7-Benzyl-oxymethyl-9-bromo-6-chloro-9-deaza-purine.

The title compound, C(14)H(11)BrClN(3)O, crystallizes with two independent mol-ecules in the asymmetric unit. In the crystal, the molecules are linked by C-N⋯Br halogen bonds, as well as weak methyl-ene C-H⋯π, phenyl C-H⋯π, C-H⋯Br and phenyl C-H⋯O(ether) inter-actions.

Related literature

For synthetic details, see Clinch et al. (2010 ▶). For Br⋯N halogen bonding, see: Kubicki (2004 ▶); Metrangolo et al. (2008 ▶). For a related structure, see: Sakore & Sobell (1969 ▶).

Experimental

Crystal data

C14H11BrClN3O

M = 352.62

Triclinic,

a = 7.8999 (2) Å

b = 11.5023 (4) Å

c = 15.5571 (5) Å

α = 86.111 (2)°

β = 84.564 (2)°

γ = 89.037 (2)°

V = 1403.95 (8) Å3

Z = 4

Mo Kα radiation

μ = 3.12 mm−1

T = 118 K

0.41 × 0.21 × 0.02 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.606, T max = 0.747

40101 measured reflections

9403 independent reflections

6435 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.081

S = 1.01

9403 reflections

361 parameters

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.45 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT and SADABS (Bruker, 2005 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050879/wn2368sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050879/wn2368Isup2.hkl

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

C14H11BrClN3O	Z = 4
Mr = 352.62	F(000) = 704
Triclinic, P1	Dx = 1.668 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8999 (2) Å	Cell parameters from 7237 reflections
b = 11.5023 (4) Å	θ = 2.3–28.2°
c = 15.5571 (5) Å	µ = 3.12 mm−1
α = 86.111 (2)°	T = 118 K
β = 84.564 (2)°	Plate, colourless
γ = 89.037 (2)°	0.41 × 0.21 × 0.02 mm
V = 1403.95 (8) Å3

Bruker APEXII CCD diffractometer	9403 independent reflections
Radiation source: fine-focus sealed tube	6435 reflections with I > 2σ(I)
graphite	Rint = 0.060
Detector resolution: 8.333 pixels mm-1	θmax = 32.0°, θmin = 2.8°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (Blessing, 1995)	k = −17→17
Tmin = 0.606, Tmax = 0.747	l = −23→23
40101 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0269P)2 + 0.5143P] where P = (Fo2 + 2Fc2)/3
9403 reflections	(Δ/σ)max = 0.002
361 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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
Br9	0.07829 (3)	−0.13291 (2)	0.558649 (16)	0.02240 (6)
Cl6	0.55993 (8)	0.24034 (6)	0.75030 (4)	0.03239 (15)
N1	0.6523 (2)	0.0585 (2)	0.66667 (15)	0.0294 (5)
C2	0.6243 (3)	−0.0336 (3)	0.62176 (19)	0.0337 (7)
H2	0.7222	−0.0760	0.6010	0.040*
N3	0.4768 (2)	−0.07252 (19)	0.60296 (14)	0.0271 (5)
C4	0.3419 (3)	−0.0102 (2)	0.63424 (15)	0.0204 (5)
C5	0.3551 (3)	0.0859 (2)	0.68449 (15)	0.0194 (5)
C6	0.5190 (3)	0.1184 (2)	0.69711 (16)	0.0226 (5)
N7	0.1938 (2)	0.12957 (17)	0.70536 (13)	0.0200 (4)
C8	0.0815 (3)	0.0629 (2)	0.66795 (15)	0.0207 (5)
H8	−0.0383	0.0745	0.6720	0.025*
C9	0.1670 (3)	−0.0223 (2)	0.62432 (15)	0.0187 (5)
C10	0.1459 (3)	0.2263 (2)	0.75875 (16)	0.0244 (5)
H10A	0.2034	0.2975	0.7321	0.029*
H10B	0.0218	0.2400	0.7592	0.029*
O11	0.1867 (2)	0.20846 (15)	0.84366 (11)	0.0265 (4)
C12	0.0892 (4)	0.1195 (3)	0.89288 (19)	0.0465 (8)
H12A	0.1187	0.0426	0.8702	0.056*
H12B	−0.0336	0.1344	0.8888	0.056*
C13	0.1286 (4)	0.1199 (3)	0.98518 (18)	0.0343 (6)
C14	0.0310 (4)	0.1865 (2)	1.0417 (2)	0.0362 (7)
H14	−0.0592	0.2333	1.0215	0.043*
C15	0.0629 (4)	0.1861 (3)	1.12723 (19)	0.0377 (7)
H15	−0.0061	0.2318	1.1656	0.045*
C16	0.1938 (4)	0.1200 (3)	1.1573 (2)	0.0395 (7)
H16	0.2158	0.1200	1.2163	0.047*
C17	0.2929 (4)	0.0539 (3)	1.1013 (2)	0.0446 (8)
H17	0.3841	0.0082	1.1215	0.054*
C18	0.2602 (4)	0.0536 (3)	1.0156 (2)	0.0410 (7)
H18	0.3289	0.0073	0.9773	0.049*
Br9'	0.59248 (3)	0.72770 (2)	0.500913 (16)	0.02152 (6)
Cl6'	1.15241 (7)	0.36355 (6)	0.28870 (4)	0.02845 (14)
N1'	1.2108 (2)	0.54047 (18)	0.37585 (13)	0.0228 (4)
C2'	1.1644 (3)	0.6305 (2)	0.42386 (17)	0.0257 (5)
H2'	1.2547	0.6744	0.4411	0.031*
N3'	1.0089 (2)	0.66584 (18)	0.45013 (13)	0.0223 (4)
C4'	0.8857 (3)	0.6018 (2)	0.42261 (15)	0.0182 (5)
C5'	0.9182 (3)	0.5069 (2)	0.37055 (14)	0.0175 (4)
C6'	1.0881 (3)	0.4791 (2)	0.34985 (15)	0.0197 (5)
N7'	0.7642 (2)	0.46355 (17)	0.35311 (12)	0.0190 (4)
C8'	0.6378 (3)	0.5300 (2)	0.39368 (15)	0.0199 (5)
H8'	0.5194	0.5186	0.3921	0.024*
C9'	0.7066 (3)	0.6140 (2)	0.43611 (15)	0.0190 (5)
C10'	0.7317 (3)	0.3645 (2)	0.30284 (16)	0.0225 (5)
H10C	0.8014	0.2971	0.3222	0.027*
H10D	0.6107	0.3427	0.3150	0.027*
O11'	0.76778 (19)	0.38677 (15)	0.21388 (11)	0.0250 (4)
C12'	0.6421 (3)	0.4559 (3)	0.17201 (17)	0.0320 (6)
H12C	0.6546	0.5392	0.1820	0.038*
H12D	0.5264	0.4312	0.1953	0.038*
C13'	0.6698 (3)	0.4377 (2)	0.07720 (17)	0.0271 (6)
C14'	0.5969 (3)	0.3438 (3)	0.04404 (19)	0.0361 (7)
H14'	0.5247	0.2928	0.0810	0.043*
C15'	0.6289 (4)	0.3240 (3)	−0.04277 (19)	0.0408 (7)
H15'	0.5790	0.2592	−0.0652	0.049*
C16'	0.7331 (3)	0.3979 (3)	−0.09698 (19)	0.0371 (7)
H16'	0.7555	0.3842	−0.1565	0.045*
C17'	0.8045 (4)	0.4920 (3)	−0.06387 (19)	0.0397 (7)
H17'	0.8758	0.5434	−0.1008	0.048*
C18'	0.7726 (3)	0.5115 (3)	0.02262 (18)	0.0357 (7)
H18'	0.8221	0.5766	0.0448	0.043*

	U11	U22	U33	U12	U13	U23
Br9	0.01902 (11)	0.02210 (13)	0.02763 (14)	−0.00162 (8)	−0.00850 (9)	−0.00370 (10)
Cl6	0.0302 (3)	0.0355 (4)	0.0336 (4)	−0.0109 (3)	−0.0062 (3)	−0.0109 (3)
N1	0.0160 (9)	0.0408 (14)	0.0332 (13)	−0.0029 (8)	−0.0051 (8)	−0.0111 (11)
C2	0.0144 (11)	0.0463 (18)	0.0423 (18)	0.0040 (10)	−0.0035 (10)	−0.0164 (14)
N3	0.0163 (9)	0.0343 (13)	0.0323 (13)	0.0021 (8)	−0.0042 (8)	−0.0107 (10)
C4	0.0173 (10)	0.0242 (13)	0.0198 (13)	−0.0013 (8)	−0.0034 (8)	0.0004 (10)
C5	0.0167 (10)	0.0251 (13)	0.0166 (12)	−0.0010 (8)	−0.0030 (8)	−0.0005 (10)
C6	0.0216 (11)	0.0289 (14)	0.0182 (12)	−0.0054 (9)	−0.0058 (9)	−0.0025 (10)
N7	0.0170 (9)	0.0223 (11)	0.0213 (11)	0.0000 (7)	−0.0034 (7)	−0.0049 (8)
C8	0.0149 (10)	0.0263 (13)	0.0214 (13)	−0.0008 (8)	−0.0044 (8)	−0.0019 (10)
C9	0.0174 (10)	0.0204 (12)	0.0191 (12)	−0.0024 (8)	−0.0052 (8)	−0.0022 (9)
C10	0.0272 (12)	0.0232 (13)	0.0230 (14)	0.0031 (9)	−0.0011 (9)	−0.0045 (11)
O11	0.0326 (9)	0.0286 (10)	0.0185 (9)	−0.0086 (7)	−0.0009 (7)	−0.0031 (8)
C12	0.062 (2)	0.051 (2)	0.0268 (17)	−0.0310 (16)	−0.0012 (14)	0.0029 (14)
C13	0.0421 (15)	0.0349 (16)	0.0258 (15)	−0.0169 (12)	−0.0013 (11)	0.0004 (12)
C14	0.0421 (16)	0.0290 (16)	0.0390 (18)	−0.0022 (12)	−0.0110 (13)	−0.0023 (13)
C15	0.0475 (17)	0.0343 (17)	0.0324 (17)	−0.0003 (13)	−0.0042 (13)	−0.0100 (13)
C16	0.0494 (17)	0.0420 (18)	0.0281 (16)	−0.0092 (14)	−0.0097 (13)	0.0007 (14)
C17	0.0379 (16)	0.049 (2)	0.047 (2)	−0.0003 (14)	−0.0113 (14)	0.0032 (16)
C18	0.0364 (15)	0.0460 (19)	0.0393 (19)	−0.0044 (13)	0.0072 (13)	−0.0086 (15)
Br9'	0.01786 (10)	0.02498 (14)	0.02185 (13)	0.00062 (8)	−0.00097 (8)	−0.00401 (10)
Cl6'	0.0234 (3)	0.0316 (3)	0.0305 (4)	0.0022 (2)	0.0014 (2)	−0.0094 (3)
N1'	0.0177 (9)	0.0271 (12)	0.0235 (12)	−0.0024 (8)	−0.0023 (7)	−0.0005 (9)
C2'	0.0148 (10)	0.0315 (14)	0.0315 (15)	−0.0057 (9)	−0.0052 (9)	−0.0012 (11)
N3'	0.0187 (9)	0.0254 (11)	0.0235 (11)	−0.0034 (8)	−0.0044 (8)	−0.0029 (9)
C4'	0.0177 (10)	0.0192 (12)	0.0178 (12)	−0.0013 (8)	−0.0034 (8)	0.0009 (9)
C5'	0.0166 (9)	0.0222 (12)	0.0142 (11)	−0.0025 (8)	−0.0035 (8)	−0.0017 (9)
C6'	0.0199 (10)	0.0236 (12)	0.0151 (12)	0.0011 (9)	0.0007 (8)	0.0001 (10)
N7'	0.0151 (8)	0.0243 (11)	0.0187 (11)	−0.0031 (7)	−0.0040 (7)	−0.0045 (8)
C8'	0.0122 (9)	0.0282 (13)	0.0189 (12)	−0.0001 (8)	−0.0013 (8)	0.0021 (10)
C9'	0.0188 (10)	0.0224 (12)	0.0158 (12)	−0.0008 (8)	−0.0014 (8)	−0.0007 (9)
C10'	0.0236 (11)	0.0229 (13)	0.0219 (13)	−0.0037 (9)	−0.0056 (9)	−0.0037 (10)
O11'	0.0226 (8)	0.0349 (10)	0.0187 (9)	0.0060 (7)	−0.0058 (6)	−0.0064 (8)
C12'	0.0312 (13)	0.0412 (17)	0.0249 (15)	0.0107 (11)	−0.0078 (10)	−0.0060 (12)
C13'	0.0260 (12)	0.0348 (15)	0.0219 (14)	0.0063 (10)	−0.0079 (10)	−0.0055 (11)
C14'	0.0411 (15)	0.0394 (17)	0.0282 (16)	−0.0068 (12)	−0.0063 (12)	0.0005 (13)
C15'	0.0510 (17)	0.0438 (19)	0.0299 (17)	−0.0083 (14)	−0.0098 (13)	−0.0089 (14)
C16'	0.0405 (15)	0.0497 (19)	0.0226 (15)	0.0026 (13)	−0.0079 (11)	−0.0064 (13)
C17'	0.0404 (16)	0.052 (2)	0.0272 (16)	−0.0108 (13)	−0.0059 (12)	0.0008 (14)
C18'	0.0412 (15)	0.0386 (17)	0.0294 (16)	−0.0075 (12)	−0.0114 (12)	−0.0052 (13)

Br9—C9	1.870 (2)	Br9'—C9'	1.873 (2)
Cl6—C6	1.726 (2)	Cl6'—C6'	1.728 (2)
N1—C6	1.316 (3)	N1'—C6'	1.318 (3)
N1—C2	1.341 (3)	N1'—C2'	1.344 (3)
C2—N3	1.320 (3)	C2'—N3'	1.324 (3)
C2—H2	0.9500	C2'—H2'	0.9500
N3—C4	1.345 (3)	N3'—C4'	1.348 (3)
C4—C5	1.407 (3)	C4'—C5'	1.409 (3)
C4—C9	1.415 (3)	C4'—C9'	1.417 (3)
C5—N7	1.380 (3)	C5'—N7'	1.379 (3)
C5—C6	1.390 (3)	C5'—C6'	1.388 (3)
N7—C8	1.377 (3)	N7'—C8'	1.379 (3)
N7—C10	1.457 (3)	N7'—C10'	1.465 (3)
C8—C9	1.363 (3)	C8'—C9'	1.355 (3)
C8—H8	0.9500	C8'—H8'	0.9500
C10—O11	1.390 (3)	C10'—O11'	1.394 (3)
C10—H10A	0.9900	C10'—H10C	0.9900
C10—H10B	0.9900	C10'—H10D	0.9900
O11—C12	1.427 (3)	O11'—C12'	1.438 (3)
C12—C13	1.498 (4)	C12'—C13'	1.499 (4)
C12—H12A	0.9900	C12'—H12C	0.9900
C12—H12B	0.9900	C12'—H12D	0.9900
C13—C14	1.378 (4)	C13'—C18'	1.377 (4)
C13—C18	1.380 (4)	C13'—C14'	1.385 (4)
C14—C15	1.377 (4)	C14'—C15'	1.384 (4)
C14—H14	0.9500	C14'—H14'	0.9500
C15—C16	1.372 (4)	C15'—C16'	1.381 (4)
C15—H15	0.9500	C15'—H15'	0.9500
C16—C17	1.376 (4)	C16'—C17'	1.380 (4)
C16—H16	0.9500	C16'—H16'	0.9500
C17—C18	1.382 (4)	C17'—C18'	1.378 (4)
C17—H17	0.9500	C17'—H17'	0.9500
C18—H18	0.9500	C18'—H18'	0.9500
C6—N1—C2	117.6 (2)	C6'—N1'—C2'	117.19 (19)
N3—C2—N1	127.8 (2)	N3'—C2'—N1'	128.2 (2)
N3—C2—H2	116.1	N3'—C2'—H2'	115.9
N1—C2—H2	116.1	N1'—C2'—H2'	115.9
C2—N3—C4	113.9 (2)	C2'—N3'—C4'	113.4 (2)
N3—C4—C5	123.5 (2)	N3'—C4'—C5'	123.7 (2)
N3—C4—C9	130.0 (2)	N3'—C4'—C9'	129.7 (2)
C5—C4—C9	106.56 (19)	C5'—C4'—C9'	106.58 (19)
N7—C5—C6	135.4 (2)	N7'—C5'—C6'	135.8 (2)
N7—C5—C4	108.42 (18)	N7'—C5'—C4'	108.19 (18)
C6—C5—C4	116.1 (2)	C6'—C5'—C4'	116.05 (19)
N1—C6—C5	121.1 (2)	N1'—C6'—C5'	121.4 (2)
N1—C6—Cl6	116.47 (17)	N1'—C6'—Cl6'	115.92 (17)
C5—C6—Cl6	122.42 (19)	C5'—C6'—Cl6'	122.65 (18)
C8—N7—C5	107.50 (19)	C8'—N7'—C5'	107.52 (19)
C8—N7—C10	124.96 (19)	C8'—N7'—C10'	123.80 (18)
C5—N7—C10	127.53 (19)	C5'—N7'—C10'	128.67 (19)
C9—C8—N7	110.16 (19)	C9'—C8'—N7'	110.33 (19)
C9—C8—H8	124.9	C9'—C8'—H8'	124.8
N7—C8—H8	124.9	N7'—C8'—H8'	124.8
C8—C9—C4	107.4 (2)	C8'—C9'—C4'	107.4 (2)
C8—C9—Br9	128.03 (17)	C8'—C9'—Br9'	127.83 (17)
C4—C9—Br9	124.56 (18)	C4'—C9'—Br9'	124.78 (17)
O11—C10—N7	113.9 (2)	O11'—C10'—N7'	113.58 (19)
O11—C10—H10A	108.8	O11'—C10'—H10C	108.9
N7—C10—H10A	108.8	N7'—C10'—H10C	108.9
O11—C10—H10B	108.8	O11'—C10'—H10D	108.9
N7—C10—H10B	108.8	N7'—C10'—H10D	108.9
H10A—C10—H10B	107.7	H10C—C10'—H10D	107.7
C10—O11—C12	113.6 (2)	C10'—O11'—C12'	115.05 (18)
O11—C12—C13	108.2 (2)	O11'—C12'—C13'	107.2 (2)
O11—C12—H12A	110.1	O11'—C12'—H12C	110.3
C13—C12—H12A	110.1	C13'—C12'—H12C	110.3
O11—C12—H12B	110.1	O11'—C12'—H12D	110.3
C13—C12—H12B	110.1	C13'—C12'—H12D	110.3
H12A—C12—H12B	108.4	H12C—C12'—H12D	108.5
C14—C13—C18	118.8 (3)	C18'—C13'—C14'	119.2 (3)
C14—C13—C12	119.8 (3)	C18'—C13'—C12'	120.5 (2)
C18—C13—C12	121.4 (3)	C14'—C13'—C12'	120.2 (3)
C15—C14—C13	120.7 (3)	C15'—C14'—C13'	120.2 (3)
C15—C14—H14	119.7	C15'—C14'—H14'	119.9
C13—C14—H14	119.7	C13'—C14'—H14'	119.9
C16—C15—C14	120.4 (3)	C16'—C15'—C14'	120.3 (3)
C16—C15—H15	119.8	C16'—C15'—H15'	119.9
C14—C15—H15	119.8	C14'—C15'—H15'	119.9
C15—C16—C17	119.3 (3)	C17'—C16'—C15'	119.4 (3)
C15—C16—H16	120.3	C17'—C16'—H16'	120.3
C17—C16—H16	120.3	C15'—C16'—H16'	120.3
C16—C17—C18	120.3 (3)	C18'—C17'—C16'	120.2 (3)
C16—C17—H17	119.9	C18'—C17'—H17'	119.9
C18—C17—H17	119.9	C16'—C17'—H17'	119.9
C13—C18—C17	120.5 (3)	C13'—C18'—C17'	120.7 (3)
C13—C18—H18	119.8	C13'—C18'—H18'	119.7
C17—C18—H18	119.8	C17'—C18'—H18'	119.7
C6—N1—C2—N3	0.7 (5)	C6'—N1'—C2'—N3'	1.0 (4)
N1—C2—N3—C4	−0.4 (4)	N1'—C2'—N3'—C4'	−1.0 (4)
C2—N3—C4—C5	−1.7 (4)	C2'—N3'—C4'—C5'	−0.4 (3)
C2—N3—C4—C9	177.1 (3)	C2'—N3'—C4'—C9'	−178.8 (2)
N3—C4—C5—N7	179.8 (2)	N3'—C4'—C5'—N7'	−178.6 (2)
C9—C4—C5—N7	0.8 (3)	C9'—C4'—C5'—N7'	0.1 (3)
N3—C4—C5—C6	3.3 (4)	N3'—C4'—C5'—C6'	1.7 (3)
C9—C4—C5—C6	−175.7 (2)	C9'—C4'—C5'—C6'	−179.6 (2)
C2—N1—C6—C5	1.2 (4)	C2'—N1'—C6'—C5'	0.5 (3)
C2—N1—C6—Cl6	−177.1 (2)	C2'—N1'—C6'—Cl6'	−179.70 (19)
N7—C5—C6—N1	−178.2 (3)	N7'—C5'—C6'—N1'	178.7 (2)
C4—C5—C6—N1	−3.0 (4)	C4'—C5'—C6'—N1'	−1.7 (3)
N7—C5—C6—Cl6	0.0 (4)	N7'—C5'—C6'—Cl6'	−1.0 (4)
C4—C5—C6—Cl6	175.20 (18)	C4'—C5'—C6'—Cl6'	178.51 (17)
C6—C5—N7—C8	174.8 (3)	C6'—C5'—N7'—C8'	179.5 (3)
C4—C5—N7—C8	−0.7 (3)	C4'—C5'—N7'—C8'	−0.1 (3)
C6—C5—N7—C10	−6.7 (4)	C6'—C5'—N7'—C10'	0.6 (4)
C4—C5—N7—C10	177.9 (2)	C4'—C5'—N7'—C10'	−179.0 (2)
C5—N7—C8—C9	0.3 (3)	C5'—N7'—C8'—C9'	0.1 (3)
C10—N7—C8—C9	−178.3 (2)	C10'—N7'—C8'—C9'	179.0 (2)
N7—C8—C9—C4	0.2 (3)	N7'—C8'—C9'—C4'	0.0 (3)
N7—C8—C9—Br9	−177.46 (17)	N7'—C8'—C9'—Br9'	179.70 (17)
N3—C4—C9—C8	−179.5 (3)	N3'—C4'—C9'—C8'	178.6 (2)
C5—C4—C9—C8	−0.6 (3)	C5'—C4'—C9'—C8'	−0.1 (3)
N3—C4—C9—Br9	−1.8 (4)	N3'—C4'—C9'—Br9'	−1.1 (4)
C5—C4—C9—Br9	177.16 (17)	C5'—C4'—C9'—Br9'	−179.77 (17)
C8—N7—C10—O11	116.7 (2)	C8'—N7'—C10'—O11'	107.8 (2)
C5—N7—C10—O11	−61.7 (3)	C5'—N7'—C10'—O11'	−73.4 (3)
N7—C10—O11—C12	−68.2 (3)	N7'—C10'—O11'—C12'	−77.3 (2)
C10—O11—C12—C13	−172.6 (2)	C10'—O11'—C12'—C13'	−161.5 (2)
O11—C12—C13—C14	91.4 (3)	O11'—C12'—C13'—C18'	−92.3 (3)
O11—C12—C13—C18	−89.4 (3)	O11'—C12'—C13'—C14'	85.3 (3)
C18—C13—C14—C15	−0.7 (4)	C18'—C13'—C14'—C15'	0.7 (4)
C12—C13—C14—C15	178.6 (3)	C12'—C13'—C14'—C15'	−177.0 (3)
C13—C14—C15—C16	0.7 (4)	C13'—C14'—C15'—C16'	−0.3 (5)
C14—C15—C16—C17	−0.2 (5)	C14'—C15'—C16'—C17'	−0.2 (5)
C15—C16—C17—C18	−0.3 (5)	C15'—C16'—C17'—C18'	0.3 (4)
C14—C13—C18—C17	0.2 (4)	C14'—C13'—C18'—C17'	−0.6 (4)
C12—C13—C18—C17	−179.0 (3)	C12'—C13'—C18'—C17'	177.0 (3)
C16—C17—C18—C13	0.3 (5)	C16'—C17'—C18'—C13'	0.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Br9i	0.95	2.90	3.805 (3)	159
C8—H8···N1ii	0.95	2.46	3.394 (3)	166
C8'—H8'···N1'ii	0.95	2.48	3.410 (3)	166
C10'—H10C···Br9iii	0.99	2.78	3.700 (2)	156
C15—H15···O11'iv	0.95	2.60	3.497 (4)	158
C10—H10A···Cg1v	0.99	2.60	3.466 (3)	146
C14—H14···Cg2iv	0.95	2.87	3.794 (3)	165

C—N···Br	C—N	N···Br	C···Br	C—N···Br
C2—N3···Br9'vi	1.320 (3)	2.964 (2)	3.457 (3)	100.45 (17)
C2'—N3'···Brvii	1.324 (3)	3.043 (2)	3.565 (3)	102.17 (14)

Table 1

Selected torsion angles (°)

C5—N7—C8—C9	0.3 (3)
N7—C10—O11—C12	−68.2 (3)
C10—O11—C12—C13	−172.6 (2)
C5′—N7′—C8′—C9′	0.1 (3)
N7′—C10′—O11′—C12′	−77.3 (2)
C10′—O11′—C12′—C13′	−161.5 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Br9i	0.95	2.90	3.805 (3)	159
C8—H8⋯N1ii	0.95	2.46	3.394 (3)	166
C8′—H8′⋯N1′ii	0.95	2.48	3.410 (3)	166
C10′—H10C⋯Br9iii	0.99	2.78	3.700 (2)	156
C15—H15⋯O11′iv	0.95	2.60	3.497 (4)	158
C10—H10A⋯Cg1v	0.99	2.60	3.466 (3)	146
C14—H14⋯Cg2iv	0.95	2.87	3.794 (3)	165

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) . Cg1 and Cg2 are the centroids of the N7′,C4′,C5′,C8′,C9′ and C13′–C18′ rings, respectively.

Table 3

C—N⋯Br inter­actions (Å, °)

C—N⋯Br	C—N	N⋯Br	C⋯Br	C—N⋯Br
C2—N3⋯Br9′vi	1.320 (3)	2.964 (2)	3.457 (3)	100.45 (17)
C2′—N3′⋯Brvii	1.324 (3)	3.043 (2)	3.565 (3)	102.17 (14)

Symmetry codes: (vi) ; (vii) .