Effect of conjugated system extension on structural features and electron-density distribution in charge–transfer di­fluoro­borates

A com­parative structural study of two related donor–acceptor pyridine-based BF₂ com­plexes, namely, 3-(di­methyl­amino)-1,1-di­fluoro-1H-pyrido[1,2-c][1,3,5,2]oxadi­aza­borinin-9-ium-1-uide, C₈H₁₀BF₂N₃O (1), and 3-{(1E,3E)-4-[4-(di­methyl­amino)­phen­yl]buta-1,3-dien-1-yl}-1,1-di­fluoro-1H-pyrido[1,2-c][1,3,5,2]oxadi­aza­borinin-9-ium-1-uide, C₁₈H₁₈BF₂N₃O (2), containing a di­methyl­amino group and either the shortest (in 1) or the longest (in 2) charge-transfer path known until now in this family of com­pounds, is presented. Single-crystal X-ray diffraction analysis supported by com­putational investigations shed more light on these systems, indicating, among other aspects, the predominance of C—H...F contacts in 1, the formation of anti­parallel dimers held together by π–π inter­actions in both com­pounds, and the involvement of fused BF₂-bearing rings in the charge-transfer process.

Computing details

For both structures, data collection: CrysAlis PRO (Oxford Diffraction, 2014); cell refinement: CrysAlis PRO (Oxford Diffraction, 2014); data reduction: CrysAlis PRO (Oxford Diffraction, 2014); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008), Mercury (Macrae et al., 2020) and POV-RAY (Persistence of Vision, 2004); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

3-(Dimethylamino)-1,1-difluoro-1H-pyrido[1,2-c][1,3,5,2]-oxadiazaborinin-9-ium-1-uide (1)

Crystal data

C8H10BF2N3O	Z = 2
Mr = 213.00	F(000) = 220
Triclinic, P1	Dx = 1.529 Mg m^−3
a = 7.7181 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.2139 (6) Å	Cell parameters from 28335 reflections
c = 8.7684 (6) Å	θ = 2.5–30.5°
α = 79.847 (6)°	µ = 0.13 mm^−1
β = 66.782 (7)°	T = 100 K
γ = 64.907 (7)°	Block, colorless
V = 462.62 (6) Å^3	0.37 × 0.35 × 0.24 mm

Data collection

Oxford Diffraction SuperNova Dual Source diffractometer with an Eos detector	2418 reflections with I > 2σ(I)
Radiation source: SuperNova(Mo) X-ray Source	Rint = 0.044
ω scans	θmax = 30.5°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2014)	h = −11→11
Tmin = 0.924, Tmax = 0.982	k = −11→11
28335 measured reflections	l = −12→12
2810 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.129	w = 1/[σ^2(Fo^2) + (0.074P)^2 + 0.111P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
2810 reflections	Δρmax = 0.45 e Å^−3
138 parameters	Δρmin = −0.24 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Single-crystal X-ray diffraction data were collected on an Oxford Diffraction SuperNova diffractometer with an Eos CCD detector, Mo <i.Kα radiation, λ = 0.71073 Å. Data frames were processed (unit-cell determination, intensity data integration, correction for Lorentz and polarization effects and empirical absorption correction) using the corresponding diffractometer's software package (Oxford Diffraction, 2014). Each structure was solved by direct methods using SHELXS2014/7 (Sheldrick, 2008) and refined by full-matrix least-squares methods based on F² using SHELXL2014/7 (Sheldrick, 2015). The programs Mercury (Macrae et al., 2020) and POV-Ray (Persistence of Vision Pty. Ltd, 2004) were used to prepare the molecular graphics images. All non-hydrogen atoms were refined anisotropically.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
B1	0.15455 (18)	0.78905 (15)	0.23090 (14)	0.0188 (2)
O2	0.13709 (12)	0.70576 (10)	0.39554 (9)	0.01995 (18)
C3	0.22058 (15)	0.73233 (13)	0.48953 (12)	0.0164 (2)
N4	0.29568 (14)	0.85773 (12)	0.46315 (11)	0.01862 (19)
C5	0.28404 (15)	0.97126 (13)	0.33165 (12)	0.0164 (2)
C6	0.34857 (16)	1.11463 (14)	0.31052 (13)	0.0197 (2)
H6	0.3972	1.1305	0.3887	0.024*
C7	0.34090 (17)	1.23032 (14)	0.17748 (14)	0.0210 (2)
H7	0.3832	1.3266	0.1640	0.025*
C8	0.27020 (17)	1.20624 (14)	0.06084 (14)	0.0208 (2)
H8	0.2650	1.2851	−0.0321	0.025*
C9	0.20907 (16)	1.06668 (14)	0.08436 (13)	0.0195 (2)
H9	0.1610	1.0494	0.0065	0.023*
N10	0.21565 (13)	0.95164 (11)	0.21723 (11)	0.01670 (18)
F11	0.30603 (12)	0.66520 (9)	0.11001 (9)	0.02947 (19)
F12	−0.03083 (11)	0.84862 (10)	0.20964 (9)	0.02895 (19)
N13	0.22392 (14)	0.62404 (12)	0.62289 (11)	0.01902 (19)
C14	0.30258 (17)	0.64630 (15)	0.74086 (14)	0.0224 (2)
H14A	0.4464	0.5634	0.7136	0.034*
H14B	0.2221	0.6202	0.8534	0.034*
H14C	0.2920	0.7703	0.7349	0.034*
C15	0.17249 (17)	0.46669 (14)	0.64885 (14)	0.0209 (2)
H15A	0.1228	0.4640	0.5627	0.031*
H15B	0.0654	0.4734	0.7582	0.031*
H15C	0.2948	0.3572	0.6431	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
B1	0.0235 (5)	0.0213 (5)	0.0191 (5)	−0.0118 (4)	−0.0131 (4)	0.0033 (4)
O2	0.0243 (4)	0.0259 (4)	0.0202 (4)	−0.0156 (3)	−0.0140 (3)	0.0046 (3)
C3	0.0150 (4)	0.0196 (4)	0.0177 (5)	−0.0071 (3)	−0.0085 (4)	−0.0002 (3)
N4	0.0215 (4)	0.0211 (4)	0.0200 (4)	−0.0112 (3)	−0.0121 (3)	0.0028 (3)
C5	0.0150 (4)	0.0181 (4)	0.0180 (4)	−0.0063 (3)	−0.0079 (4)	−0.0009 (3)
C6	0.0215 (5)	0.0210 (4)	0.0217 (5)	−0.0108 (4)	−0.0104 (4)	0.0003 (4)
C7	0.0211 (5)	0.0199 (4)	0.0244 (5)	−0.0100 (4)	−0.0089 (4)	0.0016 (4)
C8	0.0213 (5)	0.0211 (5)	0.0219 (5)	−0.0088 (4)	−0.0109 (4)	0.0043 (4)
C9	0.0205 (5)	0.0218 (5)	0.0194 (5)	−0.0087 (4)	−0.0114 (4)	0.0032 (4)
N10	0.0176 (4)	0.0185 (4)	0.0175 (4)	−0.0078 (3)	−0.0097 (3)	0.0018 (3)
F11	0.0409 (4)	0.0244 (3)	0.0238 (4)	−0.0160 (3)	−0.0076 (3)	−0.0028 (3)
F12	0.0332 (4)	0.0329 (4)	0.0387 (4)	−0.0203 (3)	−0.0277 (3)	0.0119 (3)
N13	0.0229 (4)	0.0225 (4)	0.0195 (4)	−0.0127 (3)	−0.0130 (3)	0.0039 (3)
C14	0.0258 (5)	0.0276 (5)	0.0217 (5)	−0.0123 (4)	−0.0155 (4)	0.0028 (4)
C15	0.0236 (5)	0.0211 (4)	0.0241 (5)	−0.0120 (4)	−0.0133 (4)	0.0047 (4)

Geometric parameters (Å, º)

B1—F12	1.3805 (12)	C7—H7	0.9500
B1—F11	1.3855 (14)	C8—C9	1.3704 (14)
B1—O2	1.4652 (13)	C8—H8	0.9500
B1—N10	1.5664 (13)	C9—N10	1.3677 (13)
O2—C3	1.3204 (11)	C9—H9	0.9500
C3—N4	1.3293 (12)	N13—C14	1.4588 (12)
C3—N13	1.3404 (13)	N13—C15	1.4629 (13)
N4—C5	1.3560 (13)	C14—H14A	0.9800
C5—N10	1.3630 (12)	C14—H14B	0.9800
C5—C6	1.4201 (13)	C14—H14C	0.9800
C6—C7	1.3723 (14)	C15—H15A	0.9800
C6—H6	0.9500	C15—H15B	0.9800
C7—C8	1.4091 (14)	C15—H15C	0.9800
F12—B1—F11	110.15 (9)	C7—C8—H8	120.7
F12—B1—O2	109.68 (9)	N10—C9—C8	121.58 (9)
F11—B1—O2	109.64 (9)	N10—C9—H9	119.2
F12—B1—N10	109.81 (8)	C8—C9—H9	119.2
F11—B1—N10	108.87 (9)	C5—N10—C9	121.13 (8)
O2—B1—N10	108.66 (8)	C5—N10—B1	120.06 (8)
C3—O2—B1	122.28 (8)	C9—N10—B1	118.72 (8)
O2—C3—N4	125.25 (9)	C3—N13—C14	120.81 (8)
O2—C3—N13	115.67 (8)	C3—N13—C15	122.67 (8)
N4—C3—N13	119.07 (9)	C14—N13—C15	116.17 (8)
C3—N4—C5	118.59 (8)	N13—C14—H14A	109.5
N4—C5—N10	122.56 (9)	N13—C14—H14B	109.5
N4—C5—C6	118.86 (9)	H14A—C14—H14B	109.5
N10—C5—C6	118.58 (9)	N13—C14—H14C	109.5
C7—C6—C5	120.15 (9)	H14A—C14—H14C	109.5
C7—C6—H6	119.9	H14B—C14—H14C	109.5
C5—C6—H6	119.9	N13—C15—H15A	109.5
C6—C7—C8	119.99 (9)	N13—C15—H15B	109.5
C6—C7—H7	120.0	H15A—C15—H15B	109.5
C8—C7—H7	120.0	N13—C15—H15C	109.5
C9—C8—C7	118.57 (9)	H15A—C15—H15C	109.5
C9—C8—H8	120.7	H15B—C15—H15C	109.5
F12—B1—O2—C3	−138.58 (9)	C6—C5—N10—C9	0.11 (15)
F11—B1—O2—C3	100.35 (11)	N4—C5—N10—B1	−2.32 (15)
N10—B1—O2—C3	−18.53 (13)	C6—C5—N10—B1	176.65 (9)
B1—O2—C3—N4	12.67 (16)	C8—C9—N10—C5	−0.15 (16)
B1—O2—C3—N13	−168.64 (9)	C8—C9—N10—B1	−176.74 (10)
O2—C3—N4—C5	1.28 (16)	F12—B1—N10—C5	133.56 (10)
N13—C3—N4—C5	−177.37 (9)	F11—B1—N10—C5	−105.77 (10)
C3—N4—C5—N10	−6.12 (16)	O2—B1—N10—C5	13.59 (13)
C3—N4—C5—C6	174.90 (9)	F12—B1—N10—C9	−49.82 (13)
N4—C5—C6—C7	179.20 (10)	F11—B1—N10—C9	70.86 (11)
N10—C5—C6—C7	0.19 (16)	O2—B1—N10—C9	−169.79 (8)
C5—C6—C7—C8	−0.44 (16)	O2—C3—N13—C14	−176.83 (9)
C6—C7—C8—C9	0.39 (16)	N4—C3—N13—C14	1.94 (15)
C7—C8—C9—N10	−0.10 (16)	O2—C3—N13—C15	10.31 (15)
N4—C5—N10—C9	−178.87 (9)	N4—C3—N13—C15	−170.92 (9)

3-{(1E,3E)-4-[4-(Dimethylamino)phenyl]buta-1,3-dien-1-yl}-1,1-difluoro-1H-pyrido[1,2-c][1,3,5,2]oxadiazaborinin-9-ium-1-uide (2)

Crystal data

C18H18BF2N3O	Z = 2
Mr = 341.16	F(000) = 356
Triclinic, P1	Dx = 1.379 Mg m^−3
a = 8.1445 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.2758 (3) Å	Cell parameters from 8425 reflections
c = 12.7398 (6) Å	θ = 2.5–28.6°
α = 93.518 (4)°	µ = 0.10 mm^−1
β = 105.066 (4)°	T = 100 K
γ = 95.613 (3)°	Block, red
V = 821.83 (6) Å^3	0.34 × 0.23 × 0.17 mm

Data collection

Oxford Diffraction SuperNova Dual Source diffractometer with an Eos detector	2965 reflections with I > 2σ(I)
Radiation source: SuperNova (Mo) X-ray Source	Rint = 0.092
ω scans	θmax = 28.9°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2014)	h = −10→10
Tmin = 0.508, Tmax = 0.983	k = −11→11
20647 measured reflections	l = −17→17
3953 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.153	w = 1/[σ^2(Fo^2) + (0.073P)^2 + 0.1888P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3953 reflections	Δρmax = 0.31 e Å^−3
228 parameters	Δρmin = −0.37 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Single-crystal X-ray diffraction data were collected on an Oxford Diffraction SuperNova diffractometer with an Eos CCD detector, Mo <i.Kα radiation, λ = 0.71073 Å. Data frames were processed (unit-cell determination, intensity data integration, correction for Lorentz and polarization effects and empirical absorption correction) using the corresponding diffractometer's software package (Oxford Diffraction, 2014). Each structure was solved by direct methods using SHELXS2014/7 (Sheldrick, 2008) and refined by full-matrix least-squares methods based on F² using SHELXL2014/7 (Sheldrick, 2015). The programs Mercury (Macrae et al., 2020) and POV-Ray (Persistence of Vision Pty. Ltd, 2004) were used to prepare the molecular graphics images. All non-hydrogen atoms were refined anisotropically.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
B1	0.2606 (2)	0.0227 (2)	0.29228 (13)	0.0232 (3)
O2	0.16721 (12)	0.10249 (13)	0.19984 (8)	0.0242 (3)
C3	0.22710 (18)	0.13520 (18)	0.11526 (11)	0.0214 (3)
N4	0.37553 (15)	0.10459 (15)	0.10316 (9)	0.0227 (3)
C5	0.48359 (18)	0.03306 (17)	0.18358 (11)	0.0210 (3)
C6	0.64306 (18)	0.00080 (18)	0.17044 (12)	0.0248 (3)
H6	0.6737	0.0263	0.1058	0.030*
C7	0.75499 (19)	−0.06748 (19)	0.25046 (13)	0.0287 (4)
H7	0.8638	−0.0879	0.2419	0.034*
C8	0.7083 (2)	−0.1069 (2)	0.34466 (12)	0.0292 (4)
H8	0.7849	−0.1532	0.4013	0.035*
C9	0.55000 (19)	−0.07757 (19)	0.35357 (12)	0.0259 (3)
H9	0.5161	−0.1070	0.4164	0.031*
N10	0.43969 (15)	−0.00762 (15)	0.27532 (9)	0.0213 (3)
F11	0.28629 (11)	0.12133 (12)	0.38840 (7)	0.0320 (3)
F12	0.17079 (11)	−0.12496 (11)	0.29893 (7)	0.0313 (2)
C13	0.11647 (18)	0.21145 (18)	0.02888 (11)	0.0230 (3)
H13	0.1608	0.2421	−0.0299	0.028*
C14	−0.04312 (18)	0.24205 (17)	0.02540 (11)	0.0218 (3)
H14	−0.0887	0.2119	0.0838	0.026*
C15	−0.14948 (18)	0.31794 (17)	−0.06164 (11)	0.0224 (3)
H15	−0.1019	0.3540	−0.1180	0.027*
C16	−0.31252 (18)	0.34050 (17)	−0.06754 (11)	0.0218 (3)
H16	−0.3568	0.3019	−0.0105	0.026*
C17	−0.42918 (18)	0.41718 (17)	−0.15110 (11)	0.0217 (3)
C18	−0.38915 (19)	0.47354 (18)	−0.24392 (11)	0.0243 (3)
H18	−0.2795	0.4614	−0.2544	0.029*
C19	−0.5044 (2)	0.54619 (19)	−0.32062 (12)	0.0261 (3)
H19	−0.4729	0.5823	−0.3828	0.031*
C20	−0.6686 (2)	0.56789 (19)	−0.30836 (11)	0.0278 (4)
C21	−0.70956 (19)	0.51175 (19)	−0.21539 (12)	0.0263 (3)
H21	−0.8188	0.5241	−0.2043	0.032*
C22	−0.59203 (19)	0.43864 (18)	−0.13978 (11)	0.0227 (3)
H22	−0.6233	0.4016	−0.0777	0.027*
N23	−0.7829 (2)	0.6411 (2)	−0.38437 (12)	0.0455 (4)
C24	−0.7416 (2)	0.6897 (2)	−0.48204 (13)	0.0371 (4)
H24A	−0.6395	0.7701	−0.4623	0.056*
H24B	−0.8379	0.7380	−0.5272	0.056*
H24C	−0.7193	0.5941	−0.5232	0.056*
C25	−0.9488 (2)	0.6653 (2)	−0.36915 (14)	0.0385 (4)
H25A	−1.0108	0.5596	−0.3642	0.058*
H25B	−1.0141	0.7172	−0.4312	0.058*
H25C	−0.9340	0.7353	−0.3017	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
B1	0.0198 (8)	0.0301 (9)	0.0202 (7)	0.0021 (6)	0.0065 (6)	0.0022 (6)
O2	0.0204 (5)	0.0333 (6)	0.0216 (5)	0.0067 (4)	0.0082 (4)	0.0049 (4)
C3	0.0206 (7)	0.0205 (7)	0.0229 (7)	−0.0013 (5)	0.0077 (5)	−0.0016 (5)
N4	0.0208 (6)	0.0241 (7)	0.0243 (6)	0.0026 (5)	0.0080 (5)	0.0023 (5)
C5	0.0188 (7)	0.0204 (7)	0.0227 (7)	−0.0014 (5)	0.0062 (5)	−0.0031 (5)
C6	0.0211 (7)	0.0250 (8)	0.0294 (7)	−0.0005 (6)	0.0106 (6)	−0.0002 (6)
C7	0.0178 (7)	0.0286 (8)	0.0376 (8)	0.0014 (6)	0.0059 (6)	−0.0054 (6)
C8	0.0239 (7)	0.0307 (9)	0.0284 (8)	0.0065 (6)	−0.0009 (6)	−0.0025 (6)
C9	0.0231 (7)	0.0314 (8)	0.0221 (7)	0.0045 (6)	0.0041 (5)	0.0010 (6)
N10	0.0189 (6)	0.0236 (7)	0.0203 (6)	0.0015 (5)	0.0044 (5)	−0.0012 (5)
F11	0.0273 (5)	0.0476 (6)	0.0222 (4)	0.0091 (4)	0.0081 (3)	−0.0037 (4)
F12	0.0210 (4)	0.0367 (6)	0.0375 (5)	0.0016 (4)	0.0094 (4)	0.0107 (4)
C13	0.0244 (7)	0.0229 (8)	0.0224 (7)	0.0024 (6)	0.0073 (5)	0.0025 (5)
C14	0.0236 (7)	0.0186 (7)	0.0226 (7)	−0.0008 (6)	0.0065 (5)	0.0000 (5)
C15	0.0248 (7)	0.0193 (7)	0.0224 (7)	0.0013 (6)	0.0058 (5)	0.0008 (5)
C16	0.0243 (7)	0.0197 (7)	0.0209 (7)	0.0017 (6)	0.0061 (5)	0.0007 (5)
C17	0.0235 (7)	0.0192 (7)	0.0212 (7)	0.0012 (6)	0.0051 (5)	−0.0006 (5)
C18	0.0241 (7)	0.0249 (8)	0.0254 (7)	0.0037 (6)	0.0093 (6)	0.0005 (6)
C19	0.0335 (8)	0.0266 (8)	0.0212 (7)	0.0068 (6)	0.0109 (6)	0.0044 (6)
C20	0.0351 (8)	0.0286 (8)	0.0211 (7)	0.0139 (7)	0.0066 (6)	0.0010 (6)
C21	0.0246 (7)	0.0298 (8)	0.0255 (7)	0.0080 (6)	0.0074 (6)	−0.0003 (6)
C22	0.0255 (7)	0.0221 (7)	0.0217 (7)	0.0018 (6)	0.0084 (5)	0.0019 (5)
N23	0.0527 (10)	0.0674 (11)	0.0278 (7)	0.0409 (9)	0.0156 (6)	0.0178 (7)
C24	0.0484 (10)	0.0363 (9)	0.0234 (8)	0.0093 (8)	0.0018 (7)	0.0045 (6)
C25	0.0339 (9)	0.0460 (11)	0.0326 (9)	0.0143 (8)	0.0001 (7)	0.0027 (7)

Geometric parameters (Å, º)

B1—F12	1.3800 (19)	C15—H15	0.9500
B1—F11	1.3859 (17)	C16—C17	1.454 (2)
B1—O2	1.4593 (19)	C16—H16	0.9500
B1—N10	1.5706 (19)	C17—C22	1.398 (2)
O2—C3	1.3250 (17)	C17—C18	1.400 (2)
C3—N4	1.3043 (19)	C18—C19	1.380 (2)
C3—C13	1.450 (2)	C18—H18	0.9500
N4—C5	1.3719 (19)	C19—C20	1.413 (2)
C5—N10	1.3599 (19)	C19—H19	0.9500
C5—C6	1.401 (2)	C20—N23	1.373 (2)
C6—C7	1.370 (2)	C20—C21	1.405 (2)
C6—H6	0.9500	C21—C22	1.384 (2)
C7—C8	1.397 (2)	C21—H21	0.9500
C7—H7	0.9500	C22—H22	0.9500
C8—C9	1.367 (2)	N23—C24	1.441 (2)
C8—H8	0.9500	N23—C25	1.445 (2)
C9—N10	1.3576 (19)	C24—H24A	0.9800
C9—H9	0.9500	C24—H24B	0.9800
C13—C14	1.338 (2)	C24—H24C	0.9800
C13—H13	0.9500	C25—H25A	0.9800
C14—C15	1.438 (2)	C25—H25B	0.9800
C14—H14	0.9500	C25—H25C	0.9800
C15—C16	1.342 (2)
F12—B1—F11	109.81 (12)	C14—C15—H15	118.3
F12—B1—O2	110.14 (12)	C15—C16—C17	127.54 (14)
F11—B1—O2	110.23 (13)	C15—C16—H16	116.2
F12—B1—N10	109.14 (13)	C17—C16—H16	116.2
F11—B1—N10	108.69 (11)	C22—C17—C18	116.60 (13)
O2—B1—N10	108.80 (11)	C22—C17—C16	119.24 (13)
C3—O2—B1	123.43 (11)	C18—C17—C16	124.15 (13)
N4—C3—O2	125.81 (14)	C19—C18—C17	121.85 (14)
N4—C3—C13	117.66 (13)	C19—C18—H18	119.1
O2—C3—C13	116.53 (12)	C17—C18—H18	119.1
C3—N4—C5	119.15 (12)	C18—C19—C20	121.18 (13)
N10—C5—N4	121.75 (12)	C18—C19—H19	119.4
N10—C5—C6	119.27 (14)	C20—C19—H19	119.4
N4—C5—C6	118.98 (13)	N23—C20—C21	121.55 (14)
C7—C6—C5	120.23 (14)	N23—C20—C19	121.17 (14)
C7—C6—H6	119.9	C21—C20—C19	117.28 (14)
C5—C6—H6	119.9	C22—C21—C20	120.50 (14)
C6—C7—C8	119.66 (14)	C22—C21—H21	119.8
C6—C7—H7	120.2	C20—C21—H21	119.8
C8—C7—H7	120.2	C21—C22—C17	122.59 (14)
C9—C8—C7	118.56 (15)	C21—C22—H22	118.7
C9—C8—H8	120.7	C17—C22—H22	118.7
C7—C8—H8	120.7	C20—N23—C24	120.56 (15)
N10—C9—C8	122.01 (14)	C20—N23—C25	120.30 (14)
N10—C9—H9	119.0	C24—N23—C25	119.10 (14)
C8—C9—H9	119.0	N23—C24—H24A	109.5
C9—N10—C5	120.25 (12)	N23—C24—H24B	109.5
C9—N10—B1	118.74 (12)	H24A—C24—H24B	109.5
C5—N10—B1	121.01 (12)	N23—C24—H24C	109.5
C14—C13—C3	125.21 (14)	H24A—C24—H24C	109.5
C14—C13—H13	117.4	H24B—C24—H24C	109.5
C3—C13—H13	117.4	N23—C25—H25A	109.5
C13—C14—C15	123.77 (14)	N23—C25—H25B	109.5
C13—C14—H14	118.1	H25A—C25—H25B	109.5
C15—C14—H14	118.1	N23—C25—H25C	109.5
C16—C15—C14	123.46 (14)	H25A—C25—H25C	109.5
C16—C15—H15	118.3	H25B—C25—H25C	109.5
F12—B1—O2—C3	−117.06 (14)	F11—B1—N10—C5	−122.52 (14)
F11—B1—O2—C3	121.62 (13)	O2—B1—N10—C5	−2.47 (18)
N10—B1—O2—C3	2.52 (18)	N4—C3—C13—C14	175.79 (13)
B1—O2—C3—N4	−1.3 (2)	O2—C3—C13—C14	−4.1 (2)
B1—O2—C3—C13	178.54 (12)	C3—C13—C14—C15	−179.99 (12)
O2—C3—N4—C5	−0.4 (2)	C13—C14—C15—C16	176.36 (13)
C13—C3—N4—C5	179.76 (11)	C14—C15—C16—C17	179.24 (12)
C3—N4—C5—N10	0.4 (2)	C15—C16—C17—C22	−176.11 (13)
C3—N4—C5—C6	−179.82 (12)	C15—C16—C17—C18	3.4 (2)
N10—C5—C6—C7	−1.5 (2)	C22—C17—C18—C19	−0.2 (2)
N4—C5—C6—C7	178.66 (12)	C16—C17—C18—C19	−179.71 (13)
C5—C6—C7—C8	0.9 (2)	C17—C18—C19—C20	0.4 (2)
C6—C7—C8—C9	0.7 (2)	C18—C19—C20—N23	179.58 (15)
C7—C8—C9—N10	−1.8 (2)	C18—C19—C20—C21	−0.3 (2)
C8—C9—N10—C5	1.2 (2)	N23—C20—C21—C22	−179.85 (15)
C8—C9—N10—B1	−179.69 (13)	C19—C20—C21—C22	0.1 (2)
N4—C5—N10—C9	−179.69 (12)	C20—C21—C22—C17	0.1 (2)
C6—C5—N10—C9	0.5 (2)	C18—C17—C22—C21	−0.1 (2)
N4—C5—N10—B1	1.2 (2)	C16—C17—C22—C21	179.46 (12)
C6—C5—N10—B1	−178.60 (12)	C21—C20—N23—C24	−176.59 (15)
F12—B1—N10—C9	−61.37 (16)	C19—C20—N23—C24	3.5 (3)
F11—B1—N10—C9	58.37 (18)	C21—C20—N23—C25	1.2 (3)
O2—B1—N10—C9	178.42 (11)	C19—C20—N23—C25	−178.69 (15)
F12—B1—N10—C5	117.74 (14)