organic compounds
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
The 19H15N4+·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.
of the title molecular salt, CRelated literature
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
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536812033661/hb6907sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812033661/hb6907Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812033661/hb6907Isup3.cml
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.
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 The largest difference peak is 1.52 Å from atom I1.
Data collection: APEX2 (Bruker, 2009); cell
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).Fig. 1. The molecular structure of the title compound with 50% probability displacement ellipsoids. | |
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. |
C19H15N4+·I− | F(000) = 3360 |
Mr = 426.25 | Dx = 1.569 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9972 reflections |
a = 9.6541 (4) Å | θ = 2.9–32.1° |
b = 30.9983 (14) Å | µ = 1.78 mm−1 |
c = 24.3469 (10) Å | T = 100 K |
β = 97.930 (1)° | Plate, orange |
V = 7216.4 (5) Å3 | 0.37 × 0.21 × 0.06 mm |
Z = 16 |
Bruker APEX DUO CCD diffractometer | 16492 independent reflections |
Radiation source: fine-focus sealed tube | 13800 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
ϕ and ω scans | θmax = 27.5°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −12→12 |
Tmin = 0.556, Tmax = 0.907 | k = −40→40 |
71406 measured reflections | l = −31→31 |
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)] = 0.075 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.172 | H-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 parameters | Δρmax = 5.04 e Å−3 |
0 restraints | Δρmin = −2.28 e Å−3 |
C19H15N4+·I− | V = 7216.4 (5) Å3 |
Mr = 426.25 | Z = 16 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.6541 (4) Å | µ = 1.78 mm−1 |
b = 30.9983 (14) Å | T = 100 K |
c = 24.3469 (10) Å | 0.37 × 0.21 × 0.06 mm |
β = 97.930 (1)° |
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 = 0.907 | Rint = 0.048 |
71406 measured reflections |
R[F2 > 2σ(F2)] = 0.075 | 0 restraints |
wR(F2) = 0.172 | H-atom parameters constrained |
S = 1.26 | w = 1/[σ2(Fo2) + (0.0155P)2 + 127.6P] where P = (Fo2 + 2Fc2)/3 |
16492 reflections | Δρmax = 5.04 e Å−3 |
868 parameters | Δρmin = −2.28 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
I1 | 0.93818 (5) | 0.258521 (17) | 0.25097 (2) | 0.01657 (12) | |
I2 | 0.57535 (5) | 0.489539 (17) | 0.22730 (2) | 0.01779 (12) | |
I3 | 0.52640 (5) | 0.251333 (18) | 0.47905 (2) | 0.02025 (13) | |
I4 | 1.0000 | 0.5000 | 0.5000 | 0.02196 (17) | |
I5 | 1.0000 | 0.5000 | 0.0000 | 0.0287 (2) | |
N1A | 0.8507 (6) | 0.2267 (2) | 0.0944 (3) | 0.0170 (14) | |
N2A | 0.7386 (6) | 0.2201 (2) | 0.1187 (3) | 0.0153 (13) | |
N3A | 0.6758 (6) | 0.2575 (2) | 0.1261 (3) | 0.0154 (13) | |
N4A | 0.7434 (6) | 0.2896 (2) | 0.1059 (3) | 0.0147 (13) | |
C1A | 1.0411 (8) | 0.2688 (3) | 0.0272 (3) | 0.0207 (17) | |
H1AA | 1.0390 | 0.2381 | 0.0275 | 0.025* | |
C2A | 1.1314 (8) | 0.2904 (3) | −0.0032 (3) | 0.0236 (19) | |
H2AA | 1.1922 | 0.2747 | −0.0233 | 0.028* | |
C3A | 1.1321 (8) | 0.3348 (3) | −0.0039 (3) | 0.0233 (19) | |
H3AA | 1.1925 | 0.3495 | −0.0253 | 0.028* | |
C4A | 1.0467 (9) | 0.3586 (3) | 0.0260 (3) | 0.0216 (18) | |
H4AA | 1.0494 | 0.3892 | 0.0253 | 0.026* | |
C5A | 0.9562 (8) | 0.3372 (3) | 0.0572 (3) | 0.0165 (16) | |
H5AA | 0.8977 | 0.3533 | 0.0780 | 0.020* | |
C6A | 0.9524 (8) | 0.2926 (3) | 0.0577 (3) | 0.0148 (15) | |
C7A | 0.8506 (7) | 0.2698 (3) | 0.0858 (3) | 0.0148 (15) | |
C8A | 0.6944 (8) | 0.1775 (3) | 0.1328 (3) | 0.0172 (16) | |
C9A | 0.5735 (10) | 0.1609 (3) | 0.1037 (3) | 0.026 (2) | |
H9AA | 0.5180 | 0.1773 | 0.0759 | 0.032* | |
C10A | 0.5358 (12) | 0.1190 (4) | 0.1166 (4) | 0.037 (3) | |
H10A | 0.4523 | 0.1066 | 0.0978 | 0.044* | |
C11A | 0.6195 (10) | 0.0951 (3) | 0.1565 (4) | 0.027 (2) | |
H11A | 0.5936 | 0.0665 | 0.1649 | 0.032* | |
C12A | 0.7401 (10) | 0.1130 (3) | 0.1841 (4) | 0.029 (2) | |
H12A | 0.7968 | 0.0966 | 0.2115 | 0.034* | |
C13A | 0.7799 (9) | 0.1545 (3) | 0.1723 (4) | 0.0241 (18) | |
H13A | 0.8637 | 0.1667 | 0.1909 | 0.029* | |
C14A | 0.5483 (7) | 0.2627 (3) | 0.1496 (3) | 0.0147 (15) | |
C15A | 0.4442 (8) | 0.2876 (3) | 0.1199 (4) | 0.0219 (18) | |
H15A | 0.4576 | 0.3011 | 0.0860 | 0.026* | |
C16A | 0.3204 (9) | 0.2921 (3) | 0.1418 (3) | 0.0231 (18) | |
H16A | 0.2477 | 0.3094 | 0.1229 | 0.028* | |
C17A | 0.3004 (8) | 0.2720 (3) | 0.1905 (3) | 0.0203 (17) | |
H17A | 0.2132 | 0.2747 | 0.2042 | 0.024* | |
C18A | 0.4077 (8) | 0.2476 (3) | 0.2201 (3) | 0.0195 (17) | |
H18A | 0.3943 | 0.2342 | 0.2541 | 0.023* | |
C19A | 0.5340 (8) | 0.2429 (3) | 0.1994 (3) | 0.0173 (16) | |
H19A | 0.6084 | 0.2266 | 0.2189 | 0.021* | |
N1B | 0.6359 (6) | 0.2296 (2) | 0.3374 (3) | 0.0138 (13) | |
N2B | 0.6802 (6) | 0.2683 (2) | 0.3522 (2) | 0.0115 (12) | |
N3B | 0.8016 (6) | 0.2657 (2) | 0.3865 (3) | 0.0157 (13) | |
N4B | 0.8386 (7) | 0.2251 (2) | 0.3944 (3) | 0.0151 (13) | |
C1B | 0.6439 (9) | 0.1366 (3) | 0.3153 (3) | 0.0222 (18) | |
H1BA | 0.5938 | 0.1535 | 0.2867 | 0.027* | |
C2B | 0.6349 (10) | 0.0917 (3) | 0.3136 (4) | 0.0254 (19) | |
H2BA | 0.5765 | 0.0782 | 0.2839 | 0.030* | |
C3B | 0.7092 (9) | 0.0668 (3) | 0.3539 (4) | 0.0231 (18) | |
H3BA | 0.7038 | 0.0363 | 0.3516 | 0.028* | |
C4B | 0.7924 (9) | 0.0864 (3) | 0.3981 (4) | 0.0244 (19) | |
H4BA | 0.8420 | 0.0693 | 0.4267 | 0.029* | |
C5B | 0.8022 (9) | 0.1307 (3) | 0.4001 (3) | 0.0209 (17) | |
H5BA | 0.8614 | 0.1440 | 0.4297 | 0.025* | |
C6B | 0.7271 (8) | 0.1562 (3) | 0.3596 (3) | 0.0122 (14) | |
C7B | 0.7345 (7) | 0.2032 (3) | 0.3648 (3) | 0.0131 (14) | |
C8B | 0.6083 (8) | 0.3072 (3) | 0.3318 (3) | 0.0150 (15) | |
C9B | 0.6795 (9) | 0.3391 (3) | 0.3069 (3) | 0.0201 (17) | |
H9BA | 0.7771 | 0.3369 | 0.3055 | 0.024* | |
C10B | 0.6032 (10) | 0.3740 (3) | 0.2844 (4) | 0.0248 (19) | |
H10B | 0.6485 | 0.3964 | 0.2671 | 0.030* | |
C11B | 0.4610 (10) | 0.3766 (3) | 0.2870 (4) | 0.0250 (19) | |
H11B | 0.4099 | 0.4009 | 0.2712 | 0.030* | |
C12B | 0.3925 (9) | 0.3448 (3) | 0.3120 (4) | 0.0246 (19) | |
H12B | 0.2949 | 0.3471 | 0.3132 | 0.030* | |
C13B | 0.4661 (8) | 0.3090 (3) | 0.3357 (3) | 0.0176 (16) | |
H13B | 0.4210 | 0.2870 | 0.3538 | 0.021* | |
C14B | 0.8811 (8) | 0.3016 (3) | 0.4122 (3) | 0.0164 (16) | |
C15B | 1.0164 (9) | 0.3075 (3) | 0.3998 (4) | 0.027 (2) | |
H15B | 1.0562 | 0.2883 | 0.3760 | 0.032* | |
C16B | 1.0896 (9) | 0.3421 (4) | 0.4234 (4) | 0.032 (2) | |
H16B | 1.1821 | 0.3472 | 0.4158 | 0.039* | |
C17B | 1.0297 (9) | 0.3702 (3) | 0.4586 (3) | 0.0241 (19) | |
H17B | 1.0807 | 0.3946 | 0.4738 | 0.029* | |
C18B | 0.8969 (9) | 0.3625 (3) | 0.4713 (3) | 0.0210 (17) | |
H18B | 0.8577 | 0.3812 | 0.4959 | 0.025* | |
C19B | 0.8205 (8) | 0.3274 (3) | 0.4481 (3) | 0.0197 (17) | |
H19B | 0.7295 | 0.3215 | 0.4568 | 0.024* | |
N1C | 0.8767 (7) | 0.5227 (2) | 0.1441 (3) | 0.0156 (13) | |
N2C | 0.8347 (7) | 0.4841 (2) | 0.1274 (3) | 0.0158 (13) | |
N3C | 0.7115 (7) | 0.4867 (2) | 0.0944 (3) | 0.0140 (13) | |
N4C | 0.6703 (7) | 0.5273 (2) | 0.0900 (3) | 0.0165 (14) | |
C1C | 0.8953 (9) | 0.6160 (3) | 0.1564 (3) | 0.0211 (17) | |
H1CA | 0.9776 | 0.5996 | 0.1676 | 0.025* | |
C2C | 0.8951 (10) | 0.6600 (3) | 0.1653 (4) | 0.028 (2) | |
H2CA | 0.9771 | 0.6739 | 0.1829 | 0.033* | |
C3C | 0.7753 (10) | 0.6838 (3) | 0.1485 (4) | 0.0243 (19) | |
H3CA | 0.7757 | 0.7142 | 0.1540 | 0.029* | |
C4C | 0.6547 (10) | 0.6635 (3) | 0.1236 (4) | 0.0247 (19) | |
H4CA | 0.5726 | 0.6800 | 0.1126 | 0.030* | |
C5C | 0.6532 (9) | 0.6196 (3) | 0.1146 (4) | 0.0224 (18) | |
H5CA | 0.5704 | 0.6058 | 0.0975 | 0.027* | |
C6C | 0.7737 (8) | 0.5955 (3) | 0.1308 (3) | 0.0157 (15) | |
C7C | 0.7730 (8) | 0.5489 (3) | 0.1213 (3) | 0.0146 (15) | |
C8C | 0.9108 (9) | 0.4455 (3) | 0.1465 (3) | 0.0155 (15) | |
C9C | 0.8409 (10) | 0.4135 (3) | 0.1721 (3) | 0.0215 (18) | |
H9CA | 0.7437 | 0.4156 | 0.1744 | 0.026* | |
C10C | 0.9187 (11) | 0.3784 (3) | 0.1941 (4) | 0.027 (2) | |
H10C | 0.8738 | 0.3554 | 0.2105 | 0.033* | |
C11C | 1.0619 (10) | 0.3766 (3) | 0.1923 (4) | 0.029 (2) | |
H11C | 1.1147 | 0.3529 | 0.2086 | 0.035* | |
C12C | 1.1282 (10) | 0.4091 (3) | 0.1668 (4) | 0.028 (2) | |
H12C | 1.2258 | 0.4073 | 0.1651 | 0.034* | |
C13C | 1.0522 (9) | 0.4445 (3) | 0.1437 (3) | 0.0201 (17) | |
H13C | 1.0966 | 0.4673 | 0.1266 | 0.024* | |
C14C | 0.6317 (8) | 0.4508 (3) | 0.0688 (3) | 0.0161 (16) | |
C15C | 0.4901 (9) | 0.4498 (3) | 0.0739 (4) | 0.027 (2) | |
H15C | 0.4465 | 0.4725 | 0.0914 | 0.033* | |
C16C | 0.4160 (10) | 0.4139 (4) | 0.0520 (4) | 0.032 (2) | |
H16C | 0.3195 | 0.4114 | 0.0555 | 0.038* | |
C17C | 0.4797 (9) | 0.3819 (3) | 0.0254 (3) | 0.0245 (19) | |
H17C | 0.4272 | 0.3576 | 0.0108 | 0.029* | |
C18C | 0.6188 (9) | 0.3850 (3) | 0.0198 (3) | 0.0227 (18) | |
H18C | 0.6620 | 0.3627 | 0.0016 | 0.027* | |
C19C | 0.6970 (9) | 0.4203 (3) | 0.0404 (3) | 0.0193 (17) | |
H19C | 0.7921 | 0.4234 | 0.0351 | 0.023* | |
N1D | 0.6524 (6) | 0.5202 (2) | 0.3844 (3) | 0.0157 (13) | |
N2D | 0.7624 (6) | 0.5296 (2) | 0.3600 (3) | 0.0161 (14) | |
N3D | 0.8316 (6) | 0.4933 (2) | 0.3514 (3) | 0.0142 (13) | |
N4D | 0.7692 (6) | 0.4598 (2) | 0.3707 (3) | 0.0141 (13) | |
C1D | 0.4534 (8) | 0.4737 (3) | 0.4414 (3) | 0.0205 (17) | |
H1DA | 0.4416 | 0.5040 | 0.4367 | 0.025* | |
C2D | 0.3652 (8) | 0.4506 (3) | 0.4708 (4) | 0.0238 (19) | |
H2DA | 0.2926 | 0.4649 | 0.4862 | 0.029* | |
C3D | 0.3834 (8) | 0.4068 (3) | 0.4776 (3) | 0.0222 (19) | |
H3DA | 0.3241 | 0.3912 | 0.4986 | 0.027* | |
C4D | 0.4863 (9) | 0.3849 (3) | 0.4545 (3) | 0.0222 (18) | |
H4DA | 0.4972 | 0.3546 | 0.4592 | 0.027* | |
C5D | 0.5737 (8) | 0.4080 (3) | 0.4242 (3) | 0.0186 (16) | |
H5DA | 0.6433 | 0.3934 | 0.4072 | 0.022* | |
C6D | 0.5585 (8) | 0.4527 (3) | 0.4188 (3) | 0.0160 (16) | |
C7D | 0.6582 (8) | 0.4777 (3) | 0.3911 (3) | 0.0164 (16) | |
C8D | 0.8017 (8) | 0.5739 (3) | 0.3502 (4) | 0.0186 (17) | |
C9D | 0.8910 (9) | 0.5946 (3) | 0.3897 (3) | 0.0225 (18) | |
H9DA | 0.9335 | 0.5801 | 0.4221 | 0.027* | |
C10D | 0.9173 (11) | 0.6380 (3) | 0.3806 (4) | 0.030 (2) | |
H10D | 0.9802 | 0.6534 | 0.4071 | 0.036* | |
C11D | 0.8547 (9) | 0.6591 (3) | 0.3342 (4) | 0.0262 (19) | |
H11D | 0.8722 | 0.6889 | 0.3295 | 0.031* | |
C12D | 0.7651 (9) | 0.6369 (3) | 0.2938 (4) | 0.027 (2) | |
H12D | 0.7231 | 0.6516 | 0.2614 | 0.033* | |
C13D | 0.7376 (9) | 0.5937 (3) | 0.3007 (4) | 0.0234 (18) | |
H13D | 0.6782 | 0.5780 | 0.2734 | 0.028* | |
C14D | 0.9600 (8) | 0.4902 (3) | 0.3280 (4) | 0.0182 (16) | |
C15D | 1.0620 (9) | 0.4632 (3) | 0.3549 (3) | 0.0213 (18) | |
H15D | 1.0481 | 0.4479 | 0.3876 | 0.026* | |
C16D | 1.1867 (9) | 0.4595 (3) | 0.3318 (4) | 0.027 (2) | |
H16D | 1.2583 | 0.4410 | 0.3488 | 0.032* | |
C17D | 1.2077 (9) | 0.4822 (3) | 0.2849 (4) | 0.0240 (19) | |
H17D | 1.2935 | 0.4796 | 0.2702 | 0.029* | |
C18D | 1.1012 (8) | 0.5089 (3) | 0.2594 (3) | 0.0211 (17) | |
H18D | 1.1152 | 0.5245 | 0.2270 | 0.025* | |
C19D | 0.9749 (8) | 0.5131 (3) | 0.2805 (4) | 0.0206 (17) | |
H19D | 0.9021 | 0.5310 | 0.2629 | 0.025* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.0169 (2) | 0.0156 (3) | 0.0177 (2) | 0.00108 (19) | 0.00432 (18) | 0.0040 (2) |
I2 | 0.0174 (2) | 0.0146 (3) | 0.0220 (3) | 0.0025 (2) | 0.00503 (19) | 0.0049 (2) |
I3 | 0.0233 (3) | 0.0208 (3) | 0.0167 (2) | −0.0055 (2) | 0.00297 (19) | 0.0000 (2) |
I4 | 0.0230 (4) | 0.0236 (4) | 0.0189 (4) | 0.0050 (3) | 0.0015 (3) | −0.0013 (3) |
I5 | 0.0431 (5) | 0.0245 (4) | 0.0181 (4) | −0.0207 (4) | 0.0031 (3) | −0.0041 (3) |
N1A | 0.012 (3) | 0.023 (4) | 0.016 (3) | 0.000 (3) | 0.005 (2) | 0.004 (3) |
N2A | 0.012 (3) | 0.017 (4) | 0.018 (3) | 0.000 (3) | 0.006 (2) | 0.002 (3) |
N3A | 0.015 (3) | 0.012 (3) | 0.019 (3) | −0.001 (3) | 0.001 (2) | 0.002 (3) |
N4A | 0.015 (3) | 0.018 (4) | 0.012 (3) | −0.001 (3) | 0.006 (2) | 0.004 (3) |
C1A | 0.019 (4) | 0.025 (5) | 0.018 (4) | 0.001 (3) | 0.004 (3) | 0.000 (3) |
C2A | 0.017 (4) | 0.038 (6) | 0.019 (4) | −0.001 (4) | 0.010 (3) | 0.000 (4) |
C3A | 0.012 (3) | 0.040 (6) | 0.017 (4) | −0.005 (4) | 0.002 (3) | 0.006 (4) |
C4A | 0.024 (4) | 0.023 (5) | 0.016 (4) | −0.007 (3) | −0.004 (3) | 0.007 (3) |
C5A | 0.016 (3) | 0.023 (4) | 0.010 (3) | −0.001 (3) | 0.002 (3) | 0.003 (3) |
C6A | 0.012 (3) | 0.015 (4) | 0.017 (4) | −0.002 (3) | 0.001 (3) | 0.003 (3) |
C7A | 0.012 (3) | 0.019 (4) | 0.014 (4) | 0.000 (3) | 0.005 (3) | 0.003 (3) |
C8A | 0.024 (4) | 0.016 (4) | 0.014 (4) | 0.000 (3) | 0.010 (3) | 0.000 (3) |
C9A | 0.041 (5) | 0.027 (5) | 0.011 (4) | −0.015 (4) | 0.002 (3) | 0.003 (3) |
C10A | 0.053 (6) | 0.041 (6) | 0.014 (4) | −0.024 (5) | −0.001 (4) | 0.008 (4) |
C11A | 0.047 (5) | 0.019 (4) | 0.018 (4) | −0.011 (4) | 0.015 (4) | −0.001 (3) |
C12A | 0.034 (5) | 0.020 (5) | 0.031 (5) | 0.002 (4) | 0.000 (4) | 0.008 (4) |
C13A | 0.020 (4) | 0.017 (4) | 0.034 (5) | 0.001 (3) | 0.001 (3) | 0.004 (4) |
C14A | 0.009 (3) | 0.018 (4) | 0.017 (4) | −0.002 (3) | 0.004 (3) | −0.005 (3) |
C15A | 0.019 (4) | 0.024 (5) | 0.022 (4) | 0.005 (3) | 0.004 (3) | −0.001 (4) |
C16A | 0.021 (4) | 0.031 (5) | 0.017 (4) | 0.004 (4) | 0.003 (3) | −0.001 (4) |
C17A | 0.015 (4) | 0.023 (5) | 0.023 (4) | −0.003 (3) | 0.006 (3) | −0.007 (4) |
C18A | 0.019 (4) | 0.017 (4) | 0.024 (4) | −0.009 (3) | 0.010 (3) | −0.002 (3) |
C19A | 0.016 (3) | 0.015 (4) | 0.022 (4) | 0.001 (3) | 0.005 (3) | 0.000 (3) |
N1B | 0.016 (3) | 0.011 (3) | 0.014 (3) | −0.001 (3) | 0.001 (2) | 0.003 (3) |
N2B | 0.017 (3) | 0.009 (3) | 0.009 (3) | 0.000 (2) | 0.002 (2) | 0.003 (2) |
N3B | 0.012 (3) | 0.014 (3) | 0.021 (3) | −0.001 (3) | 0.000 (2) | −0.001 (3) |
N4B | 0.016 (3) | 0.013 (3) | 0.017 (3) | 0.000 (3) | 0.005 (2) | 0.004 (3) |
C1B | 0.026 (4) | 0.020 (4) | 0.019 (4) | −0.001 (4) | −0.003 (3) | 0.006 (3) |
C2B | 0.034 (5) | 0.015 (4) | 0.027 (5) | −0.006 (4) | 0.002 (4) | −0.003 (4) |
C3B | 0.030 (4) | 0.016 (4) | 0.026 (4) | 0.000 (4) | 0.014 (4) | −0.003 (4) |
C4B | 0.032 (5) | 0.024 (5) | 0.018 (4) | 0.008 (4) | 0.005 (3) | 0.003 (4) |
C5B | 0.026 (4) | 0.021 (4) | 0.014 (4) | 0.003 (3) | −0.003 (3) | 0.006 (3) |
C6B | 0.015 (3) | 0.015 (4) | 0.008 (3) | 0.000 (3) | 0.006 (3) | 0.002 (3) |
C7B | 0.012 (3) | 0.013 (4) | 0.015 (3) | 0.000 (3) | 0.002 (3) | 0.004 (3) |
C8B | 0.020 (4) | 0.010 (4) | 0.013 (4) | 0.004 (3) | −0.001 (3) | −0.004 (3) |
C9B | 0.023 (4) | 0.016 (4) | 0.022 (4) | 0.002 (3) | 0.005 (3) | 0.001 (3) |
C10B | 0.038 (5) | 0.012 (4) | 0.025 (4) | 0.004 (4) | 0.009 (4) | 0.005 (3) |
C11B | 0.039 (5) | 0.013 (4) | 0.023 (4) | 0.010 (4) | 0.002 (4) | 0.002 (3) |
C12B | 0.019 (4) | 0.026 (5) | 0.028 (5) | 0.007 (4) | −0.002 (3) | −0.003 (4) |
C13B | 0.017 (4) | 0.017 (4) | 0.018 (4) | 0.001 (3) | 0.001 (3) | −0.001 (3) |
C14B | 0.013 (3) | 0.016 (4) | 0.019 (4) | −0.004 (3) | 0.001 (3) | −0.001 (3) |
C15B | 0.024 (4) | 0.033 (5) | 0.027 (5) | −0.008 (4) | 0.011 (4) | −0.018 (4) |
C16B | 0.021 (4) | 0.046 (6) | 0.031 (5) | −0.020 (4) | 0.011 (4) | −0.015 (5) |
C17B | 0.027 (4) | 0.026 (5) | 0.018 (4) | −0.008 (4) | −0.005 (3) | −0.008 (4) |
C18B | 0.024 (4) | 0.025 (5) | 0.014 (4) | −0.002 (4) | 0.004 (3) | −0.006 (3) |
C19B | 0.015 (4) | 0.022 (4) | 0.024 (4) | −0.003 (3) | 0.006 (3) | −0.006 (3) |
N1C | 0.018 (3) | 0.012 (3) | 0.017 (3) | 0.000 (3) | 0.003 (2) | 0.001 (3) |
N2C | 0.016 (3) | 0.011 (3) | 0.021 (3) | 0.000 (3) | 0.001 (3) | 0.001 (3) |
N3C | 0.020 (3) | 0.012 (3) | 0.010 (3) | 0.000 (3) | 0.001 (2) | 0.001 (3) |
N4C | 0.019 (3) | 0.013 (3) | 0.017 (3) | 0.003 (3) | 0.000 (3) | 0.001 (3) |
C1C | 0.022 (4) | 0.021 (4) | 0.020 (4) | 0.003 (3) | 0.007 (3) | 0.001 (3) |
C2C | 0.032 (5) | 0.022 (5) | 0.031 (5) | −0.005 (4) | 0.008 (4) | −0.004 (4) |
C3C | 0.041 (5) | 0.009 (4) | 0.027 (5) | 0.000 (4) | 0.022 (4) | 0.000 (3) |
C4C | 0.032 (5) | 0.020 (5) | 0.025 (4) | 0.009 (4) | 0.015 (4) | 0.011 (4) |
C5C | 0.022 (4) | 0.022 (5) | 0.022 (4) | 0.002 (3) | 0.002 (3) | 0.001 (4) |
C6C | 0.024 (4) | 0.013 (4) | 0.012 (3) | −0.001 (3) | 0.008 (3) | 0.003 (3) |
C7C | 0.020 (4) | 0.018 (4) | 0.007 (3) | −0.002 (3) | 0.006 (3) | 0.004 (3) |
C8C | 0.029 (4) | 0.011 (4) | 0.007 (3) | 0.003 (3) | 0.002 (3) | 0.005 (3) |
C9C | 0.035 (5) | 0.018 (4) | 0.013 (4) | 0.002 (4) | 0.007 (3) | −0.001 (3) |
C10C | 0.050 (6) | 0.018 (5) | 0.017 (4) | 0.010 (4) | 0.012 (4) | 0.006 (3) |
C11C | 0.040 (5) | 0.029 (5) | 0.017 (4) | 0.017 (4) | 0.001 (4) | 0.004 (4) |
C12C | 0.032 (5) | 0.026 (5) | 0.026 (5) | 0.010 (4) | 0.001 (4) | −0.006 (4) |
C13C | 0.027 (4) | 0.021 (4) | 0.011 (4) | 0.001 (3) | −0.001 (3) | 0.000 (3) |
C14C | 0.020 (4) | 0.017 (4) | 0.010 (3) | −0.003 (3) | −0.001 (3) | 0.000 (3) |
C15C | 0.022 (4) | 0.028 (5) | 0.032 (5) | −0.004 (4) | 0.004 (4) | −0.009 (4) |
C16C | 0.024 (4) | 0.041 (6) | 0.030 (5) | −0.013 (4) | 0.003 (4) | −0.009 (4) |
C17C | 0.031 (4) | 0.029 (5) | 0.012 (4) | −0.013 (4) | −0.003 (3) | −0.004 (3) |
C18C | 0.033 (5) | 0.023 (5) | 0.010 (4) | −0.004 (4) | −0.001 (3) | 0.000 (3) |
C19C | 0.025 (4) | 0.021 (4) | 0.011 (4) | −0.002 (3) | 0.002 (3) | −0.002 (3) |
N1D | 0.015 (3) | 0.017 (4) | 0.017 (3) | 0.000 (3) | 0.008 (2) | 0.000 (3) |
N2D | 0.014 (3) | 0.012 (3) | 0.023 (3) | 0.001 (3) | 0.005 (3) | 0.001 (3) |
N3D | 0.013 (3) | 0.014 (3) | 0.016 (3) | −0.001 (3) | 0.005 (2) | 0.003 (3) |
N4D | 0.015 (3) | 0.016 (3) | 0.012 (3) | 0.000 (3) | 0.003 (2) | 0.001 (3) |
C1D | 0.017 (4) | 0.020 (4) | 0.025 (4) | 0.000 (3) | 0.005 (3) | 0.004 (3) |
C2D | 0.011 (3) | 0.040 (6) | 0.022 (4) | −0.002 (3) | 0.008 (3) | 0.000 (4) |
C3D | 0.019 (4) | 0.035 (5) | 0.013 (4) | −0.012 (4) | 0.002 (3) | 0.006 (4) |
C4D | 0.027 (4) | 0.023 (5) | 0.018 (4) | −0.009 (4) | 0.008 (3) | 0.000 (3) |
C5D | 0.023 (4) | 0.019 (4) | 0.015 (4) | 0.001 (3) | 0.004 (3) | 0.001 (3) |
C6D | 0.017 (4) | 0.019 (4) | 0.013 (3) | −0.003 (3) | 0.004 (3) | 0.006 (3) |
C7D | 0.014 (3) | 0.017 (4) | 0.018 (4) | 0.001 (3) | 0.000 (3) | 0.003 (3) |
C8D | 0.016 (4) | 0.011 (4) | 0.031 (4) | 0.001 (3) | 0.010 (3) | 0.000 (3) |
C9D | 0.032 (4) | 0.022 (5) | 0.015 (4) | −0.005 (4) | 0.008 (3) | 0.004 (3) |
C10D | 0.041 (5) | 0.026 (5) | 0.023 (4) | −0.010 (4) | 0.005 (4) | −0.003 (4) |
C11D | 0.031 (5) | 0.016 (4) | 0.036 (5) | 0.001 (4) | 0.020 (4) | 0.004 (4) |
C12D | 0.028 (4) | 0.020 (5) | 0.036 (5) | 0.007 (4) | 0.011 (4) | 0.008 (4) |
C13D | 0.026 (4) | 0.024 (5) | 0.022 (4) | 0.002 (4) | 0.007 (3) | −0.001 (4) |
C14D | 0.012 (3) | 0.016 (4) | 0.028 (4) | 0.000 (3) | 0.006 (3) | −0.001 (3) |
C15D | 0.022 (4) | 0.023 (5) | 0.019 (4) | 0.008 (3) | 0.006 (3) | 0.004 (3) |
C16D | 0.019 (4) | 0.036 (6) | 0.025 (4) | 0.009 (4) | 0.001 (3) | −0.006 (4) |
C17D | 0.020 (4) | 0.031 (5) | 0.022 (4) | −0.004 (4) | 0.006 (3) | −0.009 (4) |
C18D | 0.022 (4) | 0.022 (5) | 0.020 (4) | −0.003 (3) | 0.005 (3) | −0.004 (3) |
C19D | 0.017 (4) | 0.017 (4) | 0.027 (4) | −0.001 (3) | 0.004 (3) | −0.002 (4) |
N1A—N2A | 1.318 (9) | N1C—N2C | 1.310 (9) |
N1A—C7A | 1.353 (11) | N1C—C7C | 1.348 (10) |
N2A—N3A | 1.333 (9) | N2C—N3C | 1.342 (9) |
N2A—C8A | 1.442 (11) | N2C—C8C | 1.448 (10) |
N3A—N4A | 1.322 (9) | N3C—N4C | 1.320 (9) |
N3A—C14A | 1.437 (9) | N3C—C14C | 1.447 (10) |
N4A—C7A | 1.350 (10) | N4C—C7C | 1.343 (10) |
C1A—C2A | 1.392 (12) | C1C—C2C | 1.382 (13) |
C1A—C6A | 1.416 (11) | C1C—C6C | 1.403 (12) |
C1A—H1AA | 0.9500 | C1C—H1CA | 0.9500 |
C2A—C3A | 1.375 (14) | C2C—C3C | 1.386 (13) |
C2A—H2AA | 0.9500 | C2C—H2CA | 0.9500 |
C3A—C4A | 1.384 (13) | C3C—C4C | 1.388 (13) |
C3A—H3AA | 0.9500 | C3C—H3CA | 0.9500 |
C4A—C5A | 1.402 (11) | C4C—C5C | 1.379 (13) |
C4A—H4AA | 0.9500 | C4C—H4CA | 0.9500 |
C5A—C6A | 1.382 (12) | C5C—C6C | 1.394 (11) |
C5A—H5AA | 0.9500 | C5C—H5CA | 0.9500 |
C6A—C7A | 1.457 (10) | C6C—C7C | 1.462 (11) |
C8A—C13A | 1.378 (12) | C8C—C13C | 1.376 (11) |
C8A—C9A | 1.380 (12) | C8C—C9C | 1.395 (12) |
C9A—C10A | 1.397 (13) | C9C—C10C | 1.386 (12) |
C9A—H9AA | 0.9500 | C9C—H9CA | 0.9500 |
C10A—C11A | 1.389 (14) | C10C—C11C | 1.391 (13) |
C10A—H10A | 0.9500 | C10C—H10C | 0.9500 |
C11A—C12A | 1.378 (13) | C11C—C12C | 1.384 (14) |
C11A—H11A | 0.9500 | C11C—H11C | 0.9500 |
C12A—C13A | 1.383 (13) | C12C—C13C | 1.396 (12) |
C12A—H12A | 0.9500 | C12C—H12C | 0.9500 |
C13A—H13A | 0.9500 | C13C—H13C | 0.9500 |
C14A—C19A | 1.381 (11) | C14C—C19C | 1.373 (12) |
C14A—C15A | 1.390 (11) | C14C—C15C | 1.390 (11) |
C15A—C16A | 1.381 (11) | C15C—C16C | 1.390 (13) |
C15A—H15A | 0.9500 | C15C—H15C | 0.9500 |
C16A—C17A | 1.377 (12) | C16C—C17C | 1.375 (14) |
C16A—H16A | 0.9500 | C16C—H16C | 0.9500 |
C17A—C18A | 1.400 (12) | C17C—C18C | 1.371 (12) |
C17A—H17A | 0.9500 | C17C—H17C | 0.9500 |
C18A—C19A | 1.389 (11) | C18C—C19C | 1.384 (12) |
C18A—H18A | 0.9500 | C18C—H18C | 0.9500 |
C19A—H19A | 0.9500 | C19C—H19C | 0.9500 |
N1B—N2B | 1.307 (9) | N1D—N2D | 1.318 (9) |
N1B—C7B | 1.357 (9) | N1D—C7D | 1.328 (11) |
N2B—N3B | 1.344 (8) | N2D—N3D | 1.338 (9) |
N2B—C8B | 1.446 (10) | N2D—C8D | 1.452 (10) |
N3B—N4B | 1.317 (9) | N3D—N4D | 1.319 (9) |
N3B—C14B | 1.443 (10) | N3D—C14D | 1.438 (9) |
N4B—C7B | 1.337 (10) | N4D—C7D | 1.361 (10) |
C1B—C6B | 1.393 (11) | C1D—C6D | 1.383 (11) |
C1B—C2B | 1.393 (12) | C1D—C2D | 1.386 (11) |
C1B—H1BA | 0.9500 | C1D—H1DA | 0.9500 |
C2B—C3B | 1.372 (13) | C2D—C3D | 1.377 (14) |
C2B—H2BA | 0.9500 | C2D—H2DA | 0.9500 |
C3B—C4B | 1.390 (13) | C3D—C4D | 1.385 (13) |
C3B—H3BA | 0.9500 | C3D—H3DA | 0.9500 |
C4B—C5B | 1.379 (13) | C4D—C5D | 1.393 (11) |
C4B—H4BA | 0.9500 | C4D—H4DA | 0.9500 |
C5B—C6B | 1.388 (10) | C5D—C6D | 1.396 (12) |
C5B—H5BA | 0.9500 | C5D—H5DA | 0.9500 |
C6B—C7B | 1.463 (11) | C6D—C7D | 1.470 (11) |
C8B—C9B | 1.389 (12) | C8D—C9D | 1.362 (12) |
C8B—C13B | 1.390 (11) | C8D—C13D | 1.417 (12) |
C9B—C10B | 1.379 (12) | C9D—C10D | 1.393 (13) |
C9B—H9BA | 0.9500 | C9D—H9DA | 0.9500 |
C10B—C11B | 1.385 (13) | C10D—C11D | 1.370 (13) |
C10B—H10B | 0.9500 | C10D—H10D | 0.9500 |
C11B—C12B | 1.376 (13) | C11D—C12D | 1.399 (14) |
C11B—H11B | 0.9500 | C11D—H11D | 0.9500 |
C12B—C13B | 1.398 (12) | C12D—C13D | 1.378 (13) |
C12B—H12B | 0.9500 | C12D—H12D | 0.9500 |
C13B—H13B | 0.9500 | C13D—H13D | 0.9500 |
C14B—C19B | 1.374 (11) | C14D—C19D | 1.382 (12) |
C14B—C15B | 1.392 (11) | C14D—C15D | 1.387 (11) |
C15B—C16B | 1.366 (13) | C15D—C16D | 1.402 (12) |
C15B—H15B | 0.9500 | C15D—H15D | 0.9500 |
C16B—C17B | 1.401 (13) | C16D—C17D | 1.378 (13) |
C16B—H16B | 0.9500 | C16D—H16D | 0.9500 |
C17B—C18B | 1.379 (12) | C17D—C18D | 1.398 (12) |
C17B—H17B | 0.9500 | C17D—H17D | 0.9500 |
C18B—C19B | 1.390 (12) | C18D—C19D | 1.392 (11) |
C18B—H18B | 0.9500 | C18D—H18D | 0.9500 |
C19B—H19B | 0.9500 | C19D—H19D | 0.9500 |
N2A—N1A—C7A | 103.9 (6) | N2C—N1C—C7C | 104.0 (6) |
N1A—N2A—N3A | 110.0 (6) | N1C—N2C—N3C | 110.0 (6) |
N1A—N2A—C8A | 122.5 (7) | N1C—N2C—C8C | 122.3 (6) |
N3A—N2A—C8A | 127.4 (6) | N3C—N2C—C8C | 127.6 (7) |
N4A—N3A—N2A | 110.3 (6) | N4C—N3C—N2C | 109.8 (6) |
N4A—N3A—C14A | 124.0 (7) | N4C—N3C—C14C | 124.2 (6) |
N2A—N3A—C14A | 125.6 (7) | N2C—N3C—C14C | 126.0 (7) |
N3A—N4A—C7A | 103.7 (7) | N3C—N4C—C7C | 103.8 (6) |
C2A—C1A—C6A | 119.6 (8) | C2C—C1C—C6C | 119.9 (8) |
C2A—C1A—H1AA | 120.2 | C2C—C1C—H1CA | 120.1 |
C6A—C1A—H1AA | 120.2 | C6C—C1C—H1CA | 120.1 |
C3A—C2A—C1A | 119.6 (8) | C1C—C2C—C3C | 119.9 (9) |
C3A—C2A—H2AA | 120.2 | C1C—C2C—H2CA | 120.0 |
C1A—C2A—H2AA | 120.2 | C3C—C2C—H2CA | 120.0 |
C2A—C3A—C4A | 121.5 (8) | C2C—C3C—C4C | 120.2 (8) |
C2A—C3A—H3AA | 119.3 | C2C—C3C—H3CA | 119.9 |
C4A—C3A—H3AA | 119.3 | C4C—C3C—H3CA | 119.9 |
C3A—C4A—C5A | 119.6 (9) | C5C—C4C—C3C | 120.5 (8) |
C3A—C4A—H4AA | 120.2 | C5C—C4C—H4CA | 119.8 |
C5A—C4A—H4AA | 120.2 | C3C—C4C—H4CA | 119.8 |
C6A—C5A—C4A | 119.7 (8) | C4C—C5C—C6C | 119.7 (8) |
C6A—C5A—H5AA | 120.1 | C4C—C5C—H5CA | 120.2 |
C4A—C5A—H5AA | 120.1 | C6C—C5C—H5CA | 120.2 |
C5A—C6A—C1A | 120.0 (7) | C5C—C6C—C1C | 119.8 (8) |
C5A—C6A—C7A | 120.6 (7) | C5C—C6C—C7C | 119.9 (7) |
C1A—C6A—C7A | 119.3 (7) | C1C—C6C—C7C | 120.2 (7) |
N4A—C7A—N1A | 112.1 (7) | N4C—C7C—N1C | 112.5 (7) |
N4A—C7A—C6A | 123.4 (7) | N4C—C7C—C6C | 124.7 (7) |
N1A—C7A—C6A | 124.5 (7) | N1C—C7C—C6C | 122.8 (7) |
C13A—C8A—C9A | 123.2 (8) | C13C—C8C—C9C | 123.4 (8) |
C13A—C8A—N2A | 118.2 (7) | C13C—C8C—N2C | 117.7 (7) |
C9A—C8A—N2A | 118.4 (7) | C9C—C8C—N2C | 118.4 (7) |
C8A—C9A—C10A | 117.4 (9) | C10C—C9C—C8C | 117.4 (8) |
C8A—C9A—H9AA | 121.3 | C10C—C9C—H9CA | 121.3 |
C10A—C9A—H9AA | 121.3 | C8C—C9C—H9CA | 121.3 |
C11A—C10A—C9A | 120.5 (9) | C9C—C10C—C11C | 120.5 (9) |
C11A—C10A—H10A | 119.7 | C9C—C10C—H10C | 119.8 |
C9A—C10A—H10A | 119.7 | C11C—C10C—H10C | 119.8 |
C12A—C11A—C10A | 119.9 (9) | C12C—C11C—C10C | 120.6 (8) |
C12A—C11A—H11A | 120.1 | C12C—C11C—H11C | 119.7 |
C10A—C11A—H11A | 120.1 | C10C—C11C—H11C | 119.7 |
C11A—C12A—C13A | 120.9 (9) | C11C—C12C—C13C | 120.2 (9) |
C11A—C12A—H12A | 119.6 | C11C—C12C—H12C | 119.9 |
C13A—C12A—H12A | 119.6 | C13C—C12C—H12C | 119.9 |
C8A—C13A—C12A | 118.1 (8) | C8C—C13C—C12C | 117.9 (8) |
C8A—C13A—H13A | 121.0 | C8C—C13C—H13C | 121.1 |
C12A—C13A—H13A | 121.0 | C12C—C13C—H13C | 121.1 |
C19A—C14A—C15A | 123.5 (7) | C19C—C14C—C15C | 123.8 (8) |
C19A—C14A—N3A | 119.7 (7) | C19C—C14C—N3C | 119.5 (7) |
C15A—C14A—N3A | 116.9 (7) | C15C—C14C—N3C | 116.7 (7) |
C16A—C15A—C14A | 117.2 (8) | C14C—C15C—C16C | 116.3 (9) |
C16A—C15A—H15A | 121.4 | C14C—C15C—H15C | 121.8 |
C14A—C15A—H15A | 121.4 | C16C—C15C—H15C | 121.8 |
C17A—C16A—C15A | 121.2 (8) | C17C—C16C—C15C | 121.2 (9) |
C17A—C16A—H16A | 119.4 | C17C—C16C—H16C | 119.4 |
C15A—C16A—H16A | 119.4 | C15C—C16C—H16C | 119.4 |
C16A—C17A—C18A | 120.4 (8) | C18C—C17C—C16C | 120.2 (8) |
C16A—C17A—H17A | 119.8 | C18C—C17C—H17C | 119.9 |
C18A—C17A—H17A | 119.8 | C16C—C17C—H17C | 119.9 |
C19A—C18A—C17A | 119.7 (8) | C17C—C18C—C19C | 120.8 (9) |
C19A—C18A—H18A | 120.2 | C17C—C18C—H18C | 119.6 |
C17A—C18A—H18A | 120.2 | C19C—C18C—H18C | 119.6 |
C14A—C19A—C18A | 118.0 (7) | C14C—C19C—C18C | 117.4 (8) |
C14A—C19A—H19A | 121.0 | C14C—C19C—H19C | 121.3 |
C18A—C19A—H19A | 121.0 | C18C—C19C—H19C | 121.3 |
N2B—N1B—C7B | 103.7 (6) | N2D—N1D—C7D | 104.6 (6) |
N1B—N2B—N3B | 110.0 (6) | N1D—N2D—N3D | 109.6 (6) |
N1B—N2B—C8B | 123.2 (6) | N1D—N2D—C8D | 121.8 (6) |
N3B—N2B—C8B | 126.7 (6) | N3D—N2D—C8D | 128.3 (6) |
N4B—N3B—N2B | 110.0 (6) | N4D—N3D—N2D | 110.1 (6) |
N4B—N3B—C14B | 123.8 (6) | N4D—N3D—C14D | 123.3 (7) |
N2B—N3B—C14B | 126.2 (7) | N2D—N3D—C14D | 126.5 (7) |
N3B—N4B—C7B | 103.7 (6) | N3D—N4D—C7D | 103.3 (6) |
C6B—C1B—C2B | 119.2 (8) | C6D—C1D—C2D | 119.8 (8) |
C6B—C1B—H1BA | 120.4 | C6D—C1D—H1DA | 120.1 |
C2B—C1B—H1BA | 120.4 | C2D—C1D—H1DA | 120.1 |
C3B—C2B—C1B | 121.0 (8) | C3D—C2D—C1D | 119.7 (8) |
C3B—C2B—H2BA | 119.5 | C3D—C2D—H2DA | 120.1 |
C1B—C2B—H2BA | 119.5 | C1D—C2D—H2DA | 120.1 |
C2B—C3B—C4B | 119.9 (8) | C2D—C3D—C4D | 121.4 (8) |
C2B—C3B—H3BA | 120.1 | C2D—C3D—H3DA | 119.3 |
C4B—C3B—H3BA | 120.1 | C4D—C3D—H3DA | 119.3 |
C5B—C4B—C3B | 119.5 (8) | C3D—C4D—C5D | 119.0 (9) |
C5B—C4B—H4BA | 120.3 | C3D—C4D—H4DA | 120.5 |
C3B—C4B—H4BA | 120.3 | C5D—C4D—H4DA | 120.5 |
C4B—C5B—C6B | 121.1 (8) | C4D—C5D—C6D | 119.7 (8) |
C4B—C5B—H5BA | 119.5 | C4D—C5D—H5DA | 120.1 |
C6B—C5B—H5BA | 119.5 | C6D—C5D—H5DA | 120.1 |
C5B—C6B—C1B | 119.3 (8) | C1D—C6D—C5D | 120.3 (7) |
C5B—C6B—C7B | 119.5 (7) | C1D—C6D—C7D | 119.7 (8) |
C1B—C6B—C7B | 121.2 (7) | C5D—C6D—C7D | 120.0 (7) |
N4B—C7B—N1B | 112.6 (7) | N1D—C7D—N4D | 112.4 (7) |
N4B—C7B—C6B | 125.0 (7) | N1D—C7D—C6D | 124.2 (7) |
N1B—C7B—C6B | 122.3 (7) | N4D—C7D—C6D | 123.4 (7) |
C9B—C8B—C13B | 123.6 (8) | C9D—C8D—C13D | 123.8 (8) |
C9B—C8B—N2B | 120.0 (7) | C9D—C8D—N2D | 118.9 (8) |
C13B—C8B—N2B | 116.2 (7) | C13D—C8D—N2D | 117.3 (7) |
C10B—C9B—C8B | 117.5 (8) | C8D—C9D—C10D | 117.1 (8) |
C10B—C9B—H9BA | 121.2 | C8D—C9D—H9DA | 121.5 |
C8B—C9B—H9BA | 121.2 | C10D—C9D—H9DA | 121.5 |
C9B—C10B—C11B | 120.5 (8) | C11D—C10D—C9D | 121.5 (9) |
C9B—C10B—H10B | 119.8 | C11D—C10D—H10D | 119.3 |
C11B—C10B—H10B | 119.8 | C9D—C10D—H10D | 119.3 |
C12B—C11B—C10B | 121.1 (8) | C10D—C11D—C12D | 120.4 (9) |
C12B—C11B—H11B | 119.4 | C10D—C11D—H11D | 119.8 |
C10B—C11B—H11B | 119.4 | C12D—C11D—H11D | 119.8 |
C11B—C12B—C13B | 120.3 (8) | C13D—C12D—C11D | 120.1 (9) |
C11B—C12B—H12B | 119.9 | C13D—C12D—H12D | 119.9 |
C13B—C12B—H12B | 119.9 | C11D—C12D—H12D | 119.9 |
C8B—C13B—C12B | 117.0 (8) | C12D—C13D—C8D | 117.2 (8) |
C8B—C13B—H13B | 121.5 | C12D—C13D—H13D | 121.4 |
C12B—C13B—H13B | 121.5 | C8D—C13D—H13D | 121.4 |
C19B—C14B—C15B | 123.7 (8) | C19D—C14D—C15D | 123.9 (7) |
C19B—C14B—N3B | 118.5 (7) | C19D—C14D—N3D | 119.5 (7) |
C15B—C14B—N3B | 117.8 (7) | C15D—C14D—N3D | 116.6 (7) |
C16B—C15B—C14B | 117.4 (8) | C14D—C15D—C16D | 116.9 (8) |
C16B—C15B—H15B | 121.3 | C14D—C15D—H15D | 121.6 |
C14B—C15B—H15B | 121.3 | C16D—C15D—H15D | 121.6 |
C15B—C16B—C17B | 120.7 (8) | C17D—C16D—C15D | 121.6 (8) |
C15B—C16B—H16B | 119.7 | C17D—C16D—H16D | 119.2 |
C17B—C16B—H16B | 119.7 | C15D—C16D—H16D | 119.2 |
C18B—C17B—C16B | 120.3 (8) | C16D—C17D—C18D | 119.1 (8) |
C18B—C17B—H17B | 119.8 | C16D—C17D—H17D | 120.4 |
C16B—C17B—H17B | 119.8 | C18D—C17D—H17D | 120.4 |
C17B—C18B—C19B | 120.1 (8) | C19D—C18D—C17D | 121.3 (8) |
C17B—C18B—H18B | 120.0 | C19D—C18D—H18D | 119.3 |
C19B—C18B—H18B | 120.0 | C17D—C18D—H18D | 119.3 |
C14B—C19B—C18B | 117.8 (7) | C14D—C19D—C18D | 117.2 (8) |
C14B—C19B—H19B | 121.1 | C14D—C19D—H19D | 121.4 |
C18B—C19B—H19B | 121.1 | C18D—C19D—H19D | 121.4 |
C7A—N1A—N2A—N3A | −1.8 (8) | C7C—N1C—N2C—N3C | 1.6 (8) |
C7A—N1A—N2A—C8A | 176.8 (7) | C7C—N1C—N2C—C8C | −174.8 (7) |
N1A—N2A—N3A—N4A | 1.3 (8) | N1C—N2C—N3C—N4C | −1.1 (8) |
C8A—N2A—N3A—N4A | −177.3 (7) | C8C—N2C—N3C—N4C | 175.0 (7) |
N1A—N2A—N3A—C14A | 177.8 (7) | N1C—N2C—N3C—C14C | −179.1 (7) |
C8A—N2A—N3A—C14A | −0.7 (12) | C8C—N2C—N3C—C14C | −3.0 (12) |
N2A—N3A—N4A—C7A | −0.1 (8) | N2C—N3C—N4C—C7C | 0.1 (8) |
C14A—N3A—N4A—C7A | −176.7 (7) | C14C—N3C—N4C—C7C | 178.1 (7) |
C6A—C1A—C2A—C3A | −0.9 (12) | C6C—C1C—C2C—C3C | −0.5 (13) |
C1A—C2A—C3A—C4A | 1.3 (13) | C1C—C2C—C3C—C4C | 1.1 (13) |
C2A—C3A—C4A—C5A | −0.7 (12) | C2C—C3C—C4C—C5C | −0.8 (13) |
C3A—C4A—C5A—C6A | −0.4 (11) | C3C—C4C—C5C—C6C | 0.1 (13) |
C4A—C5A—C6A—C1A | 0.8 (11) | C4C—C5C—C6C—C1C | 0.4 (12) |
C4A—C5A—C6A—C7A | −174.5 (7) | C4C—C5C—C6C—C7C | −179.8 (7) |
C2A—C1A—C6A—C5A | −0.2 (12) | C2C—C1C—C6C—C5C | −0.2 (12) |
C2A—C1A—C6A—C7A | 175.2 (7) | C2C—C1C—C6C—C7C | −179.9 (8) |
N3A—N4A—C7A—N1A | −1.1 (8) | N3C—N4C—C7C—N1C | 0.9 (8) |
N3A—N4A—C7A—C6A | 178.1 (7) | N3C—N4C—C7C—C6C | −178.3 (7) |
N2A—N1A—C7A—N4A | 1.8 (9) | N2C—N1C—C7C—N4C | −1.5 (8) |
N2A—N1A—C7A—C6A | −177.4 (7) | N2C—N1C—C7C—C6C | 177.7 (7) |
C5A—C6A—C7A—N4A | 9.7 (12) | C5C—C6C—C7C—N4C | 10.8 (12) |
C1A—C6A—C7A—N4A | −165.7 (7) | C1C—C6C—C7C—N4C | −169.4 (7) |
C5A—C6A—C7A—N1A | −171.3 (7) | C5C—C6C—C7C—N1C | −168.3 (7) |
C1A—C6A—C7A—N1A | 13.3 (12) | C1C—C6C—C7C—N1C | 11.5 (11) |
N1A—N2A—C8A—C13A | 65.3 (10) | N1C—N2C—C8C—C13C | −49.9 (10) |
N3A—N2A—C8A—C13A | −116.3 (9) | N3C—N2C—C8C—C13C | 134.4 (8) |
N1A—N2A—C8A—C9A | −110.5 (9) | N1C—N2C—C8C—C9C | 123.0 (8) |
N3A—N2A—C8A—C9A | 67.9 (11) | N3C—N2C—C8C—C9C | −52.6 (11) |
C13A—C8A—C9A—C10A | 1.8 (14) | C13C—C8C—C9C—C10C | −2.3 (12) |
N2A—C8A—C9A—C10A | 177.4 (8) | N2C—C8C—C9C—C10C | −174.8 (7) |
C8A—C9A—C10A—C11A | −1.2 (15) | C8C—C9C—C10C—C11C | 2.6 (13) |
C9A—C10A—C11A—C12A | 0.5 (15) | C9C—C10C—C11C—C12C | −2.3 (14) |
C10A—C11A—C12A—C13A | −0.3 (15) | C10C—C11C—C12C—C13C | 1.4 (14) |
C9A—C8A—C13A—C12A | −1.7 (13) | C9C—C8C—C13C—C12C | 1.5 (12) |
N2A—C8A—C13A—C12A | −177.3 (8) | N2C—C8C—C13C—C12C | 174.0 (7) |
C11A—C12A—C13A—C8A | 0.9 (14) | C11C—C12C—C13C—C8C | −1.0 (13) |
N4A—N3A—C14A—C19A | −133.8 (8) | N4C—N3C—C14C—C19C | 133.0 (8) |
N2A—N3A—C14A—C19A | 50.1 (11) | N2C—N3C—C14C—C19C | −49.3 (11) |
N4A—N3A—C14A—C15A | 46.7 (10) | N4C—N3C—C14C—C15C | −45.9 (11) |
N2A—N3A—C14A—C15A | −129.5 (8) | N2C—N3C—C14C—C15C | 131.8 (8) |
C19A—C14A—C15A—C16A | −0.7 (13) | C19C—C14C—C15C—C16C | 4.9 (14) |
N3A—C14A—C15A—C16A | 178.9 (8) | N3C—C14C—C15C—C16C | −176.3 (8) |
C14A—C15A—C16A—C17A | −1.1 (13) | C14C—C15C—C16C—C17C | −1.9 (15) |
C15A—C16A—C17A—C18A | 2.2 (14) | C15C—C16C—C17C—C18C | −0.2 (15) |
C16A—C17A—C18A—C19A | −1.4 (13) | C16C—C17C—C18C—C19C | −0.4 (13) |
C15A—C14A—C19A—C18A | 1.4 (12) | C15C—C14C—C19C—C18C | −5.5 (13) |
N3A—C14A—C19A—C18A | −178.2 (7) | N3C—C14C—C19C—C18C | 175.7 (7) |
C17A—C18A—C19A—C14A | −0.4 (12) | C17C—C18C—C19C—C14C | 3.1 (12) |
C7B—N1B—N2B—N3B | 0.8 (8) | C7D—N1D—N2D—N3D | 1.1 (8) |
C7B—N1B—N2B—C8B | 178.6 (7) | C7D—N1D—N2D—C8D | −173.9 (7) |
N1B—N2B—N3B—N4B | 0.3 (8) | N1D—N2D—N3D—N4D | −0.9 (8) |
C8B—N2B—N3B—N4B | −177.4 (7) | C8D—N2D—N3D—N4D | 173.7 (7) |
N1B—N2B—N3B—C14B | −178.9 (7) | N1D—N2D—N3D—C14D | −177.3 (7) |
C8B—N2B—N3B—C14B | 3.5 (12) | C8D—N2D—N3D—C14D | −2.6 (12) |
N2B—N3B—N4B—C7B | −1.3 (8) | N2D—N3D—N4D—C7D | 0.3 (8) |
C14B—N3B—N4B—C7B | 177.9 (7) | C14D—N3D—N4D—C7D | 176.8 (7) |
C6B—C1B—C2B—C3B | −1.6 (14) | C6D—C1D—C2D—C3D | 0.3 (12) |
C1B—C2B—C3B—C4B | 1.6 (14) | C1D—C2D—C3D—C4D | −1.6 (13) |
C2B—C3B—C4B—C5B | −1.8 (13) | C2D—C3D—C4D—C5D | 0.6 (12) |
C3B—C4B—C5B—C6B | 2.0 (13) | C3D—C4D—C5D—C6D | 1.6 (12) |
C4B—C5B—C6B—C1B | −2.0 (12) | C2D—C1D—C6D—C5D | 1.8 (12) |
C4B—C5B—C6B—C7B | 176.7 (8) | C2D—C1D—C6D—C7D | −175.5 (7) |
C2B—C1B—C6B—C5B | 1.8 (12) | C4D—C5D—C6D—C1D | −2.8 (12) |
C2B—C1B—C6B—C7B | −177.0 (8) | C4D—C5D—C6D—C7D | 174.6 (7) |
N3B—N4B—C7B—N1B | 1.8 (9) | N2D—N1D—C7D—N4D | −1.0 (9) |
N3B—N4B—C7B—C6B | 179.4 (7) | N2D—N1D—C7D—C6D | 177.6 (7) |
N2B—N1B—C7B—N4B | −1.7 (8) | N3D—N4D—C7D—N1D | 0.4 (8) |
N2B—N1B—C7B—C6B | −179.3 (7) | N3D—N4D—C7D—C6D | −178.2 (7) |
C5B—C6B—C7B—N4B | 22.8 (12) | C1D—C6D—C7D—N1D | −2.3 (12) |
C1B—C6B—C7B—N4B | −158.5 (8) | C5D—C6D—C7D—N1D | −179.7 (7) |
C5B—C6B—C7B—N1B | −159.9 (7) | C1D—C6D—C7D—N4D | 176.1 (7) |
C1B—C6B—C7B—N1B | 18.9 (11) | C5D—C6D—C7D—N4D | −1.3 (12) |
N1B—N2B—C8B—C9B | −125.6 (8) | N1D—N2D—C8D—C9D | 90.2 (9) |
N3B—N2B—C8B—C9B | 51.8 (11) | N3D—N2D—C8D—C9D | −83.9 (11) |
N1B—N2B—C8B—C13B | 50.8 (10) | N1D—N2D—C8D—C13D | −86.3 (10) |
N3B—N2B—C8B—C13B | −131.8 (8) | N3D—N2D—C8D—C13D | 99.6 (9) |
C13B—C8B—C9B—C10B | −1.0 (12) | C13D—C8D—C9D—C10D | 1.2 (13) |
N2B—C8B—C9B—C10B | 175.1 (7) | N2D—C8D—C9D—C10D | −175.1 (8) |
C8B—C9B—C10B—C11B | 0.1 (13) | C8D—C9D—C10D—C11D | 0.9 (14) |
C9B—C10B—C11B—C12B | 0.2 (14) | C9D—C10D—C11D—C12D | −2.0 (14) |
C10B—C11B—C12B—C13B | 0.3 (14) | C10D—C11D—C12D—C13D | 1.0 (13) |
C9B—C8B—C13B—C12B | 1.5 (12) | C11D—C12D—C13D—C8D | 1.0 (13) |
N2B—C8B—C13B—C12B | −174.8 (7) | C9D—C8D—C13D—C12D | −2.1 (13) |
C11B—C12B—C13B—C8B | −1.1 (12) | N2D—C8D—C13D—C12D | 174.2 (7) |
N4B—N3B—C14B—C19B | −116.9 (9) | N4D—N3D—C14D—C19D | 137.6 (8) |
N2B—N3B—C14B—C19B | 62.2 (11) | N2D—N3D—C14D—C19D | −46.4 (11) |
N4B—N3B—C14B—C15B | 61.9 (11) | N4D—N3D—C14D—C15D | −41.5 (11) |
N2B—N3B—C14B—C15B | −119.0 (9) | N2D—N3D—C14D—C15D | 134.4 (8) |
C19B—C14B—C15B—C16B | −2.7 (15) | C19D—C14D—C15D—C16D | 0.0 (13) |
N3B—C14B—C15B—C16B | 178.6 (9) | N3D—C14D—C15D—C16D | 179.1 (8) |
C14B—C15B—C16B—C17B | 0.2 (16) | C14D—C15D—C16D—C17D | 1.0 (14) |
C15B—C16B—C17B—C18B | 1.8 (16) | C15D—C16D—C17D—C18D | −1.1 (14) |
C16B—C17B—C18B—C19B | −1.5 (14) | C16D—C17D—C18D—C19D | 0.2 (13) |
C15B—C14B—C19B—C18B | 3.1 (14) | C15D—C14D—C19D—C18D | −0.8 (13) |
N3B—C14B—C19B—C18B | −178.3 (7) | N3D—C14D—C19D—C18D | −179.9 (7) |
C17B—C18B—C19B—C14B | −0.9 (13) | C17D—C18D—C19D—C14D | 0.7 (13) |
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 | D···A | D—H···A |
C19B—H19B···I3 | 0.95 | 3.03 | 3.844 (8) | 145 |
C3A—H3AA···Cg1i | 0.95 | 2.87 | 3.636 (8) | 138 |
C5A—H5AA···Cg2 | 0.95 | 2.89 | 3.547 (9) | 127 |
C16A—H16A···Cg3ii | 0.95 | 2.85 | 3.657 (9) | 144 |
C16D—H16D···Cg4iii | 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. |
Experimental details
Crystal data | |
Chemical formula | C19H15N4+·I− |
Mr | 426.25 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 9.6541 (4), 30.9983 (14), 24.3469 (10) |
β (°) | 97.930 (1) |
V (Å3) | 7216.4 (5) |
Z | 16 |
Radiation type | Mo Kα |
µ (mm−1) | 1.78 |
Crystal size (mm) | 0.37 × 0.21 × 0.06 |
Data collection | |
Diffractometer | Bruker APEX DUO CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.556, 0.907 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 71406, 16492, 13800 |
Rint | 0.048 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.075, 0.172, 1.26 |
No. of reflections | 16492 |
No. of parameters | 868 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + (0.0155P)2 + 127.6P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 5.04, −2.28 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
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 | D···A | D—H···A |
C19B—H19B···I3 | 0.95 | 3.03 | 3.844 (8) | 145 |
C3A—H3AA···Cg1i | 0.95 | 2.87 | 3.636 (8) | 138 |
C5A—H5AA···Cg2 | 0.95 | 2.89 | 3.547 (9) | 127 |
C16A—H16A···Cg3ii | 0.95 | 2.85 | 3.657 (9) | 144 |
C16D—H16D···Cg4iii | 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. |
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
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Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
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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.