organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

2,3,5-Tri­phenyl-2H-tetra­zol-3-ium tetra­phenyl­borate

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia
*Correspondence e-mail: hkfun@usm.my

(Received 19 July 2012; accepted 20 July 2012; online 28 July 2012)

In the title salt, C19H15N4+·C24H20B, the tetra­phenyl­borate anion is in a tetra­hedral geometry around the B atom [C—B—C angles of 107.10 (9)–111.79 (9)°]. In the cation, the tetra­zole ring makes dihedral angles of 3.04 (7), 51.75 (7) and 51.13 (7)° with the attached phenyl rings. In the crystal, C—H⋯π inter­actions link the cations and anions into ion pairs.

Related literature

For applications of tetra­phenyl borate, see: Mostafa (2007[Mostafa, G. A. H. (2007). Ann. Chim. 97, 1247-1256.]); Mostafa & Al-Majed (2008[Mostafa, G. A. E. & Al-Majed, A. (2008). J. Pharm. Biomed. Anal. 48, 57-61.]); Mohamed et al. (2010[Mohamed, G. G., Ali, T. A., El-Shahat, M. F., Al-Sabagh, A. M., Migahed, M. A. & Khaled, E. (2010). Anal. Chim. Acta, 673, 79-87.], 2011[Mohamed, G. G., El-shahat, M. F., Al-Sabagh, A. M., Migahed, M. A. & Ali, T. A. (2011). Analyst, 136, 1488-1495.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C19H15N4+·C24H20B

  • Mr = 618.56

  • Monoclinic, P 21 /c

  • a = 9.8809 (1) Å

  • b = 22.6572 (3) Å

  • c = 16.0090 (2) Å

  • β = 110.441 (1)°

  • V = 3358.31 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 100 K

  • 0.32 × 0.31 × 0.22 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.978, Tmax = 0.985

  • 37785 measured reflections

  • 9808 independent reflections

  • 7628 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.121

  • S = 1.03

  • 9808 reflections

  • 433 parameters

  • H-atom parameters constrained

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C38–C43 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C10—H10ACg1i 0.95 2.93 3.7784 (15) 149
Symmetry code: (i) -x+2, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Tetraphenl borate reacted with triphenyltetrazolium chloride to form ion-associate complex which is used as an electroactive material for the determination of triphenyltetrazolium chloride (Mostafa, 2007; Mostafa & Al-Majed, 2008). Furthermore, tetraphenyl borate is also used as screen printing electrode (Mohamed et al., 2010, 2011).

The molecular structure of the title compound is shown in Fig. 1. The asymmetric unit of the title compound, C19H15N4+.C24H20B-, consists of a 2,3,5-triphenyl-2H-tetrazol-3-ium cation and a tetraphenylborate anion. The tetraphenylborate anion is in a tetrahedral coordination geometry with B—C distances of 1.6483 (17)–1.6529 (18) Å and C—B—C tetrahedral angles of 107.10 (9)–111.79 (9)°. The dihedral angles between the phenyl rings [C20–C25 = A; C26–C31 = B; C32–C37 = C and C38–C43 = D] are A/B = 87.74 (6)°, A/C = 80.72 (6)°, A/D = 64.32 (6)°, B/C = 68.66 (6)°, B/D = 58.60 (6)° and C/D = 55.52 (7)°. In the cation, the tetrazole ring [N1–N4/C1; r.m.s. deviation = 0.004 Å] makes dihedral angles of 3.04 (7), 51.75 (7) and 51.13 (7)° with the attached C2–C7 (E), C8–C13 (F) and C14–C19 (G) phenyl rings, respectively. The dihedral angles between E and F rings, E and G rings, and F and G rings are 48.95 (7), 49.48 (7) and 59.49 (7)°, respectively.

In the crystal, no significant hydrogen bonds are observed, but a C—H···π interaction (Table 1) occurs, involving Cg1 which is the centroid of the C38–C43 ring.

Related literature top

For applications of tetraphenyl borate, see: Mostafa (2007); Mostafa & Al-Majed (2008); Mohamed et al. (2010, 2011). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

Upon the addition of triphenyltetrazolium chloride solution (50 ml, 1×10-2 M) to a solution of sodium tetraphenyl borate (50 ml), a whitish precipitate was formed. The precipitate was filtered off, washed with cold deionized water until no chloride ion was detected in the washing solution. The precipitate was dried under vacuum to give the title ion-pairs complex. Yellow blocks suitable for an X-ray structural analysis were obtained by slow evaporation from ethanol.

Refinement top

All H atoms were positioned geometrically (C—H = 0.95 Å) and refined using a riding model with Uiso(H) = 1.2Ueq(C). Two outliers, (5 24 8) and (5 18 5) were omitted in the final refinement.

Structure description top

Tetraphenl borate reacted with triphenyltetrazolium chloride to form ion-associate complex which is used as an electroactive material for the determination of triphenyltetrazolium chloride (Mostafa, 2007; Mostafa & Al-Majed, 2008). Furthermore, tetraphenyl borate is also used as screen printing electrode (Mohamed et al., 2010, 2011).

The molecular structure of the title compound is shown in Fig. 1. The asymmetric unit of the title compound, C19H15N4+.C24H20B-, consists of a 2,3,5-triphenyl-2H-tetrazol-3-ium cation and a tetraphenylborate anion. The tetraphenylborate anion is in a tetrahedral coordination geometry with B—C distances of 1.6483 (17)–1.6529 (18) Å and C—B—C tetrahedral angles of 107.10 (9)–111.79 (9)°. The dihedral angles between the phenyl rings [C20–C25 = A; C26–C31 = B; C32–C37 = C and C38–C43 = D] are A/B = 87.74 (6)°, A/C = 80.72 (6)°, A/D = 64.32 (6)°, B/C = 68.66 (6)°, B/D = 58.60 (6)° and C/D = 55.52 (7)°. In the cation, the tetrazole ring [N1–N4/C1; r.m.s. deviation = 0.004 Å] makes dihedral angles of 3.04 (7), 51.75 (7) and 51.13 (7)° with the attached C2–C7 (E), C8–C13 (F) and C14–C19 (G) phenyl rings, respectively. The dihedral angles between E and F rings, E and G rings, and F and G rings are 48.95 (7), 49.48 (7) and 59.49 (7)°, respectively.

In the crystal, no significant hydrogen bonds are observed, but a C—H···π interaction (Table 1) occurs, involving Cg1 which is the centroid of the C38–C43 ring.

For applications of tetraphenyl borate, see: Mostafa (2007); Mostafa & Al-Majed (2008); Mohamed et al. (2010, 2011). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with atom labels and 50% probability displacement ellipsoids.
2,3,5-Triphenyl-2H-tetrazol-3-ium tetraphenylborate top
Crystal data top
C19H15N4+·C24H20BF(000) = 1304
Mr = 618.56Dx = 1.223 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9953 reflections
a = 9.8809 (1) Åθ = 2.3–29.9°
b = 22.6572 (3) ŵ = 0.07 mm1
c = 16.0090 (2) ÅT = 100 K
β = 110.441 (1)°Block, yellow
V = 3358.31 (7) Å30.32 × 0.31 × 0.22 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
9808 independent reflections
Radiation source: fine-focus sealed tube7628 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
φ and ω scansθmax = 30.1°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1313
Tmin = 0.978, Tmax = 0.985k = 3115
37785 measured reflectionsl = 1922
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0506P)2 + 1.1876P]
where P = (Fo2 + 2Fc2)/3
9808 reflections(Δ/σ)max = 0.001
433 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C19H15N4+·C24H20BV = 3358.31 (7) Å3
Mr = 618.56Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.8809 (1) ŵ = 0.07 mm1
b = 22.6572 (3) ÅT = 100 K
c = 16.0090 (2) Å0.32 × 0.31 × 0.22 mm
β = 110.441 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
9808 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
7628 reflections with I > 2σ(I)
Tmin = 0.978, Tmax = 0.985Rint = 0.029
37785 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.121H-atom parameters constrained
S = 1.03Δρmax = 0.33 e Å3
9808 reflectionsΔρmin = 0.25 e Å3
433 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
xyzUiso*/Ueq
B10.80855 (14)0.91994 (6)0.75446 (9)0.0166 (2)
N10.84759 (11)0.86398 (5)0.23476 (7)0.0195 (2)
N20.97900 (11)0.84218 (4)0.26305 (7)0.0180 (2)
N30.99069 (11)0.80074 (4)0.20630 (7)0.0182 (2)
N40.86703 (11)0.79398 (5)0.14081 (7)0.0193 (2)
C10.78000 (13)0.83373 (5)0.15918 (8)0.0183 (2)
C20.62910 (12)0.84201 (5)0.10218 (8)0.0192 (2)
C30.57066 (14)0.80618 (6)0.02706 (9)0.0261 (3)
H3A0.62790.77650.01370.031*
C40.42804 (15)0.81438 (7)0.02773 (9)0.0307 (3)
H4A0.38730.79020.07890.037*
C50.34501 (14)0.85772 (7)0.00796 (10)0.0309 (3)
H5A0.24730.86300.04550.037*
C60.40334 (14)0.89346 (7)0.06610 (10)0.0300 (3)
H6A0.34580.92330.07890.036*
C70.54578 (14)0.88581 (6)0.12175 (9)0.0247 (3)
H7A0.58600.91020.17270.030*
C81.09045 (12)0.85755 (5)0.34642 (8)0.0185 (2)
C91.12262 (13)0.91679 (6)0.36390 (8)0.0212 (2)
H9A1.07470.94640.32210.025*
C101.22789 (13)0.93117 (6)0.44512 (9)0.0241 (3)
H10A1.25280.97130.45950.029*
C111.29656 (14)0.88727 (7)0.50507 (9)0.0270 (3)
H11A1.36830.89760.56030.032*
C121.26162 (15)0.82821 (7)0.48527 (9)0.0283 (3)
H12A1.30990.79850.52690.034*
C131.15675 (14)0.81254 (6)0.40508 (8)0.0228 (3)
H13A1.13120.77240.39080.027*
C141.11995 (12)0.76850 (5)0.21228 (8)0.0189 (2)
C151.24583 (13)0.79961 (6)0.22342 (9)0.0239 (3)
H15A1.24870.84140.22770.029*
C161.36759 (14)0.76719 (7)0.22813 (9)0.0282 (3)
H16A1.45580.78700.23570.034*
C171.36125 (14)0.70611 (6)0.22188 (9)0.0279 (3)
H17A1.44570.68430.22660.034*
C181.23252 (14)0.67671 (6)0.20882 (9)0.0273 (3)
H18A1.22890.63490.20340.033*
C191.10881 (14)0.70779 (6)0.20366 (9)0.0232 (3)
H19A1.01990.68810.19460.028*
C200.64315 (12)0.93994 (5)0.74430 (8)0.0173 (2)
C210.56120 (13)0.97844 (6)0.67707 (8)0.0219 (2)
H21A0.59870.99010.63240.026*
C220.42720 (14)1.00029 (6)0.67289 (9)0.0264 (3)
H22A0.37531.02620.62590.032*
C230.36946 (13)0.98437 (6)0.73711 (10)0.0272 (3)
H23A0.27800.99900.73450.033*
C240.44726 (14)0.94681 (6)0.80501 (10)0.0268 (3)
H24A0.40940.93580.84980.032*
C250.58108 (13)0.92496 (6)0.80817 (9)0.0221 (2)
H25A0.63210.89900.85520.026*
C260.91901 (12)0.97161 (5)0.81252 (7)0.0166 (2)
C270.87021 (13)1.02357 (5)0.84049 (8)0.0184 (2)
H27A0.76931.03110.82010.022*
C280.96281 (13)1.06457 (5)0.89671 (8)0.0209 (2)
H28A0.92431.09890.91410.025*
C291.11130 (13)1.05563 (6)0.92752 (8)0.0220 (2)
H29A1.17481.08300.96710.026*
C301.16490 (13)1.00586 (6)0.89918 (8)0.0221 (2)
H30A1.26620.99950.91810.027*
C311.07066 (13)0.96529 (5)0.84317 (8)0.0191 (2)
H31A1.11030.93170.82460.023*
C320.84247 (12)0.85738 (5)0.81111 (8)0.0168 (2)
C330.93272 (13)0.85443 (5)0.90081 (8)0.0200 (2)
H33A0.98800.88830.92720.024*
C340.94493 (15)0.80416 (6)0.95301 (9)0.0249 (3)
H34A1.00900.80411.01320.030*
C350.86451 (14)0.75428 (6)0.91792 (9)0.0255 (3)
H35A0.86990.72040.95390.031*
C360.77569 (13)0.75493 (5)0.82884 (9)0.0234 (3)
H36A0.72050.72090.80320.028*
C370.76686 (13)0.80496 (5)0.77680 (8)0.0210 (2)
H37A0.70740.80370.71560.025*
C380.82089 (13)0.91126 (5)0.65512 (8)0.0186 (2)
C390.93787 (14)0.93094 (6)0.63216 (9)0.0224 (2)
H39A1.01600.94990.67650.027*
C400.94472 (16)0.92393 (6)0.54703 (9)0.0295 (3)
H40A1.02620.93820.53470.035*
C410.83374 (17)0.89645 (6)0.48087 (9)0.0319 (3)
H41A0.83780.89170.42280.038*
C420.71608 (16)0.87582 (7)0.50041 (9)0.0312 (3)
H42A0.63900.85660.45560.037*
C430.71068 (14)0.88322 (6)0.58572 (8)0.0248 (3)
H43A0.62890.86870.59750.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
B10.0146 (6)0.0176 (6)0.0184 (6)0.0008 (5)0.0070 (5)0.0009 (5)
N10.0170 (5)0.0187 (5)0.0225 (5)0.0009 (4)0.0065 (4)0.0021 (4)
N20.0173 (5)0.0168 (5)0.0199 (5)0.0006 (4)0.0063 (4)0.0002 (4)
N30.0160 (4)0.0182 (5)0.0205 (5)0.0000 (4)0.0063 (4)0.0000 (4)
N40.0159 (5)0.0190 (5)0.0220 (5)0.0000 (4)0.0052 (4)0.0008 (4)
C10.0180 (5)0.0167 (5)0.0213 (5)0.0002 (4)0.0080 (4)0.0023 (4)
C20.0158 (5)0.0194 (5)0.0222 (6)0.0001 (4)0.0062 (4)0.0042 (5)
C30.0217 (6)0.0246 (6)0.0287 (6)0.0013 (5)0.0047 (5)0.0024 (5)
C40.0238 (6)0.0338 (8)0.0276 (7)0.0025 (6)0.0004 (5)0.0000 (6)
C50.0173 (6)0.0377 (8)0.0334 (7)0.0025 (6)0.0035 (5)0.0106 (6)
C60.0216 (6)0.0312 (7)0.0381 (7)0.0076 (6)0.0114 (6)0.0061 (6)
C70.0212 (6)0.0254 (6)0.0278 (6)0.0024 (5)0.0090 (5)0.0012 (5)
C80.0154 (5)0.0211 (6)0.0184 (5)0.0010 (4)0.0053 (4)0.0000 (4)
C90.0225 (6)0.0198 (6)0.0232 (6)0.0008 (5)0.0101 (5)0.0011 (5)
C100.0226 (6)0.0248 (6)0.0268 (6)0.0053 (5)0.0111 (5)0.0061 (5)
C110.0204 (6)0.0350 (7)0.0234 (6)0.0004 (5)0.0049 (5)0.0063 (5)
C120.0271 (7)0.0316 (7)0.0216 (6)0.0069 (6)0.0028 (5)0.0021 (5)
C130.0239 (6)0.0203 (6)0.0230 (6)0.0010 (5)0.0065 (5)0.0019 (5)
C140.0153 (5)0.0213 (6)0.0199 (5)0.0035 (4)0.0057 (4)0.0012 (5)
C150.0197 (6)0.0217 (6)0.0301 (6)0.0001 (5)0.0084 (5)0.0039 (5)
C160.0175 (6)0.0324 (7)0.0348 (7)0.0010 (5)0.0094 (5)0.0059 (6)
C170.0217 (6)0.0324 (7)0.0302 (7)0.0089 (5)0.0097 (5)0.0045 (6)
C180.0260 (6)0.0223 (6)0.0331 (7)0.0051 (5)0.0100 (5)0.0001 (5)
C190.0196 (6)0.0209 (6)0.0286 (6)0.0002 (5)0.0077 (5)0.0007 (5)
C200.0154 (5)0.0156 (5)0.0207 (5)0.0015 (4)0.0061 (4)0.0042 (4)
C210.0192 (6)0.0236 (6)0.0223 (6)0.0022 (5)0.0067 (5)0.0013 (5)
C220.0191 (6)0.0250 (6)0.0298 (7)0.0047 (5)0.0017 (5)0.0043 (5)
C230.0145 (5)0.0241 (6)0.0431 (8)0.0005 (5)0.0103 (5)0.0100 (6)
C240.0224 (6)0.0234 (6)0.0411 (7)0.0021 (5)0.0193 (6)0.0044 (6)
C250.0204 (6)0.0195 (6)0.0290 (6)0.0005 (5)0.0121 (5)0.0011 (5)
C260.0166 (5)0.0169 (5)0.0174 (5)0.0001 (4)0.0071 (4)0.0023 (4)
C270.0176 (5)0.0189 (5)0.0185 (5)0.0014 (4)0.0062 (4)0.0003 (4)
C280.0238 (6)0.0180 (5)0.0215 (6)0.0011 (5)0.0087 (5)0.0001 (5)
C290.0222 (6)0.0206 (6)0.0224 (6)0.0065 (5)0.0068 (5)0.0005 (5)
C300.0154 (5)0.0247 (6)0.0259 (6)0.0018 (5)0.0069 (5)0.0029 (5)
C310.0175 (5)0.0173 (5)0.0242 (6)0.0007 (4)0.0093 (5)0.0020 (5)
C320.0143 (5)0.0176 (5)0.0206 (5)0.0009 (4)0.0089 (4)0.0020 (4)
C330.0217 (6)0.0169 (5)0.0223 (6)0.0015 (5)0.0088 (5)0.0005 (4)
C340.0299 (7)0.0217 (6)0.0225 (6)0.0003 (5)0.0085 (5)0.0020 (5)
C350.0298 (7)0.0170 (6)0.0336 (7)0.0010 (5)0.0162 (6)0.0039 (5)
C360.0211 (6)0.0153 (5)0.0371 (7)0.0020 (5)0.0145 (5)0.0051 (5)
C370.0169 (5)0.0199 (6)0.0263 (6)0.0005 (5)0.0075 (5)0.0044 (5)
C380.0195 (5)0.0177 (5)0.0196 (5)0.0061 (4)0.0080 (4)0.0018 (4)
C390.0248 (6)0.0198 (6)0.0255 (6)0.0063 (5)0.0124 (5)0.0039 (5)
C400.0383 (8)0.0256 (7)0.0337 (7)0.0118 (6)0.0239 (6)0.0081 (6)
C410.0489 (9)0.0290 (7)0.0235 (6)0.0183 (6)0.0196 (6)0.0044 (5)
C420.0385 (8)0.0314 (7)0.0212 (6)0.0101 (6)0.0071 (6)0.0027 (5)
C430.0248 (6)0.0271 (6)0.0224 (6)0.0040 (5)0.0082 (5)0.0019 (5)
Geometric parameters (Å, º) top
B1—C201.6483 (17)C20—C211.4022 (17)
B1—C261.6483 (18)C20—C251.4054 (17)
B1—C381.6487 (17)C21—C221.3931 (17)
B1—C321.6529 (18)C21—H21A0.9500
N1—N21.3132 (14)C22—C231.387 (2)
N1—C11.3474 (15)C22—H22A0.9500
N2—N31.3392 (14)C23—C241.383 (2)
N2—C81.4452 (15)C23—H23A0.9500
N3—N41.3118 (14)C24—C251.3962 (17)
N3—C141.4452 (15)C24—H24A0.9500
N4—C11.3468 (16)C25—H25A0.9500
C1—C21.4631 (16)C26—C271.4036 (16)
C2—C71.3930 (18)C26—C311.4117 (16)
C2—C31.3977 (18)C27—C281.3911 (17)
C3—C41.3880 (18)C27—H27A0.9500
C3—H3A0.9500C28—C291.3898 (17)
C4—C51.385 (2)C28—H28A0.9500
C4—H4A0.9500C29—C301.3878 (18)
C5—C61.384 (2)C29—H29A0.9500
C5—H5A0.9500C30—C311.3903 (17)
C6—C71.3889 (18)C30—H30A0.9500
C6—H6A0.9500C31—H31A0.9500
C7—H7A0.9500C32—C331.4027 (16)
C8—C91.3853 (17)C32—C371.4083 (17)
C8—C131.3862 (17)C33—C341.3928 (17)
C9—C101.3908 (18)C33—H33A0.9500
C9—H9A0.9500C34—C351.3828 (18)
C10—C111.3841 (19)C34—H34A0.9500
C10—H10A0.9500C35—C361.3893 (19)
C11—C121.391 (2)C35—H35A0.9500
C11—H11A0.9500C36—C371.3915 (18)
C12—C131.3852 (18)C36—H36A0.9500
C12—H12A0.9500C37—H37A0.9500
C13—H13A0.9500C38—C391.4024 (17)
C14—C191.3828 (17)C38—C431.4068 (18)
C14—C151.3860 (17)C39—C401.3971 (18)
C15—C161.3889 (18)C39—H39A0.9500
C15—H15A0.9500C40—C411.379 (2)
C16—C171.387 (2)C40—H40A0.9500
C16—H16A0.9500C41—C421.386 (2)
C17—C181.3854 (19)C41—H41A0.9500
C17—H17A0.9500C42—C431.3953 (18)
C18—C191.3880 (18)C42—H42A0.9500
C18—H18A0.9500C43—H43A0.9500
C19—H19A0.9500
C20—B1—C26107.39 (9)C21—C20—B1122.26 (10)
C20—B1—C38110.02 (9)C25—C20—B1122.10 (10)
C26—B1—C38111.79 (9)C22—C21—C20122.85 (12)
C20—B1—C32107.10 (9)C22—C21—H21A118.6
C26—B1—C32109.40 (9)C20—C21—H21A118.6
C38—B1—C32110.96 (9)C23—C22—C21120.14 (13)
N2—N1—C1103.80 (10)C23—C22—H22A119.9
N1—N2—N3109.81 (9)C21—C22—H22A119.9
N1—N2—C8124.79 (10)C24—C23—C22118.90 (12)
N3—N2—C8125.24 (10)C24—C23—H23A120.6
N4—N3—N2110.31 (9)C22—C23—H23A120.6
N4—N3—C14123.29 (10)C23—C24—C25120.39 (12)
N2—N3—C14126.37 (10)C23—C24—H24A119.8
N3—N4—C1103.59 (10)C25—C24—H24A119.8
N4—C1—N1112.48 (10)C24—C25—C20122.45 (12)
N4—C1—C2122.61 (11)C24—C25—H25A118.8
N1—C1—C2124.92 (11)C20—C25—H25A118.8
C7—C2—C3120.54 (11)C27—C26—C31114.55 (11)
C7—C2—C1120.31 (11)C27—C26—B1122.82 (10)
C3—C2—C1119.14 (11)C31—C26—B1122.51 (10)
C4—C3—C2119.29 (13)C28—C27—C26123.02 (11)
C4—C3—H3A120.4C28—C27—H27A118.5
C2—C3—H3A120.4C26—C27—H27A118.5
C5—C4—C3120.14 (13)C29—C28—C27120.44 (12)
C5—C4—H4A119.9C29—C28—H28A119.8
C3—C4—H4A119.9C27—C28—H28A119.8
C6—C5—C4120.52 (12)C30—C29—C28118.59 (11)
C6—C5—H5A119.7C30—C29—H29A120.7
C4—C5—H5A119.7C28—C29—H29A120.7
C5—C6—C7120.11 (13)C29—C30—C31120.14 (11)
C5—C6—H6A119.9C29—C30—H30A119.9
C7—C6—H6A119.9C31—C30—H30A119.9
C6—C7—C2119.40 (13)C30—C31—C26123.20 (11)
C6—C7—H7A120.3C30—C31—H31A118.4
C2—C7—H7A120.3C26—C31—H31A118.4
C9—C8—C13123.73 (11)C33—C32—C37114.85 (11)
C9—C8—N2117.85 (11)C33—C32—B1122.48 (10)
C13—C8—N2118.41 (11)C37—C32—B1122.07 (10)
C8—C9—C10117.37 (12)C34—C33—C32122.95 (12)
C8—C9—H9A121.3C34—C33—H33A118.5
C10—C9—H9A121.3C32—C33—H33A118.5
C11—C10—C9120.36 (12)C35—C34—C33120.50 (12)
C11—C10—H10A119.8C35—C34—H34A119.7
C9—C10—H10A119.8C33—C34—H34A119.7
C10—C11—C12120.72 (12)C34—C35—C36118.41 (12)
C10—C11—H11A119.6C34—C35—H35A120.8
C12—C11—H11A119.6C36—C35—H35A120.8
C13—C12—C11120.25 (12)C35—C36—C37120.54 (12)
C13—C12—H12A119.9C35—C36—H36A119.7
C11—C12—H12A119.9C37—C36—H36A119.7
C12—C13—C8117.57 (12)C36—C37—C32122.67 (12)
C12—C13—H13A121.2C36—C37—H37A118.7
C8—C13—H13A121.2C32—C37—H37A118.7
C19—C14—C15123.73 (11)C39—C38—C43114.71 (11)
C19—C14—N3117.29 (11)C39—C38—B1124.08 (11)
C15—C14—N3118.95 (11)C43—C38—B1121.21 (11)
C14—C15—C16117.35 (12)C40—C39—C38123.01 (13)
C14—C15—H15A121.3C40—C39—H39A118.5
C16—C15—H15A121.3C38—C39—H39A118.5
C17—C16—C15120.47 (12)C41—C40—C39120.28 (13)
C17—C16—H16A119.8C41—C40—H40A119.9
C15—C16—H16A119.8C39—C40—H40A119.9
C18—C17—C16120.43 (12)C40—C41—C42118.92 (12)
C18—C17—H17A119.8C40—C41—H41A120.5
C16—C17—H17A119.8C42—C41—H41A120.5
C17—C18—C19120.54 (13)C41—C42—C43120.14 (13)
C17—C18—H18A119.7C41—C42—H42A119.9
C19—C18—H18A119.7C43—C42—H42A119.9
C14—C19—C18117.45 (12)C42—C43—C38122.93 (13)
C14—C19—H19A121.3C42—C43—H43A118.5
C18—C19—H19A121.3C38—C43—H43A118.5
C21—C20—C25115.27 (11)
C1—N1—N2—N30.55 (12)C38—B1—C20—C25149.98 (11)
C1—N1—N2—C8175.09 (11)C32—B1—C20—C2529.28 (15)
N1—N2—N3—N41.01 (13)C25—C20—C21—C220.38 (18)
C8—N2—N3—N4174.60 (10)B1—C20—C21—C22173.49 (11)
N1—N2—N3—C14177.07 (10)C20—C21—C22—C230.3 (2)
C8—N2—N3—C147.32 (18)C21—C22—C23—C240.2 (2)
N2—N3—N4—C10.99 (13)C22—C23—C24—C250.6 (2)
C14—N3—N4—C1177.16 (11)C23—C24—C25—C200.5 (2)
N3—N4—C1—N10.66 (13)C21—C20—C25—C240.01 (18)
N3—N4—C1—C2179.49 (11)B1—C20—C25—C24173.13 (11)
N2—N1—C1—N40.07 (13)C20—B1—C26—C273.63 (15)
N2—N1—C1—C2179.92 (11)C38—B1—C26—C27117.14 (12)
N4—C1—C2—C7176.73 (12)C32—B1—C26—C27119.54 (12)
N1—C1—C2—C73.44 (19)C20—B1—C26—C31172.03 (10)
N4—C1—C2—C32.08 (18)C38—B1—C26—C3167.20 (14)
N1—C1—C2—C3177.75 (12)C32—B1—C26—C3156.12 (14)
C7—C2—C3—C40.4 (2)C31—C26—C27—C282.43 (17)
C1—C2—C3—C4179.25 (12)B1—C26—C27—C28173.54 (11)
C2—C3—C4—C50.1 (2)C26—C27—C28—C290.57 (19)
C3—C4—C5—C60.4 (2)C27—C28—C29—C301.63 (18)
C4—C5—C6—C70.5 (2)C28—C29—C30—C311.80 (18)
C5—C6—C7—C20.1 (2)C29—C30—C31—C260.22 (19)
C3—C2—C7—C60.34 (19)C27—C26—C31—C302.26 (17)
C1—C2—C7—C6179.13 (12)B1—C26—C31—C30173.72 (11)
N1—N2—C8—C953.50 (16)C20—B1—C32—C33105.11 (12)
N3—N2—C8—C9131.52 (12)C26—B1—C32—C3310.99 (15)
N1—N2—C8—C13125.11 (13)C38—B1—C32—C33134.80 (11)
N3—N2—C8—C1349.87 (16)C20—B1—C32—C3765.54 (13)
C13—C8—C9—C100.15 (19)C26—B1—C32—C37178.36 (10)
N2—C8—C9—C10178.68 (11)C38—B1—C32—C3754.56 (14)
C8—C9—C10—C110.09 (18)C37—C32—C33—C341.34 (17)
C9—C10—C11—C120.0 (2)B1—C32—C33—C34169.93 (11)
C10—C11—C12—C130.3 (2)C32—C33—C34—C351.2 (2)
C11—C12—C13—C80.5 (2)C33—C34—C35—C362.3 (2)
C9—C8—C13—C120.44 (19)C34—C35—C36—C370.83 (19)
N2—C8—C13—C12178.96 (11)C35—C36—C37—C321.84 (19)
N4—N3—C14—C1951.05 (16)C33—C32—C37—C362.83 (17)
N2—N3—C14—C19131.10 (13)B1—C32—C37—C36168.48 (11)
N4—N3—C14—C15126.99 (13)C20—B1—C38—C39137.58 (11)
N2—N3—C14—C1550.86 (17)C26—B1—C38—C3918.35 (16)
C19—C14—C15—C161.55 (19)C32—B1—C38—C39104.08 (13)
N3—C14—C15—C16179.46 (11)C20—B1—C38—C4341.86 (15)
C14—C15—C16—C170.1 (2)C26—B1—C38—C43161.09 (11)
C15—C16—C17—C181.5 (2)C32—B1—C38—C4376.48 (13)
C16—C17—C18—C191.4 (2)C43—C38—C39—C400.58 (18)
C15—C14—C19—C181.7 (2)B1—C38—C39—C40178.89 (11)
N3—C14—C19—C18179.61 (11)C38—C39—C40—C410.2 (2)
C17—C18—C19—C140.2 (2)C39—C40—C41—C420.2 (2)
C26—B1—C20—C2184.50 (13)C40—C41—C42—C430.3 (2)
C38—B1—C20—C2137.38 (15)C41—C42—C43—C380.1 (2)
C32—B1—C20—C21158.07 (11)C39—C38—C43—C420.49 (18)
C26—B1—C20—C2588.14 (13)B1—C38—C43—C42179.00 (12)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C38–C43 ring.
D—H···AD—HH···AD···AD—H···A
C10—H10A···Cg1i0.952.933.7784 (15)149
Symmetry code: (i) x+2, y+2, z+1.

Experimental details

Crystal data
Chemical formulaC19H15N4+·C24H20B
Mr618.56
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)9.8809 (1), 22.6572 (3), 16.0090 (2)
β (°) 110.441 (1)
V3)3358.31 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.32 × 0.31 × 0.22
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.978, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections
37785, 9808, 7628
Rint0.029
(sin θ/λ)max1)0.706
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.121, 1.03
No. of reflections9808
No. of parameters433
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.25

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C38–C43 ring.
D—H···AD—HH···AD···AD—H···A
C10—H10A···Cg1i0.952.933.7784 (15)149
Symmetry code: (i) x+2, y+2, z+1.
 

Footnotes

Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC also thanks the Malaysian Government and USM for the award of a research fellowship. The authors thank the Deanship of Scientific Research at King Saud University for funding the work through the research group project No. RGP-VPP-037.

References

First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationCosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationMohamed, G. G., Ali, T. A., El-Shahat, M. F., Al-Sabagh, A. M., Migahed, M. A. & Khaled, E. (2010). Anal. Chim. Acta, 673, 79–87.  Web of Science CrossRef CAS PubMed Google Scholar
First citationMohamed, G. G., El-shahat, M. F., Al-Sabagh, A. M., Migahed, M. A. & Ali, T. A. (2011). Analyst, 136, 1488–1495.  Web of Science CrossRef CAS PubMed Google Scholar
First citationMostafa, G. A. H. (2007). Ann. Chim. 97, 1247–1256.  Web of Science CrossRef CAS Google Scholar
First citationMostafa, G. A. E. & Al-Majed, A. (2008). J. Pharm. Biomed. Anal. 48, 57–61.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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