FK228 from Burkholderia thailandensis MSMB43.

FK228 [systematic name: (1S,4S,7Z,10S,16E,21R)-7-ethyl-idene-4,21-di(propan-2-yl)-2-oxa-12,13-dithia-5,8,20,23-tetra-za--bicyclo[8.7.6]tricos-16-ene-3,6,9,19,22-pentone], C(24)H(36)N(4)O(6)S(2), also known as FR901228, depsipeptide, NSC 630176, romidepsin, and marketed as Istodax by Celgene Corporation, is crystallized from ethyl acetate in P2(1) as compared to the absolute configuration of FK228, first crystallized from methanol in P2(1)2(1)2(1) [Shigematsu et al. (1994 ▶). J. Anti-biot.47, 311-314]. A slight difference is observed between the absolute configuration of FK228 and the present structure. The molecular structure is stabilized by intramolecular N-H⋯O hydrogen bonds. In the crystal, molecules are linked via N-H⋯O hydrogen bonds.

Related literature

For diverse natural products, see: Nguyen et al. (2008 ▶); Knappe et al. (2008 ▶); Seyedsayamdost et al. (2010 ▶); Biggins et al. (2011 ▶); Klausmeyer et al. (2011 ▶); Wang et al. (2011 ▶, 2012 ▶). For large-scale genome sequencing, see: Yu et al. (2006 ▶); Mukhopadhyay et al. (2010 ▶); Zhuo et al. (2012 ▶). For the initial discovery of FK228 from Chromobacterium violaceum No. 968 and its crystal structure report, see: Shigematsu et al. (1994 ▶); Ueda, Nakajima, Hori, Fujita et al. (1994 ▶). For the biological activities and mode of action of FK228, see: Furumai et al. (2002 ▶); Ueda, Manda et al. (1994 ▶); Ueda, Nakajima, Hori, Goto & Okuhara (1994 ▶). For biosynthetic studies of FK228, see: Cheng et al. (2007 ▶); Potharla et al. (2011 ▶); Wesener et al. (2011 ▶). For clinical application of FK228, see: Robey et al. (2011 ▶); StatBite (2010 ▶).

Experimental

Crystal data

C24H36N4O6S2

M = 540.69

Monoclinic,

a = 9.1085 (2) Å

b = 16.2431 (4) Å

c = 9.4192 (2) Å

β = 92.096 (1)°

V = 1392.64 (5) Å3

Z = 2

Cu Kα radiation

μ = 2.10 mm−1

T = 100 K

0.26 × 0.14 × 0.07 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: analytical (SADABS; Sheldrick, 2003 ▶) T min = 0.611, T max = 0.867

22577 measured reflections

4918 independent reflections

4859 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.065

S = 1.02

4918 reflections

343 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.15 e Å−3

Absolute structure: Flack (1983 ▶), 2188 Friedel pairs

Flack parameter: 0.022 (9)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681203601X/jj2148sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203601X/jj2148Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681203601X/jj2148Isup3.cdx

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

C24H36N4O6S2	F(000) = 576
Mr = 540.69	Dx = 1.289 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2yb	Cell parameters from 999 reflections
a = 9.1085 (2) Å	θ = 4.7–69.8°
b = 16.2431 (4) Å	µ = 2.10 mm−1
c = 9.4192 (2) Å	T = 100 K
β = 92.096 (1)°	Block, colourless
V = 1392.64 (5) Å3	0.26 × 0.14 × 0.07 mm
Z = 2

Bruker SMART APEXII area-detector diffractometer	4918 independent reflections
Radiation source: fine-focus sealed tube	4859 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
0.50° ω and 0.5 ° φ scans	θmax = 69.8°, θmin = 4.7°
Absorption correction: analytical (SADABS; Sheldrick, 2003)	h = −10→11
Tmin = 0.611, Tmax = 0.867	k = −19→19
22577 measured reflections	l = −11→11

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)] = 0.025	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.065	w = 1/[σ2(Fo2) + (0.0447P)2 + 0.2408P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
4918 reflections	Δρmax = 0.29 e Å−3
343 parameters	Δρmin = −0.15 e Å−3
1 restraint	Absolute structure: Flack (1983), 2188 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.022 (9)

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
S1	0.21741 (4)	0.87614 (3)	0.41260 (4)	0.02391 (9)
S2	0.21966 (4)	0.75561 (3)	0.35057 (4)	0.02177 (9)
O1	0.47759 (11)	0.86900 (7)	−0.17912 (11)	0.0166 (2)
O2	0.54893 (12)	0.83426 (7)	−0.39718 (11)	0.0228 (2)
O3	0.73140 (12)	1.08712 (7)	−0.12864 (11)	0.0188 (2)
O4	0.48889 (12)	1.02648 (7)	0.11054 (12)	0.0234 (2)
O5	0.68455 (11)	0.76827 (7)	−0.04745 (11)	0.0206 (2)
O6	0.74839 (11)	0.82368 (7)	0.32442 (11)	0.0175 (2)
N1	0.72350 (14)	0.94804 (8)	−0.11503 (13)	0.0155 (2)
H3	0.724 (2)	0.9060 (13)	−0.063 (2)	0.019*
N2	0.70812 (14)	0.97489 (8)	0.18875 (13)	0.0170 (3)
H4	0.750 (2)	0.9394 (13)	0.237 (2)	0.020*
N3	0.54236 (14)	0.69120 (8)	0.09041 (13)	0.0153 (2)
H16	0.467 (2)	0.6595 (13)	0.099 (2)	0.018*
N4	0.51449 (14)	0.83271 (8)	0.23715 (14)	0.0159 (3)
H18	0.454 (2)	0.8103 (13)	0.195 (2)	0.019*
C1	0.37318 (16)	0.80077 (9)	−0.18177 (16)	0.0171 (3)
H1	0.3247	0.7979	−0.2786	0.021*
C2	0.56600 (16)	0.87327 (10)	−0.28962 (14)	0.0168 (3)
C3	0.68786 (16)	0.93675 (10)	−0.26594 (15)	0.0167 (3)
H2	0.6488	0.9905	−0.3027	0.020*
C4	0.74312 (15)	1.02321 (10)	−0.05887 (15)	0.0157 (3)
C5	0.78862 (16)	1.02503 (9)	0.09680 (15)	0.0172 (3)
C6	0.55899 (17)	0.97821 (9)	0.18570 (15)	0.0169 (3)
C7	0.48646 (16)	0.91621 (10)	0.28501 (15)	0.0171 (3)
H5A	0.5281	0.9234	0.3839	0.021*
C8	0.32175 (17)	0.93220 (10)	0.28278 (16)	0.0200 (3)
H6	0.2808	0.9185	0.1869	0.024*
H7	0.3061	0.9918	0.2977	0.024*
C9	0.05712 (16)	0.74578 (10)	0.23338 (17)	0.0216 (3)
H8	0.0435	0.6869	0.2092	0.026*
H9	−0.0295	0.7635	0.2860	0.026*
C10	0.06058 (16)	0.79491 (11)	0.09558 (17)	0.0214 (3)
H10	−0.0326	0.7857	0.0404	0.026*
H11	0.0667	0.8543	0.1189	0.026*
C11	0.18736 (16)	0.77249 (10)	0.00426 (16)	0.0190 (3)
H12	0.2182	0.7166	0.0052	0.023*
C12	0.25928 (16)	0.82409 (10)	−0.07712 (17)	0.0190 (3)
H13	0.2369	0.8810	−0.0687	0.023*
C13	0.45645 (17)	0.71982 (10)	−0.15341 (15)	0.0172 (3)
H14	0.3854	0.6764	−0.1291	0.021*
H15	0.5048	0.7027	−0.2411	0.021*
C14	0.57163 (16)	0.72764 (9)	−0.03355 (15)	0.0162 (3)
C15	0.64392 (16)	0.70259 (9)	0.21230 (15)	0.0154 (3)
H17	0.7451	0.6916	0.1792	0.018*
C16	0.64070 (16)	0.79203 (9)	0.26422 (14)	0.0153 (3)
C17	0.82380 (17)	0.91592 (10)	−0.35219 (16)	0.0199 (3)
H19	0.7900	0.9098	−0.4539	0.024*
C18	0.93314 (19)	0.98732 (11)	−0.34389 (17)	0.0274 (4)
H22	0.8836	1.0383	−0.3742	0.041*
H21	1.0145	0.9761	−0.4063	0.041*
H20	0.9714	0.9934	−0.2459	0.041*
C19	0.89729 (19)	0.83572 (11)	−0.30681 (18)	0.0257 (4)
H24	0.9370	0.8410	−0.2091	0.039*
H25	0.9773	0.8234	−0.3703	0.039*
H23	0.8250	0.7910	−0.3118	0.039*
C20	0.90281 (18)	1.07072 (10)	0.14031 (17)	0.0230 (3)
H26	0.9536	1.1000	0.0699	0.028*
C21	0.9578 (2)	1.07966 (13)	0.2911 (2)	0.0358 (4)
H27	0.8802	1.0637	0.3550	0.054*
H29	0.9856	1.1371	0.3093	0.054*
H28	1.0436	1.0441	0.3079	0.054*
C22	0.61246 (18)	0.63859 (10)	0.32827 (17)	0.0201 (3)
H30	0.5052	0.6402	0.3475	0.024*
C23	0.65029 (19)	0.55289 (10)	0.27385 (19)	0.0253 (3)
H31	0.5935	0.5418	0.1855	0.038*
H32	0.6262	0.5117	0.3453	0.038*
H33	0.7555	0.5502	0.2558	0.038*
C24	0.6992 (2)	0.65666 (11)	0.46668 (18)	0.0301 (4)
H35	0.8045	0.6571	0.4488	0.045*
H34	0.6786	0.6140	0.5368	0.045*
H36	0.6700	0.7105	0.5033	0.045*

	U11	U22	U33	U12	U13	U23
S1	0.02086 (19)	0.0278 (2)	0.02363 (18)	0.00080 (16)	0.00810 (13)	−0.00407 (16)
S2	0.01743 (17)	0.02238 (19)	0.02566 (19)	0.00194 (15)	0.00309 (13)	0.00550 (15)
O1	0.0174 (5)	0.0153 (5)	0.0171 (5)	−0.0017 (4)	0.0011 (4)	0.0016 (4)
O2	0.0244 (6)	0.0277 (6)	0.0161 (5)	−0.0058 (5)	−0.0005 (4)	−0.0013 (5)
O3	0.0221 (5)	0.0140 (5)	0.0204 (5)	−0.0002 (4)	0.0005 (4)	0.0020 (4)
O4	0.0225 (6)	0.0182 (6)	0.0295 (6)	0.0029 (4)	−0.0013 (5)	0.0046 (5)
O5	0.0159 (5)	0.0223 (6)	0.0236 (5)	−0.0028 (4)	0.0004 (4)	0.0032 (4)
O6	0.0171 (5)	0.0176 (5)	0.0175 (5)	0.0001 (4)	−0.0034 (4)	−0.0004 (4)
N1	0.0191 (6)	0.0142 (6)	0.0132 (6)	−0.0004 (5)	0.0006 (5)	0.0013 (5)
N2	0.0199 (6)	0.0152 (6)	0.0157 (6)	0.0017 (5)	−0.0022 (5)	0.0012 (5)
N3	0.0141 (6)	0.0140 (6)	0.0179 (6)	−0.0013 (5)	0.0000 (5)	−0.0006 (5)
N4	0.0139 (6)	0.0150 (6)	0.0187 (6)	−0.0002 (5)	−0.0011 (5)	−0.0017 (5)
C1	0.0168 (7)	0.0170 (8)	0.0174 (7)	−0.0040 (6)	−0.0028 (5)	0.0020 (6)
C2	0.0189 (7)	0.0183 (7)	0.0130 (6)	0.0034 (6)	−0.0021 (5)	0.0040 (6)
C3	0.0181 (7)	0.0177 (7)	0.0144 (6)	−0.0005 (6)	−0.0001 (5)	0.0015 (6)
C4	0.0111 (6)	0.0171 (7)	0.0190 (7)	−0.0007 (5)	0.0030 (5)	0.0001 (6)
C5	0.0182 (7)	0.0141 (7)	0.0192 (7)	0.0018 (6)	0.0004 (5)	−0.0011 (6)
C6	0.0206 (7)	0.0128 (7)	0.0172 (7)	0.0004 (6)	0.0010 (6)	−0.0048 (6)
C7	0.0184 (7)	0.0171 (7)	0.0159 (7)	0.0006 (6)	0.0010 (5)	−0.0021 (6)
C8	0.0196 (7)	0.0167 (7)	0.0238 (7)	0.0023 (6)	0.0033 (6)	−0.0011 (6)
C9	0.0143 (7)	0.0229 (9)	0.0278 (8)	−0.0014 (6)	0.0033 (6)	0.0025 (7)
C10	0.0146 (7)	0.0220 (8)	0.0275 (8)	0.0015 (6)	−0.0007 (6)	0.0041 (7)
C11	0.0163 (7)	0.0173 (8)	0.0231 (7)	0.0001 (6)	−0.0024 (6)	0.0012 (6)
C12	0.0159 (7)	0.0161 (7)	0.0246 (8)	0.0016 (6)	−0.0038 (6)	0.0022 (6)
C13	0.0189 (7)	0.0170 (7)	0.0157 (7)	−0.0014 (6)	0.0013 (5)	−0.0001 (6)
C14	0.0166 (7)	0.0135 (7)	0.0185 (7)	0.0027 (6)	0.0010 (5)	−0.0012 (6)
C15	0.0127 (7)	0.0160 (7)	0.0173 (7)	0.0008 (5)	−0.0007 (5)	−0.0003 (6)
C16	0.0164 (7)	0.0181 (7)	0.0114 (6)	−0.0009 (6)	0.0014 (5)	0.0014 (6)
C17	0.0196 (7)	0.0263 (8)	0.0141 (6)	−0.0025 (7)	0.0017 (5)	−0.0025 (6)
C18	0.0245 (8)	0.0333 (10)	0.0249 (8)	−0.0088 (7)	0.0087 (7)	−0.0060 (7)
C19	0.0219 (8)	0.0319 (9)	0.0235 (8)	0.0026 (7)	0.0035 (6)	−0.0028 (7)
C20	0.0228 (8)	0.0198 (8)	0.0259 (8)	−0.0017 (6)	−0.0038 (6)	0.0025 (6)
C21	0.0375 (10)	0.0349 (11)	0.0338 (10)	−0.0069 (8)	−0.0157 (8)	−0.0019 (8)
C22	0.0214 (8)	0.0171 (8)	0.0215 (7)	−0.0006 (6)	−0.0021 (6)	0.0021 (6)
C23	0.0248 (8)	0.0166 (8)	0.0340 (9)	0.0021 (6)	−0.0072 (7)	0.0032 (7)
C24	0.0458 (11)	0.0210 (9)	0.0226 (8)	−0.0021 (8)	−0.0097 (7)	0.0059 (7)

S1—C8	1.8200 (16)	C9—H9	0.9900
S1—S2	2.0434 (6)	C10—C11	1.510 (2)
S2—C9	1.8211 (15)	C10—H10	0.9900
O1—C2	1.3408 (17)	C10—H11	0.9900
O1—C1	1.4599 (18)	C11—C12	1.325 (2)
O2—C2	1.2003 (19)	C11—H12	0.9500
O3—C4	1.2311 (19)	C12—H13	0.9500
O4—C6	1.2208 (19)	C13—C14	1.518 (2)
O5—C14	1.2331 (19)	C13—H14	0.9900
O6—C16	1.2277 (19)	C13—H15	0.9900
N1—C4	1.340 (2)	C15—C16	1.534 (2)
N1—C3	1.4580 (18)	C15—C22	1.542 (2)
N1—H3	0.84 (2)	C15—H17	1.0000
N2—C6	1.359 (2)	C17—C19	1.519 (2)
N2—C5	1.413 (2)	C17—C18	1.529 (2)
N2—H4	0.82 (2)	C17—H19	1.0000
N3—C14	1.344 (2)	C18—H22	0.9800
N3—C15	1.4596 (18)	C18—H21	0.9800
N3—H16	0.87 (2)	C18—H20	0.9800
N4—C16	1.342 (2)	C19—H24	0.9800
N4—C7	1.455 (2)	C19—H25	0.9800
N4—H18	0.76 (2)	C19—H23	0.9800
C1—C12	1.505 (2)	C20—C21	1.496 (2)
C1—C13	1.537 (2)	C20—H26	0.9500
C1—H1	1.0000	C21—H27	0.9800
C2—C3	1.525 (2)	C21—H29	0.9800
C3—C17	1.543 (2)	C21—H28	0.9800
C3—H2	1.0000	C22—C23	1.527 (2)
C4—C5	1.509 (2)	C22—C24	1.528 (2)
C5—C20	1.330 (2)	C22—H30	1.0000
C6—C7	1.540 (2)	C23—H31	0.9800
C7—C8	1.522 (2)	C23—H32	0.9800
C7—H5A	1.0000	C23—H33	0.9800
C8—H6	0.9900	C24—H35	0.9800
C8—H7	0.9900	C24—H34	0.9800
C9—C10	1.525 (2)	C24—H36	0.9800
C9—H8	0.9900
C8—S1—S2	106.04 (5)	C11—C12—C1	125.93 (15)
C9—S2—S1	103.94 (6)	C11—C12—H13	117.0
C2—O1—C1	115.81 (12)	C1—C12—H13	117.0
C4—N1—C3	121.41 (13)	C14—C13—C1	112.39 (13)
C4—N1—H3	120.8 (13)	C14—C13—H14	109.1
C3—N1—H3	117.6 (13)	C1—C13—H14	109.1
C6—N2—C5	120.32 (13)	C14—C13—H15	109.1
C6—N2—H4	118.8 (14)	C1—C13—H15	109.1
C5—N2—H4	120.4 (14)	H14—C13—H15	107.9
C14—N3—C15	119.16 (13)	O5—C14—N3	121.37 (13)
C14—N3—H16	122.0 (13)	O5—C14—C13	121.48 (13)
C15—N3—H16	118.8 (13)	N3—C14—C13	117.09 (13)
C16—N4—C7	123.97 (13)	N3—C15—C16	110.61 (12)
C16—N4—H18	117.8 (15)	N3—C15—C22	110.05 (12)
C7—N4—H18	118.2 (15)	C16—C15—C22	113.98 (12)
O1—C1—C12	105.19 (12)	N3—C15—H17	107.3
O1—C1—C13	109.24 (12)	C16—C15—H17	107.3
C12—C1—C13	116.69 (13)	C22—C15—H17	107.3
O1—C1—H1	108.5	O6—C16—N4	123.09 (14)
C12—C1—H1	108.5	O6—C16—C15	121.31 (14)
C13—C1—H1	108.5	N4—C16—C15	115.59 (13)
O2—C2—O1	124.40 (14)	C19—C17—C18	110.89 (14)
O2—C2—C3	123.47 (13)	C19—C17—C3	113.19 (13)
O1—C2—C3	112.08 (12)	C18—C17—C3	109.91 (13)
N1—C3—C2	111.25 (12)	C19—C17—H19	107.5
N1—C3—C17	112.74 (12)	C18—C17—H19	107.5
C2—C3—C17	111.62 (13)	C3—C17—H19	107.5
N1—C3—H2	106.9	C17—C18—H22	109.5
C2—C3—H2	106.9	C17—C18—H21	109.5
C17—C3—H2	106.9	H22—C18—H21	109.5
O3—C4—N1	123.36 (13)	C17—C18—H20	109.5
O3—C4—C5	121.16 (14)	H22—C18—H20	109.5
N1—C4—C5	115.42 (13)	H21—C18—H20	109.5
C20—C5—N2	123.37 (14)	C17—C19—H24	109.5
C20—C5—C4	119.61 (14)	C17—C19—H25	109.5
N2—C5—C4	116.99 (13)	H24—C19—H25	109.5
O4—C6—N2	122.62 (14)	C17—C19—H23	109.5
O4—C6—C7	123.05 (14)	H24—C19—H23	109.5
N2—C6—C7	114.33 (13)	H25—C19—H23	109.5
N4—C7—C8	109.81 (13)	C5—C20—C21	125.28 (16)
N4—C7—C6	109.72 (11)	C5—C20—H26	117.4
C8—C7—C6	108.94 (12)	C21—C20—H26	117.4
N4—C7—H5A	109.4	C20—C21—H27	109.5
C8—C7—H5A	109.4	C20—C21—H29	109.5
C6—C7—H5A	109.4	H27—C21—H29	109.5
C7—C8—S1	116.36 (11)	C20—C21—H28	109.5
C7—C8—H6	108.2	H27—C21—H28	109.5
S1—C8—H6	108.2	H29—C21—H28	109.5
C7—C8—H7	108.2	C23—C22—C24	110.22 (14)
S1—C8—H7	108.2	C23—C22—C15	109.06 (13)
H6—C8—H7	107.4	C24—C22—C15	111.79 (13)
C10—C9—S2	115.36 (11)	C23—C22—H30	108.6
C10—C9—H8	108.4	C24—C22—H30	108.6
S2—C9—H8	108.4	C15—C22—H30	108.6
C10—C9—H9	108.4	C22—C23—H31	109.5
S2—C9—H9	108.4	C22—C23—H32	109.5
H8—C9—H9	107.5	H31—C23—H32	109.5
C11—C10—C9	113.50 (13)	C22—C23—H33	109.5
C11—C10—H10	108.9	H31—C23—H33	109.5
C9—C10—H10	108.9	H32—C23—H33	109.5
C11—C10—H11	108.9	C22—C24—H35	109.5
C9—C10—H11	108.9	C22—C24—H34	109.5
H10—C10—H11	107.7	H35—C24—H34	109.5
C12—C11—C10	125.57 (15)	C22—C24—H36	109.5
C12—C11—H12	117.2	H35—C24—H36	109.5
C10—C11—H12	117.2	H34—C24—H36	109.5
C8—S1—S2—C9	−90.18 (7)	S1—S2—C9—C10	65.73 (12)
C2—O1—C1—C12	−162.59 (12)	S2—C9—C10—C11	59.05 (17)
C2—O1—C1—C13	71.42 (15)	C9—C10—C11—C12	−145.87 (15)
C1—O1—C2—O2	12.5 (2)	C10—C11—C12—C1	−172.08 (15)
C1—O1—C2—C3	−170.18 (12)	O1—C1—C12—C11	−146.55 (14)
C4—N1—C3—C2	−135.83 (14)	C13—C1—C12—C11	−25.3 (2)
C4—N1—C3—C17	97.90 (17)	O1—C1—C13—C14	43.45 (16)
O2—C2—C3—N1	−155.37 (14)	C12—C1—C13—C14	−75.63 (16)
O1—C2—C3—N1	27.23 (17)	C15—N3—C14—O5	2.3 (2)
O2—C2—C3—C17	−28.5 (2)	C15—N3—C14—C13	−175.03 (12)
O1—C2—C3—C17	154.12 (12)	C1—C13—C14—O5	−70.20 (18)
C3—N1—C4—O3	0.7 (2)	C1—C13—C14—N3	107.10 (15)
C3—N1—C4—C5	−176.38 (12)	C14—N3—C15—C16	68.10 (16)
C6—N2—C5—C20	131.38 (16)	C14—N3—C15—C22	−165.07 (13)
C6—N2—C5—C4	−50.66 (19)	C7—N4—C16—O6	−4.9 (2)
O3—C4—C5—C20	−46.7 (2)	C7—N4—C16—C15	176.20 (12)
N1—C4—C5—C20	130.44 (16)	N3—C15—C16—O6	−152.01 (13)
O3—C4—C5—N2	135.23 (15)	C22—C15—C16—O6	83.37 (17)
N1—C4—C5—N2	−47.60 (18)	N3—C15—C16—N4	26.90 (17)
C5—N2—C6—O4	−3.8 (2)	C22—C15—C16—N4	−97.72 (15)
C5—N2—C6—C7	176.31 (12)	N1—C3—C17—C19	61.93 (18)
C16—N4—C7—C8	−160.22 (13)	C2—C3—C17—C19	−64.14 (16)
C16—N4—C7—C6	80.06 (16)	N1—C3—C17—C18	−62.66 (17)
O4—C6—C7—N4	114.64 (16)	C2—C3—C17—C18	171.27 (12)
N2—C6—C7—N4	−65.46 (16)	N2—C5—C20—C21	−3.5 (3)
O4—C6—C7—C8	−5.61 (19)	C4—C5—C20—C21	178.62 (16)
N2—C6—C7—C8	174.30 (12)	N3—C15—C22—C23	66.98 (16)
N4—C7—C8—S1	68.66 (14)	C16—C15—C22—C23	−168.10 (12)
C6—C7—C8—S1	−171.15 (10)	N3—C15—C22—C24	−170.88 (13)
S2—S1—C8—C7	−69.44 (12)	C16—C15—C22—C24	−45.97 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H3···O5	0.84 (2)	2.27 (2)	3.0123 (18)	147.1 (17)
N2—H4···O6	0.82 (2)	2.05 (2)	2.7867 (18)	149.1 (18)
N3—H16···O3i	0.87 (2)	2.18 (2)	3.0449 (17)	175.9 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H3⋯O5	0.84 (2)	2.27 (2)	3.0123 (18)	147.1 (17)
N2—H4⋯O6	0.82 (2)	2.05 (2)	2.7867 (18)	149.1 (18)
N3—H16⋯O3i	0.87 (2)	2.18 (2)	3.0449 (17)	175.9 (18)

Symmetry code: (i) .