Bis{4-[(1,3-benzodioxol-5-yl)meth-yl]piperazin-1-yl}methane.

In the title compound, C25H32N4O4, both piperazine rings adopt a chair conformation. One of dioxolane ring systems is essentially planar [dihedral angle = 0.9 (2)°] while the other adopts a slightly disordered envelope conformation, the mean plane of the dioxolane ring being twisted by 3.6 (2)° from that of the benzene ring. The dihedral angle between the benzene rings is 69.9 (5)°. No classical hydrogen bonds were observed.

Related literature

For the biological activity of piperazines, see: Choudhary et al. (2006 ▶); Kharb et al. (2012 ▶); Millan et al. (2001 ▶); Brockunier et al. (2004 ▶); Bogatcheva et al. (2006 ▶); Elliott (2011 ▶). For related structures, see: Capuano et al. (2000 ▶). For puckering parameters, see Cremer & Pople (1975 ▶).

Experimental

Crystal data

C25H32N4O4

M = 452.55

Orthorhombic,

a = 38.8025 (10) Å

b = 9.7675 (2) Å

c = 6.09571 (13) Å

V = 2310.29 (10) Å3

Z = 4

Cu Kα radiation

μ = 0.72 mm−1

T = 173 K

0.38 × 0.21 × 0.11 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.836, T max = 1.000

13559 measured reflections

4199 independent reflections

3869 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.108

S = 1.02

4199 reflections

307 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack parameter determined using 1513 quotients [(I+)−(I−)]/[(I+)+(I−)] (Parsons & Flack, 2004 ▶)

Absolute structure parameter: −0.03 (15)

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813028109/fj2646sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813028109/fj2646Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813028109/fj2646Isup3.cml

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

C25H32N4O4	Dx = 1.312 Mg m−3
Mr = 452.55	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pn21a	Cell parameters from 5154 reflections
a = 38.8025 (10) Å	θ = 4.5–72.4°
b = 9.7675 (2) Å	µ = 0.72 mm−1
c = 6.09571 (13) Å	T = 173 K
V = 2310.29 (10) Å3	Irregular, colourless
Z = 4	0.38 × 0.21 × 0.11 mm
F(000) = 968

Agilent Xcalibur (Eos, Gemini) diffractometer	4199 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3869 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1	Rint = 0.046
ω scans	θmax = 72.6°, θmin = 4.6°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −43→48
Tmin = 0.836, Tmax = 1.000	k = −11→12
13559 measured reflections	l = −5→7

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0485P)2 + 0.6698P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.041	(Δ/σ)max < 0.001
wR(F2) = 0.108	Δρmax = 0.22 e Å−3
S = 1.02	Δρmin = −0.17 e Å−3
4199 reflections	Extinction correction: SHELXL2012 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
307 parameters	Extinction coefficient: 0.0016 (2)
1 restraint	Absolute structure: Flack parameter determined using 1513 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004)
Hydrogen site location: mixed	Absolute structure parameter: −0.03 (15)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq
O1	0.31516 (6)	0.5691 (3)	1.0003 (4)	0.0425 (5)
O2	0.31379 (7)	0.7799 (3)	0.8258 (4)	0.0534 (7)
O3	0.75845 (6)	0.5660 (3)	0.1266 (4)	0.0452 (6)
O4	0.77389 (6)	0.4101 (3)	−0.1424 (4)	0.0431 (6)
N1	0.50857 (6)	0.5885 (3)	0.2715 (4)	0.0316 (6)
N2	0.43489 (6)	0.5829 (3)	0.2856 (4)	0.0283 (5)
N3	0.56439 (6)	0.5613 (3)	0.1084 (4)	0.0305 (5)
N4	0.62717 (6)	0.6657 (3)	−0.0775 (4)	0.0287 (5)
C0AA	0.54264 (8)	0.5299 (4)	0.2949 (5)	0.0359 (7)
C2	0.48991 (8)	0.5896 (4)	0.4788 (5)	0.0388 (8)
H2A	0.5031	0.6394	0.5879	0.047*
H2B	0.4868	0.4965	0.5306	0.047*
C3	0.45513 (8)	0.6567 (4)	0.4487 (5)	0.0363 (7)
H3A	0.4429	0.6576	0.5875	0.044*
H3B	0.4583	0.7508	0.4018	0.044*
C4	0.45353 (7)	0.5831 (4)	0.0781 (4)	0.0320 (6)
H4A	0.4566	0.6766	0.0279	0.038*
H4B	0.4403	0.5341	−0.0317	0.038*
C5	0.48843 (8)	0.5158 (3)	0.1056 (5)	0.0335 (7)
H5A	0.4854	0.4211	0.1496	0.040*
H5B	0.5007	0.5169	−0.0332	0.040*
C6	0.40051 (8)	0.6420 (3)	0.2635 (5)	0.0336 (7)
H6A	0.3892	0.6021	0.1368	0.040*
H6B	0.4026	0.7397	0.2382	0.040*
C7	0.37846 (7)	0.6181 (3)	0.4645 (5)	0.0290 (6)
C8	0.37856 (7)	0.4919 (3)	0.5700 (5)	0.0291 (6)
H8	0.3930	0.4234	0.5177	0.035*
C9	0.35775 (7)	0.4641 (3)	0.7517 (5)	0.0304 (6)
H9	0.3578	0.3789	0.8197	0.036*
C10	0.33726 (7)	0.5687 (3)	0.8245 (4)	0.0297 (6)
C11	0.30024 (9)	0.7027 (4)	1.0040 (6)	0.0445 (8)
H11A	0.2754	0.6961	0.9910	0.053*
H11B	0.3056	0.7478	1.1416	0.053*
C12	0.33670 (8)	0.6945 (3)	0.7208 (5)	0.0331 (7)
C13	0.35674 (8)	0.7227 (3)	0.5419 (5)	0.0337 (7)
H13	0.3560	0.8079	0.4740	0.040*
C14	0.59693 (8)	0.4870 (3)	0.1253 (5)	0.0342 (7)
H14A	0.5924	0.3894	0.1294	0.041*
H14B	0.6085	0.5122	0.2605	0.041*
C15	0.62001 (8)	0.5196 (3)	−0.0679 (5)	0.0332 (7)
H15A	0.6415	0.4695	−0.0540	0.040*
H15B	0.6089	0.4909	−0.2027	0.040*
C16	0.59437 (7)	0.7386 (3)	−0.0990 (5)	0.0311 (6)
H16A	0.5830	0.7110	−0.2337	0.037*
H16B	0.5986	0.8364	−0.1065	0.037*
C17	0.57131 (7)	0.7078 (3)	0.0934 (5)	0.0320 (6)
H17A	0.5823	0.7388	0.2275	0.038*
H17B	0.5498	0.7570	0.0770	0.038*
C18	0.65041 (7)	0.7011 (3)	−0.2577 (5)	0.0341 (7)
H18A	0.6544	0.7991	−0.2567	0.041*
H18B	0.6395	0.6779	−0.3959	0.041*
C19	0.68447 (7)	0.6275 (3)	−0.2412 (5)	0.0310 (6)
C20	0.70492 (8)	0.6439 (4)	−0.0521 (5)	0.0333 (7)
H20	0.6987	0.7043	0.0590	0.040*
C21	0.73433 (7)	0.5672 (4)	−0.0390 (4)	0.0314 (6)
C22	0.78104 (9)	0.4551 (4)	0.0760 (6)	0.0439 (8)
H22A	0.7775	0.3806	0.1787	0.053*
H22B	0.8048	0.4848	0.0872	0.053*
C23	0.74391 (7)	0.4755 (3)	−0.2007 (5)	0.0323 (7)
C24	0.72513 (8)	0.4605 (4)	−0.3887 (5)	0.0367 (7)
H24	0.7320	0.4014	−0.4999	0.044*
C25	0.69508 (8)	0.5383 (3)	−0.4056 (5)	0.0325 (7)
H25	0.6817	0.5302	−0.5314	0.039*
H0AA	0.5513 (8)	0.564 (4)	0.426 (5)	0.031 (9)*
H0AB	0.5410 (9)	0.429 (4)	0.313 (6)	0.040 (10)*

	U11	U22	U33	U12	U13	U23
O1	0.0476 (13)	0.0446 (14)	0.0352 (11)	0.0079 (11)	0.0122 (10)	0.0003 (10)
O2	0.0654 (17)	0.0392 (15)	0.0557 (16)	0.0191 (12)	0.0233 (13)	0.0014 (12)
O3	0.0382 (12)	0.0574 (16)	0.0399 (12)	0.0129 (12)	−0.0079 (9)	−0.0052 (12)
O4	0.0318 (12)	0.0503 (14)	0.0471 (14)	0.0094 (10)	0.0022 (10)	−0.0030 (11)
N1	0.0285 (12)	0.0389 (15)	0.0275 (12)	−0.0058 (11)	−0.0001 (9)	0.0010 (11)
N2	0.0286 (12)	0.0321 (13)	0.0240 (11)	−0.0032 (10)	0.0007 (9)	−0.0009 (10)
N3	0.0267 (12)	0.0288 (13)	0.0361 (13)	−0.0029 (10)	−0.0018 (9)	0.0050 (11)
N4	0.0266 (12)	0.0259 (13)	0.0336 (13)	−0.0005 (10)	−0.0013 (9)	0.0018 (10)
C0AA	0.0338 (16)	0.0421 (19)	0.0318 (15)	−0.0032 (14)	−0.0035 (12)	0.0075 (14)
C2	0.0345 (15)	0.055 (2)	0.0270 (14)	−0.0094 (15)	−0.0037 (12)	−0.0020 (15)
C3	0.0354 (16)	0.0444 (19)	0.0290 (15)	−0.0069 (14)	0.0037 (12)	−0.0073 (13)
C4	0.0331 (15)	0.0372 (16)	0.0258 (13)	−0.0052 (13)	−0.0004 (11)	−0.0007 (13)
C5	0.0332 (15)	0.0394 (18)	0.0280 (15)	−0.0034 (13)	0.0005 (12)	−0.0041 (13)
C6	0.0344 (16)	0.0326 (16)	0.0338 (15)	0.0020 (13)	0.0008 (12)	0.0037 (13)
C7	0.0280 (13)	0.0308 (16)	0.0282 (14)	0.0000 (12)	−0.0032 (11)	−0.0020 (11)
C8	0.0259 (14)	0.0281 (16)	0.0333 (15)	0.0029 (11)	−0.0011 (11)	−0.0044 (11)
C9	0.0304 (15)	0.0276 (14)	0.0333 (16)	−0.0002 (12)	−0.0040 (12)	0.0019 (12)
C10	0.0262 (13)	0.0356 (16)	0.0273 (13)	−0.0020 (12)	−0.0006 (11)	−0.0027 (12)
C11	0.0441 (18)	0.044 (2)	0.0451 (19)	0.0063 (16)	0.0116 (15)	−0.0095 (16)
C12	0.0326 (15)	0.0330 (16)	0.0337 (15)	0.0053 (13)	−0.0020 (12)	−0.0068 (12)
C13	0.0359 (15)	0.0263 (15)	0.0387 (16)	0.0031 (13)	−0.0018 (13)	0.0010 (13)
C14	0.0326 (16)	0.0265 (15)	0.0435 (17)	−0.0010 (12)	−0.0020 (12)	0.0064 (13)
C15	0.0298 (15)	0.0261 (15)	0.0437 (17)	0.0030 (12)	0.0007 (13)	0.0031 (13)
C16	0.0299 (15)	0.0245 (15)	0.0389 (16)	0.0005 (11)	−0.0055 (12)	0.0038 (12)
C17	0.0269 (14)	0.0290 (16)	0.0401 (16)	0.0022 (12)	−0.0029 (12)	−0.0008 (13)
C18	0.0313 (15)	0.0340 (17)	0.0369 (16)	−0.0019 (13)	−0.0020 (12)	0.0048 (13)
C19	0.0292 (14)	0.0316 (15)	0.0323 (15)	−0.0042 (12)	0.0028 (11)	0.0048 (12)
C20	0.0321 (15)	0.0352 (17)	0.0325 (15)	0.0010 (13)	0.0024 (12)	−0.0015 (13)
C21	0.0313 (14)	0.0359 (16)	0.0269 (14)	−0.0035 (13)	0.0009 (11)	0.0040 (13)
C22	0.0359 (17)	0.054 (2)	0.0422 (19)	0.0114 (16)	0.0030 (14)	0.0095 (16)
C23	0.0260 (14)	0.0335 (17)	0.0374 (16)	−0.0005 (12)	0.0064 (12)	0.0051 (13)
C24	0.0326 (16)	0.0390 (17)	0.0385 (17)	−0.0052 (13)	0.0093 (13)	−0.0031 (14)
C25	0.0305 (15)	0.0373 (17)	0.0298 (15)	−0.0070 (12)	−0.0001 (11)	0.0036 (12)

O1—C10	1.373 (3)	C7—C8	1.390 (4)
O1—C11	1.428 (4)	C7—C13	1.406 (4)
O2—C11	1.422 (4)	C8—H8	0.9300
O2—C12	1.377 (4)	C8—C9	1.397 (4)
O3—C21	1.377 (3)	C9—H9	0.9300
O3—C22	1.427 (4)	C9—C10	1.369 (4)
O4—C22	1.429 (4)	C10—C12	1.382 (5)
O4—C23	1.374 (4)	C11—H11A	0.9700
N1—C0AA	1.447 (4)	C11—H11B	0.9700
N1—C2	1.456 (4)	C12—C13	1.367 (4)
N1—C5	1.462 (4)	C13—H13	0.9300
N2—C3	1.458 (4)	C14—H14A	0.9700
N2—C4	1.457 (3)	C14—H14B	0.9700
N2—C6	1.460 (4)	C14—C15	1.513 (4)
N3—C0AA	1.449 (4)	C15—H15A	0.9700
N3—C14	1.460 (4)	C15—H15B	0.9700
N3—C17	1.459 (4)	C16—H16A	0.9700
N4—C15	1.455 (4)	C16—H16B	0.9700
N4—C16	1.464 (4)	C16—C17	1.505 (4)
N4—C18	1.462 (4)	C17—H17A	0.9700
C0AA—H0AA	0.93 (3)	C17—H17B	0.9700
C0AA—H0AB	0.99 (4)	C18—H18A	0.9700
C2—H2A	0.9700	C18—H18B	0.9700
C2—H2B	0.9700	C18—C19	1.508 (4)
C2—C3	1.512 (4)	C19—C20	1.409 (4)
C3—H3A	0.9700	C19—C25	1.390 (4)
C3—H3B	0.9700	C20—H20	0.9300
C4—H4A	0.9700	C20—C21	1.367 (5)
C4—H4B	0.9700	C21—C23	1.382 (4)
C4—C5	1.515 (4)	C22—H22A	0.9700
C5—H5A	0.9700	C22—H22B	0.9700
C5—H5B	0.9700	C23—C24	1.366 (5)
C6—H6A	0.9700	C24—H24	0.9300
C6—H6B	0.9700	C24—C25	1.396 (5)
C6—C7	1.512 (4)	C25—H25	0.9300
C10—O1—C11	105.5 (3)	O1—C11—H11B	109.9
C12—O2—C11	105.8 (3)	O2—C11—O1	108.8 (2)
C21—O3—C22	105.4 (3)	O2—C11—H11A	109.9
C23—O4—C22	105.2 (2)	O2—C11—H11B	109.9
C0AA—N1—C2	111.8 (2)	H11A—C11—H11B	108.3
C0AA—N1—C5	111.4 (3)	O2—C12—C10	109.7 (3)
C2—N1—C5	109.8 (2)	C13—C12—O2	128.0 (3)
C3—N2—C6	111.1 (2)	C13—C12—C10	122.4 (3)
C4—N2—C3	108.9 (2)	C7—C13—H13	121.2
C4—N2—C6	111.9 (2)	C12—C13—C7	117.5 (3)
C0AA—N3—C14	110.1 (2)	C12—C13—H13	121.2
C0AA—N3—C17	111.3 (3)	N3—C14—H14A	109.5
C14—N3—C17	109.4 (2)	N3—C14—H14B	109.5
C15—N4—C16	108.3 (2)	N3—C14—C15	110.6 (3)
C15—N4—C18	112.3 (3)	H14A—C14—H14B	108.1
C16—N4—C18	110.7 (2)	C15—C14—H14A	109.5
N1—C0AA—N3	111.8 (3)	C15—C14—H14B	109.5
N1—C0AA—H0AA	106 (2)	N4—C15—C14	110.5 (3)
N1—C0AA—H0AB	110 (2)	N4—C15—H15A	109.5
N3—C0AA—H0AA	113 (2)	N4—C15—H15B	109.5
N3—C0AA—H0AB	109 (2)	C14—C15—H15A	109.5
H0AA—C0AA—H0AB	106 (3)	C14—C15—H15B	109.5
N1—C2—H2A	109.7	H15A—C15—H15B	108.1
N1—C2—H2B	109.7	N4—C16—H16A	109.6
N1—C2—C3	110.0 (3)	N4—C16—H16B	109.6
H2A—C2—H2B	108.2	N4—C16—C17	110.5 (2)
C3—C2—H2A	109.7	H16A—C16—H16B	108.1
C3—C2—H2B	109.7	C17—C16—H16A	109.6
N2—C3—C2	110.4 (3)	C17—C16—H16B	109.6
N2—C3—H3A	109.6	N3—C17—C16	110.7 (2)
N2—C3—H3B	109.6	N3—C17—H17A	109.5
C2—C3—H3A	109.6	N3—C17—H17B	109.5
C2—C3—H3B	109.6	C16—C17—H17A	109.5
H3A—C3—H3B	108.1	C16—C17—H17B	109.5
N2—C4—H4A	109.6	H17A—C17—H17B	108.1
N2—C4—H4B	109.6	N4—C18—H18A	109.2
N2—C4—C5	110.3 (2)	N4—C18—H18B	109.2
H4A—C4—H4B	108.1	N4—C18—C19	112.2 (2)
C5—C4—H4A	109.6	H18A—C18—H18B	107.9
C5—C4—H4B	109.6	C19—C18—H18A	109.2
N1—C5—C4	110.1 (3)	C19—C18—H18B	109.2
N1—C5—H5A	109.6	C20—C19—C18	119.6 (3)
N1—C5—H5B	109.6	C25—C19—C18	120.7 (3)
C4—C5—H5A	109.6	C25—C19—C20	119.6 (3)
C4—C5—H5B	109.6	C19—C20—H20	121.5
H5A—C5—H5B	108.2	C21—C20—C19	117.1 (3)
N2—C6—H6A	109.1	C21—C20—H20	121.5
N2—C6—H6B	109.1	O3—C21—C23	109.5 (3)
N2—C6—C7	112.4 (2)	C20—C21—O3	127.9 (3)
H6A—C6—H6B	107.9	C20—C21—C23	122.6 (3)
C7—C6—H6A	109.1	O3—C22—O4	108.4 (3)
C7—C6—H6B	109.1	O3—C22—H22A	110.0
C8—C7—C6	120.7 (3)	O3—C22—H22B	110.0
C8—C7—C13	119.4 (3)	O4—C22—H22A	110.0
C13—C7—C6	119.9 (3)	O4—C22—H22B	110.0
C7—C8—H8	118.7	H22A—C22—H22B	108.4
C7—C8—C9	122.5 (3)	O4—C23—C21	110.2 (3)
C9—C8—H8	118.7	C24—C23—O4	128.2 (3)
C8—C9—H9	121.7	C24—C23—C21	121.6 (3)
C10—C9—C8	116.6 (3)	C23—C24—H24	121.6
C10—C9—H9	121.7	C23—C24—C25	116.7 (3)
O1—C10—C12	110.2 (3)	C25—C24—H24	121.6
C9—C10—O1	128.2 (3)	C19—C25—C24	122.4 (3)
C9—C10—C12	121.6 (3)	C19—C25—H25	118.8
O1—C11—H11A	109.9	C24—C25—H25	118.8
O1—C10—C12—O2	−0.7 (4)	C9—C10—C12—C13	−0.8 (5)
O1—C10—C12—C13	179.1 (3)	C10—O1—C11—O2	0.5 (3)
O2—C12—C13—C7	179.6 (3)	C10—C12—C13—C7	−0.1 (4)
O3—C21—C23—O4	1.5 (4)	C11—O1—C10—C9	179.9 (3)
O3—C21—C23—C24	−177.3 (3)	C11—O1—C10—C12	0.1 (3)
O4—C23—C24—C25	179.0 (3)	C11—O2—C12—C10	1.0 (4)
N1—C2—C3—N2	59.5 (4)	C11—O2—C12—C13	−178.8 (3)
N2—C4—C5—N1	−59.0 (3)	C12—O2—C11—O1	−0.9 (4)
N2—C6—C7—C8	−42.1 (4)	C13—C7—C8—C9	0.1 (4)
N2—C6—C7—C13	140.0 (3)	C14—N3—C0AA—N1	−173.1 (3)
N3—C14—C15—N4	59.2 (3)	C14—N3—C17—C16	57.2 (3)
N4—C16—C17—N3	−59.4 (3)	C15—N4—C16—C17	59.5 (3)
N4—C18—C19—C20	−58.0 (4)	C15—N4—C18—C19	−58.6 (3)
N4—C18—C19—C25	118.7 (3)	C16—N4—C15—C14	−59.4 (3)
C0AA—N1—C2—C3	177.7 (3)	C16—N4—C18—C19	−179.8 (3)
C0AA—N1—C5—C4	−177.6 (3)	C17—N3—C0AA—N1	65.3 (3)
C0AA—N3—C14—C15	−179.6 (3)	C17—N3—C14—C15	−56.9 (3)
C0AA—N3—C17—C16	179.1 (2)	C18—N4—C15—C14	178.0 (2)
C2—N1—C0AA—N3	−164.6 (3)	C18—N4—C16—C17	−176.9 (2)
C2—N1—C5—C4	58.0 (3)	C18—C19—C20—C21	175.4 (3)
C3—N2—C4—C5	59.2 (3)	C18—C19—C25—C24	−175.0 (3)
C3—N2—C6—C7	−69.1 (3)	C19—C20—C21—O3	179.3 (3)
C4—N2—C3—C2	−59.5 (3)	C19—C20—C21—C23	−0.8 (5)
C4—N2—C6—C7	169.0 (3)	C20—C19—C25—C24	1.7 (5)
C5—N1—C0AA—N3	72.2 (3)	C20—C21—C23—O4	−178.4 (3)
C5—N1—C2—C3	−58.2 (4)	C20—C21—C23—C24	2.9 (5)
C6—N2—C3—C2	176.9 (2)	C21—O3—C22—O4	11.6 (4)
C6—N2—C4—C5	−177.7 (3)	C21—C23—C24—C25	−2.5 (5)
C6—C7—C8—C9	−177.8 (3)	C22—O3—C21—C20	171.8 (3)
C6—C7—C13—C12	178.3 (3)	C22—O3—C21—C23	−8.1 (3)
C7—C8—C9—C10	−0.9 (4)	C22—O4—C23—C21	5.7 (4)
C8—C7—C13—C12	0.4 (4)	C22—O4—C23—C24	−175.6 (3)
C8—C9—C10—O1	−178.6 (3)	C23—O4—C22—O3	−10.7 (4)
C8—C9—C10—C12	1.2 (4)	C23—C24—C25—C19	0.2 (5)
C9—C10—C12—O2	179.4 (3)	C25—C19—C20—C21	−1.4 (4)