{(1R,2R)-N,N'-Bis[2-(N-methyl-anilino)benzyl-idene]cyclo-hexane-1,2-diamine-κN,N'}dichloridoiron(II).

In the title compound, [FeCl(2)(C(34)H(36)N(4))], the Fe(II) ion is coordinated by two Cl atoms and by two N atoms from a (1R,2R)-N,N'-bis[2-(N-methyl-anilino)benzyl-idene]cyclo-hexane-1,2-diamine ligand in a distorted tetra-hedral geometry. The mol-ecule has approximate C(2) point symmetry. The dihedral angles between the phenyl and benzene rings on either side of the ligand are 64.56 (14) and 65.61 (13)°.

Related literature

For background to chiral diimine-based catalysts, see: Li et al. (1993 ▶). For the application of n class="Chemical">iron complexes in enanti­o­selective oxidation, see: Muthupandi et al. (2009 ▶). For related structures, see: Yan et al. (2009 ▶); Chaggar et al. (2003 ▶); Sui-Seng et al. (2008 ▶, 2009 ▶).

Experimental

Crystal data

[FeCl2(C34H36N4)]

M = 627.42

Orthorhombic,

a = 13.040 (3) Å

b = 13.228 (3) Å

c = 20.602 (4) Å

V = 3553.6 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.60 mm−1

T = 298 K

0.24 × 0.21 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Rigaku, 1995 ▶) T min = 0.866, T max = 0.897

33683 measured reflections

8057 independent reflections

6495 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.093

S = 1.03

8057 reflections

370 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 3578 Friedel pairs

Flack parameter: 0.010 (12)

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536811053773/lh5395sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811053773/lh5395Isup2.hkl

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

C34H36Cl2FeN4	Dx = 1.173 Mg m−3
Mr = 627.42	Melting point: not measured K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 26371 reflections
a = 13.040 (3) Å	θ = 3.1–27.5°
b = 13.228 (3) Å	µ = 0.60 mm−1
c = 20.602 (4) Å	T = 298 K
V = 3553.6 (12) Å3	Block, brown
Z = 4	0.24 × 0.21 × 0.18 mm
F(000) = 1312

Rigaku RAXIS-RAPID diffractometer	8057 independent reflections
Radiation source: fine-focus sealed tube	6495 reflections with I > 2σ(I)
graphite	Rint = 0.043
Detector resolution: 0 pixels mm-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −16→14
Absorption correction: multi-scan ABSCOR, Rigaku (1995).	k = −17→16
Tmin = 0.866, Tmax = 0.897	l = −26→26
33683 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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.0508P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
8057 reflections	Δρmax = 0.18 e Å−3
370 parameters	Δρmin = −0.18 e Å−3
1 restraint	Absolute structure: Flack (1983) 3578 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.010 (12)

Experimental. 1H NMR (300 MHz, CDCl3, 298 K) δ (p.p.m.): 8.27 (s, 2H, CH=N), 7.89 (d, 2H, J = 9.0 Hz, ArH), 7.37 (t, 2H, J = 9.0 Hz, ArH), 7.21–7.06 (m, 10H, ArH), 6.74 (t, 2H, J = 9.0 Hz), 6.56 (d, J = 9.0 Hz, 2H), 3.27 (m, 2H, NCHCH2), 1.03 (s, 6H, NCH3), 1.75–1.37 (m, 8H,CH2).

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
Fe1	0.56631 (2)	0.42985 (2)	0.460486 (15)	0.04245 (9)
Cl1	0.67993 (5)	0.48063 (5)	0.53572 (3)	0.06293 (17)
Cl2	0.46852 (6)	0.54282 (5)	0.40817 (3)	0.06693 (18)
N1	0.47736 (13)	0.30362 (14)	0.49010 (8)	0.0402 (4)
N2	0.63149 (13)	0.31650 (13)	0.40093 (8)	0.0394 (4)
N3	0.45490 (16)	0.25188 (18)	0.67965 (10)	0.0584 (5)
N4	0.67088 (15)	0.36560 (17)	0.21363 (10)	0.0566 (5)
C1	0.48832 (16)	0.21737 (16)	0.44434 (10)	0.0394 (5)
H1	0.4472	0.2329	0.4058	0.090*
C2	0.60131 (15)	0.21292 (15)	0.42297 (10)	0.0374 (4)
H2	0.6419	0.1980	0.4619	0.090*
C3	0.62008 (19)	0.12705 (19)	0.37537 (12)	0.0506 (6)
H3A	0.6927	0.1233	0.3653	0.090*
H3B	0.5833	0.1404	0.3353	0.090*
C4	0.5846 (2)	0.02654 (18)	0.40358 (13)	0.0597 (6)
H4A	0.5955	−0.0267	0.3720	0.090*
H4B	0.6248	0.0108	0.4419	0.090*
C5	0.4727 (2)	0.0309 (2)	0.42142 (13)	0.0638 (7)
H5A	0.4519	−0.0333	0.4400	0.090*
H5B	0.4321	0.0424	0.3827	0.090*
C6	0.45287 (17)	0.11521 (17)	0.47001 (12)	0.0518 (5)
H6A	0.4887	0.1003	0.5101	0.090*
H6B	0.3801	0.1183	0.4795	0.090*
C7	0.43205 (15)	0.29153 (16)	0.54426 (10)	0.0430 (4)
H7	0.4067	0.2276	0.5540	0.090*
C8	0.41725 (16)	0.37204 (19)	0.59235 (11)	0.0490 (5)
C9	0.42638 (18)	0.3503 (2)	0.65930 (11)	0.0530 (5)
C10	0.4029 (2)	0.4271 (3)	0.70306 (13)	0.0722 (8)
H10	0.4077	0.4143	0.7473	0.090*
C11	0.3730 (3)	0.5202 (3)	0.68277 (17)	0.0858 (10)
H11	0.3569	0.5695	0.7133	0.090*
C12	0.3661 (2)	0.5428 (2)	0.61802 (17)	0.0752 (8)
H12	0.3463	0.6069	0.6045	0.090*
C13	0.3893 (2)	0.4683 (2)	0.57297 (13)	0.0613 (7)
H13	0.3860	0.4834	0.5289	0.090*
C14	0.54177 (18)	0.2032 (2)	0.65208 (11)	0.0534 (6)
C15	0.62253 (18)	0.2577 (2)	0.62606 (12)	0.0556 (6)
H15	0.6210	0.3280	0.6266	0.090*
C16	0.7052 (2)	0.2078 (3)	0.59926 (15)	0.0754 (9)
H16	0.7585	0.2449	0.5810	0.090*
C17	0.7097 (3)	0.1044 (4)	0.59921 (17)	0.0973 (12)
H17	0.7665	0.0717	0.5818	0.090*
C18	0.6305 (4)	0.0490 (3)	0.62469 (18)	0.0957 (12)
H18	0.6334	−0.0212	0.6241	0.090*
C19	0.5460 (3)	0.0972 (2)	0.65142 (15)	0.0754 (8)
H19	0.4924	0.0595	0.6688	0.090*
C20	0.4310 (2)	0.2244 (3)	0.74653 (14)	0.0802 (9)
H20A	0.4540	0.1567	0.7548	0.090*
H20B	0.3582	0.2283	0.7532	0.090*
H20C	0.4650	0.2702	0.7756	0.090*
C21	0.67820 (17)	0.32672 (17)	0.34710 (10)	0.0428 (5)
H21	0.6876	0.2690	0.3220	0.090*
C22	0.71833 (16)	0.42188 (18)	0.32147 (11)	0.0449 (5)
C23	0.72020 (16)	0.43670 (19)	0.25358 (11)	0.0480 (5)
C24	0.77257 (19)	0.5197 (2)	0.22871 (13)	0.0561 (6)
H24	0.7750	0.5299	0.1841	0.090*
C25	0.82048 (19)	0.5866 (2)	0.26927 (15)	0.0632 (7)
H25	0.8567	0.6405	0.2516	0.090*
C26	0.81626 (18)	0.5757 (2)	0.33613 (14)	0.0595 (6)
H26	0.8470	0.6231	0.3632	0.090*
C27	0.76565 (18)	0.4933 (2)	0.36163 (12)	0.0526 (6)
H27	0.7629	0.4851	0.4064	0.090*
C28	0.56550 (18)	0.34379 (18)	0.22359 (10)	0.0486 (5)
C29	0.5025 (2)	0.4097 (2)	0.25693 (13)	0.0566 (6)
H29	0.5288	0.4705	0.2724	0.090*
C30	0.3998 (2)	0.3856 (3)	0.26745 (15)	0.0700 (8)
H30	0.3583	0.4297	0.2909	0.090*
C31	0.3597 (2)	0.2980 (3)	0.24368 (17)	0.0771 (9)
H31	0.2909	0.2826	0.2502	0.090*
C32	0.4222 (3)	0.2325 (3)	0.20982 (18)	0.0840 (9)
H32	0.3950	0.1726	0.1936	0.090*
C33	0.5235 (2)	0.2540 (2)	0.19977 (16)	0.0716 (8)
H33	0.5646	0.2088	0.1770	0.090*
C34	0.7164 (2)	0.3395 (2)	0.15165 (12)	0.0630 (7)
H34A	0.6741	0.2906	0.1300	0.090*
H34B	0.7835	0.3115	0.1586	0.090*
H34C	0.7219	0.3990	0.1253	0.090*

	U11	U22	U33	U12	U13	U23
Fe1	0.04618 (16)	0.04382 (15)	0.03736 (16)	−0.00461 (14)	0.00017 (14)	−0.00167 (13)
Cl1	0.0632 (3)	0.0743 (4)	0.0513 (3)	−0.0149 (3)	−0.0097 (3)	−0.0089 (3)
Cl2	0.0795 (4)	0.0616 (4)	0.0597 (4)	0.0074 (3)	−0.0054 (3)	0.0132 (3)
N1	0.0368 (8)	0.0509 (9)	0.0329 (9)	−0.0012 (8)	−0.0005 (7)	−0.0017 (7)
N2	0.0381 (9)	0.0468 (9)	0.0332 (9)	−0.0033 (8)	0.0024 (7)	0.0020 (8)
N3	0.0528 (12)	0.0846 (12)	0.0379 (10)	−0.0104 (11)	0.0079 (9)	0.0083 (10)
N4	0.0578 (11)	0.0741 (13)	0.0378 (10)	−0.0103 (11)	0.0137 (9)	−0.0027 (10)
C1	0.0380 (10)	0.0486 (11)	0.0316 (11)	−0.0053 (9)	−0.0035 (8)	−0.0027 (8)
C2	0.0372 (10)	0.0438 (11)	0.0311 (11)	−0.0044 (9)	−0.0003 (8)	0.0032 (8)
C3	0.0572 (14)	0.0499 (13)	0.0448 (13)	0.0004 (11)	0.0026 (11)	−0.0015 (10)
C4	0.0765 (18)	0.0461 (12)	0.0565 (14)	−0.0036 (13)	0.0015 (13)	−0.0069 (11)
C5	0.0762 (17)	0.0527 (13)	0.0625 (17)	−0.0221 (13)	0.0004 (13)	−0.0053 (12)
C6	0.0529 (13)	0.0542 (12)	0.0482 (13)	−0.0153 (11)	0.0038 (11)	0.0003 (10)
C7	0.0361 (9)	0.0568 (11)	0.0361 (11)	−0.0058 (10)	0.0008 (10)	0.0039 (9)
C8	0.0379 (11)	0.0658 (14)	0.0432 (12)	0.0008 (11)	0.0059 (10)	−0.0051 (11)
C9	0.0391 (11)	0.0815 (13)	0.0385 (12)	−0.0058 (12)	0.0052 (10)	−0.0067 (11)
C10	0.0643 (16)	0.109 (2)	0.0431 (14)	−0.0046 (18)	0.0051 (11)	−0.0205 (16)
C11	0.077 (2)	0.106 (3)	0.074 (2)	0.020 (2)	0.0004 (16)	−0.043 (2)
C12	0.0716 (18)	0.0737 (19)	0.080 (2)	0.0170 (15)	−0.0006 (15)	−0.0148 (16)
C13	0.0557 (14)	0.0734 (16)	0.0549 (15)	0.0050 (13)	0.0040 (12)	−0.0078 (13)
C14	0.0522 (13)	0.0743 (15)	0.0335 (12)	−0.0071 (13)	−0.0066 (10)	0.0073 (11)
C15	0.0426 (12)	0.0819 (17)	0.0422 (13)	−0.0105 (12)	−0.0049 (10)	0.0031 (12)
C16	0.0499 (15)	0.122 (3)	0.0544 (17)	0.0069 (18)	−0.0055 (13)	0.0040 (18)
C17	0.093 (2)	0.143 (4)	0.0558 (19)	0.050 (3)	−0.0125 (18)	0.003 (2)
C18	0.132 (3)	0.089 (2)	0.067 (2)	0.035 (2)	−0.018 (2)	0.0068 (18)
C19	0.100 (2)	0.0679 (17)	0.0582 (17)	−0.0066 (17)	−0.0133 (16)	0.0156 (13)
C20	0.0707 (17)	0.124 (3)	0.0462 (15)	−0.0200 (19)	0.0112 (14)	0.0218 (16)
C21	0.0436 (11)	0.0499 (11)	0.0348 (11)	−0.0003 (10)	0.0023 (9)	0.0023 (9)
C22	0.0402 (11)	0.0511 (12)	0.0432 (12)	−0.0032 (11)	0.0079 (9)	0.0032 (11)
C23	0.0410 (10)	0.0596 (13)	0.0434 (12)	0.0028 (11)	0.0097 (9)	0.0013 (11)
C24	0.0546 (13)	0.0602 (15)	0.0535 (15)	−0.0043 (12)	0.0110 (11)	0.0140 (12)
C25	0.0465 (12)	0.0663 (16)	0.0767 (19)	−0.0040 (13)	0.0122 (12)	0.0160 (14)
C26	0.0462 (12)	0.0576 (13)	0.0748 (18)	−0.0101 (13)	0.0001 (12)	−0.0028 (14)
C27	0.0442 (12)	0.0638 (14)	0.0499 (14)	−0.0023 (11)	0.0044 (10)	0.0017 (12)
C28	0.0535 (12)	0.0562 (12)	0.0360 (11)	−0.0035 (12)	0.0073 (10)	−0.0001 (9)
C29	0.0557 (13)	0.0644 (15)	0.0495 (14)	−0.0069 (12)	0.0031 (11)	−0.0041 (12)
C30	0.0477 (13)	0.094 (2)	0.0688 (19)	−0.0002 (15)	0.0054 (13)	−0.0116 (16)
C31	0.0597 (16)	0.092 (2)	0.079 (2)	−0.0274 (16)	0.0053 (15)	−0.0091 (18)
C32	0.075 (2)	0.084 (2)	0.093 (2)	−0.0273 (18)	0.0032 (19)	−0.0236 (18)
C33	0.0713 (18)	0.0674 (16)	0.076 (2)	−0.0087 (15)	0.0074 (15)	−0.0168 (15)
C34	0.0601 (14)	0.0901 (19)	0.0388 (13)	0.0146 (15)	0.0097 (11)	0.0029 (13)

Fe1—N2	2.1157 (18)	C13—H13	0.9300
Fe1—N1	2.1227 (18)	C14—C15	1.384 (4)
Fe1—Cl2	2.2408 (8)	C14—C19	1.403 (4)
Fe1—Cl1	2.2468 (7)	C15—C16	1.379 (4)
N1—C7	1.273 (3)	C15—H15	0.9300
N1—C1	1.487 (3)	C16—C17	1.369 (6)
N2—C21	1.272 (3)	C16—H16	0.9300
N2—C2	1.496 (3)	C17—C18	1.370 (6)
N3—C9	1.417 (3)	C17—H17	0.9300
N3—C14	1.422 (3)	C18—C19	1.387 (5)
N3—C20	1.459 (3)	C18—H18	0.9300
N4—C23	1.406 (3)	C19—H19	0.9300
N4—C28	1.419 (3)	C20—H20A	0.9600
N4—C34	1.450 (3)	C20—H20B	0.9600
C1—C6	1.523 (3)	C20—H20C	0.9600
C1—C2	1.539 (3)	C21—C22	1.462 (3)
C1—H1	0.9800	C21—H21	0.9300
C2—C3	1.520 (3)	C22—C27	1.400 (4)
C2—H2	0.9800	C22—C23	1.413 (3)
C3—C4	1.523 (4)	C23—C24	1.391 (3)
C3—H3A	0.9700	C24—C25	1.368 (4)
C3—H3B	0.9700	C24—H24	0.9300
C4—C5	1.505 (4)	C25—C26	1.386 (4)
C4—H4A	0.9700	C25—H25	0.9300
C4—H4B	0.9700	C26—C27	1.378 (4)
C5—C6	1.521 (4)	C26—H26	0.9300
C5—H5A	0.9700	C27—H27	0.9300
C5—H5B	0.9700	C28—C29	1.381 (3)
C6—H6A	0.9700	C28—C33	1.396 (4)
C6—H6B	0.9700	C29—C30	1.394 (4)
C7—C8	1.467 (3)	C29—H29	0.9300
C7—H7	0.9300	C30—C31	1.362 (5)
C8—C13	1.384 (4)	C30—H30	0.9300
C8—C9	1.414 (3)	C31—C32	1.379 (5)
C9—C10	1.393 (4)	C31—H31	0.9300
C10—C11	1.358 (5)	C32—C33	1.368 (4)
C10—H10	0.9300	C32—H32	0.9300
C11—C12	1.370 (5)	C33—H33	0.9300
C11—H11	0.9300	C34—H34A	0.9600
C12—C13	1.386 (4)	C34—H34B	0.9600
C12—H12	0.9300	C34—H34C	0.9600
N2—Fe1—N1	80.14 (7)	C8—C13—C12	121.2 (3)
N2—Fe1—Cl2	114.98 (5)	C8—C13—H13	119.4
N1—Fe1—Cl2	110.60 (5)	C12—C13—H13	119.4
N2—Fe1—Cl1	110.31 (5)	C15—C14—C19	119.2 (3)
N1—Fe1—Cl1	113.40 (5)	C15—C14—N3	121.7 (3)
Cl2—Fe1—Cl1	120.51 (3)	C19—C14—N3	119.2 (3)
C7—N1—C1	120.27 (18)	C16—C15—C14	120.0 (3)
C7—N1—Fe1	127.20 (15)	C16—C15—H15	120.0
C1—N1—Fe1	111.65 (12)	C14—C15—H15	120.0
C21—N2—C2	119.19 (18)	C17—C16—C15	120.8 (3)
C21—N2—Fe1	128.50 (15)	C17—C16—H16	119.6
C2—N2—Fe1	111.55 (12)	C15—C16—H16	119.6
C9—N3—C14	120.5 (2)	C16—C17—C18	120.1 (3)
C9—N3—C20	116.9 (2)	C16—C17—H17	119.9
C14—N3—C20	115.8 (2)	C18—C17—H17	120.0
C23—N4—C28	119.64 (18)	C17—C18—C19	120.3 (4)
C23—N4—C34	119.2 (2)	C17—C18—H18	119.8
C28—N4—C34	118.4 (2)	C19—C18—H18	119.8
N1—C1—C6	115.56 (17)	C18—C19—C14	119.6 (3)
N1—C1—C2	107.62 (16)	C18—C19—H19	120.2
C6—C1—C2	110.85 (18)	C14—C19—H19	120.2
N1—C1—H1	107.5	N3—C20—H20A	109.5
C6—C1—H1	107.5	N3—C20—H20B	109.5
C2—C1—H1	107.5	H20A—C20—H20B	109.5
N2—C2—C3	116.49 (17)	N3—C20—H20C	109.5
N2—C2—C1	107.68 (16)	H20A—C20—H20C	109.5
C3—C2—C1	111.54 (17)	H20B—C20—H20C	109.5
N2—C2—H2	106.9	N2—C21—C22	125.3 (2)
C3—C2—H2	106.9	N2—C21—H21	117.4
C1—C2—H2	106.9	C22—C21—H21	117.4
C2—C3—C4	110.92 (19)	C27—C22—C23	118.9 (2)
C2—C3—H3A	109.5	C27—C22—C21	121.7 (2)
C4—C3—H3A	109.5	C23—C22—C21	118.9 (2)
C2—C3—H3B	109.5	C24—C23—N4	122.5 (2)
C4—C3—H3B	109.5	C24—C23—C22	118.9 (2)
H3A—C3—H3B	108.0	N4—C23—C22	118.6 (2)
C5—C4—C3	110.7 (2)	C25—C24—C23	120.6 (2)
C5—C4—H4A	109.5	C25—C24—H24	119.7
C3—C4—H4A	109.5	C23—C24—H24	119.7
C5—C4—H4B	109.5	C24—C25—C26	121.5 (2)
C3—C4—H4B	109.5	C24—C25—H25	119.3
H4A—C4—H4B	108.1	C26—C25—H25	119.3
C4—C5—C6	110.7 (2)	C27—C26—C25	118.7 (2)
C4—C5—H5A	109.5	C27—C26—H26	120.7
C6—C5—H5A	109.5	C25—C26—H26	120.7
C4—C5—H5B	109.5	C26—C27—C22	121.3 (2)
C6—C5—H5B	109.5	C26—C27—H27	119.3
H5A—C5—H5B	108.1	C22—C27—H27	119.3
C5—C6—C1	111.74 (19)	C29—C28—C33	118.6 (2)
C5—C6—H6A	109.3	C29—C28—N4	121.3 (2)
C1—C6—H6A	109.3	C33—C28—N4	120.1 (2)
C5—C6—H6B	109.3	C28—C29—C30	120.3 (3)
C1—C6—H6B	109.3	C28—C29—H29	119.9
H6A—C6—H6B	107.9	C30—C29—H29	119.9
N1—C7—C8	124.2 (2)	C31—C30—C29	120.5 (3)
N1—C7—H7	117.9	C31—C30—H30	119.7
C8—C7—H7	117.9	C29—C30—H30	119.7
C13—C8—C9	119.4 (2)	C30—C31—C32	119.3 (3)
C13—C8—C7	120.5 (2)	C30—C31—H31	120.3
C9—C8—C7	120.0 (2)	C32—C31—H31	120.3
C10—C9—C8	117.7 (3)	C33—C32—C31	121.1 (3)
C10—C9—N3	122.4 (2)	C33—C32—H32	119.5
C8—C9—N3	119.9 (2)	C31—C32—H32	119.5
C11—C10—C9	121.7 (3)	C32—C33—C28	120.2 (3)
C11—C10—H10	119.1	C32—C33—H33	119.9
C9—C10—H10	119.1	C28—C33—H33	119.9
C10—C11—C12	121.1 (3)	N4—C34—H34A	109.5
C10—C11—H11	119.5	N4—C34—H34B	109.5
C12—C11—H11	119.5	H34A—C34—H34B	109.5
C11—C12—C13	118.9 (3)	N4—C34—H34C	109.5
C11—C12—H12	120.6	H34A—C34—H34C	109.5
C13—C12—H12	120.6	H34B—C34—H34C	109.5