organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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Crystal structure of (2-{[3,5-bis­­(1,1-di­methyl­eth­yl)-4-hy­dr­oxy­phen­yl](5-methyl-2H-pyrrol-2-yl­­idene)meth­yl}-5-methyl-1H-pyrrolido-κ2N,N′)di­fluoridoboron

CROSSMARK_Color_square_no_text.svg

aResearch Reactor Institute, Kyoto University, 2-1 Asashiro-Nishi, Kumatori, Osaka 590-0494, Japan, bNihon University Junior College, 7-24-1 Narashinodai, Funabashi, Chiba 274-8501, Japan, cDepartment of Engineering, The University of Tokushima, Minami-Josanjima, Tokushima 770-8506, Japan, dLaboratory of Pharmaceutical & Medicinal Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigakunishi, Gifu, 501-1196, Japan, and eNiigata University of Pharmacy and Applied Life Sciences, 265-1 Higashijima, Akiha-ku, Niigata 956-8603, Japan
*Correspondence e-mail: morimoto@rri.kyoto-u.ac.jp

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 18 August 2015; accepted 23 August 2015; online 29 August 2015)

The title compound, C25H31BF2N2O, is a potential boron tracedrug in boron neutron capture therapy (BNCT), in which the B atom adopts a distorted BN2F2 tetra­hedral geometry: it is soluble in dimethyl sulfoxide, di­methyl­formamide and methanol. The pyrrolyl­idene­methyl­pyrrole triple fused ring system is almost planar (r.m.s. deviation = 0.031 Å) and subtends a dihedral angle of 47.09 (5)° with the plane of the pendant phenol ring. The phenol –OH group is blocked from forming hydrogen bonds by the adjacent bulky tert-butyl groups. In the crystal, inversion dimers linked by pairs of very weak C—H⋯F inter­actions generate R22(22) loops.

1. Related literature

For background to tracer compounds for BNCT, see: Hori et al. (2010[Hori, H., Uto, Y. & Nakata, E. (2010). Anticancer Res. 30, 3233-3242.], 2012[Hori, H., Uto, Y. & Nakata, E. (2012). Anticancer Res. 32, 2235-2239.]). For further synthetic details, see: Nakata et al. (2011[Nakata, E., Koizumi, M., Yamashita, Y., Onaka, K., Sakurai, Y., Kondo, N., Ono, K., Uto, Y. & Hori, H. (2011). Anticancer Res. 31, 2477-2481.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C25H31BF2N2O

  • Mr = 424.34

  • Triclinic, [P \overline 1]

  • a = 9.2518 (2) Å

  • b = 10.0975 (2) Å

  • c = 12.5142 (3) Å

  • α = 79.364 (6)°

  • β = 89.613 (6)°

  • γ = 83.367 (6)°

  • V = 1141.18 (5) Å3

  • Z = 2

  • Cu Kα radiation

  • μ = 0.69 mm−1

  • T = 296 K

  • 0.16 × 0.08 × 0.04 mm

2.2. Data collection

  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Rigaku, 1995[Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.749, Tmax = 0.973

  • 13606 measured reflections

  • 4044 independent reflections

  • 3644 reflections with F2 > 2.0σ(F2)

  • Rint = 0.026

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.115

  • S = 1.09

  • 4044 reflections

  • 289 parameters

  • H-atom parameters constrained

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C12—H12C⋯F2i 0.96 2.54 3.4464 (18) 158
Symmetry code: (i) -x+1, -y+2, -z+1.

Data collection: RAPID-AUTO (Rigaku, 2011[Rigaku (2011). RAPID-AUTO and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: Il Milione (Burla et al., 2007[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609-613.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: CrystalStructure (Rigaku, 2011[Rigaku (2011). RAPID-AUTO and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); software used to prepare material for publication: CrystalStructure.

Supporting information


Chemical context top

For the synthesis of 2-{[3,5-bis­(1,1-di­methyl­ethyl)-4-hy­droxy­phenyl](5-methyl-2H-pyrrol-2-yl­idene)methyl}-5-methyl-1H-pyrrolido-κ2N,N']difluoridoboron see: Nakata, et al. (2011). The compound: CAS Registry Number 1415304-92-5. The ring compound binding BF2 is a contracted form given in IUPAC.

Structural commentary top

The traceability of boron tracedrugs is based on the neutron capture activity of the stable isotope boron-10 embedded in the drug. Thus, newly designed boron tracedrugs would be novel pharmaceuticals, the structures of which would always include natural boron (B11, 80.4%; B10, 19.6%), as tracers, embedded deeply in their skeletons or scaffolds. The compound is used at a cancer therapy by an irradiation of neutron, since B10 atom generates a high energy alpha-line within a cancer cell by fission of the atom. The compound is required to keep a suitable three-dimensional structure until reaching cancer cell via intra­venous injection and an irradiation of neutron. Our group has developed boron tracedrugs in use of boron-neutron reaction (Hori, et al. 2010, 2012), in this study a suitable compound has been reported and presents that two bulky rings tilt each other to avoid steric hindrance.

Synthesis and crystallization top

Crystals were obtained from methanol solvent at room temperature by slow evaporation. Crystal structure has no present of solvent molecule. The synthesis of the title compound was decribed by Nakata et al. (2011). The compound: CAS Registry Number 1415304-92-5. The ring compound binding BF2 is a contracted form given in IUPAC.

Refinement top

All hydrogen atoms were placed in the calculated positions and constrained their parent atoms with a C—H distances of 0.95 Å (aromatic) and 0.99 Å (methyl­ene) and with Uiso(H) = 1.2Ueq(C), and 0.98 Å for CH3 [Uiso(H)= 1.5Ueq(C)].

Related literature top

For background to tracer compounds for BNCT, see: Hori et al. (2010, 2012). For further synthetic details, see: Nakata et al. (2011).

Structure description top

For the synthesis of 2-{[3,5-bis­(1,1-di­methyl­ethyl)-4-hy­droxy­phenyl](5-methyl-2H-pyrrol-2-yl­idene)methyl}-5-methyl-1H-pyrrolido-κ2N,N']difluoridoboron see: Nakata, et al. (2011). The compound: CAS Registry Number 1415304-92-5. The ring compound binding BF2 is a contracted form given in IUPAC.

The traceability of boron tracedrugs is based on the neutron capture activity of the stable isotope boron-10 embedded in the drug. Thus, newly designed boron tracedrugs would be novel pharmaceuticals, the structures of which would always include natural boron (B11, 80.4%; B10, 19.6%), as tracers, embedded deeply in their skeletons or scaffolds. The compound is used at a cancer therapy by an irradiation of neutron, since B10 atom generates a high energy alpha-line within a cancer cell by fission of the atom. The compound is required to keep a suitable three-dimensional structure until reaching cancer cell via intra­venous injection and an irradiation of neutron. Our group has developed boron tracedrugs in use of boron-neutron reaction (Hori, et al. 2010, 2012), in this study a suitable compound has been reported and presents that two bulky rings tilt each other to avoid steric hindrance.

For background to tracer compounds for BNCT, see: Hori et al. (2010, 2012). For further synthetic details, see: Nakata et al. (2011).

Synthesis and crystallization top

Crystals were obtained from methanol solvent at room temperature by slow evaporation. Crystal structure has no present of solvent molecule. The synthesis of the title compound was decribed by Nakata et al. (2011). The compound: CAS Registry Number 1415304-92-5. The ring compound binding BF2 is a contracted form given in IUPAC.

Refinement details top

All hydrogen atoms were placed in the calculated positions and constrained their parent atoms with a C—H distances of 0.95 Å (aromatic) and 0.99 Å (methyl­ene) and with Uiso(H) = 1.2Ueq(C), and 0.98 Å for CH3 [Uiso(H)= 1.5Ueq(C)].

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2011); cell refinement: RAPID-AUTO (Rigaku, 2011); data reduction: RAPID-AUTO (Rigaku, 2011); program(s) used to solve structure: Il Milione (Burla et al., 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2011); software used to prepare material for publication: CrystalStructure (Rigaku, 2011).

Figures top
[Figure 1] Fig. 1. Molecular structure of the compound. Displacement ellipsoids are shown at the 50% probability level. H atoms are depicted as small spheres of arbitrary radius.
(2-{[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl](5-methyl-2H-pyrrol-2-ylidene)methyl}-5-methyl-1H-pyrrolido-κ2N,N')difluoridoboron top
Crystal data top
C25H31BF2N2OZ = 2
Mr = 424.34F(000) = 452.00
Triclinic, P1Dx = 1.235 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54187 Å
a = 9.2518 (2) ÅCell parameters from 11333 reflections
b = 10.0975 (2) Åθ = 3.6–68.2°
c = 12.5142 (3) ŵ = 0.69 mm1
α = 79.364 (6)°T = 296 K
β = 89.613 (6)°Platelet, orange
γ = 83.367 (6)°0.16 × 0.08 × 0.04 mm
V = 1141.18 (5) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3644 reflections with F2 > 2.0σ(F2)
Detector resolution: 10.000 pixels mm-1Rint = 0.026
ω scansθmax = 67.5°, θmin = 3.6°
Absorption correction: multi-scan
(ABSCOR; Rigaku, 1995)
h = 1010
Tmin = 0.749, Tmax = 0.973k = 1212
13606 measured reflectionsl = 1414
4044 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0594P)2 + 0.4471P]
where P = (Fo2 + 2Fc2)/3
4044 reflections(Δ/σ)max < 0.001
289 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.20 e Å3
Primary atom site location: structure-invariant direct methods
Crystal data top
C25H31BF2N2Oγ = 83.367 (6)°
Mr = 424.34V = 1141.18 (5) Å3
Triclinic, P1Z = 2
a = 9.2518 (2) ÅCu Kα radiation
b = 10.0975 (2) ŵ = 0.69 mm1
c = 12.5142 (3) ÅT = 296 K
α = 79.364 (6)°0.16 × 0.08 × 0.04 mm
β = 89.613 (6)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4044 independent reflections
Absorption correction: multi-scan
(ABSCOR; Rigaku, 1995)
3644 reflections with F2 > 2.0σ(F2)
Tmin = 0.749, Tmax = 0.973Rint = 0.026
13606 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.115H-atom parameters constrained
S = 1.09Δρmax = 0.29 e Å3
4044 reflectionsΔρmin = 0.20 e Å3
289 parameters
Special details top

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 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.16643 (10)0.79448 (8)0.09158 (7)0.0297 (2)
F20.39555 (10)0.84379 (8)0.11327 (7)0.0294 (2)
O10.22265 (12)0.68344 (10)0.86928 (8)0.0231 (2)
N10.30765 (13)0.67065 (12)0.24855 (9)0.0191 (3)
N20.21212 (13)0.91383 (12)0.23671 (9)0.0193 (3)
C10.23318 (15)0.70635 (14)0.75831 (11)0.0181 (3)
C20.18152 (15)0.60808 (13)0.70604 (11)0.0183 (3)
C30.18647 (15)0.63023 (14)0.59314 (11)0.0187 (3)
C40.24376 (15)0.74233 (13)0.53267 (11)0.0185 (3)
C50.29681 (15)0.83469 (14)0.58803 (11)0.0188 (3)
C60.29266 (15)0.82094 (13)0.70055 (11)0.0185 (3)
C70.12345 (16)0.47938 (14)0.76987 (11)0.0203 (3)
C80.00798 (17)0.51496 (15)0.83913 (12)0.0263 (3)
C90.24586 (17)0.39358 (14)0.84310 (12)0.0252 (3)
C100.07400 (18)0.38987 (15)0.69353 (12)0.0257 (3)
C110.34936 (16)0.92882 (14)0.75712 (11)0.0207 (3)
C120.47337 (17)0.86627 (15)0.83888 (12)0.0264 (3)
C130.22373 (18)1.00162 (15)0.81377 (13)0.0267 (3)
C140.41194 (18)1.03996 (15)0.67502 (12)0.0274 (3)
C150.24904 (15)0.76195 (14)0.41279 (11)0.0189 (3)
C160.30154 (15)0.65409 (14)0.36187 (11)0.0189 (3)
C170.35863 (16)0.51942 (14)0.40509 (12)0.0219 (3)
C180.39704 (17)0.45610 (15)0.31931 (12)0.0241 (3)
C190.36563 (16)0.55126 (14)0.22312 (12)0.0213 (3)
C200.16017 (16)1.04503 (14)0.19924 (12)0.0218 (3)
C210.11602 (16)1.10733 (15)0.28709 (12)0.0235 (3)
C220.14065 (16)1.01132 (14)0.38080 (12)0.0218 (3)
C230.20257 (15)0.88981 (14)0.34988 (11)0.0192 (3)
C240.38939 (18)0.53166 (16)0.10909 (12)0.0259 (3)
C250.15235 (18)1.10739 (15)0.08147 (12)0.0264 (3)
B10.27066 (19)0.80652 (16)0.16769 (13)0.0209 (3)
H10.242130.75040.89220.0277*
H30.150460.568370.556670.0224*
H50.336610.908550.54810.0225*
H8A0.039140.433060.879550.0316*
H8B0.086080.563660.792540.0316*
H8C0.019110.57040.888580.0316*
H9A0.211230.311640.880380.0302*
H9B0.27530.444290.895330.0302*
H9C0.327430.371280.799290.0302*
H10A0.0020.440510.645860.0308*
H10B0.038210.311340.735790.0308*
H10C0.154880.361820.651210.0308*
H12A0.552930.82620.801420.0317*
H12B0.438730.797810.89350.0317*
H12C0.505770.935810.872670.0317*
H13A0.258861.072880.843910.0320*
H13B0.186760.937770.870910.0320*
H13C0.147351.039550.761740.0320*
H14A0.491410.999730.637590.0329*
H14B0.446031.105120.712860.0329*
H14C0.337431.084380.623380.0329*
H170.368490.480530.478440.0262*
H180.436750.366260.324060.0289*
H210.07711.19730.282950.0282*
H220.120261.024190.451290.0261*
H24A0.438050.604460.070170.0311*
H24B0.297250.5310.07450.0311*
H24C0.448210.446880.109040.0311*
H25A0.080561.068730.045750.0316*
H25B0.24551.090070.049320.0316*
H25C0.125951.203520.073480.0316*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0432 (6)0.0228 (4)0.0232 (5)0.0056 (4)0.0130 (4)0.0026 (3)
F20.0376 (5)0.0257 (5)0.0273 (5)0.0101 (4)0.0142 (4)0.0075 (4)
O10.0345 (6)0.0206 (5)0.0158 (5)0.0088 (4)0.0015 (4)0.0040 (4)
N10.0194 (6)0.0217 (6)0.0168 (6)0.0031 (5)0.0001 (5)0.0048 (5)
N20.0195 (6)0.0208 (6)0.0173 (6)0.0034 (5)0.0001 (5)0.0018 (5)
C10.0189 (7)0.0192 (7)0.0155 (7)0.0005 (5)0.0001 (5)0.0027 (5)
C20.0172 (7)0.0167 (7)0.0199 (7)0.0008 (5)0.0001 (5)0.0018 (5)
C30.0194 (7)0.0183 (7)0.0190 (7)0.0021 (5)0.0009 (5)0.0051 (5)
C40.0182 (7)0.0189 (7)0.0183 (7)0.0010 (5)0.0008 (5)0.0037 (5)
C50.0185 (7)0.0181 (7)0.0191 (7)0.0022 (5)0.0014 (5)0.0014 (5)
C60.0176 (7)0.0182 (7)0.0198 (7)0.0009 (5)0.0003 (5)0.0042 (5)
C70.0248 (8)0.0178 (7)0.0183 (7)0.0047 (6)0.0001 (6)0.0021 (5)
C80.0284 (9)0.0232 (7)0.0274 (8)0.0073 (6)0.0057 (6)0.0021 (6)
C90.0321 (9)0.0182 (7)0.0242 (8)0.0032 (6)0.0039 (6)0.0008 (6)
C100.0325 (9)0.0218 (7)0.0239 (8)0.0099 (6)0.0005 (6)0.0027 (6)
C110.0258 (8)0.0186 (7)0.0188 (7)0.0054 (6)0.0004 (6)0.0045 (6)
C120.0302 (9)0.0247 (8)0.0259 (8)0.0080 (6)0.0040 (6)0.0058 (6)
C130.0348 (9)0.0199 (7)0.0274 (8)0.0050 (6)0.0054 (7)0.0085 (6)
C140.0363 (9)0.0245 (8)0.0241 (8)0.0133 (7)0.0010 (7)0.0056 (6)
C150.0160 (7)0.0217 (7)0.0195 (7)0.0055 (5)0.0001 (5)0.0034 (6)
C160.0188 (7)0.0234 (7)0.0151 (7)0.0051 (6)0.0002 (5)0.0036 (5)
C170.0218 (8)0.0241 (7)0.0187 (7)0.0011 (6)0.0014 (6)0.0025 (6)
C180.0253 (8)0.0211 (7)0.0248 (8)0.0027 (6)0.0003 (6)0.0048 (6)
C190.0194 (8)0.0239 (7)0.0212 (7)0.0015 (6)0.0006 (6)0.0065 (6)
C200.0196 (8)0.0220 (7)0.0225 (7)0.0029 (6)0.0013 (6)0.0005 (6)
C210.0239 (8)0.0198 (7)0.0257 (8)0.0010 (6)0.0000 (6)0.0034 (6)
C220.0219 (8)0.0245 (7)0.0193 (7)0.0019 (6)0.0017 (6)0.0053 (6)
C230.0190 (7)0.0220 (7)0.0170 (7)0.0044 (6)0.0007 (5)0.0035 (5)
C240.0285 (8)0.0277 (8)0.0219 (8)0.0006 (6)0.0021 (6)0.0078 (6)
C250.0308 (9)0.0245 (8)0.0218 (8)0.0009 (6)0.0013 (6)0.0005 (6)
B10.0268 (9)0.0209 (8)0.0159 (8)0.0063 (7)0.0005 (6)0.0034 (6)
Geometric parameters (Å, º) top
F1—B11.391 (2)C22—C231.412 (2)
F2—B11.391 (2)O1—H10.820
O1—C11.3698 (17)C3—H30.930
N1—C161.3985 (18)C5—H50.930
N1—C191.3536 (19)C8—H8A0.960
N1—B11.5515 (18)C8—H8B0.960
N2—C201.3537 (17)C8—H8C0.960
N2—C231.3960 (18)C9—H9A0.960
N2—B11.555 (2)C9—H9B0.960
C1—C21.412 (2)C9—H9C0.960
C1—C61.4132 (19)C10—H10A0.960
C2—C31.3904 (19)C10—H10B0.960
C2—C71.5453 (19)C10—H10C0.960
C3—C41.3971 (19)C12—H12A0.960
C4—C51.393 (2)C12—H12B0.960
C4—C151.4778 (19)C12—H12C0.960
C5—C61.3899 (19)C13—H13A0.960
C6—C111.544 (2)C13—H13B0.960
C7—C81.536 (2)C13—H13C0.960
C7—C91.5386 (19)C14—H14A0.960
C7—C101.536 (2)C14—H14B0.960
C11—C121.540 (2)C14—H14C0.960
C11—C131.542 (2)C17—H170.930
C11—C141.538 (2)C18—H180.930
C15—C161.399 (2)C21—H210.930
C15—C231.4045 (18)C22—H220.930
C16—C171.4096 (18)C24—H24A0.960
C17—C181.372 (2)C24—H24B0.960
C18—C191.4036 (19)C24—H24C0.960
C19—C241.488 (2)C25—H25A0.960
C20—C211.400 (2)C25—H25B0.960
C20—C251.491 (2)C25—H25C0.960
C21—C221.3784 (19)
C16—N1—C19107.94 (11)C4—C3—H3118.911
C16—N1—B1125.50 (12)C4—C5—H5118.675
C19—N1—B1126.23 (12)C6—C5—H5118.675
C20—N2—C23107.87 (12)C7—C8—H8A109.472
C20—N2—B1126.91 (11)C7—C8—H8B109.471
C23—N2—B1125.21 (11)C7—C8—H8C109.472
O1—C1—C2115.70 (12)H8A—C8—H8B109.462
O1—C1—C6121.79 (13)H8A—C8—H8C109.480
C2—C1—C6122.51 (13)H8B—C8—H8C109.471
C1—C2—C3117.24 (12)C7—C9—H9A109.472
C1—C2—C7122.35 (12)C7—C9—H9B109.469
C3—C2—C7120.40 (13)C7—C9—H9C109.475
C2—C3—C4122.18 (14)H9A—C9—H9B109.473
C3—C4—C5118.46 (13)H9A—C9—H9C109.469
C3—C4—C15120.80 (13)H9B—C9—H9C109.470
C5—C4—C15120.73 (12)C7—C10—H10A109.472
C4—C5—C6122.65 (13)C7—C10—H10B109.473
C1—C6—C5116.91 (13)C7—C10—H10C109.472
C1—C6—C11122.82 (12)H10A—C10—H10B109.472
C5—C6—C11120.27 (12)H10A—C10—H10C109.464
C2—C7—C8111.62 (11)H10B—C10—H10C109.474
C2—C7—C9109.37 (12)C11—C12—H12A109.467
C2—C7—C10111.74 (11)C11—C12—H12B109.473
C8—C7—C9109.89 (11)C11—C12—H12C109.474
C8—C7—C10107.04 (13)H12A—C12—H12B109.472
C9—C7—C10107.06 (12)H12A—C12—H12C109.466
C6—C11—C12111.63 (11)H12B—C12—H12C109.475
C6—C11—C13110.32 (12)C11—C13—H13A109.473
C6—C11—C14111.71 (12)C11—C13—H13B109.475
C12—C11—C13110.63 (12)C11—C13—H13C109.468
C12—C11—C14106.21 (12)H13A—C13—H13B109.476
C13—C11—C14106.14 (11)H13A—C13—H13C109.463
C4—C15—C16120.26 (11)H13B—C13—H13C109.472
C4—C15—C23119.79 (13)C11—C14—H14A109.471
C16—C15—C23119.95 (12)C11—C14—H14B109.473
N1—C16—C15121.13 (11)C11—C14—H14C109.466
N1—C16—C17107.58 (13)H14A—C14—H14B109.468
C15—C16—C17131.26 (13)H14A—C14—H14C109.475
C16—C17—C18107.60 (12)H14B—C14—H14C109.473
C17—C18—C19107.72 (13)C16—C17—H17126.206
N1—C19—C18109.16 (13)C18—C17—H17126.198
N1—C19—C24122.81 (12)C17—C18—H18126.137
C18—C19—C24128.03 (13)C19—C18—H18126.139
N2—C20—C21109.37 (12)C20—C21—H21126.155
N2—C20—C25123.17 (14)C22—C21—H21126.156
C21—C20—C25127.45 (12)C21—C22—H22126.369
C20—C21—C22107.69 (13)C23—C22—H22126.370
C21—C22—C23107.26 (13)C19—C24—H24A109.466
N2—C23—C15121.42 (13)C19—C24—H24B109.471
N2—C23—C22107.79 (11)C19—C24—H24C109.467
C15—C23—C22130.78 (13)H24A—C24—H24B109.474
F1—B1—F2108.79 (12)H24A—C24—H24C109.473
F1—B1—N1110.89 (13)H24B—C24—H24C109.476
F1—B1—N2110.50 (12)C20—C25—H25A109.472
F2—B1—N1109.74 (12)C20—C25—H25B109.473
F2—B1—N2110.35 (13)C20—C25—H25C109.478
N1—B1—N2106.56 (11)H25A—C25—H25B109.464
C1—O1—H1109.476H25A—C25—H25C109.468
C2—C3—H3118.907H25B—C25—H25C109.473
C16—N1—C19—C180.27 (15)C1—C2—C7—C10179.90 (11)
C16—N1—C19—C24179.62 (12)C3—C2—C7—C8120.82 (13)
C19—N1—C16—C15178.62 (12)C3—C2—C7—C9117.35 (13)
C19—N1—C16—C170.15 (15)C3—C2—C7—C101.00 (17)
C16—N1—B1—F1125.79 (14)C7—C2—C3—C4177.28 (10)
C16—N1—B1—F2113.99 (15)C2—C3—C4—C50.29 (19)
C16—N1—B1—N25.49 (19)C2—C3—C4—C15179.24 (11)
B1—N1—C16—C154.9 (2)C3—C4—C5—C61.14 (19)
B1—N1—C16—C17173.54 (12)C3—C4—C15—C1647.14 (18)
C19—N1—B1—F161.66 (19)C3—C4—C15—C23133.53 (13)
C19—N1—B1—F258.56 (19)C5—C4—C15—C16132.38 (13)
C19—N1—B1—N2178.04 (12)C5—C4—C15—C2346.95 (18)
B1—N1—C19—C18173.90 (12)C15—C4—C5—C6179.33 (11)
B1—N1—C19—C246.0 (2)C4—C5—C6—C10.86 (19)
C20—N2—C23—C15179.76 (12)C4—C5—C6—C11178.32 (11)
C20—N2—C23—C220.77 (15)C1—C6—C11—C1259.64 (16)
C23—N2—C20—C210.21 (16)C1—C6—C11—C1363.79 (15)
C23—N2—C20—C25179.57 (12)C1—C6—C11—C14178.40 (11)
C20—N2—B1—F156.02 (19)C5—C6—C11—C12121.24 (12)
C20—N2—B1—F264.34 (18)C5—C6—C11—C13115.33 (12)
C20—N2—B1—N1176.57 (13)C5—C6—C11—C142.48 (17)
B1—N2—C20—C21179.05 (12)C4—C15—C16—N1179.89 (11)
B1—N2—C20—C250.3 (2)C4—C15—C16—C171.8 (2)
C23—N2—B1—F1123.11 (13)C4—C15—C23—N2177.05 (11)
C23—N2—B1—F2116.52 (14)C4—C15—C23—C223.6 (2)
C23—N2—B1—N12.57 (19)C16—C15—C23—N22.3 (2)
B1—N2—C23—C151.0 (2)C16—C15—C23—C22177.06 (13)
B1—N2—C23—C22178.50 (12)C23—C15—C16—N10.6 (2)
O1—C1—C2—C3178.10 (10)C23—C15—C16—C17177.49 (13)
O1—C1—C2—C72.77 (17)N1—C16—C17—C180.52 (16)
O1—C1—C6—C5179.44 (10)C15—C16—C17—C18178.77 (14)
O1—C1—C6—C110.28 (19)C16—C17—C18—C190.67 (17)
C2—C1—C6—C50.85 (18)C17—C18—C19—N10.59 (17)
C2—C1—C6—C11180.00 (11)C17—C18—C19—C24179.29 (13)
C6—C1—C2—C32.16 (19)N2—C20—C21—C220.45 (17)
C6—C1—C2—C7176.96 (11)C25—C20—C21—C22178.88 (14)
C1—C2—C3—C41.87 (19)C20—C21—C22—C230.91 (16)
C1—C2—C7—C860.08 (16)C21—C22—C23—N21.04 (16)
C1—C2—C7—C961.75 (16)C21—C22—C23—C15179.55 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12C···F2i0.962.543.4464 (18)158
Symmetry code: (i) x+1, y+2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12C···F2i0.962.543.4464 (18)158
Symmetry code: (i) x+1, y+2, z+1.
 

Acknowledgements

The authors thank Dr Akihito Yamano (Rigaku Co. Ltd) for his kind technical support of data collection, and YM is grateful to the Grant-in-Aid for the project of a mol­ecular mechanism of emotional control (Customer Care Plan 2014, 2015).

References

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