In the title compound, [Zn(C
24H
29N
2O
2S)
2], the Zn atom is four-coordinated by the N atoms of the sulfonamide and quinoline groups. The crystal packing is stabilized by intermolecular C—H
O hydrogen bonds.
Supporting information
CCDC reference: 601116
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.039
- wR factor = 0.102
- Data-to-parameter ratio = 16.0
checkCIF/PLATON results
No syntax errors found
Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
identifier.
bright
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
Bis[2,4,6-triisopropyl-
N-(quinolin-8-yl)benzenesulfonamidato-
κ2N,
N']zinc(II)
top
Crystal data top
[Zn(C24H29N2O2S)2] | Z = 2 |
Mr = 884.47 | F(000) = 936 |
Triclinic, P1 | Dx = 1.358 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.9732 (6) Å | Cell parameters from 7555 reflections |
b = 14.3281 (8) Å | θ = 2.2–27.6° |
c = 17.0425 (8) Å | µ = 0.71 mm−1 |
α = 71.723 (5)° | T = 100 K |
β = 79.277 (4)° | Prism, bright yellow |
γ = 69.875 (5)° | 0.36 × 0.34 × 0.22 mm |
V = 2162.9 (2) Å3 | |
Data collection top
Oxford Diffraction Xcalibur with Sapphire CCD detector diffractometer | 8527 independent reflections |
Radiation source: fine-focus sealed tube | 7417 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Rotation method data acquisition using ω and φ scans | θmax = 26.4°, θmin = 4.1° |
Absorption correction: analytical (CrysAlis RED–CCD; Oxford Diffraction, 2004) | h = −11→12 |
Tmin = 0.803, Tmax = 0.900 | k = −13→17 |
15135 measured reflections | l = −20→21 |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.102 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0529P)2 + 1.6914P] where P = (Fo2 + 2Fc2)/3 |
8527 reflections | (Δ/σ)max = 0.001 |
532 parameters | Δρmax = 0.70 e Å−3 |
0 restraints | Δρmin = −0.64 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.7342 (2) | 0.35575 (17) | 0.13015 (14) | 0.0194 (4) | |
H1 | 0.8057 | 0.2912 | 0.1474 | 0.023* | |
C2 | 0.7669 (2) | 0.42954 (18) | 0.05860 (14) | 0.0224 (5) | |
H2 | 0.8579 | 0.4142 | 0.0280 | 0.027* | |
C3 | 0.6661 (2) | 0.52321 (18) | 0.03391 (14) | 0.0207 (5) | |
H3 | 0.6863 | 0.5735 | −0.0144 | 0.025* | |
C4 | 0.5316 (2) | 0.54511 (16) | 0.08045 (13) | 0.0169 (4) | |
C5 | 0.4237 (2) | 0.64180 (17) | 0.06052 (13) | 0.0200 (5) | |
H5 | 0.4388 | 0.6958 | 0.0139 | 0.024* | |
C6 | 0.2972 (2) | 0.65592 (17) | 0.10983 (13) | 0.0208 (5) | |
H6 | 0.2253 | 0.7210 | 0.0970 | 0.025* | |
C7 | 0.2699 (2) | 0.57786 (16) | 0.17848 (13) | 0.0178 (4) | |
H7 | 0.1795 | 0.5906 | 0.2100 | 0.021* | |
C8 | 0.3720 (2) | 0.48281 (15) | 0.20113 (12) | 0.0140 (4) | |
C9 | 0.5057 (2) | 0.46621 (16) | 0.15080 (13) | 0.0149 (4) | |
C10 | 0.0819 (2) | 0.47103 (15) | 0.34186 (12) | 0.0131 (4) | |
C11 | 0.0015 (2) | 0.56688 (16) | 0.35801 (12) | 0.0144 (4) | |
C12 | −0.1479 (2) | 0.59101 (16) | 0.36728 (13) | 0.0162 (4) | |
H12 | −0.2033 | 0.6531 | 0.3815 | 0.019* | |
C13 | −0.2186 (2) | 0.52858 (16) | 0.35665 (12) | 0.0163 (4) | |
C14 | −0.1356 (2) | 0.44076 (16) | 0.33199 (13) | 0.0167 (4) | |
H14 | −0.1830 | 0.4005 | 0.3195 | 0.020* | |
C15 | 0.0129 (2) | 0.40910 (15) | 0.32477 (12) | 0.0138 (4) | |
C16 | 0.0617 (2) | 0.64964 (16) | 0.36337 (13) | 0.0172 (4) | |
H16 | 0.1661 | 0.6294 | 0.3443 | 0.021* | |
C17 | 0.0472 (3) | 0.65508 (19) | 0.45295 (14) | 0.0248 (5) | |
H17A | −0.0541 | 0.6712 | 0.4742 | 0.030* | |
H17B | 0.0850 | 0.7091 | 0.4547 | 0.030* | |
H17C | 0.1015 | 0.5884 | 0.4874 | 0.030* | |
C18 | −0.0108 (2) | 0.75524 (17) | 0.30580 (15) | 0.0231 (5) | |
H18A | 0.0348 | 0.8054 | 0.3069 | 0.028* | |
H18B | −0.1127 | 0.7783 | 0.3247 | 0.028* | |
H18C | −0.0006 | 0.7494 | 0.2491 | 0.028* | |
C19 | −0.3814 (2) | 0.55445 (17) | 0.36640 (13) | 0.0176 (4) | |
H19 | −0.4044 | 0.4881 | 0.3917 | 0.021* | |
C20 | −0.4581 (2) | 0.6251 (2) | 0.42206 (16) | 0.0290 (5) | |
H20A | −0.4449 | 0.6933 | 0.3963 | 0.035* | |
H20B | −0.4182 | 0.5957 | 0.4761 | 0.035* | |
H20C | −0.5606 | 0.6321 | 0.4297 | 0.035* | |
C21 | −0.4387 (2) | 0.6011 (2) | 0.28080 (14) | 0.0247 (5) | |
H21A | −0.3873 | 0.5555 | 0.2452 | 0.030* | |
H21B | −0.4242 | 0.6689 | 0.2560 | 0.030* | |
H21C | −0.5412 | 0.6087 | 0.2864 | 0.030* | |
C22 | 0.0901 (2) | 0.31416 (16) | 0.29278 (13) | 0.0166 (4) | |
H22 | 0.1917 | 0.2881 | 0.3071 | 0.020* | |
C23 | 0.0235 (3) | 0.22607 (18) | 0.33142 (17) | 0.0263 (5) | |
H23A | 0.0130 | 0.2122 | 0.3920 | 0.032* | |
H23B | 0.0859 | 0.1638 | 0.3158 | 0.032* | |
H23C | −0.0708 | 0.2461 | 0.3112 | 0.032* | |
C24 | 0.0913 (3) | 0.34627 (19) | 0.19791 (15) | 0.0253 (5) | |
H24A | 0.1366 | 0.2852 | 0.1770 | 0.030* | |
H24B | 0.1455 | 0.3957 | 0.1739 | 0.030* | |
H24C | −0.0073 | 0.3785 | 0.1822 | 0.030* | |
C25 | 0.6629 (2) | 0.22830 (17) | 0.43496 (13) | 0.0186 (4) | |
H25 | 0.6522 | 0.2998 | 0.4222 | 0.022* | |
C26 | 0.7173 (2) | 0.16373 (18) | 0.51001 (14) | 0.0216 (5) | |
H26 | 0.7442 | 0.1909 | 0.5467 | 0.026* | |
C27 | 0.7313 (2) | 0.06089 (17) | 0.52975 (14) | 0.0215 (5) | |
H27 | 0.7684 | 0.0161 | 0.5804 | 0.026* | |
C28 | 0.6906 (2) | 0.02125 (17) | 0.47499 (13) | 0.0171 (4) | |
C29 | 0.6957 (2) | −0.08323 (17) | 0.49272 (13) | 0.0191 (4) | |
H29 | 0.7313 | −0.1314 | 0.5427 | 0.023* | |
C30 | 0.6491 (2) | −0.11425 (17) | 0.43781 (13) | 0.0193 (4) | |
H30 | 0.6518 | −0.1843 | 0.4504 | 0.023* | |
C31 | 0.5969 (2) | −0.04461 (16) | 0.36235 (13) | 0.0166 (4) | |
H31 | 0.5654 | −0.0686 | 0.3252 | 0.020* | |
C32 | 0.5912 (2) | 0.05744 (16) | 0.34227 (12) | 0.0140 (4) | |
C33 | 0.6380 (2) | 0.09153 (16) | 0.39991 (13) | 0.0146 (4) | |
C34 | 0.5785 (2) | 0.01577 (15) | 0.16292 (12) | 0.0129 (4) | |
C35 | 0.5211 (2) | −0.05584 (15) | 0.14998 (12) | 0.0136 (4) | |
C36 | 0.6165 (2) | −0.13954 (16) | 0.12380 (12) | 0.0156 (4) | |
H36 | 0.5797 | −0.1885 | 0.1157 | 0.019* | |
C37 | 0.7635 (2) | −0.15483 (15) | 0.10886 (12) | 0.0143 (4) | |
C38 | 0.8147 (2) | −0.08130 (16) | 0.11888 (12) | 0.0140 (4) | |
H38 | 0.9146 | −0.0901 | 0.1083 | 0.017* | |
C39 | 0.7254 (2) | 0.00507 (15) | 0.14388 (12) | 0.0133 (4) | |
C40 | 0.3620 (2) | −0.04631 (16) | 0.15953 (13) | 0.0158 (4) | |
H40 | 0.3065 | 0.0274 | 0.1565 | 0.019* | |
C41 | 0.3204 (2) | −0.11248 (18) | 0.24469 (15) | 0.0237 (5) | |
H41A | 0.3503 | −0.0949 | 0.2884 | 0.028* | |
H41B | 0.3681 | −0.1857 | 0.2479 | 0.028* | |
H41C | 0.2163 | −0.0990 | 0.2520 | 0.028* | |
C42 | 0.3195 (2) | −0.07414 (19) | 0.08969 (15) | 0.0243 (5) | |
H42A | 0.3519 | −0.0343 | 0.0359 | 0.029* | |
H42B | 0.2150 | −0.0579 | 0.0939 | 0.029* | |
H42C | 0.3644 | −0.1481 | 0.0947 | 0.029* | |
C43 | 0.8632 (2) | −0.24362 (16) | 0.07528 (13) | 0.0154 (4) | |
H43 | 0.9631 | −0.2407 | 0.0710 | 0.018* | |
C44 | 0.8289 (2) | −0.23106 (18) | −0.01217 (14) | 0.0228 (5) | |
H44A | 0.8389 | −0.1654 | −0.0489 | 0.027* | |
H44B | 0.7304 | −0.2317 | −0.0102 | 0.027* | |
H44C | 0.8954 | −0.2881 | −0.0333 | 0.027* | |
C45 | 0.8600 (3) | −0.34972 (17) | 0.13163 (15) | 0.0235 (5) | |
H45A | 0.9325 | −0.4037 | 0.1095 | 0.028* | |
H45B | 0.7650 | −0.3568 | 0.1339 | 0.028* | |
H45C | 0.8805 | −0.3566 | 0.1876 | 0.028* | |
C46 | 0.7953 (2) | 0.08566 (16) | 0.14290 (12) | 0.0145 (4) | |
H46 | 0.7179 | 0.1472 | 0.1549 | 0.017* | |
C47 | 0.8695 (2) | 0.12029 (17) | 0.05629 (13) | 0.0202 (5) | |
H47A | 0.8985 | 0.1804 | 0.0528 | 0.024* | |
H47B | 0.8029 | 0.1388 | 0.0143 | 0.024* | |
H47C | 0.9544 | 0.0638 | 0.0465 | 0.024* | |
C48 | 0.9024 (2) | 0.04560 (17) | 0.20819 (14) | 0.0201 (5) | |
H48A | 0.8539 | 0.0246 | 0.2633 | 0.024* | |
H48B | 0.9417 | 0.1003 | 0.2064 | 0.024* | |
H48C | 0.9805 | −0.0139 | 0.1968 | 0.024* | |
N1 | 0.60891 (19) | 0.37241 (13) | 0.17420 (11) | 0.0157 (4) | |
N2 | 0.35830 (18) | 0.39848 (13) | 0.26796 (10) | 0.0139 (3) | |
N3 | 0.62582 (18) | 0.19443 (13) | 0.38100 (11) | 0.0152 (4) | |
N4 | 0.54914 (18) | 0.13417 (13) | 0.26880 (10) | 0.0144 (3) | |
O1 | 0.31724 (15) | 0.48397 (11) | 0.38247 (9) | 0.0181 (3) | |
O2 | 0.29048 (15) | 0.31305 (11) | 0.40928 (9) | 0.0173 (3) | |
O3 | 0.33632 (16) | 0.09569 (12) | 0.24549 (10) | 0.0206 (3) | |
O4 | 0.44548 (16) | 0.21497 (11) | 0.13703 (9) | 0.0179 (3) | |
Zn1 | 0.52693 (2) | 0.274527 (17) | 0.273923 (14) | 0.01426 (8) | |
S2 | 0.46392 (5) | 0.12125 (4) | 0.20390 (3) | 0.01376 (12) | |
S1 | 0.27072 (5) | 0.41610 (4) | 0.35470 (3) | 0.01296 (11) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0155 (10) | 0.0189 (11) | 0.0248 (11) | −0.0058 (9) | −0.0001 (8) | −0.0077 (9) |
C2 | 0.0182 (11) | 0.0267 (12) | 0.0237 (12) | −0.0094 (9) | 0.0049 (9) | −0.0096 (10) |
C3 | 0.0238 (12) | 0.0241 (11) | 0.0168 (11) | −0.0141 (9) | 0.0021 (9) | −0.0037 (9) |
C4 | 0.0219 (11) | 0.0185 (10) | 0.0132 (10) | −0.0097 (9) | −0.0024 (8) | −0.0038 (8) |
C5 | 0.0255 (12) | 0.0175 (11) | 0.0137 (10) | −0.0086 (9) | −0.0012 (8) | 0.0022 (8) |
C6 | 0.0225 (11) | 0.0155 (10) | 0.0181 (11) | −0.0028 (9) | −0.0066 (9) | 0.0037 (8) |
C7 | 0.0156 (10) | 0.0190 (11) | 0.0153 (10) | −0.0038 (8) | 0.0000 (8) | −0.0023 (8) |
C8 | 0.0161 (10) | 0.0135 (10) | 0.0122 (9) | −0.0054 (8) | −0.0034 (8) | −0.0009 (8) |
C9 | 0.0168 (10) | 0.0157 (10) | 0.0137 (10) | −0.0057 (8) | −0.0022 (8) | −0.0049 (8) |
C10 | 0.0095 (9) | 0.0149 (10) | 0.0120 (9) | −0.0026 (8) | −0.0016 (7) | −0.0005 (8) |
C11 | 0.0152 (10) | 0.0150 (10) | 0.0105 (9) | −0.0042 (8) | −0.0021 (7) | 0.0001 (8) |
C12 | 0.0167 (10) | 0.0135 (10) | 0.0142 (10) | −0.0011 (8) | −0.0007 (8) | −0.0023 (8) |
C13 | 0.0153 (10) | 0.0174 (10) | 0.0119 (10) | −0.0033 (8) | −0.0027 (8) | 0.0010 (8) |
C14 | 0.0170 (10) | 0.0180 (10) | 0.0144 (10) | −0.0059 (8) | −0.0026 (8) | −0.0020 (8) |
C15 | 0.0151 (10) | 0.0128 (10) | 0.0112 (9) | −0.0037 (8) | −0.0016 (7) | −0.0004 (8) |
C16 | 0.0177 (10) | 0.0132 (10) | 0.0182 (11) | −0.0049 (8) | −0.0018 (8) | −0.0007 (8) |
C17 | 0.0309 (13) | 0.0259 (12) | 0.0223 (12) | −0.0139 (10) | −0.0022 (9) | −0.0072 (10) |
C18 | 0.0242 (12) | 0.0156 (11) | 0.0256 (12) | −0.0061 (9) | −0.0032 (9) | 0.0003 (9) |
C19 | 0.0130 (10) | 0.0174 (10) | 0.0202 (11) | −0.0054 (8) | −0.0011 (8) | −0.0016 (8) |
C20 | 0.0154 (11) | 0.0423 (15) | 0.0293 (13) | −0.0036 (10) | −0.0020 (9) | −0.0155 (11) |
C21 | 0.0156 (11) | 0.0359 (13) | 0.0220 (12) | −0.0075 (10) | −0.0038 (9) | −0.0066 (10) |
C22 | 0.0144 (10) | 0.0172 (10) | 0.0189 (11) | −0.0040 (8) | −0.0010 (8) | −0.0070 (8) |
C23 | 0.0203 (11) | 0.0171 (11) | 0.0410 (14) | −0.0054 (9) | 0.0026 (10) | −0.0104 (10) |
C24 | 0.0233 (12) | 0.0270 (12) | 0.0235 (12) | 0.0007 (10) | −0.0059 (9) | −0.0112 (10) |
C25 | 0.0172 (10) | 0.0176 (10) | 0.0208 (11) | −0.0058 (8) | 0.0001 (8) | −0.0056 (9) |
C26 | 0.0241 (12) | 0.0260 (12) | 0.0178 (11) | −0.0086 (9) | −0.0031 (9) | −0.0084 (9) |
C27 | 0.0208 (11) | 0.0229 (11) | 0.0167 (11) | −0.0044 (9) | −0.0047 (8) | −0.0005 (9) |
C28 | 0.0139 (10) | 0.0187 (10) | 0.0151 (10) | −0.0031 (8) | −0.0006 (8) | −0.0021 (8) |
C29 | 0.0208 (11) | 0.0163 (10) | 0.0151 (10) | −0.0037 (9) | −0.0023 (8) | 0.0010 (8) |
C30 | 0.0205 (11) | 0.0137 (10) | 0.0190 (11) | −0.0043 (8) | 0.0011 (8) | −0.0006 (8) |
C31 | 0.0182 (10) | 0.0156 (10) | 0.0141 (10) | −0.0045 (8) | 0.0003 (8) | −0.0032 (8) |
C32 | 0.0105 (9) | 0.0145 (10) | 0.0121 (9) | −0.0020 (8) | 0.0025 (7) | −0.0008 (8) |
C33 | 0.0110 (9) | 0.0150 (10) | 0.0153 (10) | −0.0034 (8) | 0.0038 (7) | −0.0038 (8) |
C34 | 0.0146 (10) | 0.0112 (9) | 0.0092 (9) | −0.0019 (8) | −0.0020 (7) | 0.0004 (7) |
C35 | 0.0129 (10) | 0.0150 (10) | 0.0100 (9) | −0.0043 (8) | −0.0023 (7) | 0.0012 (8) |
C36 | 0.0193 (10) | 0.0153 (10) | 0.0129 (10) | −0.0063 (8) | −0.0034 (8) | −0.0023 (8) |
C37 | 0.0167 (10) | 0.0130 (10) | 0.0086 (9) | −0.0014 (8) | −0.0020 (7) | 0.0001 (7) |
C38 | 0.0123 (9) | 0.0172 (10) | 0.0107 (9) | −0.0042 (8) | −0.0020 (7) | −0.0014 (8) |
C39 | 0.0125 (9) | 0.0141 (10) | 0.0096 (9) | −0.0037 (8) | −0.0030 (7) | 0.0024 (7) |
C40 | 0.0138 (10) | 0.0139 (10) | 0.0181 (10) | −0.0024 (8) | −0.0041 (8) | −0.0027 (8) |
C41 | 0.0134 (10) | 0.0250 (12) | 0.0274 (12) | −0.0066 (9) | 0.0010 (9) | −0.0007 (10) |
C42 | 0.0155 (11) | 0.0282 (12) | 0.0331 (13) | −0.0049 (9) | −0.0081 (9) | −0.0123 (10) |
C43 | 0.0140 (10) | 0.0164 (10) | 0.0142 (10) | −0.0024 (8) | −0.0009 (8) | −0.0047 (8) |
C44 | 0.0204 (11) | 0.0256 (12) | 0.0187 (11) | 0.0007 (9) | −0.0031 (9) | −0.0088 (9) |
C45 | 0.0259 (12) | 0.0154 (11) | 0.0238 (12) | −0.0033 (9) | 0.0020 (9) | −0.0036 (9) |
C46 | 0.0129 (10) | 0.0158 (10) | 0.0144 (10) | −0.0047 (8) | −0.0006 (8) | −0.0036 (8) |
C47 | 0.0236 (11) | 0.0194 (11) | 0.0177 (11) | −0.0112 (9) | 0.0015 (9) | −0.0016 (9) |
C48 | 0.0204 (11) | 0.0238 (11) | 0.0181 (11) | −0.0097 (9) | −0.0034 (8) | −0.0044 (9) |
N1 | 0.0165 (9) | 0.0136 (8) | 0.0170 (9) | −0.0046 (7) | −0.0020 (7) | −0.0039 (7) |
N2 | 0.0131 (8) | 0.0117 (8) | 0.0124 (8) | −0.0014 (7) | −0.0007 (6) | −0.0002 (7) |
N3 | 0.0131 (8) | 0.0144 (8) | 0.0158 (9) | −0.0034 (7) | −0.0004 (7) | −0.0022 (7) |
N4 | 0.0179 (9) | 0.0115 (8) | 0.0121 (8) | −0.0034 (7) | −0.0011 (7) | −0.0024 (7) |
O1 | 0.0158 (7) | 0.0199 (8) | 0.0184 (8) | −0.0050 (6) | −0.0048 (6) | −0.0033 (6) |
O2 | 0.0161 (7) | 0.0151 (7) | 0.0147 (7) | −0.0039 (6) | −0.0032 (6) | 0.0044 (6) |
O3 | 0.0138 (7) | 0.0234 (8) | 0.0266 (8) | −0.0053 (6) | 0.0032 (6) | −0.0125 (7) |
O4 | 0.0198 (8) | 0.0133 (7) | 0.0168 (7) | −0.0003 (6) | −0.0073 (6) | −0.0008 (6) |
Zn1 | 0.01452 (13) | 0.01073 (13) | 0.01461 (13) | −0.00254 (9) | −0.00126 (9) | −0.00094 (9) |
S2 | 0.0115 (2) | 0.0129 (2) | 0.0148 (2) | −0.00144 (19) | −0.00159 (18) | −0.00310 (19) |
S1 | 0.0113 (2) | 0.0129 (2) | 0.0116 (2) | −0.00289 (18) | −0.00190 (17) | 0.00059 (18) |
Geometric parameters (Å, º) top
C1—N1 | 1.319 (3) | C27—C28 | 1.411 (3) |
C1—C2 | 1.411 (3) | C27—H27 | 0.9500 |
C1—H1 | 0.9500 | C28—C33 | 1.416 (3) |
C2—C3 | 1.365 (3) | C28—C29 | 1.416 (3) |
C2—H2 | 0.9500 | C29—C30 | 1.361 (3) |
C3—C4 | 1.414 (3) | C29—H29 | 0.9500 |
C3—H3 | 0.9500 | C30—C31 | 1.417 (3) |
C4—C5 | 1.417 (3) | C30—H30 | 0.9500 |
C4—C9 | 1.420 (3) | C31—C32 | 1.377 (3) |
C5—C6 | 1.369 (3) | C31—H31 | 0.9500 |
C5—H5 | 0.9500 | C32—N4 | 1.403 (3) |
C6—C7 | 1.402 (3) | C32—C33 | 1.431 (3) |
C6—H6 | 0.9500 | C33—N3 | 1.373 (3) |
C7—C8 | 1.380 (3) | C34—C39 | 1.405 (3) |
C7—H7 | 0.9500 | C34—C35 | 1.422 (3) |
C8—N2 | 1.403 (3) | C34—S2 | 1.804 (2) |
C8—C9 | 1.433 (3) | C35—C36 | 1.391 (3) |
C9—N1 | 1.375 (3) | C35—C40 | 1.526 (3) |
C10—C11 | 1.415 (3) | C36—C37 | 1.392 (3) |
C10—C15 | 1.416 (3) | C36—H36 | 0.9500 |
C10—S1 | 1.800 (2) | C37—C38 | 1.383 (3) |
C11—C12 | 1.399 (3) | C37—C43 | 1.520 (3) |
C11—C16 | 1.533 (3) | C38—C39 | 1.392 (3) |
C12—C13 | 1.383 (3) | C38—H38 | 0.9500 |
C12—H12 | 0.9500 | C39—C46 | 1.536 (3) |
C13—C14 | 1.389 (3) | C40—C42 | 1.536 (3) |
C13—C19 | 1.525 (3) | C40—C41 | 1.537 (3) |
C14—C15 | 1.385 (3) | C40—H40 | 1.0000 |
C14—H14 | 0.9500 | C41—H41A | 0.9800 |
C15—C22 | 1.526 (3) | C41—H41B | 0.9800 |
C16—C17 | 1.531 (3) | C41—H41C | 0.9800 |
C16—C18 | 1.534 (3) | C42—H42A | 0.9800 |
C16—H16 | 1.0000 | C42—H42B | 0.9800 |
C17—H17A | 0.9800 | C42—H42C | 0.9800 |
C17—H17B | 0.9800 | C43—C45 | 1.530 (3) |
C17—H17C | 0.9800 | C43—C44 | 1.533 (3) |
C18—H18A | 0.9800 | C43—H43 | 1.0000 |
C18—H18B | 0.9800 | C44—H44A | 0.9800 |
C18—H18C | 0.9800 | C44—H44B | 0.9800 |
C19—C20 | 1.520 (3) | C44—H44C | 0.9800 |
C19—C21 | 1.529 (3) | C45—H45A | 0.9800 |
C19—H19 | 1.0000 | C45—H45B | 0.9800 |
C20—H20A | 0.9800 | C45—H45C | 0.9800 |
C20—H20B | 0.9800 | C46—C48 | 1.526 (3) |
C20—H20C | 0.9800 | C46—C47 | 1.536 (3) |
C21—H21A | 0.9800 | C46—H46 | 1.0000 |
C21—H21B | 0.9800 | C47—H47A | 0.9800 |
C21—H21C | 0.9800 | C47—H47B | 0.9800 |
C22—C24 | 1.535 (3) | C47—H47C | 0.9800 |
C22—C23 | 1.536 (3) | C48—H48A | 0.9800 |
C22—H22 | 1.0000 | C48—H48B | 0.9800 |
C23—H23A | 0.9800 | C48—H48C | 0.9800 |
C23—H23B | 0.9800 | N1—Zn1 | 2.0738 (18) |
C23—H23C | 0.9800 | N2—S1 | 1.6168 (17) |
C24—H24A | 0.9800 | N2—Zn1 | 1.9718 (17) |
C24—H24B | 0.9800 | N3—Zn1 | 2.0487 (18) |
C24—H24C | 0.9800 | N4—S2 | 1.6020 (18) |
C25—N3 | 1.322 (3) | N4—Zn1 | 1.9742 (17) |
C25—C26 | 1.399 (3) | O1—S1 | 1.4373 (16) |
C25—H25 | 0.9500 | O2—S1 | 1.4460 (14) |
C26—C27 | 1.367 (3) | O3—S2 | 1.4417 (15) |
C26—H26 | 0.9500 | O4—S2 | 1.4435 (15) |
| | | |
N1—C1—C2 | 122.9 (2) | C29—C30—C31 | 121.6 (2) |
N1—C1—H1 | 118.5 | C29—C30—H30 | 119.2 |
C2—C1—H1 | 118.5 | C31—C30—H30 | 119.2 |
C3—C2—C1 | 119.2 (2) | C32—C31—C30 | 120.7 (2) |
C3—C2—H2 | 120.4 | C32—C31—H31 | 119.6 |
C1—C2—H2 | 120.4 | C30—C31—H31 | 119.6 |
C2—C3—C4 | 119.7 (2) | C31—C32—N4 | 127.5 (2) |
C2—C3—H3 | 120.1 | C31—C32—C33 | 118.32 (18) |
C4—C3—H3 | 120.1 | N4—C32—C33 | 114.16 (18) |
C3—C4—C5 | 123.0 (2) | N3—C33—C28 | 121.61 (19) |
C3—C4—C9 | 117.8 (2) | N3—C33—C32 | 117.84 (18) |
C5—C4—C9 | 119.23 (19) | C28—C33—C32 | 120.52 (19) |
C6—C5—C4 | 118.67 (19) | C39—C34—C35 | 120.29 (18) |
C6—C5—H5 | 120.7 | C39—C34—S2 | 119.25 (15) |
C4—C5—H5 | 120.7 | C35—C34—S2 | 120.46 (15) |
C5—C6—C7 | 122.4 (2) | C36—C35—C34 | 117.65 (18) |
C5—C6—H6 | 118.8 | C36—C35—C40 | 117.10 (18) |
C7—C6—H6 | 118.8 | C34—C35—C40 | 125.22 (18) |
C8—C7—C6 | 121.2 (2) | C35—C36—C37 | 123.02 (19) |
C8—C7—H7 | 119.4 | C35—C36—H36 | 118.5 |
C6—C7—H7 | 119.4 | C37—C36—H36 | 118.5 |
C7—C8—N2 | 126.82 (19) | C38—C37—C36 | 117.63 (19) |
C7—C8—C9 | 117.51 (19) | C38—C37—C43 | 120.71 (18) |
N2—C8—C9 | 115.66 (17) | C36—C37—C43 | 121.44 (19) |
N1—C9—C4 | 121.31 (19) | C37—C38—C39 | 122.56 (19) |
N1—C9—C8 | 117.69 (18) | C37—C38—H38 | 118.7 |
C4—C9—C8 | 120.97 (19) | C39—C38—H38 | 118.7 |
C11—C10—C15 | 120.67 (18) | C38—C39—C34 | 118.66 (18) |
C11—C10—S1 | 121.57 (15) | C38—C39—C46 | 116.39 (17) |
C15—C10—S1 | 117.33 (15) | C34—C39—C46 | 124.83 (18) |
C12—C11—C10 | 117.41 (19) | C35—C40—C42 | 112.32 (17) |
C12—C11—C16 | 116.13 (18) | C35—C40—C41 | 110.87 (17) |
C10—C11—C16 | 126.42 (18) | C42—C40—C41 | 110.54 (18) |
C13—C12—C11 | 122.97 (19) | C35—C40—H40 | 107.6 |
C13—C12—H12 | 118.5 | C42—C40—H40 | 107.6 |
C11—C12—H12 | 118.5 | C41—C40—H40 | 107.6 |
C12—C13—C14 | 117.45 (19) | C40—C41—H41A | 109.5 |
C12—C13—C19 | 123.31 (19) | C40—C41—H41B | 109.5 |
C14—C13—C19 | 119.16 (19) | H41A—C41—H41B | 109.5 |
C15—C14—C13 | 123.1 (2) | C40—C41—H41C | 109.5 |
C15—C14—H14 | 118.5 | H41A—C41—H41C | 109.5 |
C13—C14—H14 | 118.5 | H41B—C41—H41C | 109.5 |
C14—C15—C10 | 117.81 (19) | C40—C42—H42A | 109.5 |
C14—C15—C22 | 117.43 (18) | C40—C42—H42B | 109.5 |
C10—C15—C22 | 124.61 (18) | H42A—C42—H42B | 109.5 |
C17—C16—C11 | 110.99 (17) | C40—C42—H42C | 109.5 |
C17—C16—C18 | 111.18 (19) | H42A—C42—H42C | 109.5 |
C11—C16—C18 | 111.06 (17) | H42B—C42—H42C | 109.5 |
C17—C16—H16 | 107.8 | C37—C43—C45 | 113.23 (17) |
C11—C16—H16 | 107.8 | C37—C43—C44 | 110.56 (17) |
C18—C16—H16 | 107.8 | C45—C43—C44 | 110.05 (18) |
C16—C17—H17A | 109.5 | C37—C43—H43 | 107.6 |
C16—C17—H17B | 109.5 | C45—C43—H43 | 107.6 |
H17A—C17—H17B | 109.5 | C44—C43—H43 | 107.6 |
C16—C17—H17C | 109.5 | C43—C44—H44A | 109.5 |
H17A—C17—H17C | 109.5 | C43—C44—H44B | 109.5 |
H17B—C17—H17C | 109.5 | H44A—C44—H44B | 109.5 |
C16—C18—H18A | 109.5 | C43—C44—H44C | 109.5 |
C16—C18—H18B | 109.5 | H44A—C44—H44C | 109.5 |
H18A—C18—H18B | 109.5 | H44B—C44—H44C | 109.5 |
C16—C18—H18C | 109.5 | C43—C45—H45A | 109.5 |
H18A—C18—H18C | 109.5 | C43—C45—H45B | 109.5 |
H18B—C18—H18C | 109.5 | H45A—C45—H45B | 109.5 |
C20—C19—C13 | 114.59 (18) | C43—C45—H45C | 109.5 |
C20—C19—C21 | 110.20 (19) | H45A—C45—H45C | 109.5 |
C13—C19—C21 | 109.42 (17) | H45B—C45—H45C | 109.5 |
C20—C19—H19 | 107.4 | C48—C46—C39 | 112.52 (17) |
C13—C19—H19 | 107.4 | C48—C46—C47 | 110.03 (17) |
C21—C19—H19 | 107.4 | C39—C46—C47 | 109.71 (17) |
C19—C20—H20A | 109.5 | C48—C46—H46 | 108.2 |
C19—C20—H20B | 109.5 | C39—C46—H46 | 108.2 |
H20A—C20—H20B | 109.5 | C47—C46—H46 | 108.2 |
C19—C20—H20C | 109.5 | C46—C47—H47A | 109.5 |
H20A—C20—H20C | 109.5 | C46—C47—H47B | 109.5 |
H20B—C20—H20C | 109.5 | H47A—C47—H47B | 109.5 |
C19—C21—H21A | 109.5 | C46—C47—H47C | 109.5 |
C19—C21—H21B | 109.5 | H47A—C47—H47C | 109.5 |
H21A—C21—H21B | 109.5 | H47B—C47—H47C | 109.5 |
C19—C21—H21C | 109.5 | C46—C48—H48A | 109.5 |
H21A—C21—H21C | 109.5 | C46—C48—H48B | 109.5 |
H21B—C21—H21C | 109.5 | H48A—C48—H48B | 109.5 |
C15—C22—C24 | 108.91 (17) | C46—C48—H48C | 109.5 |
C15—C22—C23 | 113.08 (17) | H48A—C48—H48C | 109.5 |
C24—C22—C23 | 110.56 (19) | H48B—C48—H48C | 109.5 |
C15—C22—H22 | 108.0 | C1—N1—C9 | 119.06 (18) |
C24—C22—H22 | 108.0 | C1—N1—Zn1 | 130.77 (15) |
C23—C22—H22 | 108.0 | C9—N1—Zn1 | 110.01 (13) |
C22—C23—H23A | 109.5 | C8—N2—S1 | 120.66 (14) |
C22—C23—H23B | 109.5 | C8—N2—Zn1 | 113.36 (13) |
H23A—C23—H23B | 109.5 | S1—N2—Zn1 | 117.19 (9) |
C22—C23—H23C | 109.5 | C25—N3—C33 | 118.81 (18) |
H23A—C23—H23C | 109.5 | C25—N3—Zn1 | 130.13 (15) |
H23B—C23—H23C | 109.5 | C33—N3—Zn1 | 110.64 (14) |
C22—C24—H24A | 109.5 | C32—N4—S2 | 122.86 (14) |
C22—C24—H24B | 109.5 | C32—N4—Zn1 | 113.53 (13) |
H24A—C24—H24B | 109.5 | S2—N4—Zn1 | 118.84 (10) |
C22—C24—H24C | 109.5 | N2—Zn1—N4 | 131.86 (7) |
H24A—C24—H24C | 109.5 | N2—Zn1—N3 | 122.20 (7) |
H24B—C24—H24C | 109.5 | N4—Zn1—N3 | 82.37 (7) |
N3—C25—C26 | 123.1 (2) | N2—Zn1—N1 | 82.95 (7) |
N3—C25—H25 | 118.5 | N4—Zn1—N1 | 119.23 (7) |
C26—C25—H25 | 118.5 | N3—Zn1—N1 | 123.93 (7) |
C27—C26—C25 | 119.0 (2) | O3—S2—O4 | 117.33 (9) |
C27—C26—H26 | 120.5 | O3—S2—N4 | 109.98 (9) |
C25—C26—H26 | 120.5 | O4—S2—N4 | 105.19 (9) |
C26—C27—C28 | 120.1 (2) | O3—S2—C34 | 108.33 (9) |
C26—C27—H27 | 120.0 | O4—S2—C34 | 107.71 (9) |
C28—C27—H27 | 120.0 | N4—S2—C34 | 107.94 (9) |
C27—C28—C33 | 117.4 (2) | O1—S1—O2 | 116.03 (9) |
C27—C28—C29 | 123.4 (2) | O1—S1—N2 | 110.85 (9) |
C33—C28—C29 | 119.2 (2) | O2—S1—N2 | 104.44 (9) |
C30—C29—C28 | 119.6 (2) | O1—S1—C10 | 109.21 (9) |
C30—C29—H29 | 120.2 | O2—S1—C10 | 106.29 (9) |
C28—C29—H29 | 120.2 | N2—S1—C10 | 109.79 (9) |
| | | |
N1—C1—C2—C3 | 1.0 (3) | C36—C35—C40—C42 | −40.0 (3) |
C1—C2—C3—C4 | 0.5 (3) | C34—C35—C40—C42 | 137.6 (2) |
C2—C3—C4—C5 | 177.6 (2) | C36—C35—C40—C41 | 84.2 (2) |
C2—C3—C4—C9 | −1.6 (3) | C34—C35—C40—C41 | −98.1 (2) |
C3—C4—C5—C6 | −179.4 (2) | C38—C37—C43—C45 | 125.9 (2) |
C9—C4—C5—C6 | −0.2 (3) | C36—C37—C43—C45 | −59.7 (3) |
C4—C5—C6—C7 | −0.9 (3) | C38—C37—C43—C44 | −110.1 (2) |
C5—C6—C7—C8 | 1.8 (3) | C36—C37—C43—C44 | 64.3 (2) |
C6—C7—C8—N2 | −179.8 (2) | C38—C39—C46—C48 | −67.9 (2) |
C6—C7—C8—C9 | −1.3 (3) | C34—C39—C46—C48 | 116.3 (2) |
C3—C4—C9—N1 | 1.5 (3) | C38—C39—C46—C47 | 55.0 (2) |
C5—C4—C9—N1 | −177.76 (19) | C34—C39—C46—C47 | −120.8 (2) |
C3—C4—C9—C8 | 179.82 (19) | C2—C1—N1—C9 | −1.2 (3) |
C5—C4—C9—C8 | 0.6 (3) | C2—C1—N1—Zn1 | 173.71 (16) |
C7—C8—C9—N1 | 178.60 (19) | C4—C9—N1—C1 | −0.1 (3) |
N2—C8—C9—N1 | −2.7 (3) | C8—C9—N1—C1 | −178.46 (19) |
C7—C8—C9—C4 | 0.2 (3) | C4—C9—N1—Zn1 | −175.98 (15) |
N2—C8—C9—C4 | 178.86 (18) | C8—C9—N1—Zn1 | 5.6 (2) |
C15—C10—C11—C12 | 8.3 (3) | C7—C8—N2—S1 | −36.8 (3) |
S1—C10—C11—C12 | −163.93 (15) | C9—C8—N2—S1 | 144.67 (16) |
C15—C10—C11—C16 | −169.32 (19) | C7—C8—N2—Zn1 | 176.63 (18) |
S1—C10—C11—C16 | 18.5 (3) | C9—C8—N2—Zn1 | −1.9 (2) |
C10—C11—C12—C13 | −3.8 (3) | C26—C25—N3—C33 | 1.5 (3) |
C16—C11—C12—C13 | 174.05 (18) | C26—C25—N3—Zn1 | 173.34 (16) |
C11—C12—C13—C14 | −3.0 (3) | C28—C33—N3—C25 | −0.7 (3) |
C11—C12—C13—C19 | −179.82 (19) | C32—C33—N3—C25 | 177.30 (18) |
C12—C13—C14—C15 | 5.7 (3) | C28—C33—N3—Zn1 | −174.11 (15) |
C19—C13—C14—C15 | −177.34 (19) | C32—C33—N3—Zn1 | 3.9 (2) |
C13—C14—C15—C10 | −1.3 (3) | C31—C32—N4—S2 | 15.3 (3) |
C13—C14—C15—C22 | −176.95 (19) | C33—C32—N4—S2 | −167.25 (14) |
C11—C10—C15—C14 | −5.9 (3) | C31—C32—N4—Zn1 | 170.44 (17) |
S1—C10—C15—C14 | 166.68 (15) | C33—C32—N4—Zn1 | −12.1 (2) |
C11—C10—C15—C22 | 169.40 (18) | C8—N2—Zn1—N4 | −119.55 (14) |
S1—C10—C15—C22 | −18.1 (3) | S1—N2—Zn1—N4 | 92.65 (12) |
C12—C11—C16—C17 | 73.6 (2) | C8—N2—Zn1—N3 | 129.75 (13) |
C10—C11—C16—C17 | −108.7 (2) | S1—N2—Zn1—N3 | −18.05 (14) |
C12—C11—C16—C18 | −50.6 (2) | C8—N2—Zn1—N1 | 3.82 (14) |
C10—C11—C16—C18 | 127.1 (2) | S1—N2—Zn1—N1 | −143.98 (11) |
C12—C13—C19—C20 | −24.7 (3) | C32—N4—Zn1—N2 | −115.86 (14) |
C14—C13—C19—C20 | 158.5 (2) | S2—N4—Zn1—N2 | 40.39 (15) |
C12—C13—C19—C21 | 99.6 (2) | C32—N4—Zn1—N3 | 11.14 (13) |
C14—C13—C19—C21 | −77.1 (2) | S2—N4—Zn1—N3 | 167.39 (11) |
C14—C15—C22—C24 | 80.0 (2) | C32—N4—Zn1—N1 | 135.92 (13) |
C10—C15—C22—C24 | −95.3 (2) | S2—N4—Zn1—N1 | −67.83 (13) |
C14—C15—C22—C23 | −43.3 (3) | C25—N3—Zn1—N2 | −45.2 (2) |
C10—C15—C22—C23 | 141.4 (2) | C33—N3—Zn1—N2 | 127.17 (13) |
N3—C25—C26—C27 | −1.0 (3) | C25—N3—Zn1—N4 | 179.45 (19) |
C25—C26—C27—C28 | −0.3 (3) | C33—N3—Zn1—N4 | −8.16 (13) |
C26—C27—C28—C33 | 0.9 (3) | C25—N3—Zn1—N1 | 59.2 (2) |
C26—C27—C28—C29 | −177.0 (2) | C33—N3—Zn1—N1 | −128.41 (13) |
C27—C28—C29—C30 | 177.5 (2) | C1—N1—Zn1—N2 | 179.6 (2) |
C33—C28—C29—C30 | −0.4 (3) | C9—N1—Zn1—N2 | −5.12 (14) |
C28—C29—C30—C31 | 0.7 (3) | C1—N1—Zn1—N4 | −45.9 (2) |
C29—C30—C31—C32 | −0.1 (3) | C9—N1—Zn1—N4 | 129.42 (13) |
C30—C31—C32—N4 | 176.69 (19) | C1—N1—Zn1—N3 | 55.3 (2) |
C30—C31—C32—C33 | −0.7 (3) | C9—N1—Zn1—N3 | −129.44 (13) |
C27—C28—C33—N3 | −0.4 (3) | C32—N4—S2—O3 | 54.37 (18) |
C29—C28—C33—N3 | 177.59 (18) | Zn1—N4—S2—O3 | −99.56 (11) |
C27—C28—C33—C32 | −178.42 (19) | C32—N4—S2—O4 | −178.41 (15) |
C29—C28—C33—C32 | −0.4 (3) | Zn1—N4—S2—O4 | 27.66 (13) |
C31—C32—C33—N3 | −177.10 (18) | C32—N4—S2—C34 | −63.63 (18) |
N4—C32—C33—N3 | 5.2 (3) | Zn1—N4—S2—C34 | 142.44 (10) |
C31—C32—C33—C28 | 1.0 (3) | C39—C34—S2—O3 | −159.45 (15) |
N4—C32—C33—C28 | −176.76 (17) | C35—C34—S2—O3 | 20.55 (18) |
C39—C34—C35—C36 | 4.4 (3) | C39—C34—S2—O4 | 72.71 (17) |
S2—C34—C35—C36 | −175.56 (14) | C35—C34—S2—O4 | −107.29 (16) |
C39—C34—C35—C40 | −173.24 (18) | C39—C34—S2—N4 | −40.40 (18) |
S2—C34—C35—C40 | 6.8 (3) | C35—C34—S2—N4 | 139.60 (16) |
C34—C35—C36—C37 | −0.9 (3) | C8—N2—S1—O1 | −49.64 (18) |
C40—C35—C36—C37 | 176.92 (18) | Zn1—N2—S1—O1 | 95.71 (11) |
C35—C36—C37—C38 | −1.6 (3) | C8—N2—S1—O2 | −175.29 (15) |
C35—C36—C37—C43 | −176.21 (18) | Zn1—N2—S1—O2 | −29.95 (12) |
C36—C37—C38—C39 | 0.8 (3) | C8—N2—S1—C10 | 71.10 (17) |
C43—C37—C38—C39 | 175.39 (18) | Zn1—N2—S1—C10 | −143.55 (10) |
C37—C38—C39—C34 | 2.7 (3) | C11—C10—S1—O1 | 0.19 (19) |
C37—C38—C39—C46 | −173.44 (18) | C15—C10—S1—O1 | −172.29 (15) |
C35—C34—C39—C38 | −5.3 (3) | C11—C10—S1—O2 | 126.05 (16) |
S2—C34—C39—C38 | 174.72 (14) | C15—C10—S1—O2 | −46.42 (18) |
C35—C34—C39—C46 | 170.47 (18) | C11—C10—S1—N2 | −121.54 (16) |
S2—C34—C39—C46 | −9.5 (3) | C15—C10—S1—N2 | 65.98 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C20—H20B···O1i | 0.98 | 2.55 | 3.533 (3) | 179 |
C29—H29···O2ii | 0.95 | 2.55 | 3.158 (3) | 123 |
C30—H30···O2ii | 0.95 | 2.54 | 3.165 (3) | 123 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y, −z+1. |