In the title compound, C
19H
21NO
2, the asymmetric unit contains two independent molecules (
A and
B) linked by a strong N—H
O hydrogen bond. The molecular assembly in the structure is established by N—H
O, C—H
O and C—H
π (arene) interactions. Intermolecular N—H
O hydrogen bonds involving different types of molecules generate an infinite
ABAB… chain running parallel to the [001] direction. The combination of N—H
O and C—H
O hydrogen bonds results into a two-dimensional supramolecular framework of
R56(32) rings in the (011) plane.
Supporting information
CCDC reference: 620757
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C)= 0.004 Å
- R factor = 0.058
- wR factor = 0.137
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); 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 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2003).
syn-
N-[2-Methyl-1-(4-methyl-phenyl)-3-oxo-3-phenyl-propyl]-acetamide
top
Crystal data top
C19H21NO2 | F(000) = 1264 |
Mr = 295.37 | Dx = 1.180 Mg m−3 |
Monoclinic, P21/c | Melting point: 392(1) K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 18.3820 (18) Å | Cell parameters from 1457 reflections |
b = 11.7845 (12) Å | θ = 2.2–20.3° |
c = 16.4961 (16) Å | µ = 0.08 mm−1 |
β = 111.444 (2)° | T = 153 K |
V = 3326.1 (6) Å3 | Block, colourless |
Z = 8 | 0.35 × 0.12 × 0.10 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 5844 independent reflections |
Radiation source: fine-focus sealed tube | 4060 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.063 |
φ and ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −21→13 |
Tmin = 0.984, Tmax = 0.992 | k = −14→12 |
17160 measured reflections | l = −19→19 |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.049P)2 + 0.971P] where P = (Fo2 + 2Fc2)/3 |
5844 reflections | (Δ/σ)max = 0.001 |
398 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.26 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.92272 (10) | 0.29281 (14) | 0.75960 (11) | 0.0284 (4) | |
O2 | 0.89252 (10) | 0.55527 (14) | 0.51629 (10) | 0.0245 (4) | |
O3 | 0.59270 (10) | 0.46821 (15) | 0.20451 (12) | 0.0346 (5) | |
O4 | 0.82350 (10) | 0.70969 (16) | 0.22105 (11) | 0.0331 (5) | |
N1 | 0.86134 (11) | 0.61008 (16) | 0.63124 (12) | 0.0184 (5) | |
H1A | 0.8524 | 0.6672 | 0.6588 | 0.022* | |
N2 | 0.82371 (11) | 0.59357 (16) | 0.32983 (12) | 0.0208 (5) | |
H2A | 0.8523 | 0.5585 | 0.3763 | 0.025* | |
C1 | 0.89244 (13) | 0.3571 (2) | 0.87911 (15) | 0.0196 (6) | |
C2 | 0.86978 (14) | 0.4449 (2) | 0.92152 (16) | 0.0257 (6) | |
H2 | 0.8640 | 0.5181 | 0.8990 | 0.031* | |
C3 | 0.85588 (15) | 0.4229 (2) | 0.99721 (16) | 0.0290 (6) | |
H3 | 0.8406 | 0.4816 | 1.0252 | 0.035* | |
C4 | 0.86454 (15) | 0.3149 (2) | 1.03111 (16) | 0.0298 (7) | |
H4 | 0.8559 | 0.3009 | 1.0823 | 0.036* | |
C5 | 0.88608 (14) | 0.2271 (2) | 0.98907 (16) | 0.0278 (6) | |
H5 | 0.8912 | 0.1539 | 1.0115 | 0.033* | |
C6 | 0.90010 (13) | 0.2483 (2) | 0.91357 (16) | 0.0236 (6) | |
H6 | 0.9148 | 0.1891 | 0.8856 | 0.028* | |
C7 | 0.90873 (13) | 0.3745 (2) | 0.79742 (15) | 0.0201 (6) | |
C8 | 0.91163 (13) | 0.4925 (2) | 0.76189 (15) | 0.0197 (6) | |
H8 | 0.8927 | 0.5470 | 0.7945 | 0.024* | |
C9 | 0.99618 (14) | 0.5212 (2) | 0.77561 (16) | 0.0267 (6) | |
H9A | 0.9988 | 0.5969 | 0.7554 | 0.032* | |
H9B | 1.0153 | 0.4686 | 0.7436 | 0.032* | |
H9C | 1.0276 | 0.5161 | 0.8365 | 0.032* | |
C10 | 0.85753 (13) | 0.49703 (19) | 0.66543 (14) | 0.0177 (5) | |
H10 | 0.8774 | 0.4429 | 0.6334 | 0.021* | |
C11 | 0.77339 (14) | 0.4650 (2) | 0.65028 (15) | 0.0195 (6) | |
C12 | 0.73356 (14) | 0.5158 (2) | 0.69802 (16) | 0.0262 (6) | |
H12 | 0.7594 | 0.5677 | 0.7415 | 0.031* | |
C13 | 0.65607 (15) | 0.4902 (2) | 0.68167 (16) | 0.0294 (6) | |
H13 | 0.6308 | 0.5254 | 0.7145 | 0.035* | |
C14 | 0.61508 (15) | 0.4132 (2) | 0.61753 (17) | 0.0282 (6) | |
C15 | 0.65518 (15) | 0.3625 (2) | 0.57051 (16) | 0.0264 (6) | |
H15 | 0.6293 | 0.3106 | 0.5271 | 0.032* | |
C16 | 0.73307 (14) | 0.3874 (2) | 0.58670 (15) | 0.0219 (6) | |
H16 | 0.7585 | 0.3514 | 0.5544 | 0.026* | |
C17 | 0.53060 (16) | 0.3865 (3) | 0.59915 (19) | 0.0427 (8) | |
H17A | 0.5074 | 0.4474 | 0.6199 | 0.051* | |
H17B | 0.5269 | 0.3175 | 0.6283 | 0.051* | |
H17C | 0.5036 | 0.3777 | 0.5375 | 0.051* | |
C18 | 0.87772 (13) | 0.6312 (2) | 0.56014 (15) | 0.0194 (5) | |
C19 | 0.87637 (14) | 0.7538 (2) | 0.53587 (16) | 0.0237 (6) | |
H19A | 0.8358 | 0.7662 | 0.4801 | 0.028* | |
H19B | 0.9259 | 0.7744 | 0.5330 | 0.028* | |
H19C | 0.8665 | 0.7996 | 0.5789 | 0.028* | |
C20 | 0.61483 (14) | 0.3157 (2) | 0.30375 (16) | 0.0242 (6) | |
C25 | 0.53540 (15) | 0.3028 (2) | 0.28765 (17) | 0.0324 (7) | |
H25 | 0.4998 | 0.3552 | 0.2527 | 0.039* | |
C24 | 0.50918 (16) | 0.2128 (3) | 0.32327 (19) | 0.0393 (7) | |
H24 | 0.4561 | 0.2048 | 0.3121 | 0.047* | |
C23 | 0.56162 (16) | 0.1347 (2) | 0.37538 (18) | 0.0340 (7) | |
H23 | 0.5437 | 0.0740 | 0.3990 | 0.041* | |
C22 | 0.64029 (16) | 0.1468 (2) | 0.39237 (18) | 0.0315 (7) | |
H22 | 0.6756 | 0.0947 | 0.4281 | 0.038* | |
C21 | 0.66707 (15) | 0.2362 (2) | 0.35645 (16) | 0.0260 (6) | |
H21 | 0.7202 | 0.2433 | 0.3675 | 0.031* | |
C26 | 0.64032 (15) | 0.4132 (2) | 0.26224 (16) | 0.0241 (6) | |
C27 | 0.72715 (14) | 0.4412 (2) | 0.29046 (16) | 0.0215 (6) | |
H27 | 0.7549 | 0.4090 | 0.3484 | 0.026* | |
C28 | 0.75770 (15) | 0.3859 (2) | 0.22520 (16) | 0.0307 (7) | |
H28A | 0.7520 | 0.3050 | 0.2267 | 0.037* | |
H28B | 0.8119 | 0.4045 | 0.2403 | 0.037* | |
H28C | 0.7284 | 0.4135 | 0.1677 | 0.037* | |
C29 | 0.73956 (13) | 0.5696 (2) | 0.29407 (15) | 0.0198 (6) | |
H29 | 0.7181 | 0.5991 | 0.2344 | 0.024* | |
C30 | 0.70310 (13) | 0.6356 (2) | 0.34910 (14) | 0.0186 (5) | |
C31 | 0.68545 (14) | 0.7496 (2) | 0.33124 (15) | 0.0225 (6) | |
H31 | 0.6906 | 0.7821 | 0.2823 | 0.027* | |
C32 | 0.66027 (14) | 0.8155 (2) | 0.38530 (16) | 0.0258 (6) | |
H32 | 0.6489 | 0.8917 | 0.3719 | 0.031* | |
C33 | 0.65165 (14) | 0.7704 (2) | 0.45909 (16) | 0.0242 (6) | |
C34 | 0.66784 (14) | 0.6560 (2) | 0.47525 (16) | 0.0248 (6) | |
H34 | 0.6615 | 0.6230 | 0.5235 | 0.030* | |
C35 | 0.69305 (13) | 0.5896 (2) | 0.42168 (15) | 0.0212 (6) | |
H35 | 0.7034 | 0.5131 | 0.4344 | 0.025* | |
C36 | 0.62573 (17) | 0.8425 (3) | 0.51910 (18) | 0.0391 (7) | |
H36A | 0.6481 | 0.9169 | 0.5234 | 0.047* | |
H36B | 0.6429 | 0.8082 | 0.5758 | 0.047* | |
H36C | 0.5698 | 0.8482 | 0.4963 | 0.047* | |
C37 | 0.85815 (15) | 0.6673 (2) | 0.29361 (16) | 0.0223 (6) | |
C38 | 0.94058 (14) | 0.6983 (2) | 0.34834 (17) | 0.0278 (6) | |
H38A | 0.9620 | 0.6420 | 0.3928 | 0.033* | |
H38B | 0.9412 | 0.7709 | 0.3749 | 0.033* | |
H38C | 0.9714 | 0.7018 | 0.3123 | 0.033* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0350 (11) | 0.0204 (10) | 0.0336 (10) | 0.0032 (8) | 0.0169 (9) | 0.0018 (8) |
O2 | 0.0315 (11) | 0.0235 (10) | 0.0225 (9) | 0.0019 (8) | 0.0145 (8) | −0.0028 (8) |
O3 | 0.0244 (11) | 0.0314 (11) | 0.0387 (11) | 0.0025 (8) | 0.0004 (9) | 0.0072 (9) |
O4 | 0.0361 (12) | 0.0369 (12) | 0.0273 (11) | −0.0036 (9) | 0.0130 (9) | 0.0119 (9) |
N1 | 0.0252 (12) | 0.0162 (11) | 0.0178 (11) | 0.0010 (8) | 0.0126 (9) | −0.0016 (9) |
N2 | 0.0220 (12) | 0.0208 (12) | 0.0197 (11) | 0.0009 (9) | 0.0077 (9) | 0.0047 (9) |
C1 | 0.0155 (13) | 0.0206 (14) | 0.0205 (13) | −0.0017 (10) | 0.0040 (11) | 0.0005 (11) |
C2 | 0.0312 (16) | 0.0232 (15) | 0.0233 (14) | −0.0037 (11) | 0.0105 (12) | 0.0026 (12) |
C3 | 0.0353 (17) | 0.0273 (16) | 0.0256 (15) | −0.0071 (12) | 0.0123 (13) | −0.0052 (12) |
C4 | 0.0328 (17) | 0.0340 (17) | 0.0217 (14) | −0.0158 (12) | 0.0089 (12) | −0.0010 (12) |
C5 | 0.0267 (15) | 0.0234 (15) | 0.0270 (15) | −0.0101 (11) | 0.0025 (12) | 0.0058 (12) |
C6 | 0.0185 (14) | 0.0224 (15) | 0.0263 (14) | −0.0026 (10) | 0.0041 (11) | 0.0011 (11) |
C7 | 0.0153 (13) | 0.0191 (14) | 0.0232 (13) | 0.0015 (10) | 0.0038 (11) | −0.0026 (11) |
C8 | 0.0202 (14) | 0.0170 (13) | 0.0212 (13) | −0.0010 (10) | 0.0068 (11) | −0.0008 (10) |
C9 | 0.0246 (15) | 0.0223 (15) | 0.0292 (15) | −0.0018 (11) | 0.0051 (12) | 0.0002 (11) |
C10 | 0.0229 (14) | 0.0136 (13) | 0.0184 (13) | −0.0004 (10) | 0.0097 (11) | −0.0024 (10) |
C11 | 0.0240 (14) | 0.0171 (13) | 0.0180 (13) | 0.0028 (10) | 0.0084 (11) | 0.0057 (10) |
C12 | 0.0229 (15) | 0.0343 (16) | 0.0213 (14) | −0.0023 (12) | 0.0077 (11) | −0.0063 (12) |
C13 | 0.0247 (16) | 0.0420 (18) | 0.0254 (14) | −0.0014 (12) | 0.0137 (12) | −0.0018 (13) |
C14 | 0.0216 (15) | 0.0319 (17) | 0.0302 (15) | −0.0012 (12) | 0.0084 (12) | 0.0078 (12) |
C15 | 0.0261 (16) | 0.0210 (15) | 0.0276 (15) | −0.0031 (11) | 0.0043 (12) | −0.0006 (12) |
C16 | 0.0269 (15) | 0.0181 (14) | 0.0220 (13) | 0.0027 (11) | 0.0105 (11) | 0.0014 (11) |
C17 | 0.0301 (18) | 0.053 (2) | 0.0452 (19) | −0.0069 (14) | 0.0141 (14) | 0.0032 (16) |
C18 | 0.0156 (13) | 0.0216 (14) | 0.0197 (13) | −0.0011 (10) | 0.0049 (11) | −0.0010 (11) |
C19 | 0.0261 (15) | 0.0235 (14) | 0.0230 (14) | −0.0011 (11) | 0.0106 (11) | 0.0001 (11) |
C20 | 0.0217 (15) | 0.0219 (15) | 0.0262 (14) | −0.0024 (11) | 0.0054 (11) | −0.0054 (11) |
C25 | 0.0203 (16) | 0.0345 (17) | 0.0369 (16) | 0.0025 (12) | 0.0038 (12) | 0.0026 (13) |
C24 | 0.0216 (16) | 0.048 (2) | 0.0469 (18) | −0.0104 (13) | 0.0104 (14) | 0.0032 (15) |
C23 | 0.0309 (17) | 0.0303 (17) | 0.0394 (17) | −0.0119 (13) | 0.0113 (13) | −0.0002 (13) |
C22 | 0.0300 (17) | 0.0201 (15) | 0.0402 (17) | −0.0031 (12) | 0.0077 (13) | −0.0020 (13) |
C21 | 0.0210 (14) | 0.0211 (15) | 0.0342 (15) | −0.0039 (11) | 0.0080 (12) | −0.0035 (12) |
C26 | 0.0228 (15) | 0.0202 (14) | 0.0246 (14) | 0.0021 (11) | 0.0031 (12) | −0.0056 (11) |
C27 | 0.0194 (14) | 0.0210 (14) | 0.0227 (13) | 0.0032 (10) | 0.0058 (11) | 0.0038 (11) |
C28 | 0.0282 (16) | 0.0306 (16) | 0.0306 (15) | 0.0052 (12) | 0.0078 (12) | −0.0016 (13) |
C29 | 0.0185 (14) | 0.0208 (14) | 0.0181 (13) | −0.0013 (10) | 0.0045 (11) | 0.0049 (11) |
C30 | 0.0114 (13) | 0.0240 (14) | 0.0175 (13) | −0.0029 (10) | 0.0016 (10) | 0.0004 (11) |
C31 | 0.0254 (15) | 0.0196 (14) | 0.0220 (13) | −0.0021 (11) | 0.0080 (11) | 0.0053 (11) |
C32 | 0.0264 (15) | 0.0161 (14) | 0.0316 (15) | 0.0027 (11) | 0.0066 (12) | −0.0004 (11) |
C33 | 0.0197 (14) | 0.0290 (15) | 0.0229 (14) | 0.0006 (11) | 0.0065 (11) | −0.0026 (12) |
C34 | 0.0213 (15) | 0.0314 (16) | 0.0218 (14) | 0.0016 (11) | 0.0079 (11) | 0.0048 (12) |
C35 | 0.0181 (14) | 0.0186 (14) | 0.0260 (14) | 0.0009 (10) | 0.0069 (11) | 0.0046 (11) |
C36 | 0.0430 (19) | 0.0395 (18) | 0.0377 (17) | 0.0049 (14) | 0.0184 (15) | −0.0031 (14) |
C37 | 0.0288 (15) | 0.0184 (14) | 0.0257 (14) | 0.0007 (11) | 0.0172 (12) | 0.0014 (11) |
C38 | 0.0279 (16) | 0.0264 (16) | 0.0347 (15) | −0.0071 (12) | 0.0180 (13) | −0.0004 (12) |
Geometric parameters (Å, º) top
O1—C7 | 1.224 (3) | C18—O2 | 1.242 (3) |
O2—C18 | 1.242 (3) | C18—C19 | 1.497 (3) |
O3—C26 | 1.218 (3) | C19—H19A | 0.96 |
O4—C37 | 1.237 (3) | C19—H19B | 0.96 |
N1—C18 | 1.337 (3) | C19—H19C | 0.96 |
N1—C10 | 1.458 (3) | C20—C25 | 1.393 (3) |
N1—H1A | 0.86 | C20—C21 | 1.395 (3) |
N2—C37 | 1.338 (3) | C20—C26 | 1.498 (3) |
N2—C29 | 1.468 (3) | C25—C24 | 1.382 (4) |
N2—H2A | 0.86 | C25—H25 | 0.93 |
C1—C6 | 1.388 (3) | C24—C23 | 1.382 (4) |
C1—C2 | 1.395 (3) | C24—H24 | 0.93 |
C1—C7 | 1.498 (3) | C23—C22 | 1.376 (4) |
C2—C3 | 1.387 (3) | C23—H23 | 0.93 |
C2—H2 | 0.93 | C22—C21 | 1.385 (4) |
C3—C4 | 1.376 (4) | C22—H22 | 0.93 |
C3—H3 | 0.93 | C21—H21 | 0.93 |
C4—C5 | 1.381 (4) | C26—C27 | 1.526 (3) |
C4—H4 | 0.93 | C27—C29 | 1.528 (3) |
C5—C6 | 1.384 (3) | C27—C28 | 1.530 (3) |
C5—H5 | 0.93 | C27—H27 | 0.98 |
C6—H6 | 0.93 | C28—H28A | 0.96 |
C7—C8 | 1.517 (3) | C28—H28B | 0.96 |
C8—C9 | 1.525 (3) | C28—H28C | 0.96 |
C8—C10 | 1.538 (3) | C29—C30 | 1.524 (3) |
C8—H8 | 0.98 | C29—H29 | 0.98 |
C9—H9A | 0.96 | C30—C35 | 1.387 (3) |
C9—H9B | 0.96 | C30—C31 | 1.388 (3) |
C9—H9C | 0.96 | C31—C32 | 1.384 (3) |
C10—C11 | 1.521 (3) | C31—H31 | 0.93 |
C10—H10 | 0.98 | C32—C33 | 1.389 (3) |
C11—C16 | 1.385 (3) | C32—H32 | 0.93 |
C11—C12 | 1.391 (3) | C33—C34 | 1.386 (3) |
C12—C13 | 1.383 (3) | C33—C36 | 1.507 (3) |
C12—H12 | 0.93 | C34—C35 | 1.381 (3) |
C13—C14 | 1.388 (4) | C34—H34 | 0.93 |
C13—H13 | 0.93 | C35—H35 | 0.93 |
C14—C15 | 1.386 (4) | C36—H36A | 0.96 |
C14—C17 | 1.503 (4) | C36—H36B | 0.96 |
C15—C16 | 1.388 (3) | C36—H36C | 0.96 |
C15—H15 | 0.93 | C37—C38 | 1.498 (3) |
C16—H16 | 0.93 | C38—H38A | 0.96 |
C17—H17A | 0.96 | C38—H38B | 0.96 |
C17—H17B | 0.96 | C38—H38C | 0.96 |
C17—H17C | 0.96 | | |
| | | |
C18—N1—C10 | 124.58 (19) | H19A—C19—H19B | 109.5 |
C18—N1—H1A | 117.7 | C18—C19—H19C | 109.5 |
C10—N1—H1A | 117.7 | H19A—C19—H19C | 109.5 |
C37—N2—C29 | 123.2 (2) | H19B—C19—H19C | 109.5 |
C37—N2—H2A | 118.4 | C25—C20—C21 | 118.7 (2) |
C29—N2—H2A | 118.4 | C25—C20—C26 | 118.5 (2) |
C6—C1—C2 | 118.9 (2) | C21—C20—C26 | 122.7 (2) |
C6—C1—C7 | 118.1 (2) | C24—C25—C20 | 120.4 (3) |
C2—C1—C7 | 123.0 (2) | C24—C25—H25 | 119.8 |
C3—C2—C1 | 120.0 (2) | C20—C25—H25 | 119.8 |
C3—C2—H2 | 120.0 | C25—C24—C23 | 120.2 (3) |
C1—C2—H2 | 120.0 | C25—C24—H24 | 119.9 |
C4—C3—C2 | 120.4 (3) | C23—C24—H24 | 119.9 |
C4—C3—H3 | 119.8 | C22—C23—C24 | 120.0 (3) |
C2—C3—H3 | 119.8 | C22—C23—H23 | 120.0 |
C3—C4—C5 | 120.0 (2) | C24—C23—H23 | 120.0 |
C3—C4—H4 | 120.0 | C23—C22—C21 | 120.2 (3) |
C5—C4—H4 | 120.0 | C23—C22—H22 | 119.9 |
C4—C5—C6 | 119.9 (2) | C21—C22—H22 | 119.9 |
C4—C5—H5 | 120.0 | C22—C21—C20 | 120.4 (2) |
C6—C5—H5 | 120.0 | C22—C21—H21 | 119.8 |
C5—C6—C1 | 120.7 (2) | C20—C21—H21 | 119.8 |
C5—C6—H6 | 119.6 | O3—C26—C20 | 120.7 (2) |
C1—C6—H6 | 119.6 | O3—C26—C27 | 119.7 (2) |
O1—C7—C1 | 119.9 (2) | C20—C26—C27 | 119.6 (2) |
O1—C7—C8 | 118.7 (2) | C26—C27—C29 | 110.51 (19) |
C1—C7—C8 | 121.3 (2) | C26—C27—C28 | 107.8 (2) |
C7—C8—C9 | 108.89 (19) | C29—C27—C28 | 111.2 (2) |
C7—C8—C10 | 109.32 (19) | C26—C27—H27 | 109.1 |
C9—C8—C10 | 112.59 (19) | C29—C27—H27 | 109.1 |
C7—C8—H8 | 108.7 | C28—C27—H27 | 109.1 |
C9—C8—H8 | 108.7 | C27—C28—H28A | 109.5 |
C10—C8—H8 | 108.7 | C27—C28—H28B | 109.5 |
C8—C9—H9A | 109.5 | H28A—C28—H28B | 109.5 |
C8—C9—H9B | 109.5 | C27—C28—H28C | 109.5 |
H9A—C9—H9B | 109.5 | H28A—C28—H28C | 109.5 |
C8—C9—H9C | 109.5 | H28B—C28—H28C | 109.5 |
H9A—C9—H9C | 109.5 | N2—C29—C30 | 106.90 (18) |
H9B—C9—H9C | 109.5 | N2—C29—C27 | 109.07 (18) |
N1—C10—C11 | 110.65 (18) | C30—C29—C27 | 115.91 (19) |
N1—C10—C8 | 109.12 (18) | N2—C29—H29 | 108.2 |
C11—C10—C8 | 113.27 (19) | C30—C29—H29 | 108.2 |
N1—C10—H10 | 107.9 | C27—C29—H29 | 108.2 |
C11—C10—H10 | 107.9 | C35—C30—C31 | 117.8 (2) |
C8—C10—H10 | 107.9 | C35—C30—C29 | 122.8 (2) |
C16—C11—C12 | 117.8 (2) | C31—C30—C29 | 119.2 (2) |
C16—C11—C10 | 121.2 (2) | C32—C31—C30 | 120.9 (2) |
C12—C11—C10 | 120.9 (2) | C32—C31—H31 | 119.5 |
C13—C12—C11 | 120.9 (2) | C30—C31—H31 | 119.5 |
C13—C12—H12 | 119.6 | C31—C32—C33 | 121.5 (2) |
C11—C12—H12 | 119.6 | C31—C32—H32 | 119.3 |
C12—C13—C14 | 121.7 (2) | C33—C32—H32 | 119.3 |
C12—C13—H13 | 119.2 | C34—C33—C32 | 117.1 (2) |
C14—C13—H13 | 119.2 | C34—C33—C36 | 121.3 (2) |
C15—C14—C13 | 117.2 (2) | C32—C33—C36 | 121.7 (2) |
C15—C14—C17 | 121.2 (3) | C35—C34—C33 | 121.8 (2) |
C13—C14—C17 | 121.6 (2) | C35—C34—H34 | 119.1 |
C14—C15—C16 | 121.6 (2) | C33—C34—H34 | 119.1 |
C14—C15—H15 | 119.2 | C34—C35—C30 | 120.9 (2) |
C16—C15—H15 | 119.2 | C34—C35—H35 | 119.6 |
C11—C16—C15 | 120.9 (2) | C30—C35—H35 | 119.6 |
C11—C16—H16 | 119.5 | C33—C36—H36A | 109.5 |
C15—C16—H16 | 119.5 | C33—C36—H36B | 109.5 |
C14—C17—H17A | 109.5 | H36A—C36—H36B | 109.5 |
C14—C17—H17B | 109.5 | C33—C36—H36C | 109.5 |
H17A—C17—H17B | 109.5 | H36A—C36—H36C | 109.5 |
C14—C17—H17C | 109.5 | H36B—C36—H36C | 109.5 |
H17A—C17—H17C | 109.5 | O4—C37—N2 | 122.3 (2) |
H17B—C17—H17C | 109.5 | O4—C37—C38 | 122.3 (2) |
O2—C18—N1 | 123.0 (2) | N2—C37—C38 | 115.4 (2) |
O2—C18—N1 | 123.0 (2) | C37—C38—H38A | 109.5 |
O2—C18—C19 | 121.7 (2) | C37—C38—H38B | 109.5 |
O2—C18—C19 | 121.7 (2) | H38A—C38—H38B | 109.5 |
N1—C18—C19 | 115.3 (2) | C37—C38—H38C | 109.5 |
C18—C19—H19A | 109.5 | H38A—C38—H38C | 109.5 |
C18—C19—H19B | 109.5 | H38B—C38—H38C | 109.5 |
| | | |
C6—C1—C2—C3 | 0.5 (4) | C10—N1—C18—C19 | 178.5 (2) |
C7—C1—C2—C3 | −179.7 (2) | C21—C20—C25—C24 | −0.1 (4) |
C1—C2—C3—C4 | 0.2 (4) | C26—C20—C25—C24 | 178.7 (2) |
C2—C3—C4—C5 | −1.0 (4) | C20—C25—C24—C23 | 0.1 (4) |
C3—C4—C5—C6 | 1.0 (4) | C25—C24—C23—C22 | 0.4 (4) |
C4—C5—C6—C1 | −0.3 (4) | C24—C23—C22—C21 | −0.8 (4) |
C2—C1—C6—C5 | −0.5 (3) | C23—C22—C21—C20 | 0.9 (4) |
C7—C1—C6—C5 | 179.8 (2) | C25—C20—C21—C22 | −0.4 (4) |
C6—C1—C7—O1 | 5.2 (3) | C26—C20—C21—C22 | −179.2 (2) |
C2—C1—C7—O1 | −174.5 (2) | C25—C20—C26—O3 | −12.4 (4) |
C6—C1—C7—C8 | −172.3 (2) | C21—C20—C26—O3 | 166.4 (2) |
C2—C1—C7—C8 | 8.0 (3) | C25—C20—C26—C27 | 169.8 (2) |
O1—C7—C8—C9 | −69.0 (3) | C21—C20—C26—C27 | −11.5 (3) |
C1—C7—C8—C9 | 108.5 (2) | O3—C26—C27—C29 | 40.8 (3) |
O1—C7—C8—C10 | 54.4 (3) | C20—C26—C27—C29 | −141.3 (2) |
C1—C7—C8—C10 | −128.1 (2) | O3—C26—C27—C28 | −80.9 (3) |
C18—N1—C10—C11 | −108.4 (2) | C20—C26—C27—C28 | 97.0 (3) |
C18—N1—C10—C8 | 126.3 (2) | C37—N2—C29—C30 | −101.4 (2) |
C7—C8—C10—N1 | −179.21 (18) | C37—N2—C29—C27 | 132.6 (2) |
C9—C8—C10—N1 | −58.1 (3) | C26—C27—C29—N2 | 174.28 (18) |
C7—C8—C10—C11 | 57.0 (3) | C28—C27—C29—N2 | −66.1 (2) |
C9—C8—C10—C11 | 178.20 (19) | C26—C27—C29—C30 | 53.6 (3) |
N1—C10—C11—C16 | 105.7 (2) | C28—C27—C29—C30 | 173.3 (2) |
C8—C10—C11—C16 | −131.4 (2) | N2—C29—C30—C35 | −91.7 (2) |
N1—C10—C11—C12 | −72.2 (3) | C27—C29—C30—C35 | 30.1 (3) |
C8—C10—C11—C12 | 50.7 (3) | N2—C29—C30—C31 | 82.3 (2) |
C16—C11—C12—C13 | −0.6 (4) | C27—C29—C30—C31 | −155.9 (2) |
C10—C11—C12—C13 | 177.3 (2) | C35—C30—C31—C32 | 1.4 (3) |
C11—C12—C13—C14 | 0.1 (4) | C29—C30—C31—C32 | −172.9 (2) |
C12—C13—C14—C15 | 0.3 (4) | C30—C31—C32—C33 | −0.1 (4) |
C12—C13—C14—C17 | −179.3 (2) | C31—C32—C33—C34 | −1.3 (4) |
C13—C14—C15—C16 | 0.0 (4) | C31—C32—C33—C36 | 178.8 (2) |
C17—C14—C15—C16 | 179.5 (2) | C32—C33—C34—C35 | 1.3 (4) |
C12—C11—C16—C15 | 0.9 (3) | C36—C33—C34—C35 | −178.7 (2) |
C10—C11—C16—C15 | −177.0 (2) | C33—C34—C35—C30 | −0.1 (4) |
C14—C15—C16—C11 | −0.6 (4) | C31—C30—C35—C34 | −1.3 (3) |
O2—O2—C18—N1 | 0.0 (2) | C29—C30—C35—C34 | 172.8 (2) |
O2—O2—C18—C19 | 0.0 (3) | C29—N2—C37—O4 | −9.8 (4) |
C10—N1—C18—O2 | −1.0 (4) | C29—N2—C37—C38 | 168.1 (2) |
C10—N1—C18—O2 | −1.0 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O2 | 0.86 | 2.15 | 2.902 (3) | 145 |
N1—H1A···O4i | 0.86 | 1.96 | 2.818 (3) | 175 |
C5—H5···O2ii | 0.93 | 2.47 | 3.354 (3) | 160 |
C34—H34···Cg1i | 0.93 | 2.75 | 3.564 (3) | 146 |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, −y+1/2, z+1/2. |