1-[2-(4-Nitro-phen-yl)-5-(5-phenyl-1,2-oxazol-3-yl)-1,2,3,4-tetra-hydro-quinolin-4-yl]pyrrolidin-2-one monohydrate.

The title compound, C(28)H(24)N(4)O(4)·H(2)O, crystallizes with two organic mol-ecules and two solvent water mol-ecules in the asymmetric unit. The most obvious difference between the mol-ecules is the torsion angles between the isoxazole ring and the benzene and phenyl rings [47.0 (2)/56.4 (2) and 33.3 (2)/11.0 (2)°, respectively]. Another important difference is observed in the rotation of the nitro group with respect to the phenyl groups [3.5 (6) and 31.1 (6)°]. The pyrrolidinone fragment is cis oriented with respect to the 4-nitro-phenyl fragment. In the crystal, mol-ecules are linked into centrosymmetric R(4) (2)(8) and R(4) (4)(20) motifs by O-H⋯O and N-H⋯O inter-actions.

Related literature

For pharmacological activity of quinoline, see: Shi et al. (2008 ▶); Lunniss et al. (2009 ▶); He et al. (2005 ▶); Eswaran et al. (2010 ▶). For the synthesis and medicinal uses of quinolines, see: Kalita et al. (2006 ▶); Kouznetsov et al. (2005 ▶); Sankaran et al. (2010 ▶). For reactions of isoxazoles see: Taldone et al. (2008 ▶); Narlawar et al. (2008 ▶); Velaparthi et al. (2008 ▶); Rizzi et al. (2008 ▶); Lautens & Roy (2000 ▶); Broggini et al. (2005 ▶); Kotera et al. (1970 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C28H24N4O4·H2O

M = 498.53

Triclinic,

a = 13.516 (8) Å

b = 14.193 (6) Å

c = 14.987 (11) Å

α = 70.151 (10)°

β = 79.62 (2)°

γ = 69.700 (9)°

V = 2530 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.39 × 0.17 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer

21159 measured reflections

11596 independent reflections

7891 reflections with I > 2σ(I)

R int = 0.090

Refinement

R[F 2 > 2σ(F 2)] = 0.098

wR(F 2) = 0.240

S = 1.16

11596 reflections

691 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.33 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810052463/om2389sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052463/om2389Isup2.hkl

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

C28H24N4O4·H2O	Z = 4
Mr = 498.53	F(000) = 1048
Triclinic, P1	Dx = 1.309 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 13.516 (8) Å	Cell parameters from 7466 reflections
b = 14.193 (6) Å	θ = 1.6–27.7°
c = 14.987 (11) Å	µ = 0.09 mm−1
α = 70.151 (10)°	T = 293 K
β = 79.62 (2)°	Prism, yellow
γ = 69.700 (9)°	0.39 × 0.17 × 0.12 mm
V = 2530 (3) Å3

Nonius KappaCCD diffractometer	7891 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.090
graphite	θmax = 27.7°, θmin = 1.6°
φ and ω scans with κ offsets	h = 0→17
21159 measured reflections	k = −16→18
11596 independent reflections	l = −18→19

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)] = 0.098	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.240	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ2(Fo2) + (0.0836P)2 + 2.2406P] where P = (Fo2 + 2Fc2)/3
11596 reflections	(Δ/σ)max < 0.001
691 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.

	x	y	z	Uiso*/Ueq
O1	0.1893 (4)	0.5828 (4)	0.0899 (4)	0.151 (2)
O2	0.2061 (4)	0.4662 (4)	0.0265 (4)	0.1459 (19)
O3	1.18855 (17)	0.0338 (2)	0.28972 (19)	0.0595 (7)
O4	0.9406 (2)	0.1193 (2)	0.07318 (17)	0.0621 (7)
O5	−0.4045 (3)	0.5670 (3)	0.1648 (3)	0.1073 (13)
O6	−0.3530 (3)	0.7007 (3)	0.0855 (3)	0.0982 (11)
O7	0.1570 (2)	0.12322 (19)	0.5951 (2)	0.0675 (7)
O8	0.49271 (17)	0.14888 (18)	0.61723 (17)	0.0540 (6)
N1	0.2355 (3)	0.4985 (3)	0.0794 (3)	0.0850 (11)
N2	0.6331 (2)	0.2718 (2)	0.3431 (2)	0.0473 (7)
H2N	0.589 (3)	0.264 (3)	0.388 (3)	0.077 (14)*
N3	1.1088 (2)	0.1043 (2)	0.3322 (2)	0.0582 (8)
N4	0.90577 (19)	0.22917 (19)	0.16467 (17)	0.0405 (6)
N5	−0.3424 (3)	0.6164 (3)	0.1471 (3)	0.0681 (9)
N6	0.0703 (2)	0.5391 (2)	0.3501 (2)	0.0548 (8)
H6N	0.039 (3)	0.603 (3)	0.331 (3)	0.060 (11)*
N7	0.2327 (2)	0.21999 (18)	0.46358 (18)	0.0399 (6)
N8	0.4633 (2)	0.2353 (2)	0.5345 (2)	0.0511 (7)
C1	0.3325 (3)	0.4336 (3)	0.1285 (3)	0.0596 (9)
C2	0.3650 (3)	0.4683 (3)	0.1888 (3)	0.0616 (10)
H2	0.3254	0.5318	0.2002	0.074*
C3	0.4581 (3)	0.4079 (3)	0.2332 (3)	0.0538 (9)
H3	0.4811	0.4315	0.2742	0.065*
C4	0.5168 (2)	0.3135 (3)	0.2172 (2)	0.0447 (7)
C5	0.4787 (3)	0.2782 (4)	0.1591 (3)	0.0767 (13)
H5	0.5159	0.2128	0.1505	0.092*
C6	0.3876 (4)	0.3372 (4)	0.1137 (4)	0.0863 (15)
H6	0.3633	0.3129	0.0741	0.104*
C7	0.6221 (2)	0.2472 (3)	0.2599 (2)	0.0445 (7)
H7	0.6272	0.1726	0.2780	0.053*
C8	0.7137 (2)	0.2665 (3)	0.1879 (2)	0.0460 (8)
H8A	0.7118	0.3392	0.1728	0.055*
H8B	0.7061	0.2548	0.1297	0.055*
C9	0.8203 (2)	0.1933 (2)	0.2269 (2)	0.0382 (7)
H9	0.8288	0.1225	0.2253	0.046*
C10	0.8255 (2)	0.1874 (2)	0.3297 (2)	0.0352 (6)
C11	0.7322 (2)	0.2302 (2)	0.3808 (2)	0.0374 (7)
C12	0.7374 (3)	0.2340 (2)	0.4721 (2)	0.0438 (7)
H12	0.6758	0.2628	0.5055	0.053*
C13	0.8327 (3)	0.1955 (2)	0.5127 (2)	0.0464 (8)
H13	0.8354	0.2013	0.5721	0.056*
C14	0.9243 (3)	0.1482 (2)	0.4654 (2)	0.0452 (7)
H14	0.9881	0.1197	0.4941	0.054*
C15	0.9209 (2)	0.1434 (2)	0.3746 (2)	0.0380 (7)
C16	1.0207 (2)	0.0866 (2)	0.3289 (2)	0.0402 (7)
C17	1.0388 (2)	0.0063 (2)	0.2874 (2)	0.0407 (7)
H17	0.9888	−0.0202	0.2779	0.049*
C18	1.1431 (2)	−0.0240 (2)	0.2643 (2)	0.0429 (7)
C19	1.2137 (2)	−0.1041 (2)	0.2210 (2)	0.0470 (8)
C20	1.1780 (3)	−0.1278 (3)	0.1532 (3)	0.0616 (10)
H20	1.1094	−0.0925	0.1346	0.074*
C21	1.2446 (4)	−0.2045 (3)	0.1127 (3)	0.0763 (12)
H21	1.2205	−0.2210	0.0673	0.092*
C22	1.3470 (4)	−0.2560 (3)	0.1400 (4)	0.0783 (13)
H22	1.3920	−0.3065	0.1123	0.094*
C23	1.3819 (3)	−0.2328 (3)	0.2078 (3)	0.0695 (12)
H23	1.4508	−0.2678	0.2259	0.083*
C24	1.3166 (3)	−0.1586 (3)	0.2491 (3)	0.0558 (9)
H24	1.3407	−0.1443	0.2959	0.067*
C25	0.9335 (3)	0.3197 (3)	0.1655 (3)	0.0564 (9)
H25A	0.9496	0.3119	0.2287	0.068*
H25B	0.8764	0.3847	0.1444	0.068*
C26	1.0301 (4)	0.3184 (4)	0.0966 (4)	0.0884 (15)
H26A	1.0248	0.3888	0.0546	0.106*
H26B	1.0934	0.2921	0.1308	0.106*
C27	1.0343 (3)	0.2479 (4)	0.0412 (3)	0.0712 (12)
H27A	1.1048	0.1988	0.0386	0.085*
H27B	1.0150	0.2886	−0.0232	0.085*
C28	0.9561 (3)	0.1901 (3)	0.0928 (2)	0.0475 (8)
C29	−0.2518 (2)	0.5753 (3)	0.2061 (2)	0.0485 (8)
C30	−0.2560 (3)	0.5056 (3)	0.2951 (3)	0.0528 (9)
H30	−0.3141	0.4813	0.3177	0.063*
C31	−0.1722 (3)	0.4724 (2)	0.3505 (2)	0.0483 (8)
H31	−0.1750	0.4265	0.4117	0.058*
C32	−0.0837 (2)	0.5060 (2)	0.3171 (2)	0.0404 (7)
C33	−0.0809 (3)	0.5730 (3)	0.2250 (3)	0.0583 (9)
H33	−0.0210	0.5939	0.2002	0.070*
C34	−0.1656 (3)	0.6091 (3)	0.1698 (3)	0.0630 (10)
H34	−0.1640	0.6556	0.1088	0.076*
C35	0.0048 (2)	0.4706 (2)	0.3819 (2)	0.0433 (7)
H35	−0.0272	0.4730	0.4455	0.052*
C36	0.0762 (2)	0.3586 (2)	0.3899 (2)	0.0422 (7)
H36A	0.1121	0.3552	0.3284	0.051*
H36B	0.0338	0.3111	0.4095	0.051*
C37	0.1584 (2)	0.3241 (2)	0.4628 (2)	0.0368 (7)
H37	0.1205	0.3172	0.5258	0.044*
C38	0.2140 (2)	0.4068 (2)	0.4446 (2)	0.0340 (6)
C39	0.1663 (3)	0.5109 (2)	0.3872 (2)	0.0411 (7)
C40	0.2179 (3)	0.5872 (2)	0.3665 (2)	0.0515 (9)
H40	0.1864	0.6553	0.3287	0.062*
C41	0.3136 (3)	0.5631 (3)	0.4009 (3)	0.0518 (8)
H41	0.3474	0.6143	0.3851	0.062*
C42	0.3605 (3)	0.4633 (3)	0.4591 (2)	0.0472 (8)
H42	0.4249	0.4477	0.4833	0.057*
C43	0.3107 (2)	0.3856 (2)	0.4816 (2)	0.0375 (7)
C44	0.3630 (2)	0.2837 (2)	0.5516 (2)	0.0379 (7)
C45	0.3240 (2)	0.2333 (2)	0.6422 (2)	0.0426 (7)
H45	0.2557	0.2527	0.6699	0.051*
C46	0.4071 (3)	0.1506 (2)	0.6807 (2)	0.0443 (7)
C47	0.4233 (3)	0.0707 (3)	0.7737 (3)	0.0532 (9)
C48	0.3381 (4)	0.0623 (4)	0.8380 (3)	0.0809 (13)
H48	0.2702	0.1046	0.8209	0.097*
C49	0.3530 (5)	−0.0096 (5)	0.9289 (4)	0.0997 (17)
H49	0.2951	−0.0155	0.9720	0.120*
C50	0.4522 (5)	−0.0710 (4)	0.9544 (4)	0.0913 (16)
H50	0.4618	−0.1184	1.0151	0.110*
C51	0.5376 (5)	−0.0636 (3)	0.8917 (4)	0.0815 (14)
H51	0.6052	−0.1052	0.9098	0.098*
C52	0.5234 (3)	0.0061 (3)	0.8010 (3)	0.0646 (10)
H52	0.5817	0.0097	0.7578	0.077*
C53	0.3095 (3)	0.2023 (3)	0.3841 (3)	0.0539 (9)
H53A	0.3517	0.2498	0.3662	0.065*
H53B	0.2747	0.2113	0.3292	0.065*
C54	0.3765 (4)	0.0892 (3)	0.4239 (3)	0.0801 (13)
H54A	0.3990	0.0543	0.3749	0.096*
H54B	0.4386	0.0859	0.4503	0.096*
C55	0.3063 (3)	0.0394 (3)	0.4998 (3)	0.0656 (11)
H55A	0.3457	−0.0095	0.5539	0.079*
H55B	0.2745	0.0018	0.4759	0.079*
C56	0.2227 (3)	0.1298 (2)	0.5272 (3)	0.0484 (8)
O1W	0.0770 (3)	0.0833 (3)	0.9068 (2)	0.0812 (9)
H1WA	0.034 (5)	0.092 (5)	0.953 (5)	0.13 (2)*
H1WB	0.077 (5)	0.012 (6)	0.904 (5)	0.16 (3)*
O2W	0.0413 (3)	0.2325 (2)	0.7199 (3)	0.1003 (13)
H2WA	0.050 (4)	0.194 (4)	0.773 (4)	0.092 (18)*
H2WB	0.071 (6)	0.191 (6)	0.676 (6)	0.17 (3)*

	U11	U22	U33	U12	U13	U23
O1	0.112 (3)	0.108 (3)	0.223 (6)	0.031 (3)	−0.097 (4)	−0.061 (3)
O2	0.110 (3)	0.141 (4)	0.199 (5)	−0.002 (3)	−0.100 (3)	−0.059 (4)
O3	0.0358 (12)	0.0650 (15)	0.0817 (18)	−0.0172 (11)	0.0031 (12)	−0.0290 (14)
O4	0.0702 (17)	0.0703 (17)	0.0508 (15)	−0.0192 (13)	0.0074 (12)	−0.0327 (13)
O5	0.066 (2)	0.099 (3)	0.153 (4)	−0.0306 (19)	−0.044 (2)	−0.009 (2)
O6	0.094 (2)	0.085 (2)	0.093 (2)	−0.0120 (18)	−0.047 (2)	0.0057 (19)
O7	0.0827 (19)	0.0509 (14)	0.0628 (17)	−0.0323 (13)	0.0064 (15)	−0.0031 (12)
O8	0.0400 (12)	0.0549 (14)	0.0518 (14)	−0.0061 (10)	−0.0069 (11)	−0.0043 (11)
N1	0.064 (2)	0.083 (3)	0.102 (3)	−0.009 (2)	−0.037 (2)	−0.018 (2)
N2	0.0372 (15)	0.0636 (17)	0.0402 (15)	−0.0123 (13)	0.0027 (13)	−0.0208 (13)
N3	0.0425 (16)	0.0625 (18)	0.077 (2)	−0.0169 (14)	−0.0022 (15)	−0.0299 (16)
N4	0.0400 (14)	0.0430 (13)	0.0326 (13)	−0.0107 (11)	0.0035 (11)	−0.0093 (11)
N5	0.0507 (19)	0.063 (2)	0.078 (2)	−0.0022 (16)	−0.0216 (17)	−0.0137 (18)
N6	0.0608 (19)	0.0260 (13)	0.071 (2)	−0.0093 (13)	−0.0264 (16)	0.0001 (13)
N7	0.0441 (14)	0.0292 (12)	0.0431 (14)	−0.0093 (10)	−0.0047 (11)	−0.0081 (10)
N8	0.0393 (15)	0.0532 (16)	0.0481 (16)	−0.0086 (12)	−0.0032 (12)	−0.0052 (13)
C1	0.0437 (19)	0.066 (2)	0.068 (2)	−0.0122 (17)	−0.0178 (18)	−0.0163 (19)
C2	0.054 (2)	0.057 (2)	0.068 (3)	−0.0062 (17)	−0.0077 (19)	−0.0221 (19)
C3	0.052 (2)	0.060 (2)	0.054 (2)	−0.0148 (17)	−0.0061 (16)	−0.0252 (17)
C4	0.0364 (16)	0.0546 (19)	0.0473 (18)	−0.0152 (14)	−0.0011 (14)	−0.0204 (15)
C5	0.069 (3)	0.072 (3)	0.098 (3)	0.001 (2)	−0.033 (2)	−0.046 (2)
C6	0.077 (3)	0.087 (3)	0.112 (4)	−0.006 (2)	−0.047 (3)	−0.050 (3)
C7	0.0393 (17)	0.0489 (17)	0.0470 (18)	−0.0125 (14)	−0.0029 (14)	−0.0178 (14)
C8	0.0408 (17)	0.0587 (19)	0.0368 (17)	−0.0098 (15)	−0.0060 (13)	−0.0163 (15)
C9	0.0369 (16)	0.0419 (15)	0.0348 (16)	−0.0123 (12)	0.0016 (12)	−0.0121 (12)
C10	0.0404 (16)	0.0344 (14)	0.0307 (15)	−0.0147 (12)	−0.0011 (12)	−0.0069 (11)
C11	0.0413 (16)	0.0367 (14)	0.0335 (15)	−0.0160 (12)	0.0009 (12)	−0.0073 (12)
C12	0.0503 (19)	0.0446 (16)	0.0335 (16)	−0.0141 (14)	0.0039 (14)	−0.0121 (13)
C13	0.066 (2)	0.0429 (16)	0.0297 (16)	−0.0169 (15)	−0.0071 (15)	−0.0079 (13)
C14	0.0485 (18)	0.0425 (16)	0.0410 (18)	−0.0125 (14)	−0.0126 (14)	−0.0048 (14)
C15	0.0404 (16)	0.0351 (14)	0.0370 (16)	−0.0137 (12)	−0.0031 (13)	−0.0066 (12)
C16	0.0377 (16)	0.0418 (16)	0.0365 (16)	−0.0131 (13)	−0.0073 (13)	−0.0029 (13)
C17	0.0363 (16)	0.0426 (16)	0.0395 (17)	−0.0122 (13)	−0.0060 (13)	−0.0058 (13)
C18	0.0384 (16)	0.0425 (16)	0.0430 (18)	−0.0136 (13)	−0.0056 (13)	−0.0045 (13)
C19	0.0409 (17)	0.0422 (16)	0.0453 (19)	−0.0103 (14)	0.0038 (14)	−0.0035 (14)
C20	0.055 (2)	0.062 (2)	0.062 (2)	−0.0146 (18)	−0.0012 (18)	−0.0163 (19)
C21	0.091 (3)	0.072 (3)	0.070 (3)	−0.028 (2)	0.009 (2)	−0.030 (2)
C22	0.075 (3)	0.057 (2)	0.088 (3)	−0.014 (2)	0.025 (3)	−0.026 (2)
C23	0.046 (2)	0.058 (2)	0.079 (3)	−0.0073 (17)	0.011 (2)	−0.007 (2)
C24	0.0414 (18)	0.0536 (19)	0.058 (2)	−0.0124 (15)	0.0034 (16)	−0.0050 (16)
C25	0.064 (2)	0.0487 (19)	0.054 (2)	−0.0239 (17)	0.0065 (17)	−0.0111 (16)
C26	0.085 (3)	0.094 (3)	0.092 (3)	−0.054 (3)	0.028 (3)	−0.026 (3)
C27	0.066 (3)	0.082 (3)	0.055 (2)	−0.028 (2)	0.0201 (19)	−0.014 (2)
C28	0.0420 (17)	0.0532 (19)	0.0345 (17)	−0.0055 (14)	−0.0004 (14)	−0.0080 (14)
C29	0.0374 (17)	0.0462 (17)	0.053 (2)	−0.0043 (14)	−0.0078 (15)	−0.0109 (15)
C30	0.0391 (18)	0.0516 (19)	0.063 (2)	−0.0141 (15)	0.0049 (16)	−0.0160 (17)
C31	0.0485 (19)	0.0426 (17)	0.0433 (18)	−0.0126 (14)	−0.0006 (15)	−0.0028 (14)
C32	0.0384 (16)	0.0337 (14)	0.0409 (17)	−0.0032 (12)	−0.0028 (13)	−0.0091 (12)
C33	0.0453 (19)	0.072 (2)	0.047 (2)	−0.0236 (17)	−0.0020 (16)	0.0013 (17)
C34	0.058 (2)	0.071 (2)	0.041 (2)	−0.0227 (19)	−0.0103 (17)	0.0115 (17)
C35	0.0453 (18)	0.0355 (15)	0.0422 (17)	−0.0048 (13)	−0.0077 (14)	−0.0083 (13)
C36	0.0415 (17)	0.0330 (14)	0.0496 (19)	−0.0109 (12)	−0.0063 (14)	−0.0084 (13)
C37	0.0369 (15)	0.0288 (13)	0.0393 (16)	−0.0077 (11)	0.0008 (12)	−0.0080 (12)
C38	0.0372 (15)	0.0289 (13)	0.0346 (15)	−0.0093 (11)	0.0011 (12)	−0.0107 (11)
C39	0.0509 (18)	0.0309 (14)	0.0405 (17)	−0.0116 (13)	−0.0046 (14)	−0.0098 (12)
C40	0.073 (2)	0.0301 (15)	0.049 (2)	−0.0182 (15)	−0.0061 (17)	−0.0053 (13)
C41	0.066 (2)	0.0447 (18)	0.054 (2)	−0.0321 (17)	0.0001 (17)	−0.0122 (15)
C42	0.0481 (18)	0.0510 (18)	0.0490 (19)	−0.0236 (15)	−0.0006 (15)	−0.0159 (15)
C43	0.0403 (16)	0.0349 (14)	0.0363 (16)	−0.0123 (12)	0.0033 (13)	−0.0119 (12)
C44	0.0344 (15)	0.0398 (15)	0.0414 (17)	−0.0125 (12)	−0.0012 (13)	−0.0139 (13)
C45	0.0382 (16)	0.0457 (17)	0.0423 (17)	−0.0137 (13)	−0.0010 (13)	−0.0113 (14)
C46	0.0464 (18)	0.0449 (17)	0.0445 (18)	−0.0192 (14)	−0.0052 (14)	−0.0109 (14)
C47	0.063 (2)	0.0492 (18)	0.049 (2)	−0.0230 (17)	−0.0108 (17)	−0.0072 (15)
C48	0.076 (3)	0.083 (3)	0.064 (3)	−0.026 (2)	0.003 (2)	0.001 (2)
C49	0.111 (4)	0.105 (4)	0.063 (3)	−0.044 (3)	0.009 (3)	0.003 (3)
C50	0.135 (5)	0.076 (3)	0.058 (3)	−0.040 (3)	−0.026 (3)	0.004 (2)
C51	0.108 (4)	0.060 (2)	0.077 (3)	−0.029 (2)	−0.042 (3)	0.000 (2)
C52	0.077 (3)	0.050 (2)	0.065 (2)	−0.0218 (19)	−0.024 (2)	−0.0033 (18)
C53	0.057 (2)	0.0459 (18)	0.056 (2)	−0.0086 (15)	0.0027 (17)	−0.0228 (16)
C54	0.081 (3)	0.049 (2)	0.092 (3)	0.007 (2)	−0.002 (3)	−0.030 (2)
C55	0.075 (3)	0.0348 (17)	0.082 (3)	−0.0026 (17)	−0.024 (2)	−0.0159 (18)
C56	0.059 (2)	0.0346 (16)	0.053 (2)	−0.0185 (15)	−0.0155 (17)	−0.0050 (14)
O1W	0.082 (2)	0.093 (2)	0.066 (2)	−0.0288 (18)	0.0151 (17)	−0.0289 (17)
O2W	0.129 (3)	0.0466 (16)	0.083 (3)	−0.0045 (17)	0.016 (2)	−0.0025 (17)

O1—N1	1.191 (5)	C23—H23	0.9300
O2—N1	1.217 (6)	C24—H24	0.9300
O3—C18	1.357 (4)	C25—C26	1.511 (5)
O3—N3	1.416 (4)	C25—H25A	0.9700
O4—C28	1.228 (4)	C25—H25B	0.9700
O5—N5	1.212 (5)	C26—C27	1.483 (7)
O6—N5	1.217 (5)	C26—H26A	0.9700
O7—C56	1.225 (4)	C26—H26B	0.9700
O8—C46	1.358 (4)	C27—C28	1.505 (5)
O8—N8	1.416 (4)	C27—H27A	0.9700
N1—C1	1.469 (5)	C27—H27B	0.9700
N2—C11	1.399 (4)	C29—C34	1.365 (5)
N2—C7	1.449 (4)	C29—C30	1.370 (5)
N2—H2N	0.82 (4)	C30—C31	1.377 (5)
N3—C16	1.311 (4)	C30—H30	0.9300
N4—C28	1.345 (4)	C31—C32	1.388 (5)
N4—C25	1.463 (4)	C31—H31	0.9300
N4—C9	1.470 (4)	C32—C33	1.387 (5)
N5—C29	1.472 (5)	C32—C35	1.515 (5)
N6—C39	1.378 (4)	C33—C34	1.381 (5)
N6—C35	1.446 (4)	C33—H33	0.9300
N6—H6N	0.83 (4)	C34—H34	0.9300
N7—C56	1.346 (4)	C35—C36	1.523 (4)
N7—C53	1.461 (4)	C35—H35	0.9800
N7—C37	1.468 (3)	C36—C37	1.538 (4)
N8—C44	1.312 (4)	C36—H36A	0.9700
C1—C2	1.360 (5)	C36—H36B	0.9700
C1—C6	1.384 (6)	C37—C38	1.529 (4)
C2—C3	1.388 (5)	C37—H37	0.9800
C2—H2	0.9300	C38—C43	1.407 (4)
C3—C4	1.376 (5)	C38—C39	1.420 (4)
C3—H3	0.9300	C39—C40	1.404 (5)
C4—C5	1.382 (5)	C40—C41	1.368 (5)
C4—C7	1.519 (5)	C40—H40	0.9300
C5—C6	1.372 (6)	C41—C42	1.380 (5)
C5—H5	0.9300	C41—H41	0.9300
C6—H6	0.9300	C42—C43	1.401 (4)
C7—C8	1.526 (4)	C42—H42	0.9300
C7—H7	0.9800	C43—C44	1.490 (4)
C8—C9	1.533 (4)	C44—C45	1.407 (4)
C8—H8A	0.9700	C45—C46	1.352 (4)
C8—H8B	0.9700	C45—H45	0.9300
C9—C10	1.527 (4)	C46—C47	1.464 (5)
C9—H9	0.9800	C47—C48	1.373 (6)
C10—C15	1.405 (4)	C47—C52	1.386 (5)
C10—C11	1.409 (4)	C48—C49	1.396 (7)
C11—C12	1.402 (4)	C48—H48	0.9300
C12—C13	1.376 (5)	C49—C50	1.360 (8)
C12—H12	0.9300	C49—H49	0.9300
C13—C14	1.385 (5)	C50—C51	1.360 (7)
C13—H13	0.9300	C50—H50	0.9300
C14—C15	1.395 (5)	C51—C52	1.383 (6)
C14—H14	0.9300	C51—H51	0.9300
C15—C16	1.493 (4)	C52—H52	0.9300
C16—C17	1.407 (4)	C53—C54	1.512 (5)
C17—C18	1.340 (4)	C53—H53A	0.9700
C17—H17	0.9300	C53—H53B	0.9700
C18—C19	1.466 (5)	C54—C55	1.492 (6)
C19—C20	1.377 (5)	C54—H54A	0.9700
C19—C24	1.398 (5)	C54—H54B	0.9700
C20—C21	1.392 (6)	C55—C56	1.509 (5)
C20—H20	0.9300	C55—H55A	0.9700
C21—C22	1.384 (7)	C55—H55B	0.9700
C21—H21	0.9300	O1W—H1WA	0.83 (7)
C22—C23	1.368 (7)	O1W—H1WB	1.02 (8)
C22—H22	0.9300	O2W—H2WA	0.80 (6)
C23—C24	1.369 (6)	O2W—H2WB	0.98 (8)
C18—O3—N3	108.5 (2)	H26A—C26—H26B	108.6
C46—O8—N8	108.4 (2)	C26—C27—C28	105.7 (3)
O1—N1—O2	121.6 (4)	C26—C27—H27A	110.6
O1—N1—C1	119.3 (4)	C28—C27—H27A	110.6
O2—N1—C1	119.0 (4)	C26—C27—H27B	110.6
C11—N2—C7	118.4 (3)	C28—C27—H27B	110.6
C11—N2—H2N	107 (3)	H27A—C27—H27B	108.7
C7—N2—H2N	117 (3)	O4—C28—N4	125.6 (3)
C16—N3—O3	105.1 (3)	O4—C28—C27	126.2 (3)
C28—N4—C25	113.5 (3)	N4—C28—C27	108.2 (3)
C28—N4—C9	122.3 (3)	C34—C29—C30	122.0 (3)
C25—N4—C9	123.6 (2)	C34—C29—N5	118.2 (3)
O5—N5—O6	123.6 (4)	C30—C29—N5	119.8 (3)
O5—N5—C29	118.5 (3)	C29—C30—C31	118.5 (3)
O6—N5—C29	117.8 (4)	C29—C30—H30	120.7
C39—N6—C35	121.3 (3)	C31—C30—H30	120.7
C39—N6—H6N	116 (3)	C30—C31—C32	121.5 (3)
C35—N6—H6N	117 (3)	C30—C31—H31	119.3
C56—N7—C53	112.7 (3)	C32—C31—H31	119.3
C56—N7—C37	123.1 (3)	C33—C32—C31	118.0 (3)
C53—N7—C37	122.9 (2)	C33—C32—C35	122.4 (3)
C44—N8—O8	105.4 (2)	C31—C32—C35	119.6 (3)
C2—C1—C6	121.4 (4)	C34—C33—C32	121.0 (3)
C2—C1—N1	119.5 (4)	C34—C33—H33	119.5
C6—C1—N1	119.1 (4)	C32—C33—H33	119.5
C1—C2—C3	119.3 (3)	C29—C34—C33	118.9 (3)
C1—C2—H2	120.4	C29—C34—H34	120.5
C3—C2—H2	120.4	C33—C34—H34	120.5
C4—C3—C2	120.7 (3)	N6—C35—C32	111.8 (3)
C4—C3—H3	119.7	N6—C35—C36	107.9 (3)
C2—C3—H3	119.7	C32—C35—C36	112.7 (3)
C3—C4—C5	118.5 (3)	N6—C35—H35	108.1
C3—C4—C7	122.8 (3)	C32—C35—H35	108.1
C5—C4—C7	118.7 (3)	C36—C35—H35	108.1
C6—C5—C4	121.7 (4)	C35—C36—C37	110.2 (3)
C6—C5—H5	119.1	C35—C36—H36A	109.6
C4—C5—H5	119.1	C37—C36—H36A	109.6
C5—C6—C1	118.3 (4)	C35—C36—H36B	109.6
C5—C6—H6	120.9	C37—C36—H36B	109.6
C1—C6—H6	120.9	H36A—C36—H36B	108.1
N2—C7—C4	111.8 (3)	N7—C37—C38	112.6 (2)
N2—C7—C8	107.4 (3)	N7—C37—C36	109.7 (2)
C4—C7—C8	110.6 (3)	C38—C37—C36	111.5 (2)
N2—C7—H7	109.0	N7—C37—H37	107.6
C4—C7—H7	109.0	C38—C37—H37	107.6
C8—C7—H7	109.0	C36—C37—H37	107.6
C7—C8—C9	111.2 (3)	C43—C38—C39	117.7 (3)
C7—C8—H8A	109.4	C43—C38—C37	123.6 (2)
C9—C8—H8A	109.4	C39—C38—C37	118.7 (3)
C7—C8—H8B	109.4	N6—C39—C40	118.8 (3)
C9—C8—H8B	109.4	N6—C39—C38	121.5 (3)
H8A—C8—H8B	108.0	C40—C39—C38	119.7 (3)
N4—C9—C10	111.4 (2)	C41—C40—C39	121.1 (3)
N4—C9—C8	109.1 (2)	C41—C40—H40	119.4
C10—C9—C8	111.8 (2)	C39—C40—H40	119.4
N4—C9—H9	108.1	C40—C41—C42	120.4 (3)
C10—C9—H9	108.1	C40—C41—H41	119.8
C8—C9—H9	108.1	C42—C41—H41	119.8
C15—C10—C11	118.4 (3)	C41—C42—C43	119.9 (3)
C15—C10—C9	122.4 (3)	C41—C42—H42	120.1
C11—C10—C9	119.1 (3)	C43—C42—H42	120.1
N2—C11—C12	118.0 (3)	C42—C43—C38	121.2 (3)
N2—C11—C10	122.3 (3)	C42—C43—C44	115.5 (3)
C12—C11—C10	119.7 (3)	C38—C43—C44	123.2 (3)
C13—C12—C11	120.8 (3)	N8—C44—C45	111.6 (3)
C13—C12—H12	119.6	N8—C44—C43	118.7 (3)
C11—C12—H12	119.6	C45—C44—C43	129.3 (3)
C12—C13—C14	120.2 (3)	C46—C45—C44	105.4 (3)
C12—C13—H13	119.9	C46—C45—H45	127.3
C14—C13—H13	119.9	C44—C45—H45	127.3
C13—C14—C15	119.9 (3)	C45—C46—O8	109.1 (3)
C13—C14—H14	120.1	C45—C46—C47	134.1 (3)
C15—C14—H14	120.1	O8—C46—C47	116.7 (3)
C14—C15—C10	120.8 (3)	C48—C47—C52	118.6 (4)
C14—C15—C16	117.8 (3)	C48—C47—C46	119.5 (4)
C10—C15—C16	121.4 (3)	C52—C47—C46	121.8 (3)
N3—C16—C17	111.6 (3)	C47—C48—C49	120.1 (5)
N3—C16—C15	118.9 (3)	C47—C48—H48	119.9
C17—C16—C15	129.2 (3)	C49—C48—H48	119.9
C18—C17—C16	105.6 (3)	C50—C49—C48	120.1 (5)
C18—C17—H17	127.2	C50—C49—H49	120.0
C16—C17—H17	127.2	C48—C49—H49	120.0
C17—C18—O3	109.2 (3)	C51—C50—C49	120.6 (4)
C17—C18—C19	133.9 (3)	C51—C50—H50	119.7
O3—C18—C19	116.8 (3)	C49—C50—H50	119.7
C20—C19—C24	119.4 (3)	C50—C51—C52	119.8 (5)
C20—C19—C18	119.9 (3)	C50—C51—H51	120.1
C24—C19—C18	120.7 (3)	C52—C51—H51	120.1
C19—C20—C21	120.0 (4)	C51—C52—C47	120.8 (4)
C19—C20—H20	120.0	C51—C52—H52	119.6
C21—C20—H20	120.0	C47—C52—H52	119.6
C22—C21—C20	119.8 (4)	N7—C53—C54	102.8 (3)
C22—C21—H21	120.1	N7—C53—H53A	111.2
C20—C21—H21	120.1	C54—C53—H53A	111.2
C23—C22—C21	120.0 (4)	N7—C53—H53B	111.2
C23—C22—H22	120.0	C54—C53—H53B	111.2
C21—C22—H22	120.0	H53A—C53—H53B	109.1
C22—C23—C24	120.6 (4)	C55—C54—C53	104.9 (3)
C22—C23—H23	119.7	C55—C54—H54A	110.8
C24—C23—H23	119.7	C53—C54—H54A	110.8
C23—C24—C19	120.1 (4)	C55—C54—H54B	110.8
C23—C24—H24	119.9	C53—C54—H54B	110.8
C19—C24—H24	119.9	H54A—C54—H54B	108.8
N4—C25—C26	103.4 (3)	C54—C55—C56	105.0 (3)
N4—C25—H25A	111.1	C54—C55—H55A	110.8
C26—C25—H25A	111.1	C56—C55—H55A	110.8
N4—C25—H25B	111.1	C54—C55—H55B	110.8
C26—C25—H25B	111.1	C56—C55—H55B	110.8
H25A—C25—H25B	109.0	H55A—C55—H55B	108.8
C27—C26—C25	106.8 (3)	O7—C56—N7	125.6 (3)
C27—C26—H26A	110.4	O7—C56—C55	126.5 (3)
C25—C26—H26A	110.4	N7—C56—C55	107.9 (3)
C27—C26—H26B	110.4	H1WA—O1W—H1WB	102 (6)
C25—C26—H26B	110.4	H2WA—O2W—H2WB	108 (6)
C18—O3—N3—C16	−0.9 (4)	C26—C27—C28—N4	4.8 (5)
C46—O8—N8—C44	−0.3 (3)	O5—N5—C29—C34	159.1 (4)
O1—N1—C1—C2	3.3 (7)	O6—N5—C29—C34	−23.9 (5)
O2—N1—C1—C2	−179.0 (5)	O5—N5—C29—C30	−21.3 (6)
O1—N1—C1—C6	−178.1 (6)	O6—N5—C29—C30	155.7 (4)
O2—N1—C1—C6	−0.4 (7)	C34—C29—C30—C31	2.6 (5)
C6—C1—C2—C3	3.0 (7)	N5—C29—C30—C31	−176.9 (3)
N1—C1—C2—C3	−178.4 (4)	C29—C30—C31—C32	−1.6 (5)
C1—C2—C3—C4	−0.5 (6)	C30—C31—C32—C33	−1.1 (5)
C2—C3—C4—C5	−2.6 (6)	C30—C31—C32—C35	177.7 (3)
C2—C3—C4—C7	176.7 (3)	C31—C32—C33—C34	2.9 (6)
C3—C4—C5—C6	3.3 (7)	C35—C32—C33—C34	−175.9 (3)
C7—C4—C5—C6	−176.0 (4)	C30—C29—C34—C33	−0.9 (6)
C4—C5—C6—C1	−0.9 (8)	N5—C29—C34—C33	178.6 (4)
C2—C1—C6—C5	−2.3 (8)	C32—C33—C34—C29	−1.9 (6)
N1—C1—C6—C5	179.1 (5)	C39—N6—C35—C32	−167.4 (3)
C11—N2—C7—C4	−169.6 (3)	C39—N6—C35—C36	−42.9 (4)
C11—N2—C7—C8	−48.1 (4)	C33—C32—C35—N6	19.1 (4)
C3—C4—C7—N2	21.5 (5)	C31—C32—C35—N6	−159.7 (3)
C5—C4—C7—N2	−159.1 (4)	C33—C32—C35—C36	−102.7 (4)
C3—C4—C7—C8	−98.1 (4)	C31—C32—C35—C36	78.6 (4)
C5—C4—C7—C8	81.2 (4)	N6—C35—C36—C37	60.8 (3)
N2—C7—C8—C9	62.6 (3)	C32—C35—C36—C37	−175.3 (2)
C4—C7—C8—C9	−175.2 (3)	C56—N7—C37—C38	138.2 (3)
C28—N4—C9—C10	142.5 (3)	C53—N7—C37—C38	−55.9 (4)
C25—N4—C9—C10	−46.8 (4)	C56—N7—C37—C36	−96.9 (3)
C28—N4—C9—C8	−93.6 (3)	C53—N7—C37—C36	68.9 (4)
C25—N4—C9—C8	77.1 (4)	C35—C36—C37—N7	−174.8 (2)
C7—C8—C9—N4	−168.3 (3)	C35—C36—C37—C38	−49.4 (3)
C7—C8—C9—C10	−44.7 (4)	N7—C37—C38—C43	−37.9 (4)
N4—C9—C10—C15	−44.4 (4)	C36—C37—C38—C43	−161.7 (3)
C8—C9—C10—C15	−166.7 (3)	N7—C37—C38—C39	142.0 (3)
N4—C9—C10—C11	133.7 (3)	C36—C37—C38—C39	18.2 (4)
C8—C9—C10—C11	11.4 (4)	C35—N6—C39—C40	−169.0 (3)
C7—N2—C11—C12	−165.9 (3)	C35—N6—C39—C38	11.7 (5)
C7—N2—C11—C10	15.5 (4)	C43—C38—C39—N6	−178.4 (3)
C15—C10—C11—N2	−177.5 (3)	C37—C38—C39—N6	1.7 (4)
C9—C10—C11—N2	4.4 (4)	C43—C38—C39—C40	2.4 (4)
C15—C10—C11—C12	4.0 (4)	C37—C38—C39—C40	−177.5 (3)
C9—C10—C11—C12	−174.1 (3)	N6—C39—C40—C41	−179.5 (3)
N2—C11—C12—C13	−179.2 (3)	C38—C39—C40—C41	−0.2 (5)
C10—C11—C12—C13	−0.6 (4)	C39—C40—C41—C42	−1.6 (5)
C11—C12—C13—C14	−2.8 (5)	C40—C41—C42—C43	1.2 (5)
C12—C13—C14—C15	2.7 (5)	C41—C42—C43—C38	1.1 (5)
C13—C14—C15—C10	0.9 (5)	C41—C42—C43—C44	−174.8 (3)
C13—C14—C15—C16	−176.8 (3)	C39—C38—C43—C42	−2.8 (4)
C11—C10—C15—C14	−4.2 (4)	C37—C38—C43—C42	177.1 (3)
C9—C10—C15—C14	173.9 (3)	C39—C38—C43—C44	172.8 (3)
C11—C10—C15—C16	173.4 (3)	C37—C38—C43—C44	−7.3 (4)
C9—C10—C15—C16	−8.5 (4)	O8—N8—C44—C45	0.0 (4)
O3—N3—C16—C17	0.9 (4)	O8—N8—C44—C43	173.6 (3)
O3—N3—C16—C15	175.7 (3)	C42—C43—C44—N8	−54.3 (4)
C14—C15—C16—N3	−45.5 (4)	C38—C43—C44—N8	129.9 (3)
C10—C15—C16—N3	136.9 (3)	C42—C43—C44—C45	118.0 (4)
C14—C15—C16—C17	128.3 (3)	C38—C43—C44—C45	−57.8 (5)
C10—C15—C16—C17	−49.4 (4)	N8—C44—C45—C46	0.4 (4)
N3—C16—C17—C18	−0.6 (4)	C43—C44—C45—C46	−172.4 (3)
C15—C16—C17—C18	−174.7 (3)	C44—C45—C46—O8	−0.6 (4)
C16—C17—C18—O3	0.0 (3)	C44—C45—C46—C47	175.6 (4)
C16—C17—C18—C19	178.8 (3)	N8—O8—C46—C45	0.6 (4)
N3—O3—C18—C17	0.6 (4)	N8—O8—C46—C47	−176.3 (3)
N3—O3—C18—C19	−178.4 (3)	C45—C46—C47—C48	9.7 (6)
C17—C18—C19—C20	33.9 (5)	O8—C46—C47—C48	−174.3 (4)
O3—C18—C19—C20	−147.4 (3)	C45—C46—C47—C52	−167.0 (4)
C17—C18—C19—C24	−144.8 (4)	O8—C46—C47—C52	8.9 (5)
O3—C18—C19—C24	33.9 (4)	C52—C47—C48—C49	0.4 (7)
C24—C19—C20—C21	−0.7 (5)	C46—C47—C48—C49	−176.5 (4)
C18—C19—C20—C21	−179.4 (3)	C47—C48—C49—C50	0.5 (9)
C19—C20—C21—C22	−0.6 (6)	C48—C49—C50—C51	−0.4 (9)
C20—C21—C22—C23	1.0 (6)	C49—C50—C51—C52	−0.7 (8)
C21—C22—C23—C24	−0.1 (6)	C50—C51—C52—C47	1.7 (7)
C22—C23—C24—C19	−1.2 (6)	C48—C47—C52—C51	−1.5 (6)
C20—C19—C24—C23	1.6 (5)	C46—C47—C52—C51	175.3 (4)
C18—C19—C24—C23	−179.7 (3)	C56—N7—C53—C54	−20.9 (4)
C28—N4—C25—C26	−13.2 (4)	C37—N7—C53—C54	172.0 (3)
C9—N4—C25—C26	175.3 (3)	N7—C53—C54—C55	25.6 (4)
N4—C25—C26—C27	15.4 (5)	C53—C54—C55—C56	−22.0 (5)
C25—C26—C27—C28	−12.7 (5)	C53—N7—C56—O7	−172.8 (3)
C25—N4—C28—O4	−174.6 (3)	C37—N7—C56—O7	−5.7 (5)
C9—N4—C28—O4	−3.0 (5)	C53—N7—C56—C55	7.2 (4)
C25—N4—C28—C27	5.5 (4)	C37—N7—C56—C55	174.3 (3)
C9—N4—C28—C27	177.1 (3)	C54—C55—C56—O7	−170.2 (4)
C26—C27—C28—O4	−175.0 (4)	C54—C55—C56—N7	9.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O4i	0.83 (7)	2.07 (7)	2.904 (5)	173 (6)
O1W—H1WB···O4ii	1.03 (8)	1.87 (8)	2.877 (5)	167 (6)
O2W—H2WB···O7	0.97 (8)	1.80 (9)	2.754 (5)	165 (8)
N6—H6N···O2Wiii	0.83 (4)	2.13 (4)	2.958 (5)	179 (5)
O2W—H2WA···O1W	0.80 (6)	2.09 (6)	2.883 (6)	175 (6)
C3—H3···N2	0.93	2.52	2.848 (6)	101
C9—H9···O4	0.98	2.50	2.857 (4)	101
C33—H33···N6	0.93	2.51	2.830 (6)	100
C37—H37···O7	0.98	2.49	2.872 (4)	103
C52—H52···O8	0.93	2.50	2.811 (5)	100

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O4i	0.83 (7)	2.07 (7)	2.904 (5)	173 (6)
O1W—H1WB⋯O4ii	1.03 (8)	1.87 (8)	2.877 (5)	167 (6)
O2W—H2WB⋯O7	0.97 (8)	1.80 (9)	2.754 (5)	165 (8)
N6—H6N⋯O2Wiii	0.83 (4)	2.13 (4)	2.958 (5)	179 (5)
O2W—H2WA⋯O1W	0.80 (6)	2.09 (6)	2.883 (6)	175 (6)

Symmetry codes: (i) ; (ii) ; (iii) .