In the title compound, C
24H
23NO
5S, the pyran ring bearing the amino group adopts a flattened boat conformation. In the crystal structure, the molecules are linked by N—H
O hydrogen bonds.
Supporting information
CCDC reference: 610921
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.046
- wR factor = 0.137
- Data-to-parameter ratio = 12.6
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.93
| Author Response: ...We have collected data on kappa IP diffractometer and
processed using Denzo; and it is known that the DENZO image processing
package has problems with certain strong reflections.
They are often excluded from the data set leading to a lower value for
the above parameter.
|
Alert level C
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 25.03
From the CIF: _diffrn_reflns_theta_full 25.03
From the CIF: _reflns_number_total 3585
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 3864
Completeness (_total/calc) 92.78%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.93
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 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
3 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
Please specify the role of each of the co-authors
for your paper.
| Author Response: ... All the authors have been approved and each author has a
genuine role for the contribution to this paper.
|
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: XPRESS (MacScience, 2002); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and ORTEPII (Johnson, 1976); software used to prepare material for publication: PLATON.
Ethyl 2-amino-3-ethoxycarbonyl-7,8-dimethyl-4-[4-(methylsulfanyl)phenyl]-
5-oxo-4
H-pyrano[3,2-
c]chromene-3-carboxylate
top
Crystal data top
C24H23NO5S | F(000) = 920 |
Mr = 437.50 | Dx = 1.330 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2y b c | Cell parameters from 6677 reflections |
a = 17.295 (5) Å | θ = 2.4–25.0° |
b = 7.494 (4) Å | µ = 0.18 mm−1 |
c = 17.127 (9) Å | T = 295 K |
β = 100.220 (3)° | Block, pale yellow |
V = 2184.6 (18) Å3 | 0.25 × 0.22 × 0.22 mm |
Z = 4 | |
Data collection top
MacScience DIPLabo 32001 diffractometer | 3119 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.022 |
Graphite monochromator | θmax = 25.0°, θmin = 2.4° |
Detector resolution: 10.0 pixels mm-1 | h = −20→20 |
ω scans | k = −8→8 |
6677 measured reflections | l = −18→19 |
3585 independent reflections | |
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)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.137 | w = 1/[σ2(Fo2) + (0.0787P)2 + 0.3836P] where P = (Fo2 + 2Fc2)/3 |
S = 1.16 | (Δ/σ)max = 0.001 |
3585 reflections | Δρmax = 0.35 e Å−3 |
285 parameters | Δρmin = −0.29 e Å−3 |
0 restraints | Extinction correction: SHELXL97 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.034 (3) |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All e.s.d.'s are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F^2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F^2, conventional
R-factors R are based on F, with F set to zero for
negative F^2. The observed criterion of F^2 > σ(F^2)
is used only for calculating -R-factor-obs etc. and is not
relevant to the choice of reflections for refinement. R-factors based
on F^2 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 | |
O1 | 0.03361 (8) | 0.7325 (2) | 0.07855 (8) | 0.0591 (5) | |
O7 | 0.13296 (7) | 0.63853 (19) | 0.31098 (7) | 0.0477 (5) | |
O17 | 0.14808 (9) | 0.8061 (3) | 0.04893 (9) | 0.0722 (7) | |
O20 | 0.37041 (8) | 0.7585 (2) | 0.39742 (8) | 0.0629 (6) | |
O21 | 0.38344 (7) | 0.8268 (2) | 0.27269 (8) | 0.0494 (5) | |
N18 | 0.22616 (10) | 0.6544 (3) | 0.41751 (10) | 0.0618 (7) | |
C2 | 0.11363 (11) | 0.7526 (3) | 0.09969 (11) | 0.0503 (7) | |
C3 | 0.15042 (10) | 0.7102 (2) | 0.17979 (10) | 0.0402 (6) | |
C4 | 0.23881 (10) | 0.7208 (2) | 0.20106 (10) | 0.0384 (6) | |
C5 | 0.26278 (10) | 0.7160 (3) | 0.29035 (11) | 0.0417 (6) | |
C6 | 0.21131 (10) | 0.6724 (3) | 0.33893 (10) | 0.0430 (6) | |
C8 | 0.10400 (10) | 0.6707 (2) | 0.23270 (10) | 0.0397 (6) | |
C9 | 0.01980 (10) | 0.6620 (3) | 0.21244 (11) | 0.0433 (6) | |
C10 | −0.03074 (11) | 0.6298 (3) | 0.26646 (13) | 0.0486 (7) | |
C11 | −0.11060 (11) | 0.6270 (3) | 0.23975 (14) | 0.0534 (7) | |
C12 | −0.14311 (11) | 0.6533 (3) | 0.16009 (14) | 0.0526 (7) | |
C13 | −0.09410 (11) | 0.6848 (3) | 0.10491 (13) | 0.0549 (7) | |
C14 | −0.01341 (11) | 0.6911 (3) | 0.13350 (12) | 0.0476 (6) | |
C15 | −0.23117 (12) | 0.6505 (3) | 0.13435 (16) | 0.0665 (9) | |
C16 | −0.12544 (14) | 0.7132 (5) | 0.01821 (16) | 0.0809 (10) | |
C19 | 0.34194 (11) | 0.7652 (3) | 0.32682 (11) | 0.0450 (6) | |
C22 | 0.46362 (11) | 0.8810 (3) | 0.30270 (13) | 0.0543 (7) | |
C23 | 0.50346 (13) | 0.9049 (3) | 0.23295 (14) | 0.0633 (8) | |
C24 | 0.27734 (9) | 0.5733 (2) | 0.15926 (10) | 0.0369 (5) | |
C25 | 0.26733 (11) | 0.3960 (3) | 0.17714 (12) | 0.0481 (7) | |
C26 | 0.30086 (12) | 0.2609 (3) | 0.13971 (12) | 0.0506 (7) | |
C27 | 0.34564 (10) | 0.3010 (3) | 0.08190 (10) | 0.0409 (6) | |
C28 | 0.35672 (10) | 0.4778 (3) | 0.06401 (10) | 0.0425 (6) | |
C29 | 0.32280 (10) | 0.6121 (3) | 0.10267 (11) | 0.0410 (6) | |
S30 | 0.38284 (3) | 0.11681 (8) | 0.03578 (3) | 0.0560 (2) | |
C31 | 0.43785 (14) | 0.2134 (4) | −0.03192 (15) | 0.0706 (9) | |
H4 | 0.25530 | 0.83600 | 0.18240 | 0.0460* | |
H10 | −0.01050 | 0.61050 | 0.31980 | 0.0580* | |
H11 | −0.14390 | 0.60700 | 0.27590 | 0.0640* | |
H15A | −0.24880 | 0.76540 | 0.11370 | 0.1000* | |
H15B | −0.25550 | 0.62270 | 0.17900 | 0.1000* | |
H15C | −0.24520 | 0.56160 | 0.09400 | 0.1000* | |
H16A | −0.08280 | 0.74120 | −0.00880 | 0.1220* | |
H16B | −0.16240 | 0.81000 | 0.01200 | 0.1220* | |
H16C | −0.15110 | 0.60640 | −0.00400 | 0.1220* | |
H18A | 0.27300 | 0.67090 | 0.44330 | 0.0740* | |
H18B | 0.18890 | 0.62620 | 0.44250 | 0.0740* | |
H22A | 0.49040 | 0.79050 | 0.33800 | 0.0650* | |
H22B | 0.46420 | 0.99210 | 0.33190 | 0.0650* | |
H23A | 0.50460 | 0.79300 | 0.20590 | 0.0950* | |
H23B | 0.55620 | 0.94610 | 0.25070 | 0.0950* | |
H23C | 0.47520 | 0.99110 | 0.19740 | 0.0950* | |
H25 | 0.23730 | 0.36700 | 0.21530 | 0.0580* | |
H26 | 0.29360 | 0.14270 | 0.15310 | 0.0610* | |
H28 | 0.38690 | 0.50720 | 0.02600 | 0.0510* | |
H29 | 0.33090 | 0.73060 | 0.09020 | 0.0490* | |
H31A | 0.40440 | 0.28990 | −0.06810 | 0.1060* | |
H31B | 0.45840 | 0.12060 | −0.06100 | 0.1060* | |
H31C | 0.48050 | 0.28190 | −0.00310 | 0.1060* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0452 (7) | 0.0910 (12) | 0.0411 (8) | 0.0071 (7) | 0.0075 (6) | 0.0061 (7) |
O7 | 0.0399 (7) | 0.0665 (10) | 0.0378 (8) | −0.0020 (6) | 0.0099 (5) | 0.0065 (6) |
O17 | 0.0568 (9) | 0.1185 (15) | 0.0449 (9) | 0.0122 (9) | 0.0191 (7) | 0.0235 (8) |
O20 | 0.0508 (8) | 0.0969 (13) | 0.0393 (9) | −0.0046 (8) | 0.0037 (6) | −0.0042 (7) |
O21 | 0.0412 (7) | 0.0630 (9) | 0.0436 (8) | −0.0085 (6) | 0.0066 (5) | −0.0022 (6) |
N18 | 0.0499 (9) | 0.1006 (15) | 0.0360 (10) | 0.0000 (9) | 0.0109 (7) | 0.0041 (9) |
C2 | 0.0446 (10) | 0.0655 (14) | 0.0423 (11) | 0.0092 (9) | 0.0117 (8) | 0.0038 (9) |
C3 | 0.0416 (9) | 0.0428 (10) | 0.0377 (10) | 0.0047 (7) | 0.0114 (7) | −0.0006 (7) |
C4 | 0.0407 (9) | 0.0405 (10) | 0.0358 (10) | −0.0006 (7) | 0.0114 (7) | −0.0001 (7) |
C5 | 0.0418 (9) | 0.0473 (11) | 0.0373 (10) | 0.0007 (8) | 0.0103 (7) | −0.0054 (7) |
C6 | 0.0438 (9) | 0.0514 (12) | 0.0344 (11) | 0.0031 (8) | 0.0086 (7) | −0.0012 (8) |
C8 | 0.0426 (9) | 0.0409 (10) | 0.0359 (10) | 0.0035 (7) | 0.0080 (7) | 0.0009 (7) |
C9 | 0.0403 (9) | 0.0412 (11) | 0.0492 (11) | 0.0029 (8) | 0.0103 (8) | 0.0006 (8) |
C10 | 0.0456 (10) | 0.0476 (12) | 0.0546 (12) | 0.0027 (8) | 0.0143 (8) | 0.0056 (8) |
C11 | 0.0426 (10) | 0.0499 (13) | 0.0709 (15) | 0.0012 (8) | 0.0185 (9) | 0.0064 (9) |
C12 | 0.0421 (10) | 0.0428 (12) | 0.0721 (14) | 0.0016 (8) | 0.0081 (9) | −0.0012 (9) |
C13 | 0.0461 (10) | 0.0585 (14) | 0.0573 (13) | 0.0032 (9) | 0.0017 (9) | −0.0039 (10) |
C14 | 0.0442 (10) | 0.0532 (12) | 0.0458 (11) | 0.0040 (8) | 0.0090 (8) | 0.0006 (8) |
C15 | 0.0444 (11) | 0.0626 (15) | 0.0904 (18) | −0.0018 (10) | 0.0060 (11) | 0.0002 (12) |
C16 | 0.0553 (13) | 0.119 (2) | 0.0622 (16) | 0.0077 (14) | −0.0065 (11) | 0.0021 (14) |
C19 | 0.0450 (10) | 0.0508 (12) | 0.0399 (11) | 0.0031 (8) | 0.0092 (8) | −0.0060 (8) |
C22 | 0.0423 (10) | 0.0614 (14) | 0.0573 (13) | −0.0083 (9) | 0.0039 (8) | −0.0061 (9) |
C23 | 0.0526 (11) | 0.0685 (16) | 0.0696 (15) | −0.0101 (10) | 0.0132 (10) | 0.0068 (11) |
C24 | 0.0346 (8) | 0.0438 (10) | 0.0327 (9) | −0.0009 (7) | 0.0074 (6) | −0.0013 (7) |
C25 | 0.0510 (11) | 0.0497 (12) | 0.0490 (12) | −0.0045 (8) | 0.0234 (8) | 0.0017 (8) |
C26 | 0.0605 (12) | 0.0404 (11) | 0.0549 (12) | −0.0034 (9) | 0.0212 (9) | 0.0019 (8) |
C27 | 0.0367 (8) | 0.0483 (12) | 0.0372 (10) | 0.0030 (7) | 0.0054 (7) | −0.0042 (7) |
C28 | 0.0408 (9) | 0.0515 (12) | 0.0381 (10) | 0.0011 (8) | 0.0152 (7) | 0.0020 (8) |
C29 | 0.0431 (9) | 0.0415 (11) | 0.0402 (11) | −0.0012 (7) | 0.0125 (7) | 0.0030 (7) |
S30 | 0.0615 (4) | 0.0522 (4) | 0.0563 (4) | 0.0091 (2) | 0.0162 (2) | −0.0092 (2) |
C31 | 0.0704 (14) | 0.0854 (18) | 0.0626 (15) | 0.0199 (13) | 0.0296 (11) | −0.0052 (12) |
Geometric parameters (Å, º) top
S30—C27 | 1.767 (2) | C22—C23 | 1.492 (3) |
S30—C31 | 1.779 (3) | C24—C29 | 1.383 (2) |
O1—C2 | 1.375 (2) | C24—C25 | 1.381 (3) |
O1—C14 | 1.384 (2) | C25—C26 | 1.380 (3) |
O7—C6 | 1.378 (2) | C26—C27 | 1.394 (3) |
O7—C8 | 1.367 (2) | C27—C28 | 1.381 (3) |
O17—C2 | 1.206 (3) | C28—C29 | 1.390 (3) |
O20—C19 | 1.223 (2) | C4—H4 | 0.9804 |
O21—C19 | 1.351 (2) | C10—H10 | 0.9298 |
O21—C22 | 1.449 (2) | C11—H11 | 0.9295 |
N18—C6 | 1.331 (2) | C15—H15A | 0.9598 |
N18—H18A | 0.8600 | C15—H15B | 0.9589 |
N18—H18B | 0.8608 | C15—H15C | 0.9596 |
C2—C3 | 1.442 (3) | C16—H16A | 0.9607 |
C3—C8 | 1.346 (2) | C16—H16B | 0.9602 |
C3—C4 | 1.509 (2) | C16—H16C | 0.9604 |
C4—C24 | 1.532 (2) | C22—H22A | 0.9699 |
C4—C5 | 1.512 (3) | C22—H22B | 0.9704 |
C5—C6 | 1.362 (3) | C23—H23A | 0.9599 |
C5—C19 | 1.448 (3) | C23—H23B | 0.9599 |
C8—C9 | 1.437 (2) | C23—H23C | 0.9598 |
C9—C14 | 1.389 (3) | C25—H25 | 0.9298 |
C9—C10 | 1.402 (3) | C26—H26 | 0.9291 |
C10—C11 | 1.376 (3) | C28—H28 | 0.9303 |
C11—C12 | 1.394 (3) | C29—H29 | 0.9298 |
C12—C13 | 1.397 (3) | C31—H31A | 0.9592 |
C12—C15 | 1.509 (3) | C31—H31B | 0.9596 |
C13—C16 | 1.503 (3) | C31—H31C | 0.9602 |
C13—C14 | 1.395 (3) | | |
| | | |
S30···H23Ci | 3.0874 | C31···H28 | 2.6303 |
S30···H22Aii | 3.0809 | H4···O17 | 2.6852 |
S30···H18Aiii | 3.1143 | H4···O21 | 2.4681 |
O17···C29 | 3.332 (3) | H4···H26x | 2.4680 |
O17···C24 | 3.180 (2) | H4···H29 | 2.3579 |
O17···N18iv | 2.838 (2) | H10···O7 | 2.5211 |
O20···N18 | 2.694 (2) | H11···H15B | 2.3145 |
O21···C29 | 3.329 (2) | H11···C3viii | 3.0759 |
O21···C24 | 3.080 (2) | H11···H25vii | 2.5524 |
O1···H16A | 2.2863 | H15A···C16 | 2.9356 |
O7···H10 | 2.5211 | H15A···H16B | 2.5104 |
O17···H4 | 2.6852 | H15B···H11 | 2.3145 |
O17···H18Biv | 2.1296 | H15B···C5viii | 3.0990 |
O20···H22A | 2.4798 | H15B···C19viii | 3.0610 |
O20···H18A | 2.0872 | H15B···H25vii | 2.5546 |
O20···H28v | 2.7913 | H15C···C16 | 2.8670 |
O20···H22B | 2.7570 | H15C···H16C | 2.5589 |
O20···H31Cvi | 2.8809 | H15C···C28ix | 3.0461 |
O21···H4 | 2.4681 | H16A···O1 | 2.2863 |
N18···O20 | 2.694 (2) | H16B···C15 | 2.8494 |
N18···O17v | 2.838 (2) | H16B···H15A | 2.5104 |
C3···C11vii | 3.531 (3) | H16B···H18Bvii | 2.5611 |
C5···C15vii | 3.580 (3) | H16C···C15 | 2.9675 |
C8···C11vii | 3.451 (3) | H16C···H15C | 2.5589 |
C9···C10vii | 3.526 (3) | H18A···O20 | 2.0872 |
C10···C9viii | 3.526 (3) | H18A···C19 | 2.5971 |
C11···C3viii | 3.531 (3) | H18A···S30xi | 3.1143 |
C11···C8viii | 3.451 (3) | H18B···H16Bviii | 2.5611 |
C15···C19viii | 3.592 (3) | H18B···O17v | 2.1296 |
C15···C5viii | 3.580 (3) | H22A···O20 | 2.4798 |
C19···C15vii | 3.592 (3) | H22A···S30vi | 3.0809 |
C22···C28vi | 3.588 (3) | H22A···C27vi | 2.9238 |
C22···C27vi | 3.583 (3) | H22A···H23Cii | 2.4256 |
C24···O21 | 3.080 (2) | H22B···O20 | 2.7570 |
C24···O17 | 3.180 (2) | H22B···H23Avi | 2.4329 |
C27···C22ii | 3.583 (3) | H23A···H22Bii | 2.4329 |
C28···C22ii | 3.588 (3) | H23C···S30x | 3.0874 |
C29···O17 | 3.332 (3) | H23C···H22Avi | 2.4256 |
C29···O21 | 3.329 (2) | H25···C3 | 2.9863 |
C3···H11vii | 3.0759 | H25···C5 | 2.9130 |
C3···H25 | 2.9863 | H25···C11viii | 3.0377 |
C5···H25 | 2.9130 | H25···C15viii | 3.0613 |
C5···H15Bvii | 3.0990 | H25···H11viii | 2.5524 |
C11···H25vii | 3.0377 | H25···H15Bviii | 2.5546 |
C15···H16C | 2.9675 | H26···H4i | 2.4680 |
C15···H31Aix | 3.0425 | H28···C31 | 2.6303 |
C15···H25vii | 3.0613 | H28···H31A | 2.3482 |
C15···H16B | 2.8494 | H28···H31C | 2.4507 |
C16···H15C | 2.8670 | H28···O20iv | 2.7913 |
C16···H15A | 2.9356 | H29···H4 | 2.3579 |
C19···H15Bvii | 3.0610 | H31A···C28 | 2.9059 |
C19···H18A | 2.5971 | H31A···H28 | 2.3482 |
C27···H22Aii | 2.9238 | H31A···C15ix | 3.0425 |
C28···H31A | 2.9059 | H31C···C28 | 2.9887 |
C28···H15Cix | 3.0461 | H31C···H28 | 2.4507 |
C28···H31C | 2.9887 | H31C···O20ii | 2.8809 |
| | | |
C27—S30—C31 | 104.64 (12) | S30—C27—C26 | 116.19 (17) |
C2—O1—C14 | 122.06 (15) | C26—C27—C28 | 118.75 (19) |
C6—O7—C8 | 118.35 (14) | C27—C28—C29 | 120.13 (17) |
C19—O21—C22 | 116.37 (15) | C24—C29—C28 | 121.46 (19) |
C6—N18—H18A | 119.98 | C3—C4—H4 | 107.96 |
C6—N18—H18B | 120.02 | C5—C4—H4 | 107.89 |
H18A—N18—H18B | 120.00 | C24—C4—H4 | 107.89 |
O17—C2—C3 | 124.61 (18) | C9—C10—H10 | 120.34 |
O1—C2—O17 | 116.70 (17) | C11—C10—H10 | 120.33 |
O1—C2—C3 | 118.69 (16) | C10—C11—H11 | 119.02 |
C2—C3—C8 | 118.29 (16) | C12—C11—H11 | 118.99 |
C2—C3—C4 | 118.37 (15) | C12—C15—H15A | 109.48 |
C4—C3—C8 | 123.27 (15) | C12—C15—H15B | 109.46 |
C3—C4—C5 | 109.09 (14) | C12—C15—H15C | 109.47 |
C3—C4—C24 | 110.80 (13) | H15A—C15—H15B | 109.46 |
C5—C4—C24 | 113.04 (14) | H15A—C15—H15C | 109.53 |
C6—C5—C19 | 117.91 (17) | H15B—C15—H15C | 109.44 |
C4—C5—C6 | 122.14 (16) | C13—C16—H16A | 109.49 |
C4—C5—C19 | 119.91 (16) | C13—C16—H16B | 109.44 |
O7—C6—N18 | 109.50 (15) | C13—C16—H16C | 109.49 |
O7—C6—C5 | 122.75 (15) | H16A—C16—H16B | 109.54 |
N18—C6—C5 | 127.75 (17) | H16A—C16—H16C | 109.36 |
C3—C8—C9 | 123.18 (16) | H16B—C16—H16C | 109.51 |
O7—C8—C9 | 114.08 (15) | O21—C22—H22A | 110.26 |
O7—C8—C3 | 122.73 (16) | O21—C22—H22B | 110.19 |
C10—C9—C14 | 118.09 (17) | C23—C22—H22A | 110.23 |
C8—C9—C14 | 117.00 (16) | C23—C22—H22B | 110.22 |
C8—C9—C10 | 124.90 (17) | H22A—C22—H22B | 108.58 |
C9—C10—C11 | 119.3 (2) | C22—C23—H23A | 109.48 |
C10—C11—C12 | 122.0 (2) | C22—C23—H23B | 109.45 |
C11—C12—C13 | 119.87 (18) | C22—C23—H23C | 109.46 |
C11—C12—C15 | 119.7 (2) | H23A—C23—H23B | 109.52 |
C13—C12—C15 | 120.5 (2) | H23A—C23—H23C | 109.48 |
C12—C13—C16 | 122.45 (19) | H23B—C23—H23C | 109.44 |
C12—C13—C14 | 117.2 (2) | C24—C25—H25 | 119.23 |
C14—C13—C16 | 120.32 (19) | C26—C25—H25 | 119.22 |
O1—C14—C9 | 120.38 (17) | C25—C26—H26 | 119.90 |
O1—C14—C13 | 116.15 (18) | C27—C26—H26 | 119.83 |
C9—C14—C13 | 123.46 (18) | C27—C28—H28 | 119.98 |
O21—C19—C5 | 111.58 (16) | C29—C28—H28 | 119.89 |
O20—C19—C5 | 126.87 (18) | C24—C29—H29 | 119.30 |
O20—C19—O21 | 121.53 (18) | C28—C29—H29 | 119.24 |
O21—C22—C23 | 107.37 (17) | S30—C31—H31A | 109.46 |
C4—C24—C25 | 120.55 (15) | S30—C31—H31B | 109.48 |
C4—C24—C29 | 121.62 (15) | S30—C31—H31C | 109.47 |
C25—C24—C29 | 117.83 (17) | H31A—C31—H31B | 109.53 |
C24—C25—C26 | 121.55 (18) | H31A—C31—H31C | 109.44 |
C25—C26—C27 | 120.3 (2) | H31B—C31—H31C | 109.44 |
S30—C27—C28 | 125.05 (14) | | |
| | | |
C31—S30—C27—C26 | −178.80 (16) | C6—C5—C19—O21 | −172.11 (19) |
C31—S30—C27—C28 | 2.23 (19) | C4—C5—C19—O21 | 5.7 (3) |
C2—O1—C14—C13 | 176.40 (19) | C19—C5—C6—O7 | 174.27 (19) |
C14—O1—C2—C3 | 6.9 (3) | C4—C5—C6—N18 | 176.1 (2) |
C2—O1—C14—C9 | −2.3 (3) | C19—C5—C6—N18 | −6.1 (4) |
C14—O1—C2—O17 | −172.8 (2) | O7—C8—C9—C14 | −179.17 (18) |
C6—O7—C8—C3 | 9.4 (2) | O7—C8—C9—C10 | 2.1 (3) |
C6—O7—C8—C9 | −169.49 (17) | C3—C8—C9—C10 | −176.78 (19) |
C8—O7—C6—C5 | −8.0 (3) | C3—C8—C9—C14 | 2.0 (3) |
C8—O7—C6—N18 | 172.36 (17) | C10—C9—C14—O1 | 176.7 (2) |
C22—O21—C19—C5 | 179.70 (17) | C8—C9—C14—O1 | −2.2 (3) |
C22—O21—C19—O20 | 1.1 (3) | C10—C9—C14—C13 | −1.9 (3) |
C19—O21—C22—C23 | 167.64 (18) | C8—C9—C14—C13 | 179.2 (2) |
O17—C2—C3—C8 | 172.8 (2) | C14—C9—C10—C11 | 0.4 (3) |
O1—C2—C3—C4 | 175.99 (16) | C8—C9—C10—C11 | 179.2 (2) |
O17—C2—C3—C4 | −4.4 (3) | C9—C10—C11—C12 | 0.7 (3) |
O1—C2—C3—C8 | −6.8 (3) | C10—C11—C12—C15 | −179.4 (2) |
C2—C3—C4—C24 | −68.67 (19) | C10—C11—C12—C13 | −0.4 (3) |
C4—C3—C8—C9 | 179.52 (16) | C15—C12—C13—C16 | −1.3 (4) |
C2—C3—C4—C5 | 166.27 (17) | C15—C12—C13—C14 | 178.0 (2) |
C4—C3—C8—O7 | 0.8 (2) | C11—C12—C13—C14 | −1.0 (3) |
C2—C3—C8—C9 | 2.5 (3) | C11—C12—C13—C16 | 179.7 (2) |
C8—C3—C4—C24 | 114.32 (17) | C12—C13—C14—O1 | −176.45 (19) |
C8—C3—C4—C5 | −10.7 (2) | C16—C13—C14—C9 | −178.4 (2) |
C2—C3—C8—O7 | −176.24 (16) | C12—C13—C14—C9 | 2.2 (3) |
C3—C4—C5—C19 | −165.76 (18) | C16—C13—C14—O1 | 2.9 (3) |
C24—C4—C5—C6 | −111.8 (2) | C4—C24—C25—C26 | 179.38 (17) |
C5—C4—C24—C25 | 57.7 (2) | C4—C24—C29—C28 | −179.03 (16) |
C3—C4—C5—C6 | 11.9 (3) | C25—C24—C29—C28 | 0.8 (3) |
C24—C4—C5—C19 | 70.5 (2) | C29—C24—C25—C26 | −0.5 (3) |
C3—C4—C24—C29 | 114.74 (17) | C24—C25—C26—C27 | −0.5 (3) |
C3—C4—C24—C25 | −65.1 (2) | C25—C26—C27—S30 | −177.96 (15) |
C5—C4—C24—C29 | −122.46 (18) | C25—C26—C27—C28 | 1.1 (3) |
C6—C5—C19—O20 | 6.4 (4) | S30—C27—C28—C29 | 178.21 (14) |
C4—C5—C19—O20 | −175.9 (2) | C26—C27—C28—C29 | −0.7 (3) |
C4—C5—C6—O7 | −3.4 (3) | C27—C28—C29—C24 | −0.2 (3) |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, y−1/2, −z+1/2; (iii) x, −y+1/2, z−1/2; (iv) x, −y+3/2, z−1/2; (v) x, −y+3/2, z+1/2; (vi) −x+1, y+1/2, −z+1/2; (vii) −x, y+1/2, −z+1/2; (viii) −x, y−1/2, −z+1/2; (ix) −x, −y+1, −z; (x) x, y+1, z; (xi) x, −y+1/2, z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N18—H18A···O20 | 0.86 | 2.09 | 2.694 (2) | 127 |
N18—H18B···O17v | 0.86 | 2.13 | 2.838 (2) | 139 |
C16—H16A···O1 | 0.96 | 2.29 | 2.765 (3) | 110 |
Symmetry code: (v) x, −y+3/2, z+1/2. |