(E)-N′-[5-Chloro-3-meth­oxy-2-(4-methyl­phenyl­sulfon­yloxy)benzyl­idene]isonicotinohydrazide acetic acid solvate: hydrogen-bonded network of alternating R⁴₄(42), R⁵₅(33) and R⁶₆(40) rings

In the title compound, C₂₁H₁₈ClN₃O₅S·C₂H₄O₂, a combination of O—H...O, N—H...O, C—H...O and C—H...N hydrogen bonds links the components into a complex network containing alternating R₄⁴(42), R₅⁵(33) and R₆⁶(40) rings.

S1. Comment

There has been steady growth of interest in the structure and reactivity of Schiff bases owing to their potential biological activities, such as antibacterial and antitumor (Kahwa et al., 1986; Santos et al., 2001). Isonicotinohydrazide forms a variety of Schiff bases with aldehydes, and the synthesis and crystal structures of some of them have been reported (Wardell, de Souza, Ferreira et al., 2005; Wardell, de Souza, Wardell et al., 2005; Wardell et al., 2006; Low et al., 2006). In order to obtain more detailed information on the structural conformation of the molecule, which may be of value in structure–activity analysis, we report here the synthesis and structure of the title compound, (I).

Within the hydrazine component in (I), both N atoms (N17 and N27) have effectively planar coordination, and the N—N bond distance (Table 1) is typical of the value in hydrazines with both N atoms having planar coordination (the mean value is 1.401 Å; Allen et al., 1987). In addition, the central spacer unit between atoms C17 and C21 (Fig. 1) adopts a nearly planar all-trans conformation, as shown by the key torsion angles (Table 1).

In (I), (Fig. 1), the acetic acid molecule is effectively tethered to the hydrazone component by a combination of two independent hydrogen bonds, one of O—H···O and one of N—H···O type (Fig. 2 and Table 2). Acetic acid atom O41 acts as a hydrogen-bond donor to hydrazone atom O17. At the same time, hydrazone atom N17 in the molecule at (x, y, z) acts as a hydrogen-bond donor to acetic acid atom O42 in the molecule at (2 - x, 1 - y, -1/2 + z). In addition, atom C33 in the molecule at (x, y, z) acts as a hydrogen-bond donor to atom O25 in the molecule at (x, y, 1 + z), so generating by translation a C₂²(8)C(9)R₅⁵(33) chain of fused rings (Bernstein et al., 1995) running parallel to the [001] direction.

Atom C24 in the molecule at (1 + x, y, z) acts as a hydrogen-bond donor to pyridyl atom N11 in the molecule at (x, y, z), so forming a C(13) chain running parallel to the [100] direction. In addition, atom C33 in the molecule at (x, y, -1 + z) in turn acts as a hydrogen-bond donor to atom O25 in the molecule at (x, y, z), so forming a C(9) chain running parallel to the [001] direction. The combination of the [100] and [001] chains then generate a sheet parallel to (010) containing R₄⁴(42) rings (Fig. 3). In combination with the C₂²(8)C(9)R₅⁵(33) chain of rings (Fig. 2), these hydrogen bonds then generate a complex network containing alternating R₄⁴(42), R₅⁵(33) and R₆⁶(40) rings (Fig. 4).

Related literature

For related literature, see: Allen et al. (1987); Bernstein et al. (1995); Kahwa et al. (1986); Low et al. (2006); Santos et al. (2001); Wardell et al. (2006); Wardell, de Souza, Ferreira, Vasconcelos, Low & Glidewell (2005); Wardell, de Souza, Wardell, Low & Glidewell (2005).

S2. Experimental

An anhydrous ethanol solution (50 ml) of 4-chloro-2-formyl-6-methoxyphenyl 4-methylbenzenesulfonate (3.41 g, 10 mmol) was added to an anhydrous ethanol solution (50 ml) of isonicotinohydrazide (1.37 g, 10 mmol) and the mixture was stirred at 350 K for 3 h under N₂, giving a white precipitate. The product was isolated, recrystallized from ethanol, and then dried in a vacuum to give pure compound (I) in 72% yield. Colourless single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of a solution of ethanol and acetic acid (80:20 v/v).

S3. Refinement

H atoms were included in calculated positions and refined using a riding-model approximation [constrained C—H and N—H bond lengths and U_iso(H) parameters: 0.93 Å and 1.2U_eq(C) for Csp² H atoms; 0.96 Å and 1.5U_eq(C) for methyl H atoms; 0.82 Å and 1.5U_eq(O) for the hydroxy H atom; 0.86 Å and 1.2U_eq(N) for the imine H atom]. Please check treatment of U_iso(H) for NH; this has an s.u. value and is not 1.2U_eq.

Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures

	Fig. 1. The independent components of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Part of the crystal structure of (I), showing the formation of a hydrogen-bonded chain of rings along [001]. For the sake of clarity, H atoms not involved in the motifs shown have been omitted. Atoms marked with an asterisk (*), a hash (#) or an ampersand (&) are at the symmetry positions (2 - x, 1 - y, 1/2 + z), (2 - x, 1 - y, -1/2 + z) and (x, y, -1 + z), respectively.
	Fig. 3. Part of the crystal structure of (I), showing the formation of a hydrogen-bonded (010) sheet. For the sake of clarity, H atoms not involved in the motifs shown have been omitted. Atoms marked with an asterisk (*), a hash (#) or an ampersand (&) are at the symmetry positions (1 + x, y, z), (x, y, -1 + z) and (1 + x, y, -1 + z), respectively.
	Fig. 4. Part of the crystal structure of (I), showing the complex network containing alternating R4^4(42), R5^5(33) and R6^6(40) rings. For the sake of clarity, H atoms not involved in the motifs shown have been omitted.

(E)—N'-[5-Chloro-3-methoxy-2-(4- methylphenylsulfonyloxy)benzylidene]isonicotinohydrazide acetic acid solvate

Crystal data

C21H18ClN3O5S·C2H4O2	F(000) = 1080
Mr = 519.96	Dx = 1.416 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2260 reflections
a = 14.886 (3) Å	θ = 2.2–19.8°
b = 23.190 (4) Å	µ = 0.29 mm^−1
c = 7.0638 (14) Å	T = 294 K
V = 2438.5 (8) Å^3	Block, colorless
Z = 4	0.26 × 0.20 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	4793 independent reflections
Radiation source: fine-focus sealed tube	2849 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
ϕ and ω scans	θmax = 26.4°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→18
Tmin = 0.912, Tmax = 0.955	k = −28→28
13425 measured reflections	l = −8→8

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.048	w = 1/[σ^2(Fo^2) + (0.0334P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.092	(Δ/σ)max < 0.001
S = 0.97	Δρmax = 0.20 e Å^−3
4793 reflections	Δρmin = −0.20 e Å^−3
322 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0027 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2080 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.01 (7)

Special details

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 > 2σ(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 (Ų)

	x	y	z	Uiso*/Ueq
N11	1.33949 (17)	0.46505 (14)	0.7920 (5)	0.0550 (9)
C12	1.3086 (2)	0.51545 (17)	0.7335 (6)	0.0525 (11)
H12	1.3505	0.5428	0.6947	0.063*
C13	1.2188 (2)	0.53074 (14)	0.7255 (6)	0.0459 (10)
H13	1.2012	0.5670	0.6836	0.055*
C14	1.15569 (18)	0.49012 (14)	0.7822 (5)	0.0365 (8)
C15	1.1866 (2)	0.43721 (14)	0.8455 (5)	0.0446 (10)
H15	1.1466	0.4089	0.8854	0.053*
C16	1.2780 (2)	0.42734 (16)	0.8483 (6)	0.0531 (11)
H16	1.2978	0.3918	0.8927	0.064*
C17	1.05883 (19)	0.50592 (15)	0.7789 (6)	0.0394 (8)
O17	1.03472 (14)	0.55587 (9)	0.8076 (4)	0.0530 (7)
N17	1.00106 (16)	0.46234 (12)	0.7474 (5)	0.0414 (7)
H17	1.0205	0.4285	0.7187	0.050*
N27	0.91027 (15)	0.47280 (11)	0.7619 (5)	0.0411 (7)
C27	0.8587 (2)	0.43109 (14)	0.7159 (5)	0.0398 (9)
H27	0.8832	0.3964	0.6742	0.048*
C21	0.76158 (19)	0.43778 (13)	0.7286 (5)	0.0347 (8)
C22	0.7222 (2)	0.49220 (13)	0.7489 (5)	0.0386 (8)
H22	0.7581	0.5250	0.7548	0.046*
C23	0.6301 (2)	0.49711 (13)	0.7604 (6)	0.0420 (9)
Cl1	0.58199 (6)	0.56505 (4)	0.78214 (17)	0.0626 (3)
C24	0.5741 (2)	0.45001 (13)	0.7525 (6)	0.0429 (9)
H24	0.5121	0.4545	0.7607	0.051*
C25	0.6115 (2)	0.39588 (14)	0.7322 (5)	0.0373 (9)
C26	0.70505 (19)	0.39018 (13)	0.7225 (5)	0.0367 (9)
O25	0.56453 (13)	0.34591 (9)	0.7199 (4)	0.0514 (7)
C25A	0.4709 (2)	0.34770 (14)	0.7663 (7)	0.0623 (11)
H25A	0.4632	0.3655	0.8880	0.093*
H25B	0.4474	0.3092	0.7697	0.093*
H25C	0.4393	0.3697	0.6723	0.093*
O26	0.74011 (13)	0.33444 (9)	0.6966 (3)	0.0420 (6)
S1	0.77402 (6)	0.29942 (4)	0.87993 (16)	0.0496 (3)
O1	0.81179 (15)	0.24898 (9)	0.7992 (5)	0.0708 (9)
O2	0.82839 (15)	0.33729 (10)	0.9892 (4)	0.0582 (8)
C31	0.6772 (2)	0.28251 (14)	1.0071 (6)	0.0448 (10)
C32	0.6561 (3)	0.31365 (16)	1.1667 (6)	0.0609 (11)
H32	0.6927	0.3439	1.2059	0.073*
C33	0.5802 (3)	0.29948 (17)	1.2677 (7)	0.0725 (13)
H33	0.5661	0.3206	1.3757	0.087*
C34	0.5242 (3)	0.25491 (18)	1.2137 (7)	0.0620 (11)
C35	0.5469 (3)	0.22472 (17)	1.0517 (7)	0.0606 (12)
H35	0.5098	0.1949	1.0115	0.073*
C36	0.6225 (2)	0.23737 (15)	0.9482 (6)	0.0521 (11)
H36	0.6368	0.2161	0.8407	0.063*
C37	0.4414 (3)	0.2396 (2)	1.3262 (8)	0.0946 (16)
H37A	0.4222	0.2014	1.2933	0.142*
H37B	0.3943	0.2665	1.2979	0.142*
H37C	0.4550	0.2411	1.4590	0.142*
C41	0.8649 (3)	0.64038 (16)	0.9429 (7)	0.0504 (11)
O41	0.87442 (16)	0.60544 (11)	0.7997 (4)	0.0619 (8)
H41	0.9248	0.5912	0.8022	0.093*
O42	0.91765 (18)	0.64319 (11)	1.0741 (4)	0.0610 (8)
C42	0.7810 (3)	0.67561 (18)	0.9299 (7)	0.0738 (14)
H42A	0.7332	0.6562	0.9952	0.111*
H42B	0.7649	0.6806	0.7994	0.111*
H42C	0.7910	0.7126	0.9870	0.111*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0361 (18)	0.065 (2)	0.064 (2)	0.0033 (17)	0.0011 (17)	0.001 (2)
C12	0.035 (2)	0.068 (3)	0.055 (3)	−0.013 (2)	0.008 (2)	0.000 (2)
C13	0.033 (2)	0.048 (2)	0.057 (3)	0.0005 (16)	0.0049 (19)	−0.001 (2)
C14	0.0269 (17)	0.047 (2)	0.036 (2)	0.0015 (15)	0.0016 (18)	−0.0045 (19)
C15	0.035 (2)	0.047 (2)	0.052 (3)	−0.0006 (16)	−0.0012 (17)	0.002 (2)
C16	0.041 (2)	0.056 (2)	0.062 (3)	0.0068 (19)	−0.006 (2)	−0.001 (2)
C17	0.0302 (19)	0.049 (2)	0.039 (2)	−0.0013 (17)	0.0006 (19)	0.000 (2)
O17	0.0395 (13)	0.0407 (13)	0.079 (2)	0.0048 (11)	0.0003 (13)	−0.0090 (14)
N17	0.0226 (15)	0.0413 (16)	0.060 (2)	0.0017 (13)	0.0024 (15)	−0.0047 (17)
N27	0.0202 (15)	0.0489 (17)	0.054 (2)	0.0026 (12)	0.0026 (14)	−0.0033 (17)
C27	0.0297 (19)	0.045 (2)	0.044 (3)	0.0050 (16)	0.0042 (16)	−0.0028 (19)
C21	0.0243 (17)	0.0426 (19)	0.037 (2)	0.0027 (15)	0.0000 (15)	−0.0015 (19)
C22	0.0361 (19)	0.0390 (19)	0.041 (2)	−0.0034 (15)	−0.0006 (17)	0.0026 (18)
C23	0.0301 (18)	0.046 (2)	0.050 (3)	0.0090 (15)	0.0008 (18)	0.003 (2)
Cl1	0.0496 (6)	0.0502 (5)	0.0882 (8)	0.0136 (4)	0.0036 (6)	0.0006 (6)
C24	0.0270 (17)	0.052 (2)	0.049 (3)	0.0034 (16)	0.0011 (18)	0.003 (2)
C25	0.0290 (18)	0.045 (2)	0.038 (2)	−0.0043 (16)	−0.0016 (16)	0.0000 (18)
C26	0.0268 (19)	0.043 (2)	0.040 (2)	0.0046 (15)	−0.0010 (16)	−0.0048 (18)
O25	0.0251 (12)	0.0514 (14)	0.078 (2)	−0.0034 (11)	0.0020 (12)	−0.0053 (14)
C25A	0.0278 (19)	0.071 (2)	0.088 (3)	−0.0106 (17)	0.007 (2)	0.003 (3)
O26	0.0299 (12)	0.0441 (13)	0.0519 (17)	0.0056 (10)	−0.0008 (11)	−0.0082 (12)
S1	0.0359 (5)	0.0413 (5)	0.0717 (8)	0.0057 (5)	−0.0040 (5)	−0.0049 (6)
O1	0.0479 (16)	0.0467 (14)	0.118 (3)	0.0205 (12)	0.0066 (17)	−0.0144 (17)
O2	0.0457 (16)	0.0529 (15)	0.076 (2)	−0.0052 (13)	−0.0236 (14)	−0.0009 (14)
C31	0.040 (2)	0.035 (2)	0.059 (3)	0.0060 (17)	−0.0035 (19)	−0.003 (2)
C32	0.061 (3)	0.053 (2)	0.069 (3)	−0.005 (2)	−0.002 (2)	−0.012 (2)
C33	0.073 (3)	0.079 (3)	0.066 (3)	−0.003 (2)	0.010 (3)	−0.026 (3)
C34	0.050 (3)	0.078 (3)	0.059 (3)	0.004 (2)	0.004 (2)	0.003 (3)
C35	0.051 (3)	0.055 (3)	0.076 (4)	−0.002 (2)	−0.001 (2)	−0.004 (2)
C36	0.045 (2)	0.050 (2)	0.061 (3)	0.000 (2)	0.003 (2)	−0.006 (2)
C37	0.062 (3)	0.132 (4)	0.089 (4)	−0.008 (3)	0.013 (3)	−0.006 (3)
C41	0.047 (3)	0.041 (2)	0.064 (3)	0.0059 (19)	0.001 (2)	0.004 (2)
O41	0.0542 (17)	0.0609 (17)	0.071 (2)	0.0195 (13)	−0.0139 (16)	−0.0171 (18)
O42	0.0635 (19)	0.0542 (16)	0.065 (2)	0.0082 (14)	−0.0044 (16)	−0.0024 (15)
C42	0.062 (3)	0.070 (3)	0.089 (4)	0.029 (2)	0.002 (2)	0.005 (3)

Geometric parameters (Å, º)

S1—O1	1.418 (2)	C24—H24	0.9300
S1—O2	1.422 (2)	C16—H16	0.9300
S1—O26	1.610 (2)	C13—C12	1.385 (4)
S1—C31	1.743 (4)	C13—H13	0.9300
Cl1—C23	1.738 (3)	C36—C35	1.373 (5)
N17—C17	1.346 (4)	C36—C31	1.390 (5)
N17—N27	1.377 (3)	C36—H36	0.9300
N17—H17	0.8600	C12—H12	0.9300
O17—C17	1.229 (3)	C32—C31	1.375 (5)
O26—C26	1.406 (3)	C32—C33	1.377 (5)
C26—C21	1.389 (4)	C32—H32	0.9300
C26—C25	1.401 (4)	C34—C33	1.381 (5)
C21—C22	1.399 (4)	C34—C35	1.384 (5)
C21—C27	1.457 (4)	C34—C37	1.510 (6)
C22—C23	1.377 (4)	C35—H35	0.9300
C22—H22	0.9300	C33—H33	0.9300
O25—C25	1.356 (3)	O41—C41	1.304 (4)
O25—C25A	1.433 (3)	O41—H41	0.8200
N27—C27	1.277 (4)	O42—C41	1.216 (4)
C27—H27	0.9300	C25A—H25A	0.9600
C25—C24	1.381 (4)	C25A—H25B	0.9600
C14—C15	1.385 (4)	C25A—H25C	0.9600
C14—C13	1.389 (4)	C41—C42	1.495 (5)
C14—C17	1.488 (4)	C42—H42A	0.9600
N11—C12	1.322 (4)	C42—H42B	0.9600
N11—C16	1.327 (4)	C42—H42C	0.9600
C15—C16	1.380 (4)	C37—H37A	0.9600
C15—H15	0.9300	C37—H37B	0.9600
C24—C23	1.376 (4)	C37—H37C	0.9600
O1—S1—O2	120.13 (15)	C35—C36—C31	118.8 (4)
O1—S1—O26	102.53 (17)	C35—C36—H36	120.6
O2—S1—O26	107.68 (13)	C31—C36—H36	120.6
O1—S1—C31	110.46 (16)	C24—C23—C22	122.4 (3)
O2—S1—C31	109.27 (19)	C24—C23—Cl1	118.2 (2)
O26—S1—C31	105.61 (14)	C22—C23—Cl1	119.4 (3)
C17—N17—N27	118.9 (3)	N11—C12—C13	125.1 (3)
C17—N17—H17	120.6	N11—C12—H12	117.5
N27—N17—H17	120.6	C13—C12—H12	117.5
C26—O26—S1	118.4 (2)	C31—C32—C33	119.2 (4)
C21—C26—C25	121.7 (3)	C31—C32—H32	120.4
C21—C26—O26	120.7 (3)	C33—C32—H32	120.4
C25—C26—O26	117.5 (3)	C33—C34—C35	117.4 (4)
C26—C21—C22	117.8 (3)	C33—C34—C37	121.6 (5)
C26—C21—C27	121.0 (3)	C35—C34—C37	121.0 (4)
C22—C21—C27	121.2 (3)	C32—C31—C36	120.5 (4)
C23—C22—C21	119.8 (3)	C32—C31—S1	119.5 (3)
C23—C22—H22	120.1	C36—C31—S1	120.0 (3)
C21—C22—H22	120.1	C36—C35—C34	122.1 (4)
C25—O25—C25A	117.5 (2)	C36—C35—H35	118.9
C27—N27—N17	115.9 (3)	C34—C35—H35	118.9
N27—C27—C21	120.0 (3)	C32—C33—C34	122.0 (4)
N27—C27—H27	120.0	C32—C33—H33	119.0
C21—C27—H27	120.0	C34—C33—H33	119.0
O25—C25—C24	125.1 (3)	C41—O41—H41	109.5
O25—C25—C26	115.4 (3)	O25—C25A—H25A	109.5
C24—C25—C26	119.5 (3)	O25—C25A—H25B	109.5
C15—C14—C13	118.0 (3)	H25A—C25A—H25B	109.5
C15—C14—C17	123.0 (3)	O25—C25A—H25C	109.5
C13—C14—C17	118.9 (3)	H25A—C25A—H25C	109.5
O17—C17—N17	123.3 (3)	H25B—C25A—H25C	109.5
O17—C17—C14	120.8 (3)	O42—C41—O41	123.6 (4)
N17—C17—C14	115.9 (3)	O42—C41—C42	123.9 (4)
C12—N11—C16	115.8 (3)	O41—C41—C42	112.5 (4)
C16—C15—C14	118.6 (3)	C41—C42—H42A	109.5
C16—C15—H15	120.7	C41—C42—H42B	109.5
C14—C15—H15	120.7	H42A—C42—H42B	109.5
C23—C24—C25	118.7 (3)	C41—C42—H42C	109.5
C23—C24—H24	120.6	H42A—C42—H42C	109.5
C25—C24—H24	120.6	H42B—C42—H42C	109.5
N11—C16—C15	124.5 (3)	C34—C37—H37A	109.5
N11—C16—H16	117.7	C34—C37—H37B	109.5
C15—C16—H16	117.7	H37A—C37—H37B	109.5
C12—C13—C14	117.9 (3)	C34—C37—H37C	109.5
C12—C13—H13	121.1	H37A—C37—H37C	109.5
C14—C13—H13	121.1	H37B—C37—H37C	109.5
O1—S1—O26—C26	−174.7 (2)	O25—C25—C24—C23	−179.1 (3)
O2—S1—O26—C26	−47.0 (2)	C26—C25—C24—C23	0.8 (5)
C31—S1—O26—C26	69.6 (2)	C12—N11—C16—C15	1.3 (6)
S1—O26—C26—C21	85.7 (3)	C14—C15—C16—N11	−0.8 (6)
S1—O26—C26—C25	−97.4 (3)	C15—C14—C13—C12	0.9 (5)
C25—C26—C21—C22	1.3 (5)	C17—C14—C13—C12	178.7 (3)
O26—C26—C21—C22	178.1 (3)	C25—C24—C23—C22	−0.1 (6)
C25—C26—C21—C27	−179.2 (3)	C25—C24—C23—Cl1	179.0 (3)
O26—C26—C21—C27	−2.4 (5)	C21—C22—C23—C24	0.0 (6)
C26—C21—C22—C23	−0.6 (5)	C21—C22—C23—Cl1	−179.1 (3)
C27—C21—C22—C23	179.9 (3)	C16—N11—C12—C13	−0.7 (6)
C17—N17—N27—C27	174.6 (3)	C14—C13—C12—N11	−0.3 (6)
N17—N27—C27—C21	179.3 (3)	C33—C32—C31—C36	0.1 (6)
C26—C21—C27—N27	−164.9 (3)	C33—C32—C31—S1	−179.1 (3)
C22—C21—C27—N27	14.5 (5)	C35—C36—C31—C32	0.3 (6)
C25A—O25—C25—C24	−12.3 (5)	C35—C36—C31—S1	179.6 (3)
C25A—O25—C25—C26	167.9 (3)	O1—S1—C31—C32	146.7 (3)
C21—C26—C25—O25	178.4 (3)	O2—S1—C31—C32	12.4 (3)
O26—C26—C25—O25	1.5 (4)	O26—S1—C31—C32	−103.1 (3)
C21—C26—C25—C24	−1.4 (5)	O1—S1—C31—C36	−32.6 (4)
O26—C26—C25—C24	−178.3 (3)	O2—S1—C31—C36	−166.8 (3)
N27—N17—C17—O17	−5.1 (6)	O26—S1—C31—C36	77.6 (3)
N27—N17—C17—C14	173.3 (3)	C31—C36—C35—C34	−0.9 (6)
C15—C14—C17—O17	146.3 (4)	C33—C34—C35—C36	0.9 (6)
C13—C14—C17—O17	−31.4 (6)	C37—C34—C35—C36	−179.2 (4)
C15—C14—C17—N17	−32.2 (6)	C31—C32—C33—C34	−0.1 (6)
C13—C14—C17—N17	150.1 (3)	C35—C34—C33—C32	−0.4 (6)
C13—C14—C15—C16	−0.3 (5)	C37—C34—C33—C32	179.7 (4)
C17—C14—C15—C16	−178.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O41—H41···O17	0.82	1.83	2.649 (3)	177
N17—H17···O42^i	0.86	2.16	2.992 (4)	163
C33—H33···O25^ii	0.93	2.50	3.378 (6)	157
C24—H24···N11^iii	0.93	2.59	3.521 (4)	178

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