Crystal structure of (diethyl ether-κO)[5,10,15,20-tetra­kis­(2-iso­thio­cyanato­phen­yl)porphyrinato-κ4N]zinc diethyl ether solvate

Leben, L.; Schaub, E.; Näther, C.; Herges, R.

doi:10.1107/S2056989018014238

Crystal structure of (diethyl ether-κO)[5,10,15,20-tetrakis(2-isothiocyanatophenyl)porphyrinato-κ⁴N]zinc diethyl ether solvate

L. Leben, E. Schaub, C. Näther and R. Herges

The synthesis and crystal structure of 5,10,15,20-tetrakis α,α,α,α 2-isothiocyanatophenyl zinc(II) porphyrin are reported. The crystal structure consists of discrete porphyrin complexes that are located on a twofold rotation axis with the Zn^II cation in a square-pyramidal coordination environment defined by the porphyrin N atoms at the basal sites and a diethyl ether molecule at the apical site.

Keywords: crystal structure; picket fence porphyrin; zinc(II) porphyrin; atropisomer; isothiocyanate.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989018014238/wm5466sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989018014238/wm5466Isup2.hkl Contains datablock I

CCDC reference: 1872076

checkCIF report

Key indicators

Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.003 Å
Disorder in solvent or counterion
R factor = 0.036
wR factor = 0.103
Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level A
PLAT430_ALERT_2_A Short Inter D...A Contact  O2       ..O2       .       0.59 Ang.
                                                2-x,y,3/2-z  =      2_756 Check

Author Response: This O atom belongs to a diethylether solvate molecule, that is disord



Alert level C
PLAT260_ALERT_2_C Large Average Ueq of Residue Including        O2      0.120 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.313 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          6 Note
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          1 Check

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          5 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          5 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          2 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT230_ALERT_2_G Hirshfeld Test Diff for    S1       --C17      .        6.9 s.u.
PLAT230_ALERT_2_G Hirshfeld Test Diff for    S2       --C24      .        6.0 s.u.
PLAT300_ALERT_4_G Atom Site Occupancy of O2         Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C41        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C42        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C43        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C44        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H41A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H41B       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H41C       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H42A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H42B       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H43A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H43B       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H44A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H44B       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H44C       Constrained at        0.5 Check
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2  )       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ...... Resd  2          7.50 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  O2       ..C42              1.11 Ang.
                                                2-x,y,3/2-z  =      2_756 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  O2       ..C41              1.91 Ang.
                                                2-x,y,3/2-z  =      2_756 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  O2       ..C43              1.99 Ang.
                                                2-x,y,3/2-z  =      2_756 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  O2       ..C44              3.01 Ang.
                                                2-x,y,3/2-z  =      2_756 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  C41      ..C44              0.76 Ang.
                                                2-x,y,3/2-z  =      2_756 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  C41      ..C43              0.90 Ang.
                                                2-x,y,3/2-z  =      2_756 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  C42      ..C43              0.70 Ang.
                                                2-x,y,3/2-z  =      2_756 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  C42      ..C42              1.92 Ang.
                                                2-x,y,3/2-z  =      2_756 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  C42      ..C44              2.11 Ang.
                                                2-x,y,3/2-z  =      2_756 Check
PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) .       1.26 Ratio
PLAT773_ALERT_2_G Check long C-C Bond in CIF: C42      --C42             1.92 Ang.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #        103 Check
              C42  -O2   -C43     2.756   1.555   1.555             26.40 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #        107 Check
              C43  -O2   -C41     1.555   1.555   2.756             27.30 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #        110 Check
              C43  -C41  -C42     2.756   1.555   1.555             18.10 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #        113 Check
              C42  -C41  -O2      1.555   1.555   2.756             35.60 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #        131 Check
              O2   -C42  -O2      2.756   1.555   1.555             20.80 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #        132 Check
              C43  -C42  -C41     2.756   1.555   1.555             23.00 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #        137 Check
              O2   -C42  -C42     1.555   1.555   2.756             35.30 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #        152 Check
              C41  -C43  -C44     2.756   1.555   1.555             26.40 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #        153 Check
              C42  -C43  -O2      2.756   1.555   1.555             44.90 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #        165 Check
              C41  -C44  -C43     2.756   1.555   1.555             32.00 Deg.
PLAT794_ALERT_5_G Tentative Bond Valency for Zn1       (II)      .       1.88 Info
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         26 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          5 Info

   1 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  48 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  17 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
  31 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Computing details top

Data collection: X-AREA (Stoe, 2008); cell refinement: X-AREA (Stoe, 2008); data reduction: X-AREA (Stoe, 2008); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: XP (Sheldrick, 2008) and DIAMOND (Brandenburg, 2014); software used to prepare material for publication: publCIF (Westrip, 2010).

(Diethyl ether-κO)[5,10,15,20-tetrakis(2-isothiocyanatophenyl)porphyrinato-κ⁴N]zinc diethyl ether solvate top

Crystal data top

[Zn(C₄₈H₂₄N₈S₄)(C₄H₁₀O)]·C₄H₁₀O	F(000) = 2184
M_r = 1054.60	D_x = 1.380 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 19.8830 (4) Å	Cell parameters from 39705 reflections
b = 17.1781 (3) Å	θ = 1.6–27.0°
c = 14.8684 (3) Å	µ = 0.70 mm⁻¹
β = 91.667 (1)°	T = 200 K
V = 5076.18 (17) Å³	Block, red
Z = 4	0.14 × 0.11 × 0.07 mm

Data collection top

Stoe IPDS-2 diffractometer	5042 reflections with I > 2σ(I)
ω scans	R_int = 0.039
Absorption correction: numerical (X-Red and X-Shape; Stoe, 2008)	θ_max = 27.0°, θ_min = 1.6°
T_min = 0.807, T_max = 0.951	h = −25→25
39705 measured reflections	k = −21→21
5530 independent reflections	l = −18→18

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.036	w = 1/[σ²(F_o²) + (0.0603P)² + 2.7141P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.103	(Δ/σ)_max = 0.001
S = 1.05	Δρ_max = 0.39 e Å⁻³
5530 reflections	Δρ_min = −0.35 e Å⁻³
346 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
26 restraints	Extinction coefficient: 0.0011 (2)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Zn1	0.5000	0.64166 (2)	0.7500	0.03835 (10)
N1	0.40708 (7)	0.62138 (9)	0.68826 (9)	0.0400 (3)
N2	0.54332 (7)	0.62541 (9)	0.62706 (9)	0.0392 (3)
C1	0.34674 (8)	0.61377 (10)	0.72962 (11)	0.0405 (3)
C2	0.29355 (9)	0.60302 (11)	0.66268 (12)	0.0460 (4)
H2	0.2471	0.5962	0.6736	0.055*
C3	0.32240 (9)	0.60449 (12)	0.58175 (12)	0.0464 (4)
H3	0.3001	0.5983	0.5248	0.056*
C4	0.39333 (8)	0.61718 (10)	0.59772 (11)	0.0407 (3)
C5	0.44062 (9)	0.62460 (10)	0.53022 (11)	0.0408 (3)
C6	0.51067 (9)	0.62744 (10)	0.54465 (11)	0.0405 (3)
C7	0.55953 (9)	0.62818 (12)	0.47508 (12)	0.0472 (4)
H7	0.5503	0.6310	0.4121	0.057*
C8	0.62118 (9)	0.62418 (12)	0.51605 (12)	0.0473 (4)
H8	0.6632	0.6226	0.4873	0.057*
C9	0.61077 (8)	0.62273 (10)	0.61146 (11)	0.0407 (3)
C10	0.66219 (8)	0.61682 (10)	0.67757 (11)	0.0406 (3)
C11	0.41493 (9)	0.62820 (11)	0.43487 (11)	0.0423 (4)
C12	0.37604 (9)	0.69080 (12)	0.40320 (12)	0.0479 (4)
C13	0.35525 (11)	0.69580 (14)	0.31334 (13)	0.0578 (5)
H13	0.3294	0.7392	0.2928	0.069*
C14	0.37198 (10)	0.63815 (14)	0.25443 (13)	0.0578 (5)
H14	0.3579	0.6417	0.1929	0.069*
C15	0.40929 (10)	0.57473 (13)	0.28425 (13)	0.0539 (5)
H15	0.4204	0.5345	0.2435	0.065*
C16	0.43038 (9)	0.57010 (12)	0.37372 (12)	0.0474 (4)
H16	0.4559	0.5263	0.3937	0.057*
N3	0.35733 (9)	0.75046 (11)	0.46079 (11)	0.0581 (4)
C17	0.33979 (10)	0.77941 (12)	0.52739 (14)	0.0531 (4)
S1	0.31534 (3)	0.82304 (4)	0.61376 (4)	0.07149 (18)
C18	0.73280 (8)	0.61190 (11)	0.64634 (11)	0.0422 (4)
C19	0.76769 (9)	0.67895 (11)	0.62281 (12)	0.0456 (4)
C20	0.83405 (10)	0.67559 (14)	0.59531 (14)	0.0564 (5)
H20	0.8569	0.7217	0.5787	0.068*
C21	0.86599 (10)	0.60474 (15)	0.59256 (15)	0.0617 (5)
H21	0.9114	0.6020	0.5748	0.074*
C22	0.83267 (11)	0.53773 (14)	0.61539 (16)	0.0629 (5)
H22	0.8551	0.4890	0.6131	0.075*
C23	0.76637 (10)	0.54120 (12)	0.64176 (14)	0.0529 (4)
H23	0.7436	0.4946	0.6569	0.063*
N4	0.73517 (9)	0.75053 (11)	0.62762 (13)	0.0587 (4)
C24	0.72587 (9)	0.81716 (12)	0.63222 (14)	0.0510 (4)
S2	0.71060 (3)	0.90666 (3)	0.63860 (5)	0.07015 (18)
O1	0.5000	0.76596 (11)	0.7500	0.0511 (4)
C31	0.54792 (10)	0.81107 (12)	0.70173 (15)	0.0555 (5)
H31A	0.5892	0.7798	0.6939	0.067*
H31B	0.5604	0.8578	0.7374	0.067*
C32	0.52032 (14)	0.83590 (17)	0.61075 (17)	0.0761 (7)
H32A	0.5068	0.7898	0.5759	0.114*
H32B	0.5550	0.8644	0.5788	0.114*
H32C	0.4812	0.8697	0.6184	0.114*
O2	0.9968 (9)	0.5749 (3)	0.7693 (6)	0.092 (3)	0.5
C41	1.0756 (8)	0.5710 (9)	0.6491 (11)	0.155 (6)	0.5
H41A	1.0997	0.6007	0.6059	0.233*	0.5
H41B	1.1070	0.5431	0.6873	0.233*	0.5
H41C	1.0464	0.5346	0.6182	0.233*	0.5
C42	1.0345 (7)	0.6237 (9)	0.7061 (9)	0.114 (4)	0.5
H42A	1.0636	0.6605	0.7364	0.136*	0.5
H42B	1.0035	0.6521	0.6679	0.136*	0.5
C43	0.9492 (8)	0.6115 (8)	0.8328 (10)	0.124 (5)	0.5
H43A	0.9091	0.6246	0.7988	0.148*	0.5
H43B	0.9660	0.6586	0.8600	0.148*	0.5
C44	0.9249 (6)	0.5580 (6)	0.8994 (8)	0.117 (3)	0.5
H44A	0.8920	0.5822	0.9363	0.176*	0.5
H44B	0.9064	0.5111	0.8736	0.176*	0.5
H44C	0.9642	0.5455	0.9356	0.176*	0.5

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.03477 (15)	0.04689 (17)	0.03351 (15)	0.000	0.00291 (10)	0.000
N1	0.0356 (7)	0.0494 (8)	0.0350 (7)	−0.0013 (6)	0.0024 (5)	0.0005 (6)
N2	0.0361 (7)	0.0477 (8)	0.0339 (7)	0.0002 (6)	0.0028 (5)	0.0001 (5)
C1	0.0360 (8)	0.0453 (9)	0.0404 (8)	−0.0008 (6)	0.0033 (6)	0.0012 (7)
C2	0.0384 (8)	0.0556 (10)	0.0440 (9)	−0.0045 (7)	0.0012 (7)	−0.0001 (8)
C3	0.0407 (9)	0.0590 (11)	0.0394 (8)	−0.0046 (7)	−0.0009 (7)	−0.0013 (7)
C4	0.0387 (8)	0.0468 (9)	0.0364 (8)	−0.0011 (7)	−0.0008 (6)	−0.0003 (7)
C5	0.0408 (8)	0.0458 (9)	0.0359 (8)	−0.0009 (7)	0.0016 (6)	−0.0009 (6)
C6	0.0419 (8)	0.0465 (9)	0.0332 (8)	−0.0009 (7)	0.0032 (6)	0.0005 (6)
C7	0.0429 (9)	0.0639 (11)	0.0350 (8)	−0.0039 (8)	0.0049 (7)	0.0007 (7)
C8	0.0408 (9)	0.0634 (11)	0.0382 (9)	−0.0031 (8)	0.0074 (7)	−0.0001 (8)
C9	0.0384 (8)	0.0464 (9)	0.0377 (8)	−0.0012 (7)	0.0066 (6)	−0.0003 (7)
C10	0.0380 (8)	0.0440 (8)	0.0401 (8)	−0.0010 (6)	0.0052 (6)	−0.0005 (7)
C11	0.0395 (8)	0.0507 (10)	0.0365 (8)	−0.0032 (7)	0.0013 (6)	−0.0006 (7)
C12	0.0472 (9)	0.0573 (11)	0.0393 (8)	0.0030 (8)	0.0031 (7)	−0.0016 (7)
C13	0.0524 (11)	0.0778 (14)	0.0431 (10)	0.0109 (10)	−0.0023 (8)	0.0054 (9)
C14	0.0482 (10)	0.0903 (16)	0.0346 (9)	0.0001 (10)	−0.0016 (7)	−0.0027 (9)
C15	0.0495 (10)	0.0705 (13)	0.0418 (9)	−0.0087 (9)	0.0040 (7)	−0.0132 (9)
C16	0.0465 (9)	0.0516 (10)	0.0443 (9)	−0.0033 (7)	0.0032 (7)	−0.0037 (7)
N3	0.0655 (10)	0.0604 (10)	0.0485 (9)	0.0124 (8)	0.0023 (7)	−0.0006 (8)
C17	0.0506 (10)	0.0545 (11)	0.0540 (11)	0.0066 (8)	−0.0021 (8)	0.0003 (9)
S1	0.0758 (4)	0.0729 (4)	0.0663 (4)	0.0059 (3)	0.0115 (3)	−0.0197 (3)
C18	0.0377 (8)	0.0522 (9)	0.0368 (8)	−0.0008 (7)	0.0036 (6)	−0.0005 (7)
C19	0.0423 (9)	0.0526 (10)	0.0417 (8)	−0.0045 (7)	−0.0004 (7)	−0.0002 (7)
C20	0.0430 (9)	0.0734 (13)	0.0529 (10)	−0.0128 (9)	0.0049 (8)	0.0062 (9)
C21	0.0389 (9)	0.0876 (16)	0.0592 (12)	0.0013 (10)	0.0104 (8)	0.0032 (11)
C22	0.0483 (10)	0.0702 (14)	0.0707 (13)	0.0137 (10)	0.0129 (9)	0.0031 (11)
C23	0.0463 (10)	0.0548 (11)	0.0579 (11)	0.0035 (8)	0.0105 (8)	0.0038 (8)
N4	0.0569 (10)	0.0526 (10)	0.0665 (11)	−0.0068 (8)	0.0004 (8)	0.0012 (8)
C24	0.0418 (9)	0.0569 (12)	0.0543 (10)	−0.0058 (8)	0.0004 (7)	0.0018 (8)
S2	0.0700 (4)	0.0529 (3)	0.0870 (4)	0.0033 (2)	−0.0071 (3)	−0.0033 (3)
O1	0.0499 (10)	0.0455 (10)	0.0586 (11)	0.000	0.0160 (8)	0.000
C31	0.0510 (10)	0.0541 (11)	0.0620 (12)	−0.0087 (8)	0.0112 (9)	0.0022 (9)
C32	0.0862 (18)	0.0802 (16)	0.0623 (14)	−0.0162 (14)	0.0082 (12)	0.0123 (12)
O2	0.073 (3)	0.087 (2)	0.116 (8)	0.005 (3)	−0.004 (7)	−0.006 (3)
C41	0.152 (10)	0.135 (10)	0.179 (13)	0.050 (8)	−0.008 (10)	−0.063 (9)
C42	0.091 (7)	0.125 (8)	0.122 (9)	−0.016 (5)	−0.039 (6)	0.025 (7)
C43	0.125 (11)	0.099 (8)	0.145 (13)	0.046 (7)	−0.036 (9)	−0.035 (8)
C44	0.108 (6)	0.071 (5)	0.175 (11)	−0.013 (4)	0.030 (7)	−0.002 (6)

Geometric parameters (Å, º) top

Zn1—N2	2.0622 (13)	C20—C21	1.374 (3)
Zn1—N2ⁱ	2.0622 (13)	C20—H20	0.9500
Zn1—N1ⁱ	2.0684 (14)	C21—C22	1.376 (3)
Zn1—N1	2.0685 (14)	C21—H21	0.9500
Zn1—O1	2.1352 (19)	C22—C23	1.387 (3)
N1—C4	1.368 (2)	C22—H22	0.9500
N1—C1	1.370 (2)	C23—H23	0.9500
N2—C9	1.368 (2)	N4—C24	1.162 (3)
N2—C6	1.370 (2)	C24—S2	1.571 (2)
C1—C10ⁱ	1.397 (2)	O1—C31	1.436 (2)
C1—C2	1.443 (2)	O1—C31ⁱ	1.436 (2)
C2—C3	1.348 (2)	C31—C32	1.507 (3)
C2—H2	0.9500	C31—H31A	0.9900
C3—C4	1.440 (2)	C31—H31B	0.9900
C3—H3	0.9500	C32—H32A	0.9800
C4—C5	1.401 (2)	C32—H32B	0.9800
C5—C6	1.404 (2)	C32—H32C	0.9800
C5—C11	1.494 (2)	O2—C42ⁱⁱ	1.11 (2)
C6—C7	1.440 (2)	O2—C42	1.479 (12)
C7—C8	1.355 (3)	O2—C43	1.495 (11)
C7—H7	0.9500	O2—C41ⁱⁱ	1.912 (18)
C8—C9	1.440 (2)	C41—C44ⁱⁱ	0.755 (17)
C8—H8	0.9500	C41—C43ⁱⁱ	0.900 (18)
C9—C10	1.401 (2)	C41—C42	1.499 (14)
C10—C1ⁱ	1.397 (2)	C41—O2ⁱⁱ	1.912 (18)
C10—C18	1.494 (2)	C41—H41A	0.9600
C11—C16	1.391 (3)	C41—H41B	0.9599
C11—C12	1.398 (3)	C41—H41C	0.9600
C12—C13	1.390 (3)	C42—C43ⁱⁱ	0.703 (16)
C12—N3	1.393 (2)	C42—O2ⁱⁱ	1.11 (2)
C13—C14	1.370 (3)	C42—C42ⁱⁱ	1.92 (3)
C13—H13	0.9500	C42—H42A	0.9601
C14—C15	1.384 (3)	C42—H42B	0.9599
C14—H14	0.9500	C43—C42ⁱⁱ	0.703 (16)
C15—C16	1.385 (3)	C43—C41ⁱⁱ	0.900 (18)
C15—H15	0.9500	C43—C44	1.446 (14)
C16—H16	0.9500	C43—H43A	0.9599
N3—C17	1.170 (3)	C43—H43B	0.9600
C17—S1	1.576 (2)	C44—C41ⁱⁱ	0.755 (17)
C18—C23	1.389 (3)	C44—H44A	0.9600
C18—C19	1.394 (3)	C44—H44B	0.9600
C19—N4	1.392 (3)	C44—H44C	0.9599
C19—C20	1.394 (3)

N2—Zn1—N2ⁱ	164.44 (8)	C31—O1—Zn1	122.65 (11)
N2—Zn1—N1ⁱ	88.85 (6)	C31ⁱ—O1—Zn1	122.65 (11)
N2ⁱ—Zn1—N1ⁱ	88.54 (6)	O1—C31—C32	111.82 (17)
N2—Zn1—N1	88.54 (6)	O1—C31—H31A	109.3
N2ⁱ—Zn1—N1	88.85 (6)	C32—C31—H31A	109.3
N1ⁱ—Zn1—N1	160.61 (8)	O1—C31—H31B	109.3
N2—Zn1—O1	97.78 (4)	C32—C31—H31B	109.3
N2ⁱ—Zn1—O1	97.78 (4)	H31A—C31—H31B	107.9
N1ⁱ—Zn1—O1	99.69 (4)	C31—C32—H32A	109.5
N1—Zn1—O1	99.69 (4)	C31—C32—H32B	109.5
C4—N1—C1	106.50 (14)	H32A—C32—H32B	109.5
C4—N1—Zn1	126.59 (11)	C31—C32—H32C	109.5
C1—N1—Zn1	126.82 (11)	H32A—C32—H32C	109.5
C9—N2—C6	106.88 (13)	H32B—C32—H32C	109.5
C9—N2—Zn1	126.26 (11)	C42ⁱⁱ—O2—C42	94.7 (13)
C6—N2—Zn1	126.16 (11)	C42ⁱⁱ—O2—C43	26.4 (9)
N1—C1—C10ⁱ	125.29 (15)	C42—O2—C43	120.3 (9)
N1—C1—C2	109.66 (14)	C42ⁱⁱ—O2—C41ⁱⁱ	51.6 (8)
C10ⁱ—C1—C2	125.05 (16)	C42—O2—C41ⁱⁱ	146.0 (10)
C3—C2—C1	106.91 (15)	C43—O2—C41ⁱⁱ	27.3 (8)
C3—C2—H2	126.5	C44ⁱⁱ—C41—C43ⁱⁱ	122 (3)
C1—C2—H2	126.5	C44ⁱⁱ—C41—C42	137 (3)
C2—C3—C4	107.20 (15)	C43ⁱⁱ—C41—C42	18.1 (13)
C2—C3—H3	126.4	C44ⁱⁱ—C41—O2ⁱⁱ	129 (2)
C4—C3—H3	126.4	C43ⁱⁱ—C41—O2ⁱⁱ	49.6 (12)
N1—C4—C5	125.53 (15)	C42—C41—O2ⁱⁱ	35.6 (7)
N1—C4—C3	109.70 (14)	C44ⁱⁱ—C41—H41A	60.7
C5—C4—C3	124.76 (16)	C43ⁱⁱ—C41—H41A	94.4
C4—C5—C6	125.25 (16)	C42—C41—H41A	110.3
C4—C5—C11	117.74 (15)	O2ⁱⁱ—C41—H41A	143.7
C6—C5—C11	116.99 (15)	C44ⁱⁱ—C41—H41B	114.2
N2—C6—C5	125.30 (15)	C43ⁱⁱ—C41—H41B	124.1
N2—C6—C7	109.32 (15)	C42—C41—H41B	108.7
C5—C6—C7	125.28 (16)	O2ⁱⁱ—C41—H41B	97.5
C8—C7—C6	107.28 (16)	H41A—C41—H41B	109.5
C8—C7—H7	126.4	C44ⁱⁱ—C41—H41C	50.2
C6—C7—H7	126.4	C43ⁱⁱ—C41—H41C	108.5
C7—C8—C9	106.85 (15)	C42—C41—H41C	109.4
C7—C8—H8	126.6	O2ⁱⁱ—C41—H41C	82.6
C9—C8—H8	126.6	H41A—C41—H41C	109.5
N2—C9—C10	125.61 (15)	H41B—C41—H41C	109.5
N2—C9—C8	109.64 (15)	C43ⁱⁱ—C42—O2ⁱⁱ	109 (2)
C10—C9—C8	124.73 (16)	C43ⁱⁱ—C42—O2	127 (2)
C1ⁱ—C10—C9	125.76 (16)	O2ⁱⁱ—C42—O2	20.8 (8)
C1ⁱ—C10—C18	116.90 (15)	C43ⁱⁱ—C42—C41	23 (2)
C9—C10—C18	117.33 (15)	O2ⁱⁱ—C42—C41	92.9 (12)
C16—C11—C12	117.55 (16)	O2—C42—C41	108.1 (13)
C16—C11—C5	120.98 (17)	C43ⁱⁱ—C42—C42ⁱⁱ	156 (3)
C12—C11—C5	121.45 (16)	O2ⁱⁱ—C42—C42ⁱⁱ	50.1 (8)
C13—C12—N3	117.92 (18)	O2—C42—C42ⁱⁱ	35.3 (7)
C13—C12—C11	121.16 (18)	C41—C42—C42ⁱⁱ	142.7 (10)
N3—C12—C11	120.92 (16)	C43ⁱⁱ—C42—H42A	107.4
C14—C13—C12	119.9 (2)	O2ⁱⁱ—C42—H42A	132.6
C14—C13—H13	120.0	O2—C42—H42A	112.6
C12—C13—H13	120.0	C41—C42—H42A	109.5
C13—C14—C15	120.15 (18)	C42ⁱⁱ—C42—H42A	96.5
C13—C14—H14	119.9	C43ⁱⁱ—C42—H42B	88.1
C15—C14—H14	119.9	O2ⁱⁱ—C42—H42B	102.7
C14—C15—C16	119.83 (18)	O2—C42—H42B	109.6
C14—C15—H15	120.1	C41—C42—H42B	108.8
C16—C15—H15	120.1	C42ⁱⁱ—C42—H42B	86.7
C15—C16—C11	121.34 (19)	H42A—C42—H42B	108.1
C15—C16—H16	119.3	C42ⁱⁱ—C43—C41ⁱⁱ	138 (3)
C11—C16—H16	119.3	C42ⁱⁱ—C43—C44	158 (2)
C17—N3—C12	157.6 (2)	C41ⁱⁱ—C43—C44	26.4 (16)
N3—C17—S1	176.6 (2)	C42ⁱⁱ—C43—O2	44.9 (18)
C23—C18—C19	117.82 (16)	C41ⁱⁱ—C43—O2	103.2 (17)
C23—C18—C10	121.48 (16)	C44—C43—O2	113.4 (10)
C19—C18—C10	120.68 (17)	C42ⁱⁱ—C43—H43A	83.7
N4—C19—C20	119.79 (18)	C41ⁱⁱ—C43—H43A	83.3
N4—C19—C18	118.78 (16)	C44—C43—H43A	102.7
C20—C19—C18	121.44 (19)	O2—C43—H43A	107.3
C21—C20—C19	119.2 (2)	C42ⁱⁱ—C43—H43B	86.1
C21—C20—H20	120.4	C41ⁱⁱ—C43—H43B	135.5
C19—C20—H20	120.4	C44—C43—H43B	111.5
C20—C21—C22	120.49 (18)	O2—C43—H43B	113.6
C20—C21—H21	119.8	H43A—C43—H43B	107.3
C22—C21—H21	119.8	C41ⁱⁱ—C44—C43	32.0 (18)
C21—C22—C23	120.1 (2)	C41ⁱⁱ—C44—H44A	115.3
C21—C22—H22	119.9	C43—C44—H44A	111.3
C23—C22—H22	119.9	C41ⁱⁱ—C44—H44B	82.6
C22—C23—C18	120.90 (19)	C43—C44—H44B	113.0
C22—C23—H23	119.5	H44A—C44—H44B	109.5
C18—C23—H23	119.5	C41ⁱⁱ—C44—H44C	126.1
C24—N4—C19	161.5 (2)	C43—C44—H44C	104.0
N4—C24—S2	178.01 (19)	H44A—C44—H44C	109.5
C31—O1—C31ⁱ	114.7 (2)	H44B—C44—H44C	109.5

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+2, y, −z+3/2.

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Crystal structure of (diethyl ether-κO)[5,10,15,20-tetra­kis­(2-iso­thio­cyanato­phen­yl)porphyrinato-κ4N]zinc diethyl ether solvate

Supporting information

Key indicators

checkCIF/PLATON results

Crystal structure of (diethyl ether-κO)[5,10,15,20-tetrakis(2-isothiocyanatophenyl)porphyrinato-κ⁴N]zinc diethyl ether solvate