(S)-(-)-1-Phenyl-ethanaminium 4-(4,4-di-fluoro-1,3,5,7-tetra-methyl-3a,4a-diaza-4-borata-s-indacen-8-yl)benzoate.

The title compound, C(8)H(12)N(+)·C(20)H(18)BF(2)N(2)O(2) (-), crystallizes with a significant amount of void space [4.0 (5)%] in the unit cell. The structure displays N-H⋯O hydrogen bonding between the components. The plane formed by the benzoic acid moiety of the BODIPY-CO(2) (-) is twisted by 80.71 (6)° relative to the plane formed by the ring C and N atoms of the tetramethyldipyrrin portion of the molecule.

Related literature

For the use of crystalline materials that contain emissive transition metal complexes for sensing small mol­ecules, see: McGee & Mann (2007 ▶); Smith & Mann (2009 ▶). The boron dipyrrin family of dyes could be an alternative to these often costly transition metal complexes and can also be easily modified at the meso position, see: Erten-Ela et al. (2008 ▶); Ulrich et al. (2008 ▶). We have found that to sense small mol­ecules effectively, empty channels must be present in the crystal structure to allow the analyte mol­ecules to penetrate the crystalline lattice, see: McGee & Mann (2007 ▶); McGee et al. (2007 ▶); Smith & Mann (2009 ▶). For factors that could facilitate inefficient packing, see: Lancaster et al. (2006 ▶); Imai et al. (2007 ▶, 2008 ▶); Brock et al. (1991 ▶); Tominaga et al. (2011 ▶). Mol­ecules such as methanol and water have mol­ecular volumes consistent with their possible incorporation in the void cavities, see: Buss et al. (1998 ▶) For details of the synthesis, see: Tomasulo et al. (2008 ▶). For refinement details, see: Flack (1983 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). The amount and location of the void space was analyzed with PLATON/VOID (Spek, 2009) ▶. For Wallach’s rule, see: Herbstein (2005 ▶).

Experimental

Crystal data

C8H12N+·C20H18BF2N2O2 −

M = 489.36

Monoclinic,

a = 12.492 (5) Å

b = 6.629 (4) Å

c = 16.042 (7) Å

β = 96.74 (3)°

V = 1319.2 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.50 × 0.30 × 0.03 mm

Data collection

Siemens SMART Platform CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T min = 0.958, T max = 0.997

11639 measured reflections

4593 independent reflections

3331 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.130

S = 1.03

4593 reflections

327 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b ▶); molecular graphics: SHELXTL (Sheldrick, 2008b ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811019167/fl2344sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811019167/fl2344Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C8H12N+·C20H18BF2N2O2−	F(000) = 516
Mr = 489.36	Dx = 1.232 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 12.492 (5) Å	Cell parameters from 2034 reflections
b = 6.629 (4) Å	θ = 2.6–26.8°
c = 16.042 (7) Å	µ = 0.09 mm−1
β = 96.74 (3)°	T = 173 K
V = 1319.2 (11) Å3	Block, orange
Z = 2	0.50 × 0.30 × 0.03 mm

Siemens SMART Platform CCD diffractometer	4593 independent reflections
Radiation source: normal-focus sealed tube	3331 reflections with I > 2σ(I)
graphite	Rint = 0.052
area detector, ω scans per φ	θmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −14→14
Tmin = 0.958, Tmax = 0.997	k = −7→7
11639 measured reflections	l = −19→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.071P)2] where P = (Fo2 + 2Fc2)/3
4593 reflections	(Δ/σ)max < 0.001
327 parameters	Δρmax = 0.23 e Å−3
1 restraint	Δρmin = −0.21 e Å−3

Experimental. Cell errors are from iterative updates since the crystal is believed to have been moving during the data collection.

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.Errors in the CIF check pertaining to the Flack parameter should be ignored. Not only is this structure a light atom structure, but the chirality of the amine is known explicitly from the synthesis of the material to be S at C27.This same argument can be used to ignore the other errors regarding the Friedel data. Merging the data with the MERG 4 command did not significantly decrease the number of errors received in the cif report, and in fact made the number of significant errors increase. Consequently, the structure was not refined with the MERG 4 command. The number of Friedel pairs calculated by using the MERG 2 and MERG 4 commands was 2071 which is in very close agreement with the number calculated in this CIF of 2052.

	x	y	z	Uiso*/Ueq	Occ. (<1)
B1	0.7689 (3)	0.7133 (6)	0.9400 (2)	0.0381 (10)
O1	0.18036 (17)	0.6656 (3)	0.50847 (14)	0.0419 (6)
O2	0.12408 (15)	0.9456 (3)	0.56863 (13)	0.0352 (5)
N1	0.75434 (19)	0.8879 (4)	0.87528 (16)	0.0341 (7)
N2	0.66680 (19)	0.5761 (4)	0.92351 (15)	0.0332 (6)
N3	0.08689 (18)	1.2997 (4)	0.46613 (15)	0.0337 (6)
H1N3	0.1243	1.3954	0.4928	0.051*
H2N3	0.0955	1.1883	0.4948	0.051*
H3N3	0.0190	1.3327	0.4598	0.051*
F1	0.86211 (14)	0.6040 (3)	0.93019 (12)	0.0528 (6)
F2	0.77597 (15)	0.7887 (3)	1.02279 (11)	0.0529 (5)
C1	0.8260 (2)	1.0396 (5)	0.8678 (2)	0.0355 (8)
C2	0.7862 (2)	1.1611 (5)	0.7977 (2)	0.0395 (8)
H2A	0.8207	1.2778	0.7792	0.047*
C3	0.6896 (2)	1.0825 (4)	0.76100 (19)	0.0328 (7)
C4	0.6676 (2)	0.9086 (4)	0.81062 (18)	0.0282 (7)
C5	0.5803 (2)	0.7722 (4)	0.80429 (18)	0.0277 (7)
C6	0.5779 (2)	0.6109 (4)	0.86052 (19)	0.0295 (7)
C7	0.4972 (2)	0.4591 (5)	0.8716 (2)	0.0348 (8)
C8	0.5405 (3)	0.3394 (5)	0.9380 (2)	0.0414 (9)
H8A	0.5062	0.2260	0.9595	0.050*
C9	0.6438 (3)	0.4127 (5)	0.9687 (2)	0.0397 (8)
C10	0.9285 (3)	1.0655 (6)	0.9256 (2)	0.0513 (10)
H10A	0.9346	0.9575	0.9676	0.077*	0.50
H10B	0.9278	1.1965	0.9538	0.077*	0.50
H10C	0.9901	1.0593	0.8931	0.077*	0.50
H10D	0.9671	1.1847	0.9087	0.077*	0.50
H10E	0.9739	0.9457	0.9225	0.077*	0.50
H10F	0.9115	1.0829	0.9833	0.077*	0.50
C11	0.6218 (3)	1.1628 (5)	0.6827 (2)	0.0434 (9)
H11A	0.5569	1.0798	0.6706	0.065*	0.50
H11B	0.6640	1.1574	0.6349	0.065*	0.50
H11C	0.6010	1.3027	0.6922	0.065*	0.50
H11D	0.6577	1.2801	0.6612	0.065*	0.50
H11E	0.5506	1.2025	0.6969	0.065*	0.50
H11F	0.6136	1.0572	0.6396	0.065*	0.50
C12	0.7212 (3)	0.3300 (6)	1.0401 (2)	0.0530 (10)
H12A	0.7868	0.4123	1.0469	0.080*	0.50
H12B	0.7398	0.1904	1.0277	0.080*	0.50
H12C	0.6871	0.3335	1.0921	0.080*	0.50
H12D	0.6890	0.2119	1.0642	0.080*	0.50
H12E	0.7360	0.4338	1.0835	0.080*	0.50
H12F	0.7887	0.2906	1.0190	0.080*	0.50
C13	0.3869 (2)	0.4326 (5)	0.8233 (2)	0.0378 (8)
H13A	0.3758	0.5351	0.7791	0.057*	0.50
H13B	0.3318	0.4476	0.8616	0.057*	0.50
H13C	0.3815	0.2980	0.7980	0.057*	0.50
H13D	0.3502	0.3187	0.8467	0.057*	0.50
H13E	0.3943	0.4062	0.7642	0.057*	0.50
H13F	0.3446	0.5558	0.8278	0.057*	0.50
C14	0.4866 (2)	0.7945 (5)	0.73731 (18)	0.0269 (7)
C15	0.4026 (2)	0.9297 (5)	0.7490 (2)	0.0326 (7)
H15A	0.4089	1.0165	0.7964	0.039*
C16	0.3101 (2)	0.9367 (5)	0.69111 (19)	0.0340 (8)
H16A	0.2543	1.0291	0.6998	0.041*
C17	0.2975 (2)	0.8110 (5)	0.62063 (19)	0.0298 (7)
C18	0.3830 (2)	0.6827 (4)	0.60732 (19)	0.0307 (7)
H18A	0.3778	0.5996	0.5588	0.037*
C19	0.4763 (2)	0.6762 (5)	0.6652 (2)	0.0341 (8)
H19A	0.5337	0.5891	0.6549	0.041*
C20	0.1934 (2)	0.8065 (5)	0.56131 (19)	0.0329 (7)
C21	0.0487 (2)	1.1316 (4)	0.3262 (2)	0.0332 (8)
C22	−0.0024 (3)	1.1990 (6)	0.2490 (2)	0.0523 (10)
H22A	0.0091	1.3334	0.2314	0.063*
C23	−0.0698 (3)	1.0721 (7)	0.1975 (2)	0.0626 (11)
H23A	−0.1026	1.1198	0.1447	0.075*
C24	−0.0894 (3)	0.8777 (6)	0.2223 (2)	0.0460 (9)
H24A	−0.1359	0.7919	0.1872	0.055*
C25	−0.0400 (2)	0.8084 (6)	0.2998 (2)	0.0419 (8)
H25A	−0.0546	0.6758	0.3179	0.050*
C26	0.0303 (2)	0.9322 (5)	0.3508 (2)	0.0360 (8)
H26A	0.0657	0.8818	0.4022	0.043*
C27	0.1249 (2)	1.2695 (5)	0.38100 (19)	0.0355 (8)
H27A	0.1254	1.4040	0.3528	0.043*
C28	0.2423 (3)	1.1901 (6)	0.3944 (2)	0.0503 (10)
H28A	0.2703	1.1790	0.3400	0.075*
H28B	0.2436	1.0572	0.4212	0.075*
H28C	0.2872	1.2840	0.4305	0.075*

	U11	U22	U33	U12	U13	U23
B1	0.031 (2)	0.047 (2)	0.035 (2)	0.0018 (18)	−0.0001 (18)	0.0033 (19)
O1	0.0409 (13)	0.0309 (12)	0.0498 (15)	−0.0021 (10)	−0.0126 (11)	−0.0074 (11)
O2	0.0266 (11)	0.0357 (12)	0.0418 (13)	0.0041 (10)	−0.0020 (10)	0.0034 (11)
N1	0.0251 (14)	0.0388 (16)	0.0381 (16)	−0.0008 (12)	0.0020 (13)	−0.0019 (12)
N2	0.0304 (15)	0.0352 (15)	0.0343 (15)	0.0052 (12)	0.0050 (13)	0.0051 (13)
N3	0.0267 (13)	0.0294 (14)	0.0438 (15)	−0.0009 (12)	−0.0005 (12)	−0.0014 (13)
F1	0.0297 (10)	0.0592 (13)	0.0687 (13)	0.0124 (9)	0.0027 (10)	0.0105 (11)
F2	0.0584 (13)	0.0623 (13)	0.0363 (11)	−0.0085 (11)	−0.0020 (10)	−0.0023 (10)
C1	0.0268 (17)	0.0419 (19)	0.0379 (19)	−0.0046 (16)	0.0047 (15)	−0.0066 (17)
C2	0.0328 (19)	0.0349 (18)	0.052 (2)	−0.0082 (16)	0.0087 (17)	−0.0048 (18)
C3	0.0311 (17)	0.0290 (17)	0.0389 (18)	0.0012 (14)	0.0064 (15)	−0.0026 (15)
C4	0.0239 (16)	0.0301 (17)	0.0291 (17)	0.0049 (14)	−0.0028 (14)	−0.0018 (14)
C5	0.0251 (16)	0.0257 (16)	0.0330 (17)	0.0046 (13)	0.0056 (14)	−0.0031 (14)
C6	0.0238 (16)	0.0296 (17)	0.0343 (17)	0.0046 (13)	0.0005 (14)	−0.0018 (14)
C7	0.0338 (18)	0.0289 (17)	0.043 (2)	0.0017 (15)	0.0103 (16)	−0.0016 (15)
C8	0.045 (2)	0.0311 (18)	0.050 (2)	−0.0004 (16)	0.0142 (18)	0.0072 (17)
C9	0.042 (2)	0.0372 (19)	0.041 (2)	0.0118 (16)	0.0102 (17)	0.0093 (17)
C10	0.0333 (19)	0.063 (2)	0.056 (2)	−0.0136 (19)	0.0016 (18)	−0.013 (2)
C11	0.0370 (19)	0.041 (2)	0.051 (2)	0.0012 (16)	0.0022 (17)	0.0151 (17)
C12	0.057 (2)	0.056 (2)	0.046 (2)	0.012 (2)	0.0080 (19)	0.0130 (19)
C13	0.0349 (18)	0.0301 (17)	0.049 (2)	−0.0040 (15)	0.0084 (16)	0.0002 (16)
C14	0.0242 (16)	0.0241 (15)	0.0316 (17)	0.0002 (13)	−0.0002 (14)	0.0050 (14)
C15	0.0310 (17)	0.0293 (16)	0.0366 (19)	0.0034 (14)	−0.0001 (15)	−0.0054 (15)
C16	0.0270 (17)	0.0322 (17)	0.0419 (19)	0.0077 (14)	−0.0001 (15)	−0.0080 (16)
C17	0.0272 (16)	0.0257 (16)	0.0355 (17)	−0.0024 (14)	−0.0003 (14)	0.0030 (15)
C18	0.0276 (17)	0.0291 (16)	0.0338 (18)	0.0026 (14)	−0.0034 (15)	−0.0069 (14)
C19	0.0280 (17)	0.0302 (17)	0.045 (2)	0.0046 (14)	0.0066 (16)	−0.0038 (16)
C20	0.0283 (17)	0.0266 (17)	0.043 (2)	−0.0045 (15)	0.0014 (15)	0.0068 (17)
C21	0.0281 (17)	0.0317 (18)	0.041 (2)	0.0054 (13)	0.0091 (15)	0.0045 (15)
C22	0.063 (3)	0.044 (2)	0.048 (2)	0.009 (2)	0.001 (2)	0.0098 (19)
C23	0.064 (3)	0.077 (3)	0.044 (2)	0.011 (2)	−0.006 (2)	0.012 (2)
C24	0.039 (2)	0.057 (2)	0.040 (2)	−0.0001 (17)	−0.0010 (17)	−0.0107 (18)
C25	0.0387 (19)	0.045 (2)	0.042 (2)	−0.0037 (17)	0.0055 (17)	−0.0009 (18)
C26	0.0354 (18)	0.0354 (18)	0.0366 (19)	−0.0029 (16)	0.0019 (16)	0.0021 (16)
C27	0.0332 (17)	0.0316 (17)	0.0436 (19)	−0.0035 (14)	0.0124 (16)	0.0035 (15)
C28	0.0337 (19)	0.049 (2)	0.071 (3)	−0.0027 (17)	0.0181 (19)	−0.006 (2)

B1—F1	1.396 (4)	C12—H12A	0.9800
B1—F2	1.413 (4)	C12—H12B	0.9800
B1—N1	1.551 (5)	C12—H12C	0.9800
B1—N2	1.563 (5)	C12—H12D	0.9800
O1—C20	1.259 (4)	C12—H12E	0.9800
O2—C20	1.279 (4)	C12—H12F	0.9800
N1—C1	1.361 (4)	C13—H13A	0.9800
N1—C4	1.416 (4)	C13—H13B	0.9800
N2—C9	1.353 (4)	C13—H13C	0.9800
N2—C6	1.430 (4)	C13—H13D	0.9800
N3—C27	1.511 (4)	C13—H13E	0.9800
N3—H1N3	0.8701	C13—H13F	0.9800
N3—H2N3	0.8701	C14—C19	1.391 (4)
N3—H3N3	0.8701	C14—C15	1.409 (4)
C1—C2	1.424 (5)	C15—C16	1.395 (4)
C1—C10	1.500 (5)	C15—H15A	0.9500
C2—C3	1.381 (4)	C16—C17	1.399 (4)
C2—H2A	0.9500	C16—H16A	0.9500
C3—C4	1.445 (4)	C17—C18	1.401 (4)
C3—C11	1.526 (4)	C17—C20	1.520 (4)
C4—C5	1.410 (4)	C18—C19	1.403 (4)
C5—C6	1.402 (4)	C18—H18A	0.9500
C5—C14	1.501 (4)	C19—H19A	0.9500
C6—C7	1.450 (4)	C21—C22	1.398 (5)
C7—C8	1.386 (4)	C21—C26	1.406 (4)
C7—C13	1.510 (4)	C21—C27	1.523 (4)
C8—C9	1.412 (5)	C22—C23	1.391 (5)
C8—H8A	0.9500	C22—H22A	0.9500
C9—C12	1.513 (5)	C23—C24	1.379 (6)
C10—H10A	0.9800	C23—H23A	0.9500
C10—H10B	0.9800	C24—C25	1.398 (4)
C10—H10C	0.9800	C24—H24A	0.9500
C10—H10D	0.9800	C25—C26	1.395 (5)
C10—H10E	0.9800	C25—H25A	0.9500
C10—H10F	0.9800	C26—H26A	0.9500
C11—H11A	0.9800	C27—C28	1.548 (4)
C11—H11B	0.9800	C27—H27A	1.0000
C11—H11C	0.9800	C28—H28A	0.9800
C11—H11D	0.9800	C28—H28B	0.9800
C11—H11E	0.9800	C28—H28C	0.9800
C11—H11F	0.9800
F1—B1—F2	109.2 (3)	C9—C12—H12C	109.5
F1—B1—N1	110.2 (3)	H12A—C12—H12C	109.5
F2—B1—N1	110.8 (3)	H12B—C12—H12C	109.5
F1—B1—N2	110.7 (3)	C9—C12—H12D	109.5
F2—B1—N2	109.0 (3)	H12A—C12—H12D	141.1
N1—B1—N2	107.0 (3)	H12B—C12—H12D	56.3
C1—N1—C4	108.6 (3)	H12C—C12—H12D	56.3
C1—N1—B1	125.7 (3)	C9—C12—H12E	109.5
C4—N1—B1	125.6 (3)	H12A—C12—H12E	56.3
C9—N2—C6	108.2 (3)	H12B—C12—H12E	141.1
C9—N2—B1	126.5 (3)	H12C—C12—H12E	56.3
C6—N2—B1	125.2 (3)	H12D—C12—H12E	109.5
C27—N3—H1N3	109.5	C9—C12—H12F	109.5
C27—N3—H2N3	109.5	H12A—C12—H12F	56.3
H1N3—N3—H2N3	109.5	H12B—C12—H12F	56.3
C27—N3—H3N3	109.5	H12C—C12—H12F	141.1
H1N3—N3—H3N3	109.5	H12D—C12—H12F	109.5
H2N3—N3—H3N3	109.5	H12E—C12—H12F	109.5
N1—C1—C2	108.4 (3)	C7—C13—H13A	109.5
N1—C1—C10	123.6 (3)	C7—C13—H13B	109.5
C2—C1—C10	128.1 (3)	H13A—C13—H13B	109.5
C3—C2—C1	109.3 (3)	C7—C13—H13C	109.5
C3—C2—H2A	125.4	H13A—C13—H13C	109.5
C1—C2—H2A	125.4	H13B—C13—H13C	109.5
C2—C3—C4	106.2 (3)	C7—C13—H13D	109.5
C2—C3—C11	126.3 (3)	H13A—C13—H13D	141.1
C4—C3—C11	127.4 (3)	H13B—C13—H13D	56.3
C5—C4—N1	120.6 (3)	H13C—C13—H13D	56.3
C5—C4—C3	131.9 (3)	C7—C13—H13E	109.5
N1—C4—C3	107.6 (3)	H13A—C13—H13E	56.3
C6—C5—C4	121.2 (3)	H13B—C13—H13E	141.1
C6—C5—C14	117.5 (3)	H13C—C13—H13E	56.3
C4—C5—C14	121.3 (3)	H13D—C13—H13E	109.5
C5—C6—N2	120.3 (3)	C7—C13—H13F	109.5
C5—C6—C7	132.6 (3)	H13A—C13—H13F	56.3
N2—C6—C7	107.1 (3)	H13B—C13—H13F	56.3
C8—C7—C6	106.1 (3)	H13C—C13—H13F	141.1
C8—C7—C13	125.3 (3)	H13D—C13—H13F	109.5
C6—C7—C13	128.6 (3)	H13E—C13—H13F	109.5
C7—C8—C9	109.2 (3)	C19—C14—C15	118.1 (3)
C7—C8—H8A	125.4	C19—C14—C5	121.9 (3)
C9—C8—H8A	125.4	C15—C14—C5	119.9 (3)
N2—C9—C8	109.4 (3)	C16—C15—C14	120.3 (3)
N2—C9—C12	122.7 (3)	C16—C15—H15A	119.9
C8—C9—C12	128.0 (3)	C14—C15—H15A	119.9
C1—C10—H10A	109.5	C15—C16—C17	121.6 (3)
C1—C10—H10B	109.5	C15—C16—H16A	119.2
H10A—C10—H10B	109.5	C17—C16—H16A	119.2
C1—C10—H10C	109.5	C16—C17—C18	118.0 (3)
H10A—C10—H10C	109.5	C16—C17—C20	121.6 (3)
H10B—C10—H10C	109.5	C18—C17—C20	120.3 (3)
C1—C10—H10D	109.5	C17—C18—C19	120.5 (3)
H10A—C10—H10D	141.1	C17—C18—H18A	119.8
H10B—C10—H10D	56.3	C19—C18—H18A	119.8
H10C—C10—H10D	56.3	C14—C19—C18	121.4 (3)
C1—C10—H10E	109.5	C14—C19—H19A	119.3
H10A—C10—H10E	56.3	C18—C19—H19A	119.3
H10B—C10—H10E	141.1	O1—C20—O2	124.1 (3)
H10C—C10—H10E	56.3	O1—C20—C17	118.0 (3)
H10D—C10—H10E	109.5	O2—C20—C17	117.9 (3)
C1—C10—H10F	109.5	C22—C21—C26	118.5 (3)
H10A—C10—H10F	56.3	C22—C21—C27	120.6 (3)
H10B—C10—H10F	56.3	C26—C21—C27	120.9 (3)
H10C—C10—H10F	141.1	C23—C22—C21	120.9 (4)
H10D—C10—H10F	109.5	C23—C22—H22A	119.5
H10E—C10—H10F	109.5	C21—C22—H22A	119.5
C3—C11—H11A	109.5	C24—C23—C22	120.6 (4)
C3—C11—H11B	109.5	C24—C23—H23A	119.7
H11A—C11—H11B	109.5	C22—C23—H23A	119.7
C3—C11—H11C	109.5	C23—C24—C25	119.3 (3)
H11A—C11—H11C	109.5	C23—C24—H24A	120.4
H11B—C11—H11C	109.5	C25—C24—H24A	120.4
C3—C11—H11D	109.5	C26—C25—C24	120.6 (3)
H11A—C11—H11D	141.1	C26—C25—H25A	119.7
H11B—C11—H11D	56.3	C24—C25—H25A	119.7
H11C—C11—H11D	56.3	C25—C26—C21	120.0 (3)
C3—C11—H11E	109.5	C25—C26—H26A	120.0
H11A—C11—H11E	56.3	C21—C26—H26A	120.0
H11B—C11—H11E	141.1	N3—C27—C21	111.1 (2)
H11C—C11—H11E	56.3	N3—C27—C28	108.2 (3)
H11D—C11—H11E	109.5	C21—C27—C28	113.2 (3)
C3—C11—H11F	109.5	N3—C27—H27A	108.1
H11A—C11—H11F	56.3	C21—C27—H27A	108.1
H11B—C11—H11F	56.3	C28—C27—H27A	108.1
H11C—C11—H11F	141.1	C27—C28—H28A	109.5
H11D—C11—H11F	109.5	C27—C28—H28B	109.5
H11E—C11—H11F	109.5	H28A—C28—H28B	109.5
C9—C12—H12A	109.5	C27—C28—H28C	109.5
C9—C12—H12B	109.5	H28A—C28—H28C	109.5
H12A—C12—H12B	109.5	H28B—C28—H28C	109.5
F1—B1—N1—C1	−58.8 (4)	N2—C6—C7—C8	−1.2 (3)
F2—B1—N1—C1	62.1 (4)	C5—C6—C7—C13	−0.6 (5)
N2—B1—N1—C1	−179.3 (3)	N2—C6—C7—C13	177.9 (3)
F1—B1—N1—C4	116.8 (3)	C6—C7—C8—C9	0.6 (3)
F2—B1—N1—C4	−122.3 (3)	C13—C7—C8—C9	−178.5 (3)
N2—B1—N1—C4	−3.7 (4)	C6—N2—C9—C8	−0.9 (3)
F1—B1—N2—C9	63.6 (4)	B1—N2—C9—C8	175.4 (3)
F2—B1—N2—C9	−56.4 (4)	C6—N2—C9—C12	179.0 (3)
N1—B1—N2—C9	−176.2 (3)	B1—N2—C9—C12	−4.7 (5)
F1—B1—N2—C6	−120.6 (3)	C7—C8—C9—N2	0.2 (4)
F2—B1—N2—C6	119.3 (3)	C7—C8—C9—C12	−179.7 (3)
N1—B1—N2—C6	−0.5 (4)	C6—C5—C14—C19	−78.9 (3)
C4—N1—C1—C2	0.0 (3)	C4—C5—C14—C19	101.3 (4)
B1—N1—C1—C2	176.2 (3)	C6—C5—C14—C15	97.2 (3)
C4—N1—C1—C10	−179.8 (3)	C4—C5—C14—C15	−82.6 (3)
B1—N1—C1—C10	−3.6 (5)	C19—C14—C15—C16	2.7 (4)
N1—C1—C2—C3	−0.7 (3)	C5—C14—C15—C16	−173.5 (3)
C10—C1—C2—C3	179.1 (3)	C14—C15—C16—C17	0.2 (5)
C1—C2—C3—C4	1.0 (3)	C15—C16—C17—C18	−2.8 (4)
C1—C2—C3—C11	−178.0 (3)	C15—C16—C17—C20	175.1 (3)
C1—N1—C4—C5	−179.0 (2)	C16—C17—C18—C19	2.5 (4)
B1—N1—C4—C5	4.8 (4)	C20—C17—C18—C19	−175.5 (3)
C1—N1—C4—C3	0.6 (3)	C15—C14—C19—C18	−3.1 (4)
B1—N1—C4—C3	−175.6 (3)	C5—C14—C19—C18	173.1 (3)
C2—C3—C4—C5	178.6 (3)	C17—C18—C19—C14	0.5 (4)
C11—C3—C4—C5	−2.4 (5)	C16—C17—C20—O1	−167.4 (3)
C2—C3—C4—N1	−1.0 (3)	C18—C17—C20—O1	10.5 (4)
C11—C3—C4—N1	177.9 (3)	C16—C17—C20—O2	12.2 (4)
N1—C4—C5—C6	−1.2 (4)	C18—C17—C20—O2	−170.0 (3)
C3—C4—C5—C6	179.2 (3)	C26—C21—C22—C23	−0.1 (5)
N1—C4—C5—C14	178.7 (2)	C27—C21—C22—C23	178.2 (3)
C3—C4—C5—C14	−0.9 (5)	C21—C22—C23—C24	1.3 (6)
C4—C5—C6—N2	−2.8 (4)	C22—C23—C24—C25	−0.5 (5)
C14—C5—C6—N2	177.3 (2)	C23—C24—C25—C26	−1.5 (5)
C4—C5—C6—C7	175.5 (3)	C24—C25—C26—C21	2.7 (5)
C14—C5—C6—C7	−4.3 (4)	C22—C21—C26—C25	−1.9 (4)
C9—N2—C6—C5	−180.0 (2)	C27—C21—C26—C25	179.9 (3)
B1—N2—C6—C5	3.6 (4)	C22—C21—C27—N3	121.2 (3)
C9—N2—C6—C7	1.3 (3)	C26—C21—C27—N3	−60.6 (4)
B1—N2—C6—C7	−175.1 (3)	C22—C21—C27—C28	−116.8 (3)
C5—C6—C7—C8	−179.7 (3)	C26—C21—C27—C28	61.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···O1i	0.87	1.93	2.743 (4)	155
N3—H2N3···O2	0.87	2.00	2.872 (3)	178
N3—H3N3···O2ii	0.87	1.94	2.801 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N3⋯O1i	0.87	1.93	2.743 (4)	155
N3—H2N3⋯O2	0.87	2.00	2.872 (3)	178
N3—H3N3⋯O2ii	0.87	1.94	2.801 (3)	169

Symmetry codes: (i) ; (ii) .