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
CCDC reference: 1508888
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·2C4H9NO | F(000) = 1064 |
Mr = 504.98 | Dx = 1.412 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 17.0284 (10) Å | Cell parameters from 22285 reflections |
b = 7.8695 (3) Å | θ = 2.3–29.6° |
c = 22.0555 (15) Å | µ = 0.30 mm−1 |
β = 126.512 (4)° | T = 150 K |
V = 2375.5 (3) Å3 | Block, colorless |
Z = 4 | 0.52 × 0.24 × 0.22 mm |
Data collection top
Stoe IPDS 2 diffractometer | 6403 independent reflections |
Radiation source: fine-focus sealed tube | 4489 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.046 |
Detector resolution: 6.67 pixels mm-1 | θmax = 29.3°, θmin = 1.9° |
rotation method scans | h = −23→23 |
Absorption correction: numerical (X-RED; Stoe & Cie, 2007) | k = −10→9 |
Tmin = 0.900, Tmax = 0.951 | l = −30→30 |
29007 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | Hydrogen site location: mixed |
wR(F2) = 0.089 | H 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 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cl1 | 0.94954 (2) | 0.82572 (5) | 0.03001 (2) | 0.02809 (10) | |
S1 | 0.85099 (2) | 0.44549 (5) | −0.01785 (2) | 0.02066 (9) | |
O2 | 0.51868 (7) | 0.80290 (14) | −0.01654 (6) | 0.0254 (2) | |
O5 | 0.94797 (7) | 0.41606 (14) | 0.04965 (6) | 0.0268 (2) | |
O4 | 0.78044 (8) | 0.31176 (14) | −0.04502 (7) | 0.0294 (2) | |
O1 | 0.52868 (8) | 0.54943 (15) | −0.05694 (7) | 0.0283 (2) | |
H1 | 0.4707 (15) | 0.541 (2) | −0.0747 (11) | 0.034* | |
C5 | 0.79940 (10) | 0.62115 (19) | −0.00268 (8) | 0.0198 (3) | |
C2 | 0.71114 (10) | 0.88927 (18) | 0.02380 (8) | 0.0197 (3) | |
C1 | 0.66417 (9) | 0.72889 (18) | −0.00387 (7) | 0.0186 (3) | |
O6 | 0.34340 (8) | 0.48991 (15) | −0.12879 (6) | 0.0309 (3) | |
O3 | 0.79677 (9) | 1.12568 (16) | 0.19929 (7) | 0.0367 (3) | |
N2 | 0.86172 (9) | 0.49057 (18) | −0.08342 (7) | 0.0243 (3) | |
H4 | 0.9148 (14) | 0.546 (2) | −0.0670 (10) | 0.029* | |
H3 | 0.8088 (14) | 0.527 (2) | −0.1231 (11) | 0.029* | |
N1 | 0.67190 (9) | 1.01612 (16) | 0.03902 (7) | 0.0242 (3) | |
H2 | 0.6180 (14) | 0.996 (2) | 0.0299 (10) | 0.029* | |
C6 | 0.71031 (10) | 0.59981 (19) | −0.01466 (8) | 0.0194 (3) | |
H6 | 0.6782 (12) | 0.491 (2) | −0.0319 (9) | 0.023* | |
C4 | 0.84218 (9) | 0.78248 (19) | 0.01988 (8) | 0.0210 (3) | |
C12 | 0.80436 (11) | 1.1899 (2) | 0.14547 (9) | 0.0248 (3) | |
C7 | 0.56470 (9) | 0.69865 (19) | −0.02485 (8) | 0.0198 (3) | |
C8 | 0.71500 (11) | 1.18424 (19) | 0.06581 (9) | 0.0240 (3) | |
H8 | 0.7315 (13) | 1.233 (2) | 0.0341 (10) | 0.029* | |
H7 | 0.6623 (13) | 1.255 (2) | 0.0579 (10) | 0.029* | |
C3 | 0.80082 (10) | 0.91277 (19) | 0.03327 (8) | 0.0217 (3) | |
H5 | 0.8307 (12) | 1.019 (2) | 0.0478 (10) | 0.026* | |
C11 | 0.89355 (13) | 1.2579 (3) | 0.17839 (10) | 0.0399 (4) | |
H11 | 0.9162 (15) | 1.305 (3) | 0.1526 (12) | 0.048* | |
C9 | 0.88513 (15) | 1.1546 (3) | 0.26768 (10) | 0.0436 (5) | |
H9 | 0.8926 (16) | 1.113 (3) | 0.3115 (12) | 0.052* | |
C10 | 0.94551 (14) | 1.2350 (3) | 0.25797 (11) | 0.0479 (5) | |
H10 | 1.0076 (18) | 1.271 (3) | 0.2979 (13) | 0.058* | |
N3A | 0.2105 (2) | 0.4222 (3) | −0.24255 (16) | 0.0423 (10) | 0.596 (6) |
C13A | 0.2935 (3) | 0.5065 (5) | −0.2008 (2) | 0.0317 (9) | 0.596 (6) |
C15A | 0.1478 (5) | 0.4209 (9) | −0.3249 (3) | 0.077 (2) | 0.596 (6) |
H15A | 0.169756 | 0.331735 | −0.342725 | 0.115* | 0.596 (6) |
H15B | 0.151512 | 0.531479 | −0.343534 | 0.115* | 0.596 (6) |
H15C | 0.080203 | 0.398574 | −0.343764 | 0.115* | 0.596 (6) |
C14A | 0.1835 (8) | 0.3230 (17) | −0.2070 (6) | 0.068 (5) | 0.596 (6) |
H14A | 0.241411 | 0.294392 | −0.156289 | 0.102* | 0.596 (6) |
H14B | 0.153185 | 0.218342 | −0.235950 | 0.102* | 0.596 (6) |
H14C | 0.136723 | 0.384915 | −0.203162 | 0.102* | 0.596 (6) |
C16A | 0.3242 (11) | 0.614 (2) | −0.2403 (8) | 0.053 (3) | 0.596 (6) |
H16A | 0.338784 | 0.539960 | −0.268165 | 0.080* | 0.596 (6) |
H16B | 0.382601 | 0.679429 | −0.202769 | 0.080* | 0.596 (6) |
H16C | 0.271129 | 0.691810 | −0.275437 | 0.080* | 0.596 (6) |
N3B | 0.2592 (3) | 0.5220 (5) | −0.2521 (2) | 0.0331 (13) | 0.404 (6) |
C13B | 0.2698 (3) | 0.4509 (7) | −0.1925 (3) | 0.0260 (12) | 0.404 (6) |
C15B | 0.1812 (5) | 0.4767 (12) | −0.3312 (4) | 0.0499 (18) | 0.404 (6) |
H15D | 0.199281 | 0.372373 | −0.344388 | 0.075* | 0.404 (6) |
H15E | 0.172582 | 0.569167 | −0.364396 | 0.075* | 0.404 (6) |
H15F | 0.119973 | 0.458375 | −0.337217 | 0.075* | 0.404 (6) |
C16B | 0.1859 (12) | 0.326 (2) | −0.2068 (9) | 0.054 (5)* | 0.404 (6) |
H16D | 0.192714 | 0.311060 | −0.159777 | 0.080* | 0.404 (6) |
H16E | 0.192127 | 0.215076 | −0.224015 | 0.080* | 0.404 (6) |
H16F | 0.121667 | 0.374434 | −0.245423 | 0.080* | 0.404 (6) |
C14B | 0.3349 (17) | 0.643 (3) | −0.2362 (11) | 0.045 (3) | 0.404 (6) |
H14D | 0.389422 | 0.580518 | −0.229541 | 0.067* | 0.404 (6) |
H14E | 0.358387 | 0.705564 | −0.189915 | 0.067* | 0.404 (6) |
H14F | 0.307566 | 0.722309 | −0.278335 | 0.067* | 0.404 (6) |
O7 | 0.68747 (10) | 0.6082 (2) | −0.21179 (8) | 0.0595 (4) | |
N4A | 0.54305 (14) | 0.7347 (2) | −0.26861 (11) | 0.0317 (6) | 0.866 (6) |
C17A | 0.60767 (15) | 0.6445 (3) | −0.27117 (13) | 0.0290 (6) | 0.866 (6) |
N4B | 0.5436 (8) | 0.6830 (13) | −0.3073 (7) | 0.026 (4) | 0.134 (6) |
C17B | 0.6096 (10) | 0.7058 (17) | −0.2351 (8) | 0.026 (4) | 0.134 (6) |
C20 | 0.57910 (16) | 0.5933 (3) | −0.34752 (11) | 0.0448 (5) | |
H20A | 0.563667 | 0.695046 | −0.378376 | 0.067* | 0.866 (6) |
H20B | 0.521611 | 0.519204 | −0.372252 | 0.067* | 0.866 (6) |
H20C | 0.633380 | 0.532300 | −0.341709 | 0.067* | 0.866 (6) |
H20D | 0.524904 | 0.581859 | −0.401169 | 0.067* | 0.134 (6) |
H20E | 0.631703 | 0.659671 | −0.342007 | 0.067* | 0.134 (6) |
H20F | 0.603666 | 0.480309 | −0.325449 | 0.067* | 0.134 (6) |
C19 | 0.44588 (14) | 0.7752 (3) | −0.33632 (12) | 0.0530 (6) | |
H19A | 0.420194 | 0.874700 | −0.326684 | 0.079* | 0.866 (6) |
H19B | 0.402275 | 0.678121 | −0.349799 | 0.079* | 0.866 (6) |
H19C | 0.449909 | 0.799926 | −0.377941 | 0.079* | 0.866 (6) |
H19D | 0.398200 | 0.755273 | −0.390600 | 0.079* | 0.134 (6) |
H19E | 0.420263 | 0.730668 | −0.309752 | 0.079* | 0.134 (6) |
H19F | 0.457823 | 0.897458 | −0.326848 | 0.079* | 0.134 (6) |
C18 | 0.57031 (19) | 0.7897 (3) | −0.19500 (12) | 0.0544 (6) | |
H18A | 0.536523 | 0.896086 | −0.200830 | 0.082* | 0.866 (6) |
H18B | 0.641095 | 0.807792 | −0.160634 | 0.082* | 0.866 (6) |
H18C | 0.551574 | 0.702097 | −0.174249 | 0.082* | 0.866 (6) |
H18D | 0.623658 | 0.802747 | −0.141222 | 0.082* | 0.134 (6) |
H18E | 0.543252 | 0.901654 | −0.217274 | 0.082* | 0.134 (6) |
H18F | 0.519007 | 0.718158 | −0.200990 | 0.082* | 0.134 (6) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.01917 (16) | 0.0315 (2) | 0.0384 (2) | −0.00577 (14) | 0.01975 (15) | −0.00679 (16) |
S1 | 0.01740 (15) | 0.02147 (17) | 0.02635 (17) | 0.00245 (13) | 0.01477 (14) | 0.00096 (14) |
O2 | 0.0214 (5) | 0.0247 (6) | 0.0358 (6) | 0.0018 (4) | 0.0201 (5) | −0.0013 (5) |
O5 | 0.0207 (5) | 0.0337 (6) | 0.0276 (5) | 0.0081 (4) | 0.0153 (5) | 0.0070 (5) |
O4 | 0.0279 (5) | 0.0223 (5) | 0.0468 (7) | −0.0011 (4) | 0.0270 (5) | −0.0046 (5) |
O1 | 0.0191 (5) | 0.0280 (6) | 0.0417 (6) | −0.0054 (4) | 0.0202 (5) | −0.0102 (5) |
C5 | 0.0170 (6) | 0.0214 (7) | 0.0222 (7) | 0.0011 (5) | 0.0123 (5) | 0.0008 (5) |
C2 | 0.0182 (6) | 0.0219 (7) | 0.0203 (6) | 0.0008 (5) | 0.0121 (6) | 0.0002 (5) |
C1 | 0.0169 (6) | 0.0208 (7) | 0.0199 (6) | 0.0003 (5) | 0.0119 (5) | 0.0012 (5) |
O6 | 0.0217 (5) | 0.0358 (6) | 0.0302 (6) | −0.0021 (4) | 0.0127 (5) | −0.0061 (5) |
O3 | 0.0461 (7) | 0.0363 (7) | 0.0341 (6) | −0.0058 (5) | 0.0274 (6) | 0.0003 (5) |
N2 | 0.0169 (5) | 0.0330 (7) | 0.0230 (6) | 0.0019 (5) | 0.0118 (5) | 0.0001 (5) |
N1 | 0.0209 (6) | 0.0224 (6) | 0.0347 (7) | −0.0024 (5) | 0.0195 (5) | −0.0052 (5) |
C6 | 0.0176 (6) | 0.0191 (7) | 0.0222 (7) | 0.0006 (5) | 0.0123 (5) | 0.0005 (5) |
C4 | 0.0151 (6) | 0.0268 (7) | 0.0222 (7) | −0.0012 (5) | 0.0117 (5) | 0.0001 (6) |
C12 | 0.0298 (7) | 0.0227 (7) | 0.0294 (7) | 0.0013 (6) | 0.0217 (6) | −0.0019 (6) |
C7 | 0.0177 (6) | 0.0217 (7) | 0.0216 (6) | 0.0003 (5) | 0.0125 (5) | 0.0008 (6) |
C8 | 0.0250 (7) | 0.0185 (7) | 0.0320 (8) | 0.0007 (6) | 0.0189 (6) | −0.0013 (6) |
C3 | 0.0201 (6) | 0.0213 (8) | 0.0255 (7) | −0.0025 (5) | 0.0146 (6) | −0.0020 (6) |
C11 | 0.0302 (8) | 0.0604 (13) | 0.0325 (9) | −0.0084 (8) | 0.0205 (8) | −0.0072 (8) |
C9 | 0.0516 (11) | 0.0480 (12) | 0.0261 (8) | 0.0034 (9) | 0.0204 (9) | 0.0015 (8) |
C10 | 0.0338 (9) | 0.0708 (15) | 0.0307 (9) | −0.0013 (9) | 0.0146 (8) | −0.0106 (10) |
N3A | 0.0352 (17) | 0.0355 (17) | 0.0335 (17) | 0.0026 (12) | 0.0081 (15) | −0.0048 (12) |
C13A | 0.0336 (19) | 0.0262 (19) | 0.038 (2) | 0.0080 (14) | 0.0227 (18) | 0.0005 (15) |
C15A | 0.069 (4) | 0.072 (4) | 0.031 (2) | 0.022 (3) | −0.002 (2) | −0.009 (2) |
C14A | 0.030 (3) | 0.047 (4) | 0.074 (5) | −0.0164 (18) | 0.0014 (18) | 0.002 (2) |
C16A | 0.057 (7) | 0.053 (6) | 0.067 (5) | 0.013 (5) | 0.046 (5) | 0.010 (4) |
N3B | 0.029 (2) | 0.037 (2) | 0.029 (2) | 0.0069 (16) | 0.0143 (18) | 0.0062 (16) |
C13B | 0.019 (2) | 0.024 (2) | 0.030 (3) | 0.0008 (17) | 0.011 (2) | −0.003 (2) |
C15B | 0.041 (4) | 0.063 (5) | 0.027 (3) | 0.016 (3) | 0.010 (3) | 0.007 (3) |
C14B | 0.039 (4) | 0.053 (7) | 0.043 (5) | −0.006 (4) | 0.025 (4) | 0.011 (4) |
O7 | 0.0288 (7) | 0.0857 (12) | 0.0418 (8) | 0.0153 (7) | 0.0089 (6) | 0.0190 (8) |
N4A | 0.0327 (11) | 0.0340 (10) | 0.0303 (10) | 0.0060 (7) | 0.0198 (9) | 0.0060 (8) |
C17A | 0.0261 (12) | 0.0284 (11) | 0.0309 (12) | 0.0003 (8) | 0.0161 (10) | 0.0031 (9) |
N4B | 0.020 (6) | 0.020 (5) | 0.027 (7) | −0.006 (4) | 0.008 (5) | 0.001 (4) |
C17B | 0.030 (8) | 0.024 (6) | 0.032 (8) | −0.012 (5) | 0.023 (7) | −0.004 (6) |
C20 | 0.0631 (13) | 0.0406 (11) | 0.0448 (11) | −0.0010 (9) | 0.0397 (10) | −0.0039 (9) |
C19 | 0.0355 (10) | 0.0655 (14) | 0.0560 (12) | 0.0209 (9) | 0.0262 (9) | 0.0351 (11) |
C18 | 0.0810 (16) | 0.0517 (13) | 0.0484 (12) | 0.0046 (11) | 0.0483 (12) | −0.0022 (10) |
Geometric parameters (Å, º) top
Cl1—C4 | 1.7383 (13) | C16A—H16A | 0.9800 |
S1—O4 | 1.4329 (11) | C16A—H16B | 0.9800 |
S1—O5 | 1.4393 (10) | C16A—H16C | 0.9800 |
S1—N2 | 1.6017 (13) | N3B—C13B | 1.338 (7) |
S1—C5 | 1.7732 (15) | N3B—C14B | 1.46 (2) |
O2—C7 | 1.2213 (17) | N3B—C15B | 1.475 (9) |
O1—C7 | 1.3189 (18) | C13B—C16B | 1.604 (17) |
O1—H1 | 0.82 (2) | C15B—H15D | 0.9800 |
C5—C6 | 1.3865 (18) | C15B—H15E | 0.9800 |
C5—C4 | 1.400 (2) | C15B—H15F | 0.9800 |
C2—N1 | 1.3500 (19) | C16B—H16D | 0.9800 |
C2—C1 | 1.423 (2) | C16B—H16E | 0.9800 |
C2—C3 | 1.4249 (19) | C16B—H16F | 0.9800 |
C1—C6 | 1.3886 (19) | C14B—H14D | 0.9800 |
C1—C7 | 1.4857 (18) | C14B—H14E | 0.9800 |
O6—C13B | 1.243 (5) | C14B—H14F | 0.9800 |
O6—C13A | 1.287 (4) | O7—C17A | 1.235 (2) |
O3—C12 | 1.3655 (19) | O7—C17B | 1.342 (15) |
O3—C9 | 1.375 (2) | N4A—C17A | 1.338 (3) |
N2—H4 | 0.867 (19) | N4A—C19 | 1.459 (3) |
N2—H3 | 0.848 (19) | N4A—C18 | 1.463 (3) |
N1—C8 | 1.4568 (19) | C17A—C20 | 1.503 (3) |
N1—H2 | 0.829 (19) | N4B—C17B | 1.30 (2) |
C6—H6 | 0.961 (18) | N4B—C20 | 1.514 (14) |
C4—C3 | 1.372 (2) | N4B—C19 | 1.561 (12) |
C12—C11 | 1.344 (2) | C17B—C18 | 1.539 (15) |
C12—C8 | 1.491 (2) | C20—H20A | 0.9800 |
C8—H8 | 0.976 (19) | C20—H20B | 0.9800 |
C8—H7 | 0.980 (18) | C20—H20C | 0.9800 |
C3—H5 | 0.927 (18) | C20—H20D | 0.9800 |
C11—C10 | 1.431 (3) | C20—H20E | 0.9800 |
C11—H11 | 0.93 (2) | C20—H20F | 0.9800 |
C9—C10 | 1.329 (3) | C19—H19A | 0.9800 |
C9—H9 | 0.95 (2) | C19—H19B | 0.9800 |
C10—H10 | 0.93 (2) | C19—H19C | 0.9800 |
N3A—C13A | 1.317 (5) | C19—H19D | 0.9800 |
N3A—C14A | 1.366 (12) | C19—H19E | 0.9800 |
N3A—C15A | 1.460 (6) | C19—H19F | 0.9800 |
C13A—C16A | 1.513 (15) | C18—H18A | 0.9800 |
C15A—H15A | 0.9800 | C18—H18B | 0.9800 |
C15A—H15B | 0.9800 | C18—H18C | 0.9800 |
C15A—H15C | 0.9800 | C18—H18D | 0.9800 |
C14A—H14A | 0.9800 | C18—H18E | 0.9800 |
C14A—H14B | 0.9800 | C18—H18F | 0.9800 |
C14A—H14C | 0.9800 | | |
| | | |
O4—S1—O5 | 118.35 (7) | H16A—C16A—H16C | 109.5 |
O4—S1—N2 | 107.62 (7) | H16B—C16A—H16C | 109.5 |
O5—S1—N2 | 107.00 (7) | C13B—N3B—C14B | 116.7 (9) |
O4—S1—C5 | 105.38 (6) | C13B—N3B—C15B | 124.1 (5) |
O5—S1—C5 | 108.83 (7) | C14B—N3B—C15B | 119.0 (9) |
N2—S1—C5 | 109.46 (7) | O6—C13B—N3B | 117.6 (5) |
C7—O1—H1 | 111.7 (14) | O6—C13B—C16B | 123.7 (7) |
C6—C5—C4 | 117.17 (13) | N3B—C13B—C16B | 118.7 (7) |
C6—C5—S1 | 118.58 (11) | N3B—C15B—H15D | 109.5 |
C4—C5—S1 | 124.24 (10) | N3B—C15B—H15E | 109.5 |
N1—C2—C1 | 121.84 (12) | H15D—C15B—H15E | 109.5 |
N1—C2—C3 | 120.89 (13) | N3B—C15B—H15F | 109.5 |
C1—C2—C3 | 117.26 (12) | H15D—C15B—H15F | 109.5 |
C6—C1—C2 | 119.44 (12) | H15E—C15B—H15F | 109.5 |
C6—C1—C7 | 119.08 (13) | C13B—C16B—H16D | 109.5 |
C2—C1—C7 | 121.43 (12) | C13B—C16B—H16E | 109.5 |
C12—O3—C9 | 106.54 (14) | H16D—C16B—H16E | 109.5 |
S1—N2—H4 | 112.7 (12) | C13B—C16B—H16F | 109.5 |
S1—N2—H3 | 112.5 (13) | H16D—C16B—H16F | 109.5 |
H4—N2—H3 | 117.8 (18) | H16E—C16B—H16F | 109.5 |
C2—N1—C8 | 124.60 (12) | N3B—C14B—H14D | 109.5 |
C2—N1—H2 | 116.2 (13) | N3B—C14B—H14E | 109.5 |
C8—N1—H2 | 119.1 (13) | H14D—C14B—H14E | 109.5 |
C5—C6—C1 | 123.04 (14) | N3B—C14B—H14F | 109.5 |
C5—C6—H6 | 118.8 (10) | H14D—C14B—H14F | 109.5 |
C1—C6—H6 | 118.1 (10) | H14E—C14B—H14F | 109.5 |
C3—C4—C5 | 121.95 (12) | C17A—N4A—C19 | 122.2 (2) |
C3—C4—Cl1 | 117.48 (11) | C17A—N4A—C18 | 118.5 (2) |
C5—C4—Cl1 | 120.56 (11) | C19—N4A—C18 | 119.3 (2) |
C11—C12—O3 | 109.79 (14) | O7—C17A—N4A | 119.4 (2) |
C11—C12—C8 | 132.95 (15) | O7—C17A—C20 | 123.0 (2) |
O3—C12—C8 | 117.08 (13) | N4A—C17A—C20 | 117.6 (2) |
O2—C7—O1 | 122.93 (12) | C17B—N4B—C20 | 115.2 (11) |
O2—C7—C1 | 124.06 (13) | C17B—N4B—C19 | 111.8 (13) |
O1—C7—C1 | 112.94 (12) | C20—N4B—C19 | 132.5 (8) |
N1—C8—C12 | 114.83 (13) | N4B—C17B—O7 | 109.0 (13) |
N1—C8—H8 | 111.1 (11) | N4B—C17B—C18 | 114.0 (12) |
C12—C8—H8 | 107.8 (10) | O7—C17B—C18 | 134.0 (11) |
N1—C8—H7 | 105.0 (11) | C17A—C20—H20A | 109.5 |
C12—C8—H7 | 112.2 (10) | C17A—C20—H20B | 109.5 |
H8—C8—H7 | 105.6 (15) | H20A—C20—H20B | 109.5 |
C4—C3—C2 | 120.94 (13) | C17A—C20—H20C | 109.5 |
C4—C3—H5 | 119.9 (11) | H20A—C20—H20C | 109.5 |
C2—C3—H5 | 119.2 (11) | H20B—C20—H20C | 109.5 |
C12—C11—C10 | 106.73 (17) | N4B—C20—H20D | 109.5 |
C12—C11—H11 | 124.9 (13) | N4B—C20—H20E | 109.5 |
C10—C11—H11 | 128.3 (13) | H20D—C20—H20E | 109.5 |
C10—C9—O3 | 110.40 (17) | N4B—C20—H20F | 109.5 |
C10—C9—H9 | 132.6 (14) | H20D—C20—H20F | 109.5 |
O3—C9—H9 | 117.0 (14) | H20E—C20—H20F | 109.5 |
C9—C10—C11 | 106.54 (17) | N4A—C19—H19A | 109.5 |
C9—C10—H10 | 123.1 (14) | N4A—C19—H19B | 109.5 |
C11—C10—H10 | 130.3 (15) | H19A—C19—H19B | 109.5 |
C13A—N3A—C14A | 118.3 (5) | N4A—C19—H19C | 109.5 |
C13A—N3A—C15A | 124.0 (4) | H19A—C19—H19C | 109.5 |
C14A—N3A—C15A | 117.7 (5) | H19B—C19—H19C | 109.5 |
O6—C13A—N3A | 117.3 (4) | N4B—C19—H19D | 109.5 |
O6—C13A—C16A | 124.5 (7) | N4B—C19—H19E | 109.5 |
N3A—C13A—C16A | 118.2 (7) | H19D—C19—H19E | 109.5 |
N3A—C15A—H15A | 109.5 | N4B—C19—H19F | 109.5 |
N3A—C15A—H15B | 109.5 | H19D—C19—H19F | 109.5 |
H15A—C15A—H15B | 109.5 | H19E—C19—H19F | 109.5 |
N3A—C15A—H15C | 109.5 | N4A—C18—H18A | 109.5 |
H15A—C15A—H15C | 109.5 | N4A—C18—H18B | 109.5 |
H15B—C15A—H15C | 109.5 | H18A—C18—H18B | 109.5 |
N3A—C14A—H14A | 109.5 | N4A—C18—H18C | 109.5 |
N3A—C14A—H14B | 109.5 | H18A—C18—H18C | 109.5 |
H14A—C14A—H14B | 109.5 | H18B—C18—H18C | 109.5 |
N3A—C14A—H14C | 109.5 | C17B—C18—H18D | 109.5 |
H14A—C14A—H14C | 109.5 | C17B—C18—H18E | 109.5 |
H14B—C14A—H14C | 109.5 | H18D—C18—H18E | 109.5 |
C13A—C16A—H16A | 109.5 | C17B—C18—H18F | 109.5 |
C13A—C16A—H16B | 109.5 | H18D—C18—H18F | 109.5 |
H16A—C16A—H16B | 109.5 | H18E—C18—H18F | 109.5 |
C13A—C16A—H16C | 109.5 | | |
| | | |
O4—S1—C5—C6 | 3.02 (13) | C11—C12—C8—N1 | 130.2 (2) |
O5—S1—C5—C6 | −124.88 (12) | O3—C12—C8—N1 | −55.28 (18) |
N2—S1—C5—C6 | 118.50 (12) | C5—C4—C3—C2 | −0.7 (2) |
O4—S1—C5—C4 | −176.11 (12) | Cl1—C4—C3—C2 | 177.92 (11) |
O5—S1—C5—C4 | 56.00 (14) | N1—C2—C3—C4 | 178.13 (14) |
N2—S1—C5—C4 | −60.63 (14) | C1—C2—C3—C4 | −3.3 (2) |
N1—C2—C1—C6 | −176.49 (13) | O3—C12—C11—C10 | 0.0 (2) |
C3—C2—C1—C6 | 5.0 (2) | C8—C12—C11—C10 | 174.84 (17) |
N1—C2—C1—C7 | 6.4 (2) | C12—O3—C9—C10 | 0.7 (2) |
C3—C2—C1—C7 | −172.20 (13) | O3—C9—C10—C11 | −0.7 (3) |
C1—C2—N1—C8 | −178.57 (14) | C12—C11—C10—C9 | 0.4 (2) |
C3—C2—N1—C8 | −0.1 (2) | C14A—N3A—C13A—O6 | −0.4 (8) |
C4—C5—C6—C1 | −1.3 (2) | C15A—N3A—C13A—O6 | −176.9 (4) |
S1—C5—C6—C1 | 179.52 (11) | C14A—N3A—C13A—C16A | 178.9 (9) |
C2—C1—C6—C5 | −2.8 (2) | C15A—N3A—C13A—C16A | 2.4 (8) |
C7—C1—C6—C5 | 174.46 (13) | C14B—N3B—C13B—O6 | −1.3 (12) |
C6—C5—C4—C3 | 3.1 (2) | C15B—N3B—C13B—O6 | 173.9 (5) |
S1—C5—C4—C3 | −177.80 (12) | C14B—N3B—C13B—C16B | 176.8 (13) |
C6—C5—C4—Cl1 | −175.56 (11) | C15B—N3B—C13B—C16B | −8.0 (10) |
S1—C5—C4—Cl1 | 3.58 (18) | C19—N4A—C17A—O7 | −177.17 (19) |
C9—O3—C12—C11 | −0.5 (2) | C18—N4A—C17A—O7 | 1.0 (3) |
C9—O3—C12—C8 | −176.19 (14) | C19—N4A—C17A—C20 | 3.4 (3) |
C6—C1—C7—O2 | 178.88 (14) | C18—N4A—C17A—C20 | −178.42 (18) |
C2—C1—C7—O2 | −4.0 (2) | C20—N4B—C17B—O7 | −14.1 (11) |
C6—C1—C7—O1 | −4.13 (19) | C19—N4B—C17B—O7 | 172.9 (6) |
C2—C1—C7—O1 | 173.04 (13) | C20—N4B—C17B—C18 | −177.3 (6) |
C2—N1—C8—C12 | −71.88 (19) | C19—N4B—C17B—C18 | 9.7 (11) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O6 | 0.82 (2) | 1.79 (2) | 2.5953 (15) | 166 (2) |
N1—H2···O2 | 0.829 (19) | 2.041 (19) | 2.7055 (16) | 136.7 (17) |
N1—H2···O2i | 0.829 (19) | 2.679 (19) | 3.3002 (16) | 132.9 (16) |
N2—H3···O7 | 0.848 (19) | 1.923 (19) | 2.7715 (18) | 178.7 (18) |
N2—H4···O5ii | 0.867 (19) | 2.15 (2) | 2.9536 (16) | 153.6 (17) |
N2—H4···Cl1 | 0.867 (19) | 2.873 (19) | 3.3166 (14) | 113.6 (14) |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+2, −y+1, −z. |