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

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.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.115
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT414_ALERT_2_B Short Intra D-H..H-X       H1     ..  H13B    ..       1.87 Ang.
PLAT420_ALERT_2_B D-H Without Acceptor        O1     -   H1     ..     Please Check
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          2 Check

Alert level C
PLAT414_ALERT_2_C Short Intra D-H..H-X       H1     ..  H12B    ..       1.93 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.599         50 Report

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00600 Degree
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          81 %

   0 ALERT level A = Most likely a serious problem - resolve or explain
   3 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check


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Alert level A
PUBL022_ALERT_1_A There is a mismatched ~ on line 229
              BN~2~F~2 tetrahedral geometry: it is soluble in DMSO, DMF and methanol.
              If you require a ~ then it should be escaped
              with a \, i.e. \~
              Otherwise there must be a matching closing ~, e.g. C~2~H~4~

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S1. Chemical context

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.

S2. Structural commentary

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.

S3. Synthesis and crystallization

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.

S4. Refinement

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

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

Structure description

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

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

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

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

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

Crystal data

C25H31BF2N2O	Z = 2
Mr = 424.34	F(000) = 452.00
Triclinic, P1	Dx = 1.235 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54187 Å
a = 9.2518 (2) Å	Cell parameters from 11333 reflections
b = 10.0975 (2) Å	θ = 3.6–68.2°
c = 12.5142 (3) Å	µ = 0.69 mm^−1
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) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	3644 reflections with F^2 > 2.0σ(F^2)
Detector resolution: 10.000 pixels mm^-1	Rint = 0.026
ω scans	θmax = 67.5°, θmin = 3.6°
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	h = −10→10
Tmin = 0.749, Tmax = 0.973	k = −12→12
13606 measured reflections	l = −14→14
4044 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0594P)^2 + 0.4471P] where P = (Fo^2 + 2Fc^2)/3
4044 reflections	(Δ/σ)max < 0.001
289 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3
Primary atom site location: structure-invariant direct methods

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
F1	0.16643 (10)	0.79448 (8)	0.09158 (7)	0.0297 (2)
F2	0.39555 (10)	0.84379 (8)	0.11327 (7)	0.0294 (2)
O1	0.22265 (12)	0.68344 (10)	0.86928 (8)	0.0231 (2)
N1	0.30765 (13)	0.67065 (12)	0.24855 (9)	0.0191 (3)
N2	0.21212 (13)	0.91383 (12)	0.23671 (9)	0.0193 (3)
C1	0.23318 (15)	0.70635 (14)	0.75831 (11)	0.0181 (3)
C2	0.18152 (15)	0.60808 (13)	0.70604 (11)	0.0183 (3)
C3	0.18647 (15)	0.63023 (14)	0.59314 (11)	0.0187 (3)
C4	0.24376 (15)	0.74233 (13)	0.53267 (11)	0.0185 (3)
C5	0.29681 (15)	0.83469 (14)	0.58803 (11)	0.0188 (3)
C6	0.29266 (15)	0.82094 (13)	0.70055 (11)	0.0185 (3)
C7	0.12345 (16)	0.47938 (14)	0.76987 (11)	0.0203 (3)
C8	−0.00798 (17)	0.51496 (15)	0.83913 (12)	0.0263 (3)
C9	0.24586 (17)	0.39358 (14)	0.84310 (12)	0.0252 (3)
C10	0.07400 (18)	0.38987 (15)	0.69353 (12)	0.0257 (3)
C11	0.34936 (16)	0.92882 (14)	0.75712 (11)	0.0207 (3)
C12	0.47337 (17)	0.86627 (15)	0.83888 (12)	0.0264 (3)
C13	0.22373 (18)	1.00162 (15)	0.81377 (13)	0.0267 (3)
C14	0.41194 (18)	1.03996 (15)	0.67502 (12)	0.0274 (3)
C15	0.24904 (15)	0.76195 (14)	0.41279 (11)	0.0189 (3)
C16	0.30154 (15)	0.65409 (14)	0.36187 (11)	0.0189 (3)
C17	0.35863 (16)	0.51942 (14)	0.40509 (12)	0.0219 (3)
C18	0.39704 (17)	0.45610 (15)	0.31931 (12)	0.0241 (3)
C19	0.36563 (16)	0.55126 (14)	0.22312 (12)	0.0213 (3)
C20	0.16017 (16)	1.04503 (14)	0.19924 (12)	0.0218 (3)
C21	0.11602 (16)	1.10733 (15)	0.28709 (12)	0.0235 (3)
C22	0.14065 (16)	1.01132 (14)	0.38080 (12)	0.0218 (3)
C23	0.20257 (15)	0.88981 (14)	0.34988 (11)	0.0192 (3)
C24	0.38939 (18)	0.53166 (16)	0.10909 (12)	0.0259 (3)
C25	0.15235 (18)	1.10739 (15)	0.08147 (12)	0.0264 (3)
B1	0.27066 (19)	0.80652 (16)	0.16769 (13)	0.0209 (3)
H1	0.24213	0.7504	0.8922	0.0277*
H3	0.15046	0.56837	0.55667	0.0224*
H5	0.33661	0.90855	0.5481	0.0225*
H8A	−0.03914	0.43306	0.87955	0.0316*
H8B	−0.08608	0.56366	0.79254	0.0316*
H8C	0.01911	0.5704	0.88858	0.0316*
H9A	0.21123	0.31164	0.88038	0.0302*
H9B	0.2753	0.44429	0.89533	0.0302*
H9C	0.32743	0.37128	0.79929	0.0302*
H10A	−0.002	0.44051	0.64586	0.0308*
H10B	0.03821	0.31134	0.73579	0.0308*
H10C	0.15488	0.36182	0.65121	0.0308*
H12A	0.55293	0.8262	0.80142	0.0317*
H12B	0.43873	0.79781	0.8935	0.0317*
H12C	0.50577	0.93581	0.87267	0.0317*
H13A	0.25886	1.07288	0.84391	0.0320*
H13B	0.18676	0.93777	0.87091	0.0320*
H13C	0.14735	1.03955	0.76174	0.0320*
H14A	0.49141	0.99973	0.63759	0.0329*
H14B	0.44603	1.10512	0.71286	0.0329*
H14C	0.33743	1.08438	0.62338	0.0329*
H17	0.36849	0.48053	0.47844	0.0262*
H18	0.43675	0.36626	0.32406	0.0289*
H21	0.0771	1.1973	0.28295	0.0282*
H22	0.12026	1.02419	0.45129	0.0261*
H24A	0.43805	0.60446	0.07017	0.0311*
H24B	0.29725	0.531	0.0745	0.0311*
H24C	0.44821	0.44688	0.10904	0.0311*
H25A	0.08056	1.06873	0.04575	0.0316*
H25B	0.2455	1.09007	0.04932	0.0316*
H25C	0.12595	1.20352	0.07348	0.0316*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0432 (6)	0.0228 (4)	0.0232 (5)	−0.0056 (4)	−0.0130 (4)	−0.0026 (3)
F2	0.0376 (5)	0.0257 (5)	0.0273 (5)	−0.0101 (4)	0.0142 (4)	−0.0075 (4)
O1	0.0345 (6)	0.0206 (5)	0.0158 (5)	−0.0088 (4)	0.0015 (4)	−0.0040 (4)
N1	0.0194 (6)	0.0217 (6)	0.0168 (6)	−0.0031 (5)	0.0001 (5)	−0.0048 (5)
N2	0.0195 (6)	0.0208 (6)	0.0173 (6)	−0.0034 (5)	0.0001 (5)	−0.0018 (5)
C1	0.0189 (7)	0.0192 (7)	0.0155 (7)	0.0005 (5)	0.0001 (5)	−0.0027 (5)
C2	0.0172 (7)	0.0167 (7)	0.0199 (7)	−0.0008 (5)	0.0001 (5)	−0.0018 (5)
C3	0.0194 (7)	0.0183 (7)	0.0190 (7)	−0.0021 (5)	−0.0009 (5)	−0.0051 (5)
C4	0.0182 (7)	0.0189 (7)	0.0183 (7)	−0.0010 (5)	0.0008 (5)	−0.0037 (5)
C5	0.0185 (7)	0.0181 (7)	0.0191 (7)	−0.0022 (5)	0.0014 (5)	−0.0014 (5)
C6	0.0176 (7)	0.0182 (7)	0.0198 (7)	−0.0009 (5)	−0.0003 (5)	−0.0042 (5)
C7	0.0248 (8)	0.0178 (7)	0.0183 (7)	−0.0047 (6)	−0.0001 (6)	−0.0021 (5)
C8	0.0284 (9)	0.0232 (7)	0.0274 (8)	−0.0073 (6)	0.0057 (6)	−0.0021 (6)
C9	0.0321 (9)	0.0182 (7)	0.0242 (8)	−0.0032 (6)	−0.0039 (6)	−0.0008 (6)
C10	0.0325 (9)	0.0218 (7)	0.0239 (8)	−0.0099 (6)	−0.0005 (6)	−0.0027 (6)
C11	0.0258 (8)	0.0186 (7)	0.0188 (7)	−0.0054 (6)	0.0004 (6)	−0.0045 (6)
C12	0.0302 (9)	0.0247 (8)	0.0259 (8)	−0.0080 (6)	−0.0040 (6)	−0.0058 (6)
C13	0.0348 (9)	0.0199 (7)	0.0274 (8)	−0.0050 (6)	0.0054 (7)	−0.0085 (6)
C14	0.0363 (9)	0.0245 (8)	0.0241 (8)	−0.0133 (7)	0.0010 (7)	−0.0056 (6)
C15	0.0160 (7)	0.0217 (7)	0.0195 (7)	−0.0055 (5)	−0.0001 (5)	−0.0034 (6)
C16	0.0188 (7)	0.0234 (7)	0.0151 (7)	−0.0051 (6)	−0.0002 (5)	−0.0036 (5)
C17	0.0218 (8)	0.0241 (7)	0.0187 (7)	−0.0011 (6)	−0.0014 (6)	−0.0025 (6)
C18	0.0253 (8)	0.0211 (7)	0.0248 (8)	0.0027 (6)	−0.0003 (6)	−0.0048 (6)
C19	0.0194 (8)	0.0239 (7)	0.0212 (7)	−0.0015 (6)	0.0006 (6)	−0.0065 (6)
C20	0.0196 (8)	0.0220 (7)	0.0225 (7)	−0.0029 (6)	−0.0013 (6)	−0.0005 (6)
C21	0.0239 (8)	0.0198 (7)	0.0257 (8)	0.0010 (6)	0.0000 (6)	−0.0034 (6)
C22	0.0219 (8)	0.0245 (7)	0.0193 (7)	−0.0019 (6)	0.0017 (6)	−0.0053 (6)
C23	0.0190 (7)	0.0220 (7)	0.0170 (7)	−0.0044 (6)	0.0007 (5)	−0.0035 (5)
C24	0.0285 (8)	0.0277 (8)	0.0219 (8)	0.0006 (6)	0.0021 (6)	−0.0078 (6)
C25	0.0308 (9)	0.0245 (8)	0.0218 (8)	−0.0009 (6)	−0.0013 (6)	−0.0005 (6)
B1	0.0268 (9)	0.0209 (8)	0.0159 (8)	−0.0063 (7)	0.0005 (6)	−0.0034 (6)

Geometric parameters (Å, º)

F1—B1	1.391 (2)	C22—C23	1.412 (2)
F2—B1	1.391 (2)	O1—H1	0.820
O1—C1	1.3698 (17)	C3—H3	0.930
N1—C16	1.3985 (18)	C5—H5	0.930
N1—C19	1.3536 (19)	C8—H8A	0.960
N1—B1	1.5515 (18)	C8—H8B	0.960
N2—C20	1.3537 (17)	C8—H8C	0.960
N2—C23	1.3960 (18)	C9—H9A	0.960
N2—B1	1.555 (2)	C9—H9B	0.960
C1—C2	1.412 (2)	C9—H9C	0.960
C1—C6	1.4132 (19)	C10—H10A	0.960
C2—C3	1.3904 (19)	C10—H10B	0.960
C2—C7	1.5453 (19)	C10—H10C	0.960
C3—C4	1.3971 (19)	C12—H12A	0.960
C4—C5	1.393 (2)	C12—H12B	0.960
C4—C15	1.4778 (19)	C12—H12C	0.960
C5—C6	1.3899 (19)	C13—H13A	0.960
C6—C11	1.544 (2)	C13—H13B	0.960
C7—C8	1.536 (2)	C13—H13C	0.960
C7—C9	1.5386 (19)	C14—H14A	0.960
C7—C10	1.536 (2)	C14—H14B	0.960
C11—C12	1.540 (2)	C14—H14C	0.960
C11—C13	1.542 (2)	C17—H17	0.930
C11—C14	1.538 (2)	C18—H18	0.930
C15—C16	1.399 (2)	C21—H21	0.930
C15—C23	1.4045 (18)	C22—H22	0.930
C16—C17	1.4096 (18)	C24—H24A	0.960
C17—C18	1.372 (2)	C24—H24B	0.960
C18—C19	1.4036 (19)	C24—H24C	0.960
C19—C24	1.488 (2)	C25—H25A	0.960
C20—C21	1.400 (2)	C25—H25B	0.960
C20—C25	1.491 (2)	C25—H25C	0.960
C21—C22	1.3784 (19)
C16—N1—C19	107.94 (11)	C4—C3—H3	118.911
C16—N1—B1	125.50 (12)	C4—C5—H5	118.675
C19—N1—B1	126.23 (12)	C6—C5—H5	118.675
C20—N2—C23	107.87 (12)	C7—C8—H8A	109.472
C20—N2—B1	126.91 (11)	C7—C8—H8B	109.471
C23—N2—B1	125.21 (11)	C7—C8—H8C	109.472
O1—C1—C2	115.70 (12)	H8A—C8—H8B	109.462
O1—C1—C6	121.79 (13)	H8A—C8—H8C	109.480
C2—C1—C6	122.51 (13)	H8B—C8—H8C	109.471
C1—C2—C3	117.24 (12)	C7—C9—H9A	109.472
C1—C2—C7	122.35 (12)	C7—C9—H9B	109.469
C3—C2—C7	120.40 (13)	C7—C9—H9C	109.475
C2—C3—C4	122.18 (14)	H9A—C9—H9B	109.473
C3—C4—C5	118.46 (13)	H9A—C9—H9C	109.469
C3—C4—C15	120.80 (13)	H9B—C9—H9C	109.470
C5—C4—C15	120.73 (12)	C7—C10—H10A	109.472
C4—C5—C6	122.65 (13)	C7—C10—H10B	109.473
C1—C6—C5	116.91 (13)	C7—C10—H10C	109.472
C1—C6—C11	122.82 (12)	H10A—C10—H10B	109.472
C5—C6—C11	120.27 (12)	H10A—C10—H10C	109.464
C2—C7—C8	111.62 (11)	H10B—C10—H10C	109.474
C2—C7—C9	109.37 (12)	C11—C12—H12A	109.467
C2—C7—C10	111.74 (11)	C11—C12—H12B	109.473
C8—C7—C9	109.89 (11)	C11—C12—H12C	109.474
C8—C7—C10	107.04 (13)	H12A—C12—H12B	109.472
C9—C7—C10	107.06 (12)	H12A—C12—H12C	109.466
C6—C11—C12	111.63 (11)	H12B—C12—H12C	109.475
C6—C11—C13	110.32 (12)	C11—C13—H13A	109.473
C6—C11—C14	111.71 (12)	C11—C13—H13B	109.475
C12—C11—C13	110.63 (12)	C11—C13—H13C	109.468
C12—C11—C14	106.21 (12)	H13A—C13—H13B	109.476
C13—C11—C14	106.14 (11)	H13A—C13—H13C	109.463
C4—C15—C16	120.26 (11)	H13B—C13—H13C	109.472
C4—C15—C23	119.79 (13)	C11—C14—H14A	109.471
C16—C15—C23	119.95 (12)	C11—C14—H14B	109.473
N1—C16—C15	121.13 (11)	C11—C14—H14C	109.466
N1—C16—C17	107.58 (13)	H14A—C14—H14B	109.468
C15—C16—C17	131.26 (13)	H14A—C14—H14C	109.475
C16—C17—C18	107.60 (12)	H14B—C14—H14C	109.473
C17—C18—C19	107.72 (13)	C16—C17—H17	126.206
N1—C19—C18	109.16 (13)	C18—C17—H17	126.198
N1—C19—C24	122.81 (12)	C17—C18—H18	126.137
C18—C19—C24	128.03 (13)	C19—C18—H18	126.139
N2—C20—C21	109.37 (12)	C20—C21—H21	126.155
N2—C20—C25	123.17 (14)	C22—C21—H21	126.156
C21—C20—C25	127.45 (12)	C21—C22—H22	126.369
C20—C21—C22	107.69 (13)	C23—C22—H22	126.370
C21—C22—C23	107.26 (13)	C19—C24—H24A	109.466
N2—C23—C15	121.42 (13)	C19—C24—H24B	109.471
N2—C23—C22	107.79 (11)	C19—C24—H24C	109.467
C15—C23—C22	130.78 (13)	H24A—C24—H24B	109.474
F1—B1—F2	108.79 (12)	H24A—C24—H24C	109.473
F1—B1—N1	110.89 (13)	H24B—C24—H24C	109.476
F1—B1—N2	110.50 (12)	C20—C25—H25A	109.472
F2—B1—N1	109.74 (12)	C20—C25—H25B	109.473
F2—B1—N2	110.35 (13)	C20—C25—H25C	109.478
N1—B1—N2	106.56 (11)	H25A—C25—H25B	109.464
C1—O1—H1	109.476	H25A—C25—H25C	109.468
C2—C3—H3	118.907	H25B—C25—H25C	109.473
C16—N1—C19—C18	0.27 (15)	C1—C2—C7—C10	179.90 (11)
C16—N1—C19—C24	−179.62 (12)	C3—C2—C7—C8	−120.82 (13)
C19—N1—C16—C15	178.62 (12)	C3—C2—C7—C9	117.35 (13)
C19—N1—C16—C17	0.15 (15)	C3—C2—C7—C10	−1.00 (17)
C16—N1—B1—F1	−125.79 (14)	C7—C2—C3—C4	−177.28 (10)
C16—N1—B1—F2	113.99 (15)	C2—C3—C4—C5	−0.29 (19)
C16—N1—B1—N2	−5.49 (19)	C2—C3—C4—C15	179.24 (11)
B1—N1—C16—C15	4.9 (2)	C3—C4—C5—C6	−1.14 (19)
B1—N1—C16—C17	−173.54 (12)	C3—C4—C15—C16	−47.14 (18)
C19—N1—B1—F1	61.66 (19)	C3—C4—C15—C23	133.53 (13)
C19—N1—B1—F2	−58.56 (19)	C5—C4—C15—C16	132.38 (13)
C19—N1—B1—N2	−178.04 (12)	C5—C4—C15—C23	−46.95 (18)
B1—N1—C19—C18	173.90 (12)	C15—C4—C5—C6	179.33 (11)
B1—N1—C19—C24	−6.0 (2)	C4—C5—C6—C1	0.86 (19)
C20—N2—C23—C15	−179.76 (12)	C4—C5—C6—C11	−178.32 (11)
C20—N2—C23—C22	0.77 (15)	C1—C6—C11—C12	59.64 (16)
C23—N2—C20—C21	−0.21 (16)	C1—C6—C11—C13	−63.79 (15)
C23—N2—C20—C25	−179.57 (12)	C1—C6—C11—C14	178.40 (11)
C20—N2—B1—F1	−56.02 (19)	C5—C6—C11—C12	−121.24 (12)
C20—N2—B1—F2	64.34 (18)	C5—C6—C11—C13	115.33 (12)
C20—N2—B1—N1	−176.57 (13)	C5—C6—C11—C14	−2.48 (17)
B1—N2—C20—C21	179.05 (12)	C4—C15—C16—N1	−179.89 (11)
B1—N2—C20—C25	−0.3 (2)	C4—C15—C16—C17	−1.8 (2)
C23—N2—B1—F1	123.11 (13)	C4—C15—C23—N2	177.05 (11)
C23—N2—B1—F2	−116.52 (14)	C4—C15—C23—C22	−3.6 (2)
C23—N2—B1—N1	2.57 (19)	C16—C15—C23—N2	−2.3 (2)
B1—N2—C23—C15	1.0 (2)	C16—C15—C23—C22	177.06 (13)
B1—N2—C23—C22	−178.50 (12)	C23—C15—C16—N1	−0.6 (2)
O1—C1—C2—C3	178.10 (10)	C23—C15—C16—C17	177.49 (13)
O1—C1—C2—C7	−2.77 (17)	N1—C16—C17—C18	−0.52 (16)
O1—C1—C6—C5	−179.44 (10)	C15—C16—C17—C18	−178.77 (14)
O1—C1—C6—C11	−0.28 (19)	C16—C17—C18—C19	0.67 (17)
C2—C1—C6—C5	0.85 (18)	C17—C18—C19—N1	−0.59 (17)
C2—C1—C6—C11	180.00 (11)	C17—C18—C19—C24	179.29 (13)
C6—C1—C2—C3	−2.16 (19)	N2—C20—C21—C22	−0.45 (17)
C6—C1—C2—C7	176.96 (11)	C25—C20—C21—C22	178.88 (14)
C1—C2—C3—C4	1.87 (19)	C20—C21—C22—C23	0.91 (16)
C1—C2—C7—C8	60.08 (16)	C21—C22—C23—N2	−1.04 (16)
C1—C2—C7—C9	−61.75 (16)	C21—C22—C23—C15	179.55 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12C···F2^i	0.96	2.54	3.4464 (18)	158

Symmetry code: (i) −x+1, −y+2, −z+1.