organic compounds
7,9-Didodecyl-6-methyl-3H,7H,8H,9H,9aH-[1,2,4]triazolo[4,3-b][1,2,4]triazepin-8-one
aLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Mohammed V University, Rabat, Morocco, bMedicinal Chemistry Laboratory, Faculty of Medicine and Pharmacy, Mohammed V University in Rabat, 10170 Rabat, Morocco, and cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
*Correspondence e-mail: youness.chimie14@gmail.com
The title compound, C30H55N5O, forms a micellar structure in the crystal with the dodecyl chains intercalating and the bicyclic cores forming dimers across centres of symmetry, via weak C—H⋯N hydrogen bonds, and slipped π-stacking interactions between the five-membered rings.
Keywords: crystal structure; diazepine; triazole; hydrogen bonding; π-stacking interactions; micellar structure.
CCDC reference: 1508860
Structure description
Triazolotriazepine derivatives have been used as potent inhibitors of bone resorption (Chikazu et al., 2000). They also exhibit antifungal activity (Gupta et al., 2011). In a continuation of our previous work on the preparation of new nitrogen-bridged heterocycles, we report herein the of the title compound obtained by alkylation reaction under (Essassi et al., 1977; Harmaoui et al., 2015; El Bakri et al., 2016a,b).
The title compound (Fig. 1) forms a micellar structure in the crystal, with the dodecyl chains intercalating (Fig. 2) and the bicyclic cores forming dimers across centres of symmetry, via C2—H2⋯N5(−x, −y, 1 − z) hydrogen bonds, and slipped π-stacking interactions between the five-membered rings of the same two molecules (Table 1 and Fig. 3). The distance between the centroids of the two rings is 3.572 (1) Å, while the separation between the planes of the two rings is 3.062 (1) Å. A puckering analysis of the seven-membered ring yielded the parameters q2 = 0.843 (1) Å, q3 = 0.243 (1) Å, φ2 = 30.07 (9)° and φ3 = 121.0 (3)°. The total puckering amplitude is 0.888 (1) Å, and the ring is bowl-shaped.
Synthesis and crystallization
To a solution of 6-methyl-7H-[1,2,4]triazolo[4,3-b][1,2,4]triazepin-8(9H)-one (0.2 g, 1.21 mmol) in N,N-dimethylformamide (10 ml), was added potassium carbonate (0.16 g, 1.21 mmol), dodecane bromide (0.35 ml, 1.21 mmol) and a catalytic amount of tetra n-butylammonium bromide. The reaction mixture was stirred for 12 h. The solution was then concentrated to dryness under reduced pressure, and the residue was extracted with dichloromethane. The precipitate formed under cooling was filtered and recrystallized from ethanol solution, to give crystals of the title compound with a yield of 60%.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1508860
https://doi.org/10.1107/S241431461601587X/bh4015sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431461601587X/bh4015Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S241431461601587X/bh4015Isup3.cdx
Supporting information file. DOI: https://doi.org/10.1107/S241431461601587X/bh4015Isup4.cml
Data collection: APEX3 (Bruker, 2016); cell
SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C30H55N5O | Z = 2 |
Mr = 501.79 | F(000) = 556 |
Triclinic, P1 | Dx = 1.088 Mg m−3 |
a = 8.8895 (7) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 8.9652 (7) Å | Cell parameters from 9089 reflections |
c = 19.6555 (15) Å | θ = 5.0–72.6° |
α = 95.093 (3)° | µ = 0.51 mm−1 |
β = 95.922 (3)° | T = 150 K |
γ = 98.563 (3)° | Plate, colourless |
V = 1532.1 (2) Å3 | 0.24 × 0.22 × 0.09 mm |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 5705 independent reflections |
Radiation source: INCOATEC IµS micro-focus source | 4818 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.033 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 72.6°, θmin = 5.0° |
ω scans | h = −9→10 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −11→10 |
Tmin = 0.84, Tmax = 0.95 | l = −21→24 |
11896 measured reflections |
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)] = 0.046 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.135 | All H-atom parameters refined |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0697P)2 + 0.2812P] where P = (Fo2 + 2Fc2)/3 |
5705 reflections | (Δ/σ)max = 0.002 |
545 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
x | y | z | Uiso*/Ueq | ||
O1 | 0.45566 (11) | 0.27197 (11) | 0.49999 (5) | 0.0424 (3) | |
N1 | 0.02842 (13) | 0.34896 (12) | 0.41655 (6) | 0.0341 (3) | |
N2 | −0.01039 (13) | 0.19478 (12) | 0.42508 (6) | 0.0339 (3) | |
N3 | 0.24079 (13) | 0.12205 (12) | 0.44702 (6) | 0.0341 (3) | |
N4 | −0.14934 (14) | −0.03199 (13) | 0.40412 (6) | 0.0416 (3) | |
N5 | 0.00352 (14) | −0.04911 (13) | 0.42035 (6) | 0.0379 (3) | |
C1 | 0.31635 (15) | 0.24759 (15) | 0.48942 (7) | 0.0332 (3) | |
C2 | 0.21506 (15) | 0.35300 (14) | 0.51936 (7) | 0.0318 (3) | |
H2 | 0.1329 (18) | 0.2876 (18) | 0.5376 (8) | 0.034 (4)* | |
C3 | 0.13968 (15) | 0.42197 (14) | 0.45922 (7) | 0.0323 (3) | |
C4 | 0.08281 (15) | 0.08795 (14) | 0.43266 (7) | 0.0327 (3) | |
C5 | −0.15362 (17) | 0.11278 (16) | 0.40653 (8) | 0.0397 (3) | |
H5 | −0.244 (2) | 0.1628 (19) | 0.3975 (8) | 0.043 (4)* | |
C6 | 0.19538 (19) | 0.58068 (16) | 0.44484 (8) | 0.0398 (3) | |
H6A | 0.134 (2) | 0.609 (2) | 0.4066 (10) | 0.056 (5)* | |
H6B | 0.190 (2) | 0.652 (2) | 0.4837 (10) | 0.052 (5)* | |
H6C | 0.303 (2) | 0.592 (2) | 0.4360 (10) | 0.058 (5)* | |
C7 | 0.30173 (16) | 0.47174 (15) | 0.57624 (7) | 0.0349 (3) | |
H7A | 0.387 (2) | 0.537 (2) | 0.5580 (9) | 0.044 (4)* | |
H7B | 0.2302 (18) | 0.5415 (18) | 0.5891 (8) | 0.035 (4)* | |
C8 | 0.35884 (18) | 0.40684 (15) | 0.64135 (7) | 0.0367 (3) | |
H8A | 0.276 (2) | 0.334 (2) | 0.6556 (9) | 0.048 (5)* | |
H8B | 0.436 (2) | 0.341 (2) | 0.6285 (9) | 0.048 (5)* | |
C9 | 0.42445 (19) | 0.53097 (16) | 0.69965 (8) | 0.0417 (4) | |
H9A | 0.506 (2) | 0.608 (2) | 0.6840 (10) | 0.057 (5)* | |
H9B | 0.341 (2) | 0.589 (2) | 0.7127 (10) | 0.057 (5)* | |
C10 | 0.49422 (19) | 0.47228 (16) | 0.76379 (8) | 0.0405 (3) | |
H10A | 0.422 (2) | 0.392 (2) | 0.7769 (10) | 0.054 (5)* | |
H10B | 0.579 (2) | 0.421 (2) | 0.7539 (10) | 0.054 (5)* | |
C11 | 0.55100 (18) | 0.59269 (16) | 0.82448 (8) | 0.0411 (3) | |
H11A | 0.627 (2) | 0.678 (2) | 0.8093 (9) | 0.052 (5)* | |
H11B | 0.458 (2) | 0.638 (2) | 0.8377 (10) | 0.054 (5)* | |
C12 | 0.62686 (19) | 0.52907 (17) | 0.88617 (8) | 0.0410 (3) | |
H12A | 0.559 (2) | 0.441 (2) | 0.8985 (9) | 0.046 (5)* | |
H12B | 0.715 (2) | 0.482 (2) | 0.8725 (10) | 0.055 (5)* | |
C13 | 0.67791 (18) | 0.64442 (17) | 0.94923 (8) | 0.0395 (3) | |
H13A | 0.748 (2) | 0.736 (2) | 0.9361 (9) | 0.047 (5)* | |
H13B | 0.585 (2) | 0.686 (2) | 0.9639 (9) | 0.051 (5)* | |
C14 | 0.75696 (19) | 0.57803 (17) | 1.00942 (8) | 0.0405 (3) | |
H14A | 0.687 (2) | 0.490 (2) | 1.0206 (9) | 0.049 (5)* | |
H14B | 0.848 (2) | 0.536 (2) | 0.9943 (9) | 0.049 (5)* | |
C15 | 0.80604 (18) | 0.69082 (17) | 1.07346 (8) | 0.0393 (3) | |
H15A | 0.717 (2) | 0.731 (2) | 1.0884 (9) | 0.043 (4)* | |
H15B | 0.8740 (19) | 0.782 (2) | 1.0627 (8) | 0.041 (4)* | |
C16 | 0.88550 (19) | 0.62427 (18) | 1.13337 (8) | 0.0416 (3) | |
H16A | 0.977 (2) | 0.585 (2) | 1.1186 (10) | 0.053 (5)* | |
H16B | 0.820 (2) | 0.538 (2) | 1.1450 (10) | 0.052 (5)* | |
C17 | 0.93187 (19) | 0.73634 (18) | 1.19785 (8) | 0.0432 (4) | |
H17A | 0.840 (2) | 0.776 (2) | 1.2122 (10) | 0.054 (5)* | |
H17B | 0.999 (2) | 0.826 (2) | 1.1865 (9) | 0.047 (5)* | |
C18 | 1.0118 (2) | 0.6687 (2) | 1.25739 (9) | 0.0542 (4) | |
H18A | 0.946 (2) | 0.580 (3) | 1.2698 (11) | 0.063 (6)* | |
H18B | 1.110 (3) | 0.631 (3) | 1.2441 (11) | 0.069 (6)* | |
H18C | 1.038 (3) | 0.739 (3) | 1.2985 (12) | 0.078 (7)* | |
C19 | 0.33053 (18) | 0.01086 (16) | 0.41839 (7) | 0.0377 (3) | |
H19A | 0.269 (2) | −0.090 (2) | 0.4172 (9) | 0.047 (5)* | |
H19B | 0.423 (2) | 0.018 (2) | 0.4497 (10) | 0.053 (5)* | |
C20 | 0.36916 (18) | 0.04379 (16) | 0.34731 (8) | 0.0389 (3) | |
H20A | 0.425 (2) | 0.147 (2) | 0.3486 (10) | 0.058 (5)* | |
H20B | 0.275 (2) | 0.044 (2) | 0.3159 (9) | 0.051 (5)* | |
C21 | 0.46416 (16) | −0.06797 (16) | 0.31747 (7) | 0.0365 (3) | |
H21A | 0.4037 (18) | −0.1743 (19) | 0.3148 (8) | 0.036 (4)* | |
H21B | 0.558 (2) | −0.0686 (19) | 0.3493 (9) | 0.042 (4)* | |
C22 | 0.50409 (17) | −0.03997 (17) | 0.24531 (8) | 0.0392 (3) | |
H22A | 0.584 (2) | −0.106 (2) | 0.2336 (9) | 0.051 (5)* | |
H22B | 0.550 (2) | 0.066 (2) | 0.2436 (9) | 0.045 (4)* | |
C23 | 0.36489 (17) | −0.07753 (18) | 0.19116 (8) | 0.0398 (3) | |
H23A | 0.313 (2) | −0.182 (2) | 0.1939 (9) | 0.046 (5)* | |
H23B | 0.291 (2) | −0.007 (2) | 0.2020 (9) | 0.052 (5)* | |
C24 | 0.39822 (17) | −0.06601 (17) | 0.11712 (8) | 0.0392 (3) | |
H24A | 0.475 (2) | −0.136 (2) | 0.1071 (9) | 0.052 (5)* | |
H24B | 0.444 (2) | 0.039 (2) | 0.1127 (9) | 0.044 (4)* | |
C25 | 0.25471 (17) | −0.11520 (18) | 0.06640 (8) | 0.0396 (3) | |
H25A | 0.209 (2) | −0.218 (2) | 0.0731 (9) | 0.046 (5)* | |
H25B | 0.179 (2) | −0.048 (2) | 0.0759 (10) | 0.056 (5)* | |
C26 | 0.27837 (18) | −0.10872 (18) | −0.00890 (8) | 0.0401 (3) | |
H26A | 0.354 (2) | −0.178 (2) | −0.0212 (10) | 0.060 (5)* | |
H26B | 0.323 (2) | −0.002 (2) | −0.0143 (9) | 0.047 (5)* | |
C27 | 0.13099 (18) | −0.16044 (19) | −0.05681 (8) | 0.0410 (3) | |
H27A | 0.086 (2) | −0.264 (2) | −0.0495 (9) | 0.051 (5)* | |
H27B | 0.056 (2) | −0.093 (2) | −0.0457 (10) | 0.059 (5)* | |
C28 | 0.14696 (19) | −0.15499 (19) | −0.13293 (8) | 0.0441 (4) | |
H28A | 0.222 (2) | −0.224 (2) | −0.1459 (10) | 0.057 (5)* | |
H28B | 0.194 (2) | −0.049 (2) | −0.1405 (10) | 0.056 (5)* | |
C29 | −0.0032 (2) | −0.2072 (2) | −0.17858 (8) | 0.0499 (4) | |
H29A | −0.049 (2) | −0.312 (3) | −0.1713 (11) | 0.069 (6)* | |
H29B | −0.078 (3) | −0.138 (3) | −0.1629 (12) | 0.079 (7)* | |
C30 | 0.0099 (3) | −0.1989 (3) | −0.25445 (10) | 0.0656 (5) | |
H30A | 0.082 (3) | −0.266 (3) | −0.2704 (13) | 0.089 (8)* | |
H30B | 0.049 (3) | −0.092 (3) | −0.2641 (14) | 0.095 (8)* | |
H30C | −0.093 (3) | −0.240 (3) | −0.2837 (13) | 0.084 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0316 (6) | 0.0416 (6) | 0.0510 (6) | 0.0038 (4) | −0.0038 (4) | 0.0024 (4) |
N1 | 0.0359 (6) | 0.0248 (5) | 0.0383 (6) | 0.0008 (4) | −0.0058 (5) | 0.0038 (4) |
N2 | 0.0337 (6) | 0.0255 (5) | 0.0378 (6) | −0.0013 (4) | −0.0073 (4) | 0.0020 (4) |
N3 | 0.0341 (6) | 0.0303 (6) | 0.0358 (6) | 0.0047 (4) | −0.0026 (4) | 0.0007 (4) |
N4 | 0.0411 (7) | 0.0325 (6) | 0.0447 (7) | −0.0037 (5) | −0.0089 (5) | 0.0001 (5) |
N5 | 0.0415 (7) | 0.0293 (6) | 0.0384 (6) | −0.0008 (5) | −0.0042 (5) | 0.0004 (5) |
C1 | 0.0317 (7) | 0.0296 (6) | 0.0361 (7) | 0.0024 (5) | −0.0039 (5) | 0.0052 (5) |
C2 | 0.0310 (7) | 0.0257 (6) | 0.0358 (7) | 0.0012 (5) | −0.0047 (5) | 0.0031 (5) |
C3 | 0.0309 (7) | 0.0272 (6) | 0.0365 (7) | 0.0033 (5) | −0.0040 (5) | 0.0022 (5) |
C4 | 0.0352 (7) | 0.0289 (6) | 0.0310 (6) | 0.0016 (5) | −0.0025 (5) | 0.0009 (5) |
C5 | 0.0367 (8) | 0.0321 (7) | 0.0438 (8) | −0.0030 (5) | −0.0099 (6) | 0.0002 (6) |
C6 | 0.0403 (9) | 0.0300 (7) | 0.0447 (8) | −0.0009 (6) | −0.0085 (6) | 0.0067 (6) |
C7 | 0.0339 (7) | 0.0267 (6) | 0.0398 (7) | 0.0014 (5) | −0.0088 (6) | 0.0008 (5) |
C8 | 0.0414 (8) | 0.0270 (6) | 0.0380 (7) | 0.0026 (6) | −0.0065 (6) | 0.0003 (5) |
C9 | 0.0442 (9) | 0.0296 (7) | 0.0452 (8) | 0.0026 (6) | −0.0137 (6) | −0.0017 (6) |
C10 | 0.0449 (9) | 0.0309 (7) | 0.0413 (8) | 0.0043 (6) | −0.0075 (6) | −0.0022 (6) |
C11 | 0.0402 (8) | 0.0346 (7) | 0.0436 (8) | 0.0054 (6) | −0.0103 (6) | −0.0037 (6) |
C12 | 0.0442 (9) | 0.0352 (7) | 0.0402 (8) | 0.0069 (6) | −0.0051 (6) | −0.0037 (6) |
C13 | 0.0372 (8) | 0.0363 (7) | 0.0414 (8) | 0.0064 (6) | −0.0055 (6) | −0.0042 (6) |
C14 | 0.0414 (8) | 0.0378 (8) | 0.0396 (8) | 0.0069 (6) | −0.0025 (6) | −0.0030 (6) |
C15 | 0.0365 (8) | 0.0382 (8) | 0.0407 (8) | 0.0061 (6) | −0.0021 (6) | −0.0026 (6) |
C16 | 0.0416 (9) | 0.0399 (8) | 0.0411 (8) | 0.0057 (6) | −0.0009 (6) | 0.0001 (6) |
C17 | 0.0407 (9) | 0.0443 (8) | 0.0406 (8) | 0.0019 (6) | −0.0021 (6) | −0.0013 (6) |
C18 | 0.0572 (11) | 0.0587 (11) | 0.0419 (9) | 0.0027 (9) | −0.0048 (8) | 0.0031 (8) |
C19 | 0.0408 (8) | 0.0325 (7) | 0.0399 (7) | 0.0119 (6) | −0.0018 (6) | 0.0022 (5) |
C20 | 0.0435 (8) | 0.0336 (7) | 0.0406 (7) | 0.0131 (6) | 0.0006 (6) | 0.0035 (6) |
C21 | 0.0329 (7) | 0.0327 (7) | 0.0425 (7) | 0.0094 (5) | −0.0052 (6) | −0.0005 (5) |
C22 | 0.0326 (8) | 0.0391 (8) | 0.0447 (8) | 0.0076 (6) | 0.0014 (6) | −0.0013 (6) |
C23 | 0.0331 (8) | 0.0450 (8) | 0.0411 (8) | 0.0079 (6) | 0.0030 (6) | 0.0031 (6) |
C24 | 0.0365 (8) | 0.0395 (8) | 0.0414 (8) | 0.0073 (6) | 0.0048 (6) | 0.0007 (6) |
C25 | 0.0377 (8) | 0.0432 (8) | 0.0389 (7) | 0.0095 (6) | 0.0052 (6) | 0.0035 (6) |
C26 | 0.0403 (8) | 0.0414 (8) | 0.0392 (8) | 0.0092 (6) | 0.0056 (6) | 0.0027 (6) |
C27 | 0.0402 (8) | 0.0449 (8) | 0.0389 (8) | 0.0110 (6) | 0.0045 (6) | 0.0028 (6) |
C28 | 0.0501 (9) | 0.0434 (8) | 0.0395 (8) | 0.0113 (7) | 0.0051 (6) | 0.0024 (6) |
C29 | 0.0544 (10) | 0.0536 (10) | 0.0419 (8) | 0.0169 (8) | −0.0010 (7) | −0.0005 (7) |
C30 | 0.0879 (16) | 0.0689 (13) | 0.0408 (9) | 0.0264 (12) | −0.0031 (9) | −0.0010 (8) |
O1—C1 | 1.2177 (17) | C15—H15B | 0.993 (18) |
N1—C3 | 1.2840 (17) | C16—C17 | 1.526 (2) |
N1—N2 | 1.4031 (15) | C16—H16A | 0.99 (2) |
N2—C4 | 1.3646 (17) | C16—H16B | 0.96 (2) |
N2—C5 | 1.3684 (17) | C17—C18 | 1.525 (2) |
N3—C1 | 1.3804 (16) | C17—H17A | 0.99 (2) |
N3—C4 | 1.3858 (18) | C17—H17B | 0.981 (19) |
N3—C19 | 1.4753 (18) | C18—H18A | 0.98 (2) |
N4—C5 | 1.3009 (19) | C18—H18B | 1.03 (2) |
N4—N5 | 1.3976 (18) | C18—H18C | 0.97 (2) |
N5—C4 | 1.3112 (17) | C19—C20 | 1.516 (2) |
C1—C2 | 1.5212 (19) | C19—H19A | 0.982 (19) |
C2—C3 | 1.5226 (17) | C19—H19B | 0.968 (19) |
C2—C7 | 1.5309 (17) | C20—C21 | 1.5202 (19) |
C2—H2 | 0.985 (16) | C20—H20A | 0.98 (2) |
C3—C6 | 1.4967 (18) | C20—H20B | 0.989 (19) |
C5—H5 | 0.985 (17) | C21—C22 | 1.530 (2) |
C6—H6A | 0.96 (2) | C21—H21A | 1.016 (16) |
C6—H6B | 0.96 (2) | C21—H21B | 0.990 (17) |
C6—H6C | 0.98 (2) | C22—C23 | 1.522 (2) |
C7—C8 | 1.5232 (19) | C22—H22A | 1.021 (19) |
C7—H7A | 1.003 (18) | C22—H22B | 0.982 (18) |
C7—H7B | 0.991 (17) | C23—C24 | 1.524 (2) |
C8—C9 | 1.5278 (18) | C23—H23A | 0.989 (19) |
C8—H8A | 0.986 (19) | C23—H23B | 1.01 (2) |
C8—H8B | 1.008 (18) | C24—C25 | 1.519 (2) |
C9—C10 | 1.518 (2) | C24—H24A | 1.020 (19) |
C9—H9A | 1.02 (2) | C24—H24B | 0.988 (18) |
C9—H9B | 1.01 (2) | C25—C26 | 1.521 (2) |
C10—C11 | 1.5257 (19) | C25—H25A | 0.978 (19) |
C10—H10A | 0.96 (2) | C25—H25B | 0.99 (2) |
C10—H10B | 0.96 (2) | C26—C27 | 1.518 (2) |
C11—C12 | 1.523 (2) | C26—H26A | 1.01 (2) |
C11—H11A | 1.03 (2) | C26—H26B | 1.002 (19) |
C11—H11B | 1.02 (2) | C27—C28 | 1.522 (2) |
C12—C13 | 1.5259 (19) | C27—H27A | 0.988 (19) |
C12—H12A | 0.987 (19) | C27—H27B | 0.99 (2) |
C12—H12B | 0.99 (2) | C28—C29 | 1.516 (2) |
C13—C14 | 1.525 (2) | C28—H28A | 1.01 (2) |
C13—H13A | 1.025 (19) | C28—H28B | 1.01 (2) |
C13—H13B | 1.02 (2) | C29—C30 | 1.515 (3) |
C14—C15 | 1.5254 (19) | C29—H29A | 1.00 (2) |
C14—H14A | 0.99 (2) | C29—H29B | 1.03 (2) |
C14—H14B | 1.01 (2) | C30—H30A | 1.00 (3) |
C15—C16 | 1.523 (2) | C30—H30B | 1.01 (3) |
C15—H15A | 0.980 (19) | C30—H30C | 1.03 (3) |
C3—N1—N2 | 115.03 (11) | C17—C16—H16A | 109.8 (11) |
C4—N2—C5 | 104.47 (11) | C15—C16—H16B | 109.9 (11) |
C4—N2—N1 | 129.11 (11) | C17—C16—H16B | 108.4 (11) |
C5—N2—N1 | 123.86 (11) | H16A—C16—H16B | 105.7 (16) |
C1—N3—C4 | 123.85 (12) | C18—C17—C16 | 113.25 (14) |
C1—N3—C19 | 119.05 (11) | C18—C17—H17A | 110.1 (11) |
C4—N3—C19 | 116.98 (11) | C16—C17—H17A | 109.5 (11) |
C5—N4—N5 | 107.30 (11) | C18—C17—H17B | 109.8 (10) |
C4—N5—N4 | 106.66 (11) | C16—C17—H17B | 109.1 (10) |
O1—C1—N3 | 120.92 (13) | H17A—C17—H17B | 104.8 (15) |
O1—C1—C2 | 123.27 (12) | C17—C18—H18A | 110.8 (12) |
N3—C1—C2 | 115.79 (11) | C17—C18—H18B | 111.2 (12) |
C1—C2—C3 | 106.74 (11) | H18A—C18—H18B | 106.4 (17) |
C1—C2—C7 | 113.06 (11) | C17—C18—H18C | 112.9 (14) |
C3—C2—C7 | 113.32 (10) | H18A—C18—H18C | 106.9 (19) |
C1—C2—H2 | 106.2 (9) | H18B—C18—H18C | 108.4 (18) |
C3—C2—H2 | 106.8 (9) | N3—C19—C20 | 111.16 (11) |
C7—C2—H2 | 110.2 (9) | N3—C19—H19A | 107.4 (10) |
N1—C3—C6 | 115.35 (12) | C20—C19—H19A | 111.3 (10) |
N1—C3—C2 | 123.32 (11) | N3—C19—H19B | 107.0 (11) |
C6—C3—C2 | 121.31 (11) | C20—C19—H19B | 110.3 (11) |
N5—C4—N2 | 110.79 (12) | H19A—C19—H19B | 109.4 (15) |
N5—C4—N3 | 125.37 (12) | C19—C20—C21 | 111.94 (12) |
N2—C4—N3 | 123.71 (11) | C19—C20—H20A | 110.7 (11) |
N4—C5—N2 | 110.77 (13) | C21—C20—H20A | 109.0 (11) |
N4—C5—H5 | 127.7 (10) | C19—C20—H20B | 110.6 (11) |
N2—C5—H5 | 121.5 (10) | C21—C20—H20B | 110.3 (11) |
C3—C6—H6A | 111.4 (11) | H20A—C20—H20B | 103.9 (15) |
C3—C6—H6B | 110.8 (11) | C20—C21—C22 | 113.66 (12) |
H6A—C6—H6B | 106.8 (16) | C20—C21—H21A | 108.5 (9) |
C3—C6—H6C | 110.5 (11) | C22—C21—H21A | 108.0 (9) |
H6A—C6—H6C | 109.9 (16) | C20—C21—H21B | 110.2 (10) |
H6B—C6—H6C | 107.3 (16) | C22—C21—H21B | 110.8 (10) |
C8—C7—C2 | 114.45 (11) | H21A—C21—H21B | 105.3 (13) |
C8—C7—H7A | 111.5 (10) | C23—C22—C21 | 112.44 (12) |
C2—C7—H7A | 110.5 (10) | C23—C22—H22A | 109.6 (10) |
C8—C7—H7B | 107.4 (9) | C21—C22—H22A | 107.8 (10) |
C2—C7—H7B | 107.5 (9) | C23—C22—H22B | 108.1 (10) |
H7A—C7—H7B | 105.0 (13) | C21—C22—H22B | 111.3 (10) |
C7—C8—C9 | 112.14 (11) | H22A—C22—H22B | 107.5 (14) |
C7—C8—H8A | 110.3 (10) | C22—C23—C24 | 115.38 (13) |
C9—C8—H8A | 111.2 (11) | C22—C23—H23A | 109.4 (10) |
C7—C8—H8B | 107.1 (10) | C24—C23—H23A | 107.6 (10) |
C9—C8—H8B | 112.5 (10) | C22—C23—H23B | 108.3 (11) |
H8A—C8—H8B | 103.2 (14) | C24—C23—H23B | 108.4 (11) |
C10—C9—C8 | 114.01 (12) | H23A—C23—H23B | 107.6 (14) |
C10—C9—H9A | 107.9 (11) | C25—C24—C23 | 111.74 (12) |
C8—C9—H9A | 110.8 (11) | C25—C24—H24A | 108.6 (10) |
C10—C9—H9B | 108.4 (11) | C23—C24—H24A | 107.7 (10) |
C8—C9—H9B | 109.4 (11) | C25—C24—H24B | 111.0 (10) |
H9A—C9—H9B | 106.1 (16) | C23—C24—H24B | 108.8 (10) |
C9—C10—C11 | 115.08 (12) | H24A—C24—H24B | 109.0 (14) |
C9—C10—H10A | 109.2 (11) | C24—C25—C26 | 115.11 (13) |
C11—C10—H10A | 110.7 (12) | C24—C25—H25A | 109.3 (10) |
C9—C10—H10B | 110.8 (11) | C26—C25—H25A | 109.2 (10) |
C11—C10—H10B | 107.8 (12) | C24—C25—H25B | 109.2 (11) |
H10A—C10—H10B | 102.6 (16) | C26—C25—H25B | 106.4 (11) |
C12—C11—C10 | 112.89 (12) | H25A—C25—H25B | 107.4 (15) |
C12—C11—H11A | 109.5 (10) | C27—C26—C25 | 112.44 (13) |
C10—C11—H11A | 109.6 (10) | C27—C26—H26A | 107.9 (11) |
C12—C11—H11B | 110.0 (11) | C25—C26—H26A | 109.1 (11) |
C10—C11—H11B | 107.1 (11) | C27—C26—H26B | 111.3 (10) |
H11A—C11—H11B | 107.7 (15) | C25—C26—H26B | 107.3 (10) |
C11—C12—C13 | 114.47 (12) | H26A—C26—H26B | 108.7 (15) |
C11—C12—H12A | 110.3 (10) | C26—C27—C28 | 114.92 (13) |
C13—C12—H12A | 110.1 (10) | C26—C27—H27A | 110.5 (10) |
C11—C12—H12B | 109.4 (11) | C28—C27—H27A | 108.8 (11) |
C13—C12—H12B | 110.2 (11) | C26—C27—H27B | 108.8 (11) |
H12A—C12—H12B | 101.7 (15) | C28—C27—H27B | 106.4 (11) |
C14—C13—C12 | 113.11 (12) | H27A—C27—H27B | 107.2 (15) |
C14—C13—H13A | 110.3 (10) | C29—C28—C27 | 112.92 (14) |
C12—C13—H13A | 109.7 (10) | C29—C28—H28A | 108.3 (11) |
C14—C13—H13B | 109.5 (10) | C27—C28—H28A | 108.1 (11) |
C12—C13—H13B | 108.6 (11) | C29—C28—H28B | 111.5 (11) |
H13A—C13—H13B | 105.3 (15) | C27—C28—H28B | 108.9 (11) |
C13—C14—C15 | 113.90 (13) | H28A—C28—H28B | 106.8 (15) |
C13—C14—H14A | 108.4 (11) | C30—C29—C28 | 113.61 (17) |
C15—C14—H14A | 109.7 (11) | C30—C29—H29A | 109.4 (12) |
C13—C14—H14B | 109.1 (10) | C28—C29—H29A | 111.7 (12) |
C15—C14—H14B | 110.1 (11) | C30—C29—H29B | 109.6 (13) |
H14A—C14—H14B | 105.3 (15) | C28—C29—H29B | 106.6 (13) |
C16—C15—C14 | 113.75 (13) | H29A—C29—H29B | 105.6 (18) |
C16—C15—H15A | 108.9 (10) | C29—C30—H30A | 110.3 (14) |
C14—C15—H15A | 109.7 (10) | C29—C30—H30B | 111.4 (15) |
C16—C15—H15B | 109.2 (10) | H30A—C30—H30B | 108 (2) |
C14—C15—H15B | 110.7 (10) | C29—C30—H30C | 111.0 (14) |
H15A—C15—H15B | 104.1 (14) | H30A—C30—H30C | 105 (2) |
C15—C16—C17 | 113.71 (13) | H30B—C30—H30C | 111 (2) |
C15—C16—H16A | 109.0 (11) | ||
C3—N1—N2—C4 | −48.18 (19) | N5—N4—C5—N2 | −1.22 (17) |
C3—N1—N2—C5 | 152.86 (14) | C4—N2—C5—N4 | 1.05 (16) |
C5—N4—N5—C4 | 0.89 (16) | N1—N2—C5—N4 | 164.34 (12) |
C4—N3—C1—O1 | −179.78 (12) | C1—C2—C7—C8 | −66.68 (17) |
C19—N3—C1—O1 | 4.44 (19) | C3—C2—C7—C8 | 171.69 (12) |
C4—N3—C1—C2 | −1.58 (19) | C2—C7—C8—C9 | −172.05 (13) |
C19—N3—C1—C2 | −177.36 (11) | C7—C8—C9—C10 | −175.44 (14) |
O1—C1—C2—C3 | 112.27 (14) | C8—C9—C10—C11 | −176.11 (14) |
N3—C1—C2—C3 | −65.88 (14) | C9—C10—C11—C12 | −177.18 (14) |
O1—C1—C2—C7 | −12.99 (19) | C10—C11—C12—C13 | −177.03 (14) |
N3—C1—C2—C7 | 168.86 (11) | C11—C12—C13—C14 | −178.55 (14) |
N2—N1—C3—C6 | 172.28 (12) | C12—C13—C14—C15 | −178.85 (14) |
N2—N1—C3—C2 | −5.9 (2) | C13—C14—C15—C16 | −179.78 (14) |
C1—C2—C3—N1 | 75.46 (16) | C14—C15—C16—C17 | −178.91 (14) |
C7—C2—C3—N1 | −159.43 (14) | C15—C16—C17—C18 | −179.79 (14) |
C1—C2—C3—C6 | −102.59 (15) | C1—N3—C19—C20 | −94.60 (15) |
C7—C2—C3—C6 | 22.51 (19) | C4—N3—C19—C20 | 89.34 (15) |
N4—N5—C4—N2 | −0.24 (15) | N3—C19—C20—C21 | 178.96 (11) |
N4—N5—C4—N3 | −176.25 (12) | C19—C20—C21—C22 | 179.29 (12) |
C5—N2—C4—N5 | −0.46 (16) | C20—C21—C22—C23 | −69.87 (16) |
N1—N2—C4—N5 | −162.53 (12) | C21—C22—C23—C24 | −174.73 (12) |
C5—N2—C4—N3 | 175.63 (13) | C22—C23—C24—C25 | 176.29 (13) |
N1—N2—C4—N3 | 13.6 (2) | C23—C24—C25—C26 | −179.37 (13) |
C1—N3—C4—N5 | −148.14 (14) | C24—C25—C26—C27 | 179.54 (13) |
C19—N3—C4—N5 | 27.72 (19) | C25—C26—C27—C28 | 179.41 (13) |
C1—N3—C4—N2 | 36.3 (2) | C26—C27—C28—C29 | −179.83 (13) |
C19—N3—C4—N2 | −147.79 (13) | C27—C28—C29—C30 | 178.61 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···N5i | 0.985 (16) | 2.544 (16) | 3.4749 (18) | 157.5 (12) |
Symmetry code: (i) −x, −y, −z+1. |
Acknowledgements
The support of NSF–MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.
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