Crystal structure, Hirshfeld surface analysis and DFT studies of 6-bromo-3-(12-bromo­dodec­yl)-2-(4-nitro­phen­yl)-4H-imidazo[4,5-b]pyridine

In the title mol­ecule, the imidazolo­pyridine and phenyl rings are nearly co-planar, and the 12-bromo­dodecyl side chain is directed so as to give the complete mol­ecule a V-shape.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.035
• wR factor = 0.095
• Data-to-parameter ratio = 22.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          3 Report

Alert level G
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          2 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          1 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )         6% Note
PLAT367_ALERT_2_G Long?  C(sp?)-C(sp?) Bond  C22      - C23      .       1.53 Ang.
PLAT434_ALERT_2_G Short Inter HL..HL Contact Br1      ..Br1              3.57 Ang.
                                                 4-x,2-y,-z  =      2_975 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        135 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          8 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   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
   3 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/1 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

6-Bromo-3-(12-bromododecyl)-2-(4-nitrophenyl)-3H-imidazo[4,5-b]pyridine

Crystal data

C24H30Br2N4O2	Z = 2
Mr = 566.34	F(000) = 576
Triclinic, P1	Dx = 1.522 Mg m^−3
a = 6.3291 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8911 (17) Å	Cell parameters from 9900 reflections
c = 21.133 (4) Å	θ = 2.2–29.0°
α = 76.480 (2)°	µ = 3.31 mm^−1
β = 84.965 (3)°	T = 150 K
γ = 73.891 (2)°	Column, light orange
V = 1235.4 (4) Å^3	0.48 × 0.23 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer	6598 independent reflections
Radiation source: fine-focus sealed tube	5337 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
Detector resolution: 8.3333 pixels mm^-1	θmax = 29.3°, θmin = 2.0°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −13→13
Tmin = 0.23, Tmax = 0.56	l = −29→29
24139 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.095	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0494P)^2 + 0.370P] where P = (Fo^2 + 2Fc^2)/3
6598 reflections	(Δ/σ)max = 0.002
293 parameters	Δρmax = 0.72 e Å^−3
0 restraints	Δρmin = −0.80 e Å^−3

Special details

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = -30.00 and 210.00°. The scan time was 10 sec/frame.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.99 Å). All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. Br2 is disordered over two sites in a 0.902 (3)/0.098 (32) ratio with the two components refined with restraints that they have comparable geometries.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1	1.82823 (3)	0.88087 (2)	0.00828 (2)	0.02928 (7)
Br2	−0.34993 (9)	0.51084 (14)	0.63610 (3)	0.05439 (19)	0.902 (3)
Br2A	−0.3773 (9)	0.5733 (11)	0.6273 (3)	0.05439 (19)	0.098 (3)
O1	0.4691 (3)	0.16270 (19)	0.13274 (10)	0.0470 (4)
O2	0.3734 (3)	0.2314 (2)	0.22339 (9)	0.0468 (4)
N1	1.3755 (3)	0.79656 (18)	0.15128 (8)	0.0244 (3)
N2	1.1281 (3)	0.64593 (18)	0.16156 (8)	0.0239 (3)
N3	1.2508 (3)	0.55633 (18)	0.06847 (8)	0.0234 (3)
N4	0.4845 (3)	0.23168 (19)	0.17246 (10)	0.0317 (4)
C1	1.3664 (3)	0.6514 (2)	0.07409 (9)	0.0222 (4)
C2	1.5326 (3)	0.6991 (2)	0.03550 (10)	0.0241 (4)
H2	1.588946	0.665956	−0.002911	0.029*
C3	1.6108 (3)	0.7989 (2)	0.05705 (10)	0.0241 (4)
C4	1.5370 (3)	0.8446 (2)	0.11371 (10)	0.0250 (4)
H4	1.599544	0.910484	0.126734	0.030*
C5	1.2880 (3)	0.7032 (2)	0.13151 (9)	0.0223 (4)
C6	1.1134 (3)	0.5596 (2)	0.12076 (9)	0.0225 (4)
C7	0.9500 (3)	0.4757 (2)	0.13404 (9)	0.0223 (4)
C8	0.9326 (3)	0.3904 (2)	0.09185 (10)	0.0256 (4)
H8	1.027479	0.386290	0.054538	0.031*
C9	0.7781 (3)	0.3117 (2)	0.10385 (10)	0.0266 (4)
H9	0.764906	0.253965	0.074998	0.032*
C10	0.6431 (3)	0.3189 (2)	0.15897 (10)	0.0249 (4)
C11	0.6535 (3)	0.4038 (2)	0.20136 (10)	0.0272 (4)
H11	0.557276	0.407835	0.238384	0.033*
C12	0.8083 (3)	0.4831 (2)	0.18856 (10)	0.0254 (4)
H12	0.817963	0.542629	0.216954	0.031*
C13	1.2921 (3)	0.8451 (2)	0.21174 (10)	0.0277 (4)
H13A	1.407583	0.875235	0.229259	0.033*
H13B	1.259112	0.763605	0.244503	0.033*
C14	1.0856 (4)	0.9702 (2)	0.20091 (10)	0.0303 (4)
H14A	0.979474	0.946902	0.176234	0.036*
H14B	1.124005	1.057448	0.174668	0.036*
C15	0.9786 (4)	1.0010 (2)	0.26569 (11)	0.0354 (5)
H15A	1.093787	1.003377	0.293931	0.042*
H15B	0.872569	1.097574	0.257308	0.042*
C16	0.8594 (4)	0.8905 (3)	0.30167 (12)	0.0422 (6)
H16A	0.766800	0.873698	0.270434	0.051*
H16B	0.970288	0.798211	0.317524	0.051*
C17	0.7154 (5)	0.9319 (3)	0.35888 (13)	0.0481 (7)
H17A	0.608784	1.026430	0.343710	0.058*
H17B	0.808726	0.943166	0.391508	0.058*
C18	0.5895 (5)	0.8219 (3)	0.39151 (13)	0.0498 (7)
H18A	0.499382	0.809373	0.358399	0.060*
H18B	0.697061	0.727992	0.407038	0.060*
C19	0.4406 (5)	0.8604 (3)	0.44815 (14)	0.0551 (8)
H19A	0.334976	0.955515	0.433229	0.066*
H19B	0.530537	0.869341	0.482227	0.066*
C20	0.3130 (5)	0.7502 (3)	0.47773 (13)	0.0511 (7)
H20A	0.418487	0.653915	0.489418	0.061*
H20B	0.215232	0.746721	0.444409	0.061*
C21	0.1746 (5)	0.7810 (3)	0.53790 (14)	0.0504 (7)
H21A	0.268887	0.794690	0.569570	0.060*
H21B	0.057909	0.872000	0.525371	0.060*
C22	0.0687 (5)	0.6614 (3)	0.57043 (12)	0.0434 (6)
H22A	0.182702	0.568038	0.577361	0.052*
H22B	−0.041627	0.656911	0.541078	0.052*
C23	−0.0432 (5)	0.6828 (3)	0.63564 (12)	0.0434 (6)
H23A	0.059462	0.705909	0.661635	0.052*
H23B	−0.173900	0.766726	0.627551	0.052*
C24	−0.1145 (4)	0.5542 (3)	0.67503 (11)	0.0404 (5)	0.902 (3)
H24A	−0.164784	0.571989	0.718783	0.049*	0.902 (3)
H24B	0.014190	0.468801	0.680713	0.049*	0.902 (3)
C24A	−0.1145 (4)	0.5542 (3)	0.67503 (11)	0.0404 (5)	0.098 (3)
H24C	−0.150774	0.561926	0.720811	0.049*	0.098 (3)
H24D	−0.001810	0.462587	0.673847	0.049*	0.098 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02318 (11)	0.02607 (11)	0.04000 (13)	−0.01178 (8)	0.00655 (8)	−0.00638 (8)
Br2	0.0548 (2)	0.0723 (6)	0.04320 (19)	−0.0293 (3)	−0.00326 (15)	−0.0109 (3)
Br2A	0.0548 (2)	0.0723 (6)	0.04320 (19)	−0.0293 (3)	−0.00326 (15)	−0.0109 (3)
O1	0.0496 (11)	0.0440 (10)	0.0645 (12)	−0.0309 (8)	0.0154 (9)	−0.0294 (9)
O2	0.0465 (10)	0.0549 (11)	0.0518 (11)	−0.0357 (9)	0.0175 (8)	−0.0171 (9)
N1	0.0216 (8)	0.0245 (8)	0.0304 (8)	−0.0099 (6)	0.0014 (7)	−0.0087 (7)
N2	0.0224 (8)	0.0255 (8)	0.0276 (8)	−0.0119 (7)	0.0019 (6)	−0.0073 (7)
N3	0.0196 (8)	0.0236 (8)	0.0301 (8)	−0.0089 (6)	0.0003 (6)	−0.0082 (7)
N4	0.0279 (9)	0.0267 (9)	0.0437 (11)	−0.0140 (7)	0.0035 (8)	−0.0074 (8)
C1	0.0182 (9)	0.0219 (9)	0.0274 (9)	−0.0062 (7)	−0.0007 (7)	−0.0063 (7)
C2	0.0187 (9)	0.0224 (9)	0.0306 (10)	−0.0058 (7)	0.0013 (7)	−0.0053 (8)
C3	0.0170 (9)	0.0210 (9)	0.0334 (10)	−0.0066 (7)	0.0015 (7)	−0.0033 (8)
C4	0.0216 (9)	0.0211 (9)	0.0344 (10)	−0.0091 (7)	−0.0002 (8)	−0.0066 (8)
C5	0.0202 (9)	0.0219 (9)	0.0266 (9)	−0.0080 (7)	−0.0005 (7)	−0.0059 (7)
C6	0.0194 (9)	0.0228 (9)	0.0263 (9)	−0.0072 (7)	−0.0020 (7)	−0.0049 (7)
C7	0.0188 (9)	0.0211 (9)	0.0274 (9)	−0.0065 (7)	−0.0014 (7)	−0.0044 (7)
C8	0.0218 (9)	0.0252 (9)	0.0322 (10)	−0.0091 (8)	0.0033 (8)	−0.0088 (8)
C9	0.0232 (10)	0.0243 (9)	0.0366 (11)	−0.0095 (8)	0.0006 (8)	−0.0114 (8)
C10	0.0207 (9)	0.0214 (9)	0.0340 (10)	−0.0098 (7)	0.0004 (8)	−0.0039 (8)
C11	0.0231 (10)	0.0302 (10)	0.0292 (10)	−0.0108 (8)	0.0020 (8)	−0.0050 (8)
C12	0.0245 (10)	0.0275 (10)	0.0274 (10)	−0.0109 (8)	−0.0010 (8)	−0.0070 (8)
C13	0.0288 (11)	0.0302 (10)	0.0292 (10)	−0.0116 (8)	0.0019 (8)	−0.0129 (8)
C14	0.0322 (11)	0.0288 (10)	0.0312 (10)	−0.0111 (9)	0.0041 (8)	−0.0073 (9)
C15	0.0383 (13)	0.0298 (11)	0.0386 (12)	−0.0096 (9)	0.0092 (10)	−0.0117 (9)
C16	0.0457 (14)	0.0465 (14)	0.0412 (13)	−0.0219 (12)	0.0138 (11)	−0.0168 (11)
C17	0.0528 (16)	0.0397 (14)	0.0486 (15)	−0.0129 (12)	0.0184 (12)	−0.0102 (11)
C18	0.0584 (17)	0.0536 (16)	0.0413 (14)	−0.0229 (14)	0.0172 (12)	−0.0148 (12)
C19	0.0665 (19)	0.0431 (15)	0.0488 (15)	−0.0142 (13)	0.0258 (14)	−0.0070 (12)
C20	0.0589 (18)	0.0568 (17)	0.0365 (13)	−0.0198 (14)	0.0158 (12)	−0.0089 (12)
C21	0.0590 (17)	0.0378 (14)	0.0466 (15)	−0.0096 (12)	0.0208 (13)	−0.0058 (11)
C22	0.0490 (15)	0.0473 (14)	0.0335 (12)	−0.0146 (12)	0.0101 (11)	−0.0101 (11)
C23	0.0486 (15)	0.0449 (14)	0.0370 (12)	−0.0135 (12)	0.0122 (11)	−0.0129 (11)
C24	0.0434 (14)	0.0483 (14)	0.0307 (11)	−0.0158 (11)	0.0009 (10)	−0.0069 (10)
C24A	0.0434 (14)	0.0483 (14)	0.0307 (11)	−0.0158 (11)	0.0009 (10)	−0.0069 (10)

Geometric parameters (Å, º)

Br1—C3	1.8954 (19)	C14—H14A	0.9900
Br2—C24	1.953 (3)	C14—H14B	0.9900
Br2A—C24A	1.962 (5)	C15—C16	1.520 (3)
O1—N4	1.224 (2)	C15—H15A	0.9900
O2—N4	1.233 (2)	C15—H15B	0.9900
N1—C5	1.357 (2)	C16—C17	1.514 (3)
N1—C4	1.361 (2)	C16—H16A	0.9900
N1—C13	1.473 (3)	C16—H16B	0.9900
N2—C5	1.336 (2)	C17—C18	1.526 (4)
N2—C6	1.372 (3)	C17—H17A	0.9900
N3—C6	1.346 (2)	C17—H17B	0.9900
N3—C1	1.372 (2)	C18—C19	1.511 (4)
N4—C10	1.465 (2)	C18—H18A	0.9900
C1—C2	1.392 (3)	C18—H18B	0.9900
C1—C5	1.423 (3)	C19—C20	1.520 (4)
C2—C3	1.396 (3)	C19—H19A	0.9900
C2—H2	0.9500	C19—H19B	0.9900
C3—C4	1.376 (3)	C20—C21	1.521 (4)
C4—H4	0.9500	C20—H20A	0.9900
C6—C7	1.467 (3)	C20—H20B	0.9900
C7—C8	1.393 (3)	C21—C22	1.517 (4)
C7—C12	1.400 (3)	C21—H21A	0.9900
C8—C9	1.383 (3)	C21—H21B	0.9900
C8—H8	0.9500	C22—C23	1.526 (3)
C9—C10	1.387 (3)	C22—H22A	0.9900
C9—H9	0.9500	C22—H22B	0.9900
C10—C11	1.380 (3)	C23—C24A	1.507 (3)
C11—C12	1.389 (3)	C23—C24	1.507 (3)
C11—H11	0.9500	C23—H23A	0.9900
C12—H12	0.9500	C23—H23B	0.9900
C13—C14	1.521 (3)	C24—H24A	0.9900
C13—H13A	0.9900	C24—H24B	0.9900
C13—H13B	0.9900	C24A—H24C	0.9900
C14—C15	1.531 (3)	C24A—H24D	0.9900
C5—N1—C4	118.57 (17)	C17—C16—C15	115.0 (2)
C5—N1—C13	119.67 (16)	C17—C16—H16A	108.5
C4—N1—C13	121.75 (17)	C15—C16—H16A	108.5
C5—N2—C6	100.79 (16)	C17—C16—H16B	108.5
C6—N3—C1	102.17 (16)	C15—C16—H16B	108.5
O1—N4—O2	123.30 (19)	H16A—C16—H16B	107.5
O1—N4—C10	118.48 (18)	C16—C17—C18	113.4 (2)
O2—N4—C10	118.22 (18)	C16—C17—H17A	108.9
N3—C1—C2	132.04 (18)	C18—C17—H17A	108.9
N3—C1—C5	107.59 (16)	C16—C17—H17B	108.9
C2—C1—C5	120.37 (18)	C18—C17—H17B	108.9
C1—C2—C3	115.51 (18)	H17A—C17—H17B	107.7
C1—C2—H2	122.2	C19—C18—C17	115.1 (2)
C3—C2—H2	122.2	C19—C18—H18A	108.5
C4—C3—C2	123.24 (18)	C17—C18—H18A	108.5
C4—C3—Br1	115.85 (15)	C19—C18—H18B	108.5
C2—C3—Br1	120.92 (15)	C17—C18—H18B	108.5
N1—C4—C3	120.73 (18)	H18A—C18—H18B	107.5
N1—C4—H4	119.6	C18—C19—C20	113.3 (3)
C3—C4—H4	119.6	C18—C19—H19A	108.9
N2—C5—N1	126.94 (18)	C20—C19—H19A	108.9
N2—C5—C1	111.52 (17)	C18—C19—H19B	108.9
N1—C5—C1	121.53 (17)	C20—C19—H19B	108.9
N3—C6—N2	117.92 (17)	H19A—C19—H19B	107.7
N3—C6—C7	121.76 (17)	C19—C20—C21	114.2 (3)
N2—C6—C7	120.31 (17)	C19—C20—H20A	108.7
C8—C7—C12	119.67 (18)	C21—C20—H20A	108.7
C8—C7—C6	120.18 (18)	C19—C20—H20B	108.7
C12—C7—C6	120.14 (18)	C21—C20—H20B	108.7
C9—C8—C7	120.52 (19)	H20A—C20—H20B	107.6
C9—C8—H8	119.7	C22—C21—C20	113.0 (2)
C7—C8—H8	119.7	C22—C21—H21A	109.0
C8—C9—C10	118.46 (19)	C20—C21—H21A	109.0
C8—C9—H9	120.8	C22—C21—H21B	109.0
C10—C9—H9	120.8	C20—C21—H21B	109.0
C11—C10—C9	122.63 (18)	H21A—C21—H21B	107.8
C11—C10—N4	119.21 (18)	C21—C22—C23	112.7 (2)
C9—C10—N4	118.16 (18)	C21—C22—H22A	109.0
C10—C11—C12	118.37 (19)	C23—C22—H22A	109.0
C10—C11—H11	120.8	C21—C22—H22B	109.0
C12—C11—H11	120.8	C23—C22—H22B	109.0
C11—C12—C7	120.34 (19)	H22A—C22—H22B	107.8
C11—C12—H12	119.8	C24A—C23—C22	114.3 (2)
C7—C12—H12	119.8	C24—C23—C22	114.3 (2)
N1—C13—C14	112.14 (17)	C24—C23—H23A	108.7
N1—C13—H13A	109.2	C22—C23—H23A	108.7
C14—C13—H13A	109.2	C24—C23—H23B	108.7
N1—C13—H13B	109.2	C22—C23—H23B	108.7
C14—C13—H13B	109.2	H23A—C23—H23B	107.6
H13A—C13—H13B	107.9	C23—C24—Br2	114.01 (18)
C13—C14—C15	111.20 (18)	C23—C24—H24A	108.8
C13—C14—H14A	109.4	Br2—C24—H24A	108.8
C15—C14—H14A	109.4	C23—C24—H24B	108.8
C13—C14—H14B	109.4	Br2—C24—H24B	108.8
C15—C14—H14B	109.4	H24A—C24—H24B	107.6
H14A—C14—H14B	108.0	C23—C24A—Br2A	99.5 (3)
C16—C15—C14	113.51 (19)	C23—C24A—H24C	111.9
C16—C15—H15A	108.9	Br2A—C24A—H24C	111.9
C14—C15—H15A	108.9	C23—C24A—H24D	111.9
C16—C15—H15B	108.9	Br2A—C24A—H24D	111.9
C14—C15—H15B	108.9	H24C—C24A—H24D	109.6
H15A—C15—H15B	107.7
C6—N3—C1—C2	−179.2 (2)	C6—C7—C8—C9	−179.63 (18)
C6—N3—C1—C5	0.9 (2)	C7—C8—C9—C10	−0.5 (3)
N3—C1—C2—C3	179.6 (2)	C8—C9—C10—C11	1.5 (3)
C5—C1—C2—C3	−0.4 (3)	C8—C9—C10—N4	−178.13 (18)
C1—C2—C3—C4	2.3 (3)	O1—N4—C10—C11	176.3 (2)
C1—C2—C3—Br1	−177.37 (13)	O2—N4—C10—C11	−3.8 (3)
C5—N1—C4—C3	−0.3 (3)	O1—N4—C10—C9	−4.1 (3)
C13—N1—C4—C3	−179.31 (18)	O2—N4—C10—C9	175.81 (19)
C2—C3—C4—N1	−2.0 (3)	C9—C10—C11—C12	−1.0 (3)
Br1—C3—C4—N1	177.68 (14)	N4—C10—C11—C12	178.54 (18)
C6—N2—C5—N1	−178.66 (19)	C10—C11—C12—C7	−0.3 (3)
C6—N2—C5—C1	−0.1 (2)	C8—C7—C12—C11	1.2 (3)
C4—N1—C5—N2	−179.38 (18)	C6—C7—C12—C11	−179.94 (18)
C13—N1—C5—N2	−0.4 (3)	C5—N1—C13—C14	−83.3 (2)
C4—N1—C5—C1	2.2 (3)	C4—N1—C13—C14	95.7 (2)
C13—N1—C5—C1	−178.80 (18)	N1—C13—C14—C15	169.76 (17)
N3—C1—C5—N2	−0.5 (2)	C13—C14—C15—C16	−74.4 (3)
C2—C1—C5—N2	179.53 (17)	C14—C15—C16—C17	−168.7 (2)
N3—C1—C5—N1	178.14 (17)	C15—C16—C17—C18	177.0 (2)
C2—C1—C5—N1	−1.8 (3)	C16—C17—C18—C19	−179.0 (3)
C1—N3—C6—N2	−1.0 (2)	C17—C18—C19—C20	178.2 (3)
C1—N3—C6—C7	178.18 (17)	C18—C19—C20—C21	175.8 (3)
C5—N2—C6—N3	0.7 (2)	C19—C20—C21—C22	−173.9 (3)
C5—N2—C6—C7	−178.50 (17)	C20—C21—C22—C23	172.0 (3)
N3—C6—C7—C8	−0.5 (3)	C21—C22—C23—C24A	−169.6 (2)
N2—C6—C7—C8	178.74 (18)	C21—C22—C23—C24	−169.6 (2)
N3—C6—C7—C12	−179.32 (18)	C22—C23—C24—Br2	−66.7 (3)
N2—C6—C7—C12	−0.1 (3)	C22—C23—C24A—Br2A	−76.3 (3)
C12—C7—C8—C9	−0.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1^i	0.95	2.43	3.171 (3)	135
C24—H24A···O2^ii	0.99	2.53	3.372 (3)	142

Symmetry codes: (i) x+1, y+1, z; (ii) −x, −y+1, −z+1.