Di-μ-iodo-1:2κ⁴I:I-diiodo-2κ²I-tris­(1,10-phenanthroline)-1κ²N,N′;2κ²N,N′-bis­muth(III)sodium(I)

The title compound, [BiNaI₄(C₁₂H₈N₂)₃], contains a bimetallic neutral cluster, with the metal atoms bridged by two iodide ions. The NaN₄I₂ coordination is irregular and the BiN₂I₄ coordination is distorted octa­hedral. A number of π–π stacking inter­actions involving the phenanthroline rings help to establish the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.012 Å
• R factor = 0.032
• wR factor = 0.077
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Bi1    -   I1      ..      11.97 su

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Bi1    -   I2      ..       6.00 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Bi1    -   I3      ..       9.51 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Bi1    -   I4      ..       7.23 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Bi1
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         12

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Di-µ-iodo-1:2κ⁴I:I-diiodo-2κ²I-tris(1,10'-phenanthroline)- 1κ²N,N';2κ²N,N'-bismuth(III)sodium(I)

Crystal data

[BiNaI4(C12H8N2)3]	F(000) = 2352
Mr = 1280.18	Dx = 2.236 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5357 reflections
a = 14.464 (2) Å	θ = 2.5–26.7°
b = 15.579 (2) Å	µ = 7.93 mm^−1
c = 17.467 (3) Å	T = 298 K
β = 104.906 (2)°	Block, orange–red
V = 3803.3 (10) Å^3	0.35 × 0.33 × 0.30 mm
Z = 4

Data collection

Siemens SMART CCD diffractometer	6685 independent reflections
Radiation source: fine-focus sealed tube	4689 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→16
Tmin = 0.078, Tmax = 0.093	k = −17→18
19705 measured reflections	l = −11→20

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.077	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0325P)^2 + 0.5298P] where P = (Fo^2 + 2Fc^2)/3
6685 reflections	(Δ/σ)max < 0.001
433 parameters	Δρmax = 1.17 e Å^−3
0 restraints	Δρmin = −1.14 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Bi1	0.477712 (19)	0.413381 (17)	0.238773 (15)	0.03602 (9)
Na1	0.1495 (2)	0.4162 (2)	0.26034 (16)	0.0549 (8)
I1	0.42869 (4)	0.40756 (4)	0.06019 (3)	0.05548 (15)
I2	0.32610 (3)	0.55115 (3)	0.24410 (3)	0.04653 (14)
I3	0.34994 (4)	0.28517 (3)	0.29081 (3)	0.04862 (15)
I4	0.64612 (5)	0.29385 (5)	0.26549 (4)	0.0865 (2)
N1	0.5654 (4)	0.4593 (4)	0.3772 (3)	0.0413 (15)
N2	0.5740 (4)	0.5527 (4)	0.2471 (4)	0.0453 (15)
N3	0.1286 (4)	0.3403 (4)	0.3803 (4)	0.0474 (16)
N4	0.1346 (4)	0.5148 (4)	0.3697 (4)	0.0492 (16)
N5	−0.0152 (4)	0.4552 (5)	0.1913 (4)	0.0563 (18)
N6	0.1045 (4)	0.3709 (4)	0.1189 (3)	0.0469 (16)
C1	0.5731 (6)	0.4101 (5)	0.4415 (4)	0.048 (2)
H1	0.5540	0.3530	0.4349	0.058*
C2	0.6089 (5)	0.4423 (6)	0.5180 (4)	0.055 (2)
H2	0.6174	0.4059	0.5614	0.066*
C3	0.6311 (5)	0.5255 (6)	0.5286 (5)	0.054 (2)
H3	0.6519	0.5475	0.5796	0.065*
C4	0.6232 (5)	0.5800 (5)	0.4630 (5)	0.048 (2)
C5	0.5946 (5)	0.5418 (4)	0.3878 (4)	0.0364 (17)
C6	0.5946 (5)	0.5921 (4)	0.3185 (5)	0.0420 (18)
C7	0.6190 (5)	0.6795 (5)	0.3277 (6)	0.056 (2)
C8	0.6208 (6)	0.7247 (6)	0.2596 (7)	0.070 (3)
H8	0.6345	0.7832	0.2628	0.084*
C9	0.6026 (6)	0.6844 (6)	0.1879 (6)	0.070 (3)
H9	0.6069	0.7140	0.1427	0.084*
C10	0.5774 (6)	0.5973 (5)	0.1839 (5)	0.059 (2)
H10	0.5626	0.5701	0.1348	0.071*
C11	0.6441 (6)	0.6687 (6)	0.4694 (6)	0.062 (2)
H11	0.6602	0.6944	0.5191	0.075*
C12	0.6412 (6)	0.7160 (6)	0.4058 (6)	0.065 (3)
H12	0.6538	0.7745	0.4119	0.078*
C13	0.1256 (6)	0.2558 (5)	0.3880 (6)	0.062 (2)
H13	0.1288	0.2220	0.3449	0.074*
C14	0.1179 (6)	0.2146 (6)	0.4570 (6)	0.065 (2)
H14	0.1152	0.1550	0.4594	0.078*
C15	0.1145 (6)	0.2631 (6)	0.5205 (6)	0.067 (3)
H15	0.1073	0.2369	0.5665	0.080*
C16	0.1218 (5)	0.3520 (5)	0.5174 (5)	0.050 (2)
C17	0.1265 (5)	0.3877 (5)	0.4453 (4)	0.0381 (17)
C18	0.1317 (5)	0.4805 (5)	0.4397 (4)	0.0406 (18)
C19	0.1360 (6)	0.5304 (6)	0.5066 (5)	0.057 (2)
C20	0.1395 (7)	0.6198 (6)	0.4979 (6)	0.072 (3)
H20	0.1415	0.6556	0.5410	0.086*
C21	0.1398 (7)	0.6538 (6)	0.4273 (7)	0.074 (3)
H21	0.1400	0.7129	0.4204	0.089*
C22	0.1399 (6)	0.5993 (6)	0.3657 (6)	0.066 (2)
H22	0.1440	0.6234	0.3180	0.079*
C23	0.1247 (7)	0.4045 (7)	0.5842 (5)	0.072 (3)
H23	0.1207	0.3798	0.6317	0.086*
C24	0.1334 (7)	0.4901 (7)	0.5788 (5)	0.075 (3)
H24	0.1379	0.5238	0.6236	0.090*
C25	−0.0761 (7)	0.4937 (7)	0.2250 (5)	0.082 (3)
H25	−0.0539	0.5082	0.2782	0.098*
C26	−0.1695 (6)	0.5141 (7)	0.1880 (5)	0.088 (3)
H26	−0.2095	0.5386	0.2160	0.105*
C27	−0.2012 (6)	0.4974 (6)	0.1098 (5)	0.072 (3)
H27	−0.2632	0.5121	0.0826	0.086*
C28	−0.1403 (6)	0.4579 (5)	0.0697 (5)	0.048 (2)
C29	−0.0477 (5)	0.4365 (4)	0.1134 (4)	0.0424 (18)
C30	0.0170 (5)	0.3948 (4)	0.0747 (4)	0.0368 (17)
C31	−0.0144 (5)	0.3795 (4)	−0.0072 (4)	0.0401 (18)
C32	0.0523 (6)	0.3408 (5)	−0.0441 (5)	0.053 (2)
H32	0.0357	0.3312	−0.0985	0.063*
C33	0.1407 (6)	0.3180 (5)	0.0010 (5)	0.055 (2)
H33	0.1851	0.2921	−0.0217	0.066*
C34	0.1625 (6)	0.3348 (5)	0.0817 (5)	0.058 (2)
H34	0.2229	0.3191	0.1119	0.070*
C35	−0.1684 (6)	0.4409 (5)	−0.0132 (5)	0.053 (2)
H35	−0.2299	0.4552	−0.0421	0.064*
C36	−0.1080 (6)	0.4048 (4)	−0.0499 (4)	0.048 (2)
H36	−0.1274	0.3961	−0.1044	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Bi1	0.03831 (16)	0.03966 (16)	0.02954 (15)	0.00096 (12)	0.00774 (11)	−0.00082 (13)
Na1	0.0480 (18)	0.083 (2)	0.0316 (16)	0.0045 (15)	0.0066 (14)	−0.0005 (16)
I1	0.0661 (4)	0.0664 (4)	0.0344 (3)	0.0070 (3)	0.0136 (3)	0.0024 (3)
I2	0.0462 (3)	0.0472 (3)	0.0463 (3)	0.0086 (2)	0.0120 (2)	0.0066 (3)
I3	0.0565 (3)	0.0437 (3)	0.0454 (3)	−0.0046 (2)	0.0126 (3)	0.0043 (2)
I4	0.0756 (4)	0.1149 (6)	0.0669 (4)	0.0495 (4)	0.0144 (4)	−0.0088 (4)
N1	0.048 (4)	0.045 (4)	0.030 (3)	−0.001 (3)	0.008 (3)	−0.001 (3)
N2	0.039 (4)	0.051 (4)	0.044 (4)	−0.007 (3)	0.008 (3)	0.003 (3)
N3	0.052 (4)	0.046 (4)	0.046 (4)	−0.002 (3)	0.016 (3)	−0.008 (3)
N4	0.051 (4)	0.047 (4)	0.050 (4)	−0.001 (3)	0.015 (3)	0.007 (3)
N5	0.043 (4)	0.093 (5)	0.033 (4)	0.004 (4)	0.011 (3)	−0.010 (4)
N6	0.044 (4)	0.063 (4)	0.035 (4)	0.003 (3)	0.011 (3)	0.000 (3)
C1	0.069 (5)	0.040 (4)	0.036 (4)	−0.001 (4)	0.015 (4)	0.000 (4)
C2	0.040 (5)	0.090 (7)	0.029 (4)	0.011 (4)	0.000 (4)	0.016 (5)
C3	0.045 (5)	0.072 (6)	0.038 (5)	0.007 (4)	−0.003 (4)	−0.017 (5)
C4	0.032 (4)	0.059 (5)	0.048 (5)	0.007 (4)	0.004 (4)	−0.017 (4)
C5	0.031 (4)	0.037 (4)	0.038 (4)	0.003 (3)	0.004 (3)	−0.002 (4)
C6	0.032 (4)	0.037 (4)	0.055 (5)	0.002 (3)	0.007 (4)	−0.007 (4)
C7	0.033 (4)	0.049 (5)	0.081 (7)	0.000 (4)	0.007 (4)	0.012 (5)
C8	0.043 (5)	0.051 (6)	0.113 (9)	−0.007 (4)	0.014 (6)	0.009 (6)
C9	0.046 (5)	0.077 (7)	0.085 (7)	−0.008 (5)	0.012 (5)	0.045 (6)
C10	0.051 (5)	0.068 (6)	0.060 (6)	−0.011 (4)	0.019 (4)	0.014 (5)
C11	0.050 (5)	0.066 (6)	0.067 (6)	−0.001 (4)	0.008 (5)	−0.029 (5)
C12	0.046 (5)	0.047 (5)	0.091 (8)	−0.008 (4)	−0.002 (5)	−0.017 (6)
C13	0.057 (5)	0.048 (6)	0.079 (7)	0.001 (4)	0.014 (5)	−0.014 (5)
C14	0.064 (6)	0.049 (6)	0.076 (7)	−0.003 (4)	0.008 (5)	0.012 (5)
C15	0.053 (5)	0.088 (7)	0.058 (6)	−0.012 (5)	0.011 (5)	0.020 (6)
C16	0.044 (5)	0.051 (5)	0.052 (5)	−0.008 (4)	0.011 (4)	0.010 (4)
C17	0.029 (4)	0.047 (5)	0.038 (4)	−0.001 (3)	0.008 (3)	−0.001 (4)
C18	0.037 (4)	0.047 (5)	0.042 (5)	0.005 (3)	0.018 (4)	−0.001 (4)
C19	0.055 (5)	0.060 (6)	0.061 (6)	0.001 (4)	0.024 (5)	−0.011 (5)
C20	0.085 (7)	0.052 (6)	0.089 (8)	−0.007 (5)	0.040 (6)	−0.032 (6)
C21	0.080 (7)	0.044 (6)	0.110 (9)	0.004 (5)	0.046 (7)	0.002 (6)
C22	0.066 (6)	0.057 (6)	0.079 (7)	0.006 (5)	0.025 (5)	0.015 (5)
C23	0.085 (7)	0.091 (8)	0.046 (5)	−0.004 (6)	0.032 (5)	−0.004 (6)
C24	0.096 (8)	0.087 (7)	0.050 (6)	−0.011 (6)	0.032 (5)	−0.029 (6)
C25	0.074 (7)	0.139 (9)	0.033 (5)	0.014 (6)	0.014 (5)	−0.013 (6)
C26	0.052 (6)	0.159 (10)	0.047 (6)	0.025 (6)	0.005 (5)	−0.004 (7)
C27	0.050 (5)	0.099 (7)	0.061 (6)	0.023 (5)	0.004 (5)	0.010 (6)
C28	0.052 (5)	0.044 (5)	0.044 (5)	0.007 (4)	0.005 (4)	0.005 (4)
C29	0.041 (4)	0.048 (5)	0.035 (4)	−0.009 (3)	0.003 (4)	0.004 (4)
C30	0.043 (4)	0.030 (4)	0.038 (4)	0.001 (3)	0.012 (4)	0.001 (3)
C31	0.047 (5)	0.032 (4)	0.036 (4)	−0.009 (3)	0.002 (4)	−0.005 (3)
C32	0.064 (6)	0.049 (5)	0.038 (5)	0.002 (4)	0.001 (4)	−0.008 (4)
C33	0.059 (5)	0.063 (6)	0.044 (5)	0.009 (4)	0.013 (4)	−0.009 (4)
C34	0.046 (5)	0.075 (6)	0.049 (5)	0.007 (4)	0.003 (4)	−0.008 (5)
C35	0.050 (5)	0.047 (5)	0.049 (5)	0.013 (4)	−0.011 (4)	0.004 (4)
C36	0.056 (5)	0.043 (5)	0.039 (4)	−0.004 (4)	−0.001 (4)	−0.002 (4)

Geometric parameters (Å, º)

Bi1—N1	2.528 (6)	C11—H11	0.9300
Bi1—N2	2.563 (6)	C12—H12	0.9300
Bi1—I4	3.0056 (7)	C13—C14	1.396 (11)
Bi1—I3	3.0159 (6)	C13—H13	0.9300
Bi1—I1	3.0171 (7)	C14—C15	1.354 (12)
Bi1—I2	3.0869 (6)	C14—H14	0.9300
Na1—N5	2.453 (7)	C15—C16	1.391 (11)
Na1—N6	2.490 (6)	C15—H15	0.9300
Na1—N3	2.492 (7)	C16—C17	1.393 (10)
Na1—N4	2.503 (7)	C16—C23	1.417 (11)
Na1—I2	3.376 (3)	C17—C18	1.452 (10)
Na1—I3	3.473 (3)	C18—C19	1.392 (10)
N1—C1	1.339 (8)	C19—C20	1.404 (11)
N1—C5	1.350 (8)	C19—C24	1.417 (12)
N2—C10	1.317 (9)	C20—C21	1.342 (12)
N2—C6	1.354 (9)	C20—H20	0.9300
N3—C13	1.324 (9)	C21—C22	1.370 (12)
N3—C17	1.362 (8)	C21—H21	0.9300
N4—C22	1.322 (9)	C22—H22	0.9300
N4—C18	1.345 (9)	C23—C24	1.346 (11)
N5—C25	1.322 (10)	C23—H23	0.9300
N5—C29	1.353 (9)	C24—H24	0.9300
N6—C34	1.312 (9)	C25—C26	1.377 (12)
N6—C30	1.354 (8)	C25—H25	0.9300
C1—C2	1.396 (10)	C26—C27	1.348 (11)
C1—H1	0.9300	C26—H26	0.9300
C2—C3	1.338 (10)	C27—C28	1.401 (11)
C2—H2	0.9300	C27—H27	0.9300
C3—C4	1.406 (10)	C28—C29	1.400 (9)
C3—H3	0.9300	C28—C35	1.425 (10)
C4—C5	1.405 (9)	C29—C30	1.442 (10)
C4—C11	1.413 (10)	C30—C31	1.405 (9)
C5—C6	1.441 (10)	C31—C32	1.424 (10)
C6—C7	1.406 (10)	C31—C36	1.424 (10)
C7—C8	1.390 (12)	C32—C33	1.366 (10)
C7—C12	1.436 (12)	C32—H32	0.9300
C8—C9	1.365 (12)	C33—C34	1.388 (10)
C8—H8	0.9300	C33—H33	0.9300
C9—C10	1.401 (11)	C34—H34	0.9300
C9—H9	0.9300	C35—C36	1.334 (10)
C10—H10	0.9300	C35—H35	0.9300
C11—C12	1.324 (11)	C36—H36	0.9300
N1—Bi1—N2	64.82 (19)	C9—C10—H10	118.8
N1—Bi1—I4	80.77 (13)	C12—C11—C4	121.2 (8)
N2—Bi1—I4	96.25 (13)	C12—C11—H11	119.4
N1—Bi1—I3	95.44 (13)	C4—C11—H11	119.4
N2—Bi1—I3	155.52 (14)	C11—C12—C7	121.8 (8)
I4—Bi1—I3	94.47 (2)	C11—C12—H12	119.1
N1—Bi1—I1	157.54 (14)	C7—C12—H12	119.1
N2—Bi1—I1	93.65 (14)	N3—C13—C14	123.9 (8)
I4—Bi1—I1	96.169 (18)	N3—C13—H13	118.1
I3—Bi1—I1	107.003 (17)	C14—C13—H13	118.1
N1—Bi1—I2	87.71 (13)	C15—C14—C13	118.6 (8)
N2—Bi1—I2	77.85 (13)	C15—C14—H14	120.7
I4—Bi1—I2	168.439 (19)	C13—C14—H14	120.7
I3—Bi1—I2	87.493 (19)	C14—C15—C16	120.3 (9)
I1—Bi1—I2	94.140 (16)	C14—C15—H15	119.9
N5—Na1—N6	67.0 (2)	C16—C15—H15	119.9
N5—Na1—N3	102.6 (2)	C15—C16—C17	117.1 (8)
N6—Na1—N3	130.0 (2)	C15—C16—C23	121.9 (8)
N5—Na1—N4	87.7 (2)	C17—C16—C23	121.0 (7)
N6—Na1—N4	151.6 (2)	N3—C17—C16	123.6 (7)
N3—Na1—N4	66.2 (2)	N3—C17—C18	118.1 (6)
N5—Na1—I2	117.67 (19)	C16—C17—C18	118.3 (7)
N6—Na1—I2	95.94 (17)	N4—C18—C19	122.5 (7)
N3—Na1—I2	128.64 (17)	N4—C18—C17	118.1 (7)
N4—Na1—I2	84.12 (16)	C19—C18—C17	119.4 (7)
N5—Na1—I3	152.56 (19)	C18—C19—C20	117.2 (8)
N6—Na1—I3	88.88 (16)	C18—C19—C24	119.7 (8)
N3—Na1—I3	82.47 (16)	C20—C19—C24	123.1 (9)
N4—Na1—I3	118.43 (17)	C21—C20—C19	119.9 (9)
I2—Na1—I3	76.06 (6)	C21—C20—H20	120.0
Bi1—I2—Na1	97.37 (5)	C19—C20—H20	120.0
Bi1—I3—Na1	96.69 (5)	C20—C21—C22	118.6 (9)
C1—N1—C5	118.3 (6)	C20—C21—H21	120.7
C1—N1—Bi1	123.5 (5)	C22—C21—H21	120.7
C5—N1—Bi1	117.5 (4)	N4—C22—C21	124.3 (9)
C10—N2—C6	119.2 (7)	N4—C22—H22	117.8
C10—N2—Bi1	122.5 (5)	C21—C22—H22	117.8
C6—N2—Bi1	115.0 (5)	C24—C23—C16	119.9 (8)
C13—N3—C17	116.5 (7)	C24—C23—H23	120.1
C13—N3—Na1	124.8 (6)	C16—C23—H23	120.1
C17—N3—Na1	118.5 (5)	C23—C24—C19	121.7 (8)
C22—N4—C18	117.3 (7)	C23—C24—H24	119.2
C22—N4—Na1	123.6 (6)	C19—C24—H24	119.2
C18—N4—Na1	118.6 (5)	N5—C25—C26	125.6 (8)
C25—N5—C29	116.5 (7)	N5—C25—H25	117.2
C25—N5—Na1	124.6 (5)	C26—C25—H25	117.2
C29—N5—Na1	118.9 (5)	C27—C26—C25	117.9 (9)
C34—N6—C30	117.3 (6)	C27—C26—H26	121.1
C34—N6—Na1	125.1 (5)	C25—C26—H26	121.1
C30—N6—Na1	117.1 (5)	C26—C27—C28	119.8 (8)
N1—C1—C2	121.8 (7)	C26—C27—H27	120.1
N1—C1—H1	119.1	C28—C27—H27	120.1
C2—C1—H1	119.1	C27—C28—C29	117.9 (7)
C3—C2—C1	119.8 (8)	C27—C28—C35	122.6 (7)
C3—C2—H2	120.1	C29—C28—C35	119.5 (7)
C1—C2—H2	120.1	N5—C29—C28	122.2 (7)
C2—C3—C4	120.4 (7)	N5—C29—C30	117.9 (6)
C2—C3—H3	119.8	C28—C29—C30	119.8 (7)
C4—C3—H3	119.8	N6—C30—C31	122.9 (6)
C5—C4—C3	116.7 (7)	N6—C30—C29	118.7 (6)
C5—C4—C11	119.6 (8)	C31—C30—C29	118.3 (6)
C3—C4—C11	123.7 (8)	C30—C31—C32	117.0 (6)
N1—C5—C4	122.5 (7)	C30—C31—C36	120.1 (7)
N1—C5—C6	118.0 (6)	C32—C31—C36	122.9 (7)
C4—C5—C6	119.4 (7)	C33—C32—C31	119.4 (7)
N2—C6—C7	122.2 (8)	C33—C32—H32	120.3
N2—C6—C5	118.7 (6)	C31—C32—H32	120.3
C7—C6—C5	119.0 (7)	C32—C33—C34	118.1 (8)
C8—C7—C6	117.0 (9)	C32—C33—H33	120.9
C8—C7—C12	124.3 (8)	C34—C33—H33	120.9
C6—C7—C12	118.7 (8)	N6—C34—C33	125.2 (7)
C9—C8—C7	120.7 (8)	N6—C34—H34	117.4
C9—C8—H8	119.6	C33—C34—H34	117.4
C7—C8—H8	119.6	C36—C35—C28	121.1 (7)
C8—C9—C10	118.5 (8)	C36—C35—H35	119.4
C8—C9—H9	120.7	C28—C35—H35	119.4
C10—C9—H9	120.7	C35—C36—C31	121.1 (7)
N2—C10—C9	122.3 (9)	C35—C36—H36	119.5
N2—C10—H10	118.8	C31—C36—H36	119.5