2,4-Di(butyl­ureido)-6-methyl-s-triazine

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.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](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

Author Response:

 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

Author Response:

 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

---

Computing details

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

Crystal data

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) Å^3	Plate, colourless
Z = 8	0.50 × 0.10 × 0.04 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.187	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ^2(Fo^2) + (0.010P)^2] where P = (Fo^2 + 2Fc^2)/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

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 F^{2 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 F}2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of F}2 > σ(F^{2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F}2 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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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···N108^i	2.861 (6)	H105···C214	2.6746
O118···N116^ii	2.818 (5)	H105···H210	2.1032
O118···C104^iii	3.160 (7)	H105···N101	1.9616
O110···H107	2.8545	H105···C102	2.5553
O110···H104^i	1.9860	H106···C120^iv	2.9593
O110···H116^i	2.9049	H106···C121^iv	3.0051
O110···H118^iv	2.6799	H106···H118^iv	2.1886
O110···H106	2.7031	H106···O110	2.7031
O110···H207	2.4721	H106···C109^vi	2.9478
O118···H117	2.3882	H107···O110	2.8545
O118···H103^v	2.8024	H107···H110	2.5404
O118···H115^ii	1.9452	H108···N101^vi	2.7460
N101···N111	2.653 (6)	H108···H105	2.4845
N101···C104^vi	3.314 (8)	H108···H114	2.2647
N103···C117^vi	3.293 (8)	H108···N111^vi	2.9418
N103···N119	2.690 (7)	H108···C102^vi	3.0762
N108···O110^vii	2.861 (6)	H110···H124^xi	2.2660
N111···N101	2.653 (6)	H110···H107	2.5404
N116···C106^iii	3.328 (8)	H110···C123^xi	3.0648
N116···O118^ii	2.818 (5)	H111···H114^iii	2.5667
N119···C102^iii	3.415 (8)	H111···H105	2.1788
N119···N103	2.690 (7)	H111···N111	2.6311
N101···H105	1.9616	H113···H113^viii	2.3559
N101···H108^iii	2.7460	H114···H111^vi	2.5667
N103···H116	2.0131	H114···H108	2.2647
N105···H103^iii	2.8122	H115···O118^ii	1.9452
N108···H206^iii	2.8887	H115···C117^ii	2.8798
N111···H111	2.6311	H116···N103	2.0131
N111···H210	2.6775	H116···O110^vii	2.9049
N111···H108^iii	2.9418	H116···C104	2.5914
N119···H122	2.7523	H117···H121	2.5457
C102···N119^vi	3.415 (8)	H117···O118	2.3882
C102···C117^vi	3.420 (8)	H117···H122^iii	2.4896
C104···N101^iii	3.314 (8)	H118···C112^ix	2.8641
C104···C117^vi	3.418 (9)	H118···O110^ix	2.6799
C104···O118^vi	3.160 (7)	H118···H207^ix	2.1315
C106···N116^vi	3.328 (8)	H118···H106^ix	2.1886
C107···C215^viii	3.588 (16)	H119···H125	2.5559
C112···C121^iv	3.585 (8)	H119···C112^ix	3.0692
C117···C102^iii	3.420 (8)	H119···H123^iii	2.5286
C117···N103^iii	3.293 (8)	H119···H207^ix	2.4397
C117···C104^iii	3.418 (9)	H120···H123	2.5278
C121···C112^ix	3.585 (8)	H121···H117	2.5457
C102···H108^iii	3.0762	H122···H117^vi	2.4896
C102···H105	2.5553	H122···N119	2.7523
C104···H116	2.5914	H123···H120	2.5278
C109···H106^iii	2.9478	H123···H119^vi	2.5286
C109···H206^iii	2.7132	H124···H110^x	2.2660
C109···H104^i	2.9284	H124···H213^x	2.4615
C112···H118^iv	2.8641	H125···H119	2.5559
C112···H119^iv	3.0692	H206···N108^vi	2.8887
C114···H105	2.7231	H206···C109^vi	2.7132
C215···C107^viii	3.588 (16)	H207···O110	2.4721
C117···H115^ii	2.8798	H207···C120^iv	2.8520
C120···H207^ix	2.8520	H207···C121^iv	2.9654
C120···H106^ix	2.9593	H207···H118^iv	2.1315
C121···H207^ix	2.9654	H207···H119^iv	2.4397
C121···H106^ix	3.0051	H208···H211^iii	2.5930
C123···H110^x	3.0648	H208···H213	2.2122
C214···H105	2.6746	H209···H212	2.4667
H101···H210	2.5427	H210···N111	2.6775
H103···N105^vi	2.8122	H210···H101	2.5427
H103···O118^v	2.8024	H210···H105	2.1032
H104···C109^vii	2.9284	H211···H208^vi	2.5930
H104···O110^vii	1.9860	H212···H209	2.4667
H105···C114	2.7231	H213···H208	2.2122
H105···H108	2.4845	H213···H124^xi	2.4615
H105···H111	2.1788	H214···H214^viii	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)

D—H···A	D—H	H···A	D···A	D—H···A
N108—H104···O110^vii	0.88	1.99	2.861 (6)	173
N111—H105···N101	0.88	1.96	2.653 (6)	135
N116—H115···O118^ii	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.