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

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COMMUNICATIONS
ISSN: 2056-9890

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

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 21 July 2012; accepted 26 July 2012; online 1 August 2012)

The asymmetric unit of the title mol­ecular salt, C19H15N4+·I, contains four 2,3,5-triphenyl-2H-tetra­zol-3-ium cations and five iodide anions, with two of the latter lying on crystallographic inversion centres. In each cation, the tetra­zole ring is essentially planar (r.m.s. deviations = 0.004–0.007 Å). The dihedral angles between the tetra­zole ring and its three attached benzene rings in the four independent cations are: 12.9 (4), 67.0 (4), 48.1 (4); 20.8 (4), 51.1 (4), 62.3 (4); 11.4 (4), 52.3 (4), 47.3 (4) and 6.0 (4), 85.7 (4), 43.5 (4)°. A C—H⋯I hydrogen bond and C—H⋯π inter­actions are observed in the crystal.

Related literature

For the biological activity of the triphenyl­tetra­zolium ion, see: Mostafa (2007[Mostafa, G. A. E. (2007). Talanta, 71, 1449-1454.]); Hassanien et al. (2003[Hassanien, M. M., Abou-El-Sherbini, Kh. S. & Mostafa, G. A. E. (2003). Talanta, 59, 383-392.]); Abbas et al. (2001[Abbas, M. N., Mostafa, G. A. E. & Homoda, A. M. A. (2001). Talanta, 55, 647-656.]). 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+·I

  • Mr = 426.25

  • Monoclinic, P 21 /c

  • a = 9.6541 (4) Å

  • b = 30.9983 (14) Å

  • c = 24.3469 (10) Å

  • β = 97.930 (1)°

  • V = 7216.4 (5) Å3

  • Z = 16

  • Mo Kα radiation

  • μ = 1.78 mm−1

  • T = 100 K

  • 0.37 × 0.21 × 0.06 mm

Data collection
  • Bruker APEX DUO CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009)[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.] Tmin = 0.556, Tmax = 0.907

  • 71406 measured reflections

  • 16492 independent reflections

  • 13800 reflections with I > 2σ(I)

  • Rint = 0.048

Refinement
  • R[F2 > 2σ(F2)] = 0.075

  • wR(F2) = 0.172

  • S = 1.26

  • 16492 reflections

  • 868 parameters

  • H-atom parameters constrained

  • Δρmax = 5.04 e Å−3

  • Δρmin = −2.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C1C–C6C, C8C–C13C, C1A–C6A and C1D–C6D rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C19B—H19B⋯I3 0.95 3.03 3.844 (8) 145
C3A—H3AACg1i 0.95 2.87 3.636 (8) 138
C5A—H5AACg2 0.95 2.89 3.547 (9) 127
C16A—H16ACg3ii 0.95 2.85 3.657 (9) 144
C16D—H16DCg4iii 0.95 2.96 3.769 (10) 144
Symmetry codes: (i) -x+2, -y+1, -z; (ii) x-1, y, z; (iii) x+1, y, z.

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

2,3,5-Triphenyltetrazolium ion is used as indicator of bacterial dehydrogenase activity and as a reagent in colorimetric determination method for glucose dehydrogenase. It is also used as ion-pair reagent for determination of antimony in waste water (Mostafa, 2007; Hassanien et al., 2003; Abbas et al., 2001).

The molecular structure of the title compound is shown in Fig. 1. The asymmetric unit of the title compound, C19H15N4+, I-, contains four crystallographically independent 2,3,5-triphenyl-2H-tetrazol-3-ium cations, three fully occupied iodine anions (I1, I2 & I3) and two half-occupied iodine anions (I4 & I5). In the cation A, B, C and D, the tetrazole ring [N1–N4/C7] is essentially planar with r.m.s. deviations of 0.007, 0.007, 0.006 and 0.004 Å, respectively. The dihedral angles between the tetrazole ring and benzene rings [C1–C6, C8–C13 & C14–C19] are 12.9 (4), 67.0 (4) and 48.1 (4)° in cation A, 20.8 (4), 51.1 (4) and 62.3 (4)° in cation B, 11.4 (4), 52.3 (4) and 47.3 (4)° in cation C and 6.0 (4), 85.7 (4) and 43.5 (4)° in cation D.

In the crystal (Fig. 2), intermolecular C19B—H19B···I3 hydrogen bond and C—H···π interactions are observed, involving Cg1, Cg2, Cg3 and Cg4 which are the centroids of C1C–C6C, C8C–C13C, C1A–C6A and C1D–C6D rings, respectively.

Related literature top

For the biological activity of the triphenyltetrazolium ion, see: Mostafa (2007); Hassanien et al. (2003); Abbas et al. (2001). For the 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, 1X10-2 M) to a solution of potassium iodide (50 ml), a yellowish precipitate was formed. The precipitate was filtered off, washed with cold deionized water until no chloride ions were detected in the washing solution. The precipitate was dried under vacuum to give the title ion-pair complex. Orange plates were obtained by slow evaporation of an ethanol solution.

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). Ten outliers, (1 11 8), (1 16 3), (2 18 5), (0 1 22), (0 12 0), (0 5 22), (1 1 24), (2 7 7), (0 9 18) and (1 1 24) were omitted in the final refinement. The largest difference peak is 1.52 Å from atom I1.

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 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. The crystal packing of the title compound. The dashed lines represent the hydrogen bonds. For clarity sake, hydrogen atoms not involved in hydrogen bonding have been omitted.
2,3,5-Triphenyl-2H-tetrazol-3-ium iodide top
Crystal data top
C19H15N4+·IF(000) = 3360
Mr = 426.25Dx = 1.569 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9972 reflections
a = 9.6541 (4) Åθ = 2.9–32.1°
b = 30.9983 (14) ŵ = 1.78 mm1
c = 24.3469 (10) ÅT = 100 K
β = 97.930 (1)°Plate, orange
V = 7216.4 (5) Å30.37 × 0.21 × 0.06 mm
Z = 16
Data collection top
Bruker APEX DUO CCD
diffractometer
16492 independent reflections
Radiation source: fine-focus sealed tube13800 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
ϕ and ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1212
Tmin = 0.556, Tmax = 0.907k = 4040
71406 measured reflectionsl = 3131
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)] = 0.075Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172H-atom parameters constrained
S = 1.26 w = 1/[σ2(Fo2) + (0.0155P)2 + 127.6P]
where P = (Fo2 + 2Fc2)/3
16492 reflections(Δ/σ)max < 0.001
868 parametersΔρmax = 5.04 e Å3
0 restraintsΔρmin = 2.28 e Å3
Crystal data top
C19H15N4+·IV = 7216.4 (5) Å3
Mr = 426.25Z = 16
Monoclinic, P21/cMo Kα radiation
a = 9.6541 (4) ŵ = 1.78 mm1
b = 30.9983 (14) ÅT = 100 K
c = 24.3469 (10) Å0.37 × 0.21 × 0.06 mm
β = 97.930 (1)°
Data collection top
Bruker APEX DUO CCD
diffractometer
16492 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
13800 reflections with I > 2σ(I)
Tmin = 0.556, Tmax = 0.907Rint = 0.048
71406 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0750 restraints
wR(F2) = 0.172H-atom parameters constrained
S = 1.26 w = 1/[σ2(Fo2) + (0.0155P)2 + 127.6P]
where P = (Fo2 + 2Fc2)/3
16492 reflectionsΔρmax = 5.04 e Å3
868 parametersΔρmin = 2.28 e Å3
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
I10.93818 (5)0.258521 (17)0.25097 (2)0.01657 (12)
I20.57535 (5)0.489539 (17)0.22730 (2)0.01779 (12)
I30.52640 (5)0.251333 (18)0.47905 (2)0.02025 (13)
I41.00000.50000.50000.02196 (17)
I51.00000.50000.00000.0287 (2)
N1A0.8507 (6)0.2267 (2)0.0944 (3)0.0170 (14)
N2A0.7386 (6)0.2201 (2)0.1187 (3)0.0153 (13)
N3A0.6758 (6)0.2575 (2)0.1261 (3)0.0154 (13)
N4A0.7434 (6)0.2896 (2)0.1059 (3)0.0147 (13)
C1A1.0411 (8)0.2688 (3)0.0272 (3)0.0207 (17)
H1AA1.03900.23810.02750.025*
C2A1.1314 (8)0.2904 (3)0.0032 (3)0.0236 (19)
H2AA1.19220.27470.02330.028*
C3A1.1321 (8)0.3348 (3)0.0039 (3)0.0233 (19)
H3AA1.19250.34950.02530.028*
C4A1.0467 (9)0.3586 (3)0.0260 (3)0.0216 (18)
H4AA1.04940.38920.02530.026*
C5A0.9562 (8)0.3372 (3)0.0572 (3)0.0165 (16)
H5AA0.89770.35330.07800.020*
C6A0.9524 (8)0.2926 (3)0.0577 (3)0.0148 (15)
C7A0.8506 (7)0.2698 (3)0.0858 (3)0.0148 (15)
C8A0.6944 (8)0.1775 (3)0.1328 (3)0.0172 (16)
C9A0.5735 (10)0.1609 (3)0.1037 (3)0.026 (2)
H9AA0.51800.17730.07590.032*
C10A0.5358 (12)0.1190 (4)0.1166 (4)0.037 (3)
H10A0.45230.10660.09780.044*
C11A0.6195 (10)0.0951 (3)0.1565 (4)0.027 (2)
H11A0.59360.06650.16490.032*
C12A0.7401 (10)0.1130 (3)0.1841 (4)0.029 (2)
H12A0.79680.09660.21150.034*
C13A0.7799 (9)0.1545 (3)0.1723 (4)0.0241 (18)
H13A0.86370.16670.19090.029*
C14A0.5483 (7)0.2627 (3)0.1496 (3)0.0147 (15)
C15A0.4442 (8)0.2876 (3)0.1199 (4)0.0219 (18)
H15A0.45760.30110.08600.026*
C16A0.3204 (9)0.2921 (3)0.1418 (3)0.0231 (18)
H16A0.24770.30940.12290.028*
C17A0.3004 (8)0.2720 (3)0.1905 (3)0.0203 (17)
H17A0.21320.27470.20420.024*
C18A0.4077 (8)0.2476 (3)0.2201 (3)0.0195 (17)
H18A0.39430.23420.25410.023*
C19A0.5340 (8)0.2429 (3)0.1994 (3)0.0173 (16)
H19A0.60840.22660.21890.021*
N1B0.6359 (6)0.2296 (2)0.3374 (3)0.0138 (13)
N2B0.6802 (6)0.2683 (2)0.3522 (2)0.0115 (12)
N3B0.8016 (6)0.2657 (2)0.3865 (3)0.0157 (13)
N4B0.8386 (7)0.2251 (2)0.3944 (3)0.0151 (13)
C1B0.6439 (9)0.1366 (3)0.3153 (3)0.0222 (18)
H1BA0.59380.15350.28670.027*
C2B0.6349 (10)0.0917 (3)0.3136 (4)0.0254 (19)
H2BA0.57650.07820.28390.030*
C3B0.7092 (9)0.0668 (3)0.3539 (4)0.0231 (18)
H3BA0.70380.03630.35160.028*
C4B0.7924 (9)0.0864 (3)0.3981 (4)0.0244 (19)
H4BA0.84200.06930.42670.029*
C5B0.8022 (9)0.1307 (3)0.4001 (3)0.0209 (17)
H5BA0.86140.14400.42970.025*
C6B0.7271 (8)0.1562 (3)0.3596 (3)0.0122 (14)
C7B0.7345 (7)0.2032 (3)0.3648 (3)0.0131 (14)
C8B0.6083 (8)0.3072 (3)0.3318 (3)0.0150 (15)
C9B0.6795 (9)0.3391 (3)0.3069 (3)0.0201 (17)
H9BA0.77710.33690.30550.024*
C10B0.6032 (10)0.3740 (3)0.2844 (4)0.0248 (19)
H10B0.64850.39640.26710.030*
C11B0.4610 (10)0.3766 (3)0.2870 (4)0.0250 (19)
H11B0.40990.40090.27120.030*
C12B0.3925 (9)0.3448 (3)0.3120 (4)0.0246 (19)
H12B0.29490.34710.31320.030*
C13B0.4661 (8)0.3090 (3)0.3357 (3)0.0176 (16)
H13B0.42100.28700.35380.021*
C14B0.8811 (8)0.3016 (3)0.4122 (3)0.0164 (16)
C15B1.0164 (9)0.3075 (3)0.3998 (4)0.027 (2)
H15B1.05620.28830.37600.032*
C16B1.0896 (9)0.3421 (4)0.4234 (4)0.032 (2)
H16B1.18210.34720.41580.039*
C17B1.0297 (9)0.3702 (3)0.4586 (3)0.0241 (19)
H17B1.08070.39460.47380.029*
C18B0.8969 (9)0.3625 (3)0.4713 (3)0.0210 (17)
H18B0.85770.38120.49590.025*
C19B0.8205 (8)0.3274 (3)0.4481 (3)0.0197 (17)
H19B0.72950.32150.45680.024*
N1C0.8767 (7)0.5227 (2)0.1441 (3)0.0156 (13)
N2C0.8347 (7)0.4841 (2)0.1274 (3)0.0158 (13)
N3C0.7115 (7)0.4867 (2)0.0944 (3)0.0140 (13)
N4C0.6703 (7)0.5273 (2)0.0900 (3)0.0165 (14)
C1C0.8953 (9)0.6160 (3)0.1564 (3)0.0211 (17)
H1CA0.97760.59960.16760.025*
C2C0.8951 (10)0.6600 (3)0.1653 (4)0.028 (2)
H2CA0.97710.67390.18290.033*
C3C0.7753 (10)0.6838 (3)0.1485 (4)0.0243 (19)
H3CA0.77570.71420.15400.029*
C4C0.6547 (10)0.6635 (3)0.1236 (4)0.0247 (19)
H4CA0.57260.68000.11260.030*
C5C0.6532 (9)0.6196 (3)0.1146 (4)0.0224 (18)
H5CA0.57040.60580.09750.027*
C6C0.7737 (8)0.5955 (3)0.1308 (3)0.0157 (15)
C7C0.7730 (8)0.5489 (3)0.1213 (3)0.0146 (15)
C8C0.9108 (9)0.4455 (3)0.1465 (3)0.0155 (15)
C9C0.8409 (10)0.4135 (3)0.1721 (3)0.0215 (18)
H9CA0.74370.41560.17440.026*
C10C0.9187 (11)0.3784 (3)0.1941 (4)0.027 (2)
H10C0.87380.35540.21050.033*
C11C1.0619 (10)0.3766 (3)0.1923 (4)0.029 (2)
H11C1.11470.35290.20860.035*
C12C1.1282 (10)0.4091 (3)0.1668 (4)0.028 (2)
H12C1.22580.40730.16510.034*
C13C1.0522 (9)0.4445 (3)0.1437 (3)0.0201 (17)
H13C1.09660.46730.12660.024*
C14C0.6317 (8)0.4508 (3)0.0688 (3)0.0161 (16)
C15C0.4901 (9)0.4498 (3)0.0739 (4)0.027 (2)
H15C0.44650.47250.09140.033*
C16C0.4160 (10)0.4139 (4)0.0520 (4)0.032 (2)
H16C0.31950.41140.05550.038*
C17C0.4797 (9)0.3819 (3)0.0254 (3)0.0245 (19)
H17C0.42720.35760.01080.029*
C18C0.6188 (9)0.3850 (3)0.0198 (3)0.0227 (18)
H18C0.66200.36270.00160.027*
C19C0.6970 (9)0.4203 (3)0.0404 (3)0.0193 (17)
H19C0.79210.42340.03510.023*
N1D0.6524 (6)0.5202 (2)0.3844 (3)0.0157 (13)
N2D0.7624 (6)0.5296 (2)0.3600 (3)0.0161 (14)
N3D0.8316 (6)0.4933 (2)0.3514 (3)0.0142 (13)
N4D0.7692 (6)0.4598 (2)0.3707 (3)0.0141 (13)
C1D0.4534 (8)0.4737 (3)0.4414 (3)0.0205 (17)
H1DA0.44160.50400.43670.025*
C2D0.3652 (8)0.4506 (3)0.4708 (4)0.0238 (19)
H2DA0.29260.46490.48620.029*
C3D0.3834 (8)0.4068 (3)0.4776 (3)0.0222 (19)
H3DA0.32410.39120.49860.027*
C4D0.4863 (9)0.3849 (3)0.4545 (3)0.0222 (18)
H4DA0.49720.35460.45920.027*
C5D0.5737 (8)0.4080 (3)0.4242 (3)0.0186 (16)
H5DA0.64330.39340.40720.022*
C6D0.5585 (8)0.4527 (3)0.4188 (3)0.0160 (16)
C7D0.6582 (8)0.4777 (3)0.3911 (3)0.0164 (16)
C8D0.8017 (8)0.5739 (3)0.3502 (4)0.0186 (17)
C9D0.8910 (9)0.5946 (3)0.3897 (3)0.0225 (18)
H9DA0.93350.58010.42210.027*
C10D0.9173 (11)0.6380 (3)0.3806 (4)0.030 (2)
H10D0.98020.65340.40710.036*
C11D0.8547 (9)0.6591 (3)0.3342 (4)0.0262 (19)
H11D0.87220.68890.32950.031*
C12D0.7651 (9)0.6369 (3)0.2938 (4)0.027 (2)
H12D0.72310.65160.26140.033*
C13D0.7376 (9)0.5937 (3)0.3007 (4)0.0234 (18)
H13D0.67820.57800.27340.028*
C14D0.9600 (8)0.4902 (3)0.3280 (4)0.0182 (16)
C15D1.0620 (9)0.4632 (3)0.3549 (3)0.0213 (18)
H15D1.04810.44790.38760.026*
C16D1.1867 (9)0.4595 (3)0.3318 (4)0.027 (2)
H16D1.25830.44100.34880.032*
C17D1.2077 (9)0.4822 (3)0.2849 (4)0.0240 (19)
H17D1.29350.47960.27020.029*
C18D1.1012 (8)0.5089 (3)0.2594 (3)0.0211 (17)
H18D1.11520.52450.22700.025*
C19D0.9749 (8)0.5131 (3)0.2805 (4)0.0206 (17)
H19D0.90210.53100.26290.025*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0169 (2)0.0156 (3)0.0177 (2)0.00108 (19)0.00432 (18)0.0040 (2)
I20.0174 (2)0.0146 (3)0.0220 (3)0.0025 (2)0.00503 (19)0.0049 (2)
I30.0233 (3)0.0208 (3)0.0167 (2)0.0055 (2)0.00297 (19)0.0000 (2)
I40.0230 (4)0.0236 (4)0.0189 (4)0.0050 (3)0.0015 (3)0.0013 (3)
I50.0431 (5)0.0245 (4)0.0181 (4)0.0207 (4)0.0031 (3)0.0041 (3)
N1A0.012 (3)0.023 (4)0.016 (3)0.000 (3)0.005 (2)0.004 (3)
N2A0.012 (3)0.017 (4)0.018 (3)0.000 (3)0.006 (2)0.002 (3)
N3A0.015 (3)0.012 (3)0.019 (3)0.001 (3)0.001 (2)0.002 (3)
N4A0.015 (3)0.018 (4)0.012 (3)0.001 (3)0.006 (2)0.004 (3)
C1A0.019 (4)0.025 (5)0.018 (4)0.001 (3)0.004 (3)0.000 (3)
C2A0.017 (4)0.038 (6)0.019 (4)0.001 (4)0.010 (3)0.000 (4)
C3A0.012 (3)0.040 (6)0.017 (4)0.005 (4)0.002 (3)0.006 (4)
C4A0.024 (4)0.023 (5)0.016 (4)0.007 (3)0.004 (3)0.007 (3)
C5A0.016 (3)0.023 (4)0.010 (3)0.001 (3)0.002 (3)0.003 (3)
C6A0.012 (3)0.015 (4)0.017 (4)0.002 (3)0.001 (3)0.003 (3)
C7A0.012 (3)0.019 (4)0.014 (4)0.000 (3)0.005 (3)0.003 (3)
C8A0.024 (4)0.016 (4)0.014 (4)0.000 (3)0.010 (3)0.000 (3)
C9A0.041 (5)0.027 (5)0.011 (4)0.015 (4)0.002 (3)0.003 (3)
C10A0.053 (6)0.041 (6)0.014 (4)0.024 (5)0.001 (4)0.008 (4)
C11A0.047 (5)0.019 (4)0.018 (4)0.011 (4)0.015 (4)0.001 (3)
C12A0.034 (5)0.020 (5)0.031 (5)0.002 (4)0.000 (4)0.008 (4)
C13A0.020 (4)0.017 (4)0.034 (5)0.001 (3)0.001 (3)0.004 (4)
C14A0.009 (3)0.018 (4)0.017 (4)0.002 (3)0.004 (3)0.005 (3)
C15A0.019 (4)0.024 (5)0.022 (4)0.005 (3)0.004 (3)0.001 (4)
C16A0.021 (4)0.031 (5)0.017 (4)0.004 (4)0.003 (3)0.001 (4)
C17A0.015 (4)0.023 (5)0.023 (4)0.003 (3)0.006 (3)0.007 (4)
C18A0.019 (4)0.017 (4)0.024 (4)0.009 (3)0.010 (3)0.002 (3)
C19A0.016 (3)0.015 (4)0.022 (4)0.001 (3)0.005 (3)0.000 (3)
N1B0.016 (3)0.011 (3)0.014 (3)0.001 (3)0.001 (2)0.003 (3)
N2B0.017 (3)0.009 (3)0.009 (3)0.000 (2)0.002 (2)0.003 (2)
N3B0.012 (3)0.014 (3)0.021 (3)0.001 (3)0.000 (2)0.001 (3)
N4B0.016 (3)0.013 (3)0.017 (3)0.000 (3)0.005 (2)0.004 (3)
C1B0.026 (4)0.020 (4)0.019 (4)0.001 (4)0.003 (3)0.006 (3)
C2B0.034 (5)0.015 (4)0.027 (5)0.006 (4)0.002 (4)0.003 (4)
C3B0.030 (4)0.016 (4)0.026 (4)0.000 (4)0.014 (4)0.003 (4)
C4B0.032 (5)0.024 (5)0.018 (4)0.008 (4)0.005 (3)0.003 (4)
C5B0.026 (4)0.021 (4)0.014 (4)0.003 (3)0.003 (3)0.006 (3)
C6B0.015 (3)0.015 (4)0.008 (3)0.000 (3)0.006 (3)0.002 (3)
C7B0.012 (3)0.013 (4)0.015 (3)0.000 (3)0.002 (3)0.004 (3)
C8B0.020 (4)0.010 (4)0.013 (4)0.004 (3)0.001 (3)0.004 (3)
C9B0.023 (4)0.016 (4)0.022 (4)0.002 (3)0.005 (3)0.001 (3)
C10B0.038 (5)0.012 (4)0.025 (4)0.004 (4)0.009 (4)0.005 (3)
C11B0.039 (5)0.013 (4)0.023 (4)0.010 (4)0.002 (4)0.002 (3)
C12B0.019 (4)0.026 (5)0.028 (5)0.007 (4)0.002 (3)0.003 (4)
C13B0.017 (4)0.017 (4)0.018 (4)0.001 (3)0.001 (3)0.001 (3)
C14B0.013 (3)0.016 (4)0.019 (4)0.004 (3)0.001 (3)0.001 (3)
C15B0.024 (4)0.033 (5)0.027 (5)0.008 (4)0.011 (4)0.018 (4)
C16B0.021 (4)0.046 (6)0.031 (5)0.020 (4)0.011 (4)0.015 (5)
C17B0.027 (4)0.026 (5)0.018 (4)0.008 (4)0.005 (3)0.008 (4)
C18B0.024 (4)0.025 (5)0.014 (4)0.002 (4)0.004 (3)0.006 (3)
C19B0.015 (4)0.022 (4)0.024 (4)0.003 (3)0.006 (3)0.006 (3)
N1C0.018 (3)0.012 (3)0.017 (3)0.000 (3)0.003 (2)0.001 (3)
N2C0.016 (3)0.011 (3)0.021 (3)0.000 (3)0.001 (3)0.001 (3)
N3C0.020 (3)0.012 (3)0.010 (3)0.000 (3)0.001 (2)0.001 (3)
N4C0.019 (3)0.013 (3)0.017 (3)0.003 (3)0.000 (3)0.001 (3)
C1C0.022 (4)0.021 (4)0.020 (4)0.003 (3)0.007 (3)0.001 (3)
C2C0.032 (5)0.022 (5)0.031 (5)0.005 (4)0.008 (4)0.004 (4)
C3C0.041 (5)0.009 (4)0.027 (5)0.000 (4)0.022 (4)0.000 (3)
C4C0.032 (5)0.020 (5)0.025 (4)0.009 (4)0.015 (4)0.011 (4)
C5C0.022 (4)0.022 (5)0.022 (4)0.002 (3)0.002 (3)0.001 (4)
C6C0.024 (4)0.013 (4)0.012 (3)0.001 (3)0.008 (3)0.003 (3)
C7C0.020 (4)0.018 (4)0.007 (3)0.002 (3)0.006 (3)0.004 (3)
C8C0.029 (4)0.011 (4)0.007 (3)0.003 (3)0.002 (3)0.005 (3)
C9C0.035 (5)0.018 (4)0.013 (4)0.002 (4)0.007 (3)0.001 (3)
C10C0.050 (6)0.018 (5)0.017 (4)0.010 (4)0.012 (4)0.006 (3)
C11C0.040 (5)0.029 (5)0.017 (4)0.017 (4)0.001 (4)0.004 (4)
C12C0.032 (5)0.026 (5)0.026 (5)0.010 (4)0.001 (4)0.006 (4)
C13C0.027 (4)0.021 (4)0.011 (4)0.001 (3)0.001 (3)0.000 (3)
C14C0.020 (4)0.017 (4)0.010 (3)0.003 (3)0.001 (3)0.000 (3)
C15C0.022 (4)0.028 (5)0.032 (5)0.004 (4)0.004 (4)0.009 (4)
C16C0.024 (4)0.041 (6)0.030 (5)0.013 (4)0.003 (4)0.009 (4)
C17C0.031 (4)0.029 (5)0.012 (4)0.013 (4)0.003 (3)0.004 (3)
C18C0.033 (5)0.023 (5)0.010 (4)0.004 (4)0.001 (3)0.000 (3)
C19C0.025 (4)0.021 (4)0.011 (4)0.002 (3)0.002 (3)0.002 (3)
N1D0.015 (3)0.017 (4)0.017 (3)0.000 (3)0.008 (2)0.000 (3)
N2D0.014 (3)0.012 (3)0.023 (3)0.001 (3)0.005 (3)0.001 (3)
N3D0.013 (3)0.014 (3)0.016 (3)0.001 (3)0.005 (2)0.003 (3)
N4D0.015 (3)0.016 (3)0.012 (3)0.000 (3)0.003 (2)0.001 (3)
C1D0.017 (4)0.020 (4)0.025 (4)0.000 (3)0.005 (3)0.004 (3)
C2D0.011 (3)0.040 (6)0.022 (4)0.002 (3)0.008 (3)0.000 (4)
C3D0.019 (4)0.035 (5)0.013 (4)0.012 (4)0.002 (3)0.006 (4)
C4D0.027 (4)0.023 (5)0.018 (4)0.009 (4)0.008 (3)0.000 (3)
C5D0.023 (4)0.019 (4)0.015 (4)0.001 (3)0.004 (3)0.001 (3)
C6D0.017 (4)0.019 (4)0.013 (3)0.003 (3)0.004 (3)0.006 (3)
C7D0.014 (3)0.017 (4)0.018 (4)0.001 (3)0.000 (3)0.003 (3)
C8D0.016 (4)0.011 (4)0.031 (4)0.001 (3)0.010 (3)0.000 (3)
C9D0.032 (4)0.022 (5)0.015 (4)0.005 (4)0.008 (3)0.004 (3)
C10D0.041 (5)0.026 (5)0.023 (4)0.010 (4)0.005 (4)0.003 (4)
C11D0.031 (5)0.016 (4)0.036 (5)0.001 (4)0.020 (4)0.004 (4)
C12D0.028 (4)0.020 (5)0.036 (5)0.007 (4)0.011 (4)0.008 (4)
C13D0.026 (4)0.024 (5)0.022 (4)0.002 (4)0.007 (3)0.001 (4)
C14D0.012 (3)0.016 (4)0.028 (4)0.000 (3)0.006 (3)0.001 (3)
C15D0.022 (4)0.023 (5)0.019 (4)0.008 (3)0.006 (3)0.004 (3)
C16D0.019 (4)0.036 (6)0.025 (4)0.009 (4)0.001 (3)0.006 (4)
C17D0.020 (4)0.031 (5)0.022 (4)0.004 (4)0.006 (3)0.009 (4)
C18D0.022 (4)0.022 (5)0.020 (4)0.003 (3)0.005 (3)0.004 (3)
C19D0.017 (4)0.017 (4)0.027 (4)0.001 (3)0.004 (3)0.002 (4)
Geometric parameters (Å, º) top
N1A—N2A1.318 (9)N1C—N2C1.310 (9)
N1A—C7A1.353 (11)N1C—C7C1.348 (10)
N2A—N3A1.333 (9)N2C—N3C1.342 (9)
N2A—C8A1.442 (11)N2C—C8C1.448 (10)
N3A—N4A1.322 (9)N3C—N4C1.320 (9)
N3A—C14A1.437 (9)N3C—C14C1.447 (10)
N4A—C7A1.350 (10)N4C—C7C1.343 (10)
C1A—C2A1.392 (12)C1C—C2C1.382 (13)
C1A—C6A1.416 (11)C1C—C6C1.403 (12)
C1A—H1AA0.9500C1C—H1CA0.9500
C2A—C3A1.375 (14)C2C—C3C1.386 (13)
C2A—H2AA0.9500C2C—H2CA0.9500
C3A—C4A1.384 (13)C3C—C4C1.388 (13)
C3A—H3AA0.9500C3C—H3CA0.9500
C4A—C5A1.402 (11)C4C—C5C1.379 (13)
C4A—H4AA0.9500C4C—H4CA0.9500
C5A—C6A1.382 (12)C5C—C6C1.394 (11)
C5A—H5AA0.9500C5C—H5CA0.9500
C6A—C7A1.457 (10)C6C—C7C1.462 (11)
C8A—C13A1.378 (12)C8C—C13C1.376 (11)
C8A—C9A1.380 (12)C8C—C9C1.395 (12)
C9A—C10A1.397 (13)C9C—C10C1.386 (12)
C9A—H9AA0.9500C9C—H9CA0.9500
C10A—C11A1.389 (14)C10C—C11C1.391 (13)
C10A—H10A0.9500C10C—H10C0.9500
C11A—C12A1.378 (13)C11C—C12C1.384 (14)
C11A—H11A0.9500C11C—H11C0.9500
C12A—C13A1.383 (13)C12C—C13C1.396 (12)
C12A—H12A0.9500C12C—H12C0.9500
C13A—H13A0.9500C13C—H13C0.9500
C14A—C19A1.381 (11)C14C—C19C1.373 (12)
C14A—C15A1.390 (11)C14C—C15C1.390 (11)
C15A—C16A1.381 (11)C15C—C16C1.390 (13)
C15A—H15A0.9500C15C—H15C0.9500
C16A—C17A1.377 (12)C16C—C17C1.375 (14)
C16A—H16A0.9500C16C—H16C0.9500
C17A—C18A1.400 (12)C17C—C18C1.371 (12)
C17A—H17A0.9500C17C—H17C0.9500
C18A—C19A1.389 (11)C18C—C19C1.384 (12)
C18A—H18A0.9500C18C—H18C0.9500
C19A—H19A0.9500C19C—H19C0.9500
N1B—N2B1.307 (9)N1D—N2D1.318 (9)
N1B—C7B1.357 (9)N1D—C7D1.328 (11)
N2B—N3B1.344 (8)N2D—N3D1.338 (9)
N2B—C8B1.446 (10)N2D—C8D1.452 (10)
N3B—N4B1.317 (9)N3D—N4D1.319 (9)
N3B—C14B1.443 (10)N3D—C14D1.438 (9)
N4B—C7B1.337 (10)N4D—C7D1.361 (10)
C1B—C6B1.393 (11)C1D—C6D1.383 (11)
C1B—C2B1.393 (12)C1D—C2D1.386 (11)
C1B—H1BA0.9500C1D—H1DA0.9500
C2B—C3B1.372 (13)C2D—C3D1.377 (14)
C2B—H2BA0.9500C2D—H2DA0.9500
C3B—C4B1.390 (13)C3D—C4D1.385 (13)
C3B—H3BA0.9500C3D—H3DA0.9500
C4B—C5B1.379 (13)C4D—C5D1.393 (11)
C4B—H4BA0.9500C4D—H4DA0.9500
C5B—C6B1.388 (10)C5D—C6D1.396 (12)
C5B—H5BA0.9500C5D—H5DA0.9500
C6B—C7B1.463 (11)C6D—C7D1.470 (11)
C8B—C9B1.389 (12)C8D—C9D1.362 (12)
C8B—C13B1.390 (11)C8D—C13D1.417 (12)
C9B—C10B1.379 (12)C9D—C10D1.393 (13)
C9B—H9BA0.9500C9D—H9DA0.9500
C10B—C11B1.385 (13)C10D—C11D1.370 (13)
C10B—H10B0.9500C10D—H10D0.9500
C11B—C12B1.376 (13)C11D—C12D1.399 (14)
C11B—H11B0.9500C11D—H11D0.9500
C12B—C13B1.398 (12)C12D—C13D1.378 (13)
C12B—H12B0.9500C12D—H12D0.9500
C13B—H13B0.9500C13D—H13D0.9500
C14B—C19B1.374 (11)C14D—C19D1.382 (12)
C14B—C15B1.392 (11)C14D—C15D1.387 (11)
C15B—C16B1.366 (13)C15D—C16D1.402 (12)
C15B—H15B0.9500C15D—H15D0.9500
C16B—C17B1.401 (13)C16D—C17D1.378 (13)
C16B—H16B0.9500C16D—H16D0.9500
C17B—C18B1.379 (12)C17D—C18D1.398 (12)
C17B—H17B0.9500C17D—H17D0.9500
C18B—C19B1.390 (12)C18D—C19D1.392 (11)
C18B—H18B0.9500C18D—H18D0.9500
C19B—H19B0.9500C19D—H19D0.9500
N2A—N1A—C7A103.9 (6)N2C—N1C—C7C104.0 (6)
N1A—N2A—N3A110.0 (6)N1C—N2C—N3C110.0 (6)
N1A—N2A—C8A122.5 (7)N1C—N2C—C8C122.3 (6)
N3A—N2A—C8A127.4 (6)N3C—N2C—C8C127.6 (7)
N4A—N3A—N2A110.3 (6)N4C—N3C—N2C109.8 (6)
N4A—N3A—C14A124.0 (7)N4C—N3C—C14C124.2 (6)
N2A—N3A—C14A125.6 (7)N2C—N3C—C14C126.0 (7)
N3A—N4A—C7A103.7 (7)N3C—N4C—C7C103.8 (6)
C2A—C1A—C6A119.6 (8)C2C—C1C—C6C119.9 (8)
C2A—C1A—H1AA120.2C2C—C1C—H1CA120.1
C6A—C1A—H1AA120.2C6C—C1C—H1CA120.1
C3A—C2A—C1A119.6 (8)C1C—C2C—C3C119.9 (9)
C3A—C2A—H2AA120.2C1C—C2C—H2CA120.0
C1A—C2A—H2AA120.2C3C—C2C—H2CA120.0
C2A—C3A—C4A121.5 (8)C2C—C3C—C4C120.2 (8)
C2A—C3A—H3AA119.3C2C—C3C—H3CA119.9
C4A—C3A—H3AA119.3C4C—C3C—H3CA119.9
C3A—C4A—C5A119.6 (9)C5C—C4C—C3C120.5 (8)
C3A—C4A—H4AA120.2C5C—C4C—H4CA119.8
C5A—C4A—H4AA120.2C3C—C4C—H4CA119.8
C6A—C5A—C4A119.7 (8)C4C—C5C—C6C119.7 (8)
C6A—C5A—H5AA120.1C4C—C5C—H5CA120.2
C4A—C5A—H5AA120.1C6C—C5C—H5CA120.2
C5A—C6A—C1A120.0 (7)C5C—C6C—C1C119.8 (8)
C5A—C6A—C7A120.6 (7)C5C—C6C—C7C119.9 (7)
C1A—C6A—C7A119.3 (7)C1C—C6C—C7C120.2 (7)
N4A—C7A—N1A112.1 (7)N4C—C7C—N1C112.5 (7)
N4A—C7A—C6A123.4 (7)N4C—C7C—C6C124.7 (7)
N1A—C7A—C6A124.5 (7)N1C—C7C—C6C122.8 (7)
C13A—C8A—C9A123.2 (8)C13C—C8C—C9C123.4 (8)
C13A—C8A—N2A118.2 (7)C13C—C8C—N2C117.7 (7)
C9A—C8A—N2A118.4 (7)C9C—C8C—N2C118.4 (7)
C8A—C9A—C10A117.4 (9)C10C—C9C—C8C117.4 (8)
C8A—C9A—H9AA121.3C10C—C9C—H9CA121.3
C10A—C9A—H9AA121.3C8C—C9C—H9CA121.3
C11A—C10A—C9A120.5 (9)C9C—C10C—C11C120.5 (9)
C11A—C10A—H10A119.7C9C—C10C—H10C119.8
C9A—C10A—H10A119.7C11C—C10C—H10C119.8
C12A—C11A—C10A119.9 (9)C12C—C11C—C10C120.6 (8)
C12A—C11A—H11A120.1C12C—C11C—H11C119.7
C10A—C11A—H11A120.1C10C—C11C—H11C119.7
C11A—C12A—C13A120.9 (9)C11C—C12C—C13C120.2 (9)
C11A—C12A—H12A119.6C11C—C12C—H12C119.9
C13A—C12A—H12A119.6C13C—C12C—H12C119.9
C8A—C13A—C12A118.1 (8)C8C—C13C—C12C117.9 (8)
C8A—C13A—H13A121.0C8C—C13C—H13C121.1
C12A—C13A—H13A121.0C12C—C13C—H13C121.1
C19A—C14A—C15A123.5 (7)C19C—C14C—C15C123.8 (8)
C19A—C14A—N3A119.7 (7)C19C—C14C—N3C119.5 (7)
C15A—C14A—N3A116.9 (7)C15C—C14C—N3C116.7 (7)
C16A—C15A—C14A117.2 (8)C14C—C15C—C16C116.3 (9)
C16A—C15A—H15A121.4C14C—C15C—H15C121.8
C14A—C15A—H15A121.4C16C—C15C—H15C121.8
C17A—C16A—C15A121.2 (8)C17C—C16C—C15C121.2 (9)
C17A—C16A—H16A119.4C17C—C16C—H16C119.4
C15A—C16A—H16A119.4C15C—C16C—H16C119.4
C16A—C17A—C18A120.4 (8)C18C—C17C—C16C120.2 (8)
C16A—C17A—H17A119.8C18C—C17C—H17C119.9
C18A—C17A—H17A119.8C16C—C17C—H17C119.9
C19A—C18A—C17A119.7 (8)C17C—C18C—C19C120.8 (9)
C19A—C18A—H18A120.2C17C—C18C—H18C119.6
C17A—C18A—H18A120.2C19C—C18C—H18C119.6
C14A—C19A—C18A118.0 (7)C14C—C19C—C18C117.4 (8)
C14A—C19A—H19A121.0C14C—C19C—H19C121.3
C18A—C19A—H19A121.0C18C—C19C—H19C121.3
N2B—N1B—C7B103.7 (6)N2D—N1D—C7D104.6 (6)
N1B—N2B—N3B110.0 (6)N1D—N2D—N3D109.6 (6)
N1B—N2B—C8B123.2 (6)N1D—N2D—C8D121.8 (6)
N3B—N2B—C8B126.7 (6)N3D—N2D—C8D128.3 (6)
N4B—N3B—N2B110.0 (6)N4D—N3D—N2D110.1 (6)
N4B—N3B—C14B123.8 (6)N4D—N3D—C14D123.3 (7)
N2B—N3B—C14B126.2 (7)N2D—N3D—C14D126.5 (7)
N3B—N4B—C7B103.7 (6)N3D—N4D—C7D103.3 (6)
C6B—C1B—C2B119.2 (8)C6D—C1D—C2D119.8 (8)
C6B—C1B—H1BA120.4C6D—C1D—H1DA120.1
C2B—C1B—H1BA120.4C2D—C1D—H1DA120.1
C3B—C2B—C1B121.0 (8)C3D—C2D—C1D119.7 (8)
C3B—C2B—H2BA119.5C3D—C2D—H2DA120.1
C1B—C2B—H2BA119.5C1D—C2D—H2DA120.1
C2B—C3B—C4B119.9 (8)C2D—C3D—C4D121.4 (8)
C2B—C3B—H3BA120.1C2D—C3D—H3DA119.3
C4B—C3B—H3BA120.1C4D—C3D—H3DA119.3
C5B—C4B—C3B119.5 (8)C3D—C4D—C5D119.0 (9)
C5B—C4B—H4BA120.3C3D—C4D—H4DA120.5
C3B—C4B—H4BA120.3C5D—C4D—H4DA120.5
C4B—C5B—C6B121.1 (8)C4D—C5D—C6D119.7 (8)
C4B—C5B—H5BA119.5C4D—C5D—H5DA120.1
C6B—C5B—H5BA119.5C6D—C5D—H5DA120.1
C5B—C6B—C1B119.3 (8)C1D—C6D—C5D120.3 (7)
C5B—C6B—C7B119.5 (7)C1D—C6D—C7D119.7 (8)
C1B—C6B—C7B121.2 (7)C5D—C6D—C7D120.0 (7)
N4B—C7B—N1B112.6 (7)N1D—C7D—N4D112.4 (7)
N4B—C7B—C6B125.0 (7)N1D—C7D—C6D124.2 (7)
N1B—C7B—C6B122.3 (7)N4D—C7D—C6D123.4 (7)
C9B—C8B—C13B123.6 (8)C9D—C8D—C13D123.8 (8)
C9B—C8B—N2B120.0 (7)C9D—C8D—N2D118.9 (8)
C13B—C8B—N2B116.2 (7)C13D—C8D—N2D117.3 (7)
C10B—C9B—C8B117.5 (8)C8D—C9D—C10D117.1 (8)
C10B—C9B—H9BA121.2C8D—C9D—H9DA121.5
C8B—C9B—H9BA121.2C10D—C9D—H9DA121.5
C9B—C10B—C11B120.5 (8)C11D—C10D—C9D121.5 (9)
C9B—C10B—H10B119.8C11D—C10D—H10D119.3
C11B—C10B—H10B119.8C9D—C10D—H10D119.3
C12B—C11B—C10B121.1 (8)C10D—C11D—C12D120.4 (9)
C12B—C11B—H11B119.4C10D—C11D—H11D119.8
C10B—C11B—H11B119.4C12D—C11D—H11D119.8
C11B—C12B—C13B120.3 (8)C13D—C12D—C11D120.1 (9)
C11B—C12B—H12B119.9C13D—C12D—H12D119.9
C13B—C12B—H12B119.9C11D—C12D—H12D119.9
C8B—C13B—C12B117.0 (8)C12D—C13D—C8D117.2 (8)
C8B—C13B—H13B121.5C12D—C13D—H13D121.4
C12B—C13B—H13B121.5C8D—C13D—H13D121.4
C19B—C14B—C15B123.7 (8)C19D—C14D—C15D123.9 (7)
C19B—C14B—N3B118.5 (7)C19D—C14D—N3D119.5 (7)
C15B—C14B—N3B117.8 (7)C15D—C14D—N3D116.6 (7)
C16B—C15B—C14B117.4 (8)C14D—C15D—C16D116.9 (8)
C16B—C15B—H15B121.3C14D—C15D—H15D121.6
C14B—C15B—H15B121.3C16D—C15D—H15D121.6
C15B—C16B—C17B120.7 (8)C17D—C16D—C15D121.6 (8)
C15B—C16B—H16B119.7C17D—C16D—H16D119.2
C17B—C16B—H16B119.7C15D—C16D—H16D119.2
C18B—C17B—C16B120.3 (8)C16D—C17D—C18D119.1 (8)
C18B—C17B—H17B119.8C16D—C17D—H17D120.4
C16B—C17B—H17B119.8C18D—C17D—H17D120.4
C17B—C18B—C19B120.1 (8)C19D—C18D—C17D121.3 (8)
C17B—C18B—H18B120.0C19D—C18D—H18D119.3
C19B—C18B—H18B120.0C17D—C18D—H18D119.3
C14B—C19B—C18B117.8 (7)C14D—C19D—C18D117.2 (8)
C14B—C19B—H19B121.1C14D—C19D—H19D121.4
C18B—C19B—H19B121.1C18D—C19D—H19D121.4
C7A—N1A—N2A—N3A1.8 (8)C7C—N1C—N2C—N3C1.6 (8)
C7A—N1A—N2A—C8A176.8 (7)C7C—N1C—N2C—C8C174.8 (7)
N1A—N2A—N3A—N4A1.3 (8)N1C—N2C—N3C—N4C1.1 (8)
C8A—N2A—N3A—N4A177.3 (7)C8C—N2C—N3C—N4C175.0 (7)
N1A—N2A—N3A—C14A177.8 (7)N1C—N2C—N3C—C14C179.1 (7)
C8A—N2A—N3A—C14A0.7 (12)C8C—N2C—N3C—C14C3.0 (12)
N2A—N3A—N4A—C7A0.1 (8)N2C—N3C—N4C—C7C0.1 (8)
C14A—N3A—N4A—C7A176.7 (7)C14C—N3C—N4C—C7C178.1 (7)
C6A—C1A—C2A—C3A0.9 (12)C6C—C1C—C2C—C3C0.5 (13)
C1A—C2A—C3A—C4A1.3 (13)C1C—C2C—C3C—C4C1.1 (13)
C2A—C3A—C4A—C5A0.7 (12)C2C—C3C—C4C—C5C0.8 (13)
C3A—C4A—C5A—C6A0.4 (11)C3C—C4C—C5C—C6C0.1 (13)
C4A—C5A—C6A—C1A0.8 (11)C4C—C5C—C6C—C1C0.4 (12)
C4A—C5A—C6A—C7A174.5 (7)C4C—C5C—C6C—C7C179.8 (7)
C2A—C1A—C6A—C5A0.2 (12)C2C—C1C—C6C—C5C0.2 (12)
C2A—C1A—C6A—C7A175.2 (7)C2C—C1C—C6C—C7C179.9 (8)
N3A—N4A—C7A—N1A1.1 (8)N3C—N4C—C7C—N1C0.9 (8)
N3A—N4A—C7A—C6A178.1 (7)N3C—N4C—C7C—C6C178.3 (7)
N2A—N1A—C7A—N4A1.8 (9)N2C—N1C—C7C—N4C1.5 (8)
N2A—N1A—C7A—C6A177.4 (7)N2C—N1C—C7C—C6C177.7 (7)
C5A—C6A—C7A—N4A9.7 (12)C5C—C6C—C7C—N4C10.8 (12)
C1A—C6A—C7A—N4A165.7 (7)C1C—C6C—C7C—N4C169.4 (7)
C5A—C6A—C7A—N1A171.3 (7)C5C—C6C—C7C—N1C168.3 (7)
C1A—C6A—C7A—N1A13.3 (12)C1C—C6C—C7C—N1C11.5 (11)
N1A—N2A—C8A—C13A65.3 (10)N1C—N2C—C8C—C13C49.9 (10)
N3A—N2A—C8A—C13A116.3 (9)N3C—N2C—C8C—C13C134.4 (8)
N1A—N2A—C8A—C9A110.5 (9)N1C—N2C—C8C—C9C123.0 (8)
N3A—N2A—C8A—C9A67.9 (11)N3C—N2C—C8C—C9C52.6 (11)
C13A—C8A—C9A—C10A1.8 (14)C13C—C8C—C9C—C10C2.3 (12)
N2A—C8A—C9A—C10A177.4 (8)N2C—C8C—C9C—C10C174.8 (7)
C8A—C9A—C10A—C11A1.2 (15)C8C—C9C—C10C—C11C2.6 (13)
C9A—C10A—C11A—C12A0.5 (15)C9C—C10C—C11C—C12C2.3 (14)
C10A—C11A—C12A—C13A0.3 (15)C10C—C11C—C12C—C13C1.4 (14)
C9A—C8A—C13A—C12A1.7 (13)C9C—C8C—C13C—C12C1.5 (12)
N2A—C8A—C13A—C12A177.3 (8)N2C—C8C—C13C—C12C174.0 (7)
C11A—C12A—C13A—C8A0.9 (14)C11C—C12C—C13C—C8C1.0 (13)
N4A—N3A—C14A—C19A133.8 (8)N4C—N3C—C14C—C19C133.0 (8)
N2A—N3A—C14A—C19A50.1 (11)N2C—N3C—C14C—C19C49.3 (11)
N4A—N3A—C14A—C15A46.7 (10)N4C—N3C—C14C—C15C45.9 (11)
N2A—N3A—C14A—C15A129.5 (8)N2C—N3C—C14C—C15C131.8 (8)
C19A—C14A—C15A—C16A0.7 (13)C19C—C14C—C15C—C16C4.9 (14)
N3A—C14A—C15A—C16A178.9 (8)N3C—C14C—C15C—C16C176.3 (8)
C14A—C15A—C16A—C17A1.1 (13)C14C—C15C—C16C—C17C1.9 (15)
C15A—C16A—C17A—C18A2.2 (14)C15C—C16C—C17C—C18C0.2 (15)
C16A—C17A—C18A—C19A1.4 (13)C16C—C17C—C18C—C19C0.4 (13)
C15A—C14A—C19A—C18A1.4 (12)C15C—C14C—C19C—C18C5.5 (13)
N3A—C14A—C19A—C18A178.2 (7)N3C—C14C—C19C—C18C175.7 (7)
C17A—C18A—C19A—C14A0.4 (12)C17C—C18C—C19C—C14C3.1 (12)
C7B—N1B—N2B—N3B0.8 (8)C7D—N1D—N2D—N3D1.1 (8)
C7B—N1B—N2B—C8B178.6 (7)C7D—N1D—N2D—C8D173.9 (7)
N1B—N2B—N3B—N4B0.3 (8)N1D—N2D—N3D—N4D0.9 (8)
C8B—N2B—N3B—N4B177.4 (7)C8D—N2D—N3D—N4D173.7 (7)
N1B—N2B—N3B—C14B178.9 (7)N1D—N2D—N3D—C14D177.3 (7)
C8B—N2B—N3B—C14B3.5 (12)C8D—N2D—N3D—C14D2.6 (12)
N2B—N3B—N4B—C7B1.3 (8)N2D—N3D—N4D—C7D0.3 (8)
C14B—N3B—N4B—C7B177.9 (7)C14D—N3D—N4D—C7D176.8 (7)
C6B—C1B—C2B—C3B1.6 (14)C6D—C1D—C2D—C3D0.3 (12)
C1B—C2B—C3B—C4B1.6 (14)C1D—C2D—C3D—C4D1.6 (13)
C2B—C3B—C4B—C5B1.8 (13)C2D—C3D—C4D—C5D0.6 (12)
C3B—C4B—C5B—C6B2.0 (13)C3D—C4D—C5D—C6D1.6 (12)
C4B—C5B—C6B—C1B2.0 (12)C2D—C1D—C6D—C5D1.8 (12)
C4B—C5B—C6B—C7B176.7 (8)C2D—C1D—C6D—C7D175.5 (7)
C2B—C1B—C6B—C5B1.8 (12)C4D—C5D—C6D—C1D2.8 (12)
C2B—C1B—C6B—C7B177.0 (8)C4D—C5D—C6D—C7D174.6 (7)
N3B—N4B—C7B—N1B1.8 (9)N2D—N1D—C7D—N4D1.0 (9)
N3B—N4B—C7B—C6B179.4 (7)N2D—N1D—C7D—C6D177.6 (7)
N2B—N1B—C7B—N4B1.7 (8)N3D—N4D—C7D—N1D0.4 (8)
N2B—N1B—C7B—C6B179.3 (7)N3D—N4D—C7D—C6D178.2 (7)
C5B—C6B—C7B—N4B22.8 (12)C1D—C6D—C7D—N1D2.3 (12)
C1B—C6B—C7B—N4B158.5 (8)C5D—C6D—C7D—N1D179.7 (7)
C5B—C6B—C7B—N1B159.9 (7)C1D—C6D—C7D—N4D176.1 (7)
C1B—C6B—C7B—N1B18.9 (11)C5D—C6D—C7D—N4D1.3 (12)
N1B—N2B—C8B—C9B125.6 (8)N1D—N2D—C8D—C9D90.2 (9)
N3B—N2B—C8B—C9B51.8 (11)N3D—N2D—C8D—C9D83.9 (11)
N1B—N2B—C8B—C13B50.8 (10)N1D—N2D—C8D—C13D86.3 (10)
N3B—N2B—C8B—C13B131.8 (8)N3D—N2D—C8D—C13D99.6 (9)
C13B—C8B—C9B—C10B1.0 (12)C13D—C8D—C9D—C10D1.2 (13)
N2B—C8B—C9B—C10B175.1 (7)N2D—C8D—C9D—C10D175.1 (8)
C8B—C9B—C10B—C11B0.1 (13)C8D—C9D—C10D—C11D0.9 (14)
C9B—C10B—C11B—C12B0.2 (14)C9D—C10D—C11D—C12D2.0 (14)
C10B—C11B—C12B—C13B0.3 (14)C10D—C11D—C12D—C13D1.0 (13)
C9B—C8B—C13B—C12B1.5 (12)C11D—C12D—C13D—C8D1.0 (13)
N2B—C8B—C13B—C12B174.8 (7)C9D—C8D—C13D—C12D2.1 (13)
C11B—C12B—C13B—C8B1.1 (12)N2D—C8D—C13D—C12D174.2 (7)
N4B—N3B—C14B—C19B116.9 (9)N4D—N3D—C14D—C19D137.6 (8)
N2B—N3B—C14B—C19B62.2 (11)N2D—N3D—C14D—C19D46.4 (11)
N4B—N3B—C14B—C15B61.9 (11)N4D—N3D—C14D—C15D41.5 (11)
N2B—N3B—C14B—C15B119.0 (9)N2D—N3D—C14D—C15D134.4 (8)
C19B—C14B—C15B—C16B2.7 (15)C19D—C14D—C15D—C16D0.0 (13)
N3B—C14B—C15B—C16B178.6 (9)N3D—C14D—C15D—C16D179.1 (8)
C14B—C15B—C16B—C17B0.2 (16)C14D—C15D—C16D—C17D1.0 (14)
C15B—C16B—C17B—C18B1.8 (16)C15D—C16D—C17D—C18D1.1 (14)
C16B—C17B—C18B—C19B1.5 (14)C16D—C17D—C18D—C19D0.2 (13)
C15B—C14B—C19B—C18B3.1 (14)C15D—C14D—C19D—C18D0.8 (13)
N3B—C14B—C19B—C18B178.3 (7)N3D—C14D—C19D—C18D179.9 (7)
C17B—C18B—C19B—C14B0.9 (13)C17D—C18D—C19D—C14D0.7 (13)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2, Cg3 and Cg4 are the centroids of the C1C–C6C, C8C–C13C, C1A–C6A and C1D–C6D rings, respectively.
D—H···AD—HH···AD···AD—H···A
C19B—H19B···I30.953.033.844 (8)145
C3A—H3AA···Cg1i0.952.873.636 (8)138
C5A—H5AA···Cg20.952.893.547 (9)127
C16A—H16A···Cg3ii0.952.853.657 (9)144
C16D—H16D···Cg4iii0.952.963.769 (10)144
Symmetry codes: (i) x+2, y+1, z; (ii) x1, y, z; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC19H15N4+·I
Mr426.25
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)9.6541 (4), 30.9983 (14), 24.3469 (10)
β (°) 97.930 (1)
V3)7216.4 (5)
Z16
Radiation typeMo Kα
µ (mm1)1.78
Crystal size (mm)0.37 × 0.21 × 0.06
Data collection
DiffractometerBruker APEX DUO CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.556, 0.907
No. of measured, independent and
observed [I > 2σ(I)] reflections
71406, 16492, 13800
Rint0.048
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.075, 0.172, 1.26
No. of reflections16492
No. of parameters868
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0155P)2 + 127.6P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)5.04, 2.28

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

Hydrogen-bond geometry (Å, º) top
Cg1, Cg2, Cg3 and Cg4 are the centroids of the C1C–C6C, C8C–C13C, C1A–C6A and C1D–C6D rings, respectively.
D—H···AD—HH···AD···AD—H···A
C19B—H19B···I30.953.033.844 (8)145
C3A—H3AA···Cg1i0.952.873.636 (8)138
C5A—H5AA···Cg20.952.893.547 (9)127
C16A—H16A···Cg3ii0.952.853.657 (9)144
C16D—H16D···Cg4iii0.952.963.769 (10)144
Symmetry codes: (i) x+2, y+1, z; (ii) x1, y, z; (iii) x+1, y, z.
 

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 and the Research Center, College of Pharmacy, King Saud University, for funding.

References

First citationAbbas, M. N., Mostafa, G. A. E. & Homoda, A. M. A. (2001). Talanta, 55, 647–656.  Web of Science CrossRef PubMed CAS
First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.  CrossRef CAS Web of Science IUCr Journals
First citationHassanien, M. M., Abou-El-Sherbini, Kh. S. & Mostafa, G. A. E. (2003). Talanta, 59, 383–392.  Web of Science CrossRef PubMed CAS
First citationMostafa, G. A. E. (2007). Talanta, 71, 1449–1454.  Web of Science CrossRef PubMed CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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