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In the title compound, C
22H
30FNO
3S, molecules are linked
via C—H
O interactions.
Supporting information
CCDC reference: 624959
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.003 Å
- R factor = 0.052
- wR factor = 0.135
- Data-to-parameter ratio = 19.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.14
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.08
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 28.22
From the CIF: _reflns_number_total 5040
Count of symmetry unique reflns 2934
Completeness (_total/calc) 171.78%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 2106
Fraction of Friedel pairs measured 0.718
Are heavy atom types Z>Si present yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . S
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
5 ALERT level G = General alerts; check
4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.
(-)-
N-[(3
S)-3-(4-Fluorophenyl-4-methyl)hexanoyl]bornane-10,2-sultam
top
Crystal data top
C22H30FNO3S | Dx = 1.282 Mg m−3 |
Mr = 407.53 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 8616 reflections |
a = 11.3245 (11) Å | θ = 2.3–28.2° |
b = 12.7667 (12) Å | µ = 0.18 mm−1 |
c = 14.6079 (14) Å | T = 292 K |
V = 2112.0 (3) Å3 | Block, colorless |
Z = 4 | 0.30 × 0.20 × 0.20 mm |
F(000) = 872 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 4546 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.088 |
Graphite monochromator | θmax = 28.2°, θmin = 2.1° |
φ and ω scans | h = −15→15 |
20597 measured reflections | k = −16→16 |
5040 independent reflections | l = −18→19 |
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)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.135 | w = 1/[σ2(Fo2) + (0.0809P)2 + 0.1599P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
5040 reflections | Δρmax = 0.46 e Å−3 |
257 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 1860 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.00 (8) |
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 | 0.1916 (3) | 0.0560 (2) | 0.75902 (16) | 0.0685 (7) | |
H1A | 0.2329 | 0.0053 | 0.7225 | 0.103* | |
H1B | 0.2301 | 0.1227 | 0.7539 | 0.103* | |
H1C | 0.1116 | 0.0619 | 0.7378 | 0.103* | |
C2 | 0.1181 (3) | −0.0802 (2) | 0.8659 (2) | 0.0725 (8) | |
H2A | 0.0371 | −0.0649 | 0.8516 | 0.109* | |
H2B | 0.1231 | −0.1078 | 0.9269 | 0.109* | |
H2C | 0.1479 | −0.1309 | 0.8233 | 0.109* | |
C3 | 0.19178 (18) | 0.02082 (16) | 0.85927 (15) | 0.0446 (4) | |
C4 | 0.15373 (17) | 0.10367 (15) | 0.93181 (12) | 0.0379 (4) | |
C5 | 0.1754 (2) | 0.04420 (19) | 1.02179 (16) | 0.0568 (6) | |
H5A | 0.1118 | −0.0044 | 1.0348 | 0.068* | |
H5B | 0.1844 | 0.0920 | 1.0729 | 0.068* | |
C6 | 0.2924 (2) | −0.01437 (17) | 1.00108 (18) | 0.0588 (6) | |
H6A | 0.3557 | 0.0104 | 1.0402 | 0.071* | |
H6B | 0.2833 | −0.0893 | 1.0096 | 0.071* | |
C7 | 0.31688 (19) | 0.01203 (16) | 0.90072 (18) | 0.0502 (5) | |
H7 | 0.3681 | −0.0385 | 0.8695 | 0.060* | |
C8 | 0.36080 (19) | 0.12625 (16) | 0.89566 (18) | 0.0492 (5) | |
H8A | 0.4281 | 0.1375 | 0.9356 | 0.059* | |
H8B | 0.3820 | 0.1456 | 0.8336 | 0.059* | |
C9 | 0.25183 (17) | 0.18723 (14) | 0.92891 (13) | 0.0378 (4) | |
H9 | 0.2662 | 0.2137 | 0.9909 | 0.045* | |
C10 | 0.0361 (2) | 0.1575 (2) | 0.9208 (2) | 0.0586 (6) | |
H10A | 0.0035 | 0.1755 | 0.9802 | 0.070* | |
H10B | −0.0193 | 0.1121 | 0.8894 | 0.070* | |
C11 | 0.28128 (19) | 0.36214 (15) | 0.85980 (14) | 0.0436 (4) | |
C12 | 0.2384 (2) | 0.44681 (16) | 0.79556 (15) | 0.0478 (5) | |
H12A | 0.1534 | 0.4536 | 0.8016 | 0.057* | |
H12B | 0.2553 | 0.4261 | 0.7330 | 0.057* | |
C13 | 0.29629 (19) | 0.55384 (15) | 0.81447 (14) | 0.0420 (4) | |
H13 | 0.3817 | 0.5426 | 0.8185 | 0.050* | |
C14 | 0.2738 (2) | 0.63270 (18) | 0.73547 (16) | 0.0522 (5) | |
H14 | 0.1901 | 0.6523 | 0.7361 | 0.063* | |
C15 | 0.3034 (3) | 0.5881 (2) | 0.64179 (18) | 0.0716 (7) | |
H15A | 0.3043 | 0.6435 | 0.5974 | 0.107* | |
H15B | 0.2449 | 0.5371 | 0.6249 | 0.107* | |
H15C | 0.3796 | 0.5553 | 0.6439 | 0.107* | |
C16 | 0.3478 (3) | 0.7315 (2) | 0.7518 (2) | 0.0781 (8) | |
H16A | 0.4300 | 0.7151 | 0.7447 | 0.117* | |
H16B | 0.3339 | 0.7570 | 0.8127 | 0.117* | |
H16C | 0.3258 | 0.7843 | 0.7082 | 0.117* | |
C17 | 0.25565 (18) | 0.59911 (15) | 0.90541 (14) | 0.0407 (4) | |
C18 | 0.1361 (2) | 0.61424 (19) | 0.92399 (17) | 0.0525 (5) | |
H18 | 0.0805 | 0.5918 | 0.8815 | 0.063* | |
C19 | 0.3360 (2) | 0.63260 (17) | 0.97089 (16) | 0.0490 (5) | |
H19 | 0.4162 | 0.6222 | 0.9606 | 0.059* | |
C20 | 0.0980 (2) | 0.6615 (2) | 1.00337 (18) | 0.0583 (6) | |
H20 | 0.0180 | 0.6711 | 1.0149 | 0.070* | |
C21 | 0.3003 (2) | 0.6811 (2) | 1.05118 (17) | 0.0586 (6) | |
H21 | 0.3553 | 0.7039 | 1.0940 | 0.070* | |
C22 | 0.1830 (2) | 0.69424 (19) | 1.06563 (17) | 0.0582 (6) | |
F1 | 0.14542 (18) | 0.74158 (17) | 1.14378 (12) | 0.0892 (5) | |
N1 | 0.21036 (14) | 0.27366 (13) | 0.87017 (11) | 0.0384 (3) | |
O1 | 0.03626 (15) | 0.25901 (18) | 0.76051 (13) | 0.0745 (6) | |
O2 | 0.0127 (2) | 0.36272 (18) | 0.89918 (19) | 0.0949 (8) | |
O3 | 0.37576 (17) | 0.36433 (13) | 0.89679 (14) | 0.0674 (5) | |
S1 | 0.06260 (4) | 0.27339 (5) | 0.85509 (4) | 0.05335 (17) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0924 (19) | 0.0718 (17) | 0.0412 (11) | 0.0021 (14) | −0.0069 (12) | −0.0149 (12) |
C2 | 0.0809 (18) | 0.0497 (14) | 0.0869 (19) | −0.0217 (12) | −0.0210 (16) | −0.0071 (13) |
C3 | 0.0500 (11) | 0.0380 (10) | 0.0458 (10) | −0.0034 (8) | −0.0058 (9) | −0.0069 (8) |
C4 | 0.0402 (9) | 0.0394 (9) | 0.0340 (8) | −0.0005 (8) | 0.0031 (7) | 0.0036 (7) |
C5 | 0.0811 (16) | 0.0468 (11) | 0.0425 (11) | −0.0049 (11) | 0.0020 (10) | 0.0117 (9) |
C6 | 0.0657 (14) | 0.0402 (11) | 0.0705 (16) | −0.0039 (10) | −0.0217 (12) | 0.0182 (11) |
C7 | 0.0469 (11) | 0.0335 (10) | 0.0702 (14) | 0.0052 (8) | −0.0021 (10) | −0.0009 (9) |
C8 | 0.0381 (9) | 0.0399 (10) | 0.0694 (14) | −0.0001 (8) | −0.0050 (9) | 0.0081 (10) |
C9 | 0.0456 (9) | 0.0307 (8) | 0.0371 (8) | −0.0003 (7) | −0.0070 (8) | 0.0025 (7) |
C10 | 0.0432 (11) | 0.0570 (13) | 0.0756 (15) | 0.0046 (10) | 0.0177 (11) | 0.0255 (12) |
C11 | 0.0532 (11) | 0.0327 (9) | 0.0448 (10) | −0.0004 (8) | −0.0089 (9) | 0.0009 (8) |
C12 | 0.0604 (13) | 0.0355 (10) | 0.0476 (10) | −0.0014 (9) | −0.0119 (9) | 0.0045 (9) |
C13 | 0.0457 (10) | 0.0344 (9) | 0.0457 (10) | 0.0002 (8) | −0.0028 (8) | 0.0054 (8) |
C14 | 0.0611 (13) | 0.0395 (11) | 0.0560 (12) | 0.0046 (9) | 0.0060 (10) | 0.0124 (9) |
C15 | 0.101 (2) | 0.0616 (15) | 0.0527 (13) | −0.0047 (14) | 0.0053 (14) | 0.0113 (12) |
C16 | 0.118 (2) | 0.0424 (12) | 0.0741 (18) | −0.0158 (16) | 0.0139 (17) | 0.0085 (12) |
C17 | 0.0461 (10) | 0.0300 (8) | 0.0460 (10) | −0.0001 (7) | −0.0048 (8) | 0.0070 (8) |
C18 | 0.0466 (11) | 0.0541 (12) | 0.0567 (13) | −0.0038 (10) | −0.0078 (10) | 0.0002 (10) |
C19 | 0.0458 (10) | 0.0445 (11) | 0.0566 (12) | −0.0003 (9) | −0.0090 (9) | 0.0037 (9) |
C20 | 0.0512 (12) | 0.0574 (13) | 0.0663 (15) | 0.0043 (10) | 0.0052 (11) | 0.0047 (12) |
C21 | 0.0695 (15) | 0.0524 (12) | 0.0538 (13) | −0.0065 (11) | −0.0160 (11) | −0.0020 (10) |
C22 | 0.0772 (16) | 0.0474 (12) | 0.0502 (12) | 0.0044 (11) | 0.0024 (11) | 0.0035 (10) |
F1 | 0.1095 (14) | 0.0925 (13) | 0.0657 (10) | 0.0084 (11) | 0.0124 (9) | −0.0213 (9) |
N1 | 0.0377 (7) | 0.0340 (7) | 0.0434 (8) | 0.0047 (6) | −0.0046 (6) | 0.0039 (7) |
O1 | 0.0561 (10) | 0.0887 (14) | 0.0788 (12) | −0.0065 (9) | −0.0289 (9) | 0.0313 (11) |
O2 | 0.0819 (14) | 0.0706 (13) | 0.132 (2) | 0.0370 (11) | 0.0434 (14) | 0.0205 (13) |
O3 | 0.0669 (11) | 0.0434 (8) | 0.0918 (13) | −0.0120 (8) | −0.0369 (10) | 0.0159 (9) |
S1 | 0.0363 (2) | 0.0531 (3) | 0.0706 (4) | 0.0110 (2) | 0.0071 (2) | 0.0184 (3) |
Geometric parameters (Å, º) top
C1—C3 | 1.532 (3) | C11—C12 | 1.512 (3) |
C1—H1A | 0.9600 | C12—C13 | 1.541 (3) |
C1—H1B | 0.9600 | C12—H12A | 0.9700 |
C1—H1C | 0.9600 | C12—H12B | 0.9700 |
C2—C3 | 1.539 (3) | C13—C17 | 1.520 (3) |
C2—H2A | 0.9600 | C13—C14 | 1.553 (3) |
C2—H2B | 0.9600 | C13—H13 | 0.9800 |
C2—H2C | 0.9600 | C14—C15 | 1.520 (4) |
C3—C7 | 1.545 (3) | C14—C16 | 1.533 (4) |
C3—C4 | 1.558 (3) | C14—H14 | 0.9800 |
C4—C10 | 1.508 (3) | C15—H15A | 0.9600 |
C4—C5 | 1.538 (3) | C15—H15B | 0.9600 |
C4—C9 | 1.541 (3) | C15—H15C | 0.9600 |
C5—C6 | 1.551 (4) | C16—H16A | 0.9600 |
C5—H5A | 0.9700 | C16—H16B | 0.9600 |
C5—H5B | 0.9700 | C16—H16C | 0.9600 |
C6—C7 | 1.530 (4) | C17—C19 | 1.388 (3) |
C6—H6A | 0.9700 | C17—C18 | 1.394 (3) |
C6—H6B | 0.9700 | C18—C20 | 1.376 (4) |
C7—C8 | 1.542 (3) | C18—H18 | 0.9300 |
C7—H7 | 0.9800 | C19—C21 | 1.386 (4) |
C8—C9 | 1.538 (3) | C19—H19 | 0.9300 |
C8—H8A | 0.9700 | C20—C22 | 1.389 (4) |
C8—H8B | 0.9700 | C20—H20 | 0.9300 |
C9—N1 | 1.475 (2) | C21—C22 | 1.355 (4) |
C9—H9 | 0.9800 | C21—H21 | 0.9300 |
C10—S1 | 1.789 (2) | C22—F1 | 1.360 (3) |
C10—H10A | 0.9700 | N1—S1 | 1.6878 (16) |
C10—H10B | 0.9700 | O1—S1 | 1.425 (2) |
C11—O3 | 1.199 (3) | O2—S1 | 1.427 (2) |
C11—N1 | 1.394 (3) | | |
| | | |
C3—C1—H1A | 109.5 | O3—C11—N1 | 118.95 (18) |
C3—C1—H1B | 109.5 | O3—C11—C12 | 123.4 (2) |
H1A—C1—H1B | 109.5 | N1—C11—C12 | 117.49 (17) |
C3—C1—H1C | 109.5 | C11—C12—C13 | 112.71 (17) |
H1A—C1—H1C | 109.5 | C11—C12—H12A | 109.1 |
H1B—C1—H1C | 109.5 | C13—C12—H12A | 109.1 |
C3—C2—H2A | 109.5 | C11—C12—H12B | 109.1 |
C3—C2—H2B | 109.5 | C13—C12—H12B | 109.1 |
H2A—C2—H2B | 109.5 | H12A—C12—H12B | 107.8 |
C3—C2—H2C | 109.5 | C17—C13—C12 | 111.41 (17) |
H2A—C2—H2C | 109.5 | C17—C13—C14 | 110.69 (17) |
H2B—C2—H2C | 109.5 | C12—C13—C14 | 111.84 (17) |
C1—C3—C2 | 107.8 (2) | C17—C13—H13 | 107.6 |
C1—C3—C7 | 113.4 (2) | C12—C13—H13 | 107.6 |
C2—C3—C7 | 114.32 (19) | C14—C13—H13 | 107.6 |
C1—C3—C4 | 116.81 (19) | C15—C14—C16 | 109.2 (2) |
C2—C3—C4 | 112.09 (19) | C15—C14—C13 | 112.95 (19) |
C7—C3—C4 | 92.08 (15) | C16—C14—C13 | 109.2 (2) |
C10—C4—C5 | 117.21 (18) | C15—C14—H14 | 108.5 |
C10—C4—C9 | 108.56 (17) | C16—C14—H14 | 108.5 |
C5—C4—C9 | 104.49 (16) | C13—C14—H14 | 108.5 |
C10—C4—C3 | 118.79 (19) | C14—C15—H15A | 109.5 |
C5—C4—C3 | 101.65 (16) | C14—C15—H15B | 109.5 |
C9—C4—C3 | 104.59 (15) | H15A—C15—H15B | 109.5 |
C4—C5—C6 | 101.99 (18) | C14—C15—H15C | 109.5 |
C4—C5—H5A | 111.4 | H15A—C15—H15C | 109.5 |
C6—C5—H5A | 111.4 | H15B—C15—H15C | 109.5 |
C4—C5—H5B | 111.4 | C14—C16—H16A | 109.5 |
C6—C5—H5B | 111.4 | C14—C16—H16B | 109.5 |
H5A—C5—H5B | 109.2 | H16A—C16—H16B | 109.5 |
C7—C6—C5 | 103.61 (17) | C14—C16—H16C | 109.5 |
C7—C6—H6A | 111.0 | H16A—C16—H16C | 109.5 |
C5—C6—H6A | 111.0 | H16B—C16—H16C | 109.5 |
C7—C6—H6B | 111.0 | C19—C17—C18 | 117.4 (2) |
C5—C6—H6B | 111.0 | C19—C17—C13 | 121.41 (19) |
H6A—C6—H6B | 109.0 | C18—C17—C13 | 121.13 (18) |
C6—C7—C8 | 108.2 (2) | C20—C18—C17 | 122.0 (2) |
C6—C7—C3 | 103.05 (19) | C20—C18—H18 | 119.0 |
C8—C7—C3 | 102.02 (17) | C17—C18—H18 | 119.0 |
C6—C7—H7 | 114.1 | C21—C19—C17 | 122.0 (2) |
C8—C7—H7 | 114.1 | C21—C19—H19 | 119.0 |
C3—C7—H7 | 114.1 | C17—C19—H19 | 119.0 |
C9—C8—C7 | 101.81 (17) | C18—C20—C22 | 117.8 (2) |
C9—C8—H8A | 111.4 | C18—C20—H20 | 121.1 |
C7—C8—H8A | 111.4 | C22—C20—H20 | 121.1 |
C9—C8—H8B | 111.4 | C22—C21—C19 | 118.2 (2) |
C7—C8—H8B | 111.4 | C22—C21—H21 | 120.9 |
H8A—C8—H8B | 109.3 | C19—C21—H21 | 120.9 |
N1—C9—C8 | 116.78 (17) | C21—C22—F1 | 119.5 (2) |
N1—C9—C4 | 107.73 (15) | C21—C22—C20 | 122.7 (2) |
C8—C9—C4 | 103.69 (15) | F1—C22—C20 | 117.8 (2) |
N1—C9—H9 | 109.4 | C11—N1—C9 | 119.08 (15) |
C8—C9—H9 | 109.4 | C11—N1—S1 | 123.96 (13) |
C4—C9—H9 | 109.4 | C9—N1—S1 | 112.96 (12) |
C4—C10—S1 | 106.61 (14) | O1—S1—O2 | 117.24 (15) |
C4—C10—H10A | 110.4 | O1—S1—N1 | 109.52 (10) |
S1—C10—H10A | 110.4 | O2—S1—N1 | 109.41 (14) |
C4—C10—H10B | 110.4 | O1—S1—C10 | 112.26 (14) |
S1—C10—H10B | 110.4 | O2—S1—C10 | 110.62 (12) |
H10A—C10—H10B | 108.6 | N1—S1—C10 | 95.63 (10) |
| | | |
C1—C3—C4—C10 | 54.5 (3) | C11—C12—C13—C14 | 166.99 (18) |
C2—C3—C4—C10 | −70.5 (2) | C17—C13—C14—C15 | −175.2 (2) |
C7—C3—C4—C10 | 172.17 (18) | C12—C13—C14—C15 | −50.4 (3) |
C1—C3—C4—C5 | −175.2 (2) | C17—C13—C14—C16 | 63.1 (3) |
C2—C3—C4—C5 | 59.8 (2) | C12—C13—C14—C16 | −172.0 (2) |
C7—C3—C4—C5 | −57.58 (18) | C12—C13—C17—C19 | 127.7 (2) |
C1—C3—C4—C9 | −66.7 (2) | C14—C13—C17—C19 | −107.2 (2) |
C2—C3—C4—C9 | 168.30 (18) | C12—C13—C17—C18 | −56.1 (2) |
C7—C3—C4—C9 | 50.94 (18) | C14—C13—C17—C18 | 69.0 (3) |
C10—C4—C5—C6 | 170.8 (2) | C19—C17—C18—C20 | 0.7 (3) |
C9—C4—C5—C6 | −69.0 (2) | C13—C17—C18—C20 | −175.6 (2) |
C3—C4—C5—C6 | 39.6 (2) | C18—C17—C19—C21 | −1.2 (3) |
C4—C5—C6—C7 | −4.3 (2) | C13—C17—C19—C21 | 175.2 (2) |
C5—C6—C7—C8 | 74.6 (2) | C17—C18—C20—C22 | 0.0 (4) |
C5—C6—C7—C3 | −32.9 (2) | C17—C19—C21—C22 | 0.9 (4) |
C1—C3—C7—C6 | 175.3 (2) | C19—C21—C22—F1 | −180.0 (2) |
C2—C3—C7—C6 | −60.6 (2) | C19—C21—C22—C20 | −0.2 (4) |
C4—C3—C7—C6 | 54.85 (18) | C18—C20—C22—C21 | −0.3 (4) |
C1—C3—C7—C8 | 63.2 (2) | C18—C20—C22—F1 | 179.5 (2) |
C2—C3—C7—C8 | −172.8 (2) | O3—C11—N1—C9 | 2.2 (3) |
C4—C3—C7—C8 | −57.33 (19) | C12—C11—N1—C9 | 177.20 (17) |
C6—C7—C8—C9 | −64.5 (2) | O3—C11—N1—S1 | 158.06 (19) |
C3—C7—C8—C9 | 43.8 (2) | C12—C11—N1—S1 | −26.9 (3) |
C7—C8—C9—N1 | −128.20 (19) | C8—C9—N1—C11 | −67.0 (2) |
C7—C8—C9—C4 | −9.9 (2) | C4—C9—N1—C11 | 176.95 (17) |
C10—C4—C9—N1 | −30.1 (2) | C8—C9—N1—S1 | 134.64 (15) |
C5—C4—C9—N1 | −155.86 (16) | C4—C9—N1—S1 | 18.55 (18) |
C3—C4—C9—N1 | 97.71 (17) | C11—N1—S1—O1 | 85.08 (19) |
C10—C4—C9—C8 | −154.45 (19) | C9—N1—S1—O1 | −117.74 (15) |
C5—C4—C9—C8 | 79.7 (2) | C11—N1—S1—O2 | −44.70 (19) |
C3—C4—C9—C8 | −26.7 (2) | C9—N1—S1—O2 | 112.48 (16) |
C5—C4—C10—S1 | 146.37 (17) | C11—N1—S1—C10 | −158.90 (18) |
C9—C4—C10—S1 | 28.4 (2) | C9—N1—S1—C10 | −1.72 (16) |
C3—C4—C10—S1 | −90.8 (2) | C4—C10—S1—O1 | 97.8 (2) |
O3—C11—C12—C13 | −25.8 (3) | C4—C10—S1—O2 | −129.1 (2) |
N1—C11—C12—C13 | 159.43 (18) | C4—C10—S1—N1 | −15.94 (19) |
C11—C12—C13—C17 | −68.5 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1B···N1 | 0.96 | 2.58 | 3.226 (3) | 125 |
C12—H12A···O2 | 0.97 | 2.43 | 3.158 (3) | 131 |
C10—H10A···O3i | 0.97 | 2.36 | 3.236 (3) | 150 |
C8—H8A···O2ii | 0.97 | 2.60 | 3.458 (3) | 148 |
C6—H6A···O2ii | 0.97 | 2.56 | 3.477 (3) | 157 |
Symmetry codes: (i) x−1/2, −y+1/2, −z+2; (ii) x+1/2, −y+1/2, −z+2. |
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