(5,15-Dianthracen-9-yl-10,20-dihexyl­porphyrinato)nickel(II): a planar nickel(II) porphyrin

The title compound, [Ni(C₆₀H₅₂N₄)], is an example of a meso tetra­substituted nickel(II) porphyrin with both meso aryl and alkyl residues. The mol­ecule exhibits a planar macrocycle with an average deviation of the 24 macrocycle atoms from their least-squares plane (Δ24) of 0.01 Å and an average Ni—N bond length of 1.960 (2) Å. The Ni^II atom lies on a center of inversion. The structure presents a rare example for a planar nickel(II) porphyrin, as meso-substituted nickel(II) porphyrins with either only meso-aryl or with meso-alkyl residues typically exhibit a ruffled conformation.

Key indicators

• Single-crystal X-ray study
• T = 118 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.087
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C5H    --  C5I     ..       5.11 su
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          7
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.595         25
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          1

Alert level G
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          9

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

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

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S1. Comment

In continuation of studies on the conformational flexibility of porphyrins (Senge, 2006) the structure of the title compound was determined as an example for a meso substituted porphyrin with both meso alkyl and meso aryl subsitutents (Senge et al., 2010) and in relation to current synthetic studies on anthracenyl porphyrins (Volz & Schäffer, 1985; Davis et al., 2008; Sooambar et al., 2009).

The structure of (I), is shown in Fig. 1. The molecule exhibits a completely planar macrocycle with an average deviation of the 24 macrocycle atoms from their least-squares-plane (Δ24) of 0.01 Å and an average Ni—N bond length of 1.960 (2) Å. All geometrical parameters are typical for a planar nickel(II) porphyrin (Senge et al., 2000). No individual macrocycle atom was displaced more then 0.015 Å from the mean plane. Likewise, differences in bond angles and lenghts between the meso aryl and meso alkyl quadrants are minimal. The anthracenyl residues are almost orthogonal to the plane of the four nitrogen atoms (96.2°) similarly to the situation found in related zinc(II) systems with meso aryl residues (Sooambar et al., 2009). In the crystal packing there are no close contacts (not shown). The anthracene residues prevent π-stacking of the porphyrins and the hexyl side chains are oriented between neighboring anthracenyl substituents and hinder π-stacking as well.

The structure presents a rare example for a planar nickel(II) porphyrin. Typically, meso substituted nickel(II) porphyrins with only meso aryl residues (Fleischer et al., 1964; Hoard, 1973; Lee & Scheidt, 1987) and those with meso alkyl residues (Senge et al., 1999; Runge et al., 1999) exhibit a ruffled conformation. Only (5,10,15,20-tetramethylporphyrinato)nickel(II) exbihits an almost planar conformation as well (Gallucci et al., 1982).

Related literature

For the conformation of porphyrins, see: Senge (2006). For porphyrins with mixed meso substituents, see: Senge et al. (2010). For Ni(II) porphyrin structures, see: Fleischer et al. (1964);; Gallucci et al. (1982); Hoard (1973); Lee & Scheidt (1987); Senge et al. (1999, 2000) and Runge et al. (1999). For anthracenyl porphyrins see: Volz & Schäffer (1985); Davis et al. (2008); Sooambar et al. (2009). For the handling of the crystals, see: Hope (1994).

S2. Experimental

The compound was prepared via metallation of the respective free base porphyrin and crystallized via liquid diffusion of methanol into a solution of the porphyrin in methylene chloride. Crystals were handled as described by Hope (1994).

S3. Refinement

Hydrogen atoms were located in difference maps and refined using a standard riding model.

Computing details

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97 (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures

Fig. 1. : View of the molecular structure of I in the crystals. Thermal ellipsoids are drawn for 50% occupancy.

(5,15-Dianthracen-9-yl-10,20-dihexylporphyrinato)nickel(II)

Crystal data

[Ni(C60H52N4)]	Z = 1
Mr = 887.77	F(000) = 468
Triclinic, P1	Dx = 1.329 Mg m^−3
Hall symbol: -P 1	Melting point: n/d K
a = 7.797 (3) Å	Mo Kα radiation, λ = 0.71075 Å
b = 9.387 (3) Å	Cell parameters from 3864 reflections
c = 15.285 (5) Å	θ = 2.4–31.2°
α = 97.246 (6)°	µ = 0.48 mm^−1
β = 91.222 (4)°	T = 118 K
γ = 91.402 (6)°	Prism, red
V = 1109.1 (7) Å^3	0.50 × 0.20 × 0.05 mm

Data collection

Rigaku Saturn724 diffractometer	3233 reflections with I > 2σ(I)
Radiation source: Sealed Tube	Rint = 0.070
Graphite Monochromator monochromator	θmax = 25.0°, θmin = 3.0°
Detector resolution: 28.5714 pixels mm^-1	h = −9→9
dtprofit.ref scans	k = −11→11
17330 measured reflections	l = −18→18
3875 independent reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.087	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0371P)^2] where P = (Fo^2 + 2Fc^2)/3
3875 reflections	(Δ/σ)max < 0.001
296 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.40 e Å^−3
0 constraints

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
Ni	0.0000	0.5000	0.0000	0.01798 (12)
N21	0.1442 (2)	0.47152 (16)	0.10290 (10)	0.0185 (4)
N22	0.1822 (2)	0.62389 (16)	−0.03788 (10)	0.0192 (4)
C5	−0.0499 (3)	0.31349 (19)	0.17545 (13)	0.0185 (4)
C6	0.1022 (3)	0.3901 (2)	0.16960 (13)	0.0198 (5)
C7	0.2375 (3)	0.3969 (2)	0.23403 (13)	0.0247 (5)
H7A	0.2383	0.3500	0.2856	0.030*
C8	0.3643 (3)	0.4817 (2)	0.20886 (14)	0.0243 (5)
H8A	0.4707	0.5059	0.2391	0.029*
C9	0.3069 (3)	0.5284 (2)	0.12716 (13)	0.0194 (5)
C10	0.4031 (3)	0.6194 (2)	0.08102 (13)	0.0204 (5)
C11	0.3407 (3)	0.6617 (2)	0.00254 (13)	0.0197 (5)
C12	0.4362 (3)	0.7542 (2)	−0.04785 (14)	0.0244 (5)
H12A	0.5476	0.7949	−0.0337	0.029*
C13	0.3384 (3)	0.7725 (2)	−0.11872 (14)	0.0248 (5)
H13A	0.3677	0.8283	−0.1642	0.030*
C14	0.1820 (3)	0.69232 (19)	−0.11298 (13)	0.0190 (5)
C5A	−0.0738 (3)	0.2335 (2)	0.25355 (13)	0.0205 (5)
C5B	−0.0381 (3)	0.0855 (2)	0.24777 (14)	0.0230 (5)
C5C	0.0207 (3)	0.0055 (2)	0.16833 (15)	0.0263 (5)
H5CA	0.0405	0.0534	0.1181	0.032*
C5D	0.0488 (3)	−0.1376 (2)	0.16363 (16)	0.0334 (6)
H5DA	0.0880	−0.1884	0.1104	0.040*
C5E	0.0197 (3)	−0.2119 (2)	0.23800 (17)	0.0360 (6)
H5EA	0.0382	−0.3122	0.2338	0.043*
C5F	−0.0339 (3)	−0.1403 (2)	0.31441 (16)	0.0321 (6)
H5FA	−0.0517	−0.1913	0.3635	0.038*
C5G	−0.0645 (3)	0.0104 (2)	0.32312 (14)	0.0255 (5)
C5H	−0.1190 (3)	0.0864 (2)	0.40177 (14)	0.0276 (5)
H5HA	−0.1338	0.0367	0.4516	0.033*
C5I	−0.1523 (3)	0.2321 (2)	0.40970 (13)	0.0230 (5)
C5J	−0.2098 (3)	0.3101 (2)	0.48906 (14)	0.0318 (6)
H5JA	−0.2196	0.2628	0.5402	0.038*
C5K	−0.2508 (3)	0.4502 (2)	0.49355 (15)	0.0393 (6)
H5KA	−0.2877	0.5003	0.5475	0.047*
C5L	−0.2383 (3)	0.5230 (2)	0.41624 (15)	0.0347 (6)
H5LA	−0.2719	0.6200	0.4186	0.042*
C5M	−0.1797 (3)	0.4549 (2)	0.34139 (15)	0.0298 (5)
H5MA	−0.1677	0.5061	0.2920	0.036*
C5N	−0.1344 (3)	0.3070 (2)	0.33320 (13)	0.0230 (5)
C10A	0.5771 (3)	0.6803 (2)	0.11646 (13)	0.0235 (5)
H10A	0.6577	0.6781	0.0671	0.028*
H10B	0.6232	0.6189	0.1591	0.028*
C10B	0.5667 (3)	0.8359 (2)	0.16236 (13)	0.0265 (5)
H10C	0.6835	0.8805	0.1670	0.032*
H10D	0.4955	0.8913	0.1250	0.032*
C10C	0.4915 (3)	0.8477 (2)	0.25444 (14)	0.0279 (5)
H10E	0.5718	0.8051	0.2943	0.033*
H10F	0.3823	0.7909	0.2514	0.033*
C10D	0.4574 (3)	1.0030 (2)	0.29382 (14)	0.0287 (5)
H10G	0.5637	1.0622	0.2916	0.034*
H10H	0.3681	1.0425	0.2574	0.034*
C10E	0.4000 (3)	1.0138 (2)	0.38747 (15)	0.0356 (6)
H10I	0.4938	0.9824	0.4246	0.043*
H10J	0.3004	0.9473	0.3904	0.043*
C10F	0.3500 (3)	1.1641 (2)	0.42523 (14)	0.0316 (6)
H10K	0.3292	1.1666	0.4884	0.047*
H10L	0.2453	1.1900	0.3950	0.047*
H10M	0.4430	1.2326	0.4166	0.047*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni	0.0227 (2)	0.0162 (2)	0.0154 (2)	−0.00037 (16)	0.00200 (15)	0.00351 (15)
N21	0.0227 (10)	0.0156 (8)	0.0174 (9)	−0.0013 (7)	0.0034 (7)	0.0021 (7)
N22	0.0240 (10)	0.0184 (9)	0.0155 (9)	0.0016 (8)	0.0008 (7)	0.0030 (7)
C5	0.0243 (12)	0.0137 (10)	0.0171 (10)	−0.0003 (9)	0.0026 (9)	0.0004 (8)
C6	0.0279 (13)	0.0145 (10)	0.0170 (11)	0.0015 (9)	0.0004 (9)	0.0020 (8)
C7	0.0307 (13)	0.0231 (11)	0.0212 (11)	−0.0003 (10)	−0.0011 (10)	0.0069 (9)
C8	0.0244 (12)	0.0235 (11)	0.0252 (12)	−0.0005 (9)	−0.0043 (9)	0.0048 (9)
C9	0.0219 (12)	0.0161 (10)	0.0198 (11)	0.0005 (9)	0.0000 (9)	0.0005 (9)
C10	0.0215 (12)	0.0177 (10)	0.0211 (11)	0.0032 (9)	0.0025 (9)	−0.0015 (9)
C11	0.0208 (12)	0.0171 (10)	0.0204 (11)	−0.0007 (9)	0.0021 (9)	−0.0005 (9)
C12	0.0243 (12)	0.0245 (11)	0.0246 (12)	−0.0043 (9)	0.0021 (9)	0.0047 (9)
C13	0.0282 (13)	0.0248 (11)	0.0221 (11)	−0.0045 (10)	0.0024 (9)	0.0061 (9)
C14	0.0249 (12)	0.0138 (10)	0.0184 (10)	−0.0005 (9)	0.0027 (9)	0.0028 (8)
C5A	0.0206 (12)	0.0199 (11)	0.0209 (11)	−0.0033 (9)	−0.0013 (9)	0.0036 (9)
C5B	0.0215 (12)	0.0224 (11)	0.0254 (12)	−0.0028 (9)	−0.0011 (9)	0.0050 (9)
C5C	0.0235 (12)	0.0243 (12)	0.0312 (13)	−0.0006 (10)	0.0029 (10)	0.0029 (10)
C5D	0.0297 (14)	0.0295 (13)	0.0400 (14)	0.0025 (11)	0.0049 (11)	0.0001 (11)
C5E	0.0338 (15)	0.0204 (12)	0.0548 (17)	0.0030 (10)	0.0046 (12)	0.0073 (11)
C5F	0.0275 (14)	0.0275 (12)	0.0445 (15)	0.0023 (10)	0.0012 (11)	0.0166 (11)
C5G	0.0227 (12)	0.0242 (12)	0.0308 (12)	−0.0018 (9)	−0.0011 (10)	0.0088 (10)
C5H	0.0259 (13)	0.0333 (13)	0.0259 (12)	−0.0043 (10)	−0.0008 (10)	0.0135 (10)
C5I	0.0234 (12)	0.0244 (11)	0.0218 (11)	−0.0032 (9)	0.0020 (9)	0.0056 (9)
C5J	0.0353 (14)	0.0375 (14)	0.0232 (12)	−0.0075 (11)	0.0003 (10)	0.0075 (10)
C5K	0.0509 (17)	0.0376 (14)	0.0268 (13)	−0.0036 (12)	0.0092 (12)	−0.0069 (11)
C5L	0.0490 (17)	0.0188 (11)	0.0359 (14)	0.0024 (11)	0.0132 (12)	−0.0006 (10)
C5M	0.0370 (14)	0.0257 (12)	0.0282 (13)	−0.0016 (10)	0.0020 (10)	0.0090 (10)
C5N	0.0238 (12)	0.0220 (11)	0.0234 (11)	−0.0015 (9)	0.0003 (9)	0.0035 (9)
C10A	0.0212 (12)	0.0290 (12)	0.0209 (11)	−0.0013 (9)	0.0002 (9)	0.0059 (9)
C10B	0.0222 (12)	0.0306 (12)	0.0262 (12)	−0.0058 (10)	−0.0007 (10)	0.0035 (10)
C10C	0.0286 (13)	0.0284 (12)	0.0269 (12)	−0.0013 (10)	−0.0015 (10)	0.0048 (10)
C10D	0.0265 (13)	0.0316 (12)	0.0282 (12)	−0.0031 (10)	−0.0030 (10)	0.0057 (10)
C10E	0.0428 (16)	0.0354 (13)	0.0285 (13)	0.0020 (11)	0.0001 (11)	0.0033 (11)
C10F	0.0368 (15)	0.0288 (12)	0.0289 (13)	0.0039 (11)	0.0004 (11)	0.0019 (10)

Geometric parameters (Å, º)

Ni—N22	1.9570 (17)	C5E—H5EA	0.9500
Ni—N22^i	1.9570 (17)	C5F—C5G	1.430 (3)
Ni—N21^i	1.9632 (17)	C5F—H5FA	0.9500
Ni—N21	1.9632 (17)	C5G—C5H	1.399 (3)
N21—C6	1.389 (2)	C5H—C5I	1.389 (3)
N21—C9	1.389 (3)	C5H—H5HA	0.9500
N22—C14	1.384 (2)	C5I—C5J	1.423 (3)
N22—C11	1.388 (3)	C5I—C5N	1.446 (3)
C5—C6	1.382 (3)	C5J—C5K	1.354 (3)
C5—C14^i	1.385 (3)	C5J—H5JA	0.9500
C5—C5A	1.501 (3)	C5K—C5L	1.442 (3)
C6—C7	1.423 (3)	C5K—H5KA	0.9500
C7—C8	1.346 (3)	C5L—C5M	1.333 (3)
C7—H7A	0.9500	C5L—H5LA	0.9500
C8—C9	1.441 (3)	C5M—C5N	1.433 (3)
C8—H8A	0.9500	C5M—H5MA	0.9500
C9—C10	1.390 (3)	C10A—C10B	1.544 (3)
C10—C11	1.392 (3)	C10A—H10A	0.9900
C10—C10A	1.521 (3)	C10A—H10B	0.9900
C11—C12	1.436 (3)	C10B—C10C	1.529 (3)
C12—C13	1.343 (3)	C10B—H10C	0.9900
C12—H12A	0.9500	C10B—H10D	0.9900
C13—C14	1.427 (3)	C10C—C10D	1.538 (3)
C13—H13A	0.9500	C10C—H10E	0.9900
C14—C5^i	1.385 (3)	C10C—H10F	0.9900
C5A—C5B	1.416 (3)	C10D—C10E	1.501 (3)
C5A—C5N	1.417 (3)	C10D—H10G	0.9900
C5B—C5C	1.435 (3)	C10D—H10H	0.9900
C5B—C5G	1.440 (3)	C10E—C10F	1.518 (3)
C5C—C5D	1.359 (3)	C10E—H10I	0.9900
C5C—H5CA	0.9500	C10E—H10J	0.9900
C5D—C5E	1.426 (3)	C10F—H10K	0.9800
C5D—H5DA	0.9500	C10F—H10L	0.9800
C5E—C5F	1.352 (3)	C10F—H10M	0.9800
N22—Ni—N22^i	180.00 (8)	C5H—C5G—C5F	122.4 (2)
N22—Ni—N21^i	91.02 (7)	C5H—C5G—C5B	119.23 (19)
N22^i—Ni—N21^i	88.98 (7)	C5F—C5G—C5B	118.4 (2)
N22—Ni—N21	88.98 (7)	C5I—C5H—C5G	122.40 (19)
N22^i—Ni—N21	91.02 (7)	C5I—C5H—H5HA	118.8
N21^i—Ni—N21	180.00 (9)	C5G—C5H—H5HA	118.8
C6—N21—C9	104.27 (16)	C5H—C5I—C5J	122.86 (19)
C6—N21—Ni	126.74 (14)	C5H—C5I—C5N	118.78 (19)
C9—N21—Ni	128.98 (13)	C5J—C5I—C5N	118.31 (19)
C14—N22—C11	104.18 (16)	C5K—C5J—C5I	121.6 (2)
C14—N22—Ni	127.19 (14)	C5K—C5J—H5JA	119.2
C11—N22—Ni	128.63 (13)	C5I—C5J—H5JA	119.2
C6—C5—C14^i	123.17 (18)	C5J—C5K—C5L	119.8 (2)
C6—C5—C5A	118.53 (18)	C5J—C5K—H5KA	120.1
C14^i—C5—C5A	118.30 (18)	C5L—C5K—H5KA	120.1
C5—C6—N21	126.01 (18)	C5M—C5L—C5K	120.3 (2)
C5—C6—C7	123.21 (18)	C5M—C5L—H5LA	119.8
N21—C6—C7	110.77 (18)	C5K—C5L—H5LA	119.8
C8—C7—C6	107.78 (19)	C5L—C5M—C5N	122.0 (2)
C8—C7—H7A	126.1	C5L—C5M—H5MA	119.0
C6—C7—H7A	126.1	C5N—C5M—H5MA	119.0
C7—C8—C9	106.63 (19)	C5A—C5N—C5M	122.31 (19)
C7—C8—H8A	126.7	C5A—C5N—C5I	119.88 (18)
C9—C8—H8A	126.7	C5M—C5N—C5I	117.81 (18)
N21—C9—C10	125.85 (19)	C10—C10A—C10B	112.21 (17)
N21—C9—C8	110.55 (17)	C10—C10A—H10A	109.2
C10—C9—C8	123.6 (2)	C10B—C10A—H10A	109.2
C9—C10—C11	121.1 (2)	C10—C10A—H10B	109.2
C9—C10—C10A	121.00 (19)	C10B—C10A—H10B	109.2
C11—C10—C10A	117.87 (18)	H10A—C10A—H10B	107.9
N22—C11—C10	126.47 (18)	C10C—C10B—C10A	113.98 (17)
N22—C11—C12	110.47 (18)	C10C—C10B—H10C	108.8
C10—C11—C12	123.1 (2)	C10A—C10B—H10C	108.8
C13—C12—C11	107.1 (2)	C10C—C10B—H10D	108.8
C13—C12—H12A	126.4	C10A—C10B—H10D	108.8
C11—C12—H12A	126.4	H10C—C10B—H10D	107.7
C12—C13—C14	107.17 (19)	C10B—C10C—C10D	113.40 (17)
C12—C13—H13A	126.4	C10B—C10C—H10E	108.9
C14—C13—H13A	126.4	C10D—C10C—H10E	108.9
N22—C14—C5^i	125.85 (19)	C10B—C10C—H10F	108.9
N22—C14—C13	111.04 (18)	C10D—C10C—H10F	108.9
C5^i—C14—C13	123.11 (18)	H10E—C10C—H10F	107.7
C5B—C5A—C5N	120.05 (18)	C10E—C10D—C10C	112.63 (18)
C5B—C5A—C5	120.47 (18)	C10E—C10D—H10G	109.1
C5N—C5A—C5	119.47 (17)	C10C—C10D—H10G	109.1
C5A—C5B—C5C	122.32 (19)	C10E—C10D—H10H	109.1
C5A—C5B—C5G	119.53 (19)	C10C—C10D—H10H	109.1
C5C—C5B—C5G	118.13 (18)	H10G—C10D—H10H	107.8
C5D—C5C—C5B	121.2 (2)	C10D—C10E—C10F	113.70 (18)
C5D—C5C—H5CA	119.4	C10D—C10E—H10I	108.8
C5B—C5C—H5CA	119.4	C10F—C10E—H10I	108.8
C5C—C5D—C5E	120.5 (2)	C10D—C10E—H10J	108.8
C5C—C5D—H5DA	119.8	C10F—C10E—H10J	108.8
C5E—C5D—H5DA	119.8	H10I—C10E—H10J	107.7
C5F—C5E—C5D	120.3 (2)	C10E—C10F—H10K	109.5
C5F—C5E—H5EA	119.9	C10E—C10F—H10L	109.5
C5D—C5E—H5EA	119.9	H10K—C10F—H10L	109.5
C5E—C5F—C5G	121.6 (2)	C10E—C10F—H10M	109.5
C5E—C5F—H5FA	119.2	H10K—C10F—H10M	109.5
C5G—C5F—H5FA	119.2	H10L—C10F—H10M	109.5

Symmetry code: (i) −x, −y+1, −z.