The absolute configuration of the title compound, C
25H
28N
2O
4S, has been determined. The molecules are interconnected by weak C—H
O hydrogen bonds. The 1,4-dihydropyridine (1,4-DHP) ring adopts the usual shallow boat conformation. The thiophene ring is nearly planar.
Supporting information
CCDC reference: 613678
Key indicators
- Single-crystal X-ray study
- T = 183 K
- Mean (C-C) = 0.002 Å
- R factor = 0.038
- wR factor = 0.096
- Data-to-parameter ratio = 29.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.02 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C31
PLAT480_ALERT_4_C Long H...A H-Bond Reported H52B .. O31 .. 2.61 Ang.
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 32.94
From the CIF: _reflns_number_total 8488
Count of symmetry unique reflns 4809
Completeness (_total/calc) 176.50%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 3679
Fraction of Friedel pairs measured 0.765
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 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
2 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
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97.
(4
S,1'
R)-Diethyl
6-methyl-2-[(1'-phenylethylimino)methyl]-4-(2-thienyl)-
1,4-dihydropyridine-3,5-dicarboxylate
top
Crystal data top
C25H28N2O4S | F(000) = 480 |
Mr = 452.55 | Dx = 1.243 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 8192 reflections |
a = 10.3023 (2) Å | θ = 1.4–32.9° |
b = 8.1925 (1) Å | µ = 0.17 mm−1 |
c = 14.3279 (2) Å | T = 183 K |
β = 90.420 (1)° | Prism, yellow |
V = 1209.27 (3) Å3 | 0.60 × 0.28 × 0.10 mm |
Z = 2 | |
Data collection top
Siemens SMART CCD diffractometer | 8488 independent reflections |
Radiation source: fine-focus sealed tube | 7741 reflections with F2 > 2σ(F2) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 8.3 pixels mm-1 | θmax = 32.9°, θmin = 1.4° |
ω scans | h = −15→15 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | k = −12→12 |
Tmin = 0.902, Tmax = 0.984 | l = −21→21 |
21384 measured 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)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.096 | w = 1/[σ2(Fo2) + (0.0718P)2 + 0.1736P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.002 |
8488 reflections | Δρmax = 0.29 e Å−3 |
293 parameters | Δρmin = −0.25 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
18 constraints | Absolute structure parameter: −0.02 (5) |
Primary atom site location: structure-invariant direct methods | |
Special details top
Experimental. Data were collected at low temperature using a Siemens SMART CCD
diffractometer equipped with a Siemens LT-2 device. A full sphere of
reciprocal space was scanned by 0.3° steps in ω with a crystal-to-detector
distance of 3.97 cm, 30 sec per frame. Preliminary orientation matrix was
obtained from the first 100 frames using SMART (Siemens, 1995). The
collected frames were integrated using the preliminary orientation matrix
which was updated every 100 frames. Final cell parameters were obtained by
refinement on the position of 8192 reflections with I>10σ(I) after
integration of all the frames data using SAINT (Siemens, 1995). The
structure was solved by direct methods (Bruker, 1997) and refined by
full-matrix least squares on all F2 data using SHELXL97 (Sheldrick,
1997). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.82634 (9) | 0.19568 (12) | 0.65811 (6) | 0.02143 (18) | |
H1 | 0.8526 | 0.1843 | 0.6002 | 0.026* | |
C2 | 0.91848 (10) | 0.20743 (13) | 0.72868 (8) | 0.01951 (19) | |
C3 | 0.88365 (10) | 0.26973 (14) | 0.81283 (7) | 0.01904 (18) | |
C4 | 0.75096 (10) | 0.34772 (13) | 0.82234 (7) | 0.01810 (18) | |
H4 | 0.7216 | 0.3355 | 0.8883 | 0.022* | |
C5 | 0.65377 (10) | 0.26238 (13) | 0.75834 (8) | 0.01947 (19) | |
C6 | 0.69453 (11) | 0.20123 (14) | 0.67545 (8) | 0.0209 (2) | |
C21 | 1.04892 (10) | 0.14778 (14) | 0.70305 (8) | 0.02062 (19) | |
H21 | 1.1208 | 0.1650 | 0.7438 | 0.025* | |
N21 | 1.06425 (9) | 0.07323 (13) | 0.62596 (7) | 0.02289 (19) | |
C22 | 1.19897 (11) | 0.02348 (15) | 0.60427 (8) | 0.0222 (2) | |
H22 | 1.2599 | 0.0811 | 0.6478 | 0.027* | |
C23 | 1.22912 (14) | 0.07478 (17) | 0.50423 (9) | 0.0311 (3) | |
H23A | 1.1678 | 0.0219 | 0.4613 | 0.037* | |
H23B | 1.3178 | 0.0417 | 0.4887 | 0.037* | |
H23C | 1.2211 | 0.1936 | 0.4986 | 0.037* | |
C24 | 1.21492 (11) | −0.15966 (15) | 0.61698 (8) | 0.0215 (2) | |
C25 | 1.12376 (12) | −0.27136 (16) | 0.58286 (8) | 0.0255 (2) | |
H25 | 1.0476 | −0.2330 | 0.5522 | 0.031* | |
C26 | 1.14348 (13) | −0.43801 (17) | 0.59340 (10) | 0.0307 (3) | |
H26 | 1.0808 | −0.5129 | 0.5701 | 0.037* | |
C27 | 1.25475 (15) | −0.49568 (18) | 0.63801 (11) | 0.0348 (3) | |
H27 | 1.2683 | −0.6097 | 0.6452 | 0.042* | |
C28 | 1.34542 (14) | −0.38586 (19) | 0.67185 (11) | 0.0350 (3) | |
H28 | 1.4218 | −0.4247 | 0.7021 | 0.042* | |
C29 | 1.32564 (12) | −0.21887 (18) | 0.66196 (9) | 0.0284 (2) | |
H29 | 1.3882 | −0.1445 | 0.6861 | 0.034* | |
C31 | 0.97165 (11) | 0.26957 (17) | 0.89544 (8) | 0.0251 (2) | |
O31 | 1.08580 (10) | 0.2429 (3) | 0.89629 (8) | 0.0671 (5) | |
O32 | 0.90602 (9) | 0.29994 (17) | 0.97255 (6) | 0.0396 (3) | |
C32 | 0.97702 (14) | 0.2995 (3) | 1.06036 (9) | 0.0417 (4) | |
H32A | 1.0354 | 0.3953 | 1.0643 | 0.050* | |
H32B | 1.0300 | 0.1991 | 1.0662 | 0.050* | |
C33 | 0.87731 (17) | 0.3061 (3) | 1.13581 (11) | 0.0547 (5) | |
H33A | 0.8228 | 0.4030 | 1.1272 | 0.066* | |
H33B | 0.9208 | 0.3116 | 1.1968 | 0.066* | |
H33C | 0.8230 | 0.2079 | 1.1329 | 0.066* | |
C41 | 0.75991 (11) | 0.52828 (14) | 0.79939 (8) | 0.0206 (2) | |
S41 | 0.64813 (4) | 0.66562 (4) | 0.84143 (3) | 0.03845 (9) | |
C42 | 0.84689 (13) | 0.60559 (16) | 0.74241 (9) | 0.0278 (2) | |
H42 | 0.9170 | 0.5514 | 0.7128 | 0.033* | |
C43 | 0.82115 (15) | 0.77616 (17) | 0.73223 (10) | 0.0331 (3) | |
H43 | 0.8712 | 0.8474 | 0.6945 | 0.040* | |
C44 | 0.71712 (17) | 0.82465 (17) | 0.78252 (12) | 0.0386 (3) | |
H44 | 0.6862 | 0.9338 | 0.7848 | 0.046* | |
C51 | 0.51740 (11) | 0.25516 (15) | 0.78774 (9) | 0.0241 (2) | |
O51 | 0.42990 (9) | 0.18162 (17) | 0.74929 (8) | 0.0415 (3) | |
O52 | 0.49943 (8) | 0.34241 (13) | 0.86598 (7) | 0.02920 (19) | |
C52 | 0.36871 (12) | 0.3491 (2) | 0.90292 (11) | 0.0362 (3) | |
H52A | 0.3438 | 0.2417 | 0.9289 | 0.043* | |
H52B | 0.3060 | 0.3786 | 0.8530 | 0.043* | |
C53 | 0.36926 (16) | 0.4765 (2) | 0.97809 (12) | 0.0445 (4) | |
H53A | 0.4328 | 0.4468 | 1.0264 | 0.053* | |
H53B | 0.2827 | 0.4836 | 1.0058 | 0.053* | |
H53C | 0.3926 | 0.5824 | 0.9512 | 0.053* | |
C61 | 0.61176 (13) | 0.13429 (18) | 0.59786 (9) | 0.0305 (3) | |
H61A | 0.6050 | 0.0155 | 0.6044 | 0.037* | |
H61B | 0.6513 | 0.1607 | 0.5377 | 0.037* | |
H61C | 0.5250 | 0.1829 | 0.6008 | 0.037* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0216 (4) | 0.0252 (5) | 0.0175 (4) | 0.0008 (3) | −0.0004 (3) | −0.0011 (3) |
C2 | 0.0194 (4) | 0.0192 (4) | 0.0199 (4) | −0.0003 (4) | 0.0003 (3) | 0.0002 (4) |
C3 | 0.0172 (4) | 0.0198 (4) | 0.0201 (4) | −0.0005 (4) | 0.0004 (3) | −0.0006 (4) |
C4 | 0.0175 (4) | 0.0182 (4) | 0.0186 (4) | −0.0003 (4) | 0.0004 (3) | −0.0004 (4) |
C5 | 0.0173 (4) | 0.0177 (4) | 0.0234 (5) | −0.0007 (4) | −0.0012 (3) | 0.0010 (4) |
C6 | 0.0206 (5) | 0.0201 (5) | 0.0219 (5) | −0.0010 (4) | −0.0026 (4) | 0.0011 (4) |
C21 | 0.0193 (4) | 0.0215 (5) | 0.0211 (5) | −0.0003 (4) | 0.0006 (4) | 0.0002 (4) |
N21 | 0.0208 (4) | 0.0246 (5) | 0.0232 (4) | 0.0021 (4) | 0.0009 (3) | −0.0035 (4) |
C22 | 0.0197 (5) | 0.0246 (5) | 0.0223 (5) | 0.0011 (4) | 0.0015 (4) | −0.0042 (4) |
C23 | 0.0338 (6) | 0.0313 (6) | 0.0284 (6) | 0.0021 (5) | 0.0081 (5) | 0.0020 (5) |
C24 | 0.0206 (5) | 0.0255 (5) | 0.0184 (5) | 0.0008 (4) | 0.0023 (4) | −0.0020 (4) |
C25 | 0.0224 (5) | 0.0298 (6) | 0.0243 (5) | −0.0001 (4) | 0.0000 (4) | −0.0036 (4) |
C26 | 0.0306 (6) | 0.0279 (6) | 0.0338 (6) | −0.0055 (5) | 0.0033 (5) | −0.0036 (5) |
C27 | 0.0417 (7) | 0.0266 (6) | 0.0362 (7) | 0.0024 (5) | 0.0025 (6) | 0.0049 (5) |
C28 | 0.0319 (6) | 0.0351 (7) | 0.0378 (7) | 0.0056 (5) | −0.0067 (5) | 0.0057 (6) |
C29 | 0.0241 (5) | 0.0330 (6) | 0.0281 (6) | 0.0001 (5) | −0.0040 (4) | 0.0000 (5) |
C31 | 0.0205 (5) | 0.0338 (6) | 0.0210 (5) | 0.0000 (4) | −0.0002 (4) | −0.0053 (4) |
O31 | 0.0204 (5) | 0.1516 (17) | 0.0292 (5) | 0.0146 (7) | −0.0046 (4) | −0.0232 (7) |
O32 | 0.0258 (4) | 0.0739 (8) | 0.0191 (4) | 0.0126 (5) | −0.0031 (3) | −0.0067 (5) |
C32 | 0.0295 (6) | 0.0758 (12) | 0.0197 (5) | 0.0090 (7) | −0.0050 (5) | −0.0076 (6) |
C33 | 0.0410 (8) | 0.1003 (17) | 0.0229 (6) | 0.0011 (9) | 0.0003 (6) | −0.0121 (8) |
C41 | 0.0221 (5) | 0.0186 (5) | 0.0212 (5) | −0.0003 (4) | −0.0012 (4) | −0.0018 (4) |
S41 | 0.04164 (19) | 0.02131 (14) | 0.0527 (2) | 0.00598 (13) | 0.01728 (15) | 0.00094 (14) |
C42 | 0.0341 (6) | 0.0219 (5) | 0.0273 (6) | −0.0047 (5) | 0.0036 (5) | 0.0006 (4) |
C43 | 0.0439 (7) | 0.0224 (6) | 0.0332 (6) | −0.0077 (5) | 0.0009 (5) | 0.0041 (5) |
C44 | 0.0502 (8) | 0.0182 (5) | 0.0474 (8) | 0.0005 (5) | 0.0045 (7) | 0.0024 (5) |
C51 | 0.0200 (5) | 0.0232 (5) | 0.0290 (6) | −0.0011 (4) | −0.0002 (4) | 0.0021 (4) |
O51 | 0.0229 (4) | 0.0543 (7) | 0.0474 (6) | −0.0119 (4) | −0.0001 (4) | −0.0135 (5) |
O52 | 0.0180 (4) | 0.0383 (5) | 0.0314 (5) | −0.0024 (4) | 0.0053 (3) | −0.0044 (4) |
C52 | 0.0196 (5) | 0.0487 (8) | 0.0404 (7) | 0.0008 (5) | 0.0090 (5) | 0.0028 (6) |
C53 | 0.0372 (8) | 0.0496 (9) | 0.0471 (9) | 0.0059 (7) | 0.0194 (7) | −0.0007 (7) |
C61 | 0.0278 (6) | 0.0382 (7) | 0.0253 (6) | −0.0057 (5) | −0.0041 (4) | −0.0039 (5) |
Geometric parameters (Å, º) top
N1—C6 | 1.3830 (14) | C28—H28 | 0.9500 |
N1—C2 | 1.3853 (14) | C29—H29 | 0.9500 |
N1—H1 | 0.8800 | C31—O31 | 1.1961 (15) |
C2—C3 | 1.3599 (15) | C31—O32 | 1.3231 (15) |
C2—C21 | 1.4788 (15) | O32—C32 | 1.4506 (16) |
C3—C31 | 1.4856 (15) | C32—C33 | 1.498 (2) |
C3—C4 | 1.5160 (15) | C32—H32A | 0.9900 |
C4—C41 | 1.5183 (16) | C32—H32B | 0.9900 |
C4—C5 | 1.5228 (15) | C33—H33A | 0.9800 |
C4—H4 | 1.0000 | C33—H33B | 0.9800 |
C5—C6 | 1.3583 (16) | C33—H33C | 0.9800 |
C5—C51 | 1.4709 (15) | C41—C42 | 1.3716 (17) |
C6—C61 | 1.4999 (16) | C41—S41 | 1.7220 (12) |
C21—N21 | 1.2730 (15) | S41—C44 | 1.7098 (15) |
C21—H21 | 0.9500 | C42—C43 | 1.4296 (19) |
N21—C22 | 1.4817 (15) | C42—H42 | 0.9500 |
C22—C24 | 1.5201 (17) | C43—C44 | 1.355 (2) |
C22—C23 | 1.5278 (17) | C43—H43 | 0.9500 |
C22—H22 | 1.0000 | C44—H44 | 0.9500 |
C23—H23A | 0.9800 | C51—O51 | 1.2132 (15) |
C23—H23B | 0.9800 | C51—O52 | 1.3435 (15) |
C23—H23C | 0.9800 | O52—C52 | 1.4516 (14) |
C24—C29 | 1.3932 (17) | C52—C53 | 1.500 (2) |
C24—C25 | 1.3971 (17) | C52—H52A | 0.9900 |
C25—C26 | 1.3884 (19) | C52—H52B | 0.9900 |
C25—H25 | 0.9500 | C53—H53A | 0.9800 |
C26—C27 | 1.391 (2) | C53—H53B | 0.9800 |
C26—H26 | 0.9500 | C53—H53C | 0.9800 |
C27—C28 | 1.382 (2) | C61—H61A | 0.9800 |
C27—H27 | 0.9500 | C61—H61B | 0.9800 |
C28—C29 | 1.390 (2) | C61—H61C | 0.9800 |
| | | |
C6—N1—C2 | 122.35 (9) | C28—C29—H29 | 119.7 |
C6—N1—H1 | 118.8 | C24—C29—H29 | 119.7 |
C2—N1—H1 | 118.8 | O31—C31—O32 | 122.29 (11) |
C3—C2—N1 | 119.30 (10) | O31—C31—C3 | 127.04 (11) |
C3—C2—C21 | 126.19 (10) | O32—C31—C3 | 110.64 (10) |
N1—C2—C21 | 114.51 (9) | C31—O32—C32 | 117.79 (10) |
C2—C3—C31 | 122.86 (10) | O32—C32—C33 | 106.36 (12) |
C2—C3—C4 | 118.81 (10) | O32—C32—H32A | 110.5 |
C31—C3—C4 | 118.30 (9) | C33—C32—H32A | 110.5 |
C3—C4—C41 | 109.57 (9) | O32—C32—H32B | 110.5 |
C3—C4—C5 | 109.98 (9) | C33—C32—H32B | 110.5 |
C41—C4—C5 | 110.95 (9) | H32A—C32—H32B | 108.6 |
C3—C4—H4 | 108.8 | C32—C33—H33A | 109.5 |
C41—C4—H4 | 108.8 | C32—C33—H33B | 109.5 |
C5—C4—H4 | 108.8 | H33A—C33—H33B | 109.5 |
C6—C5—C51 | 122.52 (10) | C32—C33—H33C | 109.5 |
C6—C5—C4 | 119.33 (9) | H33A—C33—H33C | 109.5 |
C51—C5—C4 | 118.11 (9) | H33B—C33—H33C | 109.5 |
C5—C6—N1 | 118.65 (10) | C42—C41—C4 | 128.30 (11) |
C5—C6—C61 | 127.24 (10) | C42—C41—S41 | 110.36 (9) |
N1—C6—C61 | 114.11 (10) | C4—C41—S41 | 121.27 (8) |
N21—C21—C2 | 119.52 (10) | C44—S41—C41 | 92.51 (7) |
N21—C21—H21 | 120.2 | C41—C42—C43 | 112.99 (13) |
C2—C21—H21 | 120.2 | C41—C42—H42 | 123.5 |
C21—N21—C22 | 115.87 (10) | C43—C42—H42 | 123.5 |
N21—C22—C24 | 110.30 (10) | C44—C43—C42 | 112.28 (13) |
N21—C22—C23 | 108.56 (10) | C44—C43—H43 | 123.9 |
C24—C22—C23 | 111.18 (10) | C42—C43—H43 | 123.9 |
N21—C22—H22 | 108.9 | C43—C44—S41 | 111.86 (11) |
C24—C22—H22 | 108.9 | C43—C44—H44 | 124.1 |
C23—C22—H22 | 108.9 | S41—C44—H44 | 124.1 |
C22—C23—H23A | 109.5 | O51—C51—O52 | 122.46 (11) |
C22—C23—H23B | 109.5 | O51—C51—C5 | 126.73 (12) |
H23A—C23—H23B | 109.5 | O52—C51—C5 | 110.81 (10) |
C22—C23—H23C | 109.5 | C51—O52—C52 | 117.27 (10) |
H23A—C23—H23C | 109.5 | O52—C52—C53 | 106.83 (12) |
H23B—C23—H23C | 109.5 | O52—C52—H52A | 110.4 |
C29—C24—C25 | 118.68 (12) | C53—C52—H52A | 110.4 |
C29—C24—C22 | 119.11 (11) | O52—C52—H52B | 110.4 |
C25—C24—C22 | 122.19 (10) | C53—C52—H52B | 110.4 |
C26—C25—C24 | 120.57 (12) | H52A—C52—H52B | 108.6 |
C26—C25—H25 | 119.7 | C52—C53—H53A | 109.5 |
C24—C25—H25 | 119.7 | C52—C53—H53B | 109.5 |
C25—C26—C27 | 120.22 (13) | H53A—C53—H53B | 109.5 |
C25—C26—H26 | 119.9 | C52—C53—H53C | 109.5 |
C27—C26—H26 | 119.9 | H53A—C53—H53C | 109.5 |
C28—C27—C26 | 119.51 (13) | H53B—C53—H53C | 109.5 |
C28—C27—H27 | 120.2 | C6—C61—H61A | 109.5 |
C26—C27—H27 | 120.2 | C6—C61—H61B | 109.5 |
C27—C28—C29 | 120.44 (13) | H61A—C61—H61B | 109.5 |
C27—C28—H28 | 119.8 | C6—C61—H61C | 109.5 |
C29—C28—H28 | 119.8 | H61A—C61—H61C | 109.5 |
C28—C29—C24 | 120.57 (13) | H61B—C61—H61C | 109.5 |
| | | |
C6—N1—C2—C3 | −18.34 (16) | C24—C25—C26—C27 | −0.1 (2) |
C6—N1—C2—C21 | 161.45 (10) | C25—C26—C27—C28 | 0.1 (2) |
N1—C2—C3—C31 | 172.89 (11) | C26—C27—C28—C29 | 0.3 (2) |
C21—C2—C3—C31 | −6.87 (18) | C27—C28—C29—C24 | −0.7 (2) |
N1—C2—C3—C4 | −9.11 (16) | C25—C24—C29—C28 | 0.60 (19) |
C21—C2—C3—C4 | 171.14 (10) | C22—C24—C29—C28 | −177.75 (12) |
C2—C3—C4—C41 | −89.68 (12) | C2—C3—C31—O31 | 13.4 (2) |
C31—C3—C4—C41 | 88.41 (12) | C4—C3—C31—O31 | −164.64 (17) |
C2—C3—C4—C5 | 32.53 (14) | C2—C3—C31—O32 | −165.04 (12) |
C31—C3—C4—C5 | −149.38 (10) | C4—C3—C31—O32 | 16.95 (17) |
C3—C4—C5—C6 | −33.13 (14) | O31—C31—O32—C32 | −0.3 (3) |
C41—C4—C5—C6 | 88.25 (12) | C3—C31—O32—C32 | 178.22 (13) |
C3—C4—C5—C51 | 149.14 (10) | C31—O32—C32—C33 | −169.84 (16) |
C41—C4—C5—C51 | −89.47 (12) | C3—C4—C41—C42 | 26.82 (16) |
C51—C5—C6—N1 | −172.45 (10) | C5—C4—C41—C42 | −94.81 (14) |
C4—C5—C6—N1 | 9.93 (15) | C3—C4—C41—S41 | −156.54 (8) |
C51—C5—C6—C61 | 6.63 (18) | C5—C4—C41—S41 | 81.83 (11) |
C4—C5—C6—C61 | −171.00 (12) | C42—C41—S41—C44 | 0.31 (11) |
C2—N1—C6—C5 | 17.82 (16) | C4—C41—S41—C44 | −176.88 (10) |
C2—N1—C6—C61 | −161.37 (11) | C4—C41—C42—C43 | 176.18 (11) |
C3—C2—C21—N21 | 170.99 (11) | S41—C41—C42—C43 | −0.76 (15) |
N1—C2—C21—N21 | −8.78 (16) | C41—C42—C43—C44 | 0.95 (18) |
C2—C21—N21—C22 | 177.70 (10) | C42—C43—C44—S41 | −0.69 (18) |
C21—N21—C22—C24 | 105.97 (12) | C41—S41—C44—C43 | 0.23 (13) |
C21—N21—C22—C23 | −131.98 (11) | C6—C5—C51—O51 | 8.5 (2) |
N21—C22—C24—C29 | −136.56 (11) | C4—C5—C51—O51 | −173.80 (13) |
C23—C22—C24—C29 | 102.95 (13) | C6—C5—C51—O52 | −171.81 (11) |
N21—C22—C24—C25 | 45.16 (15) | C4—C5—C51—O52 | 5.84 (14) |
C23—C22—C24—C25 | −75.33 (14) | O51—C51—O52—C52 | −1.29 (19) |
C29—C24—C25—C26 | −0.19 (18) | C5—C51—O52—C52 | 179.05 (11) |
C22—C24—C25—C26 | 178.10 (12) | C51—O52—C52—C53 | −169.68 (12) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C52—H52B···O31i | 0.99 | 2.61 | 3.043 (2) | 107 |
C22—H22···O51ii | 1.00 | 2.41 | 3.403 (2) | 171 |
C21—H21···O31 | 0.95 | 2.31 | 2.898 (2) | 120 |
C4—H4···O32 | 1.00 | 2.26 | 2.699 (1) | 105 |
C4—H4···O52 | 1.00 | 2.31 | 2.671 (1) | 100 |
C61—H61C···O51 | 0.98 | 2.35 | 2.903 (2) | 115 |
N1—H1···N21 | 0.88 | 2.39 | 2.691 (1) | 100 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z. |