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Sildenafil citrate is well known as Viagra for the treatment of erectile dysfuncion. In the title compound (systematic name: 1-{[3-(6,7-Di­hydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo­[4,3-d]­pyrimidin-5-yl)-4-ethoxy­phenyl]­sulfonyl}-4-methyl­piper­az­in­ium citrate monohydrate), C22H31N6O4S+·C6H7O7-·H2O, the pyrazolopyrimidone ring system and the benzene ring are almost coplanar, enabling an intramolecular hydrogen bond between the pyrazolopyrimidone NH group and the O atom of the ethoxy group. One of the N atoms of the piperazine ring is protonated and the citrate mol­ecule exists as an anion. The crystal packing is stabilized by several hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805002564/hg6131sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805002564/hg6131Isup2.hkl
Contains datablock I

CCDC reference: 264096

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.079
  • wR factor = 0.154
  • Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 34 Perc.
Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.782 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.03 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.65 Ratio PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.70 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.24 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C41 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.

1-{[3-(6,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)- 4-ethoxyphenyl]sulfonyl}-4-methylpiperazinium citrate monohydrate top
Crystal data top
C22H31N6O4S+·C6H7O7·H2OF(000) = 2896
Mr = 684.72Dx = 1.416 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 8732 reflections
a = 24.002 (4) Åθ = 2.0–23.1°
b = 10.9833 (17) ŵ = 0.17 mm1
c = 24.364 (3) ÅT = 173 K
V = 6422.9 (17) Å3Needle, colourless
Z = 80.26 × 0.12 × 0.11 mm
Data collection top
Stoe IPDS-II two-circle
diffractometer
5856 independent reflections
Radiation source: fine-focus sealed tube1970 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.098
ω scansθmax = 25.4°, θmin = 1.9°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 2828
Tmin = 0.937, Tmax = 0.951k = 1313
44385 measured reflectionsl = 2927
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)] = 0.079Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154H-atom parameters constrained
S = 0.78 w = 1/[σ2(Fo2) + (0.0407P)2]
where P = (Fo2 + 2Fc2)/3
5856 reflections(Δ/σ)max < 0.001
428 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.42 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.51081 (6)0.50964 (15)0.29812 (6)0.0445 (4)
O10.46362 (14)0.5885 (4)0.29471 (17)0.0515 (11)
O20.50684 (18)0.3861 (4)0.27829 (17)0.0606 (13)
N110.56093 (17)0.5749 (4)0.26385 (18)0.0330 (11)
C120.6124 (2)0.5013 (5)0.2576 (2)0.0376 (14)
H12A0.60280.41640.24780.045*
H12B0.63340.50020.29260.045*
C130.6476 (2)0.5571 (5)0.2131 (2)0.0430 (15)
H13A0.62760.55120.17760.052*
H13B0.68280.51090.20970.052*
N140.66068 (18)0.6888 (4)0.22483 (19)0.0372 (12)
H140.68160.69200.25690.045*
C150.6074 (2)0.7577 (5)0.2344 (2)0.0391 (15)
H15A0.61620.84300.24430.047*
H15B0.58520.75860.20020.047*
C160.5742 (2)0.7012 (5)0.2790 (2)0.0389 (15)
H16A0.59570.70240.31370.047*
H16B0.53930.74780.28470.047*
C170.6948 (3)0.7416 (6)0.1798 (3)0.0536 (18)
H17A0.72900.69380.17540.080*
H17B0.70440.82590.18890.080*
H17C0.67340.73980.14560.080*
C210.5329 (2)0.5069 (5)0.3659 (2)0.0393 (14)
C220.5178 (2)0.5976 (5)0.4018 (2)0.0394 (15)
H220.49260.65850.38960.047*
C230.5382 (2)0.6037 (5)0.4554 (2)0.0385 (15)
C240.5757 (2)0.5122 (6)0.4726 (2)0.0379 (14)
C250.5904 (2)0.4195 (6)0.4369 (3)0.0431 (15)
H250.61480.35700.44910.052*
C260.5705 (2)0.4163 (6)0.3842 (3)0.0460 (16)
H260.58200.35330.36000.055*
O270.59346 (15)0.5167 (4)0.52518 (17)0.0434 (11)
C280.6344 (2)0.4316 (6)0.5457 (3)0.0497 (17)
H28A0.66940.43860.52440.060*
H28B0.62040.34720.54230.060*
C290.6448 (3)0.4610 (7)0.6038 (3)0.063 (2)
H29A0.67240.40440.61880.094*
H29B0.60990.45370.62450.094*
H29C0.65880.54450.60670.094*
C310.5178 (2)0.7057 (5)0.4897 (2)0.0371 (14)
N320.54446 (19)0.7278 (5)0.53903 (19)0.0427 (13)
H320.57290.68020.54680.051*
C330.5318 (3)0.8150 (6)0.5771 (2)0.0452 (16)
O330.55788 (19)0.8276 (4)0.61949 (18)0.0551 (12)
C340.4839 (2)0.8840 (5)0.5588 (2)0.0399 (14)
C350.4605 (2)0.8619 (5)0.5079 (2)0.0384 (15)
N360.47678 (18)0.7724 (4)0.47275 (19)0.0393 (12)
N370.4565 (2)0.9798 (5)0.5815 (2)0.0480 (13)
C370.4657 (3)1.0358 (6)0.6346 (2)0.062 (2)
H37A0.48631.11210.62980.093*
H37B0.48730.98040.65790.093*
H37C0.42981.05290.65210.093*
N380.4156 (2)1.0183 (5)0.5475 (2)0.0509 (14)
C390.4177 (3)0.9500 (6)0.5026 (3)0.0438 (16)
C400.3769 (2)0.9660 (6)0.4569 (3)0.0509 (18)
H40A0.39260.93010.42300.061*
H40B0.37141.05420.45030.061*
C410.3207 (3)0.9077 (6)0.4684 (3)0.0580 (19)
H41A0.32660.82190.47930.070*
H41B0.30300.95030.49970.070*
C420.2820 (3)0.9114 (9)0.4202 (3)0.098 (3)
H42A0.24670.87250.43010.146*
H42B0.29890.86780.38930.146*
H42C0.27520.99630.40970.146*
C10.6952 (3)0.7525 (6)0.4388 (3)0.0519 (18)
O110.6764 (2)0.7142 (6)0.4812 (2)0.100 (2)
O120.6703 (2)0.8386 (5)0.41230 (19)0.0703 (15)
H120.64460.86740.43180.084*
C20.7480 (3)0.7061 (5)0.4127 (2)0.0430 (16)
H2A0.77970.75180.42860.052*
H2B0.75260.61970.42330.052*
C30.7523 (2)0.7140 (4)0.3512 (3)0.0350 (14)
O30.70777 (15)0.6480 (3)0.32673 (16)0.0367 (10)
H30.70900.57510.33710.044*
C40.8086 (2)0.6625 (5)0.3308 (3)0.0468 (17)
H4A0.83950.71140.34630.056*
H4B0.81290.57760.34390.056*
C50.8118 (2)0.6649 (7)0.2691 (3)0.0549 (19)
O510.82320 (19)0.7579 (4)0.2438 (2)0.0765 (16)
O520.79846 (19)0.5650 (4)0.24213 (19)0.0582 (13)
H520.78450.51430.26400.070*
C60.7474 (3)0.8472 (5)0.3322 (3)0.0417 (15)
O610.78086 (16)0.9203 (4)0.35450 (18)0.0492 (11)
O620.71438 (16)0.8711 (3)0.29353 (16)0.0420 (10)
O1W0.8948 (6)0.7871 (11)0.1605 (6)0.311 (7)
H1WA0.91450.73010.17280.374*
H1WB0.87210.77770.18640.374*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0363 (7)0.0502 (10)0.0471 (9)0.0069 (8)0.0012 (8)0.0099 (9)
O10.028 (2)0.068 (3)0.058 (3)0.007 (2)0.003 (2)0.014 (3)
O20.057 (3)0.058 (3)0.066 (3)0.026 (2)0.011 (2)0.023 (3)
N110.029 (2)0.027 (3)0.044 (3)0.001 (2)0.002 (2)0.000 (2)
C120.037 (3)0.027 (3)0.050 (4)0.009 (3)0.002 (3)0.003 (3)
C130.044 (3)0.040 (4)0.045 (4)0.003 (3)0.002 (3)0.002 (3)
N140.034 (3)0.037 (3)0.041 (3)0.001 (2)0.001 (2)0.000 (2)
C150.033 (3)0.034 (3)0.050 (4)0.006 (3)0.005 (3)0.001 (3)
C160.045 (3)0.035 (3)0.037 (4)0.009 (3)0.003 (3)0.006 (3)
C170.064 (4)0.049 (4)0.048 (4)0.002 (4)0.013 (3)0.006 (3)
C210.038 (3)0.034 (3)0.046 (4)0.006 (3)0.015 (3)0.003 (3)
C220.040 (3)0.036 (4)0.042 (4)0.004 (3)0.005 (3)0.006 (3)
C230.037 (3)0.040 (4)0.038 (4)0.001 (3)0.004 (3)0.001 (3)
C240.037 (3)0.037 (4)0.039 (4)0.000 (3)0.009 (3)0.002 (3)
C250.040 (3)0.041 (4)0.048 (4)0.004 (3)0.003 (3)0.006 (3)
C260.043 (4)0.039 (4)0.055 (4)0.008 (3)0.016 (3)0.000 (3)
O270.048 (2)0.038 (3)0.044 (3)0.014 (2)0.004 (2)0.003 (2)
C280.038 (4)0.036 (4)0.075 (5)0.009 (3)0.003 (3)0.010 (4)
C290.049 (4)0.082 (6)0.057 (5)0.009 (4)0.011 (3)0.002 (4)
C310.043 (4)0.037 (3)0.031 (3)0.005 (3)0.002 (3)0.001 (3)
N320.042 (3)0.047 (3)0.038 (3)0.011 (3)0.007 (2)0.002 (3)
C330.071 (5)0.039 (4)0.026 (4)0.003 (3)0.002 (3)0.003 (3)
O330.072 (3)0.050 (3)0.043 (3)0.001 (2)0.016 (2)0.002 (2)
C340.051 (4)0.034 (3)0.035 (3)0.004 (3)0.000 (3)0.002 (3)
C350.043 (4)0.036 (3)0.036 (4)0.005 (3)0.006 (3)0.001 (3)
N360.039 (3)0.036 (3)0.043 (3)0.008 (2)0.002 (2)0.001 (2)
N370.053 (3)0.047 (3)0.044 (3)0.006 (3)0.000 (3)0.004 (3)
C370.100 (6)0.045 (4)0.040 (4)0.006 (4)0.002 (4)0.009 (3)
N380.058 (3)0.048 (3)0.047 (3)0.010 (3)0.005 (3)0.008 (3)
C390.052 (4)0.044 (4)0.036 (4)0.002 (3)0.012 (3)0.001 (3)
C400.048 (4)0.054 (4)0.050 (4)0.012 (3)0.010 (3)0.011 (3)
C410.050 (4)0.053 (4)0.071 (5)0.006 (4)0.005 (4)0.014 (4)
C420.071 (5)0.120 (8)0.102 (7)0.009 (6)0.023 (5)0.032 (6)
C10.068 (5)0.045 (4)0.042 (4)0.002 (4)0.014 (4)0.010 (4)
O110.093 (4)0.113 (5)0.095 (5)0.016 (4)0.018 (4)0.052 (4)
O120.078 (4)0.072 (4)0.060 (3)0.034 (3)0.021 (3)0.008 (3)
C20.047 (4)0.021 (3)0.061 (4)0.002 (3)0.019 (3)0.005 (3)
C30.027 (3)0.016 (3)0.062 (4)0.008 (2)0.011 (3)0.005 (3)
O30.031 (2)0.026 (2)0.054 (3)0.0013 (18)0.0065 (19)0.003 (2)
C40.030 (3)0.024 (3)0.087 (5)0.004 (3)0.005 (3)0.006 (4)
C50.027 (3)0.040 (4)0.099 (6)0.006 (3)0.016 (4)0.003 (4)
O510.067 (3)0.043 (3)0.120 (4)0.013 (3)0.039 (3)0.008 (3)
O520.067 (3)0.036 (3)0.072 (3)0.000 (2)0.021 (3)0.008 (3)
C60.045 (4)0.026 (3)0.054 (4)0.003 (3)0.004 (3)0.002 (3)
O610.043 (2)0.028 (2)0.077 (3)0.004 (2)0.009 (2)0.005 (2)
O620.047 (2)0.029 (2)0.050 (3)0.0028 (18)0.007 (2)0.003 (2)
O1W0.42 (2)0.199 (12)0.311 (16)0.052 (13)0.035 (14)0.013 (12)
Geometric parameters (Å, º) top
S1—O11.428 (4)N32—H320.8800
S1—O21.443 (4)C33—O331.216 (7)
S1—N111.630 (5)C33—C341.447 (8)
S1—C211.734 (6)C34—N371.359 (7)
N11—C161.470 (7)C34—C351.385 (8)
N11—C121.485 (6)C35—N361.361 (7)
C12—C131.506 (7)C35—C391.417 (8)
C12—H12A0.9900N37—N381.352 (6)
C12—H12B0.9900N37—C371.450 (7)
C13—N141.507 (7)C37—H37A0.9800
C13—H13A0.9900C37—H37B0.9800
C13—H13B0.9900C37—H37C0.9800
N14—C171.486 (7)N38—C391.328 (8)
N14—C151.504 (7)C39—C401.493 (8)
N14—H140.9300C40—C411.519 (8)
C15—C161.484 (8)C40—H40A0.9900
C15—H15A0.9900C40—H40B0.9900
C15—H15B0.9900C41—C421.497 (9)
C16—H16A0.9900C41—H41A0.9900
C16—H16B0.9900C41—H41B0.9900
C17—H17A0.9800C42—H42A0.9800
C17—H17B0.9800C42—H42B0.9800
C17—H17C0.9800C42—H42C0.9800
C21—C221.373 (7)C1—O111.204 (7)
C21—C261.417 (8)C1—O121.293 (7)
C22—C231.398 (8)C1—C21.506 (9)
C22—H220.9500O12—H120.8400
C23—C241.413 (8)C2—C31.505 (8)
C23—C311.481 (8)C2—H2A0.9900
C24—O271.350 (6)C2—H2B0.9900
C24—C251.385 (8)C3—O31.423 (6)
C25—C261.370 (8)C3—C61.540 (8)
C25—H250.9500C3—C41.546 (7)
C26—H260.9500O3—H30.8400
O27—C281.446 (6)C4—C51.506 (9)
C28—C291.472 (8)C4—H4A0.9900
C28—H28A0.9900C4—H4B0.9900
C28—H28B0.9900C5—O511.224 (8)
C29—H29A0.9800C5—O521.318 (8)
C29—H29B0.9800O52—H520.8400
C29—H29C0.9800C6—O611.258 (7)
C31—N361.295 (7)C6—O621.259 (7)
C31—N321.383 (7)O1W—H1WA0.8401
N32—C331.367 (7)O1W—H1WB0.8401
O1—S1—O2119.9 (3)N36—C31—C23120.0 (5)
O1—S1—N11106.8 (3)N32—C31—C23118.0 (5)
O2—S1—N11106.9 (2)C33—N32—C31127.6 (5)
O1—S1—C21107.9 (3)C33—N32—H32116.2
O2—S1—C21108.8 (3)C31—N32—H32116.2
N11—S1—C21105.7 (2)O33—C33—N32122.8 (6)
C16—N11—C12111.0 (4)O33—C33—C34127.6 (6)
C16—N11—S1116.5 (4)N32—C33—C34109.6 (5)
C12—N11—S1115.3 (4)N37—C34—C35107.7 (5)
N11—C12—C13108.6 (4)N37—C34—C33131.8 (6)
N11—C12—H12A110.0C35—C34—C33120.4 (5)
C13—C12—H12A110.0N36—C35—C34125.0 (5)
N11—C12—H12B110.0N36—C35—C39130.1 (6)
C13—C12—H12B110.0C34—C35—C39104.9 (5)
H12A—C12—H12B108.4C31—N36—C35115.2 (5)
C12—C13—N14111.7 (5)N38—N37—C34110.2 (5)
C12—C13—H13A109.3N38—N37—C37121.7 (5)
N14—C13—H13A109.3C34—N37—C37128.1 (5)
C12—C13—H13B109.3N37—C37—H37A109.5
N14—C13—H13B109.3N37—C37—H37B109.5
H13A—C13—H13B107.9H37A—C37—H37B109.5
C17—N14—C15112.8 (5)N37—C37—H37C109.5
C17—N14—C13110.4 (5)H37A—C37—H37C109.5
C15—N14—C13109.6 (4)H37B—C37—H37C109.5
C17—N14—H14108.0C39—N38—N37107.5 (5)
C15—N14—H14108.0N38—C39—C35109.7 (6)
C13—N14—H14108.0N38—C39—C40121.6 (6)
C16—C15—N14111.1 (5)C35—C39—C40128.6 (6)
C16—C15—H15A109.4C39—C40—C41113.2 (5)
N14—C15—H15A109.4C39—C40—H40A108.9
C16—C15—H15B109.4C41—C40—H40A108.9
N14—C15—H15B109.4C39—C40—H40B108.9
H15A—C15—H15B108.0C41—C40—H40B108.9
N11—C16—C15109.0 (5)H40A—C40—H40B107.7
N11—C16—H16A109.9C42—C41—C40113.2 (6)
C15—C16—H16A109.9C42—C41—H41A108.9
N11—C16—H16B109.9C40—C41—H41A108.9
C15—C16—H16B109.9C42—C41—H41B108.9
H16A—C16—H16B108.3C40—C41—H41B108.9
N14—C17—H17A109.5H41A—C41—H41B107.7
N14—C17—H17B109.5C41—C42—H42A109.5
H17A—C17—H17B109.5C41—C42—H42B109.5
N14—C17—H17C109.5H42A—C42—H42B109.5
H17A—C17—H17C109.5C41—C42—H42C109.5
H17B—C17—H17C109.5H42A—C42—H42C109.5
C22—C21—C26118.5 (5)H42B—C42—H42C109.5
C22—C21—S1120.9 (5)O11—C1—O12120.6 (7)
C26—C21—S1120.5 (5)O11—C1—C2124.1 (6)
C21—C22—C23122.6 (6)O12—C1—C2115.3 (6)
C21—C22—H22118.7C1—O12—H12109.5
C23—C22—H22118.7C3—C2—C1117.3 (5)
C22—C23—C24117.8 (5)C3—C2—H2A108.0
C22—C23—C31116.6 (5)C1—C2—H2A108.0
C24—C23—C31125.6 (5)C3—C2—H2B108.0
O27—C24—C25122.9 (6)C1—C2—H2B108.0
O27—C24—C23117.2 (5)H2A—C2—H2B107.2
C25—C24—C23119.9 (5)O3—C3—C2109.6 (5)
C26—C25—C24121.3 (6)O3—C3—C6107.5 (4)
C26—C25—H25119.4C2—C3—C6110.4 (5)
C24—C25—H25119.4O3—C3—C4109.6 (4)
C25—C26—C21119.9 (6)C2—C3—C4111.1 (5)
C25—C26—H26120.0C6—C3—C4108.5 (5)
C21—C26—H26120.0C3—O3—H3109.5
C24—O27—C28121.3 (5)C5—C4—C3111.0 (5)
O27—C28—C29107.8 (5)C5—C4—H4A109.4
O27—C28—H28A110.1C3—C4—H4A109.4
C29—C28—H28A110.1C5—C4—H4B109.4
O27—C28—H28B110.1C3—C4—H4B109.4
C29—C28—H28B110.1H4A—C4—H4B108.0
H28A—C28—H28B108.5O51—C5—O52119.9 (7)
C28—C29—H29A109.5O51—C5—C4122.0 (7)
C28—C29—H29B109.5O52—C5—C4118.0 (6)
H29A—C29—H29B109.5C5—O52—H52109.5
C28—C29—H29C109.5O61—C6—O62126.3 (6)
H29A—C29—H29C109.5O61—C6—C3115.3 (5)
H29B—C29—H29C109.5O62—C6—C3118.1 (5)
N36—C31—N32122.0 (5)H1WA—O1W—H1WB90.4
O1—S1—N11—C1653.1 (4)C31—N32—C33—C340.9 (8)
O2—S1—N11—C16177.4 (4)O33—C33—C34—N372.0 (11)
C21—S1—N11—C1661.6 (4)N32—C33—C34—N37178.9 (6)
O1—S1—N11—C12174.1 (4)O33—C33—C34—C35176.9 (6)
O2—S1—N11—C1244.7 (5)N32—C33—C34—C354.0 (8)
C21—S1—N11—C1271.1 (5)N37—C34—C35—N36179.7 (5)
C16—N11—C12—C1360.3 (6)C33—C34—C35—N364.3 (9)
S1—N11—C12—C13164.5 (4)N37—C34—C35—C390.4 (6)
N11—C12—C13—N1456.5 (6)C33—C34—C35—C39176.4 (5)
C12—C13—N14—C17179.3 (5)N32—C31—N36—C352.6 (8)
C12—C13—N14—C1554.6 (6)C23—C31—N36—C35178.6 (5)
C17—N14—C15—C16179.2 (5)C34—C35—N36—C310.7 (8)
C13—N14—C15—C1655.8 (6)C39—C35—N36—C31179.9 (6)
C12—N11—C16—C1562.2 (6)C35—C34—N37—N381.2 (7)
S1—N11—C16—C15163.1 (4)C33—C34—N37—N38176.6 (6)
N14—C15—C16—N1159.6 (6)C35—C34—N37—C37179.5 (6)
O1—S1—C21—C2219.7 (5)C33—C34—N37—C375.1 (11)
O2—S1—C21—C22151.2 (4)C34—N37—N38—C391.6 (7)
N11—S1—C21—C2294.3 (5)C37—N37—N38—C39179.9 (5)
O1—S1—C21—C26165.6 (4)N37—N38—C39—C351.4 (7)
O2—S1—C21—C2634.0 (5)N37—N38—C39—C40178.2 (5)
N11—S1—C21—C2680.4 (5)N36—C35—C39—N38178.7 (6)
C26—C21—C22—C230.1 (8)C34—C35—C39—N380.6 (7)
S1—C21—C22—C23174.9 (4)N36—C35—C39—C402.2 (11)
C21—C22—C23—C240.1 (8)C34—C35—C39—C40177.1 (6)
C21—C22—C23—C31179.2 (5)N38—C39—C40—C4178.7 (8)
C22—C23—C24—O27177.6 (5)C35—C39—C40—C4197.5 (7)
C31—C23—C24—O271.6 (8)C39—C40—C41—C42173.4 (6)
C22—C23—C24—C251.0 (8)O11—C1—C2—C3151.0 (7)
C31—C23—C24—C25178.2 (5)O12—C1—C2—C328.9 (8)
O27—C24—C25—C26178.3 (5)C1—C2—C3—O358.5 (6)
C23—C24—C25—C261.9 (9)C1—C2—C3—C659.8 (7)
C24—C25—C26—C211.9 (9)C1—C2—C3—C4179.8 (5)
C22—C21—C26—C251.0 (8)O3—C3—C4—C556.0 (7)
S1—C21—C26—C25175.8 (5)C2—C3—C4—C5177.3 (5)
C25—C24—O27—C287.3 (8)C6—C3—C4—C561.1 (7)
C23—C24—O27—C28176.2 (5)C3—C4—C5—O5180.0 (7)
C24—O27—C28—C29179.8 (5)C3—C4—C5—O5295.9 (6)
C22—C23—C31—N3610.5 (8)O3—C3—C6—O61173.5 (5)
C24—C23—C31—N36168.7 (5)C2—C3—C6—O6153.9 (7)
C22—C23—C31—N32168.3 (5)C4—C3—C6—O6168.0 (7)
C24—C23—C31—N3212.5 (8)O3—C3—C6—O6212.1 (7)
N36—C31—N32—C332.6 (9)C2—C3—C6—O62131.6 (6)
C23—C31—N32—C33178.6 (5)C4—C3—C6—O62106.4 (6)
C31—N32—C33—O33179.9 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N14—H14···O30.931.882.764 (6)159
N14—H14···O620.932.302.911 (6)123
N32—H32···O270.881.942.622 (6)134
O12—H12···N38i0.841.982.771 (7)157
O3—H3···O61ii0.841.772.605 (5)173
O52—H52···O62ii0.841.732.490 (6)149
O1W—H1WA···O1iii0.842.112.946 (13)179
O1W—H1WB···O510.841.842.678 (16)179
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+3/2, y1/2, z; (iii) x+1/2, y, z+1/2.
 

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