Crystal structure of 5-{3-[2,6-dimethyl-4-(5-methyl-1,2,4-oxa­diazol-3-yl)phen­oxy]prop­yl}-N-(11-hy­droxy­undec­yl)isoxazole-3-carboxamide hemihydrate

The crystal structure and supra­molecular features of 5-{3-[2,6-dimethyl-4-(5-methyl-1,2,4-oxa­diazol-3-yl)phen­oxy]prop­yl}-N-(11-hy­droxy­undec­yl)isoxazole-3-carboxamide hemihydrate, a derivative of anti­viral `WIN compounds', are reported.

Computing details

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

5-{3-[2,6-Dimethyl-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]propyl}-N-(11-hydroxyundecyl)isoxazole-3-carboxamide hemihydrate

Crystal data

2C29H42N4O5·H2O	Z = 1
Mr = 1071.34	F(000) = 578
Triclinic, P1	Dx = 1.245 Mg m^−3
a = 6.7137 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.0263 (5) Å	Cell parameters from 5261 reflections
c = 16.6757 (8) Å	θ = 2.5–30.3°
α = 113.889 (4)°	µ = 0.09 mm^−1
β = 94.515 (4)°	T = 170 K
γ = 90.976 (4)°	Needle, clear colourless
V = 1429.29 (12) Å^3	0.42 × 0.15 × 0.09 mm

Data collection

Agilent SuperNova, Single source at offset, Eos diffractometer	7670 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	5463 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.016
Detector resolution: 16.0107 pixels mm^-1	θmax = 30.6°, θmin = 2.5°
ω scans	h = −8→9
Absorption correction: analytical [CrysAlisPro (Agilent, 2013), based on expressions derived by Clark & Reid (1995)]	k = −19→20
Tmin = 0.990, Tmax = 0.998	l = −23→23
13976 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.148	w = 1/[σ^2(Fo^2) + (0.0537P)^2 + 0.3588P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
7670 reflections	Δρmax = 0.36 e Å^−3
364 parameters	Δρmin = −0.26 e Å^−3
3 restraints

Special details

Experimental. Absorption correction: [CrysAlisPro (Agilent, 2013). Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N26	0.4579 (2)	0.58797 (10)	0.29818 (9)	0.0368 (3)
H26	0.5168	0.5282	0.2794	0.044*
O15	1.50948 (17)	0.80964 (8)	0.69521 (7)	0.0345 (3)
O23	0.98187 (18)	0.57258 (8)	0.43787 (8)	0.0419 (3)
C33	−0.5511 (2)	0.30398 (12)	−0.11261 (10)	0.0345 (4)
H33A	−0.6504	0.3164	−0.0691	0.041*
H33B	−0.5519	0.3632	−0.1305	0.041*
C28	0.1978 (2)	0.49429 (12)	0.17862 (10)	0.0333 (3)
H28A	0.2024	0.4347	0.1960	0.040*
H28B	0.2944	0.4832	0.1342	0.040*
C27	0.2593 (2)	0.59363 (13)	0.25821 (10)	0.0367 (4)
H27A	0.2598	0.6531	0.2406	0.044*
H27B	0.1607	0.6061	0.3021	0.044*
C35	−0.8237 (3)	0.20232 (12)	−0.23541 (10)	0.0364 (4)
H35A	−0.8320	0.2614	−0.2534	0.044*
H35B	−0.9211	0.2122	−0.1915	0.044*
O25	0.4853 (2)	0.75915 (9)	0.38872 (8)	0.0472 (3)
C31	−0.2796 (2)	0.40101 (12)	0.01197 (10)	0.0333 (3)
H31A	−0.3782	0.4129	0.0558	0.040*
H31B	−0.2810	0.4607	−0.0053	0.040*
C7	2.0845 (2)	0.78185 (12)	0.79254 (10)	0.0327 (3)
C30	−0.0726 (2)	0.39840 (12)	0.05502 (10)	0.0337 (3)
H30A	0.0267	0.3889	0.0119	0.040*
H30B	−0.0698	0.3374	0.0707	0.040*
O3	2.54720 (19)	0.71434 (9)	0.87183 (8)	0.0418 (3)
C32	−0.3442 (2)	0.30171 (12)	−0.06881 (10)	0.0348 (4)
H32A	−0.3433	0.2421	−0.0514	0.042*
H32B	−0.2450	0.2897	−0.1124	0.042*
C12	2.0006 (3)	0.87875 (12)	0.82186 (10)	0.0365 (4)
H12	2.0747	0.9378	0.8653	0.044*
N6	2.3818 (2)	0.85718 (11)	0.90254 (9)	0.0388 (3)
N4	2.3705 (2)	0.68521 (11)	0.81288 (9)	0.0389 (3)
C29	−0.0119 (2)	0.49672 (12)	0.13743 (10)	0.0339 (3)
H29A	−0.1090	0.5053	0.1813	0.041*
H29B	−0.0178	0.5580	0.1222	0.041*
C10	1.7059 (2)	0.80337 (12)	0.72431 (10)	0.0311 (3)
C34	−0.6142 (2)	0.20383 (12)	−0.19294 (10)	0.0357 (4)
H34A	−0.5177	0.1933	−0.2374	0.043*
H34B	−0.6067	0.1444	−0.1754	0.043*
C8	1.9776 (2)	0.69561 (12)	0.72722 (10)	0.0323 (3)
H8	2.0353	0.6295	0.7065	0.039*
N22	0.7992 (2)	0.55954 (11)	0.38631 (9)	0.0413 (4)
C9	1.7885 (2)	0.70490 (12)	0.69204 (10)	0.0314 (3)
C24	0.5515 (2)	0.67201 (12)	0.36269 (10)	0.0331 (3)
C36	−0.8799 (3)	0.10077 (13)	−0.31550 (11)	0.0409 (4)
H36A	−0.7808	0.0904	−0.3588	0.049*
H36B	−0.8732	0.0420	−0.2971	0.049*
C18	1.2226 (2)	0.70293 (12)	0.53997 (10)	0.0337 (3)
H18A	1.3308	0.6702	0.5025	0.040*
H18B	1.2189	0.6737	0.5849	0.040*
C20	0.8824 (2)	0.73138 (12)	0.46614 (10)	0.0313 (3)
H20	0.8742	0.8051	0.4895	0.038*
C5	2.2806 (2)	0.77262 (12)	0.83423 (10)	0.0329 (3)
C21	0.7448 (2)	0.65460 (12)	0.40427 (10)	0.0309 (3)
C11	1.8104 (3)	0.89102 (12)	0.78886 (10)	0.0354 (4)
C37	−1.0859 (3)	0.09851 (13)	−0.35931 (10)	0.0387 (4)
H37A	−1.1872	0.1026	−0.3181	0.046*
H37B	−1.0970	0.1597	−0.3744	0.046*
C17	1.2696 (3)	0.82027 (12)	0.58603 (11)	0.0380 (4)
H17A	1.2454	0.8517	0.5428	0.046*
H17B	1.1780	0.8511	0.6326	0.046*
C19	1.0283 (2)	0.67627 (12)	0.48446 (10)	0.0314 (3)
C16	1.4831 (3)	0.84709 (13)	0.62690 (11)	0.0380 (4)
H16A	1.5766	0.8139	0.5817	0.046*
H16B	1.5111	0.9236	0.6519	0.046*
C2	2.5404 (3)	0.81666 (13)	0.92158 (11)	0.0374 (4)
C13	1.6694 (3)	0.61197 (12)	0.62341 (11)	0.0401 (4)
H13A	1.5376	0.6064	0.6431	0.060*
H13B	1.7401	0.5484	0.6146	0.060*
H13C	1.6528	0.6205	0.5678	0.060*
C1	2.7090 (3)	0.86781 (15)	0.98960 (12)	0.0469 (4)
H1A	2.7096	0.8402	1.0350	0.070*
H1B	2.6934	0.9433	1.0165	0.070*
H1C	2.8354	0.8537	0.9623	0.070*
C14	1.7185 (3)	0.99591 (13)	0.82549 (12)	0.0475 (5)
H14A	1.7798	1.0371	0.8854	0.071*
H14B	1.5742	0.9857	0.8268	0.071*
H14C	1.7419	1.0330	0.7880	0.071*
O100	−1.4973 (6)	−0.0308 (2)	−0.5193 (2)	0.0642 (9)	0.5
H10A	−1.586 (8)	0.012 (4)	−0.504 (4)	0.096*	0.5
H10B	−1.503 (9)	−0.0960 (10)	−0.548 (3)	0.096*	0.5
O38	−1.1236 (2)	0.00445 (10)	−0.43770 (9)	0.0517 (4)
H38	−1.238 (2)	0.006 (2)	−0.4585 (15)	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N26	0.0317 (8)	0.0351 (7)	0.0377 (7)	0.0030 (6)	−0.0097 (6)	0.0109 (6)
O15	0.0290 (6)	0.0373 (6)	0.0372 (6)	0.0034 (5)	−0.0018 (5)	0.0159 (5)
O23	0.0362 (7)	0.0310 (6)	0.0464 (7)	0.0040 (5)	−0.0147 (5)	0.0066 (5)
C33	0.0279 (8)	0.0327 (8)	0.0349 (8)	0.0021 (6)	−0.0032 (6)	0.0067 (6)
C28	0.0285 (8)	0.0344 (8)	0.0335 (8)	0.0024 (6)	−0.0040 (6)	0.0114 (6)
C27	0.0296 (9)	0.0393 (9)	0.0353 (8)	0.0039 (7)	−0.0063 (7)	0.0109 (7)
C35	0.0291 (8)	0.0341 (8)	0.0362 (8)	0.0043 (7)	−0.0038 (7)	0.0055 (6)
O25	0.0417 (7)	0.0386 (6)	0.0514 (7)	0.0096 (6)	−0.0092 (6)	0.0104 (5)
C31	0.0280 (8)	0.0327 (8)	0.0331 (8)	0.0018 (6)	−0.0032 (6)	0.0084 (6)
C7	0.0304 (8)	0.0343 (8)	0.0336 (8)	0.0039 (6)	0.0003 (6)	0.0145 (6)
C30	0.0291 (8)	0.0341 (8)	0.0335 (8)	0.0019 (6)	−0.0024 (6)	0.0102 (6)
O3	0.0372 (7)	0.0394 (6)	0.0455 (7)	0.0085 (5)	−0.0034 (5)	0.0150 (5)
C32	0.0298 (9)	0.0353 (8)	0.0314 (8)	0.0017 (7)	−0.0030 (6)	0.0064 (6)
C12	0.0367 (9)	0.0308 (8)	0.0366 (8)	0.0010 (7)	−0.0048 (7)	0.0098 (6)
N6	0.0373 (8)	0.0369 (7)	0.0375 (7)	0.0054 (6)	−0.0039 (6)	0.0114 (6)
N4	0.0345 (8)	0.0379 (7)	0.0417 (7)	0.0047 (6)	−0.0034 (6)	0.0147 (6)
C29	0.0281 (8)	0.0343 (8)	0.0329 (8)	0.0011 (6)	−0.0047 (6)	0.0086 (6)
C10	0.0285 (8)	0.0327 (8)	0.0316 (7)	0.0034 (6)	−0.0004 (6)	0.0133 (6)
C34	0.0293 (8)	0.0344 (8)	0.0328 (8)	0.0055 (7)	−0.0035 (6)	0.0038 (6)
C8	0.0329 (9)	0.0300 (7)	0.0334 (8)	0.0051 (6)	0.0029 (6)	0.0120 (6)
N22	0.0348 (8)	0.0352 (7)	0.0421 (8)	0.0040 (6)	−0.0131 (6)	0.0067 (6)
C9	0.0326 (9)	0.0304 (7)	0.0302 (7)	0.0017 (6)	0.0009 (6)	0.0116 (6)
C24	0.0301 (8)	0.0370 (8)	0.0314 (7)	0.0006 (7)	−0.0029 (6)	0.0141 (6)
C36	0.0328 (9)	0.0357 (8)	0.0389 (9)	0.0042 (7)	−0.0078 (7)	0.0013 (7)
C18	0.0278 (8)	0.0345 (8)	0.0339 (8)	0.0029 (6)	−0.0032 (6)	0.0099 (6)
C20	0.0287 (8)	0.0297 (7)	0.0320 (7)	0.0015 (6)	−0.0006 (6)	0.0095 (6)
C5	0.0321 (9)	0.0341 (8)	0.0334 (8)	0.0039 (7)	0.0025 (6)	0.0147 (6)
C21	0.0277 (8)	0.0329 (8)	0.0294 (7)	0.0026 (6)	−0.0012 (6)	0.0106 (6)
C11	0.0355 (9)	0.0298 (7)	0.0373 (8)	0.0041 (7)	−0.0022 (7)	0.0110 (6)
C37	0.0308 (9)	0.0386 (9)	0.0355 (8)	0.0003 (7)	−0.0039 (7)	0.0049 (7)
C17	0.0330 (9)	0.0354 (8)	0.0414 (9)	0.0001 (7)	−0.0076 (7)	0.0134 (7)
C19	0.0292 (8)	0.0302 (7)	0.0302 (7)	0.0025 (6)	−0.0008 (6)	0.0082 (6)
C16	0.0351 (9)	0.0383 (8)	0.0413 (9)	−0.0027 (7)	−0.0082 (7)	0.0192 (7)
C2	0.0366 (9)	0.0378 (8)	0.0367 (8)	0.0060 (7)	0.0005 (7)	0.0143 (7)
C13	0.0367 (10)	0.0320 (8)	0.0429 (9)	0.0028 (7)	−0.0029 (7)	0.0076 (7)
C1	0.0397 (10)	0.0508 (10)	0.0451 (10)	0.0044 (8)	−0.0072 (8)	0.0164 (8)
C14	0.0488 (12)	0.0321 (8)	0.0512 (10)	0.0087 (8)	−0.0088 (9)	0.0085 (7)
O100	0.0418 (18)	0.0401 (18)	0.085 (3)	−0.0014 (17)	−0.0171 (18)	0.0032 (16)
O38	0.0355 (7)	0.0480 (7)	0.0479 (7)	−0.0014 (6)	−0.0147 (6)	−0.0013 (6)

Geometric parameters (Å, º)

N26—H26	0.8800	C10—C9	1.406 (2)
N26—C27	1.4614 (19)	C10—C11	1.394 (2)
N26—C24	1.3352 (19)	C34—H34A	0.9900
O15—C10	1.3854 (18)	C34—H34B	0.9900
O15—C16	1.4356 (19)	C8—H8	0.9500
O23—N22	1.4056 (17)	C8—C9	1.387 (2)
O23—C19	1.3591 (18)	N22—C21	1.308 (2)
C33—H33A	0.9900	C9—C13	1.504 (2)
C33—H33B	0.9900	C24—C21	1.494 (2)
C33—C32	1.525 (2)	C36—H36A	0.9900
C33—C34	1.521 (2)	C36—H36B	0.9900
C28—H28A	0.9900	C36—C37	1.506 (2)
C28—H28B	0.9900	C18—H18A	0.9900
C28—C27	1.507 (2)	C18—H18B	0.9900
C28—C29	1.524 (2)	C18—C17	1.523 (2)
C27—H27A	0.9900	C18—C19	1.487 (2)
C27—H27B	0.9900	C20—H20	0.9500
C35—H35A	0.9900	C20—C21	1.412 (2)
C35—H35B	0.9900	C20—C19	1.349 (2)
C35—C34	1.520 (2)	C11—C14	1.510 (2)
C35—C36	1.522 (2)	C37—H37A	0.9900
O25—C24	1.2242 (19)	C37—H37B	0.9900
C31—H31A	0.9900	C37—O38	1.4329 (19)
C31—H31B	0.9900	C17—H17A	0.9900
C31—C30	1.521 (2)	C17—H17B	0.9900
C31—C32	1.520 (2)	C17—C16	1.510 (2)
C7—C12	1.391 (2)	C16—H16A	0.9900
C7—C8	1.394 (2)	C16—H16B	0.9900
C7—C5	1.473 (2)	C2—C1	1.481 (2)
C30—H30A	0.9900	C13—H13A	0.9800
C30—H30B	0.9900	C13—H13B	0.9800
C30—C29	1.521 (2)	C13—H13C	0.9800
O3—N4	1.4194 (18)	C1—H1A	0.9800
O3—C2	1.339 (2)	C1—H1B	0.9800
C32—H32A	0.9900	C1—H1C	0.9800
C32—H32B	0.9900	C14—H14A	0.9800
C12—H12	0.9500	C14—H14B	0.9800
C12—C11	1.392 (2)	C14—H14C	0.9800
N6—C5	1.387 (2)	O100—O100^i	0.847 (5)
N6—C2	1.293 (2)	O100—H10A	0.834 (10)
N4—C5	1.304 (2)	O100—H10B	0.841 (10)
C29—H29A	0.9900	O38—H38	0.819 (10)
C29—H29B	0.9900
C27—N26—H26	119.5	C8—C9—C10	118.41 (14)
C24—N26—H26	119.5	C8—C9—C13	121.52 (14)
C24—N26—C27	121.03 (13)	N26—C24—C21	116.22 (14)
C10—O15—C16	115.72 (13)	O25—C24—N26	123.45 (15)
C19—O23—N22	109.09 (11)	O25—C24—C21	120.32 (14)
H33A—C33—H33B	107.7	C35—C36—H36A	108.9
C32—C33—H33A	108.9	C35—C36—H36B	108.9
C32—C33—H33B	108.9	H36A—C36—H36B	107.7
C34—C33—H33A	108.9	C37—C36—C35	113.23 (14)
C34—C33—H33B	108.9	C37—C36—H36A	108.9
C34—C33—C32	113.38 (13)	C37—C36—H36B	108.9
H28A—C28—H28B	107.9	H18A—C18—H18B	107.8
C27—C28—H28A	109.1	C17—C18—H18A	109.1
C27—C28—H28B	109.1	C17—C18—H18B	109.1
C27—C28—C29	112.36 (13)	C19—C18—H18A	109.1
C29—C28—H28A	109.1	C19—C18—H18B	109.1
C29—C28—H28B	109.1	C19—C18—C17	112.46 (13)
N26—C27—C28	111.29 (13)	C21—C20—H20	127.9
N26—C27—H27A	109.4	C19—C20—H20	127.9
N26—C27—H27B	109.4	C19—C20—C21	104.27 (13)
C28—C27—H27A	109.4	N6—C5—C7	121.88 (14)
C28—C27—H27B	109.4	N4—C5—C7	123.71 (14)
H27A—C27—H27B	108.0	N4—C5—N6	114.37 (14)
H35A—C35—H35B	107.8	N22—C21—C24	120.05 (14)
C34—C35—H35A	109.1	N22—C21—C20	112.71 (14)
C34—C35—H35B	109.1	C20—C21—C24	127.21 (14)
C34—C35—C36	112.48 (13)	C12—C11—C10	118.13 (14)
C36—C35—H35A	109.1	C12—C11—C14	120.24 (15)
C36—C35—H35B	109.1	C10—C11—C14	121.58 (15)
H31A—C31—H31B	107.7	C36—C37—H37A	109.6
C30—C31—H31A	108.8	C36—C37—H37B	109.6
C30—C31—H31B	108.8	H37A—C37—H37B	108.1
C32—C31—H31A	108.8	O38—C37—C36	110.40 (13)
C32—C31—H31B	108.8	O38—C37—H37A	109.6
C32—C31—C30	113.69 (13)	O38—C37—H37B	109.6
C12—C7—C8	119.31 (15)	C18—C17—H17A	109.1
C12—C7—C5	118.79 (14)	C18—C17—H17B	109.1
C8—C7—C5	121.86 (14)	H17A—C17—H17B	107.8
C31—C30—H30A	108.9	C16—C17—C18	112.46 (14)
C31—C30—H30B	108.9	C16—C17—H17A	109.1
C31—C30—C29	113.32 (13)	C16—C17—H17B	109.1
H30A—C30—H30B	107.7	O23—C19—C18	115.49 (13)
C29—C30—H30A	108.9	C20—C19—O23	109.31 (13)
C29—C30—H30B	108.9	C20—C19—C18	135.17 (14)
C2—O3—N4	106.40 (12)	O15—C16—C17	108.21 (14)
C33—C32—H32A	108.8	O15—C16—H16A	110.1
C33—C32—H32B	108.8	O15—C16—H16B	110.1
C31—C32—C33	113.98 (13)	C17—C16—H16A	110.1
C31—C32—H32A	108.8	C17—C16—H16B	110.1
C31—C32—H32B	108.8	H16A—C16—H16B	108.4
H32A—C32—H32B	107.7	O3—C2—C1	117.70 (15)
C7—C12—H12	119.3	N6—C2—O3	113.45 (15)
C7—C12—C11	121.41 (15)	N6—C2—C1	128.85 (16)
C11—C12—H12	119.3	C9—C13—H13A	109.5
C2—N6—C5	102.68 (13)	C9—C13—H13B	109.5
C5—N4—O3	103.10 (12)	C9—C13—H13C	109.5
C28—C29—H29A	109.0	H13A—C13—H13B	109.5
C28—C29—H29B	109.0	H13A—C13—H13C	109.5
C30—C29—C28	112.80 (13)	H13B—C13—H13C	109.5
C30—C29—H29A	109.0	C2—C1—H1A	109.5
C30—C29—H29B	109.0	C2—C1—H1B	109.5
H29A—C29—H29B	107.8	C2—C1—H1C	109.5
O15—C10—C9	117.88 (13)	H1A—C1—H1B	109.5
O15—C10—C11	120.18 (14)	H1A—C1—H1C	109.5
C11—C10—C9	121.74 (14)	H1B—C1—H1C	109.5
C33—C34—H34A	108.7	C11—C14—H14A	109.5
C33—C34—H34B	108.7	C11—C14—H14B	109.5
C35—C34—C33	114.39 (13)	C11—C14—H14C	109.5
C35—C34—H34A	108.7	H14A—C14—H14B	109.5
C35—C34—H34B	108.7	H14A—C14—H14C	109.5
H34A—C34—H34B	107.6	H14B—C14—H14C	109.5
C7—C8—H8	119.5	O100^i—O100—H10A	45 (5)
C9—C8—C7	120.98 (14)	O100^i—O100—H10B	166 (4)
C9—C8—H8	119.5	H10A—O100—H10B	132 (6)
C21—N22—O23	104.61 (12)	C37—O38—H38	107.1 (18)
C10—C9—C13	120.03 (14)
N26—C24—C21—N22	−9.9 (2)	C34—C33—C32—C31	−179.60 (14)
N26—C24—C21—C20	172.31 (15)	C34—C35—C36—C37	−179.10 (15)
O15—C10—C9—C8	−173.62 (14)	C8—C7—C12—C11	1.5 (3)
O15—C10—C9—C13	4.2 (2)	C8—C7—C5—N6	−176.35 (15)
O15—C10—C11—C12	174.16 (14)	C8—C7—C5—N4	1.3 (3)
O15—C10—C11—C14	−3.2 (3)	N22—O23—C19—C18	−177.78 (14)
O23—N22—C21—C24	−178.41 (14)	N22—O23—C19—C20	0.63 (18)
O23—N22—C21—C20	−0.32 (19)	C9—C10—C11—C12	−0.6 (2)
C27—N26—C24—O25	−4.6 (3)	C9—C10—C11—C14	−177.98 (16)
C27—N26—C24—C21	174.35 (14)	C24—N26—C27—C28	171.58 (14)
C27—C28—C29—C30	177.88 (14)	C36—C35—C34—C33	179.91 (15)
C35—C36—C37—O38	175.68 (15)	C18—C17—C16—O15	−64.32 (18)
O25—C24—C21—N22	169.10 (16)	C5—C7—C12—C11	−175.97 (15)
O25—C24—C21—C20	−8.7 (3)	C5—C7—C8—C9	176.58 (15)
C31—C30—C29—C28	−178.56 (14)	C5—N6—C2—O3	−0.4 (2)
C7—C12—C11—C10	−0.8 (3)	C5—N6—C2—C1	179.90 (18)
C7—C12—C11—C14	176.62 (17)	C21—C20—C19—O23	−0.78 (18)
C7—C8—C9—C10	−0.5 (2)	C21—C20—C19—C18	177.18 (18)
C7—C8—C9—C13	−178.27 (15)	C11—C10—C9—C8	1.2 (2)
C30—C31—C32—C33	−179.69 (14)	C11—C10—C9—C13	179.01 (15)
O3—N4—C5—C7	−178.08 (14)	C17—C18—C19—O23	176.76 (14)
O3—N4—C5—N6	−0.30 (19)	C17—C18—C19—C20	−1.1 (3)
C32—C33—C34—C35	177.44 (14)	C19—O23—N22—C21	−0.18 (18)
C32—C31—C30—C29	−178.21 (14)	C19—C18—C17—C16	−168.20 (14)
C12—C7—C8—C9	−0.8 (2)	C19—C20—C21—N22	0.69 (19)
C12—C7—C5—N6	1.1 (2)	C19—C20—C21—C24	178.63 (16)
C12—C7—C5—N4	178.67 (16)	C16—O15—C10—C9	−100.42 (16)
N4—O3—C2—N6	0.2 (2)	C16—O15—C10—C11	84.64 (18)
N4—O3—C2—C1	179.98 (15)	C2—O3—N4—C5	0.04 (17)
C29—C28—C27—N26	178.10 (14)	C2—N6—C5—C7	178.26 (15)
C10—O15—C16—C17	164.12 (13)	C2—N6—C5—N4	0.4 (2)

Symmetry code: (i) −x−3, −y, −z−1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28A···O3^ii	0.99	2.64	3.2567 (19)	120
C20—H20···O38^iii	0.95	2.56	3.505 (2)	175
C13—H13B···O23^ii	0.98	2.51	3.416 (2)	154
C1—H1B···N6	0.98	2.65	3.622 (2)	174
O100—H10B···O25^iv	0.84 (1)	1.87 (1)	2.710 (3)	180 (6)
O38—H38···O100	0.82 (1)	1.90 (1)	2.695 (4)	164 (2)

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