Ethyl 2-(6-bromo-2-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)acetate

The title imidazo [4,5-b] pyridine derivative, C₁₆H₁₄BrN₃O₂, crystallizes with two independent mol­ecules (1 and 2) in the asymmetric unit. In mol­ecule 1, the pendant phenyl ring is inclined to the imidazo[4,5-b]pyridine core by 43.10 (4)° while in mol­ecule 2 the corresponding angle is 49.43 (4)°. The two mol­ecules differ primarily in the conformations of the ester substituents. In the crystal, mol­ecules are linked via C—H...N and C—H...O hydrogen bonds, forming sheets parallel to the ab plane.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.031
• wR factor = 0.080
• Data-to-parameter ratio = 19.9

checkCIF/PLATON results

No syntax errors found



Alert level G
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         31 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         12 Note

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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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: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012), Mercury (Macrae et al., 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Ethyl 2-(6-bromo-2-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)acetate

Crystal data

C16H14BrN3O2	F(000) = 1456
Mr = 360.21	Dx = 1.567 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.1444 (14) Å	Cell parameters from 9951 reflections
b = 7.6970 (5) Å	θ = 2.2–28.7°
c = 21.2671 (14) Å	µ = 2.70 mm^−1
β = 118.073 (1)°	T = 150 K
V = 3054.0 (3) Å^3	Block, colourless
Z = 8	0.36 × 0.24 × 0.16 mm

Data collection

Bruker SMART APEX CCD diffractometer	7958 independent reflections
Radiation source: fine-focus sealed tube	6411 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
Detector resolution: 8.3333 pixels mm^-1	θmax = 28.8°, θmin = 1.9°
φ and ω scans	h = −28→28
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −10→10
Tmin = 0.52, Tmax = 0.68	l = −28→28
56392 measured reflections

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.080	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0421P)^2 + 0.9304P] where P = (Fo^2 + 2Fc^2)/3
7958 reflections	(Δ/σ)max = 0.002
399 parameters	Δρmax = 0.78 e Å^−3
0 restraints	Δρmin = −0.64 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 20 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.

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

	x	y	z	Uiso*/Ueq
Br1	0.03279 (2)	0.34558 (3)	−0.09058 (2)	0.03671 (6)
O1	0.38784 (7)	0.20747 (17)	0.19067 (9)	0.0438 (4)
O2	0.45553 (6)	0.44806 (16)	0.22466 (7)	0.0314 (3)
N1	0.23565 (8)	0.43626 (19)	0.07421 (8)	0.0276 (3)
N2	0.17346 (7)	0.29001 (18)	0.19504 (7)	0.0230 (3)
N3	0.27629 (7)	0.38736 (18)	0.19942 (8)	0.0232 (3)
C1	0.22566 (9)	0.3863 (2)	0.12858 (9)	0.0229 (3)
C2	0.17676 (10)	0.4227 (2)	0.01076 (10)	0.0297 (4)
H2	0.1796	0.4571	−0.0307	0.036*
C3	0.11122 (10)	0.3601 (2)	0.00294 (9)	0.0267 (3)
C4	0.10175 (9)	0.3103 (2)	0.06064 (9)	0.0252 (3)
H4	0.0572	0.2689	0.0554	0.030*
C5	0.16211 (9)	0.3251 (2)	0.12659 (9)	0.0222 (3)
C6	0.24160 (9)	0.3287 (2)	0.23677 (9)	0.0224 (3)
C7	0.27518 (9)	0.3096 (2)	0.31450 (9)	0.0247 (3)
C8	0.23533 (10)	0.3596 (2)	0.34853 (10)	0.0270 (4)
H8	0.1897	0.4123	0.3219	0.032*
C9	0.26230 (11)	0.3323 (2)	0.42127 (10)	0.0342 (4)
H9	0.2350	0.3663	0.4441	0.041*
C10	0.32864 (12)	0.2560 (3)	0.46039 (10)	0.0409 (5)
H10	0.3467	0.2365	0.5100	0.049*
C11	0.36882 (11)	0.2077 (3)	0.42727 (11)	0.0430 (5)
H11	0.4147	0.1563	0.4544	0.052*
C12	0.34243 (10)	0.2341 (2)	0.35440 (10)	0.0331 (4)
H12	0.3702	0.2008	0.3319	0.040*
C13	0.34645 (9)	0.4662 (2)	0.22469 (10)	0.0270 (4)
H13A	0.3674	0.4875	0.2766	0.032*
H13B	0.3409	0.5800	0.2010	0.032*
C14	0.39738 (9)	0.3549 (2)	0.21071 (9)	0.0236 (3)
C15	0.51121 (9)	0.3649 (2)	0.21269 (11)	0.0322 (4)
H15A	0.5119	0.2387	0.2219	0.039*
H15B	0.5586	0.4133	0.2463	0.039*
C16	0.49801 (13)	0.3934 (4)	0.13880 (13)	0.0544 (6)
H16A	0.5367	0.3402	0.1324	0.082*
H16B	0.4964	0.5185	0.1294	0.082*
H16C	0.4521	0.3406	0.1055	0.082*
Br2	0.44606 (2)	0.61495 (3)	0.59602 (2)	0.04201 (7)
O3	0.09890 (6)	0.65678 (15)	0.26396 (7)	0.0287 (3)
O4	0.04948 (6)	0.87883 (14)	0.29441 (6)	0.0232 (2)
N4	0.25938 (8)	0.82785 (18)	0.43947 (8)	0.0258 (3)
N5	0.32621 (7)	0.75523 (18)	0.31553 (7)	0.0224 (3)
N6	0.22554 (7)	0.85498 (17)	0.31455 (7)	0.0204 (3)
C17	0.27181 (8)	0.8110 (2)	0.38410 (9)	0.0208 (3)
C18	0.31420 (10)	0.7737 (2)	0.50126 (9)	0.0283 (4)
H18	0.3098	0.7840	0.5435	0.034*
C19	0.37712 (9)	0.7032 (2)	0.50626 (9)	0.0274 (4)
C20	0.38933 (9)	0.6896 (2)	0.44782 (9)	0.0249 (3)
H20	0.4325	0.6430	0.4513	0.030*
C21	0.33398 (8)	0.7488 (2)	0.38388 (8)	0.0214 (3)
C22	0.26099 (8)	0.8176 (2)	0.27574 (8)	0.0199 (3)
C23	0.22979 (8)	0.84618 (19)	0.19843 (9)	0.0203 (3)
C24	0.27120 (9)	0.9308 (2)	0.17252 (9)	0.0228 (3)
H24	0.3180	0.9697	0.2048	0.027*
C25	0.24465 (9)	0.9582 (2)	0.10030 (9)	0.0270 (4)
H25	0.2728	1.0177	0.0832	0.032*
C26	0.17650 (10)	0.8986 (2)	0.05261 (10)	0.0304 (4)
H26	0.1583	0.9165	0.0029	0.036*
C27	0.13536 (10)	0.8131 (2)	0.07791 (10)	0.0313 (4)
H27	0.0889	0.7722	0.0453	0.038*
C28	0.16135 (9)	0.7866 (2)	0.15052 (9)	0.0266 (3)
H28	0.1328	0.7284	0.1675	0.032*
C29	0.15676 (8)	0.9377 (2)	0.29260 (9)	0.0213 (3)
H29A	0.1425	1.0014	0.2475	0.026*
H29B	0.1610	1.0229	0.3293	0.026*
C30	0.09915 (8)	0.8050 (2)	0.28196 (8)	0.0202 (3)
C31	−0.00920 (8)	0.7680 (2)	0.28889 (9)	0.0246 (3)
H31A	−0.0262	0.6938	0.2459	0.029*
H31B	−0.0497	0.8413	0.2840	0.029*
C32	0.01568 (10)	0.6550 (2)	0.35418 (10)	0.0322 (4)
H32A	−0.0255	0.5936	0.3530	0.048*
H32B	0.0380	0.7277	0.3970	0.048*
H32C	0.0507	0.5704	0.3550	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.04049 (11)	0.04320 (12)	0.02440 (10)	−0.00655 (8)	0.01359 (8)	0.00355 (7)
O1	0.0337 (7)	0.0225 (6)	0.0865 (12)	−0.0059 (5)	0.0375 (8)	−0.0132 (7)
O2	0.0226 (6)	0.0299 (6)	0.0477 (8)	−0.0078 (5)	0.0215 (6)	−0.0128 (6)
N1	0.0310 (8)	0.0275 (7)	0.0340 (8)	−0.0030 (6)	0.0233 (7)	−0.0006 (6)
N2	0.0227 (7)	0.0250 (7)	0.0244 (7)	−0.0007 (5)	0.0137 (6)	−0.0001 (5)
N3	0.0200 (7)	0.0241 (7)	0.0306 (7)	−0.0019 (5)	0.0161 (6)	−0.0026 (6)
C1	0.0237 (8)	0.0211 (7)	0.0306 (9)	−0.0005 (6)	0.0182 (7)	−0.0015 (6)
C2	0.0386 (10)	0.0299 (9)	0.0309 (9)	−0.0019 (7)	0.0249 (8)	0.0007 (7)
C3	0.0300 (9)	0.0263 (8)	0.0258 (9)	0.0000 (7)	0.0148 (7)	0.0008 (6)
C4	0.0243 (8)	0.0276 (8)	0.0279 (9)	−0.0014 (6)	0.0157 (7)	0.0014 (7)
C5	0.0230 (8)	0.0217 (7)	0.0274 (8)	0.0007 (6)	0.0166 (7)	0.0011 (6)
C6	0.0230 (8)	0.0202 (7)	0.0276 (8)	0.0011 (6)	0.0148 (7)	−0.0014 (6)
C7	0.0243 (8)	0.0204 (7)	0.0278 (9)	−0.0044 (6)	0.0110 (7)	−0.0024 (6)
C8	0.0281 (9)	0.0259 (8)	0.0291 (9)	−0.0049 (7)	0.0152 (7)	−0.0018 (7)
C9	0.0435 (11)	0.0326 (9)	0.0291 (9)	−0.0115 (8)	0.0192 (9)	−0.0046 (7)
C10	0.0494 (12)	0.0365 (11)	0.0261 (10)	−0.0097 (9)	0.0088 (9)	0.0014 (8)
C11	0.0353 (11)	0.0358 (10)	0.0370 (11)	0.0012 (8)	−0.0004 (9)	0.0027 (8)
C12	0.0273 (9)	0.0301 (9)	0.0362 (10)	0.0003 (7)	0.0103 (8)	−0.0036 (8)
C13	0.0227 (8)	0.0248 (8)	0.0395 (10)	−0.0058 (6)	0.0197 (7)	−0.0083 (7)
C14	0.0181 (7)	0.0236 (8)	0.0297 (9)	−0.0033 (6)	0.0116 (7)	−0.0024 (6)
C15	0.0179 (8)	0.0332 (9)	0.0485 (12)	−0.0003 (7)	0.0181 (8)	−0.0024 (8)
C16	0.0421 (13)	0.0772 (17)	0.0538 (15)	0.0154 (12)	0.0307 (12)	0.0026 (12)
Br2	0.04307 (12)	0.04776 (13)	0.02611 (10)	0.00104 (9)	0.00875 (9)	0.00918 (8)
O3	0.0278 (6)	0.0227 (6)	0.0422 (7)	−0.0029 (5)	0.0219 (6)	−0.0076 (5)
O4	0.0197 (5)	0.0206 (5)	0.0349 (7)	−0.0003 (4)	0.0176 (5)	−0.0019 (5)
N4	0.0296 (7)	0.0279 (7)	0.0250 (7)	−0.0025 (6)	0.0170 (6)	−0.0016 (6)
N5	0.0208 (7)	0.0257 (7)	0.0228 (7)	−0.0004 (5)	0.0121 (6)	−0.0035 (5)
N6	0.0179 (6)	0.0230 (7)	0.0235 (7)	−0.0009 (5)	0.0125 (6)	−0.0027 (5)
C17	0.0207 (7)	0.0196 (7)	0.0243 (8)	−0.0033 (6)	0.0124 (6)	−0.0024 (6)
C18	0.0348 (9)	0.0295 (9)	0.0249 (9)	−0.0045 (7)	0.0176 (8)	−0.0007 (7)
C19	0.0297 (9)	0.0265 (8)	0.0217 (8)	−0.0033 (7)	0.0087 (7)	0.0013 (6)
C20	0.0213 (8)	0.0259 (8)	0.0266 (9)	−0.0011 (6)	0.0105 (7)	−0.0003 (6)
C21	0.0216 (8)	0.0210 (7)	0.0245 (8)	−0.0033 (6)	0.0132 (7)	−0.0032 (6)
C22	0.0195 (7)	0.0196 (7)	0.0237 (8)	−0.0033 (6)	0.0128 (6)	−0.0045 (6)
C23	0.0205 (7)	0.0195 (7)	0.0233 (8)	0.0007 (6)	0.0123 (6)	−0.0026 (6)
C24	0.0200 (7)	0.0216 (7)	0.0286 (8)	−0.0004 (6)	0.0129 (7)	−0.0030 (6)
C25	0.0327 (9)	0.0253 (8)	0.0305 (9)	−0.0005 (7)	0.0211 (8)	0.0004 (7)
C26	0.0348 (10)	0.0340 (9)	0.0229 (9)	0.0010 (8)	0.0140 (8)	0.0006 (7)
C27	0.0252 (9)	0.0392 (10)	0.0258 (9)	−0.0058 (7)	0.0089 (7)	−0.0064 (7)
C28	0.0232 (8)	0.0319 (9)	0.0263 (9)	−0.0053 (7)	0.0131 (7)	−0.0041 (7)
C29	0.0180 (7)	0.0208 (7)	0.0279 (8)	−0.0005 (6)	0.0131 (7)	−0.0014 (6)
C30	0.0179 (7)	0.0226 (8)	0.0211 (8)	0.0007 (6)	0.0101 (6)	0.0002 (6)
C31	0.0179 (7)	0.0264 (8)	0.0322 (9)	−0.0020 (6)	0.0141 (7)	−0.0007 (7)
C32	0.0304 (9)	0.0356 (10)	0.0360 (10)	−0.0025 (8)	0.0200 (8)	0.0029 (8)

Geometric parameters (Å, º)

Br1—C3	1.9011 (18)	Br2—C19	1.9004 (17)
O1—C14	1.196 (2)	O3—C30	1.2025 (19)
O2—C14	1.3305 (19)	O4—C30	1.3258 (19)
O2—C15	1.464 (2)	O4—C31	1.4644 (19)
N1—C1	1.326 (2)	N4—C17	1.328 (2)
N1—C2	1.342 (2)	N4—C18	1.346 (2)
N2—C6	1.323 (2)	N5—C22	1.323 (2)
N2—C5	1.386 (2)	N5—C21	1.385 (2)
N3—C1	1.378 (2)	N6—C17	1.378 (2)
N3—C6	1.386 (2)	N6—C22	1.381 (2)
N3—C13	1.452 (2)	N6—C29	1.4489 (19)
C1—C5	1.406 (2)	C17—C21	1.401 (2)
C2—C3	1.401 (2)	C18—C19	1.394 (3)
C2—H2	0.9500	C18—H18	0.9500
C3—C4	1.387 (2)	C19—C20	1.387 (2)
C4—C5	1.387 (2)	C20—C21	1.389 (2)
C4—H4	0.9500	C20—H20	0.9500
C6—C7	1.467 (2)	C22—C23	1.472 (2)
C7—C12	1.394 (2)	C23—C24	1.396 (2)
C7—C8	1.399 (2)	C23—C28	1.398 (2)
C8—C9	1.390 (3)	C24—C25	1.381 (2)
C8—H8	0.9500	C24—H24	0.9500
C9—C10	1.381 (3)	C25—C26	1.393 (3)
C9—H9	0.9500	C25—H25	0.9500
C10—C11	1.385 (3)	C26—C27	1.386 (3)
C10—H10	0.9500	C26—H26	0.9500
C11—C12	1.393 (3)	C27—C28	1.389 (2)
C11—H11	0.9500	C27—H27	0.9500
C12—H12	0.9500	C28—H28	0.9500
C13—C14	1.511 (2)	C29—C30	1.523 (2)
C13—H13A	0.9900	C29—H29A	0.9900
C13—H13B	0.9900	C29—H29B	0.9900
C15—C16	1.477 (3)	C31—C32	1.508 (2)
C15—H15A	0.9900	C31—H31A	0.9900
C15—H15B	0.9900	C31—H31B	0.9900
C16—H16A	0.9800	C32—H32A	0.9800
C16—H16B	0.9800	C32—H32B	0.9800
C16—H16C	0.9800	C32—H32C	0.9800
C14—O2—C15	117.40 (13)	C30—O4—C31	117.07 (12)
C1—N1—C2	113.65 (14)	C17—N4—C18	113.36 (15)
C6—N2—C5	104.84 (13)	C22—N5—C21	104.92 (13)
C1—N3—C6	106.05 (13)	C17—N6—C22	106.23 (13)
C1—N3—C13	122.69 (14)	C17—N6—C29	123.50 (13)
C6—N3—C13	130.39 (15)	C22—N6—C29	130.06 (14)
N1—C1—N3	126.24 (15)	N4—C17—N6	126.23 (15)
N1—C1—C5	127.80 (16)	N4—C17—C21	127.87 (15)
N3—C1—C5	105.95 (14)	N6—C17—C21	105.89 (14)
N1—C2—C3	122.95 (16)	N4—C18—C19	123.22 (16)
N1—C2—H2	118.5	N4—C18—H18	118.4
C3—C2—H2	118.5	C19—C18—H18	118.4
C4—C3—C2	122.45 (17)	C20—C19—C18	122.31 (16)
C4—C3—Br1	119.41 (13)	C20—C19—Br2	119.65 (13)
C2—C3—Br1	118.14 (13)	C18—C19—Br2	117.99 (13)
C5—C4—C3	115.11 (15)	C19—C20—C21	115.21 (15)
C5—C4—H4	122.4	C19—C20—H20	122.4
C3—C4—H4	122.4	C21—C20—H20	122.4
N2—C5—C4	131.91 (15)	N5—C21—C20	131.96 (15)
N2—C5—C1	110.07 (14)	N5—C21—C17	110.08 (14)
C4—C5—C1	118.02 (15)	C20—C21—C17	117.94 (15)
N2—C6—N3	113.08 (14)	N5—C22—N6	112.88 (14)
N2—C6—C7	122.00 (15)	N5—C22—C23	123.58 (14)
N3—C6—C7	124.91 (15)	N6—C22—C23	123.53 (14)
C12—C7—C8	119.34 (17)	C24—C23—C28	119.45 (15)
C12—C7—C6	122.80 (16)	C24—C23—C22	118.44 (14)
C8—C7—C6	117.74 (15)	C28—C23—C22	122.08 (14)
C9—C8—C7	120.19 (18)	C25—C24—C23	120.56 (15)
C9—C8—H8	119.9	C25—C24—H24	119.7
C7—C8—H8	119.9	C23—C24—H24	119.7
C10—C9—C8	120.21 (19)	C24—C25—C26	119.93 (16)
C10—C9—H9	119.9	C24—C25—H25	120.0
C8—C9—H9	119.9	C26—C25—H25	120.0
C9—C10—C11	120.00 (19)	C27—C26—C25	119.81 (17)
C9—C10—H10	120.0	C27—C26—H26	120.1
C11—C10—H10	120.0	C25—C26—H26	120.1
C10—C11—C12	120.40 (19)	C26—C27—C28	120.61 (17)
C10—C11—H11	119.8	C26—C27—H27	119.7
C12—C11—H11	119.8	C28—C27—H27	119.7
C11—C12—C7	119.85 (19)	C27—C28—C23	119.62 (16)
C11—C12—H12	120.1	C27—C28—H28	120.2
C7—C12—H12	120.1	C23—C28—H28	120.2
N3—C13—C14	112.88 (13)	N6—C29—C30	111.38 (13)
N3—C13—H13A	109.0	N6—C29—H29A	109.4
C14—C13—H13A	109.0	C30—C29—H29A	109.4
N3—C13—H13B	109.0	N6—C29—H29B	109.4
C14—C13—H13B	109.0	C30—C29—H29B	109.4
H13A—C13—H13B	107.8	H29A—C29—H29B	108.0
O1—C14—O2	125.04 (16)	O3—C30—O4	125.81 (15)
O1—C14—C13	126.29 (15)	O3—C30—C29	124.54 (14)
O2—C14—C13	108.66 (13)	O4—C30—C29	109.65 (13)
O2—C15—C16	110.81 (16)	O4—C31—C32	110.30 (13)
O2—C15—H15A	109.5	O4—C31—H31A	109.6
C16—C15—H15A	109.5	C32—C31—H31A	109.6
O2—C15—H15B	109.5	O4—C31—H31B	109.6
C16—C15—H15B	109.5	C32—C31—H31B	109.6
H15A—C15—H15B	108.1	H31A—C31—H31B	108.1
C15—C16—H16A	109.5	C31—C32—H32A	109.5
C15—C16—H16B	109.5	C31—C32—H32B	109.5
H16A—C16—H16B	109.5	H32A—C32—H32B	109.5
C15—C16—H16C	109.5	C31—C32—H32C	109.5
H16A—C16—H16C	109.5	H32A—C32—H32C	109.5
H16B—C16—H16C	109.5	H32B—C32—H32C	109.5
C2—N1—C1—N3	−179.53 (16)	C18—N4—C17—N6	179.81 (15)
C2—N1—C1—C5	−0.8 (3)	C18—N4—C17—C21	−1.4 (2)
C6—N3—C1—N1	178.59 (16)	C22—N6—C17—N4	179.21 (15)
C13—N3—C1—N1	8.2 (2)	C29—N6—C17—N4	3.9 (2)
C6—N3—C1—C5	−0.39 (17)	C22—N6—C17—C21	0.22 (16)
C13—N3—C1—C5	−170.75 (14)	C29—N6—C17—C21	−175.04 (13)
C1—N1—C2—C3	−0.5 (2)	C17—N4—C18—C19	−1.4 (2)
N1—C2—C3—C4	1.3 (3)	N4—C18—C19—C20	2.6 (3)
N1—C2—C3—Br1	−179.18 (13)	N4—C18—C19—Br2	−174.78 (13)
C2—C3—C4—C5	−0.6 (3)	C18—C19—C20—C21	−0.9 (2)
Br1—C3—C4—C5	179.82 (12)	Br2—C19—C20—C21	176.44 (12)
C6—N2—C5—C4	179.93 (18)	C22—N5—C21—C20	177.30 (17)
C6—N2—C5—C1	−0.04 (18)	C22—N5—C21—C17	−0.68 (17)
C3—C4—C5—N2	179.51 (17)	C19—C20—C21—N5	−179.45 (16)
C3—C4—C5—C1	−0.5 (2)	C19—C20—C21—C17	−1.6 (2)
N1—C1—C5—N2	−178.69 (16)	N4—C17—C21—N5	−178.69 (15)
N3—C1—C5—N2	0.28 (18)	N6—C17—C21—N5	0.28 (17)
N1—C1—C5—C4	1.3 (3)	N4—C17—C21—C20	3.0 (3)
N3—C1—C5—C4	−179.69 (14)	N6—C17—C21—C20	−178.02 (14)
C5—N2—C6—N3	−0.23 (18)	C21—N5—C22—N6	0.84 (17)
C5—N2—C6—C7	179.86 (14)	C21—N5—C22—C23	−179.91 (14)
C1—N3—C6—N2	0.40 (18)	C17—N6—C22—N5	−0.69 (18)
C13—N3—C6—N2	169.74 (15)	C29—N6—C22—N5	174.15 (14)
C1—N3—C6—C7	−179.69 (15)	C17—N6—C22—C23	−179.94 (14)
C13—N3—C6—C7	−10.4 (3)	C29—N6—C22—C23	−5.1 (2)
N2—C6—C7—C12	135.06 (18)	N5—C22—C23—C24	−46.9 (2)
N3—C6—C7—C12	−44.8 (2)	N6—C22—C23—C24	132.28 (16)
N2—C6—C7—C8	−40.7 (2)	N5—C22—C23—C28	131.04 (17)
N3—C6—C7—C8	139.38 (16)	N6—C22—C23—C28	−49.8 (2)
C12—C7—C8—C9	−0.7 (2)	C28—C23—C24—C25	1.0 (2)
C6—C7—C8—C9	175.21 (15)	C22—C23—C24—C25	179.01 (15)
C7—C8—C9—C10	0.1 (3)	C23—C24—C25—C26	−1.1 (2)
C8—C9—C10—C11	0.6 (3)	C24—C25—C26—C27	0.5 (3)
C9—C10—C11—C12	−0.6 (3)	C25—C26—C27—C28	0.2 (3)
C10—C11—C12—C7	0.0 (3)	C26—C27—C28—C23	−0.3 (3)
C8—C7—C12—C11	0.7 (3)	C24—C23—C28—C27	−0.3 (2)
C6—C7—C12—C11	−175.04 (17)	C22—C23—C28—C27	−178.23 (16)
C1—N3—C13—C14	−77.4 (2)	C17—N6—C29—C30	−83.16 (18)
C6—N3—C13—C14	114.83 (18)	C22—N6—C29—C30	102.78 (18)
C15—O2—C14—O1	1.7 (3)	C31—O4—C30—O3	3.0 (2)
C15—O2—C14—C13	−178.48 (15)	C31—O4—C30—C29	−178.06 (13)
N3—C13—C14—O1	−10.3 (3)	N6—C29—C30—O3	−29.5 (2)
N3—C13—C14—O2	169.93 (15)	N6—C29—C30—O4	151.51 (13)
C14—O2—C15—C16	89.1 (2)	C30—O4—C31—C32	77.07 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O3	0.95	2.55	3.450 (2)	158
C13—H13A···N5	0.99	2.52	3.105 (2)	117
C15—H15A···O2^i	0.99	2.46	3.418 (2)	164
C24—H24···O1^ii	0.95	2.46	3.142 (2)	129
C28—H28···O3	0.95	2.53	3.400 (2)	152
C31—H31A···O4^iii	0.99	2.54	3.379 (2)	142

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x, y+1, z; (iii) −x, y−1/2, −z+1/2.