2,2′,4,4′,6,6′-Hexamethyl-N-(3-phthalimidoprop­yl)-N,N′-(propane-1,3-di­yl)dibenzene­sulfonamide

Wang, Y.-X.; Cheng, P.-F.; Wang, C.-J.

doi:10.1107/S1600536808036003

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2289

doi:10.1107/S1600536808036003

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2,2′,4,4′,6,6′-Hexamethyl-N-(3-phthalimidopropyl)-N,N′-(propane-1,3-diyl)dibenzenesulfonamide

Yu-Xia Wang,^a ^* Peng-Fei Cheng ^a and Chao-Jie Wang ^a

^aCollege of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, People's Republic of China
^*Correspondence e-mail: hgxywyx@126.com

(Received 2 November 2008; accepted 3 November 2008; online 8 November 2008)

In the title compound, C₃₂H₃₈N₃O₆S₂, an intermediate in the synthesis of polyamine drugs, the dihedral angle between the phenyl rings of the two 2,4,6-trimethylbenzenesulfonyl groups is 27.1 (3)°. In the crystal structure, molecules are linked by intermolecular N—H⋯O hydrogen bonds, thereby forming an infinite one-dimensional chain propagating along [010].

Related literature

Polyamines are essential growth factors for cells, existing mainly as polycations at physiological pH, see: Cullis et al. (1999 ); Seiler et al. (1996 ); Tsen et al. (2008 ).

Experimental

Crystal data

C₃₂H₃₉N₃O₆S₂
M_r = 625.78
Monoclinic, C 2/c
a = 32.042 (3) Å
b = 9.9782 (8) Å
c = 25.105 (2) Å
β = 127.917 (1)°
V = 6332.1 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 (2) K
0.18 × 0.15 × 0.13 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.962, T_max = 0.973
17128 measured reflections
6212 independent reflections
4574 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.219
S = 1.09
6212 reflections
388 parameters
44 restraints
H-atom parameters constrained
Δρ_max = 0.80 e Å⁻³
Δρ_min = −0.57 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯O5ⁱ	0.86	2.53	3.192 (4)	134
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036003/hb2835sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808036003/hb2835Isup2.hkl

checkCIF report

Comment top

Polyamines are essential growth factors for cells, which exist mainly as polycations at physiological pH (Cullis et al., 1999; Seiler et al., 1996; Tsen et al., 2008). As part of our studies in this area, herein we report the synthesis and structure of the title compound, (I).

The compound (I) consists of a polyamine chain with two 2,4,6-trimethylbenzenesulfonyl group acting as protecting groups (Fig. 1). In the structure of (I), the two phenyl ring of two 2,4,6-trimethylbenzenesulfonyl group are nonparallel due to steric hindrance, charactrtized by a dihedral angel of 27.1 (3) °.

In the crystal, molecules are linked through intermolecular N–H···O hydrogen bonds to construct an infinite one-dimensional chain (Fig. 2 and Table 1).

Related literature top

Polyamines are essential growth factors for cells, existing mainly as polycations at physiological pH, see: Cullis et al. (1999); Seiler et al. (1996); Tsen et al. (2008).

Experimental top

Propane-1,3-diamine 1.85 g (25 mmol) was dissolved in 2 M sodium hydroxide and the solution was cooled to 0 °C, a solution of 2,4,6-trimethylbenzenesulfonyl chloride 10.9 g (50 mmol) in CH₂Cl₂ (25 ml) was added dropwise. The reaction mixture was then stirred at room temperture for 18 h. The organic phase was separated from the aqueous phase and washed with 0.5 M HCl solution and brine. The CH₂Cl₂ layer was dried over sodium sulfate, filtered and the solvent removed in vacuo, and the residue purified by chromatography.

A mixture of N¹,N³—Bis(mesitylenesulfonyl)-1,3-propyl-diamine 1.05 g (2.33 mmol) and 60% NaH (5.35 mmol, 0.22 g) in DMF 20 ml was stirred at 0 °C for 0.5 h, then warmed to room temperature for 0.5 h. N-(3-bromopropyl)phthalimide 1.57 g (5.82 mmol) was added and the reaction mixture was stirred at 40 °C for 4 h, then EtoH (2.5 ml) and water (5 ml) were added, the solvent was removed in vacuo at 80 °C, the residue was dissolved in CHCl₃ and washed with water, the organic layer was dried over anhydrous sodium sulfate and filtered, then concentrated in vacuo, the residue was purified by chromatography. Colorless rod crystal of (I) were obtained.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of (I). Displacement ellipsoids for the non-hydrogen atoms are drawn at the 50% probability level.
	Fig. 2. One-dimensional structure of (I), Hydrogen bonds are shown as dashed lines. For clarity, H atoms not involved in hydrogen bonds are omitted.

2,2',4,4',6,6'-Hexamethyl-N-(3-phthalimidopropyl)-N,N'- (propane-1,3-diyl)dibenzenesulfonamide top

Crystal data top

C₃₂H₃₉N₃O₆S₂	F(000) = 2656
M_r = 625.78	D_x = 1.313 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6528 reflections
a = 32.042 (3) Å	θ = 2.4–28.1°
b = 9.9782 (8) Å	µ = 0.22 mm⁻¹
c = 25.105 (2) Å	T = 296 K
β = 127.917 (1)°	Block, colourless
V = 6332.1 (9) Å³	0.18 × 0.15 × 0.13 mm
Z = 8

Data collection top

Bruker SMART CCD diffractometer	6212 independent reflections
Radiation source: fine-focus sealed tube	4574 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω scans	θ_max = 26.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −25→39
T_min = 0.962, T_max = 0.973	k = −12→11
17128 measured reflections	l = −30→21

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.219	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.1169P)² + 7.2057P] where P = (F_o² + 2F_c²)/3
6212 reflections	(Δ/σ)_max < 0.001
388 parameters	Δρ_max = 0.80 e Å⁻³
44 restraints	Δρ_min = −0.57 e Å⁻³

Crystal data top

C₃₂H₃₉N₃O₆S₂	V = 6332.1 (9) Å³
M_r = 625.78	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 32.042 (3) Å	µ = 0.22 mm⁻¹
b = 9.9782 (8) Å	T = 296 K
c = 25.105 (2) Å	0.18 × 0.15 × 0.13 mm
β = 127.917 (1)°

Data collection top

Bruker SMART CCD diffractometer	6212 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	4574 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.973	R_int = 0.022
17128 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	44 restraints
wR(F²) = 0.219	H-atom parameters constrained
S = 1.10	Δρ_max = 0.80 e Å⁻³
6212 reflections	Δρ_min = −0.57 e Å⁻³
388 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
S1	0.15326 (3)	0.47012 (8)	0.46771 (4)	0.0531 (3)
S2	0.06920 (4)	0.72487 (9)	0.64731 (6)	0.0655 (3)
C1	0.14805 (12)	0.2922 (3)	0.45787 (15)	0.0464 (7)
C2	0.10216 (14)	0.2310 (3)	0.40203 (16)	0.0539 (8)
C3	0.10074 (16)	0.0918 (4)	0.39911 (18)	0.0635 (9)
H3A	0.0703	0.0502	0.3626	0.076*
C4	0.1424 (2)	0.0131 (4)	0.4479 (2)	0.0757 (9)
C5	0.18654 (16)	0.0764 (4)	0.50242 (19)	0.0637 (9)
H5A	0.2148	0.0242	0.5361	0.076*
C6	0.19082 (13)	0.2140 (3)	0.50937 (17)	0.0546 (8)
C7	0.24128 (15)	0.2685 (4)	0.57208 (19)	0.0734 (10)
H7A	0.2644	0.1956	0.5992	0.110*
H7B	0.2334	0.3194	0.5974	0.110*
H7C	0.2583	0.3253	0.5597	0.110*
C8	0.1398 (2)	−0.1383 (4)	0.4422 (2)	0.0849 (10)
H8A	0.1062	−0.1645	0.4014	0.127*
H8B	0.1439	−0.1763	0.4803	0.127*
H8C	0.1676	−0.1700	0.4413	0.127*
C9	0.05315 (15)	0.3038 (5)	0.34304 (18)	0.0761 (11)
H9A	0.0273	0.2393	0.3114	0.114*
H9B	0.0627	0.3598	0.3210	0.114*
H9C	0.0385	0.3580	0.3595	0.114*
C10	0.10008 (13)	0.4624 (3)	0.51695 (17)	0.0581 (8)
H10A	0.0998	0.3656	0.5203	0.070*
H10B	0.0691	0.4888	0.4724	0.070*
C11	0.09849 (17)	0.5273 (4)	0.5705 (2)	0.0732 (10)
H11A	0.0740	0.4792	0.5740	0.088*
H11B	0.1333	0.5236	0.6140	0.088*
C12	0.08133 (16)	0.6696 (4)	0.55154 (18)	0.0698 (10)
H12A	0.0432	0.6719	0.5171	0.084*
H12B	0.0972	0.7070	0.5321	0.084*
C13	0.05511 (12)	0.8878 (3)	0.66060 (17)	0.0512 (7)
C14	0.08566 (13)	0.9494 (4)	0.72467 (17)	0.0554 (8)
C15	0.07141 (15)	1.0790 (4)	0.7284 (2)	0.0718 (10)
H15A	0.0910	1.1211	0.7702	0.086*
C16	0.03042 (19)	1.1470 (5)	0.6740 (3)	0.1001 (12)
C17	0.00179 (16)	1.0841 (4)	0.6122 (2)	0.0822 (12)
H17A	−0.0259	1.1306	0.5745	0.099*
C18	0.01232 (15)	0.9547 (5)	0.6035 (2)	0.0743 (9)
C19	−0.02361 (16)	0.8980 (5)	0.5329 (2)	0.0848 (10)
H19A	−0.0494	0.9641	0.5028	0.127*
H19B	−0.0413	0.8201	0.5326	0.127*
H19C	−0.0030	0.8737	0.5185	0.127*
C20	0.0171 (2)	1.2887 (5)	0.6807 (3)	0.1087 (13)
H20A	0.0404	1.3153	0.7273	0.163*
H20B	−0.0188	1.2922	0.6646	0.163*
H20C	0.0215	1.3484	0.6545	0.163*
C21	0.13243 (15)	0.8889 (5)	0.78906 (18)	0.0743 (11)
H21A	0.1462	0.9517	0.8253	0.111*
H21B	0.1593	0.8679	0.7844	0.111*
H21C	0.1217	0.8085	0.7987	0.111*
C22	0.14972 (14)	0.8142 (4)	0.65501 (19)	0.0644 (9)
H22A	0.1754	0.7424	0.6717	0.077*
H22B	0.1547	0.8552	0.6936	0.077*
C23	0.16017 (16)	0.9152 (4)	0.62171 (19)	0.0692 (10)
H23A	0.1295	0.9732	0.5946	0.083*
H23B	0.1647	0.8699	0.5914	0.083*
C24	0.20845 (15)	1.0008 (4)	0.67022 (18)	0.0644 (9)
H24A	0.2389	0.9430	0.6991	0.077*
H24B	0.2152	1.0570	0.6447	0.077*
C25	0.16924 (18)	1.1983 (4)	0.68724 (19)	0.0795 (9)
C26	0.17520 (14)	1.2568 (3)	0.74571 (17)	0.0596 (8)
C27	0.15189 (16)	1.3666 (4)	0.7500 (2)	0.0748 (11)
H27A	0.1280	1.4190	0.7123	0.090*
C28	0.16498 (18)	1.3968 (4)	0.8121 (2)	0.0789 (11)
H28A	0.1497	1.4712	0.8162	0.095*
C29	0.20005 (17)	1.3201 (4)	0.8680 (2)	0.0719 (10)
H29A	0.2080	1.3429	0.9093	0.086*
C30	0.22369 (14)	1.2090 (4)	0.86355 (18)	0.0636 (9)
H30A	0.2474	1.1565	0.9013	0.076*
C31	0.21105 (12)	1.1789 (3)	0.80191 (16)	0.0528 (7)
C32	0.22889 (12)	1.0682 (3)	0.78088 (16)	0.0522 (7)
O1	0.20542 (11)	0.5116 (3)	0.49361 (14)	0.0727 (7)
O2	0.11048 (11)	0.5309 (3)	0.40790 (13)	0.0741 (7)
O3	0.10576 (13)	0.6647 (3)	0.71039 (18)	0.0900 (9)
O4	0.14220 (13)	1.2330 (3)	0.62932 (13)	0.0890 (8)
O5	0.26026 (10)	0.9802 (3)	0.81456 (12)	0.0691 (7)
O6	0.02164 (12)	0.6529 (3)	0.59969 (18)	0.0939 (10)
N1	0.20210 (11)	1.0851 (3)	0.71198 (13)	0.0566 (7)
N2	0.09614 (12)	0.7566 (3)	0.61035 (16)	0.0662 (8)
N3	0.14813 (10)	0.5046 (3)	0.52664 (13)	0.0523 (6)
H3B	0.1729	0.5466	0.5626	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0687 (5)	0.0447 (4)	0.0570 (5)	0.0021 (4)	0.0443 (4)	0.0024 (3)
S2	0.0762 (6)	0.0477 (5)	0.0974 (7)	−0.0042 (4)	0.0659 (6)	−0.0118 (5)
C1	0.0573 (17)	0.0451 (15)	0.0488 (16)	0.0052 (13)	0.0387 (15)	0.0006 (13)
C2	0.0663 (19)	0.0585 (19)	0.0489 (16)	0.0028 (15)	0.0414 (16)	−0.0046 (14)
C3	0.082 (2)	0.061 (2)	0.0574 (19)	−0.0106 (18)	0.0483 (19)	−0.0156 (16)
C4	0.127 (3)	0.0491 (15)	0.094 (2)	0.0034 (17)	0.089 (2)	−0.0075 (15)
C5	0.085 (2)	0.0552 (19)	0.068 (2)	0.0204 (18)	0.056 (2)	0.0112 (17)
C6	0.0643 (19)	0.0556 (18)	0.0589 (18)	0.0071 (15)	0.0454 (17)	0.0024 (15)
C7	0.060 (2)	0.078 (3)	0.062 (2)	0.0080 (19)	0.0281 (18)	0.0070 (19)
C8	0.131 (3)	0.0509 (15)	0.098 (2)	0.0032 (17)	0.083 (2)	−0.0078 (15)
C9	0.064 (2)	0.090 (3)	0.054 (2)	0.005 (2)	0.0263 (18)	−0.0025 (19)
C10	0.0620 (19)	0.0545 (18)	0.0641 (19)	−0.0097 (15)	0.0420 (17)	−0.0172 (15)
C11	0.079 (2)	0.067 (2)	0.087 (3)	−0.0039 (19)	0.058 (2)	−0.010 (2)
C12	0.069 (2)	0.076 (2)	0.065 (2)	0.0016 (19)	0.0412 (19)	−0.0101 (16)
C13	0.0510 (16)	0.0481 (16)	0.0657 (19)	0.0003 (13)	0.0415 (16)	−0.0056 (14)
C14	0.0531 (17)	0.062 (2)	0.0628 (19)	0.0002 (15)	0.0417 (16)	−0.0057 (16)
C15	0.067 (2)	0.069 (2)	0.089 (3)	−0.0076 (18)	0.053 (2)	−0.029 (2)
C16	0.083 (2)	0.068 (2)	0.151 (3)	0.0135 (17)	0.073 (2)	−0.015 (2)
C17	0.061 (2)	0.074 (2)	0.098 (3)	0.0204 (19)	0.042 (2)	0.009 (2)
C18	0.0549 (15)	0.093 (2)	0.0681 (17)	0.0012 (15)	0.0343 (14)	−0.0060 (16)
C19	0.0613 (16)	0.097 (2)	0.0718 (17)	0.0007 (15)	0.0288 (14)	−0.0062 (16)
C20	0.088 (2)	0.070 (2)	0.155 (3)	0.0145 (17)	0.069 (2)	−0.015 (2)
C21	0.070 (2)	0.099 (3)	0.059 (2)	0.007 (2)	0.0428 (19)	0.004 (2)
C22	0.065 (2)	0.062 (2)	0.077 (2)	0.0052 (17)	0.0488 (19)	−0.0013 (18)
C23	0.079 (2)	0.071 (2)	0.069 (2)	−0.0127 (19)	0.051 (2)	−0.0134 (18)
C24	0.068 (2)	0.071 (2)	0.067 (2)	−0.0084 (18)	0.0480 (19)	−0.0093 (18)
C25	0.1013 (19)	0.0670 (16)	0.0558 (13)	0.0131 (14)	0.0410 (14)	0.0110 (12)
C26	0.0613 (19)	0.0478 (17)	0.0597 (19)	−0.0017 (15)	0.0321 (17)	0.0019 (14)
C27	0.077 (2)	0.054 (2)	0.082 (3)	0.0068 (18)	0.043 (2)	0.0018 (18)
C28	0.094 (3)	0.051 (2)	0.108 (3)	0.002 (2)	0.070 (3)	−0.009 (2)
C29	0.087 (3)	0.063 (2)	0.081 (3)	−0.018 (2)	0.059 (2)	−0.020 (2)
C30	0.064 (2)	0.065 (2)	0.0557 (19)	−0.0042 (17)	0.0340 (17)	−0.0022 (16)
C31	0.0471 (16)	0.0491 (17)	0.0546 (17)	−0.0055 (13)	0.0274 (14)	−0.0026 (14)
C32	0.0422 (15)	0.0573 (18)	0.0510 (16)	−0.0027 (14)	0.0255 (14)	0.0013 (14)
O1	0.0816 (17)	0.0666 (16)	0.0918 (18)	−0.0112 (13)	0.0644 (15)	−0.0050 (14)
O2	0.0906 (18)	0.0586 (15)	0.0659 (15)	0.0090 (13)	0.0444 (14)	0.0070 (12)
O3	0.115 (2)	0.0606 (16)	0.125 (3)	0.0143 (16)	0.090 (2)	0.0101 (17)
O4	0.1081 (18)	0.0715 (15)	0.0585 (12)	0.0151 (13)	0.0364 (13)	0.0111 (11)
O5	0.0614 (14)	0.0711 (16)	0.0638 (14)	0.0187 (12)	0.0329 (12)	0.0094 (12)
O6	0.096 (2)	0.0750 (18)	0.146 (3)	−0.0360 (16)	0.092 (2)	−0.0488 (19)
N1	0.0579 (15)	0.0545 (15)	0.0524 (15)	−0.0013 (12)	0.0314 (13)	−0.0031 (12)
N2	0.0697 (18)	0.0615 (17)	0.088 (2)	−0.0128 (14)	0.0592 (17)	−0.0233 (14)
N3	0.0554 (15)	0.0481 (14)	0.0540 (14)	−0.0052 (11)	0.0339 (13)	−0.0116 (11)

Geometric parameters (Å, º) top

S1—O2	1.404 (3)	C15—H15A	0.9300
S1—O1	1.432 (3)	C16—C17	1.375 (7)
S1—N3	1.623 (3)	C16—C20	1.516 (6)
S1—C1	1.786 (3)	C17—C18	1.385 (6)
S2—O3	1.400 (3)	C17—H17A	0.9300
S2—O6	1.424 (3)	C18—C19	1.510 (5)
S2—N2	1.640 (3)	C19—H19A	0.9600
S2—C13	1.773 (3)	C19—H19B	0.9600
C1—C2	1.403 (5)	C19—H19C	0.9600
C1—C6	1.408 (4)	C20—H20A	0.9600
C2—C3	1.390 (5)	C20—H20B	0.9600
C2—C9	1.526 (5)	C20—H20C	0.9600
C3—C4	1.374 (6)	C21—H21A	0.9600
C3—H3A	0.9300	C21—H21B	0.9600
C4—C5	1.377 (6)	C21—H21C	0.9600
C4—C8	1.515 (5)	C22—N2	1.473 (5)
C5—C6	1.379 (5)	C22—C23	1.474 (5)
C5—H5A	0.9300	C22—H22A	0.9700
C6—C7	1.503 (5)	C22—H22B	0.9700
C7—H7A	0.9600	C23—C24	1.513 (5)
C7—H7B	0.9600	C23—H23A	0.9700
C7—H7C	0.9600	C23—H23B	0.9700
C8—H8A	0.9600	C24—N1	1.453 (4)
C8—H8B	0.9600	C24—H24A	0.9700
C8—H8C	0.9600	C24—H24B	0.9700
C9—H9A	0.9600	C25—O4	1.199 (4)
C9—H9B	0.9600	C25—N1	1.402 (5)
C9—H9C	0.9600	C25—C26	1.479 (6)
C10—N3	1.465 (4)	C26—C27	1.367 (5)
C10—C11	1.520 (5)	C26—C31	1.386 (5)
C10—H10A	0.9700	C27—C28	1.375 (6)
C10—H10B	0.9700	C27—H27A	0.9300
C11—C12	1.491 (6)	C28—C29	1.371 (6)
C11—H11A	0.9700	C28—H28A	0.9300
C11—H11B	0.9700	C29—C30	1.385 (5)
C12—N2	1.516 (4)	C29—H29A	0.9300
C12—H12A	0.9700	C30—C31	1.371 (5)
C12—H12B	0.9700	C30—H30A	0.9300
C13—C18	1.402 (5)	C31—C32	1.482 (5)
C13—C14	1.410 (5)	C32—O5	1.205 (4)
C14—C15	1.393 (5)	C32—N1	1.390 (4)
C14—C21	1.498 (5)	N3—H3B	0.8600
C15—C16	1.359 (7)

O2—S1—O1	117.42 (17)	C17—C16—C20	120.9 (5)
O2—S1—N3	107.70 (16)	C16—C17—C18	123.0 (4)
O1—S1—N3	105.58 (15)	C16—C17—H17A	118.5
O2—S1—C1	109.56 (15)	C18—C17—H17A	118.5
O1—S1—C1	109.49 (15)	C17—C18—C13	117.6 (4)
N3—S1—C1	106.49 (14)	C17—C18—C19	116.8 (4)
O3—S2—O6	116.9 (2)	C13—C18—C19	125.6 (4)
O3—S2—N2	110.94 (18)	C18—C19—H19A	109.5
O6—S2—N2	106.63 (18)	C18—C19—H19B	109.5
O3—S2—C13	108.23 (17)	H19A—C19—H19B	109.5
O6—S2—C13	110.82 (17)	C18—C19—H19C	109.5
N2—S2—C13	102.29 (16)	H19A—C19—H19C	109.5
C2—C1—C6	120.5 (3)	H19B—C19—H19C	109.5
C2—C1—S1	121.5 (2)	C16—C20—H20A	109.5
C6—C1—S1	118.0 (2)	C16—C20—H20B	109.5
C3—C2—C1	117.9 (3)	H20A—C20—H20B	109.5
C3—C2—C9	116.3 (3)	C16—C20—H20C	109.5
C1—C2—C9	125.8 (3)	H20A—C20—H20C	109.5
C4—C3—C2	122.8 (4)	H20B—C20—H20C	109.5
C4—C3—H3A	118.6	C14—C21—H21A	109.5
C2—C3—H3A	118.6	C14—C21—H21B	109.5
C3—C4—C5	117.7 (3)	H21A—C21—H21B	109.5
C3—C4—C8	121.3 (4)	C14—C21—H21C	109.5
C5—C4—C8	121.0 (4)	H21A—C21—H21C	109.5
C4—C5—C6	123.0 (3)	H21B—C21—H21C	109.5
C4—C5—H5A	118.5	N2—C22—C23	113.6 (3)
C6—C5—H5A	118.5	N2—C22—H22A	108.9
C5—C6—C1	118.1 (3)	C23—C22—H22A	108.9
C5—C6—C7	116.9 (3)	N2—C22—H22B	108.9
C1—C6—C7	125.1 (3)	C23—C22—H22B	108.9
C6—C7—H7A	109.5	H22A—C22—H22B	107.7
C6—C7—H7B	109.5	C22—C23—C24	113.9 (3)
H7A—C7—H7B	109.5	C22—C23—H23A	108.8
C6—C7—H7C	109.5	C24—C23—H23A	108.8
H7A—C7—H7C	109.5	C22—C23—H23B	108.8
H7B—C7—H7C	109.5	C24—C23—H23B	108.8
C4—C8—H8A	109.5	H23A—C23—H23B	107.7
C4—C8—H8B	109.5	N1—C24—C23	112.4 (3)
H8A—C8—H8B	109.5	N1—C24—H24A	109.1
C4—C8—H8C	109.5	C23—C24—H24A	109.1
H8A—C8—H8C	109.5	N1—C24—H24B	109.1
H8B—C8—H8C	109.5	C23—C24—H24B	109.1
C2—C9—H9A	109.5	H24A—C24—H24B	107.9
C2—C9—H9B	109.5	O4—C25—N1	123.8 (4)
H9A—C9—H9B	109.5	O4—C25—C26	130.2 (4)
C2—C9—H9C	109.5	N1—C25—C26	105.9 (3)
H9A—C9—H9C	109.5	C27—C26—C31	121.3 (4)
H9B—C9—H9C	109.5	C27—C26—C25	130.6 (3)
N3—C10—C11	109.5 (3)	C31—C26—C25	108.0 (3)
N3—C10—H10A	109.8	C26—C27—C28	117.7 (4)
C11—C10—H10A	109.8	C26—C27—H27A	121.2
N3—C10—H10B	109.8	C28—C27—H27A	121.2
C11—C10—H10B	109.8	C29—C28—C27	121.6 (4)
H10A—C10—H10B	108.2	C29—C28—H28A	119.2
C12—C11—C10	109.3 (3)	C27—C28—H28A	119.2
C12—C11—H11A	109.8	C28—C29—C30	120.6 (4)
C10—C11—H11A	109.8	C28—C29—H29A	119.7
C12—C11—H11B	109.8	C30—C29—H29A	119.7
C10—C11—H11B	109.8	C31—C30—C29	118.0 (3)
H11A—C11—H11B	108.3	C31—C30—H30A	121.0
C11—C12—N2	113.7 (3)	C29—C30—H30A	121.0
C11—C12—H12A	108.8	C30—C31—C26	120.8 (3)
N2—C12—H12A	108.8	C30—C31—C32	130.9 (3)
C11—C12—H12B	108.8	C26—C31—C32	108.4 (3)
N2—C12—H12B	108.8	O5—C32—N1	124.9 (3)
H12A—C12—H12B	107.7	O5—C32—C31	129.1 (3)
C18—C13—C14	121.0 (3)	N1—C32—C31	105.9 (3)
C18—C13—S2	116.5 (3)	C32—N1—C25	111.7 (3)
C14—C13—S2	122.4 (3)	C32—N1—C24	125.1 (3)
C15—C14—C13	117.0 (3)	C25—N1—C24	123.2 (3)
C15—C14—C21	116.9 (3)	C22—N2—C12	119.1 (3)
C13—C14—C21	126.0 (3)	C22—N2—S2	114.7 (2)
C16—C15—C14	123.4 (4)	C12—N2—S2	118.8 (2)
C16—C15—H15A	118.3	C10—N3—S1	118.2 (2)
C14—C15—H15A	118.3	C10—N3—H3B	120.9
C15—C16—C17	117.9 (4)	S1—N3—H3B	120.9
C15—C16—C20	121.2 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O5ⁱ	0.86	2.53	3.192 (4)	134

Symmetry code: (i) −x+1/2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₃₂H₃₉N₃O₆S₂
M_r	625.78
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	32.042 (3), 9.9782 (8), 25.105 (2)
β (°)	127.917 (1)
V (Å³)	6332.1 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.18 × 0.15 × 0.13

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.962, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	17128, 6212, 4574
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.219, 1.10
No. of reflections	6212
No. of parameters	388
No. of restraints	44
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.80, −0.57

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O5ⁱ	0.86	2.53	3.192 (4)	134

Symmetry code: (i) −x+1/2, y−1/2, −z+3/2.

Acknowledgements

This work was supported by the Basic Research Foundation for Natural Science of Henan University.

References

Bruker (2001). SAINT-Plus and SMART. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
Cullis, P. M., Green, R. E., Merson-Davies, L. & Travis, N. (1999). Chem. Biol. 6, 717–729. Web of Science CrossRef PubMed CAS Google Scholar
Seiler, N., Delcros, J.-G. & Moulinoux, J. P. (1996). Int. J. Biochem. Cell Biol. 28, 843–861. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tsen, C., Iltis, M., Kaur, N., Bayer, C., Dekcros, J-G., von Kalm, L. & Phanstiel IV, O. (2008). J. Med. Chem. 51, 324–330. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 64| Part 12| December 2008| Page o2289

doi:10.1107/S1600536808036003

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2,2′,4,4′,6,6′-Hexa­methyl-N-(3-phthalimidoprop­yl)-N,N′-(propane-1,3-di­yl)di­benzene­sulfonamide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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organic compounds

2,2′,4,4′,6,6′-Hexamethyl-N-(3-phthalimidopropyl)-N,N′-(propane-1,3-diyl)dibenzenesulfonamide