Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
Trimethoprim sulfate trihydrate, 2C14H19N4O3+·SO42−·3H2O [(TMPH+)2(SO4)2−·3H2O, TMPH+ = 2,4-di­amino-5-(3,4,5-methoxy­benzyl)­pyrimidin-1-ium], is an antibacterial agent. In its N1-protonated form, it inhibits the bacterial di­hydro­folate reductase enzyme. The asymmetric unit contains two TMPH cations, a sulfate anion and three water mol­ecules. The TMPH cations are each paired about their respective inversion centres via N—H...N hydrogen bonds. These pairs are further bridged by a network of hydrogen bonds involving the sulfate anion and water mol­ecules. Both the TMPH cations make hydrogen bonds with water mol­ecules through the 2-amino groups, reminiscent of TMP-di­hydro­folate reductase complexes. The pyrimidine plane makes a dihedral angle of 75.89 (8)° with the phenyl ring in one TMPH cation, the corresponding angle in the other moiety being 69.96 (8)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801018657/cv6071sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801018657/cv6071Isup2.hkl
Contains datablock I

CCDC reference: 177210

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.036
  • wR factor = 0.092
  • Data-to-parameter ratio = 9.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: MolEN (Fair, 1990); cell refinement: MolEN; data reduction: MolEN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP (Johnson, 1976); software used to prepare material for publication: PLATON (Spek, 1997).

(I) top
Crystal data top
2C14H19N4O3+·SO4·3H2OF(000) = 1552
Mr = 732.78Dx = 1.438 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
a = 7.229 (1) ÅCell parameters from 35 reflections
b = 23.242 (1) Åθ = 3–70.8°
c = 20.373 (1) ŵ = 0.17 mm1
β = 98.59 (1)°T = 293 K
V = 3384.6 (5) Å3Needle, colourless
Z = 40.3 × 0.2 × 0.2 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.014
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 1.3°
Graphite monochromatorh = 08
ω–2θ scansk = 027
6445 measured reflectionsl = 2423
5951 independent reflections4 standard reflections every 60 min
5134 reflections with I > 2σ(I) intensity decay: none
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: inferred from neighbouring sites
wR(F2) = 0.092See text
S = 1.06 w = 1/[σ2(Fo2) + (0.0402P)2 + 1.9477P]
where P = (Fo2 + 2Fc2)/3
5951 reflections(Δ/σ)max < 0.001
627 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.34 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
O30.2086 (2)0.25126 (6)0.31273 (6)0.0388 (5)
O40.15474 (18)0.16421 (5)0.39394 (6)0.0310 (4)
O50.12160 (19)0.18298 (5)0.52203 (6)0.0317 (4)
N10.1165 (2)0.44433 (7)0.60943 (8)0.0269 (5)
N20.4164 (2)0.48104 (8)0.59187 (9)0.0317 (5)
N30.2813 (2)0.45343 (6)0.50171 (7)0.0243 (4)
N40.1480 (3)0.42782 (7)0.41176 (8)0.0294 (5)
C20.2703 (3)0.45939 (7)0.56726 (8)0.0244 (5)
C40.1318 (2)0.43258 (7)0.47728 (8)0.0231 (5)
C50.0373 (2)0.41617 (7)0.51969 (8)0.0239 (5)
C60.0351 (3)0.42325 (8)0.58539 (9)0.0269 (5)
C70.2069 (3)0.39311 (8)0.49325 (10)0.0280 (6)
C80.1871 (2)0.33190 (8)0.46688 (9)0.0241 (5)
C90.2058 (2)0.32122 (8)0.40121 (9)0.0262 (5)
C100.1928 (2)0.26531 (8)0.37706 (8)0.0267 (5)
C110.1632 (2)0.21970 (7)0.41838 (9)0.0249 (5)
C120.1480 (2)0.23072 (8)0.48494 (9)0.0250 (5)
C130.1592 (2)0.28677 (8)0.50898 (9)0.0248 (5)
C140.2066 (4)0.29777 (11)0.26603 (11)0.0447 (8)
C150.0336 (3)0.14312 (10)0.37733 (13)0.0415 (7)
C160.1226 (3)0.19124 (10)0.59154 (10)0.0324 (6)
O3A0.7323 (2)0.25401 (6)0.27892 (6)0.0419 (5)
O4A0.73218 (18)0.17080 (5)0.18802 (6)0.0320 (4)
O5A0.6587 (2)0.19370 (6)0.05887 (6)0.0350 (4)
N1A0.4728 (2)0.42514 (7)0.07646 (7)0.0262 (5)
N2A0.6395 (3)0.46965 (8)0.14905 (8)0.0328 (5)
N3A0.7644 (2)0.46739 (6)0.03793 (7)0.0247 (4)
N4A0.8883 (2)0.46221 (8)0.07139 (8)0.0326 (5)
C2A0.6277 (2)0.45456 (7)0.08727 (8)0.0237 (5)
C4A0.7473 (2)0.44981 (7)0.02405 (8)0.0230 (5)
C5A0.5838 (2)0.41962 (7)0.03831 (8)0.0223 (5)
C6A0.4510 (3)0.40909 (7)0.01403 (9)0.0248 (5)
C7A0.5570 (3)0.40095 (8)0.10692 (9)0.0251 (5)
C8A0.6161 (2)0.33949 (7)0.12627 (8)0.0226 (5)
C9A0.6548 (3)0.32691 (8)0.19363 (9)0.0281 (6)
C10A0.6911 (3)0.27082 (8)0.21422 (8)0.0281 (5)
C11A0.6890 (2)0.22668 (8)0.16779 (9)0.0258 (5)
C12A0.6538 (2)0.23953 (8)0.10047 (8)0.0240 (5)
C13A0.6173 (2)0.29617 (8)0.07973 (8)0.0234 (5)
C14A0.7351 (4)0.29752 (12)0.32819 (10)0.0469 (8)
C15A0.5799 (4)0.14029 (11)0.20911 (14)0.0456 (8)
C16A0.6522 (3)0.20627 (9)0.00964 (9)0.0317 (6)
S10.06550 (6)0.46246 (2)0.25336 (2)0.0243 (1)
O60.1140 (2)0.52387 (6)0.26534 (6)0.0347 (4)
O70.0962 (2)0.43137 (6)0.31571 (7)0.0426 (5)
O80.1317 (2)0.45910 (7)0.22252 (8)0.0479 (5)
O90.1836 (2)0.43906 (6)0.20703 (7)0.0447 (5)
O1'0.2813 (2)0.06925 (8)0.29492 (8)0.0446 (5)
O2'0.5571 (3)0.45244 (8)0.29707 (8)0.0487 (6)
O3'0.1171 (2)0.15968 (7)0.22232 (8)0.0468 (5)
H10.114 (3)0.4514 (10)0.6511 (12)0.047 (7)*
H20.147 (3)0.2944 (8)0.5538 (10)0.024 (5)*
H60.021 (3)0.2149 (9)0.5999 (10)0.037 (6)*
H100.142 (3)0.4145 (9)0.6172 (10)0.032 (5)*
H110.242 (3)0.2074 (9)0.6132 (10)0.038 (6)*
H120.312 (3)0.3934 (8)0.5302 (10)0.030 (5)*
H140.236 (3)0.4178 (9)0.4593 (10)0.029 (5)*
H150.225 (3)0.3521 (9)0.3736 (10)0.030 (5)*
H210.252 (4)0.4383 (10)0.3872 (12)0.045 (7)*
H240.025 (3)0.1062 (12)0.3600 (12)0.053 (7)*
H260.108 (3)0.1545 (10)0.6097 (11)0.041 (6)*
H300.052 (3)0.4219 (10)0.3905 (12)0.046 (7)*
H320.096 (4)0.1425 (12)0.4169 (14)0.067 (8)*
H330.101 (3)0.1687 (11)0.3447 (12)0.050 (7)*
H340.087 (4)0.3192 (11)0.2638 (12)0.057 (7)*
H350.317 (4)0.3246 (13)0.2777 (13)0.069 (8)*
H390.219 (4)0.2776 (14)0.2271 (15)0.078 (9)*
H400.502 (3)0.4976 (10)0.5649 (12)0.041 (6)*
H410.405 (3)0.4915 (10)0.6324 (12)0.042 (6)*
H30.623 (3)0.4259 (8)0.1399 (10)0.026 (5)*
H40.424 (3)0.4034 (9)0.1095 (10)0.032 (5)*
H50.654 (3)0.1703 (10)0.0320 (11)0.040 (6)*
H70.336 (3)0.3901 (9)0.0112 (9)0.028 (5)*
H80.551 (3)0.4600 (8)0.1774 (10)0.023 (5)*
H130.651 (3)0.3576 (9)0.2248 (10)0.032 (5)*
H170.758 (3)0.2311 (10)0.0165 (11)0.046 (6)*
H180.627 (3)0.1044 (12)0.2217 (12)0.052 (7)*
H190.535 (3)0.2244 (9)0.0269 (10)0.034 (5)*
H200.542 (4)0.1595 (13)0.2462 (14)0.071 (9)*
H220.989 (3)0.4805 (10)0.0587 (11)0.042 (6)*
H230.726 (4)0.4948 (11)0.1610 (12)0.056 (7)*
H270.885 (3)0.4524 (10)0.1137 (12)0.041 (6)*
H280.617 (4)0.3126 (11)0.3286 (12)0.054 (7)*
H290.776 (3)0.2781 (10)0.3695 (13)0.051 (7)*
H310.590 (3)0.3050 (8)0.0338 (10)0.027 (5)*
H360.474 (4)0.1388 (12)0.1740 (15)0.073 (9)*
H370.391 (3)0.4184 (10)0.1098 (12)0.043 (6)*
H380.830 (4)0.3295 (13)0.3197 (14)0.072 (9)*
H1'0.230 (3)0.1004 (9)0.2760 (9)0.016 (4)*
H2'0.207 (4)0.0376 (14)0.2864 (14)0.075 (9)*
H3'0.467 (4)0.4452 (11)0.2783 (13)0.046 (8)*
H4'0.639 (4)0.4542 (12)0.2687 (15)0.070 (9)*
H5'0.143 (5)0.1885 (16)0.2604 (18)0.103 (12)*
H6'0.030 (7)0.158 (2)0.217 (2)0.169 (19)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0575 (9)0.0392 (8)0.0199 (7)0.0030 (7)0.0063 (6)0.0029 (6)
O40.0333 (7)0.0257 (7)0.0320 (7)0.0040 (5)0.0015 (5)0.0060 (5)
O50.0431 (8)0.0262 (7)0.0266 (7)0.0013 (6)0.0078 (6)0.0039 (5)
N10.0348 (9)0.0278 (8)0.0172 (8)0.0011 (7)0.0009 (6)0.0027 (6)
N20.0359 (9)0.0393 (10)0.0201 (8)0.0059 (8)0.0051 (7)0.0042 (7)
N30.0289 (8)0.0240 (8)0.0195 (7)0.0007 (6)0.0021 (6)0.0018 (6)
N40.0316 (9)0.0370 (9)0.0196 (8)0.0052 (7)0.0036 (7)0.0017 (7)
C20.0319 (9)0.0201 (8)0.0210 (8)0.0030 (7)0.0032 (7)0.0007 (7)
C40.0301 (9)0.0172 (8)0.0218 (9)0.0030 (7)0.0031 (7)0.0009 (7)
C50.0276 (9)0.0177 (8)0.0258 (9)0.0024 (7)0.0017 (7)0.0019 (7)
C60.0314 (10)0.0220 (9)0.0253 (9)0.0004 (7)0.0028 (8)0.0005 (7)
C70.0261 (9)0.0264 (10)0.0307 (10)0.0025 (7)0.0020 (8)0.0017 (8)
C80.0187 (8)0.0271 (9)0.0257 (9)0.0026 (7)0.0003 (7)0.0009 (7)
C90.0257 (9)0.0275 (10)0.0245 (9)0.0012 (7)0.0012 (7)0.0051 (8)
C100.0262 (9)0.0349 (10)0.0182 (8)0.0039 (8)0.0004 (7)0.0003 (7)
C110.0223 (8)0.0242 (9)0.0270 (9)0.0043 (7)0.0003 (7)0.0043 (7)
C120.0226 (9)0.0274 (9)0.0248 (9)0.0034 (7)0.0031 (7)0.0036 (7)
C130.0236 (9)0.0289 (10)0.0221 (9)0.0032 (7)0.0041 (7)0.0024 (7)
C140.0615 (16)0.0503 (14)0.0232 (11)0.0020 (12)0.0089 (10)0.0047 (10)
C150.0429 (12)0.0337 (12)0.0478 (13)0.0099 (10)0.0061 (11)0.0068 (11)
C160.0335 (11)0.0377 (11)0.0276 (10)0.0047 (9)0.0098 (8)0.0055 (9)
O3A0.0645 (10)0.0408 (8)0.0181 (7)0.0053 (7)0.0012 (6)0.0052 (6)
O4A0.0336 (7)0.0297 (7)0.0330 (7)0.0064 (6)0.0058 (6)0.0093 (6)
O5A0.0539 (9)0.0268 (7)0.0240 (7)0.0087 (6)0.0051 (6)0.0016 (5)
N1A0.0273 (8)0.0286 (8)0.0208 (8)0.0032 (6)0.0026 (6)0.0009 (6)
N2A0.0366 (10)0.0387 (10)0.0226 (8)0.0048 (8)0.0029 (7)0.0046 (7)
N3A0.0246 (7)0.0256 (8)0.0239 (8)0.0017 (6)0.0036 (6)0.0006 (6)
N4A0.0297 (9)0.0412 (10)0.0253 (9)0.0093 (7)0.0008 (7)0.0009 (7)
C2A0.0279 (9)0.0200 (8)0.0237 (9)0.0024 (7)0.0051 (7)0.0016 (7)
C4A0.0252 (9)0.0193 (8)0.0243 (9)0.0014 (7)0.0027 (7)0.0012 (7)
C5A0.0259 (9)0.0179 (8)0.0228 (9)0.0003 (7)0.0031 (7)0.0001 (7)
C6A0.0272 (9)0.0215 (9)0.0257 (9)0.0027 (7)0.0035 (7)0.0016 (7)
C7A0.0295 (10)0.0240 (9)0.0221 (9)0.0025 (8)0.0045 (7)0.0010 (7)
C8A0.0190 (8)0.0266 (9)0.0224 (9)0.0019 (7)0.0039 (6)0.0023 (7)
C9A0.0330 (10)0.0300 (10)0.0212 (9)0.0019 (8)0.0034 (7)0.0030 (8)
C10A0.0295 (9)0.0358 (10)0.0183 (9)0.0002 (8)0.0012 (7)0.0043 (7)
C11A0.0232 (9)0.0275 (9)0.0265 (9)0.0024 (7)0.0028 (7)0.0058 (7)
C12A0.0218 (8)0.0274 (9)0.0227 (9)0.0008 (7)0.0034 (7)0.0008 (7)
C13A0.0230 (9)0.0279 (9)0.0190 (9)0.0003 (7)0.0022 (7)0.0025 (7)
C14A0.0536 (14)0.0671 (16)0.0175 (10)0.0191 (13)0.0028 (10)0.0026 (10)
C15A0.0494 (14)0.0316 (12)0.0571 (15)0.0006 (10)0.0121 (12)0.0112 (11)
C16A0.0352 (11)0.0367 (11)0.0226 (9)0.0064 (9)0.0028 (8)0.0045 (8)
S10.0301 (2)0.0267 (2)0.0162 (2)0.0033 (2)0.0037 (2)0.0009 (2)
O60.0503 (8)0.0314 (7)0.0229 (7)0.0094 (6)0.0068 (6)0.0036 (5)
O70.0601 (10)0.0434 (9)0.0257 (7)0.0091 (7)0.0106 (7)0.0121 (6)
O80.0363 (8)0.0499 (9)0.0532 (9)0.0071 (7)0.0074 (7)0.0013 (7)
O90.0654 (10)0.0383 (8)0.0364 (8)0.0052 (7)0.0275 (7)0.0052 (6)
O1'0.0429 (9)0.0411 (9)0.0443 (9)0.0021 (8)0.0111 (7)0.0043 (7)
O2'0.0396 (9)0.0735 (12)0.0321 (8)0.0057 (9)0.0026 (8)0.0048 (8)
O3'0.0428 (9)0.0461 (9)0.0493 (9)0.0063 (7)0.0000 (7)0.0085 (7)
Geometric parameters (Å, º) top
S1—O91.4684 (15)C5—C61.351 (2)
S1—O61.4812 (15)C7—C81.520 (3)
S1—O71.4494 (15)C8—C91.387 (3)
S1—O81.4716 (16)C8—C131.389 (3)
O3—C141.439 (3)C9—C101.388 (3)
O3—C101.372 (2)C10—C111.390 (2)
O4—C111.381 (2)C11—C121.400 (3)
O4—C151.439 (3)C12—C131.390 (3)
O5—C121.372 (2)C6—H100.95 (2)
O5—C161.428 (2)C7—H120.99 (2)
O3A—C14A1.423 (3)C7—H140.95 (2)
O3A—C10A1.364 (2)C9—H150.93 (2)
O4A—C15A1.428 (3)C13—H20.95 (2)
O4A—C11A1.384 (2)C14—H351.01 (3)
O5A—C16A1.420 (2)C14—H340.99 (3)
O5A—C12A1.365 (2)C14—H390.94 (3)
O1'—H2'0.91 (3)C15—H330.97 (2)
O1'—H1'0.88 (2)C15—H320.98 (3)
O2'—H3'0.72 (3)C15—H240.93 (3)
O2'—H4'0.89 (3)C16—H260.94 (2)
N1—C61.357 (3)C16—H60.95 (2)
N1—C21.346 (2)C16—H110.98 (2)
N2—C21.334 (3)C4A—C5A1.441 (2)
N3—C21.333 (2)C5A—C6A1.346 (3)
N3—C41.346 (2)C5A—C7A1.504 (2)
N4—C41.327 (2)C7A—C8A1.526 (2)
N1—H10.86 (2)C8A—C9A1.390 (2)
N2—H400.86 (2)C8A—C13A1.384 (2)
N2—H410.85 (2)C9A—C10A1.383 (3)
O3'—H6'1.05 (5)C10A—C11A1.394 (3)
O3'—H5'1.02 (4)C11A—C12A1.390 (2)
N4—H300.88 (2)C12A—C13A1.396 (3)
N4—H210.87 (3)C6A—H70.95 (2)
N1A—C2A1.358 (2)C7A—H40.97 (2)
N1A—C6A1.357 (2)C7A—H30.96 (2)
N2A—C2A1.322 (2)C9A—H130.96 (2)
N3A—C4A1.350 (2)C13A—H310.95 (2)
N3A—C2A1.334 (2)C14A—H280.92 (3)
N4A—C4A1.326 (2)C14A—H381.04 (3)
N1A—H370.85 (2)C14A—H290.96 (3)
N2A—H230.92 (3)C15A—H360.97 (3)
N2A—H80.83 (2)C15A—H200.95 (3)
N4A—H220.91 (2)C15A—H180.92 (3)
N4A—H270.90 (2)C16A—H50.95 (2)
C4—C51.439 (2)C16A—H170.98 (2)
C5—C71.509 (3)C16A—H190.96 (2)
S1···N1i3.5122 (17)C13···H62.79 (2)
S1···H2'ii2.67 (3)C13A···H11viii2.90 (2)
S1···H1i2.78 (2)C13A···H6xii2.90 (2)
S1···H23iii2.77 (3)C13A···H172.79 (2)
S1···H3'2.90 (3)C13A···H192.73 (2)
S1···H4'iv3.15 (3)C14···H152.52 (2)
S1···H27iv2.96 (2)C14···H5'2.58 (4)
S1···H303.18 (2)C14···H283.07 (3)
O1'···O6v3.121 (2)C14A···H5vi3.08 (2)
O1'···O8v2.781 (2)C14A···H34vii3.07 (3)
O1'···N1Avi2.778 (2)C14A···H132.52 (2)
O1'···O3'2.737 (2)C15···H5'3.05 (4)
O1'···O43.214 (2)C15A···H6'vii2.83 (5)
O1'···C15A3.401 (3)C16···H4vi3.08 (2)
O1'···C2Avi3.247 (2)C16···H22.532 (19)
O1'···N2Avi2.818 (3)C16···H39vi2.84 (3)
O2'···N2i3.038 (3)C16A···H312.524 (19)
O2'···O93.045 (2)C16A···H29viii2.77 (3)
O2'···N4vii2.974 (3)H1···H412.28 (3)
O2'···O8vii2.900 (3)H1···O6i1.80 (2)
O3···O42.6786 (18)H1···S1i2.78 (2)
O3···O3'2.828 (2)H1···O7i2.81 (2)
O3'···C143.368 (3)H1'···H37vi2.48 (3)
O3'···O4Aiv2.778 (2)H1'···H5'2.15 (4)
O3'···O1'2.737 (2)H1'···O3'1.87 (2)
O3'···C6viii3.370 (2)H1'···H6'2.47 (5)
O3'···O32.828 (2)H2···H62.32 (3)
O3A···C15A3.123 (3)H2···C52.993 (19)
O3A···O4A2.6776 (18)H2···H112.40 (3)
O4···O1'3.214 (2)H2···C162.532 (19)
O4···N1Avi3.090 (2)H2'···H37vi2.54 (4)
O4···O52.6915 (18)H2'···H8vi2.49 (4)
O4···C6Avi3.131 (2)H2'···O8v1.90 (3)
O4···O32.6786 (18)H2'···O6v2.42 (3)
O4A···O3A2.6776 (18)H2'···H4'xiv2.57 (4)
O4A···O3'vii2.778 (2)H2'···S1v2.67 (3)
O4A···O5A2.6591 (18)H3···N4A2.67 (2)
O5···C153.134 (3)H3···H272.13 (3)
O5···O42.6915 (18)H3···O8vii2.38 (2)
O5···C6Avi3.363 (2)H3···H132.33 (3)
O5A···O4A2.6591 (18)H3'···O92.33 (3)
O6···N1i2.654 (2)H3'···H41i2.43 (4)
O6···N2Aiii3.174 (2)H3'···S12.90 (3)
O6···O1'ii3.121 (2)H3'···O72.91 (3)
O7···N42.826 (2)H4···H72.47 (3)
O7···C143.398 (3)H4···C16viii3.08 (2)
O7···C93.131 (2)H4'···H2'ix2.57 (4)
O7···N1i3.260 (2)H4'···S1vii3.15 (3)
O8···C7Aiv3.295 (3)H4'···H132.42 (4)
O8···O2'iv2.900 (3)H4'···O8vii2.03 (3)
O8···O1'ii2.781 (2)H4'···H21vii2.45 (4)
O8···N4Aiv3.105 (2)H5···C14Aviii3.08 (2)
O9···O2'3.045 (2)H5···C4xii2.84 (2)
O9···N2Aiii2.826 (2)H5'···O31.83 (4)
O1'···H8vi2.06 (2)H5'···H392.27 (5)
O1'···H242.88 (2)H5'···C142.58 (4)
O1'···H37vi2.00 (2)H5'···C153.05 (4)
O2'···H21vii2.15 (3)H5'···C102.95 (4)
O2'···H41i2.33 (2)H5'···O42.77 (4)
O2'···H132.79 (2)H5'···H1'2.15 (4)
O3···H5'1.83 (4)H6···C12Axiii2.86 (2)
O3'···H392.84 (3)H6···H22.32 (3)
O3'···H1'1.87 (2)H6···C13Axiii2.90 (2)
O3'···H10viii2.78 (2)H6···C132.79 (2)
O3A···H33vii2.59 (2)H6'···C11Aiv2.66 (5)
O3A···H202.62 (3)H6'···O4Aiv1.76 (5)
O4···H5'2.77 (4)H6'···H1'2.47 (5)
O4···H7vi2.51 (2)H6'···C15Aiv2.83 (5)
O4···H37vi2.58 (2)H7···O5viii2.46 (2)
O4A···H6'vii1.76 (5)H7···H42.47 (3)
O5···H322.63 (3)H7···O4viii2.51 (2)
O5···H7vi2.46 (2)H7···C11viii3.10 (2)
O6···H2'ii2.42 (3)H8···H372.16 (3)
O6···H1i1.80 (2)H8···O1'viii2.06 (2)
O6···H41i2.75 (2)H8···H2'viii2.49 (4)
O6···H23iii2.60 (3)H10···O3'vi2.78 (2)
O6···H18ix2.63 (3)H10···H122.35 (3)
O7···H152.31 (2)H11···H22.40 (3)
O7···H342.81 (3)H11···C8Avi2.89 (2)
O7···H1i2.81 (2)H11···C13Avi2.90 (2)
O7···H3'2.91 (3)H11···H39vi2.38 (4)
O7···H302.00 (2)H11···C132.81 (2)
O8···H3iv2.38 (2)H12···H102.35 (3)
O8···H4'iv2.03 (3)H13···H4'2.42 (4)
O8···H2'ii1.90 (3)H13···H282.40 (3)
O8···H27iv2.24 (2)H13···H32.33 (3)
O8···H13iv2.84 (2)H13···O2'2.79 (2)
O9···H3'2.33 (3)H13···O8vii2.84 (2)
O9···H27iv2.67 (2)H13···H382.26 (4)
O9···H23iii1.96 (3)H13···C14A2.52 (2)
N1···O6i2.654 (2)H14···H152.31 (3)
N1···S1i3.5122 (17)H14···H302.33 (3)
N1···O7i3.260 (2)H14···C2i2.92 (2)
N1A···O1'viii2.778 (2)H14···N42.81 (2)
N1A···O4viii3.090 (2)H15···C142.52 (2)
N2···O2'i3.038 (3)H15···H142.31 (3)
N2···N3x3.080 (2)H15···O72.31 (2)
N2A···O1'viii2.818 (3)H15···H352.25 (3)
N2A···O9iii2.826 (2)H15···H342.43 (3)
N2A···O6iii3.174 (2)H17···H312.42 (3)
N3···N2x3.080 (2)H17···C12xii2.95 (2)
N3A···N4Axi3.155 (2)H17···C13A2.79 (2)
N4···O2'iv2.974 (3)H17···H29viii2.36 (3)
N4···O72.826 (2)H17···C13xii2.90 (2)
N4···C83.360 (3)H18···O6xiv2.63 (3)
N4A···N3Axi3.155 (2)H19···C13A2.73 (2)
N4A···O8vii3.105 (2)H19···C12viii3.03 (2)
N3···H40x2.23 (2)H19···C11viii3.04 (2)
N3A···H22xi2.25 (2)H19···H312.25 (3)
N3A···H32xii2.94 (3)H19···C8viii2.82 (2)
N4···H142.81 (2)H19···C9viii2.81 (2)
N4···H38iv2.95 (3)H19···C10viii2.93 (2)
N4A···H32.67 (2)H19···C13viii2.93 (2)
C2A···O1'viii3.247 (2)H20···O3A2.62 (3)
C2A···C15xii3.492 (3)H20···C10A2.91 (3)
C2A···C5Aiii3.513 (2)H21···H4'iv2.45 (4)
C4···C5i3.580 (2)H21···O2'iv2.15 (3)
C4A···C6Aiii3.573 (2)H22···H22xi2.58 (3)
C5···C4i3.580 (2)H22···N3Axi2.25 (2)
C5A···C2Aiii3.513 (2)H23···O9iii1.96 (3)
C6···O3'vi3.370 (2)H23···O6iii2.60 (3)
C6A···C13A3.361 (3)H23···S1iii2.77 (3)
C6A···O5viii3.363 (2)H24···O1'2.88 (2)
C6A···O4viii3.131 (2)H27···O8vii2.24 (2)
C6A···C4Aiii3.573 (2)H27···O9vii2.67 (2)
C7A···O8vii3.295 (3)H27···S1vii2.96 (2)
C8···N43.360 (3)H27···H32.13 (3)
C8···C16Avi3.441 (3)H27···C7A2.64 (2)
C9···C16Avi3.517 (3)H28···C9A2.82 (2)
C9···O73.131 (2)H28···H352.28 (4)
C9···C14Aiv3.547 (3)H28···C143.07 (3)
C10···C14Aiv3.393 (3)H28···H132.40 (3)
C13A···C6A3.361 (3)H29···C10vii3.01 (2)
C14···O73.398 (3)H29···C16Avi2.77 (3)
C14···O3'3.368 (3)H29···H17vi2.36 (3)
C14···C16viii3.525 (3)H30···C83.00 (2)
C14A···C9vii3.547 (3)H30···O72.00 (2)
C14A···C10vii3.393 (3)H30···C72.68 (2)
C14A···C16Avi3.446 (3)H30···H142.33 (3)
C15···C2Axiii3.492 (3)H30···S13.18 (2)
C15···O53.134 (3)H30···C92.98 (2)
C15A···O1'3.401 (3)H31···C5A2.666 (19)
C15A···O3A3.123 (3)H31···C6A2.742 (19)
C16···C14vi3.525 (3)H31···C16A2.524 (19)
C16A···C14Aviii3.446 (3)H31···H172.42 (3)
C16A···C8viii3.441 (3)H31···H192.25 (3)
C16A···C9viii3.517 (3)H32···O52.63 (3)
C2···H14i2.92 (2)H32···C122.92 (3)
C2A···H32xii3.01 (3)H32···C2Axiii3.01 (3)
C4···H5xiii2.84 (2)H32···N3Axiii2.94 (3)
C5···H22.993 (19)H33···O3Aiv2.59 (2)
C5A···H312.666 (19)H33···C103.09 (2)
C6A···H312.742 (19)H34···O72.81 (3)
C7···H302.68 (2)H34···C92.80 (2)
C7A···H272.64 (2)H34···C14Aiv3.07 (3)
C8···H19vi2.82 (2)H34···H152.43 (3)
C8···H303.00 (2)H34···H38iv2.33 (4)
C8A···H11viii2.89 (2)H35···H282.28 (4)
C9···H38iv2.97 (3)H35···H152.25 (3)
C9···H19vi2.81 (2)H35···C92.75 (3)
C9···H342.80 (2)H37···H1'viii2.48 (3)
C9···H352.75 (3)H37···H2'viii2.54 (4)
C9···H302.98 (2)H37···O4viii2.58 (2)
C9A···H382.69 (3)H37···H82.16 (3)
C9A···H282.82 (2)H37···O1'viii2.00 (2)
C10···H333.09 (2)H38···C9A2.69 (3)
C10···H29iv3.01 (2)H38···N4vii2.95 (3)
C10···H38iv3.09 (3)H38···H132.26 (4)
C10···H19vi2.93 (2)H38···H34vii2.33 (4)
C10···H5'2.95 (4)H38···C9vii2.97 (3)
C10A···H202.91 (3)H38···C10vii3.09 (3)
C11···H7vi3.10 (2)H39···O3'2.84 (3)
C11···H19vi3.04 (2)H39···H5'2.27 (5)
C11A···H6'vii2.66 (5)H39···C16viii2.84 (3)
C12···H17xiii2.95 (2)H39···H11viii2.38 (4)
C12···H322.92 (3)H40···N3x2.23 (2)
C12···H19vi3.03 (2)H41···O2'i2.33 (2)
C12A···H6xii2.86 (2)H41···O6i2.75 (2)
C13···H17xiii2.90 (2)H41···H3'i2.43 (4)
C13···H19vi2.93 (2)H41···H12.28 (3)
C13···H112.81 (2)
O6—S1—O7109.54 (8)O3—C14—H34109.3 (15)
O6—S1—O8108.17 (9)O3—C14—H39101 (2)
O6—S1—O9108.47 (8)H34—C14—H35111 (2)
O7—S1—O8111.07 (9)H34—C14—H39114 (2)
O7—S1—O9110.55 (8)H35—C14—H39110 (2)
O8—S1—O9108.97 (9)O4—C15—H32110.3 (17)
C10—O3—C14117.31 (16)O4—C15—H24106.7 (14)
C11—O4—C15113.10 (14)H32—C15—H33109 (2)
C12—O5—C16117.19 (15)O4—C15—H33108.3 (14)
C10A—O3A—C14A117.13 (16)H24—C15—H32111 (2)
C11A—O4A—C15A113.94 (15)H24—C15—H33111 (2)
C12A—O5A—C16A116.72 (15)H6—C16—H26108.5 (19)
H1'—O1'—H2'113 (2)O5—C16—H11111.7 (12)
H3'—O2'—H4'108 (3)O5—C16—H26106.4 (14)
C2—N1—C6119.88 (16)H6—C16—H11110.3 (18)
C2—N3—C4118.48 (16)O5—C16—H6111.4 (12)
C6—N1—H1121.7 (15)H11—C16—H26108.2 (18)
C2—N1—H1118.2 (15)N2A—C2A—N3A120.83 (16)
C2—N2—H40117.8 (16)N1A—C2A—N3A121.77 (15)
H40—N2—H41117 (2)N1A—C2A—N2A117.40 (16)
C2—N2—H41120.3 (15)N4A—C4A—C5A121.58 (15)
H5'—O3'—H6'100 (3)N3A—C4A—C5A121.89 (14)
H21—N4—H30116 (2)N3A—C4A—N4A116.52 (14)
C4—N4—H21119.5 (17)C4A—C5A—C7A123.47 (15)
C4—N4—H30123.3 (16)C6A—C5A—C7A120.54 (16)
C2A—N1A—C6A120.30 (15)C4A—C5A—C6A115.99 (15)
C2A—N3A—C4A118.43 (14)N1A—C6A—C5A121.56 (18)
C2A—N1A—H37117.2 (16)C5A—C7A—C8A116.13 (15)
C6A—N1A—H37122.4 (16)C7A—C8A—C13A122.29 (15)
C2A—N2A—H23124.5 (16)C9A—C8A—C13A120.16 (16)
C2A—N2A—H8116.1 (15)C7A—C8A—C9A117.34 (15)
H8—N2A—H23118 (2)C8A—C9A—C10A119.93 (16)
H22—N4A—H27122 (2)O3A—C10A—C11A115.06 (16)
C4A—N4A—H27121.1 (14)O3A—C10A—C9A124.56 (16)
C4A—N4A—H22117.0 (14)C9A—C10A—C11A120.38 (16)
N2—C2—N3118.93 (18)C10A—C11A—C12A119.57 (17)
N1—C2—N3122.17 (18)O4A—C11A—C12A119.70 (16)
N1—C2—N2118.90 (16)O4A—C11A—C10A120.62 (16)
N3—C4—C5122.04 (15)O5A—C12A—C11A115.29 (16)
N3—C4—N4116.55 (16)O5A—C12A—C13A124.71 (15)
N4—C4—C5121.42 (16)C11A—C12A—C13A120.00 (16)
C6—C5—C7121.82 (16)C8A—C13A—C12A119.94 (15)
C4—C5—C7122.84 (15)N1A—C6A—H7114.2 (11)
C4—C5—C6115.34 (15)C5A—C6A—H7124.3 (11)
N1—C6—C5122.09 (18)C5A—C7A—H3110.9 (12)
C5—C7—C8114.83 (16)C5A—C7A—H4107.4 (12)
C7—C8—C9119.40 (16)C8A—C7A—H3107.1 (12)
C9—C8—C13120.31 (17)H3—C7A—H4108.6 (18)
C7—C8—C13120.23 (16)C8A—C7A—H4106.4 (12)
C8—C9—C10119.89 (17)C8A—C9A—H13118.4 (12)
O3—C10—C11116.06 (16)C10A—C9A—H13121.6 (12)
O3—C10—C9123.42 (16)C12A—C13A—H31120.3 (11)
C9—C10—C11120.52 (16)C8A—C13A—H31119.8 (11)
O4—C11—C12120.96 (15)O3A—C14A—H38109.3 (16)
C10—C11—C12119.24 (16)O3A—C14A—H28111.1 (16)
O4—C11—C10119.77 (15)O3A—C14A—H29104.7 (14)
C11—C12—C13120.25 (16)H28—C14A—H38111 (2)
O5—C12—C13124.72 (16)H29—C14A—H38111 (2)
O5—C12—C11115.02 (15)H28—C14A—H29109 (2)
C8—C13—C12119.77 (17)O4A—C15A—H18105.3 (14)
N1—C6—H10116.6 (13)O4A—C15A—H36110.8 (18)
C5—C6—H10121.3 (13)H18—C15A—H20110 (2)
H12—C7—H14108.9 (17)O4A—C15A—H20109.4 (18)
C8—C7—H12107.3 (11)H20—C15A—H36108 (3)
C5—C7—H14109.1 (13)H18—C15A—H36113 (2)
C8—C7—H14109.2 (13)O5A—C16A—H17110.4 (13)
C5—C7—H12107.4 (12)O5A—C16A—H19110.3 (12)
C10—C9—H15120.9 (13)H5—C16A—H19106.4 (18)
C8—C9—H15119.2 (13)H17—C16A—H19110.5 (18)
C8—C13—H2119.8 (11)H5—C16A—H17112.3 (19)
C12—C13—H2120.4 (11)O5A—C16A—H5106.8 (14)
O3—C14—H35112.2 (16)
C14—O3—C10—C910.8 (2)C13—C8—C9—C101.3 (2)
C14—O3—C10—C11169.46 (17)C8—C9—C10—O3179.60 (15)
C15—O4—C11—C10100.71 (18)C8—C9—C10—C110.7 (2)
C15—O4—C11—C1281.2 (2)C9—C10—C11—C120.5 (2)
C16—O5—C12—C11174.34 (15)C9—C10—C11—O4178.57 (14)
C16—O5—C12—C135.9 (2)O3—C10—C11—C12179.22 (14)
C14A—O3A—C10A—C11A179.66 (19)O3—C10—C11—O41.1 (2)
C14A—O3A—C10A—C9A0.9 (3)O4—C11—C12—C13179.17 (14)
C15A—O4A—C11A—C12A102.13 (19)C10—C11—C12—O5179.11 (14)
C15A—O4A—C11A—C10A81.6 (2)O4—C11—C12—O51.0 (2)
C16A—O5A—C12A—C11A170.57 (15)C10—C11—C12—C131.1 (2)
C16A—O5A—C12A—C13A9.3 (2)O5—C12—C13—C8179.71 (15)
C6—N1—C2—N31.2 (3)C11—C12—C13—C80.5 (2)
C6—N1—C2—N2178.73 (17)N4A—C4A—C5A—C6A179.40 (17)
C2—N1—C6—C50.6 (3)N3A—C4A—C5A—C7A178.07 (16)
C2—N3—C4—C50.6 (2)N3A—C4A—C5A—C6A1.2 (2)
C4—N3—C2—N2178.73 (16)N4A—C4A—C5A—C7A1.3 (3)
C2—N3—C4—N4179.41 (16)C7A—C5A—C6A—N1A179.47 (16)
C4—N3—C2—N11.2 (2)C4A—C5A—C6A—N1A1.2 (2)
C6A—N1A—C2A—N2A179.09 (17)C4A—C5A—C7A—C8A94.5 (2)
C2A—N1A—C6A—C5A2.7 (3)C6A—C5A—C7A—C8A86.3 (2)
C6A—N1A—C2A—N3A1.6 (3)C5A—C7A—C8A—C13A26.8 (2)
C2A—N3A—C4A—N4A178.40 (16)C5A—C7A—C8A—C9A158.37 (17)
C2A—N3A—C4A—C5A2.2 (2)C13A—C8A—C9A—C10A1.2 (3)
C4A—N3A—C2A—N1A0.7 (2)C7A—C8A—C13A—C12A173.37 (15)
C4A—N3A—C2A—N2A178.49 (16)C7A—C8A—C9A—C10A173.67 (19)
N3—C4—C5—C7179.55 (16)C9A—C8A—C13A—C12A1.3 (2)
N3—C4—C5—C60.1 (2)C8A—C9A—C10A—C11A0.1 (3)
N4—C4—C5—C6179.96 (17)C8A—C9A—C10A—O3A179.34 (18)
N4—C4—C5—C70.5 (3)C9A—C10A—C11A—O4A177.54 (18)
C6—C5—C7—C8107.2 (2)O3A—C10A—C11A—C12A178.17 (15)
C4—C5—C6—N10.1 (3)O3A—C10A—C11A—O4A1.9 (3)
C7—C5—C6—N1179.54 (17)C9A—C10A—C11A—C12A1.3 (3)
C4—C5—C7—C873.3 (2)O4A—C11A—C12A—O5A2.3 (2)
C5—C7—C8—C9120.65 (17)O4A—C11A—C12A—C13A177.52 (14)
C5—C7—C8—C1362.3 (2)C10A—C11A—C12A—O5A178.62 (16)
C9—C8—C13—C120.7 (2)C10A—C11A—C12A—C13A1.2 (2)
C7—C8—C13—C12177.69 (15)O5A—C12A—C13A—C8A179.87 (15)
C7—C8—C9—C10178.34 (15)C11A—C12A—C13A—C8A0.0 (2)
Symmetry codes: (i) x, y+1, z+1; (ii) x, y+1/2, z+1/2; (iii) x+1, y+1, z; (iv) x1, y, z; (v) x, y1/2, z+1/2; (vi) x, y+1/2, z+1/2; (vii) x+1, y, z; (viii) x, y+1/2, z1/2; (ix) x+1, y+1/2, z+1/2; (x) x1, y+1, z+1; (xi) x+2, y+1, z; (xii) x+1, y+1/2, z1/2; (xiii) x1, y+1/2, z+1/2; (xiv) x+1, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O6i0.86 (2)1.80 (2)2.654 (2)172 (2)
O1—H1···O30.88 (2)1.87 (2)2.737 (2)170.3 (18)
O1—H2···O6v0.91 (3)2.42 (3)3.121 (2)133 (3)
O1—H2···O8v0.91 (3)1.90 (3)2.781 (2)160 (3)
O2—H3···O90.72 (3)2.33 (3)3.045 (2)169 (3)
O2—H4···O8vii0.89 (3)2.03 (3)2.900 (3)167 (3)
O3—H5···O31.02 (4)1.83 (4)2.828 (2)166 (3)
O3—H6···O4Aiv1.05 (5)1.76 (5)2.778 (2)162 (4)
N2A—H8···O1viii0.83 (2)2.06 (2)2.818 (3)152 (2)
N4—H21···O2iv0.87 (3)2.15 (3)2.974 (3)157 (2)
N4A—H22···N3Axi0.91 (2)2.25 (2)3.155 (2)173.1 (18)
N2A—H23···O9iii0.92 (3)1.96 (3)2.826 (2)156 (2)
N4A—H27···O8vii0.90 (2)2.24 (2)3.105 (2)161 (2)
N4—H30···O70.88 (2)2.00 (2)2.826 (2)155 (2)
N1A—H37···O1viii0.85 (2)2.00 (2)2.778 (2)152 (2)
N1A—H37···O4viii0.85 (2)2.58 (2)3.090 (2)120.1 (19)
N2—H40···N3x0.86 (2)2.23 (2)3.080 (2)176 (2)
N2—H41···O2i0.85 (2)2.33 (2)3.038 (3)140 (2)
C7A—H3···O8vii0.96 (2)2.38 (2)3.295 (3)158.5 (17)
C6A—H7···O4viii0.95 (2)2.51 (2)3.131 (2)123.2 (14)
C6A—H7···O5viii0.95 (2)2.46 (2)3.363 (2)158.3 (17)
C9—H15···O70.93 (2)2.31 (2)3.131 (2)146.7 (18)
C15—H33···O3Aiv0.97 (2)2.59 (2)3.537 (3)167 (2)
Symmetry codes: (i) x, y+1, z+1; (iii) x+1, y+1, z; (iv) x1, y, z; (v) x, y1/2, z+1/2; (vii) x+1, y, z; (viii) x, y+1/2, z1/2; (x) x1, y+1, z+1; (xi) x+2, y+1, z.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds