organic compounds
N-[5-(Diphenylamino)penta-2,4-diyn-1-yl]benzamide
aDepartment of Material Science and Chemistry, Wakayama University, Sakaedani, Wakayama, 640-8510, Japan
*Correspondence e-mail: okuno@center.wakayama-u.ac.jp
In the title compound, C24H18N2O1, the ynamine moiety has a near-planar structure (r.m.s. deviation = 0.0200 Å), and makes dihedral angles of 52.99 (7) and 27.91 (7)° with the phenyl rings. In the crystal, the molecules exhibit a dimeric form owing to bifurcated C—H⋯π interactions within a centrosymmetric dimer. Intermolecular N—H⋯O hydrogen bonds are also formed along the b-axis direction.
CCDC reference: 1533495
Structure description
The title compound is a diacetylene derivative. Solid-state polymerization is known to proceed for some diacetylene derivatives in a specific molecular arrangement. Mainly, two conditions for the molecular arrangement are required for the polymerization: (i) the molecules stack one-dimensionally with repeating intervals of 4.8–5.6 Å; (ii) the diacetylene moieties of the molecules have an inclination angle of 40–50° with the stacking axis. In order to realize such an ideal stacking structure, several kinds of intermolecular hydrogen bonds are utilized (Lauher et al., 2008). In the title compound, a phenylamide group is introduced to control the molecular arrangement.
In the title compound, Fig. 1, the ynamine moiety has a near-planar structure (r.m.s. deviation = 0.0200 Å), making dihedral angles with the C1–C6 and C7–C12 phenyl rings of 52.99 (7) and 27.91 (7)°, respectively. The N2—C13 bond length is in good agreement with those reported (Tokutome et al., 2012, 2013; Tabata & Okuno (2011); Tabata et al., 2012). The N1/O1/C18/C19 amide group has an almost planar form (r.m.s. deviation = 0.0027 Å) and makes a dihedral angle of 17.63 (8)° with the C19–C24 phenyl ring.
In the crystal, the molecules make a dimeric form owing to bifurcated C—H⋯π interactions within a centrosymmetric dimer, where the H3⋯C14i and H3⋯C15i [symmetry code: (i) −x + 1, −y + 1, −z + 1] distances are 2.81 and 2.74 Å, as shown in Fig. 2. Intermolecular N—H⋯O hydrogen bonds (Table 1) are also formed along the b-axis direction. Although the intermolecular N—H⋯O hydrogen bonds are formed as designed, the C—H⋯π interactions are thought to prevent a regular stack with translation.
Synthesis and crystallization
A mixture of N-ethynyl-N-phenylaniline (1.16 g, 6.0 mmol) and N-(prop-2-yn-1-yl)benzamide (0.80 g, 5.0 mmol) in acetone (35 ml) were reacted in the presence of Cu-TMEDA catalyst and oxygen for 12 h at 253 K. (Hay, 1962) The solution was concentrated and extracted with chloroform. The organic layer was washed with ammonium hydroxide and dried over sodium sulfate. After filtration, it was concentrated under reduced pressure. The residual solid was purified by (SiO2) to give 0.87 g (50%) of the title compound as a colourless solid. Single crystals of sufficient quality were obtained by slow evaporation from a dichloromethane–hexane solution.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1533495
https://doi.org/10.1107/S2414314617002772/ff4013sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617002772/ff4013Isup2.hkl
Data collection: CrystalClear (Rigaku, 2008); cell
CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXD2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: CrystalStructure (Rigaku, 2014).C24H18N2O | F(000) = 736.00 |
Mr = 350.42 | Dx = 1.262 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71075 Å |
a = 12.486 (7) Å | Cell parameters from 4684 reflections |
b = 9.738 (5) Å | θ = 2.1–31.2° |
c = 16.089 (9) Å | µ = 0.08 mm−1 |
β = 109.518 (6)° | T = 93 K |
V = 1843.8 (17) Å3 | Block, colorless |
Z = 4 | 0.10 × 0.07 × 0.04 mm |
Rigaku Saturn724+ diffractometer | 2929 reflections with F2 > 2.0σ(F2) |
Detector resolution: 7.111 pixels mm-1 | Rint = 0.062 |
ω scans | θmax = 27.5°, θmin = 3.3° |
Absorption correction: numerical (NUMABS; Rigaku, 1999) | h = −16→16 |
Tmin = 0.995, Tmax = 0.997 | k = −12→12 |
14614 measured reflections | l = −20→20 |
4155 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.162 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0816P)2 + 0.1006P] where P = (Fo2 + 2Fc2)/3 |
4155 reflections | (Δ/σ)max < 0.001 |
248 parameters | Δρmax = 0.58 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
Primary atom site location: structure-invariant direct methods |
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement was performed 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 sigma(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
O1 | 0.02051 (13) | 0.30092 (14) | 0.22465 (9) | 0.0308 (4) | |
N1 | 0.00394 (14) | 0.51968 (17) | 0.26271 (10) | 0.0229 (4) | |
N2 | 0.41255 (13) | 0.36679 (17) | 0.68882 (10) | 0.0248 (4) | |
C1 | 0.51710 (16) | 0.3440 (2) | 0.67100 (12) | 0.0224 (4) | |
C2 | 0.55674 (17) | 0.4437 (2) | 0.62730 (13) | 0.0276 (4) | |
C3 | 0.65474 (18) | 0.4186 (2) | 0.60743 (14) | 0.0300 (5) | |
C4 | 0.71294 (17) | 0.2951 (2) | 0.63095 (13) | 0.0285 (5) | |
C5 | 0.67219 (18) | 0.1961 (2) | 0.67443 (13) | 0.0286 (5) | |
C6 | 0.57419 (17) | 0.2200 (2) | 0.69492 (13) | 0.0256 (4) | |
C7 | 0.40326 (16) | 0.34256 (19) | 0.77368 (12) | 0.0212 (4) | |
C8 | 0.30013 (16) | 0.30123 (19) | 0.78110 (12) | 0.0228 (4) | |
C9 | 0.29067 (17) | 0.2862 (2) | 0.86391 (12) | 0.0263 (4) | |
C10 | 0.38291 (19) | 0.3101 (2) | 0.93921 (13) | 0.0287 (5) | |
C11 | 0.48588 (18) | 0.3483 (2) | 0.93129 (13) | 0.0285 (5) | |
C12 | 0.49718 (16) | 0.3653 (2) | 0.84927 (13) | 0.0250 (4) | |
C13 | 0.31941 (16) | 0.3997 (2) | 0.62021 (12) | 0.0233 (4) | |
C14 | 0.23749 (16) | 0.4286 (2) | 0.55789 (12) | 0.0249 (4) | |
C15 | 0.14353 (16) | 0.4492 (2) | 0.48386 (12) | 0.0234 (4) | |
C16 | 0.06265 (16) | 0.4636 (2) | 0.41808 (12) | 0.0227 (4) | |
C17 | −0.03368 (16) | 0.4829 (2) | 0.33613 (12) | 0.0233 (4) | |
C18 | 0.03405 (16) | 0.42482 (19) | 0.21431 (12) | 0.0221 (4) | |
C19 | 0.08670 (16) | 0.47240 (19) | 0.14822 (12) | 0.0215 (4) | |
C20 | 0.13380 (17) | 0.6029 (2) | 0.15128 (13) | 0.0265 (4) | |
C21 | 0.18493 (18) | 0.6402 (2) | 0.09050 (13) | 0.0315 (5) | |
C22 | 0.18987 (18) | 0.5483 (2) | 0.02646 (14) | 0.0323 (5) | |
C23 | 0.14320 (18) | 0.4188 (2) | 0.02273 (13) | 0.0302 (5) | |
C24 | 0.09132 (17) | 0.3809 (2) | 0.08340 (12) | 0.0256 (4) | |
H1 | 0.012 (2) | 0.605 (3) | 0.2538 (16) | 0.045 (7)* | |
H2 | 0.51728 | 0.52822 | 0.61112 | 0.0331* | |
H3 | 0.68247 | 0.48659 | 0.57742 | 0.0360* | |
H4 | 0.78019 | 0.27874 | 0.61726 | 0.0342* | |
H5 | 0.71144 | 0.11141 | 0.69036 | 0.0343* | |
H6 | 0.54645 | 0.15216 | 0.725 | 0.0308* | |
H8 | 0.23673 | 0.2835 | 0.72973 | 0.0274* | |
H9 | 0.2201 | 0.25907 | 0.86913 | 0.0315* | |
H10 | 0.37561 | 0.3005 | 0.99583 | 0.0344* | |
H11 | 0.54967 | 0.36294 | 0.98291 | 0.0342* | |
H12 | 0.568 | 0.39214 | 0.84442 | 0.0300* | |
H17A | −0.07853 | 0.39704 | 0.32181 | 0.0280* | |
H17B | −0.08371 | 0.55628 | 0.34498 | 0.0280* | |
H20 | 0.13076 | 0.66645 | 0.19525 | 0.0318* | |
H21 | 0.21675 | 0.72936 | 0.09278 | 0.0378* | |
H22 | 0.22535 | 0.57409 | −0.01502 | 0.0387* | |
H23 | 0.1466 | 0.35561 | −0.02132 | 0.0362* | |
H24 | 0.0589 | 0.292 | 0.08048 | 0.0307* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0386 (9) | 0.0184 (7) | 0.0381 (8) | −0.0005 (6) | 0.0164 (7) | 0.0003 (6) |
N1 | 0.0270 (9) | 0.0173 (8) | 0.0230 (8) | 0.0018 (7) | 0.0065 (7) | 0.0017 (7) |
N2 | 0.0176 (8) | 0.0343 (9) | 0.0223 (8) | 0.0021 (7) | 0.0062 (7) | 0.0071 (7) |
C1 | 0.0184 (9) | 0.0279 (10) | 0.0200 (9) | −0.0014 (7) | 0.0051 (7) | −0.0019 (8) |
C2 | 0.0263 (10) | 0.0272 (10) | 0.0303 (11) | −0.0004 (8) | 0.0110 (9) | 0.0035 (9) |
C3 | 0.0280 (11) | 0.0343 (11) | 0.0321 (11) | −0.0063 (9) | 0.0157 (9) | −0.0004 (9) |
C4 | 0.0207 (10) | 0.0366 (12) | 0.0290 (11) | −0.0012 (8) | 0.0093 (9) | −0.0095 (9) |
C5 | 0.0266 (11) | 0.0283 (11) | 0.0284 (10) | 0.0041 (8) | 0.0057 (9) | −0.0050 (9) |
C6 | 0.0255 (10) | 0.0238 (10) | 0.0264 (10) | −0.0028 (8) | 0.0071 (8) | −0.0006 (8) |
C7 | 0.0205 (9) | 0.0219 (9) | 0.0213 (9) | 0.0032 (7) | 0.0069 (8) | 0.0021 (7) |
C8 | 0.0202 (9) | 0.0236 (9) | 0.0234 (9) | 0.0000 (7) | 0.0055 (8) | 0.0022 (8) |
C9 | 0.0239 (10) | 0.0274 (11) | 0.0289 (11) | −0.0012 (8) | 0.0106 (9) | 0.0007 (8) |
C10 | 0.0360 (12) | 0.0304 (11) | 0.0206 (9) | 0.0040 (9) | 0.0107 (9) | 0.0027 (8) |
C11 | 0.0278 (11) | 0.0310 (11) | 0.0222 (10) | 0.0037 (9) | 0.0022 (8) | 0.0006 (8) |
C12 | 0.0183 (9) | 0.0268 (10) | 0.0283 (10) | −0.0010 (8) | 0.0054 (8) | 0.0028 (8) |
C13 | 0.0199 (9) | 0.0284 (10) | 0.0233 (9) | 0.0008 (8) | 0.0093 (8) | 0.0042 (8) |
C14 | 0.0212 (10) | 0.0326 (11) | 0.0233 (9) | 0.0005 (8) | 0.0105 (8) | 0.0034 (8) |
C15 | 0.0206 (10) | 0.0283 (10) | 0.0251 (10) | 0.0038 (8) | 0.0126 (8) | 0.0038 (8) |
C16 | 0.0201 (9) | 0.0261 (10) | 0.0240 (9) | 0.0013 (8) | 0.0100 (8) | 0.0018 (8) |
C17 | 0.0196 (9) | 0.0248 (10) | 0.0241 (9) | 0.0029 (8) | 0.0053 (8) | 0.0016 (8) |
C18 | 0.0204 (9) | 0.0188 (9) | 0.0222 (9) | 0.0030 (7) | 0.0006 (7) | −0.0010 (8) |
C19 | 0.0182 (9) | 0.0210 (9) | 0.0219 (9) | 0.0034 (7) | 0.0021 (7) | 0.0019 (8) |
C20 | 0.0243 (10) | 0.0267 (10) | 0.0246 (10) | −0.0030 (8) | 0.0028 (8) | −0.0014 (8) |
C21 | 0.0258 (11) | 0.0346 (12) | 0.0306 (11) | −0.0061 (9) | 0.0047 (9) | 0.0042 (9) |
C22 | 0.0250 (11) | 0.0428 (13) | 0.0292 (11) | 0.0044 (9) | 0.0094 (9) | 0.0093 (10) |
C23 | 0.0283 (11) | 0.0344 (11) | 0.0267 (10) | 0.0089 (9) | 0.0076 (9) | 0.0010 (9) |
C24 | 0.0234 (10) | 0.0245 (10) | 0.0262 (10) | 0.0058 (8) | 0.0048 (8) | 0.0017 (8) |
O1—C18 | 1.237 (2) | C19—C24 | 1.388 (3) |
N1—C17 | 1.454 (3) | C20—C21 | 1.383 (3) |
N1—C18 | 1.340 (3) | C21—C22 | 1.382 (3) |
N2—C1 | 1.444 (3) | C22—C23 | 1.382 (3) |
N2—C7 | 1.428 (3) | C23—C24 | 1.390 (3) |
N2—C13 | 1.348 (2) | N1—H1 | 0.85 (3) |
C1—C2 | 1.383 (3) | C2—H2 | 0.950 |
C1—C6 | 1.390 (3) | C3—H3 | 0.950 |
C2—C3 | 1.386 (3) | C4—H4 | 0.950 |
C3—C4 | 1.391 (3) | C5—H5 | 0.950 |
C4—C5 | 1.384 (3) | C6—H6 | 0.950 |
C5—C6 | 1.389 (3) | C8—H8 | 0.950 |
C7—C8 | 1.392 (3) | C9—H9 | 0.950 |
C7—C12 | 1.397 (2) | C10—H10 | 0.950 |
C8—C9 | 1.384 (3) | C11—H11 | 0.950 |
C9—C10 | 1.384 (3) | C12—H12 | 0.950 |
C10—C11 | 1.384 (4) | C17—H17A | 0.990 |
C11—C12 | 1.383 (3) | C17—H17B | 0.990 |
C13—C14 | 1.202 (2) | C20—H20 | 0.950 |
C14—C15 | 1.379 (2) | C21—H21 | 0.950 |
C15—C16 | 1.202 (2) | C22—H22 | 0.950 |
C16—C17 | 1.470 (2) | C23—H23 | 0.950 |
C18—C19 | 1.498 (3) | C24—H24 | 0.950 |
C19—C20 | 1.395 (3) | ||
O1···C16 | 3.373 (3) | C17···H5x | 3.3890 |
O1···C17 | 2.762 (3) | C17···H8viii | 3.3058 |
O1···C24 | 2.810 (3) | C17···H20i | 3.2884 |
N1···C15 | 3.468 (3) | C17···H24iii | 3.3524 |
N1···C20 | 2.906 (3) | C18···H1i | 3.24 (3) |
C1···C4 | 2.770 (3) | C18···H8ii | 3.1877 |
C1···C12 | 2.968 (3) | C18···H9ii | 3.3078 |
C1···C14 | 3.455 (3) | C19···H8ii | 3.1300 |
C2···C5 | 2.781 (3) | C19···H23ix | 3.3890 |
C2···C13 | 2.958 (3) | C20···H17Aiii | 3.0108 |
C3···C6 | 2.772 (3) | C20···H23ix | 3.4498 |
C6···C7 | 3.065 (3) | C21···H12iv | 2.9248 |
C6···C12 | 3.269 (3) | C21···H17Aiii | 3.3558 |
C6···C13 | 3.474 (3) | C21···H24ix | 3.4170 |
C7···C10 | 2.777 (3) | C22···H4xvi | 3.3317 |
C7···C14 | 3.498 (3) | C22···H10xvii | 3.4938 |
C8···C11 | 2.772 (3) | C22···H11iv | 3.4167 |
C8···C13 | 2.845 (3) | C22···H12iv | 3.0977 |
C9···C12 | 2.776 (3) | C22···H24ix | 3.3848 |
C16···C18 | 3.199 (3) | C23···H9xvii | 3.3216 |
C19···C22 | 2.780 (4) | C23···H10xvii | 3.2823 |
C20···C23 | 2.770 (3) | C24···H8ii | 2.9232 |
C21···C24 | 2.769 (3) | C24···H17Bi | 3.3765 |
O1···N1i | 2.771 (3) | H1···O1iii | 2.00 (3) |
O1···C8ii | 3.447 (3) | H1···C4iv | 3.46 (2) |
O1···C9ii | 3.474 (3) | H1···C18iii | 3.24 (3) |
O1···C17i | 3.268 (3) | H1···H4iv | 2.9546 |
N1···O1iii | 2.771 (3) | H1···H8viii | 3.3814 |
C3···C15iv | 3.554 (4) | H1···H9viii | 3.1978 |
C4···C20iv | 3.528 (3) | H1···H17Aiii | 3.3077 |
C6···C12v | 3.578 (3) | H1···H24iii | 3.5752 |
C8···O1vi | 3.447 (3) | H2···C3iv | 3.4927 |
C9···O1vi | 3.474 (3) | H2···C7vii | 3.5441 |
C12···C6vii | 3.578 (3) | H2···C8vii | 3.5540 |
C14···C23vi | 3.564 (3) | H2···C9vii | 3.4025 |
C15···C3iv | 3.554 (4) | H2···C10vii | 3.2279 |
C15···C16viii | 3.543 (3) | H2···C11vii | 3.1878 |
C16···C15viii | 3.543 (3) | H2···C12vii | 3.3599 |
C16···C16viii | 3.557 (3) | H2···H2iv | 3.4989 |
C17···O1iii | 3.268 (3) | H2···H3iv | 3.2230 |
C19···C23ix | 3.414 (3) | H2···H6vii | 3.2317 |
C20···C4iv | 3.528 (3) | H2···H11vii | 3.5730 |
C22···C24ix | 3.432 (3) | H3···C9vii | 3.0499 |
C23···C14ii | 3.564 (3) | H3···C10vii | 3.2432 |
C23···C19ix | 3.414 (3) | H3···C13iv | 3.3597 |
C23···C24ix | 3.458 (3) | H3···C14iv | 2.8059 |
C24···C22ix | 3.432 (3) | H3···C15iv | 2.7413 |
C24···C23ix | 3.458 (3) | H3···C16iv | 3.1961 |
O1···H1 | 3.00 (3) | H3···H2iv | 3.2230 |
O1···H17A | 2.4780 | H3···H9vii | 2.9258 |
O1···H24 | 2.5220 | H3···H10vii | 3.2692 |
N1···H20 | 2.6223 | H4···O1xii | 3.0210 |
N2···H2 | 2.6146 | H4···N1iv | 3.3719 |
N2···H6 | 2.6176 | H4···C15iv | 3.4072 |
N2···H8 | 2.6222 | H4···C16iv | 3.3491 |
N2···H12 | 2.6170 | H4···C22xi | 3.3317 |
C1···H3 | 3.2457 | H4···H1iv | 2.9546 |
C1···H5 | 3.2575 | H4···H11ii | 3.2716 |
C1···H12 | 2.6877 | H4···H20iv | 2.8948 |
C2···H4 | 3.2697 | H4···H21xi | 3.4262 |
C2···H6 | 3.2681 | H4···H22xi | 2.5702 |
C2···H12 | 3.4852 | H5···C7v | 3.1294 |
C3···H5 | 3.2559 | H5···C8v | 3.0658 |
C4···H2 | 3.2717 | H5···C9v | 3.2831 |
C4···H6 | 3.2634 | H5···C10v | 3.5636 |
C5···H3 | 3.2538 | H5···C12v | 3.4389 |
C6···H2 | 3.2698 | H5···C17xii | 3.3890 |
C6···H4 | 3.2637 | H5···H8v | 3.4222 |
C6···H12 | 2.9540 | H5···H11ii | 3.2830 |
C7···H6 | 2.8606 | H5···H17Axii | 2.7660 |
C7···H9 | 3.2552 | H5···H17Bxii | 3.3385 |
C7···H11 | 3.2560 | H5···H20iv | 3.0863 |
C8···H10 | 3.2632 | H5···H22xi | 3.1939 |
C8···H12 | 3.2759 | H6···N2v | 3.0712 |
C9···H11 | 3.2474 | H6···C7v | 3.0781 |
C10···H8 | 3.2631 | H6···C12v | 3.0155 |
C10···H12 | 3.2649 | H6···C13v | 3.5021 |
C11···H9 | 3.2481 | H6···H2v | 3.2317 |
C12···H6 | 3.0831 | H6···H12v | 2.9384 |
C12···H8 | 3.2756 | H6···H21iv | 3.5884 |
C12···H10 | 3.2641 | H8···O1vi | 2.7971 |
C13···H2 | 2.8167 | H8···C17viii | 3.3058 |
C13···H8 | 2.5819 | H8···C18vi | 3.1877 |
C14···H2 | 3.4466 | H8···C19vi | 3.1300 |
C14···H8 | 3.1079 | H8···C24vi | 2.9232 |
C15···H17A | 3.1485 | H8···H1viii | 3.3814 |
C15···H17B | 3.1456 | H8···H5vii | 3.4222 |
C16···H1 | 2.86 (3) | H8···H17Bviii | 2.4485 |
C18···H17A | 2.5817 | H8···H24vi | 2.7703 |
C18···H17B | 3.2072 | H9···O1vi | 2.8433 |
C18···H20 | 2.7085 | H9···C14vi | 3.4887 |
C18···H24 | 2.6176 | H9···C15vi | 3.1005 |
C19···H1 | 2.55 (3) | H9···C16vi | 3.1969 |
C19···H21 | 3.2652 | H9···C18vi | 3.3078 |
C19···H23 | 3.2645 | H9···C23xiii | 3.3216 |
C20···H1 | 2.59 (3) | H9···H1viii | 3.1978 |
C20···H22 | 3.2540 | H9···H3v | 2.9258 |
C20···H24 | 3.2601 | H9···H22xiii | 3.5787 |
C21···H23 | 3.2515 | H9···H23xiii | 2.4318 |
C22···H20 | 3.2532 | H10···N2vi | 3.3987 |
C22···H24 | 3.2569 | H10···C1vi | 3.1174 |
C23···H21 | 3.2511 | H10···C2vi | 3.4708 |
C24···H20 | 3.2591 | H10···C6vi | 3.3378 |
C24···H22 | 3.2586 | H10···C13vi | 3.0389 |
H1···H17A | 2.7192 | H10···C14vi | 3.1782 |
H1···H17B | 2.2293 | H10···C22xiii | 3.4938 |
H1···H20 | 2.0941 | H10···C23xiii | 3.2823 |
H2···H3 | 2.3366 | H10···H3v | 3.2692 |
H3···H4 | 2.3396 | H10···H11xiv | 3.3934 |
H4···H5 | 2.3345 | H10···H22xiii | 3.2294 |
H5···H6 | 2.3408 | H10···H23xiii | 2.8308 |
H6···H12 | 2.9798 | H11···C3vi | 3.3907 |
H8···H9 | 2.3326 | H11···C4vi | 2.9920 |
H9···H10 | 2.3332 | H11···C5vi | 3.0027 |
H10···H11 | 2.3320 | H11···C6vi | 3.4181 |
H11···H12 | 2.3321 | H11···C10xiv | 3.4217 |
H20···H21 | 2.3300 | H11···C11xiv | 3.2281 |
H21···H22 | 2.3303 | H11···C22iv | 3.4167 |
H22···H23 | 2.3317 | H11···H2v | 3.5730 |
H23···H24 | 2.3375 | H11···H4vi | 3.2716 |
O1···H1i | 2.00 (3) | H11···H5vi | 3.2830 |
O1···H4x | 3.0210 | H11···H10xiv | 3.3934 |
O1···H8ii | 2.7971 | H11···H11xiv | 3.0695 |
O1···H9ii | 2.8433 | H11···H22iv | 2.7503 |
O1···H17Bi | 2.8537 | H12···C21iv | 2.9248 |
O1···H20i | 2.9274 | H12···C22iv | 3.0977 |
N1···H4iv | 3.3719 | H12···H6vii | 2.9384 |
N2···H6vii | 3.0712 | H12···H21iv | 2.7981 |
N2···H10ii | 3.3987 | H12···H22iv | 3.0931 |
C1···H10ii | 3.1174 | H17A···C5x | 3.3469 |
C2···H10ii | 3.4708 | H17A···C20i | 3.0108 |
C3···H2iv | 3.4927 | H17A···C21i | 3.3558 |
C3···H11ii | 3.3907 | H17A···H1i | 3.3077 |
C3···H20iv | 3.5010 | H17A···H5x | 2.7660 |
C4···H1iv | 3.46 (2) | H17A···H20i | 2.3287 |
C4···H11ii | 2.9920 | H17A···H21i | 3.0195 |
C4···H20iv | 2.8499 | H17B···O1iii | 2.8537 |
C4···H22xi | 3.1086 | H17B···C8viii | 3.1112 |
C5···H11ii | 3.0027 | H17B···C13viii | 3.2031 |
C5···H17Axii | 3.3469 | H17B···C14viii | 2.8558 |
C5···H20iv | 2.9654 | H17B···C15viii | 3.0852 |
C5···H22xi | 3.4379 | H17B···C24iii | 3.3765 |
C6···H10ii | 3.3378 | H17B···H5x | 3.3385 |
C6···H11ii | 3.4181 | H17B···H8viii | 2.4485 |
C6···H21iv | 3.5731 | H17B···H24iii | 2.5602 |
C7···H2v | 3.5441 | H20···O1iii | 2.9274 |
C7···H5vii | 3.1294 | H20···C3iv | 3.5010 |
C7···H6vii | 3.0781 | H20···C4iv | 2.8499 |
C8···H2v | 3.5540 | H20···C5iv | 2.9654 |
C8···H5vii | 3.0658 | H20···C17iii | 3.2884 |
C8···H17Bviii | 3.1112 | H20···H4iv | 2.8948 |
C9···H2v | 3.4025 | H20···H5iv | 3.0863 |
C9···H3v | 3.0499 | H20···H17Aiii | 2.3287 |
C9···H5vii | 3.2831 | H21···C6iv | 3.5731 |
C9···H23xiii | 3.0533 | H21···C12iv | 3.5003 |
C10···H2v | 3.2279 | H21···C14xviii | 3.4014 |
C10···H3v | 3.2432 | H21···C15xviii | 3.5546 |
C10···H5vii | 3.5636 | H21···H4xvi | 3.4262 |
C10···H11xiv | 3.4217 | H21···H6iv | 3.5884 |
C10···H22xiii | 3.4622 | H21···H12iv | 2.7981 |
C10···H23xiii | 3.2492 | H21···H17Aiii | 3.0195 |
C11···H2v | 3.1878 | H22···C4xvi | 3.1086 |
C11···H11xiv | 3.2281 | H22···C5xvi | 3.4379 |
C11···H22iv | 3.4844 | H22···C10xvii | 3.4622 |
C12···H2v | 3.3599 | H22···C11iv | 3.4844 |
C12···H5vii | 3.4389 | H22···H4xvi | 2.5702 |
C12···H6vii | 3.0155 | H22···H5xvi | 3.1939 |
C12···H21iv | 3.5003 | H22···H9xvii | 3.5787 |
C13···H3iv | 3.3597 | H22···H10xvii | 3.2294 |
C13···H6vii | 3.5021 | H22···H11iv | 2.7503 |
C13···H10ii | 3.0389 | H22···H12iv | 3.0931 |
C13···H17Bviii | 3.2031 | H22···H24ix | 3.5928 |
C13···H23vi | 3.5690 | H23···C9xvii | 3.0533 |
C14···H3iv | 2.8059 | H23···C10xvii | 3.2492 |
C14···H9ii | 3.4887 | H23···C13ii | 3.5690 |
C14···H10ii | 3.1782 | H23···C14ii | 3.0996 |
C14···H17Bviii | 2.8558 | H23···C15ii | 2.9697 |
C14···H21xv | 3.4014 | H23···C16ii | 3.3206 |
C14···H23vi | 3.0996 | H23···C19ix | 3.3890 |
C14···H24vi | 3.2035 | H23···C20ix | 3.4498 |
C15···H3iv | 2.7413 | H23···H9xvii | 2.4318 |
C15···H4iv | 3.4072 | H23···H10xvii | 2.8308 |
C15···H9ii | 3.1005 | H24···C14ii | 3.2035 |
C15···H17Bviii | 3.0852 | H24···C15ii | 3.1854 |
C15···H21xv | 3.5546 | H24···C16i | 3.5434 |
C15···H23vi | 2.9697 | H24···C17i | 3.3524 |
C15···H24vi | 3.1854 | H24···C21ix | 3.4170 |
C16···H3iv | 3.1961 | H24···C22ix | 3.3848 |
C16···H4iv | 3.3491 | H24···H1i | 3.5752 |
C16···H9ii | 3.1969 | H24···H8ii | 2.7703 |
C16···H23vi | 3.3206 | H24···H17Bi | 2.5602 |
C16···H24iii | 3.5434 | H24···H22ix | 3.5928 |
C17—N1—C18 | 122.13 (17) | C18—N1—H1 | 120 (2) |
C1—N2—C7 | 122.14 (14) | C1—C2—H2 | 120.416 |
C1—N2—C13 | 117.63 (17) | C3—C2—H2 | 120.421 |
C7—N2—C13 | 119.93 (18) | C2—C3—H3 | 119.640 |
N2—C1—C2 | 119.60 (17) | C4—C3—H3 | 119.651 |
N2—C1—C6 | 119.50 (19) | C3—C4—H4 | 120.235 |
C2—C1—C6 | 120.9 (2) | C5—C4—H4 | 120.231 |
C1—C2—C3 | 119.16 (19) | C4—C5—H5 | 119.828 |
C2—C3—C4 | 120.7 (2) | C6—C5—H5 | 119.814 |
C3—C4—C5 | 119.5 (2) | C1—C6—H6 | 120.311 |
C4—C5—C6 | 120.36 (19) | C5—C6—H6 | 120.311 |
C1—C6—C5 | 119.4 (2) | C7—C8—H8 | 120.256 |
N2—C7—C8 | 120.19 (15) | C9—C8—H8 | 120.261 |
N2—C7—C12 | 119.58 (19) | C8—C9—H9 | 119.637 |
C8—C7—C12 | 120.19 (19) | C10—C9—H9 | 119.637 |
C7—C8—C9 | 119.48 (16) | C9—C10—H10 | 120.281 |
C8—C9—C10 | 120.7 (2) | C11—C10—H10 | 120.288 |
C9—C10—C11 | 119.4 (2) | C10—C11—H11 | 119.538 |
C10—C11—C12 | 120.92 (17) | C12—C11—H11 | 119.542 |
C7—C12—C11 | 119.2 (2) | C7—C12—H12 | 120.393 |
N2—C13—C14 | 178.7 (2) | C11—C12—H12 | 120.383 |
C13—C14—C15 | 174.6 (2) | N1—C17—H17A | 109.264 |
C14—C15—C16 | 177.9 (2) | N1—C17—H17B | 109.266 |
C15—C16—C17 | 178.1 (2) | C16—C17—H17A | 109.270 |
N1—C17—C16 | 111.75 (17) | C16—C17—H17B | 109.274 |
O1—C18—N1 | 121.1 (2) | H17A—C17—H17B | 107.935 |
O1—C18—C19 | 120.60 (19) | C19—C20—H20 | 119.896 |
N1—C18—C19 | 118.29 (17) | C21—C20—H20 | 119.889 |
C18—C19—C20 | 122.46 (18) | C20—C21—H21 | 119.898 |
C18—C19—C24 | 118.24 (17) | C22—C21—H21 | 119.896 |
C20—C19—C24 | 119.3 (2) | C21—C22—H22 | 119.989 |
C19—C20—C21 | 120.2 (2) | C23—C22—H22 | 119.981 |
C20—C21—C22 | 120.2 (2) | C22—C23—H23 | 119.987 |
C21—C22—C23 | 120.0 (2) | C24—C23—H23 | 119.985 |
C22—C23—C24 | 120.0 (2) | C19—C24—H24 | 119.887 |
C19—C24—C23 | 120.24 (19) | C23—C24—H24 | 119.871 |
C17—N1—H1 | 118 (2) | ||
C17—N1—C18—O1 | 7.2 (2) | N2—C7—C12—C11 | 176.76 (15) |
C17—N1—C18—C19 | −171.73 (13) | C8—C7—C12—C11 | −1.0 (3) |
C18—N1—C17—C16 | 84.99 (19) | C12—C7—C8—C9 | 1.6 (3) |
C1—N2—C7—C8 | −149.21 (16) | C7—C8—C9—C10 | −0.8 (3) |
C1—N2—C7—C12 | 33.1 (2) | C8—C9—C10—C11 | −0.6 (3) |
C7—N2—C1—C2 | −132.38 (16) | C9—C10—C11—C12 | 1.3 (3) |
C7—N2—C1—C6 | 50.1 (2) | C10—C11—C12—C7 | −0.5 (3) |
C13—N2—C1—C2 | 53.8 (2) | O1—C18—C19—C20 | −160.81 (15) |
C13—N2—C1—C6 | −123.66 (17) | O1—C18—C19—C24 | 17.2 (2) |
C13—N2—C7—C8 | 24.5 (3) | N1—C18—C19—C20 | 18.1 (2) |
C13—N2—C7—C12 | −153.28 (16) | N1—C18—C19—C24 | −163.86 (14) |
N2—C1—C2—C3 | −177.48 (13) | C18—C19—C20—C21 | 177.75 (14) |
N2—C1—C6—C5 | 177.35 (13) | C18—C19—C24—C23 | −177.58 (13) |
C2—C1—C6—C5 | −0.1 (3) | C20—C19—C24—C23 | 0.5 (2) |
C6—C1—C2—C3 | −0.0 (3) | C24—C19—C20—C21 | −0.3 (2) |
C1—C2—C3—C4 | −0.0 (3) | C19—C20—C21—C22 | −0.1 (3) |
C2—C3—C4—C5 | 0.2 (3) | C20—C21—C22—C23 | 0.3 (3) |
C3—C4—C5—C6 | −0.3 (3) | C21—C22—C23—C24 | −0.0 (3) |
C4—C5—C6—C1 | 0.3 (3) | C22—C23—C24—C19 | −0.4 (3) |
N2—C7—C8—C9 | −176.13 (15) |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x, −y+1/2, z−1/2; (iii) −x, y+1/2, −z+1/2; (iv) −x+1, −y+1, −z+1; (v) −x+1, y−1/2, −z+3/2; (vi) x, −y+1/2, z+1/2; (vii) −x+1, y+1/2, −z+3/2; (viii) −x, −y+1, −z+1; (ix) −x, −y+1, −z; (x) x−1, −y+1/2, z−1/2; (xi) −x+1, y−1/2, −z+1/2; (xii) x+1, −y+1/2, z+1/2; (xiii) x, y, z+1; (xiv) −x+1, −y+1, −z+2; (xv) x, −y+3/2, z+1/2; (xvi) −x+1, y+1/2, −z+1/2; (xvii) x, y, z−1; (xviii) x, −y+3/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···C14iv | 0.95 | 2.81 | 3.673 (4) | 152 |
C3—H3···C15iv | 0.95 | 2.74 | 3.554 (4) | 144 |
N1—H1···O1iii | 0.85 (3) | 2.00 (3) | 2.771 (3) | 149 (3) |
Symmetry codes: (iii) −x, y+1/2, −z+1/2; (iv) −x+1, −y+1, −z+1. |
Funding information
Funding for this research was provided by: Japan Science and Technology Agency, Research for Promoting Technological Seedshttps://doi.org/10.13039/501100002241
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