{N,N-Bis[3-(phenyl­ysulfan­yl)-1-(phenyl­sulfon­yl)indol-2-ylmeth­yl]amino}acetaldehyde dimethyl acetal

Yogavel, M.; Velmurugan, D.; Srinivasan, P.C.; Fun, H.-K.

doi:10.1107/S160053680502790X

{N,N-Bis[3-(phenylysulfanyl)-1-(phenylsulfonyl)indol-2-ylmethyl]amino}acetaldehyde dimethyl acetal

M. Yogavel, D. Velmurugan, P. C. Srinivasan and H.-K. Fun

The structure of the title compound, C₄₆H₄₁N₃O₆S₄, is stabilized by C—H

O, C—H

S and C—H

N interactions, and the packing of the molecules is stabilized by several C—H

π interactions, and face-to-face and edge-to-face π–π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680502790X/bt6700sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680502790X/bt6700Isup2.hkl Contains datablock I

CCDC reference: 287458

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
Disorder in main residue
R factor = 0.074
wR factor = 0.207
Data-to-parameter ratio = 19.7

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT241_ALERT_2_A Check High      Ueq as Compared to Neighbors for        C49

Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.95
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.63 Ratio
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        O6A

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         49 Perc.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) .....         10 Ang.
PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) .....         10 Ang.
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S2
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C34
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        O6B
PLAT301_ALERT_3_C Main Residue  Disorder .........................       2.00 Perc.
PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........        O6B
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........        CGA
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........        CGB
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........        CGC
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........        CGD
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........        CGH

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C46 H38 N3 O6 S4
            Atom count from _chemical_formula_moiety:C46 H41 N3 O6 S4

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

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

Comment top

Indole is a heterocyclic compound and is present in a large number of natural products. Many of these natural products and their synthetic derivatives have a wide range of biological activities, such as antibacterial (Okabe & Adachi, 1998), antitumour (Schollmeyer et al., 1995), antidepressant (Grinev et al., 1984), antimicrobial (El-Sayed et al., 1986; Gadaginamath & Patil, 1999) and anti-inflammatory (Rodriguez et al., 1985). Indoles have been proved to display high aldose reductose inhibitory activity (Rajeswaran et al., 1999). The interaction of phenylsulfonyl indole with the calf-thymus DNA by spectroscopic methods has also been studied (Sivaraman et al., 1996). The structure determination of the title compound, (I), was undertaken as part of our studies on indole derivatives.

The dihedral angle between the indole groups (AB and EF) and the phenyl rings (C, D, G and H) are AB/C = 75.0 (1)°, EF/G = 84.0 (1)°, AB/D = 84.9 (1)° and EF/H = 66.6 (1)°. The dihedral angle between rings C/D and G/H are 69.5 (1) and 77.8 (1)°, respectively. Atom N25 deviates by 0.217 (3) Å from the plane through atoms C26, C29 and S3, and the sum of the angles around N25 is 353.8 (2)°. This slight pyramidalization behaviour is also observed in related indole dervatives (Sankaranarayan et al., 2000, 2001; Sankaranarayan, Yogavel, Velmurugan, Sekar, Babu et al., 2003; Sankaranarayan, Yogavel, Velmurugan, Sekar, Srinivasan et al., 2003; SethuSankar et al., 2002; Ganesh et al., 2003; Krishna et al., 2003).

The molecular structure is stabilized by C—H···O, C—H···S and C—H···N interactions. The phenyl rings C of the molecules at (x, y, z) and (−x, −y, −z) are stacked in a face-to-face manner, with their centroids separated by 3.772 (2) Å. Several intermolecular edge-to-face interactions and several C—H···π interactions are also observed (Table 2). CgA, CgB, CgC, CgD and CgH are the centroid of the rings A, B, C, D and H, respectively. Thus, the crystal packing is stabilized by C—H···π, face-to-face π–π and edge-to-face π–π interactions.

Experimental top

To a solution of aminoacetaldehyde dimethyl acetal (4.4 ml, 40 mmol) in chloroform (40 ml) was added a solution of 1-phenylsulfonyl-2-bromomethyl-3-phenylthioindole (10 mmol) in chloroform (15 ml) and the mixture was stirred at room temperature for 4 h. Work-up of the reaction and crystallization of the residue in methanol afforded the title compound (yield 4.1 g, 85%) as the sole product.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 35% probability displacement ellipsoids. H atoms have been omitted. Dashed lines indicate the minor component of the disordered O atom.
	Fig. 2. The crystal structure of (I), viewed down the a axis. The π–π interactions are indicated as dashed lines. h atoms have been omitted.

{N,N-Bis[3-(phenylysulfanyl)-1-(phenylsulfonyl)indol-2- ylmethyl]amino}acetaldehyde dimethyl acetal top

Crystal data top

C₄₆H₄₁N₃O₆S₄	F(000) = 1788
M_r = 857.03	D_x = 1.318 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.7146 (1) Å	Cell parameters from 8042 reflections
b = 23.8939 (1) Å	θ = 1.5–28.5°
c = 16.8782 (3) Å	µ = 0.27 mm⁻¹
β = 91.846 (1)°	T = 293 K
V = 4318.81 (9) Å³	Block, colourless
Z = 4	0.40 × 0.36 × 0.28 mm

Data collection top

Siemens SMART CCD area-detector diffractometer	5223 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.066
Graphite monochromator	θ_max = 28.5°, θ_min = 1.5°
ω scans	h = −14→12
29148 measured reflections	k = −31→30
10689 independent reflections	l = −15→22

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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.207	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0814P)² + 1.9503P] where P = (F_o² + 2F_c²)/3
10689 reflections	(Δ/σ)_max < 0.001
543 parameters	Δρ_max = 0.56 e Å⁻³
4 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₄₆H₄₁N₃O₆S₄	V = 4318.81 (9) Å³
M_r = 857.03	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.7146 (1) Å	µ = 0.27 mm⁻¹
b = 23.8939 (1) Å	T = 293 K
c = 16.8782 (3) Å	0.40 × 0.36 × 0.28 mm
β = 91.846 (1)°

Data collection top

Siemens SMART CCD area-detector diffractometer	5223 reflections with I > 2σ(I)
29148 measured reflections	R_int = 0.066
10689 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.074	4 restraints
wR(F²) = 0.207	H-atom parameters constrained
S = 1.01	Δρ_max = 0.56 e Å⁻³
10689 reflections	Δρ_min = −0.45 e Å⁻³
543 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	Occ. (<1)
S1	0.03094 (9)	0.12078 (4)	0.13018 (6)	0.0519 (3)
S2	−0.18950 (12)	0.19653 (5)	0.40502 (7)	0.0763 (4)
O1	0.0408 (3)	0.15635 (12)	0.06275 (16)	0.0704 (8)
O2	0.1399 (2)	0.10436 (11)	0.17259 (15)	0.0606 (7)
N1	−0.0581 (3)	0.15581 (12)	0.19493 (17)	0.0459 (7)
C2	−0.0559 (3)	0.15283 (14)	0.2791 (2)	0.0460 (8)
C3	−0.1495 (4)	0.18668 (15)	0.3059 (2)	0.0542 (10)
C4	−0.2142 (3)	0.21075 (15)	0.2391 (2)	0.0518 (9)
C5	−0.1577 (3)	0.19132 (14)	0.1704 (2)	0.0485 (9)
C6	−0.2015 (4)	0.20612 (16)	0.0951 (3)	0.0636 (11)
H6	−0.1645	0.1929	0.0497	0.076*
C7	−0.3021 (4)	0.24121 (18)	0.0914 (3)	0.0773 (14)
H7	−0.3334	0.2525	0.0419	0.093*
C8	−0.3600 (4)	0.26087 (19)	0.1593 (4)	0.0800 (14)
H8	−0.4287	0.2845	0.1537	0.096*
C9	−0.3179 (4)	0.24626 (17)	0.2332 (3)	0.0707 (12)
H9	−0.3565	0.2594	0.2781	0.085*
C10	−0.0550 (3)	0.06121 (16)	0.1031 (2)	0.0487 (9)
C11	−0.1143 (4)	0.05786 (19)	0.0297 (2)	0.0600 (10)
H11	−0.1152	0.0883	−0.0047	0.072*
C12	−0.1726 (4)	0.0084 (2)	0.0084 (3)	0.0732 (13)
H12	−0.2129	0.0054	−0.0411	0.088*
C13	−0.1717 (4)	−0.03645 (19)	0.0592 (3)	0.0670 (12)
H13	−0.2106	−0.0697	0.0438	0.080*
C14	−0.1146 (4)	−0.03243 (18)	0.1315 (3)	0.0693 (12)
H14	−0.1156	−0.0628	0.1659	0.083*
C15	−0.0547 (4)	0.01622 (16)	0.1547 (2)	0.0575 (10)
H15	−0.0147	0.0188	0.2043	0.069*
C16	−0.1135 (4)	0.25987 (17)	0.4320 (2)	0.0644 (11)
C17	−0.0037 (5)	0.2780 (2)	0.3980 (3)	0.0780 (13)
H17	0.0305	0.2577	0.3570	0.094*
C18	0.0541 (6)	0.3262 (3)	0.4254 (3)	0.1011 (18)
H18	0.1279	0.3382	0.4035	0.121*
C19	0.0020 (9)	0.3562 (3)	0.4853 (4)	0.119 (2)
H19	0.0405	0.3889	0.5031	0.143*
C20	−0.1057 (8)	0.3388 (3)	0.5191 (4)	0.119 (2)
H20	−0.1382	0.3591	0.5607	0.143*
C21	−0.1665 (5)	0.2910 (2)	0.4919 (3)	0.0902 (16)
H21	−0.2415	0.2800	0.5133	0.108*
C22	0.0393 (3)	0.12299 (14)	0.3287 (2)	0.0489 (9)
H22A	0.1205	0.1299	0.3069	0.059*
H22B	0.0401	0.1392	0.3814	0.059*
N23	0.0229 (3)	0.06191 (11)	0.33627 (17)	0.0468 (7)
C46	−0.0882 (4)	0.04992 (17)	0.3836 (3)	0.0697 (12)
H46A	−0.1529	0.0766	0.3685	0.084*
H46B	−0.0660	0.0565	0.4390	0.084*
S3	0.22991 (8)	−0.05614 (4)	0.24818 (6)	0.0475 (2)
S4	0.35781 (12)	0.13191 (5)	0.41117 (7)	0.0744 (4)
O3	0.2462 (3)	−0.06861 (11)	0.16620 (15)	0.0618 (7)
O4	0.1103 (2)	−0.06092 (10)	0.28230 (16)	0.0570 (7)
N25	0.2763 (3)	0.00993 (11)	0.26098 (18)	0.0486 (7)
C26	0.2513 (3)	0.04376 (14)	0.3282 (2)	0.0453 (8)
C27	0.3448 (3)	0.08208 (15)	0.3358 (2)	0.0547 (10)
C28	0.4339 (4)	0.07319 (16)	0.2742 (3)	0.0586 (10)
C29	0.3905 (3)	0.02902 (15)	0.2280 (3)	0.0561 (10)
C30	0.4548 (4)	0.00988 (19)	0.1624 (3)	0.0737 (13)
H30	0.4249	−0.0198	0.1317	0.088*
C31	0.5658 (5)	0.0372 (2)	0.1452 (4)	0.0967 (19)
H31	0.6115	0.0252	0.1024	0.116*
C32	0.6093 (5)	0.0820 (2)	0.1904 (4)	0.0970 (18)
H32	0.6832	0.0997	0.1774	0.116*
C33	0.5451 (4)	0.10017 (19)	0.2537 (3)	0.0807 (15)
H33	0.5746	0.1305	0.2833	0.097*
C34	0.3360 (3)	−0.09629 (14)	0.3041 (2)	0.0500 (9)
C35	0.4387 (4)	−0.11872 (19)	0.2684 (3)	0.0762 (13)
H35	0.4524	−0.1114	0.2153	0.091*
C36	0.5205 (5)	−0.1518 (2)	0.3115 (3)	0.1027 (19)
H36	0.5893	−0.1675	0.2878	0.123*
C37	0.4997 (6)	−0.1614 (2)	0.3894 (4)	0.1038 (19)
H37	0.5550	−0.1838	0.4187	0.125*
C38	0.3983 (5)	−0.1385 (2)	0.4256 (3)	0.0983 (17)
H38	0.3861	−0.1454	0.4790	0.118*
C39	0.3158 (4)	−0.1057 (2)	0.3833 (3)	0.0742 (13)
H39	0.2473	−0.0901	0.4075	0.089*
C40	0.3675 (4)	0.19614 (16)	0.3591 (3)	0.0587 (10)
C41	0.3227 (4)	0.20433 (18)	0.2826 (3)	0.0674 (12)
H41	0.2875	0.1747	0.2541	0.081*
C42	0.3300 (4)	0.2566 (2)	0.2484 (3)	0.0850 (15)
H42	0.2997	0.2622	0.1968	0.102*
C43	0.3826 (6)	0.3005 (2)	0.2911 (5)	0.100 (2)
H43	0.3876	0.3358	0.2681	0.120*
C44	0.4271 (6)	0.2921 (2)	0.3667 (4)	0.0974 (18)
H44	0.4627	0.3218	0.3950	0.117*
C45	0.4197 (4)	0.24078 (18)	0.4010 (3)	0.0769 (13)
H45	0.4499	0.2356	0.4527	0.092*
C24	0.1356 (3)	0.03938 (15)	0.3768 (2)	0.0506 (9)
H24A	0.1215	0.0004	0.3896	0.061*
H24B	0.1499	0.0594	0.4262	0.061*
C47	−0.1432 (4)	−0.0087 (2)	0.3762 (3)	0.0951 (18)
H47	−0.1674	−0.0212	0.3226	0.114*
C49	−0.3618 (5)	0.0004 (4)	0.4082 (5)	0.165 (3)
O6A	−0.2349 (5)	−0.0104 (3)	0.4316 (3)	0.097 (3)	0.561 (11)
O6B	−0.2672 (5)	−0.0177 (3)	0.3562 (5)	0.107 (5)	0.439 (11)
O5	−0.0696 (4)	−0.04492 (13)	0.42085 (19)	0.0891 (10)
C48	−0.0968 (6)	−0.1033 (2)	0.4066 (4)	0.108 (2)
H48A	−0.1754	−0.1126	0.4290	0.163*
H48B	−0.0320	−0.1259	0.4308	0.163*
H48C	−0.1011	−0.1102	0.3506	0.163*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0467 (5)	0.0590 (6)	0.0506 (6)	0.0006 (4)	0.0100 (4)	0.0039 (5)
S2	0.0897 (9)	0.0701 (8)	0.0712 (8)	0.0003 (6)	0.0356 (7)	−0.0031 (6)
O1	0.0751 (19)	0.080 (2)	0.0567 (17)	−0.0003 (16)	0.0165 (14)	0.0183 (15)
O2	0.0406 (14)	0.0768 (19)	0.0645 (18)	0.0034 (13)	0.0034 (12)	−0.0032 (14)
N1	0.0463 (17)	0.0418 (16)	0.0500 (18)	0.0022 (13)	0.0061 (14)	0.0009 (13)
C2	0.046 (2)	0.042 (2)	0.050 (2)	−0.0057 (16)	0.0077 (17)	0.0054 (16)
C3	0.052 (2)	0.046 (2)	0.065 (3)	0.0001 (18)	0.0121 (19)	−0.0013 (19)
C4	0.044 (2)	0.040 (2)	0.072 (3)	−0.0030 (16)	0.0092 (19)	0.0033 (18)
C5	0.043 (2)	0.0379 (19)	0.065 (3)	−0.0057 (16)	0.0023 (18)	0.0049 (17)
C6	0.074 (3)	0.046 (2)	0.070 (3)	−0.001 (2)	−0.005 (2)	0.007 (2)
C7	0.074 (3)	0.056 (3)	0.100 (4)	0.002 (2)	−0.024 (3)	0.018 (3)
C8	0.062 (3)	0.055 (3)	0.122 (5)	0.010 (2)	−0.005 (3)	0.019 (3)
C9	0.057 (3)	0.050 (2)	0.106 (4)	0.008 (2)	0.018 (3)	0.004 (2)
C10	0.043 (2)	0.057 (2)	0.046 (2)	0.0081 (17)	0.0050 (16)	−0.0071 (18)
C11	0.055 (2)	0.073 (3)	0.052 (2)	0.014 (2)	0.0032 (19)	−0.001 (2)
C12	0.062 (3)	0.100 (4)	0.057 (3)	0.011 (3)	−0.007 (2)	−0.019 (3)
C13	0.064 (3)	0.066 (3)	0.070 (3)	0.000 (2)	0.002 (2)	−0.018 (2)
C14	0.078 (3)	0.055 (3)	0.074 (3)	0.000 (2)	−0.010 (2)	−0.002 (2)
C15	0.064 (3)	0.055 (2)	0.053 (2)	0.0082 (19)	−0.005 (2)	−0.0053 (19)
C16	0.075 (3)	0.062 (3)	0.056 (3)	0.018 (2)	0.006 (2)	0.001 (2)
C17	0.100 (4)	0.072 (3)	0.062 (3)	−0.001 (3)	0.002 (3)	0.000 (2)
C18	0.130 (5)	0.092 (4)	0.080 (4)	−0.020 (4)	−0.020 (4)	0.007 (3)
C19	0.195 (8)	0.070 (4)	0.090 (5)	−0.001 (5)	−0.037 (5)	−0.006 (3)
C20	0.179 (7)	0.093 (5)	0.083 (4)	0.044 (5)	−0.011 (5)	−0.030 (4)
C21	0.109 (4)	0.087 (4)	0.076 (3)	0.024 (3)	0.014 (3)	−0.019 (3)
C22	0.053 (2)	0.043 (2)	0.052 (2)	−0.0039 (16)	0.0031 (17)	0.0005 (16)
N23	0.0475 (17)	0.0408 (17)	0.0525 (18)	−0.0019 (13)	0.0087 (14)	0.0072 (13)
C46	0.067 (3)	0.062 (3)	0.082 (3)	−0.002 (2)	0.025 (2)	0.012 (2)
S3	0.0482 (5)	0.0395 (5)	0.0545 (6)	0.0017 (4)	−0.0036 (4)	0.0030 (4)
S4	0.0992 (9)	0.0587 (7)	0.0638 (7)	−0.0232 (6)	−0.0233 (6)	0.0077 (5)
O3	0.0782 (19)	0.0551 (16)	0.0513 (16)	0.0067 (14)	−0.0087 (13)	−0.0023 (12)
O4	0.0484 (15)	0.0489 (15)	0.0736 (18)	−0.0038 (12)	0.0013 (13)	0.0014 (13)
N25	0.0479 (17)	0.0388 (16)	0.059 (2)	−0.0038 (13)	0.0065 (15)	0.0052 (14)
C26	0.049 (2)	0.0400 (19)	0.047 (2)	0.0003 (16)	−0.0046 (17)	0.0068 (16)
C27	0.055 (2)	0.043 (2)	0.065 (3)	−0.0056 (18)	−0.012 (2)	0.0095 (18)
C28	0.048 (2)	0.045 (2)	0.082 (3)	−0.0039 (17)	−0.004 (2)	0.017 (2)
C29	0.048 (2)	0.043 (2)	0.078 (3)	0.0060 (17)	0.009 (2)	0.0157 (19)
C30	0.071 (3)	0.057 (3)	0.094 (4)	0.012 (2)	0.022 (3)	0.013 (2)
C31	0.078 (3)	0.076 (4)	0.140 (5)	0.015 (3)	0.058 (3)	0.030 (3)
C32	0.061 (3)	0.076 (4)	0.156 (6)	−0.002 (3)	0.037 (3)	0.032 (4)
C33	0.050 (3)	0.062 (3)	0.130 (5)	−0.006 (2)	0.002 (3)	0.024 (3)
C34	0.055 (2)	0.0387 (19)	0.056 (2)	0.0033 (17)	−0.0037 (18)	0.0039 (17)
C35	0.091 (3)	0.080 (3)	0.057 (3)	0.037 (3)	−0.004 (2)	0.001 (2)
C36	0.105 (4)	0.114 (4)	0.088 (4)	0.064 (4)	−0.006 (3)	0.002 (3)
C37	0.110 (4)	0.113 (5)	0.086 (4)	0.053 (4)	−0.017 (3)	0.023 (3)
C38	0.108 (4)	0.122 (5)	0.065 (3)	0.026 (4)	−0.006 (3)	0.034 (3)
C39	0.068 (3)	0.087 (3)	0.067 (3)	0.015 (2)	0.005 (2)	0.022 (2)
C40	0.058 (2)	0.049 (2)	0.068 (3)	−0.0013 (18)	0.000 (2)	0.003 (2)
C41	0.057 (2)	0.058 (3)	0.087 (3)	−0.004 (2)	−0.002 (2)	0.016 (2)
C42	0.071 (3)	0.082 (4)	0.102 (4)	0.018 (3)	0.008 (3)	0.036 (3)
C43	0.107 (4)	0.041 (3)	0.155 (6)	0.020 (3)	0.051 (4)	0.017 (3)
C44	0.126 (5)	0.045 (3)	0.123 (5)	0.002 (3)	0.036 (4)	−0.018 (3)
C45	0.094 (3)	0.053 (3)	0.084 (3)	−0.004 (2)	0.013 (3)	−0.013 (2)
C24	0.064 (2)	0.039 (2)	0.049 (2)	−0.0059 (17)	−0.0015 (18)	0.0044 (16)
C47	0.064 (3)	0.082 (4)	0.141 (5)	−0.023 (3)	0.013 (3)	0.045 (3)
C49	0.105 (6)	0.175 (8)	0.216 (9)	0.013 (5)	0.028 (6)	0.047 (7)
O6A	0.077 (5)	0.139 (6)	0.076 (5)	−0.038 (4)	0.004 (3)	0.039 (4)
O6B	0.087 (7)	0.094 (6)	0.138 (10)	−0.027 (5)	−0.023 (6)	0.038 (6)
O5	0.132 (3)	0.059 (2)	0.077 (2)	−0.0175 (19)	0.016 (2)	−0.0035 (16)
C48	0.145 (5)	0.057 (3)	0.126 (5)	−0.031 (3)	0.038 (4)	−0.011 (3)

Geometric parameters (Å, º) top

S1—O2	1.406 (3)	S3—N25	1.667 (3)
S1—O1	1.427 (3)	S3—C34	1.742 (4)
S1—N1	1.695 (3)	S4—C27	1.744 (4)
S1—C10	1.748 (4)	S4—C40	1.773 (4)
S2—C3	1.757 (4)	N25—C26	1.425 (4)
S2—C16	1.771 (5)	N25—C29	1.435 (4)
N1—C5	1.415 (4)	C26—C27	1.360 (5)
N1—C2	1.421 (4)	C26—C24	1.511 (5)
C2—C3	1.376 (5)	C27—C28	1.450 (5)
C2—C22	1.482 (5)	C28—C29	1.384 (6)
C3—C4	1.425 (5)	C28—C33	1.408 (5)
C4—C9	1.399 (5)	C29—C30	1.400 (6)
C4—C5	1.405 (5)	C30—C31	1.396 (6)
C5—C6	1.386 (5)	C30—H30	0.9300
C6—C7	1.365 (6)	C31—C32	1.385 (8)
C6—H6	0.9300	C31—H31	0.9300
C7—C8	1.403 (7)	C32—C33	1.361 (7)
C7—H7	0.9300	C32—H32	0.9300
C8—C9	1.357 (6)	C33—H33	0.9300
C8—H8	0.9300	C34—C35	1.380 (5)
C9—H9	0.9300	C34—C39	1.380 (5)
C10—C11	1.376 (5)	C35—C36	1.372 (6)
C10—C15	1.384 (5)	C35—H35	0.9300
C11—C12	1.379 (6)	C36—C37	1.359 (7)
C11—H11	0.9300	C36—H36	0.9300
C12—C13	1.372 (6)	C37—C38	1.377 (7)
C12—H12	0.9300	C37—H37	0.9300
C13—C14	1.351 (6)	C38—C39	1.365 (6)
C13—H13	0.9300	C38—H38	0.9300
C14—C15	1.379 (5)	C39—H39	0.9300
C14—H14	0.9300	C40—C41	1.377 (6)
C15—H15	0.9300	C40—C45	1.387 (6)
C16—C21	1.392 (6)	C41—C42	1.378 (6)
C16—C17	1.394 (6)	C41—H41	0.9300
C17—C18	1.380 (7)	C42—C43	1.383 (8)
C17—H17	0.9300	C42—H42	0.9300
C18—C19	1.371 (8)	C43—C44	1.362 (8)
C18—H18	0.9300	C43—H43	0.9300
C19—C20	1.369 (9)	C44—C45	1.360 (7)
C19—H19	0.9300	C44—H44	0.9300
C20—C21	1.384 (8)	C45—H45	0.9300
C20—H20	0.9300	C24—H24A	0.9700
C21—H21	0.9300	C24—H24B	0.9700
C22—N23	1.476 (4)	C47—O5	1.378 (6)
C22—H22A	0.9700	C47—O6B	1.3779 (10)
C22—H22B	0.9700	C47—O6A	1.3784 (10)
N23—C24	1.471 (4)	C47—H47	0.9800
N23—C46	1.483 (5)	C49—O6A	1.4277 (10)
C46—C47	1.524 (6)	C49—O6B	1.4292 (10)
C46—H46A	0.9700	O5—C48	1.443 (5)
C46—H46B	0.9700	C48—H48A	0.9600
S3—O4	1.426 (3)	C48—H48B	0.9600
S3—O3	1.432 (3)	C48—H48C	0.9600

O2—S1—O1	119.39 (17)	C27—S4—C40	103.55 (19)
O2—S1—N1	106.56 (15)	C26—N25—C29	108.2 (3)
O1—S1—N1	106.12 (16)	C26—N25—S3	125.3 (2)
O2—S1—C10	109.14 (17)	C29—N25—S3	120.3 (2)
O1—S1—C10	109.16 (18)	C27—C26—N25	107.5 (3)
N1—S1—C10	105.56 (15)	C27—C26—C24	127.5 (3)
C3—S2—C16	103.58 (19)	N25—C26—C24	124.8 (3)
C5—N1—C2	108.1 (3)	C26—C27—C28	109.5 (3)
C5—N1—S1	122.8 (2)	C26—C27—S4	124.8 (3)
C2—N1—S1	128.9 (2)	C28—C27—S4	125.7 (3)
C3—C2—N1	108.1 (3)	C29—C28—C33	118.8 (4)
C3—C2—C22	126.3 (3)	C29—C28—C27	107.4 (3)
N1—C2—C22	125.3 (3)	C33—C28—C27	133.8 (4)
C2—C3—C4	108.6 (3)	C28—C29—C30	122.0 (4)
C2—C3—S2	126.5 (3)	C28—C29—N25	107.4 (3)
C4—C3—S2	124.9 (3)	C30—C29—N25	130.6 (4)
C9—C4—C5	120.2 (4)	C31—C30—C29	117.2 (5)
C9—C4—C3	131.8 (4)	C31—C30—H30	121.4
C5—C4—C3	108.0 (3)	C29—C30—H30	121.4
C6—C5—C4	122.0 (4)	C32—C31—C30	121.3 (5)
C6—C5—N1	130.7 (4)	C32—C31—H31	119.3
C4—C5—N1	107.2 (3)	C30—C31—H31	119.3
C7—C6—C5	116.3 (4)	C33—C32—C31	120.6 (4)
C7—C6—H6	121.9	C33—C32—H32	119.7
C5—C6—H6	121.9	C31—C32—H32	119.7
C6—C7—C8	122.5 (4)	C32—C33—C28	120.0 (5)
C6—C7—H7	118.8	C32—C33—H33	120.0
C8—C7—H7	118.8	C28—C33—H33	120.0
C9—C8—C7	121.5 (4)	C35—C34—C39	120.8 (4)
C9—C8—H8	119.3	C35—C34—S3	119.5 (3)
C7—C8—H8	119.3	C39—C34—S3	119.7 (3)
C8—C9—C4	117.5 (4)	C36—C35—C34	119.8 (4)
C8—C9—H9	121.3	C36—C35—H35	120.1
C4—C9—H9	121.3	C34—C35—H35	120.1
C11—C10—C15	120.9 (4)	C37—C36—C35	119.2 (5)
C11—C10—S1	120.5 (3)	C37—C36—H36	120.4
C15—C10—S1	118.5 (3)	C35—C36—H36	120.4
C10—C11—C12	118.5 (4)	C36—C37—C38	121.2 (5)
C10—C11—H11	120.8	C36—C37—H37	119.4
C12—C11—H11	120.8	C38—C37—H37	119.4
C13—C12—C11	120.8 (4)	C39—C38—C37	120.2 (5)
C13—C12—H12	119.6	C39—C38—H38	119.9
C11—C12—H12	119.6	C37—C38—H38	119.9
C14—C13—C12	120.2 (4)	C38—C39—C34	118.7 (4)
C14—C13—H13	119.9	C38—C39—H39	120.6
C12—C13—H13	119.9	C34—C39—H39	120.6
C13—C14—C15	120.7 (4)	C41—C40—C45	119.4 (4)
C13—C14—H14	119.7	C41—C40—S4	124.3 (3)
C15—C14—H14	119.7	C45—C40—S4	116.3 (3)
C14—C15—C10	119.0 (4)	C42—C41—C40	119.9 (5)
C14—C15—H15	120.5	C42—C41—H41	120.1
C10—C15—H15	120.5	C40—C41—H41	120.1
C21—C16—C17	120.2 (5)	C41—C42—C43	119.8 (5)
C21—C16—S2	116.6 (4)	C41—C42—H42	120.1
C17—C16—S2	123.2 (3)	C43—C42—H42	120.1
C18—C17—C16	119.8 (5)	C44—C43—C42	120.1 (5)
C18—C17—H17	120.1	C44—C43—H43	120.0
C16—C17—H17	120.1	C42—C43—H43	120.0
C19—C18—C17	119.6 (6)	C45—C44—C43	120.5 (5)
C19—C18—H18	120.2	C45—C44—H44	119.8
C17—C18—H18	120.2	C43—C44—H44	119.8
C18—C19—C20	121.1 (6)	C44—C45—C40	120.3 (5)
C18—C19—H19	119.5	C44—C45—H45	119.8
C20—C19—H19	119.5	C40—C45—H45	119.8
C19—C20—C21	120.4 (6)	N23—C24—C26	113.4 (3)
C19—C20—H20	119.8	N23—C24—H24A	108.9
C21—C20—H20	119.8	C26—C24—H24A	108.9
C20—C21—C16	118.9 (6)	N23—C24—H24B	108.9
C20—C21—H21	120.6	C26—C24—H24B	108.9
C16—C21—H21	120.6	H24A—C24—H24B	107.7
N23—C22—C2	116.3 (3)	O5—C47—O6B	124.5 (5)
N23—C22—H22A	108.2	O5—C47—O6A	91.1 (4)
C2—C22—H22A	108.2	O6B—C47—O6A	57.2 (4)
N23—C22—H22B	108.2	O5—C47—C46	108.6 (4)
C2—C22—H22B	108.2	O6B—C47—C46	122.1 (5)
H22A—C22—H22B	107.4	O6A—C47—C46	104.7 (4)
C24—N23—C22	107.7 (3)	O5—C47—H47	116.4
C24—N23—C46	109.9 (3)	O6B—C47—H47	60.1
C22—N23—C46	109.7 (3)	O6A—C47—H47	116.4
N23—C46—C47	116.7 (3)	C46—C47—H47	116.4
N23—C46—H46A	108.1	O6A—C49—O6B	55.0 (4)
C47—C46—H46A	108.1	C47—O6A—C49	120.0 (4)
N23—C46—H46B	108.1	C47—O6B—C49	120.0 (4)
C47—C46—H46B	108.1	C47—O5—C48	114.0 (4)
H46A—C46—H46B	107.3	O5—C48—H48A	109.5
O4—S3—O3	120.82 (17)	O5—C48—H48B	109.5
O4—S3—N25	106.94 (15)	H48A—C48—H48B	109.5
O3—S3—N25	106.10 (16)	O5—C48—H48C	109.5
O4—S3—C34	108.42 (17)	H48A—C48—H48C	109.5
O3—S3—C34	108.16 (17)	H48B—C48—H48C	109.5
N25—S3—C34	105.36 (16)

O2—S1—N1—C5	162.5 (3)	C29—N25—C26—C27	0.5 (4)
O1—S1—N1—C5	34.3 (3)	S3—N25—C26—C27	152.7 (3)
C10—S1—N1—C5	−81.5 (3)	C29—N25—C26—C24	176.3 (3)
O2—S1—N1—C2	−22.6 (3)	S3—N25—C26—C24	−31.6 (5)
O1—S1—N1—C2	−150.9 (3)	N25—C26—C27—C28	−1.0 (4)
C10—S1—N1—C2	93.3 (3)	C24—C26—C27—C28	−176.6 (3)
C5—N1—C2—C3	−1.5 (4)	N25—C26—C27—S4	−178.3 (3)
S1—N1—C2—C3	−176.9 (3)	C24—C26—C27—S4	6.1 (5)
C5—N1—C2—C22	−175.7 (3)	C40—S4—C27—C26	−124.9 (3)
S1—N1—C2—C22	8.8 (5)	C40—S4—C27—C28	58.2 (4)
N1—C2—C3—C4	1.2 (4)	C26—C27—C28—C29	1.1 (4)
C22—C2—C3—C4	175.4 (3)	S4—C27—C28—C29	178.4 (3)
N1—C2—C3—S2	178.2 (3)	C26—C27—C28—C33	179.2 (4)
C22—C2—C3—S2	−7.6 (6)	S4—C27—C28—C33	−3.6 (6)
C16—S2—C3—C2	98.3 (4)	C33—C28—C29—C30	1.1 (6)
C16—S2—C3—C4	−85.1 (4)	C27—C28—C29—C30	179.5 (4)
C2—C3—C4—C9	177.7 (4)	C33—C28—C29—N25	−179.2 (3)
S2—C3—C4—C9	0.5 (6)	C27—C28—C29—N25	−0.8 (4)
C2—C3—C4—C5	−0.4 (4)	C26—N25—C29—C28	0.2 (4)
S2—C3—C4—C5	−177.6 (3)	S3—N25—C29—C28	−153.6 (3)
C9—C4—C5—C6	−0.1 (5)	C26—N25—C29—C30	179.9 (4)
C3—C4—C5—C6	178.3 (3)	S3—N25—C29—C30	26.2 (5)
C9—C4—C5—N1	−178.8 (3)	C28—C29—C30—C31	0.1 (6)
C3—C4—C5—N1	−0.5 (4)	N25—C29—C30—C31	−179.6 (4)
C2—N1—C5—C6	−177.4 (4)	C29—C30—C31—C32	−0.9 (7)
S1—N1—C5—C6	−1.6 (5)	C30—C31—C32—C33	0.6 (8)
C2—N1—C5—C4	1.2 (4)	C31—C32—C33—C28	0.6 (8)
S1—N1—C5—C4	177.0 (2)	C29—C28—C33—C32	−1.4 (6)
C4—C5—C6—C7	0.7 (6)	C27—C28—C33—C32	−179.3 (4)
N1—C5—C6—C7	179.1 (4)	O4—S3—C34—C35	152.0 (3)
C5—C6—C7—C8	−0.9 (6)	O3—S3—C34—C35	19.4 (4)
C6—C7—C8—C9	0.6 (7)	N25—S3—C34—C35	−93.8 (4)
C7—C8—C9—C4	0.1 (6)	O4—S3—C34—C39	−27.4 (4)
C5—C4—C9—C8	−0.3 (6)	O3—S3—C34—C39	−160.1 (3)
C3—C4—C9—C8	−178.2 (4)	N25—S3—C34—C39	86.8 (3)
O2—S1—C10—C11	−140.5 (3)	C39—C34—C35—C36	1.4 (7)
O1—S1—C10—C11	−8.4 (3)	S3—C34—C35—C36	−178.0 (4)
N1—S1—C10—C11	105.3 (3)	C34—C35—C36—C37	−0.9 (9)
O2—S1—C10—C15	35.1 (3)	C35—C36—C37—C38	0.0 (10)
O1—S1—C10—C15	167.2 (3)	C36—C37—C38—C39	0.4 (10)
N1—S1—C10—C15	−79.1 (3)	C37—C38—C39—C34	0.1 (8)
C15—C10—C11—C12	−0.7 (5)	C35—C34—C39—C38	−1.1 (7)
S1—C10—C11—C12	174.8 (3)	S3—C34—C39—C38	178.3 (4)
C10—C11—C12—C13	0.2 (6)	C27—S4—C40—C41	23.7 (4)
C11—C12—C13—C14	0.7 (7)	C27—S4—C40—C45	−159.0 (3)
C12—C13—C14—C15	−1.1 (7)	C45—C40—C41—C42	0.0 (6)
C13—C14—C15—C10	0.6 (6)	S4—C40—C41—C42	177.3 (3)
C11—C10—C15—C14	0.3 (6)	C40—C41—C42—C43	0.1 (7)
S1—C10—C15—C14	−175.3 (3)	C41—C42—C43—C44	0.0 (8)
C3—S2—C16—C21	153.3 (4)	C42—C43—C44—C45	−0.3 (8)
C3—S2—C16—C17	−28.7 (4)	C43—C44—C45—C40	0.4 (8)
C21—C16—C17—C18	1.7 (7)	C41—C40—C45—C44	−0.3 (7)
S2—C16—C17—C18	−176.2 (4)	S4—C40—C45—C44	−177.7 (4)
C16—C17—C18—C19	−0.8 (8)	C22—N23—C24—C26	−67.2 (4)
C17—C18—C19—C20	0.9 (9)	C46—N23—C24—C26	173.3 (3)
C18—C19—C20—C21	−1.9 (10)	C27—C26—C24—N23	101.6 (4)
C19—C20—C21—C16	2.7 (9)	N25—C26—C24—N23	−73.2 (4)
C17—C16—C21—C20	−2.6 (7)	N23—C46—C47—O5	77.5 (5)
S2—C16—C21—C20	175.4 (4)	N23—C46—C47—O6B	−126.0 (5)
C3—C2—C22—N23	106.1 (4)	N23—C46—C47—O6A	173.8 (4)
N1—C2—C22—N23	−80.7 (4)	O5—C47—O6A—C49	−154.1 (7)
C2—C22—N23—C24	171.4 (3)	O6B—C47—O6A—C49	−22.7 (6)
C2—C22—N23—C46	−69.0 (4)	C46—C47—O6A—C49	96.3 (7)
C24—N23—C46—C47	−80.3 (5)	O6B—C49—O6A—C47	22.4 (6)
C22—N23—C46—C47	161.5 (4)	O5—C47—O6B—C49	88.1 (9)
O4—S3—N25—C26	35.2 (3)	O6A—C47—O6B—C49	22.7 (6)
O3—S3—N25—C26	165.4 (3)	C46—C47—O6B—C49	−64.6 (9)
C34—S3—N25—C26	−80.0 (3)	O6A—C49—O6B—C47	−22.4 (6)
O4—S3—N25—C29	−175.8 (3)	O6B—C47—O5—C48	35.9 (7)
O3—S3—N25—C29	−45.6 (3)	O6A—C47—O5—C48	85.8 (5)
C34—S3—N25—C29	69.0 (3)	C46—C47—O5—C48	−168.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.93	2.37	2.923 (5)	118
C11—H11···O1	0.93	2.57	2.924 (5)	103
C15—H15···N23	0.93	2.48	3.334 (4)	153
C22—H22A···O2	0.97	2.36	2.913 (4)	115
C22—H22B···S2	0.97	2.85	3.311 (4)	110
C24—H24A···O4	0.97	2.33	2.887 (4)	116
C24—H24A···O5	0.97	2.39	3.090 (5)	129
C24—H24B···S4	0.97	2.84	3.287 (4)	109
C30—H30···O3	0.93	2.33	2.920 (5)	121
C35—H35···O3	0.93	2.55	2.904 (5)	103
C32—H32···CgAⁱ	0.93	2.95	3.728 (5)	143
C32—H32···CgBⁱ	0.93	3.09	3.752 (5)	129
C31—H31···CgCⁱ	0.93	2.99	3.680 (6)	132
C7—H7···CgDⁱⁱ	0.93	3.09	3.661 (5)	122
C9—H9···CgHⁱⁱⁱ	0.93	3.02	3.682 (5)	130

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

Experimental details

Crystal data
Chemical formula	C₄₆H₄₁N₃O₆S₄
M_r	857.03
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.7146 (1), 23.8939 (1), 16.8782 (3)
β (°)	91.846 (1)
V (Å³)	4318.81 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.40 × 0.36 × 0.28

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	29148, 10689, 5223
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.672

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.074, 0.207, 1.01
No. of reflections	10689
No. of parameters	543
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.45

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai, 1997) and PLATON (Spek, 2003), SHELXL97 and PARST (Nardelli, 1995).

Selected bond lengths (Å) top

S1—O2	1.406 (3)	S3—O4	1.426 (3)
S1—O1	1.427 (3)	S3—O3	1.432 (3)
N1—C5	1.415 (4)	N25—C26	1.425 (4)
N1—C2	1.421 (4)	N25—C29	1.435 (4)