Crystal structures of 1,1′-bis­(carb­oxy­meth­yl)-4,4′-bipyridinium derivatives

The crystal structures of 2-[1′-(carb­oxy­meth­yl)-4,4′-bi­pyridine-1,1′-diium-1-yl]acetate tetra­fluoro­borate, C₁₄H₁₃N₂O₄⁺·BF₄⁻ or (Hbcbpy)(BF₄), and neutral 1,1′-bis­(carboxyl­atometh­yl)-4,4′-bi­pyridine-1,1′-diium (bcbpy), C₁₄H₂₀N₂O₈, are reported.

Computing details

1,1'-Bis(carboxylatomethyl)-4,4'-bipyridine-1,1'-diium (bcbpy)

Crystal data

C14H20N2O8	F(000) = 364.00
Mr = 344.32	Dx = 1.458 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71075 Å
a = 6.2521 (2) Å	Cell parameters from 7055 reflections
b = 11.4122 (4) Å	θ = 3.3–27.5°
c = 11.1413 (4) Å	µ = 0.12 mm^−1
β = 99.4832 (14)°	T = 296 K
V = 784.07 (5) Å^3	Block, yellow
Z = 2	0.48 × 0.46 × 0.42 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	1678 reflections with F^2 > 2.0σ(F^2)
Detector resolution: 10.000 pixels mm^-1	Rint = 0.022
ω scans	θmax = 27.5°, θmin = 3.5°
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	h = −8→7
Tmin = 0.788, Tmax = 0.951	k = −14→14
7476 measured reflections	l = −14→14
1793 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0813P)^2 + 0.1761P] where P = (Fo^2 + 2Fc^2)/3
1793 reflections	(Δ/σ)max < 0.001
125 parameters	Δρmax = 0.40 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3
Primary atom site location: structure-invariant direct methods

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. 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).

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

	x	y	z	Uiso*/Ueq
O1	0.51613 (14)	0.68508 (8)	0.03041 (7)	0.0252 (2)
O2	0.48570 (13)	0.70887 (7)	0.22699 (7)	0.0228 (2)
O3	0.80684 (15)	0.87902 (8)	0.29910 (8)	0.0270 (2)
O4	0.41417 (14)	0.74797 (8)	0.46745 (8)	0.0277 (2)
N1	0.17838 (14)	0.54278 (8)	0.22070 (8)	0.0176 (2)
C7	0.28870 (17)	0.46929 (10)	0.30354 (10)	0.0207 (3)
H7	0.411238	0.430906	0.286205	0.025*
C6	0.22108 (18)	0.45072 (9)	0.41363 (10)	0.0204 (3)
H6	0.297168	0.399296	0.469856	0.025*
C5	0.03839 (16)	0.50899 (9)	0.44103 (9)	0.0165 (3)
C4	−0.07103 (17)	0.58473 (10)	0.35318 (9)	0.0194 (3)
H4	−0.193261	0.624817	0.368421	0.023*
C3	0.00173 (17)	0.60021 (10)	0.24390 (10)	0.0199 (3)
H3	−0.071887	0.650736	0.185822	0.024*
C2	0.26195 (17)	0.56648 (10)	0.10675 (9)	0.0195 (3)
H2A	0.143316	0.591106	0.044479	0.023*
H2B	0.322475	0.495057	0.079110	0.023*
C1	0.43789 (17)	0.66260 (9)	0.12460 (9)	0.0183 (2)
H9	0.709 (3)	0.8291 (18)	0.2700 (17)	0.041 (5)*
H8	0.860 (3)	0.8538 (18)	0.369 (2)	0.049 (5)*
H10	0.400 (3)	0.7365 (16)	0.387 (2)	0.041 (5)*
H11	0.285 (3)	0.7551 (15)	0.4820 (18)	0.043 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0241 (4)	0.0337 (5)	0.0190 (4)	−0.0043 (3)	0.0071 (3)	0.0034 (3)
O2	0.0228 (4)	0.0264 (4)	0.0193 (4)	−0.0036 (3)	0.0037 (3)	−0.0010 (3)
O3	0.0265 (5)	0.0282 (5)	0.0259 (5)	−0.0060 (3)	0.0033 (3)	0.0055 (3)
O4	0.0210 (5)	0.0380 (5)	0.0241 (5)	0.0000 (3)	0.0041 (3)	−0.0065 (4)
N1	0.0185 (5)	0.0185 (4)	0.0162 (4)	−0.0025 (3)	0.0045 (3)	0.0000 (3)
C7	0.0206 (5)	0.0204 (5)	0.0221 (5)	0.0028 (4)	0.0067 (4)	0.0023 (4)
C6	0.0215 (5)	0.0198 (5)	0.0209 (5)	0.0032 (4)	0.0059 (4)	0.0039 (4)
C5	0.0173 (5)	0.0155 (5)	0.0171 (5)	−0.0023 (4)	0.0037 (4)	−0.0004 (4)
C4	0.0180 (5)	0.0212 (5)	0.0193 (5)	0.0016 (4)	0.0045 (4)	0.0013 (4)
C3	0.0191 (5)	0.0219 (5)	0.0186 (5)	0.0016 (4)	0.0029 (4)	0.0025 (4)
C2	0.0214 (5)	0.0230 (5)	0.0151 (5)	−0.0017 (4)	0.0058 (4)	−0.0003 (4)
C1	0.0162 (5)	0.0209 (5)	0.0182 (5)	0.0013 (4)	0.0035 (4)	0.0026 (4)

Geometric parameters (Å, º)

O1—C1	1.2553 (13)	C6—C5	1.3982 (14)
O2—C1	1.2479 (14)	C6—H6	0.9300
O3—H9	0.86 (2)	C5—C4	1.3973 (15)
O3—H8	0.85 (2)	C5—C5^i	1.4856 (19)
O4—H10	0.89 (2)	C4—C3	1.3794 (14)
O4—H11	0.85 (2)	C4—H4	0.9300
N1—C3	1.3454 (14)	C3—H3	0.9300
N1—C7	1.3495 (15)	C2—C1	1.5429 (15)
N1—C2	1.4753 (13)	C2—H2A	0.9700
C7—C6	1.3780 (14)	C2—H2B	0.9700
C7—H7	0.9300
H9—O3—H8	105.7 (19)	C3—C4—H4	119.9
H10—O4—H11	105.3 (18)	C5—C4—H4	119.9
C3—N1—C7	120.97 (9)	N1—C3—C4	120.51 (10)
C3—N1—C2	119.62 (9)	N1—C3—H3	119.7
C7—N1—C2	119.27 (9)	C4—C3—H3	119.7
N1—C7—C6	120.47 (10)	N1—C2—C1	111.44 (8)
N1—C7—H7	119.8	N1—C2—H2A	109.3
C6—C7—H7	119.8	C1—C2—H2A	109.3
C7—C6—C5	120.17 (10)	N1—C2—H2B	109.3
C7—C6—H6	119.9	C1—C2—H2B	109.3
C5—C6—H6	119.9	H2A—C2—H2B	108.0
C4—C5—C6	117.68 (9)	O2—C1—O1	127.60 (10)
C4—C5—C5^i	120.85 (11)	O2—C1—C2	118.49 (9)
C6—C5—C5^i	121.47 (12)	O1—C1—C2	113.91 (9)
C3—C4—C5	120.19 (10)
C3—N1—C7—C6	0.60 (17)	C7—N1—C3—C4	−0.25 (16)
C2—N1—C7—C6	176.33 (10)	C2—N1—C3—C4	−175.96 (10)
N1—C7—C6—C5	−0.68 (17)	C5—C4—C3—N1	−0.02 (17)
C7—C6—C5—C4	0.41 (16)	C3—N1—C2—C1	92.74 (11)
C7—C6—C5—C5^i	−179.89 (11)	C7—N1—C2—C1	−83.05 (12)
C6—C5—C4—C3	−0.07 (16)	N1—C2—C1—O2	−1.12 (14)
C5^i—C5—C4—C3	−179.76 (11)	N1—C2—C1—O1	179.23 (9)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H9···O2	0.859 (19)	1.96 (2)	2.8135 (12)	172.1 (19)
O3—H8···O1^ii	0.85 (2)	1.95 (2)	2.7888 (11)	171 (2)
O4—H10···O2	0.89 (2)	1.97 (2)	2.8233 (12)	158.9 (18)
O4—H11···O1^iii	0.85 (2)	1.97 (2)	2.8007 (13)	164.1 (17)

Symmetry codes: (ii) x+1/2, −y+3/2, z+1/2; (iii) x−1/2, −y+3/2, z+1/2.

2-[1'-(Carboxymethyl)-4,4'-bipyridine-1,1'-diium-1-yl]acetate tetrafluoroborate (HbcbpyBF4)

Crystal data

C14H13N2O4.5^+·BF4^−	F(000) = 756
Mr = 368.08	Dx = 1.519 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71075 Å
a = 7.6794 (16) Å	Cell parameters from 2543 reflections
b = 20.987 (4) Å	θ = 5.6–27.4°
c = 10.0514 (19) Å	µ = 0.14 mm^−1
β = 95.123 (3)°	T = 100 K
V = 1613.5 (5) Å^3	Platelet, colorless
Z = 4	0.60 × 0.40 × 0.40 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	3119 reflections with I > 2σ(I)
Detector resolution: 10.000 pixels mm^-1	Rint = 0.032
ω scans	θmax = 27.4°, θmin = 3.2°
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	h = −9→9
Tmin = 0.656, Tmax = 0.987	k = −27→27
15631 measured reflections	l = −13→13
3652 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: mixed
wR(F^2) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0594P)^2 + 1.2013P] where P = (Fo^2 + 2Fc^2)/3
3652 reflections	(Δ/σ)max < 0.001
292 parameters	Δρmax = 0.72 e Å^−3
1 restraint	Δρmin = −0.56 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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O4	−0.12434 (15)	0.59508 (5)	0.51560 (12)	0.0246 (3)
O3	−0.18392 (15)	0.49606 (6)	0.58466 (13)	0.0278 (3)
C14	−0.0977 (2)	0.54581 (7)	0.59083 (16)	0.0212 (3)
C13	0.0546 (2)	0.54866 (8)	0.69960 (17)	0.0232 (3)
H13	0.006964	0.550938	0.787824	0.028*
H13A	0.123093	0.508798	0.697034	0.028*
N2	0.17293 (17)	0.60349 (6)	0.68628 (13)	0.0206 (3)
C10	0.3334 (2)	0.59435 (8)	0.64492 (17)	0.0224 (3)
H10	0.368960	0.552814	0.621280	0.027*
C9	0.4466 (2)	0.64527 (8)	0.63679 (17)	0.0233 (3)
H9	0.559646	0.638678	0.607859	0.028*
C8	0.3941 (2)	0.70639 (8)	0.67125 (16)	0.0211 (3)
C5	0.5167 (2)	0.76126 (8)	0.67427 (16)	0.0221 (3)
N1	0.75008 (18)	0.86160 (6)	0.68917 (14)	0.0227 (3)
C12	0.2245 (2)	0.71446 (8)	0.70921 (17)	0.0249 (4)
H12	0.183872	0.755753	0.729713	0.030*
C7	0.6207 (2)	0.86054 (8)	0.77144 (18)	0.0252 (3)
H7	0.611023	0.894042	0.833916	0.030*
C1	1.0355 (2)	0.88901 (7)	0.80414 (16)	0.0208 (3)
O1	1.14297 (16)	0.93451 (6)	0.84102 (13)	0.0305 (3)
O2	1.04698 (15)	0.83348 (5)	0.84064 (12)	0.0240 (3)
C11	0.1169 (2)	0.66241 (8)	0.71677 (17)	0.0246 (3)
H11	0.002372	0.667885	0.743615	0.029*
C6	0.5025 (2)	0.81110 (8)	0.76520 (17)	0.0250 (3)
H6	0.410968	0.810802	0.822826	0.030*
C2	0.8844 (2)	0.91214 (8)	0.70692 (18)	0.0246 (3)
H2	0.832748	0.951166	0.742328	0.029*
H2A	0.927993	0.922573	0.619744	0.029*
F1A	0.2612 (3)	0.83677 (18)	0.3422 (3)	0.0623 (9)	0.662 (3)
C4	0.6512 (2)	0.76409 (8)	0.58975 (17)	0.0272 (4)
H4	0.663465	0.731336	0.526009	0.033*
F2A	0.1745 (3)	0.84329 (14)	0.5476 (2)	0.0524 (7)	0.662 (3)
C3	0.7663 (2)	0.81476 (9)	0.59933 (18)	0.0283 (4)
H3	0.858056	0.816631	0.541966	0.034*
B1A	0.2445 (7)	0.8769 (2)	0.4484 (4)	0.0336 (9)	0.662 (3)
F3A	0.4096 (3)	0.89999 (11)	0.4970 (2)	0.0540 (7)	0.662 (3)
F4A	0.1333 (5)	0.92664 (13)	0.4093 (3)	0.0938 (13)	0.662 (3)
B1B	0.1633 (13)	0.8772 (5)	0.4399 (9)	0.037 (2)	0.338 (3)
H1B	−0.259900	0.581900	0.413100	0.050*
F1B	0.2530 (6)	0.9024 (3)	0.5528 (4)	0.0615 (15)	0.338 (3)
F2B	0.2596 (6)	0.8794 (4)	0.3323 (4)	0.0537 (15)	0.338 (3)
F3B	0.1320 (8)	0.8129 (3)	0.4697 (7)	0.0718 (17)	0.338 (3)
F4B	0.0007 (6)	0.9038 (2)	0.4137 (3)	0.0508 (13)	0.338 (3)
O5B	0.5838 (6)	0.9583 (2)	0.5161 (4)	0.0446 (11)	0.352 (2)
O5A	−0.1551 (12)	0.9609 (5)	0.4223 (9)	0.036 (2)	0.148 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O4	0.0198 (6)	0.0195 (6)	0.0340 (6)	−0.0016 (4)	−0.0005 (5)	0.0036 (5)
O3	0.0219 (6)	0.0218 (6)	0.0396 (7)	−0.0056 (5)	0.0020 (5)	0.0037 (5)
C14	0.0158 (7)	0.0200 (7)	0.0285 (8)	−0.0005 (6)	0.0057 (6)	−0.0001 (6)
C13	0.0203 (8)	0.0192 (7)	0.0303 (8)	−0.0010 (6)	0.0034 (6)	0.0037 (6)
N2	0.0172 (6)	0.0193 (6)	0.0251 (7)	−0.0003 (5)	0.0008 (5)	−0.0002 (5)
C10	0.0166 (7)	0.0206 (7)	0.0297 (8)	0.0028 (6)	0.0005 (6)	−0.0042 (6)
C9	0.0168 (7)	0.0238 (8)	0.0294 (8)	0.0001 (6)	0.0024 (6)	−0.0057 (6)
C8	0.0192 (7)	0.0204 (8)	0.0236 (7)	−0.0014 (6)	0.0002 (6)	−0.0026 (6)
C5	0.0183 (7)	0.0201 (7)	0.0273 (8)	−0.0001 (6)	−0.0016 (6)	−0.0016 (6)
N1	0.0200 (7)	0.0181 (6)	0.0294 (7)	−0.0015 (5)	−0.0019 (5)	−0.0004 (5)
C12	0.0213 (8)	0.0194 (8)	0.0339 (9)	0.0018 (6)	0.0022 (6)	−0.0047 (7)
C7	0.0216 (8)	0.0204 (8)	0.0330 (9)	0.0016 (6)	0.0005 (6)	−0.0059 (7)
C1	0.0185 (7)	0.0186 (7)	0.0260 (8)	−0.0003 (6)	0.0053 (6)	−0.0016 (6)
O1	0.0262 (6)	0.0195 (6)	0.0438 (7)	−0.0050 (5)	−0.0087 (5)	0.0016 (5)
O2	0.0231 (6)	0.0179 (6)	0.0311 (6)	−0.0008 (4)	0.0021 (5)	0.0012 (5)
C11	0.0190 (8)	0.0229 (8)	0.0322 (8)	0.0025 (6)	0.0046 (6)	−0.0045 (7)
C6	0.0198 (8)	0.0229 (8)	0.0325 (9)	0.0007 (6)	0.0041 (6)	−0.0048 (7)
C2	0.0216 (8)	0.0176 (7)	0.0338 (9)	−0.0031 (6)	−0.0011 (6)	0.0010 (6)
F1A	0.0304 (11)	0.099 (2)	0.0589 (15)	−0.0085 (14)	0.0125 (10)	−0.0396 (17)
C4	0.0267 (9)	0.0260 (8)	0.0291 (8)	−0.0052 (7)	0.0044 (7)	−0.0081 (7)
F2A	0.0353 (11)	0.0829 (18)	0.0405 (11)	−0.0104 (11)	0.0127 (9)	0.0096 (12)
C3	0.0265 (9)	0.0294 (9)	0.0294 (9)	−0.0051 (7)	0.0054 (7)	−0.0055 (7)
B1A	0.034 (2)	0.0352 (19)	0.032 (2)	0.000 (2)	0.007 (2)	0.0040 (14)
F3A	0.0532 (13)	0.0619 (14)	0.0449 (11)	−0.0261 (10)	−0.0073 (9)	0.0120 (10)
F4A	0.122 (3)	0.0458 (15)	0.103 (2)	0.0258 (17)	−0.054 (2)	0.0037 (14)
B1B	0.028 (4)	0.058 (5)	0.026 (4)	−0.009 (5)	0.011 (4)	−0.004 (3)
F1B	0.049 (3)	0.100 (4)	0.034 (2)	0.000 (2)	−0.0034 (17)	−0.020 (2)
F2B	0.033 (2)	0.103 (4)	0.0269 (19)	−0.027 (3)	0.0100 (15)	−0.006 (3)
F3B	0.075 (4)	0.059 (3)	0.085 (4)	−0.002 (3)	0.026 (3)	0.021 (3)
F4B	0.038 (2)	0.091 (3)	0.0237 (17)	0.009 (2)	0.0002 (14)	−0.0136 (18)
O5B	0.050 (3)	0.041 (2)	0.041 (2)	−0.004 (2)	−0.0052 (19)	0.0051 (19)
O5A	0.040 (5)	0.037 (5)	0.030 (4)	−0.001 (4)	0.000 (4)	0.002 (4)

Geometric parameters (Å, º)

O4—C14	1.287 (2)	C12—H12	0.9500
O4—H1B	1.4248	C7—C6	1.376 (2)
O3—C14	1.2350 (19)	C7—H7	0.9500
C14—C13	1.529 (2)	C1—O2	1.2226 (19)
C13—N2	1.480 (2)	C1—O1	1.2944 (19)
C13—H13	0.9900	C1—C2	1.528 (2)
C13—H13A	0.9900	C11—H11	0.9500
N2—C10	1.349 (2)	C6—H6	0.9500
N2—C11	1.353 (2)	C2—H2	0.9900
C10—C9	1.384 (2)	C2—H2A	0.9900
C10—H10	0.9500	F1A—B1A	1.375 (5)
C9—C8	1.398 (2)	C4—C3	1.381 (2)
C9—H9	0.9500	C4—H4	0.9500
C8—C12	1.399 (2)	F2A—B1A	1.370 (5)
C8—C5	1.486 (2)	C3—H3	0.9500
C5—C4	1.396 (2)	B1A—F4A	1.384 (5)
C5—C6	1.400 (2)	B1A—F3A	1.404 (6)
N1—C3	1.348 (2)	B1B—F2B	1.364 (9)
N1—C7	1.349 (2)	B1B—F4B	1.372 (12)
N1—C2	1.479 (2)	B1B—F1B	1.380 (10)
C12—C11	1.376 (2)	B1B—F3B	1.406 (11)
C14—O4—H1B	109.7	O2—C1—O1	126.19 (15)
O3—C14—O4	126.40 (15)	O2—C1—C2	121.66 (14)
O3—C14—C13	116.20 (14)	O1—C1—C2	112.15 (13)
O4—C14—C13	117.40 (14)	N2—C11—C12	120.56 (15)
N2—C13—C14	113.73 (13)	N2—C11—H11	119.7
N2—C13—H13	108.8	C12—C11—H11	119.7
C14—C13—H13	108.8	C7—C6—C5	120.26 (15)
N2—C13—H13A	108.8	C7—C6—H6	119.9
C14—C13—H13A	108.8	C5—C6—H6	119.9
H13—C13—H13A	107.7	N1—C2—C1	109.32 (13)
C10—N2—C11	121.13 (14)	N1—C2—H2	109.8
C10—N2—C13	120.19 (13)	C1—C2—H2	109.8
C11—N2—C13	118.68 (13)	N1—C2—H2A	109.8
N2—C10—C9	120.27 (15)	C1—C2—H2A	109.8
N2—C10—H10	119.9	H2—C2—H2A	108.3
C9—C10—H10	119.9	C3—C4—C5	119.62 (16)
C10—C9—C8	119.83 (14)	C3—C4—H4	120.2
C10—C9—H9	120.1	C5—C4—H4	120.2
C8—C9—H9	120.1	N1—C3—C4	120.75 (16)
C9—C8—C12	118.34 (15)	N1—C3—H3	119.6
C9—C8—C5	121.34 (14)	C4—C3—H3	119.6
C12—C8—C5	120.25 (14)	F2A—B1A—F1A	108.7 (4)
C4—C5—C6	118.07 (15)	F2A—B1A—F4A	108.8 (4)
C4—C5—C8	121.48 (15)	F1A—B1A—F4A	109.9 (4)
C6—C5—C8	120.43 (15)	F2A—B1A—F3A	109.0 (3)
C3—N1—C7	121.07 (14)	F1A—B1A—F3A	109.7 (4)
C3—N1—C2	119.89 (14)	F4A—B1A—F3A	110.7 (4)
C7—N1—C2	118.82 (14)	F2B—B1B—F4B	112.4 (7)
C11—C12—C8	119.80 (15)	F2B—B1B—F1B	111.9 (7)
C11—C12—H12	120.1	F4B—B1B—F1B	112.4 (7)
C8—C12—H12	120.1	F2B—B1B—F3B	108.5 (8)
N1—C7—C6	120.23 (15)	F4B—B1B—F3B	105.1 (7)
N1—C7—H7	119.9	F1B—B1B—F3B	106.0 (8)
C6—C7—H7	119.9
O3—C14—C13—N2	168.93 (14)	C2—N1—C7—C6	−174.36 (15)
O4—C14—C13—N2	−11.5 (2)	C10—N2—C11—C12	−1.5 (2)
C14—C13—N2—C10	−107.12 (17)	C13—N2—C11—C12	178.25 (15)
C14—C13—N2—C11	73.10 (19)	C8—C12—C11—N2	−0.8 (3)
C11—N2—C10—C9	2.0 (2)	N1—C7—C6—C5	0.6 (3)
C13—N2—C10—C9	−177.78 (15)	C4—C5—C6—C7	−1.1 (2)
N2—C10—C9—C8	−0.2 (2)	C8—C5—C6—C7	177.33 (15)
C10—C9—C8—C12	−2.0 (2)	C3—N1—C2—C1	−84.48 (19)
C10—C9—C8—C5	175.02 (15)	C7—N1—C2—C1	90.16 (17)
C9—C8—C5—C4	30.3 (2)	O2—C1—C2—N1	10.3 (2)
C12—C8—C5—C4	−152.72 (17)	O1—C1—C2—N1	−169.22 (14)
C9—C8—C5—C6	−148.12 (17)	C6—C5—C4—C3	0.9 (3)
C12—C8—C5—C6	28.9 (2)	C8—C5—C4—C3	−177.53 (16)
C9—C8—C12—C11	2.5 (2)	C7—N1—C3—C4	−0.4 (3)
C5—C8—C12—C11	−174.60 (15)	C2—N1—C3—C4	174.09 (16)
C3—N1—C7—C6	0.2 (3)	C5—C4—C3—N1	−0.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1^i	0.99	2.43	3.387 (2)	161
C10—H10···O3^ii	0.95	2.61	3.126 (2)	114
C10—H10···O1^i	0.95	2.51	3.362 (2)	149
C12—H12···O2^iii	0.95	2.28	3.188 (2)	159
C7—H7···O3^iv	0.95	2.34	3.208 (2)	151
C2—H2···O3^iv	0.99	2.36	3.231 (2)	146
C4—H4···O2^v	0.95	2.41	3.278 (2)	151
O4—H1B···O2^vi	1.42	2.39	3.3044 (17)	118.1
O1—H1B···O4^vii	1.05	1.42	2.4694 (18)	172.0

Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) −x, −y+1, −z+1; (iii) x−1, y, z; (iv) −x+1/2, y+1/2, −z+3/2; (v) x−1/2, −y+3/2, z−1/2; (vi) x−3/2, −y+3/2, z−1/2; (vii) x−9/2, −y−7/2, z−7/2.