1,4-Ditosyl-1,4-diazepane.

In the title compound, C(19)H(24)N(2)O(4)S(2), the dihedral angle formed by the benzene rings is 82.88 (7)°, and the mol-ecular conformation is enforced by weak intra-molecular C-H⋯O contacts. Two C atoms of the 1,4-diazepane ring are disordered over two sets of sites with a refined occupancy ratio of 0.534 (13):0.466 (13). In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O inter-actions into chains parallel to the a axis.

Related literature

For related structures, see: Romba et al. (2002 ▶). For the biological activity of heterocyclic compounds, see: Xu et al. (2006 ▶); Yu et al. (2009 ▶).

Experimental

Crystal data

C19H24N2O4S2

M = 408.52

Orthorhombic,

a = 6.3407 (13) Å

b = 10.367 (2) Å

c = 30.516 (6) Å

V = 2005.9 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 173 K

0.20 × 0.20 × 0.10 mm

Data collection

Rigaku Mercury CCD/AFC diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ▶) T min = 0.944, T max = 0.971

11747 measured reflections

3531 independent reflections

3430 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.083

S = 1.07

3531 reflections

265 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 1442 Friedel pairs

Flack parameter: −0.03 (7)

Data collection: CrystalClear (Rigaku, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812020958/rz2746sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020958/rz2746Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812020958/rz2746Isup3.cml

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

C19H24N2O4S2	F(000) = 864
Mr = 408.52	Dx = 1.353 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7269 reflections
a = 6.3407 (13) Å	θ = 1.7–27.5°
b = 10.367 (2) Å	µ = 0.29 mm−1
c = 30.516 (6) Å	T = 173 K
V = 2005.9 (7) Å3	Block, colourless
Z = 4	0.20 × 0.20 × 0.10 mm

Rigaku Mercury CCD/AFC diffractometer	3531 independent reflections
Radiation source: Sealed Tube	3430 reflections with I > 2σ(I)
Graphite Monochromator monochromator	Rint = 0.035
φ and ω scans	θmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	h = −7→7
Tmin = 0.944, Tmax = 0.971	k = −8→12
11747 measured reflections	l = −36→35

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)] = 0.036	H-atom parameters constrained
wR(F2) = 0.083	w = 1/[σ2(Fo2) + (0.035P)2 + 0.4874P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
3531 reflections	Δρmax = 0.13 e Å−3
265 parameters	Δρmin = −0.20 e Å−3
6 restraints	Absolute structure: Flack (1983), 1442 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.03 (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	Occ. (<1)
S1	0.84854 (9)	−0.00702 (6)	0.40081 (2)	0.04437 (16)
S2	0.83732 (9)	0.12928 (5)	0.22154 (2)	0.03921 (15)
O1	0.7421 (3)	0.08375 (18)	0.42783 (6)	0.0594 (5)
O2	1.0685 (3)	0.0089 (2)	0.39251 (7)	0.0716 (6)
O3	0.7251 (3)	0.24688 (15)	0.21378 (6)	0.0501 (4)
O4	1.0600 (2)	0.13432 (18)	0.22902 (6)	0.0532 (5)
N1	0.7323 (3)	−0.0080 (2)	0.35377 (6)	0.0439 (5)
N2	0.7313 (3)	0.06018 (17)	0.26359 (6)	0.0388 (5)
C1	0.6335 (4)	−0.1951 (3)	0.44536 (8)	0.0511 (6)
H1	0.5214	−0.1374	0.4464	0.061*
C2	0.6164 (5)	−0.3155 (3)	0.46458 (8)	0.0603 (8)
H2	0.4911	−0.3386	0.4783	0.072*
C3	0.7831 (6)	−0.4029 (3)	0.46375 (8)	0.0618 (8)
C4	0.9649 (5)	−0.3682 (3)	0.44218 (9)	0.0589 (7)
H4	1.0765	−0.4263	0.4408	0.071*
C5	0.9853 (4)	−0.2489 (3)	0.42246 (8)	0.0495 (6)
H5	1.1091	−0.2274	0.4079	0.059*
C6	0.8205 (4)	−0.1615 (2)	0.42453 (7)	0.0419 (5)
C8A	0.8715 (15)	−0.0801 (9)	0.3232 (2)	0.044 (2)	0.466 (13)
H8A1	0.8801	−0.1695	0.3323	0.053*	0.466 (13)
H8A2	1.0125	−0.0438	0.3241	0.053*	0.466 (13)
C9A	0.7867 (18)	−0.0729 (7)	0.2768 (3)	0.040 (2)	0.466 (13)
H9A1	0.8920	−0.1065	0.2568	0.048*	0.466 (13)
H9A2	0.6624	−0.1270	0.2745	0.048*	0.466 (13)
C8B	0.7774 (14)	−0.1092 (6)	0.31983 (19)	0.0377 (15)	0.534 (13)
H8B1	0.6480	−0.1544	0.3126	0.045*	0.534 (13)
H8B2	0.8765	−0.1714	0.3316	0.045*	0.534 (13)
C9B	0.8687 (11)	−0.0489 (7)	0.2785 (3)	0.0353 (17)	0.534 (13)
H9B1	1.0098	−0.0173	0.2844	0.042*	0.534 (13)
H9B2	0.8778	−0.1135	0.2556	0.042*	0.534 (13)
C10	0.5022 (4)	0.0686 (3)	0.26975 (8)	0.0517 (7)
H10A	0.4390	−0.0144	0.2633	0.062*
H10B	0.4447	0.1312	0.2494	0.062*
C11	0.4459 (4)	0.1078 (3)	0.31613 (9)	0.0518 (7)
H11A	0.5150	0.1891	0.3226	0.062*
H11B	0.2950	0.1226	0.3175	0.062*
C12	0.5040 (4)	0.0126 (3)	0.35127 (8)	0.0536 (7)
H12A	0.4535	0.0438	0.3793	0.064*
H12B	0.4350	−0.0691	0.3453	0.064*
C13	0.7984 (4)	0.0278 (2)	0.17594 (7)	0.0394 (5)
C14	0.9546 (4)	−0.0588 (2)	0.16374 (8)	0.0449 (6)
H14	1.0803	−0.0630	0.1794	0.054*
C15	0.9215 (4)	−0.1392 (3)	0.12792 (8)	0.0515 (6)
H15	1.0266	−0.1968	0.1196	0.062*
C16	0.7342 (5)	−0.1350 (3)	0.10436 (9)	0.0521 (6)
C17	0.5795 (4)	−0.0506 (3)	0.11791 (9)	0.0543 (7)
H17	0.4521	−0.0486	0.1028	0.065*
C18	0.6080 (4)	0.0313 (2)	0.15328 (8)	0.0469 (6)
H18	0.5015	0.0877	0.1618	0.056*
C19	0.7052 (6)	−0.2180 (3)	0.06426 (9)	0.0691 (9)
H19A	0.5637	−0.2509	0.0636	0.104*
H19B	0.8030	−0.2887	0.0652	0.104*
H19C	0.7305	−0.1673	0.0385	0.104*
C7	0.7658 (6)	−0.5318 (3)	0.48659 (10)	0.0877 (12)
H7A	0.7705	−0.5997	0.4652	0.131*
H7B	0.6349	−0.5359	0.5023	0.131*
H7C	0.8810	−0.5415	0.5067	0.131*

	U11	U22	U33	U12	U13	U23
S1	0.0326 (3)	0.0467 (3)	0.0537 (3)	−0.0031 (3)	0.0021 (3)	0.0001 (3)
S2	0.0305 (3)	0.0333 (3)	0.0538 (3)	−0.0003 (2)	−0.0042 (3)	0.0032 (3)
O1	0.0676 (13)	0.0522 (11)	0.0584 (11)	0.0016 (9)	−0.0065 (9)	−0.0171 (9)
O2	0.0299 (9)	0.0798 (14)	0.1052 (15)	−0.0070 (10)	0.0024 (10)	0.0327 (13)
O3	0.0498 (10)	0.0296 (8)	0.0710 (12)	0.0033 (7)	−0.0041 (9)	0.0093 (8)
O4	0.0271 (8)	0.0608 (11)	0.0717 (12)	−0.0036 (8)	−0.0061 (8)	−0.0080 (10)
N1	0.0411 (11)	0.0450 (11)	0.0457 (10)	0.0089 (9)	0.0087 (9)	−0.0023 (10)
N2	0.0373 (11)	0.0326 (10)	0.0464 (11)	0.0048 (8)	−0.0031 (9)	0.0025 (9)
C1	0.0479 (15)	0.0597 (16)	0.0458 (13)	−0.0042 (13)	0.0092 (12)	−0.0037 (12)
C2	0.073 (2)	0.0680 (18)	0.0401 (14)	−0.0238 (16)	0.0104 (14)	−0.0042 (13)
C3	0.094 (2)	0.0522 (16)	0.0395 (14)	−0.0121 (16)	−0.0093 (15)	−0.0031 (12)
C4	0.077 (2)	0.0505 (15)	0.0497 (15)	0.0081 (16)	−0.0049 (14)	−0.0054 (13)
C5	0.0482 (15)	0.0590 (16)	0.0413 (14)	0.0046 (13)	0.0025 (12)	−0.0031 (12)
C6	0.0394 (13)	0.0492 (14)	0.0370 (12)	−0.0026 (11)	0.0018 (11)	−0.0036 (10)
C8A	0.035 (4)	0.050 (4)	0.048 (4)	0.011 (4)	0.005 (3)	0.006 (3)
C9A	0.046 (5)	0.031 (3)	0.043 (4)	−0.001 (3)	−0.004 (4)	0.001 (3)
C8B	0.036 (4)	0.041 (3)	0.036 (3)	0.002 (3)	0.003 (3)	−0.005 (2)
C9B	0.035 (4)	0.030 (3)	0.041 (3)	0.006 (2)	−0.001 (3)	0.001 (3)
C10	0.0334 (13)	0.0642 (17)	0.0576 (16)	−0.0106 (12)	−0.0099 (11)	0.0107 (14)
C11	0.0268 (11)	0.0530 (16)	0.0758 (18)	0.0059 (11)	−0.0004 (12)	−0.0106 (13)
C12	0.0353 (13)	0.0765 (19)	0.0491 (14)	−0.0133 (13)	0.0033 (11)	−0.0035 (15)
C13	0.0356 (12)	0.0383 (12)	0.0442 (12)	−0.0016 (10)	−0.0024 (10)	0.0101 (10)
C14	0.0402 (13)	0.0438 (13)	0.0506 (14)	0.0029 (11)	−0.0007 (12)	0.0061 (12)
C15	0.0561 (16)	0.0442 (14)	0.0543 (15)	0.0045 (13)	0.0055 (13)	0.0047 (13)
C16	0.0640 (17)	0.0446 (13)	0.0477 (14)	−0.0054 (13)	−0.0038 (13)	0.0051 (13)
C17	0.0542 (16)	0.0577 (16)	0.0511 (14)	−0.0062 (13)	−0.0158 (13)	0.0090 (13)
C18	0.0413 (14)	0.0464 (14)	0.0529 (14)	0.0032 (11)	−0.0066 (11)	0.0019 (11)
C19	0.092 (2)	0.0543 (17)	0.0613 (18)	−0.0067 (17)	−0.0096 (17)	−0.0056 (14)
C7	0.140 (4)	0.063 (2)	0.0591 (18)	−0.028 (2)	−0.021 (2)	0.0131 (15)

S1—O1	1.4216 (19)	C8B—C9B	1.522 (7)
S1—O2	1.4273 (18)	C8B—H8B1	0.9700
S1—N1	1.614 (2)	C8B—H8B2	0.9700
S1—C6	1.766 (2)	C9B—H9B1	0.9700
S2—O4	1.4313 (17)	C9B—H9B2	0.9700
S2—O3	1.4313 (16)	C10—C11	1.515 (4)
S2—N2	1.616 (2)	C10—H10A	0.9700
S2—C13	1.762 (2)	C10—H10B	0.9700
N1—C12	1.465 (3)	C11—C12	1.504 (4)
N1—C8A	1.486 (6)	C11—H11A	0.9700
N1—C8B	1.502 (5)	C11—H11B	0.9700
N2—C10	1.467 (3)	C12—H12A	0.9700
N2—C9A	1.480 (7)	C12—H12B	0.9700
N2—C9B	1.499 (6)	C13—C14	1.388 (3)
C1—C2	1.384 (4)	C13—C18	1.392 (3)
C1—C6	1.389 (4)	C14—C15	1.391 (4)
C1—H1	0.9300	C14—H14	0.9300
C2—C3	1.392 (4)	C15—C16	1.389 (4)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.375 (4)	C16—C17	1.378 (4)
C3—C7	1.511 (4)	C16—C19	1.507 (4)
C4—C5	1.381 (4)	C17—C18	1.385 (4)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.385 (3)	C18—H18	0.9300
C5—H5	0.9300	C19—H19A	0.9600
C8A—C9A	1.516 (8)	C19—H19B	0.9600
C8A—H8A1	0.9700	C19—H19C	0.9600
C8A—H8A2	0.9700	C7—H7A	0.9600
C9A—H9A1	0.9700	C7—H7B	0.9600
C9A—H9A2	0.9700	C7—H7C	0.9600
O1—S1—O2	119.36 (13)	C9B—C8B—H8B2	109.5
O1—S1—N1	107.66 (11)	H8B1—C8B—H8B2	108.0
O2—S1—N1	106.80 (12)	N2—C9B—C8B	109.9 (5)
O1—S1—C6	108.33 (12)	N2—C9B—H9B1	109.7
O2—S1—C6	106.02 (12)	C8B—C9B—H9B1	109.7
N1—S1—C6	108.25 (11)	N2—C9B—H9B2	109.7
O4—S2—O3	119.05 (11)	C8B—C9B—H9B2	109.7
O4—S2—N2	107.45 (11)	H9B1—C9B—H9B2	108.2
O3—S2—N2	107.59 (10)	N2—C10—C11	111.7 (2)
O4—S2—C13	106.62 (11)	N2—C10—H10A	109.3
O3—S2—C13	107.95 (11)	C11—C10—H10A	109.3
N2—S2—C13	107.71 (10)	N2—C10—H10B	109.3
C12—N1—C8A	128.8 (4)	C11—C10—H10B	109.3
C12—N1—C8B	104.7 (4)	H10A—C10—H10B	107.9
C12—N1—S1	119.77 (16)	C12—C11—C10	115.6 (2)
C8A—N1—S1	106.9 (3)	C12—C11—H11A	108.4
C8B—N1—S1	122.1 (3)	C10—C11—H11A	108.4
C10—N2—C9A	104.8 (5)	C12—C11—H11B	108.4
C10—N2—C9B	125.6 (3)	C10—C11—H11B	108.4
C10—N2—S2	119.14 (16)	H11A—C11—H11B	107.4
C9A—N2—S2	122.1 (5)	N1—C12—C11	112.0 (2)
C9B—N2—S2	109.5 (3)	N1—C12—H12A	109.2
C2—C1—C6	119.2 (3)	C11—C12—H12A	109.2
C2—C1—H1	120.4	N1—C12—H12B	109.2
C6—C1—H1	120.4	C11—C12—H12B	109.2
C1—C2—C3	121.3 (3)	H12A—C12—H12B	107.9
C1—C2—H2	119.3	C14—C13—C18	120.2 (2)
C3—C2—H2	119.3	C14—C13—S2	119.87 (18)
C4—C3—C2	118.4 (3)	C18—C13—S2	119.90 (19)
C4—C3—C7	120.9 (3)	C13—C14—C15	119.4 (2)
C2—C3—C7	120.8 (3)	C13—C14—H14	120.3
C3—C4—C5	121.4 (3)	C15—C14—H14	120.3
C3—C4—H4	119.3	C16—C15—C14	121.1 (3)
C5—C4—H4	119.3	C16—C15—H15	119.4
C4—C5—C6	119.7 (3)	C14—C15—H15	119.4
C4—C5—H5	120.1	C17—C16—C15	118.3 (3)
C6—C5—H5	120.1	C17—C16—C19	121.3 (3)
C5—C6—C1	120.0 (2)	C15—C16—C19	120.5 (3)
C5—C6—S1	119.9 (2)	C16—C17—C18	122.0 (3)
C1—C6—S1	120.1 (2)	C16—C17—H17	119.0
N1—C8A—C9A	110.6 (7)	C18—C17—H17	119.0
N1—C8A—H8A1	109.5	C17—C18—C13	119.0 (2)
C9A—C8A—H8A1	109.5	C17—C18—H18	120.5
N1—C8A—H8A2	109.5	C13—C18—H18	120.5
C9A—C8A—H8A2	109.5	C16—C19—H19A	109.5
H8A1—C8A—H8A2	108.1	C16—C19—H19B	109.5
N2—C9A—C8A	112.6 (6)	H19A—C19—H19B	109.5
N2—C9A—H9A1	109.1	C16—C19—H19C	109.5
C8A—C9A—H9A1	109.1	H19A—C19—H19C	109.5
N2—C9A—H9A2	109.1	H19B—C19—H19C	109.5
C8A—C9A—H9A2	109.1	C3—C7—H7A	109.5
H9A1—C9A—H9A2	107.8	C3—C7—H7B	109.5
N1—C8B—C9B	110.9 (6)	H7A—C7—H7B	109.5
N1—C8B—H8B1	109.5	C3—C7—H7C	109.5
C9B—C8B—H8B1	109.5	H7A—C7—H7C	109.5
N1—C8B—H8B2	109.5	H7B—C7—H7C	109.5
O1—S1—N1—C12	−34.0 (3)	S1—N1—C8A—C9A	−173.6 (8)
O2—S1—N1—C12	−163.3 (2)	C10—N2—C9A—C8A	−98.8 (10)
C6—S1—N1—C12	82.9 (2)	C9B—N2—C9A—C8A	60.8 (13)
O1—S1—N1—C8A	167.7 (5)	S2—N2—C9A—C8A	121.8 (9)
O2—S1—N1—C8A	38.4 (5)	N1—C8A—C9A—N2	48.4 (15)
C6—S1—N1—C8A	−75.4 (5)	C12—N1—C8B—C9B	101.7 (7)
O1—S1—N1—C8B	−168.7 (4)	C8A—N1—C8B—C9B	−57.8 (9)
O2—S1—N1—C8B	62.0 (4)	S1—N1—C8B—C9B	−118.0 (6)
C6—S1—N1—C8B	−51.8 (4)	C10—N2—C9B—C8B	−30.9 (10)
O4—S2—N2—C10	165.87 (18)	C9A—N2—C9B—C8B	−55.4 (14)
O3—S2—N2—C10	36.5 (2)	S2—N2—C9B—C8B	176.4 (6)
C13—S2—N2—C10	−79.6 (2)	N1—C8B—C9B—N2	−51.2 (11)
O4—S2—N2—C9A	−60.1 (4)	C9A—N2—C10—C11	87.3 (4)
O3—S2—N2—C9A	170.6 (4)	C9B—N2—C10—C11	77.9 (6)
C13—S2—N2—C9A	54.4 (4)	S2—N2—C10—C11	−131.8 (2)
O4—S2—N2—C9B	−39.4 (4)	N2—C10—C11—C12	−65.3 (3)
O3—S2—N2—C9B	−168.8 (4)	C8A—N1—C12—C11	−73.4 (6)
C13—S2—N2—C9B	75.1 (4)	C8B—N1—C12—C11	−84.8 (3)
C6—C1—C2—C3	0.5 (4)	S1—N1—C12—C11	133.74 (19)
C1—C2—C3—C4	−1.8 (4)	C10—C11—C12—N1	62.6 (3)
C1—C2—C3—C7	177.3 (3)	O4—S2—C13—C14	20.1 (2)
C2—C3—C4—C5	1.3 (4)	O3—S2—C13—C14	149.10 (19)
C7—C3—C4—C5	−177.7 (3)	N2—S2—C13—C14	−95.0 (2)
C3—C4—C5—C6	0.4 (4)	O4—S2—C13—C18	−162.33 (19)
C4—C5—C6—C1	−1.7 (4)	O3—S2—C13—C18	−33.3 (2)
C4—C5—C6—S1	178.10 (19)	N2—S2—C13—C18	82.6 (2)
C2—C1—C6—C5	1.2 (4)	C18—C13—C14—C15	1.9 (4)
C2—C1—C6—S1	−178.58 (19)	S2—C13—C14—C15	179.45 (18)
O1—S1—C6—C5	−143.5 (2)	C13—C14—C15—C16	−0.5 (4)
O2—S1—C6—C5	−14.2 (2)	C14—C15—C16—C17	−1.3 (4)
N1—S1—C6—C5	100.1 (2)	C14—C15—C16—C19	176.9 (2)
O1—S1—C6—C1	36.3 (2)	C15—C16—C17—C18	1.6 (4)
O2—S1—C6—C1	165.6 (2)	C19—C16—C17—C18	−176.5 (3)
N1—S1—C6—C1	−80.1 (2)	C16—C17—C18—C13	−0.3 (4)
C12—N1—C8A—C9A	30.8 (12)	C14—C13—C18—C17	−1.5 (4)
C8B—N1—C8A—C9A	56.6 (10)	S2—C13—C18—C17	−179.09 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O3	0.97	2.40	2.886 (3)	110
C12—H12A···O1	0.97	2.39	2.878 (3)	111
C10—H10B···O4i	0.97	2.52	3.142 (3)	122
C12—H12A···O2i	0.97	2.50	3.035 (3)	115

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯O3	0.97	2.40	2.886 (3)	110
C12—H12A⋯O1	0.97	2.39	2.878 (3)	111
C10—H10B⋯O4i	0.97	2.52	3.142 (3)	122
C12—H12A⋯O2i	0.97	2.50	3.035 (3)	115

Symmetry code: (i) .