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A salt of vandetanib, namely, 4-({4-[(4-bromo-2-fluoro­phen­yl)amino]-6-meth­oxy­quinazolin-7-yl}meth­oxy)-1-methyl­piperazin-1-ium 2-(butyl­amino)-4-phen­oxy-6-sulfamoylbenzoate aceto­nitrile monosolvate, C22H25BrFN4O2+·C17H19N2O5S·C2H3N, com­posed of kinase inhibitor vandetanib and sulfamyl diuretic bumetanide in a 1:1 molar ratio, is reported. There is proton transfer between the piperidine ring of vandetanib and the carboxyl group of bumetanide to form the salt. In the vandetanib cation, the arene and pyrimidine rings are not coplanar, their planes subtending a dihedral angle of 60.47 (14)°. The roles of the inter­molecular inter­actions in the crystal packing were clarified using Hirshfeld surface analysis, and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H...H (40.5%), O...H/H...C (20.7%), C...H/ H...C (18.8%) and N...C/C...N (9.0%) contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229624000676/dg3049sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229624000676/dg3049Isup2.hkl
Contains datablock I

mol

MDL mol file https://doi.org/10.1107/S2053229624000676/dg3049Isup3.mol
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229624000676/dg3049Isup4.cml
Supplementary material

CCDC reference: 2327307

Computing details top

4-({4-[(4-Bromo-2-fluorophenyl)amino]-6-methoxyquinazolin-7-yl}methoxy)-1-methylpiperazin-1-ium 2-(butylamino)-4-phenoxy-6-sulfamoylbenzoate acetonitrile monosolvate top
Crystal data top
C22H25BrFN4O2+·C17H19N2O5S·C2H3NZ = 2
Mr = 880.82F(000) = 916
Triclinic, P1Dx = 1.410 Mg m3
a = 12.5755 (3) ÅCu Kα radiation, λ = 1.54184 Å
b = 12.6649 (3) ÅCell parameters from 10183 reflections
c = 14.4336 (2) Åθ = 3.3–75.7°
α = 68.909 (2)°µ = 2.34 mm1
β = 82.733 (2)°T = 200 K
γ = 75.557 (2)°Block, clear light colourless
V = 2075.30 (8) Å30.15 × 0.13 × 0.11 mm
Data collection top
XtaLAB Synergy R, DW system, HyPix
diffractometer
8229 independent reflections
Mirror monochromator6803 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm-1Rint = 0.041
ω scansθmax = 76.5°, θmin = 3.3°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2022)
h = 1315
Tmin = 0.650, Tmax = 1.000k = 1515
23536 measured reflectionsl = 1718
Refinement top
Refinement on F2Primary atom site location: iterative
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.053H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.156 w = 1/[σ2(Fo2) + (0.0823P)2 + 1.8341P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
8229 reflectionsΔρmax = 1.37 e Å3
539 parametersΔρmin = 0.69 e Å3
0 restraints
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.67091 (4)1.46322 (4)0.55377 (3)0.06337 (16)
F10.90103 (16)1.06014 (18)0.56148 (14)0.0496 (5)
O60.9323 (2)0.8108 (2)0.17554 (16)0.0459 (5)
O70.94456 (17)0.59723 (18)0.28619 (15)0.0365 (4)
N30.7903 (2)1.0507 (2)0.40976 (17)0.0320 (5)
H30.8070611.0691700.3456660.038*
N40.76464 (19)0.9065 (2)0.55885 (17)0.0328 (5)
N50.8055 (2)0.7049 (2)0.57422 (17)0.0354 (5)
N60.95552 (19)0.2753 (2)0.14596 (18)0.0300 (5)
H60.889 (4)0.269 (4)0.154 (3)0.052 (11)*
C180.7067 (3)1.3330 (3)0.5111 (2)0.0429 (7)
C190.6480 (3)1.3332 (3)0.4356 (2)0.0409 (7)
H190.5913021.3978930.4049360.049*
C200.6741 (2)1.2371 (3)0.4062 (2)0.0358 (6)
H200.6337321.2358400.3553380.043*
C210.7573 (2)1.1427 (2)0.44869 (19)0.0317 (6)
C220.8149 (3)1.1470 (3)0.5229 (2)0.0367 (6)
C230.7897 (3)1.2409 (3)0.5549 (2)0.0434 (7)
H230.8292401.2418160.6063590.052*
C240.7980 (2)0.9368 (2)0.46350 (19)0.0284 (5)
C250.8389 (2)0.8517 (2)0.41621 (19)0.0286 (5)
C260.8414 (2)0.7361 (2)0.4753 (2)0.0305 (5)
C270.7704 (2)0.7918 (3)0.6073 (2)0.0353 (6)
H270.7452940.7713580.6750440.042*
C280.8724 (2)0.8789 (2)0.3139 (2)0.0309 (6)
H280.8720580.9569770.2734680.037*
C290.9052 (2)0.7924 (3)0.2739 (2)0.0319 (6)
C300.9103 (2)0.6745 (2)0.3346 (2)0.0313 (6)
C310.8797 (2)0.6469 (2)0.4339 (2)0.0327 (6)
H310.8843610.5681310.4747300.039*
C320.8885 (5)0.9218 (4)0.1080 (3)0.0732 (14)
H32A0.8105010.9457090.1252150.110*
H32B0.8965140.9191080.0404310.110*
H32C0.9282080.9776520.1115510.110*
C330.9330 (2)0.4798 (2)0.3374 (2)0.0329 (6)
H33A0.8553640.4782240.3591400.039*
H33B0.9785120.4434420.3966750.039*
C340.9713 (2)0.4156 (2)0.2642 (2)0.0287 (5)
H341.0492670.4204490.2427160.034*
C350.9031 (2)0.4671 (3)0.1723 (2)0.0333 (6)
H35A0.9047440.5501460.1398790.040*
H35B0.8257770.4615980.1918820.040*
C360.9473 (2)0.4033 (2)0.0993 (2)0.0315 (6)
H36A0.8982770.4345110.0425770.038*
H36B1.0209250.4177660.0732190.038*
C371.0150 (2)0.2235 (2)0.2405 (2)0.0324 (6)
H37A1.0935160.2260820.2257120.039*
H37B1.0103120.1411570.2718790.039*
C380.9672 (2)0.2877 (2)0.3122 (2)0.0321 (6)
H38A1.0095710.2526610.3733740.039*
H38B0.8900980.2806500.3308460.039*
C391.0067 (3)0.2172 (3)0.0731 (2)0.0404 (7)
H39A1.0090360.1338500.1028930.061*
H39B1.0815770.2293070.0549180.061*
H39C0.9631330.2500610.0135430.061*
S10.69507 (5)0.65651 (6)0.97649 (5)0.03338 (17)
O10.7221 (2)0.7233 (2)1.02794 (17)0.0484 (6)
O20.78010 (16)0.6105 (2)0.91622 (18)0.0454 (5)
O30.26954 (16)0.68389 (18)0.93466 (16)0.0391 (5)
O40.21762 (15)0.83186 (18)0.79706 (14)0.0341 (4)
O50.70675 (14)0.87738 (16)0.81418 (14)0.0284 (4)
N10.6492 (2)0.5500 (3)1.0531 (2)0.0413 (6)
H1A0.667 (3)0.486 (4)1.041 (3)0.045 (10)*
H1B0.601 (4)0.566 (4)1.090 (4)0.071 (15)*
N20.55352 (19)1.0113 (2)0.67886 (19)0.0371 (5)
H20.6224641.0175690.6717530.044*
C10.5861 (2)0.7474 (2)0.89793 (19)0.0274 (5)
C20.4838 (2)0.7193 (2)0.90942 (19)0.0276 (5)
H2A0.4707550.6499430.9592460.033*
C30.4009 (2)0.7946 (2)0.84654 (19)0.0265 (5)
C40.4219 (2)0.8931 (2)0.77032 (19)0.0279 (5)
H40.3646850.9432270.7276260.033*
C50.5260 (2)0.9198 (2)0.75542 (19)0.0279 (5)
C60.6053 (2)0.8477 (2)0.82435 (19)0.0259 (5)
C70.2887 (2)0.7672 (2)0.8607 (2)0.0281 (5)
C80.7085 (2)0.9688 (2)0.8463 (2)0.0287 (5)
C90.6389 (3)0.9926 (3)0.9218 (3)0.0435 (7)
H90.5850010.9484380.9524340.052*
C100.6489 (3)1.0820 (3)0.9522 (3)0.0507 (8)
H100.6004811.0999221.0032140.061*
C110.7283 (3)1.1451 (3)0.9089 (3)0.0481 (8)
H110.7352411.2054180.9307070.058*
C120.7976 (3)1.1199 (3)0.8339 (3)0.0451 (7)
H120.8524161.1629070.8039430.054*
C130.7872 (2)1.0316 (3)0.8021 (2)0.0350 (6)
H130.8343961.0148370.7500010.042*
C140.4764 (3)1.0987 (3)0.6087 (2)0.0405 (7)
H14A0.4287231.0607250.5875780.049*
H14B0.5172901.1403480.5490290.049*
C150.4046 (3)1.1863 (3)0.6551 (3)0.0599 (10)
H15A0.3500001.2412300.6064490.072*
H15B0.3635281.1436400.7140630.072*
C160.4657 (4)1.2545 (4)0.6859 (4)0.0672 (11)
H16A0.5050291.2999490.6271860.081*
H16B0.5209781.2006710.7343380.081*
C170.3891 (5)1.3354 (5)0.7321 (4)0.0852 (15)
H17A0.3340521.3884430.6843790.128*
H17B0.4310301.3801090.7503090.128*
H17C0.3521301.2902360.7917450.128*
N70.5526 (5)0.4934 (7)0.8103 (6)0.147 (3)
C400.7623 (5)0.4550 (5)0.7872 (4)0.0795 (14)
H40A0.7942890.4517200.8470010.119*
H40B0.7836640.5172870.7297710.119*
H40C0.7893710.3807410.7762010.119*
C410.6450 (6)0.4773 (6)0.8000 (4)0.0929 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0945 (3)0.0491 (2)0.0617 (3)0.0288 (2)0.0219 (2)0.0364 (2)
F10.0553 (11)0.0514 (11)0.0438 (10)0.0098 (9)0.0118 (8)0.0165 (9)
O60.0671 (15)0.0393 (12)0.0308 (10)0.0120 (11)0.0130 (10)0.0163 (9)
O70.0463 (11)0.0309 (10)0.0367 (10)0.0104 (9)0.0051 (9)0.0176 (9)
N30.0442 (13)0.0302 (12)0.0245 (10)0.0100 (10)0.0034 (9)0.0131 (9)
N40.0367 (12)0.0346 (13)0.0286 (11)0.0094 (10)0.0027 (9)0.0130 (10)
N50.0458 (14)0.0334 (13)0.0282 (11)0.0108 (11)0.0003 (10)0.0108 (10)
N60.0234 (11)0.0359 (13)0.0374 (12)0.0104 (9)0.0025 (9)0.0191 (10)
C180.061 (2)0.0356 (16)0.0392 (16)0.0231 (15)0.0185 (14)0.0191 (13)
C190.0459 (17)0.0356 (16)0.0420 (16)0.0136 (13)0.0108 (13)0.0151 (13)
C200.0416 (15)0.0338 (15)0.0346 (14)0.0144 (12)0.0046 (12)0.0128 (12)
C210.0405 (15)0.0319 (14)0.0254 (12)0.0160 (12)0.0070 (11)0.0103 (11)
C220.0472 (16)0.0360 (15)0.0289 (13)0.0162 (13)0.0011 (12)0.0098 (12)
C230.061 (2)0.0467 (18)0.0312 (14)0.0247 (16)0.0071 (13)0.0176 (13)
C240.0273 (12)0.0316 (14)0.0278 (12)0.0078 (10)0.0006 (10)0.0113 (11)
C250.0284 (12)0.0328 (14)0.0277 (12)0.0075 (11)0.0002 (10)0.0139 (11)
C260.0300 (13)0.0329 (14)0.0282 (13)0.0060 (11)0.0033 (10)0.0098 (11)
C270.0405 (15)0.0360 (15)0.0270 (13)0.0086 (12)0.0018 (11)0.0089 (11)
C280.0352 (14)0.0302 (14)0.0291 (13)0.0119 (11)0.0026 (11)0.0105 (11)
C290.0336 (14)0.0366 (15)0.0279 (13)0.0105 (12)0.0027 (10)0.0132 (11)
C300.0307 (13)0.0322 (14)0.0364 (14)0.0071 (11)0.0003 (11)0.0185 (12)
C310.0372 (14)0.0287 (14)0.0331 (14)0.0063 (11)0.0044 (11)0.0112 (11)
C320.131 (4)0.047 (2)0.0298 (17)0.008 (2)0.014 (2)0.0132 (16)
C330.0368 (14)0.0295 (14)0.0337 (14)0.0062 (11)0.0001 (11)0.0134 (11)
C340.0274 (12)0.0291 (14)0.0316 (13)0.0054 (10)0.0019 (10)0.0131 (11)
C350.0324 (14)0.0308 (14)0.0367 (14)0.0016 (11)0.0064 (11)0.0132 (12)
C360.0318 (13)0.0335 (14)0.0310 (13)0.0086 (11)0.0050 (11)0.0110 (11)
C370.0338 (14)0.0290 (14)0.0347 (14)0.0078 (11)0.0009 (11)0.0110 (11)
C380.0335 (14)0.0318 (14)0.0306 (13)0.0086 (11)0.0016 (11)0.0102 (11)
C390.0385 (15)0.0475 (18)0.0434 (16)0.0118 (13)0.0062 (13)0.0262 (14)
S10.0252 (3)0.0334 (4)0.0369 (3)0.0073 (3)0.0053 (2)0.0045 (3)
O10.0534 (13)0.0492 (13)0.0456 (12)0.0212 (11)0.0196 (10)0.0073 (10)
O20.0251 (10)0.0432 (12)0.0543 (13)0.0019 (9)0.0035 (9)0.0060 (10)
O30.0309 (10)0.0341 (11)0.0458 (12)0.0141 (8)0.0005 (9)0.0015 (9)
O40.0276 (9)0.0439 (12)0.0308 (9)0.0135 (8)0.0028 (8)0.0085 (9)
O50.0225 (8)0.0325 (10)0.0349 (9)0.0116 (7)0.0043 (7)0.0148 (8)
N10.0384 (14)0.0341 (15)0.0422 (15)0.0066 (11)0.0002 (12)0.0036 (12)
N20.0269 (11)0.0375 (13)0.0381 (13)0.0115 (10)0.0014 (9)0.0007 (11)
C10.0251 (12)0.0278 (13)0.0295 (12)0.0052 (10)0.0011 (10)0.0106 (10)
C20.0274 (12)0.0264 (13)0.0302 (13)0.0108 (10)0.0020 (10)0.0088 (10)
C30.0266 (12)0.0287 (13)0.0283 (12)0.0107 (10)0.0018 (10)0.0127 (11)
C40.0274 (12)0.0297 (13)0.0277 (12)0.0081 (10)0.0039 (10)0.0090 (11)
C50.0287 (13)0.0269 (13)0.0278 (12)0.0093 (10)0.0031 (10)0.0082 (10)
C60.0218 (11)0.0279 (13)0.0314 (12)0.0081 (10)0.0023 (9)0.0134 (11)
C70.0289 (13)0.0286 (13)0.0308 (13)0.0099 (10)0.0012 (10)0.0134 (11)
C80.0246 (12)0.0298 (13)0.0328 (13)0.0064 (10)0.0028 (10)0.0113 (11)
C90.0417 (16)0.0490 (19)0.0491 (17)0.0189 (14)0.0113 (14)0.0262 (15)
C100.059 (2)0.057 (2)0.0525 (19)0.0261 (17)0.0132 (16)0.0343 (17)
C110.062 (2)0.0420 (18)0.0505 (19)0.0193 (16)0.0032 (16)0.0225 (15)
C120.0514 (18)0.0367 (16)0.0500 (18)0.0213 (14)0.0023 (14)0.0101 (14)
C130.0357 (14)0.0327 (15)0.0364 (14)0.0149 (12)0.0041 (11)0.0086 (12)
C140.0371 (15)0.0423 (17)0.0351 (15)0.0154 (13)0.0049 (12)0.0006 (13)
C150.0454 (19)0.045 (2)0.079 (3)0.0088 (16)0.0128 (18)0.0069 (19)
C160.065 (3)0.062 (3)0.075 (3)0.018 (2)0.004 (2)0.022 (2)
C170.114 (4)0.067 (3)0.076 (3)0.018 (3)0.017 (3)0.033 (3)
N70.114 (4)0.238 (8)0.178 (6)0.108 (5)0.087 (4)0.161 (6)
C400.103 (4)0.088 (4)0.066 (3)0.056 (3)0.007 (3)0.027 (3)
C410.120 (5)0.121 (5)0.082 (3)0.083 (4)0.049 (3)0.068 (3)
Geometric parameters (Å, º) top
Br1—C181.896 (3)C38—H38B0.9900
F1—C221.346 (4)C39—H39A0.9800
O6—C291.366 (3)C39—H39B0.9800
O6—C321.412 (5)C39—H39C0.9800
O7—C301.355 (3)S1—O11.429 (2)
O7—C331.438 (3)S1—O21.435 (2)
N3—H30.8800S1—N11.591 (3)
N3—C211.419 (3)S1—C11.777 (3)
N3—C241.355 (4)O3—C71.250 (3)
N4—C241.331 (3)O4—C71.271 (3)
N4—C271.355 (4)O5—C61.394 (3)
N5—C261.385 (4)O5—C81.400 (3)
N5—C271.310 (4)N1—H1A0.86 (4)
N6—H60.85 (4)N1—H1B0.79 (5)
N6—C361.497 (4)N2—H20.8800
N6—C371.490 (4)N2—C51.367 (3)
N6—C391.487 (4)N2—C141.448 (4)
C18—C191.391 (5)C1—C21.394 (4)
C18—C231.370 (5)C1—C61.384 (4)
C19—H190.9500C2—H2A0.9500
C19—C201.380 (4)C2—C31.392 (4)
C20—H200.9500C3—C41.392 (4)
C20—C211.383 (4)C3—C71.508 (3)
C21—C221.390 (4)C4—H40.9500
C22—C231.377 (4)C4—C51.403 (4)
C23—H230.9500C5—C61.401 (4)
C24—C251.434 (4)C8—C91.380 (4)
C25—C261.399 (4)C8—C131.373 (4)
C25—C281.423 (4)C9—H90.9500
C26—C311.416 (4)C9—C101.391 (5)
C27—H270.9500C10—H100.9500
C28—H280.9500C10—C111.381 (5)
C28—C291.368 (4)C11—H110.9500
C29—C301.424 (4)C11—C121.380 (5)
C30—C311.375 (4)C12—H120.9500
C31—H310.9500C12—C131.391 (4)
C32—H32A0.9800C13—H130.9500
C32—H32B0.9800C14—H14A0.9900
C32—H32C0.9800C14—H14B0.9900
C33—H33A0.9900C14—C151.542 (6)
C33—H33B0.9900C15—H15A0.9900
C33—C341.518 (4)C15—H15B0.9900
C34—H341.0000C15—C161.492 (6)
C34—C351.519 (4)C16—H16A0.9900
C34—C381.527 (4)C16—H16B0.9900
C35—H35A0.9900C16—C171.502 (7)
C35—H35B0.9900C17—H17A0.9800
C35—C361.520 (4)C17—H17B0.9800
C36—H36A0.9900C17—H17C0.9800
C36—H36B0.9900N7—C411.129 (8)
C37—H37A0.9900C40—H40A0.9800
C37—H37B0.9900C40—H40B0.9800
C37—C381.516 (4)C40—H40C0.9800
C38—H38A0.9900C40—C411.432 (8)
C29—O6—C32116.7 (2)C37—C38—C34110.1 (2)
C30—O7—C33118.1 (2)C37—C38—H38A109.6
C21—N3—H3117.4C37—C38—H38B109.6
C24—N3—H3117.4H38A—C38—H38B108.1
C24—N3—C21125.1 (2)N6—C39—H39A109.5
C24—N4—C27116.2 (2)N6—C39—H39B109.5
C27—N5—C26114.7 (2)N6—C39—H39C109.5
C36—N6—H6103 (3)H39A—C39—H39B109.5
C37—N6—H6113 (3)H39A—C39—H39C109.5
C37—N6—C36112.9 (2)H39B—C39—H39C109.5
C39—N6—H6106 (3)O1—S1—O2117.84 (15)
C39—N6—C36109.7 (2)O1—S1—N1110.14 (16)
C39—N6—C37111.6 (2)O1—S1—C1106.95 (13)
C19—C18—Br1119.1 (3)O2—S1—N1106.94 (16)
C23—C18—Br1119.6 (3)O2—S1—C1107.57 (13)
C23—C18—C19121.4 (3)N1—S1—C1106.90 (14)
C18—C19—H19120.8C6—O5—C8115.58 (19)
C20—C19—C18118.4 (3)S1—N1—H1A117 (3)
C20—C19—H19120.8S1—N1—H1B115 (4)
C19—C20—H20119.1H1A—N1—H1B126 (4)
C19—C20—C21121.8 (3)C5—N2—H2117.9
C21—C20—H20119.1C5—N2—C14124.1 (2)
C20—C21—N3120.5 (3)C14—N2—H2117.9
C20—C21—C22117.8 (3)C2—C1—S1121.3 (2)
C22—C21—N3121.3 (3)C6—C1—S1118.17 (19)
F1—C22—C21119.5 (3)C6—C1—C2120.5 (2)
F1—C22—C23118.7 (3)C1—C2—H2A120.6
C23—C22—C21121.7 (3)C3—C2—C1118.8 (2)
C18—C23—C22118.9 (3)C3—C2—H2A120.6
C18—C23—H23120.6C2—C3—C7119.2 (2)
C22—C23—H23120.6C4—C3—C2120.5 (2)
N3—C24—C25119.6 (2)C4—C3—C7120.3 (2)
N4—C24—N3119.1 (2)C3—C4—H4119.4
N4—C24—C25121.3 (3)C3—C4—C5121.2 (2)
C26—C25—C24116.6 (2)C5—C4—H4119.4
C26—C25—C28119.4 (2)N2—C5—C4124.0 (2)
C28—C25—C24124.0 (3)N2—C5—C6118.7 (2)
N5—C26—C25122.0 (2)C6—C5—C4117.2 (2)
N5—C26—C31117.9 (3)O5—C6—C5117.9 (2)
C25—C26—C31120.1 (2)C1—C6—O5120.6 (2)
N4—C27—H27115.4C1—C6—C5121.5 (2)
N5—C27—N4129.3 (3)O3—C7—O4123.3 (2)
N5—C27—H27115.4O3—C7—C3118.9 (2)
C25—C28—H28120.0O4—C7—C3117.8 (2)
C29—C28—C25120.0 (3)C9—C8—O5122.5 (2)
C29—C28—H28120.0C13—C8—O5116.6 (2)
O6—C29—C28124.2 (3)C13—C8—C9120.9 (3)
O6—C29—C30115.2 (2)C8—C9—H9120.5
C28—C29—C30120.6 (2)C8—C9—C10119.0 (3)
O7—C30—C29114.8 (2)C10—C9—H9120.5
O7—C30—C31125.2 (3)C9—C10—H10119.6
C31—C30—C29120.0 (2)C11—C10—C9120.7 (3)
C26—C31—H31120.0C11—C10—H10119.6
C30—C31—C26119.9 (3)C10—C11—H11120.2
C30—C31—H31120.0C12—C11—C10119.5 (3)
O6—C32—H32A109.5C12—C11—H11120.2
O6—C32—H32B109.5C11—C12—H12119.9
O6—C32—H32C109.5C11—C12—C13120.2 (3)
H32A—C32—H32B109.5C13—C12—H12119.9
H32A—C32—H32C109.5C8—C13—C12119.8 (3)
H32B—C32—H32C109.5C8—C13—H13120.1
O7—C33—H33A110.4C12—C13—H13120.1
O7—C33—H33B110.4N2—C14—H14A109.4
O7—C33—C34106.6 (2)N2—C14—H14B109.4
H33A—C33—H33B108.6N2—C14—C15111.1 (3)
C34—C33—H33A110.4H14A—C14—H14B108.0
C34—C33—H33B110.4C15—C14—H14A109.4
C33—C34—H34108.3C15—C14—H14B109.4
C33—C34—C35112.5 (2)C14—C15—H15A108.5
C33—C34—C38111.2 (2)C14—C15—H15B108.5
C35—C34—H34108.3H15A—C15—H15B107.5
C35—C34—C38108.2 (2)C16—C15—C14115.2 (3)
C38—C34—H34108.3C16—C15—H15A108.5
C34—C35—H35A109.5C16—C15—H15B108.5
C34—C35—H35B109.5C15—C16—H16A109.4
C34—C35—C36110.7 (2)C15—C16—H16B109.4
H35A—C35—H35B108.1C15—C16—C17111.2 (4)
C36—C35—H35A109.5H16A—C16—H16B108.0
C36—C35—H35B109.5C17—C16—H16A109.4
N6—C36—C35112.4 (2)C17—C16—H16B109.4
N6—C36—H36A109.1C16—C17—H17A109.5
N6—C36—H36B109.1C16—C17—H17B109.5
C35—C36—H36A109.1C16—C17—H17C109.5
C35—C36—H36B109.1H17A—C17—H17B109.5
H36A—C36—H36B107.9H17A—C17—H17C109.5
N6—C37—H37A109.3H17B—C17—H17C109.5
N6—C37—H37B109.3H40A—C40—H40B109.5
N6—C37—C38111.5 (2)H40A—C40—H40C109.5
H37A—C37—H37B108.0H40B—C40—H40C109.5
C38—C37—H37A109.3C41—C40—H40A109.5
C38—C37—H37B109.3C41—C40—H40B109.5
C34—C38—H38A109.6C41—C40—H40C109.5
C34—C38—H38B109.6N7—C41—C40179.0 (6)
Br1—C18—C19—C20179.2 (2)C33—C34—C38—C37175.1 (2)
Br1—C18—C23—C22179.9 (2)C34—C35—C36—N654.6 (3)
F1—C22—C23—C18175.7 (3)C35—C34—C38—C3760.8 (3)
O6—C29—C30—O71.9 (4)C36—N6—C37—C3852.4 (3)
O6—C29—C30—C31177.0 (3)C37—N6—C36—C3550.8 (3)
O7—C30—C31—C26177.6 (2)C38—C34—C35—C3659.1 (3)
O7—C33—C34—C3560.8 (3)C39—N6—C36—C35175.9 (2)
O7—C33—C34—C38177.6 (2)C39—N6—C37—C38176.4 (2)
N3—C21—C22—F12.6 (4)S1—C1—C2—C3179.1 (2)
N3—C21—C22—C23174.0 (3)S1—C1—C6—O51.5 (3)
N3—C24—C25—C26178.0 (2)S1—C1—C6—C5175.7 (2)
N3—C24—C25—C280.3 (4)O1—S1—C1—C2118.4 (2)
N4—C24—C25—C260.2 (4)O1—S1—C1—C661.7 (2)
N4—C24—C25—C28177.9 (3)O2—S1—C1—C2114.1 (2)
N5—C26—C31—C30176.3 (3)O2—S1—C1—C665.8 (2)
N6—C37—C38—C3457.8 (3)O5—C8—C9—C10177.4 (3)
C18—C19—C20—C211.0 (4)O5—C8—C13—C12176.7 (3)
C19—C18—C23—C220.1 (5)N1—S1—C1—C20.4 (3)
C19—C20—C21—N3173.1 (3)N1—S1—C1—C6179.6 (2)
C19—C20—C21—C220.0 (4)N2—C5—C6—O53.6 (4)
C20—C21—C22—F1175.7 (2)N2—C5—C6—C1173.8 (3)
C20—C21—C22—C230.9 (4)N2—C14—C15—C1661.9 (4)
C21—N3—C24—N45.5 (4)C1—C2—C3—C43.3 (4)
C21—N3—C24—C25176.2 (2)C1—C2—C3—C7177.8 (2)
C21—C22—C23—C180.9 (4)C2—C1—C6—O5178.5 (2)
C23—C18—C19—C201.0 (4)C2—C1—C6—C54.2 (4)
C24—N3—C21—C20127.7 (3)C2—C3—C4—C50.7 (4)
C24—N3—C21—C2259.4 (4)C2—C3—C7—O37.2 (4)
C24—N4—C27—N50.9 (5)C2—C3—C7—O4174.0 (2)
C24—C25—C26—N50.5 (4)C3—C4—C5—N2176.2 (3)
C24—C25—C26—C31179.5 (2)C3—C4—C5—C64.3 (4)
C24—C25—C28—C29176.7 (3)C4—C3—C7—O3174.0 (3)
C25—C26—C31—C302.7 (4)C4—C3—C7—O44.8 (4)
C25—C28—C29—O6175.8 (3)C4—C5—C6—O5176.0 (2)
C25—C28—C29—C302.5 (4)C4—C5—C6—C16.7 (4)
C26—N5—C27—N40.2 (5)C5—N2—C14—C1577.1 (4)
C26—C25—C28—C290.9 (4)C6—O5—C8—C929.6 (4)
C27—N4—C24—N3177.4 (2)C6—O5—C8—C13153.5 (2)
C27—N4—C24—C250.8 (4)C6—C1—C2—C30.9 (4)
C27—N5—C26—C250.5 (4)C7—C3—C4—C5179.5 (2)
C27—N5—C26—C31179.5 (3)C8—O5—C6—C1106.0 (3)
C28—C25—C26—N5177.3 (2)C8—O5—C6—C576.6 (3)
C28—C25—C26—C311.7 (4)C8—C9—C10—C111.1 (6)
C28—C29—C30—O7179.6 (2)C9—C8—C13—C120.4 (5)
C28—C29—C30—C311.5 (4)C9—C10—C11—C120.8 (6)
C29—C30—C31—C261.1 (4)C10—C11—C12—C130.1 (5)
C30—O7—C33—C34176.8 (2)C11—C12—C13—C80.7 (5)
C32—O6—C29—C2822.9 (5)C13—C8—C9—C100.5 (5)
C32—O6—C29—C30155.5 (3)C14—N2—C5—C46.0 (5)
C33—O7—C30—C29168.9 (2)C14—N2—C5—C6173.5 (3)
C33—O7—C30—C319.9 (4)C14—C15—C16—C17178.8 (4)
C33—C34—C35—C36177.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O3i0.86 (4)2.02 (5)2.830 (4)158 (4)
N1—H1B···N7i0.79 (5)2.37 (5)3.046 (8)144 (5)
N3—H3···O4ii0.882..012.818 (3)153
N6—H6···O3iii0.85 (5)2.34 (5)3.050 (3)142 (4)
N6—H6···O4iii0.85 (5)1.97 (5)2.734 (3)149 (5)
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+1, y+2, z+1; (iii) x+1, y+1, z+1.
 

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