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In the crystal structure of the title compound, 2,4-diamino-5-(4-chloro­phen­yl)-6-ethyl­pyrimidin-1-ium 3-carb­oxy-4-hydroxy­benzene­sulfonate monohydrate, C12H14ClN4+·C7H5O6S·H2O, the asymmetric unit contains two crystallographically independent protonated pyrimethamine (PMN) mol­ecules, a pair of sulfosalicylate anions and two water mol­ecules. Both the PMN molecules are protonated at one of the pyrimidine N atoms. The component species inter­act through numerous inter­molecular N—H...O, N—H...N and O—H...O hydrogen bonds and C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805012237/hb6180sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805012237/hb6180Isup2.hkl
Contains datablock I

CCDC reference: 249472

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.036
  • wR factor = 0.106
  • Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.55 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.59 PLAT420_ALERT_2_C D-H Without Acceptor N4A - H4B ... ? PLAT420_ALERT_2_C D-H Without Acceptor N4B - H42B ... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 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 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990); software used to prepare material for publication: PLATON.

2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidin-1-ium 3-carboxy-4-hydroxybenzenesulfonate monohydrate top
Crystal data top
C12H14ClN4+·C7H5O6S·H2OF(000) = 2016
Mr = 484.92Dx = 1.508 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 15.2350 (15) Åθ = 11.3–13.8°
b = 19.3290 (12) ŵ = 0.33 mm1
c = 15.8750 (14) ÅT = 273 K
β = 113.960 (6)°Block, colourless
V = 4272.0 (7) Å30.30 × 0.25 × 0.12 mm
Z = 8
Data collection top
MACH3 single-crystal
diffractometer
4891 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.013
Graphite monochromatorθmax = 25.0°, θmin = 2.1°
ω–2θ scansh = 1816
Absorption correction: ψ scan
(North et al., 1968)
k = 122
Tmin = 0.939, Tmax = 0.959l = 118
8317 measured reflections3 standard reflections every 60 min
7493 independent reflections intensity decay: 3%
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: geom and difmap
wR(F2) = 0.106H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0512P)2 + 1.7056P]
where P = (Fo2 + 2Fc2)/3
7493 reflections(Δ/σ)max = 0.041
583 parametersΔρmax = 0.20 e Å3
3 restraintsΔρmin = 0.30 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

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
Cl1A0.53687 (7)0.02379 (6)0.14346 (6)0.0895 (4)
N1A0.94831 (14)0.05468 (11)0.36215 (13)0.0357 (7)
N2A0.97735 (15)0.09162 (12)0.50795 (14)0.0419 (8)
N3A0.82484 (14)0.10253 (11)0.39525 (14)0.0360 (7)
N4A0.67496 (15)0.11300 (13)0.28176 (16)0.0519 (9)
C2A0.91565 (17)0.08355 (13)0.42101 (16)0.0324 (8)
C4A0.76465 (17)0.09162 (13)0.30674 (17)0.0347 (8)
C5A0.79425 (17)0.05781 (13)0.24250 (16)0.0356 (8)
C6A0.88823 (17)0.03926 (13)0.27276 (17)0.0349 (8)
C7A0.9347 (2)0.00337 (15)0.21735 (19)0.0471 (10)
C8A0.9952 (3)0.0512 (2)0.1886 (2)0.0769 (14)
C9A0.72409 (17)0.03913 (14)0.14738 (17)0.0377 (8)
C10A0.6883 (2)0.08819 (16)0.07809 (19)0.0505 (10)
C11A0.6294 (2)0.06887 (18)0.01108 (19)0.0571 (10)
C12A0.6059 (2)0.00108 (19)0.03023 (19)0.0529 (10)
C13A0.6376 (2)0.04850 (18)0.0374 (2)0.0574 (11)
C14A0.6964 (2)0.02910 (16)0.1261 (2)0.0515 (10)
Cl1B0.35204 (6)0.51266 (5)0.46041 (5)0.0693 (3)
N1B0.03756 (13)0.36502 (11)0.02113 (13)0.0347 (7)
N2B0.06301 (14)0.34015 (12)0.17127 (14)0.0404 (7)
N3B0.09149 (13)0.35764 (10)0.06531 (13)0.0318 (7)
N4B0.24358 (14)0.37516 (12)0.04198 (14)0.0432 (8)
C2B0.00196 (17)0.35413 (12)0.08587 (16)0.0309 (8)
C4B0.15012 (16)0.37408 (12)0.02183 (16)0.0299 (8)
C5B0.11548 (16)0.39086 (13)0.09056 (16)0.0310 (8)
C6B0.01960 (16)0.38418 (13)0.06701 (16)0.0317 (8)
C7B0.03125 (18)0.40001 (14)0.12807 (17)0.0392 (9)
C8B0.0719 (2)0.47196 (16)0.1132 (2)0.0596 (12)
C9B0.18037 (16)0.41929 (13)0.18274 (16)0.0316 (8)
C10B0.20430 (19)0.48856 (14)0.19109 (17)0.0430 (9)
C11B0.2575 (2)0.51767 (15)0.27600 (18)0.0481 (10)
C12B0.28642 (18)0.47656 (15)0.35269 (16)0.0390 (9)
C13B0.26557 (19)0.40744 (15)0.34650 (17)0.0440 (9)
C14B0.21304 (18)0.37849 (14)0.26125 (17)0.0401 (9)
S10.22679 (4)0.20183 (4)0.40074 (4)0.0329 (2)
O1C0.16861 (12)0.27869 (11)0.33613 (12)0.0553 (7)
O2C0.21380 (12)0.25975 (12)0.15943 (12)0.0539 (7)
O3C0.10011 (12)0.22455 (11)0.11594 (12)0.0504 (7)
O4C0.23097 (12)0.18781 (12)0.31353 (12)0.0572 (7)
O5C0.28170 (12)0.26253 (10)0.44603 (12)0.0448 (6)
O6C0.25639 (12)0.14254 (10)0.46282 (12)0.0461 (6)
C15C0.08015 (17)0.25897 (14)0.34718 (17)0.0377 (8)
C16C0.05682 (16)0.24065 (13)0.27368 (16)0.0306 (8)
C17C0.03750 (16)0.22213 (12)0.29075 (16)0.0293 (7)
C18C0.10668 (15)0.22089 (12)0.37966 (15)0.0275 (7)
C19C0.08290 (17)0.23830 (14)0.45299 (16)0.0355 (8)
C20C0.00903 (17)0.25723 (15)0.43694 (17)0.0415 (9)
C21C0.13100 (17)0.24227 (14)0.17841 (16)0.0353 (8)
S1'0.54195 (4)0.30120 (4)0.22338 (4)0.0322 (2)
O1D0.60540 (12)0.31566 (11)0.61474 (11)0.0501 (7)
O2D0.78522 (12)0.29390 (12)0.65774 (12)0.0574 (8)
O3D0.84116 (11)0.28657 (10)0.54965 (11)0.0432 (6)
O4D0.51241 (12)0.22906 (9)0.20020 (11)0.0399 (6)
O5D0.63050 (12)0.31695 (11)0.21477 (12)0.0509 (7)
O6D0.46340 (12)0.34788 (10)0.17242 (11)0.0437 (6)
C15D0.59641 (17)0.31423 (14)0.52697 (16)0.0349 (8)
C16D0.67398 (15)0.30398 (13)0.50242 (15)0.0282 (7)
C17D0.65751 (15)0.30203 (12)0.40912 (15)0.0280 (7)
C18D0.56568 (16)0.31041 (13)0.34170 (15)0.0296 (8)
C19D0.48965 (17)0.32228 (14)0.36715 (17)0.0385 (8)
C20D0.50476 (17)0.32450 (16)0.45830 (17)0.0426 (9)
C21D0.77091 (17)0.29456 (14)0.57648 (16)0.0329 (8)
O1W0.19039 (15)0.09007 (11)0.61402 (16)0.0655 (8)
O2W0.14433 (14)0.02199 (11)0.43180 (16)0.0627 (8)
H1A1.008500.045500.381100.0430*
H2A0.958400.109000.547500.0500*
H2B1.036300.079400.524700.0500*
H4A0.658000.132400.321500.0620*
H4B0.633700.107300.226000.0620*
H7A0.885100.016800.162800.0570*
H7B0.974700.034000.253800.0570*
H8A0.955200.086700.149300.0920*
H8B1.025200.025500.155700.0920*
H8C1.043700.072000.242200.0920*
H10A0.704000.134600.091600.0610*
H11A0.606100.101900.057500.0690*
H13A0.619700.094500.023600.0690*
H14A0.717700.062400.172300.0620*
H1B0.098100.359600.036200.0420*
H10B0.184200.516100.138600.0520*
H11B0.273500.564400.281000.0580*
H13B0.286500.380200.399300.0530*
H14B0.199600.331400.256500.0480*
H21A0.042100.333200.213400.0480*
H22B0.123600.337900.184600.0480*
H41A0.264100.365700.000200.0520*
H42B0.283600.385400.096900.0520*
H71A0.013400.394900.192000.0470*
H72B0.083000.367100.116100.0470*
H81A0.020300.504900.133600.0710*
H82B0.110700.478200.147600.0710*
H83C0.110700.478800.048800.0710*
H1C0.204500.277400.281200.0660*
H3C0.144400.226800.064800.0610*
H17C0.053700.210600.242000.0350*
H19C0.129600.236900.513000.0430*
H20C0.024200.269100.486200.0500*
H1D0.661300.307600.649400.0600*
H3D0.892400.283900.594900.0520*
H17D0.708600.295200.392200.0340*
H19D0.428100.328700.321900.0460*
H20D0.453400.333000.474400.0510*
H11W0.179700.118000.654000.0790*
H12W0.221200.115900.587700.0790*
H21W0.180600.060500.422200.0750*
H22W0.177500.002200.493600.0750*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.0680 (6)0.1414 (10)0.0415 (5)0.0247 (6)0.0041 (4)0.0343 (5)
N1A0.0277 (11)0.0474 (14)0.0297 (11)0.0017 (9)0.0093 (9)0.0038 (10)
N2A0.0334 (12)0.0599 (16)0.0280 (11)0.0001 (10)0.0080 (9)0.0070 (10)
N3A0.0285 (11)0.0478 (14)0.0291 (11)0.0013 (10)0.0091 (9)0.0058 (10)
N4A0.0314 (12)0.0793 (19)0.0394 (13)0.0085 (12)0.0085 (10)0.0121 (13)
C2A0.0329 (13)0.0334 (15)0.0303 (13)0.0036 (11)0.0122 (11)0.0014 (11)
C4A0.0324 (13)0.0358 (15)0.0357 (14)0.0014 (11)0.0136 (12)0.0011 (12)
C5A0.0363 (14)0.0386 (16)0.0293 (13)0.0015 (11)0.0105 (11)0.0025 (11)
C6A0.0375 (14)0.0364 (15)0.0307 (13)0.0027 (11)0.0137 (11)0.0024 (11)
C7A0.0460 (16)0.0564 (19)0.0377 (15)0.0048 (14)0.0157 (13)0.0070 (14)
C8A0.082 (2)0.096 (3)0.072 (2)0.016 (2)0.051 (2)0.023 (2)
C9A0.0317 (13)0.0485 (17)0.0294 (13)0.0016 (12)0.0087 (11)0.0047 (12)
C10A0.0500 (17)0.0499 (19)0.0402 (16)0.0045 (14)0.0067 (13)0.0018 (14)
C11A0.0519 (18)0.072 (2)0.0322 (15)0.0032 (16)0.0015 (13)0.0020 (15)
C12A0.0388 (16)0.081 (2)0.0338 (16)0.0071 (16)0.0095 (13)0.0189 (16)
C13A0.0558 (19)0.058 (2)0.0548 (19)0.0162 (16)0.0189 (16)0.0213 (17)
C14A0.0515 (18)0.054 (2)0.0409 (16)0.0065 (14)0.0105 (14)0.0048 (14)
Cl1B0.0786 (6)0.0828 (6)0.0313 (4)0.0241 (5)0.0067 (4)0.0162 (4)
N1B0.0236 (10)0.0455 (14)0.0316 (11)0.0070 (9)0.0076 (9)0.0067 (10)
N2B0.0292 (11)0.0580 (15)0.0270 (11)0.0022 (10)0.0042 (9)0.0068 (10)
N3B0.0285 (11)0.0355 (12)0.0281 (11)0.0032 (9)0.0080 (9)0.0031 (9)
N4B0.0271 (11)0.0691 (17)0.0315 (12)0.0090 (11)0.0098 (9)0.0126 (11)
C2B0.0317 (13)0.0265 (14)0.0298 (13)0.0024 (10)0.0077 (11)0.0026 (11)
C4B0.0269 (12)0.0311 (14)0.0282 (13)0.0040 (10)0.0077 (10)0.0020 (10)
C5B0.0294 (13)0.0346 (15)0.0262 (12)0.0033 (10)0.0085 (10)0.0007 (11)
C6B0.0301 (13)0.0338 (14)0.0281 (13)0.0064 (11)0.0085 (10)0.0003 (11)
C7B0.0309 (13)0.0524 (18)0.0324 (14)0.0034 (12)0.0108 (11)0.0042 (13)
C8B0.064 (2)0.059 (2)0.058 (2)0.0051 (16)0.0270 (17)0.0078 (16)
C9B0.0250 (12)0.0394 (15)0.0268 (13)0.0023 (11)0.0068 (10)0.0035 (11)
C10B0.0506 (16)0.0429 (17)0.0262 (13)0.0083 (13)0.0059 (12)0.0019 (12)
C11B0.0572 (18)0.0424 (17)0.0364 (16)0.0147 (14)0.0106 (14)0.0062 (13)
C12B0.0337 (14)0.0527 (18)0.0248 (13)0.0074 (12)0.0060 (11)0.0081 (12)
C13B0.0426 (15)0.0511 (19)0.0264 (14)0.0016 (13)0.0019 (12)0.0071 (13)
C14B0.0398 (15)0.0362 (16)0.0368 (15)0.0005 (12)0.0077 (12)0.0006 (12)
S10.0202 (3)0.0503 (4)0.0236 (3)0.0022 (3)0.0041 (2)0.0016 (3)
O1C0.0287 (9)0.1014 (17)0.0341 (10)0.0200 (10)0.0110 (8)0.0019 (11)
O2C0.0273 (10)0.0922 (16)0.0340 (10)0.0172 (10)0.0041 (8)0.0008 (10)
O3C0.0323 (10)0.0843 (15)0.0247 (9)0.0186 (10)0.0013 (8)0.0042 (9)
O4C0.0286 (9)0.1109 (18)0.0294 (10)0.0126 (10)0.0091 (8)0.0081 (11)
O5C0.0327 (9)0.0564 (13)0.0334 (10)0.0142 (9)0.0011 (8)0.0071 (9)
O6C0.0317 (9)0.0473 (12)0.0486 (11)0.0097 (8)0.0054 (8)0.0110 (9)
C15C0.0269 (12)0.0515 (17)0.0342 (14)0.0073 (12)0.0119 (11)0.0020 (12)
C16C0.0235 (12)0.0362 (15)0.0284 (13)0.0017 (10)0.0066 (10)0.0033 (11)
C17C0.0275 (12)0.0344 (14)0.0241 (12)0.0027 (10)0.0086 (10)0.0026 (10)
C18C0.0221 (11)0.0313 (14)0.0253 (12)0.0002 (10)0.0056 (10)0.0016 (10)
C19C0.0302 (13)0.0479 (17)0.0237 (12)0.0019 (12)0.0061 (10)0.0018 (12)
C20C0.0341 (14)0.0625 (19)0.0277 (13)0.0106 (13)0.0124 (11)0.0008 (13)
C21C0.0270 (13)0.0448 (17)0.0294 (13)0.0074 (11)0.0067 (11)0.0019 (12)
S1'0.0244 (3)0.0486 (4)0.0195 (3)0.0013 (3)0.0048 (2)0.0043 (3)
O1D0.0343 (10)0.0926 (16)0.0247 (9)0.0020 (10)0.0133 (8)0.0031 (10)
O2D0.0337 (10)0.1144 (19)0.0190 (9)0.0050 (11)0.0054 (8)0.0034 (10)
O3D0.0249 (9)0.0787 (14)0.0216 (9)0.0068 (9)0.0049 (7)0.0069 (9)
O4D0.0397 (10)0.0484 (12)0.0263 (9)0.0001 (8)0.0079 (8)0.0021 (8)
O5D0.0327 (10)0.0913 (16)0.0295 (10)0.0078 (10)0.0133 (8)0.0069 (10)
O6D0.0378 (10)0.0565 (13)0.0265 (9)0.0066 (9)0.0025 (8)0.0106 (8)
C15D0.0359 (14)0.0454 (16)0.0233 (12)0.0029 (12)0.0120 (11)0.0014 (11)
C16D0.0252 (11)0.0355 (14)0.0209 (11)0.0035 (10)0.0064 (9)0.0026 (10)
C17D0.0242 (11)0.0340 (14)0.0240 (12)0.0020 (10)0.0079 (10)0.0010 (10)
C18D0.0276 (12)0.0361 (15)0.0219 (12)0.0021 (10)0.0067 (10)0.0026 (10)
C19D0.0265 (12)0.0580 (18)0.0267 (13)0.0023 (12)0.0063 (11)0.0005 (12)
C20D0.0263 (13)0.071 (2)0.0318 (14)0.0036 (13)0.0131 (11)0.0011 (13)
C21D0.0298 (12)0.0459 (16)0.0212 (13)0.0005 (11)0.0084 (10)0.0028 (11)
O1W0.0715 (15)0.0596 (14)0.0753 (15)0.0042 (12)0.0401 (13)0.0120 (12)
O2W0.0432 (11)0.0616 (14)0.0790 (16)0.0005 (10)0.0203 (11)0.0096 (12)
Geometric parameters (Å, º) top
Cl1A—C12A1.741 (3)C10A—C11A1.384 (4)
Cl1B—C12B1.738 (3)C11A—C12A1.360 (5)
S1—O5C1.451 (2)C12A—C13A1.372 (5)
S1—O6C1.458 (2)C13A—C14A1.379 (4)
S1—C18C1.760 (3)C7A—H7A0.9703
S1—O4C1.4373 (19)C7A—H7B0.9703
S1'—O4D1.4655 (19)C8A—H8B0.9604
S1'—O5D1.443 (2)C8A—H8A0.9605
S1'—C18D1.772 (2)C8A—H8C0.9597
S1'—O6D1.454 (2)C10A—H10A0.9307
O1C—C15C1.342 (3)C11A—H11A0.9296
O2C—C21C1.220 (3)C13A—H13A0.9297
O3C—C21C1.304 (3)C14A—H14A0.9296
O1C—H1C0.8202C4B—C5B1.429 (4)
O3C—H3C0.8194C5B—C9B1.499 (3)
O1D—C15D1.344 (3)C5B—C6B1.359 (4)
O2D—C21D1.218 (3)C6B—C7B1.498 (4)
O3D—C21D1.312 (3)C7B—C8B1.502 (4)
O1D—H1D0.8196C9B—C14B1.385 (3)
O3D—H3D0.8201C9B—C10B1.380 (4)
O1W—H11W0.8971C10B—C11B1.380 (4)
O1W—H12W0.8964C11B—C12B1.368 (4)
N1A—C6A1.373 (3)C12B—C13B1.368 (4)
N1A—C2A1.345 (3)C13B—C14B1.380 (4)
N2A—C2A1.326 (3)C7B—H72B0.9699
N3A—C2A1.325 (4)C7B—H71A0.9704
N3A—C4A1.347 (3)C8B—H83C0.9598
N4A—C4A1.325 (4)C8B—H82B0.9614
N1A—H1A0.8595C8B—H81A0.9599
N2A—H2A0.8589C10B—H10B0.9296
N2A—H2B0.8597C11B—H11B0.9305
O2W—H21W0.9752C13B—H13B0.9297
O2W—H22W0.9806C14B—H14B0.9293
N4A—H4A0.8589C15C—C20C1.397 (4)
N4A—H4B0.8596C15C—C16C1.396 (4)
N1B—C2B1.359 (3)C16C—C21C1.476 (3)
N1B—C6B1.365 (3)C16C—C17C1.396 (4)
N2B—C2B1.324 (3)C17C—C18C1.377 (3)
N3B—C2B1.327 (3)C18C—C19C1.394 (3)
N3B—C4B1.345 (3)C19C—C20C1.368 (4)
N4B—C4B1.327 (3)C17C—H17C0.9299
N1B—H1B0.8600C19C—H19C0.9295
N2B—H21A0.8602C20C—H20C0.9297
N2B—H22B0.8603C15D—C16D1.401 (4)
N4B—H41A0.8599C15D—C20D1.393 (4)
N4B—H42B0.8598C16D—C21D1.479 (3)
C4A—C5A1.430 (4)C16D—C17D1.399 (3)
C5A—C6A1.360 (4)C17D—C18D1.383 (3)
C5A—C9A1.497 (3)C18D—C19D1.392 (4)
C6A—C7A1.504 (4)C19D—C20D1.370 (4)
C7A—C8A1.501 (5)C17D—H17D0.9302
C9A—C10A1.385 (4)C19D—H19D0.9293
C9A—C14A1.384 (4)C20D—H20D0.9311
O6C—S1—C18C107.77 (11)N1B—C2B—N3B121.6 (2)
O4C—S1—O6C112.35 (13)N3B—C4B—C5B122.8 (2)
O4C—S1—C18C107.79 (11)N3B—C4B—N4B116.8 (2)
O4C—S1—O5C112.81 (12)N4B—C4B—C5B120.4 (2)
O5C—S1—C18C105.70 (12)C6B—C5B—C9B120.8 (2)
O5C—S1—O6C110.05 (11)C4B—C5B—C9B121.8 (2)
O5D—S1'—O6D113.98 (12)C4B—C5B—C6B117.2 (2)
O4D—S1'—C18D105.75 (11)N1B—C6B—C5B118.3 (2)
O4D—S1'—O6D110.56 (11)C5B—C6B—C7B125.7 (2)
O5D—S1'—C18D106.45 (12)N1B—C6B—C7B115.9 (2)
O4D—S1'—O5D112.37 (12)C6B—C7B—C8B112.1 (2)
O6D—S1'—C18D107.16 (11)C10B—C9B—C14B118.8 (2)
C15C—O1C—H1C109.32C5B—C9B—C14B121.6 (2)
C21C—O3C—H3C109.46C5B—C9B—C10B119.6 (2)
C15D—O1D—H1D109.44C9B—C10B—C11B121.1 (2)
C21D—O3D—H3D109.57C10B—C11B—C12B118.8 (3)
H11W—O1W—H12W105.93Cl1B—C12B—C11B119.4 (2)
C2A—N1A—C6A121.9 (2)C11B—C12B—C13B121.5 (2)
C2A—N3A—C4A117.5 (2)Cl1B—C12B—C13B119.13 (19)
C2A—N1A—H1A119.04C12B—C13B—C14B119.5 (2)
C6A—N1A—H1A119.05C9B—C14B—C13B120.3 (2)
C2A—N2A—H2A120.01H71A—C7B—H72B107.88
C2A—N2A—H2B119.96C6B—C7B—H72B109.40
H2A—N2A—H2B120.03C8B—C7B—H72B109.03
H21W—O2W—H22W111.08C8B—C7B—H71A109.14
H4A—N4A—H4B120.00C6B—C7B—H71A109.20
C4A—N4A—H4B120.15H81A—C8B—H83C109.49
C4A—N4A—H4A119.85H82B—C8B—H83C109.45
C2B—N1B—C6B122.2 (2)C7B—C8B—H81A109.41
C2B—N3B—C4B117.6 (2)C7B—C8B—H83C109.35
C6B—N1B—H1B118.93C7B—C8B—H82B109.66
C2B—N1B—H1B118.88H81A—C8B—H82B109.47
H21A—N2B—H22B120.00C9B—C10B—H10B119.44
C2B—N2B—H22B119.98C11B—C10B—H10B119.42
C2B—N2B—H21A120.01C12B—C11B—H11B120.62
H41A—N4B—H42B120.06C10B—C11B—H11B120.59
C4B—N4B—H41A120.09C12B—C13B—H13B120.26
C4B—N4B—H42B119.85C14B—C13B—H13B120.29
N1A—C2A—N2A117.8 (2)C13B—C14B—H14B119.84
N2A—C2A—N3A119.9 (2)C9B—C14B—H14B119.85
N1A—C2A—N3A122.3 (2)C16C—C15C—C20C119.4 (3)
N3A—C4A—C5A122.5 (2)O1C—C15C—C20C117.5 (2)
N3A—C4A—N4A116.5 (2)O1C—C15C—C16C123.1 (2)
N4A—C4A—C5A121.0 (2)C15C—C16C—C21C120.1 (2)
C4A—C5A—C9A121.8 (2)C15C—C16C—C17C119.6 (2)
C4A—C5A—C6A117.4 (2)C17C—C16C—C21C120.2 (2)
C6A—C5A—C9A120.7 (2)C16C—C17C—C18C120.2 (2)
C5A—C6A—C7A126.4 (2)C17C—C18C—C19C120.1 (2)
N1A—C6A—C7A115.5 (2)S1—C18C—C19C119.64 (18)
N1A—C6A—C5A118.2 (2)S1—C18C—C17C120.16 (19)
C6A—C7A—C8A112.7 (3)C18C—C19C—C20C120.2 (2)
C10A—C9A—C14A118.4 (2)C15C—C20C—C19C120.5 (2)
C5A—C9A—C10A121.7 (2)O2C—C21C—O3C122.8 (2)
C5A—C9A—C14A119.9 (2)O3C—C21C—C16C114.3 (2)
C9A—C10A—C11A120.7 (3)O2C—C21C—C16C122.9 (2)
C10A—C11A—C12A119.4 (3)C16C—C17C—H17C119.99
Cl1A—C12A—C13A119.2 (3)C18C—C17C—H17C119.85
Cl1A—C12A—C11A119.4 (2)C18C—C19C—H19C119.91
C11A—C12A—C13A121.4 (3)C20C—C19C—H19C119.90
C12A—C13A—C14A119.0 (3)C19C—C20C—H20C119.66
C9A—C14A—C13A121.0 (3)C15C—C20C—H20C119.82
C6A—C7A—H7B108.99C16D—C15D—C20D119.5 (2)
H7A—C7A—H7B107.82O1D—C15D—C20D117.1 (2)
C6A—C7A—H7A109.05O1D—C15D—C16D123.3 (2)
C8A—C7A—H7A109.14C15D—C16D—C21D118.6 (2)
C8A—C7A—H7B108.98C17D—C16D—C21D122.0 (2)
H8A—C8A—H8B109.44C15D—C16D—C17D119.3 (2)
C7A—C8A—H8C109.58C16D—C17D—C18D120.4 (2)
H8B—C8A—H8C109.50S1'—C18D—C17D121.03 (19)
C7A—C8A—H8B109.47S1'—C18D—C19D119.25 (18)
C7A—C8A—H8A109.36C17D—C18D—C19D119.6 (2)
H8A—C8A—H8C109.49C18D—C19D—C20D120.6 (2)
C9A—C10A—H10A119.69C15D—C20D—C19D120.5 (3)
C11A—C10A—H10A119.66O2D—C21D—O3D121.6 (2)
C12A—C11A—H11A120.23O2D—C21D—C16D122.3 (2)
C10A—C11A—H11A120.37O3D—C21D—C16D116.1 (2)
C14A—C13A—H13A120.49C18D—C17D—H17D119.69
C12A—C13A—H13A120.47C16D—C17D—H17D119.89
C9A—C14A—H14A119.54C18D—C19D—H19D119.67
C13A—C14A—H14A119.42C20D—C19D—H19D119.74
N1B—C2B—N2B118.4 (2)C19D—C20D—H20D119.72
N2B—C2B—N3B120.0 (2)C15D—C20D—H20D119.82
O6C—S1—C18C—C17C123.2 (2)N4B—C4B—C5B—C6B175.7 (2)
O4C—S1—C18C—C19C178.3 (2)C9B—C5B—C6B—C7B3.1 (4)
O5C—S1—C18C—C19C57.5 (2)C4B—C5B—C9B—C10B79.7 (3)
O6C—S1—C18C—C19C60.2 (2)C6B—C5B—C9B—C10B96.0 (3)
O4C—S1—C18C—C17C1.7 (2)C4B—C5B—C6B—C7B179.1 (2)
O5C—S1—C18C—C17C119.1 (2)C9B—C5B—C6B—N1B173.1 (2)
O6D—S1'—C18D—C17D148.3 (2)C4B—C5B—C6B—N1B2.8 (4)
O4D—S1'—C18D—C17D93.8 (2)C6B—C5B—C9B—C14B80.4 (3)
O5D—S1'—C18D—C17D26.0 (2)C4B—C5B—C9B—C14B103.8 (3)
O6D—S1'—C18D—C19D35.5 (2)N1B—C6B—C7B—C8B81.4 (3)
O4D—S1'—C18D—C19D82.5 (2)C5B—C6B—C7B—C8B94.9 (3)
O5D—S1'—C18D—C19D157.8 (2)C10B—C9B—C14B—C13B2.3 (4)
C6A—N1A—C2A—N3A3.9 (4)C5B—C9B—C14B—C13B174.1 (3)
C2A—N1A—C6A—C5A3.9 (4)C5B—C9B—C10B—C11B174.8 (3)
C2A—N1A—C6A—C7A176.6 (2)C14B—C9B—C10B—C11B1.8 (4)
C6A—N1A—C2A—N2A174.8 (2)C9B—C10B—C11B—C12B0.1 (5)
C2A—N3A—C4A—C5A3.1 (4)C10B—C11B—C12B—Cl1B179.1 (2)
C2A—N3A—C4A—N4A177.9 (2)C10B—C11B—C12B—C13B1.5 (5)
C4A—N3A—C2A—N2A178.4 (2)C11B—C12B—C13B—C14B0.9 (5)
C4A—N3A—C2A—N1A0.3 (4)Cl1B—C12B—C13B—C14B179.6 (2)
C6B—N1B—C2B—N2B175.6 (2)C12B—C13B—C14B—C9B1.0 (4)
C6B—N1B—C2B—N3B4.0 (4)C16C—C15C—C20C—C19C0.5 (4)
C2B—N1B—C6B—C7B175.0 (2)O1C—C15C—C16C—C21C0.1 (4)
C2B—N1B—C6B—C5B1.6 (4)C20C—C15C—C16C—C21C179.9 (3)
C2B—N3B—C4B—N4B177.9 (2)O1C—C15C—C20C—C19C179.3 (3)
C2B—N3B—C4B—C5B3.1 (3)C20C—C15C—C16C—C17C1.2 (4)
C4B—N3B—C2B—N2B178.0 (2)O1C—C15C—C16C—C17C178.6 (2)
C4B—N3B—C2B—N1B1.6 (3)C21C—C16C—C17C—C18C179.8 (2)
N4A—C4A—C5A—C9A5.8 (4)C15C—C16C—C21C—O2C0.7 (4)
N3A—C4A—C5A—C9A173.2 (2)C17C—C16C—C21C—O3C0.8 (4)
N3A—C4A—C5A—C6A3.0 (4)C15C—C16C—C21C—O3C179.5 (2)
N4A—C4A—C5A—C6A178.1 (2)C17C—C16C—C21C—O2C178.1 (3)
C4A—C5A—C9A—C10A77.2 (4)C15C—C16C—C17C—C18C1.0 (4)
C6A—C5A—C9A—C10A106.8 (3)C16C—C17C—C18C—S1176.77 (19)
C4A—C5A—C9A—C14A105.3 (3)C16C—C17C—C18C—C19C0.2 (4)
C9A—C5A—C6A—C7A3.8 (4)S1—C18C—C19C—C20C176.1 (2)
C4A—C5A—C6A—N1A0.6 (4)C17C—C18C—C19C—C20C0.5 (4)
C6A—C5A—C9A—C14A70.7 (4)C18C—C19C—C20C—C15C0.4 (4)
C4A—C5A—C6A—C7A180.0 (2)C20D—C15D—C16D—C17D2.0 (4)
C9A—C5A—C6A—N1A176.7 (2)C20D—C15D—C16D—C21D178.8 (3)
C5A—C6A—C7A—C8A104.8 (3)O1D—C15D—C20D—C19D178.6 (3)
N1A—C6A—C7A—C8A74.7 (3)O1D—C15D—C16D—C21D0.3 (4)
C5A—C9A—C10A—C11A174.9 (3)C16D—C15D—C20D—C19D2.2 (4)
C5A—C9A—C14A—C13A175.1 (3)O1D—C15D—C16D—C17D178.9 (2)
C10A—C9A—C14A—C13A2.5 (5)C15D—C16D—C17D—C18D0.3 (4)
C14A—C9A—C10A—C11A2.6 (5)C17D—C16D—C21D—O2D177.5 (3)
C9A—C10A—C11A—C12A0.7 (5)C17D—C16D—C21D—O3D2.2 (4)
C10A—C11A—C12A—C13A1.5 (5)C15D—C16D—C21D—O2D1.6 (4)
C10A—C11A—C12A—Cl1A176.8 (3)C21D—C16D—C17D—C18D179.4 (2)
Cl1A—C12A—C13A—C14A176.6 (3)C15D—C16D—C21D—O3D178.7 (2)
C11A—C12A—C13A—C14A1.6 (5)C16D—C17D—C18D—C19D1.3 (4)
C12A—C13A—C14A—C9A0.4 (5)C16D—C17D—C18D—S1'174.89 (19)
N3B—C4B—C5B—C6B5.3 (4)S1'—C18D—C19D—C20D175.1 (2)
N3B—C4B—C5B—C9B170.6 (2)C17D—C18D—C19D—C20D1.2 (4)
N4B—C4B—C5B—C9B8.4 (4)C18D—C19D—C20D—C15D0.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O2Wi0.861.952.803 (3)176
N1B—H1B···O6Cii0.862.213.048 (3)164
O1C—H1C···O2C0.821.912.628 (3)146
O1C—H1C···O5Diii0.822.422.973 (3)125
O1D—H1D···O2D0.821.862.575 (3)145
O1D—H1D···O4Civ0.822.382.953 (2)127
N2A—H2A···O6Div0.862.122.946 (3)160
N2A—H2B···O1Wi0.862.202.989 (3)152
O3C—H3C···O5Cii0.821.772.576 (3)166
O3D—H3D···O4Div0.821.932.747 (2)176
N4A—H4A···N3Biv0.862.403.216 (3)158
O1W—H11W···O5Dv0.901.912.794 (3)167
O1W—H12W···O6C0.902.313.124 (3)151
N2B—H21A···O4Dii0.862.223.029 (3)156
O2W—H21W···O6C0.981.912.811 (3)152
N2B—H22B···O2Dvi0.862.472.901 (3)112
N2B—H22B···O4Cii0.862.263.096 (3)164
O2W—H22W···O1W0.982.502.991 (3)110
N4B—H41A···N3Aii0.862.293.080 (3)152
C7A—H7B···O6Dvii0.972.563.507 (3)164
C13B—H13B···O5C0.932.403.176 (3)141
C17C—H17C···O4C0.932.512.897 (3)105
C17C—H17C···O1Dii0.932.503.429 (3)177
C17D—H17D···O1Ci0.932.403.325 (3)175
C19C—H19C···O2Civ0.932.573.477 (3)166
Symmetry codes: (i) x+1, y, z; (ii) x1/2, y+1/2, z1/2; (iii) x1, y, z; (iv) x+1/2, y+1/2, z+1/2; (v) x1/2, y+1/2, z+1/2; (vi) x1, y, z1; (vii) x+3/2, y1/2, z+1/2.
 

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