9-{[4-(Dimethyl-amino)-benz-yl]amino}-5-(3,4,5-trimeth-oxy-phen-yl)-5,5a,8a,9-tetra-hydro-furo[3',4':6,7]naphtho-[2,3-d][1,3]dioxol-6(8H)-one.

In the title compound, C(31)H(34)N(2)O(7), the fused tetra-hydro-furan and six-membered rings each display an envelope conformation. The dihedral angles between the benzene ring of the benzo[d][1,3]dioxole and the other two benzene rings are 89.68 (3) and 63.38 (2)°. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules.

Related literature

For details of the synthesis and biological activity of podophyllotoxin (systematic name (10R,11R,15R,16R)-16-hy­droxy-10-(3,4,5-trimeth­oxy­phen­yl)-4,6,13-trioxatetra­cyclo­[7.7.0.03,7.011,15]hexa­deca-1,3(7),8-trien-12-one) derivatives, see: Yu et al. (2008 ▶); Zhao et al. (2009 ▶); Lu et al. (2010 ▶). For related structures, see: Zhang et al. (1994 ▶); Feng et al. (2008 ▶); Zuo et al. (2009 ▶).

Experimental

Crystal data

C31H34N2O7

M = 546.60

Monoclinic,

a = 10.188 (2) Å

b = 11.530 (3) Å

c = 11.691 (3) Å

β = 96.192 (4)°

V = 1365.4 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 113 K

0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2007 ▶) T min = 0.981, T max = 0.989

17611 measured reflections

6335 independent reflections

4878 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.061

S = 1.02

6335 reflections

370 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811019234/cv5091sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811019234/cv5091Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811019234/cv5091Isup3.cml

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

C31H34N2O7	F(000) = 580
Mr = 546.60	Dx = 1.329 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4484 reflections
a = 10.188 (2) Å	θ = 1.8–28.1°
b = 11.530 (3) Å	µ = 0.09 mm−1
c = 11.691 (3) Å	T = 113 K
β = 96.192 (4)°	Prism, colourless
V = 1365.4 (6) Å3	0.20 × 0.18 × 0.12 mm
Z = 2

Rigaku Saturn CCD area-detector diffractometer	6335 independent reflections
Radiation source: rotating anode	4878 reflections with I > 2σ(I)
multilayer	Rint = 0.034
Detector resolution: 14.63 pixels mm-1	θmax = 27.8°, θmin = 1.8°
ω and φ scans	h = −13→13
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2007)	k = −15→15
Tmin = 0.981, Tmax = 0.989	l = −15→15
17611 measured reflections

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.061	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.024P)2] where P = (Fo2 + 2Fc2)/3
6335 reflections	(Δ/σ)max = 0.005
370 parameters	Δρmax = 0.16 e Å−3
2 restraints	Δρmin = −0.21 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
O1	0.52128 (9)	0.59140 (8)	0.21947 (8)	0.0240 (2)
O2	0.52819 (9)	0.39712 (8)	0.27006 (7)	0.0233 (2)
O3	0.14528 (9)	0.64023 (8)	0.82671 (7)	0.0235 (2)
O4	0.14154 (9)	0.44619 (9)	0.83314 (8)	0.0282 (2)
O5	0.53808 (8)	0.28789 (8)	0.99527 (8)	0.0213 (2)
O6	0.74780 (8)	0.42130 (8)	0.99096 (7)	0.0214 (2)
O7	0.77467 (8)	0.56748 (8)	0.81392 (8)	0.0235 (2)
N1	−0.02700 (11)	1.09298 (11)	0.83706 (10)	0.0263 (3)
N2	0.14526 (11)	0.72761 (10)	0.48482 (9)	0.0210 (3)
C1	0.53397 (14)	0.47595 (12)	0.17577 (12)	0.0244 (3)
H1A	0.4615	0.4596	0.1145	0.029*
H1B	0.6191	0.4675	0.1430	0.029*
C2	0.46171 (12)	0.57629 (12)	0.31872 (11)	0.0181 (3)
C3	0.40468 (12)	0.65809 (12)	0.38261 (10)	0.0187 (3)
H3	0.3992	0.7370	0.3591	0.022*
C4	0.35439 (12)	0.62146 (11)	0.48439 (10)	0.0158 (3)
C5	0.27834 (12)	0.71177 (11)	0.54717 (10)	0.0167 (3)
H5	0.3268	0.7873	0.5483	0.020*
C6	0.27250 (13)	0.67110 (11)	0.67159 (10)	0.0166 (3)
H6	0.3641	0.6717	0.7122	0.020*
C7	0.18142 (14)	0.73142 (12)	0.74730 (11)	0.0219 (3)
H7A	0.2274	0.7963	0.7902	0.026*
H7B	0.1021	0.7620	0.7007	0.026*
C8	0.16817 (12)	0.53318 (12)	0.78400 (11)	0.0202 (3)
C9	0.22116 (12)	0.54719 (12)	0.66907 (11)	0.0164 (3)
H9	0.1437	0.5439	0.6088	0.020*
C10	0.32353 (12)	0.46168 (11)	0.63313 (10)	0.0160 (3)
H10	0.2802	0.3843	0.6197	0.019*
C11	0.36598 (12)	0.50503 (12)	0.51885 (10)	0.0160 (3)
C12	0.42322 (12)	0.42254 (12)	0.45006 (11)	0.0179 (3)
H12	0.4305	0.3433	0.4723	0.022*
C13	0.46778 (12)	0.46049 (12)	0.35037 (11)	0.0177 (3)
C14	0.11461 (15)	0.84675 (13)	0.44324 (12)	0.0265 (3)
H14A	0.0420	0.8443	0.3797	0.032*
H14B	0.1932	0.8807	0.4130	0.032*
C15	0.07453 (13)	0.92169 (12)	0.53913 (11)	0.0218 (3)
C16	0.15867 (13)	1.00166 (12)	0.59750 (12)	0.0234 (3)
H16	0.2414	1.0168	0.5701	0.028*
C17	0.12671 (13)	1.06049 (13)	0.69451 (12)	0.0240 (3)
H17	0.1869	1.1151	0.7314	0.029*
C18	0.00521 (12)	1.03947 (12)	0.73842 (11)	0.0204 (3)
C19	−0.08234 (13)	0.96224 (12)	0.67618 (11)	0.0217 (3)
H19	−0.1670	0.9491	0.7008	0.026*
C20	−0.04779 (13)	0.90515 (12)	0.58008 (11)	0.0216 (3)
H20	−0.1091	0.8530	0.5406	0.026*
C21	0.07587 (14)	1.15428 (13)	0.91019 (12)	0.0274 (3)
H21A	0.1551	1.1057	0.9220	0.041*
H21B	0.0443	1.1713	0.9847	0.041*
H21C	0.0972	1.2270	0.8730	0.041*
C22	−0.14462 (14)	1.05611 (15)	0.88653 (12)	0.0321 (4)
H22A	−0.2228	1.0745	0.8333	0.048*
H22B	−0.1499	1.0966	0.9596	0.048*
H22C	−0.1407	0.9723	0.9002	0.048*
C23	0.44248 (12)	0.44741 (11)	0.72446 (10)	0.0160 (3)
C24	0.43331 (13)	0.37052 (11)	0.81531 (11)	0.0175 (3)
H24	0.3558	0.3252	0.8181	0.021*
C25	0.53765 (12)	0.36013 (11)	0.90182 (11)	0.0164 (3)
C26	0.65162 (12)	0.42673 (12)	0.89914 (10)	0.0163 (3)
C27	0.66085 (12)	0.50269 (11)	0.80689 (11)	0.0176 (3)
C28	0.55777 (12)	0.51155 (11)	0.71925 (11)	0.0168 (3)
H28	0.5658	0.5614	0.6557	0.020*
C29	0.41589 (13)	0.23341 (13)	1.01374 (11)	0.0260 (3)
H29A	0.3478	0.2928	1.0183	0.039*
H29B	0.4272	0.1894	1.0858	0.039*
H29C	0.3890	0.1807	0.9497	0.039*
C30	0.87104 (13)	0.37267 (14)	0.96535 (13)	0.0309 (4)
H30A	0.8542	0.3019	0.9197	0.046*
H30B	0.9254	0.3539	1.0373	0.046*
H30C	0.9176	0.4290	0.9216	0.046*
C31	0.78655 (14)	0.65140 (14)	0.72551 (12)	0.0301 (4)
H31A	0.7865	0.6119	0.6513	0.045*
H31B	0.8693	0.6944	0.7426	0.045*
H31C	0.7120	0.7054	0.7221	0.045*
H2	0.1326 (14)	0.6802 (12)	0.4235 (10)	0.033 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0322 (6)	0.0216 (5)	0.0202 (5)	0.0008 (4)	0.0114 (4)	−0.0022 (4)
O2	0.0307 (5)	0.0213 (5)	0.0195 (5)	0.0047 (4)	0.0098 (4)	−0.0025 (4)
O3	0.0282 (5)	0.0229 (5)	0.0212 (5)	0.0033 (4)	0.0106 (4)	0.0016 (4)
O4	0.0291 (6)	0.0260 (6)	0.0319 (6)	−0.0013 (5)	0.0136 (5)	0.0057 (5)
O5	0.0240 (5)	0.0214 (5)	0.0187 (5)	−0.0029 (4)	0.0036 (4)	0.0054 (4)
O6	0.0164 (5)	0.0301 (6)	0.0177 (5)	0.0007 (4)	0.0017 (4)	0.0006 (4)
O7	0.0188 (5)	0.0261 (6)	0.0253 (5)	−0.0074 (4)	0.0013 (4)	0.0065 (4)
N1	0.0224 (6)	0.0318 (7)	0.0243 (6)	−0.0011 (5)	0.0013 (5)	−0.0075 (6)
N2	0.0236 (6)	0.0206 (6)	0.0179 (6)	0.0047 (5)	−0.0019 (5)	−0.0031 (5)
C1	0.0325 (8)	0.0221 (8)	0.0198 (7)	0.0017 (7)	0.0087 (6)	−0.0015 (6)
C2	0.0170 (6)	0.0225 (8)	0.0153 (6)	−0.0025 (6)	0.0033 (5)	−0.0005 (6)
C3	0.0218 (7)	0.0157 (7)	0.0185 (7)	−0.0005 (6)	0.0024 (6)	0.0003 (6)
C4	0.0149 (6)	0.0174 (7)	0.0151 (6)	−0.0003 (5)	0.0012 (5)	−0.0014 (5)
C5	0.0166 (6)	0.0155 (7)	0.0181 (7)	−0.0001 (6)	0.0026 (5)	−0.0017 (6)
C6	0.0172 (6)	0.0172 (7)	0.0157 (6)	0.0002 (6)	0.0035 (5)	−0.0017 (6)
C7	0.0276 (8)	0.0190 (7)	0.0203 (7)	−0.0006 (6)	0.0077 (6)	0.0033 (6)
C8	0.0162 (6)	0.0223 (8)	0.0225 (7)	0.0003 (6)	0.0042 (5)	0.0018 (6)
C9	0.0145 (6)	0.0187 (7)	0.0160 (6)	−0.0017 (6)	0.0018 (5)	−0.0010 (6)
C10	0.0176 (7)	0.0148 (7)	0.0156 (6)	−0.0020 (6)	0.0022 (5)	−0.0002 (5)
C11	0.0135 (6)	0.0194 (7)	0.0149 (6)	−0.0008 (6)	0.0003 (5)	−0.0016 (6)
C12	0.0182 (7)	0.0158 (7)	0.0197 (7)	0.0007 (6)	0.0014 (5)	0.0001 (6)
C13	0.0158 (6)	0.0205 (7)	0.0165 (7)	0.0026 (6)	0.0009 (5)	−0.0048 (6)
C14	0.0296 (8)	0.0280 (8)	0.0215 (7)	0.0096 (7)	0.0008 (6)	0.0042 (6)
C15	0.0252 (7)	0.0199 (7)	0.0202 (7)	0.0073 (6)	0.0018 (6)	0.0051 (6)
C16	0.0211 (7)	0.0220 (8)	0.0278 (8)	0.0037 (6)	0.0055 (6)	0.0080 (6)
C17	0.0215 (7)	0.0202 (8)	0.0296 (8)	−0.0006 (6)	0.0000 (6)	0.0023 (6)
C18	0.0200 (7)	0.0182 (7)	0.0224 (7)	0.0044 (6)	−0.0006 (5)	0.0023 (6)
C19	0.0173 (7)	0.0243 (8)	0.0230 (7)	0.0019 (6)	0.0007 (6)	0.0047 (6)
C20	0.0222 (7)	0.0198 (7)	0.0214 (7)	0.0025 (6)	−0.0041 (6)	0.0010 (6)
C21	0.0271 (8)	0.0246 (8)	0.0292 (8)	0.0025 (7)	−0.0030 (6)	−0.0054 (7)
C22	0.0289 (8)	0.0447 (10)	0.0230 (7)	−0.0014 (8)	0.0040 (6)	−0.0040 (7)
C23	0.0185 (6)	0.0152 (7)	0.0147 (6)	0.0017 (5)	0.0039 (5)	−0.0012 (5)
C24	0.0185 (7)	0.0154 (7)	0.0193 (7)	−0.0021 (5)	0.0059 (5)	−0.0012 (6)
C25	0.0217 (7)	0.0138 (7)	0.0146 (6)	0.0014 (6)	0.0067 (5)	0.0020 (5)
C26	0.0160 (6)	0.0181 (7)	0.0148 (6)	0.0022 (5)	0.0017 (5)	−0.0026 (6)
C27	0.0161 (6)	0.0164 (7)	0.0209 (7)	−0.0006 (5)	0.0052 (5)	−0.0013 (6)
C28	0.0204 (7)	0.0145 (7)	0.0160 (6)	−0.0002 (5)	0.0048 (5)	0.0028 (6)
C29	0.0313 (8)	0.0253 (8)	0.0225 (7)	−0.0079 (7)	0.0088 (6)	0.0050 (6)
C30	0.0242 (8)	0.0364 (9)	0.0311 (8)	0.0124 (7)	−0.0007 (6)	−0.0026 (7)
C31	0.0271 (8)	0.0318 (9)	0.0316 (8)	−0.0096 (7)	0.0041 (7)	0.0113 (7)

O1—C2	1.3773 (15)	C11—C12	1.4118 (18)
O1—C1	1.4367 (17)	C12—C13	1.3676 (17)
O2—C13	1.3852 (15)	C12—H12	0.9500
O2—C1	1.4349 (16)	C14—C15	1.5063 (19)
O3—C8	1.3610 (16)	C14—H14A	0.9900
O3—C7	1.4753 (15)	C14—H14B	0.9900
O4—C8	1.2014 (16)	C15—C16	1.387 (2)
O5—C25	1.3734 (15)	C15—C20	1.3955 (18)
O5—C29	1.4314 (15)	C16—C17	1.3901 (19)
O6—C26	1.3746 (15)	C16—H16	0.9500
O6—C30	1.4359 (16)	C17—C18	1.4113 (18)
O7—C27	1.3744 (15)	C17—H17	0.9500
O7—C31	1.4305 (16)	C18—C19	1.4064 (19)
N1—C18	1.3784 (16)	C19—C20	1.3802 (18)
N1—C22	1.4494 (17)	C19—H19	0.9500
N1—C21	1.4615 (17)	C20—H20	0.9500
N2—C14	1.4792 (18)	C21—H21A	0.9800
N2—C5	1.4798 (16)	C21—H21B	0.9800
N2—H2	0.900 (9)	C21—H21C	0.9800
C1—H1A	0.9900	C22—H22A	0.9800
C1—H1B	0.9900	C22—H22B	0.9800
C2—C3	1.3707 (18)	C22—H22C	0.9800
C2—C13	1.3851 (19)	C23—C24	1.3945 (17)
C3—C4	1.4100 (17)	C23—C28	1.3949 (18)
C3—H3	0.9500	C24—C25	1.3912 (17)
C4—C11	1.4030 (18)	C24—H24	0.9500
C4—C5	1.5317 (18)	C25—C26	1.3954 (18)
C5—C6	1.5356 (17)	C26—C27	1.4004 (17)
C5—H5	1.0000	C27—C28	1.3896 (17)
C6—C7	1.5184 (17)	C28—H28	0.9500
C6—C9	1.5206 (18)	C29—H29A	0.9800
C6—H6	1.0000	C29—H29B	0.9800
C7—H7A	0.9900	C29—H29C	0.9800
C7—H7B	0.9900	C30—H30A	0.9800
C8—C9	1.5098 (18)	C30—H30B	0.9800
C9—C10	1.5268 (17)	C30—H30C	0.9800
C9—H9	1.0000	C31—H31A	0.9800
C10—C11	1.5319 (16)	C31—H31B	0.9800
C10—C23	1.5351 (17)	C31—H31C	0.9800
C10—H10	1.0000
C2—O1—C1	104.30 (10)	C15—C14—H14A	109.5
C13—O2—C1	104.16 (10)	N2—C14—H14B	109.5
C8—O3—C7	110.56 (9)	C15—C14—H14B	109.5
C25—O5—C29	117.25 (10)	H14A—C14—H14B	108.1
C26—O6—C30	114.88 (9)	C16—C15—C20	116.70 (12)
C27—O7—C31	117.45 (10)	C16—C15—C14	123.00 (13)
C18—N1—C22	118.96 (12)	C20—C15—C14	120.05 (13)
C18—N1—C21	119.05 (11)	C15—C16—C17	122.62 (12)
C22—N1—C21	118.69 (11)	C15—C16—H16	118.7
C14—N2—C5	115.23 (11)	C17—C16—H16	118.7
C14—N2—H2	107.1 (10)	C16—C17—C18	120.32 (13)
C5—N2—H2	111.3 (10)	C16—C17—H17	119.8
O2—C1—O1	107.52 (10)	C18—C17—H17	119.8
O2—C1—H1A	110.2	N1—C18—C19	121.42 (12)
O1—C1—H1A	110.2	N1—C18—C17	121.65 (12)
O2—C1—H1B	110.2	C19—C18—C17	116.92 (12)
O1—C1—H1B	110.2	C20—C19—C18	121.33 (12)
H1A—C1—H1B	108.5	C20—C19—H19	119.3
C3—C2—O1	128.56 (12)	C18—C19—H19	119.3
C3—C2—C13	121.80 (12)	C19—C20—C15	121.99 (13)
O1—C2—C13	109.63 (11)	C19—C20—H20	119.0
C2—C3—C4	117.89 (12)	C15—C20—H20	119.0
C2—C3—H3	121.1	N1—C21—H21A	109.5
C4—C3—H3	121.1	N1—C21—H21B	109.5
C11—C4—C3	120.13 (12)	H21A—C21—H21B	109.5
C11—C4—C5	122.96 (11)	N1—C21—H21C	109.5
C3—C4—C5	116.71 (12)	H21A—C21—H21C	109.5
N2—C5—C4	109.38 (10)	H21B—C21—H21C	109.5
N2—C5—C6	112.16 (10)	N1—C22—H22A	109.5
C4—C5—C6	108.64 (10)	N1—C22—H22B	109.5
N2—C5—H5	108.9	H22A—C22—H22B	109.5
C4—C5—H5	108.9	N1—C22—H22C	109.5
C6—C5—H5	108.9	H22A—C22—H22C	109.5
C7—C6—C9	102.19 (10)	H22B—C22—H22C	109.5
C7—C6—C5	120.06 (11)	C24—C23—C28	119.75 (12)
C9—C6—C5	108.48 (10)	C24—C23—C10	119.03 (11)
C7—C6—H6	108.5	C28—C23—C10	121.21 (11)
C9—C6—H6	108.5	C25—C24—C23	119.99 (12)
C5—C6—H6	108.5	C25—C24—H24	120.0
O3—C7—C6	104.48 (10)	C23—C24—H24	120.0
O3—C7—H7A	110.9	O5—C25—C24	124.55 (12)
C6—C7—H7A	110.9	O5—C25—C26	114.86 (11)
O3—C7—H7B	110.9	C24—C25—C26	120.58 (12)
C6—C7—H7B	110.9	O6—C26—C25	118.83 (11)
H7A—C7—H7B	108.9	O6—C26—C27	121.91 (12)
O4—C8—O3	121.68 (11)	C25—C26—C27	119.12 (11)
O4—C8—C9	129.48 (13)	O7—C27—C28	124.74 (12)
O3—C8—C9	108.74 (11)	O7—C27—C26	114.84 (11)
C8—C9—C6	103.80 (10)	C28—C27—C26	120.38 (11)
C8—C9—C10	119.75 (11)	C27—C28—C23	120.12 (12)
C6—C9—C10	111.61 (10)	C27—C28—H28	119.9
C8—C9—H9	107.0	C23—C28—H28	119.9
C6—C9—H9	107.0	O5—C29—H29A	109.5
C10—C9—H9	107.0	O5—C29—H29B	109.5
C9—C10—C11	107.14 (10)	H29A—C29—H29B	109.5
C9—C10—C23	112.91 (10)	O5—C29—H29C	109.5
C11—C10—C23	111.45 (10)	H29A—C29—H29C	109.5
C9—C10—H10	108.4	H29B—C29—H29C	109.5
C11—C10—H10	108.4	O6—C30—H30A	109.5
C23—C10—H10	108.4	O6—C30—H30B	109.5
C4—C11—C12	120.54 (11)	H30A—C30—H30B	109.5
C4—C11—C10	122.67 (11)	O6—C30—H30C	109.5
C12—C11—C10	116.74 (12)	H30A—C30—H30C	109.5
C13—C12—C11	117.74 (12)	H30B—C30—H30C	109.5
C13—C12—H12	121.1	O7—C31—H31A	109.5
C11—C12—H12	121.1	O7—C31—H31B	109.5
C12—C13—O2	128.42 (12)	H31A—C31—H31B	109.5
C12—C13—C2	121.79 (12)	O7—C31—H31C	109.5
O2—C13—C2	109.74 (11)	H31A—C31—H31C	109.5
N2—C14—C15	110.65 (11)	H31B—C31—H31C	109.5
N2—C14—H14A	109.5
C13—O2—C1—O1	20.33 (13)	C1—O2—C13—C2	−11.56 (14)
C2—O1—C1—O2	−21.44 (14)	C3—C2—C13—C12	−3.4 (2)
C1—O1—C2—C3	−166.58 (13)	O1—C2—C13—C12	175.82 (11)
C1—O1—C2—C13	14.31 (14)	C3—C2—C13—O2	179.03 (11)
O1—C2—C3—C4	−177.49 (12)	O1—C2—C13—O2	−1.79 (15)
C13—C2—C3—C4	1.52 (19)	C5—N2—C14—C15	−80.58 (14)
C2—C3—C4—C11	1.34 (19)	N2—C14—C15—C16	102.22 (16)
C2—C3—C4—C5	−173.71 (11)	N2—C14—C15—C20	−71.91 (16)
C14—N2—C5—C4	−120.42 (12)	C20—C15—C16—C17	2.2 (2)
C14—N2—C5—C6	118.97 (12)	C14—C15—C16—C17	−172.16 (13)
C11—C4—C5—N2	−98.96 (14)	C15—C16—C17—C18	0.6 (2)
C3—C4—C5—N2	75.94 (14)	C22—N1—C18—C19	9.1 (2)
C11—C4—C5—C6	23.77 (16)	C21—N1—C18—C19	168.32 (13)
C3—C4—C5—C6	−161.34 (11)	C22—N1—C18—C17	−171.60 (13)
N2—C5—C6—C7	−47.32 (16)	C21—N1—C18—C17	−12.38 (19)
C4—C5—C6—C7	−168.35 (11)	C16—C17—C18—N1	177.37 (12)
N2—C5—C6—C9	69.46 (13)	C16—C17—C18—C19	−3.3 (2)
C4—C5—C6—C9	−51.57 (13)	N1—C18—C19—C20	−177.35 (12)
C8—O3—C7—C6	−19.07 (13)	C17—C18—C19—C20	3.3 (2)
C9—C6—C7—O3	30.09 (13)	C18—C19—C20—C15	−0.6 (2)
C5—C6—C7—O3	150.07 (11)	C16—C15—C20—C19	−2.2 (2)
C7—O3—C8—O4	−177.51 (12)	C14—C15—C20—C19	172.34 (12)
C7—O3—C8—C9	−0.70 (14)	C9—C10—C23—C24	83.46 (14)
O4—C8—C9—C6	−163.42 (13)	C11—C10—C23—C24	−155.89 (11)
O3—C8—C9—C6	20.10 (13)	C9—C10—C23—C28	−95.20 (13)
O4—C8—C9—C10	−38.2 (2)	C11—C10—C23—C28	25.45 (16)
O3—C8—C9—C10	145.35 (11)	C28—C23—C24—C25	1.60 (18)
C7—C6—C9—C8	−30.27 (13)	C10—C23—C24—C25	−177.08 (11)
C5—C6—C9—C8	−158.04 (10)	C29—O5—C25—C24	−10.00 (18)
C7—C6—C9—C10	−160.58 (10)	C29—O5—C25—C26	169.00 (11)
C5—C6—C9—C10	71.65 (13)	C23—C24—C25—O5	179.42 (12)
C8—C9—C10—C11	−175.07 (11)	C23—C24—C25—C26	0.46 (18)
C6—C9—C10—C11	−53.61 (13)	C30—O6—C26—C25	114.96 (13)
C8—C9—C10—C23	−51.99 (15)	C30—O6—C26—C27	−69.35 (16)
C6—C9—C10—C23	69.47 (13)	O5—C25—C26—O6	−4.51 (17)
C3—C4—C11—C12	−2.49 (19)	C24—C25—C26—O6	174.54 (11)
C5—C4—C11—C12	172.24 (11)	O5—C25—C26—C27	179.68 (11)
C3—C4—C11—C10	174.96 (11)	C24—C25—C26—C27	−1.27 (18)
C5—C4—C11—C10	−10.31 (19)	C31—O7—C27—C28	1.12 (18)
C9—C10—C11—C4	23.65 (16)	C31—O7—C27—C26	−176.55 (11)
C23—C10—C11—C4	−100.33 (14)	O6—C26—C27—O7	2.12 (17)
C9—C10—C11—C12	−158.81 (11)	C25—C26—C27—O7	177.80 (11)
C23—C10—C11—C12	77.21 (14)	O6—C26—C27—C28	−175.65 (11)
C4—C11—C12—C13	0.75 (18)	C25—C26—C27—C28	0.02 (18)
C10—C11—C12—C13	−176.85 (11)	O7—C27—C28—C23	−175.51 (12)
C11—C12—C13—O2	179.26 (12)	C26—C27—C28—C23	2.04 (19)
C11—C12—C13—C2	2.13 (19)	C24—C23—C28—C27	−2.84 (18)
C1—O2—C13—C12	171.03 (13)	C10—C23—C28—C27	175.81 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O5i	0.99	2.59	3.0292 (18)	107
C1—H1B···O6i	0.99	2.38	3.2904 (16)	153
C21—H21A···O6ii	0.98	2.51	3.3662 (18)	145
C22—H22B···O3iii	0.98	2.54	3.4909 (18)	162
C29—H29C···O1iv	0.98	2.49	3.3017 (18)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯O6i	0.99	2.38	3.2904 (16)	153
C21—H21A⋯O6ii	0.98	2.51	3.3662 (18)	145
C22—H22B⋯O3iii	0.98	2.54	3.4909 (18)	162
C29—H29C⋯O1iv	0.98	2.49	3.3017 (18)	140

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