2-Hy-droxy-11-methyl-16-[(E)-4-methyl-benzyl-idene]-13-(4-methyl-phen-yl)-1,11-diaza-penta-cyclo-[12.3.1.0.0.0]octa-deca-3(8),4,6-triene-9,15-dione.

In the title compound, C(32)H(30)N(2)O(3), the piperidin-4-one and the two fused pyrrolidine rings adopt envelope conformations. The two methyl-phenyl rings are oriented at dihedral angle of 20.36 (7) and 56.24 (7)°, respectively, with respect to the indanone ring system. In the crystal structure, inter-molecular O-H⋯N and C-H⋯O hydrogen bonds link the mol-ecules into chains propagating along [001]. Weak C-H⋯π inter-actions are also observed.

Related literature

For general background and the biological activity of pyrrolidine compounds, see: Mitchell & Teh (2005 ▶); Okazaki et al. (2004 ▶); Enyedy et al. (2001 ▶); Yee et al. (1998 ▶); Saravanan & Corey (2003 ▶); Crane & Corey (2001 ▶); Xi et al. (2004 ▶); Kagan (1975 ▶). For the synthesis, see: Kumar et al. (2010a ▶,b ▶). For ring conformations, see Cremer & Pople (1975 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C32H30N2O3

M = 490.58

Triclinic,

a = 9.3252 (6) Å

b = 12.1781 (8) Å

c = 12.9821 (8) Å

α = 67.480 (2)°

β = 86.093 (2)°

γ = 69.475 (2)°

V = 1271.68 (14) Å3

Z = 2

Cu Kα radiation

μ = 0.65 mm−1

T = 100 K

0.56 × 0.29 × 0.25 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.713, T max = 0.851

13699 measured reflections

4121 independent reflections

4004 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.134

S = 1.21

4121 reflections

342 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAIn class="Chemical">NT (Bruker, 2009 ▶); 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/S1600536810033064/ci5154sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033064/ci5154Isup2.hkl

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

C32H30N2O3	Z = 2
Mr = 490.58	F(000) = 520
Triclinic, P1	Dx = 1.281 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 9.3252 (6) Å	Cell parameters from 9995 reflections
b = 12.1781 (8) Å	θ = 5.8–67.8°
c = 12.9821 (8) Å	µ = 0.65 mm−1
α = 67.480 (2)°	T = 100 K
β = 86.093 (2)°	Plate, yellow
γ = 69.475 (2)°	0.56 × 0.29 × 0.25 mm
V = 1271.68 (14) Å3

Bruker APEXII DUO CCD area-detector diffractometer	4121 independent reflections
Radiation source: fine-focus sealed tube	4004 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 65.0°, θmin = 6.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→10
Tmin = 0.713, Tmax = 0.851	k = −14→14
13699 measured reflections	l = −15→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.134	w = 1/[σ2(Fo2) + (0.0743P)2 + 0.3694P] where P = (Fo2 + 2Fc2)/3
S = 1.21	(Δ/σ)max = 0.001
4121 reflections	Δρmax = 0.32 e Å−3
342 parameters	Δρmin = −0.40 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.069 (4)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
O1	0.69853 (13)	0.26369 (11)	0.55957 (9)	0.0290 (3)
O2	1.14244 (12)	−0.01927 (10)	0.92987 (8)	0.0219 (3)
O3	0.90572 (13)	−0.06206 (11)	0.65669 (9)	0.0296 (3)
N1	1.02023 (14)	0.19002 (11)	0.79859 (10)	0.0195 (3)
N2	0.87997 (14)	−0.05467 (11)	0.88897 (10)	0.0213 (3)
C1	1.18437 (18)	0.39376 (14)	0.46558 (13)	0.0255 (4)
H1A	1.1585	0.4127	0.5288	0.031*
C2	1.30607 (19)	0.42114 (15)	0.40771 (14)	0.0306 (4)
H2A	1.3609	0.4577	0.4332	0.037*
C3	1.3481 (2)	0.39515 (16)	0.31222 (15)	0.0344 (4)
C4	1.2616 (2)	0.34286 (17)	0.27535 (15)	0.0374 (4)
H4A	1.2859	0.3264	0.2108	0.045*
C5	1.1405 (2)	0.31491 (16)	0.33248 (14)	0.0314 (4)
H5A	1.0848	0.2800	0.3056	0.038*
C6	1.09964 (18)	0.33786 (14)	0.42997 (12)	0.0238 (4)
C7	0.97216 (17)	0.30238 (13)	0.48655 (12)	0.0230 (4)
H7A	0.9031	0.2979	0.4412	0.028*
C8	0.93923 (17)	0.27523 (13)	0.59393 (12)	0.0207 (3)
C9	0.80311 (17)	0.23458 (13)	0.62724 (12)	0.0215 (3)
C10	0.80285 (17)	0.15433 (13)	0.75147 (12)	0.0202 (3)
C11	0.85546 (16)	0.21946 (13)	0.81648 (12)	0.0202 (3)
H11A	0.8003	0.3104	0.7865	0.024*
H11B	0.8398	0.1847	0.8954	0.024*
C12	1.03611 (17)	0.27348 (14)	0.68483 (12)	0.0208 (3)
H12A	1.1432	0.2463	0.6690	0.025*
H12B	1.0074	0.3593	0.6820	0.025*
C13	0.52758 (18)	0.21075 (15)	0.92567 (13)	0.0279 (4)
H13A	0.6058	0.1488	0.9792	0.033*
C14	0.4105 (2)	0.29883 (16)	0.95461 (14)	0.0324 (4)
H14A	0.4123	0.2955	1.0273	0.039*
C15	0.29066 (19)	0.39205 (16)	0.87786 (15)	0.0333 (4)
C16	0.29137 (19)	0.39398 (16)	0.77021 (15)	0.0333 (4)
H16A	0.2117	0.4547	0.7174	0.040*
C17	0.40876 (18)	0.30691 (15)	0.74029 (14)	0.0282 (4)
H17A	0.4070	0.3106	0.6675	0.034*
C18	0.52947 (17)	0.21387 (14)	0.81723 (13)	0.0233 (4)
C19	0.65657 (17)	0.12088 (14)	0.78116 (12)	0.0227 (4)
H19A	0.6158	0.1213	0.7133	0.027*
C20	0.71422 (18)	−0.01858 (14)	0.86592 (13)	0.0250 (4)
H20A	0.6621	−0.0261	0.9342	0.030*
H20B	0.6947	−0.0732	0.8347	0.030*
C21	0.93759 (16)	0.02464 (13)	0.79105 (12)	0.0199 (3)
C22	0.98737 (18)	−0.02951 (13)	0.69987 (12)	0.0223 (3)
C23	1.14573 (18)	−0.03556 (14)	0.67710 (12)	0.0226 (3)
C24	1.23947 (19)	−0.08211 (15)	0.60366 (13)	0.0271 (4)
H24A	1.2029	−0.1121	0.5589	0.033*
C25	1.3875 (2)	−0.08246 (16)	0.59918 (13)	0.0308 (4)
H25A	1.4519	−0.1129	0.5507	0.037*
C26	1.44221 (19)	−0.03750 (16)	0.66696 (13)	0.0297 (4)
H26A	1.5428	−0.0391	0.6632	0.036*
C27	1.34872 (18)	0.00941 (15)	0.73970 (12)	0.0249 (4)
H27A	1.3855	0.0392	0.7846	0.030*
C28	1.19917 (17)	0.01076 (13)	0.74373 (11)	0.0204 (3)
C29	1.07917 (17)	0.05268 (13)	0.81917 (11)	0.0193 (3)
C30	1.4823 (3)	0.4233 (2)	0.25134 (19)	0.0510 (6)
H30A	1.5176	0.3737	0.2062	0.077*
H30B	1.5639	0.4021	0.3046	0.077*
H30C	1.4510	0.5119	0.2043	0.077*
C31	0.1659 (2)	0.4899 (2)	0.9091 (2)	0.0500 (5)
H31A	0.0674	0.4950	0.8860	0.075*
H31B	0.1772	0.5712	0.8725	0.075*
H31C	0.1737	0.4660	0.9886	0.075*
C32	0.96162 (18)	−0.19190 (14)	0.92734 (13)	0.0253 (4)
H32A	0.9288	−0.2336	0.9988	0.038*
H32B	1.0701	−0.2098	0.9341	0.038*
H32C	0.9395	−0.2223	0.8743	0.038*
H1O2	1.115 (3)	0.022 (2)	0.972 (2)	0.053 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0255 (6)	0.0357 (6)	0.0235 (6)	−0.0126 (5)	−0.0034 (4)	−0.0066 (5)
O2	0.0243 (6)	0.0219 (5)	0.0167 (5)	−0.0056 (4)	−0.0005 (4)	−0.0066 (4)
O3	0.0326 (7)	0.0326 (6)	0.0303 (6)	−0.0145 (5)	0.0000 (5)	−0.0161 (5)
N1	0.0195 (7)	0.0199 (6)	0.0185 (6)	−0.0072 (5)	0.0011 (5)	−0.0064 (5)
N2	0.0214 (7)	0.0199 (6)	0.0215 (6)	−0.0079 (5)	0.0020 (5)	−0.0062 (5)
C1	0.0284 (9)	0.0224 (8)	0.0224 (8)	−0.0100 (6)	0.0013 (6)	−0.0043 (6)
C2	0.0295 (9)	0.0241 (8)	0.0351 (9)	−0.0120 (7)	0.0003 (7)	−0.0054 (7)
C3	0.0312 (10)	0.0253 (8)	0.0404 (10)	−0.0094 (7)	0.0115 (7)	−0.0078 (7)
C4	0.0472 (11)	0.0354 (9)	0.0345 (9)	−0.0191 (8)	0.0192 (8)	−0.0171 (8)
C5	0.0397 (10)	0.0305 (9)	0.0287 (9)	−0.0176 (7)	0.0070 (7)	−0.0123 (7)
C6	0.0260 (8)	0.0199 (7)	0.0206 (7)	−0.0073 (6)	0.0005 (6)	−0.0033 (6)
C7	0.0247 (8)	0.0205 (7)	0.0224 (8)	−0.0084 (6)	−0.0025 (6)	−0.0057 (6)
C8	0.0213 (8)	0.0174 (7)	0.0211 (7)	−0.0061 (6)	−0.0017 (6)	−0.0051 (6)
C9	0.0214 (8)	0.0198 (7)	0.0224 (8)	−0.0052 (6)	−0.0009 (6)	−0.0088 (6)
C10	0.0181 (8)	0.0204 (7)	0.0217 (7)	−0.0065 (6)	0.0001 (6)	−0.0077 (6)
C11	0.0194 (8)	0.0197 (7)	0.0207 (7)	−0.0061 (6)	0.0013 (5)	−0.0075 (6)
C12	0.0216 (8)	0.0206 (7)	0.0197 (7)	−0.0092 (6)	0.0012 (6)	−0.0054 (6)
C13	0.0215 (8)	0.0297 (8)	0.0264 (8)	−0.0074 (6)	0.0029 (6)	−0.0061 (6)
C14	0.0293 (9)	0.0351 (9)	0.0309 (9)	−0.0113 (7)	0.0099 (7)	−0.0119 (7)
C15	0.0224 (9)	0.0306 (9)	0.0456 (10)	−0.0099 (7)	0.0082 (7)	−0.0137 (8)
C16	0.0209 (9)	0.0275 (8)	0.0448 (10)	−0.0048 (6)	−0.0060 (7)	−0.0091 (7)
C17	0.0244 (8)	0.0277 (8)	0.0314 (8)	−0.0098 (6)	−0.0029 (6)	−0.0090 (7)
C18	0.0177 (8)	0.0236 (8)	0.0285 (8)	−0.0104 (6)	0.0022 (6)	−0.0070 (6)
C19	0.0209 (8)	0.0245 (8)	0.0229 (7)	−0.0094 (6)	−0.0003 (6)	−0.0075 (6)
C20	0.0226 (8)	0.0244 (8)	0.0277 (8)	−0.0103 (6)	0.0025 (6)	−0.0080 (6)
C21	0.0197 (8)	0.0193 (7)	0.0197 (7)	−0.0071 (6)	0.0007 (6)	−0.0059 (6)
C22	0.0262 (8)	0.0185 (7)	0.0205 (7)	−0.0073 (6)	−0.0017 (6)	−0.0058 (6)
C23	0.0258 (8)	0.0199 (7)	0.0195 (7)	−0.0064 (6)	0.0003 (6)	−0.0060 (6)
C24	0.0329 (9)	0.0269 (8)	0.0222 (8)	−0.0095 (7)	0.0035 (6)	−0.0112 (6)
C25	0.0340 (9)	0.0314 (9)	0.0253 (8)	−0.0090 (7)	0.0109 (7)	−0.0128 (7)
C26	0.0231 (9)	0.0330 (9)	0.0310 (9)	−0.0094 (7)	0.0072 (6)	−0.0114 (7)
C27	0.0237 (8)	0.0274 (8)	0.0233 (8)	−0.0093 (6)	0.0023 (6)	−0.0095 (6)
C28	0.0213 (8)	0.0189 (7)	0.0173 (7)	−0.0056 (6)	0.0007 (5)	−0.0043 (6)
C29	0.0204 (8)	0.0197 (7)	0.0169 (7)	−0.0070 (6)	−0.0001 (5)	−0.0060 (6)
C30	0.0444 (12)	0.0444 (11)	0.0659 (14)	−0.0230 (9)	0.0275 (10)	−0.0200 (10)
C31	0.0335 (11)	0.0453 (11)	0.0627 (14)	−0.0031 (9)	0.0119 (9)	−0.0231 (10)
C32	0.0290 (9)	0.0197 (8)	0.0251 (8)	−0.0080 (6)	0.0013 (6)	−0.0067 (6)

O1—C9	1.2183 (18)	C14—C15	1.388 (2)
O2—C29	1.4033 (17)	C14—H14A	0.93
O2—H1O2	0.85 (3)	C15—C16	1.388 (3)
O3—C22	1.2211 (18)	C15—C31	1.507 (2)
N1—C12	1.4703 (18)	C16—C17	1.385 (2)
N1—C11	1.4738 (19)	C16—H16A	0.93
N1—C29	1.4845 (18)	C17—C18	1.393 (2)
N2—C32	1.4637 (19)	C17—H17A	0.93
N2—C20	1.469 (2)	C18—C19	1.515 (2)
N2—C21	1.4723 (18)	C19—C20	1.547 (2)
C1—C2	1.386 (2)	C19—H19A	0.98
C1—C6	1.403 (2)	C20—H20A	0.97
C1—H1A	0.93	C20—H20B	0.97
C2—C3	1.392 (3)	C21—C22	1.536 (2)
C2—H2A	0.93	C21—C29	1.572 (2)
C3—C4	1.390 (3)	C22—C23	1.468 (2)
C3—C30	1.505 (2)	C23—C28	1.394 (2)
C4—C5	1.380 (2)	C23—C24	1.396 (2)
C4—H4A	0.93	C24—C25	1.376 (2)
C5—C6	1.399 (2)	C24—H24A	0.93
C5—H5A	0.93	C25—C26	1.400 (2)
C6—C7	1.462 (2)	C25—H25A	0.93
C7—C8	1.344 (2)	C26—C27	1.389 (2)
C7—H7A	0.93	C26—H26A	0.93
C8—C9	1.498 (2)	C27—C28	1.387 (2)
C8—C12	1.524 (2)	C27—H27A	0.93
C9—C10	1.533 (2)	C28—C29	1.518 (2)
C10—C19	1.540 (2)	C30—H30A	0.96
C10—C21	1.5530 (19)	C30—H30B	0.96
C10—C11	1.5569 (19)	C30—H30C	0.96
C11—H11A	0.97	C31—H31A	0.96
C11—H11B	0.97	C31—H31B	0.96
C12—H12A	0.97	C31—H31C	0.96
C12—H12B	0.97	C32—H32A	0.96
C13—C14	1.384 (2)	C32—H32B	0.96
C13—C18	1.393 (2)	C32—H32C	0.96
C13—H13A	0.93
C29—O2—H1O2	112.9 (16)	C13—C18—C17	117.73 (15)
C12—N1—C11	108.58 (11)	C13—C18—C19	122.55 (14)
C12—N1—C29	114.54 (11)	C17—C18—C19	119.72 (14)
C11—N1—C29	104.38 (11)	C18—C19—C10	114.91 (12)
C32—N2—C20	112.70 (12)	C18—C19—C20	115.93 (13)
C32—N2—C21	116.01 (12)	C10—C19—C20	104.77 (11)
C20—N2—C21	107.99 (11)	C18—C19—H19A	106.9
C2—C1—C6	120.88 (15)	C10—C19—H19A	106.9
C2—C1—H1A	119.6	C20—C19—H19A	106.9
C6—C1—H1A	119.6	N2—C20—C19	106.63 (12)
C1—C2—C3	121.48 (16)	N2—C20—H20A	110.4
C1—C2—H2A	119.3	C19—C20—H20A	110.4
C3—C2—H2A	119.3	N2—C20—H20B	110.4
C4—C3—C2	117.59 (16)	C19—C20—H20B	110.4
C4—C3—C30	121.49 (17)	H20A—C20—H20B	108.6
C2—C3—C30	120.92 (18)	N2—C21—C22	114.83 (11)
C5—C4—C3	121.40 (16)	N2—C21—C10	102.80 (11)
C5—C4—H4A	119.3	C22—C21—C10	114.00 (11)
C3—C4—H4A	119.3	N2—C21—C29	114.35 (11)
C4—C5—C6	121.44 (16)	C22—C21—C29	105.28 (11)
C4—C5—H5A	119.3	C10—C21—C29	105.45 (11)
C6—C5—H5A	119.3	O3—C22—C23	127.68 (14)
C5—C6—C1	117.17 (14)	O3—C22—C21	123.96 (14)
C5—C6—C7	117.71 (14)	C23—C22—C21	108.36 (12)
C1—C6—C7	125.12 (14)	C28—C23—C24	121.26 (15)
C8—C7—C6	130.04 (14)	C28—C23—C22	110.20 (13)
C8—C7—H7A	115.0	C24—C23—C22	128.53 (14)
C6—C7—H7A	115.0	C25—C24—C23	118.28 (15)
C7—C8—C9	116.81 (13)	C25—C24—H24A	120.9
C7—C8—C12	124.92 (14)	C23—C24—H24A	120.9
C9—C8—C12	118.11 (12)	C24—C25—C26	120.64 (15)
O1—C9—C8	121.97 (13)	C24—C25—H25A	119.7
O1—C9—C10	121.88 (14)	C26—C25—H25A	119.7
C8—C9—C10	116.16 (12)	C27—C26—C25	121.11 (15)
C9—C10—C19	113.59 (12)	C27—C26—H26A	119.4
C9—C10—C21	112.47 (12)	C25—C26—H26A	119.4
C19—C10—C21	105.14 (11)	C28—C27—C26	118.36 (14)
C9—C10—C11	105.65 (11)	C28—C27—H27A	120.8
C19—C10—C11	119.93 (12)	C26—C27—H27A	120.8
C21—C10—C11	99.28 (11)	C27—C28—C23	120.35 (14)
N1—C11—C10	103.44 (11)	C27—C28—C29	127.57 (13)
N1—C11—H11A	111.1	C23—C28—C29	112.01 (13)
C10—C11—H11A	111.1	O2—C29—N1	110.03 (11)
N1—C11—H11B	111.1	O2—C29—C28	107.24 (11)
C10—C11—H11B	111.1	N1—C29—C28	116.66 (12)
H11A—C11—H11B	109.0	O2—C29—C21	113.48 (11)
N1—C12—C8	114.17 (12)	N1—C29—C21	105.34 (11)
N1—C12—H12A	108.7	C28—C29—C21	104.15 (11)
C8—C12—H12A	108.7	C3—C30—H30A	109.5
N1—C12—H12B	108.7	C3—C30—H30B	109.5
C8—C12—H12B	108.7	H30A—C30—H30B	109.5
H12A—C12—H12B	107.6	C3—C30—H30C	109.5
C14—C13—C18	120.67 (15)	H30A—C30—H30C	109.5
C14—C13—H13A	119.7	H30B—C30—H30C	109.5
C18—C13—H13A	119.7	C15—C31—H31A	109.5
C13—C14—C15	121.66 (16)	C15—C31—H31B	109.5
C13—C14—H14A	119.2	H31A—C31—H31B	109.5
C15—C14—H14A	119.2	C15—C31—H31C	109.5
C14—C15—C16	117.66 (15)	H31A—C31—H31C	109.5
C14—C15—C31	121.37 (17)	H31B—C31—H31C	109.5
C16—C15—C31	120.96 (17)	N2—C32—H32A	109.5
C17—C16—C15	121.05 (15)	N2—C32—H32B	109.5
C17—C16—H16A	119.5	H32A—C32—H32B	109.5
C15—C16—H16A	119.5	N2—C32—H32C	109.5
C16—C17—C18	121.23 (16)	H32A—C32—H32C	109.5
C16—C17—H17A	119.4	H32B—C32—H32C	109.5
C18—C17—H17A	119.4
C6—C1—C2—C3	0.4 (2)	C32—N2—C21—C22	39.35 (17)
C1—C2—C3—C4	1.3 (2)	C20—N2—C21—C22	−88.23 (14)
C1—C2—C3—C30	−178.91 (16)	C32—N2—C21—C10	163.73 (12)
C2—C3—C4—C5	−1.4 (3)	C20—N2—C21—C10	36.15 (14)
C30—C3—C4—C5	178.74 (17)	C32—N2—C21—C29	−82.52 (15)
C3—C4—C5—C6	−0.1 (3)	C20—N2—C21—C29	149.89 (12)
C4—C5—C6—C1	1.7 (2)	C9—C10—C21—N2	−155.97 (11)
C4—C5—C6—C7	−178.52 (15)	C19—C10—C21—N2	−31.88 (13)
C2—C1—C6—C5	−1.9 (2)	C11—C10—C21—N2	92.73 (12)
C2—C1—C6—C7	178.37 (14)	C9—C10—C21—C22	−31.04 (17)
C5—C6—C7—C8	156.33 (16)	C19—C10—C21—C22	93.04 (14)
C1—C6—C7—C8	−23.9 (3)	C11—C10—C21—C22	−142.35 (12)
C6—C7—C8—C9	−176.56 (14)	C9—C10—C21—C29	83.93 (13)
C6—C7—C8—C12	−1.3 (3)	C19—C10—C21—C29	−151.98 (11)
C7—C8—C9—O1	−24.1 (2)	C11—C10—C21—C29	−27.37 (13)
C12—C8—C9—O1	160.29 (14)	N2—C21—C22—O3	53.63 (19)
C7—C8—C9—C10	156.00 (13)	C10—C21—C22—O3	−64.61 (19)
C12—C8—C9—C10	−19.64 (18)	C29—C21—C22—O3	−179.69 (13)
O1—C9—C10—C19	−2.6 (2)	N2—C21—C22—C23	−125.69 (13)
C8—C9—C10—C19	177.34 (12)	C10—C21—C22—C23	116.07 (13)
O1—C9—C10—C21	116.68 (15)	C29—C21—C22—C23	0.98 (14)
C8—C9—C10—C21	−63.39 (16)	O3—C22—C23—C28	179.97 (14)
O1—C9—C10—C11	−136.04 (14)	C21—C22—C23—C28	−0.75 (16)
C8—C9—C10—C11	43.90 (15)	O3—C22—C23—C24	−1.6 (3)
C12—N1—C11—C10	76.80 (13)	C21—C22—C23—C24	177.64 (14)
C29—N1—C11—C10	−45.79 (13)	C28—C23—C24—C25	0.6 (2)
C9—C10—C11—N1	−71.79 (13)	C22—C23—C24—C25	−177.60 (15)
C19—C10—C11—N1	158.37 (12)	C23—C24—C25—C26	0.2 (2)
C21—C10—C11—N1	44.82 (13)	C24—C25—C26—C27	−0.5 (3)
C11—N1—C12—C8	−50.37 (15)	C25—C26—C27—C28	0.0 (2)
C29—N1—C12—C8	65.83 (16)	C26—C27—C28—C23	0.8 (2)
C7—C8—C12—N1	−154.02 (14)	C26—C27—C28—C29	177.55 (14)
C9—C8—C12—N1	21.23 (18)	C24—C23—C28—C27	−1.1 (2)
C18—C13—C14—C15	0.7 (3)	C22—C23—C28—C27	177.39 (13)
C13—C14—C15—C16	0.3 (3)	C24—C23—C28—C29	−178.35 (13)
C13—C14—C15—C31	−178.27 (17)	C22—C23—C28—C29	0.17 (17)
C14—C15—C16—C17	−0.8 (2)	C12—N1—C29—O2	145.71 (12)
C31—C15—C16—C17	177.68 (17)	C11—N1—C29—O2	−95.69 (12)
C15—C16—C17—C18	0.5 (3)	C12—N1—C29—C28	23.31 (17)
C14—C13—C18—C17	−1.0 (2)	C11—N1—C29—C28	141.90 (12)
C14—C13—C18—C19	178.92 (15)	C12—N1—C29—C21	−91.62 (13)
C16—C17—C18—C13	0.5 (2)	C11—N1—C29—C21	26.98 (13)
C16—C17—C18—C19	−179.51 (14)	C27—C28—C29—O2	−55.96 (19)
C13—C18—C19—C10	−81.59 (18)	C23—C28—C29—O2	121.01 (13)
C17—C18—C19—C10	98.37 (16)	C27—C28—C29—N1	67.89 (19)
C13—C18—C19—C20	41.0 (2)	C23—C28—C29—N1	−115.14 (14)
C17—C18—C19—C20	−139.06 (15)	C27—C28—C29—C21	−176.52 (14)
C9—C10—C19—C18	−91.75 (15)	C23—C28—C29—C21	0.45 (15)
C21—C10—C19—C18	144.87 (12)	N2—C21—C29—O2	9.84 (17)
C11—C10—C19—C18	34.47 (18)	C22—C21—C29—O2	−117.13 (12)
C9—C10—C19—C20	139.85 (12)	C10—C21—C29—O2	122.01 (12)
C21—C10—C19—C20	16.48 (14)	N2—C21—C29—N1	−110.58 (12)
C11—C10—C19—C20	−93.92 (15)	C22—C21—C29—N1	122.45 (11)
C32—N2—C20—C19	−155.70 (12)	C10—C21—C29—N1	1.59 (14)
C21—N2—C20—C19	−26.24 (15)	N2—C21—C29—C28	126.12 (12)
C18—C19—C20—N2	−122.78 (13)	C22—C21—C29—C28	−0.85 (14)
C10—C19—C20—N2	4.99 (15)	C10—C21—C29—C28	−121.71 (12)

Cg1 is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N2i	0.85 (2)	2.00 (2)	2.794 (2)	156 (2)
C5—H5A···O3ii	0.93	2.48	3.206 (2)	135
C11—H11B···O2i	0.97	2.36	3.258 (2)	154
C13—H13A···O2i	0.93	2.40	3.291 (2)	161
C30—H30C···Cg1iii	0.96	2.83	3.563 (3)	134

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯N2i	0.85 (2)	2.00 (2)	2.794 (2)	156 (2)
C5—H5A⋯O3ii	0.93	2.48	3.206 (2)	135
C11—H11B⋯O2i	0.97	2.36	3.258 (2)	154
C13—H13A⋯O2i	0.93	2.40	3.291 (2)	161
C30—H30C⋯Cg1iii	0.96	2.83	3.563 (3)	134

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