1,4:8,11:15,18:22,25-Tetra­ethano-29H,31H-tetra­benzo[b,g,l,q]porphine toluene tris­olvate

Aramaki, S.; Sakai, Y.; Yanagisawa, H.; Mizuguchi, J.

doi:10.1107/S1600536805004228

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1,4:8,11:15,18:22,25-Tetraethano-29H,31H-tetrabenzo[b,g,l,q]porphine toluene trisolvate

S. Aramaki, Y. Sakai, H. Yanagisawa and J. Mizuguchi

In the title compound, C₄₄H₃₈N₄·3C₇H₈, the porphine (CP) is a soluble precursor of metal-free porphyrin which exhibits an excellent field-effect transistor characteristic. The CP molecule is not entirely flat in its crystal structure (i.e. not D_2h), but is slightly deformed, as characterized by crystallographic C_i symmetry. The geometric isomer of CP could not be identified due to orientational disorder.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805004228/ob6474sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805004228/ob6474Isup2.hkl Contains datablock I

CCDC reference: 269835

checkCIF report

Key indicators

Single-crystal X-ray study
T = 93 K
Mean (C-C) = 0.009 Å
Disorder in solvent or counterion
R factor = 0.073
wR factor = 0.197
Data-to-parameter ratio = 9.6

checkCIF/PLATON results

No syntax errors found



Alert level A
THETM01_ALERT_3_A  The value of sine(theta_max)/wavelength is less than 0.550
            Calculated sin(theta_max)/wavelength =    0.5435

Author Response: Carefull re-check of our reflection data reveals that the reflection measurements were carried out, for an accidental error, up to the theta_max of 56.92 degrees.

PLAT023_ALERT_3_A Resolution (too) Low [sin(th)/Lambda < 0.6].....      56.92 Deg.

Author Response: Carefull re-check of our reflection data reveals that the reflection measurements were carried out, for an accidental error, up to the theta_max of 56.92 degrees.

PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      56.92 Deg.

Author Response: Carefull re-check of our reflection data reveals that the reflection measurements were carried out, for an accidental error, up to the theta_max of 56.92 degrees.

PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.93

Author Response: A two-dimensional detector (IP) was used in combination with Cu target as radiation. For this reason, the completeness is rather low.


Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.471     0.897
            Tmin' and Tmax expected:      0.779     0.897
            RR' =      0.605
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.58

Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           56.92
           From the CIF: _diffrn_reflns_theta_full          56.92
           From the CIF: _reflns_number_total               3020
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         3263
           Completeness (_total/calc)             92.55%
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 10 for a
            centrosymmetric structure
            sine(theta)/lambda                0.5435
            Proportion of unique data used    1.0000
            Ratio reflections to parameters   9.5570
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.93
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.56
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................       7.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C5     -   C6     ...       1.43 Ang.
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C17    -   C18    ...       1.42 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C30    -   C31    ...       1.39 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C31    -   C32    ...       1.38 Ang.
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C29
PLAT411_ALERT_2_C Short Inter H...H Contact  H20    ..  H21     ..       2.13 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       2.90 Deg.
              C33  -C31  -H31     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       8.30 Deg.
              C31  -C33  -H31     1.555   1.555   1.555

   4 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  15 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
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
  11 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: TEXSAN; molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: TEXSAN.

1,4:8,11:15,18:22,25-Tetraethano-29H,31H-tetrabenzo[b,g,l,q]porphine toluene trisolvate top

Crystal data top

C₄₄H₃₈N₄·3C₇H₈	Z = 1
M_r = 899.18	F(000) = 480
Triclinic, P1	D_x = 1.231 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.5418 Å
a = 9.986 (3) Å	Cell parameters from 8380 reflections
b = 11.682 (3) Å	θ = 4.2–56.9°
c = 12.222 (4) Å	µ = 0.54 mm⁻¹
α = 117.17 (2)°	T = 93 K
β = 103.69 (2)°	Block, dark red
γ = 92.56 (2)°	0.40 × 0.40 × 0.20 mm
V = 1213.0 (7) Å³

Data collection top

Rigaku R-AXIS RAPID imaging plate diffractometer	1754 reflections with F² > 2σ(F²)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.067
48 frames, δ ω = 15° scans	θ_max = 56.9°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = 0→10
T_min = 0.471, T_max = 0.897	k = −12→12
8409 measured reflections	l = −13→12
3020 independent reflections

Refinement top

Refinement on F²	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.073	w = 1/[σ²(F_o²) + (0.05(Max(F_o²,0) + 2F_c²)/3)²]
wR(F²) = 0.197	(Δ/σ)_max < 0.001
S = 1.26	Δρ_max = 0.45 e Å⁻³
3020 reflections	Δρ_min = −0.46 e Å⁻³
316 parameters

Special details top

Refinement. Refinement using reflections with F² > -10.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	0.4543 (4)	0.9085 (4)	0.2983 (4)	0.033 (1)
N2	0.6729 (4)	0.9136 (4)	0.5039 (4)	0.033 (1)
C1	0.6541 (5)	0.7942 (5)	0.2741 (5)	0.032 (2)
C2	0.5308 (5)	0.8277 (5)	0.2251 (5)	0.030 (2)
C3	0.4586 (5)	0.7868 (5)	0.0927 (5)	0.035 (2)
C4	0.4760 (6)	0.7001 (6)	−0.0366 (5)	0.038 (2)
C5	0.3418 (6)	0.5977 (6)	−0.1127 (5)	0.047 (2)
C6	0.2184 (6)	0.6558 (6)	−0.1131 (5)	0.045 (2)
C7	0.2502 (6)	0.8047 (6)	−0.0436 (5)	0.038 (2)
C8	0.3417 (5)	0.8424 (5)	0.0906 (5)	0.034 (2)
C9	0.4710 (6)	0.7846 (7)	−0.1034 (6)	0.051 (2)
C10	0.3463 (6)	0.8410 (6)	−0.1070 (5)	0.046 (2)
C11	0.3374 (5)	0.9207 (5)	0.2199 (5)	0.032 (2)
C12	0.2361 (5)	0.9926 (5)	0.2604 (5)	0.031 (2)
C13	0.7214 (5)	0.8334 (5)	0.4014 (5)	0.031 (2)
C14	0.8531 (5)	0.8020 (5)	0.4501 (5)	0.032 (2)
C15	0.8819 (6)	0.8603 (5)	0.5785 (5)	0.033 (2)
C16	1.0209 (5)	0.8443 (5)	0.6475 (5)	0.034 (2)
C17	1.1299 (6)	0.8963 (6)	0.6044 (6)	0.045 (2)
C18	1.0998 (6)	0.8360 (6)	0.4682 (6)	0.043 (2)
C19	0.9654 (5)	0.7335 (5)	0.3986 (5)	0.032 (2)
C20	1.0197 (6)	0.6972 (5)	0.5873 (5)	0.041 (2)
C21	0.9899 (6)	0.6352 (5)	0.4501 (5)	0.043 (2)
C22	0.7697 (5)	0.9308 (5)	0.6141 (5)	0.035 (2)
C23	0.1954 (5)	0.4492 (5)	0.1300 (5)	0.035 (2)
C24	0.2206 (6)	0.3839 (6)	0.2015 (5)	0.042 (2)
C25	0.1860 (6)	0.2495 (6)	0.1446 (6)	0.044 (2)
C26	0.1232 (6)	0.1776 (6)	0.0137 (6)	0.047 (2)
C27	0.0957 (6)	0.2413 (6)	−0.0588 (5)	0.045 (2)
C28	0.1313 (6)	0.3760 (6)	−0.0006 (5)	0.040 (2)
C29	0.2401 (7)	0.5962 (6)	0.1937 (6)	0.054 (2)
C30	0.4276 (8)	0.4140 (9)	0.5241 (6)	0.066 (2)
C31	0.5326 (8)	0.3776 (8)	0.4649 (6)	0.064 (2)
C32	0.6027 (8)	0.4643 (9)	0.4404 (6)	0.069 (3)
C33	0.5583 (11)	0.2617 (13)	0.4296 (11)	0.035 (3)	0.50
H1	0.6969	0.7378	0.2129	0.0382*
H4	0.5584	0.6629	−0.0325	0.0455*
H5A	0.3381	0.5425	−0.0752	0.0563*
H5B	0.3439	0.5471	−0.1989	0.0563*
H6A	0.1644	0.6283	−0.0721	0.0545*
H6B	0.1658	0.6262	−0.1997	0.0545*
H7	0.1687	0.8437	−0.0440	0.0451*
H9	0.5420	0.7979	−0.1383	0.0617*
H10	0.3258	0.8955	−0.1451	0.0557*
H12	0.1607	0.9897	0.1944	0.0378*
H16	1.0387	0.8861	0.7382	0.0406*
H17A	1.2187	0.8807	0.6386	0.0544*
H17B	1.1328	0.9877	0.6372	0.0544*
H18A	1.1758	0.7947	0.4442	0.0520*
H18B	1.0897	0.9015	0.4428	0.0520*
H19	0.9433	0.6937	0.3077	0.0390*
H20	1.0368	0.6517	0.6354	0.0497*
H21	0.9858	0.5444	0.3971	0.0511*
H24	0.2627	0.4328	0.2917	0.0500*
H25	0.2052	0.2067	0.1951	0.0524*
H26	0.0990	0.0851	−0.0263	0.0559*
H27	0.0521	0.1923	−0.1488	0.0541*
H28	0.1115	0.4187	−0.0512	0.0474*
H29A	0.3386	0.6186	0.2320	0.0646*
H29B	0.2153	0.6243	0.1310	0.0646*
H29C	0.1943	0.6378	0.2578	0.0646*
H30	0.3775	0.3545	0.5396	0.0797*
H31	0.5565	0.2934	0.4413	0.0507*	0.50
H32	0.6730	0.4381	0.3980	0.0824*
H33A	0.5852	0.2485	0.5024	0.0417*	0.50
H33B	0.6321	0.2503	0.3908	0.0417*	0.50
H33C	0.4766	0.2003	0.3695	0.0417*	0.50
H34	0.4783	0.9500	0.3894	0.0395*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.033 (3)	0.032 (3)	0.024 (2)	0.004 (2)	0.000 (2)	0.010 (2)
N2	0.033 (3)	0.034 (3)	0.028 (3)	0.003 (2)	0.000 (2)	0.015 (2)
C1	0.032 (3)	0.026 (3)	0.029 (3)	0.002 (2)	0.004 (3)	0.008 (3)
C2	0.028 (3)	0.029 (3)	0.026 (3)	0.005 (3)	0.007 (3)	0.007 (3)
C3	0.031 (3)	0.034 (3)	0.028 (3)	−0.000 (3)	0.002 (3)	0.010 (3)
C4	0.035 (3)	0.045 (4)	0.022 (3)	0.014 (3)	0.006 (3)	0.007 (3)
C5	0.046 (4)	0.049 (4)	0.025 (3)	0.001 (3)	0.005 (3)	0.005 (3)
C6	0.043 (4)	0.048 (4)	0.033 (3)	0.003 (3)	0.000 (3)	0.015 (3)
C7	0.032 (3)	0.041 (4)	0.025 (3)	0.008 (3)	0.002 (3)	0.007 (3)
C8	0.032 (3)	0.036 (3)	0.026 (3)	0.005 (3)	0.001 (3)	0.011 (3)
C9	0.048 (4)	0.071 (5)	0.042 (4)	0.014 (4)	0.015 (3)	0.032 (4)
C10	0.040 (4)	0.070 (5)	0.033 (3)	0.007 (3)	0.006 (3)	0.030 (3)
C11	0.033 (3)	0.032 (3)	0.021 (3)	0.004 (3)	0.000 (3)	0.007 (3)
C12	0.033 (3)	0.035 (3)	0.019 (3)	0.005 (3)	0.001 (2)	0.010 (3)
C13	0.033 (3)	0.027 (3)	0.026 (3)	0.003 (3)	0.005 (3)	0.009 (3)
C14	0.028 (3)	0.030 (3)	0.033 (3)	0.004 (3)	0.003 (3)	0.012 (3)
C15	0.033 (3)	0.031 (3)	0.028 (3)	0.007 (3)	0.002 (3)	0.012 (3)
C16	0.031 (3)	0.035 (3)	0.029 (3)	0.008 (3)	0.003 (3)	0.012 (3)
C17	0.042 (4)	0.044 (4)	0.046 (4)	0.003 (3)	0.000 (3)	0.025 (3)
C18	0.043 (4)	0.038 (4)	0.048 (4)	0.005 (3)	0.010 (3)	0.021 (3)
C19	0.033 (3)	0.032 (3)	0.022 (3)	0.004 (3)	0.004 (3)	0.007 (3)
C20	0.049 (4)	0.028 (3)	0.039 (4)	0.004 (3)	−0.005 (3)	0.018 (3)
C21	0.058 (4)	0.029 (3)	0.039 (4)	0.008 (3)	0.011 (3)	0.016 (3)
C22	0.032 (3)	0.033 (3)	0.037 (4)	0.004 (3)	0.007 (3)	0.016 (3)
C23	0.026 (3)	0.040 (4)	0.036 (3)	0.004 (3)	0.007 (3)	0.017 (3)
C24	0.035 (3)	0.050 (4)	0.029 (3)	0.003 (3)	0.005 (3)	0.012 (3)
C25	0.037 (3)	0.045 (4)	0.051 (4)	0.006 (3)	0.008 (3)	0.028 (3)
C26	0.036 (3)	0.041 (4)	0.049 (4)	−0.000 (3)	0.007 (3)	0.014 (3)
C27	0.043 (4)	0.043 (4)	0.034 (3)	−0.004 (3)	0.003 (3)	0.011 (3)
C28	0.037 (3)	0.046 (4)	0.033 (3)	0.004 (3)	0.006 (3)	0.020 (3)
C29	0.057 (4)	0.045 (4)	0.050 (4)	0.007 (3)	0.011 (3)	0.017 (3)
C30	0.065 (5)	0.080 (6)	0.028 (4)	−0.042 (5)	−0.003 (4)	0.017 (4)
C31	0.072 (5)	0.067 (5)	0.025 (4)	−0.032 (5)	−0.006 (4)	0.013 (4)
C32	0.066 (5)	0.087 (6)	0.029 (4)	−0.031 (5)	0.003 (4)	0.018 (4)
C33	0.032 (6)	0.050 (8)	0.030 (6)	0.008 (6)	0.013 (5)	0.024 (6)

Geometric parameters (Å, º) top

N1—C2	1.376 (7)	C16—H16	0.950
N1—C11	1.382 (7)	C17—C18	1.426 (9)
N1—H34	0.950	C17—H17A	0.950
N2—C13	1.392 (7)	C17—H17B	0.950
N2—C22	1.381 (7)	C18—C19	1.531 (7)
C1—C2	1.391 (8)	C18—H18A	0.950
C1—C13	1.382 (8)	C18—H18B	0.950
C1—H1	0.950	C19—C21	1.54 (1)
C2—C3	1.441 (8)	C19—H19	0.950
C3—C4	1.496 (8)	C20—C21	1.436 (8)
C3—C8	1.361 (8)	C20—H20	0.950
C4—C5	1.530 (7)	C21—H21	0.950
C4—C9	1.54 (1)	C23—C24	1.39 (1)
C4—H4	0.950	C23—C28	1.382 (7)
C5—C6	1.433 (9)	C23—C29	1.516 (9)
C5—H5A	0.950	C24—C25	1.382 (9)
C5—H5B	0.950	C24—H24	0.950
C6—C7	1.524 (9)	C25—C26	1.382 (8)
C6—H6A	0.950	C25—H25	0.950
C6—H6B	0.950	C26—C27	1.38 (1)
C7—C8	1.522 (8)	C26—H26	0.950
C7—C10	1.52 (1)	C27—C28	1.385 (9)
C7—H7	0.950	C27—H27	0.950
C8—C11	1.433 (7)	C28—H28	0.950
C9—C10	1.435 (10)	C29—H29A	0.950
C9—H9	0.950	C29—H29B	0.950
C10—H10	0.950	C29—H29C	0.950
C11—C12	1.382 (8)	C30—C31	1.39 (1)
C12—C22ⁱ	1.397 (8)	C30—C32ⁱⁱ	1.36 (1)
C12—H12	0.950	C30—H30	0.950
C13—C14	1.446 (8)	C31—C32	1.39 (1)
C14—C15	1.343 (8)	C31—C33	1.28 (2)
C14—C19	1.500 (8)	C31—H31	0.950
C15—C16	1.512 (8)	C32—H32	0.950
C15—C22	1.452 (8)	C33—H33A	0.950
C16—C17	1.53 (1)	C33—H33B	0.950
C16—C20	1.527 (8)	C33—H33C	0.950

N2···C18ⁱⁱⁱ	3.458 (7)	C9···C25^iv	3.592 (8)
N2···C33ⁱⁱ	3.49 (1)	C13···C17ⁱⁱⁱ	3.467 (8)
C1···C17ⁱⁱⁱ	3.580 (8)	C18···C22ⁱⁱⁱ	3.596 (8)

C2—N1—C11	110.0 (4)	C16—C17—H17A	108.6
C2—N1—H34	125.0	C16—C17—H17B	108.6
C11—N1—H34	125.0	C18—C17—H17A	108.6
C13—N2—C22	106.5 (4)	C18—C17—H17B	108.6
C2—C1—C13	127.5 (5)	H17A—C17—H17B	109.5
C2—C1—H1	116.2	C17—C18—C19	112.4 (6)
C13—C1—H1	116.2	C17—C18—H18A	108.7
N1—C2—C1	124.7 (5)	C17—C18—H18B	108.7
N1—C2—C3	107.0 (5)	C19—C18—H18A	108.7
C1—C2—C3	128.2 (5)	C19—C18—H18B	108.7
C2—C3—C4	137.6 (5)	H18A—C18—H18B	109.5
C2—C3—C8	107.6 (5)	C14—C19—C18	105.9 (4)
C4—C3—C8	114.8 (5)	C14—C19—C21	105.9 (6)
C3—C4—C5	106.3 (5)	C14—C19—H19	113.2
C3—C4—C9	105.7 (5)	C18—C19—C21	104.8 (5)
C3—C4—H4	113.2	C18—C19—H19	113.2
C5—C4—C9	104.6 (5)	C21—C19—H19	113.2
C5—C4—H4	113.2	C16—C20—C21	112.6 (6)
C9—C4—H4	113.2	C16—C20—H20	123.7
C4—C5—C6	112.3 (5)	C21—C20—H20	123.7
C4—C5—H5A	108.8	C19—C21—C20	112.1 (5)
C4—C5—H5B	108.8	C19—C21—H21	124.0
C6—C5—H5A	108.8	C20—C21—H21	124.0
C6—C5—H5B	108.8	N2—C22—C12ⁱ	125.8 (5)
H5A—C5—H5B	109.5	N2—C22—C15	108.8 (5)
C5—C6—C7	113.2 (5)	C12ⁱ—C22—C15	125.3 (5)
C5—C6—H6A	108.5	C24—C23—C28	118.0 (6)
C5—C6—H6B	108.5	C24—C23—C29	120.7 (5)
C7—C6—H6A	108.5	C28—C23—C29	121.3 (7)
C7—C6—H6B	108.5	C23—C24—C25	121.6 (5)
H6A—C6—H6B	109.5	C23—C24—H24	119.2
C6—C7—C8	104.7 (6)	C25—C24—H24	119.2
C6—C7—C10	105.5 (5)	C24—C25—C26	119.6 (7)
C6—C7—H7	113.5	C24—C25—H25	120.2
C8—C7—C10	105.3 (4)	C26—C25—H25	120.2
C8—C7—H7	113.5	C25—C26—C27	119.5 (6)
C10—C7—H7	113.5	C25—C26—H26	120.2
C3—C8—C7	114.2 (5)	C27—C26—H26	120.2
C3—C8—C11	108.9 (5)	C26—C27—C28	120.3 (5)
C7—C8—C11	136.9 (5)	C26—C27—H27	119.9
C4—C9—C10	112.0 (6)	C28—C27—H27	119.9
C4—C9—H9	124.0	C23—C28—C27	120.9 (7)
C10—C9—H9	124.0	C23—C28—H28	119.6
C7—C10—C9	113.3 (7)	C27—C28—H28	119.6
C7—C10—H10	123.3	C23—C29—H29A	109.5
C9—C10—H10	123.3	C23—C29—H29B	109.5
N1—C11—C8	106.5 (5)	C23—C29—H29C	109.5
N1—C11—C12	125.9 (5)	H29A—C29—H29B	109.5
C8—C11—C12	127.6 (5)	H29A—C29—H29C	109.5
C11—C12—C22ⁱ	128.3 (5)	H29B—C29—H29C	109.5
C11—C12—H12	115.9	C31—C30—C32ⁱⁱ	119.0 (9)
C22ⁱ—C12—H12	115.9	C31—C30—H30	120.5
N2—C13—C1	124.4 (5)	C32ⁱⁱ—C30—H30	120.5
N2—C13—C14	109.3 (5)	C30—C31—C32	119.9 (8)
C1—C13—C14	126.3 (5)	C30—C31—C33	118 (1)
C13—C14—C15	107.2 (5)	C30—C31—H31	120.1
C13—C14—C19	138.0 (5)	C32—C31—C33	121.6 (10)
C15—C14—C19	114.6 (5)	C32—C31—H31	120.1
C14—C15—C16	114.9 (5)	C33—C31—H31	2.9
C14—C15—C22	108.1 (5)	C30ⁱⁱ—C32—C31	121.1 (8)
C16—C15—C22	136.9 (5)	C30ⁱⁱ—C32—H32	119.5
C15—C16—C17	105.1 (6)	C31—C32—H32	119.5
C15—C16—C20	105.9 (4)	C31—C33—H33A	109.5
C15—C16—H16	113.3	C31—C33—H33B	109.5
C17—C16—C20	105.0 (5)	C31—C33—H33C	109.5
C17—C16—H16	113.3	H33A—C33—H33B	109.5
C20—C16—H16	113.3	H33A—C33—H33C	109.5
C16—C17—C18	112.9 (4)	H33B—C33—H33C	109.5

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y+2, −z+1; (iv) −x+1, −y+1, −z.

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1,4:8,11:15,18:22,25-Tetra­ethano-29H,31H-tetra­benzo[b,g,l,q]porphine toluene tris­olvate

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1,4:8,11:15,18:22,25-Tetraethano-29H,31H-tetrabenzo[b,g,l,q]porphine toluene trisolvate