In the title compound, [Zn(C
18H
17N
2O
2S)
2]·C
3H
7NO, the Zn atom is four-coordinated by the N atoms of sulfonamide and quinoline groups. Two intermolecular C—H
O hydrogen bonds connect the molecules into a three-dimensional network.
Supporting information
CCDC reference: 608369
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.040
- wR factor = 0.116
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.69 Ratio
Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.84
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.65 mm
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.49 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C34
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16A
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C35
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17B
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N5
PLAT301_ALERT_3_C Main Residue Disorder ......................... 6.00 Perc.
Alert level G
ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be
replaced by the scaled T values. Since the ratio of scaled T's
is identical to the ratio of reported T values, the scaling
does not imply a change to the absorption corrections used in
the study.
Ratio of Tmax expected/reported 0.840
Tmax scaled 0.498 Tmin scaled 0.399
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
10 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4-PC Software (Nonius, 1996); cell refinement: CAD-4-PC Software; data reduction: REDU4 (Stoe & Cie, 1987); 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[4-n-propyl-
N-(8-quinolyl)benzenesulfonamidato-k
2N,
N']zinc(II) dimethylformamide solvate
top
Crystal data top
[Zn(C18H17N2O2S)2]·C3H7NO | F(000) = 1648 |
Mr = 789.26 | Dx = 1.377 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 15.385 (2) Å | θ = 4.1–18.5° |
b = 16.928 (2) Å | µ = 2.33 mm−1 |
c = 16.170 (2) Å | T = 299 K |
β = 115.30 (1)° | Prism, green |
V = 3807.3 (8) Å3 | 0.65 × 0.35 × 0.30 mm |
Z = 4 | |
Data collection top
Nonius CAD-4 diffractometer | 5817 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.024 |
Graphite monochromator | θmax = 67.0°, θmin = 3.3° |
ω/2θ scans | h = −18→16 |
Absorption correction: ψ scan (North et al., 1968) | k = −20→6 |
Tmin = 0.474, Tmax = 0.592 | l = 0→19 |
9944 measured reflections | 3 standard reflections every 120 min |
6784 independent reflections | intensity decay: 0.5% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.0638P)2 + 1.3631P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
6784 reflections | Δρmax = 0.31 e Å−3 |
498 parameters | Δρmin = −0.48 e Å−3 |
4 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00120 (9) |
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 | Occ. (<1) |
Zn1 | 0.29231 (2) | 0.46809 (2) | 0.228831 (19) | 0.05445 (13) | |
S1 | 0.29473 (5) | 0.64739 (4) | 0.18201 (4) | 0.0690 (2) | |
S2 | 0.41590 (5) | 0.38757 (5) | 0.14429 (4) | 0.06339 (18) | |
O1 | 0.2604 (2) | 0.71667 (13) | 0.21046 (15) | 0.0973 (8) | |
O2 | 0.39349 (15) | 0.62404 (16) | 0.23451 (13) | 0.0973 (8) | |
O3 | 0.32637 (16) | 0.41238 (14) | 0.07104 (12) | 0.0823 (6) | |
O4 | 0.50245 (16) | 0.41918 (14) | 0.14496 (16) | 0.0870 (6) | |
N1 | 0.23328 (14) | 0.57107 (12) | 0.17942 (13) | 0.0560 (5) | |
N2 | 0.15225 (13) | 0.43340 (11) | 0.17865 (12) | 0.0488 (4) | |
N3 | 0.40298 (14) | 0.40763 (14) | 0.23483 (13) | 0.0599 (5) | |
N4 | 0.35530 (13) | 0.44595 (12) | 0.36783 (12) | 0.0506 (4) | |
C1 | 0.13170 (16) | 0.57049 (14) | 0.14020 (14) | 0.0495 (5) | |
C2 | 0.0696 (2) | 0.63283 (16) | 0.10374 (18) | 0.0656 (7) | |
H2 | 0.0938 | 0.6830 | 0.1030 | 0.079* | |
C3 | −0.0310 (2) | 0.62101 (18) | 0.06741 (19) | 0.0711 (7) | |
H3 | −0.0715 | 0.6639 | 0.0421 | 0.085* | |
C4 | −0.07032 (19) | 0.55042 (17) | 0.06795 (18) | 0.0639 (7) | |
H4 | −0.1368 | 0.5448 | 0.0435 | 0.077* | |
C5 | −0.01004 (16) | 0.48502 (15) | 0.10579 (15) | 0.0517 (5) | |
C6 | −0.04390 (18) | 0.40954 (17) | 0.11196 (18) | 0.0649 (7) | |
H6 | −0.1097 | 0.4007 | 0.0899 | 0.078* | |
C7 | 0.0184 (2) | 0.34944 (18) | 0.1498 (2) | 0.0735 (8) | |
H7 | −0.0041 | 0.2992 | 0.1537 | 0.088* | |
C8 | 0.11692 (18) | 0.36353 (16) | 0.18299 (18) | 0.0639 (6) | |
H8 | 0.1593 | 0.3219 | 0.2092 | 0.077* | |
C9 | 0.09121 (15) | 0.49515 (13) | 0.14129 (13) | 0.0446 (4) | |
C10 | 0.28055 (17) | 0.66509 (15) | 0.06919 (16) | 0.0574 (6) | |
C11 | 0.2349 (2) | 0.73283 (16) | 0.0225 (2) | 0.0716 (7) | |
H11 | 0.2105 | 0.7696 | 0.0498 | 0.086* | |
C12 | 0.2263 (2) | 0.74467 (18) | −0.0650 (2) | 0.0777 (8) | |
H12 | 0.1955 | 0.7900 | −0.0965 | 0.093* | |
C13 | 0.2618 (2) | 0.69166 (19) | −0.10726 (18) | 0.0702 (8) | |
C14 | 0.3078 (2) | 0.6249 (2) | −0.0595 (2) | 0.0717 (7) | |
H14 | 0.3331 | 0.5886 | −0.0865 | 0.086* | |
C15 | 0.31663 (18) | 0.61137 (18) | 0.02806 (18) | 0.0651 (7) | |
H15 | 0.3470 | 0.5659 | 0.0592 | 0.078* | |
C16A | 0.2585 (6) | 0.6983 (7) | −0.2034 (4) | 0.078 (2) | 0.705 (17) |
H16A | 0.2686 | 0.7529 | −0.2151 | 0.094* | 0.705 (17) |
H16B | 0.3103 | 0.6671 | −0.2058 | 0.094* | 0.705 (17) |
C17A | 0.1654 (7) | 0.6706 (8) | −0.2760 (4) | 0.120 (4) | 0.705 (17) |
H17A | 0.1137 | 0.7031 | −0.2756 | 0.144* | 0.705 (17) |
H17B | 0.1539 | 0.6166 | −0.2633 | 0.144* | 0.705 (17) |
C18A | 0.1652 (11) | 0.6747 (9) | −0.3716 (6) | 0.137 (6) | 0.705 (17) |
H18A | 0.1039 | 0.6575 | −0.4171 | 0.205* | 0.705 (17) |
H18B | 0.2148 | 0.6410 | −0.3729 | 0.205* | 0.705 (17) |
H18C | 0.1768 | 0.7281 | −0.3842 | 0.205* | 0.705 (17) |
C16B | 0.2253 (15) | 0.7172 (10) | −0.2076 (9) | 0.065 (4) | 0.295 (17) |
H16C | 0.1609 | 0.7388 | −0.2291 | 0.078* | 0.295 (17) |
H16D | 0.2670 | 0.7577 | −0.2132 | 0.078* | 0.295 (17) |
C17B | 0.2245 (18) | 0.6458 (8) | −0.2645 (9) | 0.087 (5) | 0.295 (17) |
H17C | 0.1819 | 0.6058 | −0.2594 | 0.105* | 0.295 (17) |
H17D | 0.2887 | 0.6235 | −0.2417 | 0.105* | 0.295 (17) |
C18B | 0.190 (3) | 0.669 (3) | −0.3661 (14) | 0.165 (17) | 0.295 (17) |
H18D | 0.1597 | 0.6250 | −0.4045 | 0.248* | 0.295 (17) |
H18E | 0.2445 | 0.6858 | −0.3766 | 0.248* | 0.295 (17) |
H18F | 0.1452 | 0.7123 | −0.3803 | 0.248* | 0.295 (17) |
C19 | 0.47013 (16) | 0.38714 (15) | 0.32365 (15) | 0.0548 (5) | |
C20 | 0.55775 (18) | 0.35077 (18) | 0.34952 (19) | 0.0691 (7) | |
H20 | 0.5801 | 0.3387 | 0.3059 | 0.083* | |
C21 | 0.61404 (19) | 0.33162 (19) | 0.4425 (2) | 0.0748 (8) | |
H21 | 0.6736 | 0.3078 | 0.4588 | 0.090* | |
C22 | 0.58473 (19) | 0.34656 (17) | 0.50807 (18) | 0.0693 (7) | |
H22 | 0.6227 | 0.3316 | 0.5682 | 0.083* | |
C23 | 0.49597 (17) | 0.38508 (15) | 0.48556 (15) | 0.0560 (6) | |
C24 | 0.4600 (2) | 0.40537 (16) | 0.54954 (16) | 0.0642 (7) | |
H24 | 0.4945 | 0.3917 | 0.6107 | 0.077* | |
C25 | 0.3754 (2) | 0.44471 (18) | 0.52260 (17) | 0.0665 (7) | |
H25 | 0.3515 | 0.4581 | 0.5647 | 0.080* | |
C26 | 0.32485 (18) | 0.46470 (16) | 0.43030 (16) | 0.0596 (6) | |
H26 | 0.2674 | 0.4924 | 0.4121 | 0.071* | |
C27 | 0.43970 (15) | 0.40610 (14) | 0.39312 (14) | 0.0491 (5) | |
C28 | 0.42453 (17) | 0.28409 (17) | 0.14068 (15) | 0.0598 (6) | |
C29 | 0.4948 (2) | 0.2497 (2) | 0.1199 (2) | 0.0731 (8) | |
H29 | 0.5357 | 0.2812 | 0.1050 | 0.088* | |
C30 | 0.5035 (2) | 0.1688 (2) | 0.1216 (2) | 0.0851 (9) | |
H30 | 0.5509 | 0.1459 | 0.1081 | 0.102* | |
C31 | 0.4424 (2) | 0.1201 (2) | 0.1431 (2) | 0.0824 (9) | |
C32 | 0.3711 (2) | 0.1563 (2) | 0.1600 (2) | 0.0833 (9) | |
H32 | 0.3278 | 0.1251 | 0.1718 | 0.100* | |
C33 | 0.3625 (2) | 0.2364 (2) | 0.1599 (2) | 0.0736 (8) | |
H33 | 0.3146 | 0.2591 | 0.1729 | 0.088* | |
C34 | 0.4525 (3) | 0.0309 (3) | 0.1465 (3) | 0.1085 (13) | |
H34A | 0.5202 | 0.0172 | 0.1726 | 0.130* | |
H34B | 0.4255 | 0.0096 | 0.1861 | 0.130* | |
C35 | 0.4030 (3) | −0.0060 (2) | 0.0539 (2) | 0.0927 (10) | |
H35A | 0.4355 | 0.0094 | 0.0165 | 0.111* | |
H35B | 0.3372 | 0.0128 | 0.0243 | 0.111* | |
C36 | 0.4035 (4) | −0.0962 (3) | 0.0618 (4) | 0.1264 (16) | |
H36A | 0.4685 | −0.1151 | 0.0852 | 0.190* | |
H36B | 0.3666 | −0.1187 | 0.0025 | 0.190* | |
H36C | 0.3759 | −0.1112 | 0.1026 | 0.190* | |
O5 | 0.7604 (3) | 0.0548 (3) | 0.1687 (2) | 0.1689 (16) | |
N5 | 0.8337 (2) | 0.08183 (18) | 0.31744 (17) | 0.0844 (7) | |
C37 | 0.8345 (4) | 0.0642 (3) | 0.2403 (3) | 0.1224 (15) | |
H37A | 0.8936 | 0.0582 | 0.2381 | 0.147* | |
C38 | 0.9208 (3) | 0.0947 (3) | 0.3995 (3) | 0.1243 (16) | |
H38A | 0.9328 | 0.0498 | 0.4392 | 0.187* | |
H38B | 0.9138 | 0.1411 | 0.4302 | 0.187* | |
H38C | 0.9738 | 0.1016 | 0.3837 | 0.187* | |
C39 | 0.7458 (3) | 0.0868 (3) | 0.3279 (3) | 0.1187 (14) | |
H39A | 0.6960 | 0.1080 | 0.2730 | 0.178* | |
H39B | 0.7550 | 0.1207 | 0.3785 | 0.178* | |
H39C | 0.7276 | 0.0351 | 0.3391 | 0.178* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.04281 (18) | 0.0773 (2) | 0.03420 (17) | −0.00153 (14) | 0.00784 (12) | 0.00671 (13) |
S1 | 0.0782 (4) | 0.0783 (4) | 0.0392 (3) | −0.0360 (3) | 0.0143 (3) | −0.0084 (3) |
S2 | 0.0622 (4) | 0.0874 (5) | 0.0434 (3) | −0.0017 (3) | 0.0253 (3) | 0.0057 (3) |
O1 | 0.152 (2) | 0.0767 (14) | 0.0749 (13) | −0.0520 (14) | 0.0600 (15) | −0.0368 (11) |
O2 | 0.0711 (12) | 0.140 (2) | 0.0494 (11) | −0.0472 (13) | −0.0041 (9) | 0.0134 (12) |
O3 | 0.0853 (13) | 0.1138 (16) | 0.0391 (9) | 0.0187 (12) | 0.0185 (9) | 0.0136 (10) |
O4 | 0.0917 (15) | 0.0968 (15) | 0.0936 (15) | −0.0165 (12) | 0.0595 (13) | 0.0032 (12) |
N1 | 0.0578 (11) | 0.0622 (12) | 0.0407 (9) | −0.0136 (9) | 0.0140 (8) | 0.0008 (8) |
N2 | 0.0440 (9) | 0.0554 (10) | 0.0375 (9) | 0.0001 (8) | 0.0085 (7) | 0.0077 (8) |
N3 | 0.0476 (10) | 0.0909 (15) | 0.0353 (9) | 0.0025 (10) | 0.0120 (8) | 0.0027 (9) |
N4 | 0.0425 (9) | 0.0681 (12) | 0.0351 (9) | −0.0071 (8) | 0.0107 (7) | 0.0027 (8) |
C1 | 0.0559 (12) | 0.0534 (12) | 0.0346 (10) | −0.0040 (10) | 0.0150 (9) | −0.0037 (9) |
C2 | 0.0846 (18) | 0.0504 (14) | 0.0609 (15) | 0.0021 (12) | 0.0302 (14) | −0.0011 (11) |
C3 | 0.0717 (17) | 0.0729 (18) | 0.0632 (16) | 0.0260 (14) | 0.0236 (14) | 0.0044 (13) |
C4 | 0.0531 (13) | 0.0816 (19) | 0.0537 (14) | 0.0143 (13) | 0.0195 (11) | 0.0023 (12) |
C5 | 0.0460 (11) | 0.0670 (15) | 0.0381 (11) | 0.0008 (10) | 0.0142 (9) | −0.0009 (10) |
C6 | 0.0471 (12) | 0.0821 (18) | 0.0568 (14) | −0.0111 (12) | 0.0139 (11) | 0.0041 (13) |
C7 | 0.0661 (16) | 0.0663 (17) | 0.0764 (18) | −0.0183 (13) | 0.0192 (14) | 0.0121 (14) |
C8 | 0.0586 (14) | 0.0574 (14) | 0.0627 (15) | 0.0006 (11) | 0.0136 (12) | 0.0169 (12) |
C9 | 0.0468 (11) | 0.0519 (12) | 0.0300 (9) | 0.0006 (9) | 0.0114 (8) | 0.0010 (8) |
C10 | 0.0567 (13) | 0.0624 (14) | 0.0435 (12) | −0.0213 (11) | 0.0123 (10) | −0.0021 (10) |
C11 | 0.096 (2) | 0.0510 (14) | 0.0634 (16) | −0.0135 (14) | 0.0300 (15) | −0.0011 (12) |
C12 | 0.099 (2) | 0.0618 (16) | 0.0592 (16) | −0.0155 (15) | 0.0208 (15) | 0.0106 (13) |
C13 | 0.0701 (16) | 0.0832 (19) | 0.0481 (13) | −0.0303 (14) | 0.0164 (12) | 0.0049 (13) |
C14 | 0.0650 (15) | 0.092 (2) | 0.0614 (16) | −0.0062 (14) | 0.0300 (13) | 0.0025 (15) |
C15 | 0.0516 (13) | 0.0797 (17) | 0.0580 (14) | 0.0002 (12) | 0.0177 (11) | 0.0138 (13) |
C16A | 0.072 (5) | 0.106 (7) | 0.053 (3) | −0.015 (4) | 0.023 (3) | 0.011 (3) |
C17A | 0.082 (5) | 0.219 (9) | 0.051 (3) | −0.046 (6) | 0.019 (3) | −0.009 (4) |
C18A | 0.142 (9) | 0.203 (13) | 0.056 (5) | −0.066 (10) | 0.033 (5) | −0.009 (5) |
C16B | 0.067 (10) | 0.067 (7) | 0.065 (7) | 0.003 (7) | 0.034 (7) | 0.011 (5) |
C17B | 0.098 (13) | 0.102 (9) | 0.060 (7) | −0.008 (8) | 0.033 (8) | −0.001 (6) |
C18B | 0.14 (2) | 0.27 (4) | 0.049 (11) | 0.08 (2) | 0.005 (10) | −0.021 (14) |
C19 | 0.0433 (11) | 0.0705 (15) | 0.0408 (11) | −0.0070 (10) | 0.0086 (9) | −0.0001 (10) |
C20 | 0.0495 (13) | 0.0899 (19) | 0.0573 (15) | 0.0024 (13) | 0.0127 (11) | −0.0025 (13) |
C21 | 0.0465 (13) | 0.0843 (19) | 0.0699 (18) | 0.0049 (13) | 0.0024 (12) | 0.0034 (15) |
C22 | 0.0582 (14) | 0.0738 (17) | 0.0498 (14) | −0.0056 (13) | −0.0020 (12) | 0.0089 (12) |
C23 | 0.0527 (12) | 0.0612 (13) | 0.0365 (11) | −0.0155 (11) | 0.0022 (9) | 0.0021 (10) |
C24 | 0.0705 (16) | 0.0734 (16) | 0.0326 (11) | −0.0186 (13) | 0.0067 (11) | 0.0036 (10) |
C25 | 0.0730 (17) | 0.0857 (18) | 0.0378 (12) | −0.0153 (14) | 0.0207 (11) | −0.0013 (12) |
C26 | 0.0538 (13) | 0.0804 (17) | 0.0415 (12) | −0.0070 (12) | 0.0175 (10) | 0.0011 (11) |
C27 | 0.0419 (11) | 0.0585 (13) | 0.0359 (10) | −0.0124 (9) | 0.0061 (8) | 0.0024 (9) |
C28 | 0.0518 (12) | 0.0892 (18) | 0.0363 (11) | −0.0073 (12) | 0.0169 (10) | −0.0020 (11) |
C29 | 0.0591 (15) | 0.099 (2) | 0.0645 (16) | −0.0061 (14) | 0.0293 (13) | −0.0035 (15) |
C30 | 0.0686 (18) | 0.106 (3) | 0.075 (2) | 0.0061 (17) | 0.0257 (16) | −0.0104 (18) |
C31 | 0.085 (2) | 0.090 (2) | 0.0530 (16) | −0.0083 (17) | 0.0103 (14) | −0.0044 (14) |
C32 | 0.086 (2) | 0.096 (2) | 0.0700 (19) | −0.0216 (18) | 0.0353 (16) | −0.0089 (16) |
C33 | 0.0713 (17) | 0.094 (2) | 0.0643 (16) | −0.0143 (15) | 0.0371 (14) | −0.0092 (15) |
C34 | 0.110 (3) | 0.112 (3) | 0.073 (2) | −0.001 (2) | 0.009 (2) | −0.009 (2) |
C35 | 0.084 (2) | 0.125 (3) | 0.082 (2) | −0.015 (2) | 0.0473 (19) | −0.018 (2) |
C36 | 0.125 (3) | 0.109 (3) | 0.161 (5) | −0.021 (3) | 0.077 (3) | −0.045 (3) |
O5 | 0.178 (4) | 0.234 (4) | 0.0634 (18) | −0.006 (3) | 0.021 (2) | −0.006 (2) |
N5 | 0.0818 (16) | 0.110 (2) | 0.0564 (14) | 0.0126 (15) | 0.0252 (12) | 0.0040 (13) |
C37 | 0.147 (4) | 0.151 (4) | 0.066 (2) | 0.015 (3) | 0.042 (3) | 0.010 (2) |
C38 | 0.097 (3) | 0.164 (4) | 0.086 (3) | 0.018 (3) | 0.014 (2) | −0.025 (3) |
C39 | 0.102 (3) | 0.151 (4) | 0.109 (3) | 0.012 (3) | 0.051 (3) | 0.027 (3) |
Geometric parameters (Å, º) top
Zn1—N3 | 1.953 (2) | C16B—H16C | 0.9700 |
Zn1—N1 | 1.970 (2) | C16B—H16D | 0.9700 |
Zn1—N2 | 2.0377 (19) | C17B—C18B | 1.548 (16) |
Zn1—N4 | 2.0663 (18) | C17B—H17C | 0.9700 |
S1—O1 | 1.440 (3) | C17B—H17D | 0.9700 |
S1—O2 | 1.443 (2) | C18B—H18D | 0.9600 |
S1—N1 | 1.591 (2) | C18B—H18E | 0.9600 |
S1—C10 | 1.768 (2) | C18B—H18F | 0.9600 |
S2—O4 | 1.431 (2) | C19—C20 | 1.375 (4) |
S2—O3 | 1.443 (2) | C19—C27 | 1.426 (3) |
S2—N3 | 1.596 (2) | C20—C21 | 1.415 (4) |
S2—C28 | 1.760 (3) | C20—H20 | 0.9300 |
N1—C1 | 1.413 (3) | C21—C22 | 1.342 (4) |
N2—C8 | 1.316 (3) | C21—H21 | 0.9300 |
N2—C9 | 1.362 (3) | C22—C23 | 1.413 (4) |
N3—C19 | 1.408 (3) | C22—H22 | 0.9300 |
N4—C26 | 1.321 (3) | C23—C24 | 1.409 (4) |
N4—C27 | 1.362 (3) | C23—C27 | 1.416 (3) |
C1—C2 | 1.376 (4) | C24—C25 | 1.357 (4) |
C1—C9 | 1.423 (3) | C24—H24 | 0.9300 |
C2—C3 | 1.415 (4) | C25—C26 | 1.398 (3) |
C2—H2 | 0.9300 | C25—H25 | 0.9300 |
C3—C4 | 1.341 (4) | C26—H26 | 0.9300 |
C3—H3 | 0.9300 | C28—C33 | 1.384 (4) |
C4—C5 | 1.405 (4) | C28—C29 | 1.390 (4) |
C4—H4 | 0.9300 | C29—C30 | 1.376 (5) |
C5—C6 | 1.399 (4) | C29—H29 | 0.9300 |
C5—C9 | 1.422 (3) | C30—C31 | 1.401 (5) |
C6—C7 | 1.352 (4) | C30—H30 | 0.9300 |
C6—H6 | 0.9300 | C31—C32 | 1.382 (5) |
C7—C8 | 1.395 (4) | C31—C34 | 1.518 (5) |
C7—H7 | 0.9300 | C32—C33 | 1.363 (5) |
C8—H8 | 0.9300 | C32—H32 | 0.9300 |
C10—C15 | 1.376 (4) | C33—H33 | 0.9300 |
C10—C11 | 1.387 (4) | C34—C35 | 1.496 (5) |
C11—C12 | 1.379 (4) | C34—H34A | 0.9700 |
C11—H11 | 0.9300 | C34—H34B | 0.9700 |
C12—C13 | 1.374 (5) | C35—C36 | 1.532 (6) |
C12—H12 | 0.9300 | C35—H35A | 0.9700 |
C13—C14 | 1.382 (4) | C35—H35B | 0.9700 |
C13—C16B | 1.535 (13) | C36—H36A | 0.9600 |
C13—C16A | 1.538 (6) | C36—H36B | 0.9600 |
C14—C15 | 1.382 (4) | C36—H36C | 0.9600 |
C14—H14 | 0.9300 | O5—C37 | 1.239 (6) |
C15—H15 | 0.9300 | N5—C37 | 1.288 (5) |
C16A—C17A | 1.487 (9) | N5—C39 | 1.435 (5) |
C16A—H16A | 0.9700 | N5—C38 | 1.444 (5) |
C16A—H16B | 0.9700 | C37—H37A | 0.9300 |
C17A—C18A | 1.546 (9) | C38—H38A | 0.9600 |
C17A—H17A | 0.9700 | C38—H38B | 0.9600 |
C17A—H17B | 0.9700 | C38—H38C | 0.9600 |
C18A—H18A | 0.9600 | C39—H39A | 0.9600 |
C18A—H18B | 0.9600 | C39—H39B | 0.9600 |
C18A—H18C | 0.9600 | C39—H39C | 0.9600 |
C16B—C17B | 1.517 (16) | | |
| | | |
N3—Zn1—N1 | 136.44 (9) | C13—C16B—H16C | 109.9 |
N3—Zn1—N2 | 128.30 (9) | C17B—C16B—H16D | 109.9 |
N1—Zn1—N2 | 82.40 (8) | C13—C16B—H16D | 109.9 |
N3—Zn1—N4 | 81.79 (8) | H16C—C16B—H16D | 108.3 |
N1—Zn1—N4 | 121.48 (8) | C16B—C17B—C18B | 110 (2) |
N2—Zn1—N4 | 107.79 (7) | C16B—C17B—H17C | 109.6 |
O1—S1—O2 | 118.21 (16) | C18B—C17B—H17C | 109.6 |
O1—S1—N1 | 112.03 (13) | C16B—C17B—H17D | 109.6 |
O2—S1—N1 | 104.92 (13) | C18B—C17B—H17D | 109.6 |
O1—S1—C10 | 106.93 (14) | H17C—C17B—H17D | 108.1 |
O2—S1—C10 | 106.74 (13) | C17B—C18B—H18D | 109.5 |
N1—S1—C10 | 107.49 (10) | C17B—C18B—H18E | 109.5 |
O4—S2—O3 | 117.14 (14) | H18D—C18B—H18E | 109.5 |
O4—S2—N3 | 113.19 (13) | C17B—C18B—H18F | 109.5 |
O3—S2—N3 | 103.98 (11) | H18D—C18B—H18F | 109.5 |
O4—S2—C28 | 106.83 (13) | H18E—C18B—H18F | 109.5 |
O3—S2—C28 | 108.76 (13) | C20—C19—N3 | 128.1 (2) |
N3—S2—C28 | 106.43 (12) | C20—C19—C27 | 118.1 (2) |
C1—N1—S1 | 123.25 (17) | N3—C19—C27 | 113.8 (2) |
C1—N1—Zn1 | 113.92 (15) | C19—C20—C21 | 120.1 (3) |
S1—N1—Zn1 | 122.83 (12) | C19—C20—H20 | 120.0 |
C8—N2—C9 | 119.4 (2) | C21—C20—H20 | 120.0 |
C8—N2—Zn1 | 128.93 (16) | C22—C21—C20 | 122.5 (3) |
C9—N2—Zn1 | 111.52 (14) | C22—C21—H21 | 118.8 |
C19—N3—S2 | 123.96 (18) | C20—C21—H21 | 118.8 |
C19—N3—Zn1 | 115.07 (16) | C21—C22—C23 | 119.8 (2) |
S2—N3—Zn1 | 120.91 (11) | C21—C22—H22 | 120.1 |
C26—N4—C27 | 119.58 (19) | C23—C22—H22 | 120.1 |
C26—N4—Zn1 | 129.30 (17) | C24—C23—C22 | 124.3 (2) |
C27—N4—Zn1 | 111.12 (14) | C24—C23—C27 | 117.3 (2) |
C2—C1—N1 | 128.3 (2) | C22—C23—C27 | 118.4 (2) |
C2—C1—C9 | 117.7 (2) | C25—C24—C23 | 120.5 (2) |
N1—C1—C9 | 114.0 (2) | C25—C24—H24 | 119.7 |
C1—C2—C3 | 120.4 (3) | C23—C24—H24 | 119.7 |
C1—C2—H2 | 119.8 | C24—C25—C26 | 118.7 (2) |
C3—C2—H2 | 119.8 | C24—C25—H25 | 120.6 |
C4—C3—C2 | 122.6 (3) | C26—C25—H25 | 120.6 |
C4—C3—H3 | 118.7 | N4—C26—C25 | 122.7 (3) |
C2—C3—H3 | 118.7 | N4—C26—H26 | 118.6 |
C3—C4—C5 | 119.3 (2) | C25—C26—H26 | 118.6 |
C3—C4—H4 | 120.4 | N4—C27—C23 | 121.1 (2) |
C5—C4—H4 | 120.4 | N4—C27—C19 | 117.83 (19) |
C6—C5—C4 | 123.6 (2) | C23—C27—C19 | 121.1 (2) |
C6—C5—C9 | 117.3 (2) | C33—C28—C29 | 119.6 (3) |
C4—C5—C9 | 119.1 (2) | C33—C28—S2 | 120.3 (2) |
C7—C6—C5 | 120.4 (2) | C29—C28—S2 | 120.1 (2) |
C7—C6—H6 | 119.8 | C30—C29—C28 | 119.4 (3) |
C5—C6—H6 | 119.8 | C30—C29—H29 | 120.3 |
C6—C7—C8 | 119.3 (3) | C28—C29—H29 | 120.3 |
C6—C7—H7 | 120.4 | C29—C30—C31 | 121.4 (3) |
C8—C7—H7 | 120.4 | C29—C30—H30 | 119.3 |
N2—C8—C7 | 122.6 (2) | C31—C30—H30 | 119.3 |
N2—C8—H8 | 118.7 | C32—C31—C30 | 117.6 (3) |
C7—C8—H8 | 118.7 | C32—C31—C34 | 120.7 (4) |
N2—C9—C5 | 121.0 (2) | C30—C31—C34 | 121.6 (4) |
N2—C9—C1 | 118.10 (19) | C33—C32—C31 | 121.7 (3) |
C5—C9—C1 | 120.9 (2) | C33—C32—H32 | 119.2 |
C15—C10—C11 | 119.9 (2) | C31—C32—H32 | 119.2 |
C15—C10—S1 | 119.3 (2) | C32—C33—C28 | 120.3 (3) |
C11—C10—S1 | 120.8 (2) | C32—C33—H33 | 119.8 |
C12—C11—C10 | 118.9 (3) | C28—C33—H33 | 119.8 |
C12—C11—H11 | 120.6 | C35—C34—C31 | 112.2 (3) |
C10—C11—H11 | 120.6 | C35—C34—H34A | 109.2 |
C13—C12—C11 | 122.1 (3) | C31—C34—H34A | 109.2 |
C13—C12—H12 | 119.0 | C35—C34—H34B | 109.2 |
C11—C12—H12 | 119.0 | C31—C34—H34B | 109.2 |
C12—C13—C14 | 118.3 (3) | H34A—C34—H34B | 107.9 |
C12—C13—C16B | 107.3 (6) | C34—C35—C36 | 110.5 (4) |
C14—C13—C16B | 133.7 (6) | C34—C35—H35A | 109.6 |
C12—C13—C16A | 127.3 (5) | C36—C35—H35A | 109.6 |
C14—C13—C16A | 114.4 (5) | C34—C35—H35B | 109.6 |
C13—C14—C15 | 120.7 (3) | C36—C35—H35B | 109.6 |
C13—C14—H14 | 119.6 | H35A—C35—H35B | 108.1 |
C15—C14—H14 | 119.6 | C35—C36—H36A | 109.5 |
C10—C15—C14 | 120.2 (3) | C35—C36—H36B | 109.5 |
C10—C15—H15 | 119.9 | H36A—C36—H36B | 109.5 |
C14—C15—H15 | 119.9 | C35—C36—H36C | 109.5 |
C17A—C16A—C13 | 112.3 (6) | H36A—C36—H36C | 109.5 |
C17A—C16A—H16A | 109.1 | H36B—C36—H36C | 109.5 |
C13—C16A—H16A | 109.1 | C37—N5—C39 | 121.8 (4) |
C17A—C16A—H16B | 109.1 | C37—N5—C38 | 122.5 (4) |
C13—C16A—H16B | 109.1 | C39—N5—C38 | 115.7 (3) |
H16A—C16A—H16B | 107.9 | O5—C37—N5 | 123.3 (5) |
C16A—C17A—C18A | 111.4 (7) | O5—C37—H37A | 118.3 |
C16A—C17A—H17A | 109.4 | N5—C37—H37A | 118.3 |
C18A—C17A—H17A | 109.4 | N5—C38—H38A | 109.5 |
C16A—C17A—H17B | 109.4 | N5—C38—H38B | 109.5 |
C18A—C17A—H17B | 109.4 | H38A—C38—H38B | 109.5 |
H17A—C17A—H17B | 108.0 | N5—C38—H38C | 109.5 |
C17A—C18A—H18A | 109.5 | H38A—C38—H38C | 109.5 |
C17A—C18A—H18B | 109.5 | H38B—C38—H38C | 109.5 |
H18A—C18A—H18B | 109.5 | N5—C39—H39A | 109.5 |
C17A—C18A—H18C | 109.5 | N5—C39—H39B | 109.5 |
H18A—C18A—H18C | 109.5 | H39A—C39—H39B | 109.5 |
H18B—C18A—H18C | 109.5 | N5—C39—H39C | 109.5 |
C17B—C16B—C13 | 108.8 (11) | H39A—C39—H39C | 109.5 |
C17B—C16B—H16C | 109.9 | H39B—C39—H39C | 109.5 |
| | | |
O1—S1—N1—C1 | 45.6 (2) | C15—C10—C11—C12 | 0.3 (4) |
O2—S1—N1—C1 | 175.04 (19) | S1—C10—C11—C12 | 179.3 (2) |
C10—S1—N1—C1 | −71.6 (2) | C10—C11—C12—C13 | −0.2 (5) |
O1—S1—N1—Zn1 | −135.56 (15) | C11—C12—C13—C14 | −0.3 (4) |
O2—S1—N1—Zn1 | −6.10 (17) | C11—C12—C13—C16B | 171.1 (9) |
C10—S1—N1—Zn1 | 107.26 (15) | C11—C12—C13—C16A | −179.0 (4) |
N3—Zn1—N1—C1 | 142.27 (15) | C12—C13—C14—C15 | 0.9 (4) |
N2—Zn1—N1—C1 | 2.16 (15) | C16B—C13—C14—C15 | −167.8 (12) |
N4—Zn1—N1—C1 | −104.08 (15) | C16A—C13—C14—C15 | 179.7 (4) |
N3—Zn1—N1—S1 | −36.69 (19) | C11—C10—C15—C14 | 0.3 (4) |
N2—Zn1—N1—S1 | −176.80 (14) | S1—C10—C15—C14 | −178.8 (2) |
N4—Zn1—N1—S1 | 76.96 (15) | C13—C14—C15—C10 | −0.8 (4) |
N3—Zn1—N2—C8 | 36.3 (3) | C12—C13—C16A—C17A | −83.3 (13) |
N1—Zn1—N2—C8 | −178.0 (2) | C14—C13—C16A—C17A | 98.0 (12) |
N4—Zn1—N2—C8 | −57.3 (2) | C16B—C13—C16A—C17A | −57 (2) |
N3—Zn1—N2—C9 | −147.86 (14) | C13—C16A—C17A—C18A | −177.8 (9) |
N1—Zn1—N2—C9 | −2.13 (14) | C12—C13—C16B—C17B | −155.8 (16) |
N4—Zn1—N2—C9 | 118.57 (15) | C14—C13—C16B—C17B | 14 (3) |
O4—S2—N3—C19 | −57.4 (3) | C16A—C13—C16B—C17B | 46 (2) |
O3—S2—N3—C19 | 174.4 (2) | C13—C16B—C17B—C18B | −178.7 (19) |
C28—S2—N3—C19 | 59.6 (2) | S2—N3—C19—C20 | 3.0 (4) |
O4—S2—N3—Zn1 | 119.70 (16) | Zn1—N3—C19—C20 | −174.3 (2) |
O3—S2—N3—Zn1 | −8.48 (19) | S2—N3—C19—C27 | −175.62 (18) |
C28—S2—N3—Zn1 | −123.25 (15) | Zn1—N3—C19—C27 | 7.1 (3) |
N1—Zn1—N3—C19 | 122.42 (17) | N3—C19—C20—C21 | −177.2 (3) |
N2—Zn1—N3—C19 | −111.69 (18) | C27—C19—C20—C21 | 1.4 (4) |
N4—Zn1—N3—C19 | −5.46 (18) | C19—C20—C21—C22 | 1.0 (5) |
N1—Zn1—N3—S2 | −55.0 (2) | C20—C21—C22—C23 | −2.1 (5) |
N2—Zn1—N3—S2 | 70.94 (18) | C21—C22—C23—C24 | −178.2 (3) |
N4—Zn1—N3—S2 | 177.16 (16) | C21—C22—C23—C27 | 0.7 (4) |
N3—Zn1—N4—C26 | −177.0 (2) | C22—C23—C24—C25 | 177.8 (3) |
N1—Zn1—N4—C26 | 42.6 (2) | C27—C23—C24—C25 | −1.1 (4) |
N2—Zn1—N4—C26 | −49.4 (2) | C23—C24—C25—C26 | 0.0 (4) |
N3—Zn1—N4—C27 | 2.83 (15) | C27—N4—C26—C25 | −0.6 (4) |
N1—Zn1—N4—C27 | −137.55 (15) | Zn1—N4—C26—C25 | 179.26 (19) |
N2—Zn1—N4—C27 | 130.52 (15) | C24—C25—C26—N4 | 1.0 (4) |
S1—N1—C1—C2 | −4.1 (3) | C26—N4—C27—C23 | −0.6 (3) |
Zn1—N1—C1—C2 | 176.9 (2) | Zn1—N4—C27—C23 | 179.47 (17) |
S1—N1—C1—C9 | 177.13 (15) | C26—N4—C27—C19 | −179.9 (2) |
Zn1—N1—C1—C9 | −1.8 (2) | Zn1—N4—C27—C19 | 0.2 (2) |
N1—C1—C2—C3 | −179.8 (2) | C24—C23—C27—N4 | 1.5 (3) |
C9—C1—C2—C3 | −1.1 (4) | C22—C23—C27—N4 | −177.5 (2) |
C1—C2—C3—C4 | 1.2 (4) | C24—C23—C27—C19 | −179.3 (2) |
C2—C3—C4—C5 | −0.1 (4) | C22—C23—C27—C19 | 1.7 (3) |
C3—C4—C5—C6 | 178.1 (3) | C20—C19—C27—N4 | 176.5 (2) |
C3—C4—C5—C9 | −1.0 (4) | N3—C19—C27—N4 | −4.7 (3) |
C4—C5—C6—C7 | −179.6 (3) | C20—C19—C27—C23 | −2.7 (4) |
C9—C5—C6—C7 | −0.5 (4) | N3—C19—C27—C23 | 176.1 (2) |
C5—C6—C7—C8 | 0.2 (4) | O4—S2—C28—C33 | 165.4 (2) |
C9—N2—C8—C7 | 0.7 (4) | O3—S2—C28—C33 | −67.2 (2) |
Zn1—N2—C8—C7 | 176.2 (2) | N3—S2—C28—C33 | 44.2 (2) |
C6—C7—C8—N2 | −0.3 (5) | O4—S2—C28—C29 | −13.5 (2) |
C8—N2—C9—C5 | −0.9 (3) | O3—S2—C28—C29 | 113.8 (2) |
Zn1—N2—C9—C5 | −177.17 (15) | N3—S2—C28—C29 | −134.7 (2) |
C8—N2—C9—C1 | 178.0 (2) | C33—C28—C29—C30 | −2.0 (4) |
Zn1—N2—C9—C1 | 1.8 (2) | S2—C28—C29—C30 | 177.0 (2) |
C6—C5—C9—N2 | 0.8 (3) | C28—C29—C30—C31 | 0.5 (5) |
C4—C5—C9—N2 | 179.9 (2) | C29—C30—C31—C32 | 1.8 (5) |
C6—C5—C9—C1 | −178.1 (2) | C29—C30—C31—C34 | −179.0 (3) |
C4—C5—C9—C1 | 1.0 (3) | C30—C31—C32—C33 | −2.8 (5) |
C2—C1—C9—N2 | −178.9 (2) | C34—C31—C32—C33 | 178.0 (3) |
N1—C1—C9—N2 | 0.0 (3) | C31—C32—C33—C28 | 1.4 (5) |
C2—C1—C9—C5 | 0.0 (3) | C29—C28—C33—C32 | 1.1 (4) |
N1—C1—C9—C5 | 178.92 (18) | S2—C28—C33—C32 | −177.9 (2) |
O1—S1—C10—C15 | 173.6 (2) | C32—C31—C34—C35 | 95.9 (4) |
O2—S1—C10—C15 | 46.2 (2) | C30—C31—C34—C35 | −83.1 (4) |
N1—S1—C10—C15 | −66.0 (2) | C31—C34—C35—C36 | −172.5 (4) |
O1—S1—C10—C11 | −5.5 (2) | C39—N5—C37—O5 | 4.4 (8) |
O2—S1—C10—C11 | −132.9 (2) | C38—N5—C37—O5 | −178.2 (5) |
N1—S1—C10—C11 | 115.0 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O1i | 0.93 | 2.24 | 3.151 (3) | 167 |
C24—H24···O2ii | 0.93 | 2.37 | 3.286 (3) | 168 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z+1. |