In the title compound, C
21H
10Br
2F
4N
2O
4S, the quinoline ring system, carrying two Br atoms, is essentially planar. The torsion angles about the N—S bonds connecting the quinoline ring to the aromatic rings are 84.0 (3) and 120.8 (3)°. Intermolecular C—H
O hydrogen bonds link molecules into a three-dimensional array.
Supporting information
CCDC reference: 613830
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.007 Å
- R factor = 0.044
- wR factor = 0.122
- Data-to-parameter ratio = 12.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.11
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT431_ALERT_2_C Short Inter HL..A Contact F2 .. O1 .. 2.93 Ang.
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 1.108
Tmax scaled 0.505 Tmin scaled 0.208
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4-PC Software (Enraf–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.
N-(5,7-Dibromo-8-quinolyl)-3,5-difluorobenzenesulfonamide
top
Crystal data top
C21H10Br2F4N2O4S2 | F(000) = 1280 |
Mr = 654.25 | Dx = 1.903 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 9.758 (1) Å | θ = 5.8–20.5° |
b = 24.091 (2) Å | µ = 6.83 mm−1 |
c = 9.851 (1) Å | T = 299 K |
β = 99.56 (1)° | Prism, light pink |
V = 2283.6 (4) Å3 | 0.30 × 0.20 × 0.10 mm |
Z = 4 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | 3269 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.047 |
Graphite monochromator | θmax = 66.9°, θmin = 3.7° |
ω/2θ scans | h = −11→1 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→28 |
Tmin = 0.188, Tmax = 0.456 | l = −11→11 |
4450 measured reflections | 3 standard reflections every 120 min |
4057 independent reflections | intensity decay: 1.0% |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0603P)2 + 3.291P] where P = (Fo2 + 2Fc2)/3 |
4057 reflections | (Δ/σ)max = 0.001 |
316 parameters | Δρmax = 0.73 e Å−3 |
0 restraints | Δρmin = −0.93 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 | 0.4927 (4) | 0.13178 (17) | 0.7813 (4) | 0.0413 (9) | |
C2 | 0.4062 (4) | 0.17712 (17) | 0.7653 (4) | 0.0460 (9) | |
C3 | 0.2722 (5) | 0.1737 (2) | 0.6877 (5) | 0.0528 (11) | |
H3 | 0.2144 | 0.2047 | 0.6779 | 0.063* | |
C4 | 0.2278 (5) | 0.1252 (2) | 0.6273 (4) | 0.0513 (10) | |
C5 | 0.3110 (4) | 0.07669 (19) | 0.6400 (4) | 0.0474 (10) | |
C6 | 0.2715 (6) | 0.0246 (2) | 0.5808 (5) | 0.0602 (12) | |
H6 | 0.1853 | 0.0205 | 0.5250 | 0.072* | |
C7 | 0.3584 (6) | −0.0194 (2) | 0.6047 (5) | 0.0676 (14) | |
H7 | 0.3335 | −0.0540 | 0.5661 | 0.081* | |
C8 | 0.4891 (6) | −0.0110 (2) | 0.6909 (5) | 0.0600 (12) | |
H8 | 0.5481 | −0.0415 | 0.7082 | 0.072* | |
C9 | 0.4448 (4) | 0.08058 (17) | 0.7213 (4) | 0.0443 (9) | |
C10 | 0.7677 (4) | 0.21637 (17) | 0.7299 (4) | 0.0450 (9) | |
C11 | 0.8431 (5) | 0.25050 (18) | 0.8284 (5) | 0.0546 (11) | |
H11 | 0.8895 | 0.2365 | 0.9114 | 0.065* | |
C12 | 0.8459 (5) | 0.3063 (2) | 0.7973 (5) | 0.0586 (12) | |
C13 | 0.7786 (5) | 0.3287 (2) | 0.6790 (6) | 0.0648 (14) | |
H13 | 0.7809 | 0.3667 | 0.6625 | 0.078* | |
C14 | 0.7067 (5) | 0.2931 (2) | 0.5844 (6) | 0.0634 (14) | |
C15 | 0.6986 (5) | 0.2362 (2) | 0.6063 (5) | 0.0540 (11) | |
H15 | 0.6490 | 0.2128 | 0.5407 | 0.065* | |
C16 | 0.7750 (4) | 0.07706 (17) | 1.0751 (4) | 0.0448 (9) | |
C17 | 0.7254 (5) | 0.02423 (18) | 1.0442 (5) | 0.0519 (10) | |
H17 | 0.6358 | 0.0182 | 0.9975 | 0.062* | |
C18 | 0.8139 (6) | −0.01898 (18) | 1.0854 (5) | 0.0572 (12) | |
C19 | 0.9450 (6) | −0.0125 (2) | 1.1547 (5) | 0.0609 (13) | |
H19 | 1.0020 | −0.0428 | 1.1823 | 0.073* | |
C20 | 0.9896 (5) | 0.0411 (2) | 1.1823 (5) | 0.0560 (11) | |
C21 | 0.9081 (5) | 0.08725 (19) | 1.1448 (4) | 0.0510 (10) | |
H21 | 0.9407 | 0.1231 | 1.1650 | 0.061* | |
N1 | 0.6334 (3) | 0.13586 (13) | 0.8532 (3) | 0.0409 (7) | |
N2 | 0.5315 (4) | 0.03532 (15) | 0.7463 (4) | 0.0527 (9) | |
O1 | 0.8845 (3) | 0.12885 (12) | 0.8493 (3) | 0.0529 (8) | |
O2 | 0.7174 (4) | 0.11836 (13) | 0.6324 (3) | 0.0564 (8) | |
O3 | 0.7397 (4) | 0.18316 (12) | 1.0750 (3) | 0.0624 (9) | |
O4 | 0.5330 (4) | 0.12307 (15) | 1.0642 (4) | 0.0631 (9) | |
F1 | 0.9212 (4) | 0.34060 (13) | 0.8914 (4) | 0.0928 (11) | |
F2 | 0.6422 (4) | 0.31312 (16) | 0.4628 (4) | 0.1037 (13) | |
F3 | 0.7680 (4) | −0.07141 (11) | 1.0545 (4) | 0.0874 (10) | |
F4 | 1.1214 (3) | 0.04933 (15) | 1.2467 (3) | 0.0830 (9) | |
Br1 | 0.45869 (5) | 0.245713 (19) | 0.85132 (6) | 0.05850 (17) | |
Br2 | 0.04437 (6) | 0.12241 (3) | 0.52693 (6) | 0.0762 (2) | |
S1 | 0.76056 (11) | 0.14484 (4) | 0.76097 (11) | 0.0430 (2) | |
S2 | 0.66461 (12) | 0.13452 (4) | 1.02820 (11) | 0.0474 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.042 (2) | 0.044 (2) | 0.038 (2) | 0.0022 (17) | 0.0061 (17) | 0.0022 (17) |
C2 | 0.049 (2) | 0.040 (2) | 0.050 (2) | 0.0039 (18) | 0.0107 (19) | 0.0007 (18) |
C3 | 0.049 (2) | 0.058 (3) | 0.049 (2) | 0.009 (2) | 0.004 (2) | 0.004 (2) |
C4 | 0.044 (2) | 0.067 (3) | 0.042 (2) | 0.001 (2) | 0.0053 (18) | 0.004 (2) |
C5 | 0.047 (2) | 0.058 (3) | 0.038 (2) | −0.006 (2) | 0.0089 (17) | 0.0011 (19) |
C6 | 0.068 (3) | 0.064 (3) | 0.047 (3) | −0.019 (3) | 0.006 (2) | −0.007 (2) |
C7 | 0.094 (4) | 0.054 (3) | 0.055 (3) | −0.016 (3) | 0.015 (3) | −0.014 (2) |
C8 | 0.082 (3) | 0.045 (2) | 0.055 (3) | 0.008 (2) | 0.017 (2) | −0.004 (2) |
C9 | 0.051 (2) | 0.042 (2) | 0.041 (2) | 0.0002 (18) | 0.0102 (18) | 0.0033 (17) |
C10 | 0.045 (2) | 0.039 (2) | 0.052 (2) | 0.0020 (17) | 0.0104 (19) | 0.0067 (18) |
C11 | 0.058 (3) | 0.047 (2) | 0.058 (3) | −0.001 (2) | 0.007 (2) | 0.006 (2) |
C12 | 0.064 (3) | 0.048 (2) | 0.065 (3) | −0.008 (2) | 0.014 (2) | 0.000 (2) |
C13 | 0.062 (3) | 0.044 (2) | 0.090 (4) | −0.003 (2) | 0.020 (3) | 0.015 (3) |
C14 | 0.053 (3) | 0.062 (3) | 0.076 (3) | 0.008 (2) | 0.013 (2) | 0.034 (3) |
C15 | 0.052 (3) | 0.053 (2) | 0.055 (3) | −0.002 (2) | 0.004 (2) | 0.012 (2) |
C16 | 0.053 (2) | 0.041 (2) | 0.040 (2) | 0.0064 (18) | 0.0062 (18) | 0.0043 (17) |
C17 | 0.065 (3) | 0.048 (2) | 0.043 (2) | −0.004 (2) | 0.009 (2) | 0.0031 (19) |
C18 | 0.088 (4) | 0.039 (2) | 0.048 (3) | 0.002 (2) | 0.022 (2) | 0.0013 (19) |
C19 | 0.086 (4) | 0.050 (3) | 0.049 (3) | 0.022 (3) | 0.019 (3) | 0.012 (2) |
C20 | 0.057 (3) | 0.066 (3) | 0.045 (2) | 0.013 (2) | 0.006 (2) | 0.009 (2) |
C21 | 0.057 (3) | 0.049 (2) | 0.045 (2) | 0.003 (2) | 0.003 (2) | 0.0022 (19) |
N1 | 0.0428 (18) | 0.0380 (17) | 0.0415 (18) | 0.0021 (14) | 0.0058 (14) | 0.0011 (14) |
N2 | 0.059 (2) | 0.046 (2) | 0.053 (2) | 0.0017 (17) | 0.0089 (17) | 0.0017 (17) |
O1 | 0.0438 (16) | 0.0439 (16) | 0.070 (2) | 0.0090 (13) | 0.0064 (14) | 0.0096 (14) |
O2 | 0.066 (2) | 0.0526 (17) | 0.0540 (18) | −0.0068 (15) | 0.0198 (15) | −0.0116 (14) |
O3 | 0.079 (2) | 0.0428 (16) | 0.058 (2) | 0.0075 (16) | −0.0094 (17) | −0.0116 (14) |
O4 | 0.0563 (19) | 0.081 (2) | 0.0554 (19) | 0.0178 (17) | 0.0200 (15) | 0.0054 (17) |
F1 | 0.124 (3) | 0.0536 (17) | 0.098 (3) | −0.0306 (18) | 0.010 (2) | −0.0098 (17) |
F2 | 0.100 (3) | 0.093 (2) | 0.105 (3) | −0.010 (2) | −0.023 (2) | 0.059 (2) |
F3 | 0.140 (3) | 0.0390 (14) | 0.084 (2) | −0.0034 (17) | 0.022 (2) | −0.0021 (14) |
F4 | 0.0626 (18) | 0.097 (2) | 0.083 (2) | 0.0171 (17) | −0.0063 (16) | 0.0157 (18) |
Br1 | 0.0614 (3) | 0.0415 (3) | 0.0715 (3) | 0.0091 (2) | 0.0076 (2) | −0.0045 (2) |
Br2 | 0.0520 (3) | 0.0997 (5) | 0.0712 (4) | −0.0011 (3) | −0.0066 (3) | 0.0009 (3) |
S1 | 0.0436 (5) | 0.0362 (5) | 0.0497 (6) | 0.0033 (4) | 0.0090 (4) | 0.0004 (4) |
S2 | 0.0540 (6) | 0.0433 (5) | 0.0437 (5) | 0.0096 (4) | 0.0047 (5) | −0.0029 (4) |
Geometric parameters (Å, º) top
C1—C2 | 1.373 (6) | C12—F1 | 1.363 (6) |
C1—C9 | 1.413 (6) | C13—C14 | 1.371 (8) |
C1—N1 | 1.440 (5) | C13—H13 | 0.9300 |
C2—C3 | 1.403 (6) | C14—F2 | 1.347 (6) |
C2—Br1 | 1.889 (4) | C14—C15 | 1.391 (7) |
C3—C4 | 1.351 (7) | C15—H15 | 0.9300 |
C3—H3 | 0.9300 | C16—C17 | 1.378 (6) |
C4—C5 | 1.416 (6) | C16—C21 | 1.387 (6) |
C4—Br2 | 1.897 (4) | C16—S2 | 1.768 (4) |
C5—C6 | 1.410 (6) | C17—C18 | 1.370 (7) |
C5—C9 | 1.417 (6) | C17—H17 | 0.9300 |
C6—C7 | 1.354 (7) | C18—C19 | 1.356 (8) |
C6—H6 | 0.9300 | C18—F3 | 1.358 (5) |
C7—C8 | 1.425 (8) | C19—C20 | 1.375 (7) |
C7—H7 | 0.9300 | C19—H19 | 0.9300 |
C8—N2 | 1.281 (6) | C20—F4 | 1.351 (6) |
C8—H8 | 0.9300 | C20—C21 | 1.381 (6) |
C9—N2 | 1.377 (5) | C21—H21 | 0.9300 |
C10—C15 | 1.376 (6) | N1—S1 | 1.670 (4) |
C10—C11 | 1.386 (6) | N1—S2 | 1.700 (3) |
C10—S1 | 1.754 (4) | O1—S1 | 1.421 (3) |
C11—C12 | 1.379 (6) | O2—S1 | 1.418 (3) |
C11—H11 | 0.9300 | O3—S2 | 1.418 (3) |
C12—C13 | 1.352 (7) | O4—S2 | 1.415 (4) |
| | | |
C2—C1—C9 | 119.5 (4) | F2—C14—C15 | 117.4 (5) |
C2—C1—N1 | 121.3 (4) | C13—C14—C15 | 123.2 (5) |
C9—C1—N1 | 119.2 (3) | C10—C15—C14 | 116.6 (5) |
C1—C2—C3 | 121.0 (4) | C10—C15—H15 | 121.7 |
C1—C2—Br1 | 121.9 (3) | C14—C15—H15 | 121.7 |
C3—C2—Br1 | 117.0 (3) | C17—C16—C21 | 122.6 (4) |
C4—C3—C2 | 119.5 (4) | C17—C16—S2 | 119.3 (3) |
C4—C3—H3 | 120.3 | C21—C16—S2 | 118.1 (3) |
C2—C3—H3 | 120.3 | C18—C17—C16 | 117.1 (4) |
C3—C4—C5 | 122.6 (4) | C18—C17—H17 | 121.5 |
C3—C4—Br2 | 117.7 (4) | C16—C17—H17 | 121.5 |
C5—C4—Br2 | 119.6 (3) | C19—C18—F3 | 118.0 (4) |
C6—C5—C4 | 125.7 (4) | C19—C18—C17 | 123.9 (4) |
C6—C5—C9 | 117.1 (4) | F3—C18—C17 | 118.1 (5) |
C4—C5—C9 | 117.1 (4) | C18—C19—C20 | 116.7 (4) |
C7—C6—C5 | 120.3 (5) | C18—C19—H19 | 121.7 |
C7—C6—H6 | 119.8 | C20—C19—H19 | 121.7 |
C5—C6—H6 | 119.8 | F4—C20—C19 | 118.4 (4) |
C6—C7—C8 | 117.7 (4) | F4—C20—C21 | 117.9 (5) |
C6—C7—H7 | 121.1 | C19—C20—C21 | 123.6 (5) |
C8—C7—H7 | 121.1 | C20—C21—C16 | 116.1 (4) |
N2—C8—C7 | 124.8 (5) | C20—C21—H21 | 121.9 |
N2—C8—H8 | 117.6 | C16—C21—H21 | 121.9 |
C7—C8—H8 | 117.6 | C1—N1—S1 | 118.4 (3) |
N2—C9—C1 | 117.8 (4) | C1—N1—S2 | 119.6 (3) |
N2—C9—C5 | 122.0 (4) | S1—N1—S2 | 122.0 (2) |
C1—C9—C5 | 120.3 (4) | C8—N2—C9 | 118.0 (4) |
C15—C10—C11 | 122.6 (4) | O2—S1—O1 | 121.4 (2) |
C15—C10—S1 | 117.9 (3) | O2—S1—N1 | 106.91 (19) |
C11—C10—S1 | 119.5 (3) | O1—S1—N1 | 105.40 (18) |
C12—C11—C10 | 116.8 (4) | O2—S1—C10 | 107.5 (2) |
C12—C11—H11 | 121.6 | O1—S1—C10 | 108.61 (19) |
C10—C11—H11 | 121.6 | N1—S1—C10 | 106.07 (18) |
C13—C12—F1 | 118.2 (4) | O4—S2—O3 | 121.4 (2) |
C13—C12—C11 | 123.8 (5) | O4—S2—N1 | 103.91 (19) |
F1—C12—C11 | 118.0 (5) | O3—S2—N1 | 108.05 (19) |
C12—C13—C14 | 117.1 (5) | O4—S2—C16 | 108.7 (2) |
C12—C13—H13 | 121.4 | O3—S2—C16 | 107.6 (2) |
C14—C13—H13 | 121.4 | N1—S2—C16 | 106.18 (18) |
F2—C14—C13 | 119.4 (5) | | |
| | | |
C9—C1—C2—C3 | −1.4 (6) | F3—C18—C19—C20 | 178.8 (4) |
N1—C1—C2—C3 | 175.9 (4) | C17—C18—C19—C20 | −0.9 (7) |
C9—C1—C2—Br1 | 176.2 (3) | C18—C19—C20—F4 | −177.6 (4) |
N1—C1—C2—Br1 | −6.5 (6) | C18—C19—C20—C21 | 0.7 (7) |
C1—C2—C3—C4 | −0.3 (7) | F4—C20—C21—C16 | 178.0 (4) |
Br1—C2—C3—C4 | −178.0 (3) | C19—C20—C21—C16 | −0.3 (7) |
C2—C3—C4—C5 | 0.6 (7) | C17—C16—C21—C20 | −0.1 (7) |
C2—C3—C4—Br2 | 178.7 (3) | S2—C16—C21—C20 | 178.5 (3) |
C3—C4—C5—C6 | 179.6 (4) | C2—C1—N1—S1 | −96.5 (4) |
Br2—C4—C5—C6 | 1.6 (6) | C9—C1—N1—S1 | 80.8 (4) |
C3—C4—C5—C9 | 0.8 (7) | C2—C1—N1—S2 | 80.6 (4) |
Br2—C4—C5—C9 | −177.2 (3) | C9—C1—N1—S2 | −102.0 (4) |
C4—C5—C6—C7 | −177.4 (5) | C7—C8—N2—C9 | 0.1 (7) |
C9—C5—C6—C7 | 1.4 (7) | C1—C9—N2—C8 | −179.3 (4) |
C5—C6—C7—C8 | 0.1 (7) | C5—C9—N2—C8 | 1.5 (6) |
C6—C7—C8—N2 | −0.9 (8) | C1—N1—S1—O2 | −30.5 (3) |
C2—C1—C9—N2 | −176.4 (4) | S2—N1—S1—O2 | 152.5 (2) |
N1—C1—C9—N2 | 6.3 (6) | C1—N1—S1—O1 | −160.9 (3) |
C2—C1—C9—C5 | 2.9 (6) | S2—N1—S1—O1 | 22.0 (3) |
N1—C1—C9—C5 | −174.5 (4) | C1—N1—S1—C10 | 84.0 (3) |
C6—C5—C9—N2 | −2.3 (6) | S2—N1—S1—C10 | −93.1 (3) |
C4—C5—C9—N2 | 176.7 (4) | C15—C10—S1—O2 | 17.5 (4) |
C6—C5—C9—C1 | 178.6 (4) | C11—C10—S1—O2 | −161.7 (4) |
C4—C5—C9—C1 | −2.5 (6) | C15—C10—S1—O1 | 150.5 (4) |
C15—C10—C11—C12 | 0.2 (7) | C11—C10—S1—O1 | −28.7 (4) |
S1—C10—C11—C12 | 179.3 (4) | C15—C10—S1—N1 | −96.6 (4) |
C10—C11—C12—C13 | 0.9 (8) | C11—C10—S1—N1 | 84.2 (4) |
C10—C11—C12—F1 | −178.9 (4) | C1—N1—S2—O4 | 6.2 (3) |
F1—C12—C13—C14 | 178.2 (5) | S1—N1—S2—O4 | −176.8 (2) |
C11—C12—C13—C14 | −1.6 (8) | C1—N1—S2—O3 | −124.0 (3) |
C12—C13—C14—F2 | −177.6 (5) | S1—N1—S2—O3 | 53.0 (3) |
C12—C13—C14—C15 | 1.2 (8) | C1—N1—S2—C16 | 120.8 (3) |
C11—C10—C15—C14 | −0.6 (7) | S1—N1—S2—C16 | −62.2 (3) |
S1—C10—C15—C14 | −179.7 (4) | C17—C16—S2—O4 | 45.2 (4) |
F2—C14—C15—C10 | 178.6 (4) | C21—C16—S2—O4 | −133.4 (4) |
C13—C14—C15—C10 | −0.2 (7) | C17—C16—S2—O3 | 178.4 (4) |
C21—C16—C17—C18 | −0.1 (7) | C21—C16—S2—O3 | −0.2 (4) |
S2—C16—C17—C18 | −178.6 (3) | C17—C16—S2—N1 | −66.1 (4) |
C16—C17—C18—C19 | 0.5 (7) | C21—C16—S2—N1 | 115.4 (4) |
C16—C17—C18—F3 | −179.1 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C19—H19···O1i | 0.93 | 2.40 | 3.264 (5) | 155 |
C7—H7···O2ii | 0.93 | 2.48 | 3.333 (6) | 152 |
Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+1, −y, −z+1. |