The title compound, C
16H
17NO
5, crystallizes with two molecules in the asymmetric unit. The dihedral angles between the furan and benzene rings are 26.38 (13) and 28.52 (14)°. The molecules are linked by N—H
O hydrogen bonds, leading to dimers.
Supporting information
CCDC reference: 289767
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.053
- wR factor = 0.159
- Data-to-parameter ratio = 17.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc.
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.13 Ratio
PLAT420_ALERT_2_C D-H Without Acceptor N2 - H201 ... ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H201 .. O2 .. 2.64 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 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
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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure and PLATON (Spek, 2003).
Dimethyl 3-(methylamino)-2-(4-methylphenyl)furan-4,5-dicarboxylate
top
Crystal data top
C16H17NO5 | F(000) = 1280.00 |
Mr = 303.31 | Dx = 1.319 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ybc | Cell parameters from 12870 reflections |
a = 15.5390 (2) Å | θ = 1.8–27.5° |
b = 17.8363 (3) Å | µ = 0.10 mm−1 |
c = 11.6349 (3) Å | T = 295 K |
β = 108.6580 (7)° | Prism, yellow |
V = 3055.23 (10) Å3 | 0.30 × 0.20 × 0.10 mm |
Z = 8 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 3442 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.050 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −20→20 |
Tmin = 0.943, Tmax = 0.990 | k = −23→23 |
28950 measured reflections | l = −15→14 |
6994 independent reflections | |
Refinement top
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.053 | w = 1/[0.0014Fo2 + 1σ(Fo2)]/(4Fo2) |
wR(F2) = 0.159 | (Δ/σ)max < 0.001 |
S = 1.01 | Δρmax = 0.57 e Å−3 |
6992 reflections | Δρmin = −0.59 e Å−3 |
397 parameters | |
Special details top
Refinement. Refinement using all reflections. The weighted R-factor (wR) and
goodness of fit (S) are based on F2. R-factor (gt) are
based on F. The threshold expression of F2 > 2.0
σ(F2) is used only for calculating R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.19334 (11) | 0.55133 (9) | 0.60462 (14) | 0.0438 (5) | |
O2 | 0.13246 (12) | 0.30854 (10) | 0.47869 (17) | 0.0586 (6) | |
O3 | 0.12175 (12) | 0.33308 (9) | 0.66288 (14) | 0.0487 (5) | |
O4 | 0.00263 (12) | 0.46164 (11) | 0.64034 (18) | 0.0569 (6) | |
O5 | 0.07660 (12) | 0.56647 (10) | 0.72350 (17) | 0.0579 (6) | |
O6 | 0.32307 (11) | 0.51294 (9) | 0.92235 (16) | 0.0467 (5) | |
O7 | 0.29690 (12) | 0.25939 (10) | 0.90574 (17) | 0.0573 (6) | |
O8 | 0.33441 (12) | 0.30705 (10) | 0.75115 (16) | 0.0511 (5) | |
O9 | 0.48171 (12) | 0.41124 (11) | 0.8276 (2) | 0.0645 (6) | |
O10 | 0.44858 (12) | 0.53331 (10) | 0.82024 (18) | 0.0605 (6) | |
N1 | 0.28585 (13) | 0.40982 (12) | 0.45587 (19) | 0.0467 (6) | |
N2 | 0.17956 (12) | 0.36918 (12) | 0.97855 (19) | 0.0436 (6) | |
C1 | 0.25200 (17) | 0.52907 (13) | 0.5430 (2) | 0.0422 (7) | |
C2 | 0.24027 (16) | 0.45424 (12) | 0.5171 (2) | 0.0390 (7) | |
C3 | 0.17029 (16) | 0.42928 (12) | 0.5638 (2) | 0.0380 (6) | |
C4 | 0.14308 (16) | 0.49067 (13) | 0.6136 (2) | 0.0409 (7) | |
C5 | 0.30801 (17) | 0.58925 (12) | 0.5188 (2) | 0.0408 (7) | |
C6 | 0.32681 (19) | 0.65345 (14) | 0.5906 (2) | 0.0514 (8) | |
C7 | 0.37400 (18) | 0.71244 (14) | 0.5623 (2) | 0.0538 (8) | |
C8 | 0.40382 (17) | 0.71026 (14) | 0.4619 (2) | 0.0493 (8) | |
C9 | 0.4521 (2) | 0.77634 (17) | 0.4303 (3) | 0.0743 (11) | |
C10 | 0.38659 (18) | 0.64553 (17) | 0.3920 (2) | 0.0538 (8) | |
C11 | 0.33968 (17) | 0.58587 (14) | 0.4190 (2) | 0.0468 (7) | |
C12 | 0.13875 (16) | 0.35145 (13) | 0.5616 (2) | 0.0412 (7) | |
C13 | 0.0852 (2) | 0.25869 (14) | 0.6658 (2) | 0.0632 (10) | |
C14 | 0.06647 (19) | 0.50340 (13) | 0.6596 (2) | 0.0433 (7) | |
C15 | 0.0045 (2) | 0.58471 (18) | 0.7720 (2) | 0.0681 (10) | |
C16 | 0.38497 (18) | 0.40661 (16) | 0.5051 (2) | 0.0575 (9) | |
C17 | 0.25543 (16) | 0.48947 (13) | 0.9677 (2) | 0.0422 (7) | |
C18 | 0.24219 (16) | 0.41455 (13) | 0.9491 (2) | 0.0390 (7) | |
C19 | 0.30580 (16) | 0.39020 (12) | 0.8905 (2) | 0.0380 (6) | |
C20 | 0.35412 (16) | 0.45188 (13) | 0.8787 (2) | 0.0404 (7) | |
C21 | 0.21895 (17) | 0.54724 (14) | 1.0280 (2) | 0.0458 (7) | |
C22 | 0.2190 (2) | 0.62213 (16) | 0.9966 (2) | 0.0616 (9) | |
C23 | 0.1877 (2) | 0.67608 (18) | 1.0574 (3) | 0.0771 (11) | |
C24 | 0.1560 (2) | 0.6579 (2) | 1.1527 (3) | 0.0749 (11) | |
C25 | 0.1273 (2) | 0.7183 (2) | 1.2243 (4) | 0.1187 (17) | |
C26 | 0.15381 (19) | 0.5835 (2) | 1.1813 (2) | 0.0670 (10) | |
C27 | 0.18474 (18) | 0.52863 (17) | 1.1206 (2) | 0.0547 (8) | |
C28 | 0.31275 (16) | 0.31266 (13) | 0.8525 (2) | 0.0392 (7) | |
C29 | 0.3510 (2) | 0.23199 (16) | 0.7162 (2) | 0.0672 (10) | |
C30 | 0.43449 (18) | 0.46157 (14) | 0.8395 (2) | 0.0433 (7) | |
C31 | 0.5268 (2) | 0.54973 (19) | 0.7831 (3) | 0.0737 (11) | |
C32 | 0.08478 (17) | 0.39031 (16) | 0.9368 (2) | 0.0526 (8) | |
H6 | 0.3073 | 0.6568 | 0.6581 | 0.064* | |
H7 | 0.3863 | 0.7547 | 0.6118 | 0.065* | |
H10 | 0.4066 | 0.6424 | 0.3249 | 0.066* | |
H11 | 0.3298 | 0.5429 | 0.3713 | 0.056* | |
H22 | 0.2401 | 0.6361 | 0.9333 | 0.077* | |
H23 | 0.1882 | 0.7260 | 1.0347 | 0.094* | |
H26 | 0.1311 | 0.5698 | 1.2433 | 0.081* | |
H27 | 0.1828 | 0.4786 | 1.1422 | 0.065* | |
H91 | 0.4085 | 0.8093 | 0.3769 | 0.090* | |
H92 | 0.4940 | 0.7589 | 0.3908 | 0.090* | |
H93 | 0.4848 | 0.8029 | 0.5030 | 0.090* | |
H101 | 0.2611 | 0.3661 | 0.4424 | 0.059* | |
H131 | 0.0201 | 0.2604 | 0.6346 | 0.083* | |
H132 | 0.1039 | 0.2408 | 0.7479 | 0.083* | |
H133 | 0.1075 | 0.2255 | 0.6169 | 0.083* | |
H151 | −0.0400 | 0.6148 | 0.7142 | 0.088* | |
H152 | 0.0288 | 0.6122 | 0.8464 | 0.088* | |
H153 | −0.0234 | 0.5394 | 0.7873 | 0.088* | |
H161 | 0.4108 | 0.4455 | 0.4694 | 0.073* | |
H162 | 0.4055 | 0.3587 | 0.4868 | 0.073* | |
H163 | 0.4036 | 0.4134 | 0.5914 | 0.074* | |
H201 | 0.1970 | 0.3294 | 1.0214 | 0.055* | |
H251 | 0.1788 | 0.7333 | 1.2915 | 0.147* | |
H252 | 0.0808 | 0.6990 | 1.2540 | 0.147* | |
H253 | 0.1043 | 0.7608 | 1.1730 | 0.147* | |
H291 | 0.4142 | 0.2201 | 0.7521 | 0.086* | |
H292 | 0.3348 | 0.2292 | 0.6295 | 0.086* | |
H293 | 0.3151 | 0.1969 | 0.7439 | 0.086* | |
H311 | 0.5792 | 0.5583 | 0.8529 | 0.095* | |
H312 | 0.5147 | 0.5937 | 0.7329 | 0.095* | |
H313 | 0.5381 | 0.5080 | 0.7378 | 0.095* | |
H321 | 0.0479 | 0.3460 | 0.9251 | 0.066* | |
H322 | 0.0717 | 0.4169 | 0.8614 | 0.066* | |
H323 | 0.0718 | 0.4220 | 0.9960 | 0.066* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0489 (10) | 0.0333 (9) | 0.0549 (11) | 0.0010 (8) | 0.0247 (9) | −0.0013 (8) |
O2 | 0.0809 (14) | 0.0455 (11) | 0.0589 (12) | −0.0111 (10) | 0.0357 (11) | −0.0128 (9) |
O3 | 0.0648 (11) | 0.0376 (10) | 0.0498 (10) | −0.0075 (8) | 0.0271 (10) | −0.0016 (8) |
O4 | 0.0491 (11) | 0.0573 (12) | 0.0698 (13) | −0.0022 (10) | 0.0268 (10) | 0.0008 (10) |
O5 | 0.0655 (12) | 0.0467 (11) | 0.0734 (13) | 0.0047 (9) | 0.0391 (11) | −0.0101 (9) |
O6 | 0.0480 (10) | 0.0392 (10) | 0.0584 (11) | −0.0053 (8) | 0.0245 (9) | −0.0060 (8) |
O7 | 0.0815 (14) | 0.0376 (10) | 0.0661 (13) | 0.0057 (9) | 0.0421 (11) | 0.0098 (9) |
O8 | 0.0686 (12) | 0.0441 (10) | 0.0496 (11) | 0.0034 (9) | 0.0316 (10) | −0.0016 (8) |
O9 | 0.0594 (12) | 0.0562 (12) | 0.0913 (15) | 0.0065 (10) | 0.0429 (12) | 0.0021 (11) |
O10 | 0.0605 (12) | 0.0455 (11) | 0.0899 (15) | −0.0079 (9) | 0.0441 (12) | 0.0021 (10) |
N1 | 0.0507 (13) | 0.0400 (12) | 0.0562 (13) | −0.0023 (10) | 0.0264 (11) | −0.0090 (10) |
N2 | 0.0425 (12) | 0.0425 (12) | 0.0503 (12) | 0.0021 (10) | 0.0210 (11) | 0.0127 (10) |
C1 | 0.0448 (14) | 0.0386 (14) | 0.0472 (15) | 0.0020 (11) | 0.0206 (13) | 0.0000 (11) |
C2 | 0.0418 (13) | 0.0356 (14) | 0.0414 (14) | 0.0014 (11) | 0.0159 (12) | −0.0003 (11) |
C3 | 0.0416 (13) | 0.0345 (13) | 0.0390 (14) | 0.0018 (11) | 0.0143 (12) | 0.0017 (11) |
C4 | 0.0423 (14) | 0.0362 (14) | 0.0466 (14) | 0.0002 (11) | 0.0176 (12) | 0.0038 (11) |
C5 | 0.0411 (14) | 0.0343 (13) | 0.0477 (15) | 0.0039 (11) | 0.0155 (12) | 0.0028 (11) |
C6 | 0.0594 (17) | 0.0444 (16) | 0.0557 (17) | −0.0018 (13) | 0.0258 (14) | −0.0044 (13) |
C7 | 0.0588 (17) | 0.0376 (15) | 0.0661 (19) | −0.0047 (13) | 0.0214 (16) | −0.0012 (13) |
C8 | 0.0400 (14) | 0.0438 (16) | 0.0613 (18) | −0.0004 (12) | 0.0124 (14) | 0.0090 (13) |
C9 | 0.072 (2) | 0.064 (2) | 0.087 (2) | −0.0183 (17) | 0.026 (2) | 0.0118 (18) |
C10 | 0.0526 (16) | 0.0601 (18) | 0.0526 (17) | −0.0016 (14) | 0.0222 (14) | 0.0067 (14) |
C11 | 0.0505 (15) | 0.0423 (15) | 0.0486 (16) | −0.0049 (12) | 0.0172 (13) | −0.0005 (12) |
C12 | 0.0402 (14) | 0.0381 (14) | 0.0469 (15) | 0.0040 (11) | 0.0162 (12) | −0.0007 (12) |
C13 | 0.086 (2) | 0.0407 (16) | 0.079 (2) | −0.0155 (15) | 0.0489 (19) | −0.0015 (14) |
C14 | 0.0499 (15) | 0.0385 (14) | 0.0448 (14) | 0.0102 (13) | 0.0199 (13) | 0.0075 (12) |
C15 | 0.076 (2) | 0.065 (2) | 0.079 (2) | 0.0221 (17) | 0.0459 (19) | −0.0007 (16) |
C16 | 0.0568 (17) | 0.0525 (17) | 0.072 (2) | 0.0052 (14) | 0.0338 (16) | −0.0046 (14) |
C17 | 0.0389 (13) | 0.0456 (15) | 0.0465 (15) | −0.0020 (11) | 0.0196 (12) | −0.0010 (12) |
C18 | 0.0403 (13) | 0.0399 (14) | 0.0383 (14) | 0.0015 (11) | 0.0145 (12) | 0.0015 (11) |
C19 | 0.0397 (14) | 0.0385 (14) | 0.0380 (13) | 0.0010 (11) | 0.0158 (11) | 0.0011 (11) |
C20 | 0.0441 (14) | 0.0357 (14) | 0.0432 (14) | 0.0018 (11) | 0.0164 (12) | −0.0018 (11) |
C21 | 0.0404 (14) | 0.0451 (16) | 0.0523 (16) | −0.0031 (12) | 0.0156 (13) | −0.0128 (12) |
C22 | 0.0603 (18) | 0.0493 (18) | 0.083 (2) | −0.0054 (14) | 0.0335 (17) | −0.0135 (15) |
C23 | 0.064 (2) | 0.0458 (19) | 0.126 (3) | −0.0053 (15) | 0.037 (2) | −0.0276 (19) |
C24 | 0.0446 (17) | 0.082 (2) | 0.098 (2) | −0.0086 (17) | 0.0240 (18) | −0.049 (2) |
C25 | 0.086 (2) | 0.114 (3) | 0.166 (4) | −0.014 (2) | 0.055 (3) | −0.090 (3) |
C26 | 0.0468 (17) | 0.093 (2) | 0.064 (2) | −0.0045 (17) | 0.0222 (15) | −0.0266 (18) |
C27 | 0.0476 (15) | 0.0644 (19) | 0.0523 (16) | −0.0006 (14) | 0.0163 (14) | −0.0114 (14) |
C28 | 0.0386 (13) | 0.0412 (15) | 0.0393 (14) | 0.0027 (11) | 0.0147 (12) | 0.0020 (11) |
C29 | 0.089 (2) | 0.0556 (19) | 0.070 (2) | 0.0118 (17) | 0.0428 (19) | −0.0110 (15) |
C30 | 0.0446 (15) | 0.0434 (15) | 0.0440 (15) | −0.0046 (13) | 0.0170 (13) | −0.0006 (12) |
C31 | 0.066 (2) | 0.068 (2) | 0.102 (2) | −0.0185 (17) | 0.048 (2) | 0.0042 (18) |
C32 | 0.0459 (16) | 0.0559 (17) | 0.0611 (18) | −0.0033 (13) | 0.0242 (14) | 0.0049 (14) |
Geometric parameters (Å, º) top
O1—C1 | 1.386 (3) | C21—C27 | 1.385 (4) |
O1—C4 | 1.358 (3) | C22—C23 | 1.373 (5) |
O2—C12 | 1.211 (3) | C23—C24 | 1.388 (5) |
O3—C12 | 1.328 (3) | C24—C25 | 1.513 (6) |
O3—C13 | 1.448 (3) | C24—C26 | 1.371 (5) |
O4—C14 | 1.203 (3) | C26—C27 | 1.381 (4) |
O5—C14 | 1.329 (3) | N1—H101 | 0.862 |
O5—C15 | 1.444 (4) | N2—H201 | 0.860 |
O6—C17 | 1.383 (3) | C6—H6 | 0.930 |
O6—C20 | 1.354 (3) | C7—H7 | 0.930 |
O7—C28 | 1.202 (3) | C9—H91 | 0.960 |
O8—C28 | 1.329 (3) | C9—H92 | 0.960 |
O8—C29 | 1.446 (3) | C9—H93 | 0.960 |
O9—C30 | 1.195 (3) | C10—H10 | 0.930 |
O10—C30 | 1.329 (3) | C11—H11 | 0.930 |
O10—C31 | 1.445 (4) | C13—H131 | 0.960 |
N1—C2 | 1.400 (3) | C13—H132 | 0.960 |
N1—C16 | 1.463 (3) | C13—H133 | 0.960 |
N2—C18 | 1.390 (3) | C15—H151 | 0.960 |
N2—C32 | 1.445 (3) | C15—H152 | 0.960 |
C1—C2 | 1.368 (3) | C15—H153 | 0.960 |
C1—C5 | 1.465 (3) | C16—H161 | 0.960 |
C2—C3 | 1.434 (3) | C16—H162 | 0.960 |
C3—C4 | 1.368 (3) | C16—H163 | 0.960 |
C3—C12 | 1.470 (3) | C22—H22 | 0.930 |
C4—C14 | 1.471 (4) | C23—H23 | 0.930 |
C5—C6 | 1.392 (3) | C25—H251 | 0.960 |
C5—C11 | 1.400 (4) | C25—H252 | 0.960 |
C6—C7 | 1.381 (4) | C25—H253 | 0.960 |
C7—C8 | 1.389 (4) | C26—H26 | 0.930 |
C8—C9 | 1.505 (4) | C27—H27 | 0.930 |
C8—C10 | 1.388 (4) | C29—H291 | 0.960 |
C10—C11 | 1.381 (4) | C29—H292 | 0.960 |
C17—C18 | 1.359 (3) | C29—H293 | 0.960 |
C17—C21 | 1.460 (3) | C31—H311 | 0.960 |
C18—C19 | 1.436 (3) | C31—H312 | 0.960 |
C19—C20 | 1.363 (3) | C31—H313 | 0.960 |
C19—C28 | 1.467 (3) | C32—H321 | 0.960 |
C20—C30 | 1.471 (4) | C32—H322 | 0.960 |
C21—C22 | 1.385 (3) | C32—H323 | 0.960 |
| | | |
C1—O1—C4 | 107.54 (19) | C18—N2—H201 | 120.5 |
C12—O3—C13 | 115.9 (2) | C32—N2—H201 | 120.6 |
C14—O5—C15 | 116.2 (2) | C5—C6—H6 | 119.7 |
C17—O6—C20 | 107.76 (19) | C7—C6—H6 | 119.6 |
C28—O8—C29 | 115.9 (2) | C6—C7—H7 | 119.2 |
C30—O10—C31 | 116.4 (2) | C8—C7—H7 | 119.1 |
C2—N1—C16 | 117.6 (2) | C8—C9—H91 | 109.5 |
C18—N2—C32 | 118.9 (2) | C8—C9—H92 | 109.3 |
O1—C1—C2 | 109.3 (2) | C8—C9—H93 | 109.6 |
O1—C1—C5 | 114.8 (2) | H91—C9—H92 | 109.5 |
C2—C1—C5 | 135.9 (2) | H91—C9—H93 | 109.5 |
N1—C2—C1 | 127.7 (2) | H92—C9—H93 | 109.5 |
N1—C2—C3 | 125.9 (2) | C8—C10—H10 | 119.2 |
C1—C2—C3 | 106.4 (2) | C11—C10—H10 | 119.1 |
C2—C3—C4 | 106.7 (2) | C5—C11—H11 | 119.7 |
C2—C3—C12 | 125.2 (2) | C10—C11—H11 | 119.9 |
C4—C3—C12 | 128.1 (2) | O3—C13—H131 | 109.7 |
O1—C4—C3 | 110.0 (2) | O3—C13—H132 | 109.3 |
O1—C4—C14 | 117.2 (2) | O3—C13—H133 | 109.4 |
C3—C4—C14 | 132.4 (2) | H131—C13—H132 | 109.5 |
C1—C5—C6 | 120.8 (2) | H131—C13—H133 | 109.5 |
C1—C5—C11 | 121.0 (2) | H132—C13—H133 | 109.5 |
C6—C5—C11 | 118.1 (2) | O5—C15—H151 | 109.2 |
C5—C6—C7 | 120.6 (2) | O5—C15—H152 | 109.7 |
C6—C7—C8 | 121.7 (2) | O5—C15—H153 | 109.6 |
C7—C8—C9 | 120.7 (2) | H151—C15—H152 | 109.5 |
C7—C8—C10 | 117.5 (2) | H151—C15—H153 | 109.5 |
C9—C8—C10 | 121.8 (3) | H152—C15—H153 | 109.5 |
C8—C10—C11 | 121.7 (2) | N1—C16—H161 | 109.7 |
C5—C11—C10 | 120.4 (2) | N1—C16—H162 | 109.3 |
O2—C12—O3 | 124.2 (2) | N1—C16—H163 | 109.4 |
O2—C12—C3 | 123.5 (2) | H161—C16—H162 | 109.5 |
O3—C12—C3 | 112.2 (2) | H161—C16—H163 | 109.5 |
O4—C14—O5 | 124.9 (2) | H162—C16—H163 | 109.5 |
O4—C14—C4 | 123.5 (2) | C21—C22—H22 | 119.8 |
O5—C14—C4 | 111.7 (2) | C23—C22—H22 | 119.6 |
O6—C17—C18 | 109.4 (2) | C22—C23—H23 | 119.3 |
O6—C17—C21 | 115.4 (2) | C24—C23—H23 | 119.1 |
C18—C17—C21 | 135.1 (2) | C24—C25—H251 | 109.4 |
N2—C18—C17 | 128.0 (2) | C24—C25—H252 | 109.3 |
N2—C18—C19 | 125.7 (2) | C24—C25—H253 | 109.7 |
C17—C18—C19 | 106.3 (2) | H251—C25—H252 | 109.5 |
C18—C19—C20 | 106.8 (2) | H251—C25—H253 | 109.5 |
C18—C19—C28 | 123.8 (2) | H252—C25—H253 | 109.5 |
C20—C19—C28 | 129.4 (2) | C24—C26—H26 | 119.2 |
O6—C20—C19 | 109.7 (2) | C27—C26—H26 | 119.3 |
O6—C20—C30 | 117.5 (2) | C21—C27—H27 | 119.6 |
C19—C20—C30 | 132.5 (2) | C26—C27—H27 | 119.7 |
C17—C21—C22 | 121.3 (2) | O8—C29—H291 | 109.4 |
C17—C21—C27 | 120.6 (2) | O8—C29—H292 | 109.5 |
C22—C21—C27 | 118.0 (2) | O8—C29—H293 | 109.6 |
C21—C22—C23 | 120.6 (3) | H291—C29—H292 | 109.5 |
C22—C23—C24 | 121.6 (3) | H291—C29—H293 | 109.5 |
C23—C24—C25 | 121.1 (3) | H292—C29—H293 | 109.5 |
C23—C24—C26 | 117.6 (3) | O10—C31—H311 | 110.2 |
C25—C24—C26 | 121.3 (3) | O10—C31—H312 | 109.1 |
C24—C26—C27 | 121.5 (3) | O10—C31—H313 | 109.0 |
C21—C27—C26 | 120.7 (2) | H311—C31—H312 | 109.5 |
O7—C28—O8 | 123.3 (2) | H311—C31—H313 | 109.5 |
O7—C28—C19 | 122.9 (2) | H312—C31—H313 | 109.5 |
O8—C28—C19 | 113.7 (2) | N2—C32—H321 | 109.4 |
O9—C30—O10 | 124.3 (2) | N2—C32—H322 | 109.3 |
O9—C30—C20 | 124.1 (2) | N2—C32—H323 | 109.8 |
O10—C30—C20 | 111.6 (2) | H321—C32—H322 | 109.5 |
C2—N1—H101 | 109.6 | H321—C32—H323 | 109.5 |
C16—N1—H101 | 112.9 | H322—C32—H323 | 109.5 |
| | | |
C1—O1—C4—C3 | 2.4 (2) | C1—C5—C6—C7 | −175.2 (2) |
C1—O1—C4—C14 | −171.06 (18) | C1—C5—C11—C10 | 175.1 (2) |
C4—O1—C1—C2 | −1.9 (2) | C6—C5—C11—C10 | −1.3 (3) |
C4—O1—C1—C5 | 176.56 (18) | C11—C5—C6—C7 | 1.1 (3) |
C13—O3—C12—O2 | −6.1 (3) | C5—C6—C7—C8 | 0.4 (3) |
C13—O3—C12—C3 | 176.5 (2) | C6—C7—C8—C9 | 177.8 (2) |
C15—O5—C14—O4 | −0.0 (2) | C6—C7—C8—C10 | −1.7 (3) |
C15—O5—C14—C4 | 179.4 (2) | C7—C8—C10—C11 | 1.5 (3) |
C17—O6—C20—C19 | 2.3 (2) | C9—C8—C10—C11 | −177.9 (2) |
C17—O6—C20—C30 | −172.52 (18) | C8—C10—C11—C5 | −0.1 (2) |
C20—O6—C17—C18 | −1.9 (2) | O6—C17—C18—N2 | −178.60 (19) |
C20—O6—C17—C21 | 175.10 (18) | O6—C17—C18—C19 | 0.7 (2) |
C29—O8—C28—O7 | −8.6 (3) | O6—C17—C21—C22 | 28.0 (3) |
C29—O8—C28—C19 | 174.1 (2) | O6—C17—C21—C27 | −150.7 (2) |
C31—O10—C30—O9 | −0.2 (3) | C18—C17—C21—C22 | −156.0 (2) |
C31—O10—C30—C20 | 179.0 (2) | C18—C17—C21—C27 | 25.3 (3) |
C16—N1—C2—C1 | 57.1 (3) | C21—C17—C18—N2 | 5.2 (4) |
C16—N1—C2—C3 | −123.8 (2) | C21—C17—C18—C19 | −175.4 (2) |
C32—N2—C18—C17 | 53.0 (3) | N2—C18—C19—C20 | −180.0 (2) |
C32—N2—C18—C19 | −126.2 (2) | N2—C18—C19—C28 | 0.4 (3) |
O1—C1—C2—N1 | 179.92 (19) | C17—C18—C19—C20 | 0.7 (2) |
O1—C1—C2—C3 | 0.6 (2) | C17—C18—C19—C28 | −178.90 (19) |
O1—C1—C5—C6 | 23.9 (3) | C18—C19—C20—O6 | −1.9 (2) |
O1—C1—C5—C11 | −152.4 (2) | C18—C19—C20—C30 | 171.9 (2) |
C2—C1—C5—C6 | −158.3 (2) | C18—C19—C28—O7 | −31.7 (3) |
C2—C1—C5—C11 | 25.5 (3) | C18—C19—C28—O8 | 145.7 (2) |
C5—C1—C2—N1 | 1.9 (4) | C20—C19—C28—O7 | 148.8 (2) |
C5—C1—C2—C3 | −177.3 (2) | C20—C19—C28—O8 | −33.8 (3) |
N1—C2—C3—C4 | −178.5 (2) | C28—C19—C20—O6 | 177.7 (2) |
N1—C2—C3—C12 | 4.0 (3) | C28—C19—C20—C30 | −8.5 (4) |
C1—C2—C3—C4 | 0.8 (2) | O6—C20—C30—O9 | 160.9 (2) |
C1—C2—C3—C12 | −176.7 (2) | O6—C20—C30—O10 | −18.3 (2) |
C2—C3—C4—O1 | −2.0 (2) | C19—C20—C30—O9 | −12.5 (4) |
C2—C3—C4—C14 | 170.1 (2) | C19—C20—C30—O10 | 168.2 (2) |
C2—C3—C12—O2 | −36.7 (3) | C17—C21—C22—C23 | −177.5 (2) |
C2—C3—C12—O3 | 140.7 (2) | C17—C21—C27—C26 | 177.2 (2) |
C4—C3—C12—O2 | 146.3 (2) | C22—C21—C27—C26 | −1.6 (3) |
C4—C3—C12—O3 | −36.3 (3) | C27—C21—C22—C23 | 1.3 (3) |
C12—C3—C4—O1 | 175.43 (19) | C21—C22—C23—C24 | 0.7 (4) |
C12—C3—C4—C14 | −12.4 (4) | C22—C23—C24—C25 | 176.0 (2) |
O1—C4—C14—O4 | 157.8 (2) | C22—C23—C24—C26 | −2.4 (4) |
O1—C4—C14—O5 | −21.6 (2) | C23—C24—C26—C27 | 2.1 (4) |
C3—C4—C14—O4 | −13.9 (4) | C25—C24—C26—C27 | −176.3 (2) |
C3—C4—C14—O5 | 166.7 (2) | C24—C26—C27—C21 | −0.2 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H101···O7i | 0.86 | 2.38 | 3.089 (3) | 140 |
N2—H201···O2ii | 0.86 | 2.64 | 3.253 (2) | 129 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2. |