Buy article online - an online subscription or single-article purchase is required to access this article.
The cation of the title salt, C24H25N52+·2ClO4-, contains a tris(2-pyridylmethyl)amine core in which one of the pyridine N atoms is protonated and a second pyridine N atom forms an additional C-N bond to another 2-pyridylmethyl group, resulting in a second pyridinium center. The protonated pyridinium hydrogen bonds to a pyridine ring of a neighboring dication. The hydrogen-bonded H atom is disordered between the two N atoms.
Supporting information
CCDC reference: 282349
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.005 Å
- R factor = 0.073
- wR factor = 0.161
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.64 Ratio
Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.02
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.62 Ratio
PLAT221_ALERT_4_C Large Solvent/Anion O Ueq(max)/Ueq(min) ... 3.52 Ratio
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl2
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT432_ALERT_2_C Short Inter X...Y Contact O8 .. C7 .. 2.94 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
Cl O4
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
5 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: TEXSAN for Windows (Molecular Structure Corporation, 1999); molecular graphics: program (reference)?; software used to prepare material for publication: TEXSAN for Windows.
Crystal data top
C24H25N52+·2ClO4− | F(000) = 1208 |
Mr = 582.40 | Dx = 1.466 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8603 reflections |
a = 13.9313 (2) Å | θ = 2.5–32.0° |
b = 10.9888 (2) Å | µ = 0.30 mm−1 |
c = 18.1280 (4) Å | T = 100 K |
β = 108.0650 (8)° | Prism, colorless |
V = 2638.38 (8) Å3 | 0.20 × 0.12 × 0.10 mm |
Z = 4 | |
Data collection top
Nonius KappaCCD (with an Oxford Cryosystems Cryostream cooler) diffractometer | 9091 independent reflections |
Radiation source: fine-focus sealed tube | 4740 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
ω scans with κ offsets | θmax = 32.1°, θmin = 3.0° |
Absorption correction: multi-scan (SCALEPACK: Otwinowski & Minor 1997) | h = 0→20 |
Tmin = 0.869, Tmax = 0.955 | k = 0→16 |
48722 measured reflections | l = −26→25 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | 0 constraints |
R[F2 > 2σ(F2)] = 0.073 | H-atom parameters constrained |
wR(F2) = 0.161 | Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo) + 0.003025|Fo|2] |
S = 0.94 | (Δ/σ)max = 0.0003 |
4740 reflections | Δρmax = 0.77 e Å−3 |
352 parameters | Δρmin = −0.57 e Å−3 |
Special details top
Refinement. Refinement of F2. The weighted R-factor wR and goodness
of fit are based on F2, conventional R-factors R are
based on F. R-factors based on F2 are statistically about
twice as large as those based on F. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cl1 | −0.04650 (6) | −0.13051 (7) | 0.27292 (4) | 0.0341 (2) | |
Cl2 | 0.36495 (6) | 0.49562 (7) | 0.62091 (4) | 0.0348 (2) | |
O1 | −0.0774 (2) | −0.2542 (3) | 0.2573 (2) | 0.0725 (9) | |
O2 | −0.1317 (2) | −0.0509 (3) | 0.2500 (2) | 0.0795 (11) | |
O3 | 0.0072 (2) | −0.1158 (2) | 0.35351 (12) | 0.0430 (7) | |
O4 | 0.0189 (2) | −0.1000 (2) | 0.22868 (12) | 0.0400 (6) | |
O5 | 0.3658 (3) | 0.3683 (2) | 0.6332 (2) | 0.0742 (10) | |
O6 | 0.4090 (3) | 0.5282 (3) | 0.5646 (2) | 0.110 (1) | |
O7 | 0.4136 (2) | 0.5569 (2) | 0.69111 (12) | 0.0329 (6) | |
O8 | 0.2608 (2) | 0.5344 (4) | 0.5979 (3) | 0.1162 (13) | |
N1 | 0.1388 (2) | 0.1485 (2) | 0.47253 (13) | 0.0208 (6) | |
N2 | 0.2301 (2) | −0.1106 (2) | 0.5972 (1) | 0.0245 (6) | |
N3 | −0.0915 (2) | 0.2702 (2) | 0.48744 (13) | 0.0235 (6) | |
N4 | 0.3828 (2) | −0.0465 (3) | 0.3983 (2) | 0.0391 (8) | |
N5 | 0.2789 (2) | 0.1525 (2) | 0.32925 (13) | 0.0223 (6) | |
C1 | 0.3145 (2) | −0.1546 (3) | 0.6479 (2) | 0.0332 (8) | |
C2 | 0.3978 (2) | −0.0822 (3) | 0.6811 (2) | 0.0377 (9) | |
C3 | 0.3947 (2) | 0.0393 (3) | 0.6608 (2) | 0.0322 (8) | |
C4 | 0.3069 (2) | 0.0852 (3) | 0.6091 (2) | 0.0272 (7) | |
C5 | 0.2255 (2) | 0.0086 (2) | 0.5784 (2) | 0.0206 (6) | |
C6 | 0.1266 (2) | 0.0532 (2) | 0.5253 (2) | 0.0203 (6) | |
C7 | −0.1304 (2) | 0.3317 (3) | 0.5360 (2) | 0.0290 (8) | |
C8 | −0.0715 (2) | 0.4091 (3) | 0.5916 (2) | 0.0293 (8) | |
C9 | 0.0295 (2) | 0.4210 (3) | 0.5961 (2) | 0.0275 (7) | |
C10 | 0.0685 (2) | 0.3580 (2) | 0.5466 (2) | 0.0249 (7) | |
C11 | 0.0066 (2) | 0.2812 (2) | 0.4915 (2) | 0.0214 (6) | |
C12 | 0.0421 (2) | 0.2095 (2) | 0.4343 (2) | 0.0231 (7) | |
C13 | 0.4319 (2) | −0.1436 (4) | 0.4395 (2) | 0.0493 (11) | |
C14 | 0.4052 (3) | −0.2620 (4) | 0.4205 (3) | 0.0536 (12) | |
C15 | 0.3228 (3) | −0.2851 (3) | 0.3571 (3) | 0.0538 (12) | |
C16 | 0.2687 (3) | −0.1889 (3) | 0.3141 (2) | 0.0452 (10) | |
C17 | 0.3028 (2) | −0.0716 (3) | 0.3367 (2) | 0.0310 (8) | |
C18 | 0.2483 (2) | 0.0349 (3) | 0.2889 (2) | 0.0273 (7) | |
C19 | 0.3424 (2) | 0.2254 (3) | 0.3053 (2) | 0.0301 (8) | |
C20 | 0.3784 (2) | 0.3312 (3) | 0.3427 (2) | 0.0347 (8) | |
C21 | 0.3502 (2) | 0.3636 (3) | 0.4063 (2) | 0.0306 (8) | |
C22 | 0.2835 (2) | 0.2913 (3) | 0.4295 (2) | 0.0255 (7) | |
C23 | 0.2487 (2) | 0.1842 (2) | 0.3906 (2) | 0.0206 (6) | |
C24 | 0.1799 (2) | 0.0971 (3) | 0.4143 (2) | 0.0261 (7) | |
H1 | 0.1741 | −0.1625 | 0.5746 | 0.015* | 0.5 |
H2 | 0.3172 | −0.2383 | 0.6616 | 0.040* | |
H3 | 0.4565 | −0.1155 | 0.7174 | 0.045* | |
H4 | 0.4517 | 0.0903 | 0.6820 | 0.039* | |
H5 | 0.3026 | 0.1687 | 0.5948 | 0.033* | |
H6 | 0.0879 | 0.0848 | 0.5557 | 0.024* | |
H7 | 0.0918 | −0.0134 | 0.4953 | 0.024* | |
H8 | −0.1996 | 0.3213 | 0.5318 | 0.035* | |
H9 | −0.0990 | 0.4527 | 0.6256 | 0.035* | |
H10 | 0.0720 | 0.4735 | 0.6339 | 0.033* | |
H11 | 0.1376 | 0.3669 | 0.5501 | 0.030* | |
H12 | −0.0073 | 0.1498 | 0.4107 | 0.028* | |
H13 | 0.0504 | 0.2631 | 0.3956 | 0.028* | |
H14 | 0.4882 | −0.1284 | 0.4841 | 0.059* | |
H15 | 0.4429 | −0.3268 | 0.4505 | 0.064* | |
H16 | 0.3027 | −0.3666 | 0.3428 | 0.065* | |
H17 | 0.2106 | −0.2028 | 0.2707 | 0.054* | |
H18 | 0.2633 | 0.0365 | 0.2412 | 0.033* | |
H19 | 0.1777 | 0.0245 | 0.2789 | 0.033* | |
H20 | 0.3619 | 0.2020 | 0.2615 | 0.036* | |
H21 | 0.4223 | 0.3817 | 0.3253 | 0.042* | |
H22 | 0.3764 | 0.4357 | 0.4343 | 0.037* | |
H23 | 0.2617 | 0.3153 | 0.4721 | 0.031* | |
H24 | 0.1255 | 0.0763 | 0.3697 | 0.031* | |
H25 | 0.2171 | 0.0258 | 0.4351 | 0.031* | |
H26 | −0.1341 | 0.2180 | 0.4495 | 0.014* | 0.5 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0342 (4) | 0.0435 (4) | 0.0235 (4) | −0.0145 (3) | 0.0074 (3) | −0.0005 (3) |
Cl2 | 0.0467 (4) | 0.0314 (4) | 0.0222 (4) | −0.0204 (3) | 0.0047 (3) | 0.0015 (3) |
O1 | 0.105 (2) | 0.060 (2) | 0.035 (2) | −0.058 (2) | −0.002 (2) | 0.0024 (13) |
O2 | 0.039 (2) | 0.117 (3) | 0.083 (2) | 0.018 (2) | 0.019 (2) | 0.007 (2) |
O3 | 0.056 (1) | 0.052 (1) | 0.0224 (12) | −0.0267 (11) | 0.0134 (10) | −0.0092 (10) |
O4 | 0.053 (1) | 0.0446 (13) | 0.0252 (12) | −0.0057 (11) | 0.0159 (10) | 0.0066 (10) |
O5 | 0.143 (3) | 0.0265 (13) | 0.066 (2) | −0.021 (2) | 0.052 (2) | −0.0044 (12) |
O6 | 0.201 (4) | 0.108 (3) | 0.044 (2) | −0.108 (3) | 0.072 (2) | −0.032 (2) |
O7 | 0.0310 (10) | 0.0398 (12) | 0.0267 (12) | −0.0074 (9) | 0.0073 (9) | −0.0084 (9) |
O8 | 0.047 (2) | 0.107 (3) | 0.139 (3) | −0.028 (2) | −0.051 (2) | 0.049 (3) |
N1 | 0.0247 (11) | 0.0220 (11) | 0.0188 (12) | −0.0047 (9) | 0.0113 (9) | −0.0005 (9) |
N2 | 0.0230 (11) | 0.0238 (11) | 0.0268 (13) | −0.0011 (9) | 0.0079 (10) | −0.0031 (10) |
N3 | 0.0296 (11) | 0.0208 (11) | 0.0192 (12) | −0.0005 (9) | 0.0063 (9) | 0.0011 (9) |
N4 | 0.0287 (13) | 0.044 (2) | 0.043 (2) | 0.0067 (12) | 0.0087 (12) | 0.0130 (13) |
N5 | 0.0181 (10) | 0.0292 (12) | 0.0196 (12) | 0.0020 (9) | 0.0059 (9) | 0.0022 (9) |
C1 | 0.033 (2) | 0.029 (2) | 0.034 (2) | 0.0063 (13) | 0.0055 (13) | −0.0002 (13) |
C2 | 0.027 (2) | 0.045 (2) | 0.037 (2) | 0.009 (1) | 0.0040 (13) | −0.003 (2) |
C3 | 0.0226 (13) | 0.041 (2) | 0.031 (2) | −0.0054 (12) | 0.0062 (12) | −0.006 (1) |
C4 | 0.0276 (13) | 0.028 (1) | 0.027 (2) | −0.0041 (12) | 0.0089 (12) | −0.0020 (12) |
C5 | 0.0208 (12) | 0.0244 (13) | 0.0190 (13) | −0.0013 (10) | 0.0100 (10) | −0.0039 (10) |
C6 | 0.0219 (12) | 0.0211 (12) | 0.021 (1) | −0.0026 (10) | 0.0104 (10) | −0.0002 (10) |
C7 | 0.032 (1) | 0.027 (1) | 0.029 (2) | 0.0020 (12) | 0.0108 (12) | 0.0002 (12) |
C8 | 0.035 (2) | 0.028 (1) | 0.025 (2) | 0.0057 (12) | 0.0104 (12) | −0.0040 (12) |
C9 | 0.034 (2) | 0.0256 (13) | 0.019 (1) | 0.0001 (12) | 0.0024 (12) | −0.0017 (11) |
C10 | 0.0265 (13) | 0.0226 (13) | 0.023 (2) | −0.0014 (11) | 0.0034 (11) | 0.0014 (11) |
C11 | 0.0277 (13) | 0.0186 (12) | 0.018 (1) | −0.0001 (10) | 0.0071 (10) | 0.0033 (10) |
C12 | 0.0279 (13) | 0.0232 (13) | 0.018 (1) | −0.0037 (11) | 0.0064 (11) | 0.0017 (11) |
C13 | 0.034 (2) | 0.056 (2) | 0.055 (2) | 0.009 (2) | 0.009 (2) | 0.020 (2) |
C14 | 0.051 (2) | 0.044 (2) | 0.070 (3) | 0.019 (2) | 0.026 (2) | 0.024 (2) |
C15 | 0.071 (3) | 0.034 (2) | 0.063 (3) | 0.008 (2) | 0.031 (2) | 0.007 (2) |
C16 | 0.057 (2) | 0.036 (2) | 0.044 (2) | 0.005 (2) | 0.018 (2) | −0.005 (2) |
C17 | 0.031 (2) | 0.035 (2) | 0.033 (2) | 0.0073 (13) | 0.0198 (13) | 0.0026 (13) |
C18 | 0.029 (1) | 0.032 (1) | 0.022 (2) | 0.0012 (12) | 0.0106 (12) | −0.0039 (12) |
C19 | 0.0243 (13) | 0.043 (2) | 0.026 (2) | 0.0010 (12) | 0.0131 (12) | 0.0060 (13) |
C20 | 0.027 (1) | 0.043 (2) | 0.035 (2) | −0.0096 (13) | 0.0119 (13) | 0.008 (1) |
C21 | 0.030 (1) | 0.031 (2) | 0.029 (2) | −0.0099 (12) | 0.0066 (12) | 0.0024 (13) |
C22 | 0.0294 (13) | 0.028 (1) | 0.021 (1) | −0.0054 (11) | 0.0098 (11) | 0.0014 (11) |
C23 | 0.0190 (11) | 0.0245 (13) | 0.0178 (13) | −0.0013 (10) | 0.0052 (10) | 0.0026 (10) |
C24 | 0.031 (1) | 0.0261 (13) | 0.026 (2) | −0.0065 (11) | 0.0163 (12) | −0.0062 (12) |
Geometric parameters (Å, º) top
Cl1—O1 | 1.427 (3) | C16—C17 | 1.391 (5) |
Cl1—O2 | 1.429 (3) | C17—C18 | 1.513 (4) |
Cl1—O3 | 1.429 (2) | C19—C20 | 1.362 (4) |
Cl1—O4 | 1.428 (2) | C20—C21 | 1.375 (4) |
Cl2—O5 | 1.417 (3) | C21—C22 | 1.383 (4) |
Cl2—O6 | 1.391 (3) | C22—C23 | 1.381 (4) |
Cl2—O7 | 1.413 (2) | C23—C24 | 1.508 (4) |
Cl2—O8 | 1.444 (4) | N2—H1 | 0.950 |
N1—C6 | 1.462 (3) | C1—H2 | 0.950 |
N1—C12 | 1.472 (3) | C2—H3 | 0.950 |
N1—C24 | 1.462 (3) | C3—H4 | 0.950 |
N2—C1 | 1.339 (4) | C4—H5 | 0.950 |
N2—C5 | 1.349 (4) | C6—H6 | 0.950 |
N3—C7 | 1.350 (4) | C6—H7 | 0.950 |
N3—C11 | 1.351 (3) | C7—H8 | 0.950 |
N4—C13 | 1.360 (4) | C8—H9 | 0.950 |
N4—C17 | 1.338 (4) | C9—H10 | 0.950 |
N5—C18 | 1.480 (4) | C10—H11 | 0.950 |
N5—C19 | 1.360 (3) | C12—H12 | 0.950 |
N5—C23 | 1.351 (3) | C12—H13 | 0.950 |
C1—C2 | 1.382 (5) | C13—H14 | 0.950 |
C2—C3 | 1.381 (5) | C14—H15 | 0.950 |
C3—C4 | 1.385 (4) | C15—H16 | 0.950 |
C4—C5 | 1.383 (4) | C16—H17 | 0.950 |
C5—C6 | 1.498 (4) | C18—H18 | 0.950 |
C7—C8 | 1.378 (4) | C18—H19 | 0.950 |
C8—C9 | 1.390 (4) | C19—H20 | 0.950 |
C9—C10 | 1.372 (4) | C20—H21 | 0.950 |
C10—C11 | 1.385 (4) | C21—H22 | 0.950 |
C11—C12 | 1.503 (4) | C22—H23 | 0.950 |
C13—C14 | 1.367 (6) | C24—H24 | 0.950 |
C14—C15 | 1.373 (6) | C24—H25 | 0.950 |
C15—C16 | 1.388 (5) | N3—H26 | 0.950 |
| | | |
O1···N5i | 2.943 (3) | O8···C7ii | 2.938 (5) |
| | | |
O1—Cl1—O2 | 110.7 (2) | C7—N3—H26 | 119.2 |
O1—Cl1—O3 | 110.0 (2) | C11—N3—H26 | 119.2 |
O1—Cl1—O4 | 108.5 (2) | N2—C1—H2 | 119.0 |
O2—Cl1—O3 | 110.6 (2) | C2—C1—H2 | 119.0 |
O2—Cl1—O4 | 108.0 (2) | C1—C2—H3 | 120.4 |
O3—Cl1—O4 | 108.9 (1) | C3—C2—H3 | 120.4 |
O5—Cl2—O6 | 112.7 (2) | C2—C3—H4 | 120.6 |
O5—Cl2—O7 | 110.5 (2) | C4—C3—H4 | 120.6 |
O5—Cl2—O8 | 107.2 (2) | C3—C4—H5 | 120.3 |
O6—Cl2—O7 | 109.9 (2) | C5—C4—H5 | 120.3 |
O6—Cl2—O8 | 110.2 (3) | N1—C6—H6 | 108.7 |
O7—Cl2—O8 | 106.1 (2) | N1—C6—H7 | 108.7 |
C6—N1—C12 | 111.1 (2) | C5—C6—H6 | 108.7 |
C6—N1—C24 | 110.2 (2) | C5—C6—H7 | 108.7 |
C12—N1—C24 | 110.0 (2) | H6—C6—H7 | 109.5 |
C1—N2—C5 | 119.1 (2) | N3—C7—H8 | 119.4 |
C7—N3—C11 | 121.6 (2) | C8—C7—H8 | 119.4 |
C13—N4—C17 | 116.3 (3) | C7—C8—H9 | 121.2 |
C18—N5—C19 | 118.2 (2) | C9—C8—H9 | 121.2 |
C18—N5—C23 | 121.1 (2) | C8—C9—H10 | 119.6 |
C19—N5—C23 | 120.7 (2) | C10—C9—H10 | 119.6 |
N2—C1—C2 | 122.0 (3) | C9—C10—H11 | 120.2 |
C1—C2—C3 | 119.2 (3) | C11—C10—H11 | 120.2 |
C2—C3—C4 | 118.7 (3) | N1—C12—H12 | 109.0 |
C3—C4—C5 | 119.5 (3) | N1—C12—H13 | 109.0 |
N2—C5—C4 | 121.4 (2) | C11—C12—H12 | 109.0 |
N2—C5—C6 | 116.2 (2) | C11—C12—H13 | 109.0 |
C4—C5—C6 | 122.4 (2) | H12—C12—H13 | 109.5 |
N1—C6—C5 | 112.7 (2) | N4—C13—H14 | 118.1 |
N3—C7—C8 | 121.1 (3) | C14—C13—H14 | 118.1 |
C7—C8—C9 | 117.6 (3) | C13—C14—H15 | 120.7 |
C8—C9—C10 | 120.9 (3) | C15—C14—H15 | 120.7 |
C9—C10—C11 | 119.7 (2) | C14—C15—H16 | 120.1 |
N3—C11—C10 | 119.1 (2) | C16—C15—H16 | 120.1 |
N3—C11—C12 | 117.3 (2) | C15—C16—H17 | 121.2 |
C10—C11—C12 | 123.6 (2) | C17—C16—H17 | 121.2 |
N1—C12—C11 | 111.2 (2) | N5—C18—H18 | 108.8 |
N4—C13—C14 | 123.8 (4) | N5—C18—H19 | 108.8 |
C13—C14—C15 | 118.6 (3) | C17—C18—H18 | 108.8 |
C14—C15—C16 | 119.8 (4) | C17—C18—H19 | 108.8 |
C15—C16—C17 | 117.6 (4) | H18—C18—H19 | 109.5 |
N4—C17—C16 | 123.8 (3) | N5—C19—H20 | 119.4 |
N4—C17—C18 | 117.3 (3) | C20—C19—H20 | 119.4 |
C16—C17—C18 | 118.9 (3) | C19—C20—H21 | 120.6 |
N5—C18—C17 | 112.1 (2) | C21—C20—H21 | 120.6 |
N5—C19—C20 | 121.3 (3) | C20—C21—H22 | 120.0 |
C19—C20—C21 | 118.8 (3) | C22—C21—H22 | 120.0 |
C20—C21—C22 | 120.0 (3) | C21—C22—H23 | 120.1 |
C21—C22—C23 | 119.8 (3) | C23—C22—H23 | 120.1 |
N5—C23—C22 | 119.4 (2) | N1—C24—H24 | 108.6 |
N5—C23—C24 | 117.3 (2) | N1—C24—H25 | 108.6 |
C22—C23—C24 | 123.2 (2) | C23—C24—H24 | 108.6 |
N1—C24—C23 | 112.8 (2) | C23—C24—H25 | 108.6 |
C1—N2—H1 | 120.4 | H24—C24—H25 | 109.5 |
C5—N2—H1 | 120.4 | | |
| | | |
N1—C6—C5—N2 | −145.6 (2) | C7—N3—C11—C10 | −0.4 (4) |
N1—C6—C5—C4 | 36.6 (3) | C7—N3—C11—C12 | −179.5 (2) |
N1—C12—C11—N3 | −134.6 (2) | C7—C8—C9—C10 | 0.2 (4) |
N1—C12—C11—C10 | 46.3 (3) | C8—C7—N3—C11 | 0.5 (4) |
N1—C24—C23—N5 | −170.6 (2) | C8—C9—C10—C11 | −0.1 (4) |
N1—C24—C23—C22 | 11.1 (4) | C9—C10—C11—C12 | 179.3 (3) |
N2—C1—C2—C3 | −0.7 (5) | C11—C12—N1—C24 | −170.3 (2) |
N2—C5—C4—C3 | −0.7 (4) | C12—N1—C24—C23 | 90.9 (3) |
N3—C7—C8—C9 | −0.4 (4) | C13—N4—C17—C16 | 0.4 (4) |
N3—C11—C10—C9 | 0.2 (4) | C13—N4—C17—C18 | −178.7 (3) |
N4—C13—C14—C15 | −1.4 (6) | C13—C14—C15—C16 | 0.0 (6) |
N4—C17—C16—C15 | −1.6 (5) | C14—C13—N4—C17 | 1.2 (5) |
N4—C17—C18—N5 | −13.3 (3) | C14—C15—C16—C17 | 1.4 (5) |
N5—C18—C17—C16 | 167.6 (3) | C15—C16—C17—C18 | 177.4 (3) |
N5—C19—C20—C21 | 0.4 (5) | C17—C18—N5—C19 | 104.2 (3) |
N5—C23—C22—C21 | −1.2 (4) | C17—C18—N5—C23 | −72.7 (3) |
C1—N2—C5—C4 | 1.6 (4) | C18—N5—C19—C20 | −176.0 (3) |
C1—N2—C5—C6 | −176.3 (2) | C18—N5—C23—C22 | 176.3 (2) |
C1—C2—C3—C4 | 1.5 (5) | C18—N5—C23—C24 | −2.0 (4) |
C2—C1—N2—C5 | −0.9 (4) | C19—N5—C23—C22 | −0.6 (4) |
C2—C3—C4—C5 | −0.8 (4) | C19—N5—C23—C24 | −178.9 (2) |
C3—C4—C5—C6 | 177.0 (3) | C19—C20—C21—C22 | −2.2 (5) |
C5—C6—N1—C12 | −166.9 (2) | C20—C19—N5—C23 | 0.9 (4) |
C5—C6—N1—C24 | 70.9 (3) | C20—C21—C22—C23 | 2.6 (4) |
C6—N1—C12—C11 | 67.3 (3) | C21—C22—C23—C24 | 177.0 (3) |
C6—N1—C24—C23 | −146.2 (2) | | |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1···N3iii | 0.95 | 1.79 | 2.706 (3) | 162 |
Symmetry code: (iii) −x, −y, −z+1. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.