Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801014854/wn6049sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801014854/wn6049Isup2.hkl |
CCDC reference: 175333
Key indicators
- Single-crystal synchrotron study
- T = 160 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.054
- wR factor = 0.135
- Data-to-parameter ratio = 16.4
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level B:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.13 From the CIF: _reflns_number_total 12222 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 14289 Completeness (_total/calc) 85.53% Alert B: < 90% complete (theta max?)
Alert Level C:
PLAT_301 Alert C Main Residue Disorder ........................ 1.00 Perc. PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(28) - C(31) = 1.45 Ang. PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(39) - C(42) = 1.46 Ang. General Notes
ABSMU_01 Radiation type not identified. Calculation of _exptl_absorpt_correction_mu not performed.
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
3 Alert Level C = Please check
Crystals of (I) were grown from a solution in dichloromethane, layered with methanol.
H atoms attached to C atoms were placed geometrically and refined using a riding model with an isotropic displacement parameter fixed at 1.2Ueq for the carbon to which they are attached (1.5Ueq for methyl groups). H11A and H11B, associated with the water molecule, were located in a difference Fourier map and refined with an isotropic displacement parameter and the O11—H distance restrained to be 0.84 (1) Å. The terminal methyl group of one 2-methoxycarbonylethyl side chain was found to be disordered and was modelled as two equally occupied sites (C62 and C62'), each refined with an isotropic displacement parameter. The O10—C62 and O10—C62' bond distances were restrained to be identical, with an s.u. of 0.02 Å.
Data collection: SMART (Siemens, 1994); cell refinement: LSCELL (Clegg, 1995); data reduction: SAINT (Siemens, 1994); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Sheldrick, 1993); software used to prepare material for publication: SHELXL97.
[Zn(C62H66N4O10Si2)(H2O)] | Z = 2 |
Mr = 1166.75 | F(000) = 1228 |
Triclinic, P1 | Dx = 1.324 Mg m−3 |
a = 12.570 (2) Å | Synchrotron radiation, λ = 0.6879 Å |
b = 14.285 (3) Å | Cell parameters from 17561 reflections |
c = 17.502 (4) Å | θ = 3.4–27.1° |
α = 85.082 (10)° | µ = 0.52 mm−1 |
β = 69.225 (12)° | T = 160 K |
γ = 87.07 (2)° | Plate, red |
V = 2926.9 (11) Å3 | 0.07 × 0.06 × 0.02 mm |
Bruker SMART CCD diffractometer | 12222 independent reflections |
Radiation source: Daresbury SRS, Station 9.8 | 8256 reflections with I > 2σ(I) |
Silicon 111 monochromator | Rint = 0.066 |
Detector resolution: 8.192 pixels mm-1 | θmax = 27.1°, θmin = 3.4° |
Thin–slice ω scans | h = −15→16 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997b) | k = −18→17 |
Tmin = 0.964, Tmax = 0.990 | l = −18→22 |
17561 measured reflections |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.92 | w = 1/[σ2(Fo2) + (0.0676P)2] where P = (Fo2 + 2Fc2)/3 |
12222 reflections | (Δ/σ)max = 0.023 |
743 parameters | Δρmax = 1.19 e Å−3 |
4 restraints | Δρmin = −1.10 e Å−3 |
[Zn(C62H66N4O10Si2)(H2O)] | γ = 87.07 (2)° |
Mr = 1166.75 | V = 2926.9 (11) Å3 |
Triclinic, P1 | Z = 2 |
a = 12.570 (2) Å | Synchrotron radiation, λ = 0.6879 Å |
b = 14.285 (3) Å | µ = 0.52 mm−1 |
c = 17.502 (4) Å | T = 160 K |
α = 85.082 (10)° | 0.07 × 0.06 × 0.02 mm |
β = 69.225 (12)° |
Bruker SMART CCD diffractometer | 12222 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997b) | 8256 reflections with I > 2σ(I) |
Tmin = 0.964, Tmax = 0.990 | Rint = 0.066 |
17561 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 4 restraints |
wR(F2) = 0.135 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.92 | Δρmax = 1.19 e Å−3 |
12222 reflections | Δρmin = −1.10 e Å−3 |
743 parameters |
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. Least-squares plane (x,y,z in crystal coordinates) through the porphyrin unit (C1 - C20, N1 - N4) and deviations from it (* indicates atom used to define plane) -7.1883 (0.0040) x + 10.7118 (0.0051) y + 1.5154 (0.0044) z = 5.2523 (0.0031) * 0.0897 (0.0027) C1 * 0.3722 (0.0026) C2 * 0.4631 (0.0026) C3 * 0.1661 (0.0027) C4 * -0.0258 (0.0027) C5 * -0.1854 (0.0028) C6 * -0.5396 (0.0027) C7 * -0.4606 (0.0027) C8 * -0.0656 (0.0027) C9 * 0.2611 (0.0029) C10 * 0.2402 (0.0027) C11 * 0.4150 (0.0026) C12 * 0.2771 (0.0026) C13 * 0.0278 (0.0027) C14 * -0.1558 (0.0027) C15 * -0.2134 (0.0027) C16 * -0.3064 (0.0027) C17 * -0.1742 (0.0026) C18 * -0.0901 (0.0027) C19 * -0.0930 (0.0026) C20 * -0.0120 (0.0023) N1 * 0.0773 (0.0024) N2 * 0.0223 (0.0024) N3 * -0.0901 (0.0023) N4 Rms deviation of fitted atoms = 0.2527 |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Zn1 | −0.75965 (3) | −0.03363 (2) | −0.06889 (2) | 0.01340 (10) | |
Si1 | −0.22319 (9) | 0.39349 (6) | −0.71803 (6) | 0.0279 (2) | |
Si2 | −1.23771 (9) | −0.50192 (7) | 0.57031 (6) | 0.0303 (2) | |
O1 | −1.0236 (2) | −0.12280 (18) | −0.18284 (14) | 0.0355 (6) | |
O2 | −0.53290 (18) | 0.10361 (15) | 0.05309 (12) | 0.0212 (5) | |
O3 | −0.3745 (2) | 0.33046 (16) | 0.04603 (15) | 0.0334 (6) | |
O4 | −0.5287 (2) | 0.42532 (16) | 0.08533 (14) | 0.0332 (6) | |
O5 | −0.9140 (3) | −0.0986 (2) | −0.50853 (17) | 0.0615 (9) | |
O6 | −1.0661 (2) | −0.1460 (2) | −0.40254 (16) | 0.0470 (7) | |
O7 | −1.2229 (2) | −0.40948 (16) | 0.03632 (15) | 0.0361 (6) | |
O8 | −1.0887 (2) | −0.47144 (16) | −0.07073 (15) | 0.0333 (6) | |
O9 | −0.5939 (3) | 0.2617 (2) | 0.2393 (2) | 0.0642 (10) | |
O10 | −0.5951 (3) | 0.13257 (19) | 0.31931 (17) | 0.0459 (7) | |
O11 | −0.63680 (19) | −0.14123 (15) | −0.11010 (14) | 0.0210 (5) | |
H11A | −0.664 (3) | −0.1942 (14) | −0.090 (2) | 0.046 (9)* | |
H11B | −0.579 (2) | −0.135 (3) | −0.097 (2) | 0.046 (9)* | |
N1 | −0.6404 (2) | 0.07446 (16) | −0.10596 (14) | 0.0131 (5) | |
N2 | −0.7850 (2) | −0.00377 (16) | −0.18002 (14) | 0.0140 (5) | |
N3 | −0.9068 (2) | −0.11268 (16) | −0.02437 (14) | 0.0155 (5) | |
N4 | −0.7602 (2) | −0.03532 (16) | 0.04996 (14) | 0.0138 (5) | |
C1 | −0.5894 (2) | 0.11158 (19) | −0.05962 (17) | 0.0140 (6) | |
C2 | −0.5207 (2) | 0.1901 (2) | −0.10161 (18) | 0.0162 (6) | |
C3 | −0.5313 (2) | 0.20206 (19) | −0.17711 (17) | 0.0156 (6) | |
C4 | −0.6026 (2) | 0.12709 (19) | −0.18121 (17) | 0.0147 (6) | |
C5 | −0.6259 (2) | 0.1033 (2) | −0.25000 (17) | 0.0149 (6) | |
C6 | −0.7036 (2) | 0.0365 (2) | −0.25159 (17) | 0.0156 (6) | |
C7 | −0.7190 (3) | 0.0031 (2) | −0.32272 (18) | 0.0171 (6) | |
C8 | −0.8108 (3) | −0.0553 (2) | −0.29349 (18) | 0.0175 (6) | |
C9 | −0.8492 (2) | −0.05648 (19) | −0.20619 (17) | 0.0144 (6) | |
C10 | −0.9538 (3) | −0.1038 (2) | −0.15226 (18) | 0.0188 (6) | |
C11 | −0.9757 (2) | −0.13275 (19) | −0.06533 (18) | 0.0157 (6) | |
C12 | −1.0711 (2) | −0.18767 (19) | −0.01454 (17) | 0.0151 (6) | |
C13 | −1.0592 (2) | −0.2031 (2) | 0.06061 (17) | 0.0146 (6) | |
C14 | −0.9559 (2) | −0.15625 (19) | 0.05430 (17) | 0.0147 (6) | |
C15 | −0.9097 (3) | −0.15124 (19) | 0.11698 (17) | 0.0160 (6) | |
C16 | −0.8198 (2) | −0.0962 (2) | 0.11630 (17) | 0.0157 (6) | |
C17 | −0.7802 (3) | −0.0879 (2) | 0.18404 (18) | 0.0175 (6) | |
C18 | −0.7006 (3) | −0.0185 (2) | 0.15846 (18) | 0.0165 (6) | |
C19 | −0.6877 (2) | 0.0098 (2) | 0.07523 (17) | 0.0141 (6) | |
C20 | −0.6007 (2) | 0.07527 (19) | 0.02337 (18) | 0.0148 (6) | |
C21 | −0.4837 (3) | 0.2838 (2) | −0.23826 (19) | 0.0250 (7) | |
H21A | −0.4593 | 0.3319 | −0.2116 | 0.038* | |
H21B | −0.5424 | 0.3106 | −0.2590 | 0.038* | |
H21C | −0.4183 | 0.2621 | −0.2839 | 0.038* | |
C22 | −0.6499 (3) | 0.0224 (2) | −0.41234 (18) | 0.0286 (8) | |
H22A | −0.6680 | −0.0235 | −0.4441 | 0.043* | |
H22B | −0.5687 | 0.0174 | −0.4203 | 0.043* | |
H22C | −0.6682 | 0.0859 | −0.4308 | 0.043* | |
C23 | −1.1440 (3) | −0.2554 (2) | 0.13378 (18) | 0.0201 (7) | |
H23A | −1.2069 | −0.2755 | 0.1188 | 0.030* | |
H23B | −1.1735 | −0.2139 | 0.1788 | 0.030* | |
H23C | −1.1064 | −0.3106 | 0.1512 | 0.030* | |
C24 | −0.8071 (3) | −0.1428 (2) | 0.26567 (19) | 0.0272 (8) | |
H24A | −0.7464 | −0.1348 | 0.2873 | 0.041* | |
H24B | −0.8129 | −0.2095 | 0.2589 | 0.041* | |
H24C | −0.8795 | −0.1198 | 0.3039 | 0.041* | |
C25 | −0.5603 (3) | 0.1549 (2) | −0.32990 (17) | 0.0167 (6) | |
C26 | −0.4480 (3) | 0.1306 (2) | −0.37082 (18) | 0.0202 (7) | |
H26A | −0.4133 | 0.0800 | −0.3486 | 0.024* | |
C27 | −0.3849 (3) | 0.1788 (2) | −0.44388 (18) | 0.0204 (7) | |
H27A | −0.3074 | 0.1618 | −0.4712 | 0.025* | |
C28 | −0.4367 (3) | 0.2528 (2) | −0.47704 (18) | 0.0200 (7) | |
C29 | −0.5506 (3) | 0.2772 (2) | −0.43475 (19) | 0.0227 (7) | |
H29A | −0.5862 | 0.3275 | −0.4565 | 0.027* | |
C30 | −0.6118 (3) | 0.2287 (2) | −0.36158 (18) | 0.0207 (7) | |
H30A | −0.6889 | 0.2459 | −0.3331 | 0.025* | |
C31 | −0.3718 (3) | 0.3018 (2) | −0.55412 (19) | 0.0237 (7) | |
C32 | −0.3174 (3) | 0.3406 (2) | −0.6182 (2) | 0.0270 (8) | |
C33 | −0.0783 (3) | 0.3943 (3) | −0.7123 (2) | 0.0398 (9) | |
H33A | −0.0514 | 0.3296 | −0.7057 | 0.060* | |
H33B | −0.0810 | 0.4283 | −0.6653 | 0.060* | |
H33C | −0.0262 | 0.4255 | −0.7627 | 0.060* | |
C34 | −0.2768 (4) | 0.5149 (3) | −0.7336 (3) | 0.0493 (11) | |
H34A | −0.3570 | 0.5131 | −0.7280 | 0.074* | |
H34B | −0.2323 | 0.5416 | −0.7885 | 0.074* | |
H34C | −0.2692 | 0.5539 | −0.6925 | 0.074* | |
C35 | −0.2282 (4) | 0.3181 (3) | −0.7983 (2) | 0.0417 (10) | |
H35A | −0.2167 | 0.2521 | −0.7819 | 0.063* | |
H35B | −0.1681 | 0.3362 | −0.8504 | 0.063* | |
H35C | −0.3025 | 0.3263 | −0.8048 | 0.063* | |
C36 | −0.9652 (2) | −0.2105 (2) | 0.19475 (17) | 0.0155 (6) | |
C37 | −0.9314 (3) | −0.3045 (2) | 0.20132 (19) | 0.0218 (7) | |
H37A | −0.8738 | −0.3310 | 0.1565 | 0.026* | |
C38 | −0.9825 (3) | −0.3594 (2) | 0.27410 (19) | 0.0244 (7) | |
H38A | −0.9601 | −0.4236 | 0.2785 | 0.029* | |
C39 | −1.0660 (3) | −0.3207 (2) | 0.34003 (18) | 0.0221 (7) | |
C40 | −1.0980 (3) | −0.2261 (2) | 0.33287 (18) | 0.0206 (7) | |
H40A | −1.1548 | −0.1991 | 0.3778 | 0.025* | |
C41 | −1.0476 (3) | −0.1718 (2) | 0.26076 (18) | 0.0194 (7) | |
H41A | −1.0696 | −0.1075 | 0.2565 | 0.023* | |
C42 | −1.1222 (3) | −0.3779 (2) | 0.4154 (2) | 0.0275 (8) | |
C43 | −1.1686 (3) | −0.4253 (2) | 0.4766 (2) | 0.0298 (8) | |
C44 | −1.2121 (4) | −0.4546 (3) | 0.6576 (2) | 0.0531 (12) | |
H44A | −1.2534 | −0.3944 | 0.6698 | 0.080* | |
H44B | −1.1305 | −0.4451 | 0.6432 | 0.080* | |
H44C | −1.2391 | −0.4992 | 0.7058 | 0.080* | |
C45 | −1.3928 (3) | −0.5024 (3) | 0.5888 (3) | 0.0485 (11) | |
H45A | −1.4254 | −0.4391 | 0.6001 | 0.073* | |
H45B | −1.4301 | −0.5464 | 0.6358 | 0.073* | |
H45C | −1.4045 | −0.5220 | 0.5401 | 0.073* | |
C46 | −1.1728 (3) | −0.6214 (3) | 0.5531 (2) | 0.0419 (10) | |
H46A | −1.0912 | −0.6190 | 0.5435 | 0.063* | |
H46B | −1.1835 | −0.6445 | 0.5053 | 0.063* | |
H46C | −1.2092 | −0.6639 | 0.6015 | 0.063* | |
C47 | −0.4532 (3) | 0.2499 (2) | −0.06896 (19) | 0.0209 (7) | |
H47A | −0.4030 | 0.2908 | −0.1147 | 0.025* | |
H47B | −0.4042 | 0.2085 | −0.0464 | 0.025* | |
C48 | −0.5285 (3) | 0.3109 (2) | −0.0025 (2) | 0.0240 (7) | |
H48A | −0.5651 | 0.3609 | −0.0281 | 0.029* | |
H48B | −0.5897 | 0.2718 | 0.0368 | 0.029* | |
C49 | −0.4673 (3) | 0.3561 (2) | 0.0439 (2) | 0.0246 (7) | |
C50 | −0.4839 (4) | 0.4645 (3) | 0.1414 (2) | 0.0438 (10) | |
H50A | −0.5326 | 0.5175 | 0.1666 | 0.066* | |
H50B | −0.4065 | 0.4864 | 0.1112 | 0.066* | |
H50C | −0.4822 | 0.4161 | 0.1842 | 0.066* | |
C51 | −0.8578 (3) | −0.1081 (2) | −0.34478 (19) | 0.0210 (7) | |
H51A | −0.8967 | −0.1645 | −0.3120 | 0.025* | |
H51B | −0.7940 | −0.1295 | −0.3927 | 0.025* | |
C52 | −0.9419 (3) | −0.0483 (2) | −0.3751 (2) | 0.0310 (8) | |
H52A | −1.0120 | −0.0356 | −0.3280 | 0.037* | |
H52B | −0.9076 | 0.0128 | −0.4005 | 0.037* | |
C53 | −0.9715 (3) | −0.0984 (3) | −0.4364 (2) | 0.0320 (8) | |
C54 | −1.1006 (4) | −0.1982 (4) | −0.4566 (3) | 0.0669 (15) | |
H54A | −1.1744 | −0.2267 | −0.4260 | 0.100* | |
H54B | −1.0437 | −0.2477 | −0.4787 | 0.100* | |
H54C | −1.1073 | −0.1557 | −0.5017 | 0.100* | |
C55 | −1.1650 (2) | −0.2219 (2) | −0.03925 (18) | 0.0170 (6) | |
H55A | −1.1866 | −0.1711 | −0.0734 | 0.020* | |
H55B | −1.2324 | −0.2348 | 0.0108 | 0.020* | |
C56 | −1.1339 (3) | −0.3107 (2) | −0.08685 (19) | 0.0214 (7) | |
H56A | −1.1794 | −0.3107 | −0.1229 | 0.026* | |
H56B | −1.0526 | −0.3086 | −0.1223 | 0.026* | |
C57 | −1.1539 (3) | −0.4007 (2) | −0.0327 (2) | 0.0241 (7) | |
C58 | −1.1065 (4) | −0.5610 (2) | −0.0221 (3) | 0.0424 (10) | |
H58A | −1.0498 | −0.6073 | −0.0514 | 0.064* | |
H58B | −1.1830 | −0.5828 | −0.0127 | 0.064* | |
H58C | −1.0986 | −0.5530 | 0.0307 | 0.064* | |
C59 | −0.6465 (3) | 0.0250 (2) | 0.21044 (18) | 0.0198 (7) | |
H59A | −0.5628 | 0.0244 | 0.1826 | 0.024* | |
H59B | −0.6641 | −0.0126 | 0.2635 | 0.024* | |
C60 | −0.6900 (3) | 0.1272 (2) | 0.2261 (2) | 0.0246 (7) | |
H60A | −0.6892 | 0.1601 | 0.1737 | 0.030* | |
H60B | −0.7699 | 0.1261 | 0.2643 | 0.030* | |
C61 | −0.6215 (3) | 0.1817 (2) | 0.2609 (2) | 0.0302 (8) | |
C62 | −0.5097 (8) | 0.1822 (7) | 0.3416 (6) | 0.043 (2)* | 0.50 |
H62A | −0.4401 | 0.1907 | 0.2935 | 0.065* | 0.50 |
H62B | −0.4920 | 0.1448 | 0.3854 | 0.065* | 0.50 |
H62C | −0.5409 | 0.2438 | 0.3606 | 0.065* | 0.50 |
C62' | −0.5431 (9) | 0.1785 (7) | 0.3677 (6) | 0.048 (3)* | 0.50 |
H62D | −0.5595 | 0.1433 | 0.4211 | 0.072* | 0.50 |
H62E | −0.5740 | 0.2427 | 0.3757 | 0.072* | 0.50 |
H62F | −0.4605 | 0.1803 | 0.3389 | 0.072* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.01236 (18) | 0.01553 (17) | 0.01190 (17) | −0.00457 (13) | −0.00401 (13) | 0.00260 (13) |
Si1 | 0.0326 (5) | 0.0224 (5) | 0.0187 (5) | −0.0059 (4) | 0.0021 (4) | 0.0059 (4) |
Si2 | 0.0286 (5) | 0.0321 (5) | 0.0243 (5) | −0.0078 (4) | −0.0047 (4) | 0.0140 (4) |
O1 | 0.0274 (14) | 0.0593 (17) | 0.0240 (13) | −0.0231 (13) | −0.0142 (11) | 0.0112 (12) |
O2 | 0.0197 (12) | 0.0270 (12) | 0.0201 (11) | −0.0088 (9) | −0.0104 (10) | 0.0017 (9) |
O3 | 0.0372 (15) | 0.0275 (13) | 0.0439 (15) | −0.0053 (11) | −0.0232 (13) | −0.0065 (11) |
O4 | 0.0466 (16) | 0.0234 (12) | 0.0326 (14) | 0.0006 (11) | −0.0162 (12) | −0.0087 (10) |
O5 | 0.058 (2) | 0.096 (3) | 0.0323 (16) | −0.0207 (19) | −0.0134 (15) | −0.0133 (16) |
O6 | 0.0521 (18) | 0.0595 (18) | 0.0317 (15) | −0.0256 (15) | −0.0124 (13) | −0.0120 (13) |
O7 | 0.0419 (16) | 0.0250 (13) | 0.0315 (14) | −0.0053 (11) | −0.0006 (12) | 0.0001 (11) |
O8 | 0.0343 (15) | 0.0263 (13) | 0.0348 (14) | 0.0026 (11) | −0.0062 (12) | −0.0059 (11) |
O9 | 0.082 (3) | 0.0319 (16) | 0.095 (3) | −0.0181 (16) | −0.051 (2) | 0.0040 (16) |
O10 | 0.063 (2) | 0.0447 (16) | 0.0455 (17) | −0.0187 (15) | −0.0368 (16) | −0.0024 (13) |
O11 | 0.0184 (12) | 0.0198 (11) | 0.0267 (12) | −0.0030 (9) | −0.0102 (10) | −0.0008 (10) |
N1 | 0.0136 (12) | 0.0158 (12) | 0.0087 (11) | −0.0021 (10) | −0.0025 (10) | 0.0011 (9) |
N2 | 0.0121 (12) | 0.0171 (12) | 0.0115 (12) | −0.0055 (10) | −0.0026 (10) | 0.0025 (10) |
N3 | 0.0153 (13) | 0.0174 (12) | 0.0145 (12) | −0.0051 (10) | −0.0066 (10) | 0.0033 (10) |
N4 | 0.0108 (12) | 0.0158 (12) | 0.0147 (12) | −0.0036 (10) | −0.0046 (10) | 0.0009 (10) |
C1 | 0.0124 (14) | 0.0134 (14) | 0.0172 (15) | −0.0024 (11) | −0.0066 (12) | 0.0002 (11) |
C2 | 0.0114 (15) | 0.0171 (14) | 0.0184 (15) | −0.0038 (12) | −0.0029 (12) | 0.0005 (12) |
C3 | 0.0151 (15) | 0.0148 (14) | 0.0153 (15) | −0.0023 (12) | −0.0035 (12) | 0.0007 (12) |
C4 | 0.0124 (14) | 0.0146 (14) | 0.0146 (14) | −0.0027 (11) | −0.0022 (12) | 0.0017 (11) |
C5 | 0.0132 (15) | 0.0172 (14) | 0.0115 (14) | −0.0026 (12) | −0.0018 (12) | 0.0051 (11) |
C6 | 0.0140 (15) | 0.0183 (15) | 0.0120 (14) | −0.0032 (12) | −0.0018 (12) | 0.0016 (12) |
C7 | 0.0173 (16) | 0.0201 (15) | 0.0136 (15) | −0.0022 (12) | −0.0046 (12) | −0.0025 (12) |
C8 | 0.0201 (16) | 0.0158 (14) | 0.0169 (15) | −0.0018 (12) | −0.0066 (13) | −0.0008 (12) |
C9 | 0.0147 (15) | 0.0140 (14) | 0.0137 (14) | −0.0031 (12) | −0.0046 (12) | 0.0042 (11) |
C10 | 0.0153 (16) | 0.0244 (16) | 0.0186 (16) | −0.0074 (13) | −0.0083 (13) | 0.0031 (13) |
C11 | 0.0140 (15) | 0.0157 (14) | 0.0177 (15) | −0.0040 (12) | −0.0060 (12) | 0.0005 (12) |
C12 | 0.0112 (14) | 0.0150 (14) | 0.0176 (15) | −0.0027 (11) | −0.0034 (12) | 0.0012 (12) |
C13 | 0.0098 (14) | 0.0163 (14) | 0.0142 (14) | −0.0031 (11) | 0.0000 (12) | 0.0010 (11) |
C14 | 0.0139 (15) | 0.0131 (14) | 0.0153 (15) | −0.0028 (11) | −0.0031 (12) | 0.0008 (11) |
C15 | 0.0176 (16) | 0.0140 (14) | 0.0154 (15) | −0.0006 (12) | −0.0054 (13) | 0.0027 (11) |
C16 | 0.0133 (15) | 0.0197 (15) | 0.0120 (14) | −0.0027 (12) | −0.0024 (12) | 0.0026 (12) |
C17 | 0.0158 (15) | 0.0207 (15) | 0.0170 (15) | −0.0011 (12) | −0.0074 (13) | 0.0015 (12) |
C18 | 0.0147 (15) | 0.0186 (15) | 0.0172 (15) | 0.0005 (12) | −0.0069 (12) | −0.0019 (12) |
C19 | 0.0123 (14) | 0.0177 (14) | 0.0133 (14) | −0.0020 (12) | −0.0057 (12) | −0.0006 (11) |
C20 | 0.0114 (14) | 0.0140 (14) | 0.0189 (15) | −0.0001 (11) | −0.0048 (12) | −0.0033 (12) |
C21 | 0.0323 (19) | 0.0197 (16) | 0.0242 (17) | −0.0138 (14) | −0.0110 (15) | 0.0045 (13) |
C22 | 0.031 (2) | 0.0364 (19) | 0.0154 (16) | −0.0146 (16) | −0.0024 (15) | −0.0032 (14) |
C23 | 0.0115 (15) | 0.0288 (17) | 0.0160 (15) | −0.0087 (13) | 0.0006 (12) | 0.0009 (13) |
C24 | 0.0301 (19) | 0.0317 (18) | 0.0245 (18) | −0.0130 (15) | −0.0168 (15) | 0.0122 (14) |
C25 | 0.0177 (16) | 0.0194 (15) | 0.0135 (15) | −0.0089 (12) | −0.0056 (13) | 0.0026 (12) |
C26 | 0.0203 (17) | 0.0205 (15) | 0.0192 (16) | −0.0019 (13) | −0.0072 (13) | 0.0039 (13) |
C27 | 0.0169 (16) | 0.0268 (17) | 0.0151 (15) | −0.0050 (13) | −0.0024 (13) | 0.0009 (13) |
C28 | 0.0246 (17) | 0.0218 (16) | 0.0139 (15) | −0.0112 (13) | −0.0074 (13) | 0.0049 (12) |
C29 | 0.0199 (17) | 0.0265 (17) | 0.0210 (16) | −0.0059 (14) | −0.0072 (14) | 0.0050 (13) |
C30 | 0.0147 (16) | 0.0260 (16) | 0.0200 (16) | −0.0035 (13) | −0.0055 (13) | 0.0044 (13) |
C31 | 0.0256 (18) | 0.0263 (17) | 0.0182 (16) | −0.0069 (14) | −0.0060 (14) | 0.0002 (14) |
C32 | 0.0276 (19) | 0.0278 (18) | 0.0229 (18) | −0.0074 (15) | −0.0054 (15) | 0.0022 (14) |
C33 | 0.032 (2) | 0.034 (2) | 0.042 (2) | −0.0134 (17) | 0.0023 (18) | −0.0014 (17) |
C34 | 0.060 (3) | 0.027 (2) | 0.048 (3) | −0.003 (2) | −0.006 (2) | 0.0122 (18) |
C35 | 0.052 (3) | 0.042 (2) | 0.029 (2) | −0.004 (2) | −0.0121 (19) | 0.0034 (17) |
C36 | 0.0148 (15) | 0.0175 (14) | 0.0145 (15) | −0.0055 (12) | −0.0057 (12) | 0.0028 (12) |
C37 | 0.0251 (18) | 0.0205 (16) | 0.0162 (16) | −0.0016 (13) | −0.0032 (14) | 0.0006 (13) |
C38 | 0.0304 (19) | 0.0176 (15) | 0.0248 (17) | −0.0073 (14) | −0.0101 (15) | 0.0065 (13) |
C39 | 0.0243 (18) | 0.0281 (17) | 0.0168 (16) | −0.0124 (14) | −0.0117 (14) | 0.0090 (13) |
C40 | 0.0173 (16) | 0.0303 (17) | 0.0143 (15) | −0.0048 (13) | −0.0054 (13) | 0.0001 (13) |
C41 | 0.0202 (17) | 0.0186 (15) | 0.0195 (16) | −0.0033 (13) | −0.0072 (13) | 0.0009 (12) |
C42 | 0.0288 (19) | 0.0297 (18) | 0.0257 (18) | −0.0110 (15) | −0.0122 (15) | 0.0062 (15) |
C43 | 0.034 (2) | 0.0317 (19) | 0.0244 (18) | −0.0149 (16) | −0.0119 (16) | 0.0124 (15) |
C44 | 0.068 (3) | 0.058 (3) | 0.034 (2) | 0.004 (2) | −0.021 (2) | 0.003 (2) |
C45 | 0.031 (2) | 0.044 (2) | 0.058 (3) | −0.0070 (19) | −0.004 (2) | 0.020 (2) |
C46 | 0.031 (2) | 0.043 (2) | 0.047 (2) | −0.0058 (18) | −0.0113 (19) | 0.0125 (19) |
C47 | 0.0191 (16) | 0.0222 (16) | 0.0224 (16) | −0.0099 (13) | −0.0083 (14) | 0.0028 (13) |
C48 | 0.0246 (18) | 0.0215 (16) | 0.0305 (18) | −0.0023 (14) | −0.0147 (15) | −0.0033 (14) |
C49 | 0.031 (2) | 0.0176 (16) | 0.0260 (18) | −0.0069 (14) | −0.0112 (15) | 0.0023 (13) |
C50 | 0.067 (3) | 0.030 (2) | 0.040 (2) | −0.008 (2) | −0.023 (2) | −0.0104 (17) |
C51 | 0.0271 (18) | 0.0194 (15) | 0.0187 (16) | −0.0068 (13) | −0.0103 (14) | −0.0004 (13) |
C52 | 0.041 (2) | 0.0268 (18) | 0.035 (2) | −0.0013 (16) | −0.0247 (18) | −0.0055 (15) |
C53 | 0.036 (2) | 0.040 (2) | 0.027 (2) | 0.0004 (17) | −0.0200 (17) | −0.0036 (16) |
C54 | 0.071 (4) | 0.079 (3) | 0.063 (3) | −0.032 (3) | −0.030 (3) | −0.026 (3) |
C55 | 0.0125 (15) | 0.0208 (15) | 0.0173 (15) | −0.0023 (12) | −0.0051 (12) | 0.0008 (12) |
C56 | 0.0182 (16) | 0.0249 (16) | 0.0205 (16) | −0.0044 (13) | −0.0053 (13) | −0.0029 (13) |
C57 | 0.0209 (17) | 0.0258 (17) | 0.0273 (18) | −0.0041 (14) | −0.0092 (15) | −0.0064 (14) |
C58 | 0.052 (3) | 0.0218 (18) | 0.052 (3) | 0.0019 (18) | −0.017 (2) | −0.0038 (17) |
C59 | 0.0210 (17) | 0.0258 (16) | 0.0137 (15) | −0.0060 (13) | −0.0072 (13) | 0.0017 (13) |
C60 | 0.0221 (18) | 0.0304 (18) | 0.0199 (17) | −0.0009 (14) | −0.0044 (14) | −0.0075 (14) |
C61 | 0.030 (2) | 0.0292 (19) | 0.0290 (19) | −0.0035 (15) | −0.0055 (16) | −0.0079 (15) |
Zn1—N4 | 2.076 (2) | C25—C30 | 1.386 (4) |
Zn1—N3 | 2.085 (2) | C26—C27 | 1.387 (4) |
Zn1—N2 | 2.086 (2) | C26—H26A | 0.9500 |
Zn1—O11 | 2.103 (2) | C27—C28 | 1.405 (4) |
Zn1—N1 | 2.104 (2) | C27—H27A | 0.9500 |
Si1—C32 | 1.851 (3) | C28—C29 | 1.400 (5) |
Si1—C33 | 1.860 (4) | C28—C31 | 1.446 (4) |
Si1—C34 | 1.862 (4) | C29—C30 | 1.384 (4) |
Si1—C35 | 1.862 (4) | C29—H29A | 0.9500 |
Si2—C43 | 1.850 (3) | C30—H30A | 0.9500 |
Si2—C44 | 1.855 (4) | C31—C32 | 1.191 (4) |
Si2—C46 | 1.855 (4) | C33—H33A | 0.9800 |
Si2—C45 | 1.860 (4) | C33—H33B | 0.9800 |
O1—C10 | 1.229 (3) | C33—H33C | 0.9800 |
O2—C20 | 1.243 (3) | C34—H34A | 0.9800 |
O3—C49 | 1.216 (4) | C34—H34B | 0.9800 |
O4—C49 | 1.322 (4) | C34—H34C | 0.9800 |
O4—C50 | 1.454 (4) | C35—H35A | 0.9800 |
O5—C53 | 1.213 (4) | C35—H35B | 0.9800 |
O6—C53 | 1.319 (4) | C35—H35C | 0.9800 |
O6—C54 | 1.444 (4) | C36—C41 | 1.384 (4) |
O7—C57 | 1.212 (4) | C36—C37 | 1.395 (4) |
O8—C57 | 1.333 (4) | C37—C38 | 1.397 (4) |
O8—C58 | 1.455 (4) | C37—H37A | 0.9500 |
O9—C61 | 1.202 (4) | C38—C39 | 1.389 (5) |
O10—C61 | 1.320 (4) | C38—H38A | 0.9500 |
O10—C62' | 1.452 (9) | C39—C40 | 1.398 (4) |
O10—C62 | 1.493 (9) | C39—C42 | 1.456 (4) |
O11—H11A | 0.84 (2) | C40—C41 | 1.383 (4) |
O11—H11B | 0.84 (2) | C40—H40A | 0.9500 |
N1—C1 | 1.351 (3) | C41—H41A | 0.9500 |
N1—C4 | 1.396 (3) | C42—C43 | 1.191 (4) |
N2—C9 | 1.346 (4) | C44—H44A | 0.9800 |
N2—C6 | 1.405 (3) | C44—H44B | 0.9800 |
N3—C11 | 1.359 (4) | C44—H44C | 0.9800 |
N3—C14 | 1.398 (4) | C45—H45A | 0.9800 |
N4—C19 | 1.356 (3) | C45—H45B | 0.9800 |
N4—C16 | 1.393 (4) | C45—H45C | 0.9800 |
C1—C2 | 1.432 (4) | C46—H46A | 0.9800 |
C1—C20 | 1.460 (4) | C46—H46B | 0.9800 |
C2—C3 | 1.370 (4) | C46—H46C | 0.9800 |
C2—C47 | 1.509 (4) | C47—C48 | 1.522 (4) |
C3—C4 | 1.453 (4) | C47—H47A | 0.9900 |
C3—C21 | 1.507 (4) | C47—H47B | 0.9900 |
C4—C5 | 1.407 (4) | C48—C49 | 1.501 (4) |
C5—C6 | 1.409 (4) | C48—H48A | 0.9900 |
C5—C25 | 1.499 (4) | C48—H48B | 0.9900 |
C6—C7 | 1.448 (4) | C50—H50A | 0.9800 |
C7—C8 | 1.377 (4) | C50—H50B | 0.9800 |
C7—C22 | 1.508 (4) | C50—H50C | 0.9800 |
C8—C9 | 1.429 (4) | C51—C52 | 1.536 (4) |
C8—C51 | 1.503 (4) | C51—H51A | 0.9900 |
C9—C10 | 1.476 (4) | C51—H51B | 0.9900 |
C10—C11 | 1.472 (4) | C52—C53 | 1.498 (4) |
C11—C12 | 1.437 (4) | C52—H52A | 0.9900 |
C12—C13 | 1.374 (4) | C52—H52B | 0.9900 |
C12—C55 | 1.508 (4) | C54—H54A | 0.9800 |
C13—C14 | 1.456 (4) | C54—H54B | 0.9800 |
C13—C23 | 1.511 (4) | C54—H54C | 0.9800 |
C14—C15 | 1.420 (4) | C55—C56 | 1.534 (4) |
C15—C16 | 1.406 (4) | C55—H55A | 0.9900 |
C15—C36 | 1.498 (4) | C55—H55B | 0.9900 |
C16—C17 | 1.454 (4) | C56—C57 | 1.507 (4) |
C17—C18 | 1.376 (4) | C56—H56A | 0.9900 |
C17—C24 | 1.504 (4) | C56—H56B | 0.9900 |
C18—C19 | 1.432 (4) | C58—H58A | 0.9800 |
C18—C59 | 1.502 (4) | C58—H58B | 0.9800 |
C19—C20 | 1.466 (4) | C58—H58C | 0.9800 |
C21—H21A | 0.9800 | C59—C60 | 1.544 (4) |
C21—H21B | 0.9800 | C59—H59A | 0.9900 |
C21—H21C | 0.9800 | C59—H59B | 0.9900 |
C22—H22A | 0.9800 | C60—C61 | 1.496 (4) |
C22—H22B | 0.9800 | C60—H60A | 0.9900 |
C22—H22C | 0.9800 | C60—H60B | 0.9900 |
C23—H23A | 0.9800 | C62—H62A | 0.9800 |
C23—H23B | 0.9800 | C62—H62B | 0.9800 |
C23—H23C | 0.9800 | C62—H62C | 0.9800 |
C24—H24A | 0.9800 | C62'—H62D | 0.9800 |
C24—H24B | 0.9800 | C62'—H62E | 0.9800 |
C24—H24C | 0.9800 | C62'—H62F | 0.9800 |
C25—C26 | 1.379 (4) | ||
N4—Zn1—N3 | 88.75 (9) | C32—C31—C28 | 178.7 (4) |
N4—Zn1—N2 | 166.17 (9) | C31—C32—Si1 | 175.2 (3) |
N3—Zn1—N2 | 90.33 (9) | Si1—C33—H33A | 109.5 |
N4—Zn1—O11 | 97.99 (9) | Si1—C33—H33B | 109.5 |
N3—Zn1—O11 | 99.99 (9) | H33A—C33—H33B | 109.5 |
N2—Zn1—O11 | 95.76 (9) | Si1—C33—H33C | 109.5 |
N4—Zn1—N1 | 90.20 (9) | H33A—C33—H33C | 109.5 |
N3—Zn1—N1 | 165.65 (9) | H33B—C33—H33C | 109.5 |
N2—Zn1—N1 | 87.28 (9) | Si1—C34—H34A | 109.5 |
O11—Zn1—N1 | 94.34 (9) | Si1—C34—H34B | 109.5 |
C32—Si1—C33 | 106.54 (17) | H34A—C34—H34B | 109.5 |
C32—Si1—C34 | 108.52 (18) | Si1—C34—H34C | 109.5 |
C33—Si1—C34 | 111.30 (19) | H34A—C34—H34C | 109.5 |
C32—Si1—C35 | 107.17 (16) | H34B—C34—H34C | 109.5 |
C33—Si1—C35 | 111.88 (19) | Si1—C35—H35A | 109.5 |
C34—Si1—C35 | 111.19 (19) | Si1—C35—H35B | 109.5 |
C43—Si2—C44 | 108.79 (18) | H35A—C35—H35B | 109.5 |
C43—Si2—C46 | 107.85 (17) | Si1—C35—H35C | 109.5 |
C44—Si2—C46 | 110.1 (2) | H35A—C35—H35C | 109.5 |
C43—Si2—C45 | 108.22 (17) | H35B—C35—H35C | 109.5 |
C44—Si2—C45 | 110.5 (2) | C41—C36—C37 | 119.9 (3) |
C46—Si2—C45 | 111.28 (19) | C41—C36—C15 | 120.3 (3) |
C49—O4—C50 | 115.7 (3) | C37—C36—C15 | 119.7 (3) |
C53—O6—C54 | 116.5 (3) | C36—C37—C38 | 119.7 (3) |
C57—O8—C58 | 114.3 (3) | C36—C37—H37A | 120.1 |
C61—O10—C62' | 119.9 (5) | C38—C37—H37A | 120.1 |
C61—O10—C62 | 111.0 (5) | C39—C38—C37 | 120.3 (3) |
C62'—O10—C62 | 19.5 (6) | C39—C38—H38A | 119.8 |
Zn1—O11—H11A | 111 (3) | C37—C38—H38A | 119.8 |
Zn1—O11—H11B | 113 (3) | C38—C39—C40 | 119.3 (3) |
H11A—O11—H11B | 108 (4) | C38—C39—C42 | 120.8 (3) |
C1—N1—C4 | 105.3 (2) | C40—C39—C42 | 119.8 (3) |
C1—N1—Zn1 | 126.86 (18) | C41—C40—C39 | 120.4 (3) |
C4—N1—Zn1 | 127.70 (18) | C41—C40—H40A | 119.8 |
C9—N2—C6 | 105.3 (2) | C39—C40—H40A | 119.8 |
C9—N2—Zn1 | 123.24 (18) | C40—C41—C36 | 120.4 (3) |
C6—N2—Zn1 | 124.55 (18) | C40—C41—H41A | 119.8 |
C11—N3—C14 | 105.2 (2) | C36—C41—H41A | 119.8 |
C11—N3—Zn1 | 127.52 (19) | C43—C42—C39 | 179.3 (4) |
C14—N3—Zn1 | 127.24 (19) | C42—C43—Si2 | 178.2 (4) |
C19—N4—C16 | 105.5 (2) | Si2—C44—H44A | 109.5 |
C19—N4—Zn1 | 126.71 (19) | Si2—C44—H44B | 109.5 |
C16—N4—Zn1 | 126.74 (19) | H44A—C44—H44B | 109.5 |
N1—C1—C2 | 112.4 (2) | Si2—C44—H44C | 109.5 |
N1—C1—C20 | 124.3 (2) | H44A—C44—H44C | 109.5 |
C2—C1—C20 | 123.3 (2) | H44B—C44—H44C | 109.5 |
C3—C2—C1 | 105.9 (2) | Si2—C45—H45A | 109.5 |
C3—C2—C47 | 126.6 (3) | Si2—C45—H45B | 109.5 |
C1—C2—C47 | 127.4 (3) | H45A—C45—H45B | 109.5 |
C2—C3—C4 | 106.8 (2) | Si2—C45—H45C | 109.5 |
C2—C3—C21 | 124.0 (3) | H45A—C45—H45C | 109.5 |
C4—C3—C21 | 129.1 (3) | H45B—C45—H45C | 109.5 |
N1—C4—C5 | 122.9 (2) | Si2—C46—H46A | 109.5 |
N1—C4—C3 | 109.4 (2) | Si2—C46—H46B | 109.5 |
C5—C4—C3 | 127.6 (2) | H46A—C46—H46B | 109.5 |
C4—C5—C6 | 127.0 (2) | Si2—C46—H46C | 109.5 |
C4—C5—C25 | 116.0 (2) | H46A—C46—H46C | 109.5 |
C6—C5—C25 | 117.0 (2) | H46B—C46—H46C | 109.5 |
N2—C6—C5 | 122.6 (3) | C2—C47—C48 | 112.8 (3) |
N2—C6—C7 | 109.5 (2) | C2—C47—H47A | 109.0 |
C5—C6—C7 | 127.7 (3) | C48—C47—H47A | 109.0 |
C8—C7—C6 | 106.4 (2) | C2—C47—H47B | 109.0 |
C8—C7—C22 | 124.1 (3) | C48—C47—H47B | 109.0 |
C6—C7—C22 | 129.5 (3) | H47A—C47—H47B | 107.8 |
C7—C8—C9 | 106.3 (3) | C49—C48—C47 | 114.6 (3) |
C7—C8—C51 | 125.8 (3) | C49—C48—H48A | 108.6 |
C9—C8—C51 | 127.9 (3) | C47—C48—H48A | 108.6 |
N2—C9—C8 | 112.5 (3) | C49—C48—H48B | 108.6 |
N2—C9—C10 | 124.5 (3) | C47—C48—H48B | 108.6 |
C8—C9—C10 | 122.8 (3) | H48A—C48—H48B | 107.6 |
O1—C10—C11 | 119.0 (3) | O3—C49—O4 | 123.6 (3) |
O1—C10—C9 | 117.8 (3) | O3—C49—C48 | 124.7 (3) |
C11—C10—C9 | 123.2 (3) | O4—C49—C48 | 111.6 (3) |
N3—C11—C12 | 112.2 (2) | O4—C50—H50A | 109.5 |
N3—C11—C10 | 124.1 (3) | O4—C50—H50B | 109.5 |
C12—C11—C10 | 123.7 (3) | H50A—C50—H50B | 109.5 |
C13—C12—C11 | 106.2 (2) | O4—C50—H50C | 109.5 |
C13—C12—C55 | 127.1 (3) | H50A—C50—H50C | 109.5 |
C11—C12—C55 | 126.7 (3) | H50B—C50—H50C | 109.5 |
C12—C13—C14 | 106.5 (2) | C8—C51—C52 | 112.6 (3) |
C12—C13—C23 | 123.9 (3) | C8—C51—H51A | 109.1 |
C14—C13—C23 | 129.5 (3) | C52—C51—H51A | 109.1 |
N3—C14—C15 | 123.0 (2) | C8—C51—H51B | 109.1 |
N3—C14—C13 | 109.8 (2) | C52—C51—H51B | 109.1 |
C15—C14—C13 | 127.2 (3) | H51A—C51—H51B | 107.8 |
C16—C15—C14 | 128.4 (3) | C53—C52—C51 | 110.3 (3) |
C16—C15—C36 | 115.5 (2) | C53—C52—H52A | 109.6 |
C14—C15—C36 | 116.1 (2) | C51—C52—H52A | 109.6 |
N4—C16—C15 | 123.3 (3) | C53—C52—H52B | 109.6 |
N4—C16—C17 | 109.9 (2) | C51—C52—H52B | 109.6 |
C15—C16—C17 | 126.7 (3) | H52A—C52—H52B | 108.1 |
C18—C17—C16 | 106.1 (2) | O5—C53—O6 | 123.1 (3) |
C18—C17—C24 | 122.1 (3) | O5—C53—C52 | 124.6 (4) |
C16—C17—C24 | 131.7 (3) | O6—C53—C52 | 112.3 (3) |
C17—C18—C19 | 106.6 (2) | O6—C54—H54A | 109.5 |
C17—C18—C59 | 126.4 (3) | O6—C54—H54B | 109.5 |
C19—C18—C59 | 126.8 (3) | H54A—C54—H54B | 109.5 |
N4—C19—C18 | 111.8 (3) | O6—C54—H54C | 109.5 |
N4—C19—C20 | 125.1 (3) | H54A—C54—H54C | 109.5 |
C18—C19—C20 | 123.0 (3) | H54B—C54—H54C | 109.5 |
O2—C20—C1 | 117.6 (3) | C12—C55—C56 | 114.4 (2) |
O2—C20—C19 | 117.4 (3) | C12—C55—H55A | 108.6 |
C1—C20—C19 | 125.0 (2) | C56—C55—H55A | 108.6 |
C3—C21—H21A | 109.5 | C12—C55—H55B | 108.6 |
C3—C21—H21B | 109.5 | C56—C55—H55B | 108.6 |
H21A—C21—H21B | 109.5 | H55A—C55—H55B | 107.6 |
C3—C21—H21C | 109.5 | C57—C56—C55 | 113.7 (3) |
H21A—C21—H21C | 109.5 | C57—C56—H56A | 108.8 |
H21B—C21—H21C | 109.5 | C55—C56—H56A | 108.8 |
C7—C22—H22A | 109.5 | C57—C56—H56B | 108.8 |
C7—C22—H22B | 109.5 | C55—C56—H56B | 108.8 |
H22A—C22—H22B | 109.5 | H56A—C56—H56B | 107.7 |
C7—C22—H22C | 109.5 | O7—C57—O8 | 123.4 (3) |
H22A—C22—H22C | 109.5 | O7—C57—C56 | 124.7 (3) |
H22B—C22—H22C | 109.5 | O8—C57—C56 | 111.9 (3) |
C13—C23—H23A | 109.5 | O8—C58—H58A | 109.5 |
C13—C23—H23B | 109.5 | O8—C58—H58B | 109.5 |
H23A—C23—H23B | 109.5 | H58A—C58—H58B | 109.5 |
C13—C23—H23C | 109.5 | O8—C58—H58C | 109.5 |
H23A—C23—H23C | 109.5 | H58A—C58—H58C | 109.5 |
H23B—C23—H23C | 109.5 | H58B—C58—H58C | 109.5 |
C17—C24—H24A | 109.5 | C18—C59—C60 | 111.1 (2) |
C17—C24—H24B | 109.5 | C18—C59—H59A | 109.4 |
H24A—C24—H24B | 109.5 | C60—C59—H59A | 109.4 |
C17—C24—H24C | 109.5 | C18—C59—H59B | 109.4 |
H24A—C24—H24C | 109.5 | C60—C59—H59B | 109.4 |
H24B—C24—H24C | 109.5 | H59A—C59—H59B | 108.0 |
C26—C25—C30 | 120.0 (3) | C61—C60—C59 | 113.9 (3) |
C26—C25—C5 | 120.0 (3) | C61—C60—H60A | 108.8 |
C30—C25—C5 | 119.9 (3) | C59—C60—H60A | 108.8 |
C25—C26—C27 | 121.0 (3) | C61—C60—H60B | 108.8 |
C25—C26—H26A | 119.5 | C59—C60—H60B | 108.8 |
C27—C26—H26A | 119.5 | H60A—C60—H60B | 107.7 |
C26—C27—C28 | 119.4 (3) | O9—C61—O10 | 122.9 (3) |
C26—C27—H27A | 120.3 | O9—C61—C60 | 124.5 (3) |
C28—C27—H27A | 120.3 | O10—C61—C60 | 112.6 (3) |
C29—C28—C27 | 119.1 (3) | O10—C62—H62A | 109.5 |
C29—C28—C31 | 121.5 (3) | O10—C62—H62B | 109.5 |
C27—C28—C31 | 119.5 (3) | O10—C62—H62C | 109.5 |
C30—C29—C28 | 120.6 (3) | O10—C62'—H62D | 109.5 |
C30—C29—H29A | 119.7 | O10—C62'—H62E | 109.5 |
C28—C29—H29A | 119.7 | H62D—C62'—H62E | 109.5 |
C29—C30—C25 | 119.9 (3) | O10—C62'—H62F | 109.5 |
C29—C30—H30A | 120.1 | H62D—C62'—H62F | 109.5 |
C25—C30—H30A | 120.1 | H62E—C62'—H62F | 109.5 |
N4—Zn1—N1—C1 | 4.2 (2) | Zn1—N3—C14—C15 | 0.5 (4) |
N3—Zn1—N1—C1 | 90.0 (4) | C11—N3—C14—C13 | −0.8 (3) |
N2—Zn1—N1—C1 | 170.6 (2) | Zn1—N3—C14—C13 | 179.09 (18) |
O11—Zn1—N1—C1 | −93.8 (2) | C12—C13—C14—N3 | 0.2 (3) |
N4—Zn1—N1—C4 | −171.2 (2) | C23—C13—C14—N3 | −176.8 (3) |
N3—Zn1—N1—C4 | −85.5 (4) | C12—C13—C14—C15 | 178.8 (3) |
N2—Zn1—N1—C4 | −4.8 (2) | C23—C13—C14—C15 | 1.7 (5) |
O11—Zn1—N1—C4 | 90.8 (2) | N3—C14—C15—C16 | 8.0 (5) |
N4—Zn1—N2—C9 | −107.5 (4) | C13—C14—C15—C16 | −170.3 (3) |
N3—Zn1—N2—C9 | −21.4 (2) | N3—C14—C15—C36 | −173.5 (3) |
O11—Zn1—N2—C9 | 78.6 (2) | C13—C14—C15—C36 | 8.1 (4) |
N1—Zn1—N2—C9 | 172.7 (2) | C19—N4—C16—C15 | 175.2 (3) |
N4—Zn1—N2—C6 | 106.1 (4) | Zn1—N4—C16—C15 | −15.8 (4) |
N3—Zn1—N2—C6 | −167.9 (2) | C19—N4—C16—C17 | −0.7 (3) |
O11—Zn1—N2—C6 | −67.8 (2) | Zn1—N4—C16—C17 | 168.33 (19) |
N1—Zn1—N2—C6 | 26.3 (2) | C14—C15—C16—N4 | 0.0 (5) |
N4—Zn1—N3—C11 | 169.8 (2) | C36—C15—C16—N4 | −178.5 (3) |
N2—Zn1—N3—C11 | 3.6 (2) | C14—C15—C16—C17 | 175.2 (3) |
O11—Zn1—N3—C11 | −92.3 (2) | C36—C15—C16—C17 | −3.3 (4) |
N1—Zn1—N3—C11 | 83.9 (4) | N4—C16—C17—C18 | 2.7 (3) |
N4—Zn1—N3—C14 | −10.1 (2) | C15—C16—C17—C18 | −173.0 (3) |
N2—Zn1—N3—C14 | −176.3 (2) | N4—C16—C17—C24 | −173.4 (3) |
O11—Zn1—N3—C14 | 87.8 (2) | C15—C16—C17—C24 | 10.8 (5) |
N1—Zn1—N3—C14 | −96.0 (4) | C16—C17—C18—C19 | −3.5 (3) |
N3—Zn1—N4—C19 | −175.8 (2) | C24—C17—C18—C19 | 173.1 (3) |
N2—Zn1—N4—C19 | −89.6 (4) | C16—C17—C18—C59 | 171.2 (3) |
O11—Zn1—N4—C19 | 84.3 (2) | C24—C17—C18—C59 | −12.2 (5) |
N1—Zn1—N4—C19 | −10.1 (2) | C16—N4—C19—C18 | −1.6 (3) |
N3—Zn1—N4—C16 | 17.4 (2) | Zn1—N4—C19—C18 | −170.64 (19) |
N2—Zn1—N4—C16 | 103.7 (4) | C16—N4—C19—C20 | 174.6 (3) |
O11—Zn1—N4—C16 | −82.5 (2) | Zn1—N4—C19—C20 | 5.6 (4) |
N1—Zn1—N4—C16 | −176.9 (2) | C17—C18—C19—N4 | 3.4 (3) |
C4—N1—C1—C2 | 1.7 (3) | C59—C18—C19—N4 | −171.3 (3) |
Zn1—N1—C1—C2 | −174.57 (19) | C17—C18—C19—C20 | −172.9 (3) |
C4—N1—C1—C20 | −177.1 (3) | C59—C18—C19—C20 | 12.4 (5) |
Zn1—N1—C1—C20 | 6.6 (4) | N1—C1—C20—O2 | 166.3 (3) |
N1—C1—C2—C3 | 0.7 (3) | C2—C1—C20—O2 | −12.4 (4) |
C20—C1—C2—C3 | 179.6 (3) | N1—C1—C20—C19 | −15.4 (4) |
N1—C1—C2—C47 | 178.8 (3) | C2—C1—C20—C19 | 165.9 (3) |
C20—C1—C2—C47 | −2.4 (5) | N4—C19—C20—O2 | −172.8 (3) |
C1—C2—C3—C4 | −2.8 (3) | C18—C19—C20—O2 | 3.1 (4) |
C47—C2—C3—C4 | 179.1 (3) | N4—C19—C20—C1 | 8.9 (5) |
C1—C2—C3—C21 | 172.8 (3) | C18—C19—C20—C1 | −175.2 (3) |
C47—C2—C3—C21 | −5.3 (5) | C4—C5—C25—C26 | 76.7 (4) |
C1—N1—C4—C5 | 172.3 (3) | C6—C5—C25—C26 | −103.2 (3) |
Zn1—N1—C4—C5 | −11.5 (4) | C4—C5—C25—C30 | −101.7 (3) |
C1—N1—C4—C3 | −3.4 (3) | C6—C5—C25—C30 | 78.4 (4) |
Zn1—N1—C4—C3 | 172.81 (19) | C30—C25—C26—C27 | −0.1 (5) |
C2—C3—C4—N1 | 4.0 (3) | C5—C25—C26—C27 | −178.5 (3) |
C21—C3—C4—N1 | −171.3 (3) | C25—C26—C27—C28 | −0.7 (5) |
C2—C3—C4—C5 | −171.5 (3) | C26—C27—C28—C29 | 1.0 (4) |
C21—C3—C4—C5 | 13.3 (5) | C26—C27—C28—C31 | −178.7 (3) |
N1—C4—C5—C6 | 11.8 (5) | C27—C28—C29—C30 | −0.5 (5) |
C3—C4—C5—C6 | −173.4 (3) | C31—C28—C29—C30 | 179.2 (3) |
N1—C4—C5—C25 | −168.1 (3) | C28—C29—C30—C25 | −0.4 (5) |
C3—C4—C5—C25 | 6.7 (4) | C26—C25—C30—C29 | 0.7 (5) |
C9—N2—C6—C5 | 174.4 (3) | C5—C25—C30—C29 | 179.1 (3) |
Zn1—N2—C6—C5 | −34.2 (4) | C16—C15—C36—C41 | 82.1 (4) |
C9—N2—C6—C7 | −1.9 (3) | C14—C15—C36—C41 | −96.6 (3) |
Zn1—N2—C6—C7 | 149.5 (2) | C16—C15—C36—C37 | −96.2 (3) |
C4—C5—C6—N2 | 12.3 (5) | C14—C15—C36—C37 | 85.1 (4) |
C25—C5—C6—N2 | −167.8 (3) | C41—C36—C37—C38 | 1.2 (5) |
C4—C5—C6—C7 | −172.0 (3) | C15—C36—C37—C38 | 179.5 (3) |
C25—C5—C6—C7 | 7.8 (5) | C36—C37—C38—C39 | −0.5 (5) |
N2—C6—C7—C8 | 1.2 (3) | C37—C38—C39—C40 | −0.2 (5) |
C5—C6—C7—C8 | −174.9 (3) | C37—C38—C39—C42 | 178.3 (3) |
N2—C6—C7—C22 | −176.9 (3) | C38—C39—C40—C41 | 0.3 (5) |
C5—C6—C7—C22 | 7.0 (5) | C42—C39—C40—C41 | −178.2 (3) |
C6—C7—C8—C9 | 0.0 (3) | C39—C40—C41—C36 | 0.3 (5) |
C22—C7—C8—C9 | 178.2 (3) | C37—C36—C41—C40 | −1.1 (4) |
C6—C7—C8—C51 | −178.8 (3) | C15—C36—C41—C40 | −179.3 (3) |
C22—C7—C8—C51 | −0.6 (5) | C3—C2—C47—C48 | 108.3 (3) |
C6—N2—C9—C8 | 1.9 (3) | C1—C2—C47—C48 | −69.3 (4) |
Zn1—N2—C9—C8 | −149.9 (2) | C2—C47—C48—C49 | 167.8 (3) |
C6—N2—C9—C10 | −172.9 (3) | C50—O4—C49—O3 | −5.9 (5) |
Zn1—N2—C9—C10 | 35.3 (4) | C50—O4—C49—C48 | 171.5 (3) |
C7—C8—C9—N2 | −1.2 (3) | C47—C48—C49—O3 | −18.5 (5) |
C51—C8—C9—N2 | 177.5 (3) | C47—C48—C49—O4 | 164.2 (3) |
C7—C8—C9—C10 | 173.7 (3) | C7—C8—C51—C52 | −84.8 (4) |
C51—C8—C9—C10 | −7.6 (5) | C9—C8—C51—C52 | 96.7 (4) |
N2—C9—C10—O1 | 156.5 (3) | C8—C51—C52—C53 | 170.9 (3) |
C8—C9—C10—O1 | −17.8 (4) | C54—O6—C53—O5 | −1.2 (6) |
N2—C9—C10—C11 | −26.3 (5) | C54—O6—C53—C52 | −178.9 (4) |
C8—C9—C10—C11 | 159.4 (3) | C51—C52—C53—O5 | −82.5 (5) |
C14—N3—C11—C12 | 1.1 (3) | C51—C52—C53—O6 | 95.1 (4) |
Zn1—N3—C11—C12 | −178.81 (19) | C13—C12—C55—C56 | −98.8 (3) |
C14—N3—C11—C10 | −177.5 (3) | C11—C12—C55—C56 | 80.7 (4) |
Zn1—N3—C11—C10 | 2.7 (4) | C12—C55—C56—C57 | 86.1 (3) |
O1—C10—C11—N3 | −177.5 (3) | C58—O8—C57—O7 | −0.5 (5) |
C9—C10—C11—N3 | 5.3 (5) | C58—O8—C57—C56 | −178.5 (3) |
O1—C10—C11—C12 | 4.1 (5) | C55—C56—C57—O7 | 26.2 (5) |
C9—C10—C11—C12 | −173.1 (3) | C55—C56—C57—O8 | −155.8 (3) |
N3—C11—C12—C13 | −1.0 (3) | C17—C18—C59—C60 | −109.1 (3) |
C10—C11—C12—C13 | 177.6 (3) | C19—C18—C59—C60 | 64.7 (4) |
N3—C11—C12—C55 | 179.5 (3) | C18—C59—C60—C61 | −167.0 (3) |
C10—C11—C12—C55 | −2.0 (5) | C62'—O10—C61—O9 | 8.0 (7) |
C11—C12—C13—C14 | 0.4 (3) | C62—O10—C61—O9 | −11.2 (7) |
C55—C12—C13—C14 | 180.0 (3) | C62'—O10—C61—C60 | −171.3 (6) |
C11—C12—C13—C23 | 177.7 (3) | C62—O10—C61—C60 | 169.5 (5) |
C55—C12—C13—C23 | −2.8 (5) | C59—C60—C61—O9 | 137.5 (4) |
C11—N3—C14—C15 | −179.4 (3) | C59—C60—C61—O10 | −43.2 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O11—H11B···O2i | 0.84 (2) | 1.92 (2) | 2.748 (3) | 168 (4) |
O11—H11A···O3i | 0.84 (2) | 2.13 (3) | 2.853 (3) | 144 (4) |
Symmetry code: (i) −x−1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | [Zn(C62H66N4O10Si2)(H2O)] |
Mr | 1166.75 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 160 |
a, b, c (Å) | 12.570 (2), 14.285 (3), 17.502 (4) |
α, β, γ (°) | 85.082 (10), 69.225 (12), 87.07 (2) |
V (Å3) | 2926.9 (11) |
Z | 2 |
Radiation type | Synchrotron, λ = 0.6879 Å |
µ (mm−1) | 0.52 |
Crystal size (mm) | 0.07 × 0.06 × 0.02 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1997b) |
Tmin, Tmax | 0.964, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17561, 12222, 8256 |
Rint | 0.066 |
(sin θ/λ)max (Å−1) | 0.663 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.135, 0.92 |
No. of reflections | 12222 |
No. of parameters | 743 |
No. of restraints | 4 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.19, −1.10 |
Computer programs: SMART (Siemens, 1994), LSCELL (Clegg, 1995), SAINT (Siemens, 1994), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP (Sheldrick, 1993), SHELXL97.
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
The bright-orange monomeric dioxoporphyrin unit aqua{5,15-bis[4-(2-trimethylsilylacetylene)phenyl]-2,8,12,18-tetrakis(2- methoxycarbonylethyl)-3,7,13,17-tetramethyl-10,20-dioxoporphyrinato}zinc(II), (I), is prepared by thallium trifluoroacetate oxidation (McCallien & Sanders, 1995) of the purple porphyrinic zinc precursor (Bampos et al., 1998). The presence of electron-withdrawing cross-conjugated carbonyl groups on the macrocyclic periphery gives (I) two characteristic properties in solution: lack of a diagnostic NMR diamagnetic ring current and an increased Lewis acidity of the central metal ion, leading to stronger binding of N– and O-ligands. Both these properties make (I) attractive as a building block in the templated construction of supramolecular architectures (Clyde-Watson et al., 1998).
(I) crystallizes with a saddle conformation (Scheidt & Lee, 1987) characterized by alternate pyrrole-ring displacements above and below the least-squares plane through the 24 atoms of the porphyrin unit (Fig. 1). Molecules of (I) are linked into centrosymmetric dimers via hydrogen bonds formed by the zinc-bound water molecule with one oxo group in the 10-position of an adjacent porphyrin and one carbonyl oxygen of a 2-methoxycarbonylethyl side chain [H11A···O3i = 2.13 (3) Å, O11—H11A···O3i = 144 (4)°; H11B···O2i = 1.92 (2) Å, O11—H11B···O2i = 168 (4)°; symmetry code: (i) -1 - x, -y, -z] (Fig. 2). The hydrogen-bond arrangement is reminiscent of that observed in the dihydrates of ethyl chlorophyllide a and b, in which magnesium-bound water molecules hydrogen bond to oxo groups of neighbouring chlorophyllide units and also via a second water molecule to the carbonyl oxygen of a methyl ester side chain, forming one-dimensional polymers (Chow et al., 1975; Serlin et al., 1975). The omission of the second water molecule in (I) allows both interactions to form between the same molecular units, giving rise to the observed dimers.
Dimers are π-stacked via interactions between hydrophobic porphyrin faces, with the stacking direction approximately perpendicular to (110). Least-squares planes through adjacent porphyrin units in the stacks are coplanar with a separation of ca 3.8 Å, and a Zn1···Zn1ii distance of 5.719 (1) Å [symmetry code: (ii) -2 - x, -y, -z] (Fig. 3). In adjacent molecules, phenyl groups of the 4-(2-trimethylsilylacetylene)phenyl substituents are twisted with respect to each other by an angle of ca 33°, adopting a geometry indicative of an edge-to-face C—H···π interaction [H30···(centroid C36—C41)ii = 3.45 Å, C30—H30···centroid = 163°] (Desiraju & Steiner, 1999). This interaction may contribute towards the stability of the π-stacks. The 4-(2-trimethylsilylacetylene)phenyl substituents in adjacent stacks are interdigitated, maximizing dispersion interactions between stacks (Fig. 4).