The molecular packing of the title compound, C
24H
30N
2O
3S, is stabilized by a hydrogen-bonded network. Both sulfonyl O atoms are involved in intermolecular hydrogen bonds of types N—H
O and C—H
O. An intermolecular N—H
N hydrogen bond is also observed.
Supporting information
CCDC reference: 630208
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.006 Å
- Disorder in main residue
- R factor = 0.057
- wR factor = 0.152
- Data-to-parameter ratio = 13.9
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C19
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT057_ALERT_3_C Correction for Absorption Required RT(exp) ... 1.12
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.89 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C22
PLAT301_ALERT_3_C Main Residue Disorder ......................... 3.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 27.70 Deg.
C20B -C19 -C20A 1.555 1.555 1.555
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
7 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
4 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
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CAD-4-PC (Nonius, 1996); cell refinement: CAD-4-PC; 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-4-yl 2,4,6-triisopropylbenzenesulfonate
top
Crystal data top
C24H30N2O3S | Z = 2 |
Mr = 426.56 | F(000) = 456 |
Triclinic, P1 | Dx = 1.219 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54180 Å |
a = 9.431 (1) Å | Cell parameters from 25 reflections |
b = 11.015 (2) Å | θ = 4.4–24.6° |
c = 12.312 (2) Å | µ = 1.45 mm−1 |
α = 77.61 (1)° | T = 299 K |
β = 80.79 (1)° | Prism, yellow |
γ = 69.11 (1)° | 0.28 × 0.13 × 0.08 mm |
V = 1162.2 (3) Å3 | |
Data collection top
Nonius CAD-4 diffractometer | Rint = 0.027 |
Radiation source: fine-focus sealed tube | θmax = 66.9°, θmin = 3.7° |
Graphite monochromator | h = −11→1 |
w/2θ scans | k = −13→12 |
4540 measured reflections | l = −14→14 |
3997 independent reflections | 3 standard reflections every 120 min |
2461 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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.152 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0729P)2] where P = (Fo2 + 2Fc2)/3 |
3997 reflections | (Δ/σ)max = 0.012 |
287 parameters | Δρmax = 0.23 e Å−3 |
1 restraint | Δρmin = −0.33 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 | Occ. (<1) |
C1 | −0.0027 (4) | 0.7925 (3) | 0.4403 (2) | 0.0460 (8) | |
C2 | −0.0206 (4) | 0.9240 (3) | 0.3868 (2) | 0.0458 (8) | |
C3 | 0.0965 (4) | 0.9681 (4) | 0.3267 (3) | 0.0578 (9) | |
H3 | 0.1950 | 0.9085 | 0.3197 | 0.069* | |
C4 | 0.0685 (5) | 1.0965 (4) | 0.2785 (3) | 0.0697 (11) | |
H4 | 0.1468 | 1.1244 | 0.2382 | 0.084* | |
C5 | −0.0790 (5) | 1.1863 (4) | 0.2901 (3) | 0.0718 (11) | |
H5 | −0.0978 | 1.2743 | 0.2579 | 0.086* | |
C6 | −0.1966 (4) | 1.1473 (4) | 0.3481 (3) | 0.0628 (10) | |
H6 | −0.2941 | 1.2088 | 0.3541 | 0.075* | |
C7 | −0.1706 (4) | 1.0152 (3) | 0.3982 (3) | 0.0467 (8) | |
C8 | −0.2653 (4) | 0.8568 (3) | 0.5061 (2) | 0.0487 (8) | |
C9 | −0.1186 (4) | 0.7584 (3) | 0.4996 (3) | 0.0519 (9) | |
H9 | −0.1037 | 0.6721 | 0.5358 | 0.062* | |
C10 | 0.2551 (4) | 0.6691 (3) | 0.2261 (2) | 0.0425 (8) | |
C11 | 0.4038 (4) | 0.6759 (3) | 0.2159 (2) | 0.0437 (8) | |
C12 | 0.4659 (4) | 0.7119 (3) | 0.1090 (3) | 0.0490 (8) | |
H12 | 0.5647 | 0.7144 | 0.1004 | 0.059* | |
C13 | 0.3887 (4) | 0.7443 (3) | 0.0145 (3) | 0.0500 (8) | |
C14 | 0.2395 (4) | 0.7478 (3) | 0.0303 (3) | 0.0558 (9) | |
H14 | 0.1843 | 0.7741 | −0.0318 | 0.067* | |
C15 | 0.1669 (4) | 0.7140 (3) | 0.1338 (3) | 0.0481 (8) | |
C16 | 0.5023 (4) | 0.6478 (4) | 0.3113 (3) | 0.0598 (10) | |
H16 | 0.4388 | 0.6389 | 0.3817 | 0.072* | |
C17 | 0.6328 (5) | 0.5173 (4) | 0.3081 (4) | 0.0890 (14) | |
H17A | 0.6951 | 0.5226 | 0.2387 | 0.107* | |
H17B | 0.5920 | 0.4475 | 0.3146 | 0.107* | |
H17C | 0.6934 | 0.4998 | 0.3689 | 0.107* | |
C18 | 0.5615 (5) | 0.7596 (5) | 0.3085 (4) | 0.0880 (14) | |
H18A | 0.4770 | 0.8395 | 0.3141 | 0.106* | |
H18B | 0.6231 | 0.7711 | 0.2397 | 0.106* | |
H18C | 0.6217 | 0.7391 | 0.3701 | 0.106* | |
C19 | 0.4656 (4) | 0.7703 (4) | −0.1008 (3) | 0.0643 (10) | |
H15 | 0.3942 | 0.7887 | −0.1567 | 0.077* | |
C20A | 0.6053 (19) | 0.6531 (15) | −0.1218 (14) | 0.104 (5) | 0.65 |
H20A | 0.5759 | 0.5765 | −0.1144 | 0.125* | 0.65 |
H20B | 0.6764 | 0.6375 | −0.0685 | 0.125* | 0.65 |
H20C | 0.6520 | 0.6709 | −0.1959 | 0.125* | 0.65 |
C20B | 0.545 (4) | 0.647 (2) | −0.148 (3) | 0.122 (13) | 0.35 |
H20D | 0.4734 | 0.6047 | −0.1507 | 0.147* | 0.35 |
H20E | 0.6232 | 0.5890 | −0.1010 | 0.147* | 0.35 |
H20F | 0.5909 | 0.6682 | −0.2216 | 0.147* | 0.35 |
C21 | 0.5289 (6) | 0.8799 (5) | −0.1172 (4) | 0.1096 (18) | |
H21A | 0.6056 | 0.8577 | −0.0668 | 0.131* | |
H21B | 0.4486 | 0.9593 | −0.1028 | 0.131* | |
H21C | 0.5733 | 0.8932 | −0.1927 | 0.131* | |
C22 | −0.0017 (4) | 0.7308 (4) | 0.1370 (3) | 0.0658 (10) | |
H22 | −0.0418 | 0.7183 | 0.2155 | 0.079* | |
C23 | −0.0209 (6) | 0.6269 (6) | 0.0841 (5) | 0.1105 (18) | |
H23A | 0.0330 | 0.5410 | 0.1228 | 0.133* | |
H23B | 0.0193 | 0.6358 | 0.0072 | 0.133* | |
H23C | −0.1272 | 0.6378 | 0.0886 | 0.133* | |
C24 | −0.0917 (5) | 0.8694 (5) | 0.0829 (5) | 0.1127 (19) | |
H24A | −0.0526 | 0.8855 | 0.0062 | 0.135* | |
H24B | −0.0821 | 0.9325 | 0.1218 | 0.135* | |
H24C | −0.1971 | 0.8778 | 0.0865 | 0.135* | |
N1 | −0.2910 (3) | 0.9808 (3) | 0.4562 (2) | 0.0514 (7) | |
N2 | −0.3833 (4) | 0.8242 (3) | 0.5675 (3) | 0.0612 (9) | |
H21N | −0.369 (4) | 0.743 (4) | 0.587 (3) | 0.073* | |
H22N | −0.471 (5) | 0.882 (4) | 0.561 (3) | 0.073* | |
O1 | 0.1448 (2) | 0.6977 (2) | 0.43644 (17) | 0.0528 (6) | |
O2 | 0.0565 (3) | 0.5618 (2) | 0.3458 (2) | 0.0663 (7) | |
O3 | 0.3139 (3) | 0.4865 (2) | 0.4031 (2) | 0.0685 (8) | |
S1 | 0.18909 (11) | 0.59108 (8) | 0.35524 (7) | 0.0531 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0408 (19) | 0.0531 (18) | 0.0394 (16) | −0.0086 (15) | −0.0004 (14) | −0.0124 (14) |
C2 | 0.0434 (19) | 0.0557 (19) | 0.0375 (16) | −0.0142 (15) | 0.0008 (14) | −0.0139 (14) |
C3 | 0.048 (2) | 0.062 (2) | 0.065 (2) | −0.0209 (17) | 0.0093 (17) | −0.0205 (17) |
C4 | 0.068 (3) | 0.067 (2) | 0.079 (3) | −0.034 (2) | 0.012 (2) | −0.015 (2) |
C5 | 0.070 (3) | 0.058 (2) | 0.084 (3) | −0.027 (2) | −0.002 (2) | 0.002 (2) |
C6 | 0.055 (2) | 0.056 (2) | 0.072 (2) | −0.0147 (18) | −0.0065 (19) | −0.0053 (18) |
C7 | 0.043 (2) | 0.0547 (19) | 0.0440 (17) | −0.0176 (16) | −0.0018 (15) | −0.0116 (14) |
C8 | 0.042 (2) | 0.060 (2) | 0.0404 (17) | −0.0143 (16) | 0.0006 (14) | −0.0094 (15) |
C9 | 0.051 (2) | 0.0529 (19) | 0.0425 (17) | −0.0120 (16) | 0.0060 (15) | −0.0049 (14) |
C10 | 0.0393 (19) | 0.0406 (16) | 0.0427 (16) | −0.0116 (14) | 0.0036 (14) | −0.0053 (13) |
C11 | 0.0419 (19) | 0.0472 (18) | 0.0407 (16) | −0.0146 (15) | −0.0030 (14) | −0.0055 (14) |
C12 | 0.0374 (19) | 0.059 (2) | 0.0519 (19) | −0.0218 (16) | −0.0004 (15) | −0.0061 (15) |
C13 | 0.046 (2) | 0.064 (2) | 0.0403 (17) | −0.0233 (17) | −0.0009 (15) | −0.0034 (15) |
C14 | 0.051 (2) | 0.068 (2) | 0.0491 (19) | −0.0221 (18) | −0.0129 (16) | 0.0008 (16) |
C15 | 0.0371 (19) | 0.0505 (18) | 0.056 (2) | −0.0149 (15) | −0.0038 (15) | −0.0078 (15) |
C16 | 0.052 (2) | 0.077 (2) | 0.050 (2) | −0.022 (2) | −0.0083 (17) | −0.0068 (17) |
C17 | 0.061 (3) | 0.103 (3) | 0.080 (3) | −0.003 (2) | −0.020 (2) | 0.001 (2) |
C18 | 0.087 (3) | 0.124 (4) | 0.072 (3) | −0.050 (3) | −0.017 (2) | −0.025 (3) |
C19 | 0.060 (3) | 0.087 (3) | 0.046 (2) | −0.034 (2) | −0.0014 (17) | 0.0018 (18) |
C20A | 0.164 (12) | 0.095 (7) | 0.045 (7) | −0.033 (8) | 0.021 (6) | −0.031 (4) |
C20B | 0.24 (4) | 0.072 (10) | 0.051 (15) | −0.050 (16) | 0.029 (16) | −0.035 (9) |
C21 | 0.131 (5) | 0.102 (4) | 0.089 (3) | −0.057 (3) | 0.042 (3) | −0.008 (3) |
C22 | 0.042 (2) | 0.079 (3) | 0.075 (3) | −0.0243 (19) | −0.0066 (18) | −0.003 (2) |
C23 | 0.075 (3) | 0.155 (5) | 0.133 (5) | −0.070 (4) | −0.002 (3) | −0.042 (4) |
C24 | 0.050 (3) | 0.116 (4) | 0.141 (5) | −0.012 (3) | −0.021 (3) | 0.022 (3) |
N1 | 0.0391 (16) | 0.0611 (17) | 0.0502 (16) | −0.0148 (13) | −0.0007 (13) | −0.0074 (13) |
N2 | 0.0460 (19) | 0.0629 (19) | 0.0633 (19) | −0.0161 (16) | 0.0112 (16) | −0.0025 (16) |
O1 | 0.0415 (13) | 0.0592 (13) | 0.0490 (12) | −0.0070 (11) | 0.0021 (10) | −0.0130 (10) |
O2 | 0.0711 (18) | 0.0702 (16) | 0.0677 (16) | −0.0434 (14) | 0.0121 (13) | −0.0117 (12) |
O3 | 0.0678 (17) | 0.0475 (13) | 0.0646 (15) | −0.0032 (12) | 0.0071 (13) | 0.0062 (11) |
S1 | 0.0552 (6) | 0.0464 (4) | 0.0501 (5) | −0.0159 (4) | 0.0110 (4) | −0.0058 (3) |
Geometric parameters (Å, º) top
C1—C9 | 1.338 (4) | C17—H17A | 0.9600 |
C1—O1 | 1.412 (3) | C17—H17B | 0.9600 |
C1—C2 | 1.418 (4) | C17—H17C | 0.9600 |
C2—C3 | 1.404 (4) | C18—H18A | 0.9600 |
C2—C7 | 1.419 (4) | C18—H18B | 0.9600 |
C3—C4 | 1.358 (5) | C18—H18C | 0.9600 |
C3—H3 | 0.9300 | C19—C20B | 1.486 (14) |
C4—C5 | 1.396 (5) | C19—C21 | 1.492 (6) |
C4—H4 | 0.9300 | C19—C20A | 1.513 (11) |
C5—C6 | 1.370 (5) | C19—H15 | 0.9800 |
C5—H5 | 0.9300 | C20A—H20A | 0.9600 |
C6—C7 | 1.403 (4) | C20A—H20B | 0.9600 |
C6—H6 | 0.9300 | C20A—H20C | 0.9600 |
C7—N1 | 1.370 (4) | C20B—H20D | 0.9600 |
C8—N1 | 1.324 (4) | C20B—H20E | 0.9600 |
C8—N2 | 1.355 (4) | C20B—H20F | 0.9600 |
C8—C9 | 1.424 (4) | C21—H21A | 0.9600 |
C9—H9 | 0.9300 | C21—H21B | 0.9600 |
C10—C15 | 1.413 (4) | C21—H21C | 0.9600 |
C10—C11 | 1.415 (4) | C22—C23 | 1.506 (6) |
C10—S1 | 1.770 (3) | C22—C24 | 1.522 (5) |
C11—C12 | 1.389 (4) | C22—H22 | 0.9800 |
C11—C16 | 1.525 (5) | C23—H23A | 0.9600 |
C12—C13 | 1.386 (4) | C23—H23B | 0.9600 |
C12—H12 | 0.9300 | C23—H23C | 0.9600 |
C13—C14 | 1.378 (5) | C24—H24A | 0.9600 |
C13—C19 | 1.505 (4) | C24—H24B | 0.9600 |
C14—C15 | 1.390 (4) | C24—H24C | 0.9600 |
C14—H14 | 0.9300 | N2—H21N | 0.84 (4) |
C15—C22 | 1.529 (5) | N2—H22N | 0.85 (4) |
C16—C18 | 1.515 (5) | O1—S1 | 1.605 (2) |
C16—C17 | 1.526 (5) | O2—S1 | 1.425 (3) |
C16—H16 | 0.9800 | O3—S1 | 1.423 (2) |
| | | |
C9—C1—O1 | 119.6 (3) | C16—C18—H18C | 109.5 |
C9—C1—C2 | 122.1 (3) | H18A—C18—H18C | 109.5 |
O1—C1—C2 | 118.2 (3) | H18B—C18—H18C | 109.5 |
C3—C2—C7 | 119.4 (3) | C20B—C19—C21 | 123.0 (18) |
C3—C2—C1 | 125.3 (3) | C20B—C19—C13 | 112.1 (16) |
C7—C2—C1 | 115.3 (3) | C21—C19—C13 | 113.6 (3) |
C4—C3—C2 | 121.1 (3) | C20B—C19—C20A | 27.7 (16) |
C4—C3—H3 | 119.4 | C21—C19—C20A | 103.0 (9) |
C2—C3—H3 | 119.4 | C13—C19—C20A | 110.6 (8) |
C3—C4—C5 | 119.4 (4) | C20B—C19—H15 | 84.0 |
C3—C4—H4 | 120.3 | C21—C19—H15 | 109.8 |
C5—C4—H4 | 120.3 | C13—C19—H15 | 109.8 |
C6—C5—C4 | 121.4 (4) | C20A—C19—H15 | 109.8 |
C6—C5—H5 | 119.3 | C19—C20A—H20A | 109.5 |
C4—C5—H5 | 119.3 | C19—C20A—H20B | 109.5 |
C5—C6—C7 | 120.3 (3) | H20A—C20A—H20B | 109.5 |
C5—C6—H6 | 119.9 | C19—C20A—H20C | 109.5 |
C7—C6—H6 | 119.9 | H20A—C20A—H20C | 109.5 |
N1—C7—C6 | 118.4 (3) | H20B—C20A—H20C | 109.5 |
N1—C7—C2 | 123.2 (3) | C19—C20B—H20D | 109.5 |
C6—C7—C2 | 118.4 (3) | C19—C20B—H20E | 109.5 |
N1—C8—N2 | 118.1 (3) | H20D—C20B—H20E | 109.5 |
N1—C8—C9 | 122.5 (3) | C19—C20B—H20F | 109.5 |
N2—C8—C9 | 119.4 (3) | H20D—C20B—H20F | 109.5 |
C1—C9—C8 | 118.7 (3) | H20E—C20B—H20F | 109.5 |
C1—C9—H9 | 120.7 | C19—C21—H21A | 109.5 |
C8—C9—H9 | 120.7 | C19—C21—H21B | 109.5 |
C15—C10—C11 | 121.1 (3) | H21A—C21—H21B | 109.5 |
C15—C10—S1 | 121.0 (2) | C19—C21—H21C | 109.5 |
C11—C10—S1 | 117.7 (2) | H21A—C21—H21C | 109.5 |
C12—C11—C10 | 117.0 (3) | H21B—C21—H21C | 109.5 |
C12—C11—C16 | 116.8 (3) | C23—C22—C24 | 111.9 (4) |
C10—C11—C16 | 126.2 (3) | C23—C22—C15 | 110.8 (3) |
C13—C12—C11 | 123.5 (3) | C24—C22—C15 | 111.0 (3) |
C13—C12—H12 | 118.2 | C23—C22—H22 | 107.7 |
C11—C12—H12 | 118.2 | C24—C22—H22 | 107.7 |
C14—C13—C12 | 117.0 (3) | C15—C22—H22 | 107.7 |
C14—C13—C19 | 121.3 (3) | C22—C23—H23A | 109.5 |
C12—C13—C19 | 121.6 (3) | C22—C23—H23B | 109.5 |
C13—C14—C15 | 123.7 (3) | H23A—C23—H23B | 109.5 |
C13—C14—H14 | 118.2 | C22—C23—H23C | 109.5 |
C15—C14—H14 | 118.2 | H23A—C23—H23C | 109.5 |
C14—C15—C10 | 117.0 (3) | H23B—C23—H23C | 109.5 |
C14—C15—C22 | 116.7 (3) | C22—C24—H24A | 109.5 |
C10—C15—C22 | 126.3 (3) | C22—C24—H24B | 109.5 |
C18—C16—C11 | 111.8 (3) | H24A—C24—H24B | 109.5 |
C18—C16—C17 | 111.3 (3) | C22—C24—H24C | 109.5 |
C11—C16—C17 | 110.0 (3) | H24A—C24—H24C | 109.5 |
C18—C16—H16 | 107.9 | H24B—C24—H24C | 109.5 |
C11—C16—H16 | 107.9 | C8—N1—C7 | 118.3 (3) |
C17—C16—H16 | 107.9 | C8—N2—H21N | 116 (3) |
C16—C17—H17A | 109.5 | C8—N2—H22N | 116 (3) |
C16—C17—H17B | 109.5 | H21N—N2—H22N | 123 (4) |
H17A—C17—H17B | 109.5 | C1—O1—S1 | 119.8 (2) |
C16—C17—H17C | 109.5 | O3—S1—O2 | 117.72 (16) |
H17A—C17—H17C | 109.5 | O3—S1—O1 | 103.69 (14) |
H17B—C17—H17C | 109.5 | O2—S1—O1 | 108.86 (14) |
C16—C18—H18A | 109.5 | O3—S1—C10 | 109.19 (15) |
C16—C18—H18B | 109.5 | O2—S1—C10 | 111.67 (16) |
H18A—C18—H18B | 109.5 | O1—S1—C10 | 104.61 (13) |
| | | |
C9—C1—C2—C3 | 177.6 (3) | S1—C10—C15—C14 | −166.5 (2) |
O1—C1—C2—C3 | 1.9 (5) | C11—C10—C15—C22 | −170.6 (3) |
C9—C1—C2—C7 | −1.6 (5) | S1—C10—C15—C22 | 14.3 (5) |
O1—C1—C2—C7 | −177.3 (3) | C12—C11—C16—C18 | 51.9 (4) |
C7—C2—C3—C4 | −0.5 (5) | C10—C11—C16—C18 | −127.9 (4) |
C1—C2—C3—C4 | −179.7 (3) | C12—C11—C16—C17 | −72.2 (4) |
C2—C3—C4—C5 | 0.7 (6) | C10—C11—C16—C17 | 108.0 (4) |
C3—C4—C5—C6 | −0.8 (6) | C14—C13—C19—C20B | −91.3 (14) |
C4—C5—C6—C7 | 0.6 (6) | C12—C13—C19—C20B | 86.6 (14) |
C5—C6—C7—N1 | 179.4 (3) | C14—C13—C19—C21 | 123.6 (4) |
C5—C6—C7—C2 | −0.3 (5) | C12—C13—C19—C21 | −58.4 (5) |
C3—C2—C7—N1 | −179.4 (3) | C14—C13—C19—C20A | −121.1 (8) |
C1—C2—C7—N1 | −0.1 (5) | C12—C13—C19—C20A | 56.8 (8) |
C3—C2—C7—C6 | 0.3 (5) | C14—C15—C22—C23 | 72.1 (4) |
C1—C2—C7—C6 | 179.6 (3) | C10—C15—C22—C23 | −108.7 (4) |
O1—C1—C9—C8 | 177.5 (3) | C14—C15—C22—C24 | −52.8 (5) |
C2—C1—C9—C8 | 1.9 (5) | C10—C15—C22—C24 | 126.3 (4) |
N1—C8—C9—C1 | −0.3 (5) | N2—C8—N1—C7 | 177.2 (3) |
N2—C8—C9—C1 | −178.8 (3) | C9—C8—N1—C7 | −1.4 (5) |
C15—C10—C11—C12 | −8.2 (4) | C6—C7—N1—C8 | −178.1 (3) |
S1—C10—C11—C12 | 167.0 (2) | C2—C7—N1—C8 | 1.6 (5) |
C15—C10—C11—C16 | 171.6 (3) | C9—C1—O1—S1 | 79.1 (3) |
S1—C10—C11—C16 | −13.2 (4) | C2—C1—O1—S1 | −105.1 (3) |
C10—C11—C12—C13 | 1.9 (5) | C1—O1—S1—O3 | −157.9 (2) |
C16—C11—C12—C13 | −178.0 (3) | C1—O1—S1—O2 | −31.8 (3) |
C11—C12—C13—C14 | 3.9 (5) | C1—O1—S1—C10 | 87.7 (2) |
C11—C12—C13—C19 | −174.1 (3) | C15—C10—S1—O3 | 141.8 (3) |
C12—C13—C14—C15 | −3.5 (5) | C11—C10—S1—O3 | −33.5 (3) |
C19—C13—C14—C15 | 174.5 (3) | C15—C10—S1—O2 | 9.8 (3) |
C13—C14—C15—C10 | −2.5 (5) | C11—C10—S1—O2 | −165.4 (2) |
C13—C14—C15—C22 | 176.7 (3) | C15—C10—S1—O1 | −107.8 (3) |
C11—C10—C15—C14 | 8.6 (5) | C11—C10—S1—O1 | 77.0 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21N···O3i | 0.84 (4) | 2.37 (4) | 3.197 (4) | 167 (4) |
N2—H22N···N1ii | 0.85 (4) | 2.22 (4) | 3.073 (4) | 175 (4) |
C9—H9···O2i | 0.93 | 2.60 | 3.522 (4) | 174 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x−1, −y+2, −z+1. |