organic compounds
(4Z)-1-Dodecyl-4-(2-oxopropylidene)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one
aHeterocyclic Organic Chemistry Laboratory URAC 21, Faculty of Sciences, Mohammed V University in Rabat, Av Ibn Battouta, BP 1014 Rabat, Morocco, and bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
*Correspondence e-mail: sebhaoui.jihad@gmail.com
In the title compound, C24H36N2O2, the orientation of the 2-oxopropylidene substituent is determined by the formation of an intramolecular N—H⋯O hydrogen bond. The benzodiazepine seven-membered ring adopts a slightly twisted boat conformation. The molecules pack in a bilayer fashion with the dodecyl chains intercalated to form the inner portion, and the benzodiazepine moieties on the outer surfaces.
Keywords: crystal structure; benzodiazepine; hydrogen bonding; bilayer.
CCDC reference: 1511185
Structure description
1,5-Benzodiazepine derivatives are an important class of et al., 1999), anxiolytics, hypnotics and sedatives (Zellou et al., 1999). The commercial applications of these compounds as dyes for acrylic fibres and in photography have also been reported (Mauget-Fa et al., 2001; Bishop et al., 2007). Two published works indicate that 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine derivatives carrying carboxamide substituents are potentially important as therapeutic and prophylactic agents for diabetes, diabetic nephropathy, or glomerulosclerosis (Finch et al., 1996; Ohtake et al., 2007).
with versatile biological actions. They are used as anticonvulsivants, myorelaxants (RudolphIn the title molecule, the seven-membered ring adopts a slightly twisted boat conformation. An analysis of the conformation (Cremer & Pople, 1975) yielded the puckering parameters q2 = 0.893 (2), q3 = 0.255 (2) Å, φ2 = 18.2 (1) and φ3 = 130.0°. The overall puckering amplitude is 0.916 (2) Å. The dodecyl chain is oriented approximately over the bicyclic portion (Fig. 1), while the orientation of the 2-oxopropylidene substituent is determined by the intramolecular hydrogen bond N1—H1⋯O2 (Table 1 and Fig. 1).
In the crystal, the dodecyl chains intercalate to form the hydrophobic portion of a bilayer, with the more polar bicyclic portions forming the outer faces (Fig. 2). Weak C5—H5⋯O1i and C2—H2⋯O2ii [symmetry codes: (i) x, y − 1, z; (ii) x − 1, y + 1, z] hydrogen bonds help in establishing the surfaces of the bilayer (Table 1 and Fig. 3).
Synthesis and crystallization
A mixture of (4Z)-2-oxopropylidene-1,5-benzodiazepin-2-one (0.01 mol), K2CO3 (0.02 mol), dodecane bromide (0.02 mol) and tetra-n-butylammonium bromide (0.001 mol) in dimethylformamide (60 ml) was stirred at room temperature for 48 h. The solution was filtered by suction filtration. The solvent was removed under reduced pressure. The residue was chromatographed on a silica-gel column using a mixture of hexane and ethyl acetate (80:20 v/v) as to afford the title compound as colourless crystals.
Refinement
Crystal and . All H atoms were found in difference maps and refined with free coordinates and Uiso parameters.
details are presented in Table 2
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Structural data
CCDC reference: 1511185
https://doi.org/10.1107/S2414314616016965/bh4017sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616016965/bh4017Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314616016965/bh4017Isup3.cdx
Supporting information file. DOI: https://doi.org/10.1107/S2414314616016965/bh4017Isup4.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 (Bruker, 2016).C24H36N2O2 | Z = 2 |
Mr = 384.55 | F(000) = 420 |
Triclinic, P1 | Dx = 1.154 Mg m−3 |
a = 8.2589 (9) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 8.3715 (9) Å | Cell parameters from 5933 reflections |
c = 18.097 (2) Å | θ = 2.5–71.6° |
α = 87.327 (6)° | µ = 0.57 mm−1 |
β = 82.242 (6)° | T = 150 K |
γ = 63.248 (7)° | Block, colourless |
V = 1106.9 (2) Å3 | 0.16 × 0.11 × 0.06 mm |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 4075 independent reflections |
Radiation source: INCOATEC IµS micro-focus source | 3242 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.037 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 71.6°, θmin = 4.9° |
ω scans | h = −10→10 |
Absorption correction: multi-scan SADABS (Bruker, 2016) | k = −10→10 |
Tmin = 0.84, Tmax = 0.96 | l = −20→22 |
8388 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)] = 0.050 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.138 | All H-atom parameters refined |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0635P)2 + 0.2871P] where P = (Fo2 + 2Fc2)/3 |
4075 reflections | (Δ/σ)max = 0.001 |
397 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
x | y | z | Uiso*/Ueq | ||
O1 | 0.49804 (17) | 0.95715 (16) | 0.11351 (8) | 0.0363 (3) | |
O2 | 0.85523 (18) | 0.18662 (16) | 0.11278 (8) | 0.0419 (3) | |
N1 | 0.5318 (2) | 0.46760 (19) | 0.12365 (8) | 0.0279 (3) | |
H1 | 0.600 (3) | 0.356 (3) | 0.1351 (13) | 0.052 (7)* | |
N2 | 0.30375 (19) | 0.84404 (17) | 0.16331 (8) | 0.0260 (3) | |
C1 | 0.2303 (2) | 0.7192 (2) | 0.16034 (9) | 0.0265 (4) | |
C2 | 0.0418 (2) | 0.7796 (2) | 0.17719 (10) | 0.0328 (4) | |
H2 | −0.037 (3) | 0.906 (3) | 0.1849 (14) | 0.055 (7)* | |
C3 | −0.0324 (3) | 0.6602 (3) | 0.18364 (11) | 0.0378 (4) | |
H3 | −0.166 (3) | 0.700 (3) | 0.1962 (11) | 0.032 (5)* | |
C4 | 0.0812 (3) | 0.4774 (3) | 0.17338 (10) | 0.0350 (4) | |
H4 | 0.025 (3) | 0.395 (3) | 0.1791 (12) | 0.044 (6)* | |
C5 | 0.2664 (3) | 0.4168 (2) | 0.15358 (10) | 0.0310 (4) | |
H5 | 0.352 (3) | 0.291 (3) | 0.1420 (12) | 0.039 (5)* | |
C6 | 0.3426 (2) | 0.5368 (2) | 0.14575 (9) | 0.0261 (3) | |
C7 | 0.6123 (2) | 0.5373 (2) | 0.06987 (9) | 0.0255 (3) | |
H7 | 0.844 (3) | 0.493 (3) | 0.0001 (11) | 0.032 (5)* | |
C8 | 0.4925 (2) | 0.7223 (2) | 0.04494 (9) | 0.0260 (4) | |
H8A | 0.380 (3) | 0.723 (3) | 0.0262 (11) | 0.037 (5)* | |
H8B | 0.556 (3) | 0.759 (3) | 0.0042 (11) | 0.033 (5)* | |
C9 | 0.4323 (2) | 0.8528 (2) | 0.10986 (9) | 0.0259 (4) | |
C10 | 0.7909 (2) | 0.4437 (2) | 0.04016 (10) | 0.0277 (4) | |
C11 | 0.9060 (2) | 0.2644 (2) | 0.06113 (10) | 0.0315 (4) | |
C12 | 1.0942 (3) | 0.1678 (3) | 0.01860 (13) | 0.0393 (5) | |
H12A | 1.181 (4) | 0.172 (3) | 0.0470 (14) | 0.059 (7)* | |
H12B | 1.116 (3) | 0.228 (3) | −0.0302 (15) | 0.058 (7)* | |
H12C | 1.119 (4) | 0.050 (4) | 0.0081 (18) | 0.087 (10)* | |
C13 | 0.2425 (3) | 0.9605 (2) | 0.23012 (10) | 0.0315 (4) | |
H13A | 0.103 (3) | 1.037 (3) | 0.2358 (12) | 0.046 (6)* | |
H13B | 0.305 (3) | 1.039 (3) | 0.2213 (11) | 0.038 (5)* | |
C14 | 0.2929 (2) | 0.8527 (2) | 0.30084 (10) | 0.0319 (4) | |
H14A | 0.228 (3) | 0.780 (3) | 0.3095 (12) | 0.041 (6)* | |
H14B | 0.251 (3) | 0.935 (3) | 0.3452 (13) | 0.051 (6)* | |
C15 | 0.4971 (2) | 0.7328 (2) | 0.30015 (10) | 0.0317 (4) | |
H15A | 0.544 (3) | 0.640 (3) | 0.2587 (12) | 0.037 (5)* | |
H15B | 0.563 (3) | 0.812 (3) | 0.2879 (12) | 0.040 (5)* | |
C16 | 0.5431 (3) | 0.6367 (3) | 0.37373 (10) | 0.0336 (4) | |
H16A | 0.472 (3) | 0.571 (3) | 0.3864 (12) | 0.043 (6)* | |
H16B | 0.498 (3) | 0.731 (3) | 0.4173 (14) | 0.052 (6)* | |
C17 | 0.7447 (3) | 0.5139 (2) | 0.37574 (10) | 0.0340 (4) | |
H17A | 0.791 (3) | 0.417 (3) | 0.3350 (14) | 0.052 (6)* | |
H17B | 0.816 (3) | 0.585 (3) | 0.3631 (12) | 0.042 (6)* | |
C18 | 0.7845 (3) | 0.4253 (3) | 0.45129 (10) | 0.0346 (4) | |
H18A | 0.707 (3) | 0.359 (3) | 0.4649 (13) | 0.051 (6)* | |
H18B | 0.737 (3) | 0.520 (3) | 0.4902 (13) | 0.047 (6)* | |
C19 | 0.9837 (3) | 0.3002 (2) | 0.45673 (10) | 0.0343 (4) | |
H19A | 1.029 (3) | 0.202 (3) | 0.4173 (13) | 0.044 (6)* | |
H19B | 1.058 (3) | 0.369 (3) | 0.4447 (13) | 0.048 (6)* | |
C20 | 1.0145 (3) | 0.2144 (2) | 0.53318 (10) | 0.0343 (4) | |
H20A | 0.939 (3) | 0.147 (3) | 0.5437 (13) | 0.049 (6)* | |
H20B | 0.967 (3) | 0.312 (3) | 0.5731 (13) | 0.043 (6)* | |
C21 | 1.2120 (3) | 0.0869 (2) | 0.54133 (10) | 0.0338 (4) | |
H21A | 1.259 (3) | −0.011 (3) | 0.5017 (13) | 0.046 (6)* | |
H21B | 1.287 (3) | 0.154 (3) | 0.5297 (12) | 0.042 (6)* | |
C22 | 1.2391 (3) | 0.0029 (3) | 0.61809 (11) | 0.0357 (4) | |
H22A | 1.159 (3) | −0.059 (3) | 0.6320 (13) | 0.052 (6)* | |
H22B | 1.193 (3) | 0.099 (3) | 0.6567 (13) | 0.048 (6)* | |
C23 | 1.4358 (3) | −0.1263 (3) | 0.62625 (12) | 0.0401 (4) | |
H23A | 1.516 (4) | −0.063 (3) | 0.6143 (14) | 0.058 (7)* | |
H23B | 1.479 (3) | −0.219 (3) | 0.5888 (14) | 0.050 (6)* | |
C24 | 1.4624 (4) | −0.2082 (3) | 0.70285 (14) | 0.0550 (6) | |
H24A | 1.600 (4) | −0.300 (4) | 0.7042 (16) | 0.077 (9)* | |
H24B | 1.426 (4) | −0.117 (4) | 0.7445 (16) | 0.066 (8)* | |
H24C | 1.388 (4) | −0.273 (4) | 0.7164 (17) | 0.082 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0366 (7) | 0.0284 (6) | 0.0495 (8) | −0.0200 (6) | −0.0030 (6) | −0.0033 (5) |
O2 | 0.0400 (8) | 0.0286 (7) | 0.0529 (9) | −0.0124 (6) | −0.0063 (6) | 0.0098 (6) |
N1 | 0.0302 (7) | 0.0216 (7) | 0.0320 (8) | −0.0118 (6) | −0.0044 (6) | 0.0038 (6) |
N2 | 0.0288 (7) | 0.0220 (7) | 0.0276 (7) | −0.0117 (6) | −0.0037 (5) | −0.0004 (5) |
C1 | 0.0315 (9) | 0.0260 (8) | 0.0250 (8) | −0.0153 (7) | −0.0049 (6) | 0.0019 (6) |
C2 | 0.0326 (9) | 0.0310 (9) | 0.0352 (10) | −0.0151 (8) | −0.0032 (7) | 0.0033 (7) |
C3 | 0.0322 (10) | 0.0435 (11) | 0.0416 (10) | −0.0213 (9) | −0.0029 (8) | 0.0045 (8) |
C4 | 0.0432 (10) | 0.0398 (10) | 0.0326 (9) | −0.0280 (9) | −0.0059 (7) | 0.0045 (8) |
C5 | 0.0424 (10) | 0.0290 (9) | 0.0271 (9) | −0.0206 (8) | −0.0062 (7) | 0.0028 (7) |
C6 | 0.0309 (8) | 0.0257 (8) | 0.0246 (8) | −0.0147 (7) | −0.0067 (6) | 0.0040 (6) |
C7 | 0.0310 (8) | 0.0235 (8) | 0.0260 (8) | −0.0148 (7) | −0.0068 (6) | 0.0000 (6) |
C8 | 0.0271 (8) | 0.0230 (8) | 0.0276 (8) | −0.0110 (7) | −0.0048 (6) | 0.0044 (6) |
C9 | 0.0254 (8) | 0.0198 (8) | 0.0317 (9) | −0.0087 (7) | −0.0070 (6) | 0.0036 (6) |
C10 | 0.0281 (8) | 0.0248 (8) | 0.0318 (9) | −0.0128 (7) | −0.0064 (7) | 0.0021 (7) |
C11 | 0.0310 (9) | 0.0257 (8) | 0.0397 (10) | −0.0128 (7) | −0.0110 (7) | −0.0001 (7) |
C12 | 0.0296 (10) | 0.0303 (10) | 0.0570 (13) | −0.0116 (8) | −0.0071 (9) | −0.0034 (9) |
C13 | 0.0363 (10) | 0.0244 (8) | 0.0317 (9) | −0.0118 (8) | −0.0023 (7) | −0.0039 (7) |
C14 | 0.0331 (9) | 0.0338 (9) | 0.0296 (9) | −0.0158 (8) | −0.0014 (7) | −0.0037 (7) |
C15 | 0.0336 (9) | 0.0332 (9) | 0.0285 (9) | −0.0155 (8) | −0.0025 (7) | −0.0013 (7) |
C16 | 0.0355 (10) | 0.0354 (9) | 0.0305 (9) | −0.0163 (8) | −0.0045 (7) | 0.0012 (8) |
C17 | 0.0378 (10) | 0.0344 (9) | 0.0305 (9) | −0.0166 (9) | −0.0059 (7) | 0.0017 (8) |
C18 | 0.0379 (10) | 0.0340 (10) | 0.0315 (10) | −0.0156 (8) | −0.0056 (7) | 0.0013 (8) |
C19 | 0.0396 (10) | 0.0347 (10) | 0.0303 (9) | −0.0181 (9) | −0.0053 (7) | 0.0016 (8) |
C20 | 0.0390 (10) | 0.0340 (10) | 0.0320 (10) | −0.0179 (9) | −0.0057 (7) | 0.0022 (8) |
C21 | 0.0381 (10) | 0.0330 (9) | 0.0314 (9) | −0.0166 (8) | −0.0067 (7) | 0.0037 (8) |
C22 | 0.0431 (11) | 0.0350 (10) | 0.0327 (10) | −0.0204 (9) | −0.0062 (8) | 0.0025 (8) |
C23 | 0.0464 (11) | 0.0379 (10) | 0.0394 (11) | −0.0200 (9) | −0.0139 (9) | 0.0040 (9) |
C24 | 0.0745 (17) | 0.0507 (13) | 0.0491 (14) | −0.0320 (13) | −0.0288 (12) | 0.0158 (11) |
O1—C9 | 1.2263 (19) | C14—H14A | 0.97 (2) |
O2—C11 | 1.247 (2) | C14—H14B | 1.00 (2) |
N1—C7 | 1.360 (2) | C15—C16 | 1.525 (3) |
N1—C6 | 1.405 (2) | C15—H15A | 1.01 (2) |
N1—H1 | 0.88 (2) | C15—H15B | 1.03 (2) |
N2—C9 | 1.362 (2) | C16—C17 | 1.517 (3) |
N2—C1 | 1.4309 (19) | C16—H16A | 0.97 (2) |
N2—C13 | 1.473 (2) | C16—H16B | 1.05 (2) |
C1—C2 | 1.396 (2) | C17—C18 | 1.528 (3) |
C1—C6 | 1.400 (2) | C17—H17A | 1.02 (2) |
C2—C3 | 1.382 (2) | C17—H17B | 1.01 (2) |
C2—H2 | 0.97 (2) | C18—C19 | 1.515 (3) |
C3—C4 | 1.394 (3) | C18—H18A | 1.03 (3) |
C3—H3 | 1.00 (2) | C18—H18B | 0.99 (2) |
C4—C5 | 1.376 (3) | C19—C20 | 1.527 (3) |
C4—H4 | 0.98 (2) | C19—H19A | 1.01 (2) |
C5—C6 | 1.399 (2) | C19—H19B | 1.01 (2) |
C5—H5 | 0.98 (2) | C20—C21 | 1.518 (3) |
C7—C10 | 1.365 (2) | C20—H20A | 1.01 (2) |
C7—C8 | 1.502 (2) | C20—H20B | 1.02 (2) |
C8—C9 | 1.515 (2) | C21—C22 | 1.525 (3) |
C8—H8A | 1.03 (2) | C21—H21A | 1.01 (2) |
C8—H8B | 0.96 (2) | C21—H21B | 1.01 (2) |
C10—C11 | 1.436 (2) | C22—C23 | 1.516 (3) |
C10—H7 | 0.97 (2) | C22—H22A | 1.01 (2) |
C11—C12 | 1.506 (3) | C22—H22B | 0.99 (2) |
C12—H12A | 0.95 (3) | C23—C24 | 1.516 (3) |
C12—H12B | 1.03 (3) | C23—H23A | 1.02 (3) |
C12—H12C | 0.94 (3) | C23—H23B | 0.96 (2) |
C13—C14 | 1.525 (3) | C24—H24A | 1.05 (3) |
C13—H13A | 1.03 (2) | C24—H24B | 1.02 (3) |
C13—H13B | 1.00 (2) | C24—H24C | 0.99 (3) |
C14—C15 | 1.524 (3) | ||
C7—N1—C6 | 125.16 (15) | C14—C15—C16 | 112.49 (15) |
C7—N1—H1 | 115.3 (16) | C14—C15—H15A | 110.6 (12) |
C6—N1—H1 | 117.0 (16) | C16—C15—H15A | 108.4 (12) |
C9—N2—C1 | 123.31 (14) | C14—C15—H15B | 107.5 (12) |
C9—N2—C13 | 119.43 (13) | C16—C15—H15B | 111.2 (12) |
C1—N2—C13 | 117.17 (13) | H15A—C15—H15B | 106.5 (16) |
C2—C1—C6 | 119.07 (15) | C17—C16—C15 | 114.65 (15) |
C2—C1—N2 | 118.86 (15) | C17—C16—H16A | 110.3 (13) |
C6—C1—N2 | 121.94 (15) | C15—C16—H16A | 110.0 (14) |
C3—C2—C1 | 120.67 (17) | C17—C16—H16B | 108.4 (13) |
C3—C2—H2 | 119.9 (15) | C15—C16—H16B | 109.6 (13) |
C1—C2—H2 | 119.4 (15) | H16A—C16—H16B | 103.3 (18) |
C2—C3—C4 | 120.01 (17) | C16—C17—C18 | 112.69 (15) |
C2—C3—H3 | 122.0 (11) | C16—C17—H17A | 109.8 (14) |
C4—C3—H3 | 117.9 (11) | C18—C17—H17A | 109.3 (14) |
C5—C4—C3 | 119.89 (16) | C16—C17—H17B | 108.9 (13) |
C5—C4—H4 | 121.9 (13) | C18—C17—H17B | 110.0 (13) |
C3—C4—H4 | 118.2 (13) | H17A—C17—H17B | 105.9 (18) |
C4—C5—C6 | 120.54 (17) | C19—C18—C17 | 115.22 (15) |
C4—C5—H5 | 123.4 (12) | C19—C18—H18A | 109.9 (13) |
C6—C5—H5 | 116.0 (12) | C17—C18—H18A | 109.4 (13) |
C5—C6—C1 | 119.64 (16) | C19—C18—H18B | 110.1 (14) |
C5—C6—N1 | 117.97 (15) | C17—C18—H18B | 108.6 (14) |
C1—C6—N1 | 122.39 (14) | H18A—C18—H18B | 103.0 (18) |
N1—C7—C10 | 121.79 (15) | C18—C19—C20 | 112.74 (15) |
N1—C7—C8 | 116.00 (14) | C18—C19—H19A | 108.9 (13) |
C10—C7—C8 | 122.22 (15) | C20—C19—H19A | 109.0 (13) |
C7—C8—C9 | 109.41 (14) | C18—C19—H19B | 108.8 (13) |
C7—C8—H8A | 109.1 (11) | C20—C19—H19B | 110.5 (13) |
C9—C8—H8A | 109.9 (11) | H19A—C19—H19B | 106.7 (18) |
C7—C8—H8B | 111.1 (12) | C21—C20—C19 | 114.78 (16) |
C9—C8—H8B | 109.7 (12) | C21—C20—H20A | 108.5 (13) |
H8A—C8—H8B | 107.6 (17) | C19—C20—H20A | 108.7 (13) |
O1—C9—N2 | 123.08 (15) | C21—C20—H20B | 108.9 (13) |
O1—C9—C8 | 121.36 (15) | C19—C20—H20B | 109.2 (12) |
N2—C9—C8 | 115.55 (13) | H20A—C20—H20B | 106.5 (17) |
C7—C10—C11 | 123.18 (16) | C20—C21—C22 | 113.78 (16) |
C7—C10—H7 | 120.6 (12) | C20—C21—H21A | 108.8 (13) |
C11—C10—H7 | 116.0 (12) | C22—C21—H21A | 109.5 (13) |
O2—C11—C10 | 122.41 (16) | C20—C21—H21B | 108.3 (12) |
O2—C11—C12 | 119.32 (17) | C22—C21—H21B | 110.3 (12) |
C10—C11—C12 | 118.27 (17) | H21A—C21—H21B | 105.8 (17) |
C11—C12—H12A | 109.1 (15) | C23—C22—C21 | 113.99 (16) |
C11—C12—H12B | 114.8 (14) | C23—C22—H22A | 109.3 (14) |
H12A—C12—H12B | 102 (2) | C21—C22—H22A | 111.5 (14) |
C11—C12—H12C | 109.9 (19) | C23—C22—H22B | 109.1 (14) |
H12A—C12—H12C | 112 (2) | C21—C22—H22B | 109.3 (13) |
H12B—C12—H12C | 109 (2) | H22A—C22—H22B | 103.0 (18) |
N2—C13—C14 | 111.77 (14) | C24—C23—C22 | 113.8 (2) |
N2—C13—H13A | 110.2 (12) | C24—C23—H23A | 109.4 (15) |
C14—C13—H13A | 108.4 (13) | C22—C23—H23A | 109.5 (14) |
N2—C13—H13B | 105.3 (12) | C24—C23—H23B | 109.9 (14) |
C14—C13—H13B | 110.9 (12) | C22—C23—H23B | 108.4 (15) |
H13A—C13—H13B | 110.3 (17) | H23A—C23—H23B | 105.5 (19) |
C15—C14—C13 | 114.11 (15) | C23—C24—H24A | 110.0 (16) |
C15—C14—H14A | 108.9 (13) | C23—C24—H24B | 113.5 (15) |
C13—C14—H14A | 110.0 (13) | H24A—C24—H24B | 108 (2) |
C15—C14—H14B | 107.8 (14) | C23—C24—H24C | 112.0 (18) |
C13—C14—H14B | 110.0 (14) | H24A—C24—H24C | 108 (2) |
H14A—C14—H14B | 105.6 (18) | H24B—C24—H24C | 106 (2) |
C9—N2—C1—C2 | −135.43 (17) | C13—N2—C9—O1 | −1.8 (3) |
C13—N2—C1—C2 | 48.1 (2) | C1—N2—C9—C8 | 1.0 (2) |
C9—N2—C1—C6 | 48.7 (2) | C13—N2—C9—C8 | 177.42 (14) |
C13—N2—C1—C6 | −127.77 (17) | C7—C8—C9—O1 | 105.68 (18) |
C6—C1—C2—C3 | 3.7 (3) | C7—C8—C9—N2 | −73.53 (18) |
N2—C1—C2—C3 | −172.29 (16) | N1—C7—C10—C11 | 1.9 (3) |
C1—C2—C3—C4 | 0.1 (3) | C8—C7—C10—C11 | −177.63 (15) |
C2—C3—C4—C5 | −2.9 (3) | C7—C10—C11—O2 | −6.3 (3) |
C3—C4—C5—C6 | 1.9 (3) | C7—C10—C11—C12 | 173.45 (16) |
C4—C5—C6—C1 | 1.9 (3) | C9—N2—C13—C14 | −115.69 (17) |
C4—C5—C6—N1 | −178.46 (16) | C1—N2—C13—C14 | 61.0 (2) |
C2—C1—C6—C5 | −4.6 (2) | N2—C13—C14—C15 | 58.3 (2) |
N2—C1—C6—C5 | 171.20 (15) | C13—C14—C15—C16 | 176.23 (14) |
C2—C1—C6—N1 | 175.74 (16) | C14—C15—C16—C17 | 179.39 (15) |
N2—C1—C6—N1 | −8.4 (2) | C15—C16—C17—C18 | 178.22 (15) |
C7—N1—C6—C5 | 133.69 (17) | C16—C17—C18—C19 | 179.72 (16) |
C7—N1—C6—C1 | −46.7 (2) | C17—C18—C19—C20 | −179.42 (15) |
C6—N1—C7—C10 | −165.76 (15) | C18—C19—C20—C21 | 179.65 (15) |
C6—N1—C7—C8 | 13.8 (2) | C19—C20—C21—C22 | −179.93 (15) |
N1—C7—C8—C9 | 63.24 (18) | C20—C21—C22—C23 | 179.33 (16) |
C10—C7—C8—C9 | −117.19 (17) | C21—C22—C23—C24 | 179.49 (17) |
C1—N2—C9—O1 | −178.22 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.88 (2) | 1.94 (2) | 2.637 (2) | 136 (2) |
C5—H5···O1i | 0.98 (2) | 2.54 (2) | 3.500 (2) | 165.6 (17) |
C2—H2···O2ii | 0.97 (2) | 2.48 (3) | 3.276 (2) | 139.4 (19) |
Symmetry codes: (i) x, y−1, z; (ii) x−1, y+1, z. |
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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