Poly[tetra-kis[μ(2)-1,3-bis-(4-pyrid-yl)propane-κN:N']dichloridobis(phenyl-acetato)dimanganese(II)].

In the title compound, [Mn(2)(C(8)H(7)O(2))(2)Cl(2)(C(13)H(14)N(2))(4)](n), the two Mn(II) atoms lie on inversion centers and are connected by the N-heterocyclic ligands into a wave-like lamellar framework structure. One Mn(II) atom is covalently bonded to two Cl atoms and the other to two benzyl-acetate anions; both Mn atoms show distorted octahedral coordinations.

Related literature

For general background to the use of poly-pyridyl ligand linkers such as 4,4′-bipyridine in the rational design and assembly of coordination polymers, see: Biradha et al. (2006 ▶). For related structures, see: Carlucci et al. (2002 ▶).

Experimental

Crystal data

[Mn2(C8H7O2)2Cl2(C13H14N2)4]

M = 1244.10

Triclinic,

a = 9.5594 (5) Å

b = 13.0091 (6) Å

c = 13.8484 (6) Å

α = 69.202 (4)°

β = 86.318 (4)°

γ = 69.910 (5)°

V = 1508.74 (13) Å3

Z = 1

Mo Kα radiation

μ = 0.56 mm−1

T = 293 K

0.48 × 0.46 × 0.23 mm

Data collection

Oxford Diffraction Xcalibur (Atlas Gemini ultra) diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.77, T max = 0.88

10180 measured reflections

5303 independent reflections

4041 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.069

S = 0.96

5303 reflections

383 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810003466/ng2721sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003466/ng2721Isup2.hkl

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

[Mn2(C8H7O2)2Cl2(C13H14N2)4]	Z = 1
Mr = 1244.10	F(000) = 650
Triclinic, P1	Dx = 1.369 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5594 (5) Å	Cell parameters from 5358 reflections
b = 13.0091 (6) Å	θ = 3.3–29.3°
c = 13.8484 (6) Å	µ = 0.56 mm−1
α = 69.202 (4)°	T = 293 K
β = 86.318 (4)°	Block, yellow
γ = 69.910 (5)°	0.48 × 0.46 × 0.23 mm
V = 1508.74 (13) Å3

Oxford Diffraction Xcalibur (Atlas Gemini ultra) diffractometer	5303 independent reflections
Radiation source: fine-focus sealed tube	4041 reflections with I > 2σ(I)
graphite	Rint = 0.021
Detector resolution: 10.3592 pixels mm-1	θmax = 25.0°, θmin = 3.4°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −13→15
Tmin = 0.77, Tmax = 0.88	l = −16→16
10180 measured reflections

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)] = 0.030	H-atom parameters constrained
wR(F2) = 0.069	w = 1/[σ2(Fo2) + (0.0355P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max < 0.001
5303 reflections	Δρmax = 0.23 e Å−3
383 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0064 (8)

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.

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
Mn1	1.0000	1.0000	0.5000	0.02534 (11)
Mn2	0.5000	0.5000	0.0000	0.02969 (12)
Cl	0.34313 (5)	0.44105 (5)	0.14744 (4)	0.04018 (14)
O1	0.75819 (12)	1.08965 (11)	0.46913 (9)	0.0362 (3)
O2	0.64269 (15)	1.08883 (14)	0.33545 (10)	0.0522 (4)
N1	1.00849 (15)	0.85804 (12)	0.42979 (11)	0.0288 (3)
N2	0.69038 (16)	0.45962 (13)	0.12058 (11)	0.0312 (4)
N3	1.05314 (16)	1.09985 (13)	0.33750 (11)	0.0299 (3)
N4	1.40150 (16)	0.69381 (14)	−0.00685 (12)	0.0352 (4)
C1	1.1512 (2)	0.71106 (18)	0.36191 (16)	0.0417 (5)
H1	1.2449	0.6678	0.3479	0.050*
C2	1.1387 (2)	0.79193 (18)	0.40728 (15)	0.0396 (5)
H2	1.2256	0.8012	0.4232	0.047*
C3	0.8877 (2)	0.84106 (17)	0.40593 (15)	0.0383 (5)
H3	0.7952	0.8851	0.4207	0.046*
C4	0.8926 (2)	0.76112 (18)	0.36018 (16)	0.0412 (5)
H4	0.8043	0.7531	0.3450	0.049*
C5	1.0260 (2)	0.69363 (16)	0.33697 (14)	0.0313 (4)
C6	1.0345 (2)	0.60283 (17)	0.29095 (15)	0.0380 (5)
H6B	1.1264	0.5864	0.2560	0.046*
H6A	0.9517	0.6335	0.2398	0.046*
C7	1.0295 (2)	0.49008 (16)	0.37315 (14)	0.0334 (4)
H7A	0.9340	0.5064	0.4039	0.040*
H7B	1.1066	0.4643	0.4273	0.040*
C8	1.0510 (2)	0.38992 (16)	0.33360 (14)	0.0324 (4)
H8B	1.1438	0.3762	0.2993	0.039*
H8A	1.0597	0.3191	0.3923	0.039*
C9	0.92566 (19)	0.41373 (15)	0.25951 (13)	0.0282 (4)
C10	0.9306 (2)	0.46458 (17)	0.15395 (14)	0.0349 (5)
H10	1.0132	0.4847	0.1270	0.042*
C11	0.8136 (2)	0.48548 (17)	0.08854 (14)	0.0357 (5)
H11	0.8204	0.5197	0.0178	0.043*
C12	0.6865 (2)	0.40978 (17)	0.22292 (15)	0.0379 (5)
H12	0.6029	0.3901	0.2480	0.045*
C13	0.7992 (2)	0.38592 (17)	0.29348 (14)	0.0368 (5)
H13	0.7904	0.3511	0.3639	0.044*
C14	1.0025 (2)	1.17152 (17)	0.15429 (14)	0.0367 (5)
H14	0.9354	1.1924	0.0991	0.044*
C15	0.9625 (2)	1.13025 (16)	0.25450 (14)	0.0339 (4)
H15	0.8686	1.1232	0.2649	0.041*
C16	1.1850 (2)	1.11445 (17)	0.31863 (15)	0.0354 (5)
H16	1.2483	1.0968	0.3749	0.043*
C17	1.2331 (2)	1.15408 (17)	0.22097 (15)	0.0391 (5)
H17	1.3266	1.1620	0.2126	0.047*
C18	1.1416 (2)	1.18203 (16)	0.13546 (15)	0.0352 (5)
C19	1.1965 (3)	1.21582 (18)	0.02808 (16)	0.0487 (6)
H19B	1.2622	1.2595	0.0242	0.058*
H19A	1.1122	1.2661	−0.0217	0.058*
C20	1.2812 (2)	1.10655 (19)	0.00013 (17)	0.0507 (6)
H20B	1.3367	1.1287	−0.0602	0.061*
H20A	1.3523	1.0496	0.0570	0.061*
C21	1.1775 (3)	1.0502 (2)	−0.02233 (18)	0.0550 (6)
H21A	1.1016	1.0501	0.0277	0.066*
H21B	1.1275	1.0973	−0.0905	0.066*
C22	1.2571 (2)	0.92665 (19)	−0.01826 (16)	0.0416 (5)
C23	1.3214 (2)	0.89998 (18)	−0.10331 (15)	0.0417 (5)
H23	1.3170	0.9596	−0.1662	0.050*
C24	1.3917 (2)	0.78443 (18)	−0.09375 (15)	0.0365 (5)
H24	1.4348	0.7688	−0.1514	0.044*
C25	1.3406 (2)	0.71987 (19)	0.07506 (15)	0.0462 (5)
H25	1.3463	0.6586	0.1370	0.055*
C26	1.2703 (2)	0.8323 (2)	0.07211 (17)	0.0516 (6)
H26	1.2310	0.8454	0.1316	0.062*
C27	0.64387 (19)	1.11445 (16)	0.41277 (14)	0.0309 (4)
C28	0.4906 (2)	1.1779 (2)	0.44208 (17)	0.0562 (6)
H28B	0.4395	1.2429	0.3804	0.067*
H28A	0.4351	1.1245	0.4604	0.067*
C29	0.47920 (19)	1.22539 (19)	0.52763 (16)	0.0391 (5)
C30	0.5024 (2)	1.1515 (2)	0.62991 (18)	0.0489 (6)
H30	0.5273	1.0713	0.6462	0.059*
C31	0.4885 (2)	1.1967 (3)	0.70858 (19)	0.0643 (7)
H31	0.5078	1.1462	0.7772	0.077*
C32	0.4469 (3)	1.3141 (3)	0.6860 (3)	0.0713 (9)
H32	0.4356	1.3440	0.7390	0.086*
C33	0.4220 (3)	1.3873 (3)	0.5859 (3)	0.0703 (8)
H33	0.3929	1.4677	0.5704	0.084*
C34	0.4393 (2)	1.3440 (2)	0.50720 (19)	0.0544 (6)
H34	0.4239	1.3955	0.4389	0.065*

	U11	U22	U33	U12	U13	U23
Mn1	0.0254 (2)	0.0287 (2)	0.0267 (2)	−0.00973 (17)	0.00331 (16)	−0.01524 (19)
Mn2	0.0266 (2)	0.0352 (2)	0.0289 (2)	−0.01084 (18)	0.00248 (17)	−0.0132 (2)
Cl	0.0320 (3)	0.0543 (3)	0.0350 (3)	−0.0170 (2)	0.0077 (2)	−0.0155 (3)
O1	0.0243 (6)	0.0468 (9)	0.0401 (8)	−0.0071 (6)	−0.0008 (6)	−0.0228 (7)
O2	0.0481 (8)	0.0678 (11)	0.0427 (9)	−0.0074 (8)	−0.0051 (7)	−0.0328 (9)
N1	0.0308 (8)	0.0281 (9)	0.0316 (9)	−0.0120 (7)	0.0024 (7)	−0.0137 (8)
N2	0.0319 (8)	0.0328 (9)	0.0306 (9)	−0.0118 (7)	0.0016 (7)	−0.0126 (8)
N3	0.0316 (8)	0.0299 (9)	0.0323 (9)	−0.0111 (7)	0.0041 (7)	−0.0157 (8)
N4	0.0369 (9)	0.0394 (10)	0.0313 (9)	−0.0116 (8)	0.0017 (7)	−0.0162 (9)
C1	0.0298 (10)	0.0485 (13)	0.0595 (14)	−0.0130 (10)	0.0121 (10)	−0.0356 (12)
C2	0.0279 (10)	0.0485 (13)	0.0573 (13)	−0.0175 (10)	0.0071 (9)	−0.0326 (12)
C3	0.0276 (10)	0.0374 (12)	0.0560 (13)	−0.0078 (9)	0.0054 (9)	−0.0272 (11)
C4	0.0290 (10)	0.0444 (13)	0.0621 (14)	−0.0134 (9)	−0.0010 (9)	−0.0313 (12)
C5	0.0374 (10)	0.0305 (11)	0.0317 (10)	−0.0139 (9)	0.0035 (8)	−0.0156 (9)
C6	0.0477 (12)	0.0397 (12)	0.0384 (12)	−0.0200 (10)	0.0090 (9)	−0.0237 (11)
C7	0.0343 (10)	0.0407 (12)	0.0330 (11)	−0.0143 (9)	0.0011 (8)	−0.0205 (10)
C8	0.0366 (10)	0.0281 (11)	0.0325 (10)	−0.0093 (9)	−0.0032 (8)	−0.0119 (9)
C9	0.0333 (10)	0.0217 (10)	0.0327 (11)	−0.0074 (8)	−0.0003 (8)	−0.0146 (9)
C10	0.0369 (11)	0.0421 (12)	0.0340 (11)	−0.0220 (10)	0.0049 (9)	−0.0153 (10)
C11	0.0419 (11)	0.0412 (12)	0.0268 (10)	−0.0196 (10)	0.0027 (9)	−0.0101 (10)
C12	0.0340 (11)	0.0458 (13)	0.0376 (12)	−0.0199 (10)	0.0063 (9)	−0.0138 (11)
C13	0.0422 (11)	0.0447 (13)	0.0263 (10)	−0.0192 (10)	0.0035 (9)	−0.0118 (10)
C14	0.0438 (12)	0.0343 (11)	0.0313 (11)	−0.0092 (9)	0.0007 (9)	−0.0144 (10)
C15	0.0292 (10)	0.0374 (12)	0.0375 (12)	−0.0110 (9)	0.0036 (9)	−0.0168 (10)
C16	0.0346 (10)	0.0369 (12)	0.0409 (12)	−0.0142 (9)	0.0028 (9)	−0.0191 (10)
C17	0.0376 (11)	0.0361 (12)	0.0499 (13)	−0.0185 (10)	0.0108 (10)	−0.0182 (11)
C18	0.0480 (12)	0.0213 (10)	0.0385 (11)	−0.0126 (9)	0.0128 (10)	−0.0141 (10)
C19	0.0703 (15)	0.0333 (12)	0.0449 (13)	−0.0235 (11)	0.0222 (11)	−0.0144 (11)
C20	0.0639 (14)	0.0472 (14)	0.0469 (13)	−0.0228 (12)	0.0251 (11)	−0.0234 (12)
C21	0.0581 (14)	0.0504 (15)	0.0564 (15)	−0.0063 (12)	0.0010 (11)	−0.0305 (13)
C22	0.0422 (11)	0.0436 (13)	0.0434 (13)	−0.0093 (10)	0.0005 (10)	−0.0253 (12)
C23	0.0496 (12)	0.0405 (13)	0.0356 (11)	−0.0136 (10)	0.0021 (9)	−0.0160 (11)
C24	0.0412 (11)	0.0404 (12)	0.0309 (11)	−0.0135 (10)	0.0042 (9)	−0.0170 (11)
C25	0.0618 (14)	0.0475 (14)	0.0290 (11)	−0.0181 (11)	0.0048 (10)	−0.0142 (11)
C26	0.0678 (15)	0.0540 (15)	0.0366 (13)	−0.0148 (12)	0.0114 (11)	−0.0276 (13)
C27	0.0320 (10)	0.0283 (11)	0.0331 (11)	−0.0114 (8)	0.0018 (9)	−0.0107 (9)
C28	0.0266 (11)	0.0852 (18)	0.0659 (15)	−0.0084 (11)	0.0010 (10)	−0.0474 (15)
C29	0.0187 (9)	0.0516 (14)	0.0517 (14)	−0.0080 (9)	0.0041 (9)	−0.0280 (12)
C30	0.0305 (11)	0.0498 (14)	0.0603 (15)	−0.0047 (10)	0.0035 (10)	−0.0213 (13)
C31	0.0351 (12)	0.100 (2)	0.0500 (14)	−0.0094 (14)	0.0028 (11)	−0.0306 (16)
C32	0.0425 (14)	0.112 (3)	0.094 (2)	−0.0270 (16)	0.0149 (14)	−0.078 (2)
C33	0.0529 (15)	0.0646 (19)	0.119 (3)	−0.0260 (14)	0.0207 (16)	−0.059 (2)
C34	0.0408 (12)	0.0527 (15)	0.0654 (16)	−0.0159 (11)	0.0111 (11)	−0.0176 (14)

Mn1—O1	2.1925 (11)	C11—H11	0.9300
Mn1—O1i	2.1925 (11)	C12—C13	1.380 (2)
Mn1—N3i	2.2891 (15)	C12—H12	0.9300
Mn1—N3	2.2891 (15)	C13—H13	0.9300
Mn1—N1	2.3504 (12)	C14—C15	1.380 (3)
Mn1—N1i	2.3505 (12)	C14—C18	1.382 (3)
Mn2—N4ii	2.3374 (15)	C14—H14	0.9300
Mn2—N4iii	2.3374 (15)	C15—H15	0.9300
Mn2—N2	2.3425 (14)	C16—C17	1.376 (3)
Mn2—N2iv	2.3425 (14)	C16—H16	0.9300
Mn2—Cliv	2.5081 (5)	C17—C18	1.381 (3)
Mn2—Cl	2.5081 (5)	C17—H17	0.9300
O1—C27	1.263 (2)	C18—C19	1.508 (3)
O2—C27	1.2309 (19)	C19—C20	1.545 (3)
N1—C3	1.330 (2)	C19—H19B	0.9700
N1—C2	1.338 (2)	C19—H19A	0.9700
N2—C12	1.337 (2)	C20—C21	1.522 (3)
N2—C11	1.340 (2)	C20—H20B	0.9700
N3—C16	1.334 (2)	C20—H20A	0.9700
N3—C15	1.341 (2)	C21—C22	1.506 (3)
N4—C24	1.333 (2)	C21—H21A	0.9700
N4—C25	1.339 (2)	C21—H21B	0.9700
N4—Mn2v	2.3374 (15)	C22—C26	1.382 (3)
C1—C2	1.374 (2)	C22—C23	1.391 (2)
C1—C5	1.378 (2)	C23—C24	1.380 (3)
C1—H1	0.9300	C23—H23	0.9300
C2—H2	0.9300	C24—H24	0.9300
C3—C4	1.384 (2)	C25—C26	1.371 (3)
C3—H3	0.9300	C25—H25	0.9300
C4—C5	1.371 (2)	C26—H26	0.9300
C4—H4	0.9300	C27—C28	1.524 (3)
C5—C6	1.507 (2)	C28—C29	1.501 (2)
C6—C7	1.518 (3)	C28—H28B	0.9700
C6—H6B	0.9700	C28—H28A	0.9700
C6—H6A	0.9700	C29—C30	1.381 (3)
C7—C8	1.532 (2)	C29—C34	1.381 (3)
C7—H7A	0.9700	C30—C31	1.391 (3)
C7—H7B	0.9700	C30—H30	0.9300
C8—C9	1.504 (2)	C31—C32	1.360 (4)
C8—H8B	0.9700	C31—H31	0.9300
C8—H8A	0.9700	C32—C33	1.354 (4)
C9—C10	1.379 (2)	C32—H32	0.9300
C9—C13	1.385 (2)	C33—C34	1.372 (3)
C10—C11	1.376 (2)	C33—H33	0.9300
C10—H10	0.9300	C34—H34	0.9300
O1—Mn1—O1i	180.00 (8)	N2—C11—H11	118.0
O1—Mn1—N3i	86.18 (5)	C10—C11—H11	118.0
O1i—Mn1—N3i	93.82 (5)	N2—C12—C13	123.72 (16)
O1—Mn1—N3	93.82 (5)	N2—C12—H12	118.1
O1i—Mn1—N3	86.18 (5)	C13—C12—H12	118.1
N3i—Mn1—N3	180.00 (7)	C12—C13—C9	120.04 (17)
O1—Mn1—N1	94.53 (4)	C12—C13—H13	120.0
O1i—Mn1—N1	85.47 (4)	C9—C13—H13	120.0
N3i—Mn1—N1	95.63 (5)	C15—C14—C18	120.39 (17)
N3—Mn1—N1	84.37 (5)	C15—C14—H14	119.8
O1—Mn1—N1i	85.47 (4)	C18—C14—H14	119.8
O1i—Mn1—N1i	94.53 (4)	N3—C15—C14	122.83 (16)
N3i—Mn1—N1i	84.37 (5)	N3—C15—H15	118.6
N3—Mn1—N1i	95.63 (5)	C14—C15—H15	118.6
N1—Mn1—N1i	179.999 (2)	N3—C16—C17	124.04 (17)
N4ii—Mn2—N4iii	180.0	N3—C16—H16	118.0
N4ii—Mn2—N2	89.48 (5)	C17—C16—H16	118.0
N4iii—Mn2—N2	90.52 (5)	C16—C17—C18	119.62 (16)
N4ii—Mn2—N2iv	90.52 (5)	C16—C17—H17	120.2
N4iii—Mn2—N2iv	89.48 (5)	C18—C17—H17	120.2
N2—Mn2—N2iv	180.0	C17—C18—C14	116.66 (17)
N4ii—Mn2—Cliv	90.26 (4)	C17—C18—C19	120.68 (17)
N4iii—Mn2—Cliv	89.74 (4)	C14—C18—C19	122.58 (18)
N2—Mn2—Cliv	91.14 (4)	C18—C19—C20	111.16 (17)
N2iv—Mn2—Cliv	88.86 (4)	C18—C19—H19B	109.4
N4ii—Mn2—Cl	89.74 (4)	C20—C19—H19B	109.4
N4iii—Mn2—Cl	90.26 (4)	C18—C19—H19A	109.4
N2—Mn2—Cl	88.86 (4)	C20—C19—H19A	109.4
N2iv—Mn2—Cl	91.14 (4)	H19B—C19—H19A	108.0
Cliv—Mn2—Cl	180.0	C21—C20—C19	112.69 (18)
C27—O1—Mn1	146.73 (11)	C21—C20—H20B	109.1
C3—N1—C2	115.84 (14)	C19—C20—H20B	109.1
C3—N1—Mn1	123.51 (11)	C21—C20—H20A	109.1
C2—N1—Mn1	120.59 (10)	C19—C20—H20A	109.1
C12—N2—C11	115.74 (15)	H20B—C20—H20A	107.8
C12—N2—Mn2	124.04 (11)	C22—C21—C20	113.31 (18)
C11—N2—Mn2	120.22 (12)	C22—C21—H21A	108.9
C16—N3—C15	116.38 (15)	C20—C21—H21A	108.9
C16—N3—Mn1	121.77 (12)	C22—C21—H21B	108.9
C15—N3—Mn1	121.06 (11)	C20—C21—H21B	108.9
C24—N4—C25	116.24 (17)	H21A—C21—H21B	107.7
C24—N4—Mn2v	122.37 (11)	C26—C22—C23	116.10 (19)
C25—N4—Mn2v	121.18 (14)	C26—C22—C21	120.97 (17)
C2—C1—C5	120.49 (17)	C23—C22—C21	122.9 (2)
C2—C1—H1	119.8	C24—C23—C22	119.6 (2)
C5—C1—H1	119.8	C24—C23—H23	120.2
N1—C2—C1	123.68 (16)	C22—C23—H23	120.2
N1—C2—H2	118.2	N4—C24—C23	124.00 (17)
C1—C2—H2	118.2	N4—C24—H24	118.0
N1—C3—C4	123.36 (16)	C23—C24—H24	118.0
N1—C3—H3	118.3	N4—C25—C26	123.3 (2)
C4—C3—H3	118.3	N4—C25—H25	118.4
C5—C4—C3	120.74 (16)	C26—C25—H25	118.4
C5—C4—H4	119.6	C25—C26—C22	120.80 (18)
C3—C4—H4	119.6	C25—C26—H26	119.6
C4—C5—C1	115.90 (15)	C22—C26—H26	119.6
C4—C5—C6	121.64 (15)	O2—C27—O1	125.80 (17)
C1—C5—C6	122.42 (16)	O2—C27—C28	114.92 (16)
C5—C6—C7	111.65 (14)	O1—C27—C28	119.24 (15)
C5—C6—H6B	109.3	C29—C28—C27	119.64 (15)
C7—C6—H6B	109.3	C29—C28—H28B	107.4
C5—C6—H6A	109.3	C27—C28—H28B	107.4
C7—C6—H6A	109.3	C29—C28—H28A	107.4
H6B—C6—H6A	108.0	C27—C28—H28A	107.4
C6—C7—C8	114.66 (14)	H28B—C28—H28A	106.9
C6—C7—H7A	108.6	C30—C29—C34	117.88 (19)
C8—C7—H7A	108.6	C30—C29—C28	120.6 (2)
C6—C7—H7B	108.6	C34—C29—C28	121.4 (2)
C8—C7—H7B	108.6	C29—C30—C31	120.1 (2)
H7A—C7—H7B	107.6	C29—C30—H30	119.9
C9—C8—C7	113.34 (15)	C31—C30—H30	119.9
C9—C8—H8B	108.9	C32—C31—C30	120.6 (3)
C7—C8—H8B	108.9	C32—C31—H31	119.7
C9—C8—H8A	108.9	C30—C31—H31	119.7
C7—C8—H8A	108.9	C33—C32—C31	119.6 (2)
H8B—C8—H8A	107.7	C33—C32—H32	120.2
C10—C9—C13	116.48 (16)	C31—C32—H32	120.2
C10—C9—C8	121.62 (15)	C32—C33—C34	120.6 (2)
C13—C9—C8	121.89 (16)	C32—C33—H33	119.7
C11—C10—C9	120.01 (16)	C34—C33—H33	119.7
C11—C10—H10	120.0	C33—C34—C29	121.1 (2)
C9—C10—H10	120.0	C33—C34—H34	119.4
N2—C11—C10	124.01 (17)	C29—C34—H34	119.4