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The formation of a quadruply hydrogen-bonded dimer of the title compound, C14H25N7O2, is prevented by an intramolecular hydrogen bond, which disrupts the linear ADADA donor-acceptor array. An infinite two-dimensional hydrogen-bonded network is formed instead.
Supporting information
CCDC reference: 225783
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.007 Å
- R factor = 0.077
- wR factor = 0.187
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
Alert level A
RINTA01_ALERT_3_A The value of Rint is greater than 0.20
Rint given 0.284
The crystals of the title compound diffracted very poorly, displaying
broad and weak reflections. Measured intensities therefore have a high
sigma(I), as is shown by R(sigma) (data item _diffrn_reflns_av_sigmaI/netI)
which amounts to 0.1998. As a consequence, R(int) will also be
relatively high. A value of R(int) which is about 1.5 that of R(sigma)
is not unusual. Upon merging 13314 measured reflections into 3141
unique reflections, shelxl-97 marked only 182 to be significantly
inconsistent.
Several batches of the compound were crystallized. A total of 6
different crystals were placed on the diffractometer. All of these
showed poor diffraction. Full data were collected for three different
crystals, all of which showed high R(int) values (up to 0.42). After
solving the structure, all data sets revealed essentially the same
structure. None of the data sets showed any of the classic signs of
twinning.
PLAT020_ALERT_3_A The value of Rint is greater than 0.10 ......... 0.28
See _vrf_RINTA01_1, given above.
Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 35 Perc.
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) ..... = 3
Alert level C
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.19
PLAT301_ALERT_3_C Main Residue Disorder ......................... 12.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT411_ALERT_2_C Short Inter H...H Contact H118 .. H207 = 2.13 Ang.
2 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
5 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: Locally modified CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SET4 (de Boer & Duisenberg, 1984); data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS86 (Sheldrick, 1986); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
2,4-Di(butylureido)-6-methyl-s-triazine
top
Crystal data top
C14H25N7O2 | F(000) = 1392 |
Mr = 323.41 | Cell parameters derived by least-squares treatment of 25 SET4 setting
angles (Boer, J.L. de & Duisenberg, A.J.M. (1984). Acta Cryst. A40,
C-410). |
Monoclinic, C2/c | Dx = 1.242 Mg m−3 |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 29.54 (2) Å | Cell parameters from 25 reflections |
b = 4.613 (5) Å | θ = 8.2–17.1° |
c = 26.89 (2) Å | µ = 0.09 mm−1 |
β = 109.34 (7)° | T = 150 K |
V = 3458 (5) Å3 | Plate, colourless |
Z = 8 | 0.50 × 0.10 × 0.04 mm |
Data collection top
Enraf-Nonius CAD-4 Turbo diffractometer | Rint = 0.284 |
Radiation source: Rotating Anode | θmax = 25.3°, θmin = 1.5° |
Graphite monochromator | h = −34→34 |
ω–scans, Δω=1.3+0.35 tan θ deg | k = 0→5 |
10715 measured reflections | l = −32→32 |
3141 independent reflections | 3 standard reflections every 60 min |
1113 reflections with I > 2σ(I) | intensity decay: 5% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.077 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.187 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.010P)2] where P = (Fo2 + 2Fc2)/3 |
3141 reflections | (Δ/σ)max < 0.001 |
205 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR
and all goodnesses of fit S are based on F2,
conventional R-factors R are based on F, with F
set to zero for negative F2. The observed criterion of F2 >
σ(F2) is used only for calculating -R-factor-obs
etc. and is not relevant to the choice of reflections for
refinement. R-factors based on F2 are statistically about
twice as large as those based on F, and R-factors based on ALL
data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O110 | 0.20496 (10) | 1.2680 (8) | 0.25259 (10) | 0.0420 (13) | |
O118 | 0.29649 (10) | 0.1593 (9) | 0.05595 (11) | 0.0429 (13) | |
N101 | 0.16478 (12) | 1.1340 (10) | 0.09115 (12) | 0.0369 (16) | |
N103 | 0.23046 (12) | 0.7976 (10) | 0.11653 (12) | 0.0350 (14) | |
N105 | 0.17994 (13) | 0.8336 (11) | 0.02639 (12) | 0.0412 (16) | |
N108 | 0.21420 (12) | 1.0755 (10) | 0.17910 (12) | 0.0368 (16) | |
N111 | 0.15293 (13) | 1.4029 (10) | 0.17320 (13) | 0.0452 (16) | |
N116 | 0.24255 (12) | 0.5148 (10) | 0.05017 (12) | 0.0378 (14) | |
N119 | 0.30069 (12) | 0.4031 (10) | 0.13072 (12) | 0.0394 (16) | |
C102 | 0.20229 (16) | 1.0012 (13) | 0.12614 (15) | 0.0367 (18) | |
C104 | 0.21721 (15) | 0.7231 (12) | 0.06525 (16) | 0.0352 (18) | |
C106 | 0.15594 (15) | 1.0353 (14) | 0.04089 (16) | 0.041 (2) | |
C107 | 0.11500 (16) | 1.1737 (14) | −0.00023 (15) | 0.055 (2) | |
C109 | 0.19004 (16) | 1.2604 (13) | 0.20325 (18) | 0.0386 (19) | |
C112 | 0.12348 (15) | 1.5801 (13) | 0.19476 (16) | 0.047 (2) | |
C113 | 0.0865 (3) | 1.741 (3) | 0.1520 (3) | 0.040 (3)* | 0.533 (8) |
C114 | 0.0512 (4) | 1.531 (3) | 0.1146 (4) | 0.052 (3)* | 0.533 (8) |
C115 | 0.0164 (4) | 1.747 (3) | 0.0687 (4) | 0.059 (4)* | 0.533 (8) |
C117 | 0.28175 (16) | 0.3506 (14) | 0.07891 (16) | 0.0394 (18) | |
C120 | 0.33908 (15) | 0.2292 (13) | 0.16491 (15) | 0.0421 (18) | |
C121 | 0.38506 (16) | 0.4007 (13) | 0.18722 (16) | 0.049 (2) | |
C122 | 0.40679 (17) | 0.5034 (14) | 0.14614 (17) | 0.053 (2) | |
C123 | 0.45301 (18) | 0.6681 (17) | 0.1697 (2) | 0.082 (3) | |
C213 | 0.0690 (3) | 1.571 (3) | 0.1575 (4) | 0.0400* | 0.467 (8) |
C214 | 0.0646 (4) | 1.700 (3) | 0.1037 (4) | 0.0520* | 0.467 (8) |
C215 | 0.0075 (5) | 1.652 (4) | 0.0728 (5) | 0.0590* | 0.467 (8) |
H101 | 0.09210 | 1.24830 | 0.01590 | 0.0830* | |
H102 | 0.09910 | 1.03020 | −0.02720 | 0.0830* | |
H103 | 0.12680 | 1.33390 | −0.01650 | 0.0830* | |
H107 | 0.10740 | 1.45520 | 0.21380 | 0.0570* | 0.533 (8) |
H108 | 0.10240 | 1.85920 | 0.13190 | 0.0480* | 0.533 (8) |
H109 | 0.06880 | 1.87440 | 0.16790 | 0.0480* | 0.533 (8) |
H110 | 0.03240 | 1.42420 | 0.13310 | 0.0630* | 0.533 (8) |
H104 | 0.24050 | 0.99530 | 0.20040 | 0.0440* | |
H105 | 0.14560 | 1.39090 | 0.13880 | 0.0540* | |
H106 | 0.14400 | 1.71990 | 0.22030 | 0.0570* | 0.533 (8) |
H114 | 0.03600 | 1.89520 | 0.05960 | 0.0890* | 0.533 (8) |
H115 | 0.23220 | 0.47770 | 0.01610 | 0.0450* | |
H116 | 0.28940 | 0.54810 | 0.14430 | 0.0470* | |
H117 | 0.34490 | 0.06160 | 0.14490 | 0.0500* | |
H118 | 0.32930 | 0.15340 | 0.19430 | 0.0500* | |
H119 | 0.40890 | 0.27900 | 0.21340 | 0.0590* | |
H120 | 0.37860 | 0.57210 | 0.20600 | 0.0590* | |
H121 | 0.41290 | 0.33300 | 0.12690 | 0.0630* | |
H122 | 0.38330 | 0.62930 | 0.12030 | 0.0630* | |
H123 | 0.44750 | 0.83440 | 0.18970 | 0.1230* | |
H124 | 0.46440 | 0.73670 | 0.14150 | 0.1230* | |
H125 | 0.47720 | 0.54040 | 0.19340 | 0.1230* | |
H111 | 0.06820 | 1.39030 | 0.09930 | 0.0630* | 0.533 (8) |
H112 | −0.00720 | 1.84020 | 0.08200 | 0.0890* | 0.533 (8) |
H113 | −0.00040 | 1.63250 | 0.03730 | 0.0890* | 0.533 (8) |
H206 | 0.13520 | 1.78250 | 0.19840 | 0.0570* | 0.467 (8) |
H207 | 0.12590 | 1.50800 | 0.23020 | 0.0570* | 0.467 (8) |
H208 | 0.05730 | 1.36870 | 0.15310 | 0.0480* | 0.467 (8) |
H209 | 0.04890 | 1.68390 | 0.17370 | 0.0480* | 0.467 (8) |
H210 | 0.08450 | 1.59300 | 0.08650 | 0.0630* | 0.467 (8) |
H211 | 0.07330 | 1.90770 | 0.10630 | 0.0630* | 0.467 (8) |
H212 | −0.01090 | 1.78750 | 0.08670 | 0.0890* | 0.467 (8) |
H213 | −0.00130 | 1.45270 | 0.07820 | 0.0890* | 0.467 (8) |
H214 | 0.00050 | 1.68760 | 0.03510 | 0.0890* | 0.467 (8) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O110 | 0.054 (2) | 0.052 (3) | 0.0187 (15) | 0.000 (2) | 0.0102 (13) | −0.0035 (18) |
O118 | 0.051 (2) | 0.050 (3) | 0.0272 (17) | 0.008 (2) | 0.0121 (15) | −0.0018 (18) |
N101 | 0.041 (2) | 0.051 (4) | 0.0170 (18) | 0.006 (2) | 0.0074 (16) | −0.007 (2) |
N103 | 0.044 (2) | 0.040 (3) | 0.0192 (19) | −0.002 (2) | 0.0082 (16) | −0.001 (2) |
N105 | 0.041 (2) | 0.056 (4) | 0.022 (2) | 0.010 (3) | 0.0044 (17) | 0.003 (2) |
N108 | 0.038 (2) | 0.051 (4) | 0.0190 (18) | 0.004 (2) | 0.0063 (15) | −0.004 (2) |
N111 | 0.048 (2) | 0.063 (4) | 0.025 (2) | 0.015 (3) | 0.0125 (18) | −0.005 (2) |
N116 | 0.042 (2) | 0.049 (3) | 0.0207 (19) | 0.008 (2) | 0.0083 (17) | 0.000 (2) |
N119 | 0.050 (2) | 0.044 (4) | 0.0220 (19) | 0.010 (2) | 0.0088 (17) | −0.001 (2) |
C102 | 0.041 (3) | 0.047 (4) | 0.021 (2) | −0.003 (3) | 0.009 (2) | −0.005 (3) |
C104 | 0.039 (3) | 0.042 (4) | 0.023 (2) | 0.000 (3) | 0.008 (2) | −0.002 (3) |
C106 | 0.036 (3) | 0.061 (5) | 0.024 (2) | 0.004 (3) | 0.008 (2) | 0.003 (3) |
C107 | 0.055 (3) | 0.077 (6) | 0.026 (3) | 0.016 (4) | 0.004 (2) | 0.001 (3) |
C109 | 0.040 (3) | 0.043 (4) | 0.034 (3) | −0.001 (3) | 0.014 (2) | −0.009 (3) |
C112 | 0.052 (3) | 0.056 (5) | 0.033 (3) | 0.012 (3) | 0.013 (2) | −0.005 (3) |
C117 | 0.044 (3) | 0.053 (4) | 0.020 (2) | −0.003 (3) | 0.009 (2) | 0.001 (3) |
C120 | 0.048 (3) | 0.052 (4) | 0.022 (2) | 0.009 (3) | 0.006 (2) | 0.005 (3) |
C121 | 0.053 (3) | 0.070 (5) | 0.023 (2) | 0.001 (3) | 0.012 (2) | 0.005 (3) |
C122 | 0.057 (3) | 0.062 (5) | 0.042 (3) | 0.008 (4) | 0.021 (2) | 0.013 (3) |
C123 | 0.060 (4) | 0.113 (7) | 0.080 (4) | −0.014 (4) | 0.033 (3) | 0.008 (4) |
Geometric parameters (Å, º) top
O110—C109 | 1.252 (5) | C107—H101 | 0.9790 |
O118—C117 | 1.236 (7) | C112—H107 | 0.9904 |
N101—C102 | 1.341 (6) | C112—H206 | 0.9893 |
N101—C106 | 1.367 (6) | C112—H106 | 0.9896 |
N103—C102 | 1.336 (7) | C112—H207 | 0.9893 |
N103—C104 | 1.347 (5) | C213—C214 | 1.530 (15) |
N105—C104 | 1.342 (6) | C113—H109 | 0.9914 |
N105—C106 | 1.305 (7) | C113—H108 | 0.9890 |
N108—C102 | 1.392 (5) | C214—C215 | 1.630 (19) |
N108—C109 | 1.402 (7) | C114—H110 | 0.9908 |
N111—C109 | 1.304 (7) | C114—H111 | 0.9897 |
N111—C112 | 1.448 (7) | C115—H112 | 0.9818 |
N116—C104 | 1.360 (7) | C115—H113 | 0.9801 |
N116—C117 | 1.385 (7) | C115—H114 | 0.9779 |
N119—C117 | 1.340 (5) | C120—H117 | 0.9890 |
N119—C120 | 1.444 (6) | C120—H118 | 0.9907 |
N108—H104 | 0.8796 | C121—H119 | 0.9891 |
N111—H105 | 0.8792 | C121—H120 | 0.9902 |
N116—H115 | 0.8812 | C122—H121 | 0.9899 |
N119—H116 | 0.8790 | C122—H122 | 0.9911 |
C106—C107 | 1.486 (7) | C123—H123 | 0.9809 |
C112—C113 | 1.495 (11) | C123—H124 | 0.9784 |
C112—C213 | 1.590 (11) | C123—H125 | 0.9809 |
C113—C114 | 1.531 (16) | C213—H208 | 0.9886 |
C114—C115 | 1.653 (17) | C213—H209 | 0.9924 |
C120—C121 | 1.514 (7) | C214—H210 | 0.9916 |
C121—C122 | 1.525 (7) | C214—H211 | 0.9884 |
C122—C123 | 1.507 (8) | C215—H212 | 0.9800 |
C107—H102 | 0.9794 | C215—H213 | 0.9792 |
C107—H103 | 0.9798 | C215—H214 | 0.9791 |
| | | |
O110···N108i | 2.861 (6) | H105···C214 | 2.6746 |
O118···N116ii | 2.818 (5) | H105···H210 | 2.1032 |
O118···C104iii | 3.160 (7) | H105···N101 | 1.9616 |
O110···H107 | 2.8545 | H105···C102 | 2.5553 |
O110···H104i | 1.9860 | H106···C120iv | 2.9593 |
O110···H116i | 2.9049 | H106···C121iv | 3.0051 |
O110···H118iv | 2.6799 | H106···H118iv | 2.1886 |
O110···H106 | 2.7031 | H106···O110 | 2.7031 |
O110···H207 | 2.4721 | H106···C109vi | 2.9478 |
O118···H117 | 2.3882 | H107···O110 | 2.8545 |
O118···H103v | 2.8024 | H107···H110 | 2.5404 |
O118···H115ii | 1.9452 | H108···N101vi | 2.7460 |
N101···N111 | 2.653 (6) | H108···H105 | 2.4845 |
N101···C104vi | 3.314 (8) | H108···H114 | 2.2647 |
N103···C117vi | 3.293 (8) | H108···N111vi | 2.9418 |
N103···N119 | 2.690 (7) | H108···C102vi | 3.0762 |
N108···O110vii | 2.861 (6) | H110···H124xi | 2.2660 |
N111···N101 | 2.653 (6) | H110···H107 | 2.5404 |
N116···C106iii | 3.328 (8) | H110···C123xi | 3.0648 |
N116···O118ii | 2.818 (5) | H111···H114iii | 2.5667 |
N119···C102iii | 3.415 (8) | H111···H105 | 2.1788 |
N119···N103 | 2.690 (7) | H111···N111 | 2.6311 |
N101···H105 | 1.9616 | H113···H113viii | 2.3559 |
N101···H108iii | 2.7460 | H114···H111vi | 2.5667 |
N103···H116 | 2.0131 | H114···H108 | 2.2647 |
N105···H103iii | 2.8122 | H115···O118ii | 1.9452 |
N108···H206iii | 2.8887 | H115···C117ii | 2.8798 |
N111···H111 | 2.6311 | H116···N103 | 2.0131 |
N111···H210 | 2.6775 | H116···O110vii | 2.9049 |
N111···H108iii | 2.9418 | H116···C104 | 2.5914 |
N119···H122 | 2.7523 | H117···H121 | 2.5457 |
C102···N119vi | 3.415 (8) | H117···O118 | 2.3882 |
C102···C117vi | 3.420 (8) | H117···H122iii | 2.4896 |
C104···N101iii | 3.314 (8) | H118···C112ix | 2.8641 |
C104···C117vi | 3.418 (9) | H118···O110ix | 2.6799 |
C104···O118vi | 3.160 (7) | H118···H207ix | 2.1315 |
C106···N116vi | 3.328 (8) | H118···H106ix | 2.1886 |
C107···C215viii | 3.588 (16) | H119···H125 | 2.5559 |
C112···C121iv | 3.585 (8) | H119···C112ix | 3.0692 |
C117···C102iii | 3.420 (8) | H119···H123iii | 2.5286 |
C117···N103iii | 3.293 (8) | H119···H207ix | 2.4397 |
C117···C104iii | 3.418 (9) | H120···H123 | 2.5278 |
C121···C112ix | 3.585 (8) | H121···H117 | 2.5457 |
C102···H108iii | 3.0762 | H122···H117vi | 2.4896 |
C102···H105 | 2.5553 | H122···N119 | 2.7523 |
C104···H116 | 2.5914 | H123···H120 | 2.5278 |
C109···H106iii | 2.9478 | H123···H119vi | 2.5286 |
C109···H206iii | 2.7132 | H124···H110x | 2.2660 |
C109···H104i | 2.9284 | H124···H213x | 2.4615 |
C112···H118iv | 2.8641 | H125···H119 | 2.5559 |
C112···H119iv | 3.0692 | H206···N108vi | 2.8887 |
C114···H105 | 2.7231 | H206···C109vi | 2.7132 |
C215···C107viii | 3.588 (16) | H207···O110 | 2.4721 |
C117···H115ii | 2.8798 | H207···C120iv | 2.8520 |
C120···H207ix | 2.8520 | H207···C121iv | 2.9654 |
C120···H106ix | 2.9593 | H207···H118iv | 2.1315 |
C121···H207ix | 2.9654 | H207···H119iv | 2.4397 |
C121···H106ix | 3.0051 | H208···H211iii | 2.5930 |
C123···H110x | 3.0648 | H208···H213 | 2.2122 |
C214···H105 | 2.6746 | H209···H212 | 2.4667 |
H101···H210 | 2.5427 | H210···N111 | 2.6775 |
H103···N105vi | 2.8122 | H210···H101 | 2.5427 |
H103···O118v | 2.8024 | H210···H105 | 2.1032 |
H104···C109vii | 2.9284 | H211···H208vi | 2.5930 |
H104···O110vii | 1.9860 | H212···H209 | 2.4667 |
H105···C114 | 2.7231 | H213···H208 | 2.2122 |
H105···H108 | 2.4845 | H213···H124xi | 2.4615 |
H105···H111 | 2.1788 | H214···H214viii | 2.5540 |
| | | |
C102—N101—C106 | 112.6 (4) | C112—C213—C214 | 109.7 (8) |
C102—N103—C104 | 112.9 (4) | C112—C113—H108 | 109.62 |
C104—N105—C106 | 115.1 (4) | C112—C113—H109 | 109.39 |
C102—N108—C109 | 129.0 (4) | C114—C113—H108 | 109.47 |
C109—N111—C112 | 122.0 (4) | C114—C113—H109 | 109.53 |
C104—N116—C117 | 131.4 (4) | C213—C214—C215 | 100.3 (9) |
C117—N119—C120 | 122.1 (4) | C113—C114—H110 | 110.98 |
C109—N108—H104 | 115.44 | C113—C114—H111 | 111.05 |
C102—N108—H104 | 115.60 | C115—C114—H110 | 111.18 |
C109—N111—H105 | 118.94 | C115—C114—H111 | 111.14 |
C112—N111—H105 | 119.06 | H110—C114—H111 | 109.18 |
C117—N116—H115 | 114.32 | C114—C115—H112 | 109.45 |
C104—N116—H115 | 114.30 | C114—C115—H113 | 109.31 |
C117—N119—H116 | 118.96 | C114—C115—H114 | 109.57 |
C120—N119—H116 | 118.97 | H112—C115—H113 | 109.38 |
N101—C102—N108 | 118.4 (5) | H112—C115—H114 | 109.61 |
N103—C102—N108 | 114.1 (4) | H113—C115—H114 | 109.51 |
N101—C102—N103 | 127.5 (4) | N119—C120—H117 | 109.23 |
N103—C104—N116 | 118.9 (4) | N119—C120—H118 | 109.21 |
N105—C104—N116 | 115.3 (4) | C121—C120—H117 | 109.23 |
N103—C104—N105 | 125.8 (5) | C121—C120—H118 | 109.19 |
N101—C106—C107 | 115.8 (5) | H117—C120—H118 | 107.89 |
N105—C106—C107 | 118.2 (4) | C120—C121—H119 | 108.63 |
N101—C106—N105 | 126.0 (4) | C120—C121—H120 | 108.68 |
O110—C109—N108 | 117.0 (4) | C122—C121—H119 | 108.70 |
O110—C109—N111 | 124.8 (5) | C122—C121—H120 | 108.65 |
N108—C109—N111 | 118.2 (4) | H119—C121—H120 | 107.59 |
N111—C112—C113 | 110.8 (5) | C121—C122—H121 | 108.98 |
N111—C112—C213 | 110.5 (5) | C121—C122—H122 | 108.96 |
C112—C113—C114 | 110.9 (10) | C123—C122—H121 | 108.87 |
C113—C114—C115 | 103.2 (10) | C123—C122—H122 | 109.02 |
O118—C117—N119 | 123.6 (5) | H121—C122—H122 | 107.78 |
N116—C117—N119 | 117.7 (5) | C122—C123—H123 | 109.46 |
O118—C117—N116 | 118.7 (4) | C122—C123—H124 | 109.48 |
N119—C120—C121 | 112.0 (5) | C122—C123—H125 | 109.52 |
C120—C121—C122 | 114.4 (4) | H123—C123—H124 | 109.51 |
C121—C122—C123 | 113.1 (4) | H123—C123—H125 | 109.32 |
H102—C107—H103 | 109.48 | H124—C123—H125 | 109.53 |
C106—C107—H102 | 109.47 | C112—C213—H208 | 109.95 |
C106—C107—H101 | 109.45 | C112—C213—H209 | 109.72 |
H101—C107—H103 | 109.44 | C214—C213—H208 | 109.71 |
C106—C107—H103 | 109.52 | C214—C213—H209 | 109.59 |
H101—C107—H102 | 109.47 | H208—C213—H209 | 108.16 |
N111—C112—H106 | 109.56 | C213—C214—H210 | 111.70 |
H106—C112—H107 | 107.99 | C213—C214—H211 | 111.81 |
C213—C112—H206 | 109.59 | C215—C214—H210 | 111.59 |
N111—C112—H107 | 109.47 | C215—C214—H211 | 111.64 |
N111—C112—H206 | 109.61 | H210—C214—H211 | 109.58 |
N111—C112—H207 | 109.55 | C214—C215—H212 | 109.27 |
C113—C112—H106 | 109.51 | C214—C215—H213 | 109.43 |
C113—C112—H107 | 109.46 | C214—C215—H214 | 109.46 |
H206—C112—H207 | 108.10 | H212—C215—H213 | 109.53 |
C213—C112—H207 | 109.47 | H212—C215—H214 | 109.53 |
H108—C113—H109 | 107.89 | H213—C215—H214 | 109.61 |
| | | |
C106—N101—C102—N103 | 1.2 (8) | N101—C106—C107—H103 | 94.41 |
C106—N101—C102—N108 | −178.0 (5) | N105—C106—C107—H101 | 154.33 |
C102—N101—C106—N105 | 0.5 (8) | N105—C106—C107—H102 | 34.35 |
C102—N101—C106—C107 | −179.7 (5) | N105—C106—C107—H103 | −85.69 |
C104—N103—C102—N101 | −1.3 (8) | N111—C112—C113—H108 | −56.65 |
C104—N103—C102—N108 | 178.0 (4) | N111—C112—C113—H109 | −174.76 |
C102—N103—C104—N105 | −0.3 (7) | H106—C112—C113—C114 | −174.69 |
C102—N103—C104—N116 | −179.1 (5) | H106—C112—C113—H108 | 64.32 |
C106—N105—C104—N103 | 1.7 (8) | H106—C112—C113—H109 | −53.79 |
C106—N105—C104—N116 | −179.4 (5) | H107—C112—C113—C114 | −56.49 |
C104—N105—C106—N101 | −1.8 (8) | H107—C112—C113—H108 | −177.48 |
C104—N105—C106—C107 | 178.3 (5) | H107—C112—C113—H109 | 64.41 |
C109—N108—C102—N101 | 5.3 (8) | C112—C113—C114—H110 | 64.73 |
C109—N108—C102—N103 | −174.1 (5) | C112—C113—C114—H111 | −56.91 |
C102—N108—C109—O110 | 172.3 (5) | H108—C113—C114—C115 | −55.01 |
C102—N108—C109—N111 | −5.3 (8) | H108—C113—C114—H110 | −174.20 |
C112—N111—C109—O110 | −2.5 (9) | H108—C113—C114—H111 | 64.16 |
C112—N111—C109—N108 | 174.9 (5) | H109—C113—C114—C115 | 63.10 |
C109—N111—C112—C113 | 174.5 (7) | H109—C113—C114—H110 | −56.09 |
C117—N116—C104—N103 | 0.6 (8) | H109—C113—C114—H111 | −177.73 |
C117—N116—C104—N105 | −178.4 (5) | C113—C114—C115—H112 | −78.61 |
C104—N116—C117—O118 | 175.4 (5) | C113—C114—C115—H113 | 161.62 |
C104—N116—C117—N119 | −2.6 (8) | C113—C114—C115—H114 | 41.62 |
C120—N119—C117—O118 | −2.9 (8) | H110—C114—C115—H112 | 40.44 |
C120—N119—C117—N116 | 175.0 (5) | H110—C114—C115—H113 | −79.33 |
C117—N119—C120—C121 | 113.9 (5) | H110—C114—C115—H114 | 160.66 |
N111—C112—C113—C114 | 64.3 (8) | H111—C114—C115—H112 | 162.28 |
C112—C113—C114—C115 | −176.1 (7) | H111—C114—C115—H113 | 42.51 |
N119—C120—C121—C122 | −64.9 (6) | H111—C114—C115—H114 | −77.50 |
C120—C121—C122—C123 | −178.8 (5) | N119—C120—C121—H119 | 173.48 |
H104—N108—C109—N111 | 174.78 | N119—C120—C121—H120 | 56.70 |
H104—N108—C102—N101 | −174.76 | H117—C120—C121—C122 | 56.24 |
H104—N108—C102—N103 | 5.86 | H117—C120—C121—H119 | −65.38 |
H104—N108—C109—O110 | −7.66 | H117—C120—C121—H120 | 177.83 |
H105—N111—C109—O110 | 177.49 | H118—C120—C121—C122 | 174.01 |
H105—N111—C109—N108 | −5.15 | H118—C120—C121—H119 | 52.40 |
C109—N111—C112—H106 | 53.53 | H118—C120—C121—H120 | −64.39 |
H105—N111—C112—H107 | 115.30 | C120—C121—C122—H121 | −57.60 |
C109—N111—C112—H107 | −64.71 | C120—C121—C122—H122 | 59.76 |
H105—N111—C112—C113 | −5.52 | H119—C121—C122—C123 | −57.26 |
H105—N111—C112—H106 | −126.46 | H119—C121—C122—H121 | 63.98 |
H115—N116—C104—N105 | 1.60 | H119—C121—C122—H122 | −178.66 |
H115—N116—C117—O118 | −4.60 | H120—C121—C122—C123 | 59.55 |
H115—N116—C117—N119 | 177.41 | H120—C121—C122—H121 | −179.22 |
H115—N116—C104—N103 | −179.41 | H120—C121—C122—H122 | −61.85 |
C117—N119—C120—H118 | −125.01 | C121—C122—C123—H123 | −57.12 |
H116—N119—C120—C121 | −66.02 | C121—C122—C123—H124 | −177.17 |
H116—N119—C120—H117 | 172.84 | C121—C122—C123—H125 | 62.72 |
H116—N119—C120—H118 | 55.06 | H121—C122—C123—H123 | −178.41 |
H116—N119—C117—O118 | 177.05 | H121—C122—C123—H124 | 61.54 |
H116—N119—C117—N116 | −5.07 | H121—C122—C123—H125 | −58.57 |
C117—N119—C120—H117 | −7.23 | H122—C122—C123—H123 | 64.25 |
N101—C106—C107—H101 | −25.57 | H122—C122—C123—H124 | −55.80 |
N101—C106—C107—H102 | −145.55 | H122—C122—C123—H125 | −175.91 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+1/2, −y+1/2, −z; (iii) x, y−1, z; (iv) −x+1/2, y+3/2, −z+1/2; (v) −x+1/2, −y+3/2, −z; (vi) x, y+1, z; (vii) −x+1/2, y−1/2, −z+1/2; (viii) −x, −y+3, −z; (ix) −x+1/2, y−3/2, −z+1/2; (x) x+1/2, y−1/2, z; (xi) x−1/2, y+1/2, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N108—H104···O110vii | 0.88 | 1.99 | 2.861 (6) | 173 |
N111—H105···N101 | 0.88 | 1.96 | 2.653 (6) | 135 |
N116—H115···O118ii | 0.88 | 1.95 | 2.818 (5) | 170 |
N119—H116···N103 | 0.88 | 2.01 | 2.690 (7) | 133 |
C120—H117···O118 | 0.99 | 2.39 | 2.798 (6) | 104 |
Symmetry codes: (ii) −x+1/2, −y+1/2, −z; (vii) −x+1/2, y−1/2, −z+1/2. |
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