1-Ethyl-2-tosyl-4,4,6-trimethyl-2,3,3a,4-tetra-hydro-1H-pyrrolo[3,4-c]pyrano[6,5-b]quinoline-11(6H)-one monohydrate.

In the title compound, C(26)H(30)N(2)O(4)S·H(2)O, the pyrrolidine and dihydro-pyran rings adopt envelope conformations and they are cis-fused. The sulfonyl group has a distorted tetra-hedral geometry. In the crystal structure, the mol-ecules are linked into a ribbon-like structure along the a axis by O/C-H⋯O hydrogen bonds involving water mol-ecules and C-H⋯π inter-actions involving the sulfonyl-bound phenyl ring. Adjacent ribbons are cross-linked via C-H⋯O hydrogen bonds involving a sulfonyl O atom and C-H⋯π inter-actions involving the pyridinone ring.

Related literature

For the biological activity of pyran­oquinolinones, see: Duraipandiyan & Ignacimuthu (2009 ▶); Magedov et al. (2008 ▶); Marco-Contelles et al. (2006 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Duax et al. (1976 ▶). For a related structure, see: Chinnakali et al. (2007 ▶).

Experimental

Crystal data

C26H30N2O4S·H2O

M = 484.60

Triclinic,

a = 9.6964 (2) Å

b = 10.2315 (3) Å

c = 13.5500 (3) Å

α = 92.143 (1)°

β = 93.142 (1)°

γ = 115.703 (1)°

V = 1206.65 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.17 mm−1

T = 100 K

0.58 × 0.32 × 0.32 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.842, T max = 0.947

32886 measured reflections

10512 independent reflections

9074 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.108

S = 1.04

10512 reflections

320 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.57 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809030761/bq2154sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030761/bq2154Isup2.hkl

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

C26H30N2O4S·H2O	Z = 2
Mr = 484.60	F(000) = 516
Triclinic, P1	Dx = 1.334 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6964 (2) Å	Cell parameters from 9831 reflections
b = 10.2315 (3) Å	θ = 2.4–40.2°
c = 13.5500 (3) Å	µ = 0.17 mm−1
α = 92.143 (1)°	T = 100 K
β = 93.142 (1)°	Block, colourless
γ = 115.703 (1)°	0.58 × 0.32 × 0.32 mm
V = 1206.65 (5) Å3

Bruker SMART APEXII CCD area-detector diffractometer	10512 independent reflections
Radiation source: fine-focus sealed tube	9074 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 35.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −14→15
Tmin = 0.842, Tmax = 0.947	k = −16→16
32886 measured reflections	l = −21→21

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0587P)2 + 0.2725P] where P = (Fo2 + 2Fc2)/3
10512 reflections	(Δ/σ)max = 0.001
320 parameters	Δρmax = 0.57 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

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	−0.10550 (2)	0.20102 (2)	0.101937 (13)	0.01815 (5)
O1	−0.14482 (8)	0.10439 (8)	0.01424 (5)	0.02588 (13)
O2	−0.21397 (7)	0.24814 (8)	0.13802 (5)	0.02463 (12)
O3	0.36172 (7)	0.10968 (7)	0.36629 (4)	0.02095 (11)
O4	0.05379 (7)	0.31969 (7)	0.50127 (4)	0.02048 (11)
N1	−0.06215 (7)	0.11918 (7)	0.19027 (5)	0.01627 (11)
N2	0.44953 (7)	0.26770 (7)	0.49833 (5)	0.01623 (11)
C1	0.03179 (9)	0.04091 (8)	0.17054 (6)	0.01816 (12)
H1A	0.0728	0.0600	0.1062	0.022*
H1B	−0.0267	−0.0631	0.1744	0.022*
C2	0.15833 (8)	0.10586 (8)	0.25395 (5)	0.01455 (11)
H2	0.2276	0.2040	0.2370	0.017*
C3	0.07378 (8)	0.12244 (7)	0.34232 (5)	0.01382 (11)
H3	0.0114	0.0254	0.3642	0.017*
C4	−0.03588 (8)	0.18134 (8)	0.29580 (5)	0.01449 (11)
H4	0.0166	0.2877	0.2976	0.017*
C5	0.25658 (8)	0.02781 (8)	0.27888 (5)	0.01649 (12)
C6	0.32986 (8)	0.19511 (8)	0.42907 (5)	0.01509 (11)
C7	0.19301 (8)	0.20919 (8)	0.42556 (5)	0.01399 (11)
C8	0.06168 (9)	0.35827 (9)	0.08100 (5)	0.01895 (13)
C9	0.09398 (10)	0.48997 (9)	0.13299 (6)	0.02292 (14)
H9	0.0276	0.4957	0.1781	0.027*
C10	0.22655 (11)	0.61223 (10)	0.11634 (7)	0.02546 (16)
H10	0.2482	0.7000	0.1509	0.031*
C11	0.32828 (10)	0.60689 (10)	0.04910 (6)	0.02372 (15)
C12	0.29358 (11)	0.47384 (11)	−0.00188 (6)	0.02569 (16)
H12	0.3601	0.4681	−0.0469	0.031*
C13	0.16132 (10)	0.34970 (10)	0.01340 (6)	0.02375 (15)
H13	0.1396	0.2618	−0.0211	0.028*
C14	0.47103 (12)	0.74153 (12)	0.03266 (8)	0.03231 (19)
H14A	0.4436	0.8179	0.0156	0.048*
H14B	0.5221	0.7210	−0.0203	0.048*
H14C	0.5385	0.7716	0.0922	0.048*
C15	0.36409 (9)	0.03800 (9)	0.19901 (6)	0.02084 (14)
H15A	0.4236	0.1382	0.1867	0.031*
H15B	0.3051	−0.0143	0.1392	0.031*
H15C	0.4315	−0.0034	0.2207	0.031*
C16	0.16794 (11)	−0.12767 (9)	0.30705 (7)	0.02468 (15)
H16A	0.1110	−0.1286	0.3630	0.037*
H16B	0.2385	−0.1678	0.3238	0.037*
H16C	0.0984	−0.1849	0.2521	0.037*
C17	0.43494 (8)	0.35304 (8)	0.57565 (5)	0.01535 (11)
C18	0.55160 (9)	0.41818 (8)	0.65335 (6)	0.01901 (13)
H18	0.6413	0.4062	0.6529	0.023*
C19	0.53158 (10)	0.49978 (9)	0.73000 (6)	0.02148 (14)
H19	0.6081	0.5415	0.7814	0.026*
C20	0.39817 (10)	0.52082 (9)	0.73172 (6)	0.02210 (14)
H20	0.3871	0.5777	0.7830	0.027*
C21	0.28324 (9)	0.45606 (8)	0.65626 (6)	0.01910 (13)
H21	0.1941	0.4690	0.6574	0.023*
C22	0.29908 (8)	0.37079 (8)	0.57767 (5)	0.01509 (11)
C23	0.17397 (8)	0.30031 (8)	0.50003 (5)	0.01469 (11)
C24	−0.19016 (9)	0.13330 (9)	0.34164 (6)	0.01990 (13)
H24A	−0.1706	0.1584	0.4124	0.024*
H24B	−0.2427	0.1872	0.3142	0.024*
C25	−0.29541 (11)	−0.02827 (11)	0.32456 (9)	0.0329 (2)
H25A	−0.3893	−0.0501	0.3551	0.049*
H25B	−0.2457	−0.0828	0.3531	0.049*
H25C	−0.3177	−0.0540	0.2547	0.049*
C26	0.59115 (9)	0.24915 (10)	0.49227 (6)	0.02184 (14)
H26A	0.6064	0.2347	0.4241	0.033*
H26B	0.5825	0.1661	0.5270	0.033*
H26C	0.6769	0.3345	0.5218	0.033*
O1W	0.07659 (8)	0.54423 (7)	0.37852 (5)	0.02352 (12)
H1W1	0.039 (2)	0.5967 (19)	0.4179 (14)	0.057 (5)*
H2W1	0.0587 (19)	0.4646 (19)	0.4169 (13)	0.050 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.01901 (8)	0.02528 (9)	0.01322 (8)	0.01303 (7)	−0.00226 (6)	−0.00017 (6)
O1	0.0270 (3)	0.0342 (3)	0.0153 (2)	0.0138 (3)	−0.0065 (2)	−0.0055 (2)
O2	0.0232 (3)	0.0363 (3)	0.0231 (3)	0.0210 (3)	0.0015 (2)	0.0048 (2)
O3	0.0222 (2)	0.0308 (3)	0.0164 (2)	0.0188 (2)	−0.00380 (19)	−0.0072 (2)
O4	0.0218 (2)	0.0277 (3)	0.0182 (2)	0.0173 (2)	−0.00107 (19)	−0.0039 (2)
N1	0.0196 (3)	0.0198 (3)	0.0127 (2)	0.0121 (2)	−0.00137 (19)	−0.00144 (19)
N2	0.0152 (2)	0.0210 (3)	0.0139 (2)	0.0096 (2)	−0.00049 (19)	−0.0008 (2)
C1	0.0211 (3)	0.0210 (3)	0.0157 (3)	0.0133 (3)	−0.0028 (2)	−0.0045 (2)
C2	0.0162 (3)	0.0165 (3)	0.0131 (3)	0.0094 (2)	0.0002 (2)	−0.0011 (2)
C3	0.0146 (3)	0.0156 (3)	0.0129 (3)	0.0084 (2)	0.0002 (2)	−0.0003 (2)
C4	0.0159 (3)	0.0169 (3)	0.0125 (3)	0.0092 (2)	0.0000 (2)	−0.0004 (2)
C5	0.0183 (3)	0.0195 (3)	0.0145 (3)	0.0114 (2)	−0.0008 (2)	−0.0026 (2)
C6	0.0164 (3)	0.0187 (3)	0.0125 (3)	0.0100 (2)	0.0004 (2)	0.0000 (2)
C7	0.0153 (3)	0.0166 (3)	0.0121 (2)	0.0091 (2)	0.0004 (2)	0.0000 (2)
C8	0.0236 (3)	0.0244 (3)	0.0131 (3)	0.0144 (3)	0.0010 (2)	0.0019 (2)
C9	0.0298 (4)	0.0248 (3)	0.0205 (3)	0.0175 (3)	0.0048 (3)	0.0022 (3)
C10	0.0327 (4)	0.0237 (4)	0.0243 (4)	0.0162 (3)	0.0032 (3)	0.0020 (3)
C11	0.0262 (4)	0.0277 (4)	0.0190 (3)	0.0132 (3)	0.0007 (3)	0.0058 (3)
C12	0.0275 (4)	0.0329 (4)	0.0183 (3)	0.0143 (3)	0.0049 (3)	0.0017 (3)
C13	0.0275 (4)	0.0293 (4)	0.0166 (3)	0.0145 (3)	0.0037 (3)	−0.0018 (3)
C14	0.0295 (4)	0.0321 (4)	0.0327 (5)	0.0105 (4)	0.0027 (4)	0.0084 (4)
C15	0.0212 (3)	0.0283 (4)	0.0173 (3)	0.0152 (3)	0.0013 (2)	−0.0035 (3)
C16	0.0272 (4)	0.0210 (3)	0.0313 (4)	0.0152 (3)	0.0039 (3)	0.0051 (3)
C17	0.0167 (3)	0.0160 (3)	0.0129 (3)	0.0068 (2)	0.0006 (2)	0.0014 (2)
C18	0.0179 (3)	0.0199 (3)	0.0165 (3)	0.0062 (2)	−0.0020 (2)	0.0009 (2)
C19	0.0241 (3)	0.0198 (3)	0.0163 (3)	0.0064 (3)	−0.0033 (3)	−0.0011 (2)
C20	0.0283 (4)	0.0217 (3)	0.0154 (3)	0.0107 (3)	−0.0014 (3)	−0.0031 (2)
C21	0.0235 (3)	0.0200 (3)	0.0150 (3)	0.0109 (3)	0.0003 (2)	−0.0019 (2)
C22	0.0179 (3)	0.0159 (3)	0.0122 (3)	0.0082 (2)	0.0004 (2)	0.0002 (2)
C23	0.0178 (3)	0.0164 (3)	0.0121 (3)	0.0096 (2)	0.0009 (2)	0.0007 (2)
C24	0.0169 (3)	0.0283 (4)	0.0175 (3)	0.0126 (3)	0.0023 (2)	0.0020 (3)
C25	0.0183 (3)	0.0290 (4)	0.0507 (6)	0.0084 (3)	0.0073 (4)	0.0134 (4)
C26	0.0175 (3)	0.0314 (4)	0.0204 (3)	0.0147 (3)	−0.0009 (2)	−0.0011 (3)
O1W	0.0259 (3)	0.0248 (3)	0.0238 (3)	0.0147 (2)	0.0038 (2)	−0.0016 (2)

S1—O2	1.4341 (6)	C12—C13	1.3916 (13)
S1—O1	1.4389 (6)	C12—H12	0.93
S1—N1	1.6234 (6)	C13—H13	0.93
S1—C8	1.7661 (8)	C14—H14A	0.96
O3—C6	1.3381 (9)	C14—H14B	0.96
O3—C5	1.4821 (9)	C14—H14C	0.96
O4—C23	1.2648 (9)	C15—H15A	0.96
N1—C1	1.4784 (9)	C15—H15B	0.96
N1—C4	1.5052 (9)	C15—H15C	0.96
N2—C6	1.3637 (9)	C16—H16A	0.96
N2—C17	1.3911 (9)	C16—H16B	0.96
N2—C26	1.4716 (10)	C16—H16C	0.96
C1—C2	1.5196 (10)	C17—C22	1.4071 (10)
C1—H1A	0.97	C17—C18	1.4126 (10)
C1—H1B	0.97	C18—C19	1.3825 (11)
C2—C5	1.5179 (10)	C18—H18	0.93
C2—C3	1.5321 (10)	C19—C20	1.4017 (12)
C2—H2	0.98	C19—H19	0.93
C3—C7	1.5128 (10)	C20—C21	1.3822 (11)
C3—C4	1.5499 (10)	C20—H20	0.93
C3—H3	0.98	C21—C22	1.4084 (10)
C4—C24	1.5337 (10)	C21—H21	0.93
C4—H4	0.98	C22—C23	1.4640 (10)
C5—C15	1.5187 (11)	C24—C25	1.5198 (13)
C5—C16	1.5201 (11)	C24—H24A	0.97
C6—C7	1.3940 (10)	C24—H24B	0.97
C7—C23	1.4216 (10)	C25—H25A	0.96
C8—C13	1.3944 (11)	C25—H25B	0.96
C8—C9	1.3960 (11)	C25—H25C	0.96
C9—C10	1.3878 (13)	C26—H26A	0.96
C9—H9	0.93	C26—H26B	0.96
C10—C11	1.3956 (13)	C26—H26C	0.96
C10—H10	0.93	O1W—H1W1	0.933 (18)
C11—C12	1.3965 (13)	O1W—H2W1	0.940 (18)
C11—C14	1.5053 (13)
O2—S1—O1	120.48 (4)	C11—C12—H12	119.4
O2—S1—N1	106.96 (4)	C12—C13—C8	119.38 (8)
O1—S1—N1	106.25 (4)	C12—C13—H13	120.3
O2—S1—C8	107.39 (4)	C8—C13—H13	120.3
O1—S1—C8	107.16 (4)	C11—C14—H14A	109.5
N1—S1—C8	108.10 (4)	C11—C14—H14B	109.5
C6—O3—C5	122.23 (6)	H14A—C14—H14B	109.5
C1—N1—C4	112.20 (5)	C11—C14—H14C	109.5
C1—N1—S1	119.56 (5)	H14A—C14—H14C	109.5
C4—N1—S1	120.20 (5)	H14B—C14—H14C	109.5
C6—N2—C17	120.21 (6)	C5—C15—H15A	109.5
C6—N2—C26	118.97 (6)	C5—C15—H15B	109.5
C17—N2—C26	120.77 (6)	H15A—C15—H15B	109.5
N1—C1—C2	101.53 (5)	C5—C15—H15C	109.5
N1—C1—H1A	111.5	H15A—C15—H15C	109.5
C2—C1—H1A	111.5	H15B—C15—H15C	109.5
N1—C1—H1B	111.5	C5—C16—H16A	109.5
C2—C1—H1B	111.5	C5—C16—H16B	109.5
H1A—C1—H1B	109.3	H16A—C16—H16B	109.5
C5—C2—C1	118.88 (6)	C5—C16—H16C	109.5
C5—C2—C3	112.23 (6)	H16A—C16—H16C	109.5
C1—C2—C3	103.40 (6)	H16B—C16—H16C	109.5
C5—C2—H2	107.2	N2—C17—C22	119.09 (6)
C1—C2—H2	107.2	N2—C17—C18	121.27 (7)
C3—C2—H2	107.2	C22—C17—C18	119.61 (7)
C7—C3—C2	107.88 (5)	C19—C18—C17	119.61 (7)
C7—C3—C4	120.70 (6)	C19—C18—H18	120.2
C2—C3—C4	102.90 (5)	C17—C18—H18	120.2
C7—C3—H3	108.2	C18—C19—C20	121.29 (7)
C2—C3—H3	108.2	C18—C19—H19	119.4
C4—C3—H3	108.2	C20—C19—H19	119.4
N1—C4—C24	109.79 (6)	C21—C20—C19	119.20 (7)
N1—C4—C3	102.05 (5)	C21—C20—H20	120.4
C24—C4—C3	115.58 (6)	C19—C20—H20	120.4
N1—C4—H4	109.7	C20—C21—C22	120.98 (7)
C24—C4—H4	109.7	C20—C21—H21	119.5
C3—C4—H4	109.7	C22—C21—H21	119.5
O3—C5—C2	106.88 (6)	C17—C22—C21	119.29 (7)
O3—C5—C15	103.73 (6)	C17—C22—C23	120.83 (6)
C2—C5—C15	112.07 (6)	C21—C22—C23	119.88 (7)
O3—C5—C16	106.72 (6)	O4—C23—C7	122.29 (7)
C2—C5—C16	114.79 (6)	O4—C23—C22	120.33 (6)
C15—C5—C16	111.75 (6)	C7—C23—C22	117.37 (6)
O3—C6—N2	111.07 (6)	C25—C24—C4	114.19 (7)
O3—C6—C7	125.22 (6)	C25—C24—H24A	108.7
N2—C6—C7	123.71 (6)	C4—C24—H24A	108.7
C6—C7—C23	118.59 (6)	C25—C24—H24B	108.7
C6—C7—C3	116.49 (6)	C4—C24—H24B	108.7
C23—C7—C3	124.90 (6)	H24A—C24—H24B	107.6
C13—C8—C9	120.45 (8)	C24—C25—H25A	109.5
C13—C8—S1	119.77 (6)	C24—C25—H25B	109.5
C9—C8—S1	119.77 (6)	H25A—C25—H25B	109.5
C10—C9—C8	119.05 (8)	C24—C25—H25C	109.5
C10—C9—H9	120.5	H25A—C25—H25C	109.5
C8—C9—H9	120.5	H25B—C25—H25C	109.5
C9—C10—C11	121.74 (8)	N2—C26—H26A	109.5
C9—C10—H10	119.1	N2—C26—H26B	109.5
C11—C10—H10	119.1	H26A—C26—H26B	109.5
C10—C11—C12	118.13 (8)	N2—C26—H26C	109.5
C10—C11—C14	120.43 (9)	H26A—C26—H26C	109.5
C12—C11—C14	121.44 (8)	H26B—C26—H26C	109.5
C13—C12—C11	121.24 (8)	H1W1—O1W—H2W1	100.8 (14)
C13—C12—H12	119.4
O2—S1—N1—C1	171.79 (6)	C2—C3—C7—C23	151.18 (7)
O1—S1—N1—C1	41.91 (7)	C4—C3—C7—C23	33.50 (10)
C8—S1—N1—C1	−72.84 (6)	O2—S1—C8—C13	−155.91 (7)
O2—S1—N1—C4	−41.83 (7)	O1—S1—C8—C13	−25.14 (8)
O1—S1—N1—C4	−171.71 (6)	N1—S1—C8—C13	89.01 (7)
C8—S1—N1—C4	73.54 (6)	O2—S1—C8—C9	24.75 (8)
C4—N1—C1—C2	−20.95 (8)	O1—S1—C8—C9	155.53 (7)
S1—N1—C1—C2	127.93 (6)	N1—S1—C8—C9	−90.33 (7)
N1—C1—C2—C5	163.47 (6)	C13—C8—C9—C10	0.08 (12)
N1—C1—C2—C3	38.34 (7)	S1—C8—C9—C10	179.42 (7)
C5—C2—C3—C7	59.85 (7)	C8—C9—C10—C11	−0.04 (13)
C1—C2—C3—C7	−170.83 (6)	C9—C10—C11—C12	−0.07 (13)
C5—C2—C3—C4	−171.52 (6)	C9—C10—C11—C14	179.94 (8)
C1—C2—C3—C4	−42.20 (7)	C10—C11—C12—C13	0.14 (13)
C1—N1—C4—C24	−127.76 (7)	C14—C11—C12—C13	−179.87 (8)
S1—N1—C4—C24	83.59 (7)	C11—C12—C13—C8	−0.10 (13)
C1—N1—C4—C3	−4.66 (8)	C9—C8—C13—C12	−0.02 (13)
S1—N1—C4—C3	−153.32 (5)	S1—C8—C13—C12	−179.35 (7)
C7—C3—C4—N1	148.43 (6)	C6—N2—C17—C22	−4.08 (10)
C2—C3—C4—N1	28.27 (7)	C26—N2—C17—C22	178.58 (7)
C7—C3—C4—C24	−92.49 (8)	C6—N2—C17—C18	173.96 (7)
C2—C3—C4—C24	147.35 (6)	C26—N2—C17—C18	−3.38 (11)
C6—O3—C5—C2	23.11 (9)	N2—C17—C18—C19	−178.65 (7)
C6—O3—C5—C15	141.69 (7)	C22—C17—C18—C19	−0.62 (11)
C6—O3—C5—C16	−100.17 (8)	C17—C18—C19—C20	−0.76 (12)
C1—C2—C5—O3	−176.29 (6)	C18—C19—C20—C21	1.36 (12)
C3—C2—C5—O3	−55.54 (8)	C19—C20—C21—C22	−0.58 (12)
C1—C2—C5—C15	70.71 (9)	N2—C17—C22—C21	179.45 (7)
C3—C2—C5—C15	−168.54 (6)	C18—C17—C22—C21	1.38 (10)
C1—C2—C5—C16	−58.17 (9)	N2—C17—C22—C23	0.26 (10)
C3—C2—C5—C16	62.58 (8)	C18—C17—C22—C23	−177.81 (7)
C5—O3—C6—N2	−174.90 (6)	C20—C21—C22—C17	−0.78 (11)
C5—O3—C6—C7	5.28 (11)	C20—C21—C22—C23	178.41 (7)
C17—N2—C6—O3	−174.60 (6)	C6—C7—C23—O4	179.29 (7)
C26—N2—C6—O3	2.79 (10)	C3—C7—C23—O4	−1.91 (11)
C17—N2—C6—C7	5.22 (11)	C6—C7—C23—C22	−1.63 (10)
C26—N2—C6—C7	−177.39 (7)	C3—C7—C23—C22	177.18 (6)
O3—C6—C7—C23	177.57 (7)	C17—C22—C23—O4	−178.34 (7)
N2—C6—C7—C23	−2.22 (11)	C21—C22—C23—O4	2.47 (11)
O3—C6—C7—C3	−1.33 (11)	C17—C22—C23—C7	2.55 (10)
N2—C6—C7—C3	178.88 (6)	C21—C22—C23—C7	−176.63 (7)
C2—C3—C7—C6	−30.00 (8)	N1—C4—C24—C25	47.81 (9)
C4—C3—C7—C6	−147.68 (7)	C3—C4—C24—C25	−66.92 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O4i	0.94 (2)	1.86 (2)	2.7880 (10)	173 (2)
O1W—H2W1···O4	0.94 (2)	1.89 (2)	2.8247 (9)	171 (2)
C24—H24A···O4	0.97	2.31	3.0213 (11)	129
C24—H24B···O2	0.97	2.49	3.0748 (11)	119
C15—H15B···O1ii	0.96	2.42	3.3641 (11)	168
C26—H26C···O1Wiii	0.96	2.45	3.3333 (12)	152
C19—H19···Cg1iii	0.93	2.84	3.6777 (10)	151
C25—H25B···Cg2iv	0.96	2.79	3.5358 (12)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O4i	0.94 (2)	1.86 (2)	2.7880 (10)	173 (2)
O1W—H2W1⋯O4	0.94 (2)	1.89 (2)	2.8247 (9)	171 (2)
C24—H24A⋯O4	0.97	2.31	3.0213 (11)	129
C24—H24B⋯O2	0.97	2.49	3.0748 (11)	119
C15—H15B⋯O1ii	0.96	2.42	3.3641 (11)	168
C26—H26C⋯O1Wiii	0.96	2.45	3.3333 (12)	152
C19—H19⋯Cg1iii	0.93	2.84	3.6777 (10)	151
C25—H25B⋯Cg2iv	0.96	2.79	3.5358 (12)	135

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 and Cg2 are the centroids of the C8–C13 and N2/C6/C7/C23/C22/C17 rings, respectively.