Buy article online - an online subscription or single-article purchase is required to access this article.
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. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.