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The nearly planar aminoquinoline fragment and the aromatic ring of the triisopropylbenzenesulfonate group of the title compound, C
24H
30N
2O
3S, form a dihedral angle of 47.9 (2)°. Both H atoms of the amino group are involved in intermolecular hydrogen bonds of types N—H
O (2.56 Å) and N—H
N (2.26 Å), linking the molecules into dimers.
Supporting information
CCDC reference: 633662
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.007 Å
- R factor = 0.058
- wR factor = 0.182
- Data-to-parameter ratio = 15.6
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 5.40 Ratio
| Author Response: C20 and C21 of one of the isopropyl moieties are disordered and have
unusually large displacement parameters.
|
Alert level B
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.95 Ratio
Alert level C
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C22
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
1 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
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.
2-Aminoquinolin-8-yl 2,4,6-triisopropylbenzenesulfonate
top
Crystal data top
C24H30N2O3S | F(000) = 1824 |
Mr = 426.56 | Dx = 1.182 Mg m−3 |
Monoclinic, C2/c | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -C 2yc | Cell parameters from 25 reflections |
a = 40.435 (3) Å | θ = 7.4–21.9° |
b = 7.0362 (4) Å | µ = 1.40 mm−1 |
c = 17.212 (2) Å | T = 299 K |
β = 101.754 (9)° | Prism, light brown |
V = 4794.3 (7) Å3 | 0.28 × 0.10 × 0.06 mm |
Z = 8 | |
Data collection top
Nonius CAD-4 diffractometer | Rint = 0.044 |
Radiation source: fine-focus sealed tube | θmax = 67.0°, θmin = 2.2° |
Graphite monochromator | h = −47→48 |
ω/2θ scans | k = −8→0 |
4693 measured reflections | l = −20→1 |
4286 independent reflections | 3 standard reflections every 120 min |
2749 reflections with I > 2σ(I) | intensity decay: 2.5% |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.182 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0995P)2 + 1.8788P] where P = (Fo2 + 2Fc2)/3 |
4286 reflections | (Δ/σ)max = 0.001 |
275 parameters | Δρmax = 0.44 e Å−3 |
14 restraints | Δρmin = −0.38 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 | |
S1 | 0.14433 (2) | 1.04970 (12) | −0.00416 (5) | 0.0473 (3) | |
O1 | 0.14875 (6) | 1.2230 (4) | 0.03941 (15) | 0.0616 (7) | |
O2 | 0.13467 (6) | 1.0617 (4) | −0.08815 (13) | 0.0616 (7) | |
O3 | 0.18021 (5) | 0.9485 (3) | 0.01901 (13) | 0.0484 (6) | |
N1 | 0.23103 (6) | 1.0271 (4) | −0.06015 (14) | 0.0402 (6) | |
N2 | 0.27257 (7) | 1.2280 (4) | −0.08524 (17) | 0.0542 (8) | |
H21N | 0.2665 | 1.3114 | −0.0544 | 0.065* | |
H22N | 0.2890 | 1.2519 | −0.1086 | 0.065* | |
C1 | 0.18914 (8) | 0.8077 (5) | −0.03302 (18) | 0.0438 (7) | |
C2 | 0.17408 (9) | 0.6339 (5) | −0.0390 (2) | 0.0545 (9) | |
H2 | 0.1576 | 0.6068 | −0.0101 | 0.065* | |
C3 | 0.18352 (10) | 0.4965 (5) | −0.0888 (2) | 0.0600 (10) | |
H3 | 0.1729 | 0.3785 | −0.0940 | 0.072* | |
C4 | 0.20822 (9) | 0.5349 (5) | −0.1298 (2) | 0.0551 (9) | |
H4 | 0.2143 | 0.4430 | −0.1632 | 0.066* | |
C5 | 0.22462 (8) | 0.7110 (5) | −0.12217 (18) | 0.0447 (7) | |
C6 | 0.25124 (9) | 0.7555 (5) | −0.1611 (2) | 0.0552 (9) | |
H6 | 0.2581 | 0.6672 | −0.1948 | 0.066* | |
C7 | 0.26662 (9) | 0.9254 (5) | −0.1495 (2) | 0.0548 (9) | |
H7 | 0.2840 | 0.9555 | −0.1755 | 0.066* | |
C8 | 0.25625 (7) | 1.0591 (5) | −0.09706 (18) | 0.0432 (7) | |
C9 | 0.21530 (7) | 0.8547 (4) | −0.07227 (17) | 0.0397 (7) | |
C10 | 0.11674 (8) | 0.9015 (5) | 0.03667 (19) | 0.0504 (8) | |
C11 | 0.09103 (9) | 0.7956 (7) | −0.0112 (2) | 0.0678 (11) | |
C12 | 0.06730 (12) | 0.7133 (8) | 0.0265 (3) | 0.0981 (17) | |
H12 | 0.0492 | 0.6483 | −0.0042 | 0.118* | |
C13 | 0.06943 (13) | 0.7240 (10) | 0.1086 (3) | 0.106 (2) | |
C14 | 0.09612 (12) | 0.8143 (8) | 0.1526 (3) | 0.0899 (16) | |
H14 | 0.0981 | 0.8160 | 0.2074 | 0.108* | |
C15 | 0.12077 (9) | 0.9050 (6) | 0.1209 (2) | 0.0584 (9) | |
C16 | 0.08745 (12) | 0.7582 (8) | −0.1004 (3) | 0.0832 (14) | |
H16 | 0.1088 | 0.7944 | −0.1151 | 0.100* | |
C17 | 0.06000 (15) | 0.8829 (11) | −0.1465 (3) | 0.128 (2) | |
H17A | 0.0648 | 1.0134 | −0.1323 | 0.192* | |
H17B | 0.0387 | 0.8481 | −0.1342 | 0.192* | |
H17C | 0.0590 | 0.8667 | −0.2023 | 0.192* | |
C18 | 0.08115 (17) | 0.5479 (10) | −0.1210 (4) | 0.133 (3) | |
H18A | 0.0590 | 0.5130 | −0.1140 | 0.200* | |
H18B | 0.0977 | 0.4720 | −0.0868 | 0.200* | |
H18C | 0.0828 | 0.5269 | −0.1752 | 0.200* | |
C19 | 0.04188 (18) | 0.6392 (12) | 0.1484 (5) | 0.157 (3) | |
H19 | 0.0512 | 0.6430 | 0.2056 | 0.188* | |
C20 | 0.0373 (2) | 0.4316 (12) | 0.1285 (5) | 0.184 (4) | |
H20A | 0.0198 | 0.3804 | 0.1527 | 0.277* | |
H20B | 0.0580 | 0.3653 | 0.1480 | 0.277* | |
H20C | 0.0310 | 0.4166 | 0.0719 | 0.277* | |
C21 | 0.0111 (2) | 0.7641 (15) | 0.1351 (7) | 0.214 (4) | |
H21A | −0.0059 | 0.7068 | 0.1590 | 0.322* | |
H21B | 0.0026 | 0.7791 | 0.0792 | 0.322* | |
H21C | 0.0170 | 0.8863 | 0.1587 | 0.322* | |
C22 | 0.14977 (9) | 0.9931 (6) | 0.1789 (2) | 0.0620 (10) | |
H22 | 0.1669 | 1.0318 | 0.1492 | 0.074* | |
C23 | 0.16612 (12) | 0.8524 (8) | 0.2424 (2) | 0.0863 (14) | |
H23A | 0.1728 | 0.7406 | 0.2175 | 0.129* | |
H23B | 0.1502 | 0.8181 | 0.2745 | 0.129* | |
H23C | 0.1856 | 0.9096 | 0.2751 | 0.129* | |
C24 | 0.13846 (13) | 1.1697 (8) | 0.2171 (3) | 0.0933 (15) | |
H24A | 0.1208 | 1.1367 | 0.2444 | 0.140* | |
H24B | 0.1302 | 1.2623 | 0.1769 | 0.140* | |
H24C | 0.1572 | 1.2218 | 0.2543 | 0.140* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0497 (4) | 0.0512 (5) | 0.0455 (5) | −0.0090 (4) | 0.0200 (3) | 0.0033 (4) |
O1 | 0.0669 (16) | 0.0515 (15) | 0.0729 (17) | −0.0059 (12) | 0.0298 (13) | −0.0042 (12) |
O2 | 0.0690 (15) | 0.0769 (17) | 0.0408 (13) | −0.0053 (14) | 0.0158 (11) | 0.0138 (12) |
O3 | 0.0469 (12) | 0.0561 (14) | 0.0460 (12) | −0.0092 (11) | 0.0190 (9) | −0.0077 (11) |
N1 | 0.0418 (13) | 0.0387 (14) | 0.0423 (14) | −0.0033 (11) | 0.0134 (11) | −0.0022 (11) |
N2 | 0.0545 (16) | 0.0527 (17) | 0.0627 (18) | −0.0146 (14) | 0.0293 (14) | −0.0121 (14) |
C1 | 0.0505 (17) | 0.0429 (17) | 0.0389 (16) | −0.0058 (15) | 0.0113 (13) | −0.0028 (14) |
C2 | 0.064 (2) | 0.048 (2) | 0.055 (2) | −0.0134 (17) | 0.0204 (17) | 0.0034 (17) |
C3 | 0.080 (3) | 0.0377 (18) | 0.062 (2) | −0.0128 (17) | 0.0121 (19) | −0.0017 (16) |
C4 | 0.071 (2) | 0.0403 (18) | 0.053 (2) | −0.0003 (18) | 0.0104 (17) | −0.0046 (16) |
C5 | 0.0518 (18) | 0.0413 (17) | 0.0399 (16) | 0.0014 (15) | 0.0066 (14) | −0.0054 (14) |
C6 | 0.061 (2) | 0.054 (2) | 0.054 (2) | 0.0024 (17) | 0.0197 (17) | −0.0162 (17) |
C7 | 0.0548 (19) | 0.061 (2) | 0.055 (2) | −0.0024 (17) | 0.0256 (16) | −0.0080 (18) |
C8 | 0.0410 (16) | 0.0487 (18) | 0.0418 (16) | −0.0032 (15) | 0.0131 (13) | −0.0030 (15) |
C9 | 0.0404 (15) | 0.0403 (17) | 0.0383 (16) | −0.0020 (14) | 0.0073 (12) | −0.0021 (13) |
C10 | 0.0451 (17) | 0.064 (2) | 0.0452 (18) | −0.0123 (16) | 0.0155 (14) | 0.0047 (16) |
C11 | 0.058 (2) | 0.088 (3) | 0.058 (2) | −0.024 (2) | 0.0137 (17) | 0.004 (2) |
C12 | 0.071 (3) | 0.129 (4) | 0.093 (4) | −0.054 (3) | 0.012 (2) | 0.006 (3) |
C13 | 0.085 (3) | 0.162 (6) | 0.079 (3) | −0.049 (4) | 0.032 (3) | 0.023 (3) |
C14 | 0.078 (3) | 0.139 (5) | 0.060 (3) | −0.027 (3) | 0.032 (2) | 0.016 (3) |
C15 | 0.0546 (19) | 0.075 (3) | 0.050 (2) | −0.0030 (18) | 0.0212 (16) | 0.0076 (18) |
C16 | 0.077 (3) | 0.112 (4) | 0.057 (2) | −0.032 (3) | 0.005 (2) | −0.007 (2) |
C17 | 0.098 (4) | 0.190 (7) | 0.082 (4) | −0.004 (4) | −0.016 (3) | 0.006 (4) |
C18 | 0.145 (6) | 0.140 (6) | 0.111 (5) | −0.064 (5) | 0.018 (4) | −0.045 (4) |
C19 | 0.120 (5) | 0.209 (9) | 0.147 (6) | −0.070 (6) | 0.042 (4) | 0.046 (6) |
C20 | 0.170 (6) | 0.203 (7) | 0.182 (6) | −0.089 (6) | 0.037 (5) | 0.067 (6) |
C21 | 0.134 (5) | 0.271 (9) | 0.269 (8) | −0.042 (6) | 0.113 (6) | 0.003 (7) |
C22 | 0.062 (2) | 0.084 (3) | 0.0421 (19) | −0.001 (2) | 0.0153 (16) | −0.0075 (18) |
C23 | 0.088 (3) | 0.123 (4) | 0.050 (2) | 0.018 (3) | 0.017 (2) | 0.007 (3) |
C24 | 0.103 (4) | 0.107 (4) | 0.072 (3) | 0.010 (3) | 0.023 (3) | −0.022 (3) |
Geometric parameters (Å, º) top
S1—O2 | 1.421 (2) | C13—C19 | 1.542 (7) |
S1—O1 | 1.424 (3) | C14—C15 | 1.385 (5) |
S1—O3 | 1.592 (2) | C14—H14 | 0.93 |
S1—C10 | 1.773 (3) | C15—C22 | 1.510 (5) |
O3—C1 | 1.430 (4) | C16—C17 | 1.508 (7) |
N1—C8 | 1.326 (4) | C16—C18 | 1.530 (7) |
N1—C9 | 1.366 (4) | C16—H16 | 0.98 |
N2—C8 | 1.354 (4) | C17—H17A | 0.96 |
N2—H21N | 0.86 | C17—H17B | 0.96 |
N2—H22N | 0.86 | C17—H17C | 0.96 |
C1—C2 | 1.361 (4) | C18—H18A | 0.96 |
C1—C9 | 1.406 (4) | C18—H18B | 0.96 |
C2—C3 | 1.396 (5) | C18—H18C | 0.96 |
C2—H2 | 0.93 | C19—C21 | 1.502 (6) |
C3—C4 | 1.362 (5) | C19—C20 | 1.503 (6) |
C3—H3 | 0.93 | C19—H19 | 0.98 |
C4—C5 | 1.399 (5) | C20—H20A | 0.96 |
C4—H4 | 0.93 | C20—H20B | 0.96 |
C5—C6 | 1.414 (5) | C20—H20C | 0.96 |
C5—C9 | 1.426 (4) | C21—H21A | 0.96 |
C6—C7 | 1.343 (5) | C21—H21B | 0.96 |
C6—H6 | 0.93 | C21—H21C | 0.96 |
C7—C8 | 1.425 (4) | C22—C24 | 1.520 (6) |
C7—H7 | 0.93 | C22—C23 | 1.522 (6) |
C10—C11 | 1.402 (5) | C22—H22 | 0.98 |
C10—C15 | 1.426 (5) | C23—H23A | 0.96 |
C11—C12 | 1.389 (5) | C23—H23B | 0.96 |
C11—C16 | 1.536 (6) | C23—H23C | 0.96 |
C12—C13 | 1.401 (7) | C24—H24A | 0.96 |
C12—H12 | 0.93 | C24—H24B | 0.96 |
C13—C14 | 1.345 (7) | C24—H24C | 0.96 |
| | | |
O2—S1—O1 | 117.63 (16) | C10—C15—C22 | 126.3 (3) |
O2—S1—O3 | 109.20 (14) | C17—C16—C18 | 111.8 (5) |
O1—S1—O3 | 103.93 (14) | C17—C16—C11 | 109.6 (4) |
O2—S1—C10 | 111.94 (15) | C18—C16—C11 | 112.0 (4) |
O1—S1—C10 | 108.45 (15) | C17—C16—H16 | 107.8 |
O3—S1—C10 | 104.62 (14) | C18—C16—H16 | 107.8 |
C1—O3—S1 | 119.10 (19) | C11—C16—H16 | 107.8 |
C8—N1—C9 | 117.2 (3) | C16—C17—H17A | 109.5 |
C8—N2—H21N | 120.0 | C16—C17—H17B | 109.5 |
C8—N2—H22N | 120.0 | H17A—C17—H17B | 109.5 |
H21N—N2—H22N | 120.0 | C16—C17—H17C | 109.5 |
C2—C1—C9 | 122.9 (3) | H17A—C17—H17C | 109.5 |
C2—C1—O3 | 120.3 (3) | H17B—C17—H17C | 109.5 |
C9—C1—O3 | 116.7 (3) | C16—C18—H18A | 109.5 |
C1—C2—C3 | 119.7 (3) | C16—C18—H18B | 109.5 |
C1—C2—H2 | 120.2 | H18A—C18—H18B | 109.5 |
C3—C2—H2 | 120.2 | C16—C18—H18C | 109.5 |
C4—C3—C2 | 120.1 (3) | H18A—C18—H18C | 109.5 |
C4—C3—H3 | 119.9 | H18B—C18—H18C | 109.5 |
C2—C3—H3 | 119.9 | C21—C19—C20 | 118.3 (7) |
C3—C4—C5 | 120.7 (3) | C21—C19—C13 | 110.9 (6) |
C3—C4—H4 | 119.6 | C20—C19—C13 | 110.0 (6) |
C5—C4—H4 | 119.6 | C21—C19—H19 | 105.9 |
C4—C5—C6 | 122.9 (3) | C20—C19—H19 | 105.1 |
C4—C5—C9 | 120.4 (3) | C13—C19—H19 | 105.7 |
C6—C5—C9 | 116.6 (3) | C19—C20—H20A | 109.5 |
C7—C6—C5 | 120.0 (3) | C19—C20—H20B | 109.5 |
C7—C6—H6 | 120.0 | H20A—C20—H20B | 109.5 |
C5—C6—H6 | 120.0 | C19—C20—H20C | 109.5 |
C6—C7—C8 | 119.7 (3) | H20A—C20—H20C | 109.5 |
C6—C7—H7 | 120.2 | H20B—C20—H20C | 109.5 |
C8—C7—H7 | 120.2 | C19—C21—H21A | 109.5 |
N1—C8—N2 | 118.4 (3) | C19—C21—H21B | 109.5 |
N1—C8—C7 | 123.0 (3) | H21A—C21—H21B | 109.5 |
N2—C8—C7 | 118.5 (3) | C19—C21—H21C | 109.5 |
N1—C9—C1 | 120.5 (3) | H21A—C21—H21C | 109.5 |
N1—C9—C5 | 123.3 (3) | H21B—C21—H21C | 109.5 |
C1—C9—C5 | 116.1 (3) | C15—C22—C24 | 111.1 (3) |
C11—C10—C15 | 121.6 (3) | C15—C22—C23 | 111.9 (4) |
C11—C10—S1 | 122.0 (3) | C24—C22—C23 | 110.3 (4) |
C15—C10—S1 | 116.3 (3) | C15—C22—H22 | 107.8 |
C12—C11—C10 | 116.6 (4) | C24—C22—H22 | 107.8 |
C12—C11—C16 | 117.5 (4) | C23—C22—H22 | 107.8 |
C10—C11—C16 | 125.9 (3) | C22—C23—H23A | 109.5 |
C11—C12—C13 | 122.8 (4) | C22—C23—H23B | 109.5 |
C11—C12—H12 | 118.6 | H23A—C23—H23B | 109.5 |
C13—C12—H12 | 118.6 | C22—C23—H23C | 109.5 |
C14—C13—C12 | 118.1 (4) | H23A—C23—H23C | 109.5 |
C14—C13—C19 | 120.1 (5) | H23B—C23—H23C | 109.5 |
C12—C13—C19 | 121.7 (5) | C22—C24—H24A | 109.5 |
C13—C14—C15 | 123.7 (4) | C22—C24—H24B | 109.5 |
C13—C14—H14 | 118.2 | H24A—C24—H24B | 109.5 |
C15—C14—H14 | 118.2 | C22—C24—H24C | 109.5 |
C14—C15—C10 | 116.8 (4) | H24A—C24—H24C | 109.5 |
C14—C15—C22 | 116.9 (4) | H24B—C24—H24C | 109.5 |
| | | |
O2—S1—O3—C1 | −31.5 (3) | O2—S1—C10—C15 | −169.9 (3) |
O1—S1—O3—C1 | −157.8 (2) | O1—S1—C10—C15 | −38.5 (3) |
C10—S1—O3—C1 | 88.5 (2) | O3—S1—C10—C15 | 72.0 (3) |
S1—O3—C1—C2 | −72.0 (4) | C15—C10—C11—C12 | 7.6 (6) |
S1—O3—C1—C9 | 112.0 (3) | S1—C10—C11—C12 | −168.5 (4) |
C9—C1—C2—C3 | −3.0 (5) | C15—C10—C11—C16 | −170.5 (4) |
O3—C1—C2—C3 | −178.7 (3) | S1—C10—C11—C16 | 13.4 (6) |
C1—C2—C3—C4 | 1.5 (6) | C10—C11—C12—C13 | −3.6 (8) |
C2—C3—C4—C5 | 0.5 (6) | C16—C11—C12—C13 | 174.6 (6) |
C3—C4—C5—C6 | 177.6 (3) | C11—C12—C13—C14 | −1.6 (10) |
C3—C4—C5—C9 | −1.1 (5) | C11—C12—C13—C19 | 177.2 (6) |
C4—C5—C6—C7 | −178.0 (3) | C12—C13—C14—C15 | 3.1 (10) |
C9—C5—C6—C7 | 0.7 (5) | C19—C13—C14—C15 | −175.6 (6) |
C5—C6—C7—C8 | 0.8 (5) | C13—C14—C15—C10 | 0.7 (8) |
C9—N1—C8—N2 | −179.1 (3) | C13—C14—C15—C22 | −177.7 (5) |
C9—N1—C8—C7 | 1.8 (5) | C11—C10—C15—C14 | −6.2 (6) |
C6—C7—C8—N1 | −2.2 (5) | S1—C10—C15—C14 | 170.0 (4) |
C6—C7—C8—N2 | 178.8 (3) | C11—C10—C15—C22 | 171.9 (4) |
C8—N1—C9—C1 | 177.8 (3) | S1—C10—C15—C22 | −11.8 (5) |
C8—N1—C9—C5 | −0.2 (4) | C12—C11—C16—C17 | 78.2 (6) |
C2—C1—C9—N1 | −175.7 (3) | C10—C11—C16—C17 | −103.7 (5) |
O3—C1—C9—N1 | 0.1 (4) | C12—C11—C16—C18 | −46.5 (7) |
C2—C1—C9—C5 | 2.4 (5) | C10—C11—C16—C18 | 131.6 (5) |
O3—C1—C9—C5 | 178.2 (3) | C14—C13—C19—C21 | 102.5 (8) |
C4—C5—C9—N1 | 177.7 (3) | C12—C13—C19—C21 | −76.3 (10) |
C6—C5—C9—N1 | −1.0 (5) | C14—C13—C19—C20 | −124.8 (8) |
C4—C5—C9—C1 | −0.4 (4) | C12—C13—C19—C20 | 56.4 (9) |
C6—C5—C9—C1 | −179.1 (3) | C14—C15—C22—C24 | −71.7 (5) |
O2—S1—C10—C11 | 6.4 (4) | C10—C15—C22—C24 | 110.1 (5) |
O1—S1—C10—C11 | 137.8 (3) | C14—C15—C22—C23 | 52.0 (5) |
O3—S1—C10—C11 | −111.8 (3) | C10—C15—C22—C23 | −126.1 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H22N···O1i | 0.86 | 2.56 | 3.137 (4) | 125 |
N2—H21N···N1i | 0.86 | 2.26 | 3.066 (4) | 156 |
Symmetry code: (i) −x+1/2, −y+5/2, −z. |
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