(E)-1-{4-[Bis(4-meth-oxy-phen-yl)meth-yl]piperazin-1-yl}-3-(4-eth-oxy-3-meth-oxy-phen-yl)prop-2-en-1-one.

In the mol-ecule of the title compound, C(31)H(36)N(2)O(5), the piperazine ring displays a chair conformation. The dihedral angle between the benzene rings of the bis-(4-meth-oxy-phen-yl)methyl group is 83.42 (15)°. In the crystal, centrosymmetric-ally related mol-ecules are linked through pairs of C-H⋯O hydrogen bonds into dimers, generating an R(2) (2)(10) ring motif. The dimers are further connected into chains parallel to [2-10] by C-H⋯O hydrogen bonds involving the meth-oxy groups.

Related literature

For a related structure and background to cinnamic acid derivatives, see: Teng et al. (2011 ▶); Zhong et al. (2012 ▶). For synthetic details, see: Wu et al. (2008 ▶).

Experimental

Crystal data

C31H36N2O5

M = 516.62

Triclinic,

a = 8.7450 (17) Å

b = 11.635 (2) Å

c = 13.967 (3) Å

α = 84.07 (3)°

β = 78.80 (3)°

γ = 80.48 (3)°

V = 1371.1 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.975, T max = 0.992

5385 measured reflections

5029 independent reflections

2919 reflections with I > 2σ(I)

R int = 0.024

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.185

S = 1.00

5029 reflections

343 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo,1995 ▶); 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: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812012767/rz2721sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012767/rz2721Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812012767/rz2721Isup3.cml

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

C31H36N2O5	Z = 2
Mr = 516.62	F(000) = 552
Triclinic, P1	Dx = 1.251 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7450 (17) Å	Cell parameters from 25 reflections
b = 11.635 (2) Å	θ = 10–13°
c = 13.967 (3) Å	µ = 0.09 mm−1
α = 84.07 (3)°	T = 293 K
β = 78.80 (3)°	Block, colourless
γ = 80.48 (3)°	0.30 × 0.20 × 0.10 mm
V = 1371.1 (5) Å3

Enraf–Nonius CAD-4 diffractometer	2919 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 25.4°, θmin = 1.5°
ω/2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = −13→14
Tmin = 0.975, Tmax = 0.992	l = −16→16
5385 measured reflections	3 standard reflections every 200 reflections
5029 independent reflections	intensity decay: 1%

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
5029 reflections	(Δ/σ)max < 0.001
343 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.23 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
N1	0.3768 (3)	0.8993 (2)	0.66703 (15)	0.0501 (6)
O1	0.3423 (3)	1.1578 (2)	1.05560 (15)	0.0756 (7)
C1	0.2360 (3)	0.9243 (2)	0.74301 (19)	0.0524 (7)
H1A	0.2019	0.8499	0.7710	0.063*
N2	0.6239 (3)	0.7536 (2)	0.55113 (16)	0.0559 (6)
O2	−0.2833 (2)	1.2435 (2)	0.64559 (17)	0.0733 (6)
C2	0.2737 (3)	0.9857 (2)	0.82438 (19)	0.0481 (7)
O3	0.8333 (2)	0.61556 (18)	0.55887 (15)	0.0711 (7)
C3	0.2196 (4)	0.9519 (3)	0.9210 (2)	0.0589 (8)
H3A	0.1641	0.8888	0.9359	0.071*
O4	0.5773 (2)	0.47350 (19)	0.10257 (15)	0.0667 (6)
C4	0.2464 (4)	1.0103 (3)	0.9958 (2)	0.0646 (8)
H4A	0.2094	0.9858	1.0604	0.077*
O5	0.8391 (2)	0.36390 (17)	0.01711 (14)	0.0619 (6)
C5	0.3265 (3)	1.1036 (3)	0.9761 (2)	0.0552 (7)
C6	0.3837 (4)	1.1383 (3)	0.8805 (2)	0.0605 (8)
H6A	0.4403	1.2008	0.8660	0.073*
C7	0.3559 (3)	1.0790 (3)	0.8060 (2)	0.0567 (8)
H7A	0.3941	1.1031	0.7414	0.068*
C8	0.1001 (3)	0.9999 (2)	0.70365 (19)	0.0494 (7)
C9	0.1224 (3)	1.0973 (3)	0.6397 (2)	0.0649 (9)
H9A	0.2248	1.1088	0.6117	0.078*
C10	−0.0013 (4)	1.1779 (3)	0.6160 (2)	0.0667 (9)
H10A	0.0175	1.2419	0.5721	0.080*
C11	−0.1526 (3)	1.1625 (3)	0.6581 (2)	0.0549 (8)
C12	−0.1791 (3)	1.0636 (3)	0.7180 (2)	0.0590 (8)
H12A	−0.2818	1.0511	0.7440	0.071*
C13	−0.0542 (3)	0.9828 (3)	0.7396 (2)	0.0548 (7)
H13A	−0.0738	0.9156	0.7791	0.066*
C14	0.4221 (5)	1.2558 (3)	1.0382 (3)	0.0874 (11)
H14A	0.4236	1.2860	1.0994	0.131*
H14B	0.3688	1.3151	0.9981	0.131*
H14C	0.5283	1.2332	1.0052	0.131*
C15	−0.2520 (4)	1.3508 (3)	0.5941 (3)	0.0928 (12)
H15A	−0.3497	1.4010	0.5898	0.139*
H15B	−0.1949	1.3365	0.5294	0.139*
H15C	−0.1901	1.3877	0.6280	0.139*
C16	0.3460 (3)	0.8373 (3)	0.5892 (2)	0.0562 (8)
H16A	0.2593	0.8821	0.5613	0.067*
H16B	0.3155	0.7624	0.6161	0.067*
C17	0.4903 (3)	0.8181 (3)	0.5101 (2)	0.0580 (8)
H17A	0.4684	0.7745	0.4600	0.070*
H17B	0.5163	0.8929	0.4799	0.070*
C18	0.6536 (3)	0.8093 (3)	0.6328 (2)	0.0622 (8)
H18A	0.6890	0.8836	0.6095	0.075*
H18B	0.7363	0.7603	0.6618	0.075*
C19	0.5065 (3)	0.8289 (3)	0.7088 (2)	0.0567 (8)
H19A	0.4760	0.7540	0.7357	0.068*
H19B	0.5274	0.8684	0.7617	0.068*
C20	0.7246 (3)	0.6608 (2)	0.5165 (2)	0.0522 (7)
C21	0.7065 (3)	0.6159 (2)	0.4245 (2)	0.0543 (7)
H21A	0.6177	0.6441	0.3970	0.065*
C22	0.8165 (3)	0.5356 (2)	0.3813 (2)	0.0529 (7)
H22A	0.9006	0.5078	0.4133	0.063*
C23	0.8201 (3)	0.4861 (2)	0.2892 (2)	0.0493 (7)
C24	0.6896 (3)	0.5045 (2)	0.2415 (2)	0.0528 (7)
H24A	0.5957	0.5473	0.2707	0.063*
C25	0.6981 (3)	0.4607 (2)	0.1527 (2)	0.0499 (7)
C26	0.8413 (3)	0.3991 (2)	0.1071 (2)	0.0514 (7)
C27	0.9680 (3)	0.3780 (2)	0.1541 (2)	0.0567 (8)
H27A	1.0616	0.3345	0.1253	0.068*
C28	0.9569 (3)	0.4210 (3)	0.2443 (2)	0.0586 (8)
H28A	1.0437	0.4057	0.2755	0.070*
C29	0.4275 (4)	0.5266 (3)	0.1486 (3)	0.0746 (10)
H29A	0.3530	0.5298	0.1058	0.112*
H29B	0.4339	0.6044	0.1630	0.112*
H29C	0.3937	0.4816	0.2083	0.112*
C30	0.9841 (3)	0.3096 (3)	−0.0371 (2)	0.0608 (8)
H30A	1.0254	0.2398	−0.0003	0.073*
H30B	1.0614	0.3627	−0.0495	0.073*
C31	0.9514 (4)	0.2785 (3)	−0.1315 (2)	0.0776 (10)
H31A	1.0474	0.2424	−0.1698	0.116*
H31B	0.9101	0.3481	−0.1671	0.116*
H31C	0.8758	0.2252	−0.1185	0.116*

	U11	U22	U33	U12	U13	U23
N1	0.0466 (13)	0.0617 (14)	0.0413 (12)	0.0009 (11)	−0.0075 (10)	−0.0150 (11)
O1	0.1028 (18)	0.0774 (15)	0.0527 (13)	−0.0129 (13)	−0.0218 (12)	−0.0193 (11)
C1	0.0543 (17)	0.0575 (17)	0.0443 (16)	−0.0087 (14)	−0.0031 (13)	−0.0085 (13)
N2	0.0509 (14)	0.0666 (15)	0.0516 (14)	0.0084 (12)	−0.0168 (11)	−0.0243 (12)
O2	0.0480 (12)	0.0907 (17)	0.0820 (16)	−0.0089 (12)	−0.0199 (11)	0.0027 (13)
C2	0.0453 (15)	0.0527 (16)	0.0433 (16)	−0.0034 (13)	−0.0025 (12)	−0.0059 (13)
O3	0.0687 (14)	0.0777 (15)	0.0698 (14)	0.0170 (12)	−0.0324 (12)	−0.0269 (11)
C3	0.0664 (19)	0.0651 (19)	0.0446 (17)	−0.0214 (16)	0.0007 (15)	−0.0037 (14)
O4	0.0512 (12)	0.0867 (15)	0.0652 (13)	0.0084 (11)	−0.0190 (10)	−0.0328 (11)
C4	0.082 (2)	0.072 (2)	0.0382 (16)	−0.0145 (18)	−0.0020 (15)	−0.0083 (15)
O5	0.0584 (12)	0.0728 (13)	0.0546 (12)	0.0042 (10)	−0.0104 (10)	−0.0275 (10)
C5	0.0588 (18)	0.0574 (18)	0.0493 (18)	0.0018 (15)	−0.0136 (14)	−0.0130 (14)
C6	0.0627 (19)	0.0641 (19)	0.0555 (19)	−0.0144 (16)	−0.0062 (15)	−0.0098 (15)
C7	0.0614 (19)	0.070 (2)	0.0371 (15)	−0.0148 (16)	−0.0002 (13)	−0.0036 (14)
C8	0.0489 (16)	0.0621 (18)	0.0368 (15)	−0.0080 (14)	−0.0025 (12)	−0.0115 (13)
C9	0.0413 (17)	0.088 (2)	0.0596 (19)	−0.0095 (16)	0.0027 (14)	0.0016 (17)
C10	0.0535 (19)	0.086 (2)	0.0549 (19)	−0.0078 (17)	−0.0037 (15)	0.0068 (17)
C11	0.0455 (17)	0.074 (2)	0.0494 (17)	−0.0099 (15)	−0.0142 (14)	−0.0108 (15)
C12	0.0415 (16)	0.080 (2)	0.0586 (19)	−0.0167 (16)	−0.0063 (14)	−0.0132 (17)
C13	0.0539 (18)	0.0634 (18)	0.0494 (17)	−0.0183 (15)	−0.0049 (14)	−0.0082 (14)
C14	0.120 (3)	0.075 (2)	0.080 (3)	−0.015 (2)	−0.040 (2)	−0.0193 (19)
C15	0.070 (2)	0.083 (3)	0.122 (3)	−0.004 (2)	−0.023 (2)	0.011 (2)
C16	0.0521 (17)	0.0707 (19)	0.0474 (16)	0.0000 (15)	−0.0137 (14)	−0.0184 (14)
C17	0.0540 (18)	0.0681 (19)	0.0507 (17)	0.0064 (15)	−0.0127 (14)	−0.0174 (15)
C18	0.0555 (18)	0.076 (2)	0.0602 (19)	0.0048 (16)	−0.0217 (15)	−0.0292 (16)
C19	0.0618 (18)	0.0611 (18)	0.0478 (17)	0.0037 (15)	−0.0165 (15)	−0.0149 (14)
C20	0.0480 (17)	0.0551 (17)	0.0543 (18)	−0.0028 (14)	−0.0117 (14)	−0.0117 (14)
C21	0.0502 (17)	0.0605 (18)	0.0540 (18)	−0.0005 (14)	−0.0141 (14)	−0.0165 (14)
C22	0.0497 (17)	0.0577 (17)	0.0538 (17)	−0.0041 (14)	−0.0144 (14)	−0.0119 (14)
C23	0.0471 (16)	0.0502 (16)	0.0519 (17)	−0.0027 (13)	−0.0111 (13)	−0.0136 (13)
C24	0.0471 (16)	0.0548 (17)	0.0560 (18)	0.0002 (13)	−0.0068 (14)	−0.0183 (14)
C25	0.0475 (16)	0.0509 (16)	0.0534 (17)	−0.0040 (13)	−0.0118 (14)	−0.0140 (13)
C26	0.0540 (17)	0.0462 (16)	0.0542 (18)	−0.0016 (13)	−0.0096 (14)	−0.0139 (13)
C27	0.0517 (17)	0.0572 (18)	0.0590 (18)	0.0052 (14)	−0.0080 (15)	−0.0194 (14)
C28	0.0504 (17)	0.0623 (18)	0.065 (2)	0.0033 (15)	−0.0185 (15)	−0.0183 (15)
C29	0.0513 (19)	0.092 (2)	0.085 (2)	0.0076 (18)	−0.0230 (17)	−0.036 (2)
C30	0.0593 (19)	0.0576 (18)	0.0614 (19)	−0.0002 (15)	0.0004 (15)	−0.0204 (15)
C31	0.080 (2)	0.087 (2)	0.060 (2)	0.0059 (19)	−0.0003 (18)	−0.0303 (18)

N1—C16	1.454 (3)	C14—H14B	0.9600
N1—C19	1.466 (3)	C14—H14C	0.9600
N1—C1	1.471 (3)	C15—H15A	0.9600
O1—C5	1.373 (3)	C15—H15B	0.9600
O1—C14	1.409 (4)	C15—H15C	0.9600
C1—C8	1.516 (4)	C16—C17	1.509 (4)
C1—C2	1.517 (4)	C16—H16A	0.9700
C1—H1A	0.9800	C16—H16B	0.9700
N2—C20	1.342 (3)	C17—H17A	0.9700
N2—C18	1.454 (3)	C17—H17B	0.9700
N2—C17	1.462 (3)	C18—C19	1.502 (4)
O2—C11	1.383 (3)	C18—H18A	0.9700
O2—C15	1.415 (4)	C18—H18B	0.9700
C2—C7	1.375 (4)	C19—H19A	0.9700
C2—C3	1.379 (4)	C19—H19B	0.9700
O3—C20	1.233 (3)	C20—C21	1.482 (4)
C3—C4	1.379 (4)	C21—C22	1.325 (4)
C3—H3A	0.9300	C21—H21A	0.9300
O4—C25	1.358 (3)	C22—C23	1.455 (4)
O4—C29	1.414 (3)	C22—H22A	0.9300
C4—C5	1.364 (4)	C23—C28	1.380 (4)
C4—H4A	0.9300	C23—C24	1.406 (4)
O5—C26	1.366 (3)	C24—C25	1.373 (4)
O5—C30	1.429 (3)	C24—H24A	0.9300
C5—C6	1.375 (4)	C25—C26	1.406 (4)
C6—C7	1.385 (4)	C26—C27	1.370 (4)
C6—H6A	0.9300	C27—C28	1.384 (4)
C7—H7A	0.9300	C27—H27A	0.9300
C8—C13	1.384 (4)	C28—H28A	0.9300
C8—C9	1.385 (4)	C29—H29A	0.9600
C9—C10	1.378 (4)	C29—H29B	0.9600
C9—H9A	0.9300	C29—H29C	0.9600
C10—C11	1.373 (4)	C30—C31	1.494 (4)
C10—H10A	0.9300	C30—H30A	0.9700
C11—C12	1.375 (4)	C30—H30B	0.9700
C12—C13	1.377 (4)	C31—H31A	0.9600
C12—H12A	0.9300	C31—H31B	0.9600
C13—H13A	0.9300	C31—H31C	0.9600
C14—H14A	0.9600
C16—N1—C19	108.3 (2)	N1—C16—H16B	109.5
C16—N1—C1	112.1 (2)	C17—C16—H16B	109.5
C19—N1—C1	111.0 (2)	H16A—C16—H16B	108.1
C5—O1—C14	117.8 (3)	N2—C17—C16	110.5 (2)
N1—C1—C8	112.8 (2)	N2—C17—H17A	109.6
N1—C1—C2	110.6 (2)	C16—C17—H17A	109.6
C8—C1—C2	108.1 (2)	N2—C17—H17B	109.6
N1—C1—H1A	108.4	C16—C17—H17B	109.6
C8—C1—H1A	108.4	H17A—C17—H17B	108.1
C2—C1—H1A	108.4	N2—C18—C19	110.5 (2)
C20—N2—C18	119.6 (2)	N2—C18—H18A	109.6
C20—N2—C17	127.9 (2)	C19—C18—H18A	109.6
C18—N2—C17	112.1 (2)	N2—C18—H18B	109.6
C11—O2—C15	115.9 (2)	C19—C18—H18B	109.6
C7—C2—C3	117.3 (3)	H18A—C18—H18B	108.1
C7—C2—C1	122.3 (2)	N1—C19—C18	111.2 (2)
C3—C2—C1	120.3 (3)	N1—C19—H19A	109.4
C4—C3—C2	121.1 (3)	C18—C19—H19A	109.4
C4—C3—H3A	119.5	N1—C19—H19B	109.4
C2—C3—H3A	119.5	C18—C19—H19B	109.4
C25—O4—C29	117.9 (2)	H19A—C19—H19B	108.0
C5—C4—C3	120.8 (3)	O3—C20—N2	120.7 (3)
C5—C4—H4A	119.6	O3—C20—C21	120.3 (3)
C3—C4—H4A	119.6	N2—C20—C21	119.0 (2)
C26—O5—C30	117.8 (2)	C22—C21—C20	120.2 (3)
C4—C5—O1	116.1 (3)	C22—C21—H21A	119.9
C4—C5—C6	119.5 (3)	C20—C21—H21A	119.9
O1—C5—C6	124.4 (3)	C21—C22—C23	127.2 (3)
C5—C6—C7	119.2 (3)	C21—C22—H22A	116.4
C5—C6—H6A	120.4	C23—C22—H22A	116.4
C7—C6—H6A	120.4	C28—C23—C24	117.7 (2)
C2—C7—C6	122.1 (3)	C28—C23—C22	119.8 (2)
C2—C7—H7A	118.9	C24—C23—C22	122.5 (2)
C6—C7—H7A	118.9	C25—C24—C23	121.3 (3)
C13—C8—C9	116.9 (3)	C25—C24—H24A	119.3
C13—C8—C1	121.0 (3)	C23—C24—H24A	119.3
C9—C8—C1	121.7 (3)	O4—C25—C24	124.9 (2)
C10—C9—C8	122.5 (3)	O4—C25—C26	115.6 (2)
C10—C9—H9A	118.8	C24—C25—C26	119.5 (3)
C8—C9—H9A	118.8	O5—C26—C27	125.6 (3)
C11—C10—C9	119.1 (3)	O5—C26—C25	114.8 (2)
C11—C10—H10A	120.4	C27—C26—C25	119.6 (3)
C9—C10—H10A	120.4	C26—C27—C28	120.2 (3)
C10—C11—C12	119.7 (3)	C26—C27—H27A	119.9
C10—C11—O2	123.3 (3)	C28—C27—H27A	119.9
C12—C11—O2	116.9 (3)	C23—C28—C27	121.6 (3)
C11—C12—C13	120.3 (3)	C23—C28—H28A	119.2
C11—C12—H12A	119.9	C27—C28—H28A	119.2
C13—C12—H12A	119.9	O4—C29—H29A	109.5
C12—C13—C8	121.3 (3)	O4—C29—H29B	109.5
C12—C13—H13A	119.4	H29A—C29—H29B	109.5
C8—C13—H13A	119.4	O4—C29—H29C	109.5
O1—C14—H14A	109.5	H29A—C29—H29C	109.5
O1—C14—H14B	109.5	H29B—C29—H29C	109.5
H14A—C14—H14B	109.5	O5—C30—C31	107.7 (2)
O1—C14—H14C	109.5	O5—C30—H30A	110.2
H14A—C14—H14C	109.5	C31—C30—H30A	110.2
H14B—C14—H14C	109.5	O5—C30—H30B	110.2
O2—C15—H15A	109.5	C31—C30—H30B	110.2
O2—C15—H15B	109.5	H30A—C30—H30B	108.5
H15A—C15—H15B	109.5	C30—C31—H31A	109.5
O2—C15—H15C	109.5	C30—C31—H31B	109.5
H15A—C15—H15C	109.5	H31A—C31—H31B	109.5
H15B—C15—H15C	109.5	C30—C31—H31C	109.5
N1—C16—C17	110.8 (2)	H31A—C31—H31C	109.5
N1—C16—H16A	109.5	H31B—C31—H31C	109.5
C17—C16—H16A	109.5
C16—N1—C1—C8	−60.4 (3)	C1—N1—C16—C17	177.3 (2)
C19—N1—C1—C8	178.4 (2)	C20—N2—C17—C16	132.9 (3)
C16—N1—C1—C2	178.3 (2)	C18—N2—C17—C16	−54.0 (3)
C19—N1—C1—C2	57.1 (3)	N1—C16—C17—N2	57.5 (3)
N1—C1—C2—C7	47.1 (3)	C20—N2—C18—C19	−132.4 (3)
C8—C1—C2—C7	−77.0 (3)	C17—N2—C18—C19	53.9 (3)
N1—C1—C2—C3	−135.8 (3)	C16—N1—C19—C18	60.1 (3)
C8—C1—C2—C3	100.2 (3)	C1—N1—C19—C18	−176.5 (2)
C7—C2—C3—C4	0.4 (4)	N2—C18—C19—N1	−57.2 (3)
C1—C2—C3—C4	−176.9 (3)	C18—N2—C20—O3	6.9 (4)
C2—C3—C4—C5	0.4 (5)	C17—N2—C20—O3	179.5 (3)
C3—C4—C5—O1	177.9 (3)	C18—N2—C20—C21	−171.0 (3)
C3—C4—C5—C6	−1.2 (5)	C17—N2—C20—C21	1.6 (4)
C14—O1—C5—C4	−179.0 (3)	O3—C20—C21—C22	−7.5 (4)
C14—O1—C5—C6	0.2 (4)	N2—C20—C21—C22	170.4 (3)
C4—C5—C6—C7	1.2 (4)	C20—C21—C22—C23	−177.3 (3)
O1—C5—C6—C7	−177.9 (3)	C21—C22—C23—C28	167.0 (3)
C3—C2—C7—C6	−0.3 (4)	C21—C22—C23—C24	−11.1 (5)
C1—C2—C7—C6	176.9 (3)	C28—C23—C24—C25	−0.8 (4)
C5—C6—C7—C2	−0.5 (5)	C22—C23—C24—C25	177.3 (3)
N1—C1—C8—C13	143.9 (3)	C29—O4—C25—C24	−6.0 (4)
C2—C1—C8—C13	−93.4 (3)	C29—O4—C25—C26	175.1 (3)
N1—C1—C8—C9	−44.3 (3)	C23—C24—C25—O4	179.2 (3)
C2—C1—C8—C9	78.4 (3)	C23—C24—C25—C26	−1.9 (4)
C13—C8—C9—C10	3.3 (4)	C30—O5—C26—C27	−6.0 (4)
C1—C8—C9—C10	−168.8 (3)	C30—O5—C26—C25	174.8 (2)
C8—C9—C10—C11	0.9 (5)	O4—C25—C26—O5	1.9 (4)
C9—C10—C11—C12	−4.2 (5)	C24—C25—C26—O5	−177.2 (2)
C9—C10—C11—O2	174.2 (3)	O4—C25—C26—C27	−177.4 (3)
C15—O2—C11—C10	−6.2 (4)	C24—C25—C26—C27	3.6 (4)
C15—O2—C11—C12	172.3 (3)	O5—C26—C27—C28	178.3 (3)
C10—C11—C12—C13	3.2 (4)	C25—C26—C27—C28	−2.6 (4)
O2—C11—C12—C13	−175.4 (2)	C24—C23—C28—C27	1.9 (4)
C11—C12—C13—C8	1.3 (4)	C22—C23—C28—C27	−176.3 (3)
C9—C8—C13—C12	−4.4 (4)	C26—C27—C28—C23	−0.2 (5)
C1—C8—C13—C12	167.8 (2)	C26—O5—C30—C31	179.6 (2)
C19—N1—C16—C17	−60.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···O2i	0.97	2.44	3.286 (4)	146
C22—H22A···O3ii	0.93	2.60	3.476 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17A⋯O2i	0.97	2.44	3.286 (4)	146
C22—H22A⋯O3ii	0.93	2.60	3.476 (3)	157

Symmetry codes: (i) ; (ii) .