 (2)	−0.0107 (17)	0.0064 (15)	−0.0119 (19)
C8	0.0394 (14)	0.0575 (19)	0.0436 (15)	0.0041 (18)	0.0050 (12)	0.0047 (18)
C9	0.0401 (16)	0.0507 (19)	0.0545 (19)	0.0034 (14)	0.0070 (14)	−0.0064 (15)
C10	0.0508 (19)	0.061 (2)	0.069 (2)	−0.0031 (17)	0.0097 (17)	−0.0213 (19)
C11	0.0481 (17)	0.060 (2)	0.0405 (17)	−0.0053 (16)	0.0114 (14)	−0.0029 (15)
C12	0.0504 (19)	0.076 (3)	0.054 (2)	0.0059 (18)	0.0096 (15)	−0.0089 (18)
C13	0.0574 (19)	0.054 (2)	0.054 (2)	−0.0013 (16)	0.0173 (16)	−0.0109 (17)
C14	0.076 (3)	0.080 (3)	0.059 (2)	0.020 (2)	0.0159 (19)	0.001 (2)
C15	0.085 (2)	0.081 (3)	0.068 (2)	0.022 (3)	0.0179 (19)	0.000 (3)
C16	0.113 (4)	0.096 (4)	0.087 (3)	0.034 (3)	0.006 (3)	−0.009 (3)
C17	0.119 (3)	0.069 (3)	0.087 (3)	0.024 (3)	0.009 (3)	−0.003 (2)
C18	0.0442 (16)	0.050 (2)	0.058 (2)	0.0073 (16)	0.0138 (15)	−0.0114 (16)
C19	0.073 (2)	0.064 (2)	0.058 (2)	−0.0098 (19)	0.0163 (19)	−0.0172 (19)
C20	0.085 (3)	0.086 (3)	0.050 (2)	0.010 (3)	0.0065 (19)	−0.021 (2)
C21	0.084 (3)	0.066 (3)	0.059 (2)	0.019 (2)	0.023 (2)	−0.004 (2)
C22	0.085 (2)	0.054 (3)	0.072 (2)	−0.004 (2)	0.021 (2)	−0.001 (2)
C23	0.066 (2)	0.059 (2)	0.059 (2)	0.000 (2)	0.0046 (17)	−0.0117 (19)
Cl1	0.1659 (12)	0.1015 (9)	0.0667 (6)	0.0293 (11)	0.0313 (7)	0.0185 (8)
N1	0.0355 (12)	0.0528 (16)	0.0458 (14)	−0.0022 (12)	0.0081 (10)	−0.0065 (12)
O1	0.0736 (15)	0.0746 (18)	0.0527 (14)	0.0116 (14)	−0.0101 (12)	0.0034 (13)
O2	0.0509 (13)	0.0605 (16)	0.0809 (17)	−0.0127 (12)	0.0144 (12)	−0.0038 (13)
O3	0.0533 (13)	0.105 (2)	0.0488 (14)	0.0036 (14)	0.0027 (11)	−0.0200 (14)
S1	0.0395 (3)	0.0468 (4)	0.0455 (4)	−0.0012 (4)	0.0024 (3)	−0.0053 (4)

Geometric parameters (Å, º) top

C1—C3	1.537 (5)	C12—C13	1.526 (4)
C1—H1A	0.9600	C12—H12A	0.9700
C1—H1B	0.9600	C12—H12B	0.9700
C1—H1C	0.9600	C13—C18	1.506 (5)
C2—C3	1.546 (5)	C13—C14	1.537 (5)
C2—H2A	0.9600	C13—H13	0.9800
C2—H2B	0.9600	C14—C15	1.525 (6)
C2—H2C	0.9600	C14—H14A	0.9700
C3—C6	1.527 (5)	C14—H14B	0.9700
C3—C9	1.545 (5)	C15—C16	1.450 (6)
C4—C9	1.527 (5)	C15—H15A	0.9700
C4—C5	1.553 (5)	C15—H15B	0.9700
C4—H4A	0.9700	C16—C17	1.490 (6)
C4—H4B	0.9700	C16—H16A	0.9700
C5—C6	1.531 (6)	C16—H16B	0.9700
C5—H5A	0.9700	C17—H17A	0.9600
C5—H5B	0.9700	C17—H17B	0.9600
C6—C7	1.528 (5)	C17—H17C	0.9600
C6—H6	0.9800	C18—C23	1.372 (5)
C7—C8	1.541 (5)	C18—C19	1.392 (5)
C7—H7A	0.9700	C19—C20	1.378 (6)
C7—H7B	0.9700	C19—H19	0.9300
C8—N1	1.477 (4)	C20—C21	1.357 (6)
C8—C9	1.542 (4)	C20—H20	0.9300
C8—H8	0.9800	C21—C22	1.359 (5)
C9—C10	1.518 (4)	C21—Cl1	1.748 (4)
C10—S1	1.791 (3)	C22—C23	1.382 (5)
C10—H10A	0.9700	C22—H22	0.9300
C10—H10B	0.9700	C23—H23	0.9300
C11—O3	1.196 (3)	N1—S1	1.684 (2)
C11—N1	1.391 (4)	O1—S1	1.411 (2)
C11—C12	1.513 (4)	O2—S1	1.417 (2)

C3—C1—H1A	109.5	C11—C12—C13	113.4 (3)
C3—C1—H1B	109.5	C11—C12—H12A	108.9
H1A—C1—H1B	109.5	C13—C12—H12A	108.9
C3—C1—H1C	109.5	C11—C12—H12B	108.9
H1A—C1—H1C	109.5	C13—C12—H12B	108.9
H1B—C1—H1C	109.5	H12A—C12—H12B	107.7
C3—C2—H2A	109.5	C18—C13—C12	113.8 (3)
C3—C2—H2B	109.5	C18—C13—C14	112.2 (3)
H2A—C2—H2B	109.5	C12—C13—C14	109.5 (3)
C3—C2—H2C	109.5	C18—C13—H13	107.0
H2A—C2—H2C	109.5	C12—C13—H13	107.0
H2B—C2—H2C	109.5	C14—C13—H13	107.0
C6—C3—C1	114.2 (3)	C15—C14—C13	113.9 (3)
C6—C3—C9	92.0 (3)	C15—C14—H14A	108.8
C1—C3—C9	116.4 (3)	C13—C14—H14A	108.8
C6—C3—C2	113.5 (3)	C15—C14—H14B	108.8
C1—C3—C2	107.3 (4)	C13—C14—H14B	108.8
C9—C3—C2	113.1 (4)	H14A—C14—H14B	107.7
C9—C4—C5	101.6 (3)	C16—C15—C14	114.7 (3)
C9—C4—H4A	111.4	C16—C15—H15A	108.6
C5—C4—H4A	111.4	C14—C15—H15A	108.6
C9—C4—H4B	111.4	C16—C15—H15B	108.6
C5—C4—H4B	111.4	C14—C15—H15B	108.6
H4A—C4—H4B	109.3	H15A—C15—H15B	107.6
C6—C5—C4	103.1 (3)	C15—C16—C17	115.3 (4)
C6—C5—H5A	111.1	C15—C16—H16A	108.4
C4—C5—H5A	111.1	C17—C16—H16A	108.4
C6—C5—H5B	111.1	C15—C16—H16B	108.4
C4—C5—H5B	111.1	C17—C16—H16B	108.4
H5A—C5—H5B	109.1	H16A—C16—H16B	107.5
C3—C6—C7	102.3 (3)	C16—C17—H17A	109.5
C3—C6—C5	103.5 (3)	C16—C17—H17B	109.5
C7—C6—C5	108.8 (4)	H17A—C17—H17B	109.5
C3—C6—H6	113.7	C16—C17—H17C	109.5
C7—C6—H6	113.7	H17A—C17—H17C	109.5
C5—C6—H6	113.7	H17B—C17—H17C	109.5
C6—C7—C8	101.5 (3)	C23—C18—C19	116.6 (3)
C6—C7—H7A	111.5	C23—C18—C13	122.9 (3)
C8—C7—H7A	111.5	C19—C18—C13	120.5 (3)
C6—C7—H7B	111.5	C20—C19—C18	121.5 (4)
C8—C7—H7B	111.5	C20—C19—H19	119.2
H7A—C7—H7B	109.3	C18—C19—H19	119.2
N1—C8—C7	117.1 (3)	C21—C20—C19	119.7 (4)
N1—C8—C9	107.4 (2)	C21—C20—H20	120.1
C7—C8—C9	103.2 (2)	C19—C20—H20	120.1
N1—C8—H8	109.6	C20—C21—C22	120.6 (4)
C7—C8—H8	109.6	C20—C21—Cl1	119.3 (3)
C9—C8—H8	109.6	C22—C21—Cl1	120.2 (4)
C10—C9—C4	116.1 (3)	C21—C22—C23	119.4 (4)
C10—C9—C8	108.7 (2)	C21—C22—H22	120.3
C4—C9—C8	105.7 (3)	C23—C22—H22	120.3
C10—C9—C3	118.6 (3)	C18—C23—C22	122.1 (4)
C4—C9—C3	102.6 (3)	C18—C23—H23	118.9
C8—C9—C3	103.8 (3)	C22—C23—H23	118.9
C9—C10—S1	107.0 (2)	C11—N1—C8	119.3 (2)
C9—C10—H10A	110.3	C11—N1—S1	123.2 (2)
S1—C10—H10A	110.3	C8—N1—S1	112.3 (2)
C9—C10—H10B	110.3	O1—S1—O2	116.67 (16)
S1—C10—H10B	110.3	O1—S1—N1	109.84 (15)
H10A—C10—H10B	108.6	O2—S1—N1	109.53 (14)
O3—C11—N1	119.6 (3)	O1—S1—C10	112.78 (17)
O3—C11—C12	124.1 (3)	O2—S1—C10	110.01 (17)
N1—C11—C12	116.4 (3)	N1—S1—C10	96.06 (14)

C9—C4—C5—C6	−3.8 (4)	C11—C12—C13—C14	165.0 (3)
C1—C3—C6—C7	61.8 (4)	C18—C13—C14—C15	66.4 (4)
C9—C3—C6—C7	−58.4 (3)	C12—C13—C14—C15	−166.3 (3)
C2—C3—C6—C7	−174.8 (4)	C13—C14—C15—C16	164.1 (4)
C1—C3—C6—C5	174.9 (3)	C14—C15—C16—C17	−178.4 (4)
C9—C3—C6—C5	54.7 (3)	C12—C13—C18—C23	−49.7 (4)
C2—C3—C6—C5	−61.7 (5)	C14—C13—C18—C23	75.3 (4)
C4—C5—C6—C3	−33.2 (4)	C12—C13—C18—C19	131.1 (3)
C4—C5—C6—C7	75.1 (4)	C14—C13—C18—C19	−103.8 (4)
C3—C6—C7—C8	43.2 (4)	C23—C18—C19—C20	−0.5 (5)
C5—C6—C7—C8	−65.8 (3)	C13—C18—C19—C20	178.7 (3)
C6—C7—C8—N1	−126.1 (3)	C18—C19—C20—C21	−0.8 (6)
C6—C7—C8—C9	−8.4 (3)	C19—C20—C21—C22	2.2 (6)
C5—C4—C9—C10	170.1 (3)	C19—C20—C21—Cl1	−178.7 (3)
C5—C4—C9—C8	−69.4 (3)	C20—C21—C22—C23	−2.2 (6)
C5—C4—C9—C3	39.1 (4)	Cl1—C21—C22—C23	178.7 (3)
N1—C8—C9—C10	−31.2 (4)	C19—C18—C23—C22	0.4 (5)
C7—C8—C9—C10	−155.6 (3)	C13—C18—C23—C22	−178.7 (3)
N1—C8—C9—C4	−156.5 (3)	C21—C22—C23—C18	0.9 (6)
C7—C8—C9—C4	79.1 (3)	O3—C11—N1—C8	7.9 (5)
N1—C8—C9—C3	95.9 (3)	C12—C11—N1—C8	−173.7 (3)
C7—C8—C9—C3	−28.4 (3)	O3—C11—N1—S1	160.3 (3)
C6—C3—C9—C10	173.1 (3)	C12—C11—N1—S1	−21.3 (4)
C1—C3—C9—C10	54.7 (4)	C7—C8—N1—C11	−63.3 (4)
C2—C3—C9—C10	−70.2 (4)	C9—C8—N1—C11	−178.7 (3)
C6—C3—C9—C4	−57.5 (3)	C7—C8—N1—S1	141.5 (2)
C1—C3—C9—C4	−175.8 (3)	C9—C8—N1—S1	26.1 (3)
C2—C3—C9—C4	59.2 (4)	C11—N1—S1—O1	77.9 (3)
C6—C3—C9—C8	52.4 (3)	C8—N1—S1—O1	−128.0 (2)
C1—C3—C9—C8	−65.9 (4)	C11—N1—S1—O2	−51.4 (3)
C2—C3—C9—C8	169.1 (3)	C8—N1—S1—O2	102.7 (2)
C4—C9—C10—S1	142.2 (3)	C11—N1—S1—C10	−165.2 (3)
C8—C9—C10—S1	23.3 (4)	C8—N1—S1—C10	−11.1 (3)
C3—C9—C10—S1	−94.8 (3)	C9—C10—S1—O1	106.8 (3)
O3—C11—C12—C13	6.6 (5)	C9—C10—S1—O2	−121.0 (3)
N1—C11—C12—C13	−171.7 (3)	C9—C10—S1—N1	−7.7 (3)
C11—C12—C13—C18	−68.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O2	0.97	2.55	3.139 (5)	119
C1—H1A···N1	0.96	2.47	3.141 (4)	126
C20—H20···O2ⁱ	0.93	2.48	3.363 (5)	159
C10—H10A···O1ⁱⁱ	0.97	2.55	3.220 (4)	126

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

Experimental details

Crystal data
Chemical formula	C₂₃H₃₂ClNO₃S
M_r	438.01
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	292
a, b, c (Å)	9.2278 (13), 9.6269 (14), 13.1720 (19)
β (°)	99.736 (2)
V (Å³)	1153.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6334, 4179, 3478
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.120, 1.04
No. of reflections	4179
No. of parameters	265
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.19
Absolute structure	Flack (1983), 1762 Friedel pairs
Absolute structure parameter	0.08 (8)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXTL.

Selected geometric parameters (Å, º) top

C8—N1	1.477 (4)	C21—Cl1	1.748 (4)
C10—S1	1.791 (3)	N1—S1	1.684 (2)
C11—O3	1.196 (3)	O1—S1	1.411 (2)
C11—N1	1.391 (4)	O2—S1	1.417 (2)

C9—C10—S1	107.0 (2)	N1—S1—C10	96.06 (14)

C9—C4—C5—C6	−3.8 (4)	C12—C13—C18—C23	−49.7 (4)
C6—C7—C8—C9	−8.4 (3)	C14—C13—C18—C19	−103.8 (4)
N1—C8—C9—C10	−31.2 (4)	C9—C8—N1—S1	26.1 (3)
C8—C9—C10—S1	23.3 (4)	C8—N1—S1—C10	−11.1 (3)
C11—C12—C13—C14	165.0 (3)	C9—C10—S1—N1	−7.7 (3)
C14—C15—C16—C17	−178.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O2	0.97	2.55	3.139 (5)	119
C1—H1A···N1	0.96	2.47	3.141 (4)	126
C20—H20···O2ⁱ	0.93	2.48	3.363 (5)	159
C10—H10A···O1ⁱⁱ	0.97	2.55	3.220 (4)	126

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

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