Triphenyl{(E)-4-[4-(phenyldiazenyl)phenyl]-4H-1,2,4-triazol-1-yl}boron

Urakami, D.; Inoue, K.; Hayami, S.

doi:10.1107/S1600536809036071

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2425

doi:10.1107/S1600536809036071

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Triphenyl{(E)-4-[4-(phenyldiazenyl)phenyl]-4H-1,2,4-triazol-1-yl}boron

Daisuke Urakami,^a Katsuya Inoue ^a,^b and Shinya Hayami ^c ^*

^aDepartment of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima 739-8526, Japan, ^bInstitute for Advanced Materials Research, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima 739-8526, Japan, and ^cDepartment of Chemistry, Graduate School of Science and Technology, Kumamoto University, 2-39-1 Kurokami, Kumamoto 860-8555, Japan
^*Correspondence e-mail: hayami@sci.kumamoto-u.ac.jp

(Received 25 July 2009; accepted 7 September 2009; online 9 September 2009)

In the title compound, C₃₂H₂₆BN₅ or [(C₁₄H₁₁N₅)B(C₆H₅)₃], the B atom is approximately tetrahedrally coordinated. The diazo unit is in a trans conformation, which is generally more stable than a cis one for aromatic azo compounds. The crystal structure features very weak C—H⋯π interactions. The dihedral angles between the central benzene ring and the terminal rings in the heterocycle are 62.64, 73.54 and 61.60°.

Related literature

For the use of azobenzenes for holographic information storage, see: Rasmussen et al. (1999 ).

Experimental

Crystal data

C₃₂H₂₆BN₅
M_r = 491.39
Monoclinic, P 2₁ /n
a = 17.4049 (6) Å
b = 7.1284 (2) Å
c = 21.0645 (7) Å
β = 97.0810 (15)°
V = 2593.52 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 113 K
0.40 × 0.20 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (Higashi, 2001 ) T_min = 0.971, T_max = 0.993
19971 measured reflections
5668 independent reflections
4068 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.138
S = 1.03
5668 reflections
343 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H3⋯Cg1ⁱ	0.95	2.91	3.822 (2)	162
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 is the centroid of the C27–C31 ring.

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Yadokari-XG (Wakita, 2000 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809036071/bx2228sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809036071/bx2228Isup2.hkl

checkCIF report

Comment top

Photochromic materials are of interest as media for recording, storage, and reproduction of information in nonlinear optics and holography. Aromatic azo compounds occupy an important place among such materials, therefore many photoisomerizable azobenzene groups were synthesized to apply for photoswitchable systems or optical data storage device (Rasmussen et al., 1999). Here we report the synthesis and crystal structure of the title complex. The addition compound of a triazole derivative with diazobenzene and a triphenylboron contains a B atom approximately tetrahedrally coordinated with a B—N distance of 1.636 (2) Å and B—C bond lengths averaging 1.625 (2) Å. The diazo moiety forms a trans conformation, and the bond distance N4—N5 is 1.2563 (19) Å. The crystal structure is stabilized by weak C—H···π (C27/C32) interactions between phenyl hydrogens from (E)-4-(4-(phenyldiazenyl)phenyl-4H-1,2,4-triazole fragment to phenyl rings from triphenylboron fragment. Fig 2, Table 1.

Related literature top

For the use of azobenzene for holographic information storage, see: Rasmussen et al. (1999).

Experimental top

The compound (I) was synthesized by refluxed for an hour with (E)-4-(4-(phenyldiazenyl)phenyl)-4H-1,2,4-triazole (3 mmol, 0.748 g), sodium tetraphenylborate (4 mmol, 1.369 g) and iron chloride tetrahydrate (2 mmol, 0.390 g) in ethanol (50 ml). The resulting yellow solution was filtered and the single crystals of (I) suitable X-ray diffraction were obtained by slowly evaporation of ethanol.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Yadokari-XG (Wakita, 2000); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP drawing for the compound (I) showing 50% probability displacement ellipsoids.
	Fig. 2. Packing structure for the compound (I).

Triphenyl{(E)-4-[4-(phenyldiazenyl)phenyl]-4H-1,2,4- triazol-1-yl}boron top

Crystal data top

C₃₂H₂₆BN₅	F(000) = 1032
M_r = 491.39	D_x = 1.258 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 13301 reflections
a = 17.4049 (6) Å	θ = 2.7–27.4°
b = 7.1284 (2) Å	µ = 0.08 mm⁻¹
c = 21.0645 (7) Å	T = 113 K
β = 97.0810 (15)°	Block, orange
V = 2593.52 (14) Å³	0.40 × 0.20 × 0.10 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	5668 independent reflections
Radiation source: fine-focus sealed tube	4068 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ω scans	θ_max = 27.4°, θ_min = 1.4°
Absorption correction: multi-scan (Higashi, 2001)	h = −21→22
T_min = 0.971, T_max = 0.993	k = −9→8
19971 measured reflections	l = −27→27

Refinement top

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0835P)²] where P = (F_o² + 2F_c²)/3
5668 reflections	(Δ/σ)_max = 0.002
343 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₃₂H₂₆BN₅	V = 2593.52 (14) Å³
M_r = 491.39	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 17.4049 (6) Å	µ = 0.08 mm⁻¹
b = 7.1284 (2) Å	T = 113 K
c = 21.0645 (7) Å	0.40 × 0.20 × 0.10 mm
β = 97.0810 (15)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	5668 independent reflections
Absorption correction: multi-scan (Higashi, 2001)	4068 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.993	R_int = 0.050
19971 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.03	Δρ_max = 0.26 e Å⁻³
5668 reflections	Δρ_min = −0.27 e Å⁻³
343 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
B1	0.21836 (11)	0.3083 (3)	0.04914 (9)	0.0190 (4)
C1	0.29403 (9)	0.0119 (2)	0.10360 (8)	0.0197 (4)
H1	0.2800	−0.0758	0.0702	0.024*
C2	0.34594 (11)	0.1427 (2)	0.19029 (8)	0.0285 (4)
H2	0.3765	0.1618	0.2304	0.034*
C3	0.38777 (9)	−0.1882 (2)	0.17537 (8)	0.0201 (4)
C4	0.41059 (10)	−0.2207 (2)	0.23988 (8)	0.0256 (4)
H3	0.3942	−0.1399	0.2714	0.031*
C5	0.45769 (11)	−0.3730 (2)	0.25743 (8)	0.0273 (4)
H4	0.4750	−0.3949	0.3014	0.033*
C6	0.48000 (9)	−0.4945 (2)	0.21125 (8)	0.0214 (4)
C7	0.45478 (10)	−0.4616 (2)	0.14683 (8)	0.0219 (4)
H5	0.4687	−0.5460	0.1153	0.026*
C8	0.40960 (9)	−0.3068 (2)	0.12870 (8)	0.0217 (4)
H6	0.3937	−0.2820	0.0847	0.026*
C9	0.58832 (10)	−0.9199 (2)	0.21814 (8)	0.0225 (4)
C10	0.62167 (10)	−0.9365 (3)	0.28142 (8)	0.0247 (4)
H7	0.6102	−0.8473	0.3124	0.030*
C11	0.67159 (10)	−1.0832 (3)	0.29885 (9)	0.0296 (4)
H8	0.6944	−1.0950	0.3420	0.036*
C12	0.68874 (11)	−1.2142 (3)	0.25356 (9)	0.0330 (5)
H9	0.7238	−1.3137	0.2657	0.040*
C13	0.65460 (12)	−1.1989 (3)	0.19090 (10)	0.0353 (5)
H10	0.6659	−1.2888	0.1600	0.042*
C14	0.60408 (11)	−1.0529 (3)	0.17306 (9)	0.0313 (4)
H11	0.5802	−1.0435	0.1301	0.038*
C15	0.17458 (9)	0.1567 (2)	−0.00001 (8)	0.0194 (4)
C16	0.12558 (9)	0.0210 (2)	0.02111 (8)	0.0222 (4)
H12	0.1184	0.0189	0.0651	0.027*
C17	0.08711 (10)	−0.1107 (2)	−0.01958 (9)	0.0267 (4)
H13	0.0547	−0.2015	−0.0033	0.032*
C18	0.09617 (11)	−0.1094 (2)	−0.08390 (9)	0.0292 (4)
H14	0.0702	−0.1994	−0.1121	0.035*
C19	0.14345 (10)	0.0242 (3)	−0.10691 (8)	0.0286 (4)
H15	0.1495	0.0268	−0.1511	0.034*
C20	0.18194 (10)	0.1542 (2)	−0.06551 (8)	0.0230 (4)
H16	0.2143	0.2445	−0.0821	0.028*
C21	0.28127 (9)	0.4280 (2)	0.01512 (7)	0.0190 (4)
C22	0.35283 (10)	0.3533 (2)	0.00407 (8)	0.0233 (4)
H17	0.3672	0.2329	0.0208	0.028*
C23	0.40343 (10)	0.4484 (3)	−0.03036 (8)	0.0266 (4)
H18	0.4515	0.3931	−0.0367	0.032*
C24	0.38387 (10)	0.6248 (3)	−0.05563 (8)	0.0282 (4)
H19	0.4185	0.6911	−0.0790	0.034*
C25	0.31309 (10)	0.7026 (3)	−0.04624 (8)	0.0258 (4)
H20	0.2988	0.8223	−0.0636	0.031*
C26	0.26302 (10)	0.6055 (2)	−0.01144 (8)	0.0219 (4)
H21	0.2149	0.6612	−0.0054	0.026*
C27	0.15982 (10)	0.4430 (2)	0.08339 (8)	0.0195 (4)
C28	0.18757 (10)	0.5898 (2)	0.12474 (8)	0.0222 (4)
H22	0.2419	0.6043	0.1354	0.027*
C29	0.13847 (11)	0.7138 (2)	0.15035 (8)	0.0256 (4)
H23	0.1594	0.8127	0.1774	0.031*
C30	0.05859 (11)	0.6942 (3)	0.13665 (8)	0.0277 (4)
H24	0.0247	0.7785	0.1543	0.033*
C31	0.02944 (10)	0.5507 (3)	0.09706 (9)	0.0275 (4)
H25	−0.0250	0.5348	0.0876	0.033*
C32	0.07955 (10)	0.4284 (2)	0.07081 (8)	0.0241 (4)
H26	0.0581	0.3313	0.0432	0.029*
N1	0.26879 (8)	0.1851 (2)	0.10506 (6)	0.0194 (3)
N2	0.30188 (9)	0.2706 (2)	0.16050 (7)	0.0285 (4)
N3	0.34303 (8)	−0.02185 (19)	0.15713 (6)	0.0204 (3)
N4	0.52992 (8)	−0.6447 (2)	0.23468 (7)	0.0238 (3)
N5	0.53680 (8)	−0.7720 (2)	0.19453 (7)	0.0245 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
B1	0.0204 (9)	0.0185 (9)	0.0176 (9)	0.0035 (8)	0.0006 (7)	0.0034 (8)
C1	0.0226 (8)	0.0201 (8)	0.0159 (8)	0.0007 (8)	0.0001 (6)	0.0013 (7)
C2	0.0378 (10)	0.0253 (10)	0.0205 (9)	0.0030 (9)	−0.0045 (8)	−0.0015 (7)
C3	0.0211 (8)	0.0176 (8)	0.0210 (8)	0.0019 (7)	0.0000 (7)	0.0034 (7)
C4	0.0351 (10)	0.0244 (9)	0.0166 (8)	0.0058 (8)	0.0005 (7)	−0.0011 (7)
C5	0.0369 (10)	0.0268 (10)	0.0165 (9)	0.0035 (8)	−0.0036 (7)	0.0015 (7)
C6	0.0216 (8)	0.0229 (9)	0.0190 (8)	0.0015 (8)	−0.0002 (7)	0.0034 (7)
C7	0.0240 (8)	0.0227 (9)	0.0189 (8)	0.0028 (8)	0.0030 (7)	−0.0001 (7)
C8	0.0227 (8)	0.0266 (9)	0.0151 (8)	0.0009 (8)	−0.0005 (6)	0.0020 (7)
C9	0.0232 (9)	0.0229 (9)	0.0222 (9)	0.0031 (8)	0.0057 (7)	0.0046 (7)
C10	0.0266 (9)	0.0245 (9)	0.0235 (9)	0.0028 (8)	0.0050 (7)	0.0029 (7)
C11	0.0296 (10)	0.0304 (10)	0.0285 (10)	0.0027 (9)	0.0023 (8)	0.0071 (8)
C12	0.0319 (10)	0.0275 (10)	0.0409 (12)	0.0094 (9)	0.0102 (9)	0.0093 (9)
C13	0.0449 (12)	0.0287 (10)	0.0347 (11)	0.0094 (10)	0.0140 (9)	0.0002 (9)
C14	0.0403 (11)	0.0302 (10)	0.0234 (9)	0.0054 (9)	0.0041 (8)	0.0009 (8)
C15	0.0192 (8)	0.0190 (8)	0.0196 (8)	0.0061 (7)	0.0001 (6)	0.0014 (7)
C16	0.0214 (9)	0.0234 (9)	0.0215 (9)	0.0041 (8)	0.0016 (7)	0.0018 (7)
C17	0.0224 (9)	0.0216 (9)	0.0343 (10)	0.0007 (8)	−0.0031 (7)	0.0026 (8)
C18	0.0296 (10)	0.0219 (9)	0.0325 (10)	0.0030 (8)	−0.0102 (8)	−0.0068 (8)
C19	0.0350 (10)	0.0300 (10)	0.0190 (9)	0.0061 (9)	−0.0031 (7)	−0.0029 (7)
C20	0.0263 (9)	0.0220 (9)	0.0203 (9)	0.0025 (8)	0.0009 (7)	0.0001 (7)
C21	0.0223 (8)	0.0209 (8)	0.0129 (8)	−0.0009 (7)	−0.0008 (6)	−0.0022 (6)
C22	0.0241 (9)	0.0234 (9)	0.0225 (9)	0.0027 (8)	0.0029 (7)	0.0009 (7)
C23	0.0237 (9)	0.0305 (10)	0.0266 (9)	0.0036 (8)	0.0071 (7)	0.0002 (8)
C24	0.0284 (9)	0.0334 (10)	0.0238 (9)	−0.0030 (9)	0.0081 (7)	0.0029 (8)
C25	0.0303 (9)	0.0259 (9)	0.0205 (9)	0.0009 (8)	0.0008 (7)	0.0047 (7)
C26	0.0224 (8)	0.0251 (9)	0.0181 (8)	0.0030 (8)	0.0017 (7)	−0.0004 (7)
C27	0.0250 (9)	0.0181 (8)	0.0158 (8)	0.0023 (8)	0.0041 (6)	0.0037 (7)
C28	0.0248 (9)	0.0217 (9)	0.0205 (9)	0.0030 (8)	0.0044 (7)	0.0025 (7)
C29	0.0379 (10)	0.0204 (9)	0.0194 (9)	−0.0003 (8)	0.0076 (7)	−0.0004 (7)
C30	0.0345 (10)	0.0270 (9)	0.0238 (9)	0.0088 (9)	0.0125 (8)	0.0012 (8)
C31	0.0239 (9)	0.0298 (10)	0.0295 (10)	0.0021 (8)	0.0059 (7)	0.0024 (8)
C32	0.0260 (9)	0.0240 (9)	0.0225 (9)	0.0014 (8)	0.0032 (7)	−0.0008 (7)
N1	0.0217 (7)	0.0208 (7)	0.0153 (7)	−0.0017 (6)	0.0006 (5)	−0.0010 (6)
N2	0.0382 (9)	0.0267 (8)	0.0182 (7)	0.0030 (7)	−0.0063 (6)	−0.0037 (6)
N3	0.0231 (7)	0.0211 (7)	0.0165 (7)	0.0009 (6)	0.0003 (6)	0.0000 (6)
N4	0.0265 (8)	0.0247 (8)	0.0201 (7)	0.0031 (7)	0.0015 (6)	0.0025 (6)
N5	0.0269 (8)	0.0261 (8)	0.0203 (7)	0.0038 (7)	0.0023 (6)	0.0023 (6)

Geometric parameters (Å, º) top

B1—C15	1.621 (2)	C15—C20	1.401 (2)
B1—C21	1.623 (2)	C16—C17	1.387 (2)
B1—C27	1.631 (2)	C16—H12	0.9500
B1—N1	1.636 (2)	C17—C18	1.383 (3)
C1—N1	1.312 (2)	C17—H13	0.9500
C1—N3	1.349 (2)	C18—C19	1.385 (3)
C1—H1	0.9500	C18—H14	0.9500
C2—N2	1.302 (2)	C19—C20	1.387 (2)
C2—N3	1.363 (2)	C19—H15	0.9500
C2—H2	0.9500	C20—H16	0.9500
C3—C4	1.388 (2)	C21—C22	1.400 (2)
C3—C8	1.385 (2)	C21—C26	1.404 (2)
C3—N3	1.444 (2)	C22—H17	0.9500
C4—C5	1.383 (2)	C22—C23	1.385 (2)
C4—H3	0.9500	C23—C24	1.391 (2)
C5—C6	1.393 (2)	C23—H18	0.9500
C5—H4	0.9500	C24—C25	1.387 (2)
C6—C7	1.394 (2)	C24—H19	0.9500
C6—N4	1.428 (2)	C25—C26	1.390 (2)
C7—H5	0.9500	C25—H20	0.9500
C7—C8	1.381 (2)	C26—H21	0.9500
C8—H6	0.9500	C27—C28	1.408 (2)
C9—C10	1.392 (2)	C27—C32	1.393 (2)
C9—C14	1.393 (2)	C28—C29	1.384 (2)
C9—N5	1.433 (2)	C28—H22	0.9500
C10—C11	1.380 (2)	C29—C30	1.392 (3)
C10—H7	0.9500	C29—H23	0.9500
C11—C12	1.393 (3)	C30—C31	1.377 (3)
C11—H8	0.9500	C30—H24	0.9500
C12—C13	1.383 (3)	C31—C32	1.394 (2)
C12—H9	0.9500	C31—H25	0.9500
C13—C14	1.384 (3)	C32—H26	0.9500
C13—H10	0.9500	N1—N2	1.3787 (18)
C14—H11	0.9500	N4—N5	1.2563 (19)
C15—C16	1.398 (2)

B1—C15—C16	121.02 (14)	C15—C20—C19	122.11 (17)
B1—C15—C20	122.99 (15)	C15—C20—H16	118.9
B1—C21—C22	122.41 (15)	C16—C15—C20	115.98 (15)
B1—C21—C26	121.19 (14)	C16—C17—C18	119.75 (17)
B1—C27—C32	122.56 (15)	C16—C17—H13	120.1
B1—C27—C28	121.70 (15)	C17—C16—H12	118.7
B1—N1—C1	129.79 (13)	C17—C18—C19	119.48 (16)
B1—N1—N2	120.24 (13)	C17—C18—H14	120.3
C1—N1—N2	109.25 (13)	C18—C17—H13	120.1
C1—N3—C2	104.76 (14)	C18—C19—C20	120.08 (17)
C1—N3—C3	129.28 (14)	C18—C19—H15	120.0
C2—N2—N1	104.99 (14)	C19—C18—H14	120.3
C2—N3—C3	125.84 (14)	C19—C20—H16	118.9
C3—C4—C5	118.81 (16)	C20—C19—H15	120.0
C3—C4—H3	120.6	C21—B1—C27	112.21 (14)
C3—C8—C7	119.23 (15)	C21—B1—N1	105.60 (12)
C3—C8—H6	120.4	C21—C22—C23	122.48 (16)
C4—C3—C8	121.50 (16)	C21—C22—H17	118.8
C4—C3—N3	118.53 (15)	C21—C26—C25	122.20 (16)
C4—C5—C6	120.56 (16)	C21—C26—H21	118.9
C4—C5—H4	119.7	C22—C21—C26	116.02 (15)
C5—C4—H3	120.6	C22—C23—C24	120.08 (16)
C5—C6—C7	119.60 (16)	C22—C23—H18	120.0
C5—C6—N4	115.79 (14)	C23—C22—H17	118.8
C6—C5—H4	119.7	C23—C24—C25	119.10 (16)
C6—C7—C8	120.25 (16)	C23—C24—H19	120.4
C6—C7—H5	119.9	C24—C23—H18	120.0
C6—N4—N5	114.42 (14)	C24—C25—C26	120.12 (16)
C7—C6—N4	124.60 (15)	C24—C25—H20	119.9
C7—C8—H6	120.4	C25—C24—H19	120.4
C8—C3—N3	119.91 (14)	C25—C26—H21	118.9
C8—C7—H5	119.9	C26—C25—H20	119.9
C9—C10—C11	119.59 (17)	C27—B1—N1	107.85 (13)
C9—C10—H7	120.2	C27—C28—C29	122.30 (16)
C9—C14—C13	119.91 (17)	C27—C28—H22	118.9
C9—C14—H11	120.0	C27—C32—C31	122.65 (17)
C9—N5—N4	113.92 (14)	C27—C32—H26	118.7
C10—C9—C14	120.07 (16)	C28—C27—C32	115.62 (15)
C10—C9—N5	124.35 (16)	C28—C29—C30	120.25 (17)
C10—C11—C12	120.43 (18)	C28—C29—H23	119.9
C10—C11—H8	119.8	C29—C28—H22	118.9
C11—C10—H7	120.2	C29—C30—C31	119.00 (16)
C11—C12—C13	119.84 (18)	C29—C30—H24	120.5
C11—C12—H9	120.1	C30—C29—H23	119.9
C12—C11—H8	119.8	C30—C31—C32	120.17 (17)
C12—C13—C14	120.13 (18)	C30—C31—H25	119.9
C12—C13—H10	119.9	C31—C30—H24	120.5
C13—C12—H9	120.1	C31—C32—H26	118.7
C13—C14—H11	120.0	C32—C31—H25	119.9
C14—C9—N5	115.58 (15)	N1—C1—N3	109.09 (14)
C14—C13—H10	119.9	N1—C1—H1	125.5
C15—B1—C21	110.99 (13)	N2—C2—N3	111.91 (15)
C15—B1—C27	113.89 (14)	N2—C2—H2	124.0
C15—B1—N1	105.67 (13)	N3—C1—H1	125.5
C15—C16—C17	122.59 (16)	N3—C2—H2	124.0
C15—C16—H12	118.7

B1—C15—C16—C17	179.90 (15)	C20—C15—B1—C21	−9.8 (2)
B1—C15—C20—C19	−179.44 (15)	C20—C15—B1—C27	118.01 (17)
B1—C21—C22—C23	173.63 (15)	C20—C15—B1—N1	−123.80 (16)
B1—C21—C26—C25	−173.56 (15)	C20—C15—C16—C17	0.9 (2)
B1—C27—C32—C31	−176.03 (16)	C20—C19—C18—C17	0.6 (3)
B1—N1—C1—N3	170.60 (14)	C22—C21—B1—C15	−75.75 (19)
B1—N1—N2—C2	−171.42 (15)	C22—C21—B1—C27	155.54 (15)
C1—N1—B1—C15	22.6 (2)	C22—C21—B1—N1	38.3 (2)
C1—N1—B1—C21	−95.12 (19)	C22—C21—C26—C25	−0.5 (2)
C1—N1—B1—C27	144.72 (16)	C22—C23—C24—C25	−0.5 (3)
C1—N1—N2—C2	−0.18 (19)	C24—C23—C22—C21	−0.2 (3)
C1—N3—C2—N2	0.4 (2)	C24—C25—C26—C21	−0.2 (3)
C1—N3—C3—C4	−156.01 (17)	C26—C21—B1—C15	96.88 (17)
C1—N3—C3—C8	26.6 (3)	C26—C21—B1—C27	−31.8 (2)
C2—N3—C1—N1	−0.54 (18)	C26—C21—B1—N1	−149.07 (14)
C2—N3—C3—C4	28.5 (3)	C26—C21—C22—C23	0.6 (2)
C2—N3—C3—C8	−148.83 (17)	C26—C25—C24—C23	0.6 (3)
C3—C4—C5—C6	−1.8 (3)	C27—C28—C29—C30	1.3 (3)
C3—C8—C7—C6	−2.0 (3)	C28—C27—B1—C15	−176.33 (14)
C3—N3—C1—N1	−176.73 (15)	C28—C27—B1—C21	−49.2 (2)
C3—N3—C2—N2	176.80 (15)	C28—C27—B1—N1	66.73 (19)
C5—C6—C7—C8	1.7 (3)	C28—C27—C32—C31	0.1 (2)
C6—N4—N5—C9	178.72 (14)	C29—C28—C27—B1	175.07 (15)
C7—C6—C5—C4	0.2 (3)	C29—C28—C27—C32	−1.1 (2)
C7—C8—C3—C4	0.4 (3)	C30—C31—C32—C27	0.7 (3)
C7—C8—C3—N3	177.64 (15)	C31—C30—C29—C28	−0.4 (3)
C8—C3—C4—C5	1.5 (3)	C32—C27—B1—C15	−0.4 (2)
C10—C9—C14—C13	−1.7 (3)	C32—C27—B1—C21	126.77 (17)
C10—C9—N5—N4	7.0 (2)	C32—C27—B1—N1	−117.34 (16)
C10—C11—C12—C13	−1.0 (3)	C32—C31—C30—C29	−0.6 (3)
C12—C11—C10—C9	0.1 (3)	N1—N2—C2—N3	−0.2 (2)
C12—C13—C14—C9	0.8 (3)	N2—N1—B1—C15	−168.22 (13)
C14—C9—C10—C11	1.3 (3)	N2—N1—B1—C21	74.09 (17)
C14—C9—N5—N4	−173.24 (16)	N2—N1—B1—C27	−46.06 (19)
C14—C13—C12—C11	0.6 (3)	N2—N1—C1—N3	0.46 (18)
C15—C20—C19—C18	−0.3 (3)	N3—C3—C4—C5	−175.80 (16)
C16—C15—B1—C21	171.30 (14)	N4—C6—C5—C4	178.77 (16)
C16—C15—B1—C27	−60.91 (19)	N4—C6—C7—C8	−176.73 (15)
C16—C15—B1—N1	57.29 (18)	N5—C9—C10—C11	−178.98 (16)
C16—C15—C20—C19	−0.5 (2)	N5—C9—C14—C13	178.52 (17)
C16—C17—C18—C19	−0.2 (3)	N5—N4—C6—C5	166.55 (16)
C18—C17—C16—C15	−0.6 (2)	N5—N4—C6—C7	−15.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H3···Cg1ⁱ	0.95	2.91	3.822 (2)	162

Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₃₂H₂₆BN₅
M_r	491.39
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	113
a, b, c (Å)	17.4049 (6), 7.1284 (2), 21.0645 (7)
β (°)	97.0810 (15)
V (Å³)	2593.52 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.40 × 0.20 × 0.10

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (Higashi, 2001)
T_min, T_max	0.971, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	19971, 5668, 4068
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.138, 1.03
No. of reflections	5668
No. of parameters	343
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.27

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Yadokari-XG (Wakita, 2000).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H3···Cg1ⁱ	0.95	2.91	3.822 (2)	162

Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.

Acknowledgements

This work was supported by the project `Development of Molecular Devices in Ferroelectric Metallomesogens' in 2006 of the New Energy and Industrial Technology Development Organization (NEDO) of Japan and by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology of the Japanese Governement (No. 20350028).

References

Higashi, T. (2001). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rasmussen, P. H., Ramanujam, P. S., Hvilsted, S. & Berg, R. H. (1999). J. Am. Chem. Soc. 121, 4738–4743. Web of Science CrossRef CAS Google Scholar
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation,Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wakita, K. (2000). Yadokari-XG. Department of Chemistry, Graduate School of Science, University of Tokyo, Japan. Google Scholar