4-(4-Bromo­phenyl)-2,5-diethoxy­carbonyl-6-methyl­thieno­[2,3-b]­pyridine

The title compound, alternatively named diethyl 4-(4-bromo­phenyl)-6-methyl­thieno­[2,3-b]­pyridine-2,5-di­carboxyl­ate, C₂₀H₁₈BrNO₄S, crystallizes with two crystallographically independent mol­ecules in the asymmetric unit. The crystal structure is stabilized by intermolecular and intramolecular C—H...O hydrogen bonds. The thieno­[2,3-b]­pyridine moiety is planar.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.046
• wR factor = 0.132
• Data-to-parameter ratio = 9.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



PLAT_360  Alert B Short  C(sp3)-C(sp3) Bond  C(24)  -   C(25)  =       1.32 Ang.


 Alert Level C:



PLAT_360  Alert C Short  C(sp3)-C(sp3) Bond  C(354) -   C(355) =       1.42 Ang.

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           69.18
         From the CIF: _reflns_number_total               4714
         Count of symmetry unique reflns         4281
         Completeness (_total/calc)            110.11%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured       433
         Fraction of Friedel pairs measured     0.101
         Are heavy atom types Z>Si present          yes
          WARNING: Large fraction of Friedel related reflns may
                   be needed to determine absolute structure


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

Computing details

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Bergerhoff, 1996); software used to prepare material for publication: PARST (Nardelli, 1995), PARSTCIF (Nardelli, 1991) and PLATON (Spek, 1990).

Diethyl 4-(4-bromophenyl)-6-methylthieno[2,3-b]pyridine-2,5-dicarboxylate

Crystal data

C20H18BrNO4S	Dx = 1.488 Mg m^−3
Mr = 448.32	Cu Kα radiation, λ = 1.54180 Å
Orthorhombic, P212121	Cell parameters from 67 reflections
a = 7.8114 (6) Å	θ = 1.9–33.1°
b = 11.2988 (6) Å	µ = 3.99 mm^−1
c = 45.353 (2) Å	T = 293 K
V = 4002.8 (4) Å^3	Prism, pale yellow
Z = 8	0.44 × 0.38 × 0.11 mm
F(000) = 1824

Data collection

Siemens P4 four-circle diffractometer	Rint = 0.038
ω/2θ scans	θmax = 69.2°
Absorption correction: ψ scan (North et al., 1968) and XEMP (Siemens, 1989)	h = −1→9
Tmin = 0.126, Tmax = 0.645	k = −1→13
5061 measured reflections	l = −1→54
4714 independent reflections	3 standard reflections every 100 reflections
4275 reflections with F^2 > 2σ(F^2)	intensity decay: 3.6%

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (.0862P)^2 + 1.0278P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.046	(Δ/σ)max = 0.001
wR(F^2) = 0.132	Δρmax = 0.55 e Å^−3
S = 1.05	Δρmin = −0.34 e Å^−3
4714 reflections	Absolute structure: Flack (1983), 433 Friedel pairs [OK?]
493 parameters	Absolute structure parameter: −0.02 (2)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'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

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

	x	y	z	Uiso*/Ueq
Br1	−0.33858 (17)	−0.42736 (10)	0.50083 (2)	0.1412 (5)
S1	−0.41873 (18)	0.18093 (10)	0.36218 (3)	0.0663 (3)
O22	−0.5877 (7)	0.2323 (4)	0.44290 (9)	0.0943 (16)
O23	−0.5787 (7)	0.3471 (3)	0.40274 (8)	0.0887 (14)
O52	−0.0443 (6)	−0.3481 (4)	0.35038 (12)	0.1023 (16)
O53	−0.3188 (6)	−0.3856 (3)	0.35786 (11)	0.0936 (16)
N7	−0.2816 (5)	−0.0040 (4)	0.33342 (9)	0.0637 (12)
C2	−0.4706 (6)	0.1558 (4)	0.39884 (11)	0.0637 (14)
C3	−0.4302 (7)	0.0454 (4)	0.40800 (10)	0.0633 (14)
C3A	−0.3582 (6)	−0.0257 (4)	0.38542 (10)	0.0600 (12)
C4	−0.3034 (6)	−0.1446 (4)	0.38537 (11)	0.0610 (14)
C5	−0.2392 (7)	−0.1879 (4)	0.35878 (11)	0.0630 (14)
C6	−0.2304 (7)	−0.1161 (4)	0.33337 (11)	0.0630 (16)
C7A	−0.3427 (6)	0.0362 (4)	0.35873 (10)	0.0580 (12)
C21	−0.5506 (8)	0.2468 (4)	0.41730 (12)	0.0717 (17)
C24	−0.6519 (17)	0.4452 (7)	0.41891 (17)	0.151 (5)
C25	−0.7378 (14)	0.5211 (8)	0.4026 (3)	0.151 (4)
C41	−0.3128 (7)	−0.2156 (4)	0.41260 (11)	0.0647 (16)
C42	−0.4654 (8)	−0.2206 (5)	0.42859 (12)	0.0743 (17)
C43	−0.4702 (10)	−0.2844 (6)	0.45504 (13)	0.089 (2)
C44	−0.3295 (11)	−0.3425 (6)	0.46469 (13)	0.092 (2)
C45	−0.1782 (10)	−0.3402 (7)	0.44889 (15)	0.097 (3)
C46	−0.1711 (9)	−0.2788 (5)	0.42313 (14)	0.0830 (19)
C51	−0.1856 (8)	−0.3143 (5)	0.35567 (12)	0.0683 (16)
C54	−0.2889 (13)	−0.5117 (5)	0.3523 (2)	0.120 (4)
C55	−0.3419 (13)	−0.5361 (7)	0.3208 (2)	0.136 (4)
C61	−0.1697 (8)	−0.1641 (5)	0.30409 (12)	0.0783 (17)
Br2	0.06744 (11)	0.55843 (5)	0.26992 (1)	0.0901 (2)
S31	0.0557 (2)	0.00165 (13)	0.42374 (3)	0.0755 (4)
O322	−0.1490 (8)	0.3131 (5)	0.43865 (10)	0.1083 (19)
O323	−0.1368 (6)	0.1431 (5)	0.46433 (8)	0.0973 (16)
O352	0.2418 (7)	−0.0783 (4)	0.28160 (9)	0.0927 (14)
O353	0.3825 (5)	0.0862 (4)	0.29401 (8)	0.0775 (11)
N37	0.1958 (6)	−0.1058 (4)	0.37676 (9)	0.0693 (12)
C32	−0.0156 (7)	0.1447 (5)	0.41804 (10)	0.0703 (16)
C33	0.0110 (7)	0.1842 (5)	0.39014 (10)	0.0637 (14)
C33A	0.0929 (6)	0.0976 (4)	0.37190 (10)	0.0587 (12)
C34	0.1414 (6)	0.1009 (4)	0.34210 (10)	0.0580 (12)
C35	0.2141 (6)	−0.0009 (4)	0.33037 (11)	0.0600 (12)
C36	0.2390 (7)	−0.1032 (4)	0.34825 (12)	0.0637 (14)
C37A	0.1238 (6)	−0.0082 (5)	0.38743 (11)	0.0650 (16)
C321	−0.1073 (9)	0.2117 (7)	0.44131 (12)	0.085 (2)
C324	−0.2358 (12)	0.1900 (9)	0.48857 (13)	0.112 (3)
C325	−0.3370 (12)	0.0929 (10)	0.50094 (17)	0.129 (4)
C341	0.1170 (6)	0.2115 (4)	0.32473 (9)	0.0573 (14)
C342	0.1867 (7)	0.3172 (4)	0.33473 (10)	0.0633 (14)
C343	0.1701 (7)	0.4210 (4)	0.31865 (11)	0.0670 (16)
C344	0.0841 (7)	0.4161 (4)	0.29223 (10)	0.0640 (14)
C345	0.0091 (8)	0.3141 (5)	0.28213 (10)	0.0707 (16)
C346	0.0250 (7)	0.2120 (4)	0.29848 (10)	0.0660 (16)
C351	0.2794 (7)	−0.0040 (5)	0.29931 (11)	0.0677 (17)
C354	0.4483 (11)	0.0973 (7)	0.26427 (14)	0.102 (2)
C355	0.5115 (14)	0.2144 (7)	0.2601 (2)	0.130 (4)
C361	0.3197 (8)	−0.2150 (5)	0.33647 (14)	0.0807 (19)
H3	−0.44778	0.01880	0.42717	0.0760*
H24A	−0.72797	0.41405	0.43392	0.1805*
H24B	−0.56033	0.48722	0.42888	0.1805*
H25A	−0.66663	0.54778	0.38662	0.2264*
H25B	−0.77128	0.58764	0.41439	0.2264*
H25C	−0.83796	0.48327	0.39472	0.2264*
H42	−0.56273	−0.18191	0.42175	0.0895*
H43	−0.57062	−0.28688	0.46603	0.1063*
H45	−0.08220	−0.38020	0.45581	0.1166*
H46	−0.07017	−0.27883	0.41227	0.0995*
H54A	−0.35586	−0.55957	0.36576	0.1441*
H54B	−0.16879	−0.53067	0.35501	0.1441*
H55A	−0.46452	−0.53679	0.31954	0.2033*
H55B	−0.29779	−0.61164	0.31480	0.2033*
H55C	−0.29697	−0.47545	0.30820	0.2033*
H61A	−0.21045	−0.11413	0.28847	0.1174*
H61B	−0.21315	−0.24280	0.30139	0.1174*
H61C	−0.04681	−0.16578	0.30380	0.1174*
H32A	−0.31063	0.25263	0.48166	0.1344*
H32B	−0.16023	0.22248	0.50350	0.1344*
H32C	−0.41961	0.06696	0.48665	0.1936*
H32D	−0.39517	0.11974	0.51834	0.1936*
H32E	−0.26266	0.02825	0.50592	0.1936*
H33	−0.02044	0.25913	0.38361	0.0764*
H35A	0.53967	0.04057	0.26115	0.1222*
H35B	0.35800	0.08110	0.25016	0.1222*
H35C	0.42373	0.27037	0.26508	0.1954*
H35D	0.54393	0.22480	0.23984	0.1954*
H35E	0.60930	0.22678	0.27251	0.1954*
H36A	0.37013	−0.25858	0.35244	0.1208*
H36B	0.40669	−0.19490	0.32238	0.1208*
H36C	0.23372	−0.26266	0.32710	0.1208*
H342	0.24571	0.31836	0.35254	0.0757*
H343	0.21577	0.49176	0.32555	0.0805*
H345	−0.05161	0.31389	0.26449	0.0849*
H346	−0.02641	0.14265	0.29190	0.0793*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.1741 (9)	0.1560 (9)	0.0936 (5)	−0.0159 (8)	0.0029 (6)	0.0519 (5)
S1	0.0728 (7)	0.0558 (5)	0.0703 (6)	0.0056 (7)	−0.0068 (6)	0.0010 (5)
O22	0.115 (3)	0.099 (3)	0.069 (2)	0.027 (3)	0.001 (2)	−0.0081 (19)
O23	0.118 (3)	0.074 (2)	0.074 (2)	0.029 (3)	−0.011 (2)	−0.0126 (17)
O52	0.071 (2)	0.076 (2)	0.160 (4)	0.017 (2)	0.016 (3)	−0.005 (3)
O53	0.079 (2)	0.0578 (19)	0.144 (4)	−0.003 (2)	0.027 (3)	−0.009 (2)
N7	0.063 (2)	0.061 (2)	0.067 (2)	−0.002 (2)	−0.0032 (19)	0.0022 (18)
C2	0.059 (3)	0.061 (2)	0.071 (2)	−0.003 (2)	−0.008 (2)	−0.009 (2)
C3	0.065 (3)	0.063 (2)	0.062 (2)	−0.004 (3)	−0.002 (2)	−0.0007 (19)
C3A	0.058 (2)	0.058 (2)	0.064 (2)	−0.003 (2)	−0.003 (2)	0.0014 (19)
C4	0.054 (2)	0.061 (2)	0.068 (3)	0.001 (2)	−0.001 (2)	0.002 (2)
C5	0.057 (2)	0.058 (2)	0.074 (3)	−0.003 (2)	0.000 (2)	0.006 (2)
C6	0.058 (3)	0.066 (3)	0.065 (2)	−0.002 (3)	0.000 (2)	−0.003 (2)
C7A	0.055 (2)	0.054 (2)	0.065 (2)	−0.003 (2)	−0.008 (2)	0.0002 (19)
C21	0.070 (3)	0.067 (3)	0.078 (3)	0.006 (3)	−0.018 (3)	−0.009 (2)
C24	0.257 (13)	0.100 (5)	0.095 (4)	0.095 (8)	−0.025 (7)	−0.029 (4)
C25	0.148 (8)	0.117 (6)	0.188 (9)	0.062 (7)	−0.058 (8)	−0.069 (6)
C41	0.067 (3)	0.056 (2)	0.071 (3)	0.001 (3)	0.005 (2)	0.004 (2)
C42	0.076 (3)	0.068 (3)	0.079 (3)	0.000 (3)	0.009 (3)	0.003 (2)
C43	0.102 (5)	0.082 (3)	0.082 (3)	−0.017 (4)	0.017 (3)	0.005 (3)
C44	0.116 (5)	0.084 (4)	0.076 (3)	−0.002 (4)	−0.007 (4)	0.017 (3)
C45	0.101 (5)	0.098 (4)	0.093 (4)	0.007 (4)	−0.007 (4)	0.027 (4)
C46	0.077 (3)	0.081 (3)	0.091 (4)	0.006 (3)	0.007 (3)	0.019 (3)
C51	0.070 (3)	0.059 (2)	0.076 (3)	0.002 (3)	0.007 (3)	0.001 (2)
C54	0.137 (7)	0.051 (3)	0.173 (8)	−0.008 (4)	0.049 (6)	−0.007 (4)
C55	0.128 (7)	0.093 (5)	0.186 (9)	−0.023 (5)	0.062 (7)	−0.040 (6)
C61	0.086 (3)	0.077 (3)	0.072 (3)	0.010 (3)	0.008 (3)	−0.002 (3)
Br2	0.1181 (5)	0.0744 (3)	0.0779 (3)	0.0095 (4)	0.0058 (4)	0.0190 (3)
S31	0.0799 (8)	0.0889 (8)	0.0578 (5)	−0.0076 (9)	−0.0048 (6)	0.0109 (6)
O322	0.140 (4)	0.098 (3)	0.087 (3)	0.006 (4)	0.023 (3)	−0.015 (2)
O323	0.103 (3)	0.129 (3)	0.060 (2)	0.004 (3)	0.014 (2)	−0.001 (2)
O352	0.108 (3)	0.084 (2)	0.086 (2)	−0.012 (3)	0.010 (2)	−0.022 (2)
O353	0.074 (2)	0.088 (2)	0.0706 (19)	−0.010 (2)	0.0173 (17)	−0.0043 (18)
N37	0.064 (2)	0.070 (2)	0.074 (2)	0.001 (2)	−0.006 (2)	0.007 (2)
C32	0.067 (3)	0.086 (3)	0.058 (2)	−0.015 (3)	−0.003 (2)	−0.006 (2)
C33	0.065 (3)	0.069 (2)	0.057 (2)	−0.003 (3)	0.000 (2)	−0.001 (2)
C33A	0.054 (2)	0.061 (2)	0.061 (2)	−0.005 (2)	−0.006 (2)	0.0018 (19)
C34	0.057 (2)	0.057 (2)	0.060 (2)	−0.009 (2)	−0.006 (2)	−0.0004 (19)
C35	0.055 (2)	0.058 (2)	0.067 (2)	−0.005 (2)	−0.004 (2)	0.001 (2)
C36	0.053 (2)	0.061 (2)	0.077 (3)	−0.005 (2)	−0.008 (2)	0.004 (2)
C37A	0.054 (2)	0.072 (3)	0.069 (3)	−0.006 (3)	−0.008 (2)	0.011 (2)
C321	0.081 (4)	0.115 (5)	0.058 (3)	−0.009 (4)	0.000 (3)	−0.014 (3)
C324	0.125 (6)	0.151 (7)	0.060 (3)	0.002 (6)	0.013 (4)	−0.011 (4)
C325	0.121 (6)	0.175 (9)	0.092 (4)	0.001 (7)	0.035 (5)	0.015 (5)
C341	0.061 (3)	0.057 (2)	0.054 (2)	0.005 (2)	0.002 (2)	−0.0005 (18)
C342	0.065 (3)	0.061 (2)	0.064 (2)	0.001 (3)	−0.004 (2)	0.000 (2)
C343	0.073 (3)	0.058 (2)	0.070 (3)	0.002 (3)	−0.001 (3)	−0.001 (2)
C344	0.069 (3)	0.063 (2)	0.060 (2)	0.009 (3)	0.011 (2)	0.007 (2)
C345	0.082 (3)	0.076 (3)	0.054 (2)	0.005 (3)	−0.007 (2)	0.001 (2)
C346	0.071 (3)	0.067 (3)	0.060 (2)	−0.002 (3)	−0.004 (2)	−0.003 (2)
C351	0.069 (3)	0.061 (3)	0.073 (3)	0.006 (3)	−0.002 (3)	−0.001 (2)
C354	0.115 (5)	0.109 (4)	0.082 (3)	−0.014 (5)	0.042 (4)	−0.003 (3)
C355	0.155 (8)	0.112 (5)	0.124 (6)	−0.018 (6)	0.059 (6)	0.017 (5)
C361	0.075 (3)	0.066 (3)	0.101 (4)	0.013 (3)	0.007 (3)	0.006 (3)

Geometric parameters (Å, º)

Br1—C44	1.900 (6)	C43—H43	0.9298
Br2—C344	1.904 (5)	C45—H45	0.9301
S1—C7A	1.747 (5)	C46—H46	0.9296
S1—C2	1.735 (5)	C54—H54A	0.9689
S31—C32	1.729 (6)	C54—H54B	0.9702
S31—C37A	1.734 (5)	C55—H55C	0.9588
O22—C21	1.208 (7)	C55—H55A	0.9596
O23—C24	1.447 (10)	C55—H55B	0.9598
O23—C21	1.330 (6)	C61—H61B	0.9596
O52—C51	1.192 (8)	C61—H61C	0.9602
O53—C51	1.320 (7)	C61—H61A	0.9602
O53—C54	1.466 (7)	C32—C33	1.358 (7)
O322—C321	1.197 (10)	C32—C321	1.483 (8)
O323—C321	1.321 (8)	C33—C33A	1.432 (7)
O323—C324	1.445 (9)	C33A—C34	1.404 (6)
O352—C351	1.198 (7)	C33A—C37A	1.408 (7)
O353—C354	1.449 (8)	C34—C35	1.389 (6)
O353—C351	1.321 (7)	C34—C341	1.489 (6)
N7—C6	1.328 (6)	C35—C36	1.425 (7)
N7—C7A	1.324 (6)	C35—C351	1.499 (7)
N37—C36	1.337 (7)	C36—C361	1.509 (8)
N37—C37A	1.329 (7)	C33—H33	0.9299
C2—C21	1.466 (7)	C324—C325	1.464 (14)
C2—C3	1.352 (6)	C341—C346	1.391 (6)
C3—C3A	1.418 (7)	C341—C342	1.389 (6)
C3A—C4	1.410 (6)	C342—C343	1.387 (7)
C3A—C7A	1.403 (6)	C343—C344	1.375 (7)
C4—C41	1.474 (7)	C344—C345	1.372 (7)
C4—C5	1.395 (7)	C345—C346	1.377 (7)
C5—C51	1.495 (7)	C354—C355	1.425 (12)
C5—C6	1.411 (7)	C324—H32A	0.9699
C6—C61	1.511 (7)	C324—H32B	0.9704
C24—C25	1.316 (15)	C325—H32C	0.9604
C41—C42	1.396 (8)	C325—H32D	0.9598
C41—C46	1.401 (8)	C325—H32E	0.9601
C42—C43	1.400 (8)	C342—H342	0.9301
C43—C44	1.353 (11)	C343—H343	0.9297
C44—C45	1.382 (11)	C345—H345	0.9300
C45—C46	1.360 (9)	C346—H346	0.9297
C54—C55	1.513 (13)	C354—H35A	0.9697
C3—H3	0.9301	C354—H35B	0.9698
C24—H24A	0.9697	C355—H35C	0.9597
C24—H24B	0.9703	C355—H35D	0.9603
C25—H25C	0.9605	C355—H35E	0.9592
C25—H25A	0.9619	C361—H36A	0.9603
C25—H25B	0.9589	C361—H36B	0.9600
C42—H42	0.9303	C361—H36C	0.9600
C2—S1—C7A	90.7 (2)	H61A—C61—H61B	109.48
C32—S31—C37A	91.0 (2)	C6—C61—H61A	109.47
C21—O23—C24	117.8 (5)	C6—C61—H61B	109.50
C51—O53—C54	117.1 (6)	C6—C61—H61C	109.44
C321—O323—C324	118.7 (6)	S31—C32—C33	113.4 (4)
C351—O353—C354	116.9 (5)	S31—C32—C321	121.8 (4)
C6—N7—C7A	115.9 (4)	C33—C32—C321	124.7 (5)
C36—N37—C37A	116.2 (4)	C32—C33—C33A	112.5 (5)
S1—C2—C21	122.2 (4)	C33—C33A—C34	131.2 (4)
C3—C2—C21	124.8 (5)	C33—C33A—C37A	111.6 (4)
S1—C2—C3	113.0 (4)	C34—C33A—C37A	117.2 (4)
C2—C3—C3A	113.2 (4)	C33A—C34—C35	117.2 (4)
C3—C3A—C4	131.4 (4)	C33A—C34—C341	119.8 (4)
C3—C3A—C7A	112.0 (4)	C35—C34—C341	123.0 (4)
C4—C3A—C7A	116.6 (4)	C34—C35—C36	120.6 (5)
C3A—C4—C5	116.4 (4)	C34—C35—C351	121.2 (4)
C5—C4—C41	123.5 (4)	C36—C35—C351	118.0 (4)
C3A—C4—C41	120.1 (4)	N37—C36—C35	122.3 (4)
C4—C5—C6	121.5 (4)	N37—C36—C361	115.4 (5)
C4—C5—C51	121.2 (4)	C35—C36—C361	122.3 (5)
C6—C5—C51	117.3 (4)	S31—C37A—N37	121.9 (4)
N7—C6—C61	116.0 (4)	S31—C37A—C33A	111.6 (4)
C5—C6—C61	121.8 (4)	N37—C37A—C33A	126.5 (5)
N7—C6—C5	122.2 (5)	C32—C33—H33	123.75
N7—C7A—C3A	127.5 (4)	C33A—C33—H33	123.78
S1—C7A—C3A	111.1 (3)	O323—C321—C32	110.3 (6)
S1—C7A—N7	121.4 (4)	O322—C321—O323	126.4 (6)
O22—C21—C2	123.8 (5)	O322—C321—C32	123.2 (6)
O23—C21—C2	112.6 (5)	O323—C324—C325	107.8 (8)
O22—C21—O23	123.6 (5)	C342—C341—C346	118.6 (4)
O23—C24—C25	114.6 (8)	C34—C341—C346	121.5 (4)
C4—C41—C42	120.0 (5)	C34—C341—C342	119.9 (4)
C4—C41—C46	121.6 (5)	C341—C342—C343	121.3 (4)
C42—C41—C46	118.5 (5)	C342—C343—C344	118.0 (4)
C41—C42—C43	119.3 (6)	Br2—C344—C345	120.2 (4)
C42—C43—C44	120.3 (7)	Br2—C344—C343	117.5 (3)
Br1—C44—C43	119.6 (6)	C343—C344—C345	122.3 (4)
Br1—C44—C45	119.2 (6)	C344—C345—C346	119.0 (5)
C43—C44—C45	121.2 (6)	C341—C346—C345	120.7 (4)
C44—C45—C46	119.3 (7)	O352—C351—O353	124.6 (5)
C41—C46—C45	121.4 (6)	O352—C351—C35	124.3 (5)
O52—C51—C5	125.7 (5)	O353—C351—C35	111.1 (4)
O53—C51—C5	110.8 (5)	O353—C354—C355	109.1 (6)
O52—C51—O53	123.3 (5)	O323—C324—H32A	110.14
O53—C54—C55	107.2 (6)	O323—C324—H32B	110.12
C2—C3—H3	123.43	C325—C324—H32A	110.19
C3A—C3—H3	123.41	C325—C324—H32B	110.15
H24A—C24—H24B	107.59	H32A—C324—H32B	108.43
C25—C24—H24A	108.58	C324—C325—H32C	109.45
C25—C24—H24B	108.59	C324—C325—H32D	109.51
O23—C24—H24A	108.66	C324—C325—H32E	109.49
O23—C24—H24B	108.65	H32C—C325—H32D	109.46
H25A—C25—H25C	109.26	H32C—C325—H32E	109.45
H25B—C25—H25C	109.53	H32D—C325—H32E	109.47
C24—C25—H25A	109.45	C341—C342—H342	119.34
C24—C25—H25B	109.66	C343—C342—H342	119.41
C24—C25—H25C	109.53	C342—C343—H343	120.95
H25A—C25—H25B	109.39	C344—C343—H343	121.03
C43—C42—H42	120.39	C344—C345—H345	120.48
C41—C42—H42	120.36	C346—C345—H345	120.47
C42—C43—H43	119.83	C341—C346—H346	119.64
C44—C43—H43	119.82	C345—C346—H346	119.62
C44—C45—H45	120.35	O353—C354—H35A	109.86
C46—C45—H45	120.32	O353—C354—H35B	109.87
C45—C46—H46	119.31	C355—C354—H35A	109.84
C41—C46—H46	119.31	C355—C354—H35B	109.86
O53—C54—H54A	110.38	H35A—C354—H35B	108.32
O53—C54—H54B	110.31	C354—C355—H35C	109.46
H54A—C54—H54B	108.60	C354—C355—H35D	109.39
C55—C54—H54A	110.21	C354—C355—H35E	109.48
C55—C54—H54B	110.12	H35C—C355—H35D	109.45
C54—C55—H55B	109.36	H35C—C355—H35E	109.56
C54—C55—H55C	109.42	H35D—C355—H35E	109.48
H55A—C55—H55B	109.53	C36—C361—H36A	109.48
H55A—C55—H55C	109.61	C36—C361—H36B	109.46
C54—C55—H55A	109.32	C36—C361—H36C	109.51
H55B—C55—H55C	109.58	H36A—C361—H36B	109.45
H61A—C61—H61C	109.45	H36A—C361—H36C	109.46
H61B—C61—H61C	109.48	H36B—C361—H36C	109.46

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C324—H32B···O22^i	0.97	2.55	3.431 (8)	151
C54—H54B···O52	0.97	2.29	2.660 (9)	102
C24—H24A···O22	0.97	2.36	2.688 (9)	99
C324—H32A···O322	0.97	2.42	2.742 (9)	99
C354—H35B···O352	0.97	2.47	2.675 (9)	91

Symmetry code: (i) x+1/2, −y+1/2, −z+1.