Albofungin and chloro­albofungin: anti­biotic crystals with 2D but not 3D isostructurality

The potent anti­biotics albofungin [systematic name: (1S,4R,8aR)-13-amino-1,15,16-trihy­droxy-4-meth­oxy-12-methyl-3,4,8a,13-tetra­hydro-1H-xantheno[4′,3′,2′:4,5][1,3]benzodioxino[7,6-g]iso­quinoline-14,17(2H,9H)-dione, C₂₇H₂₄N₂O₉, 1] and its chlorinated analogue chloro­albofungin (the 11-chloro analogue, C₂₇H₂₃ClN₂O₉, 2) have been crystallized following their isolation from the bacterial strain Streptomyces chrestomyceticus and their structures determined by single-crystal X-ray diffraction. The novel N-amino­quinolone mol­ecular arrangement shows N—N bond lengths of 1.4202 (16) and 1.424 (2) Å in 1 and 2, respectively. The regiochemistry of chloro substitution in the A-ring is para to the quinolone O atom, with a C—Cl bond length of 1.741 (2) Å. The absolute stereochemistry at three chiral centres of the xanthone rings (i.e. 10S, 13R and 19R) is confirmed. Both com­pounds crystallize in chiral Sohncke space groups consistent with enanti­opurity, but are not fully isostructural. A preserved supra­molecular construct (SC) confers two-dimensional (2D) isostructurality, but the SC self-associates via either a twofold screw operation in 1, giving a monoclinic P2₁ structure, or a twofold rotation in 2, affording a monoclinic C2 structure with a doubled unit-cell axis.

Computing details

Data collection: SAINT (Bruker, 2016) for ye2_213K; CrysAlis PRO (Rigaku OD, 2020) for ye18a_100K. Cell refinement: APEX3 (Bruker, 2016) for ye2_213K; CrysAlis PRO (Rigaku OD, 2020) for ye18a_100K. Data reduction: SAINT (Bruker, 2016) for ye2_213K; CrysAlis PRO (Rigaku OD, 2020) for ye18a_100K. For both structures, program(s) used to solve structure: SHELXT (Sheldrick, 2015); program(s) used to refine structure: olex2.refine (Bourhis et al., 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

(1S,4R,8aR)-13-Amino-1,15,16-trihydroxy-4-methoxy-12-methyl-3,4,8a,13-tetrahydro-1H-xantheno[4',3',2':4,5][1,3]benzodioxino[7,6-g]isoquinoline-14,17(2H,9H)-dione (ye2_213K)

Crystal data

C27H24N2O9	F(000) = 546.0337
Mr = 520.50	Dx = 1.474 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54178 Å
a = 13.5302 (4) Å	Cell parameters from 8987 reflections
b = 4.6101 (1) Å	θ = 3.6–74.2°
c = 19.3371 (6) Å	µ = 0.94 mm^−1
β = 103.603 (1)°	T = 213 K
V = 1172.33 (6) Å^3	Block, yellow
Z = 2	0.1 × 0.08 × 0.08 mm

Data collection

Bruker SMART APEX3 CCD area detector diffractometer	4555 reflections with I ≥ 2u(I)
Detector resolution: 7.9 pixels mm^-1	Rint = 0.043
ω and φ scans	θmax = 74.6°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −16→16
Tmin = 0.921, Tmax = 1.000	k = −5→5
46473 measured reflections	l = −24→24
4781 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.028	w = 1/[σ^2(Fo^2) + (0.040P)^2 + 0.1387P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.075	(Δ/σ)max = 0.0001
S = 1.07	Δρmax = 0.16 e Å^−3
4781 reflections	Δρmin = −0.13 e Å^−3
377 parameters	Absolute structure: Parsons et al. (2013)
1 restraint	Absolute structure parameter: −0.00 (10)
36 constraints

Special details

Refinement. X-ray diffraction data of 1 were collected at 213K (-60^oC) on a Bruker Smart Apex 3 diffractometer and 2 at 100K on Rigaku-Oxford Diffraction Supernova both using a Cu-K? source. Both structures were solved using an embedded SHELXT program (Sheldrick 2015) and refined by internal options from within the Olex2 suite (Dolomanov et al., 2009, Bourhis et al. 2015).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.52992 (7)	−0.1409 (2)	0.06168 (5)	0.0335 (2)
O3	0.46938 (7)	0.1366 (2)	0.15833 (5)	0.0311 (2)
H3	0.4750 (15)	−0.009 (6)	0.1237 (11)	0.070 (6)*
O6	0.35990 (7)	0.6074 (2)	0.15406 (5)	0.0316 (2)
H6	0.2939 (16)	0.665 (5)	0.1450 (11)	0.063 (6)*
O8	0.18253 (7)	0.7762 (3)	0.16474 (5)	0.0457 (3)
O10	−0.00002 (8)	0.7502 (3)	0.20150 (6)	0.0458 (3)
H10	0.0360 (19)	0.730 (6)	0.1714 (13)	0.082 (8)*
O13	0.1354 (3)	0.8792 (4)	0.43994 (12)	0.0485 (6)	0.741 (8)
O15	0.29965 (7)	0.9652 (3)	0.37410 (5)	0.0409 (2)
O17	0.49648 (7)	0.9243 (3)	0.43578 (5)	0.0487 (3)
O19	0.66321 (7)	0.9037 (2)	0.42229 (5)	0.0396 (2)
O13A	0.1034 (5)	0.9070 (6)	0.4323 (4)	0.0394 (17)*	0.259 (8)
N1	0.68687 (8)	−0.0520 (3)	0.04310 (5)	0.0324 (2)
N2	0.66754 (10)	−0.2621 (3)	−0.01214 (6)	0.0399 (3)
H2a	0.6159 (16)	−0.374 (5)	−0.0033 (11)	0.060 (6)*
H2b	0.6403 (15)	−0.157 (5)	−0.0567 (11)	0.061 (6)*
C1	0.61166 (9)	−0.0009 (3)	0.07868 (6)	0.0288 (3)
C2	0.63312 (9)	0.2134 (3)	0.13460 (7)	0.0274 (2)
C3	0.55687 (9)	0.2864 (3)	0.17092 (6)	0.0264 (2)
C4	0.57410 (9)	0.5038 (3)	0.22258 (6)	0.0267 (2)
C5	0.49566 (9)	0.6082 (3)	0.25851 (6)	0.0276 (3)
C6	0.39345 (9)	0.6523 (3)	0.22449 (6)	0.0283 (3)
C7	0.32530 (9)	0.7692 (3)	0.26319 (7)	0.0312 (3)
C8	0.21927 (10)	0.8245 (3)	0.22912 (7)	0.0342 (3)
C9	0.15714 (10)	0.9410 (3)	0.27463 (7)	0.0334 (3)
C10	0.04506 (10)	0.9954 (3)	0.24175 (8)	0.0361 (3)
H10a	0.03900 (10)	1.1647 (3)	0.20952 (8)	0.0434 (4)*
C11	−0.01444 (11)	1.0569 (3)	0.29729 (9)	0.0412 (3)
H11a	−0.07988 (11)	1.1451 (3)	0.27444 (9)	0.0495 (4)*
H11b	−0.02808 (11)	0.8743 (3)	0.31927 (9)	0.0495 (4)*
C12	0.04396 (12)	1.2596 (3)	0.35431 (9)	0.0450 (4)
H12a	0.05858 (12)	1.4407 (3)	0.33211 (9)	0.0540 (4)*
H12b	0.00187 (12)	1.3066 (3)	0.38767 (9)	0.0540 (4)*
C13	0.14306 (11)	1.1245 (3)	0.39480 (8)	0.0400 (3)
H13	0.18529 (11)	1.2763 (3)	0.42382 (8)	0.0481 (4)*	0.741 (8)
H13a	0.18512 (11)	1.2655 (3)	0.42766 (8)	0.0481 (4)*	0.259 (8)
C14	0.19945 (10)	1.0037 (3)	0.34290 (8)	0.0357 (3)
C16	0.36156 (10)	0.8488 (3)	0.33420 (7)	0.0352 (3)
C17	0.46413 (10)	0.8227 (3)	0.36732 (7)	0.0362 (3)
C18	0.52891 (9)	0.7059 (3)	0.32913 (7)	0.0305 (3)
C19	0.64201 (9)	0.7110 (3)	0.36207 (7)	0.0313 (3)
H19	0.66603 (9)	0.5131 (3)	0.37728 (7)	0.031 (4)*
C20	0.69645 (9)	0.8223 (3)	0.30742 (7)	0.0313 (3)
H20a	0.67329 (9)	1.0191 (3)	0.29276 (7)	0.0376 (3)*
H20b	0.76989 (9)	0.8287 (3)	0.32797 (7)	0.0376 (3)*
C21	0.67384 (9)	0.6223 (3)	0.24387 (6)	0.0277 (2)
C22	0.74879 (9)	0.5473 (3)	0.20989 (7)	0.0301 (3)
H22	0.81386 (9)	0.6299 (3)	0.22471 (7)	0.0361 (3)*
C23	0.72899 (9)	0.3483 (3)	0.15324 (6)	0.0291 (3)
C24	0.80369 (10)	0.2677 (3)	0.11541 (7)	0.0346 (3)
H24	0.86871 (10)	0.3520 (3)	0.12814 (7)	0.0416 (3)*
C25	0.78279 (10)	0.0728 (3)	0.06167 (7)	0.0348 (3)
C26	0.85764 (12)	−0.0172 (4)	0.01966 (9)	0.0506 (4)
H26a	0.8333 (5)	0.043 (3)	−0.02944 (19)	0.0759 (6)*
H26b	0.9229 (3)	0.073 (2)	0.0396 (5)	0.0759 (6)*
H26c	0.8653 (8)	−0.2264 (5)	0.0216 (6)	0.0759 (6)*
C27	0.59860 (11)	0.8406 (4)	0.46745 (7)	0.0466 (4)
H27a	0.62233 (11)	0.9437 (4)	0.51264 (7)	0.0559 (5)*
H27b	0.60086 (11)	0.6321 (4)	0.47756 (7)	0.0559 (5)*
C28	0.1208 (2)	0.9606 (7)	0.50777 (12)	0.0623 (10)	0.741 (8)
H28a	0.1719 (11)	1.102 (4)	0.5293 (6)	0.0935 (16)*	0.741 (8)
H28b	0.0537 (7)	1.045 (5)	0.50221 (17)	0.0935 (16)*	0.741 (8)
H28c	0.1268 (18)	0.7906 (10)	0.5380 (4)	0.0935 (16)*	0.741 (8)
C28A	0.1709 (7)	0.8652 (9)	0.4982 (4)	0.055 (3)*	0.259 (8)
H28d	0.2392 (10)	0.841 (14)	0.4914 (5)	0.082 (4)*	0.259 (8)
H28e	0.169 (4)	1.033 (6)	0.5282 (13)	0.082 (4)*	0.259 (8)
H28f	0.151 (3)	0.693 (8)	0.5206 (15)	0.082 (4)*	0.259 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0366 (5)	0.0303 (5)	0.0317 (4)	−0.0022 (4)	0.0042 (4)	−0.0012 (4)
O3	0.0292 (4)	0.0270 (4)	0.0369 (5)	−0.0048 (4)	0.0071 (4)	−0.0010 (4)
O6	0.0274 (4)	0.0385 (5)	0.0266 (4)	0.0006 (4)	0.0017 (3)	−0.0034 (4)
O8	0.0304 (5)	0.0684 (8)	0.0343 (5)	0.0057 (5)	−0.0001 (4)	−0.0092 (5)
O10	0.0313 (5)	0.0478 (6)	0.0561 (7)	−0.0041 (5)	0.0056 (5)	−0.0077 (5)
O13	0.0569 (14)	0.0507 (10)	0.0414 (11)	0.0092 (9)	0.0189 (10)	0.0054 (8)
O15	0.0313 (5)	0.0592 (7)	0.0317 (5)	0.0046 (5)	0.0066 (4)	−0.0080 (5)
O17	0.0356 (5)	0.0807 (9)	0.0260 (4)	0.0106 (6)	−0.0003 (4)	−0.0104 (5)
O19	0.0347 (5)	0.0523 (6)	0.0282 (4)	−0.0001 (5)	0.0005 (3)	−0.0071 (5)
N1	0.0353 (5)	0.0352 (6)	0.0258 (5)	0.0038 (5)	0.0051 (4)	−0.0001 (5)
N2	0.0467 (7)	0.0442 (7)	0.0275 (6)	0.0017 (6)	0.0060 (5)	−0.0071 (5)
C1	0.0308 (6)	0.0270 (6)	0.0268 (6)	0.0040 (5)	0.0035 (5)	0.0056 (5)
C2	0.0290 (6)	0.0248 (6)	0.0266 (6)	0.0025 (5)	0.0031 (5)	0.0047 (5)
C3	0.0257 (5)	0.0239 (6)	0.0278 (6)	0.0004 (5)	0.0028 (4)	0.0052 (5)
C4	0.0272 (6)	0.0249 (6)	0.0267 (5)	0.0012 (5)	0.0035 (4)	0.0041 (5)
C5	0.0283 (6)	0.0263 (6)	0.0273 (6)	−0.0005 (5)	0.0044 (5)	0.0029 (5)
C6	0.0286 (6)	0.0282 (6)	0.0266 (6)	−0.0021 (5)	0.0039 (5)	0.0002 (5)
C7	0.0270 (6)	0.0365 (7)	0.0291 (6)	0.0007 (5)	0.0048 (5)	−0.0006 (5)
C8	0.0296 (6)	0.0386 (7)	0.0330 (6)	−0.0014 (5)	0.0044 (5)	−0.0033 (6)
C9	0.0281 (6)	0.0321 (7)	0.0393 (7)	0.0011 (5)	0.0068 (5)	−0.0007 (6)
C10	0.0289 (6)	0.0344 (7)	0.0438 (7)	0.0019 (6)	0.0058 (5)	0.0018 (6)
C11	0.0313 (6)	0.0381 (8)	0.0553 (9)	0.0055 (6)	0.0120 (6)	0.0014 (7)
C12	0.0442 (8)	0.0374 (8)	0.0586 (9)	0.0048 (7)	0.0225 (7)	−0.0034 (7)
C13	0.0414 (7)	0.0380 (7)	0.0441 (8)	−0.0026 (7)	0.0166 (6)	−0.0073 (7)
C14	0.0310 (6)	0.0370 (7)	0.0397 (7)	0.0011 (6)	0.0094 (5)	−0.0026 (6)
C16	0.0308 (6)	0.0444 (8)	0.0304 (6)	0.0028 (6)	0.0075 (5)	−0.0032 (6)
C17	0.0337 (6)	0.0474 (8)	0.0255 (6)	0.0019 (6)	0.0025 (5)	−0.0039 (6)
C18	0.0267 (6)	0.0352 (7)	0.0274 (6)	0.0015 (5)	0.0022 (5)	0.0028 (5)
C19	0.0300 (6)	0.0345 (7)	0.0261 (6)	0.0023 (5)	−0.0001 (5)	0.0000 (5)
C20	0.0284 (6)	0.0305 (7)	0.0325 (6)	−0.0015 (5)	0.0019 (5)	0.0000 (5)
C21	0.0280 (6)	0.0244 (6)	0.0285 (6)	0.0011 (5)	0.0020 (4)	0.0035 (5)
C22	0.0251 (5)	0.0294 (6)	0.0338 (6)	−0.0004 (5)	0.0029 (5)	0.0028 (5)
C23	0.0268 (6)	0.0298 (6)	0.0291 (6)	0.0035 (5)	0.0032 (5)	0.0050 (5)
C24	0.0276 (6)	0.0412 (8)	0.0345 (6)	0.0023 (6)	0.0061 (5)	0.0029 (6)
C25	0.0320 (6)	0.0422 (8)	0.0295 (6)	0.0048 (6)	0.0055 (5)	0.0045 (6)
C26	0.0423 (8)	0.0709 (12)	0.0411 (7)	0.0028 (8)	0.0147 (6)	−0.0062 (8)
C27	0.0349 (7)	0.0747 (12)	0.0268 (6)	0.0063 (8)	0.0005 (5)	−0.0016 (7)
C28	0.0581 (17)	0.092 (2)	0.0400 (12)	−0.0018 (16)	0.0173 (10)	0.0001 (14)

Geometric parameters (Å, º)

O1—C1	1.2558 (15)	C10—H10a	0.9900
O3—H3	0.96 (2)	C10—C11	1.513 (2)
O3—C3	1.3425 (15)	C11—H11a	0.9800
O6—H6	0.91 (2)	C11—H11b	0.9800
O6—C6	1.3465 (15)	C11—C12	1.518 (2)
O8—C8	1.2472 (16)	C12—H12a	0.9800
O10—H10	0.85 (2)	C12—H12b	0.9800
O10—C10	1.4259 (18)	C12—C13	1.518 (2)
O13—C13	1.447 (2)	C13—H13	0.9900
O13—C28	1.422 (3)	C13—H13a	0.9900
O15—C14	1.3597 (16)	C13—C14	1.5034 (19)
O15—C16	1.3744 (16)	C16—C17	1.3902 (18)
O17—C17	1.3753 (16)	C17—C18	1.3812 (19)
O17—C27	1.4265 (16)	C18—C19	1.5131 (17)
O19—C19	1.4388 (16)	C19—H19	0.9899
O19—C27	1.4039 (18)	C19—C20	1.5129 (18)
O13A—C13	1.415 (6)	C20—H20a	0.9800
O13A—C28A	1.394 (10)	C20—H20b	0.9800
N1—N2	1.4202 (16)	C20—C21	1.5090 (17)
N1—C1	1.3761 (16)	C21—C22	1.3760 (18)
N1—C25	1.3874 (18)	C22—H22	0.9400
N2—H2a	0.92 (2)	C22—C23	1.4053 (18)
N2—H2b	0.98 (2)	C23—C24	1.4291 (18)
C1—C2	1.4429 (18)	C24—H24	0.9400
C2—C3	1.4183 (17)	C24—C25	1.353 (2)
C2—C23	1.4069 (17)	C25—C26	1.4982 (19)
C3—C4	1.3954 (17)	C26—H26a	0.9700
C4—C5	1.4790 (17)	C26—H26b	0.9700
C4—C21	1.4238 (16)	C26—H26c	0.9700
C5—C6	1.3995 (16)	C27—H27a	0.9800
C5—C18	1.4074 (18)	C27—H27b	0.9800
C6—C7	1.4231 (17)	C28—H28a	0.9700
C7—C8	1.4534 (17)	C28—H28b	0.9700
C7—C16	1.3942 (18)	C28—H28c	0.9700
C8—C9	1.4551 (19)	C28A—H28d	0.9700
C9—C10	1.5211 (17)	C28A—H28e	0.9700
C9—C14	1.3410 (19)	C28A—H28f	0.9700
C3—O3—H3	105.9 (12)	C13—C14—C9	124.81 (12)
C6—O6—H6	103.4 (13)	C7—C16—O15	122.40 (11)
C10—O10—H10	102.8 (18)	C17—C16—O15	116.71 (11)
C16—O15—C14	118.53 (10)	C17—C16—C7	120.85 (12)
C27—O17—C17	112.21 (11)	C16—C17—O17	118.11 (12)
C27—O19—C19	109.91 (11)	C18—C17—O17	123.31 (11)
C1—N1—N2	117.77 (11)	C18—C17—C16	118.54 (12)
C25—N1—N2	118.23 (11)	C17—C18—C5	123.04 (11)
C25—N1—C1	123.81 (11)	C19—C18—C5	118.32 (11)
H2a—N2—N1	104.9 (13)	C19—C18—C17	118.35 (11)
H2b—N2—N1	106.8 (13)	C18—C19—O19	109.87 (10)
H2b—N2—H2a	107.2 (17)	H19—C19—O19	109.9
N1—C1—O1	119.36 (12)	H19—C19—C18	109.84 (7)
C2—C1—O1	123.91 (11)	C20—C19—O19	108.60 (11)
C2—C1—N1	116.73 (11)	C20—C19—C18	108.76 (10)
C3—C2—C1	119.47 (11)	C20—C19—H19	109.90 (7)
C23—C2—C1	120.36 (11)	H20a—C20—C19	109.92 (7)
C23—C2—C3	120.17 (11)	H20b—C20—C19	109.92 (6)
C2—C3—O3	120.08 (11)	H20b—C20—H20a	108.3
C4—C3—O3	119.41 (11)	C21—C20—C19	108.84 (11)
C4—C3—C2	120.43 (11)	C21—C20—H20a	109.92 (7)
C5—C4—C3	123.53 (11)	C21—C20—H20b	109.92 (7)
C21—C4—C3	118.02 (11)	C20—C21—C4	117.82 (11)
C21—C4—C5	118.39 (11)	C22—C21—C4	121.36 (11)
C6—C5—C4	124.43 (11)	C22—C21—C20	120.75 (11)
C18—C5—C4	117.32 (11)	H22—C22—C21	119.69 (7)
C18—C5—C6	117.68 (11)	C23—C22—C21	120.62 (11)
C5—C6—O6	120.92 (11)	C23—C22—H22	119.69 (7)
C7—C6—O6	118.95 (11)	C22—C23—C2	118.91 (11)
C7—C6—C5	119.92 (11)	C24—C23—C2	118.33 (12)
C8—C7—C6	121.37 (11)	C24—C23—C22	122.72 (11)
C16—C7—C6	119.74 (11)	H24—C24—C23	119.31 (7)
C16—C7—C8	118.78 (12)	C25—C24—C23	121.38 (12)
C7—C8—O8	122.71 (12)	C25—C24—H24	119.31 (8)
C9—C8—O8	121.22 (12)	C24—C25—N1	119.22 (12)
C9—C8—C7	116.08 (11)	C26—C25—N1	117.09 (13)
C10—C9—C8	117.97 (12)	C26—C25—C24	123.69 (13)
C14—C9—C8	120.09 (12)	H26a—C26—C25	109.5
C14—C9—C10	121.92 (12)	H26b—C26—C25	109.5
C9—C10—O10	110.71 (11)	H26b—C26—H26a	109.5
H10a—C10—O10	108.67 (8)	H26c—C26—C25	109.5
H10a—C10—C9	108.67 (8)	H26c—C26—H26a	109.5
C11—C10—O10	107.78 (12)	H26c—C26—H26b	109.5
C11—C10—C9	112.26 (12)	O19—C27—O17	111.03 (11)
C11—C10—H10a	108.67 (8)	H27a—C27—O17	109.43 (8)
H11a—C11—C10	109.44 (8)	H27a—C27—O19	109.43 (8)
H11b—C11—C10	109.44 (8)	H27b—C27—O17	109.43 (9)
H11b—C11—H11a	108.0	H27b—C27—O19	109.43 (9)
C12—C11—C10	110.98 (12)	H27b—C27—H27a	108.0
C12—C11—H11a	109.44 (8)	H28a—C28—O13	109.5
C12—C11—H11b	109.44 (9)	H28b—C28—O13	109.5
H12a—C12—C11	109.31 (9)	H28b—C28—H28a	109.5
H12b—C12—C11	109.31 (8)	H28c—C28—O13	109.5
H12b—C12—H12a	108.0	H28c—C28—H28a	109.5
C13—C12—C11	111.58 (12)	H28c—C28—H28b	109.5
C13—C12—H12a	109.31 (8)	H28d—C28A—O13A	109.5
C13—C12—H12b	109.31 (8)	H28e—C28A—O13A	109.5
H13—C13—O13	108.92 (11)	H28e—C28A—H28d	109.5
H13a—C13—O13A	111.5 (3)	H28f—C28A—O13A	109.5
C14—C13—C12	109.45 (12)	H28f—C28A—H28d	109.5
C9—C14—O15	123.98 (12)	H28f—C28A—H28e	109.5
C13—C14—O15	111.21 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1	0.96 (2)	1.67 (2)	2.5535 (13)	151 (2)
O6—H6···O8	0.91 (2)	1.72 (2)	2.5769 (14)	157 (2)
O10—H10···O8	0.85 (3)	2.03 (3)	2.7288 (15)	140 (2)
N2—H2a···O1^i	0.92 (2)	2.37 (2)	3.1466 (17)	142.0 (17)
N2—H2b···O6^i	0.98 (2)	2.24 (2)	3.1767 (15)	158.7 (17)

Symmetry code: (i) −x+1, y−1/2, −z.

(1S,4R,8aR)-13-Amino-11-chloro-1,15,16-trihydroxy-4-methoxy-12-methyl-3,4,8a,13-tetrahydro-1H-xantheno[4',3',2':4,5][1,3]benzodioxino[7,6-g]isoquinoline-14,17(2H,9H)-dione (ye18a_100K)

Crystal data

C27H23ClN2O9	F(000) = 1157.5525
Mr = 554.94	Dx = 1.591 Mg m^−3
Monoclinic, C2	Cu Kα radiation, λ = 1.54184 Å
a = 40.6637 (9) Å	Cell parameters from 4359 reflections
b = 4.52749 (12) Å	θ = 3.5–72.4°
c = 12.7049 (3) Å	µ = 2.03 mm^−1
β = 98.027 (2)°	T = 100 K
V = 2316.12 (10) Å^3	Needle, yellow
Z = 4	0.18 × 0.03 × 0.03 mm

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Atlas detector	4010 reflections with I ≥ 2u(I)
Detector resolution: 5.1788 pixels mm^-1	Rint = 0.029
ω scans	θmax = 72.6°, θmin = 2.2°
Absorption correction: multi-scan (CrysAlis PRO (Rigaku OD, 2020)	h = −49→49
Tmin = 0.820, Tmax = 1.000	k = −5→5
8597 measured reflections	l = −15→12
4376 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.034	w = 1/[σ^2(Fo^2) + (0.040P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.082	(Δ/σ)max = 0.001
S = 1.02	Δρmax = 0.25 e Å^−3
4376 reflections	Δρmin = −0.19 e Å^−3
374 parameters	Absolute structure: Parsons et al. (2013)
1 restraint	Absolute structure parameter: 0.002 (14)
28 constraints

Special details

Refinement. X-ray diffraction data of 1 were collected at 213K (-60^oC) on a Bruker Smart Apex 3 diffractometer and 2 at 100K on Rigaku-Oxford Diffraction Supernova both using a Cu-K? source. Both structures were solved using an embedded SHELXT program (Sheldrick 2015) and refined by internal options from within the Olex2 suite (Dolomanov et al., 2009, Bourhis et al. 2015).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.198485 (13)	0.49129 (11)	0.06464 (4)	0.02992 (13)
O1	0.22011 (3)	1.0756 (3)	0.47453 (12)	0.0230 (3)
N1	0.23576 (4)	0.9694 (4)	0.31406 (14)	0.0226 (4)
C1	0.21491 (5)	0.9317 (5)	0.38929 (16)	0.0198 (4)
H3	0.1867 (8)	0.909 (8)	0.537 (3)	0.050 (10)*
N2	0.26239 (5)	1.1740 (4)	0.33733 (16)	0.0273 (4)
C2	0.18820 (5)	0.7223 (5)	0.36416 (17)	0.0196 (4)
O3	0.17107 (4)	0.8000 (3)	0.53517 (12)	0.0218 (3)
C3	0.16744 (5)	0.6544 (5)	0.44249 (16)	0.0186 (4)
H10	0.1524 (8)	−0.002 (10)	0.981 (3)	0.069 (11)*
C4	0.14256 (5)	0.4413 (4)	0.42244 (16)	0.0187 (4)
C5	0.12239 (5)	0.3302 (5)	0.50324 (16)	0.0187 (4)
O6	0.16667 (4)	0.3223 (3)	0.64790 (12)	0.0223 (3)
C6	0.13493 (5)	0.2643 (5)	0.60896 (17)	0.0194 (4)
C7	0.11475 (5)	0.1114 (5)	0.67388 (17)	0.0213 (4)
O8	0.15678 (4)	0.0705 (4)	0.82323 (12)	0.0291 (4)
C8	0.12760 (5)	0.0164 (5)	0.78173 (16)	0.0237 (4)
H6	0.1683 (7)	0.256 (7)	0.708 (3)	0.036 (8)*
C9	0.10473 (5)	−0.1436 (5)	0.83946 (17)	0.0233 (5)
O10	0.13224 (4)	0.0039 (4)	1.01334 (11)	0.0302 (4)
C10	0.11600 (6)	−0.2324 (5)	0.95461 (17)	0.0259 (5)
H10a	0.13137 (6)	−0.3995 (5)	0.95592 (17)	0.0311 (6)*
C11	0.08672 (6)	−0.3217 (5)	1.00992 (18)	0.0285 (5)
H11a	0.09479 (6)	−0.4176 (5)	1.07681 (18)	0.0342 (6)*
H11b	0.07447 (6)	−0.1467 (5)	1.02528 (18)	0.0342 (6)*
C12	0.06389 (6)	−0.5294 (6)	0.94111 (18)	0.0306 (5)
H12a	0.07636 (6)	−0.7019 (6)	0.92448 (18)	0.0368 (6)*
H12b	0.04641 (6)	−0.5952 (6)	0.98029 (18)	0.0368 (6)*
O13	0.02297 (4)	−0.1782 (4)	0.85392 (14)	0.0334 (4)
C13	0.04842 (6)	−0.3834 (5)	0.83836 (18)	0.0279 (5)
H13	0.03912 (6)	−0.5361 (5)	0.78816 (18)	0.0335 (6)*
C14	0.07419 (5)	−0.2105 (5)	0.78996 (17)	0.0233 (5)
O15	0.06226 (4)	−0.1308 (4)	0.68890 (12)	0.0263 (4)
C16	0.08250 (5)	0.0280 (5)	0.63209 (16)	0.0228 (4)
O17	0.03783 (3)	0.0010 (4)	0.49037 (12)	0.0309 (4)
C17	0.06968 (5)	0.0942 (5)	0.52776 (18)	0.0247 (5)
C18	0.08955 (5)	0.2372 (5)	0.46459 (17)	0.0219 (5)
O19	0.04824 (4)	0.0928 (4)	0.31809 (12)	0.0283 (4)
C19	0.07782 (5)	0.2648 (5)	0.34700 (17)	0.0240 (5)
H19	0.07359 (5)	0.4724 (5)	0.32791 (17)	0.0288 (6)*
C20	0.10496 (5)	0.1415 (5)	0.28837 (17)	0.0212 (4)
H20a	0.10964 (5)	−0.0621 (5)	0.30904 (17)	0.0255 (5)*
H20b	0.09791 (5)	0.1476 (5)	0.21224 (17)	0.0255 (5)*
C21	0.13571 (5)	0.3293 (5)	0.31717 (17)	0.0193 (4)
H2a	0.2826 (7)	1.071 (7)	0.358 (2)	0.028 (7)*
H2b	0.2591 (7)	1.263 (8)	0.393 (3)	0.042 (9)*
C22	0.15515 (5)	0.3969 (5)	0.24019 (17)	0.0211 (4)
H22	0.15020 (5)	0.3158 (5)	0.17258 (17)	0.0253 (5)*
C23	0.18232 (5)	0.5870 (5)	0.26309 (16)	0.0203 (4)
C24	0.20483 (5)	0.6562 (5)	0.18962 (17)	0.0235 (5)
C25	0.23123 (5)	0.8393 (5)	0.21444 (17)	0.0243 (5)
C26	0.25678 (6)	0.9026 (6)	0.14341 (19)	0.0318 (6)
H26a	0.2627 (3)	1.1078 (11)	0.1487 (11)	0.0477 (9)*
H26b	0.2761 (2)	0.784 (3)	0.1647 (10)	0.0477 (9)*
H26c	0.24787 (18)	0.857 (4)	0.0713 (3)	0.0477 (9)*
C27	0.02588 (5)	0.1351 (6)	0.39095 (19)	0.0323 (6)
H27a	0.00455 (5)	0.0501 (6)	0.36291 (19)	0.0388 (7)*
H27b	0.02273 (5)	0.3450 (6)	0.40122 (19)	0.0388 (7)*
C28	−0.00812 (6)	−0.3188 (7)	0.8551 (2)	0.0503 (9)
H28a	−0.0160 (3)	−0.394 (5)	0.7855 (6)	0.0755 (13)*
H28b	−0.00562 (14)	−0.479 (4)	0.9052 (15)	0.0755 (13)*
H28c	−0.02381 (18)	−0.1787 (16)	0.8753 (19)	0.0755 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0276 (3)	0.0433 (3)	0.0203 (2)	−0.0038 (2)	0.00803 (18)	−0.0046 (3)
O1	0.0199 (7)	0.0232 (9)	0.0262 (8)	−0.0005 (6)	0.0039 (6)	−0.0001 (6)
N1	0.0170 (8)	0.0260 (10)	0.0251 (9)	−0.0001 (8)	0.0036 (6)	0.0013 (9)
C1	0.0186 (9)	0.0201 (11)	0.0204 (10)	0.0039 (8)	0.0019 (7)	0.0032 (8)
N2	0.0210 (10)	0.0332 (12)	0.0280 (10)	−0.0075 (8)	0.0041 (8)	−0.0021 (9)
C2	0.0173 (9)	0.0211 (11)	0.0208 (10)	0.0027 (8)	0.0039 (8)	0.0034 (8)
O3	0.0227 (8)	0.0213 (8)	0.0225 (8)	−0.0023 (7)	0.0064 (6)	−0.0030 (6)
C3	0.0188 (9)	0.0189 (11)	0.0183 (10)	0.0048 (8)	0.0028 (8)	0.0020 (8)
C4	0.0186 (9)	0.0179 (11)	0.0196 (10)	0.0043 (8)	0.0027 (7)	0.0012 (8)
C5	0.0189 (9)	0.0186 (10)	0.0189 (10)	0.0026 (8)	0.0037 (8)	−0.0018 (9)
O6	0.0203 (7)	0.0292 (9)	0.0173 (8)	−0.0029 (6)	0.0019 (6)	0.0011 (7)
C6	0.0166 (9)	0.0199 (11)	0.0221 (10)	0.0011 (8)	0.0037 (8)	−0.0026 (9)
C7	0.0211 (10)	0.0257 (12)	0.0178 (10)	0.0017 (9)	0.0051 (8)	−0.0023 (8)
O8	0.0228 (7)	0.0427 (11)	0.0210 (7)	−0.0054 (7)	0.0005 (6)	0.0021 (7)
C8	0.0246 (10)	0.0253 (12)	0.0214 (10)	−0.0010 (9)	0.0041 (8)	−0.0025 (10)
C9	0.0262 (11)	0.0225 (11)	0.0221 (11)	0.0011 (9)	0.0068 (8)	−0.0027 (9)
O10	0.0353 (8)	0.0350 (9)	0.0202 (7)	−0.0058 (8)	0.0037 (6)	−0.0013 (8)
C10	0.0273 (11)	0.0275 (12)	0.0235 (11)	0.0015 (9)	0.0052 (9)	0.0015 (9)
C11	0.0338 (12)	0.0320 (14)	0.0209 (11)	0.0022 (10)	0.0076 (9)	0.0050 (10)
C12	0.0340 (12)	0.0283 (13)	0.0320 (11)	−0.0023 (11)	0.0129 (9)	0.0044 (11)
O13	0.0238 (8)	0.0443 (11)	0.0341 (9)	−0.0004 (8)	0.0107 (7)	0.0023 (8)
C13	0.0300 (11)	0.0305 (13)	0.0250 (11)	−0.0062 (10)	0.0101 (9)	−0.0044 (10)
C14	0.0259 (11)	0.0250 (12)	0.0200 (10)	0.0010 (9)	0.0072 (8)	0.0002 (9)
O15	0.0217 (7)	0.0379 (10)	0.0201 (7)	−0.0068 (7)	0.0066 (6)	0.0010 (7)
C16	0.0186 (9)	0.0287 (12)	0.0222 (10)	−0.0027 (9)	0.0068 (7)	0.0017 (10)
O17	0.0164 (7)	0.0496 (11)	0.0261 (8)	−0.0089 (8)	0.0010 (6)	0.0065 (9)
C17	0.0155 (9)	0.0335 (13)	0.0251 (11)	0.0000 (9)	0.0029 (8)	−0.0008 (9)
C18	0.0181 (10)	0.0264 (12)	0.0211 (10)	0.0035 (8)	0.0027 (8)	−0.0007 (9)
O19	0.0190 (7)	0.0430 (11)	0.0221 (7)	−0.0069 (7)	−0.0001 (6)	0.0005 (7)
C19	0.0192 (10)	0.0289 (13)	0.0236 (11)	−0.0026 (9)	0.0019 (8)	0.0037 (10)
C20	0.0186 (9)	0.0250 (11)	0.0200 (10)	−0.0012 (9)	0.0023 (8)	0.0009 (9)
C21	0.0192 (9)	0.0184 (10)	0.0201 (10)	0.0009 (8)	0.0020 (7)	0.0009 (8)
C22	0.0210 (10)	0.0220 (11)	0.0199 (10)	0.0036 (8)	0.0016 (8)	−0.0011 (8)
C23	0.0212 (9)	0.0219 (11)	0.0178 (10)	0.0039 (8)	0.0032 (7)	0.0022 (8)
C24	0.0219 (10)	0.0293 (12)	0.0195 (10)	0.0040 (9)	0.0037 (8)	0.0011 (9)
C25	0.0216 (10)	0.0291 (12)	0.0221 (11)	0.0013 (9)	0.0029 (8)	0.0025 (10)
C26	0.0234 (11)	0.0463 (17)	0.0270 (11)	−0.0004 (10)	0.0080 (9)	−0.0014 (10)
C27	0.0190 (10)	0.0498 (16)	0.0280 (12)	−0.0034 (11)	0.0025 (9)	0.0051 (11)
C28	0.0264 (13)	0.077 (2)	0.0470 (17)	−0.0058 (14)	0.0041 (11)	0.0269 (16)

Geometric parameters (Å, º)

Cl1—C24	1.741 (2)	C10—C11	1.519 (3)
O1—C1	1.256 (3)	C11—C12	1.511 (3)
N1—C1	1.374 (3)	C12—C13	1.519 (3)
N1—N2	1.424 (2)	O13—C13	1.425 (3)
N1—C25	1.385 (3)	O13—C28	1.417 (3)
C1—C2	1.444 (3)	C13—C14	1.506 (3)
C2—C3	1.426 (3)	C14—O15	1.357 (3)
C2—C23	1.413 (3)	O15—C16	1.372 (3)
O3—C3	1.339 (3)	C16—C17	1.388 (3)
C3—C4	1.396 (3)	O17—C17	1.382 (2)
C4—C5	1.488 (3)	O17—C27	1.424 (3)
C4—C21	1.421 (3)	C17—C18	1.378 (3)
C5—C6	1.401 (3)	C18—C19	1.509 (3)
C5—C18	1.421 (3)	O19—C19	1.437 (2)
O6—C6	1.342 (2)	O19—C27	1.399 (3)
C6—C7	1.422 (3)	C19—C20	1.521 (3)
C7—C8	1.461 (3)	C20—C21	1.514 (3)
C7—C16	1.396 (3)	C21—C22	1.375 (3)
O8—C8	1.253 (3)	C22—C23	1.399 (3)
C8—C9	1.456 (3)	C23—C24	1.430 (3)
C9—C10	1.525 (3)	C24—C25	1.358 (3)
C9—C14	1.346 (3)	C25—C26	1.496 (3)
O10—C10	1.414 (3)
N2—N1—C1	117.47 (17)	O13—C13—C12	112.72 (19)
C25—N1—C1	124.52 (18)	C14—C13—C12	110.42 (18)
C25—N1—N2	117.82 (18)	C14—C13—O13	106.14 (19)
N1—C1—O1	119.31 (18)	C13—C14—C9	125.1 (2)
C2—C1—O1	124.20 (19)	O15—C14—C9	124.5 (2)
C2—C1—N1	116.49 (18)	O15—C14—C13	110.35 (17)
C3—C2—C1	119.21 (18)	C16—O15—C14	118.43 (16)
C23—C2—C1	120.82 (19)	O15—C16—C7	122.85 (18)
C23—C2—C3	119.97 (19)	C17—C16—C7	120.83 (19)
O3—C3—C2	120.27 (18)	C17—C16—O15	116.28 (17)
C4—C3—C2	120.43 (18)	C27—O17—C17	111.22 (17)
C4—C3—O3	119.28 (19)	O17—C17—C16	118.14 (19)
C5—C4—C3	124.26 (18)	C18—C17—C16	119.03 (18)
C21—C4—C3	117.41 (19)	C18—C17—O17	122.77 (19)
C21—C4—C5	118.31 (18)	C17—C18—C5	122.52 (19)
C6—C5—C4	124.87 (17)	C19—C18—C5	118.02 (19)
C18—C5—C4	116.34 (17)	C19—C18—C17	119.06 (18)
C18—C5—C6	117.83 (19)	C27—O19—C19	110.80 (17)
O6—C6—C5	120.95 (19)	O19—C19—C18	110.24 (18)
C7—C6—C5	119.85 (18)	C20—C19—C18	107.68 (17)
C7—C6—O6	118.98 (18)	C20—C19—O19	108.34 (18)
C8—C7—C6	121.83 (18)	C21—C20—C19	107.87 (17)
C16—C7—C6	119.90 (19)	C20—C21—C4	118.33 (19)
C16—C7—C8	118.09 (19)	C22—C21—C4	122.23 (19)
O8—C8—C7	122.1 (2)	C22—C21—C20	119.37 (18)
C9—C8—C7	116.67 (18)	C23—C22—C21	120.33 (19)
C9—C8—O8	121.28 (19)	C22—C23—C2	118.97 (19)
C10—C9—C8	119.15 (18)	C24—C23—C2	117.10 (19)
C14—C9—C8	119.3 (2)	C24—C23—C22	123.93 (19)
C14—C9—C10	121.5 (2)	C23—C24—Cl1	118.30 (16)
O10—C10—C9	111.25 (19)	C25—C24—Cl1	119.03 (17)
C11—C10—C9	111.34 (18)	C25—C24—C23	122.6 (2)
C11—C10—O10	107.19 (18)	C24—C25—N1	118.2 (2)
C12—C11—C10	110.85 (19)	C26—C25—N1	117.05 (19)
C13—C12—C11	111.9 (2)	C26—C25—C24	124.8 (2)
C28—O13—C13	112.0 (2)	O19—C27—O17	110.84 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10···O8	0.97 (3)	2.06 (4)	2.756 (2)	127 (3)
O3—H3···O1	0.80 (3)	1.83 (3)	2.561 (2)	151 (4)
O6—H6···O8	0.81 (4)	1.81 (4)	2.583 (2)	159 (3)
N2—H2b···O1^i	0.84 (4)	2.27 (3)	3.009 (2)	147 (3)
N2—H2a···O6^i	0.95 (3)	2.36 (3)	3.277 (3)	162 (2)

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