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The crystal structure of the title compound, [Zn(C50H58N6)]·CHCl3, reveals a polymeric chain in a zigzag conformation, with a single pyridyl group from each porphyrin making the connection.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801015264/ci6042sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801015264/ci6042Isup2.hkl
Contains datablock I

CCDC reference: 175342

Key indicators

  • Single-crystal X-ray study
  • T = 203 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in main residue
  • R factor = 0.065
  • wR factor = 0.169
  • Data-to-parameter ratio = 18.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_301 Alert C Main Residue Disorder ........................ 3.00 Perc.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

The formation of porphyrin assemblies using coordination chemistry has been an active area of research for the last few years. The formation of coordination polymers using zinc porphyrins with pyridyl substituents was pioneered by the Fleischer group (Shachter et al., 1988). Recently, we have explored the use of pyridyl porphyrins to prepare porphyrin assemblies (Burrell et al., 1998). In general, the number of pyridyl groups on the porphyrin has little effect on the nature of solid-state structure of the polymer obtained upon insertion of zinc. Thus, the monopyridyl porphyrin (Shachter et al., 1988) has essentially the same structure as the tetrapyridyl analogue (Krupitsky et al., 1994).

In the title compound, (I), the porphyrin has β-alkyl groups which have a different steric requirement than phenyls or pyridyls (Fig. 1). However, the same structural motif is conserved with a single pyridyl group being utilized in formation of the coordination polymer (Fig. 2). The linear chains are stacked one upon another with the closest approach being approximately 4 Å. The sheets that result from this stacking are separated by channels that contain the chloroform solvate.

Experimental top

The 5,15-bis(4-pyridyl)porphyrin was synthesized according to a previously reported method (Forsyth et al., 1995). Zinc insertion: zinc acetate (4.61 mg, 21.0 µM) dissolved in MeOH (3 ml) was added to 5,15-bis(4-pyridyl)porphyrin (15.5 mg, 20.8 microM) in CH2Cl2 (20 ml). The mixture was refluxed for 20 min, at which point thin-layer chromatography (1% MeOH/CH2Cl2) showed the reaction was complete. The solvent was removed and the residue was dissolved in CH2Cl2 (10 ml), washed with water (10 ml) and dried (MgSO4). Quantitative yield. Crystals were grown by the slow evaporation of a 1:1 solvent mixture of CHCl3/MeOH. 1H NMR (400 MHz, CDCl3): 9.95 (s, 2H), 7.06 (s br, 4H), 3.78 (t, 8H), 1.98 (quint, 8H), 1.61 (m, 8H), 1.62 (s br, 4H), 1.24 (s, 12H), 1.00 (t, 12H).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. ORTEP-3 (Farrugia, 1997) view of (I) showing displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. The polymer conformation where ZnA is generated by x - 1/2, -y + 1/2, z - 1/2 and ZnB is generated by -x + 1/2, y + 1/2, -z + 1/2.
5,15-bis(4-pyridyl)-2,8,12,18-tetra-n-butyl-3,7,13,17- tetramethylporphyrinato zinc(II) chloroform solvate top
Crystal data top
[Zn(C50H58N6)]·CHCl3F(000) = 1952
Mr = 927.76Dx = 1.300 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 17.8146 (2) ÅCell parameters from 6496 reflections
b = 13.1650 (2) Åθ = 1.5–28.3°
c = 20.2171 (4) ŵ = 0.73 mm1
β = 90.84 (1)°T = 203 K
V = 4741.00 (13) Å3Plate, red
Z = 40.30 × 0.22 × 0.02 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
10404 independent reflections
Radiation source: fine-focus sealed tube6454 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.000
ω scansθmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan
(Blessing, 1995)
h = 2323
Tmin = 0.800, Tmax = 0.986k = 017
10404 measured reflectionsl = 026
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0548P)2 + 7.9269P]
where P = (Fo2 + 2Fc2)/3
10404 reflections(Δ/σ)max = 0.020
564 parametersΔρmax = 0.78 e Å3
0 restraintsΔρmin = 1.03 e Å3
Crystal data top
[Zn(C50H58N6)]·CHCl3V = 4741.00 (13) Å3
Mr = 927.76Z = 4
Monoclinic, P21/nMo Kα radiation
a = 17.8146 (2) ŵ = 0.73 mm1
b = 13.1650 (2) ÅT = 203 K
c = 20.2171 (4) Å0.30 × 0.22 × 0.02 mm
β = 90.84 (1)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
10404 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)
6454 reflections with I > 2σ(I)
Tmin = 0.800, Tmax = 0.986Rint = 0.000
10404 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0650 restraints
wR(F2) = 0.169H-atom parameters constrained
S = 1.08Δρmax = 0.78 e Å3
10404 reflectionsΔρmin = 1.03 e Å3
564 parameters
Special details top

Experimental. One n-butyl chain was found disordered (59/41 occupation factors). The n-butyl carbon atoms (C22 and C23) were refined with two split positions, and the hydrogen atoms attach to C21, C22, C23 and C24 have been fixed taking into account the different orientation of the minor(A) and major(B) components of the disordered n-butyl chain.

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)
Zn0.60265 (3)0.09136 (3)0.87486 (2)0.02432 (13)
N10.59162 (18)0.0451 (2)0.77638 (16)0.0275 (7)
N20.67608 (18)0.0304 (2)0.88531 (15)0.0255 (7)
N30.58646 (18)0.0988 (3)0.97568 (16)0.0276 (7)
N40.51031 (18)0.1856 (2)0.86596 (16)0.0257 (7)
N50.81503 (18)0.2932 (2)0.65123 (16)0.0275 (7)
N150.3798 (3)0.4412 (3)1.1122 (2)0.0583 (13)
C10.5463 (2)0.0939 (3)0.73144 (19)0.0271 (8)
C20.5573 (2)0.0530 (3)0.6659 (2)0.0316 (9)
C30.6100 (2)0.0206 (3)0.6716 (2)0.0342 (10)
C40.6331 (2)0.0241 (3)0.7417 (2)0.0285 (9)
C50.6896 (2)0.0858 (3)0.77056 (19)0.0266 (8)
C60.7118 (2)0.0865 (3)0.8377 (2)0.0272 (8)
C70.7731 (2)0.1447 (3)0.8688 (2)0.0290 (9)
C80.7710 (2)0.1234 (3)0.9344 (2)0.0303 (9)
C90.7101 (2)0.0541 (3)0.9445 (2)0.0277 (9)
C100.6836 (2)0.0250 (3)1.0060 (2)0.0301 (9)
H100.70910.05301.04280.036*
C110.6245 (2)0.0397 (3)1.02050 (19)0.0286 (9)
C120.5972 (2)0.0571 (3)1.0867 (2)0.0327 (10)
C130.5445 (2)0.1315 (3)1.0822 (2)0.0326 (10)
C140.5371 (2)0.1571 (3)1.01127 (19)0.0281 (9)
C150.4893 (2)0.2301 (3)0.9824 (2)0.0284 (9)
C160.4756 (2)0.2435 (3)0.9140 (2)0.0277 (9)
C170.4242 (2)0.3153 (3)0.8813 (2)0.0327 (10)
C180.4285 (2)0.2988 (3)0.8151 (2)0.0306 (9)
C190.4813 (2)0.2166 (3)0.8062 (2)0.0281 (9)
C200.4980 (2)0.1734 (3)0.7457 (2)0.0296 (9)
H200.47290.20200.70900.036*
C210.5154 (3)0.0867 (4)0.6050 (2)0.0424 (11)
H21A0.55100.09730.56910.051*0.408 (19)
H21B0.49060.15170.61370.051*0.408 (19)
H21C0.54110.06030.56600.051*0.592 (19)
H21D0.51680.16110.60270.051*0.592 (19)
C22A0.4577 (10)0.0101 (16)0.5836 (8)0.055 (5)0.408 (19)
H22A0.43520.03220.54150.066*0.408 (19)
H22B0.48290.05490.57590.066*0.408 (19)
C23A0.3967 (9)0.0060 (17)0.6322 (9)0.066 (6)0.408 (19)
H23A0.36940.05760.63900.079*0.408 (19)
H23B0.41830.02740.67480.079*0.408 (19)
C22B0.4301 (7)0.0506 (10)0.6022 (6)0.050 (3)0.592 (19)
H22C0.40350.07980.63980.060*0.592 (19)
H22D0.40630.07640.56150.060*0.592 (19)
C23B0.4221 (7)0.0641 (10)0.6039 (7)0.066 (4)0.592 (19)
H23C0.44590.09400.56510.079*0.592 (19)
H23D0.44740.09110.64360.079*0.592 (19)
C240.3399 (4)0.0923 (6)0.6045 (4)0.106 (3)
H24A0.35620.11500.56140.158*0.408 (19)
H24B0.28960.06430.60070.158*0.408 (19)
H24C0.33960.14940.63490.158*0.408 (19)
H24D0.31110.04200.57990.158*0.592 (19)
H24E0.32270.09450.64980.158*0.592 (19)
H24F0.33300.15850.58420.158*0.592 (19)
C310.6376 (3)0.0827 (5)0.6143 (2)0.0606 (16)
H31A0.61000.06380.57440.091*
H31B0.62970.15430.62330.091*
H31C0.69070.07010.60820.091*
C510.7311 (2)0.1561 (3)0.72602 (19)0.0262 (9)
C520.7951 (2)0.1255 (3)0.6933 (2)0.0312 (10)
H520.81120.05760.69560.037*
C530.8351 (2)0.1957 (3)0.6574 (2)0.0307 (9)
H530.87880.17390.63620.037*
C540.7511 (2)0.3214 (3)0.6802 (2)0.0356 (10)
H540.73440.38860.67460.043*
C550.7084 (2)0.2561 (3)0.7179 (2)0.0349 (10)
H550.66440.27940.73800.042*
C710.8303 (3)0.2148 (4)0.8388 (2)0.0443 (12)
H71A0.86480.23840.87310.066*
H71B0.85800.17860.80530.066*
H71C0.80490.27260.81890.066*
C810.8247 (3)0.1589 (4)0.9879 (2)0.0439 (12)
H81A0.84930.22170.97360.053*
H81B0.79680.17381.02810.053*
C820.8846 (3)0.0776 (5)1.0029 (3)0.0739 (18)
H82A0.90910.05950.96140.089*
H82B0.85940.01661.01910.089*
C830.9440 (4)0.1074 (6)1.0522 (3)0.082 (2)
H83A0.91970.13721.09080.099*
H83B0.97060.04621.06700.099*
C841.0000 (4)0.1816 (6)1.0264 (4)0.100 (3)
H84A0.97580.24661.01870.150*
H84B1.04050.18991.05850.150*
H84C1.02010.15640.98510.150*
C1210.6213 (3)0.0045 (4)1.1456 (2)0.0375 (11)
H12A0.62610.07541.13170.045*
H12B0.58120.00171.17830.045*
C1220.6949 (3)0.0275 (4)1.1798 (2)0.0440 (12)
H12C0.68670.09011.20490.053*
H12D0.73270.04161.14620.053*
C1230.7244 (3)0.0559 (4)1.2268 (2)0.0508 (13)
H12E0.76280.02651.25630.061*
H12F0.68300.07941.25430.061*
C1240.7577 (3)0.1466 (5)1.1912 (3)0.0652 (16)
H12G0.71890.18011.16510.098*
H12H0.77840.19401.22340.098*
H12I0.79730.12371.16230.098*
C1310.5015 (3)0.1713 (4)1.1406 (2)0.0450 (12)
H13A0.51550.13321.17990.068*
H13B0.44800.16381.13210.068*
H13C0.51320.24251.14730.068*
C1510.4504 (2)0.3022 (3)1.0279 (2)0.0317 (9)
C1520.4875 (3)0.3876 (3)1.0510 (2)0.0408 (11)
H1520.53740.40051.03920.049*
C1530.4495 (3)0.4542 (4)1.0921 (3)0.0527 (14)
H1530.47520.51261.10670.063*
C1540.3455 (3)0.3584 (4)1.0903 (3)0.0573 (15)
H1540.29590.34691.10370.069*
C1550.3778 (3)0.2875 (4)1.0489 (3)0.0474 (13)
H1550.35050.22991.03520.057*
C1710.3725 (3)0.3938 (4)0.9109 (2)0.0447 (12)
H17A0.35140.43580.87590.067*
H17B0.40060.43600.94170.067*
H17C0.33230.35980.93400.067*
C1810.3889 (3)0.3553 (4)0.7601 (2)0.0408 (11)
H18A0.33710.36940.77310.049*
H18B0.38700.31250.72050.049*
C1820.4287 (3)0.4575 (5)0.7433 (3)0.0746 (19)
H18C0.39870.49280.70940.090*
H18D0.42930.50020.78300.090*
C1830.5049 (4)0.4485 (6)0.7199 (4)0.084 (2)
H18E0.50350.41270.67740.100*
H18F0.53340.40620.75130.100*
C1840.5475 (5)0.5486 (6)0.7108 (4)0.105 (3)
H18G0.51270.60110.69650.158*
H18H0.58580.53960.67770.158*
H18I0.57100.56820.75250.158*
Cl10.70050 (9)0.38210 (13)0.00052 (8)0.0716 (4)
Cl20.71226 (16)0.30932 (17)0.13248 (9)0.1208 (9)
Cl30.80486 (12)0.22346 (17)0.02792 (16)0.1368 (10)
C1S0.7187 (3)0.2770 (4)0.0496 (3)0.0608 (15)
H1S0.67920.22610.03990.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn0.0264 (2)0.0218 (2)0.0249 (2)0.0009 (2)0.00566 (17)0.0003 (2)
N10.0290 (18)0.0251 (18)0.0284 (18)0.0016 (14)0.0042 (15)0.0020 (15)
N20.0287 (18)0.0226 (17)0.0253 (18)0.0008 (14)0.0040 (14)0.0002 (14)
N30.0302 (17)0.0268 (18)0.0259 (17)0.0015 (15)0.0065 (14)0.0015 (15)
N40.0262 (17)0.0244 (17)0.0267 (18)0.0023 (14)0.0056 (14)0.0040 (14)
N50.0309 (18)0.0266 (18)0.0253 (18)0.0019 (15)0.0067 (14)0.0010 (14)
N150.066 (3)0.046 (3)0.064 (3)0.004 (2)0.027 (2)0.018 (2)
C10.030 (2)0.025 (2)0.027 (2)0.0027 (18)0.0028 (16)0.0012 (18)
C20.033 (2)0.036 (2)0.025 (2)0.0015 (19)0.0016 (18)0.0011 (18)
C30.041 (3)0.038 (3)0.024 (2)0.002 (2)0.0044 (19)0.0041 (19)
C40.026 (2)0.029 (2)0.030 (2)0.0003 (17)0.0068 (17)0.0035 (18)
C50.0258 (19)0.025 (2)0.029 (2)0.0008 (17)0.0084 (16)0.0022 (18)
C60.028 (2)0.0206 (19)0.033 (2)0.0021 (17)0.0066 (17)0.0015 (18)
C70.026 (2)0.027 (2)0.035 (2)0.0008 (17)0.0058 (18)0.0046 (18)
C80.031 (2)0.029 (2)0.030 (2)0.0012 (17)0.0005 (18)0.0036 (18)
C90.032 (2)0.022 (2)0.029 (2)0.0004 (17)0.0024 (17)0.0013 (17)
C100.034 (2)0.028 (2)0.028 (2)0.0002 (18)0.0012 (18)0.0003 (18)
C110.035 (2)0.025 (2)0.026 (2)0.0040 (18)0.0035 (17)0.0033 (17)
C120.035 (2)0.034 (2)0.029 (2)0.0070 (19)0.0058 (18)0.0023 (18)
C130.039 (2)0.030 (2)0.030 (2)0.0074 (19)0.0092 (19)0.0039 (18)
C140.030 (2)0.028 (2)0.027 (2)0.0042 (17)0.0083 (17)0.0039 (17)
C150.028 (2)0.024 (2)0.034 (2)0.0048 (17)0.0113 (18)0.0062 (17)
C160.024 (2)0.022 (2)0.037 (2)0.0006 (16)0.0073 (17)0.0022 (18)
C170.029 (2)0.025 (2)0.044 (3)0.0029 (17)0.0070 (19)0.0023 (19)
C180.027 (2)0.026 (2)0.039 (2)0.0034 (17)0.0017 (18)0.0024 (19)
C190.023 (2)0.025 (2)0.036 (2)0.0012 (16)0.0031 (17)0.0014 (18)
C200.031 (2)0.028 (2)0.029 (2)0.0026 (18)0.0026 (17)0.0031 (18)
C210.048 (3)0.048 (3)0.031 (2)0.009 (2)0.003 (2)0.001 (2)
C22A0.048 (10)0.078 (14)0.038 (8)0.021 (9)0.006 (7)0.001 (8)
C23A0.044 (9)0.089 (15)0.065 (11)0.008 (9)0.002 (8)0.022 (10)
C22B0.045 (7)0.060 (8)0.045 (6)0.015 (5)0.016 (5)0.009 (5)
C23B0.058 (7)0.059 (8)0.082 (8)0.001 (6)0.010 (6)0.018 (6)
C240.065 (5)0.116 (7)0.135 (7)0.022 (5)0.016 (5)0.026 (6)
C310.069 (4)0.080 (4)0.032 (3)0.037 (3)0.004 (2)0.013 (3)
C510.030 (2)0.023 (2)0.026 (2)0.0015 (16)0.0055 (17)0.0005 (16)
C520.037 (2)0.024 (2)0.033 (2)0.0003 (17)0.0107 (19)0.0004 (18)
C530.032 (2)0.029 (2)0.031 (2)0.0003 (18)0.0099 (18)0.0007 (18)
C540.030 (2)0.027 (2)0.050 (3)0.0028 (18)0.012 (2)0.008 (2)
C550.029 (2)0.028 (2)0.048 (3)0.0039 (18)0.014 (2)0.007 (2)
C710.041 (3)0.055 (3)0.037 (3)0.021 (2)0.003 (2)0.004 (2)
C810.039 (3)0.051 (3)0.042 (3)0.012 (2)0.003 (2)0.001 (2)
C820.064 (4)0.079 (5)0.077 (4)0.001 (3)0.029 (3)0.002 (4)
C830.061 (4)0.109 (6)0.076 (5)0.007 (4)0.022 (3)0.008 (4)
C840.083 (5)0.107 (6)0.110 (6)0.031 (5)0.011 (5)0.008 (5)
C1210.043 (3)0.039 (3)0.030 (2)0.007 (2)0.007 (2)0.001 (2)
C1220.052 (3)0.044 (3)0.036 (3)0.014 (2)0.001 (2)0.003 (2)
C1230.053 (3)0.062 (3)0.037 (3)0.007 (3)0.008 (2)0.006 (2)
C1240.061 (4)0.067 (4)0.067 (4)0.003 (3)0.010 (3)0.002 (3)
C1310.057 (3)0.049 (3)0.029 (2)0.003 (2)0.016 (2)0.001 (2)
C1510.035 (2)0.027 (2)0.033 (2)0.0004 (18)0.0114 (19)0.0026 (18)
C1520.042 (3)0.033 (3)0.048 (3)0.003 (2)0.011 (2)0.006 (2)
C1530.064 (4)0.038 (3)0.057 (3)0.003 (3)0.009 (3)0.019 (2)
C1540.052 (3)0.050 (3)0.070 (4)0.002 (3)0.035 (3)0.003 (3)
C1550.043 (3)0.035 (3)0.064 (3)0.001 (2)0.020 (2)0.009 (2)
C1710.042 (3)0.044 (3)0.048 (3)0.014 (2)0.005 (2)0.007 (2)
C1810.033 (2)0.041 (3)0.049 (3)0.013 (2)0.003 (2)0.002 (2)
C1820.063 (4)0.077 (4)0.084 (5)0.017 (3)0.001 (3)0.045 (4)
C1830.065 (4)0.091 (5)0.095 (5)0.001 (4)0.002 (4)0.038 (4)
C1840.125 (7)0.095 (6)0.095 (6)0.053 (5)0.026 (5)0.049 (5)
Cl10.0767 (10)0.0792 (11)0.0593 (9)0.0040 (8)0.0188 (8)0.0005 (8)
Cl20.215 (3)0.0942 (15)0.0530 (10)0.0451 (16)0.0115 (13)0.0024 (10)
Cl30.0775 (14)0.0852 (15)0.249 (3)0.0179 (11)0.0294 (17)0.0114 (17)
C1S0.055 (3)0.060 (4)0.067 (4)0.015 (3)0.004 (3)0.006 (3)
Geometric parameters (Å, º) top
Zn—N32.065 (3)C13—C141.477 (6)
Zn—N42.066 (3)C13—C1311.512 (6)
Zn—N22.078 (3)C14—C151.405 (6)
Zn—N12.088 (3)C15—C161.412 (6)
Zn—N5i2.182 (3)C15—C1511.498 (5)
N1—C11.367 (5)C16—C171.466 (6)
N1—C41.372 (5)C17—C181.360 (6)
N2—C91.369 (5)C17—C1711.514 (6)
N2—C61.376 (5)C18—C191.446 (5)
N3—C111.367 (5)C18—C1811.505 (6)
N3—C141.378 (5)C19—C201.385 (6)
N4—C191.369 (5)C21—C22A1.498 (19)
N4—C161.387 (5)C21—C22B1.592 (13)
N5—C531.337 (5)C22A—C23A1.49 (3)
N5—C541.341 (5)C23A—C241.617 (18)
N5—Znii2.182 (3)C22B—C23B1.52 (2)
N15—C1531.322 (7)C23B—C241.512 (13)
N15—C1541.323 (7)C51—C551.386 (5)
C1—C201.388 (5)C51—C521.387 (5)
C1—C21.446 (5)C52—C531.379 (5)
C2—C31.354 (6)C54—C551.384 (6)
C2—C211.498 (6)C81—C821.539 (7)
C3—C41.471 (6)C82—C831.495 (8)
C3—C311.506 (6)C83—C841.496 (9)
C4—C51.413 (6)C121—C1221.533 (6)
C5—C61.408 (6)C122—C1231.539 (7)
C5—C511.494 (5)C123—C1241.521 (8)
C6—C71.469 (6)C151—C1551.381 (6)
C7—C81.358 (6)C151—C1521.382 (6)
C7—C711.508 (6)C152—C1531.391 (6)
C8—C91.433 (6)C154—C1551.384 (7)
C8—C811.507 (6)C181—C1821.560 (8)
C9—C101.392 (6)C182—C1831.448 (8)
C10—C111.389 (6)C183—C1841.533 (9)
C11—C121.450 (5)Cl1—C1S1.731 (6)
C12—C131.359 (6)Cl2—C1S1.734 (6)
C12—C1211.497 (6)Cl3—C1S1.751 (6)
N3—Zn—N486.27 (13)C13—C12—C121129.3 (4)
N3—Zn—N291.89 (13)C11—C12—C121123.6 (4)
N4—Zn—N2166.24 (13)C12—C13—C14106.4 (4)
N3—Zn—N1160.42 (13)C12—C13—C131123.7 (4)
N4—Zn—N191.62 (13)C14—C13—C131129.8 (4)
N2—Zn—N185.55 (12)N3—C14—C15123.5 (4)
N3—Zn—N5i108.03 (13)N3—C14—C13109.3 (4)
N4—Zn—N5i95.62 (13)C15—C14—C13127.2 (4)
N2—Zn—N5i97.92 (13)C14—C15—C16126.0 (4)
N1—Zn—N5i91.54 (12)C14—C15—C151117.4 (4)
C1—N1—C4106.9 (3)C16—C15—C151116.6 (4)
C1—N1—Zn122.9 (3)N4—C16—C15123.0 (4)
C4—N1—Zn129.5 (3)N4—C16—C17108.7 (3)
C9—N2—C6106.6 (3)C15—C16—C17128.3 (4)
C9—N2—Zn122.3 (3)C18—C17—C16107.3 (4)
C6—N2—Zn129.7 (3)C18—C17—C171122.8 (4)
C11—N3—C14106.6 (3)C16—C17—C171129.9 (4)
C11—N3—Zn123.5 (3)C17—C18—C19106.7 (4)
C14—N3—Zn129.9 (3)C17—C18—C181128.0 (4)
C19—N4—C16106.7 (3)C19—C18—C181125.3 (4)
C19—N4—Zn123.1 (2)N4—C19—C20125.0 (4)
C16—N4—Zn129.2 (3)N4—C19—C18110.6 (3)
C53—N5—C54116.9 (3)C20—C19—C18124.4 (4)
C53—N5—Znii120.8 (3)C19—C20—C1129.4 (4)
C54—N5—Znii119.4 (3)C2—C21—C22A111.6 (7)
C153—N15—C154115.8 (4)C2—C21—C22B113.8 (5)
N1—C1—C20125.3 (4)C22A—C21—C22B30.6 (6)
N1—C1—C2110.4 (3)C23A—C22A—C21114.2 (16)
C20—C1—C2124.3 (4)C22A—C23A—C24109.3 (15)
C3—C2—C1106.9 (4)C23B—C22B—C21112.7 (11)
C3—C2—C21128.3 (4)C24—C23B—C22B109.6 (11)
C1—C2—C21124.8 (4)C23B—C24—C23A39.5 (6)
C2—C3—C4106.8 (4)C55—C51—C52117.4 (4)
C2—C3—C31123.8 (4)C55—C51—C5120.9 (3)
C4—C3—C31129.4 (4)C52—C51—C5121.7 (4)
N1—C4—C5123.9 (4)C53—C52—C51119.4 (4)
N1—C4—C3109.0 (4)N5—C53—C52123.6 (4)
C5—C4—C3127.1 (4)N5—C54—C55123.0 (4)
C6—C5—C4126.1 (4)C54—C55—C51119.6 (4)
C6—C5—C51116.3 (3)C8—C81—C82110.9 (4)
C4—C5—C51117.6 (3)C83—C82—C81115.5 (5)
N2—C6—C5123.0 (4)C82—C83—C84114.0 (6)
N2—C6—C7109.2 (3)C12—C121—C122116.3 (4)
C5—C6—C7127.8 (4)C121—C122—C123111.4 (4)
C8—C7—C6106.2 (3)C124—C123—C122113.6 (4)
C8—C7—C71123.2 (4)C155—C151—C152117.0 (4)
C6—C7—C71130.5 (4)C155—C151—C15123.0 (4)
C7—C8—C9107.6 (4)C152—C151—C15120.0 (4)
C7—C8—C81127.6 (4)C151—C152—C153118.7 (4)
C9—C8—C81124.8 (4)N15—C153—C152124.7 (5)
N2—C9—C10124.5 (4)N15—C154—C155124.3 (5)
N2—C9—C8110.4 (3)C151—C155—C154119.5 (5)
C10—C9—C8124.6 (4)C18—C181—C182112.1 (4)
C11—C10—C9128.7 (4)C183—C182—C181115.6 (5)
N3—C11—C10125.4 (4)C182—C183—C184116.0 (7)
N3—C11—C12110.7 (4)Cl1—C1S—Cl2110.1 (3)
C10—C11—C12123.8 (4)Cl1—C1S—Cl3109.6 (3)
C13—C12—C11107.0 (4)Cl2—C1S—Cl3114.3 (4)
Symmetry codes: (i) x+3/2, y+1/2, z+3/2; (ii) x+3/2, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formula[Zn(C50H58N6)]·CHCl3
Mr927.76
Crystal system, space groupMonoclinic, P21/n
Temperature (K)203
a, b, c (Å)17.8146 (2), 13.1650 (2), 20.2171 (4)
β (°) 90.84 (1)
V3)4741.00 (13)
Z4
Radiation typeMo Kα
µ (mm1)0.73
Crystal size (mm)0.30 × 0.22 × 0.02
Data collection
DiffractometerSiemens SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(Blessing, 1995)
Tmin, Tmax0.800, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
10404, 10404, 6454
Rint0.000
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.065, 0.169, 1.08
No. of reflections10404
No. of parameters564
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.78, 1.03

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.

 

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