2-Amino-4-(4-bromo-phen-yl)-8-trifluoro-methyl-3,4-dihydropyrimido[1,2-a][1,3,5]triazin-6(5H)-one.

The title compound, C(13)H(9)BrF(3)N(5)O, crystallizes with two independent mol-ecules in the asymmetric unit. The pyrimidine rings of the mol-ecules are planar [maximum deviations 0.053 (3) and 0.012 (3) Å], while the triazine rings adopt flattened half-boat conformations with the p-bromo-phenyl rings in the flagpole positions. The crystal packing is stabilized by a three-dimensional network of inter-molecular N-H⋯N, N-H⋯O and N-H⋯F hydrogen bonds.

Related literature

For the crystal structure of 7,7-dimethyl-2-phenyl-6,7-di­hydro-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amine, see: Dolzhenko et al. (2007 ▶). For the preparation of benzo-fused analogues, see: Dolzhenko et al. (2008a ▶). For the previous report in this series, see: Dolzhenko et al. (2008b ▶).

Experimental

Crystal data

C13H9BrF3N5O

M = 388.16

Orthorhombic,

a = 10.0531 (4) Å

b = 29.9108 (13) Å

c = 10.1945 (4) Å

V = 3065.4 (2) Å3

Z = 8

Mo Kα radiation

μ = 2.73 mm−1

T = 223 K

0.46 × 0.34 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.367, T max = 0.612 (expected range = 0.348–0.580)

20728 measured reflections

6287 independent reflections

4979 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.138

S = 1.04

6287 reflections

432 parameters

16 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.50 e Å−3

Δρmin = −0.74 e Å−3

Absolute structure: Flack (1983 ▶), 2044 Friedel pairs

Flack parameter: 0.011 (10)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536809007612/ng2543sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007612/ng2543Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H9BrF3N5O	Dx = 1.682 Mg m−3
Mr = 388.16	Melting point: 516 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5069 reflections
a = 10.0531 (4) Å	θ = 2.4–25.1°
b = 29.9108 (13) Å	µ = 2.73 mm−1
c = 10.1945 (4) Å	T = 223 K
V = 3065.4 (2) Å3	Block, colourless
Z = 8	0.46 × 0.34 × 0.20 mm
F(000) = 1536

Bruker SMART APEX CCD diffractometer	6287 independent reflections
Radiation source: fine-focus sealed tube	4979 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 27.5°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −12→13
Tmin = 0.367, Tmax = 0.612	k = −38→38
20728 measured reflections	l = −13→11

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.138	w = 1/[σ2(Fo2) + (0.0646P)2 + 2.1384P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
6287 reflections	Δρmax = 1.50 e Å−3
432 parameters	Δρmin = −0.73 e Å−3
16 restraints	Absolute structure: Flack (1983), 2044 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.011 (10)

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	Occ. (<1)
O1	1.0316 (3)	0.34878 (10)	1.2353 (3)	0.0346 (7)
F1	0.9317 (4)	0.36022 (11)	1.7842 (4)	0.0634 (10)
F2	0.8409 (4)	0.30866 (11)	1.6709 (4)	0.0750 (12)
F3	0.7371 (4)	0.37004 (16)	1.7065 (5)	0.0873 (14)
N1	1.0194 (3)	0.47967 (11)	1.2317 (4)	0.0259 (7)
H1N	1.012 (5)	0.4927 (15)	1.156 (3)	0.031*
N2	0.9826 (3)	0.48272 (10)	1.4583 (3)	0.0237 (7)
N3	1.0181 (3)	0.41352 (10)	1.3521 (3)	0.0232 (7)
N4	0.9342 (4)	0.41721 (11)	1.5665 (4)	0.0290 (7)
N5	0.9597 (4)	0.54572 (11)	1.3299 (4)	0.0335 (8)
H5A	0.919 (5)	0.5568 (15)	1.401 (3)	0.040*
H5B	0.982 (5)	0.5632 (14)	1.262 (4)	0.040*
C1	1.0910 (4)	0.43826 (13)	1.2510 (4)	0.0250 (8)
H1A	1.0904	0.4209	1.1683	0.030*
C2	0.9892 (4)	0.50251 (13)	1.3412 (4)	0.0249 (8)
C3	0.9789 (4)	0.43766 (13)	1.4607 (4)	0.0258 (8)
C4	0.9958 (4)	0.36750 (13)	1.3367 (5)	0.0288 (9)
C5	0.9359 (5)	0.34747 (15)	1.4486 (5)	0.0387 (10)
H5	0.9122	0.3171	1.4478	0.046*
C6	0.9137 (5)	0.37273 (15)	1.5558 (5)	0.0358 (10)
C7	0.8558 (7)	0.35237 (18)	1.6796 (6)	0.0542 (15)
C8	1.2338 (4)	0.44558 (14)	1.2947 (5)	0.0279 (9)
C9	1.3053 (5)	0.41197 (16)	1.3543 (6)	0.0454 (13)
H9	1.2654	0.3838	1.3664	0.054*
C10	1.4348 (5)	0.41866 (18)	1.3968 (6)	0.0519 (14)
H10	1.4826	0.3954	1.4372	0.062*
C11	1.4917 (4)	0.45984 (18)	1.3788 (6)	0.0441 (12)
C12	1.4249 (5)	0.49351 (18)	1.3178 (6)	0.0450 (12)
H12	1.4660	0.5214	1.3044	0.054*
C13	1.2959 (5)	0.48627 (15)	1.2758 (5)	0.0362 (10)
H13	1.2495	0.5095	1.2336	0.043*
Br1	1.66612 (4)	0.47071 (3)	1.44122 (8)	0.0697 (2)
O2	0.7222 (3)	0.09824 (9)	0.9889 (3)	0.0338 (7)
F4	1.2813 (4)	0.10516 (13)	1.0040 (5)	0.0782 (13)
F5	1.1837 (3)	0.05015 (8)	1.0941 (4)	0.0578 (10)
F6	1.2446 (3)	0.10589 (11)	1.2081 (5)	0.0631 (10)
N6	0.7243 (3)	0.22885 (11)	1.0553 (4)	0.0271 (8)
H6N	0.653 (3)	0.2463 (13)	1.073 (5)	0.032*
N7	0.9576 (3)	0.22901 (10)	1.0690 (4)	0.0261 (7)
N8	0.8395 (3)	0.16152 (10)	1.0287 (4)	0.0237 (7)
N9	1.0675 (3)	0.16188 (11)	1.0790 (4)	0.0288 (8)
N10	0.8364 (4)	0.29270 (11)	1.1091 (4)	0.0319 (8)
H10A	0.909 (3)	0.3050 (15)	1.144 (5)	0.038*
H10B	0.762 (3)	0.3090 (15)	1.104 (6)	0.038*
C20	1.1928 (5)	0.09342 (14)	1.0926 (6)	0.0377 (11)
C14	0.7273 (4)	0.18807 (12)	0.9806 (5)	0.0258 (9)
H14	0.6443	0.1713	0.9985	0.031*
C15	0.8407 (4)	0.25037 (12)	1.0759 (4)	0.0231 (8)
C16	0.9555 (4)	0.18357 (12)	1.0582 (4)	0.0246 (8)
C17	0.8279 (4)	0.11509 (13)	1.0201 (4)	0.0255 (8)
C18	0.9505 (4)	0.09218 (13)	1.0451 (5)	0.0287 (9)
H18	0.9540	0.0608	1.0441	0.034*
C19	1.0602 (4)	0.11631 (13)	1.0699 (4)	0.0291 (9)
Br2	0.74894 (14)	0.22662 (3)	0.38715 (10)	0.0924 (5)	0.899 (3)
C21	0.7359 (4)	0.19636 (19)	0.8349 (3)	0.0312 (13)	0.899 (3)
C22	0.6379 (4)	0.22284 (19)	0.7782 (4)	0.0475 (14)	0.899 (3)
H22	0.5695	0.2348	0.8304	0.057*	0.899 (3)
C23	0.6409 (4)	0.23160 (16)	0.6443 (4)	0.0599 (19)	0.899 (3)
H23	0.5747	0.2495	0.6060	0.072*	0.899 (3)
C24	0.7420 (4)	0.21389 (14)	0.5671 (3)	0.0509 (16)	0.899 (3)
C25	0.8400 (4)	0.18741 (14)	0.6238 (3)	0.0621 (19)	0.899 (3)
H25	0.9084	0.1754	0.5716	0.075*	0.899 (3)
C26	0.8370 (4)	0.17865 (16)	0.7577 (3)	0.0463 (16)	0.899 (3)
H26	0.9033	0.1607	0.7960	0.056*	0.899 (3)
Br3	0.8608 (7)	0.21715 (19)	0.3838 (6)	0.054 (2)*	0.101 (3)
C21A	0.756 (6)	0.197 (3)	0.829 (2)	0.045*	0.101 (3)
C22A	0.668 (5)	0.219 (3)	0.747 (3)	0.062*	0.101 (3)
H22A	0.5867	0.2298	0.7806	0.075*	0.101 (3)
C23A	0.699 (4)	0.225 (2)	0.616 (2)	0.062*	0.101 (3)
H23A	0.6392	0.2402	0.5601	0.075*	0.101 (3)
C24A	0.818 (3)	0.2090 (17)	0.5660 (15)	0.062*	0.101 (3)
C25A	0.907 (4)	0.1867 (17)	0.6480 (18)	0.062*	0.101 (3)
H25A	0.9876	0.1758	0.6145	0.075*	0.101 (3)
C26A	0.875 (5)	0.181 (2)	0.7796 (19)	0.062*	0.101 (3)
H26A	0.9351	0.1654	0.8350	0.075*	0.101 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0404 (17)	0.0260 (14)	0.0375 (18)	−0.0012 (12)	−0.0011 (14)	−0.0105 (13)
F1	0.103 (3)	0.0442 (17)	0.0428 (19)	−0.0128 (17)	0.0068 (19)	0.0091 (14)
F2	0.119 (3)	0.0427 (17)	0.063 (2)	−0.039 (2)	0.021 (2)	0.0051 (17)
F3	0.071 (3)	0.101 (3)	0.090 (3)	0.004 (2)	0.044 (2)	0.032 (3)
N1	0.0288 (17)	0.0241 (16)	0.0247 (18)	0.0042 (13)	−0.0028 (14)	−0.0010 (14)
N2	0.0241 (15)	0.0214 (15)	0.0255 (19)	0.0018 (12)	0.0019 (14)	0.0007 (14)
N3	0.0235 (16)	0.0197 (14)	0.0265 (19)	0.0033 (12)	−0.0003 (13)	−0.0010 (13)
N4	0.0333 (18)	0.0281 (16)	0.0258 (18)	−0.0022 (14)	0.0025 (15)	0.0023 (15)
N5	0.047 (2)	0.0229 (17)	0.031 (2)	0.0074 (15)	0.0066 (18)	0.0020 (16)
C1	0.0256 (19)	0.0257 (19)	0.024 (2)	0.0051 (15)	0.0029 (15)	−0.0009 (16)
C2	0.0203 (18)	0.0254 (18)	0.029 (2)	0.0001 (14)	−0.0008 (16)	0.0024 (16)
C3	0.0210 (17)	0.0277 (19)	0.029 (2)	0.0016 (14)	−0.0037 (16)	−0.0034 (17)
C4	0.027 (2)	0.0196 (18)	0.040 (2)	0.0005 (15)	−0.0060 (18)	−0.0055 (18)
C5	0.047 (2)	0.028 (2)	0.041 (3)	−0.0088 (18)	−0.003 (2)	0.002 (2)
C6	0.034 (2)	0.032 (2)	0.041 (3)	−0.0076 (18)	0.000 (2)	0.005 (2)
C7	0.071 (4)	0.041 (3)	0.050 (4)	−0.013 (3)	0.016 (3)	0.005 (3)
C8	0.027 (2)	0.031 (2)	0.026 (2)	0.0038 (16)	0.0029 (17)	−0.0034 (17)
C9	0.034 (2)	0.037 (2)	0.065 (4)	−0.0027 (19)	−0.006 (2)	0.019 (2)
C10	0.035 (2)	0.059 (3)	0.062 (4)	0.012 (2)	−0.008 (2)	0.018 (3)
C11	0.020 (2)	0.067 (3)	0.045 (3)	0.000 (2)	−0.009 (2)	−0.015 (3)
C12	0.033 (2)	0.044 (3)	0.058 (3)	−0.009 (2)	0.006 (2)	−0.012 (2)
C13	0.029 (2)	0.033 (2)	0.047 (3)	−0.0071 (18)	−0.001 (2)	0.000 (2)
Br1	0.0269 (2)	0.1078 (5)	0.0743 (4)	0.0028 (3)	−0.0111 (3)	−0.0396 (4)
O2	0.0328 (16)	0.0275 (14)	0.0410 (19)	−0.0115 (12)	−0.0019 (13)	−0.0060 (13)
F4	0.054 (2)	0.075 (2)	0.105 (3)	0.0289 (17)	0.040 (2)	0.035 (2)
F5	0.0513 (18)	0.0253 (13)	0.097 (3)	0.0075 (12)	−0.0090 (18)	−0.0024 (16)
F6	0.0541 (19)	0.0514 (17)	0.084 (3)	0.0087 (15)	−0.0318 (19)	−0.0024 (19)
N6	0.0182 (16)	0.0241 (16)	0.039 (2)	0.0027 (12)	−0.0038 (14)	−0.0013 (15)
N7	0.0238 (16)	0.0228 (15)	0.0317 (19)	−0.0017 (12)	−0.0012 (14)	−0.0055 (15)
N8	0.0236 (16)	0.0170 (14)	0.0306 (19)	−0.0037 (13)	0.0000 (13)	−0.0022 (13)
N9	0.0234 (16)	0.0271 (16)	0.036 (2)	−0.0004 (13)	−0.0010 (15)	−0.0021 (16)
N10	0.0282 (18)	0.0223 (17)	0.045 (2)	−0.0005 (13)	−0.0071 (16)	−0.0066 (16)
C20	0.036 (2)	0.024 (2)	0.053 (3)	0.0041 (17)	0.004 (2)	0.006 (2)
C14	0.0235 (19)	0.0188 (18)	0.035 (2)	−0.0034 (14)	−0.0021 (16)	0.0006 (16)
C15	0.0263 (19)	0.0203 (17)	0.0227 (19)	0.0001 (14)	−0.0019 (16)	0.0032 (16)
C16	0.0223 (18)	0.0272 (19)	0.024 (2)	−0.0066 (15)	0.0011 (16)	−0.0003 (16)
C17	0.033 (2)	0.0238 (18)	0.0199 (19)	−0.0006 (16)	0.0032 (16)	−0.0034 (16)
C18	0.032 (2)	0.0179 (17)	0.036 (2)	−0.0016 (16)	−0.0008 (18)	0.0034 (17)
C19	0.031 (2)	0.028 (2)	0.028 (2)	0.0018 (16)	0.0023 (18)	0.0035 (18)
Br2	0.1629 (13)	0.0842 (6)	0.0300 (3)	−0.0488 (7)	−0.0104 (5)	0.0130 (4)
C21	0.044 (3)	0.019 (2)	0.030 (3)	−0.017 (2)	−0.012 (2)	−0.0023 (19)
C22	0.053 (4)	0.051 (4)	0.039 (3)	0.004 (3)	−0.011 (3)	0.008 (3)
C23	0.084 (5)	0.051 (4)	0.045 (4)	−0.008 (4)	−0.024 (4)	0.012 (3)
C24	0.087 (5)	0.043 (3)	0.023 (3)	−0.027 (3)	−0.007 (3)	0.000 (3)
C25	0.092 (6)	0.063 (4)	0.031 (3)	−0.010 (4)	0.006 (3)	−0.011 (3)
C26	0.065 (4)	0.046 (3)	0.028 (3)	0.001 (3)	−0.003 (3)	−0.004 (2)

O1—C4	1.229 (5)	N6—H6N	0.902 (19)
F1—C7	1.331 (8)	N7—C15	1.339 (5)
F2—C7	1.319 (6)	N7—C16	1.364 (5)
F3—C7	1.334 (7)	N8—C16	1.373 (5)
N1—C2	1.344 (6)	N8—C17	1.396 (5)
N1—C1	1.446 (5)	N8—C14	1.464 (5)
N1—H1N	0.87 (2)	N9—C16	1.317 (5)
N2—C2	1.334 (6)	N9—C19	1.368 (5)
N2—C3	1.348 (5)	N10—C15	1.311 (5)
N3—C3	1.379 (5)	N10—H10A	0.89 (2)
N3—C4	1.403 (5)	N10—H10B	0.90 (2)
N3—C1	1.465 (5)	C20—C19	1.516 (6)
N4—C3	1.318 (6)	C14—C21	1.509 (5)
N4—C6	1.351 (6)	C14—C21A	1.591 (9)
N5—C2	1.331 (5)	C14—H14	0.9900
N5—H5A	0.895 (14)	C17—C18	1.433 (6)
N5—H5B	0.892 (14)	C18—C19	1.343 (6)
C1—C8	1.519 (6)	C18—H18	0.9400
C1—H1A	0.9900	Br2—C24	1.875 (3)
C4—C5	1.423 (7)	C21—C22	1.3900
C5—C6	1.347 (8)	C21—C26	1.3900
C5—H5	0.9400	C22—C23	1.3900
C6—C7	1.517 (7)	C22—H22	0.9400
C8—C9	1.377 (6)	C23—C24	1.3900
C8—C13	1.381 (6)	C23—H23	0.9400
C9—C10	1.387 (7)	C24—C25	1.3900
C9—H9	0.9400	C25—C26	1.3900
C10—C11	1.371 (8)	C25—H25	0.9400
C10—H10	0.9400	C26—H26	0.9400
C11—C12	1.361 (8)	Br3—C24A	1.921 (7)
C11—Br1	1.893 (4)	C21A—C22A	1.3900
C12—C13	1.383 (7)	C21A—C26A	1.3900
C12—H12	0.9400	C22A—C23A	1.3900
C13—H13	0.9400	C22A—H22A	0.9400
O2—C17	1.219 (5)	C23A—C24A	1.3900
F4—C20	1.316 (6)	C23A—H23A	0.9400
F5—C20	1.298 (5)	C24A—C25A	1.3900
F6—C20	1.341 (7)	C25A—C26A	1.3900
N6—C15	1.352 (5)	C25A—H25A	0.9400
N6—C14	1.439 (5)	C26A—H26A	0.9400
C2—N1—C1	115.8 (4)	F5—C20—F4	108.7 (4)
C2—N1—H1N	119 (3)	F5—C20—F6	107.1 (4)
C1—N1—H1N	123 (3)	F4—C20—F6	105.4 (4)
C2—N2—C3	117.5 (3)	F5—C20—C19	113.0 (4)
C3—N3—C4	123.9 (4)	F4—C20—C19	111.7 (4)
C3—N3—C1	116.3 (3)	F6—C20—C19	110.5 (4)
C4—N3—C1	119.7 (3)	N6—C14—N8	107.3 (3)
C3—N4—C6	116.3 (4)	N6—C14—C21	112.5 (4)
C2—N5—H5A	113 (3)	N8—C14—C21	112.0 (4)
C2—N5—H5B	126 (4)	N6—C14—C21A	112 (3)
H5A—N5—H5B	121 (5)	N8—C14—C21A	106 (2)
N1—C1—N3	106.2 (3)	C21—C14—C21A	7(2)
N1—C1—C8	112.7 (3)	N6—C14—H14	108.3
N3—C1—C8	109.8 (3)	N8—C14—H14	108.3
N1—C1—H1A	109.3	C21—C14—H14	108.3
N3—C1—H1A	109.3	C21A—C14—H14	114.4
C8—C1—H1A	109.3	N10—C15—N7	120.2 (3)
N5—C2—N2	119.8 (4)	N10—C15—N6	118.1 (3)
N5—C2—N1	118.1 (4)	N7—C15—N6	121.6 (3)
N2—C2—N1	122.0 (4)	N9—C16—N7	117.7 (3)
N4—C3—N2	119.2 (4)	N9—C16—N8	121.7 (3)
N4—C3—N3	120.7 (3)	N7—C16—N8	120.6 (3)
N2—C3—N3	120.0 (4)	O2—C17—N8	120.0 (4)
O1—C4—N3	119.7 (4)	O2—C17—C18	126.8 (4)
O1—C4—C5	127.3 (4)	N8—C17—C18	113.1 (3)
N3—C4—C5	113.0 (4)	C19—C18—C17	118.9 (4)
C6—C5—C4	119.0 (4)	C19—C18—H18	120.6
C6—C5—H5	120.5	C17—C18—H18	120.6
C4—C5—H5	120.5	C18—C19—N9	126.3 (4)
C5—C6—N4	126.3 (4)	C18—C19—C20	120.6 (4)
C5—C6—C7	120.9 (4)	N9—C19—C20	113.1 (4)
N4—C6—C7	112.8 (4)	C22—C21—C26	120.0
F2—C7—F1	107.1 (5)	C22—C21—C14	117.5 (3)
F2—C7—F3	107.7 (5)	C26—C21—C14	122.5 (3)
F1—C7—F3	106.2 (5)	C21—C22—C23	120.0
F2—C7—C6	112.7 (5)	C21—C22—H22	120.0
F1—C7—C6	112.1 (4)	C23—C22—H22	120.0
F3—C7—C6	110.8 (5)	C24—C23—C22	120.0
C9—C8—C13	118.0 (4)	C24—C23—H23	120.0
C9—C8—C1	121.2 (4)	C22—C23—H23	120.0
C13—C8—C1	120.9 (4)	C23—C24—C25	120.0
C8—C9—C10	121.5 (4)	C23—C24—Br2	120.2 (2)
C8—C9—H9	119.2	C25—C24—Br2	119.7 (2)
C10—C9—H9	119.2	C24—C25—C26	120.0
C11—C10—C9	118.7 (5)	C24—C25—H25	120.0
C11—C10—H10	120.7	C26—C25—H25	120.0
C9—C10—H10	120.7	C25—C26—C21	120.0
C12—C11—C10	121.3 (4)	C25—C26—H26	120.0
C12—C11—Br1	118.9 (4)	C21—C26—H26	120.0
C10—C11—Br1	119.7 (4)	C22A—C21A—C26A	120.0
C11—C12—C13	119.3 (5)	C22A—C21A—C14	123 (3)
C11—C12—H12	120.4	C26A—C21A—C14	117 (3)
C13—C12—H12	120.4	C21A—C22A—C23A	120.0
C8—C13—C12	121.2 (5)	C21A—C22A—H22A	120.0
C8—C13—H13	119.4	C23A—C22A—H22A	120.0
C12—C13—H13	119.4	C24A—C23A—C22A	120.0
C15—N6—C14	117.9 (3)	C24A—C23A—H23A	120.0
C15—N6—H6N	112 (3)	C22A—C23A—H23A	120.0
C14—N6—H6N	128 (3)	C23A—C24A—C25A	120.0
C15—N7—C16	117.8 (3)	C23A—C24A—Br3	119.9 (4)
C16—N8—C17	124.2 (3)	C25A—C24A—Br3	120.0 (4)
C16—N8—C14	117.9 (3)	C26A—C25A—C24A	120.0
C17—N8—C14	117.0 (3)	C26A—C25A—H25A	120.0
C16—N9—C19	115.7 (3)	C24A—C25A—H25A	120.0
C15—N10—H10A	118 (3)	C25A—C26A—C21A	120.0
C15—N10—H10B	122 (3)	C25A—C26A—H26A	120.0
H10A—N10—H10B	119 (5)	C21A—C26A—H26A	120.0
C2—N1—C1—N3	49.4 (5)	C14—N6—C15—N10	160.7 (4)
C2—N1—C1—C8	−70.9 (5)	C14—N6—C15—N7	−22.5 (6)
C3—N3—C1—N1	−45.3 (4)	C19—N9—C16—N7	178.7 (4)
C4—N3—C1—N1	136.7 (4)	C19—N9—C16—N8	−0.3 (6)
C3—N3—C1—C8	76.9 (4)	C15—N7—C16—N9	−166.1 (4)
C4—N3—C1—C8	−101.0 (4)	C15—N7—C16—N8	12.9 (6)
C3—N2—C2—N5	163.1 (4)	C17—N8—C16—N9	1.2 (6)
C3—N2—C2—N1	−13.9 (6)	C14—N8—C16—N9	−167.5 (4)
C1—N1—C2—N5	160.7 (4)	C17—N8—C16—N7	−177.8 (4)
C1—N1—C2—N2	−22.3 (6)	C14—N8—C16—N7	13.5 (6)
C6—N4—C3—N2	170.1 (4)	C16—N8—C17—O2	−177.5 (4)
C6—N4—C3—N3	−8.0 (6)	C14—N8—C17—O2	−8.7 (6)
C2—N2—C3—N4	−160.4 (4)	C16—N8—C17—C18	−0.2 (6)
C2—N2—C3—N3	17.8 (5)	C14—N8—C17—C18	168.6 (4)
C4—N3—C3—N4	9.9 (6)	O2—C17—C18—C19	175.5 (4)
C1—N3—C3—N4	−167.9 (4)	N8—C17—C18—C19	−1.6 (6)
C4—N3—C3—N2	−168.2 (3)	C17—C18—C19—N9	2.6 (7)
C1—N3—C3—N2	13.9 (5)	C17—C18—C19—C20	−178.1 (4)
C3—N3—C4—O1	178.5 (4)	C16—N9—C19—C18	−1.6 (7)
C1—N3—C4—O1	−3.8 (6)	C16—N9—C19—C20	179.1 (4)
C3—N3—C4—C5	−3.8 (5)	F5—C20—C19—C18	−4.4 (7)
C1—N3—C4—C5	174.0 (4)	F4—C20—C19—C18	118.5 (5)
O1—C4—C5—C6	174.3 (4)	F6—C20—C19—C18	−124.5 (5)
N3—C4—C5—C6	−3.2 (6)	F5—C20—C19—N9	175.0 (4)
C4—C5—C6—N4	5.0 (8)	F4—C20—C19—N9	−62.1 (6)
C4—C5—C6—C7	−177.2 (5)	F6—C20—C19—N9	54.9 (5)
C3—N4—C6—C5	0.8 (7)	N6—C14—C21—C22	−56.3 (4)
C3—N4—C6—C7	−177.1 (4)	N8—C14—C21—C22	−177.3 (3)
C5—C6—C7—F2	4.5 (8)	C21A—C14—C21—C22	−147 (25)
N4—C6—C7—F2	−177.4 (5)	N6—C14—C21—C26	123.7 (4)
C5—C6—C7—F1	125.4 (5)	N8—C14—C21—C26	2.6 (5)
N4—C6—C7—F1	−56.6 (6)	C21A—C14—C21—C26	33 (24)
C5—C6—C7—F3	−116.3 (6)	C26—C21—C22—C23	0.0
N4—C6—C7—F3	61.8 (6)	C14—C21—C22—C23	180.0 (5)
N1—C1—C8—C9	160.8 (5)	C21—C22—C23—C24	0.0
N3—C1—C8—C9	42.5 (6)	C22—C23—C24—C25	0.0
N1—C1—C8—C13	−19.2 (6)	C22—C23—C24—Br2	−178.6 (3)
N3—C1—C8—C13	−137.5 (4)	C23—C24—C25—C26	0.0
C13—C8—C9—C10	1.3 (8)	Br2—C24—C25—C26	178.6 (3)
C1—C8—C9—C10	−178.7 (5)	C24—C25—C26—C21	0.0
C8—C9—C10—C11	0.1 (9)	C22—C21—C26—C25	0.0
C9—C10—C11—C12	−1.5 (9)	C14—C21—C26—C25	−180.0 (5)
C9—C10—C11—Br1	177.8 (5)	N6—C14—C21A—C22A	−66 (4)
C10—C11—C12—C13	1.4 (9)	N8—C14—C21A—C22A	177 (3)
Br1—C11—C12—C13	−177.9 (4)	C21—C14—C21A—C22A	26 (22)
C9—C8—C13—C12	−1.4 (8)	N6—C14—C21A—C26A	114 (3)
C1—C8—C13—C12	178.6 (5)	N8—C14—C21A—C26A	−3(4)
C11—C12—C13—C8	0.1 (8)	C21—C14—C21A—C26A	−154 (27)
C15—N6—C14—N8	44.6 (5)	C26A—C21A—C22A—C23A	0.0
C15—N6—C14—C21	−79.0 (5)	C14—C21A—C22A—C23A	−180 (6)
C15—N6—C14—C21A	−71 (2)	C21A—C22A—C23A—C24A	0.0
C16—N8—C14—N6	−40.1 (5)	C22A—C23A—C24A—C25A	0.0
C17—N8—C14—N6	150.4 (3)	C22A—C23A—C24A—Br3	179 (4)
C16—N8—C14—C21	83.9 (5)	C23A—C24A—C25A—C26A	0.0
C17—N8—C14—C21	−85.6 (5)	Br3—C24A—C25A—C26A	−179 (4)
C16—N8—C14—C21A	80 (3)	C24A—C25A—C26A—C21A	0.0
C17—N8—C14—C21A	−89 (3)	C22A—C21A—C26A—C25A	0.0
C16—N7—C15—N10	168.1 (4)	C14—C21A—C26A—C25A	180 (6)
C16—N7—C15—N6	−8.7 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2i	0.87 (2)	2.15 (2)	3.005 (5)	171 (5)
N5—H5A···O2ii	0.90 (1)	2.09 (3)	2.905 (5)	152 (5)
N5—H5B···N4i	0.89 (1)	2.25 (2)	3.095 (6)	159 (5)
N5—H5B···F1i	0.89 (1)	2.46 (4)	3.054 (5)	124 (4)
N6—H6N···N7iii	0.90 (2)	2.10 (3)	2.967 (5)	160 (5)
N10—H10A···O1	0.89 (2)	2.03 (3)	2.885 (5)	162 (5)
N10—H10B···N9iii	0.90 (2)	2.15 (2)	3.041 (5)	171 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N2i	0.87 (2)	2.15 (2)	3.005 (5)	171 (5)
N5—H5A⋯O2ii	0.895 (14)	2.09 (3)	2.905 (5)	152 (5)
N5—H5B⋯N4i	0.892 (14)	2.25 (2)	3.095 (6)	159 (5)
N5—H5B⋯F1i	0.892 (14)	2.46 (4)	3.054 (5)	124 (4)
N6—H6N⋯N7iii	0.902 (19)	2.10 (3)	2.967 (5)	160 (5)
N10—H10A⋯O1	0.89 (2)	2.03 (3)	2.885 (5)	162 (5)
N10—H10B⋯N9iii	0.90 (2)	2.15 (2)	3.041 (5)	171 (5)

Symmetry codes: (i) ; (ii) ; (iii) .