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The pentacoordinated Zn atom in the title compound, [Zn(C52H36Cl4N8O4)(CH4O)]·CHCl3, is displaced from the porphyrin N4 plane towards the axial methanol ligand by 0.269 (2) Å. The average Zn—N(porphyrin) distance is 2.063 (9) Å and the axial Zn—O(MeOH) distance is 2.147 (5) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801012788/ya6045sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801012788/ya6045Isup2.hkl
Contains datablock I

CCDC reference: 172193

Key indicators

  • Single-crystal X-ray study
  • T = 110 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.069
  • wR factor = 0.187
  • Data-to-parameter ratio = 17.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_731 Alert C Bond Calc 2.073(9), Rep 2.072(3) .... 3.00 s.u-Ratio ZN -N2 1.555 1.555 PLAT_731 Alert C Bond Calc 2.067(9), Rep 2.067(4) .... 2.25 s.u-Ratio ZN -N4 1.555 1.555 PLAT_732 Alert C Angle Calc 95.56(12), Rep 95.6(3) .... 2.50 s.u-Ratio N1 -ZN -O5 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 99.52(12), Rep 99.5(3) .... 2.50 s.u-Ratio N3 -ZN -O5 1.555 1.555 1.555
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
4 Alert Level C = Please check

Comment top

Porphyrins are of biological importance and therefore commonly used as building blocks in biomimetic chemistry. Very elegant heme protein models have been synthesized to elucidate the mechanism of functioning of the native enzymes, such as P-450 cytochromes (Sono et al., 1996), dioxygen carriers (Jameson & Ibers, 1994) or cytochrome c oxidase (Yoshikawa et al., 2000). In the latter case, different porphyrins bearing four pickets on the same side of the porphyrin have been reported and have been shown to be powerful and versatile intermediates (Collman et al., 1994). We recently observed that the spatial arrangement depends not only on the nature of the pickets, but also on the number of pickets per side of the porphyrin (Didier et al., 2001). Additionally, the interactions that the pickets can establish between them via a hydrogen-bonding net may be of prime importance (Ricard et al., 2001). We now report the structure of a zinc(II) porphyrin, (I), bearing three pickets on one side and the fourth on the other side of the porphyrin.

The porphyrin complex crystallizes with a chloroform molecule and an axially coordinated methanol molecule. The porphyrin ring adopts a nearly planar conformation. The coordination geometry is square pyramidal and the Zn atom is displaced from the N4 least-squares plane by 0.269 (2) Å towards the axial methanol O atom. The mean Zn—N(porphyrin) distance is 2.063 (9) Å and the Zn—O(methanol) distance is 2.147 (5) Å [the average Zn—O(methanol) value found for 13 analogous methanol zinc porphyrins is 2.20 (4) Å].

No intramolecular hydrogen bonds are observed in crystal. The O5—HO5···O2i hydrogen bond [O5···O2i 2.726 (11), HO5···O2i 1.82 Å andO5-HO5···O2i 171.8°; symmetry code (I) 0.5 + x, 0.5 - y, 0.5 + z] links the molecules of the complex into infinite chains along the [101] direction.

Experimental top

The free base used for the preparation of the title compound was synthesized according to a previously reported procedure (Collman et al., 1997). A 150 ml three-necked round-bottomed flask equipped with a stirrer bar was charged with the αααβ-atropisomer of 5,10,15,20-tetrakis(2-aminophenyl)porphyrin (TAPP; 337 mg, 0.5 mmol), dry THF (30 ml) and six equivalents of Et3N, then cooled in an ice bath, at which time, five equivalents of chloroacetyl chloride in 30 ml of dry THF were injected dropwise. The solution was allowed to stir for 3 h, after which the THF was removed in vacuo. The α-5,10,15:β-20-[tetrakis(2-chloroacetamido)phenyl]porphyrin was purified by flash chromatography on a silica column and eluted with 3% methanol in CH2Cl2; the yield was 73%·The title compound, (I), was obtained by zinc insertion according to the usual method which consists of refluxing a chloroform solution of the free-base porphyrin with a saturated solution of zinc acetate in methanol (Smith, 1975). Crystals suitable for X-ray data collection were obtained by slow (over a three-month period) diffusion of MeOH in a CHCl3 solution of compound (I) at room temperature.

Refinement top

H atoms were inserted at calculated positions or found in the difference electron-density map (for those of the methanol molecule and those of the amide groups) and treated in the riding model approximation with isotropic displacement parameters set to 1.2 times those of the parent atoms. The highest residual electron-density peak was located near the Cl6 atom of the chloroform solvate molecule.

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. View of (I) with 50% probability displacement ellipsoids. The H atoms and the chloroform solvate molecule have been omitted for clarity.
(I) top
Crystal data top
[Zn(C52H36Cl4N8O4)(CH4O)]·CHCl3F(000) = 2440
Mr = 1195.47Dx = 1.541 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 13.078 (6) ÅCell parameters from 19872 reflections
b = 17.899 (7) Åθ = 1.0–27.5°
c = 22.79 (9) ŵ = 0.90 mm1
β = 105.009 (2)°T = 110 K
V = 5153 (21) Å3Prism, red
Z = 40.25 × 0.25 × 0.25 mm
Data collection top
KappaCCD
diffractometer
Rint = 0.033
ϕ scans (κ = 0) + additional ω scansθmax = 27.5°, θmin = 2.0°
19872 measured reflectionsh = 1616
11775 independent reflectionsk = 1623
7802 reflections with I > 2σ(I)l = 2929
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.069 w = 1/[σ2(Fo2) + (0.0845P)2 + 10.6403P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.187(Δ/σ)max < 0.001
S = 1.04Δρmax = 1.27 e Å3
11775 reflectionsΔρmin = 1.62 e Å3
676 parameters
Crystal data top
[Zn(C52H36Cl4N8O4)(CH4O)]·CHCl3V = 5153 (21) Å3
Mr = 1195.47Z = 4
Monoclinic, P21/nMo Kα radiation
a = 13.078 (6) ŵ = 0.90 mm1
b = 17.899 (7) ÅT = 110 K
c = 22.79 (9) Å0.25 × 0.25 × 0.25 mm
β = 105.009 (2)°
Data collection top
KappaCCD
diffractometer
7802 reflections with I > 2σ(I)
19872 measured reflectionsRint = 0.033
11775 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0690 restraints
wR(F2) = 0.187H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0845P)2 + 10.6403P]
where P = (Fo2 + 2Fc2)/3
11775 reflectionsΔρmax = 1.27 e Å3
676 parametersΔρmin = 1.62 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn0.18059 (4)0.19459 (3)0.100060 (19)0.01684 (13)
Cl10.13369 (10)0.02724 (7)0.00181 (5)0.0400 (3)
Cl20.04149 (11)0.11479 (7)0.11408 (5)0.0401 (3)
Cl30.42224 (13)0.38847 (8)0.16719 (6)0.0507 (4)
Cl40.37591 (14)0.08478 (11)0.00903 (6)0.0676 (5)
Cl50.56419 (19)0.21015 (12)0.26300 (11)0.0952 (8)
Cl60.6849 (2)0.33913 (15)0.30878 (10)0.1124 (10)
Cl70.6965 (2)0.28012 (14)0.19549 (12)0.1072 (9)
O10.3337 (3)0.0486 (3)0.10310 (17)0.0562 (11)
O20.1883 (3)0.27700 (18)0.21841 (13)0.0363 (8)
O30.6299 (6)0.4503 (4)0.0801 (3)0.135 (3)
O40.3142 (3)0.1403 (3)0.16143 (18)0.0551 (11)
O50.2209 (2)0.27919 (16)0.16899 (12)0.0226 (6)
N10.1751 (3)0.10855 (18)0.15861 (14)0.0182 (7)
N20.0178 (3)0.20617 (18)0.08284 (14)0.0176 (7)
N30.1756 (3)0.25910 (19)0.02443 (14)0.0198 (7)
N40.3322 (3)0.16170 (19)0.10029 (14)0.0199 (7)
N50.1742 (3)0.0121 (2)0.12119 (16)0.0273 (8)
N60.1173 (3)0.2688 (2)0.11627 (15)0.0246 (8)
N70.4979 (4)0.3648 (2)0.05881 (19)0.0426 (11)
N80.4426 (3)0.0679 (2)0.14126 (16)0.0311 (9)
C10.2593 (3)0.0649 (2)0.18932 (16)0.0179 (8)
C20.2239 (3)0.0163 (2)0.23098 (17)0.0197 (8)
C30.1207 (3)0.0315 (2)0.22560 (17)0.0192 (8)
C40.0905 (3)0.0897 (2)0.18043 (16)0.0174 (8)
C50.0113 (3)0.1214 (2)0.16199 (17)0.0181 (8)
C60.0447 (3)0.1746 (2)0.11593 (17)0.0198 (8)
C70.1498 (3)0.2066 (3)0.09787 (18)0.0252 (9)
C80.1491 (3)0.2575 (2)0.05373 (18)0.0248 (9)
C90.0444 (3)0.2573 (2)0.04498 (17)0.0195 (8)
C100.0094 (3)0.3032 (2)0.00349 (16)0.0206 (8)
C110.0915 (3)0.3021 (2)0.00659 (17)0.0190 (8)
C120.1239 (4)0.3458 (3)0.05169 (19)0.0264 (9)
C130.2258 (4)0.3297 (3)0.04753 (18)0.0271 (10)
C140.2588 (3)0.2749 (2)0.00032 (18)0.0223 (9)
C150.3611 (3)0.2444 (2)0.01932 (18)0.0226 (9)
C160.3942 (3)0.1930 (2)0.06679 (18)0.0224 (9)
C170.5004 (3)0.1628 (3)0.0870 (2)0.0277 (10)
C180.5006 (4)0.1141 (3)0.13163 (19)0.0282 (10)
C190.3949 (3)0.1126 (2)0.13985 (17)0.0215 (9)
C200.3618 (3)0.0678 (2)0.18214 (17)0.0198 (8)
C210.0871 (3)0.0995 (2)0.19834 (18)0.0207 (8)
C220.0766 (4)0.1313 (3)0.25513 (19)0.0267 (9)
C230.1439 (4)0.1132 (3)0.2909 (2)0.0310 (10)
C240.2241 (4)0.0622 (3)0.2700 (2)0.0321 (11)
C250.2371 (3)0.0289 (3)0.2139 (2)0.0288 (10)
C260.1678 (3)0.0473 (2)0.17767 (18)0.0235 (9)
C270.2514 (4)0.0336 (3)0.0896 (2)0.0414 (13)
C280.2300 (5)0.0704 (3)0.0335 (2)0.0460 (14)
C290.0872 (3)0.3568 (2)0.03416 (18)0.0214 (8)
C300.1074 (4)0.4249 (3)0.0110 (2)0.0298 (10)
C310.1747 (4)0.4768 (3)0.0462 (2)0.0346 (11)
C320.2231 (4)0.4596 (3)0.1066 (2)0.0291 (10)
C330.2057 (3)0.3920 (2)0.13123 (19)0.0238 (9)
C340.1385 (3)0.3400 (2)0.09497 (17)0.0203 (8)
C350.1417 (4)0.2421 (2)0.17327 (19)0.0277 (10)
C360.1056 (4)0.1631 (3)0.18201 (19)0.0331 (11)
C370.4386 (3)0.2695 (3)0.01499 (19)0.0264 (9)
C380.4413 (4)0.2340 (3)0.0687 (2)0.0324 (10)
C390.5086 (4)0.2594 (3)0.1028 (2)0.0397 (13)
C400.5739 (4)0.3187 (3)0.0823 (2)0.0431 (13)
C410.5750 (4)0.3558 (3)0.0295 (2)0.0410 (12)
C420.5056 (4)0.3304 (3)0.0046 (2)0.0333 (11)
C430.5547 (6)0.4195 (4)0.0916 (3)0.077 (2)
C440.5208 (7)0.4452 (4)0.1480 (3)0.083 (3)
C450.4425 (3)0.0193 (2)0.22421 (18)0.0223 (9)
C460.4768 (3)0.0357 (2)0.28542 (19)0.0255 (9)
C470.5477 (4)0.0098 (3)0.3253 (2)0.0284 (10)
C480.5872 (4)0.0731 (3)0.3047 (2)0.0286 (10)
C490.5540 (4)0.0913 (3)0.2432 (2)0.0304 (10)
C500.4818 (3)0.0459 (2)0.20367 (18)0.0238 (9)
C510.3562 (4)0.1117 (3)0.1252 (2)0.0393 (12)
C520.3084 (5)0.1264 (4)0.0585 (2)0.0539 (16)
C530.1425 (4)0.3309 (3)0.1765 (2)0.0404 (13)
C540.6770 (7)0.2590 (4)0.2656 (5)0.092 (3)
H5O0.25540.25800.20490.027*
H5N0.12320.02400.10250.033*
H6N0.06050.23930.09190.029*
H7N0.44160.34360.07370.051*
H8N0.47340.04540.11540.037*
H20.26480.01890.25670.024*
H30.07730.00880.24690.023*
H70.20670.19460.11350.030*
H80.20580.28680.03310.030*
H120.08180.37920.07880.032*
H130.26740.34990.07100.033*
H170.55770.17500.07180.033*
H180.55830.08640.15330.034*
H220.02280.16580.26960.032*
H230.13500.13530.32880.037*
H240.26970.05030.29380.039*
H250.29120.00550.20000.035*
H28A0.29620.07250.00220.055*
H28B0.20780.12150.04380.055*
H300.07500.43610.02940.036*
H310.18740.52240.02980.041*
H320.26800.49430.13070.035*
H330.23840.38110.17160.029*
H36A0.05740.16530.20800.040*
H36B0.16680.13420.20320.040*
H380.39790.19290.08200.039*
H390.50920.23610.13920.048*
H400.61940.33460.10520.052*
H410.61990.39620.01650.049*
H44A0.49410.49590.14130.100*
H44B0.58280.44620.18230.100*
H460.45160.07850.30020.031*
H470.56890.00230.36640.034*
H480.63540.10330.33150.034*
H490.58030.13380.22870.036*
H52A0.23600.10830.04790.065*
H52B0.30610.17990.05190.065*
H53A0.14920.35850.21210.048*
H53B0.07790.30220.17430.048*
H53C0.12950.36450.14210.048*
H540.73620.22710.28630.110*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn0.0146 (2)0.0212 (2)0.0141 (2)0.00009 (19)0.00265 (16)0.00104 (18)
Cl10.0427 (7)0.0485 (8)0.0281 (6)0.0024 (6)0.0078 (5)0.0058 (5)
Cl20.0504 (8)0.0312 (6)0.0332 (6)0.0109 (5)0.0011 (5)0.0038 (5)
Cl30.0693 (10)0.0421 (8)0.0432 (7)0.0021 (7)0.0192 (7)0.0106 (6)
Cl40.0629 (10)0.1104 (14)0.0281 (7)0.0351 (10)0.0094 (6)0.0021 (7)
Cl50.1065 (17)0.0740 (13)0.1310 (18)0.0452 (12)0.0775 (15)0.0468 (12)
Cl60.145 (2)0.1125 (18)0.0733 (13)0.0725 (17)0.0163 (14)0.0197 (13)
Cl70.1147 (19)0.1098 (17)0.1280 (19)0.0586 (15)0.0870 (16)0.0549 (15)
O10.046 (2)0.080 (3)0.043 (2)0.034 (2)0.0122 (18)0.012 (2)
O20.051 (2)0.0320 (18)0.0181 (15)0.0016 (16)0.0054 (14)0.0002 (14)
O30.141 (6)0.168 (7)0.113 (5)0.122 (6)0.067 (4)0.068 (5)
O40.041 (2)0.078 (3)0.047 (2)0.020 (2)0.0123 (18)0.018 (2)
O50.0256 (16)0.0222 (15)0.0173 (13)0.0020 (12)0.0005 (12)0.0022 (11)
N10.0174 (17)0.0210 (17)0.0157 (15)0.0000 (14)0.0032 (13)0.0015 (13)
N20.0167 (17)0.0200 (18)0.0154 (15)0.0004 (13)0.0030 (13)0.0013 (13)
N30.0195 (18)0.0235 (18)0.0151 (15)0.0004 (14)0.0021 (13)0.0015 (13)
N40.0186 (18)0.0227 (18)0.0181 (16)0.0005 (14)0.0041 (13)0.0030 (14)
N50.0229 (19)0.035 (2)0.0241 (18)0.0070 (16)0.0065 (15)0.0034 (16)
N60.029 (2)0.0219 (19)0.0190 (17)0.0051 (15)0.0000 (14)0.0011 (14)
N70.044 (3)0.046 (3)0.040 (2)0.021 (2)0.015 (2)0.007 (2)
N80.036 (2)0.033 (2)0.0249 (18)0.0086 (18)0.0085 (16)0.0010 (16)
C10.016 (2)0.021 (2)0.0152 (17)0.0016 (16)0.0019 (15)0.0025 (15)
C20.023 (2)0.018 (2)0.0177 (18)0.0028 (16)0.0048 (16)0.0010 (16)
C30.022 (2)0.017 (2)0.0190 (19)0.0045 (16)0.0061 (16)0.0003 (15)
C40.019 (2)0.017 (2)0.0154 (17)0.0045 (15)0.0029 (15)0.0018 (15)
C50.0159 (19)0.023 (2)0.0163 (18)0.0006 (16)0.0050 (15)0.0020 (16)
C60.017 (2)0.027 (2)0.0152 (18)0.0001 (16)0.0035 (15)0.0036 (16)
C70.016 (2)0.037 (3)0.022 (2)0.0029 (18)0.0036 (16)0.0043 (18)
C80.021 (2)0.031 (2)0.020 (2)0.0051 (18)0.0027 (17)0.0002 (17)
C90.016 (2)0.026 (2)0.0152 (18)0.0014 (16)0.0007 (15)0.0023 (16)
C100.022 (2)0.024 (2)0.0119 (17)0.0009 (17)0.0017 (15)0.0050 (16)
C110.018 (2)0.020 (2)0.0159 (17)0.0011 (16)0.0005 (15)0.0016 (16)
C120.027 (2)0.031 (2)0.022 (2)0.0024 (19)0.0070 (17)0.0068 (18)
C130.028 (2)0.035 (2)0.019 (2)0.0019 (19)0.0068 (17)0.0087 (18)
C140.022 (2)0.026 (2)0.0199 (19)0.0018 (17)0.0063 (16)0.0044 (17)
C150.022 (2)0.026 (2)0.0199 (19)0.0016 (17)0.0058 (16)0.0002 (17)
C160.019 (2)0.029 (2)0.0193 (19)0.0036 (18)0.0063 (16)0.0001 (17)
C170.019 (2)0.035 (3)0.030 (2)0.0041 (19)0.0096 (18)0.0060 (19)
C180.021 (2)0.036 (3)0.028 (2)0.0092 (19)0.0067 (18)0.0081 (19)
C190.018 (2)0.029 (2)0.0166 (18)0.0012 (17)0.0035 (15)0.0015 (17)
C200.019 (2)0.022 (2)0.0185 (18)0.0030 (16)0.0055 (16)0.0006 (16)
C210.015 (2)0.026 (2)0.0208 (19)0.0020 (16)0.0037 (16)0.0033 (16)
C220.026 (2)0.032 (2)0.024 (2)0.0025 (19)0.0100 (18)0.0006 (18)
C230.031 (3)0.040 (3)0.025 (2)0.003 (2)0.0141 (19)0.003 (2)
C240.025 (2)0.044 (3)0.031 (2)0.003 (2)0.0144 (19)0.006 (2)
C250.017 (2)0.037 (3)0.032 (2)0.0007 (19)0.0063 (18)0.007 (2)
C260.019 (2)0.027 (2)0.024 (2)0.0021 (17)0.0046 (17)0.0050 (17)
C270.041 (3)0.051 (3)0.029 (2)0.017 (3)0.004 (2)0.002 (2)
C280.051 (3)0.048 (3)0.035 (3)0.016 (3)0.004 (2)0.013 (2)
C290.019 (2)0.025 (2)0.0197 (19)0.0016 (17)0.0048 (16)0.0044 (17)
C300.034 (3)0.028 (2)0.023 (2)0.002 (2)0.0012 (19)0.0047 (18)
C310.041 (3)0.025 (2)0.035 (3)0.009 (2)0.005 (2)0.003 (2)
C320.027 (2)0.029 (2)0.031 (2)0.0056 (19)0.0062 (19)0.0096 (19)
C330.020 (2)0.026 (2)0.023 (2)0.0042 (17)0.0013 (16)0.0018 (17)
C340.021 (2)0.022 (2)0.0168 (18)0.0018 (17)0.0037 (16)0.0002 (16)
C350.030 (2)0.027 (2)0.025 (2)0.0056 (19)0.0049 (18)0.0041 (18)
C360.041 (3)0.033 (3)0.022 (2)0.003 (2)0.003 (2)0.0012 (19)
C370.020 (2)0.034 (3)0.026 (2)0.0017 (19)0.0081 (17)0.0092 (19)
C380.034 (3)0.036 (3)0.028 (2)0.005 (2)0.010 (2)0.007 (2)
C390.045 (3)0.047 (3)0.033 (3)0.012 (3)0.022 (2)0.012 (2)
C400.028 (3)0.057 (4)0.049 (3)0.004 (2)0.018 (2)0.024 (3)
C410.024 (3)0.054 (3)0.046 (3)0.006 (2)0.011 (2)0.012 (3)
C420.023 (2)0.037 (3)0.038 (3)0.004 (2)0.006 (2)0.011 (2)
C430.081 (5)0.087 (5)0.071 (5)0.056 (5)0.031 (4)0.021 (4)
C440.117 (7)0.072 (5)0.067 (4)0.054 (5)0.036 (4)0.037 (4)
C450.015 (2)0.030 (2)0.024 (2)0.0027 (17)0.0082 (16)0.0053 (17)
C460.024 (2)0.028 (2)0.025 (2)0.0033 (18)0.0059 (17)0.0010 (18)
C470.028 (2)0.032 (2)0.024 (2)0.0014 (19)0.0033 (18)0.0045 (19)
C480.024 (2)0.030 (2)0.029 (2)0.0043 (19)0.0013 (18)0.0102 (19)
C490.024 (2)0.030 (3)0.035 (2)0.0058 (19)0.0053 (19)0.005 (2)
C500.021 (2)0.026 (2)0.023 (2)0.0030 (18)0.0040 (17)0.0035 (17)
C510.035 (3)0.046 (3)0.034 (3)0.008 (2)0.003 (2)0.008 (2)
C520.053 (4)0.064 (4)0.038 (3)0.015 (3)0.001 (3)0.011 (3)
C530.042 (3)0.033 (3)0.039 (3)0.007 (2)0.003 (2)0.016 (2)
C540.068 (5)0.053 (4)0.168 (9)0.017 (4)0.055 (6)0.020 (5)
Geometric parameters (Å, º) top
Zn—N12.051 (5)C9—C101.416 (6)
Zn—N22.072 (3)C10—C111.396 (6)
Zn—N32.062 (7)C10—C291.496 (6)
Zn—N42.067 (4)C11—C121.440 (7)
Zn—O52.147 (5)C12—C131.343 (6)
Cl1—C281.781 (6)C13—C141.446 (7)
Cl2—C361.782 (7)C14—C151.406 (6)
Cl3—C441.782 (7)C15—C161.401 (7)
Cl4—C521.767 (8)C15—C371.500 (6)
Cl5—C541.703 (8)C16—C171.449 (6)
Cl6—C541.727 (9)C17—C181.339 (7)
Cl7—C541.724 (12)C18—C191.443 (6)
O1—C271.223 (6)C19—C201.406 (6)
O2—C351.223 (6)C20—C451.504 (6)
O3—C431.214 (8)C21—C221.388 (7)
O4—C511.217 (7)C21—C261.396 (6)
O5—C531.425 (6)C22—C231.383 (6)
N1—C11.384 (5)C23—C241.379 (7)
N1—C41.367 (5)C24—C251.380 (8)
N2—C61.370 (6)C25—C261.414 (6)
N2—C91.371 (5)C27—C281.528 (9)
N3—C111.378 (5)C29—C301.381 (6)
N3—C141.370 (5)C29—C341.407 (7)
N4—C161.369 (6)C30—C311.384 (7)
N4—C191.369 (6)C31—C321.393 (8)
N5—C261.416 (7)C32—C331.378 (6)
N5—C271.353 (6)C33—C341.395 (6)
N6—C341.416 (5)C35—C361.520 (7)
N6—C351.343 (7)C37—C381.389 (8)
N7—C421.406 (8)C37—C421.398 (7)
N7—C431.335 (8)C38—C391.393 (7)
N8—C501.437 (7)C39—C401.367 (8)
N8—C511.346 (7)C40—C411.372 (9)
C1—C21.449 (6)C41—C421.414 (7)
C1—C201.392 (6)C43—C441.534 (11)
C2—C31.351 (6)C45—C461.382 (8)
C3—C41.445 (6)C45—C501.403 (6)
C4—C51.408 (6)C46—C471.385 (6)
C5—C61.399 (6)C47—C481.376 (7)
C5—C211.500 (6)C48—C491.394 (8)
C6—C71.447 (6)C49—C501.387 (6)
C7—C81.359 (7)C51—C521.509 (9)
C8—C91.434 (6)
N1—Zn—N289.48 (13)N4—C19—C20125.4 (4)
N1—Zn—N3164.92 (13)N4—C19—C18109.5 (4)
N1—Zn—N488.84 (14)C20—C19—C18125.2 (4)
N3—Zn—N288.68 (13)C1—C20—C19125.4 (4)
N3—Zn—N489.11 (14)C1—C20—C45116.2 (4)
N4—Zn—N2165.12 (13)C19—C20—C45118.4 (4)
N1—Zn—O595.6 (3)C22—C21—C26118.2 (4)
N3—Zn—O599.5 (3)C22—C21—C5119.2 (4)
N4—Zn—O598.35 (13)C26—C21—C5122.6 (4)
N2—Zn—O596.52 (12)C23—C22—C21121.9 (4)
C53—O5—Zn119.9 (3)C24—C23—C22119.7 (4)
C4—N1—C1106.8 (3)C23—C24—C25120.4 (4)
C4—N1—Zn126.2 (3)C24—C25—C26119.8 (5)
C1—N1—Zn126.6 (3)C21—C26—C25120.1 (4)
C6—N2—C9106.3 (4)C21—C26—N5117.8 (4)
C6—N2—Zn125.8 (3)C25—C26—N5122.1 (4)
C9—N2—Zn126.8 (3)O1—C27—N5125.6 (5)
C14—N3—C11106.9 (3)O1—C27—C28118.7 (5)
C14—N3—Zn126.5 (3)N5—C27—C28115.7 (5)
C11—N3—Zn126.2 (3)C27—C28—Cl1117.0 (4)
C16—N4—C19106.8 (4)C30—C29—C34118.4 (4)
C16—N4—Zn126.1 (3)C30—C29—C10121.0 (4)
C19—N4—Zn126.5 (3)C34—C29—C10120.5 (4)
C27—N5—C26127.8 (4)C29—C30—C31121.8 (4)
C35—N6—C34129.3 (4)C30—C31—C32118.9 (4)
C43—N7—C42131.1 (5)C33—C32—C31121.1 (4)
C51—N8—C50119.2 (4)C32—C33—C34119.3 (4)
N1—C1—C20125.7 (4)C33—C34—C29120.5 (4)
N1—C1—C2108.8 (3)C33—C34—N6123.1 (4)
C20—C1—C2125.5 (4)C29—C34—N6116.4 (4)
C3—C2—C1107.6 (3)O2—C35—N6125.0 (4)
C2—C3—C4106.9 (4)O2—C35—C36118.0 (4)
N1—C4—C5125.7 (4)N6—C35—C36117.0 (4)
N1—C4—C3109.9 (4)C35—C36—Cl2115.5 (3)
C5—C4—C3124.5 (4)C38—C37—C42118.8 (4)
C6—C5—C4125.8 (4)C38—C37—C15119.8 (4)
C6—C5—C21118.1 (4)C42—C37—C15121.3 (4)
C4—C5—C21116.0 (4)C37—C38—C39120.4 (5)
N2—C6—C5125.4 (4)C40—C39—C38119.5 (5)
N2—C6—C7109.8 (4)C39—C40—C41122.6 (5)
C5—C6—C7124.8 (4)C40—C41—C42117.8 (5)
C8—C7—C6106.8 (4)C37—C42—N7116.1 (4)
C7—C8—C9106.9 (4)C37—C42—C41120.8 (5)
N2—C9—C10124.4 (4)N7—C42—C41123.0 (5)
N2—C9—C8110.3 (4)O3—C43—N7125.2 (7)
C10—C9—C8125.3 (4)O3—C43—C44118.1 (6)
C11—C10—C9125.8 (4)N7—C43—C44116.7 (6)
C11—C10—C29116.5 (4)C43—C44—Cl3114.8 (4)
C9—C10—C29117.7 (4)C46—C45—C50117.5 (4)
N3—C11—C10125.9 (4)C46—C45—C20120.8 (4)
N3—C11—C12109.1 (4)C50—C45—C20121.6 (4)
C10—C11—C12125.0 (4)C45—C46—C47121.7 (4)
C13—C12—C11107.6 (4)C48—C47—C46120.4 (4)
C12—C13—C14107.2 (4)C47—C48—C49119.3 (4)
N3—C14—C15126.0 (4)C50—C49—C48119.9 (4)
N3—C14—C13109.2 (4)C49—C50—C45121.2 (4)
C15—C14—C13124.7 (4)C49—C50—N8119.4 (4)
C16—C15—C14124.9 (4)C45—C50—N8119.4 (4)
C16—C15—C37119.0 (4)O4—C51—N8123.8 (5)
C14—C15—C37116.1 (4)O4—C51—C52117.9 (5)
N4—C16—C15126.1 (4)N8—C51—C52118.3 (5)
N4—C16—C17109.1 (4)C51—C52—Cl4115.2 (5)
C15—C16—C17124.7 (4)Cl5—C54—Cl7114.5 (6)
C18—C17—C16107.3 (4)Cl5—C54—Cl6111.7 (5)
C17—C18—C19107.3 (4)Cl7—C54—Cl6110.2 (5)

Experimental details

Crystal data
Chemical formula[Zn(C52H36Cl4N8O4)(CH4O)]·CHCl3
Mr1195.47
Crystal system, space groupMonoclinic, P21/n
Temperature (K)110
a, b, c (Å)13.078 (6), 17.899 (7), 22.79 (9)
β (°) 105.009 (2)
V3)5153 (21)
Z4
Radiation typeMo Kα
µ (mm1)0.90
Crystal size (mm)0.25 × 0.25 × 0.25
Data collection
DiffractometerKappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
19872, 11775, 7802
Rint0.033
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.069, 0.187, 1.04
No. of reflections11775
No. of parameters676
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0845P)2 + 10.6403P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)1.27, 1.62

Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), SHELXL97 and WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top
Zn—N12.051 (5)Zn—N42.067 (4)
Zn—N22.072 (3)Zn—O52.147 (5)
Zn—N32.062 (7)
N1—Zn—N289.48 (13)N4—Zn—N2165.12 (13)
N1—Zn—N3164.92 (13)N1—Zn—O595.6 (3)
N1—Zn—N488.84 (14)N3—Zn—O599.5 (3)
N3—Zn—N288.68 (13)N4—Zn—O598.35 (13)
N3—Zn—N489.11 (14)N2—Zn—O596.52 (12)
 

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