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The loop diuretic furosemide is used widely in the treatment of congestive heart failure and edema, and is practically insoluble in water. The physicochemical and pharmacokinetic properties of drugs can be modified by preparing the drug in an appropriate solid-state form. A new solvate of furosemide with di­methyl­acetamide (DMA) {systematic name: 4-chloro-2-[(furan-2-yl)methyl­amino]-5-sulfamoyl­benzoic acid N,N-di­methyl­acetamide disolvate}, C12H11ClN2O5S·2C4H9NO, (I), is reported. The channeled structure formed on slow crystallization contains DMA solvent mol­ecules in its channels. This structure adds to the evidence of varied conformations observed across all known structures, so supporting the idea that this flexible molecule has conformational lability. The current structure also differs from those of other previously known furosemide solvates in the number of solvent mol­ecules per furosemide mol­ecule, viz. 2:1 instead of 1:1. Desolvation of (I) gives the most stable form of furosemide, i.e. Form I.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616018398/sk3641sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616018398/sk3641Isup2.hkl
Contains datablock I

CCDC reference: 1508888

Computing details top

Data collection: X-AREA (Stoe & Cie, 2007); cell refinement: X-AREA (Stoe & Cie, 2007); data reduction: X-RED (Stoe & Cie, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015) and X-STEP32 (Stoe & Cie, 2000); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: Mercury (Macrae et al., 2006), WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).

4-Chloro-2-[(furan-2-yl)methylamino]-5-sulfamoylbenzoic acid N,N-dimethylacetamide disolvate top
Crystal data top
C12H11ClN2O5S·2C4H9NOF(000) = 1064
Mr = 504.98Dx = 1.412 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 17.0284 (10) ÅCell parameters from 22285 reflections
b = 7.8695 (3) Åθ = 2.3–29.6°
c = 22.0555 (15) ŵ = 0.30 mm1
β = 126.512 (4)°T = 150 K
V = 2375.5 (3) Å3Block, colorless
Z = 40.52 × 0.24 × 0.22 mm
Data collection top
Stoe IPDS 2
diffractometer
6403 independent reflections
Radiation source: fine-focus sealed tube4489 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.046
Detector resolution: 6.67 pixels mm-1θmax = 29.3°, θmin = 1.9°
rotation method scansh = 2323
Absorption correction: numerical
(X-RED; Stoe & Cie, 2007)
k = 109
Tmin = 0.900, Tmax = 0.951l = 3030
29007 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: mixed
wR(F2) = 0.089H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.0496P)2]
where P = (Fo2 + 2Fc2)/3
6403 reflections(Δ/σ)max = 0.001
400 parametersΔρmax = 0.42 e Å3
0 restraintsΔρmin = 0.43 e Å3
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*/UeqOcc. (<1)
Cl10.94954 (2)0.82572 (5)0.03001 (2)0.02809 (10)
S10.85099 (2)0.44549 (5)0.01785 (2)0.02066 (9)
O20.51868 (7)0.80290 (14)0.01654 (6)0.0254 (2)
O50.94797 (7)0.41606 (14)0.04965 (6)0.0268 (2)
O40.78044 (8)0.31176 (14)0.04502 (7)0.0294 (2)
O10.52868 (8)0.54943 (15)0.05694 (7)0.0283 (2)
H10.4707 (15)0.541 (2)0.0747 (11)0.034*
C50.79940 (10)0.62115 (19)0.00268 (8)0.0198 (3)
C20.71114 (10)0.88927 (18)0.02380 (8)0.0197 (3)
C10.66417 (9)0.72889 (18)0.00387 (7)0.0186 (3)
O60.34340 (8)0.48991 (15)0.12879 (6)0.0309 (3)
O30.79677 (9)1.12568 (16)0.19929 (7)0.0367 (3)
N20.86172 (9)0.49057 (18)0.08342 (7)0.0243 (3)
H40.9148 (14)0.546 (2)0.0670 (10)0.029*
H30.8088 (14)0.527 (2)0.1231 (11)0.029*
N10.67190 (9)1.01612 (16)0.03902 (7)0.0242 (3)
H20.6180 (14)0.996 (2)0.0299 (10)0.029*
C60.71031 (10)0.59981 (19)0.01466 (8)0.0194 (3)
H60.6782 (12)0.491 (2)0.0319 (9)0.023*
C40.84218 (9)0.78248 (19)0.01988 (8)0.0210 (3)
C120.80436 (11)1.1899 (2)0.14547 (9)0.0248 (3)
C70.56470 (9)0.69865 (19)0.02485 (8)0.0198 (3)
C80.71500 (11)1.18424 (19)0.06581 (9)0.0240 (3)
H80.7315 (13)1.233 (2)0.0341 (10)0.029*
H70.6623 (13)1.255 (2)0.0579 (10)0.029*
C30.80082 (10)0.91277 (19)0.03327 (8)0.0217 (3)
H50.8307 (12)1.019 (2)0.0478 (10)0.026*
C110.89355 (13)1.2579 (3)0.17839 (10)0.0399 (4)
H110.9162 (15)1.305 (3)0.1526 (12)0.048*
C90.88513 (15)1.1546 (3)0.26768 (10)0.0436 (5)
H90.8926 (16)1.113 (3)0.3115 (12)0.052*
C100.94551 (14)1.2350 (3)0.25797 (11)0.0479 (5)
H101.0076 (18)1.271 (3)0.2979 (13)0.058*
N3A0.2105 (2)0.4222 (3)0.24255 (16)0.0423 (10)0.596 (6)
C13A0.2935 (3)0.5065 (5)0.2008 (2)0.0317 (9)0.596 (6)
C15A0.1478 (5)0.4209 (9)0.3249 (3)0.077 (2)0.596 (6)
H15A0.1697560.3317350.3427250.115*0.596 (6)
H15B0.1515120.5314790.3435340.115*0.596 (6)
H15C0.0802030.3985740.3437640.115*0.596 (6)
C14A0.1835 (8)0.3230 (17)0.2070 (6)0.068 (5)0.596 (6)
H14A0.2414110.2943920.1562890.102*0.596 (6)
H14B0.1531850.2183420.2359500.102*0.596 (6)
H14C0.1367230.3849150.2031620.102*0.596 (6)
C16A0.3242 (11)0.614 (2)0.2403 (8)0.053 (3)0.596 (6)
H16A0.3387840.5399600.2681650.080*0.596 (6)
H16B0.3826010.6794290.2027690.080*0.596 (6)
H16C0.2711290.6918100.2754370.080*0.596 (6)
N3B0.2592 (3)0.5220 (5)0.2521 (2)0.0331 (13)0.404 (6)
C13B0.2698 (3)0.4509 (7)0.1925 (3)0.0260 (12)0.404 (6)
C15B0.1812 (5)0.4767 (12)0.3312 (4)0.0499 (18)0.404 (6)
H15D0.1992810.3723730.3443880.075*0.404 (6)
H15E0.1725820.5691670.3643960.075*0.404 (6)
H15F0.1199730.4583750.3372170.075*0.404 (6)
C16B0.1859 (12)0.326 (2)0.2068 (9)0.054 (5)*0.404 (6)
H16D0.1927140.3110600.1597770.080*0.404 (6)
H16E0.1921270.2150760.2240150.080*0.404 (6)
H16F0.1216670.3744340.2454230.080*0.404 (6)
C14B0.3349 (17)0.643 (3)0.2362 (11)0.045 (3)0.404 (6)
H14D0.3894220.5805180.2295410.067*0.404 (6)
H14E0.3583870.7055640.1899150.067*0.404 (6)
H14F0.3075660.7223090.2783350.067*0.404 (6)
O70.68747 (10)0.6082 (2)0.21179 (8)0.0595 (4)
N4A0.54305 (14)0.7347 (2)0.26861 (11)0.0317 (6)0.866 (6)
C17A0.60767 (15)0.6445 (3)0.27117 (13)0.0290 (6)0.866 (6)
N4B0.5436 (8)0.6830 (13)0.3073 (7)0.026 (4)0.134 (6)
C17B0.6096 (10)0.7058 (17)0.2351 (8)0.026 (4)0.134 (6)
C200.57910 (16)0.5933 (3)0.34752 (11)0.0448 (5)
H20A0.5636670.6950460.3783760.067*0.866 (6)
H20B0.5216110.5192040.3722520.067*0.866 (6)
H20C0.6333800.5323000.3417090.067*0.866 (6)
H20D0.5249040.5818590.4011690.067*0.134 (6)
H20E0.6317030.6596710.3420070.067*0.134 (6)
H20F0.6036660.4803090.3254490.067*0.134 (6)
C190.44588 (14)0.7752 (3)0.33632 (12)0.0530 (6)
H19A0.4201940.8747000.3266840.079*0.866 (6)
H19B0.4022750.6781210.3497990.079*0.866 (6)
H19C0.4499090.7999260.3779410.079*0.866 (6)
H19D0.3982000.7552730.3906000.079*0.134 (6)
H19E0.4202630.7306680.3097520.079*0.134 (6)
H19F0.4578230.8974580.3268480.079*0.134 (6)
C180.57031 (19)0.7897 (3)0.19500 (12)0.0544 (6)
H18A0.5365230.8960860.2008300.082*0.866 (6)
H18B0.6410950.8077920.1606340.082*0.866 (6)
H18C0.5515740.7020970.1742490.082*0.866 (6)
H18D0.6236580.8027470.1412220.082*0.134 (6)
H18E0.5432520.9016540.2172740.082*0.134 (6)
H18F0.5190070.7181580.2009900.082*0.134 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.01917 (16)0.0315 (2)0.0384 (2)0.00577 (14)0.01975 (15)0.00679 (16)
S10.01740 (15)0.02147 (17)0.02635 (17)0.00245 (13)0.01477 (14)0.00096 (14)
O20.0214 (5)0.0247 (6)0.0358 (6)0.0018 (4)0.0201 (5)0.0013 (5)
O50.0207 (5)0.0337 (6)0.0276 (5)0.0081 (4)0.0153 (5)0.0070 (5)
O40.0279 (5)0.0223 (5)0.0468 (7)0.0011 (4)0.0270 (5)0.0046 (5)
O10.0191 (5)0.0280 (6)0.0417 (6)0.0054 (4)0.0202 (5)0.0102 (5)
C50.0170 (6)0.0214 (7)0.0222 (7)0.0011 (5)0.0123 (5)0.0008 (5)
C20.0182 (6)0.0219 (7)0.0203 (6)0.0008 (5)0.0121 (6)0.0002 (5)
C10.0169 (6)0.0208 (7)0.0199 (6)0.0003 (5)0.0119 (5)0.0012 (5)
O60.0217 (5)0.0358 (6)0.0302 (6)0.0021 (4)0.0127 (5)0.0061 (5)
O30.0461 (7)0.0363 (7)0.0341 (6)0.0058 (5)0.0274 (6)0.0003 (5)
N20.0169 (5)0.0330 (7)0.0230 (6)0.0019 (5)0.0118 (5)0.0001 (5)
N10.0209 (6)0.0224 (6)0.0347 (7)0.0024 (5)0.0195 (5)0.0052 (5)
C60.0176 (6)0.0191 (7)0.0222 (7)0.0006 (5)0.0123 (5)0.0005 (5)
C40.0151 (6)0.0268 (7)0.0222 (7)0.0012 (5)0.0117 (5)0.0001 (6)
C120.0298 (7)0.0227 (7)0.0294 (7)0.0013 (6)0.0217 (6)0.0019 (6)
C70.0177 (6)0.0217 (7)0.0216 (6)0.0003 (5)0.0125 (5)0.0008 (6)
C80.0250 (7)0.0185 (7)0.0320 (8)0.0007 (6)0.0189 (6)0.0013 (6)
C30.0201 (6)0.0213 (8)0.0255 (7)0.0025 (5)0.0146 (6)0.0020 (6)
C110.0302 (8)0.0604 (13)0.0325 (9)0.0084 (8)0.0205 (8)0.0072 (8)
C90.0516 (11)0.0480 (12)0.0261 (8)0.0034 (9)0.0204 (9)0.0015 (8)
C100.0338 (9)0.0708 (15)0.0307 (9)0.0013 (9)0.0146 (8)0.0106 (10)
N3A0.0352 (17)0.0355 (17)0.0335 (17)0.0026 (12)0.0081 (15)0.0048 (12)
C13A0.0336 (19)0.0262 (19)0.038 (2)0.0080 (14)0.0227 (18)0.0005 (15)
C15A0.069 (4)0.072 (4)0.031 (2)0.022 (3)0.002 (2)0.009 (2)
C14A0.030 (3)0.047 (4)0.074 (5)0.0164 (18)0.0014 (18)0.002 (2)
C16A0.057 (7)0.053 (6)0.067 (5)0.013 (5)0.046 (5)0.010 (4)
N3B0.029 (2)0.037 (2)0.029 (2)0.0069 (16)0.0143 (18)0.0062 (16)
C13B0.019 (2)0.024 (2)0.030 (3)0.0008 (17)0.011 (2)0.003 (2)
C15B0.041 (4)0.063 (5)0.027 (3)0.016 (3)0.010 (3)0.007 (3)
C14B0.039 (4)0.053 (7)0.043 (5)0.006 (4)0.025 (4)0.011 (4)
O70.0288 (7)0.0857 (12)0.0418 (8)0.0153 (7)0.0089 (6)0.0190 (8)
N4A0.0327 (11)0.0340 (10)0.0303 (10)0.0060 (7)0.0198 (9)0.0060 (8)
C17A0.0261 (12)0.0284 (11)0.0309 (12)0.0003 (8)0.0161 (10)0.0031 (9)
N4B0.020 (6)0.020 (5)0.027 (7)0.006 (4)0.008 (5)0.001 (4)
C17B0.030 (8)0.024 (6)0.032 (8)0.012 (5)0.023 (7)0.004 (6)
C200.0631 (13)0.0406 (11)0.0448 (11)0.0010 (9)0.0397 (10)0.0039 (9)
C190.0355 (10)0.0655 (14)0.0560 (12)0.0209 (9)0.0262 (9)0.0351 (11)
C180.0810 (16)0.0517 (13)0.0484 (12)0.0046 (11)0.0483 (12)0.0022 (10)
Geometric parameters (Å, º) top
Cl1—C41.7383 (13)C16A—H16A0.9800
S1—O41.4329 (11)C16A—H16B0.9800
S1—O51.4393 (10)C16A—H16C0.9800
S1—N21.6017 (13)N3B—C13B1.338 (7)
S1—C51.7732 (15)N3B—C14B1.46 (2)
O2—C71.2213 (17)N3B—C15B1.475 (9)
O1—C71.3189 (18)C13B—C16B1.604 (17)
O1—H10.82 (2)C15B—H15D0.9800
C5—C61.3865 (18)C15B—H15E0.9800
C5—C41.400 (2)C15B—H15F0.9800
C2—N11.3500 (19)C16B—H16D0.9800
C2—C11.423 (2)C16B—H16E0.9800
C2—C31.4249 (19)C16B—H16F0.9800
C1—C61.3886 (19)C14B—H14D0.9800
C1—C71.4857 (18)C14B—H14E0.9800
O6—C13B1.243 (5)C14B—H14F0.9800
O6—C13A1.287 (4)O7—C17A1.235 (2)
O3—C121.3655 (19)O7—C17B1.342 (15)
O3—C91.375 (2)N4A—C17A1.338 (3)
N2—H40.867 (19)N4A—C191.459 (3)
N2—H30.848 (19)N4A—C181.463 (3)
N1—C81.4568 (19)C17A—C201.503 (3)
N1—H20.829 (19)N4B—C17B1.30 (2)
C6—H60.961 (18)N4B—C201.514 (14)
C4—C31.372 (2)N4B—C191.561 (12)
C12—C111.344 (2)C17B—C181.539 (15)
C12—C81.491 (2)C20—H20A0.9800
C8—H80.976 (19)C20—H20B0.9800
C8—H70.980 (18)C20—H20C0.9800
C3—H50.927 (18)C20—H20D0.9800
C11—C101.431 (3)C20—H20E0.9800
C11—H110.93 (2)C20—H20F0.9800
C9—C101.329 (3)C19—H19A0.9800
C9—H90.95 (2)C19—H19B0.9800
C10—H100.93 (2)C19—H19C0.9800
N3A—C13A1.317 (5)C19—H19D0.9800
N3A—C14A1.366 (12)C19—H19E0.9800
N3A—C15A1.460 (6)C19—H19F0.9800
C13A—C16A1.513 (15)C18—H18A0.9800
C15A—H15A0.9800C18—H18B0.9800
C15A—H15B0.9800C18—H18C0.9800
C15A—H15C0.9800C18—H18D0.9800
C14A—H14A0.9800C18—H18E0.9800
C14A—H14B0.9800C18—H18F0.9800
C14A—H14C0.9800
O4—S1—O5118.35 (7)H16A—C16A—H16C109.5
O4—S1—N2107.62 (7)H16B—C16A—H16C109.5
O5—S1—N2107.00 (7)C13B—N3B—C14B116.7 (9)
O4—S1—C5105.38 (6)C13B—N3B—C15B124.1 (5)
O5—S1—C5108.83 (7)C14B—N3B—C15B119.0 (9)
N2—S1—C5109.46 (7)O6—C13B—N3B117.6 (5)
C7—O1—H1111.7 (14)O6—C13B—C16B123.7 (7)
C6—C5—C4117.17 (13)N3B—C13B—C16B118.7 (7)
C6—C5—S1118.58 (11)N3B—C15B—H15D109.5
C4—C5—S1124.24 (10)N3B—C15B—H15E109.5
N1—C2—C1121.84 (12)H15D—C15B—H15E109.5
N1—C2—C3120.89 (13)N3B—C15B—H15F109.5
C1—C2—C3117.26 (12)H15D—C15B—H15F109.5
C6—C1—C2119.44 (12)H15E—C15B—H15F109.5
C6—C1—C7119.08 (13)C13B—C16B—H16D109.5
C2—C1—C7121.43 (12)C13B—C16B—H16E109.5
C12—O3—C9106.54 (14)H16D—C16B—H16E109.5
S1—N2—H4112.7 (12)C13B—C16B—H16F109.5
S1—N2—H3112.5 (13)H16D—C16B—H16F109.5
H4—N2—H3117.8 (18)H16E—C16B—H16F109.5
C2—N1—C8124.60 (12)N3B—C14B—H14D109.5
C2—N1—H2116.2 (13)N3B—C14B—H14E109.5
C8—N1—H2119.1 (13)H14D—C14B—H14E109.5
C5—C6—C1123.04 (14)N3B—C14B—H14F109.5
C5—C6—H6118.8 (10)H14D—C14B—H14F109.5
C1—C6—H6118.1 (10)H14E—C14B—H14F109.5
C3—C4—C5121.95 (12)C17A—N4A—C19122.2 (2)
C3—C4—Cl1117.48 (11)C17A—N4A—C18118.5 (2)
C5—C4—Cl1120.56 (11)C19—N4A—C18119.3 (2)
C11—C12—O3109.79 (14)O7—C17A—N4A119.4 (2)
C11—C12—C8132.95 (15)O7—C17A—C20123.0 (2)
O3—C12—C8117.08 (13)N4A—C17A—C20117.6 (2)
O2—C7—O1122.93 (12)C17B—N4B—C20115.2 (11)
O2—C7—C1124.06 (13)C17B—N4B—C19111.8 (13)
O1—C7—C1112.94 (12)C20—N4B—C19132.5 (8)
N1—C8—C12114.83 (13)N4B—C17B—O7109.0 (13)
N1—C8—H8111.1 (11)N4B—C17B—C18114.0 (12)
C12—C8—H8107.8 (10)O7—C17B—C18134.0 (11)
N1—C8—H7105.0 (11)C17A—C20—H20A109.5
C12—C8—H7112.2 (10)C17A—C20—H20B109.5
H8—C8—H7105.6 (15)H20A—C20—H20B109.5
C4—C3—C2120.94 (13)C17A—C20—H20C109.5
C4—C3—H5119.9 (11)H20A—C20—H20C109.5
C2—C3—H5119.2 (11)H20B—C20—H20C109.5
C12—C11—C10106.73 (17)N4B—C20—H20D109.5
C12—C11—H11124.9 (13)N4B—C20—H20E109.5
C10—C11—H11128.3 (13)H20D—C20—H20E109.5
C10—C9—O3110.40 (17)N4B—C20—H20F109.5
C10—C9—H9132.6 (14)H20D—C20—H20F109.5
O3—C9—H9117.0 (14)H20E—C20—H20F109.5
C9—C10—C11106.54 (17)N4A—C19—H19A109.5
C9—C10—H10123.1 (14)N4A—C19—H19B109.5
C11—C10—H10130.3 (15)H19A—C19—H19B109.5
C13A—N3A—C14A118.3 (5)N4A—C19—H19C109.5
C13A—N3A—C15A124.0 (4)H19A—C19—H19C109.5
C14A—N3A—C15A117.7 (5)H19B—C19—H19C109.5
O6—C13A—N3A117.3 (4)N4B—C19—H19D109.5
O6—C13A—C16A124.5 (7)N4B—C19—H19E109.5
N3A—C13A—C16A118.2 (7)H19D—C19—H19E109.5
N3A—C15A—H15A109.5N4B—C19—H19F109.5
N3A—C15A—H15B109.5H19D—C19—H19F109.5
H15A—C15A—H15B109.5H19E—C19—H19F109.5
N3A—C15A—H15C109.5N4A—C18—H18A109.5
H15A—C15A—H15C109.5N4A—C18—H18B109.5
H15B—C15A—H15C109.5H18A—C18—H18B109.5
N3A—C14A—H14A109.5N4A—C18—H18C109.5
N3A—C14A—H14B109.5H18A—C18—H18C109.5
H14A—C14A—H14B109.5H18B—C18—H18C109.5
N3A—C14A—H14C109.5C17B—C18—H18D109.5
H14A—C14A—H14C109.5C17B—C18—H18E109.5
H14B—C14A—H14C109.5H18D—C18—H18E109.5
C13A—C16A—H16A109.5C17B—C18—H18F109.5
C13A—C16A—H16B109.5H18D—C18—H18F109.5
H16A—C16A—H16B109.5H18E—C18—H18F109.5
C13A—C16A—H16C109.5
O4—S1—C5—C63.02 (13)C11—C12—C8—N1130.2 (2)
O5—S1—C5—C6124.88 (12)O3—C12—C8—N155.28 (18)
N2—S1—C5—C6118.50 (12)C5—C4—C3—C20.7 (2)
O4—S1—C5—C4176.11 (12)Cl1—C4—C3—C2177.92 (11)
O5—S1—C5—C456.00 (14)N1—C2—C3—C4178.13 (14)
N2—S1—C5—C460.63 (14)C1—C2—C3—C43.3 (2)
N1—C2—C1—C6176.49 (13)O3—C12—C11—C100.0 (2)
C3—C2—C1—C65.0 (2)C8—C12—C11—C10174.84 (17)
N1—C2—C1—C76.4 (2)C12—O3—C9—C100.7 (2)
C3—C2—C1—C7172.20 (13)O3—C9—C10—C110.7 (3)
C1—C2—N1—C8178.57 (14)C12—C11—C10—C90.4 (2)
C3—C2—N1—C80.1 (2)C14A—N3A—C13A—O60.4 (8)
C4—C5—C6—C11.3 (2)C15A—N3A—C13A—O6176.9 (4)
S1—C5—C6—C1179.52 (11)C14A—N3A—C13A—C16A178.9 (9)
C2—C1—C6—C52.8 (2)C15A—N3A—C13A—C16A2.4 (8)
C7—C1—C6—C5174.46 (13)C14B—N3B—C13B—O61.3 (12)
C6—C5—C4—C33.1 (2)C15B—N3B—C13B—O6173.9 (5)
S1—C5—C4—C3177.80 (12)C14B—N3B—C13B—C16B176.8 (13)
C6—C5—C4—Cl1175.56 (11)C15B—N3B—C13B—C16B8.0 (10)
S1—C5—C4—Cl13.58 (18)C19—N4A—C17A—O7177.17 (19)
C9—O3—C12—C110.5 (2)C18—N4A—C17A—O71.0 (3)
C9—O3—C12—C8176.19 (14)C19—N4A—C17A—C203.4 (3)
C6—C1—C7—O2178.88 (14)C18—N4A—C17A—C20178.42 (18)
C2—C1—C7—O24.0 (2)C20—N4B—C17B—O714.1 (11)
C6—C1—C7—O14.13 (19)C19—N4B—C17B—O7172.9 (6)
C2—C1—C7—O1173.04 (13)C20—N4B—C17B—C18177.3 (6)
C2—N1—C8—C1271.88 (19)C19—N4B—C17B—C189.7 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O60.82 (2)1.79 (2)2.5953 (15)166 (2)
N1—H2···O20.829 (19)2.041 (19)2.7055 (16)136.7 (17)
N1—H2···O2i0.829 (19)2.679 (19)3.3002 (16)132.9 (16)
N2—H3···O70.848 (19)1.923 (19)2.7715 (18)178.7 (18)
N2—H4···O5ii0.867 (19)2.15 (2)2.9536 (16)153.6 (17)
N2—H4···Cl10.867 (19)2.873 (19)3.3166 (14)113.6 (14)
Symmetry codes: (i) x+1, y+2, z; (ii) x+2, y+1, z.
 

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