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The title compound, [Zn(C50H26N8)(C5H5N)]·C6H5NO2·C3H7NO, is a nitrobenzene clathrate of a five-coordinate zinc–pyridine–porphyrin complex with different substituents at the meso positions of the metalloporphyrin core. The complex adopts a domed conformation with the central zinc ion deviating from the plane of the macrocyclic ring towards the apical pyridine ligand. The crystal packing is characterized by a layered arrangement of the porphyrin molecules with dipole–dipole interactions and weak hydrogen bonding contributing to the stabilization of the crystal structure. While the nitrobenzene solvent is well localized within the open porphyrin layers, molecules of the dimethylformamide are severely disordered in elongated interlayer channel voids
Supporting information
CCDC reference: 605244
Key indicators
- Single-crystal X-ray study
- T = 110 K
- Mean (C-C) = 0.004 Å
- R factor = 0.056
- wR factor = 0.154
- Data-to-parameter ratio = 19.2
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 5.46 Ratio
| Author Response: Due to significant rotational disorder of the pyridine and
nitrobenzene residues.
|
PLAT241_ALERT_2_A Check High Ueq as Compared to Neighbors for C61
| Author Response: Due to significant rotational disorder of the pyridine and
nitrobenzene residues.
|
Alert level B
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.62 Ratio
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT220_ALERT_2_C Large Non-Solvent N Ueq(max)/Ueq(min) ... 3.27 Ratio
| Author Response: Due to significant rotational disorder of the pyridine and
nitrobenzene residues.
|
PLAT230_ALERT_2_C Hirshfeld Test Diff for C28 - C29 .. 5.72 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C53 - C54 .. 5.16 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C27
| Author Response: Due to significant rotational disorder of the pyridine and
nitrobenzene residues.
|
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C29
| Author Response: Due to significant rotational disorder of the pyridine and
nitrobenzene residues.
|
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N59
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C25
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C28
PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C68
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C70
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.19
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C28 - C31 ... 1.45 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C36 - C39 ... 1.44 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C44 - C47 ... 1.43 Ang.
PLAT602_ALERT_4_C VERY LARGE Solvent Accessible VOID(S) in Structure !
PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... N40^A^'
PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... N48^B^'
PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... O73^C^'
PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... N24^D^'
PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... N50^E^'
PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... N32^F^'
2 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
22 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
14 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: Collect (Nonius, 1999); cell refinement: DENZO (Otwinowski and Minor, 1997); data reduction: DENZO (Otwinowski and Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-III (Burnett and Johnson, 1996) and
Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
(pyridine)[5,10,15-tris(4-cyanophenyl)-20-(2-quinolyl)porphyrinato]zinc(II)–
nitrobenzene–dimethylforrmamide (1/1/1)
top
Crystal data top
[Zn(C50H26N8)(C5H5N)]·C6H5NO2·C3H7NO | Z = 2 |
Mr = 1006.37 | F(000) = 1116 |
Triclinic, P1 | Dx = 1.305 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.2089 (2) Å | Cell parameters from 10058 reflections |
b = 15.3117 (3) Å | θ = 1.4–27.9° |
c = 17.2043 (4) Å | µ = 0.51 mm−1 |
α = 79.6017 (12)° | T = 110 K |
β = 72.0928 (11)° | Needle, red |
γ = 80.9992 (16)° | 0.35 × 0.15 × 0.10 mm |
V = 2747.42 (10) Å3 | |
Data collection top
Nonius KappaCCD diffractometer | 9650 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.044 |
Graphite monochromator | θmax = 27.9°, θmin = 2.5° |
Detector resolution: 56 microns pixels mm-1 | h = −14→14 |
1 deg. ω scans | k = −19→20 |
30139 measured reflections | l = −20→22 |
12778 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.154 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0847P)2 + 0.5255P] where P = (Fo2 + 2Fc2)/3 |
12778 reflections | (Δ/σ)max = 0.002 |
667 parameters | Δρmax = 0.94 e Å−3 |
0 restraints | Δρmin = −0.47 e Å−3 |
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. The crystal contains also some amount of severely disordered DMF solvent which
could not be modelled reliably. Its contribution to the diffraction data was
thus subtracted using the Squeeze procedure (Spek, 2003). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Zn | 0.39082 (2) | 0.823338 (17) | 0.248561 (15) | 0.02632 (10) | |
C1 | 0.4621 (2) | 0.80111 (16) | 0.06457 (15) | 0.0306 (5) | |
C2 | 0.5407 (3) | 0.74568 (18) | 0.00440 (15) | 0.0369 (6) | |
H2 | 0.5417 | 0.7507 | −0.0516 | 0.044* | |
C3 | 0.6130 (3) | 0.68499 (18) | 0.04349 (16) | 0.0376 (6) | |
H3 | 0.6755 | 0.6403 | 0.0197 | 0.045* | |
C4 | 0.5766 (2) | 0.70148 (17) | 0.12816 (15) | 0.0312 (5) | |
C5 | 0.6317 (2) | 0.65293 (16) | 0.18840 (15) | 0.0308 (5) | |
C6 | 0.6038 (2) | 0.67215 (16) | 0.26940 (15) | 0.0313 (5) | |
C7 | 0.6623 (3) | 0.62289 (18) | 0.33060 (16) | 0.0390 (6) | |
H7 | 0.7240 | 0.5725 | 0.3238 | 0.047* | |
C8 | 0.6117 (3) | 0.66269 (18) | 0.39957 (16) | 0.0383 (6) | |
H8 | 0.6315 | 0.6453 | 0.4504 | 0.046* | |
C9 | 0.5226 (2) | 0.73594 (16) | 0.38154 (15) | 0.0315 (5) | |
C10 | 0.4549 (2) | 0.79697 (17) | 0.43598 (14) | 0.0306 (5) | |
C11 | 0.3792 (2) | 0.87421 (16) | 0.41679 (14) | 0.0295 (5) | |
C12 | 0.3199 (2) | 0.93988 (17) | 0.47170 (15) | 0.0338 (5) | |
H12 | 0.3238 | 0.9373 | 0.5265 | 0.041* | |
C13 | 0.2578 (2) | 1.00580 (17) | 0.43020 (15) | 0.0331 (5) | |
H13 | 0.2108 | 1.0585 | 0.4501 | 0.040* | |
C14 | 0.2769 (2) | 0.98049 (16) | 0.34953 (14) | 0.0294 (5) | |
C15 | 0.2293 (2) | 1.03261 (16) | 0.28696 (14) | 0.0303 (5) | |
C16 | 0.2513 (2) | 1.01035 (16) | 0.20734 (14) | 0.0303 (5) | |
C17 | 0.2055 (3) | 1.06440 (18) | 0.14242 (16) | 0.0374 (6) | |
H17 | 0.1569 | 1.1210 | 0.1452 | 0.045* | |
C18 | 0.2450 (3) | 1.01914 (18) | 0.07674 (15) | 0.0359 (6) | |
H18 | 0.2291 | 1.0380 | 0.0248 | 0.043* | |
C19 | 0.3155 (2) | 0.93726 (16) | 0.10035 (14) | 0.0284 (5) | |
C20 | 0.3791 (2) | 0.87471 (16) | 0.04726 (14) | 0.0282 (5) | |
N21 | 0.48532 (19) | 0.77256 (13) | 0.13962 (12) | 0.0290 (4) | |
N22 | 0.51840 (18) | 0.74002 (13) | 0.30168 (12) | 0.0286 (4) | |
N23 | 0.35150 (19) | 0.90060 (13) | 0.34318 (12) | 0.0288 (4) | |
N24 | 0.31798 (18) | 0.93319 (13) | 0.18003 (12) | 0.0281 (4) | |
C25 | 0.7314 (2) | 0.57752 (18) | 0.16310 (15) | 0.0362 (6) | |
C26 | 0.8552 (3) | 0.5844 (3) | 0.1509 (3) | 0.0690 (11) | |
H26 | 0.8793 | 0.6379 | 0.1594 | 0.083* | |
C27 | 0.9480 (3) | 0.5148 (3) | 0.1264 (3) | 0.0793 (12) | |
H27 | 1.0342 | 0.5217 | 0.1173 | 0.095* | |
C28 | 0.9157 (3) | 0.4378 (2) | 0.11544 (19) | 0.0505 (7) | |
C29 | 0.7899 (4) | 0.4287 (2) | 0.1258 (3) | 0.0727 (11) | |
H29 | 0.7667 | 0.3754 | 0.1162 | 0.087* | |
C30 | 0.6986 (3) | 0.4990 (2) | 0.1502 (2) | 0.0623 (9) | |
H30 | 0.6124 | 0.4930 | 0.1582 | 0.075* | |
C31 | 1.0107 (3) | 0.3644 (3) | 0.0908 (2) | 0.0625 (9) | |
N32 | 1.0826 (3) | 0.3044 (2) | 0.0734 (2) | 0.0757 (9) | |
C33 | 0.4670 (2) | 0.77447 (17) | 0.52219 (15) | 0.0328 (5) | |
C34 | 0.4022 (3) | 0.70689 (18) | 0.57608 (16) | 0.0400 (6) | |
H34 | 0.3501 | 0.6764 | 0.5581 | 0.048* | |
C35 | 0.4125 (3) | 0.68333 (19) | 0.65540 (17) | 0.0472 (7) | |
H35 | 0.3672 | 0.6375 | 0.6920 | 0.057* | |
C36 | 0.4903 (3) | 0.72766 (19) | 0.68097 (17) | 0.0448 (7) | |
C37 | 0.5556 (3) | 0.7954 (2) | 0.62798 (17) | 0.0435 (6) | |
H37 | 0.6082 | 0.8256 | 0.6458 | 0.052* | |
C38 | 0.5434 (3) | 0.81870 (19) | 0.54826 (16) | 0.0396 (6) | |
H38 | 0.5876 | 0.8651 | 0.5118 | 0.048* | |
C39 | 0.5005 (4) | 0.7042 (2) | 0.7640 (2) | 0.0598 (9) | |
N40 | 0.5079 (5) | 0.6856 (2) | 0.8295 (2) | 0.0919 (13) | |
C41 | 0.1530 (2) | 1.11930 (17) | 0.30542 (15) | 0.0338 (5) | |
C42 | 0.0376 (3) | 1.12105 (19) | 0.36812 (17) | 0.0397 (6) | |
H42 | 0.0090 | 1.0668 | 0.4000 | 0.048* | |
C43 | −0.0339 (3) | 1.2008 (2) | 0.38343 (19) | 0.0469 (7) | |
H43 | −0.1112 | 1.2017 | 0.4264 | 0.056* | |
C44 | 0.0067 (3) | 1.2807 (2) | 0.33602 (19) | 0.0470 (7) | |
C45 | 0.1225 (3) | 1.2796 (2) | 0.27479 (18) | 0.0455 (7) | |
H45 | 0.1518 | 1.3337 | 0.2433 | 0.055* | |
C46 | 0.1937 (3) | 1.19906 (17) | 0.26060 (16) | 0.0370 (6) | |
H46 | 0.2725 | 1.1983 | 0.2191 | 0.044* | |
C47 | −0.0700 (4) | 1.3639 (2) | 0.3492 (2) | 0.0614 (9) | |
N48 | −0.1335 (4) | 1.4302 (2) | 0.3590 (3) | 0.0896 (11) | |
C49 | 0.3614 (2) | 0.89024 (16) | −0.03755 (14) | 0.0303 (5) | |
N50 | 0.2690 (2) | 0.85264 (15) | −0.04713 (13) | 0.0376 (5) | |
C51 | 0.2520 (3) | 0.86520 (18) | −0.12475 (16) | 0.0375 (6) | |
C52 | 0.1562 (3) | 0.8263 (2) | −0.13573 (19) | 0.0514 (7) | |
H52 | 0.1025 | 0.7928 | −0.0901 | 0.062* | |
C53 | 0.1383 (3) | 0.8359 (2) | −0.2122 (2) | 0.0531 (8) | |
H53 | 0.0723 | 0.8088 | −0.2192 | 0.064* | |
C54 | 0.2181 (3) | 0.8865 (2) | −0.2821 (2) | 0.0544 (8) | |
H54 | 0.2060 | 0.8923 | −0.3352 | 0.065* | |
C55 | 0.3079 (3) | 0.9244 (2) | −0.27146 (17) | 0.0452 (7) | |
H55 | 0.3598 | 0.9586 | −0.3175 | 0.054* | |
C56 | 0.3302 (3) | 0.91597 (17) | −0.19297 (16) | 0.0377 (6) | |
C57 | 0.4261 (3) | 0.9540 (2) | −0.17989 (17) | 0.0431 (6) | |
H57 | 0.4805 | 0.9884 | −0.2243 | 0.052* | |
C58 | 0.4416 (3) | 0.9415 (2) | −0.10247 (16) | 0.0403 (6) | |
H58 | 0.5065 | 0.9675 | −0.0930 | 0.048* | |
N59 | 0.2289 (2) | 0.75215 (15) | 0.29321 (14) | 0.0375 (5) | |
C60 | 0.1901 (4) | 0.7143 (4) | 0.2451 (3) | 0.1045 (19) | |
H60 | 0.2375 | 0.7176 | 0.1886 | 0.125* | |
C61 | 0.0816 (6) | 0.6685 (6) | 0.2717 (4) | 0.154 (4) | |
H61 | 0.0596 | 0.6394 | 0.2345 | 0.185* | |
C62 | 0.0118 (4) | 0.6666 (4) | 0.3484 (3) | 0.0980 (16) | |
H62 | −0.0616 | 0.6361 | 0.3676 | 0.118* | |
C63 | 0.0447 (4) | 0.7082 (3) | 0.3994 (3) | 0.0704 (10) | |
H63 | −0.0056 | 0.7087 | 0.4550 | 0.084* | |
C64 | 0.1537 (3) | 0.7504 (2) | 0.3694 (2) | 0.0583 (8) | |
H64 | 0.1759 | 0.7801 | 0.4061 | 0.070* | |
C65 | 0.2225 (3) | 0.1431 (2) | 0.7576 (2) | 0.0486 (7) | |
H65 | 0.2976 | 0.1508 | 0.7136 | 0.058* | |
C66 | 0.2149 (3) | 0.1580 (2) | 0.8363 (2) | 0.0509 (7) | |
H66 | 0.2857 | 0.1758 | 0.8464 | 0.061* | |
C67 | 0.1069 (3) | 0.1474 (3) | 0.8992 (2) | 0.0655 (9) | |
H67 | 0.1023 | 0.1578 | 0.9530 | 0.079* | |
C68 | 0.0046 (4) | 0.1218 (5) | 0.8846 (3) | 0.107 (2) | |
H68 | −0.0709 | 0.1145 | 0.9284 | 0.128* | |
C69 | 0.0109 (3) | 0.1064 (4) | 0.8066 (2) | 0.0868 (15) | |
H69 | −0.0599 | 0.0886 | 0.7966 | 0.104* | |
C70 | 0.1185 (3) | 0.1169 (2) | 0.74496 (19) | 0.0452 (7) | |
N71 | 0.1254 (3) | 0.10008 (18) | 0.66264 (16) | 0.0517 (6) | |
O72 | 0.0342 (2) | 0.07354 (17) | 0.65262 (16) | 0.0638 (6) | |
O73 | 0.2222 (3) | 0.1136 (2) | 0.60696 (16) | 0.0806 (8) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn | 0.02952 (15) | 0.02928 (15) | 0.02161 (14) | −0.00048 (10) | −0.01038 (10) | −0.00429 (10) |
C1 | 0.0341 (12) | 0.0338 (12) | 0.0271 (12) | −0.0025 (10) | −0.0121 (10) | −0.0072 (10) |
C2 | 0.0442 (14) | 0.0448 (15) | 0.0250 (12) | 0.0036 (12) | −0.0144 (10) | −0.0122 (11) |
C3 | 0.0457 (14) | 0.0410 (14) | 0.0279 (13) | 0.0064 (11) | −0.0140 (11) | −0.0127 (11) |
C4 | 0.0336 (12) | 0.0358 (13) | 0.0257 (12) | −0.0011 (10) | −0.0098 (9) | −0.0081 (10) |
C5 | 0.0324 (12) | 0.0317 (12) | 0.0283 (12) | 0.0020 (10) | −0.0091 (9) | −0.0082 (10) |
C6 | 0.0319 (12) | 0.0356 (13) | 0.0275 (12) | 0.0012 (10) | −0.0117 (10) | −0.0060 (10) |
C7 | 0.0441 (14) | 0.0397 (14) | 0.0319 (13) | 0.0112 (11) | −0.0153 (11) | −0.0073 (11) |
C8 | 0.0428 (14) | 0.0450 (15) | 0.0279 (13) | 0.0078 (12) | −0.0183 (11) | −0.0040 (11) |
C9 | 0.0356 (12) | 0.0336 (12) | 0.0253 (12) | 0.0011 (10) | −0.0119 (10) | −0.0031 (9) |
C10 | 0.0323 (12) | 0.0381 (13) | 0.0238 (11) | −0.0041 (10) | −0.0109 (9) | −0.0047 (10) |
C11 | 0.0334 (12) | 0.0349 (12) | 0.0209 (11) | −0.0035 (10) | −0.0083 (9) | −0.0051 (9) |
C12 | 0.0409 (13) | 0.0361 (13) | 0.0259 (12) | 0.0034 (11) | −0.0134 (10) | −0.0082 (10) |
C13 | 0.0412 (13) | 0.0342 (13) | 0.0260 (12) | 0.0008 (11) | −0.0124 (10) | −0.0086 (10) |
C14 | 0.0326 (12) | 0.0314 (12) | 0.0247 (11) | 0.0003 (10) | −0.0090 (9) | −0.0069 (9) |
C15 | 0.0335 (12) | 0.0320 (12) | 0.0259 (12) | 0.0026 (10) | −0.0104 (9) | −0.0070 (9) |
C16 | 0.0340 (12) | 0.0327 (12) | 0.0255 (12) | 0.0022 (10) | −0.0124 (9) | −0.0059 (9) |
C17 | 0.0480 (15) | 0.0361 (13) | 0.0307 (13) | 0.0073 (11) | −0.0201 (11) | −0.0061 (10) |
C18 | 0.0458 (14) | 0.0392 (14) | 0.0263 (12) | 0.0029 (11) | −0.0187 (11) | −0.0054 (10) |
C19 | 0.0316 (12) | 0.0334 (12) | 0.0228 (11) | −0.0023 (10) | −0.0122 (9) | −0.0037 (9) |
C20 | 0.0322 (12) | 0.0342 (12) | 0.0218 (11) | −0.0064 (10) | −0.0123 (9) | −0.0029 (9) |
N21 | 0.0323 (10) | 0.0332 (10) | 0.0235 (10) | −0.0001 (8) | −0.0121 (8) | −0.0053 (8) |
N22 | 0.0311 (10) | 0.0324 (10) | 0.0233 (10) | 0.0018 (8) | −0.0113 (8) | −0.0048 (8) |
N23 | 0.0319 (10) | 0.0317 (10) | 0.0236 (10) | −0.0007 (8) | −0.0106 (8) | −0.0041 (8) |
N24 | 0.0308 (10) | 0.0334 (10) | 0.0218 (9) | −0.0013 (8) | −0.0107 (8) | −0.0045 (8) |
C25 | 0.0401 (14) | 0.0417 (14) | 0.0250 (12) | 0.0075 (11) | −0.0110 (10) | −0.0077 (10) |
C26 | 0.0457 (18) | 0.068 (2) | 0.103 (3) | 0.0121 (16) | −0.0276 (19) | −0.042 (2) |
C27 | 0.0412 (18) | 0.088 (3) | 0.115 (4) | 0.0166 (18) | −0.026 (2) | −0.046 (3) |
C28 | 0.0508 (17) | 0.0552 (18) | 0.0387 (16) | 0.0144 (14) | −0.0104 (13) | −0.0112 (13) |
C29 | 0.069 (2) | 0.0446 (19) | 0.098 (3) | 0.0093 (17) | −0.014 (2) | −0.0233 (19) |
C30 | 0.0447 (17) | 0.0453 (17) | 0.087 (3) | 0.0046 (14) | −0.0041 (16) | −0.0173 (17) |
C31 | 0.061 (2) | 0.069 (2) | 0.0499 (19) | 0.0183 (18) | −0.0136 (16) | −0.0136 (17) |
N32 | 0.069 (2) | 0.0629 (19) | 0.081 (2) | 0.0175 (16) | −0.0093 (17) | −0.0177 (17) |
C33 | 0.0398 (13) | 0.0354 (13) | 0.0242 (12) | 0.0056 (10) | −0.0140 (10) | −0.0069 (10) |
C34 | 0.0576 (17) | 0.0399 (14) | 0.0288 (13) | −0.0063 (12) | −0.0217 (12) | −0.0039 (11) |
C35 | 0.077 (2) | 0.0401 (15) | 0.0306 (14) | −0.0123 (14) | −0.0255 (14) | 0.0017 (11) |
C36 | 0.0694 (19) | 0.0426 (15) | 0.0287 (14) | 0.0018 (14) | −0.0265 (13) | −0.0059 (11) |
C37 | 0.0537 (16) | 0.0515 (16) | 0.0336 (14) | −0.0042 (13) | −0.0230 (12) | −0.0096 (12) |
C38 | 0.0434 (14) | 0.0485 (16) | 0.0290 (13) | −0.0037 (12) | −0.0143 (11) | −0.0049 (11) |
C39 | 0.102 (3) | 0.0482 (18) | 0.0421 (18) | −0.0137 (18) | −0.0407 (18) | −0.0003 (14) |
N40 | 0.177 (4) | 0.075 (2) | 0.0516 (19) | −0.032 (2) | −0.072 (2) | 0.0046 (16) |
C41 | 0.0409 (13) | 0.0377 (13) | 0.0273 (12) | 0.0068 (11) | −0.0190 (10) | −0.0098 (10) |
C42 | 0.0435 (14) | 0.0429 (15) | 0.0335 (14) | 0.0042 (12) | −0.0144 (11) | −0.0093 (11) |
C43 | 0.0477 (16) | 0.0485 (16) | 0.0419 (16) | 0.0136 (13) | −0.0141 (13) | −0.0138 (13) |
C44 | 0.0551 (17) | 0.0441 (16) | 0.0455 (16) | 0.0136 (13) | −0.0230 (14) | −0.0170 (13) |
C45 | 0.0599 (18) | 0.0398 (15) | 0.0416 (16) | 0.0038 (13) | −0.0251 (14) | −0.0077 (12) |
C46 | 0.0449 (14) | 0.0381 (14) | 0.0303 (13) | 0.0036 (11) | −0.0168 (11) | −0.0069 (10) |
C47 | 0.066 (2) | 0.0503 (19) | 0.065 (2) | 0.0198 (16) | −0.0245 (17) | −0.0150 (16) |
N48 | 0.098 (3) | 0.061 (2) | 0.093 (3) | 0.0291 (19) | −0.021 (2) | −0.0113 (18) |
C49 | 0.0349 (12) | 0.0360 (13) | 0.0236 (11) | −0.0009 (10) | −0.0136 (9) | −0.0069 (9) |
N50 | 0.0436 (12) | 0.0427 (12) | 0.0298 (11) | −0.0026 (10) | −0.0155 (9) | −0.0064 (9) |
C51 | 0.0424 (14) | 0.0428 (14) | 0.0318 (13) | 0.0024 (11) | −0.0178 (11) | −0.0099 (11) |
C52 | 0.0518 (17) | 0.064 (2) | 0.0414 (16) | −0.0077 (15) | −0.0152 (13) | −0.0096 (14) |
C53 | 0.0527 (18) | 0.066 (2) | 0.0493 (18) | −0.0055 (15) | −0.0237 (14) | −0.0144 (15) |
C54 | 0.0556 (18) | 0.065 (2) | 0.0522 (19) | 0.0073 (16) | −0.0291 (15) | −0.0205 (16) |
C55 | 0.0622 (18) | 0.0463 (16) | 0.0293 (14) | 0.0045 (14) | −0.0206 (13) | −0.0065 (12) |
C56 | 0.0509 (15) | 0.0364 (13) | 0.0275 (13) | 0.0079 (12) | −0.0173 (11) | −0.0092 (10) |
C57 | 0.0534 (16) | 0.0469 (16) | 0.0281 (13) | −0.0073 (13) | −0.0118 (12) | −0.0016 (11) |
C58 | 0.0471 (15) | 0.0515 (16) | 0.0259 (13) | −0.0137 (13) | −0.0151 (11) | 0.0005 (11) |
N59 | 0.0360 (11) | 0.0394 (12) | 0.0378 (12) | −0.0051 (9) | −0.0126 (9) | −0.0030 (9) |
C60 | 0.076 (3) | 0.180 (5) | 0.075 (3) | −0.068 (3) | −0.004 (2) | −0.048 (3) |
C61 | 0.105 (4) | 0.268 (9) | 0.117 (5) | −0.110 (6) | 0.010 (4) | −0.095 (5) |
C62 | 0.068 (3) | 0.137 (4) | 0.091 (3) | −0.048 (3) | −0.012 (2) | −0.007 (3) |
C63 | 0.059 (2) | 0.077 (3) | 0.072 (2) | −0.028 (2) | −0.0114 (18) | 0.002 (2) |
C64 | 0.0590 (19) | 0.063 (2) | 0.0515 (19) | −0.0211 (17) | −0.0095 (15) | −0.0037 (16) |
C65 | 0.0420 (15) | 0.0517 (17) | 0.0529 (18) | −0.0126 (13) | −0.0096 (13) | −0.0100 (14) |
C66 | 0.0533 (18) | 0.0458 (16) | 0.061 (2) | −0.0105 (14) | −0.0232 (15) | −0.0098 (14) |
C67 | 0.058 (2) | 0.092 (3) | 0.052 (2) | −0.0029 (19) | −0.0216 (16) | −0.0196 (19) |
C68 | 0.048 (2) | 0.228 (7) | 0.051 (2) | −0.043 (3) | 0.0013 (17) | −0.040 (3) |
C69 | 0.0450 (19) | 0.171 (5) | 0.055 (2) | −0.037 (2) | −0.0106 (16) | −0.027 (3) |
C70 | 0.0403 (14) | 0.0528 (17) | 0.0456 (16) | −0.0056 (13) | −0.0120 (12) | −0.0149 (13) |
N71 | 0.0512 (15) | 0.0584 (16) | 0.0473 (15) | −0.0110 (13) | −0.0119 (12) | −0.0115 (12) |
O72 | 0.0626 (14) | 0.0719 (16) | 0.0690 (16) | −0.0144 (12) | −0.0269 (12) | −0.0208 (13) |
O73 | 0.0655 (16) | 0.124 (2) | 0.0515 (15) | −0.0305 (16) | 0.0022 (12) | −0.0257 (15) |
Geometric parameters (Å, º) top
Zn—N21 | 2.0704 (19) | C35—H35 | 0.9500 |
Zn—N22 | 2.0784 (19) | C36—C37 | 1.389 (4) |
Zn—N24 | 2.081 (2) | C36—C39 | 1.444 (4) |
Zn—N23 | 2.0819 (19) | C37—C38 | 1.397 (4) |
Zn—N59 | 2.129 (2) | C37—H37 | 0.9500 |
C1—N21 | 1.376 (3) | C38—H38 | 0.9500 |
C1—C20 | 1.395 (3) | C39—N40 | 1.136 (4) |
C1—C2 | 1.446 (3) | C41—C46 | 1.383 (4) |
C2—C3 | 1.359 (4) | C41—C42 | 1.407 (4) |
C2—H2 | 0.9500 | C42—C43 | 1.372 (4) |
C3—C4 | 1.445 (3) | C42—H42 | 0.9500 |
C3—H3 | 0.9500 | C43—C44 | 1.398 (4) |
C4—N21 | 1.370 (3) | C43—H43 | 0.9500 |
C4—C5 | 1.407 (4) | C44—C45 | 1.398 (4) |
C5—C6 | 1.406 (3) | C44—C47 | 1.434 (4) |
C5—C25 | 1.500 (3) | C45—C46 | 1.377 (4) |
C6—N22 | 1.369 (3) | C45—H45 | 0.9500 |
C6—C7 | 1.446 (4) | C46—H46 | 0.9500 |
C7—C8 | 1.356 (4) | C47—N48 | 1.152 (4) |
C7—H7 | 0.9500 | C49—N50 | 1.326 (3) |
C8—C9 | 1.437 (3) | C49—C58 | 1.399 (4) |
C8—H8 | 0.9500 | N50—C51 | 1.382 (3) |
C9—N22 | 1.379 (3) | C51—C52 | 1.382 (4) |
C9—C10 | 1.408 (3) | C51—C56 | 1.415 (4) |
C10—C11 | 1.395 (4) | C52—C53 | 1.370 (4) |
C10—C33 | 1.504 (3) | C52—H52 | 0.9500 |
C11—N23 | 1.372 (3) | C53—C54 | 1.437 (5) |
C11—C12 | 1.447 (3) | C53—H53 | 0.9500 |
C12—C13 | 1.356 (4) | C54—C55 | 1.311 (4) |
C12—H12 | 0.9500 | C54—H54 | 0.9500 |
C13—C14 | 1.452 (3) | C55—C56 | 1.428 (4) |
C13—H13 | 0.9500 | C55—H55 | 0.9500 |
C14—N23 | 1.371 (3) | C56—C57 | 1.392 (4) |
C14—C15 | 1.411 (3) | C57—C58 | 1.371 (4) |
C15—C16 | 1.410 (3) | C57—H57 | 0.9500 |
C15—C41 | 1.491 (3) | C58—H58 | 0.9500 |
C16—N24 | 1.372 (3) | N59—C60 | 1.299 (4) |
C16—C17 | 1.443 (3) | N59—C64 | 1.321 (4) |
C17—C18 | 1.354 (4) | C60—C61 | 1.410 (6) |
C17—H17 | 0.9500 | C60—H60 | 0.9500 |
C18—C19 | 1.437 (3) | C61—C62 | 1.309 (7) |
C18—H18 | 0.9500 | C61—H61 | 0.9500 |
C19—N24 | 1.370 (3) | C62—C63 | 1.335 (6) |
C19—C20 | 1.401 (3) | C62—H62 | 0.9500 |
C20—C49 | 1.504 (3) | C63—C64 | 1.385 (5) |
C25—C26 | 1.357 (4) | C63—H63 | 0.9500 |
C25—C30 | 1.383 (4) | C64—H64 | 0.9500 |
C26—C27 | 1.393 (5) | C65—C70 | 1.379 (4) |
C26—H26 | 0.9500 | C65—C66 | 1.388 (4) |
C27—C28 | 1.346 (5) | C65—H65 | 0.9500 |
C27—H27 | 0.9500 | C66—C67 | 1.363 (5) |
C28—C29 | 1.391 (5) | C66—H66 | 0.9500 |
C28—C31 | 1.448 (4) | C67—C68 | 1.374 (5) |
C29—C30 | 1.392 (5) | C67—H67 | 0.9500 |
C29—H29 | 0.9500 | C68—C69 | 1.382 (5) |
C30—H30 | 0.9500 | C68—H68 | 0.9500 |
C31—N32 | 1.142 (4) | C69—C70 | 1.349 (5) |
C33—C38 | 1.386 (4) | C69—H69 | 0.9500 |
C33—C34 | 1.390 (4) | C70—N71 | 1.462 (4) |
C34—C35 | 1.383 (4) | N71—O73 | 1.223 (3) |
C34—H34 | 0.9500 | N71—O72 | 1.226 (3) |
C35—C36 | 1.394 (4) | | |
| | | |
N21—Zn—N22 | 87.53 (8) | C34—C33—C10 | 119.3 (2) |
N21—Zn—N24 | 88.70 (8) | C35—C34—C33 | 121.0 (3) |
N22—Zn—N24 | 159.44 (8) | C35—C34—H34 | 119.5 |
N21—Zn—N23 | 159.30 (8) | C33—C34—H34 | 119.5 |
N22—Zn—N23 | 88.51 (8) | C34—C35—C36 | 119.2 (3) |
N24—Zn—N23 | 87.92 (8) | C34—C35—H35 | 120.4 |
N21—Zn—N59 | 102.01 (8) | C36—C35—H35 | 120.4 |
N22—Zn—N59 | 101.91 (8) | C37—C36—C35 | 120.6 (2) |
N24—Zn—N59 | 98.64 (8) | C37—C36—C39 | 119.8 (3) |
N23—Zn—N59 | 98.68 (8) | C35—C36—C39 | 119.5 (3) |
N21—C1—C20 | 125.6 (2) | C36—C37—C38 | 119.4 (3) |
N21—C1—C2 | 110.0 (2) | C36—C37—H37 | 120.3 |
C20—C1—C2 | 124.4 (2) | C38—C37—H37 | 120.3 |
C3—C2—C1 | 106.7 (2) | C33—C38—C37 | 120.3 (3) |
C3—C2—H2 | 126.6 | C33—C38—H38 | 119.9 |
C1—C2—H2 | 126.6 | C37—C38—H38 | 119.9 |
C2—C3—C4 | 106.9 (2) | N40—C39—C36 | 179.6 (5) |
C2—C3—H3 | 126.5 | C46—C41—C42 | 119.0 (2) |
C4—C3—H3 | 126.5 | C46—C41—C15 | 120.6 (2) |
N21—C4—C5 | 125.7 (2) | C42—C41—C15 | 120.4 (2) |
N21—C4—C3 | 110.1 (2) | C43—C42—C41 | 120.2 (3) |
C5—C4—C3 | 124.1 (2) | C43—C42—H42 | 119.9 |
C6—C5—C4 | 124.8 (2) | C41—C42—H42 | 119.9 |
C6—C5—C25 | 117.7 (2) | C42—C43—C44 | 120.2 (3) |
C4—C5—C25 | 117.4 (2) | C42—C43—H43 | 119.9 |
N22—C6—C5 | 125.3 (2) | C44—C43—H43 | 119.9 |
N22—C6—C7 | 110.2 (2) | C45—C44—C43 | 119.8 (3) |
C5—C6—C7 | 124.5 (2) | C45—C44—C47 | 119.6 (3) |
C8—C7—C6 | 106.5 (2) | C43—C44—C47 | 120.6 (3) |
C8—C7—H7 | 126.7 | C46—C45—C44 | 119.3 (3) |
C6—C7—H7 | 126.7 | C46—C45—H45 | 120.4 |
C7—C8—C9 | 107.4 (2) | C44—C45—H45 | 120.4 |
C7—C8—H8 | 126.3 | C45—C46—C41 | 121.5 (3) |
C9—C8—H8 | 126.3 | C45—C46—H46 | 119.3 |
N22—C9—C10 | 125.3 (2) | C41—C46—H46 | 119.3 |
N22—C9—C8 | 109.8 (2) | N48—C47—C44 | 178.4 (4) |
C10—C9—C8 | 124.9 (2) | N50—C49—C58 | 122.8 (2) |
C11—C10—C9 | 125.9 (2) | N50—C49—C20 | 117.1 (2) |
C11—C10—C33 | 118.6 (2) | C58—C49—C20 | 120.2 (2) |
C9—C10—C33 | 115.5 (2) | C49—N50—C51 | 118.0 (2) |
N23—C11—C10 | 125.7 (2) | N50—C51—C52 | 118.7 (3) |
N23—C11—C12 | 109.6 (2) | N50—C51—C56 | 121.9 (2) |
C10—C11—C12 | 124.7 (2) | C52—C51—C56 | 119.4 (2) |
C13—C12—C11 | 107.0 (2) | C53—C52—C51 | 120.2 (3) |
C13—C12—H12 | 126.5 | C53—C52—H52 | 119.9 |
C11—C12—H12 | 126.5 | C51—C52—H52 | 119.9 |
C12—C13—C14 | 106.9 (2) | C52—C53—C54 | 120.9 (3) |
C12—C13—H13 | 126.5 | C52—C53—H53 | 119.6 |
C14—C13—H13 | 126.5 | C54—C53—H53 | 119.6 |
N23—C14—C15 | 125.9 (2) | C55—C54—C53 | 118.9 (3) |
N23—C14—C13 | 109.5 (2) | C55—C54—H54 | 120.6 |
C15—C14—C13 | 124.6 (2) | C53—C54—H54 | 120.6 |
C14—C15—C16 | 125.0 (2) | C54—C55—C56 | 122.2 (3) |
C14—C15—C41 | 117.6 (2) | C54—C55—H55 | 118.9 |
C16—C15—C41 | 117.3 (2) | C56—C55—H55 | 118.9 |
N24—C16—C15 | 125.2 (2) | C57—C56—C51 | 117.9 (2) |
N24—C16—C17 | 109.5 (2) | C57—C56—C55 | 123.6 (3) |
C15—C16—C17 | 125.3 (2) | C51—C56—C55 | 118.5 (3) |
C18—C17—C16 | 107.0 (2) | C58—C57—C56 | 119.6 (3) |
C18—C17—H17 | 126.5 | C58—C57—H57 | 120.2 |
C16—C17—H17 | 126.5 | C56—C57—H57 | 120.2 |
C17—C18—C19 | 107.1 (2) | C57—C58—C49 | 119.7 (2) |
C17—C18—H18 | 126.4 | C57—C58—H58 | 120.1 |
C19—C18—H18 | 126.4 | C49—C58—H58 | 120.1 |
N24—C19—C20 | 125.6 (2) | C60—N59—C64 | 114.8 (3) |
N24—C19—C18 | 109.8 (2) | C60—N59—Zn | 122.1 (2) |
C20—C19—C18 | 124.5 (2) | C64—N59—Zn | 122.9 (2) |
C1—C20—C19 | 125.9 (2) | N59—C60—C61 | 123.9 (4) |
C1—C20—C49 | 116.7 (2) | N59—C60—H60 | 118.1 |
C19—C20—C49 | 117.3 (2) | C61—C60—H60 | 118.1 |
C4—N21—C1 | 106.19 (19) | C62—C61—C60 | 119.0 (5) |
C4—N21—Zn | 127.77 (16) | C62—C61—H61 | 120.5 |
C1—N21—Zn | 125.93 (16) | C60—C61—H61 | 120.5 |
C6—N22—C9 | 106.15 (19) | C61—C62—C63 | 119.4 (4) |
C6—N22—Zn | 127.81 (16) | C61—C62—H62 | 120.3 |
C9—N22—Zn | 125.64 (16) | C63—C62—H62 | 120.3 |
C14—N23—C11 | 106.89 (19) | C62—C63—C64 | 118.5 (4) |
C14—N23—Zn | 126.66 (15) | C62—C63—H63 | 120.8 |
C11—N23—Zn | 125.73 (16) | C64—C63—H63 | 120.8 |
C19—N24—C16 | 106.62 (19) | N59—C64—C63 | 124.4 (3) |
C19—N24—Zn | 125.45 (16) | N59—C64—H64 | 117.8 |
C16—N24—Zn | 127.54 (15) | C63—C64—H64 | 117.8 |
C26—C25—C30 | 118.2 (3) | C70—C65—C66 | 118.4 (3) |
C26—C25—C5 | 121.6 (3) | C70—C65—H65 | 120.8 |
C30—C25—C5 | 120.2 (3) | C66—C65—H65 | 120.8 |
C25—C26—C27 | 121.6 (3) | C67—C66—C65 | 120.6 (3) |
C25—C26—H26 | 119.2 | C67—C66—H66 | 119.7 |
C27—C26—H26 | 119.2 | C65—C66—H66 | 119.7 |
C28—C27—C26 | 120.1 (3) | C66—C67—C68 | 119.7 (3) |
C28—C27—H27 | 120.0 | C66—C67—H67 | 120.2 |
C26—C27—H27 | 120.0 | C68—C67—H67 | 120.2 |
C27—C28—C29 | 120.1 (3) | C67—C68—C69 | 120.4 (3) |
C27—C28—C31 | 120.8 (3) | C67—C68—H68 | 119.8 |
C29—C28—C31 | 119.1 (3) | C69—C68—H68 | 119.8 |
C28—C29—C30 | 119.0 (3) | C70—C69—C68 | 119.4 (3) |
C28—C29—H29 | 120.5 | C70—C69—H69 | 120.3 |
C30—C29—H29 | 120.5 | C68—C69—H69 | 120.3 |
C25—C30—C29 | 121.0 (3) | C69—C70—C65 | 121.6 (3) |
C25—C30—H30 | 119.5 | C69—C70—N71 | 119.3 (3) |
C29—C30—H30 | 119.5 | C65—C70—N71 | 119.1 (3) |
N32—C31—C28 | 177.4 (4) | O73—N71—O72 | 123.2 (3) |
C38—C33—C34 | 119.5 (2) | O73—N71—C70 | 118.1 (3) |
C38—C33—C10 | 121.2 (2) | O72—N71—C70 | 118.6 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···N40a'i | 0.95 | 2.58 | 3.439 (4) | 151 |
C7—H7···N48b'ii | 0.95 | 2.59 | 3.498 (4) | 161 |
C38—H38···O73c'iii | 0.95 | 2.47 | 3.263 (4) | 140 |
C58—H58···N24d'iv | 0.95 | 2.59 | 3.348 (3) | 137 |
C68—H68···N50e'v | 0.95 | 2.57 | 3.482 (5) | 162 |
C17—H17···N32f'vi | 0.95 | 2.96 | 3.828 (4) | 153 |
Symmetry codes: (i) x, y, z−1; (ii) x+1, y−1, z; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y+2, −z; (v) −x, −y+1, −z+1; (vi) x−1, y+1, z. |
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