N,N'-[(1S,2S)-Cyclo-hexane-1,2-di-yl]bis-(4-methyl-benzene-sulfonamide).

In the title compound, C(20)H(26)N(2)O(4)S(2), the cyclo-hexane ring has a chair conformation. The two chiral C atoms are in S configurations. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains propagating in [001]. Weak inter-molecular C-H⋯O hydrogen bonds further stabilize the crystal packing.

Related literature

For the preparation of the title compound, see: Guo et al. (1997 ▶). For asymmetric catalysis, see: Ackermann et al. (2003 ▶); Bisai et al. (2005 ▶); Costa et al. (2005 ▶); Schwarz et al. (2010 ▶). For the crystal structures of racemates of the title compound, see: Nieger et al. (2004 ▶); Pritchett et al. (1999 ▶); Tasker et al. (2005 ▶).

Experimental

Crystal data

C20H26N2O4S2

M = 422.55

Orthorhombic,

a = 11.5704 (14) Å

b = 12.2585 (15) Å

c = 15.3757 (19) Å

V = 2180.8 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 296 K

0.75 × 0.65 × 0.32 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.822, T max = 0.918

9486 measured reflections

4196 independent reflections

3748 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.094

S = 1.00

4196 reflections

256 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 1706 Friedel pairs

Flack parameter: 0.07 (7)

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia,1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811012372/cv5062sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012372/cv5062Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H26N2O4S2	F(000) = 896
Mr = 422.55	Dx = 1.287 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5610 reflections
a = 11.5704 (14) Å	θ = 2.2–27.4°
b = 12.2585 (15) Å	µ = 0.27 mm−1
c = 15.3757 (19) Å	T = 296 K
V = 2180.8 (5) Å3	Chunk, yellow
Z = 4	0.75 × 0.65 × 0.32 mm

Bruker SMART CCD diffractometer	4196 independent reflections
Radiation source: fine-focus sealed tube	3748 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.822, Tmax = 0.918	k = −15→7
9486 measured reflections	l = −18→17

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.035	w = 1/[σ2(Fo2) + (0.0445P)2 + 0.4906P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.094	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.18 e Å−3
4196 reflections	Δρmin = −0.24 e Å−3
256 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0129 (10)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1706 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.07 (7)

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.

	x	y	z	Uiso*/Ueq
S2	0.67936 (6)	0.34616 (4)	0.33373 (4)	0.05778 (17)
S1	0.62809 (5)	0.40875 (4)	0.66645 (3)	0.05630 (16)
C14	0.54709 (19)	0.41739 (18)	0.34420 (13)	0.0522 (5)
O1	0.66322 (17)	0.40834 (14)	0.75630 (9)	0.0696 (5)
O4	0.6663 (2)	0.24457 (14)	0.37717 (13)	0.0815 (6)
C7	0.4973 (2)	0.48007 (17)	0.65910 (13)	0.0546 (5)
O3	0.70891 (17)	0.34735 (14)	0.24292 (10)	0.0691 (5)
N2	0.77908 (17)	0.41378 (18)	0.38123 (10)	0.0600 (5)
H102	0.8017	0.4755	0.3500	0.090*
N1	0.72602 (17)	0.47945 (16)	0.61697 (10)	0.0553 (5)
H101	0.7469	0.5406	0.6526	0.083*
O2	0.61429 (19)	0.30761 (13)	0.62249 (11)	0.0717 (5)
C1	0.71703 (19)	0.49569 (17)	0.52189 (12)	0.0486 (5)
H1	0.6373	0.4812	0.5038	0.058*
C10	0.2880 (2)	0.5933 (2)	0.65482 (15)	0.0641 (6)
C13	0.1751 (3)	0.6529 (3)	0.6547 (2)	0.0824 (8)
H13A	0.1154	0.6058	0.6764	0.124*
H13B	0.1565	0.6749	0.5964	0.124*
H13C	0.1808	0.7163	0.6911	0.124*
C19	0.5374 (2)	0.5203 (2)	0.30984 (16)	0.0624 (6)
H19	0.6004	0.5527	0.2825	0.075*
C11	0.2962 (2)	0.4872 (2)	0.62491 (19)	0.0752 (7)
H11	0.2306	0.4529	0.6030	0.090*
C8	0.4911 (2)	0.5865 (2)	0.68795 (18)	0.0765 (7)
H8	0.5567	0.6212	0.7093	0.092*
C2	0.7466 (3)	0.6124 (2)	0.50033 (16)	0.0815 (9)
H2A	0.6980	0.6607	0.5345	0.098*
H2B	0.7301	0.6258	0.4394	0.098*
C6	0.7972 (2)	0.4147 (2)	0.47615 (13)	0.0631 (6)
H6	0.7820	0.3414	0.4989	0.076*
C18	0.4338 (2)	0.5754 (2)	0.31602 (18)	0.0728 (7)
H18	0.4279	0.6455	0.2933	0.087*
C12	0.3992 (3)	0.4310 (2)	0.62680 (17)	0.0719 (7)
H12	0.4025	0.3597	0.6062	0.086*
C17	0.3394 (2)	0.5287 (2)	0.35501 (17)	0.0723 (7)
C15	0.4543 (3)	0.3685 (2)	0.38376 (17)	0.0733 (7)
H15	0.4605	0.2985	0.4067	0.088*
C20	0.2257 (3)	0.5907 (3)	0.3615 (2)	0.1059 (11)
H20A	0.2108	0.6088	0.4212	0.159*
H20B	0.1641	0.5460	0.3396	0.159*
H20C	0.2305	0.6564	0.3277	0.159*
C9	0.3878 (3)	0.6408 (2)	0.6850 (2)	0.0810 (8)
H9	0.3850	0.7128	0.7041	0.097*
C16	0.3510 (3)	0.4257 (3)	0.38880 (19)	0.0850 (8)
H16	0.2878	0.3933	0.4159	0.102*
C5	0.9229 (3)	0.4441 (5)	0.4944 (2)	0.1246 (19)
H5A	0.9394	0.4311	0.5554	0.149*
H5B	0.9727	0.3968	0.4604	0.149*
C4	0.9504 (3)	0.5625 (6)	0.4727 (2)	0.156 (3)
H4A	1.0295	0.5782	0.4892	0.187*
H4B	0.9435	0.5733	0.4104	0.187*
C3	0.8719 (4)	0.6387 (4)	0.5182 (2)	0.1297 (18)
H3A	0.8881	0.7126	0.4992	0.156*
H3B	0.8861	0.6348	0.5803	0.156*

	U11	U22	U33	U12	U13	U23
S2	0.0767 (4)	0.0523 (3)	0.0444 (3)	0.0109 (3)	0.0052 (3)	−0.0021 (2)
S1	0.0786 (4)	0.0508 (3)	0.0395 (2)	−0.0039 (3)	0.0075 (3)	0.0023 (2)
C14	0.0620 (13)	0.0541 (11)	0.0406 (10)	−0.0011 (10)	−0.0020 (9)	−0.0021 (10)
O1	0.0994 (13)	0.0680 (9)	0.0414 (8)	−0.0018 (10)	0.0051 (8)	0.0113 (7)
O4	0.1114 (16)	0.0534 (9)	0.0798 (12)	0.0169 (10)	0.0114 (11)	0.0073 (8)
C7	0.0707 (14)	0.0495 (10)	0.0437 (11)	−0.0136 (10)	0.0092 (11)	−0.0052 (9)
O3	0.0919 (13)	0.0705 (10)	0.0449 (8)	0.0055 (10)	0.0063 (8)	−0.0122 (7)
N2	0.0655 (12)	0.0763 (12)	0.0382 (9)	0.0112 (11)	0.0029 (8)	0.0005 (9)
N1	0.0646 (11)	0.0676 (11)	0.0337 (8)	−0.0030 (9)	0.0017 (8)	0.0045 (8)
O2	0.0989 (14)	0.0533 (8)	0.0631 (10)	0.0004 (9)	0.0087 (10)	−0.0038 (8)
C1	0.0517 (11)	0.0612 (11)	0.0330 (9)	0.0032 (9)	−0.0022 (8)	0.0039 (9)
C10	0.0732 (15)	0.0639 (13)	0.0551 (13)	−0.0078 (12)	0.0077 (11)	0.0031 (11)
C13	0.0744 (17)	0.0878 (18)	0.085 (2)	−0.0004 (15)	0.0022 (15)	0.0123 (16)
C19	0.0597 (13)	0.0589 (13)	0.0687 (15)	−0.0012 (11)	0.0004 (11)	0.0099 (11)
C11	0.0691 (17)	0.0690 (15)	0.0875 (18)	−0.0214 (14)	−0.0050 (15)	−0.0062 (14)
C8	0.0723 (17)	0.0602 (14)	0.097 (2)	−0.0060 (13)	−0.0110 (15)	−0.0275 (14)
C2	0.130 (3)	0.0718 (16)	0.0428 (12)	−0.0146 (16)	−0.0041 (14)	0.0086 (11)
C6	0.0666 (14)	0.0855 (15)	0.0373 (10)	0.0252 (13)	0.0002 (9)	0.0033 (11)
C18	0.0702 (16)	0.0680 (15)	0.0803 (18)	0.0080 (13)	−0.0010 (13)	0.0064 (13)
C12	0.0838 (18)	0.0548 (13)	0.0771 (16)	−0.0185 (13)	0.0036 (14)	−0.0131 (12)
C17	0.0653 (15)	0.0912 (18)	0.0604 (15)	0.0078 (14)	−0.0004 (12)	−0.0065 (13)
C15	0.0838 (19)	0.0674 (15)	0.0688 (16)	−0.0057 (14)	0.0116 (14)	0.0111 (12)
C20	0.0752 (19)	0.132 (3)	0.110 (2)	0.024 (2)	0.0081 (19)	−0.007 (2)
C9	0.0863 (19)	0.0603 (14)	0.096 (2)	−0.0028 (14)	−0.0098 (16)	−0.0269 (14)
C16	0.0695 (18)	0.110 (2)	0.0755 (18)	−0.0133 (17)	0.0182 (14)	0.0057 (17)
C5	0.063 (2)	0.257 (6)	0.0537 (16)	0.050 (3)	−0.0093 (14)	−0.016 (3)
C4	0.079 (2)	0.334 (8)	0.0541 (17)	−0.088 (4)	0.0068 (16)	−0.014 (3)
C3	0.168 (4)	0.169 (4)	0.0517 (16)	−0.107 (3)	0.013 (2)	−0.004 (2)

S2—O4	1.4212 (19)	C11—H11	0.9300
S2—O3	1.4376 (16)	C8—C9	1.369 (4)
S2—N2	1.597 (2)	C8—H8	0.9300
S2—C14	1.769 (2)	C2—C3	1.511 (6)
S1—O2	1.4212 (17)	C2—H2A	0.9700
S1—O1	1.4401 (16)	C2—H2B	0.9700
S1—N1	1.6166 (19)	C6—C5	1.524 (5)
S1—C7	1.751 (3)	C6—H6	0.9800
C14—C15	1.372 (3)	C18—C17	1.371 (4)
C14—C19	1.372 (3)	C18—H18	0.9300
C7—C12	1.377 (3)	C12—H12	0.9300
C7—C8	1.380 (3)	C17—C16	1.371 (4)
N2—C6	1.475 (3)	C17—C20	1.523 (4)
N2—H102	0.9334	C15—C16	1.389 (4)
N1—C1	1.479 (2)	C15—H15	0.9300
N1—H101	0.9589	C20—H20A	0.9600
C1—C2	1.508 (3)	C20—H20B	0.9600
C1—C6	1.530 (3)	C20—H20C	0.9600
C1—H1	0.9800	C9—H9	0.9300
C10—C9	1.373 (4)	C16—H16	0.9300
C10—C11	1.384 (4)	C5—C4	1.523 (7)
C10—C13	1.497 (4)	C5—H5A	0.9700
C13—H13A	0.9600	C5—H5B	0.9700
C13—H13B	0.9600	C4—C3	1.478 (7)
C13—H13C	0.9600	C4—H4A	0.9700
C19—C18	1.379 (3)	C4—H4B	0.9700
C19—H19	0.9300	C3—H3A	0.9700
C11—C12	1.376 (4)	C3—H3B	0.9700
O4—S2—O3	119.38 (11)	C1—C2—H2B	109.1
O4—S2—N2	108.47 (12)	C3—C2—H2B	109.1
O3—S2—N2	105.48 (11)	H2A—C2—H2B	107.9
O4—S2—C14	107.31 (12)	N2—C6—C5	108.6 (2)
O3—S2—C14	106.81 (10)	N2—C6—C1	111.93 (17)
N2—S2—C14	109.09 (10)	C5—C6—C1	109.9 (3)
O2—S1—O1	119.01 (10)	N2—C6—H6	108.8
O2—S1—N1	108.82 (11)	C5—C6—H6	108.8
O1—S1—N1	104.81 (10)	C1—C6—H6	108.8
O2—S1—C7	107.92 (12)	C17—C18—C19	121.2 (3)
O1—S1—C7	107.91 (11)	C17—C18—H18	119.4
N1—S1—C7	107.92 (10)	C19—C18—H18	119.4
C15—C14—C19	120.6 (2)	C11—C12—C7	120.2 (2)
C15—C14—S2	120.10 (18)	C11—C12—H12	119.9
C19—C14—S2	119.28 (18)	C7—C12—H12	119.9
C12—C7—C8	119.1 (2)	C16—C17—C18	118.2 (3)
C12—C7—S1	121.16 (18)	C16—C17—C20	121.3 (3)
C8—C7—S1	119.76 (19)	C18—C17—C20	120.6 (3)
C6—N2—S2	124.00 (18)	C14—C15—C16	118.5 (2)
C6—N2—H102	117.6	C14—C15—H15	120.7
S2—N2—H102	112.8	C16—C15—H15	120.7
C1—N1—S1	119.21 (15)	C17—C20—H20A	109.5
C1—N1—H101	118.5	C17—C20—H20B	109.5
S1—N1—H101	109.1	H20A—C20—H20B	109.5
N1—C1—C2	109.21 (18)	C17—C20—H20C	109.5
N1—C1—C6	108.92 (17)	H20A—C20—H20C	109.5
C2—C1—C6	112.2 (2)	H20B—C20—H20C	109.5
N1—C1—H1	108.8	C8—C9—C10	122.6 (2)
C2—C1—H1	108.8	C8—C9—H9	118.7
C6—C1—H1	108.8	C10—C9—H9	118.7
C9—C10—C11	117.0 (3)	C17—C16—C15	121.9 (3)
C9—C10—C13	121.8 (2)	C17—C16—H16	119.1
C11—C10—C13	121.2 (3)	C15—C16—H16	119.1
C10—C13—H13A	109.5	C4—C5—C6	112.6 (3)
C10—C13—H13B	109.5	C4—C5—H5A	109.1
H13A—C13—H13B	109.5	C6—C5—H5A	109.1
C10—C13—H13C	109.5	C4—C5—H5B	109.1
H13A—C13—H13C	109.5	C6—C5—H5B	109.1
H13B—C13—H13C	109.5	H5A—C5—H5B	107.8
C14—C19—C18	119.6 (2)	C3—C4—C5	111.8 (3)
C14—C19—H19	120.2	C3—C4—H4A	109.3
C18—C19—H19	120.2	C5—C4—H4A	109.3
C12—C11—C10	121.5 (2)	C3—C4—H4B	109.3
C12—C11—H11	119.2	C5—C4—H4B	109.3
C10—C11—H11	119.2	H4A—C4—H4B	107.9
C9—C8—C7	119.6 (2)	C4—C3—C2	111.6 (3)
C9—C8—H8	120.2	C4—C3—H3A	109.3
C7—C8—H8	120.2	C2—C3—H3A	109.3
C1—C2—C3	112.3 (3)	C4—C3—H3B	109.3
C1—C2—H2A	109.1	C2—C3—H3B	109.3
C3—C2—H2A	109.1	H3A—C3—H3B	108.0
O4—S2—C14—C15	−4.0 (2)	C6—C1—C2—C3	−54.0 (3)
O3—S2—C14—C15	125.1 (2)	S2—N2—C6—C5	155.9 (3)
N2—S2—C14—C15	−121.3 (2)	S2—N2—C6—C1	−82.5 (3)
O4—S2—C14—C19	178.14 (19)	N1—C1—C6—N2	170.8 (2)
O3—S2—C14—C19	−52.7 (2)	C2—C1—C6—N2	−68.2 (3)
N2—S2—C14—C19	60.8 (2)	N1—C1—C6—C5	−68.4 (3)
O2—S1—C7—C12	8.9 (2)	C2—C1—C6—C5	52.6 (3)
O1—S1—C7—C12	−120.9 (2)	C14—C19—C18—C17	−0.9 (4)
N1—S1—C7—C12	126.37 (19)	C10—C11—C12—C7	0.1 (4)
O2—S1—C7—C8	−172.6 (2)	C8—C7—C12—C11	−1.1 (4)
O1—S1—C7—C8	57.6 (2)	S1—C7—C12—C11	177.3 (2)
N1—S1—C7—C8	−55.2 (2)	C19—C18—C17—C16	0.8 (4)
O4—S2—N2—C6	−37.9 (2)	C19—C18—C17—C20	179.9 (3)
O3—S2—N2—C6	−166.88 (18)	C19—C14—C15—C16	−0.5 (4)
C14—S2—N2—C6	78.7 (2)	S2—C14—C15—C16	−178.3 (2)
O2—S1—N1—C1	51.2 (2)	C7—C8—C9—C10	0.6 (5)
O1—S1—N1—C1	179.49 (16)	C11—C10—C9—C8	−1.6 (4)
C7—S1—N1—C1	−65.69 (18)	C13—C10—C9—C8	178.0 (3)
S1—N1—C1—C2	137.8 (2)	C18—C17—C16—C15	−0.5 (4)
S1—N1—C1—C6	−99.4 (2)	C20—C17—C16—C15	−179.7 (3)
C15—C14—C19—C18	0.7 (4)	C14—C15—C16—C17	0.4 (4)
S2—C14—C19—C18	178.6 (2)	N2—C6—C5—C4	69.8 (3)
C9—C10—C11—C12	1.2 (4)	C1—C6—C5—C4	−53.0 (3)
C13—C10—C11—C12	−178.4 (3)	C6—C5—C4—C3	55.0 (4)
C12—C7—C8—C9	0.8 (4)	C5—C4—C3—C2	−54.5 (4)
S1—C7—C8—C9	−177.7 (2)	C1—C2—C3—C4	54.7 (4)
N1—C1—C2—C3	66.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H101···O3i	0.96	2.02	2.971 (3)	171
N2—H102···O1ii	0.93	2.07	2.982 (3)	167
C11—H11···O4iii	0.93	2.55	3.214 (3)	129
C9—H9···O1iv	0.93	2.54	3.452 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H101⋯O3i	0.96	2.02	2.971 (3)	171
N2—H102⋯O1ii	0.93	2.07	2.982 (3)	167
C11—H11⋯O4iii	0.93	2.55	3.214 (3)	129
C9—H9⋯O1iv	0.93	2.54	3.452 (3)	169

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .