In the title compound, C
28H
24N
2O
4S, the indole ring system is planar, but the pyrrolidine and thiazole rings adopt an envelope and a twist conformation, respectively. The indole system makes a dihedral angle of 55.7 (1)° with the methoxyphenyl ring. The molecular packing in the crystal structure is stabilized by C—H
O and N—H
O hydrogen bonds.
Supporting information
CCDC reference: 274339
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.002 Å
- R factor = 0.047
- wR factor = 0.126
- Data-to-parameter ratio = 16.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 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
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003).
7'-(4-Methoxyphenyl)-chroman-3-spiro-6'-hexahydro-1
H-pyrrolo[1,2-
c]thiazole- 5'-spiro-3''-1''
H-indole-4,2''(3''H)-dione
top
Crystal data top
C28H24N2O4S | F(000) = 1016 |
Mr = 484.55 | Dx = 1.371 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6089 reflections |
a = 9.5561 (6) Å | θ = 2.5–27.8° |
b = 16.1035 (11) Å | µ = 0.18 mm−1 |
c = 15.2631 (10) Å | T = 273 K |
β = 91.213 (10)° | Block, colourless |
V = 2348.3 (3) Å3 | 0.26 × 0.24 × 0.18 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 4396 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.018 |
Graphite monochromator | θmax = 28.0°, θmin = 1.8° |
ω scans | h = −10→11 |
14171 measured reflections | k = −20→21 |
5134 independent reflections | l = −19→20 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0726P)2 + 0.5516P] where P = (Fo2 + 2Fc2)/3 |
5134 reflections | (Δ/σ)max < 0.001 |
317 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.21 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 | 0.56744 (5) | 0.12022 (3) | −0.08305 (3) | 0.04361 (14) | |
O2 | 0.04618 (13) | 0.12139 (7) | 0.20431 (8) | 0.0465 (3) | |
N1 | 0.36785 (13) | 0.16341 (7) | 0.01790 (8) | 0.0328 (3) | |
C3 | 0.43513 (16) | 0.16285 (9) | 0.16237 (10) | 0.0327 (3) | |
H3 | 0.4773 | 0.2181 | 0.1572 | 0.039* | |
C7 | 0.49524 (17) | 0.12477 (9) | 0.24588 (10) | 0.0344 (3) | |
N2 | 0.01777 (15) | 0.12082 (8) | −0.00367 (9) | 0.0404 (3) | |
H2 | −0.0508 | 0.0894 | −0.0199 | 0.048* | |
O4 | 0.16687 (13) | 0.02012 (6) | 0.04915 (8) | 0.0443 (3) | |
O3 | 0.31578 (13) | 0.31680 (7) | 0.20708 (8) | 0.0472 (3) | |
C21 | 0.23219 (17) | 0.26100 (9) | 0.19645 (10) | 0.0359 (3) | |
C28 | 0.14544 (17) | 0.23923 (9) | 0.01771 (9) | 0.0347 (3) | |
O1 | 0.66593 (17) | 0.02539 (9) | 0.47656 (9) | 0.0617 (4) | |
C4 | 0.46223 (16) | 0.11786 (9) | 0.07671 (9) | 0.0330 (3) | |
H4 | 0.4347 | 0.0594 | 0.0805 | 0.040* | |
C2 | 0.27354 (16) | 0.17582 (8) | 0.15966 (9) | 0.0323 (3) | |
C14 | 0.19497 (18) | 0.11365 (10) | 0.21626 (11) | 0.0391 (4) | |
H14A | 0.2232 | 0.0577 | 0.2011 | 0.047* | |
H14B | 0.2198 | 0.1229 | 0.2774 | 0.047* | |
C22 | 0.13544 (17) | 0.09311 (9) | 0.03630 (10) | 0.0357 (3) | |
C6 | 0.60442 (18) | 0.12656 (10) | 0.03482 (11) | 0.0422 (4) | |
H6A | 0.6667 | 0.0822 | 0.0537 | 0.051* | |
H6B | 0.6471 | 0.1794 | 0.0500 | 0.051* | |
C1 | 0.23109 (16) | 0.16961 (8) | 0.05781 (9) | 0.0319 (3) | |
C23 | 0.02018 (17) | 0.20747 (10) | −0.01584 (10) | 0.0368 (3) | |
C20 | 0.08286 (19) | 0.26888 (11) | 0.21687 (11) | 0.0429 (4) | |
C5 | 0.37914 (19) | 0.13225 (10) | −0.07051 (10) | 0.0410 (4) | |
H5A | 0.3407 | 0.1715 | −0.1128 | 0.049* | |
H5B | 0.3312 | 0.0795 | −0.0774 | 0.049* | |
C27 | 0.17686 (19) | 0.32234 (10) | 0.00765 (11) | 0.0414 (4) | |
H27 | 0.2618 | 0.3437 | 0.0281 | 0.050* | |
C15 | −0.00413 (19) | 0.19972 (12) | 0.21405 (10) | 0.0446 (4) | |
C11 | 0.5560 (2) | 0.14161 (11) | 0.39999 (11) | 0.0468 (4) | |
H11 | 0.5569 | 0.1746 | 0.4500 | 0.056* | |
C10 | 0.60880 (19) | 0.06227 (11) | 0.40329 (11) | 0.0437 (4) | |
C12 | 0.50146 (19) | 0.17199 (10) | 0.32158 (11) | 0.0440 (4) | |
H12 | 0.4677 | 0.2262 | 0.3197 | 0.053* | |
C24 | −0.07878 (19) | 0.25713 (12) | −0.05644 (11) | 0.0471 (4) | |
H24 | −0.1634 | 0.2356 | −0.0774 | 0.057* | |
C8 | 0.54972 (19) | 0.04487 (10) | 0.25091 (11) | 0.0427 (4) | |
H8 | 0.5472 | 0.0113 | 0.2013 | 0.051* | |
C25 | −0.0466 (2) | 0.34081 (12) | −0.06464 (12) | 0.0516 (5) | |
H25 | −0.1113 | 0.3760 | −0.0918 | 0.062* | |
C9 | 0.6075 (2) | 0.01440 (10) | 0.32813 (12) | 0.0490 (4) | |
H9 | 0.6459 | −0.0387 | 0.3296 | 0.059* | |
C26 | 0.0786 (2) | 0.37323 (11) | −0.03376 (12) | 0.0489 (4) | |
H26 | 0.0972 | 0.4295 | −0.0407 | 0.059* | |
C16 | −0.1485 (2) | 0.20856 (15) | 0.22122 (12) | 0.0576 (5) | |
H16 | −0.2067 | 0.1623 | 0.2177 | 0.069* | |
C19 | 0.0235 (2) | 0.34715 (13) | 0.23146 (13) | 0.0561 (5) | |
H19 | 0.0804 | 0.3939 | 0.2354 | 0.067* | |
C18 | −0.1193 (3) | 0.35483 (16) | 0.23999 (15) | 0.0687 (6) | |
H18 | −0.1586 | 0.4067 | 0.2501 | 0.082* | |
C13 | 0.6682 (3) | 0.07218 (16) | 0.55563 (13) | 0.0722 (6) | |
H13A | 0.7280 | 0.1196 | 0.5492 | 0.108* | |
H13B | 0.7031 | 0.0381 | 0.6029 | 0.108* | |
H13C | 0.5751 | 0.0904 | 0.5682 | 0.108* | |
C17 | −0.2036 (2) | 0.28584 (18) | 0.23349 (14) | 0.0694 (6) | |
H17 | −0.3000 | 0.2919 | 0.2375 | 0.083* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0448 (3) | 0.0425 (2) | 0.0439 (2) | 0.00119 (17) | 0.00911 (18) | −0.00049 (15) |
O2 | 0.0368 (7) | 0.0507 (7) | 0.0520 (7) | −0.0111 (5) | 0.0037 (5) | −0.0013 (5) |
N1 | 0.0298 (7) | 0.0319 (6) | 0.0366 (6) | −0.0011 (5) | −0.0011 (5) | 0.0005 (5) |
C3 | 0.0319 (9) | 0.0270 (6) | 0.0390 (7) | −0.0014 (5) | −0.0017 (6) | −0.0019 (5) |
C7 | 0.0297 (9) | 0.0331 (7) | 0.0401 (8) | −0.0004 (6) | −0.0036 (6) | −0.0032 (6) |
N2 | 0.0321 (8) | 0.0401 (7) | 0.0486 (7) | −0.0070 (5) | −0.0069 (6) | −0.0049 (5) |
O4 | 0.0399 (7) | 0.0307 (5) | 0.0622 (7) | −0.0053 (5) | −0.0040 (5) | −0.0041 (5) |
O3 | 0.0471 (8) | 0.0308 (5) | 0.0634 (7) | −0.0018 (5) | −0.0034 (6) | −0.0067 (5) |
C21 | 0.0392 (9) | 0.0322 (7) | 0.0363 (7) | 0.0024 (6) | −0.0024 (6) | −0.0012 (5) |
C28 | 0.0330 (9) | 0.0346 (7) | 0.0363 (7) | 0.0012 (6) | −0.0018 (6) | −0.0017 (6) |
O1 | 0.0740 (10) | 0.0618 (8) | 0.0484 (7) | 0.0049 (7) | −0.0167 (7) | 0.0078 (6) |
C4 | 0.0318 (9) | 0.0293 (7) | 0.0379 (7) | −0.0003 (6) | −0.0015 (6) | −0.0004 (5) |
C2 | 0.0313 (9) | 0.0286 (6) | 0.0370 (7) | −0.0019 (6) | −0.0027 (6) | −0.0006 (5) |
C14 | 0.0356 (10) | 0.0384 (8) | 0.0434 (8) | −0.0054 (6) | −0.0003 (7) | 0.0044 (6) |
C22 | 0.0322 (9) | 0.0351 (7) | 0.0399 (8) | −0.0059 (6) | 0.0003 (6) | −0.0050 (6) |
C6 | 0.0360 (10) | 0.0453 (9) | 0.0455 (9) | 0.0023 (7) | 0.0016 (7) | −0.0024 (7) |
C1 | 0.0300 (9) | 0.0272 (6) | 0.0384 (7) | −0.0033 (5) | −0.0033 (6) | −0.0016 (5) |
C23 | 0.0331 (9) | 0.0418 (8) | 0.0355 (7) | −0.0004 (6) | −0.0002 (6) | −0.0024 (6) |
C20 | 0.0397 (10) | 0.0497 (9) | 0.0392 (8) | 0.0071 (7) | 0.0015 (7) | −0.0024 (7) |
C5 | 0.0433 (10) | 0.0419 (8) | 0.0378 (8) | −0.0055 (7) | 0.0005 (7) | 0.0006 (6) |
C27 | 0.0413 (10) | 0.0365 (8) | 0.0462 (9) | −0.0013 (7) | −0.0025 (7) | 0.0010 (6) |
C15 | 0.0376 (10) | 0.0613 (10) | 0.0349 (8) | −0.0002 (8) | 0.0022 (6) | −0.0014 (7) |
C11 | 0.0506 (11) | 0.0477 (9) | 0.0416 (8) | 0.0015 (8) | −0.0080 (7) | −0.0102 (7) |
C10 | 0.0393 (10) | 0.0472 (9) | 0.0443 (9) | −0.0025 (7) | −0.0072 (7) | 0.0040 (7) |
C12 | 0.0468 (11) | 0.0369 (8) | 0.0478 (9) | 0.0065 (7) | −0.0087 (7) | −0.0088 (6) |
C24 | 0.0363 (10) | 0.0600 (10) | 0.0448 (9) | 0.0038 (8) | −0.0056 (7) | 0.0013 (7) |
C8 | 0.0505 (11) | 0.0346 (8) | 0.0427 (8) | 0.0048 (7) | −0.0036 (7) | −0.0057 (6) |
C25 | 0.0473 (12) | 0.0560 (10) | 0.0511 (10) | 0.0157 (8) | −0.0047 (8) | 0.0093 (8) |
C9 | 0.0575 (12) | 0.0367 (8) | 0.0523 (10) | 0.0096 (8) | −0.0062 (8) | −0.0002 (7) |
C26 | 0.0542 (12) | 0.0394 (8) | 0.0532 (10) | 0.0074 (8) | 0.0015 (8) | 0.0071 (7) |
C16 | 0.0383 (12) | 0.0889 (15) | 0.0458 (10) | −0.0037 (10) | 0.0035 (8) | −0.0016 (9) |
C19 | 0.0563 (13) | 0.0562 (11) | 0.0559 (11) | 0.0159 (9) | 0.0055 (9) | −0.0032 (8) |
C18 | 0.0600 (15) | 0.0817 (15) | 0.0647 (13) | 0.0331 (12) | 0.0087 (10) | −0.0026 (11) |
C13 | 0.0853 (17) | 0.0861 (16) | 0.0445 (10) | −0.0101 (13) | −0.0136 (10) | 0.0052 (10) |
C17 | 0.0408 (13) | 0.1097 (19) | 0.0577 (12) | 0.0178 (12) | 0.0056 (9) | −0.0006 (12) |
Geometric parameters (Å, º) top
S1—C5 | 1.824 (2) | C6—H6B | 0.9700 |
S1—C6 | 1.829 (2) | C23—C24 | 1.376 (2) |
O2—C15 | 1.359 (2) | C20—C15 | 1.390 (3) |
O2—C14 | 1.435 (2) | C20—C19 | 1.402 (2) |
N1—C5 | 1.446 (2) | C5—H5A | 0.9700 |
N1—C1 | 1.457 (2) | C5—H5B | 0.9700 |
N1—C4 | 1.4570 (19) | C27—C26 | 1.389 (2) |
C3—C7 | 1.516 (2) | C27—H27 | 0.9300 |
C3—C4 | 1.522 (2) | C15—C16 | 1.393 (3) |
C3—C2 | 1.558 (2) | C11—C10 | 1.374 (2) |
C3—H3 | 0.9800 | C11—C12 | 1.385 (2) |
C7—C12 | 1.383 (2) | C11—H11 | 0.9300 |
C7—C8 | 1.390 (2) | C10—C9 | 1.382 (2) |
N2—C22 | 1.344 (2) | C12—H12 | 0.9300 |
N2—C23 | 1.408 (2) | C24—C25 | 1.389 (3) |
N2—H2 | 0.8600 | C24—H24 | 0.9300 |
O4—C22 | 1.2279 (19) | C8—C9 | 1.381 (2) |
O3—C21 | 1.2110 (19) | C8—H8 | 0.9300 |
C21—C20 | 1.473 (2) | C25—C26 | 1.379 (3) |
C21—C2 | 1.537 (2) | C25—H25 | 0.9300 |
C28—C27 | 1.381 (2) | C9—H9 | 0.9300 |
C28—C23 | 1.390 (2) | C26—H26 | 0.9300 |
C28—C1 | 1.510 (2) | C16—C17 | 1.366 (3) |
O1—C10 | 1.370 (2) | C16—H16 | 0.9300 |
O1—C13 | 1.423 (3) | C19—C18 | 1.379 (3) |
C4—C6 | 1.520 (2) | C19—H19 | 0.9300 |
C4—H4 | 0.9800 | C18—C17 | 1.374 (4) |
C2—C14 | 1.530 (2) | C18—H18 | 0.9300 |
C2—C1 | 1.601 (2) | C13—H13A | 0.9600 |
C14—H14A | 0.9700 | C13—H13B | 0.9600 |
C14—H14B | 0.9700 | C13—H13C | 0.9600 |
C22—C1 | 1.565 (2) | C17—H17 | 0.9300 |
C6—H6A | 0.9700 | | |
| | | |
C5—S1—C6 | 93.52 (8) | C28—C23—N2 | 109.43 (13) |
C15—O2—C14 | 114.74 (13) | C15—C20—C19 | 118.80 (18) |
C5—N1—C1 | 120.0 (1) | C15—C20—C21 | 120.39 (15) |
C5—N1—C4 | 110.1 (1) | C19—C20—C21 | 120.55 (17) |
C1—N1—C4 | 109.0 (1) | N1—C5—S1 | 103.18 (11) |
C7—C3—C4 | 117.47 (12) | N1—C5—H5A | 111.1 |
C7—C3—C2 | 115.74 (12) | S1—C5—H5A | 111.1 |
C4—C3—C2 | 103.16 (12) | N1—C5—H5B | 111.1 |
C7—C3—H3 | 106.6 | S1—C5—H5B | 111.1 |
C4—C3—H3 | 106.6 | H5A—C5—H5B | 109.1 |
C2—C3—H3 | 106.6 | C28—C27—C26 | 118.42 (16) |
C12—C7—C8 | 116.97 (14) | C28—C27—H27 | 120.8 |
C12—C7—C3 | 119.24 (13) | C26—C27—H27 | 120.8 |
C8—C7—C3 | 123.76 (13) | O2—C15—C20 | 122.30 (16) |
C22—N2—C23 | 111.91 (13) | O2—C15—C16 | 117.16 (17) |
C22—N2—H2 | 124.0 | C20—C15—C16 | 120.54 (18) |
C23—N2—H2 | 124.0 | C10—C11—C12 | 119.43 (15) |
O3—C21—C20 | 123.17 (14) | C10—C11—H11 | 120.3 |
O3—C21—C2 | 122.49 (14) | C12—C11—H11 | 120.3 |
C20—C21—C2 | 114.34 (13) | O1—C10—C11 | 124.9 (2) |
C27—C28—C23 | 120.23 (15) | O1—C10—C9 | 115.6 (2) |
C27—C28—C1 | 130.34 (14) | C11—C10—C9 | 119.44 (15) |
C23—C28—C1 | 109.35 (13) | C7—C12—C11 | 122.44 (15) |
C10—O1—C13 | 117.50 (16) | C7—C12—H12 | 118.8 |
N1—C4—C6 | 103.98 (12) | C11—C12—H12 | 118.8 |
N1—C4—C3 | 100.09 (11) | C23—C24—C25 | 116.94 (17) |
C6—C4—C3 | 119.17 (13) | C23—C24—H24 | 121.5 |
N1—C4—H4 | 110.9 | C25—C24—H24 | 121.5 |
C6—C4—H4 | 110.9 | C9—C8—C7 | 121.24 (15) |
C3—C4—H4 | 110.9 | C9—C8—H8 | 119.4 |
C14—C2—C21 | 104.16 (12) | C7—C8—H8 | 119.4 |
C14—C2—C3 | 113.28 (12) | C26—C25—C24 | 121.94 (16) |
C21—C2—C3 | 111.86 (12) | C26—C25—H25 | 119.0 |
C14—C2—C1 | 112.96 (12) | C24—C25—H25 | 119.0 |
C21—C2—C1 | 110.41 (11) | C8—C9—C10 | 120.44 (16) |
C3—C2—C1 | 104.36 (11) | C8—C9—H9 | 119.8 |
O2—C14—C2 | 111.60 (13) | C10—C9—H9 | 119.8 |
O2—C14—H14A | 109.3 | C25—C26—C27 | 120.38 (16) |
C2—C14—H14A | 109.3 | C25—C26—H26 | 119.8 |
O2—C14—H14B | 109.3 | C27—C26—H26 | 119.8 |
C2—C14—H14B | 109.3 | C17—C16—C15 | 119.3 (2) |
H14A—C14—H14B | 108.0 | C17—C16—H16 | 120.4 |
O4—C22—N2 | 126.15 (14) | C15—C16—H16 | 120.4 |
O4—C22—C1 | 125.47 (14) | C18—C19—C20 | 120.0 (2) |
N2—C22—C1 | 108.25 (12) | C18—C19—H19 | 120.0 |
C4—C6—S1 | 104.64 (11) | C20—C19—H19 | 120.0 |
C4—C6—H6A | 110.8 | C17—C18—C19 | 120.0 (2) |
S1—C6—H6A | 110.8 | C17—C18—H18 | 120.0 |
C4—C6—H6B | 110.8 | C19—C18—H18 | 120.0 |
S1—C6—H6B | 110.8 | O1—C13—H13A | 109.5 |
H6A—C6—H6B | 108.9 | O1—C13—H13B | 109.5 |
N1—C1—C28 | 111.39 (12) | H13A—C13—H13B | 109.5 |
N1—C1—C22 | 112.55 (11) | O1—C13—H13C | 109.5 |
C28—C1—C22 | 100.97 (12) | H13A—C13—H13C | 109.5 |
N1—C1—C2 | 101.48 (11) | H13B—C13—H13C | 109.5 |
C28—C1—C2 | 118.10 (11) | C16—C17—C18 | 121.3 (2) |
C22—C1—C2 | 112.82 (11) | C16—C17—H17 | 119.3 |
C24—C23—C28 | 122.04 (15) | C18—C17—H17 | 119.3 |
C24—C23—N2 | 128.50 (15) | | |
| | | |
C4—C3—C7—C12 | 165.30 (15) | C3—C2—C1—N1 | −5.61 (13) |
C2—C3—C7—C12 | −72.33 (18) | C14—C2—C1—C28 | 108.88 (15) |
C4—C3—C7—C8 | −12.5 (2) | C21—C2—C1—C28 | −7.29 (18) |
C2—C3—C7—C8 | 109.86 (17) | C3—C2—C1—C28 | −127.65 (13) |
C5—N1—C4—C6 | 54.57 (15) | C14—C2—C1—C22 | −8.42 (17) |
C1—N1—C4—C6 | −171.95 (11) | C21—C2—C1—C22 | −124.59 (13) |
C5—N1—C4—C3 | 178.25 (12) | C3—C2—C1—C22 | 115.05 (13) |
C1—N1—C4—C3 | −48.27 (14) | C27—C28—C23—C24 | −2.8 (2) |
C7—C3—C4—N1 | 169.57 (12) | C1—C28—C23—C24 | −179.96 (14) |
C2—C3—C4—N1 | 40.95 (13) | C27—C28—C23—N2 | 175.20 (14) |
C7—C3—C4—C6 | −78.07 (17) | C1—C28—C23—N2 | −1.96 (17) |
C2—C3—C4—C6 | 153.31 (13) | C22—N2—C23—C24 | 177.76 (16) |
O3—C21—C2—C14 | 138.12 (15) | C22—N2—C23—C28 | −0.08 (18) |
C20—C21—C2—C14 | −42.31 (16) | O3—C21—C20—C15 | −171.66 (16) |
O3—C21—C2—C3 | 15.4 (2) | C2—C21—C20—C15 | 8.8 (2) |
C20—C21—C2—C3 | −165.02 (13) | O3—C21—C20—C19 | 14.3 (2) |
O3—C21—C2—C1 | −100.34 (17) | C2—C21—C20—C19 | −165.29 (15) |
C20—C21—C2—C1 | 79.23 (16) | C1—N1—C5—S1 | −170.89 (10) |
C7—C3—C2—C14 | −28.19 (17) | C4—N1—C5—S1 | −43.24 (13) |
C4—C3—C2—C14 | 101.49 (14) | C6—S1—C5—N1 | 15.87 (11) |
C7—C3—C2—C21 | 89.17 (14) | C23—C28—C27—C26 | 2.2 (2) |
C4—C3—C2—C21 | −141.15 (12) | C1—C28—C27—C26 | 178.71 (15) |
C7—C3—C2—C1 | −151.46 (11) | C14—O2—C15—C20 | 12.9 (2) |
C4—C3—C2—C1 | −21.77 (13) | C14—O2—C15—C16 | −167.10 (14) |
C15—O2—C14—C2 | −51.93 (18) | C19—C20—C15—O2 | −176.85 (15) |
C21—C2—C14—O2 | 64.87 (15) | C21—C20—C15—O2 | 9.0 (2) |
C3—C2—C14—O2 | −173.35 (12) | C19—C20—C15—C16 | 3.2 (2) |
C1—C2—C14—O2 | −54.96 (17) | C21—C20—C15—C16 | −171.00 (15) |
C23—N2—C22—O4 | −173.97 (15) | C13—O1—C10—C11 | 1.3 (3) |
C23—N2—C22—C1 | 2.00 (17) | C13—O1—C10—C9 | −179.4 (2) |
N1—C4—C6—S1 | −37.67 (13) | C12—C11—C10—O1 | 179.71 (18) |
C3—C4—C6—S1 | −147.90 (11) | C12—C11—C10—C9 | 0.5 (3) |
C5—S1—C6—C4 | 12.63 (11) | C8—C7—C12—C11 | −1.5 (3) |
C5—N1—C1—C28 | −71.78 (16) | C3—C7—C12—C11 | −179.45 (16) |
C4—N1—C1—C28 | 160.10 (11) | C10—C11—C12—C7 | 1.3 (3) |
C5—N1—C1—C22 | 40.80 (17) | C28—C23—C24—C25 | 1.6 (2) |
C4—N1—C1—C22 | −87.32 (14) | N2—C23—C24—C25 | −175.98 (16) |
C5—N1—C1—C2 | 161.65 (12) | C12—C7—C8—C9 | −0.1 (3) |
C4—N1—C1—C2 | 33.53 (13) | C3—C7—C8—C9 | 177.75 (17) |
C27—C28—C1—N1 | −54.2 (2) | C23—C24—C25—C26 | 0.0 (3) |
C23—C28—C1—N1 | 122.59 (13) | C7—C8—C9—C10 | 1.9 (3) |
C27—C28—C1—C22 | −173.88 (16) | O1—C10—C9—C8 | 178.66 (17) |
C23—C28—C1—C22 | 2.89 (15) | C11—C10—C9—C8 | −2.1 (3) |
C27—C28—C1—C2 | 62.7 (2) | C24—C25—C26—C27 | −0.5 (3) |
C23—C28—C1—C2 | −120.57 (14) | C28—C27—C26—C25 | −0.6 (3) |
O4—C22—C1—N1 | 54.2 (2) | O2—C15—C16—C17 | 178.24 (17) |
N2—C22—C1—N1 | −121.79 (14) | C20—C15—C16—C17 | −1.8 (3) |
O4—C22—C1—C28 | 173.07 (15) | C15—C20—C19—C18 | −2.0 (3) |
N2—C22—C1—C28 | −2.93 (15) | C21—C20—C19—C18 | 172.15 (18) |
O4—C22—C1—C2 | −59.9 (2) | C20—C19—C18—C17 | −0.5 (3) |
N2—C22—C1—C2 | 124.09 (13) | C15—C16—C17—C18 | −0.8 (3) |
C14—C2—C1—N1 | −129.09 (13) | C19—C18—C17—C16 | 2.0 (3) |
C21—C2—C1—N1 | 114.74 (13) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O4i | 0.86 | 2.13 | 2.949 (2) | 160 |
C9—H9···O3ii | 0.93 | 2.42 | 3.312 (2) | 160 |
Symmetry codes: (i) −x, −y, −z; (ii) −x+1, y−1/2, −z+1/2. |