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The title compound, [Zn(C44H28Cl4N4)], is a four-coordinate zinc–porphyrin complex, with 3-chloro­phenyl substituents at the meso positions of the planar metallo­porphyrin core. The mol­ecules are located on crystallographic inversion centres, exhibiting partial orientational disorder of the aryl residues. The crystal packing is stabilized by van der Waals forces and inter­molecular Cl...Cl inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806008543/kp2008sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806008543/kp2008Isup2.hkl
Contains datablock I

CCDC reference: 605248

Key indicators

  • Single-crystal X-ray study
  • T = 110 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in main residue
  • R factor = 0.061
  • wR factor = 0.171
  • Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.99 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.04 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT301_ALERT_3_C Main Residue Disorder ......................... 4.00 Perc.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 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 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: COLLECT (Nonius, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SIR97 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL97.

[Tetrakis(3-chlorophenyl)porphyrinato]zinc(II) top
Crystal data top
[Zn(C44H24Cl4N4)]F(000) = 828
Mr = 815.84Dx = 1.539 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 14.7205 (4) ÅCell parameters from 3801 reflections
b = 9.4071 (3) Åθ = 2.6–27.9°
c = 13.5925 (5) ŵ = 1.04 mm1
β = 110.7208 (17)°T = 110 K
V = 1760.50 (10) Å3Prism, violet
Z = 20.40 × 0.35 × 0.25 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
4179 independent reflections
Radiation source: fine-focus sealed tube2961 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
Detector resolution: 56 microns pixels mm-1θmax = 27.9°, θmin = 2.6°
φ scansh = 1918
Absorption correction: multi-scan
(Blessing, 1995)
k = 1212
Tmin = 0.681, Tmax = 0.781l = 1717
12967 measured reflections
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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0873P)2 + 1.8321P]
where P = (Fo2 + 2Fc2)/3
4179 reflections(Δ/σ)max < 0.001
251 parametersΔρmax = 1.49 e Å3
0 restraintsΔρmin = 0.73 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*/UeqOcc. (<1)
Zn0.00000.50000.00000.03056 (19)
C10.0188 (2)0.6401 (4)0.1948 (3)0.0337 (7)
C20.0369 (3)0.7207 (4)0.2871 (3)0.0392 (8)
H20.01350.75880.33850.047*
C30.1280 (3)0.7316 (4)0.2867 (3)0.0399 (8)
H30.18060.77960.33760.048*
C40.1312 (2)0.6577 (4)0.1958 (3)0.0346 (7)
C50.2129 (2)0.6501 (4)0.1658 (3)0.0336 (7)
C60.2158 (2)0.5855 (3)0.0737 (3)0.0323 (7)
C70.2996 (2)0.5771 (4)0.0437 (3)0.0348 (8)
H70.36190.61560.08140.042*
C80.2741 (2)0.5040 (3)0.0485 (3)0.0325 (7)
H80.31470.48180.08720.039*
C90.1727 (2)0.4668 (4)0.0758 (3)0.0323 (7)
C100.1172 (3)0.3938 (4)0.1669 (3)0.0334 (7)
N210.0404 (2)0.6032 (3)0.1398 (2)0.0324 (6)
N220.1384 (2)0.5172 (3)0.0003 (2)0.0316 (6)
C250.3050 (3)0.7174 (4)0.2380 (3)0.0374 (8)
C260.3518 (3)0.6655 (4)0.3396 (3)0.0452 (9)
H260.32610.58600.36410.054*
C270.4364 (3)0.7309 (5)0.4044 (3)0.0560 (12)
H270.46820.69560.47360.067*0.347 (3)
C280.4749 (3)0.8450 (5)0.3713 (4)0.0598 (12)
H280.53280.88840.41660.072*
C290.4284 (3)0.8972 (5)0.2708 (4)0.0592 (12)
H290.45480.97660.24700.071*0.653 (3)
C300.3440 (3)0.8341 (4)0.2042 (3)0.0461 (9)
H300.31260.87090.13540.055*
C310.1660 (2)0.3539 (4)0.2429 (3)0.0353 (8)
C320.2414 (3)0.2550 (4)0.2165 (3)0.0411 (8)
H320.26060.20870.15020.049*
C330.2891 (3)0.2235 (4)0.2861 (3)0.0445 (9)
H330.34120.15730.26660.053*
C340.2593 (3)0.2885 (4)0.3843 (3)0.0442 (9)
H340.29090.26730.43260.053*
C350.1843 (3)0.3845 (4)0.4099 (3)0.0429 (9)
C360.1370 (3)0.4189 (4)0.3417 (3)0.0390 (8)
H360.08540.48590.36150.047*
Cl10.49746 (12)0.6797 (2)0.52779 (13)0.0613 (6)0.653 (3)
Cl1'0.4805 (2)1.0225 (3)0.2402 (3)0.0602 (11)0.347 (3)
Cl20.15001 (9)0.47244 (14)0.53082 (8)0.0612 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn0.0307 (3)0.0312 (3)0.0268 (3)0.0016 (2)0.0065 (2)0.0027 (2)
C10.0360 (18)0.0319 (16)0.0308 (17)0.0004 (14)0.0088 (14)0.0034 (13)
C20.040 (2)0.0390 (18)0.0357 (18)0.0002 (16)0.0093 (16)0.0093 (15)
C30.043 (2)0.0380 (19)0.0347 (18)0.0046 (16)0.0090 (16)0.0107 (15)
C40.0339 (17)0.0319 (16)0.0321 (17)0.0015 (14)0.0044 (14)0.0061 (14)
C50.0308 (17)0.0317 (16)0.0326 (17)0.0001 (14)0.0044 (14)0.0022 (13)
C60.0327 (17)0.0307 (16)0.0288 (16)0.0001 (13)0.0051 (14)0.0001 (13)
C70.0311 (17)0.0320 (17)0.0356 (18)0.0016 (14)0.0047 (14)0.0012 (14)
C80.0323 (17)0.0321 (16)0.0305 (16)0.0008 (14)0.0079 (14)0.0004 (14)
C90.0322 (17)0.0326 (16)0.0308 (17)0.0007 (14)0.0095 (14)0.0019 (13)
C100.0373 (18)0.0306 (16)0.0302 (17)0.0006 (14)0.0095 (14)0.0003 (13)
N210.0315 (14)0.0311 (14)0.0306 (14)0.0027 (11)0.0060 (12)0.0043 (11)
N220.0324 (14)0.0317 (14)0.0277 (14)0.0000 (11)0.0069 (12)0.0000 (11)
C250.0311 (17)0.0392 (18)0.0382 (19)0.0019 (15)0.0077 (15)0.0108 (15)
C260.040 (2)0.051 (2)0.039 (2)0.0033 (17)0.0060 (16)0.0116 (17)
C270.038 (2)0.075 (3)0.043 (2)0.010 (2)0.0011 (18)0.020 (2)
C280.035 (2)0.073 (3)0.064 (3)0.010 (2)0.008 (2)0.029 (2)
C290.042 (2)0.059 (3)0.073 (3)0.012 (2)0.015 (2)0.021 (2)
C300.0364 (19)0.044 (2)0.054 (2)0.0033 (17)0.0114 (18)0.0118 (18)
C310.0338 (17)0.0363 (18)0.0341 (18)0.0049 (15)0.0098 (14)0.0063 (14)
C320.044 (2)0.0393 (19)0.0372 (19)0.0015 (16)0.0107 (17)0.0025 (15)
C330.046 (2)0.044 (2)0.044 (2)0.0041 (17)0.0171 (18)0.0033 (17)
C340.047 (2)0.047 (2)0.041 (2)0.0029 (18)0.0175 (17)0.0114 (17)
C350.052 (2)0.046 (2)0.0298 (18)0.0087 (17)0.0133 (17)0.0052 (15)
C360.041 (2)0.0392 (19)0.0350 (18)0.0008 (16)0.0110 (16)0.0047 (15)
Cl10.0462 (9)0.0831 (13)0.0392 (9)0.0075 (8)0.0040 (7)0.0040 (8)
Cl1'0.0446 (17)0.0510 (18)0.074 (2)0.0177 (13)0.0076 (15)0.0102 (15)
Cl20.0670 (7)0.0800 (8)0.0349 (5)0.0102 (6)0.0161 (5)0.0058 (5)
Geometric parameters (Å, º) top
Zn—N21i2.027 (3)C25—C301.389 (6)
Zn—N212.027 (3)C25—C261.395 (5)
Zn—N22i2.045 (3)C26—C271.389 (5)
Zn—N222.045 (3)C26—H260.9500
C1—N211.378 (4)C27—C281.362 (7)
C1—C10i1.399 (5)C27—Cl11.669 (5)
C1—C21.447 (5)C27—H270.9500
C2—C31.347 (5)C28—C291.384 (7)
C2—H20.9500C28—H280.9500
C3—C41.434 (5)C29—C301.386 (5)
C3—H30.9500C29—Cl1'1.541 (6)
C4—N211.382 (4)C29—H290.9500
C4—C51.401 (5)C30—H300.9500
C5—C61.405 (5)C31—C321.395 (5)
C5—C251.504 (5)C31—C361.398 (5)
C6—N221.383 (4)C32—C331.395 (5)
C6—C71.432 (5)C32—H320.9500
C7—C81.360 (5)C33—C341.391 (6)
C7—H70.9500C33—H330.9500
C8—C91.447 (5)C34—C351.372 (6)
C8—H80.9500C34—H340.9500
C9—N221.379 (4)C35—C361.381 (5)
C9—C101.399 (5)C35—Cl21.747 (4)
C10—C1i1.399 (5)C36—H360.9500
C10—C311.499 (5)
N21i—Zn—N21180.0C6—N22—Zn126.9 (2)
N21i—Zn—N22i90.12 (11)C30—C25—C26119.1 (3)
N21—Zn—N22i89.88 (11)C30—C25—C5120.0 (3)
N21i—Zn—N2289.88 (11)C26—C25—C5120.9 (3)
N21—Zn—N2290.12 (11)C27—C26—C25119.4 (4)
N22i—Zn—N22180.0C27—C26—H26120.3
N21—C1—C10i126.1 (3)C25—C26—H26120.3
N21—C1—C2109.3 (3)C28—C27—C26121.6 (4)
C10i—C1—C2124.7 (3)C28—C27—Cl1114.8 (3)
C3—C2—C1107.2 (3)C26—C27—Cl1123.6 (4)
C3—C2—H2126.4C28—C27—H27119.1
C1—C2—H2126.4C26—C27—H27119.4
C2—C3—C4107.7 (3)C27—C28—C29119.2 (4)
C2—C3—H3126.2C27—C28—H28120.5
C4—C3—H3126.2C29—C28—H28120.3
N21—C4—C5125.7 (3)C28—C29—C30120.5 (5)
N21—C4—C3109.5 (3)C28—C29—Cl1'114.8 (4)
C5—C4—C3124.7 (3)C30—C29—Cl1'124.6 (4)
C4—C5—C6125.5 (3)C28—C29—H29119.7
C4—C5—C25117.2 (3)C30—C29—H29119.7
C6—C5—C25117.3 (3)C25—C30—C29120.2 (4)
N22—C6—C5124.9 (3)C25—C30—H30120.0
N22—C6—C7109.8 (3)C29—C30—H30119.9
C5—C6—C7125.3 (3)C32—C31—C36118.9 (3)
C8—C7—C6107.7 (3)C32—C31—C10121.4 (3)
C8—C7—H7126.1C36—C31—C10119.6 (3)
C6—C7—H7126.1C31—C32—C33120.9 (3)
C7—C8—C9106.4 (3)C31—C32—H32119.5
C7—C8—H8126.8C33—C32—H32119.6
C9—C8—H8126.8C34—C33—C32119.6 (4)
N22—C9—C10125.1 (3)C34—C33—H33120.3
N22—C9—C8110.0 (3)C32—C33—H33120.1
C10—C9—C8124.9 (3)C35—C34—C33119.0 (3)
C1i—C10—C9125.2 (3)C35—C34—H34120.6
C1i—C10—C31117.3 (3)C33—C34—H34120.4
C9—C10—C31117.4 (3)C34—C35—C36122.4 (4)
C1—N21—C4106.4 (3)C34—C35—Cl2119.3 (3)
C1—N21—Zn126.7 (2)C36—C35—Cl2118.3 (3)
C4—N21—Zn126.8 (2)C35—C36—C31119.2 (4)
C9—N22—C6106.0 (3)C35—C36—H36120.5
C9—N22—Zn127.1 (2)C31—C36—H36120.3
Symmetry code: (i) x, y+1, z.
 

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