24-Acetyl-8,11,14-trioxa-24,27-diaza-penta-cyclo-[19.5.1.1(22,26).0(2,7).0(15,20)]octa-cosa-2,4,6,15(20),16,18-hexaen-28-one.

The title compound, C(25)H(28)N(2)O(5), is a product of the Petrenko-Kritchenko condensation of N-acetyl-piperidone with 1,5-bis-(2-formyl-phen-oxy)-3-oxapentane and ammonium acetate. The mol-ecule comprises a fused penta-cyclic system containing an aza-14-crown-3-ether macrocycle, two piperidone and two benzene rings. The aza-14-crown-3-ether ring adopts a bowl conformation. The dihedral angle between the benzene rings fused to the aza-14-crown-4-ether unit is 70.18 (4)°. The central piperidone ring has a boat conformation, whereas the terminal piperidone ring adopts a chair conformation. The conformation of the central piperidone ring is determined by two intra-molecular N-H⋯O hydrogen bonds. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions into chains along [010].

Related literature

For general background to the design, synthesis and applications of macrocyclic ligands for coordination and supra­molecular chemistry, see: Hiraoka (1978 ▶); Pedersen (1988 ▶); Gokel & Murillo (1996 ▶); Bradshaw & Izatt (1997 ▶). For related compounds, see: Levov et al. (2006 ▶, 2008 ▶); Komarova et al. (2008 ▶); Anh et al. (2008 ▶, 2012a ▶,b ▶); Hieu et al. (2011 ▶); Khieu et al. (2011 ▶); Sokol et al. (2011 ▶).

Experimental

Crystal data

C25H28N2O5

M = 436.49

Orthorhombic,

a = 17.1756 (6) Å

b = 11.1724 (4) Å

c = 22.6546 (8) Å

V = 4347.3 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.30 × 0.25 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.973, T max = 0.977

54466 measured reflections

6326 independent reflections

4682 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.106

S = 1.00

6326 reflections

293 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAIn class="Chemical">NT (Bruker, 2001 ▶); 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812027274/aa2068sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027274/aa2068Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812027274/aa2068Isup3.cml

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

C25H28N2O5	F(000) = 1856
Mr = 436.49	Dx = 1.334 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6757 reflections
a = 17.1756 (6) Å	θ = 2.4–27.6°
b = 11.1724 (4) Å	µ = 0.09 mm−1
c = 22.6546 (8) Å	T = 100 K
V = 4347.3 (3) Å3	Prism, colourless
Z = 8	0.30 × 0.25 × 0.25 mm

Bruker APEXII CCD diffractometer	6326 independent reflections
Radiation source: fine-focus sealed tube	4682 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
φ and ω scans	θmax = 30.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −24→24
Tmin = 0.973, Tmax = 0.977	k = −15→15
54466 measured reflections	l = −31→31

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)] = 0.042	Hydrogen site location: mixed
wR(F2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0483P)2 + 1.18P] where P = (Fo2 + 2Fc2)/3
6326 reflections	(Δ/σ)max < 0.001
293 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.24 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
C1	0.14643 (7)	0.45850 (10)	0.11628 (5)	0.0150 (2)
H1	0.1927	0.4136	0.1012	0.018*
C2	0.07641 (7)	0.40656 (10)	0.08499 (5)	0.0176 (2)
C3	0.08519 (8)	0.30961 (11)	0.04720 (6)	0.0242 (3)
H3	0.1359	0.2793	0.0398	0.029*
C4	0.02150 (9)	0.25559 (12)	0.01993 (6)	0.0302 (3)
H4	0.0288	0.1886	−0.0053	0.036*
C5	−0.05235 (8)	0.30019 (12)	0.02980 (6)	0.0276 (3)
H5	−0.0960	0.2627	0.0120	0.033*
C6	−0.06308 (8)	0.39996 (12)	0.06580 (6)	0.0238 (3)
H6	−0.1137	0.4321	0.0715	0.029*
C7	0.00101 (7)	0.45237 (11)	0.09343 (5)	0.0194 (2)
O8	−0.00310 (5)	0.54876 (8)	0.13029 (4)	0.0238 (2)
C9	−0.07793 (7)	0.59780 (13)	0.14482 (6)	0.0262 (3)
H9A	−0.1115	0.5361	0.1632	0.031*
H9B	−0.1042	0.6285	0.1090	0.031*
C10	−0.06217 (8)	0.69751 (13)	0.18737 (6)	0.0273 (3)
H10A	−0.0258	0.7561	0.1696	0.033*
H10B	−0.1112	0.7394	0.1973	0.033*
O11	−0.02887 (5)	0.64651 (8)	0.23893 (4)	0.0245 (2)
C12	0.01097 (7)	0.73098 (12)	0.27487 (6)	0.0244 (3)
H12A	−0.0268	0.7808	0.2968	0.029*
H12B	0.0435	0.7842	0.2501	0.029*
C13	0.06106 (7)	0.66211 (12)	0.31701 (6)	0.0235 (3)
H13A	0.0838	0.7167	0.3468	0.028*
H13B	0.0296	0.6010	0.3378	0.028*
O14	0.12189 (5)	0.60544 (8)	0.28352 (4)	0.01997 (18)
C15	0.16485 (7)	0.51843 (11)	0.31095 (5)	0.0174 (2)
C16	0.16080 (7)	0.49369 (12)	0.37114 (5)	0.0222 (3)
H16	0.1278	0.5396	0.3960	0.027*
C17	0.20549 (8)	0.40101 (12)	0.39451 (6)	0.0241 (3)
H17	0.2017	0.3825	0.4353	0.029*
C18	0.25533 (7)	0.33568 (12)	0.35910 (6)	0.0220 (3)
H18	0.2856	0.2725	0.3753	0.026*
C19	0.26073 (7)	0.36366 (11)	0.29901 (5)	0.0178 (2)
H19	0.2962	0.3205	0.2749	0.021*
C20	0.21530 (6)	0.45337 (10)	0.27385 (5)	0.0149 (2)
C21	0.21819 (6)	0.47517 (10)	0.20788 (5)	0.0139 (2)
H21	0.2596	0.4215	0.1917	0.017*
C22	0.24208 (6)	0.60694 (10)	0.19154 (5)	0.0144 (2)
H22	0.2505	0.6539	0.2286	0.017*
C23	0.31604 (7)	0.61447 (11)	0.15252 (5)	0.0174 (2)
H23A	0.3315	0.6993	0.1480	0.021*
H23B	0.3593	0.5717	0.1723	0.021*
N24	0.30278 (6)	0.56178 (9)	0.09399 (4)	0.0182 (2)
C25	0.23402 (7)	0.60548 (11)	0.06232 (5)	0.0194 (2)
H25A	0.2272	0.5590	0.0255	0.023*
H25B	0.2417	0.6905	0.0515	0.023*
C26	0.16073 (7)	0.59325 (10)	0.10078 (5)	0.0160 (2)
H26	0.1145	0.6273	0.0798	0.019*
N27	0.14364 (6)	0.43716 (9)	0.18055 (4)	0.01508 (19)
H27	0.1049 (9)	0.4816 (13)	0.1957 (6)	0.018*
C28	0.17742 (7)	0.66361 (10)	0.15626 (5)	0.0159 (2)
O28	0.14686 (5)	0.75881 (8)	0.16807 (4)	0.02178 (19)
C29	0.35168 (7)	0.48363 (12)	0.06601 (6)	0.0224 (3)
O29	0.33441 (7)	0.43974 (10)	0.01789 (4)	0.0370 (3)
C30	0.42915 (7)	0.45517 (12)	0.09395 (6)	0.0250 (3)
H30A	0.4494	0.3803	0.0774	0.037*
H30B	0.4225	0.4464	0.1367	0.037*
H30C	0.4659	0.5203	0.0859	0.037*

	U11	U22	U33	U12	U13	U23
C1	0.0160 (5)	0.0145 (5)	0.0144 (5)	0.0005 (4)	−0.0013 (4)	−0.0007 (4)
C2	0.0214 (6)	0.0161 (5)	0.0153 (5)	−0.0028 (4)	−0.0044 (4)	0.0024 (4)
C3	0.0305 (7)	0.0199 (6)	0.0223 (6)	0.0040 (5)	−0.0115 (5)	−0.0018 (5)
C4	0.0432 (8)	0.0197 (6)	0.0276 (7)	0.0000 (6)	−0.0188 (6)	−0.0032 (5)
C5	0.0351 (7)	0.0251 (7)	0.0225 (6)	−0.0113 (6)	−0.0147 (6)	0.0067 (5)
C6	0.0200 (6)	0.0304 (7)	0.0212 (6)	−0.0071 (5)	−0.0041 (5)	0.0069 (5)
C7	0.0207 (6)	0.0207 (6)	0.0167 (5)	−0.0047 (5)	−0.0024 (4)	0.0033 (4)
O8	0.0147 (4)	0.0290 (5)	0.0278 (5)	−0.0003 (3)	0.0011 (3)	−0.0074 (4)
C9	0.0138 (5)	0.0349 (7)	0.0298 (7)	0.0033 (5)	0.0000 (5)	0.0000 (6)
C10	0.0203 (6)	0.0303 (7)	0.0312 (7)	0.0083 (5)	−0.0001 (5)	0.0006 (6)
O11	0.0229 (4)	0.0251 (5)	0.0254 (5)	0.0009 (4)	−0.0005 (4)	−0.0010 (4)
C12	0.0203 (6)	0.0234 (6)	0.0296 (7)	0.0037 (5)	0.0038 (5)	−0.0072 (5)
C13	0.0199 (6)	0.0281 (7)	0.0225 (6)	0.0034 (5)	0.0066 (5)	−0.0068 (5)
O14	0.0195 (4)	0.0211 (4)	0.0193 (4)	0.0053 (3)	0.0051 (3)	−0.0004 (3)
C15	0.0157 (5)	0.0191 (5)	0.0174 (5)	−0.0020 (4)	0.0000 (4)	−0.0015 (4)
C16	0.0217 (6)	0.0274 (6)	0.0173 (6)	−0.0020 (5)	0.0013 (5)	−0.0024 (5)
C17	0.0249 (6)	0.0326 (7)	0.0148 (5)	−0.0066 (5)	−0.0036 (5)	0.0025 (5)
C18	0.0214 (6)	0.0239 (6)	0.0206 (6)	−0.0034 (5)	−0.0072 (5)	0.0030 (5)
C19	0.0169 (5)	0.0180 (5)	0.0187 (5)	−0.0025 (4)	−0.0029 (4)	−0.0023 (4)
C20	0.0147 (5)	0.0153 (5)	0.0146 (5)	−0.0034 (4)	−0.0014 (4)	−0.0018 (4)
C21	0.0137 (5)	0.0138 (5)	0.0142 (5)	−0.0004 (4)	−0.0005 (4)	−0.0015 (4)
C22	0.0145 (5)	0.0132 (5)	0.0156 (5)	−0.0009 (4)	0.0018 (4)	−0.0028 (4)
C23	0.0153 (5)	0.0187 (5)	0.0182 (5)	−0.0020 (4)	0.0027 (4)	−0.0024 (4)
N24	0.0160 (5)	0.0218 (5)	0.0167 (5)	−0.0009 (4)	0.0027 (4)	−0.0018 (4)
C25	0.0184 (5)	0.0232 (6)	0.0166 (5)	−0.0019 (5)	0.0017 (4)	0.0027 (5)
C26	0.0162 (5)	0.0152 (5)	0.0165 (5)	−0.0007 (4)	0.0006 (4)	0.0024 (4)
N27	0.0154 (4)	0.0157 (5)	0.0141 (4)	−0.0021 (4)	−0.0012 (4)	−0.0002 (3)
C28	0.0143 (5)	0.0145 (5)	0.0190 (5)	−0.0026 (4)	0.0037 (4)	0.0019 (4)
O28	0.0217 (4)	0.0150 (4)	0.0286 (5)	0.0028 (3)	0.0010 (4)	−0.0012 (3)
C29	0.0234 (6)	0.0222 (6)	0.0215 (6)	0.0003 (5)	0.0039 (5)	−0.0020 (5)
O29	0.0422 (6)	0.0448 (6)	0.0238 (5)	0.0150 (5)	−0.0044 (4)	−0.0134 (4)
C30	0.0200 (6)	0.0283 (7)	0.0266 (6)	0.0009 (5)	0.0044 (5)	−0.0053 (5)

C1—N27	1.4761 (14)	C16—C17	1.3936 (19)
C1—C2	1.5118 (16)	C16—H16	0.9500
C1—C26	1.5653 (16)	C17—C18	1.3816 (19)
C1—H1	1.0000	C17—H17	0.9500
C2—C3	1.3888 (17)	C18—C19	1.3999 (17)
C2—C7	1.4056 (17)	C18—H18	0.9500
C3—C4	1.3937 (18)	C19—C20	1.3923 (16)
C3—H3	0.9500	C19—H19	0.9500
C4—C5	1.381 (2)	C20—C21	1.5151 (15)
C4—H4	0.9500	C21—N27	1.4843 (14)
C5—C6	1.394 (2)	C21—C22	1.5725 (16)
C5—H5	0.9500	C21—H21	1.0000
C6—C7	1.3950 (17)	C22—C28	1.5076 (16)
C6—H6	0.9500	C22—C23	1.5497 (15)
C7—O8	1.3646 (15)	C22—H22	1.0000
O8—C9	1.4353 (15)	C23—N24	1.4686 (15)
C9—C10	1.498 (2)	C23—H23A	0.9900
C9—H9A	0.9900	C23—H23B	0.9900
C9—H9B	0.9900	N24—C29	1.3674 (16)
C10—O11	1.4199 (16)	N24—C25	1.4655 (15)
C10—H10A	0.9900	C25—C26	1.5370 (16)
C10—H10B	0.9900	C25—H25A	0.9900
O11—C12	1.4220 (16)	C25—H25B	0.9900
C12—C13	1.4978 (19)	C26—C28	1.5099 (16)
C12—H12A	0.9900	C26—H26	1.0000
C12—H12B	0.9900	N27—H27	0.898 (15)
C13—O14	1.4381 (14)	C28—O28	1.2159 (14)
C13—H13A	0.9900	C29—O29	1.2314 (16)
C13—H13B	0.9900	C29—C30	1.5074 (18)
O14—C15	1.3694 (14)	C30—H30A	0.9800
C15—C16	1.3930 (16)	C30—H30B	0.9800
C15—C20	1.4091 (16)	C30—H30C	0.9800
N27—C1—C2	112.01 (9)	C16—C17—H17	119.6
N27—C1—C26	112.44 (9)	C17—C18—C19	119.19 (12)
C2—C1—C26	112.88 (9)	C17—C18—H18	120.4
N27—C1—H1	106.3	C19—C18—H18	120.4
C2—C1—H1	106.3	C20—C19—C18	121.45 (11)
C26—C1—H1	106.3	C20—C19—H19	119.3
C3—C2—C7	117.89 (11)	C18—C19—H19	119.3
C3—C2—C1	120.13 (11)	C19—C20—C15	118.16 (10)
C7—C2—C1	121.96 (10)	C19—C20—C21	120.07 (10)
C2—C3—C4	121.72 (13)	C15—C20—C21	121.71 (10)
C2—C3—H3	119.1	N27—C21—C20	109.71 (9)
C4—C3—H3	119.1	N27—C21—C22	113.25 (9)
C5—C4—C3	119.53 (13)	C20—C21—C22	113.03 (9)
C5—C4—H4	120.2	N27—C21—H21	106.8
C3—C4—H4	120.2	C20—C21—H21	106.8
C4—C5—C6	120.32 (12)	C22—C21—H21	106.8
C4—C5—H5	119.8	C28—C22—C23	106.18 (9)
C6—C5—H5	119.8	C28—C22—C21	109.01 (9)
C5—C6—C7	119.60 (13)	C23—C22—C21	113.51 (9)
C5—C6—H6	120.2	C28—C22—H22	109.3
C7—C6—H6	120.2	C23—C22—H22	109.3
O8—C7—C6	124.40 (12)	C21—C22—H22	109.3
O8—C7—C2	114.73 (10)	N24—C23—C22	111.47 (9)
C6—C7—C2	120.87 (12)	N24—C23—H23A	109.3
C7—O8—C9	119.20 (10)	C22—C23—H23A	109.3
O8—C9—C10	105.64 (10)	N24—C23—H23B	109.3
O8—C9—H9A	110.6	C22—C23—H23B	109.3
C10—C9—H9A	110.6	H23A—C23—H23B	108.0
O8—C9—H9B	110.6	C29—N24—C25	118.73 (10)
C10—C9—H9B	110.6	C29—N24—C23	125.40 (10)
H9A—C9—H9B	108.7	C25—N24—C23	115.69 (9)
O11—C10—C9	107.69 (11)	N24—C25—C26	110.66 (9)
O11—C10—H10A	110.2	N24—C25—H25A	109.5
C9—C10—H10A	110.2	C26—C25—H25A	109.5
O11—C10—H10B	110.2	N24—C25—H25B	109.5
C9—C10—H10B	110.2	C26—C25—H25B	109.5
H10A—C10—H10B	108.5	H25A—C25—H25B	108.1
C10—O11—C12	113.49 (10)	C28—C26—C25	105.67 (9)
O11—C12—C13	107.48 (11)	C28—C26—C1	110.10 (9)
O11—C12—H12A	110.2	C25—C26—C1	109.95 (9)
C13—C12—H12A	110.2	C28—C26—H26	110.3
O11—C12—H12B	110.2	C25—C26—H26	110.3
C13—C12—H12B	110.2	C1—C26—H26	110.3
H12A—C12—H12B	108.5	C1—N27—C21	109.71 (9)
O14—C13—C12	107.90 (10)	C1—N27—H27	108.2 (9)
O14—C13—H13A	110.1	C21—N27—H27	108.8 (9)
C12—C13—H13A	110.1	O28—C28—C22	124.66 (11)
O14—C13—H13B	110.1	O28—C28—C26	123.82 (11)
C12—C13—H13B	110.1	C22—C28—C26	111.26 (9)
H13A—C13—H13B	108.4	O29—C29—N24	121.11 (12)
C15—O14—C13	117.69 (9)	O29—C29—C30	120.02 (12)
O14—C15—C16	123.92 (11)	N24—C29—C30	118.83 (11)
O14—C15—C20	115.27 (10)	C29—C30—H30A	109.5
C16—C15—C20	120.81 (11)	C29—C30—H30B	109.5
C15—C16—C17	119.46 (12)	H30A—C30—H30B	109.5
C15—C16—H16	120.3	C29—C30—H30C	109.5
C17—C16—H16	120.3	H30A—C30—H30C	109.5
C18—C17—C16	120.88 (12)	H30B—C30—H30C	109.5
C18—C17—H17	119.6
N27—C1—C2—C3	−111.77 (12)	C19—C20—C21—N27	110.05 (11)
C26—C1—C2—C3	120.11 (12)	C15—C20—C21—N27	−67.13 (13)
N27—C1—C2—C7	67.29 (14)	C19—C20—C21—C22	−122.51 (11)
C26—C1—C2—C7	−60.83 (14)	C15—C20—C21—C22	60.31 (14)
C7—C2—C3—C4	−2.39 (19)	N27—C21—C22—C28	5.27 (12)
C1—C2—C3—C4	176.71 (12)	C20—C21—C22—C28	−120.29 (10)
C2—C3—C4—C5	1.0 (2)	N27—C21—C22—C23	−112.85 (10)
C3—C4—C5—C6	1.3 (2)	C20—C21—C22—C23	121.59 (10)
C4—C5—C6—C7	−2.06 (19)	C28—C22—C23—N24	−53.90 (12)
C5—C6—C7—O8	−178.82 (11)	C21—C22—C23—N24	65.84 (12)
C5—C6—C7—C2	0.61 (18)	C22—C23—N24—C29	−133.39 (12)
C3—C2—C7—O8	−178.95 (11)	C22—C23—N24—C25	51.51 (13)
C1—C2—C7—O8	1.97 (16)	C29—N24—C25—C26	131.12 (11)
C3—C2—C7—C6	1.57 (18)	C23—N24—C25—C26	−53.45 (13)
C1—C2—C7—C6	−177.51 (11)	N24—C25—C26—C28	57.62 (12)
C6—C7—O8—C9	3.31 (18)	N24—C25—C26—C1	−61.17 (12)
C2—C7—O8—C9	−176.15 (11)	N27—C1—C26—C28	6.70 (13)
C7—O8—C9—C10	177.69 (11)	C2—C1—C26—C28	134.60 (10)
O8—C9—C10—O11	−63.66 (13)	N27—C1—C26—C25	122.73 (10)
C9—C10—O11—C12	161.37 (10)	C2—C1—C26—C25	−109.37 (11)
C10—O11—C12—C13	−164.28 (10)	C2—C1—N27—C21	172.45 (9)
O11—C12—C13—O14	68.21 (13)	C26—C1—N27—C21	−59.19 (12)
C12—C13—O14—C15	−166.84 (10)	C20—C21—N27—C1	179.95 (9)
C13—O14—C15—C16	−9.56 (17)	C22—C21—N27—C1	52.63 (12)
C13—O14—C15—C20	170.68 (10)	C23—C22—C28—O28	−110.25 (12)
O14—C15—C16—C17	178.30 (11)	C21—C22—C28—O28	127.11 (12)
C20—C15—C16—C17	−1.95 (18)	C23—C22—C28—C26	64.03 (11)
C15—C16—C17—C18	1.83 (19)	C21—C22—C28—C26	−58.60 (11)
C16—C17—C18—C19	0.10 (19)	C25—C26—C28—O28	108.24 (12)
C17—C18—C19—C20	−1.97 (18)	C1—C26—C28—O28	−133.08 (11)
C18—C19—C20—C15	1.83 (17)	C25—C26—C28—C22	−66.11 (11)
C18—C19—C20—C21	−175.45 (10)	C1—C26—C28—C22	52.58 (12)
O14—C15—C20—C19	179.92 (10)	C25—N24—C29—O29	−8.16 (18)
C16—C15—C20—C19	0.15 (17)	C23—N24—C29—O29	176.88 (12)
O14—C15—C20—C21	−2.85 (16)	C25—N24—C29—C30	169.51 (11)
C16—C15—C20—C21	177.38 (11)	C23—N24—C29—C30	−5.45 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N27—H27···O8	0.90 (2)	2.49 (2)	3.0337 (13)	119 (1)
N27—H27···O14	0.90 (2)	2.44 (1)	3.0193 (13)	122 (1)
C21—H21···O28i	1.00	2.48	3.4683 (14)	168
C30—H30B···O28i	0.98	2.51	3.0556 (16)	115

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N27—H27⋯O8	0.90 (2)	2.49 (2)	3.0337 (13)	119 (1)
N27—H27⋯O14	0.90 (2)	2.44 (1)	3.0193 (13)	122 (1)
C21—H21⋯O28i	1.00	2.48	3.4683 (14)	168
C30—H30B⋯O28i	0.98	2.51	3.0556 (16)	115

Symmetry code: (i) .