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The title compound, C52H66N6O4·2CH3OH, is a 5,15-diaryl­octa­alkyl­porphyrinogen. The mol­ecule is centrosymmetric, with the pyrrole rings adopting a 1,2-alternate arrangement. The methanol mol­ecules are included in the tetra­pyrrole cavity through hydrogen bonding and O—H...π inter­actions. The mol­ecules form chains in the crystal structure via phenyl C—H...π-pyrrole stacking.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806022288/xu2051sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806022288/xu2051Isup2.hkl
Contains datablock I

CCDC reference: 613862

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.044
  • wR factor = 0.145
  • Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT420_ALERT_2_B D-H Without Acceptor O3 - H3 ... ?
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.96 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.79 Ratio PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C H4 O
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 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 2 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

2,8,12,18-Tetrabutyl-3,7,13,17-tetramethyl-5,15-bis(3-nitrophenyl)porphyrinogen dimethanol top
Crystal data top
C52H66N6O4·2CH4OZ = 1
Mr = 903.19F(000) = 488
Triclinic, P1Dx = 1.187 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.2665 (1) ÅCell parameters from 7598 reflections
b = 12.2138 (1) Åθ = 1.6–25.3°
c = 13.0914 (2) ŵ = 0.08 mm1
α = 104.754 (1)°T = 150 K
β = 97.430 (1)°Plate, yellow
γ = 92.499 (1)°0.34 × 0.32 × 0.18 mm
V = 1263.42 (3) Å3
Data collection top
Siemens SMART CCD area-detector
diffractometer
4193 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 25.3°, θmin = 1.6°
ω scansh = 99
9845 measured reflectionsk = 1414
4571 independent reflectionsl = 1415
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H-atom parameters constrained
S = 0.81 w = 1/[σ2(Fo2) + (0.1122P)2 + 0.8341P]
where P = (Fo2 + 2Fc2)/3
4571 reflections(Δ/σ)max = 0.003
302 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.29 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
N10.05035 (15)0.19983 (10)0.05865 (10)0.0246 (3)
H1A0.03710.18080.00990.029*
N20.16736 (15)0.02102 (10)0.12579 (10)0.0251 (3)
H2A0.16320.01600.06030.030*
N30.29487 (18)0.38705 (12)0.16602 (12)0.0377 (3)
O10.36185 (16)0.31356 (12)0.13302 (13)0.0542 (4)
O20.37068 (18)0.44928 (13)0.21110 (15)0.0623 (4)
C10.10235 (18)0.18797 (12)0.20929 (12)0.0271 (3)
H1B0.09450.23980.28180.032*
H1C0.19470.20940.16420.032*
C20.05291 (18)0.20686 (12)0.16515 (12)0.0248 (3)
C30.21124 (18)0.23843 (12)0.21540 (12)0.0268 (3)
C40.30797 (18)0.25196 (12)0.13525 (12)0.0270 (3)
C50.20560 (17)0.22711 (12)0.03915 (12)0.0251 (3)
C60.23675 (18)0.23344 (12)0.07078 (12)0.0263 (3)
H6A0.35570.25660.06550.032*
C70.20062 (17)0.12005 (12)0.15392 (12)0.0249 (3)
C80.19775 (18)0.09359 (13)0.26268 (12)0.0279 (3)
C90.15818 (18)0.02691 (13)0.30227 (12)0.0271 (3)
C100.14160 (17)0.06905 (12)0.21585 (11)0.0252 (3)
C110.48753 (19)0.28872 (15)0.15450 (14)0.0371 (4)
H11A0.52990.27350.08610.056*
H11B0.54570.24640.20010.056*
H11C0.50420.37020.18980.056*
C120.2300 (2)0.17484 (15)0.32861 (14)0.0385 (4)
H12A0.12860.20890.34680.058*
H12B0.26880.13370.39430.058*
H12C0.31340.23480.28760.058*
C130.2659 (2)0.26280 (14)0.33410 (12)0.0335 (4)
H13A0.38230.24740.34670.040*
H13B0.20130.21060.36300.040*
C140.2462 (2)0.38553 (15)0.39457 (13)0.0370 (4)
H14A0.32150.43710.37210.044*
H14B0.13300.40400.37440.044*
C150.2803 (3)0.40757 (19)0.51534 (15)0.0544 (5)
H15A0.39420.39070.53600.065*
H15B0.20620.35540.53810.065*
C160.2571 (3)0.5298 (2)0.57354 (19)0.0733 (8)
H16A0.28080.53970.65080.110*
H16B0.14390.54650.55480.110*
H16C0.33170.58180.55240.110*
C170.1451 (2)0.09443 (14)0.41698 (12)0.0316 (4)
H17A0.10330.04650.46360.038*
H17B0.06450.16050.42960.038*
C180.3070 (2)0.13672 (19)0.44823 (15)0.0466 (5)
H18A0.34040.19340.40900.056*
H18B0.39170.07210.42560.056*
C190.3012 (3)0.1905 (2)0.56787 (17)0.0611 (6)
H19A0.40590.22440.58040.073*
H19B0.21260.25260.59160.073*
C200.2721 (3)0.1058 (2)0.63476 (17)0.0704 (7)
H20A0.26860.14480.71040.106*
H20B0.36130.04530.61330.106*
H20C0.16780.07270.62360.106*
C210.14019 (18)0.32668 (12)0.10380 (12)0.0270 (3)
C220.02973 (19)0.31210 (13)0.12786 (12)0.0285 (3)
H22A0.08650.24220.12950.034*
C230.11505 (19)0.40070 (13)0.14930 (12)0.0305 (3)
C240.0386 (2)0.50367 (13)0.15155 (13)0.0348 (4)
H24A0.10000.56260.16770.042*
C250.1306 (2)0.51662 (14)0.12921 (14)0.0370 (4)
H25A0.18710.58560.13050.044*
C260.2192 (2)0.42948 (13)0.10481 (13)0.0331 (4)
H26A0.33500.44050.08860.040*
O30.21702 (13)0.04241 (10)0.08928 (9)0.0337 (3)
H30.18150.01310.13010.051*
C280.3909 (2)0.03852 (16)0.11549 (16)0.0431 (4)
H28A0.43050.10880.07530.065*
H28B0.44170.02650.09700.065*
H28C0.41970.03050.19220.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0226 (6)0.0244 (6)0.0249 (6)0.0003 (5)0.0014 (5)0.0047 (5)
N20.0286 (6)0.0240 (6)0.0231 (6)0.0029 (5)0.0062 (5)0.0054 (5)
N30.0342 (8)0.0334 (7)0.0472 (8)0.0068 (6)0.0064 (6)0.0131 (6)
O10.0334 (7)0.0550 (8)0.0862 (11)0.0039 (6)0.0136 (7)0.0375 (8)
O20.0432 (8)0.0581 (9)0.0956 (12)0.0123 (7)0.0004 (8)0.0420 (9)
C10.0271 (8)0.0243 (7)0.0298 (8)0.0046 (6)0.0077 (6)0.0049 (6)
C20.0273 (7)0.0190 (7)0.0280 (7)0.0042 (5)0.0053 (6)0.0052 (6)
C30.0280 (8)0.0232 (7)0.0276 (7)0.0052 (6)0.0033 (6)0.0040 (6)
C40.0244 (7)0.0237 (7)0.0312 (8)0.0040 (6)0.0041 (6)0.0035 (6)
C50.0234 (7)0.0210 (7)0.0299 (8)0.0016 (5)0.0062 (6)0.0040 (6)
C60.0237 (7)0.0249 (7)0.0297 (8)0.0005 (6)0.0060 (6)0.0052 (6)
C70.0228 (7)0.0236 (7)0.0286 (7)0.0030 (5)0.0057 (5)0.0063 (6)
C80.0276 (7)0.0287 (8)0.0288 (8)0.0039 (6)0.0060 (6)0.0090 (6)
C90.0270 (7)0.0284 (8)0.0254 (7)0.0040 (6)0.0048 (6)0.0052 (6)
C100.0234 (7)0.0244 (7)0.0267 (7)0.0038 (6)0.0047 (6)0.0039 (6)
C110.0239 (8)0.0416 (9)0.0404 (9)0.0013 (7)0.0020 (7)0.0026 (7)
C120.0517 (10)0.0346 (9)0.0327 (8)0.0024 (7)0.0122 (7)0.0124 (7)
C130.0339 (8)0.0374 (9)0.0284 (8)0.0043 (7)0.0001 (6)0.0092 (7)
C140.0400 (9)0.0392 (9)0.0281 (8)0.0008 (7)0.0022 (7)0.0040 (7)
C150.0646 (13)0.0623 (13)0.0304 (9)0.0084 (10)0.0038 (9)0.0055 (9)
C160.0695 (15)0.0843 (18)0.0434 (12)0.0090 (13)0.0072 (11)0.0213 (12)
C170.0360 (9)0.0324 (8)0.0253 (8)0.0035 (7)0.0049 (6)0.0052 (6)
C180.0406 (10)0.0609 (12)0.0354 (9)0.0134 (9)0.0086 (8)0.0041 (8)
C190.0554 (13)0.0808 (16)0.0395 (11)0.0120 (11)0.0182 (9)0.0049 (10)
C200.0715 (15)0.0996 (19)0.0327 (10)0.0255 (14)0.0148 (10)0.0058 (11)
C210.0297 (8)0.0250 (7)0.0263 (7)0.0018 (6)0.0080 (6)0.0048 (6)
C220.0317 (8)0.0250 (7)0.0296 (8)0.0003 (6)0.0069 (6)0.0079 (6)
C230.0313 (8)0.0297 (8)0.0315 (8)0.0033 (6)0.0078 (6)0.0079 (6)
C240.0428 (9)0.0257 (8)0.0379 (9)0.0070 (7)0.0093 (7)0.0097 (7)
C250.0422 (9)0.0247 (8)0.0462 (10)0.0025 (7)0.0118 (7)0.0112 (7)
C260.0318 (8)0.0284 (8)0.0394 (9)0.0011 (6)0.0096 (7)0.0080 (7)
O30.0306 (6)0.0342 (6)0.0337 (6)0.0051 (5)0.0022 (5)0.0047 (5)
C280.0321 (9)0.0439 (10)0.0554 (11)0.0038 (7)0.0031 (8)0.0187 (9)
Geometric parameters (Å, º) top
N1—C21.3721 (19)C14—C151.521 (2)
N1—C51.3835 (19)C14—H14A0.9900
N1—H1A0.8800C14—H14B0.9900
N2—C71.3778 (19)C15—C161.527 (3)
N2—C101.3783 (19)C15—H15A0.9900
N2—H2A0.8800C15—H15B0.9900
N3—O21.222 (2)C16—H16A0.9800
N3—O11.2307 (19)C16—H16B0.9800
N3—C231.470 (2)C16—H16C0.9800
C1—C10i1.501 (2)C17—C181.523 (2)
C1—C21.506 (2)C17—H17A0.9900
C1—H1B0.9900C17—H17B0.9900
C1—H1C0.9900C18—C191.530 (3)
C2—C31.378 (2)C18—H18A0.9900
C3—C41.436 (2)C18—H18B0.9900
C3—C131.509 (2)C19—C201.524 (4)
C4—C51.378 (2)C19—H19A0.9900
C4—C111.502 (2)C19—H19B0.9900
C5—C61.515 (2)C20—H20A0.9800
C6—C71.518 (2)C20—H20B0.9800
C6—C211.537 (2)C20—H20C0.9800
C6—H6A1.0000C21—C221.393 (2)
C7—C81.374 (2)C21—C261.394 (2)
C8—C91.438 (2)C22—C231.385 (2)
C8—C121.508 (2)C22—H22A0.9500
C9—C101.376 (2)C23—C241.391 (2)
C9—C171.506 (2)C24—C251.385 (2)
C10—C1i1.501 (2)C24—H24A0.9500
C11—H11A0.9800C25—C261.397 (2)
C11—H11B0.9800C25—H25A0.9500
C11—H11C0.9800C26—H26A0.9500
C12—H12A0.9800O3—C281.430 (2)
C12—H12B0.9800O3—H30.8400
C12—H12C0.9800C28—H28A0.9800
C13—C141.533 (2)C28—H28B0.9800
C13—H13A0.9900C28—H28C0.9800
C13—H13B0.9900
C2—N1—C5109.98 (12)C13—C14—H14A108.8
C2—N1—H1A125.0C15—C14—H14B108.8
C5—N1—H1A125.0C13—C14—H14B108.8
C7—N2—C10109.65 (12)H14A—C14—H14B107.7
C7—N2—H2A125.2C14—C15—C16112.65 (19)
C10—N2—H2A125.2C14—C15—H15A109.1
O2—N3—O1123.14 (15)C16—C15—H15A109.1
O2—N3—C23118.78 (14)C14—C15—H15B109.1
O1—N3—C23118.08 (14)C16—C15—H15B109.1
C10i—C1—C2115.53 (12)H15A—C15—H15B107.8
C10i—C1—H1B108.4C15—C16—H16A109.5
C2—C1—H1B108.4C15—C16—H16B109.5
C10i—C1—H1C108.4H16A—C16—H16B109.5
C2—C1—H1C108.4C15—C16—H16C109.5
H1B—C1—H1C107.5H16A—C16—H16C109.5
N1—C2—C3107.98 (13)H16B—C16—H16C109.5
N1—C2—C1120.95 (13)C9—C17—C18113.43 (13)
C3—C2—C1130.96 (14)C9—C17—H17A108.9
C2—C3—C4107.11 (13)C18—C17—H17A108.9
C2—C3—C13125.22 (14)C9—C17—H17B108.9
C4—C3—C13127.50 (14)C18—C17—H17B108.9
C5—C4—C3107.57 (13)H17A—C17—H17B107.7
C5—C4—C11126.83 (14)C17—C18—C19113.98 (16)
C3—C4—C11125.59 (14)C17—C18—H18A108.8
C4—C5—N1107.36 (13)C19—C18—H18A108.8
C4—C5—C6131.15 (13)C17—C18—H18B108.8
N1—C5—C6121.34 (13)C19—C18—H18B108.8
C5—C6—C7112.87 (12)H18A—C18—H18B107.7
C5—C6—C21109.74 (11)C20—C19—C18113.0 (2)
C7—C6—C21111.83 (12)C20—C19—H19A109.0
C5—C6—H6A107.4C18—C19—H19A109.0
C7—C6—H6A107.4C20—C19—H19B109.0
C21—C6—H6A107.4C18—C19—H19B109.0
C8—C7—N2108.15 (13)H19A—C19—H19B107.8
C8—C7—C6130.28 (13)C19—C20—H20A109.5
N2—C7—C6121.55 (13)C19—C20—H20B109.5
C7—C8—C9106.98 (13)H20A—C20—H20B109.5
C7—C8—C12126.82 (14)C19—C20—H20C109.5
C9—C8—C12126.20 (14)H20A—C20—H20C109.5
C10—C9—C8107.49 (13)H20B—C20—H20C109.5
C10—C9—C17126.66 (14)C22—C21—C26118.63 (14)
C8—C9—C17125.80 (14)C22—C21—C6120.28 (13)
C9—C10—N2107.71 (13)C26—C21—C6121.00 (13)
C9—C10—C1i130.89 (14)C23—C22—C21119.23 (14)
N2—C10—C1i121.39 (13)C23—C22—H22A120.4
C4—C11—H11A109.5C21—C22—H22A120.4
C4—C11—H11B109.5C22—C23—C24123.06 (15)
H11A—C11—H11B109.5C22—C23—N3118.42 (14)
C4—C11—H11C109.5C24—C23—N3118.47 (14)
H11A—C11—H11C109.5C25—C24—C23117.22 (15)
H11B—C11—H11C109.5C25—C24—H24A121.4
C8—C12—H12A109.5C23—C24—H24A121.4
C8—C12—H12B109.5C24—C25—C26120.77 (15)
H12A—C12—H12B109.5C24—C25—H25A119.6
C8—C12—H12C109.5C26—C25—H25A119.6
H12A—C12—H12C109.5C21—C26—C25121.05 (15)
H12B—C12—H12C109.5C21—C26—H26A119.5
C3—C13—C14113.12 (13)C25—C26—H26A119.5
C3—C13—H13A109.0C28—O3—H3109.5
C14—C13—H13A109.0O3—C28—H28A109.5
C3—C13—H13B109.0O3—C28—H28B109.5
C14—C13—H13B109.0H28A—C28—H28B109.5
H13A—C13—H13B107.8O3—C28—H28C109.5
C15—C14—C13113.75 (15)H28A—C28—H28C109.5
C15—C14—H14A108.8H28B—C28—H28C109.5
Symmetry code: (i) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O30.882.222.9930 (16)147
N2—H2A···O3i0.882.253.0881 (17)160
C11—H11C···O2ii0.982.483.312 (2)143
Symmetry codes: (i) x, y, z; (ii) x, y+1, z.
 

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