Download citation
Download citation
link to html
Nine salts of the anti­folate drugs trimethoprim and pyrimethamine, namely, trimethoprimium [or 2,4-di­amino-5-(3,4,5-tri­meth­oxybenz­yl)pyrimidin-1-ium] 2,5-di­chloro­thio­phene-3-carboxyl­ate monohydrate (TMPDCTPC, 1:1), C14H19N4O3+·C5HCl2O2S, (I), trimethoprimium 3-bromo­thio­phene-2-car­box­yl­ate mono­hydrate, (TMPBTPC, 1:1:1), C14H19N4O3+·C5H2BrO2S·H2O, (II), tri­metho­primium 3-chloro­thio­phene-2-carboxyl­ate monohydrate (TMPCTPC, 1:1:1), C14H19N4O3+·C5H2ClO2S·H2O, (III), trimethoprimium 5-methyl­thio­phene-2-carboxyl­ate monohydrate (TMPMTPC, 1:1:1), C14H19N4O3+·C6H5O2S·H2O, (IV), trimethoprimium anthracene-9-carboxyl­ate sesquihydrate (TMPAC, 2:2:3), C14H19N4O3+·C15H9O2·1.5H2O, (V), pyrimethaminium [or 2,4-di­amino-5-(4-chloro­phen­yl)-6-ethyl­pyrimidin-1-ium] 2,5-di­chloro­thio­phene-3-carboxyl­ate (PMNDCTPC, 1:1), C12H14ClN4+·C5HCl2O2S, (VI), py­ri­methaminium 5-bromo­thio­phene-2-carboxyl­ate (PMNBTPC, 1:1), C12H14ClN4+·C5H2BrO2S, (VII), pyrimethaminium anthracene-9-carboxyl­ate ethanol monosolvate monohydrate (PMNAC, 1:1:1:1), C12H14ClN4+·C15H9O2·C2H5OH·H2O, (VIII), and bis­(pyrimethaminium) naphthalene-1,5-di­sulfonate (PMNNSA, 2:1), 2C12H14ClN4+·C10H6O6S22−, (IX), have been prepared and characterized by single-crystal X-ray diffraction. In all the crystal structures, the pyrimidine N1 atom is protonated. In salts (I)–(III) and (VI)–(IX), the 2-aminopyrimidinium cation inter­acts with the corresponding anion via a pair of N—H...O hydrogen bonds, generating the robust R22(8) supra­molecular heterosynthon. In salt (IV), instead of forming the R22(8) heterosynthon, the carboxyl­ate group bridges two pyrimidinium cations via N—H...O hydrogen bonds. In salt (V), one of the carboxyl­ate O atoms bridges the N1—H group and a 2-amino H atom of the pyrimidinium cation to form a smaller R21(6) ring instead of the R22(8) ring. In salt (IX), the sulfonate O atoms mimic the role of carboxyl­ate O atoms in forming an R22(8) ring motif. In salts (II)–(IX), the pyrimidinium cation forms base pairs via a pair of N—H...N hydrogen bonds, generating a ring motif [R22(8) homosynthon]. Compounds (II) and (III) are isomorphous. The quadruple DDAA (D = hydrogen-bond donor and A = hydrogen-bond acceptor) array is observed in (I). In salts (II)–(IV) and (VI)–(IX), quadruple DADA arrays are present. In salts (VI) and (VII), both DADA and DDAA arrays co-exist. The crystal structures are further stabilized by π–π stacking inter­actions [in (I), (V) and (VII)–(IX)], C—H...π inter­actions [in (IV)–(V) and (VII)–(IX)], C—Br...π inter­actions [in (II)] and C—Cl...π inter­actions [in (I), (III) and (VI)]. Cl...O and Cl...Cl halogen-bond inter­actions are present in (I) and (VI), with distances and angles of 3.0020 (18) and 3.5159 (16) Å, and 165.56 (10) and 154.81 (11)°, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618004072/cu3126sup1.cif
Contains datablocks I, II, III, IV, V, VI, VII, VIII, IX, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618004072/cu3126Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618004072/cu3126IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618004072/cu3126IIIsup4.hkl
Contains datablock III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618004072/cu3126IVsup5.hkl
Contains datablock IV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618004072/cu3126Vsup6.hkl
Contains datablock V

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618004072/cu3126VIsup7.hkl
Contains datablock VI

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618004072/cu3126VIIsup8.hkl
Contains datablock VII

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618004072/cu3126VIIIsup9.hkl
Contains datablock VIII

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618004072/cu3126IXsup10.hkl
Contains datablock IX

CCDC references: 1828709; 1828708; 1828707; 1828706; 1828705; 1828704; 1828703; 1828702; 1828701

Computing details top

For all structures, data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009), Mercury (Macrae et al., 2008) and POV-RAY for Windows (Cason, 2004); software used to prepare material for publication: PLATON (Spek, 2009).

2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidin-1-ium 2,5-dichlorothiophene-3-carboxylate (I) top
Crystal data top
C14H19N4O3+·C5HCl2O2SF(000) = 1008
Mr = 487.35Dx = 1.477 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 7.0030 (3) ÅCell parameters from 3912 reflections
b = 28.2985 (15) Åθ = 3.3–28.2°
c = 11.5070 (6) ŵ = 0.43 mm1
β = 106.080 (5)°T = 293 K
V = 2191.2 (2) Å3Prism, colorless
Z = 40.35 × 0.35 × 0.15 mm
Data collection top
Agilent SuperNova Dual Source
diffractometer with an Atlas detector
5013 independent reflections
Radiation source: SuperNova (Mo) X-ray Source3721 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.030
Detector resolution: 10.4933 pixels mm-1θmax = 27.5°, θmin = 2.8°
ω scansh = 99
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
k = 3436
Tmin = 0.849, Tmax = 1.000l = 1414
13413 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.133 w = 1/[σ2(Fo2) + (0.0502P)2 + 1.4433P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
5013 reflectionsΔρmax = 0.48 e Å3
283 parametersΔρmin = 0.55 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.77270 (12)0.42686 (3)0.43950 (6)0.0599 (2)
Cl10.87433 (10)0.47078 (3)0.64505 (7)0.0599 (2)
Cl20.47824 (19)0.38802 (5)0.32300 (9)0.1047 (4)
O10.2060 (2)0.48057 (7)0.76195 (18)0.0544 (5)
O20.4667 (3)0.47108 (9)0.83233 (17)0.0655 (6)
C170.6950 (4)0.45035 (9)0.5825 (2)0.0421 (5)
C180.4946 (3)0.44966 (9)0.6300 (2)0.0388 (5)
C190.3997 (4)0.42921 (10)0.5475 (3)0.0529 (7)
H190.26280.42590.56330.064*
C200.5310 (5)0.41526 (11)0.4441 (3)0.0606 (8)
C210.3814 (3)0.46845 (9)0.7515 (2)0.0409 (5)
O100.0432 (2)0.75213 (6)0.68018 (16)0.0502 (5)
O110.2681 (3)0.81054 (6)0.71423 (14)0.0421 (4)
O120.6186 (2)0.78919 (7)0.86405 (17)0.0542 (5)
N10.0492 (3)0.54897 (7)0.91313 (17)0.0360 (4)
H10.09670.52530.86750.043*
N20.2930 (3)0.53963 (7)1.0089 (2)0.0444 (5)
H2B0.35350.54831.06100.053*
H2A0.33360.51530.96430.053*
N30.0740 (3)0.60158 (7)1.06647 (18)0.0390 (4)
N40.1497 (3)0.66085 (8)1.1260 (2)0.0554 (6)
H4A0.08610.66941.17670.066*
H4B0.25320.67631.12160.066*
C20.1372 (3)0.56383 (8)0.9975 (2)0.0343 (5)
C40.0878 (3)0.62380 (8)1.0545 (2)0.0367 (5)
C50.1915 (3)0.60932 (8)0.96918 (19)0.0322 (5)
C60.1147 (3)0.57175 (8)0.9010 (2)0.0340 (5)
H60.17560.56100.84380.041*
C70.3745 (3)0.63392 (8)0.9574 (2)0.0355 (5)
H7A0.44130.61340.91370.043*
H7B0.46350.63851.03780.043*
C80.3403 (3)0.68138 (8)0.89392 (19)0.0309 (4)
C90.1579 (3)0.69336 (8)0.8156 (2)0.0343 (5)
H90.05210.67230.80240.041*
C100.1324 (3)0.73671 (8)0.75648 (19)0.0339 (5)
C110.2899 (3)0.76820 (8)0.77539 (19)0.0333 (5)
C120.4738 (3)0.75578 (8)0.8538 (2)0.0364 (5)
C130.4983 (3)0.71272 (8)0.9128 (2)0.0359 (5)
H130.62090.70470.96520.043*
C140.1936 (4)0.71795 (12)0.6364 (3)0.0732 (10)
H14A0.29780.73150.57250.110*
H14B0.24680.70810.70090.110*
H14C0.13830.69120.60600.110*
C150.2321 (5)0.84958 (10)0.7838 (3)0.0545 (7)
H15A0.11100.84430.80560.082*
H15B0.22050.87800.73680.082*
H15C0.34050.85260.85580.082*
C160.8042 (4)0.78110 (12)0.9510 (3)0.0655 (9)
H16A0.86130.75230.93180.098*
H16B0.78420.77861.03000.098*
H16C0.89230.80700.94980.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0698 (5)0.0656 (5)0.0391 (4)0.0036 (4)0.0063 (3)0.0038 (3)
Cl10.0461 (4)0.0705 (5)0.0631 (4)0.0135 (3)0.0152 (3)0.0055 (4)
Cl20.1467 (10)0.1179 (9)0.0704 (6)0.0195 (7)0.0649 (6)0.0407 (6)
O10.0421 (9)0.0632 (13)0.0633 (12)0.0120 (9)0.0238 (9)0.0240 (10)
O20.0560 (11)0.1049 (18)0.0432 (10)0.0314 (11)0.0266 (9)0.0203 (11)
C170.0494 (13)0.0397 (13)0.0376 (12)0.0004 (11)0.0125 (10)0.0002 (10)
C180.0441 (12)0.0374 (13)0.0393 (12)0.0064 (10)0.0189 (10)0.0027 (10)
C190.0557 (15)0.0575 (17)0.0550 (16)0.0102 (13)0.0309 (13)0.0114 (13)
C200.090 (2)0.0573 (18)0.0443 (15)0.0095 (16)0.0344 (15)0.0124 (13)
C210.0418 (12)0.0416 (13)0.0428 (13)0.0061 (10)0.0172 (10)0.0038 (11)
O100.0382 (9)0.0419 (10)0.0576 (11)0.0025 (7)0.0080 (8)0.0113 (8)
O110.0574 (10)0.0323 (9)0.0355 (8)0.0055 (8)0.0109 (7)0.0052 (7)
O120.0411 (9)0.0534 (11)0.0606 (11)0.0197 (8)0.0017 (8)0.0149 (9)
N10.0414 (10)0.0309 (10)0.0395 (10)0.0032 (8)0.0177 (8)0.0046 (8)
N20.0481 (11)0.0377 (11)0.0569 (13)0.0061 (9)0.0302 (10)0.0058 (10)
N30.0488 (11)0.0298 (10)0.0457 (11)0.0015 (8)0.0252 (9)0.0036 (8)
N40.0684 (15)0.0432 (13)0.0661 (15)0.0170 (11)0.0380 (12)0.0222 (11)
C20.0397 (11)0.0278 (11)0.0390 (12)0.0044 (9)0.0167 (9)0.0051 (9)
C40.0450 (12)0.0283 (11)0.0398 (12)0.0017 (9)0.0166 (10)0.0009 (9)
C50.0367 (11)0.0277 (11)0.0344 (11)0.0034 (9)0.0133 (9)0.0050 (9)
C60.0391 (11)0.0317 (12)0.0359 (11)0.0040 (9)0.0182 (9)0.0028 (9)
C70.0350 (11)0.0315 (12)0.0409 (12)0.0027 (9)0.0119 (9)0.0042 (10)
C80.0326 (10)0.0299 (11)0.0317 (11)0.0009 (8)0.0118 (9)0.0017 (9)
C90.0305 (10)0.0314 (11)0.0398 (12)0.0039 (9)0.0081 (9)0.0007 (9)
C100.0315 (10)0.0353 (12)0.0319 (11)0.0006 (9)0.0040 (9)0.0011 (9)
C110.0412 (11)0.0291 (11)0.0296 (10)0.0035 (9)0.0101 (9)0.0035 (9)
C120.0338 (11)0.0384 (13)0.0365 (11)0.0090 (9)0.0090 (9)0.0023 (10)
C130.0297 (10)0.0408 (13)0.0360 (11)0.0022 (9)0.0069 (9)0.0046 (10)
C140.0490 (16)0.0556 (19)0.090 (2)0.0094 (14)0.0229 (16)0.0095 (17)
C150.0746 (18)0.0369 (14)0.0536 (16)0.0044 (13)0.0207 (14)0.0019 (12)
C160.0421 (14)0.077 (2)0.0668 (19)0.0266 (14)0.0026 (13)0.0100 (16)
Geometric parameters (Å, º) top
S1—C201.711 (3)N4—H4A0.8600
S1—C171.717 (3)N4—H4B0.8600
Cl1—C171.712 (3)C4—C51.433 (3)
Cl2—C201.720 (3)C5—C61.342 (3)
O1—C211.249 (3)C5—C71.497 (3)
O2—C211.239 (3)C6—H60.9300
C17—C181.357 (3)C7—C81.516 (3)
C18—C191.424 (3)C7—H7A0.9700
C18—C211.501 (3)C7—H7B0.9700
C19—C201.346 (4)C8—C91.386 (3)
C19—H190.9300C8—C131.388 (3)
O10—C101.369 (3)C9—C101.390 (3)
O10—C141.416 (3)C9—H90.9300
O11—C111.377 (3)C10—C111.388 (3)
O11—C151.427 (3)C11—C121.397 (3)
O12—C121.367 (3)C12—C131.382 (3)
O12—C161.422 (3)C13—H130.9300
N1—C21.353 (3)C14—H14A0.9600
N1—C61.356 (3)C14—H14B0.9600
N1—H10.8600C14—H14C0.9600
N2—C21.325 (3)C15—H15A0.9600
N2—H2B0.8600C15—H15B0.9600
N2—H2A0.8600C15—H15C0.9600
N3—C21.331 (3)C16—H16A0.9600
N3—C41.336 (3)C16—H16B0.9600
N4—C41.329 (3)C16—H16C0.9600
C20—S1—C1789.79 (13)C5—C7—H7A108.4
C18—C17—Cl1129.22 (19)C8—C7—H7A108.4
C18—C17—S1113.47 (18)C5—C7—H7B108.4
Cl1—C17—S1117.31 (15)C8—C7—H7B108.4
C17—C18—C19111.0 (2)H7A—C7—H7B107.5
C17—C18—C21126.2 (2)C9—C8—C13119.8 (2)
C19—C18—C21122.8 (2)C9—C8—C7121.65 (19)
C20—C19—C18112.2 (3)C13—C8—C7118.56 (19)
C20—C19—H19123.9C8—C9—C10120.3 (2)
C18—C19—H19123.9C8—C9—H9119.8
C19—C20—S1113.5 (2)C10—C9—H9119.8
C19—C20—Cl2126.9 (3)O10—C10—C11115.45 (19)
S1—C20—Cl2119.59 (19)O10—C10—C9124.5 (2)
O2—C21—O1125.3 (2)C11—C10—C9120.07 (19)
O2—C21—C18118.7 (2)O11—C11—C10120.51 (19)
O1—C21—C18116.0 (2)O11—C11—C12120.08 (19)
C10—O10—C14117.3 (2)C10—C11—C12119.4 (2)
C11—O11—C15113.52 (18)O12—C12—C13125.4 (2)
C12—O12—C16117.4 (2)O12—C12—C11114.2 (2)
C2—N1—C6119.49 (19)C13—C12—C11120.4 (2)
C2—N1—H1120.3C12—C13—C8120.1 (2)
C6—N1—H1120.3C12—C13—H13119.9
C2—N2—H2B120.0C8—C13—H13119.9
C2—N2—H2A120.0O10—C14—H14A109.5
H2B—N2—H2A120.0O10—C14—H14B109.5
C2—N3—C4117.89 (19)H14A—C14—H14B109.5
C4—N4—H4A120.0O10—C14—H14C109.5
C4—N4—H4B120.0H14A—C14—H14C109.5
H4A—N4—H4B120.0H14B—C14—H14C109.5
N2—C2—N3120.1 (2)O11—C15—H15A109.5
N2—C2—N1117.5 (2)O11—C15—H15B109.5
N3—C2—N1122.3 (2)H15A—C15—H15B109.5
N4—C4—N3116.6 (2)O11—C15—H15C109.5
N4—C4—C5120.6 (2)H15A—C15—H15C109.5
N3—C4—C5122.7 (2)H15B—C15—H15C109.5
C6—C5—C4115.43 (19)O12—C16—H16A109.5
C6—C5—C7122.03 (19)O12—C16—H16B109.5
C4—C5—C7122.5 (2)H16A—C16—H16B109.5
C5—C6—N1122.04 (19)O12—C16—H16C109.5
C5—C6—H6119.0H16A—C16—H16C109.5
N1—C6—H6119.0H16B—C16—H16C109.5
C5—C7—C8115.49 (18)
C20—S1—C17—C180.6 (2)C2—N1—C6—C51.0 (3)
C20—S1—C17—Cl1179.16 (18)C6—C5—C7—C8105.8 (2)
Cl1—C17—C18—C19179.6 (2)C4—C5—C7—C875.0 (3)
S1—C17—C18—C190.1 (3)C5—C7—C8—C922.3 (3)
Cl1—C17—C18—C211.6 (4)C5—C7—C8—C13159.6 (2)
S1—C17—C18—C21178.6 (2)C13—C8—C9—C100.4 (3)
C17—C18—C19—C200.7 (4)C7—C8—C9—C10178.5 (2)
C21—C18—C19—C20179.4 (3)C14—O10—C10—C11165.9 (2)
C18—C19—C20—S11.1 (4)C14—O10—C10—C915.7 (4)
C18—C19—C20—Cl2178.7 (2)C8—C9—C10—O10178.2 (2)
C17—S1—C20—C191.0 (3)C8—C9—C10—C110.2 (3)
C17—S1—C20—Cl2178.8 (2)C15—O11—C11—C1099.2 (3)
C17—C18—C21—O225.0 (4)C15—O11—C11—C1283.2 (3)
C19—C18—C21—O2156.4 (3)O10—C10—C11—O113.7 (3)
C17—C18—C21—O1154.6 (3)C9—C10—C11—O11177.8 (2)
C19—C18—C21—O124.0 (4)O10—C10—C11—C12178.8 (2)
C4—N3—C2—N2177.7 (2)C9—C10—C11—C120.2 (3)
C4—N3—C2—N13.1 (3)C16—O12—C12—C136.4 (4)
C6—N1—C2—N2177.8 (2)C16—O12—C12—C11174.1 (2)
C6—N1—C2—N32.9 (3)O11—C11—C12—O121.5 (3)
C2—N3—C4—N4178.8 (2)C10—C11—C12—O12179.1 (2)
C2—N3—C4—C51.5 (3)O11—C11—C12—C13178.1 (2)
N4—C4—C5—C6179.4 (2)C10—C11—C12—C130.5 (3)
N3—C4—C5—C60.2 (3)O12—C12—C13—C8179.2 (2)
N4—C4—C5—C71.3 (3)C11—C12—C13—C80.3 (3)
N3—C4—C5—C7179.1 (2)C9—C8—C13—C120.1 (3)
C4—C5—C6—N10.4 (3)C7—C8—C13—C12178.3 (2)
C7—C5—C6—N1178.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.861.772.631 (3)174
N2—H2A···O20.861.992.829 (3)166
N2—H2B···O2i0.862.062.822 (3)147
N4—H4A···O11ii0.862.453.214 (3)148
N4—H4A···O12ii0.862.413.143 (3)144
N4—H4B···O10iii0.862.463.215 (3)147
C7—H7A···Cl2iv0.972.813.553 (2)134
Symmetry codes: (i) x1, y+1, z+2; (ii) x1/2, y+3/2, z+1/2; (iii) x+1/2, y+3/2, z+1/2; (iv) x, y+1, z+1.
2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidin-1-ium 3-bromothiophene-2-carboxylate monohydrate (II) top
Crystal data top
C14H19N4O3+·C5H2BrO2S·H2OF(000) = 1056
Mr = 515.38Dx = 1.578 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 16.9440 (8) ÅCell parameters from 4168 reflections
b = 6.8991 (3) Åθ = 3.3–28.5°
c = 19.7206 (14) ŵ = 2.04 mm1
β = 109.773 (7)°T = 293 K
V = 2169.4 (2) Å3Prism, colorless
Z = 40.60 × 0.50 × 0.40 mm
Data collection top
Agilent SuperNova Dual Source
diffractometer with an Atlas detector
4949 independent reflections
Radiation source: SuperNova (Mo) X-ray Source3766 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.030
Detector resolution: 10.4933 pixels mm-1θmax = 27.5°, θmin = 2.9°
ω scansh = 2221
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
k = 88
Tmin = 0.615, Tmax = 1.000l = 1625
12646 measured reflections
Refinement top
Refinement on F22 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.104 w = 1/[σ2(Fo2) + (0.0414P)2 + 1.5827P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
4949 reflectionsΔρmax = 0.95 e Å3
289 parametersΔρmin = 1.02 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.27564 (2)0.64387 (4)0.75131 (2)0.04939 (12)
S10.17543 (5)0.10256 (12)0.63943 (5)0.0501 (2)
O10.39515 (12)0.3500 (3)0.70669 (12)0.0442 (5)
O20.34958 (15)0.0670 (3)0.65662 (15)0.0626 (7)
C170.33875 (17)0.2275 (4)0.68118 (15)0.0365 (6)
C180.25209 (17)0.2707 (4)0.67934 (15)0.0347 (6)
C190.21719 (17)0.4243 (4)0.70302 (15)0.0356 (6)
C200.12997 (18)0.4063 (5)0.68844 (17)0.0467 (7)
H200.09740.49820.70120.056*
C210.09992 (19)0.2402 (5)0.65399 (18)0.0543 (8)
H210.04370.20450.63970.065*
N10.51777 (13)0.3354 (3)0.64391 (12)0.0327 (5)
H10.49210.30690.67350.039*
N20.46864 (15)0.0544 (3)0.58253 (14)0.0429 (6)
H2B0.46450.02540.54800.051*
H2A0.44310.03070.61260.051*
N30.55390 (12)0.2503 (3)0.54287 (11)0.0291 (5)
N40.62901 (13)0.4620 (3)0.49985 (12)0.0353 (5)
H4A0.62310.38360.46450.042*
H4B0.65640.56840.50260.042*
O100.93582 (11)0.4983 (3)0.67678 (11)0.0428 (5)
O110.97913 (11)0.8021 (3)0.61440 (11)0.0408 (5)
O120.86853 (12)1.0730 (3)0.54712 (12)0.0446 (5)
C20.51412 (15)0.2129 (4)0.58939 (14)0.0306 (6)
C40.59590 (14)0.4186 (4)0.55020 (14)0.0273 (5)
C50.60366 (14)0.5517 (4)0.60779 (14)0.0300 (6)
C60.56173 (15)0.5030 (4)0.65217 (14)0.0323 (6)
H60.56290.58650.68950.039*
C70.64434 (15)0.7480 (4)0.61243 (16)0.0343 (6)
H7A0.64340.81030.65630.041*
H7B0.60970.82540.57230.041*
C80.73412 (14)0.7551 (4)0.61201 (14)0.0303 (6)
C90.79241 (15)0.6155 (4)0.64650 (14)0.0321 (6)
H90.77700.51290.67000.039*
C100.87406 (15)0.6289 (4)0.64596 (14)0.0314 (6)
C110.89743 (15)0.7850 (4)0.61214 (14)0.0311 (6)
C120.83893 (16)0.9250 (4)0.57800 (15)0.0329 (6)
C130.75675 (16)0.9090 (4)0.57718 (15)0.0349 (6)
H130.71711.00130.55330.042*
C140.91624 (19)0.3356 (4)0.71257 (17)0.0460 (7)
H14A0.87320.25990.67870.069*
H14B0.89680.37970.75030.069*
H14C0.96550.25750.73280.069*
C150.9935 (2)0.7293 (6)0.5527 (2)0.0655 (10)
H15A0.95750.79480.51060.098*
H15B0.98170.59290.54840.098*
H15C1.05100.75080.55700.098*
C160.8101 (2)1.2158 (5)0.5092 (2)0.0568 (9)
H16A0.76641.15570.47050.085*
H16B0.83821.31080.48990.085*
H16C0.78631.27760.54140.085*
O1W0.38659 (18)0.6976 (3)0.63400 (14)0.0578 (6)
H1W0.385 (3)0.612 (4)0.6622 (19)0.087*
H2W0.360 (2)0.787 (4)0.643 (2)0.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0514 (2)0.03644 (18)0.0718 (2)0.00199 (13)0.03573 (17)0.00563 (15)
S10.0456 (4)0.0508 (5)0.0561 (5)0.0031 (4)0.0203 (4)0.0102 (4)
O10.0376 (11)0.0442 (12)0.0605 (14)0.0036 (9)0.0292 (10)0.0022 (10)
O20.0639 (15)0.0373 (12)0.108 (2)0.0054 (11)0.0578 (14)0.0108 (12)
C170.0388 (15)0.0342 (15)0.0456 (17)0.0097 (13)0.0260 (13)0.0092 (13)
C180.0369 (14)0.0326 (14)0.0403 (16)0.0063 (12)0.0207 (12)0.0054 (12)
C190.0340 (14)0.0376 (15)0.0406 (16)0.0064 (12)0.0195 (12)0.0049 (12)
C200.0367 (15)0.0515 (19)0.056 (2)0.0122 (14)0.0215 (14)0.0008 (16)
C210.0315 (15)0.071 (2)0.060 (2)0.0022 (16)0.0162 (14)0.0005 (19)
N10.0285 (11)0.0417 (13)0.0342 (12)0.0022 (10)0.0189 (9)0.0018 (10)
N20.0461 (14)0.0386 (13)0.0562 (16)0.0105 (11)0.0332 (12)0.0071 (12)
N30.0264 (10)0.0296 (11)0.0347 (12)0.0013 (9)0.0149 (9)0.0020 (9)
N40.0345 (12)0.0374 (13)0.0409 (13)0.0050 (10)0.0217 (10)0.0049 (10)
O100.0242 (9)0.0474 (12)0.0571 (13)0.0074 (8)0.0141 (8)0.0171 (10)
O110.0229 (9)0.0552 (12)0.0475 (12)0.0037 (8)0.0162 (8)0.0006 (10)
O120.0384 (11)0.0377 (11)0.0651 (14)0.0024 (9)0.0272 (10)0.0118 (10)
C20.0241 (12)0.0311 (13)0.0381 (15)0.0021 (10)0.0127 (11)0.0016 (12)
C40.0185 (11)0.0309 (13)0.0339 (14)0.0045 (10)0.0105 (10)0.0004 (11)
C50.0181 (11)0.0341 (14)0.0393 (15)0.0019 (10)0.0117 (10)0.0046 (11)
C60.0237 (12)0.0405 (15)0.0337 (14)0.0015 (11)0.0110 (10)0.0083 (12)
C70.0236 (12)0.0338 (14)0.0480 (17)0.0003 (11)0.0154 (11)0.0086 (12)
C80.0221 (12)0.0317 (14)0.0382 (15)0.0018 (10)0.0117 (11)0.0077 (11)
C90.0267 (12)0.0341 (14)0.0368 (15)0.0025 (11)0.0123 (11)0.0005 (11)
C100.0226 (11)0.0354 (14)0.0344 (15)0.0005 (11)0.0073 (10)0.0023 (12)
C110.0218 (11)0.0385 (14)0.0337 (14)0.0049 (11)0.0102 (10)0.0061 (12)
C120.0327 (13)0.0302 (13)0.0384 (15)0.0042 (11)0.0153 (12)0.0033 (12)
C130.0264 (12)0.0326 (14)0.0458 (17)0.0041 (11)0.0122 (11)0.0010 (12)
C140.0400 (16)0.0497 (18)0.0487 (18)0.0078 (14)0.0156 (14)0.0143 (15)
C150.0463 (19)0.098 (3)0.065 (2)0.010 (2)0.0351 (17)0.002 (2)
C160.061 (2)0.0453 (18)0.077 (2)0.0116 (16)0.0391 (18)0.0174 (17)
O1W0.0942 (19)0.0384 (13)0.0622 (16)0.0077 (13)0.0543 (14)0.0027 (11)
Geometric parameters (Å, º) top
Br1—C191.883 (3)O12—C161.417 (4)
S1—C211.694 (3)C4—C51.432 (4)
S1—C181.720 (3)C5—C61.343 (4)
O1—C171.247 (3)C5—C71.508 (4)
O2—C171.247 (3)C6—H60.9300
C17—C181.487 (4)C7—C81.525 (3)
C18—C191.371 (4)C7—H7A0.9700
C19—C201.412 (4)C7—H7B0.9700
C20—C211.342 (5)C8—C91.383 (4)
C20—H200.9300C8—C131.387 (4)
C21—H210.9300C9—C101.390 (3)
N1—C21.353 (3)C9—H90.9300
N1—C61.355 (3)C10—C111.393 (4)
N1—H10.8600C11—C121.385 (4)
N2—C21.318 (3)C12—C131.391 (4)
N2—H2B0.8600C13—H130.9300
N2—H2A0.8600C14—H14A0.9600
N3—C21.334 (3)C14—H14B0.9600
N3—C41.344 (3)C14—H14C0.9600
N4—C41.329 (3)C15—H15A0.9600
N4—H4A0.8600C15—H15B0.9600
N4—H4B0.8600C15—H15C0.9600
O10—C101.358 (3)C16—H16A0.9600
O10—C141.424 (3)C16—H16B0.9600
O11—C111.375 (3)C16—H16C0.9600
O11—C151.412 (4)O1W—H1W0.816 (10)
O12—C121.368 (3)O1W—H2W0.816 (10)
C21—S1—C1892.37 (15)C5—C7—H7A107.9
O2—C17—O1124.4 (2)C8—C7—H7A107.9
O2—C17—C18116.3 (3)C5—C7—H7B107.9
O1—C17—C18119.3 (2)C8—C7—H7B107.9
C19—C18—C17133.1 (3)H7A—C7—H7B107.2
C19—C18—S1109.3 (2)C9—C8—C13120.4 (2)
C17—C18—S1117.6 (2)C9—C8—C7121.5 (2)
C18—C19—C20113.9 (3)C13—C8—C7118.1 (2)
C18—C19—Br1125.5 (2)C8—C9—C10119.8 (2)
C20—C19—Br1120.6 (2)C8—C9—H9120.1
C21—C20—C19111.7 (3)C10—C9—H9120.1
C21—C20—H20124.1O10—C10—C9124.8 (2)
C19—C20—H20124.1O10—C10—C11115.2 (2)
C20—C21—S1112.7 (2)C9—C10—C11120.0 (2)
C20—C21—H21123.7O11—C11—C12120.2 (2)
S1—C21—H21123.7O11—C11—C10119.8 (2)
C2—N1—C6120.3 (2)C12—C11—C10120.0 (2)
C2—N1—H1119.9O12—C12—C11115.3 (2)
C6—N1—H1119.9O12—C12—C13124.8 (2)
C2—N2—H2B120.0C11—C12—C13120.0 (2)
C2—N2—H2A120.0C8—C13—C12119.9 (2)
H2B—N2—H2A120.0C8—C13—H13120.1
C2—N3—C4117.7 (2)C12—C13—H13120.1
C4—N4—H4A120.0O10—C14—H14A109.5
C4—N4—H4B120.0O10—C14—H14B109.5
H4A—N4—H4B120.0H14A—C14—H14B109.5
C10—O10—C14118.1 (2)O10—C14—H14C109.5
C11—O11—C15114.0 (2)H14A—C14—H14C109.5
C12—O12—C16117.3 (2)H14B—C14—H14C109.5
N2—C2—N3120.2 (2)O11—C15—H15A109.5
N2—C2—N1117.9 (2)O11—C15—H15B109.5
N3—C2—N1121.8 (2)H15A—C15—H15B109.5
N4—C4—N3117.1 (2)O11—C15—H15C109.5
N4—C4—C5120.0 (2)H15A—C15—H15C109.5
N3—C4—C5122.9 (2)H15B—C15—H15C109.5
C6—C5—C4115.4 (2)O12—C16—H16A109.5
C6—C5—C7121.1 (2)O12—C16—H16B109.5
C4—C5—C7122.8 (2)H16A—C16—H16B109.5
C5—C6—N1121.7 (2)O12—C16—H16C109.5
C5—C6—H6119.1H16A—C16—H16C109.5
N1—C6—H6119.1H16B—C16—H16C109.5
C5—C7—C8117.7 (2)H1W—O1W—H2W105 (4)
O2—C17—C18—C19177.3 (3)C6—C5—C7—C8133.3 (3)
O1—C17—C18—C192.4 (5)C4—C5—C7—C856.5 (3)
O2—C17—C18—S13.5 (3)C5—C7—C8—C936.9 (4)
O1—C17—C18—S1176.7 (2)C5—C7—C8—C13144.5 (3)
C21—S1—C18—C190.7 (2)C13—C8—C9—C100.3 (4)
C21—S1—C18—C17178.6 (2)C7—C8—C9—C10178.9 (2)
C17—C18—C19—C20178.7 (3)C14—O10—C10—C90.2 (4)
S1—C18—C19—C200.5 (3)C14—O10—C10—C11179.7 (2)
C17—C18—C19—Br11.6 (5)C8—C9—C10—O10178.7 (2)
S1—C18—C19—Br1179.20 (15)C8—C9—C10—C111.4 (4)
C18—C19—C20—C210.1 (4)C15—O11—C11—C1284.8 (3)
Br1—C19—C20—C21179.8 (2)C15—O11—C11—C1096.9 (3)
C19—C20—C21—S10.6 (4)O10—C10—C11—O112.7 (4)
C18—S1—C21—C200.8 (3)C9—C10—C11—O11177.2 (2)
C4—N3—C2—N2176.7 (2)O10—C10—C11—C12179.0 (2)
C4—N3—C2—N12.3 (4)C9—C10—C11—C121.1 (4)
C6—N1—C2—N2178.2 (2)C16—O12—C12—C11177.6 (3)
C6—N1—C2—N30.8 (4)C16—O12—C12—C132.7 (4)
C2—N3—C4—N4174.2 (2)O11—C11—C12—O121.1 (4)
C2—N3—C4—C53.8 (3)C10—C11—C12—O12179.4 (2)
N4—C4—C5—C6174.2 (2)O11—C11—C12—C13178.7 (2)
N3—C4—C5—C63.8 (3)C10—C11—C12—C130.4 (4)
N4—C4—C5—C73.5 (4)C9—C8—C13—C121.2 (4)
N3—C4—C5—C7174.6 (2)C7—C8—C13—C12177.5 (2)
C4—C5—C6—N12.3 (4)O12—C12—C13—C8178.2 (2)
C7—C5—C6—N1173.2 (2)C11—C12—C13—C81.5 (4)
C2—N1—C6—C50.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.861.992.757 (3)149
O1W—H1W···O10.82 (3)1.99 (3)2.772 (3)160 (4)
N2—H2A···O1Wi0.862.583.159 (3)126
N2—H2A···O20.862.062.865 (4)155
N2—H2B···N3ii0.862.313.169 (3)176
O1W—H2W···O2iii0.82 (1)1.97 (2)2.698 (3)149 (4)
N4—H4A···O1Wiv0.861.972.789 (3)157
Symmetry codes: (i) x, y1, z; (ii) x+1, y, z+1; (iii) x, y+1, z; (iv) x+1, y+1, z+1.
2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidin-1-ium 3-chlorothiophene-2-carboxylate monohydrate (III) top
Crystal data top
C14H19N4O3+·C5H2ClO2S·H2OF(000) = 984
Mr = 470.92Dx = 1.450 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 16.9730 (5) ÅCell parameters from 5309 reflections
b = 6.8689 (1) Åθ = 4.6–74.6°
c = 19.6051 (5) ŵ = 2.87 mm1
β = 109.321 (3)°T = 293 K
V = 2156.95 (10) Å3Plate, colorless
Z = 40.45 × 0.25 × 0.05 mm
Data collection top
Agilent SuperNova Dual Source
diffractometer with an Atlas detector
4105 independent reflections
Radiation source: SuperNova (Cu) X-ray Source3455 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.052
Detector resolution: 10.4933 pixels mm-1θmax = 70.1°, θmin = 4.7°
ω scansh = 2020
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
k = 87
Tmin = 0.440, Tmax = 1.000l = 2323
14820 measured reflections
Refinement top
Refinement on F22 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.148 w = 1/[σ2(Fo2) + (0.0884P)2 + 0.4016P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
4105 reflectionsΔρmax = 0.46 e Å3
289 parametersΔρmin = 0.62 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.98170 (11)0.3357 (3)0.35457 (10)0.0388 (4)
H11.00700.30610.32450.047*
N21.03063 (13)0.0526 (3)0.41655 (12)0.0476 (5)
H2A1.03470.02700.45140.057*
H2B1.05600.02820.38610.057*
N30.94578 (10)0.2507 (2)0.45691 (9)0.0344 (4)
N40.87118 (12)0.4649 (3)0.50105 (10)0.0400 (4)
H4A0.87680.38650.53660.048*
H4B0.84420.57220.49840.048*
O100.56563 (10)0.5009 (2)0.32300 (10)0.0487 (4)
O110.52166 (9)0.8054 (3)0.38558 (9)0.0456 (4)
O120.63167 (11)1.0778 (2)0.45337 (10)0.0497 (4)
C20.98518 (12)0.2129 (3)0.40970 (11)0.0349 (4)
C40.90427 (11)0.4202 (3)0.45006 (11)0.0321 (4)
C50.89665 (12)0.5549 (3)0.39210 (11)0.0344 (4)
C60.93857 (13)0.5047 (3)0.34669 (11)0.0381 (4)
H60.93770.58840.30920.046*
C70.85643 (13)0.7520 (3)0.38753 (13)0.0400 (5)
H7A0.85770.81440.34350.048*
H7B0.89080.82970.42770.048*
C80.76692 (12)0.7595 (3)0.38814 (11)0.0355 (4)
C90.70883 (13)0.6185 (3)0.35332 (12)0.0369 (4)
H90.72450.51540.32990.044*
C100.62700 (12)0.6320 (3)0.35360 (11)0.0353 (4)
C110.60276 (12)0.7886 (3)0.38774 (11)0.0352 (4)
C120.66160 (14)0.9302 (3)0.42249 (12)0.0375 (4)
C130.74355 (13)0.9136 (3)0.42291 (13)0.0401 (5)
H130.78291.00660.44670.048*
C140.58610 (16)0.3370 (4)0.28783 (14)0.0498 (5)
H14B0.60720.38060.25070.075*
H14C0.53700.25940.26660.075*
H14A0.62790.26040.32240.075*
C150.50660 (19)0.7330 (6)0.44742 (17)0.0680 (8)
H15A0.45090.76650.44520.102*
H15C0.54590.78930.49000.102*
H15B0.51270.59400.44920.102*
C160.68977 (19)1.2218 (4)0.49211 (17)0.0591 (7)
H16B0.71371.28510.46000.089*
H16C0.73321.16090.53070.089*
H16A0.66151.31620.51180.089*
Cl11.22878 (4)0.63107 (9)0.25208 (4)0.0592 (2)
S11.32400 (4)0.10415 (10)0.35937 (4)0.0563 (2)
O11.10469 (11)0.3519 (2)0.29058 (10)0.0498 (4)
O21.15012 (14)0.0691 (3)0.34204 (14)0.0711 (6)
C171.16110 (15)0.2302 (3)0.31712 (13)0.0440 (5)
C181.24772 (14)0.2734 (3)0.31957 (12)0.0412 (5)
C191.28319 (15)0.4295 (3)0.29664 (13)0.0441 (5)
C201.37019 (16)0.4127 (4)0.31155 (15)0.0548 (6)
H201.40290.50610.29940.066*
C211.40008 (17)0.2433 (5)0.34582 (16)0.0605 (7)
H211.45600.20730.36030.073*
O1W1.11462 (16)0.6980 (3)0.36430 (11)0.0646 (6)
H1W1.128 (3)0.608 (4)0.343 (2)0.097*
H2W1.138 (3)0.795 (4)0.356 (2)0.097*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0347 (9)0.0470 (10)0.0421 (9)0.0021 (7)0.0227 (7)0.0033 (7)
N20.0495 (11)0.0425 (10)0.0639 (12)0.0104 (8)0.0364 (10)0.0074 (8)
N30.0316 (8)0.0339 (8)0.0437 (9)0.0008 (7)0.0206 (7)0.0026 (7)
N40.0416 (10)0.0395 (9)0.0485 (9)0.0042 (7)0.0280 (8)0.0056 (7)
O100.0312 (7)0.0523 (9)0.0644 (10)0.0067 (7)0.0185 (7)0.0145 (8)
O110.0290 (7)0.0581 (9)0.0545 (9)0.0033 (7)0.0201 (7)0.0001 (7)
O120.0437 (9)0.0418 (8)0.0729 (11)0.0031 (7)0.0317 (8)0.0117 (7)
C20.0287 (9)0.0363 (10)0.0441 (10)0.0025 (8)0.0179 (8)0.0009 (8)
C40.0233 (9)0.0351 (9)0.0412 (10)0.0045 (7)0.0152 (8)0.0004 (7)
C50.0237 (9)0.0389 (10)0.0444 (10)0.0011 (7)0.0165 (8)0.0059 (8)
C60.0302 (9)0.0468 (11)0.0409 (10)0.0003 (8)0.0166 (8)0.0079 (8)
C70.0304 (10)0.0382 (11)0.0566 (12)0.0006 (8)0.0214 (9)0.0076 (9)
C80.0278 (9)0.0365 (10)0.0455 (10)0.0022 (8)0.0168 (8)0.0082 (8)
C90.0301 (10)0.0382 (10)0.0457 (11)0.0027 (8)0.0169 (8)0.0012 (8)
C100.0276 (9)0.0390 (10)0.0404 (10)0.0008 (8)0.0126 (8)0.0023 (8)
C110.0248 (9)0.0417 (10)0.0419 (10)0.0022 (8)0.0149 (8)0.0047 (8)
C120.0358 (10)0.0334 (10)0.0481 (11)0.0025 (8)0.0206 (9)0.0032 (8)
C130.0319 (10)0.0363 (10)0.0545 (12)0.0041 (8)0.0176 (9)0.0011 (8)
C140.0475 (13)0.0493 (13)0.0571 (13)0.0085 (11)0.0234 (11)0.0132 (10)
C150.0516 (15)0.100 (2)0.0673 (17)0.0113 (15)0.0396 (14)0.0013 (15)
C160.0621 (16)0.0473 (13)0.0799 (18)0.0127 (12)0.0396 (14)0.0173 (12)
Cl10.0613 (4)0.0419 (3)0.0894 (5)0.0033 (2)0.0452 (4)0.0070 (3)
S10.0533 (4)0.0574 (4)0.0641 (4)0.0006 (3)0.0274 (3)0.0102 (3)
O10.0453 (9)0.0491 (9)0.0669 (10)0.0063 (7)0.0345 (8)0.0062 (7)
O20.0744 (14)0.0432 (9)0.1214 (18)0.0098 (9)0.0671 (14)0.0078 (10)
C170.0499 (13)0.0388 (11)0.0580 (13)0.0119 (10)0.0374 (11)0.0121 (9)
C180.0434 (12)0.0406 (11)0.0474 (11)0.0077 (9)0.0257 (10)0.0062 (8)
C190.0447 (12)0.0446 (11)0.0533 (12)0.0115 (9)0.0300 (10)0.0070 (9)
C200.0424 (13)0.0637 (15)0.0664 (15)0.0143 (11)0.0288 (12)0.0027 (12)
C210.0415 (13)0.0788 (19)0.0636 (16)0.0023 (12)0.0206 (12)0.0001 (13)
O1W0.1063 (17)0.0404 (9)0.0718 (12)0.0043 (10)0.0627 (12)0.0007 (8)
Geometric parameters (Å, º) top
N1—C61.353 (3)C9—H90.9300
N1—C21.357 (3)C10—C111.399 (3)
N1—H10.8600C11—C121.399 (3)
N2—C21.326 (3)C12—C131.393 (3)
N2—H2A0.8600C13—H130.9300
N2—H2B0.8600C14—H14B0.9600
N3—C21.334 (3)C14—H14C0.9600
N3—C41.344 (3)C14—H14A0.9600
N4—C41.334 (3)C15—H15A0.9600
N4—H4A0.8600C15—H15C0.9600
N4—H4B0.8600C15—H15B0.9600
O10—C101.357 (3)C16—H16B0.9600
O10—C141.422 (3)C16—H16C0.9600
O11—C111.368 (2)C16—H16A0.9600
O11—C151.410 (3)Cl1—C191.732 (3)
O12—C121.362 (3)S1—C211.697 (3)
O12—C161.426 (3)S1—C181.723 (2)
C4—C51.438 (3)O1—C171.248 (3)
C5—C61.355 (3)O2—C171.249 (3)
C5—C71.506 (3)C17—C181.485 (3)
C6—H60.9300C18—C191.376 (3)
C7—C81.524 (3)C19—C201.412 (4)
C7—H7A0.9700C20—C211.355 (4)
C7—H7B0.9700C20—H200.9300
C8—C131.386 (3)C21—H210.9300
C8—C91.390 (3)O1W—H1W0.819 (10)
C9—C101.394 (3)O1W—H2W0.822 (10)
C6—N1—C2120.22 (17)C10—C11—C12119.46 (18)
C6—N1—H1119.9O12—C12—C13125.2 (2)
C2—N1—H1119.9O12—C12—C11115.00 (18)
C2—N2—H2A120.0C13—C12—C11119.78 (19)
C2—N2—H2B120.0C8—C13—C12120.5 (2)
H2A—N2—H2B120.0C8—C13—H13119.8
C2—N3—C4117.75 (17)C12—C13—H13119.8
C4—N4—H4A120.0O10—C14—H14B109.5
C4—N4—H4B120.0O10—C14—H14C109.5
H4A—N4—H4B120.0H14B—C14—H14C109.5
C10—O10—C14117.70 (17)O10—C14—H14A109.5
C11—O11—C15114.24 (19)H14B—C14—H14A109.5
C12—O12—C16117.34 (19)H14C—C14—H14A109.5
N2—C2—N3119.99 (19)O11—C15—H15A109.5
N2—C2—N1117.88 (18)O11—C15—H15C109.5
N3—C2—N1122.12 (19)H15A—C15—H15C109.5
N4—C4—N3117.46 (18)O11—C15—H15B109.5
N4—C4—C5119.59 (18)H15A—C15—H15B109.5
N3—C4—C5122.92 (17)H15C—C15—H15B109.5
C6—C5—C4115.20 (18)O12—C16—H16B109.5
C6—C5—C7121.06 (18)O12—C16—H16C109.5
C4—C5—C7123.11 (18)H16B—C16—H16C109.5
N1—C6—C5121.67 (18)O12—C16—H16A109.5
N1—C6—H6119.2H16B—C16—H16A109.5
C5—C6—H6119.2H16C—C16—H16A109.5
C5—C7—C8117.59 (17)C21—S1—C1892.62 (13)
C5—C7—H7A107.9O1—C17—O2124.3 (2)
C8—C7—H7A107.9O1—C17—C18119.6 (2)
C5—C7—H7B107.9O2—C17—C18116.0 (2)
C8—C7—H7B107.9C19—C18—C17132.9 (2)
H7A—C7—H7B107.2C19—C18—S1109.24 (18)
C13—C8—C9120.12 (19)C17—C18—S1117.86 (17)
C13—C8—C7118.54 (19)C18—C19—C20114.1 (2)
C9—C8—C7121.32 (19)C18—C19—Cl1124.75 (19)
C8—C9—C10119.84 (19)C20—C19—Cl1121.10 (18)
C8—C9—H9120.1C21—C20—C19111.5 (2)
C10—C9—H9120.1C21—C20—H20124.2
O10—C10—C9125.02 (19)C19—C20—H20124.2
O10—C10—C11114.68 (18)C20—C21—S1112.4 (2)
C9—C10—C11120.30 (19)C20—C21—H21123.8
O11—C11—C10120.17 (19)S1—C21—H21123.8
O11—C11—C12120.35 (19)H1W—O1W—H2W106 (4)
C4—N3—C2—N2176.4 (2)O10—C10—C11—C12178.58 (18)
C4—N3—C2—N12.5 (3)C9—C10—C11—C120.9 (3)
C6—N1—C2—N2177.7 (2)C16—O12—C12—C133.1 (3)
C6—N1—C2—N31.2 (3)C16—O12—C12—C11177.4 (2)
C2—N3—C4—N4174.28 (18)O11—C11—C12—O120.9 (3)
C2—N3—C4—C53.8 (3)C10—C11—C12—O12179.28 (18)
N4—C4—C5—C6174.32 (19)O11—C11—C12—C13178.57 (19)
N3—C4—C5—C63.7 (3)C10—C11—C12—C130.2 (3)
N4—C4—C5—C73.3 (3)C9—C8—C13—C120.9 (3)
N3—C4—C5—C7174.76 (18)C7—C8—C13—C12177.58 (19)
C2—N1—C6—C51.2 (3)O12—C12—C13—C8178.3 (2)
C4—C5—C6—N12.3 (3)C11—C12—C13—C81.1 (3)
C7—C5—C6—N1173.58 (19)O1—C17—C18—C190.9 (4)
C6—C5—C7—C8132.8 (2)O2—C17—C18—C19178.5 (3)
C4—C5—C7—C856.6 (3)O1—C17—C18—S1177.95 (17)
C5—C7—C8—C13144.5 (2)O2—C17—C18—S12.7 (3)
C5—C7—C8—C937.0 (3)C21—S1—C18—C190.64 (19)
C13—C8—C9—C100.2 (3)C21—S1—C18—C17178.45 (18)
C7—C8—C9—C10178.61 (18)C17—C18—C19—C20178.4 (2)
C14—O10—C10—C90.1 (3)S1—C18—C19—C200.5 (3)
C14—O10—C10—C11179.5 (2)C17—C18—C19—Cl12.4 (4)
C8—C9—C10—O10178.3 (2)S1—C18—C19—Cl1178.67 (13)
C8—C9—C10—C111.1 (3)C18—C19—C20—C210.0 (3)
C15—O11—C11—C1097.3 (3)Cl1—C19—C20—C21179.2 (2)
C15—O11—C11—C1284.3 (3)C19—C20—C21—S10.5 (3)
O10—C10—C11—O113.0 (3)C18—S1—C21—C200.7 (2)
C9—C10—C11—O11177.52 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.862.012.771 (3)148
O1W—H1W···O10.82 (4)2.01 (3)2.758 (3)152 (5)
N2—H2A···N3i0.862.303.162 (3)176
N2—H2B···O1Wii0.862.573.159 (3)127
N2—H2B···O20.862.072.867 (3)154
O1W—H2W···O2iii0.82 (4)1.92 (3)2.688 (3)155 (5)
N4—H4A···O1Wiv0.861.992.803 (3)158
C6—H6···O1v0.932.593.487 (3)163
Symmetry codes: (i) x+2, y, z+1; (ii) x, y1, z; (iii) x, y+1, z; (iv) x+2, y+1, z+1; (v) x+2, y+1/2, z+1/2.
2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidin-1-ium 5-methylthiophene-2-carboxylate monohydrate (IV) top
Crystal data top
C14H19N4O3+·C6H5O2S·H2OZ = 2
Mr = 450.51F(000) = 476
Triclinic, P1Dx = 1.365 Mg m3
a = 6.9417 (3) ÅCu Kα radiation, λ = 1.54184 Å
b = 9.8281 (6) ÅCell parameters from 3402 reflections
c = 16.2754 (10) Åθ = 4.5–74.3°
α = 90.813 (5)°µ = 1.70 mm1
β = 90.376 (4)°T = 293 K
γ = 99.084 (4)°Prism, colorless
V = 1096.29 (11) Å30.35 × 0.25 × 0.15 mm
Data collection top
Agilent SuperNova Dual Source
diffractometer with an Atlas detector
4155 independent reflections
Radiation source: SuperNova (Cu) X-ray Source3502 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.023
Detector resolution: 10.4933 pixels mm-1θmax = 70.1°, θmin = 4.6°
ω scansh = 68
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
k = 1111
Tmin = 0.335, Tmax = 1.000l = 1919
7519 measured reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.041 w = 1/[σ2(Fo2) + (0.0657P)2 + 0.191P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.118(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.23 e Å3
4155 reflectionsΔρmin = 0.26 e Å3
285 parametersExtinction correction: SHELXT (Sheldrick, 2015a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0102 (8)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.2859 (2)0.28247 (14)0.09902 (9)0.0406 (3)
H10.23860.19630.10160.049*
N20.0052 (2)0.32154 (15)0.03457 (10)0.0465 (4)
H2A0.06520.37640.01300.056*
H2B0.03810.23470.03650.056*
N30.24574 (18)0.50579 (13)0.06134 (8)0.0335 (3)
N40.4863 (2)0.68792 (14)0.08831 (9)0.0426 (3)
H4A0.41350.74030.06580.051*
H4B0.59910.72270.10770.051*
O100.46033 (18)0.61576 (14)0.43249 (8)0.0491 (3)
O110.7951 (2)0.77575 (13)0.47759 (7)0.0493 (3)
O121.09591 (18)0.82209 (14)0.37553 (8)0.0537 (4)
C20.1804 (2)0.37076 (16)0.06482 (9)0.0342 (3)
C40.4245 (2)0.55373 (16)0.09306 (9)0.0323 (3)
C50.5453 (2)0.46392 (17)0.12840 (9)0.0347 (3)
C60.4675 (3)0.32957 (17)0.12951 (10)0.0393 (4)
H60.54010.26700.15180.047*
C70.7450 (2)0.5151 (2)0.16288 (10)0.0414 (4)
H7A0.81560.57730.12380.050*
H7B0.81400.43720.16830.050*
C80.7490 (2)0.58913 (17)0.24565 (10)0.0356 (4)
C90.5932 (2)0.56625 (17)0.29904 (10)0.0369 (4)
H90.47970.50790.28340.044*
C100.6065 (2)0.63051 (17)0.37606 (10)0.0361 (4)
C110.7771 (2)0.71709 (17)0.39997 (10)0.0372 (4)
C120.9335 (2)0.73845 (17)0.34612 (11)0.0391 (4)
C130.9189 (2)0.67615 (18)0.26875 (11)0.0395 (4)
H131.02260.69260.23250.047*
C140.2941 (3)0.5146 (2)0.41586 (12)0.0522 (5)
H14A0.22950.53840.36700.078*
H14B0.20600.51070.46130.078*
H14C0.33440.42630.40800.078*
C150.7364 (5)0.9061 (3)0.48353 (16)0.0801 (8)
H15A0.79640.96370.44060.120*
H15B0.77570.94750.53600.120*
H15C0.59710.89600.47800.120*
C161.2567 (3)0.8507 (2)0.32168 (14)0.0557 (5)
H16A1.22020.90070.27530.084*
H16B1.29450.76570.30300.084*
H16C1.36420.90510.35030.084*
S10.00942 (7)0.16614 (5)0.27384 (3)0.05197 (17)
O10.12536 (19)0.01871 (13)0.13135 (9)0.0504 (3)
O20.1574 (2)0.11389 (16)0.10099 (9)0.0626 (4)
C170.0560 (3)0.02140 (17)0.14159 (11)0.0422 (4)
C180.1493 (3)0.05097 (18)0.20791 (11)0.0435 (4)
C190.3406 (3)0.0421 (2)0.22606 (13)0.0514 (5)
H190.43930.01510.19770.062*
C200.3753 (3)0.1290 (2)0.29276 (13)0.0535 (5)
H200.49960.13540.31190.064*
C210.2101 (3)0.2021 (2)0.32632 (12)0.0483 (4)
C220.1899 (4)0.2992 (2)0.39856 (14)0.0623 (5)
H22A0.10240.27030.43820.093*
H22B0.31530.29920.42300.093*
H22C0.13900.39050.38080.093*
O1W0.3108 (2)0.90308 (16)0.01268 (9)0.0637 (4)
H1W0.25120.93810.04920.096*
H2W0.41430.95930.01580.096*0.5
H3W0.30420.95500.02640.096*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0471 (8)0.0258 (7)0.0462 (8)0.0025 (6)0.0023 (6)0.0009 (6)
N20.0434 (8)0.0314 (7)0.0602 (10)0.0075 (6)0.0107 (7)0.0032 (6)
N30.0346 (7)0.0267 (6)0.0366 (7)0.0024 (5)0.0017 (5)0.0024 (5)
N40.0408 (7)0.0296 (7)0.0536 (9)0.0052 (6)0.0083 (6)0.0029 (6)
O100.0446 (7)0.0587 (8)0.0395 (7)0.0054 (6)0.0061 (5)0.0083 (6)
O110.0625 (8)0.0473 (7)0.0359 (6)0.0028 (6)0.0089 (6)0.0083 (5)
O120.0427 (7)0.0562 (8)0.0549 (8)0.0135 (6)0.0073 (6)0.0103 (6)
C20.0380 (8)0.0301 (8)0.0320 (8)0.0019 (6)0.0017 (6)0.0041 (6)
C40.0346 (8)0.0306 (8)0.0291 (7)0.0024 (6)0.0021 (6)0.0058 (6)
C50.0364 (8)0.0377 (8)0.0291 (7)0.0040 (7)0.0009 (6)0.0054 (6)
C60.0464 (9)0.0350 (8)0.0370 (8)0.0080 (7)0.0027 (7)0.0014 (6)
C70.0350 (8)0.0509 (10)0.0378 (9)0.0057 (7)0.0015 (7)0.0077 (7)
C80.0344 (8)0.0369 (8)0.0353 (8)0.0051 (6)0.0038 (6)0.0015 (6)
C90.0322 (8)0.0395 (9)0.0371 (8)0.0003 (6)0.0053 (6)0.0040 (7)
C100.0349 (8)0.0377 (8)0.0350 (8)0.0038 (6)0.0004 (6)0.0006 (6)
C110.0424 (9)0.0353 (8)0.0331 (8)0.0038 (7)0.0071 (7)0.0032 (6)
C120.0355 (8)0.0354 (8)0.0438 (9)0.0023 (7)0.0080 (7)0.0004 (7)
C130.0323 (8)0.0427 (9)0.0418 (9)0.0009 (7)0.0010 (7)0.0011 (7)
C140.0451 (10)0.0583 (12)0.0480 (10)0.0082 (9)0.0069 (8)0.0003 (9)
C150.118 (2)0.0599 (15)0.0661 (15)0.0277 (14)0.0115 (14)0.0236 (12)
C160.0392 (9)0.0527 (11)0.0698 (13)0.0094 (8)0.0072 (9)0.0030 (10)
S10.0426 (3)0.0530 (3)0.0588 (3)0.0041 (2)0.0025 (2)0.0106 (2)
O10.0496 (7)0.0336 (6)0.0649 (8)0.0025 (5)0.0091 (6)0.0050 (6)
O20.0618 (9)0.0577 (9)0.0601 (9)0.0146 (7)0.0024 (7)0.0132 (7)
C170.0480 (10)0.0316 (8)0.0449 (9)0.0009 (7)0.0001 (7)0.0050 (7)
C180.0455 (9)0.0363 (9)0.0469 (10)0.0004 (7)0.0011 (8)0.0056 (7)
C190.0451 (10)0.0473 (11)0.0584 (11)0.0035 (8)0.0004 (8)0.0037 (9)
C200.0460 (10)0.0531 (11)0.0610 (12)0.0051 (9)0.0103 (9)0.0061 (9)
C210.0545 (10)0.0436 (10)0.0474 (10)0.0093 (8)0.0026 (8)0.0061 (8)
C220.0682 (13)0.0621 (13)0.0588 (13)0.0177 (11)0.0012 (10)0.0072 (10)
O1W0.0704 (9)0.0620 (9)0.0617 (9)0.0204 (7)0.0031 (7)0.0059 (7)
Geometric parameters (Å, º) top
N1—C21.344 (2)C11—C121.391 (2)
N1—C61.360 (2)C12—C131.389 (2)
N1—H10.8600C13—H130.9300
N2—C21.325 (2)C14—H14A0.9600
N2—H2A0.8600C14—H14B0.9600
N2—H2B0.8600C14—H14C0.9600
N3—C21.335 (2)C15—H15A0.9600
N3—C41.3524 (19)C15—H15B0.9600
N4—C41.324 (2)C15—H15C0.9600
N4—H4A0.8600C16—H16A0.9600
N4—H4B0.8600C16—H16B0.9600
O10—C101.365 (2)C16—H16C0.9600
O10—C141.421 (2)S1—C211.720 (2)
O11—C111.378 (2)S1—C181.7263 (18)
O11—C151.406 (3)O1—C171.271 (2)
O12—C121.3657 (19)O2—C171.238 (2)
O12—C161.419 (2)C17—C181.491 (3)
C4—C51.433 (2)C18—C191.352 (3)
C5—C61.346 (2)C19—C201.416 (3)
C5—C71.500 (2)C19—H190.9300
C6—H60.9300C20—C211.361 (3)
C7—C81.520 (2)C20—H200.9300
C7—H7A0.9700C21—C221.496 (3)
C7—H7B0.9700C22—H22A0.9600
C8—C91.384 (2)C22—H22B0.9600
C8—C131.389 (2)C22—H22C0.9600
C9—C101.392 (2)O1W—H1W0.8280
C9—H90.9300O1W—H2W0.8353
C10—C111.394 (2)O1W—H3W0.8274
C2—N1—C6119.91 (14)C12—C13—C8119.85 (16)
C2—N1—H1120.0C12—C13—H13120.1
C6—N1—H1120.0C8—C13—H13120.1
C2—N2—H2A120.0O10—C14—H14A109.5
C2—N2—H2B120.0O10—C14—H14B109.5
H2A—N2—H2B120.0H14A—C14—H14B109.5
C2—N3—C4118.24 (14)O10—C14—H14C109.5
C4—N4—H4A120.0H14A—C14—H14C109.5
C4—N4—H4B120.0H14B—C14—H14C109.5
H4A—N4—H4B120.0O11—C15—H15A109.5
C10—O10—C14117.58 (13)O11—C15—H15B109.5
C11—O11—C15114.42 (15)H15A—C15—H15B109.5
C12—O12—C16117.23 (14)O11—C15—H15C109.5
N2—C2—N3119.32 (15)H15A—C15—H15C109.5
N2—C2—N1118.53 (14)H15B—C15—H15C109.5
N3—C2—N1122.15 (14)O12—C16—H16A109.5
N4—C4—N3116.99 (15)O12—C16—H16B109.5
N4—C4—C5120.98 (14)H16A—C16—H16B109.5
N3—C4—C5122.00 (14)O12—C16—H16C109.5
C6—C5—C4115.67 (14)H16A—C16—H16C109.5
C6—C5—C7121.61 (16)H16B—C16—H16C109.5
C4—C5—C7122.71 (15)C21—S1—C1892.79 (9)
C5—C6—N1121.99 (16)O2—C17—O1125.02 (18)
C5—C6—H6119.0O2—C17—C18119.02 (17)
N1—C6—H6119.0O1—C17—C18115.95 (15)
C5—C7—C8115.21 (14)C19—C18—C17128.91 (17)
C5—C7—H7A108.5C19—C18—S1110.47 (15)
C8—C7—H7A108.5C17—C18—S1120.62 (13)
C5—C7—H7B108.5C18—C19—C20113.03 (18)
C8—C7—H7B108.5C18—C19—H19123.5
H7A—C7—H7B107.5C20—C19—H19123.5
C9—C8—C13120.17 (15)C21—C20—C19113.82 (18)
C9—C8—C7121.74 (14)C21—C20—H20123.1
C13—C8—C7118.01 (15)C19—C20—H20123.1
C8—C9—C10120.00 (14)C20—C21—C22128.68 (19)
C8—C9—H9120.0C20—C21—S1109.88 (15)
C10—C9—H9120.0C22—C21—S1121.43 (16)
O10—C10—C9124.33 (14)C21—C22—H22A109.5
O10—C10—C11115.49 (14)C21—C22—H22B109.5
C9—C10—C11120.19 (15)H22A—C22—H22B109.5
O11—C11—C12119.99 (15)C21—C22—H22C109.5
O11—C11—C10120.57 (15)H22A—C22—H22C109.5
C12—C11—C10119.36 (15)H22B—C22—H22C109.5
O12—C12—C13124.34 (16)H1W—O1W—H2W97.3
O12—C12—C11115.25 (15)H1W—O1W—H3W102.7
C13—C12—C11120.41 (15)H2W—O1W—H3W75.7
C4—N3—C2—N2179.61 (14)C9—C10—C11—O11176.79 (15)
C4—N3—C2—N10.4 (2)O10—C10—C11—C12179.77 (15)
C6—N1—C2—N2179.02 (15)C9—C10—C11—C120.0 (2)
C6—N1—C2—N31.8 (2)C16—O12—C12—C132.6 (3)
C2—N3—C4—N4179.57 (14)C16—O12—C12—C11177.86 (16)
C2—N3—C4—C51.2 (2)O11—C11—C12—O121.7 (2)
N4—C4—C5—C6179.68 (15)C10—C11—C12—O12178.49 (15)
N3—C4—C5—C61.4 (2)O11—C11—C12—C13177.90 (15)
N4—C4—C5—C70.9 (2)C10—C11—C12—C131.1 (3)
N3—C4—C5—C7179.19 (14)O12—C12—C13—C8177.92 (16)
C4—C5—C6—N10.0 (2)C11—C12—C13—C81.6 (3)
C7—C5—C6—N1179.43 (14)C9—C8—C13—C121.1 (3)
C2—N1—C6—C51.5 (3)C7—C8—C13—C12175.63 (16)
C6—C5—C7—C8104.60 (19)O2—C17—C18—C198.5 (3)
C4—C5—C7—C874.8 (2)O1—C17—C18—C19171.34 (19)
C5—C7—C8—C923.7 (2)O2—C17—C18—S1172.41 (15)
C5—C7—C8—C13159.62 (16)O1—C17—C18—S17.8 (2)
C13—C8—C9—C100.0 (3)C21—S1—C18—C190.16 (15)
C7—C8—C9—C10176.59 (16)C21—S1—C18—C17179.42 (15)
C14—O10—C10—C98.6 (3)C17—C18—C19—C20178.71 (17)
C14—O10—C10—C11171.61 (16)S1—C18—C19—C200.5 (2)
C8—C9—C10—O10179.19 (16)C18—C19—C20—C211.1 (3)
C8—C9—C10—C110.6 (3)C19—C20—C21—C22177.7 (2)
C15—O11—C11—C1291.7 (2)C19—C20—C21—S11.2 (2)
C15—O11—C11—C1091.5 (2)C18—S1—C21—C200.77 (15)
O10—C10—C11—O113.4 (2)C18—S1—C21—C22178.18 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.861.872.7153 (19)167
O1W—H1W···O1i0.831.842.667 (2)178
N2—H2A···N3ii0.862.203.054 (2)170
N2—H2B···O1Wii0.862.282.946 (2)134
O1W—H2W···O1Wiii0.842.213.026 (2)164
O1W—H3W···O2ii0.832.343.103 (2)153
N4—H4A···O1W0.862.052.888 (2)164
N4—H4B···O2iv0.862.142.901 (2)147
Symmetry codes: (i) x, y+1, z; (ii) x, y+1, z; (iii) x+1, y+2, z; (iv) x+1, y+1, z.
2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidin-1-ium anthracene-9-carboxylate sesquihydrate (V) top
Crystal data top
2C14H19N4O3+·2C15H9O2·3(H2O)Z = 2
Mr = 1079.15F(000) = 1140
Triclinic, P1Dx = 1.298 Mg m3
a = 11.1680 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 16.1913 (5) ÅCell parameters from 6949 reflections
c = 16.2434 (5) Åθ = 3.2–27.3°
α = 106.203 (3)°µ = 0.09 mm1
β = 101.386 (3)°T = 293 K
γ = 90.029 (3)°Prism, yellow
V = 2760.20 (18) Å30.40 × 0.30 × 0.10 mm
Data collection top
Agilent SuperNova Dual Source
diffractometer with an Atlas detector
12640 independent reflections
Radiation source: SuperNova (Mo) X-ray Source7531 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.035
Detector resolution: 10.4933 pixels mm-1θmax = 27.5°, θmin = 2.9°
ω scansh = 1411
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
k = 1921
Tmin = 0.755, Tmax = 1.000l = 2120
29344 measured reflections
Refinement top
Refinement on F26 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.062H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.189 w = 1/[σ2(Fo2) + (0.0784P)2 + 0.7983P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
12640 reflectionsΔρmax = 0.44 e Å3
742 parametersΔρmin = 0.36 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N1A0.42349 (16)0.63275 (11)0.36066 (11)0.0443 (4)
H1A0.47820.67020.36070.053*
N2A0.55873 (17)0.58920 (13)0.46403 (12)0.0520 (5)
H2A0.57610.55790.49920.062*
H2B0.61340.62520.46120.062*
N3A0.36439 (16)0.52609 (11)0.41934 (11)0.0420 (4)
N4A0.16927 (19)0.46738 (14)0.37770 (13)0.0605 (6)
H4A0.18770.43860.41520.073*
H4B0.09660.46180.34620.073*
O10A0.11712 (17)0.59173 (11)0.04154 (11)0.0618 (5)
O11A0.00987 (17)0.73737 (12)0.00709 (12)0.0695 (5)
O12A0.06035 (19)0.80335 (12)0.14574 (15)0.0816 (6)
C2A0.44835 (19)0.58204 (13)0.41443 (13)0.0394 (4)
C4A0.25279 (19)0.52017 (13)0.36841 (13)0.0413 (5)
C5A0.22347 (19)0.56872 (14)0.30614 (13)0.0417 (5)
C6A0.3118 (2)0.62481 (14)0.30626 (14)0.0449 (5)
H6C0.29660.65910.26840.054*
C7A0.0973 (2)0.55594 (18)0.24789 (15)0.0569 (6)
H7C0.08180.49520.21680.068*
H7D0.03760.57160.28480.068*
C8A0.0767 (2)0.60631 (16)0.18165 (14)0.0487 (5)
C9A0.1128 (2)0.57437 (15)0.10240 (14)0.0477 (5)
H9A0.15400.52380.09170.057*
C10A0.0876 (2)0.61785 (15)0.03898 (14)0.0462 (5)
C11A0.0269 (2)0.69351 (15)0.05536 (15)0.0497 (5)
C12A0.0064 (2)0.72650 (15)0.13520 (17)0.0541 (6)
C13A0.0177 (2)0.68258 (17)0.19813 (16)0.0559 (6)
H13A0.00580.70440.25150.067*
C14A0.1890 (3)0.51853 (18)0.05974 (19)0.0694 (7)
H14A0.20840.50980.11640.104*
H14B0.14360.46850.05900.104*
H14C0.26320.52810.01610.104*
C150.1131 (3)0.7388 (3)0.0508 (3)0.1212 (15)
H15A0.14730.68080.07720.182*
H15B0.11510.76750.09540.182*
H15C0.15990.76900.00940.182*
C160.1003 (3)0.8407 (2)0.2258 (3)0.1082 (13)
H16A0.03320.84620.27450.162*
H16B0.16520.80430.23040.162*
H16C0.12940.89660.22640.162*
N1B0.81669 (18)0.17705 (12)0.24088 (11)0.0487 (5)
H1B0.81230.21120.20840.058*
N2B1.00200 (18)0.24533 (13)0.32005 (13)0.0540 (5)
H2C1.06550.25060.36130.065*
H2D0.99480.27970.28760.065*
N3B0.92672 (16)0.13168 (11)0.35652 (11)0.0449 (4)
N4B0.84917 (18)0.02136 (13)0.39536 (12)0.0557 (5)
H4C0.91400.02730.43560.067*
H4D0.79290.01760.38890.067*
O10B0.43317 (18)0.13067 (12)0.04335 (11)0.0677 (5)
O11B0.24001 (17)0.03684 (13)0.02539 (11)0.0709 (5)
O12B0.21985 (18)0.06858 (14)0.13037 (13)0.0767 (6)
C2B0.9147 (2)0.18401 (13)0.30644 (13)0.0419 (5)
C4B0.83605 (19)0.07198 (13)0.34354 (13)0.0412 (5)
C5B0.72803 (19)0.06269 (13)0.27621 (13)0.0414 (5)
C6B0.7245 (2)0.11616 (14)0.22588 (13)0.0465 (5)
H6D0.65790.11160.17990.056*
C7B0.6273 (2)0.00299 (16)0.26715 (15)0.0521 (6)
H7E0.59480.01240.32020.063*
H7F0.66210.05860.26230.063*
C8B0.5229 (2)0.01183 (14)0.18972 (14)0.0460 (5)
C9B0.5305 (2)0.06666 (14)0.10936 (15)0.0487 (5)
H9B0.60020.09720.10300.058*
C10B0.4346 (2)0.07654 (14)0.03770 (14)0.0490 (5)
C11B0.3312 (2)0.03009 (15)0.04715 (14)0.0490 (5)
C12B0.3243 (2)0.02495 (16)0.12817 (16)0.0523 (6)
C13B0.4205 (2)0.03424 (15)0.19955 (15)0.0512 (6)
H13B0.41580.07150.25380.061*
C14B0.5386 (3)0.17720 (19)0.0574 (2)0.0789 (9)
H14D0.52610.21130.11740.118*
H14E0.55270.21420.01980.118*
H14F0.60830.13750.04430.118*
C15B0.1335 (3)0.0844 (3)0.0284 (2)0.0997 (12)
H15D0.07320.08310.07900.150*
H15E0.10220.05970.02350.150*
H15F0.15230.14300.03170.150*
C16B0.2039 (3)0.1227 (2)0.2112 (2)0.0866 (9)
H16D0.12680.14860.20330.130*
H16E0.26880.16690.23360.130*
H16F0.20510.08950.25190.130*
O1A0.62326 (17)0.74670 (12)0.40443 (14)0.0777 (6)
O2A0.70294 (17)0.86409 (13)0.38799 (14)0.0801 (6)
C17A0.6216 (2)0.80623 (16)0.36924 (16)0.0543 (6)
C18A0.5111 (2)0.80566 (14)0.29826 (15)0.0463 (5)
C19A0.5070 (2)0.75344 (15)0.21295 (16)0.0539 (6)
C20A0.6046 (3)0.70157 (19)0.1898 (2)0.0798 (9)
H20A0.67280.70060.23280.096*
C21A0.5997 (5)0.6539 (2)0.1068 (3)0.1146 (14)
H21A0.66540.62150.09260.137*
C22A0.4952 (6)0.6527 (3)0.0407 (3)0.1171 (16)
H22A0.49230.61840.01620.141*
C23A0.4009 (4)0.7001 (2)0.0589 (2)0.0930 (11)
H23A0.33330.69850.01450.112*
C24A0.4025 (3)0.75323 (17)0.14612 (16)0.0615 (7)
C25A0.3079 (2)0.80447 (19)0.16664 (18)0.0652 (8)
H25A0.24040.80410.12260.078*
C26A0.3100 (2)0.85645 (17)0.25060 (18)0.0578 (6)
C27A0.2131 (3)0.9096 (2)0.2718 (3)0.0812 (9)
H27A0.14530.90960.22810.097*
C28A0.2171 (3)0.9592 (2)0.3528 (3)0.0983 (11)
H28A0.15190.99290.36510.118*
C29A0.3190 (3)0.9613 (2)0.4201 (2)0.0893 (10)
H29A0.32100.99700.47630.107*
C30A0.4140 (3)0.91195 (19)0.40396 (19)0.0683 (7)
H30A0.48020.91370.44940.082*
C31A0.4146 (2)0.85739 (15)0.31872 (15)0.0484 (5)
O1B0.8577 (2)0.53922 (14)0.42407 (18)0.1089 (9)
O2B0.90955 (18)0.44320 (15)0.31071 (13)0.0831 (6)
C17B0.8421 (2)0.47036 (17)0.36435 (18)0.0614 (7)
C18B0.7343 (2)0.41143 (14)0.35736 (15)0.0498 (5)
C19B0.7464 (2)0.35423 (15)0.40833 (15)0.0520 (6)
C20B0.8569 (2)0.35078 (17)0.46886 (16)0.0593 (6)
H20B0.92390.38770.47490.071*
C21B0.8655 (3)0.29486 (19)0.51724 (18)0.0722 (8)
H21B0.93830.29360.55610.087*
C22B0.7648 (4)0.2380 (2)0.5095 (2)0.0805 (9)
H22B0.77190.19980.54340.097*
C23B0.6587 (3)0.23892 (19)0.4533 (2)0.0779 (9)
H23B0.59350.20120.44910.094*
C24B0.6442 (3)0.29647 (16)0.40037 (17)0.0604 (7)
C25B0.5357 (3)0.29986 (18)0.34279 (19)0.0675 (7)
H25B0.46970.26250.33780.081*
C26B0.5224 (2)0.35731 (17)0.29236 (17)0.0599 (6)
C27B0.4101 (3)0.3622 (2)0.2337 (2)0.0750 (8)
H27B0.34330.32530.22800.090*
C280.3998 (3)0.4189 (2)0.1869 (2)0.0793 (9)
H28B0.32610.42080.14920.095*
C29B0.4982 (3)0.4751 (2)0.19389 (18)0.0740 (8)
H29B0.48930.51440.16110.089*
C30B0.6074 (3)0.47318 (18)0.24826 (17)0.0639 (7)
H30B0.67230.51100.25190.077*
C31B0.6235 (2)0.41439 (15)0.29936 (15)0.0533 (6)
O1W0.1841 (2)0.30063 (17)0.48211 (15)0.0914 (7)
H1W0.240 (3)0.277 (2)0.506 (2)0.137*
H2W0.167 (4)0.3487 (13)0.509 (3)0.137*
O2W0.8520 (3)0.30848 (16)0.16746 (17)0.1134 (9)
H4W0.866 (5)0.3533 (17)0.208 (2)0.170*
H3W0.869 (4)0.316 (3)0.1234 (18)0.170*
O3W0.9404 (2)0.88060 (17)0.47486 (18)0.1070 (9)
H5W0.956 (4)0.856 (2)0.513 (2)0.161*
H6W0.8695 (15)0.867 (3)0.448 (3)0.161*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0426 (10)0.0445 (10)0.0506 (10)0.0070 (8)0.0084 (8)0.0222 (8)
N2A0.0421 (10)0.0580 (12)0.0606 (11)0.0089 (9)0.0034 (8)0.0294 (10)
N3A0.0412 (10)0.0468 (10)0.0424 (9)0.0045 (8)0.0073 (7)0.0205 (8)
N4A0.0519 (12)0.0712 (14)0.0659 (12)0.0196 (10)0.0028 (9)0.0421 (11)
O10A0.0764 (12)0.0647 (11)0.0524 (10)0.0094 (9)0.0216 (8)0.0241 (8)
O11A0.0697 (12)0.0681 (11)0.0837 (12)0.0042 (9)0.0052 (9)0.0498 (10)
O12A0.0800 (14)0.0568 (11)0.1061 (16)0.0181 (10)0.0239 (12)0.0170 (11)
C2A0.0425 (11)0.0382 (11)0.0392 (10)0.0007 (9)0.0107 (8)0.0123 (9)
C4A0.0425 (12)0.0432 (11)0.0395 (10)0.0053 (9)0.0085 (9)0.0141 (9)
C5A0.0430 (12)0.0470 (12)0.0375 (10)0.0032 (9)0.0092 (8)0.0154 (9)
C6A0.0482 (13)0.0473 (12)0.0439 (11)0.0016 (10)0.0080 (9)0.0219 (10)
C7A0.0493 (13)0.0749 (17)0.0519 (13)0.0128 (12)0.0012 (10)0.0329 (12)
C8A0.0419 (12)0.0590 (14)0.0464 (12)0.0080 (11)0.0012 (9)0.0221 (11)
C9A0.0447 (12)0.0490 (13)0.0525 (13)0.0013 (10)0.0054 (10)0.0227 (11)
C10A0.0427 (12)0.0513 (13)0.0461 (12)0.0043 (10)0.0051 (9)0.0191 (10)
C11A0.0442 (12)0.0486 (13)0.0584 (14)0.0026 (10)0.0012 (10)0.0251 (11)
C12A0.0459 (13)0.0460 (13)0.0665 (15)0.0010 (10)0.0058 (11)0.0140 (12)
C13A0.0499 (14)0.0631 (16)0.0502 (13)0.0067 (12)0.0096 (10)0.0094 (12)
C14A0.0728 (18)0.0680 (18)0.0673 (16)0.0023 (15)0.0270 (14)0.0104 (14)
C150.087 (3)0.159 (4)0.135 (3)0.007 (3)0.019 (2)0.100 (3)
C160.090 (3)0.074 (2)0.156 (4)0.0070 (19)0.062 (3)0.000 (2)
N1B0.0617 (12)0.0470 (10)0.0383 (9)0.0080 (9)0.0035 (8)0.0183 (8)
N2B0.0535 (12)0.0550 (12)0.0551 (11)0.0111 (9)0.0092 (9)0.0194 (10)
N3B0.0448 (10)0.0440 (10)0.0454 (10)0.0016 (8)0.0045 (8)0.0153 (8)
N4B0.0547 (12)0.0566 (12)0.0568 (11)0.0090 (9)0.0077 (9)0.0310 (10)
O10B0.0864 (13)0.0625 (11)0.0467 (9)0.0114 (10)0.0066 (9)0.0084 (8)
O11B0.0624 (12)0.0848 (13)0.0586 (10)0.0007 (10)0.0111 (8)0.0257 (10)
O12B0.0639 (12)0.0863 (14)0.0745 (12)0.0256 (11)0.0122 (9)0.0155 (11)
C2B0.0470 (12)0.0409 (11)0.0371 (10)0.0030 (9)0.0116 (9)0.0077 (9)
C4B0.0444 (12)0.0401 (11)0.0390 (10)0.0008 (9)0.0063 (9)0.0125 (9)
C5B0.0463 (12)0.0409 (11)0.0350 (10)0.0014 (9)0.0029 (8)0.0111 (9)
C6B0.0528 (13)0.0473 (12)0.0371 (11)0.0043 (10)0.0014 (9)0.0137 (10)
C7B0.0500 (13)0.0568 (14)0.0509 (13)0.0083 (11)0.0006 (10)0.0252 (11)
C8B0.0458 (12)0.0461 (12)0.0465 (12)0.0087 (10)0.0018 (9)0.0192 (10)
C9B0.0469 (13)0.0454 (12)0.0560 (13)0.0004 (10)0.0072 (10)0.0204 (11)
C10B0.0600 (14)0.0421 (12)0.0443 (12)0.0028 (11)0.0055 (10)0.0151 (10)
C11B0.0479 (13)0.0502 (13)0.0466 (12)0.0028 (10)0.0016 (10)0.0180 (11)
C12B0.0470 (13)0.0529 (14)0.0585 (14)0.0037 (11)0.0087 (10)0.0201 (12)
C13B0.0558 (14)0.0493 (13)0.0458 (12)0.0060 (11)0.0074 (10)0.0110 (10)
C14B0.113 (3)0.0614 (17)0.0711 (18)0.0244 (17)0.0368 (17)0.0200 (15)
C15B0.063 (2)0.130 (3)0.082 (2)0.021 (2)0.0067 (16)0.005 (2)
C16B0.091 (2)0.082 (2)0.094 (2)0.0281 (18)0.0366 (19)0.0240 (19)
O1A0.0608 (11)0.0740 (12)0.1061 (15)0.0212 (9)0.0165 (10)0.0616 (12)
O2A0.0570 (11)0.0780 (13)0.1078 (15)0.0317 (10)0.0242 (10)0.0591 (12)
C17A0.0462 (13)0.0525 (14)0.0667 (15)0.0115 (11)0.0005 (11)0.0292 (12)
C18A0.0424 (12)0.0432 (12)0.0554 (13)0.0126 (10)0.0013 (9)0.0236 (10)
C19A0.0596 (15)0.0408 (12)0.0638 (15)0.0118 (11)0.0144 (12)0.0177 (11)
C20A0.087 (2)0.0547 (17)0.105 (2)0.0015 (15)0.0351 (19)0.0228 (17)
C21A0.158 (4)0.067 (2)0.129 (4)0.004 (2)0.080 (3)0.010 (2)
C22A0.189 (5)0.075 (2)0.086 (3)0.036 (3)0.067 (3)0.007 (2)
C23A0.127 (3)0.086 (2)0.0576 (18)0.050 (2)0.0131 (19)0.0097 (17)
C24A0.0738 (18)0.0568 (15)0.0505 (14)0.0304 (14)0.0047 (12)0.0154 (12)
C25A0.0536 (15)0.0759 (18)0.0659 (16)0.0278 (14)0.0120 (12)0.0369 (15)
C26A0.0417 (13)0.0610 (15)0.0750 (17)0.0109 (11)0.0016 (11)0.0337 (14)
C27A0.0459 (16)0.086 (2)0.121 (3)0.0007 (15)0.0115 (17)0.049 (2)
C28A0.066 (2)0.087 (2)0.151 (4)0.0074 (18)0.044 (2)0.032 (3)
C29A0.087 (2)0.080 (2)0.100 (2)0.0123 (18)0.048 (2)0.0022 (18)
C30A0.0629 (17)0.0705 (18)0.0683 (17)0.0165 (14)0.0142 (13)0.0140 (14)
C31A0.0428 (12)0.0471 (13)0.0569 (13)0.0122 (10)0.0054 (10)0.0208 (11)
O1B0.0931 (17)0.0551 (12)0.144 (2)0.0197 (11)0.0086 (15)0.0055 (14)
O2B0.0636 (12)0.1176 (18)0.0676 (12)0.0377 (12)0.0102 (10)0.0281 (12)
C17B0.0567 (16)0.0540 (15)0.0673 (16)0.0122 (12)0.0028 (13)0.0179 (13)
C18B0.0512 (13)0.0423 (12)0.0495 (12)0.0032 (10)0.0189 (10)0.0029 (10)
C19B0.0543 (14)0.0480 (13)0.0507 (13)0.0007 (11)0.0252 (11)0.0010 (11)
C20B0.0645 (16)0.0551 (15)0.0562 (14)0.0073 (12)0.0241 (12)0.0041 (12)
C21B0.091 (2)0.0682 (18)0.0601 (16)0.0163 (16)0.0282 (15)0.0138 (14)
C22B0.114 (3)0.0651 (19)0.0743 (19)0.0137 (19)0.0430 (19)0.0230 (16)
C23B0.097 (2)0.0599 (17)0.083 (2)0.0063 (16)0.0438 (19)0.0130 (16)
C24B0.0683 (17)0.0480 (14)0.0645 (15)0.0057 (12)0.0332 (13)0.0017 (12)
C25B0.0593 (17)0.0595 (16)0.0766 (18)0.0156 (13)0.0302 (14)0.0034 (14)
C26B0.0491 (14)0.0579 (15)0.0633 (15)0.0032 (12)0.0196 (12)0.0036 (12)
C27B0.0506 (16)0.0735 (19)0.0830 (19)0.0062 (14)0.0142 (14)0.0065 (17)
C280.0576 (18)0.083 (2)0.077 (2)0.0092 (16)0.0033 (14)0.0014 (17)
C29B0.076 (2)0.0735 (19)0.0629 (16)0.0119 (16)0.0098 (14)0.0067 (14)
C30B0.0637 (17)0.0614 (16)0.0612 (15)0.0013 (13)0.0134 (13)0.0081 (13)
C31B0.0506 (14)0.0494 (13)0.0510 (13)0.0010 (11)0.0170 (11)0.0045 (11)
O1W0.0707 (15)0.1076 (19)0.0831 (15)0.0086 (13)0.0105 (11)0.0244 (14)
O2W0.205 (3)0.0729 (14)0.0905 (17)0.0040 (18)0.069 (2)0.0422 (13)
O3W0.0789 (15)0.1150 (18)0.130 (2)0.0353 (14)0.0415 (14)0.0838 (17)
Geometric parameters (Å, º) top
N1A—C2A1.349 (2)C13B—H13B0.9300
N1A—C6A1.362 (3)C14B—H14D0.9600
N1A—H1A0.8600C14B—H14E0.9600
N2A—C2A1.318 (3)C14B—H14F0.9600
N2A—H2A0.8600C15B—H15D0.9600
N2A—H2B0.8600C15B—H15E0.9600
N3A—C2A1.332 (2)C15B—H15F0.9600
N3A—C4A1.340 (3)C16B—H16D0.9600
N4A—C4A1.323 (3)C16B—H16E0.9600
N4A—H4A0.8600C16B—H16F0.9600
N4A—H4B0.8600O1A—C17A1.249 (3)
O10A—C10A1.364 (3)O2A—C17A1.235 (3)
O10A—C14A1.427 (3)C17A—C18A1.512 (3)
O11A—C11A1.377 (3)C18A—C19A1.399 (3)
O11A—C151.419 (4)C18A—C31A1.400 (3)
O12A—C12A1.365 (3)C19A—C20A1.421 (4)
O12A—C161.431 (4)C19A—C24A1.428 (4)
C4A—C5A1.436 (3)C20A—C21A1.345 (5)
C5A—C6A1.340 (3)C20A—H20A0.9300
C5A—C7A1.513 (3)C21A—C22A1.417 (6)
C6A—H6C0.9300C21A—H21A0.9300
C7A—C8A1.506 (3)C22A—C23A1.335 (6)
C7A—H7C0.9700C22A—H22A0.9300
C7A—H7D0.9700C23A—C24A1.434 (4)
C8A—C13A1.384 (3)C23A—H23A0.9300
C8A—C9A1.386 (3)C24A—C25A1.379 (4)
C9A—C10A1.388 (3)C25A—C26A1.384 (4)
C9A—H9A0.9300C25A—H25A0.9300
C10A—C11A1.386 (3)C26A—C27A1.419 (4)
C11A—C12A1.382 (3)C26A—C31A1.439 (3)
C12A—C13A1.386 (3)C27A—C28A1.329 (5)
C13A—H13A0.9300C27A—H27A0.9300
C14A—H14A0.9600C28A—C29A1.407 (5)
C14A—H14B0.9600C28A—H28A0.9300
C14A—H14C0.9600C29A—C30A1.352 (4)
C15—H15A0.9600C29A—H29A0.9300
C15—H15B0.9600C30A—C31A1.421 (4)
C15—H15C0.9600C30A—H30A0.9300
C16—H16A0.9600O1B—C17B1.243 (3)
C16—H16B0.9600O2B—C17B1.252 (3)
C16—H16C0.9600C17B—C18B1.503 (3)
N1B—C2B1.348 (3)C18B—C19B1.395 (3)
N1B—C6B1.363 (3)C18B—C31B1.409 (3)
N1B—H1B0.8600C19B—C20B1.429 (4)
N2B—C2B1.333 (3)C19B—C24B1.438 (3)
N2B—H2C0.8600C20B—C21B1.347 (4)
N2B—H2D0.8600C20B—H20B0.9300
N3B—C2B1.319 (3)C21B—C22B1.416 (4)
N3B—C4B1.344 (3)C21B—H21B0.9300
N4B—C4B1.318 (3)C22B—C23B1.348 (5)
N4B—H4C0.8600C22B—H22B0.9300
N4B—H4D0.8600C23B—C24B1.424 (4)
O10B—C10B1.360 (3)C23B—H23B0.9300
O10B—C14B1.420 (3)C24B—C25B1.389 (4)
O11B—C11B1.375 (3)C25B—C26B1.391 (4)
O11B—C15B1.402 (4)C25B—H25B0.9300
O12B—C12B1.365 (3)C26B—C31B1.425 (3)
O12B—C16B1.405 (4)C26B—C27B1.434 (4)
C4B—C5B1.436 (3)C27B—C281.337 (4)
C5B—C6B1.342 (3)C27B—H27B0.9300
C5B—C7B1.505 (3)C28—C29B1.394 (4)
C6B—H6D0.9300C28—H28B0.9300
C7B—C8B1.511 (3)C29B—C30B1.363 (4)
C7B—H7E0.9700C29B—H29B0.9300
C7B—H7F0.9700C30B—C31B1.418 (4)
C8B—C13B1.377 (3)C30B—H30B0.9300
C8B—C9B1.377 (3)O1W—H1W0.820 (2)
C9B—C10B1.390 (3)O1W—H2W0.820 (2)
C9B—H9B0.9300O2W—H4W0.820 (2)
C10B—C11B1.390 (3)O2W—H3W0.820 (2)
C11B—C12B1.385 (3)O3W—H5W0.820 (2)
C12B—C13B1.390 (3)O3W—H6W0.820 (2)
C2A—N1A—C6A120.10 (17)C8B—C13B—H13B120.1
C2A—N1A—H1A120.0C12B—C13B—H13B120.1
C6A—N1A—H1A120.0O10B—C14B—H14D109.5
C2A—N2A—H2A120.0O10B—C14B—H14E109.5
C2A—N2A—H2B120.0H14D—C14B—H14E109.5
H2A—N2A—H2B120.0O10B—C14B—H14F109.5
C2A—N3A—C4A118.37 (16)H14D—C14B—H14F109.5
C4A—N4A—H4A120.0H14E—C14B—H14F109.5
C4A—N4A—H4B120.0O11B—C15B—H15D109.5
H4A—N4A—H4B120.0O11B—C15B—H15E109.5
C10A—O10A—C14A117.95 (18)H15D—C15B—H15E109.5
C11A—O11A—C15115.6 (2)O11B—C15B—H15F109.5
C12A—O12A—C16118.5 (3)H15D—C15B—H15F109.5
N2A—C2A—N3A119.51 (17)H15E—C15B—H15F109.5
N2A—C2A—N1A118.60 (18)O12B—C16B—H16D109.5
N3A—C2A—N1A121.89 (18)O12B—C16B—H16E109.5
N4A—C4A—N3A117.21 (18)H16D—C16B—H16E109.5
N4A—C4A—C5A120.70 (19)O12B—C16B—H16F109.5
N3A—C4A—C5A122.09 (18)H16D—C16B—H16F109.5
C6A—C5A—C4A115.94 (18)H16E—C16B—H16F109.5
C6A—C5A—C7A124.73 (18)O2A—C17A—O1A124.9 (2)
C4A—C5A—C7A119.30 (18)O2A—C17A—C18A118.71 (19)
C5A—C6A—N1A121.44 (18)O1A—C17A—C18A116.37 (19)
C5A—C6A—H6C119.3C19A—C18A—C31A121.0 (2)
N1A—C6A—H6C119.3C19A—C18A—C17A119.4 (2)
C8A—C7A—C5A115.62 (18)C31A—C18A—C17A119.6 (2)
C8A—C7A—H7C108.4C18A—C19A—C20A122.3 (3)
C5A—C7A—H7C108.4C18A—C19A—C24A119.1 (2)
C8A—C7A—H7D108.4C20A—C19A—C24A118.5 (3)
C5A—C7A—H7D108.4C21A—C20A—C19A121.1 (4)
H7C—C7A—H7D107.4C21A—C20A—H20A119.5
C13A—C8A—C9A119.9 (2)C19A—C20A—H20A119.5
C13A—C8A—C7A120.3 (2)C20A—C21A—C22A120.4 (4)
C9A—C8A—C7A119.7 (2)C20A—C21A—H21A119.8
C8A—C9A—C10A120.0 (2)C22A—C21A—H21A119.8
C8A—C9A—H9A120.0C23A—C22A—C21A121.0 (4)
C10A—C9A—H9A120.0C23A—C22A—H22A119.5
O10A—C10A—C11A115.16 (19)C21A—C22A—H22A119.5
O10A—C10A—C9A125.0 (2)C22A—C23A—C24A120.8 (4)
C11A—C10A—C9A119.8 (2)C22A—C23A—H23A119.6
O11A—C11A—C12A121.6 (2)C24A—C23A—H23A119.6
O11A—C11A—C10A118.1 (2)C25A—C24A—C19A119.6 (2)
C12A—C11A—C10A120.1 (2)C25A—C24A—C23A122.2 (3)
O12A—C12A—C11A115.2 (2)C19A—C24A—C23A118.2 (3)
O12A—C12A—C13A124.9 (2)C24A—C25A—C26A122.2 (2)
C11A—C12A—C13A120.0 (2)C24A—C25A—H25A118.9
C8A—C13A—C12A120.1 (2)C26A—C25A—H25A118.9
C8A—C13A—H13A119.9C25A—C26A—C27A122.3 (3)
C12A—C13A—H13A119.9C25A—C26A—C31A118.9 (2)
O10A—C14A—H14A109.5C27A—C26A—C31A118.7 (3)
O10A—C14A—H14B109.5C28A—C27A—C26A121.4 (3)
H14A—C14A—H14B109.5C28A—C27A—H27A119.3
O10A—C14A—H14C109.5C26A—C27A—H27A119.3
H14A—C14A—H14C109.5C27A—C28A—C29A120.7 (3)
H14B—C14A—H14C109.5C27A—C28A—H28A119.7
O11A—C15—H15A109.5C29A—C28A—H28A119.7
O11A—C15—H15B109.5C30A—C29A—C28A120.7 (3)
H15A—C15—H15B109.5C30A—C29A—H29A119.7
O11A—C15—H15C109.5C28A—C29A—H29A119.7
H15A—C15—H15C109.5C29A—C30A—C31A121.2 (3)
H15B—C15—H15C109.5C29A—C30A—H30A119.4
O12A—C16—H16A109.5C31A—C30A—H30A119.4
O12A—C16—H16B109.5C18A—C31A—C30A123.5 (2)
H16A—C16—H16B109.5C18A—C31A—C26A119.1 (2)
O12A—C16—H16C109.5C30A—C31A—C26A117.4 (2)
H16A—C16—H16C109.5O1B—C17B—O2B126.7 (3)
H16B—C16—H16C109.5O1B—C17B—C18B117.3 (3)
C2B—N1B—C6B120.32 (17)O2B—C17B—C18B116.0 (2)
C2B—N1B—H1B119.8C19B—C18B—C31B121.3 (2)
C6B—N1B—H1B119.8C19B—C18B—C17B119.0 (2)
C2B—N2B—H2C120.0C31B—C18B—C17B119.7 (2)
C2B—N2B—H2D120.0C18B—C19B—C20B122.6 (2)
H2C—N2B—H2D120.0C18B—C19B—C24B119.1 (2)
C2B—N3B—C4B118.65 (17)C20B—C19B—C24B118.3 (2)
C4B—N4B—H4C120.0C21B—C20B—C19B121.1 (3)
C4B—N4B—H4D120.0C21B—C20B—H20B119.5
H4C—N4B—H4D120.0C19B—C20B—H20B119.5
C10B—O10B—C14B118.3 (2)C20B—C21B—C22B120.7 (3)
C11B—O11B—C15B114.8 (2)C20B—C21B—H21B119.7
C12B—O12B—C16B118.3 (2)C22B—C21B—H21B119.7
N3B—C2B—N2B119.52 (19)C23B—C22B—C21B120.5 (3)
N3B—C2B—N1B121.91 (19)C23B—C22B—H22B119.8
N2B—C2B—N1B118.56 (19)C21B—C22B—H22B119.8
N4B—C4B—N3B117.56 (18)C22B—C23B—C24B121.4 (3)
N4B—C4B—C5B120.38 (19)C22B—C23B—H23B119.3
N3B—C4B—C5B122.07 (18)C24B—C23B—H23B119.3
C6B—C5B—C4B115.80 (19)C25B—C24B—C23B122.8 (3)
C6B—C5B—C7B124.54 (18)C25B—C24B—C19B119.0 (2)
C4B—C5B—C7B119.65 (17)C23B—C24B—C19B118.1 (3)
C5B—C6B—N1B121.19 (19)C24B—C25B—C26B122.2 (2)
C5B—C6B—H6D119.4C24B—C25B—H25B118.9
N1B—C6B—H6D119.4C26B—C25B—H25B118.9
C5B—C7B—C8B114.87 (17)C25B—C26B—C31B119.1 (2)
C5B—C7B—H7E108.5C25B—C26B—C27B122.6 (3)
C8B—C7B—H7E108.6C31B—C26B—C27B118.2 (3)
C5B—C7B—H7F108.6C28—C27B—C26B121.2 (3)
C8B—C7B—H7F108.5C28—C27B—H27B119.4
H7E—C7B—H7F107.5C26B—C27B—H27B119.4
C13B—C8B—C9B120.3 (2)C27B—C28—C29B120.8 (3)
C13B—C8B—C7B120.2 (2)C27B—C28—H28B119.6
C9B—C8B—C7B119.5 (2)C29B—C28—H28B119.6
C8B—C9B—C10B120.3 (2)C30B—C29B—C28120.7 (3)
C8B—C9B—H9B119.8C30B—C29B—H29B119.7
C10B—C9B—H9B119.8C28—C29B—H29B119.7
O10B—C10B—C11B116.0 (2)C29B—C30B—C31B120.9 (3)
O10B—C10B—C9B124.3 (2)C29B—C30B—H30B119.5
C11B—C10B—C9B119.7 (2)C31B—C30B—H30B119.5
O11B—C11B—C12B121.3 (2)C18B—C31B—C30B122.6 (2)
O11B—C11B—C10B119.0 (2)C18B—C31B—C26B119.2 (2)
C12B—C11B—C10B119.6 (2)C30B—C31B—C26B118.2 (2)
O12B—C12B—C11B115.1 (2)H1W—O1W—H2W119 (4)
O12B—C12B—C13B124.6 (2)H4W—O2W—H3W110 (5)
C11B—C12B—C13B120.3 (2)H5W—O3W—H6W109 (4)
C8B—C13B—C12B119.8 (2)
C4A—N3A—C2A—N2A179.8 (2)C11B—C12B—C13B—C8B0.3 (3)
C4A—N3A—C2A—N1A0.6 (3)O2A—C17A—C18A—C19A97.1 (3)
C6A—N1A—C2A—N2A177.6 (2)O1A—C17A—C18A—C19A82.6 (3)
C6A—N1A—C2A—N3A3.2 (3)O2A—C17A—C18A—C31A82.8 (3)
C2A—N3A—C4A—N4A176.6 (2)O1A—C17A—C18A—C31A97.5 (3)
C2A—N3A—C4A—C5A3.2 (3)C31A—C18A—C19A—C20A178.7 (2)
N4A—C4A—C5A—C6A175.4 (2)C17A—C18A—C19A—C20A1.2 (3)
N3A—C4A—C5A—C6A4.5 (3)C31A—C18A—C19A—C24A0.0 (3)
N4A—C4A—C5A—C7A2.8 (3)C17A—C18A—C19A—C24A179.92 (19)
N3A—C4A—C5A—C7A177.3 (2)C18A—C19A—C20A—C21A178.1 (3)
C4A—C5A—C6A—N1A1.9 (3)C24A—C19A—C20A—C21A0.7 (4)
C7A—C5A—C6A—N1A180.0 (2)C19A—C20A—C21A—C22A1.6 (5)
C2A—N1A—C6A—C5A1.7 (3)C20A—C21A—C22A—C23A1.5 (6)
C6A—C5A—C7A—C8A4.8 (4)C21A—C22A—C23A—C24A0.3 (5)
C4A—C5A—C7A—C8A177.2 (2)C18A—C19A—C24A—C25A0.2 (3)
C5A—C7A—C8A—C13A99.0 (3)C20A—C19A—C24A—C25A178.6 (2)
C5A—C7A—C8A—C9A83.5 (3)C18A—C19A—C24A—C23A179.2 (2)
C13A—C8A—C9A—C10A1.4 (3)C20A—C19A—C24A—C23A0.4 (3)
C7A—C8A—C9A—C10A176.2 (2)C22A—C23A—C24A—C25A178.4 (3)
C14A—O10A—C10A—C11A174.6 (2)C22A—C23A—C24A—C19A0.6 (4)
C14A—O10A—C10A—C9A5.9 (3)C19A—C24A—C25A—C26A0.3 (3)
C8A—C9A—C10A—O10A179.0 (2)C23A—C24A—C25A—C26A179.3 (2)
C8A—C9A—C10A—C11A0.4 (3)C24A—C25A—C26A—C27A179.7 (2)
C15—O11A—C11A—C12A72.9 (4)C24A—C25A—C26A—C31A0.3 (3)
C15—O11A—C11A—C10A112.1 (3)C25A—C26A—C27A—C28A179.8 (3)
O10A—C10A—C11A—O11A4.3 (3)C31A—C26A—C27A—C28A0.4 (4)
C9A—C10A—C11A—O11A176.3 (2)C26A—C27A—C28A—C29A0.8 (5)
O10A—C10A—C11A—C12A179.3 (2)C27A—C28A—C29A—C30A1.0 (5)
C9A—C10A—C11A—C12A1.2 (3)C28A—C29A—C30A—C31A0.7 (5)
C16—O12A—C12A—C11A178.4 (3)C19A—C18A—C31A—C30A179.7 (2)
C16—O12A—C12A—C13A2.8 (4)C17A—C18A—C31A—C30A0.2 (3)
O11A—C11A—C12A—O12A2.1 (3)C19A—C18A—C31A—C26A0.0 (3)
C10A—C11A—C12A—O12A177.0 (2)C17A—C18A—C31A—C26A179.89 (19)
O11A—C11A—C12A—C13A176.8 (2)C29A—C30A—C31A—C18A179.4 (2)
C10A—C11A—C12A—C13A1.9 (3)C29A—C30A—C31A—C26A0.3 (4)
C9A—C8A—C13A—C12A0.7 (3)C25A—C26A—C31A—C18A0.1 (3)
C7A—C8A—C13A—C12A176.8 (2)C27A—C26A—C31A—C18A179.5 (2)
O12A—C12A—C13A—C8A177.8 (2)C25A—C26A—C31A—C30A179.6 (2)
C11A—C12A—C13A—C8A0.9 (3)C27A—C26A—C31A—C30A0.2 (3)
C4B—N3B—C2B—N2B178.0 (2)O1B—C17B—C18B—C19B85.0 (3)
C4B—N3B—C2B—N1B2.5 (3)O2B—C17B—C18B—C19B92.6 (3)
C6B—N1B—C2B—N3B1.7 (3)O1B—C17B—C18B—C31B95.5 (3)
C6B—N1B—C2B—N2B178.8 (2)O2B—C17B—C18B—C31B86.9 (3)
C2B—N3B—C4B—N4B178.9 (2)C31B—C18B—C19B—C20B178.9 (2)
C2B—N3B—C4B—C5B1.0 (3)C17B—C18B—C19B—C20B1.6 (3)
N4B—C4B—C5B—C6B178.8 (2)C31B—C18B—C19B—C24B0.9 (3)
N3B—C4B—C5B—C6B1.4 (3)C17B—C18B—C19B—C24B178.7 (2)
N4B—C4B—C5B—C7B2.3 (3)C18B—C19B—C20B—C21B179.8 (2)
N3B—C4B—C5B—C7B177.5 (2)C24B—C19B—C20B—C21B0.1 (3)
C4B—C5B—C6B—N1B2.2 (3)C19B—C20B—C21B—C22B0.2 (4)
C7B—C5B—C6B—N1B176.6 (2)C20B—C21B—C22B—C23B0.1 (4)
C2B—N1B—C6B—C5B0.9 (3)C21B—C22B—C23B—C24B0.0 (4)
C6B—C5B—C7B—C8B5.8 (3)C22B—C23B—C24B—C25B179.1 (3)
C4B—C5B—C7B—C8B175.4 (2)C22B—C23B—C24B—C19B0.1 (4)
C5B—C7B—C8B—C13B93.9 (3)C18B—C19B—C24B—C25B0.7 (3)
C5B—C7B—C8B—C9B86.4 (3)C20B—C19B—C24B—C25B179.1 (2)
C13B—C8B—C9B—C10B0.6 (3)C18B—C19B—C24B—C23B179.7 (2)
C7B—C8B—C9B—C10B179.1 (2)C20B—C19B—C24B—C23B0.0 (3)
C14B—O10B—C10B—C11B177.7 (2)C23B—C24B—C25B—C26B179.1 (2)
C14B—O10B—C10B—C9B3.3 (3)C19B—C24B—C25B—C26B0.0 (4)
C8B—C9B—C10B—O10B178.4 (2)C24B—C25B—C26B—C31B0.4 (4)
C8B—C9B—C10B—C11B0.7 (3)C24B—C25B—C26B—C27B179.1 (2)
C15B—O11B—C11B—C12B75.8 (3)C25B—C26B—C27B—C28179.2 (3)
C15B—O11B—C11B—C10B107.3 (3)C31B—C26B—C27B—C280.3 (4)
O10B—C10B—C11B—O11B4.5 (3)C26B—C27B—C28—C29B0.1 (4)
C9B—C10B—C11B—O11B176.4 (2)C27B—C28—C29B—C30B0.4 (4)
O10B—C10B—C11B—C12B178.5 (2)C28—C29B—C30B—C31B0.4 (4)
C9B—C10B—C11B—C12B0.6 (3)C19B—C18B—C31B—C30B178.5 (2)
C16B—O12B—C12B—C11B177.2 (2)C17B—C18B—C31B—C30B2.0 (3)
C16B—O12B—C12B—C13B4.3 (4)C19B—C18B—C31B—C26B0.4 (3)
O11B—C11B—C12B—O12B2.1 (3)C17B—C18B—C31B—C26B179.1 (2)
C10B—C11B—C12B—O12B179.0 (2)C29B—C30B—C31B—C18B178.9 (2)
O11B—C11B—C12B—C13B176.5 (2)C29B—C30B—C31B—C26B0.0 (4)
C10B—C11B—C12B—C13B0.4 (3)C25B—C26B—C31B—C18B0.2 (3)
C9B—C8B—C13B—C12B0.4 (3)C27B—C26B—C31B—C18B179.3 (2)
C7B—C8B—C13B—C12B179.3 (2)C25B—C26B—C31B—C30B179.2 (2)
O12B—C12B—C13B—C8B178.8 (2)C27B—C26B—C31B—C30B0.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O1A0.861.932.743 (3)158
N1B—H1B···O2W0.861.952.776 (3)160
O1W—H1W···O1Ai0.82 (3)2.01 (3)2.799 (3)162 (3)
N2A—H2A···N3Ai0.862.173.024 (2)174
N2A—H2B···O1A0.862.413.100 (3)138
N2A—H2B···O1Wi0.862.443.214 (3)150
N2B—H2C···O1Wii0.862.082.905 (3)159
N2B—H2D···O2W0.862.423.126 (3)140
O1W—H2W···O1Bi0.82 (3)1.89 (3)2.709 (4)175 (3)
O2W—H3W···O10Aiii0.82 (4)2.28 (4)3.006 (3)148 (4)
O2W—H3W···O11Aiii0.82 (4)2.50 (4)3.198 (3)144 (4)
N4A—H4B···O2Biv0.862.052.875 (3)160
N4B—H4C···O3Wv0.862.202.943 (3)145
N4B—H4D···O2Avi0.862.162.986 (3)161
O2W—H4W···O2B0.82 (3)1.86 (3)2.676 (3)171 (3)
O3W—H5W···N3Bv0.82 (3)2.22 (3)2.906 (3)142 (3)
O3W—H6W···O2A0.82 (3)1.92 (3)2.722 (3)166 (5)
C6B—H6D···O10Bvii0.932.353.205 (3)152
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z; (iii) x+1, y+1, z; (iv) x1, y, z; (v) x+2, y+1, z+1; (vi) x, y1, z; (vii) x+1, y, z.
2,4-Diamino-5-(4-chlorophenyl)-6-ethylpyrimidin-1-ium 2,5-dichlorothiophene-3-carboxylate (VI) top
Crystal data top
C12H14ClN4+·C5HCl2O2SZ = 2
Mr = 445.74F(000) = 456
Triclinic, P1Dx = 1.520 Mg m3
a = 9.3415 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.2751 (6) ÅCell parameters from 3007 reflections
c = 11.3730 (8) Åθ = 4.2–30.1°
α = 63.919 (7)°µ = 0.60 mm1
β = 85.243 (5)°T = 293 K
γ = 83.689 (5)°Prism, colorless
V = 973.80 (12) Å30.40 × 0.40 × 0.15 mm
Data collection top
Agilent SuperNova Dual Source
diffractometer with an Atlas detector
4449 independent reflections
Radiation source: SuperNova (Mo) X-ray Source3226 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.021
Detector resolution: 10.4933 pixels mm-1θmax = 27.5°, θmin = 2.9°
ω scansh = 1212
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
k = 1013
Tmin = 0.750, Tmax = 1.000l = 1414
9378 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054H-atom parameters constrained
wR(F2) = 0.164 w = 1/[σ2(Fo2) + (0.0758P)2 + 0.5521P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
4449 reflectionsΔρmax = 0.80 e Å3
245 parametersΔρmin = 0.62 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.21115 (12)1.24181 (8)0.15984 (10)0.0874 (3)
N10.3566 (2)0.3597 (2)0.2323 (2)0.0483 (5)
H10.33200.29160.21540.058*
N20.4866 (2)0.1871 (2)0.4012 (2)0.0510 (6)
H2B0.53820.16080.46840.061*
H2A0.46580.12360.37660.061*
N30.4705 (2)0.4241 (2)0.3730 (2)0.0425 (5)
N40.4505 (3)0.6600 (2)0.3411 (2)0.0511 (6)
H4A0.49360.63210.41330.061*
H4B0.42360.75050.29650.061*
C20.4391 (3)0.3251 (3)0.3359 (2)0.0413 (5)
C40.4257 (3)0.5637 (3)0.2987 (2)0.0400 (5)
C50.3519 (3)0.6083 (3)0.1799 (2)0.0424 (5)
C60.3118 (3)0.5008 (3)0.1539 (3)0.0502 (6)
C70.2123 (4)0.5236 (3)0.0460 (3)0.0708 (10)
H7B0.15000.44450.07780.085*
H7A0.15170.61330.02480.085*
C80.2910 (5)0.5304 (5)0.0722 (4)0.0973 (13)
H8C0.22400.54310.13670.146*
H8A0.35090.44160.05190.146*
H8B0.35010.61080.10600.146*
C90.3159 (3)0.7659 (3)0.0940 (2)0.0424 (5)
C100.1991 (3)0.8414 (3)0.1257 (3)0.0523 (6)
H100.14130.79310.19990.063*
C110.1677 (3)0.9878 (3)0.0481 (3)0.0561 (7)
H110.09011.03870.07050.067*
C120.2525 (3)1.0575 (3)0.0627 (3)0.0534 (7)
C130.3672 (3)0.9858 (3)0.0977 (3)0.0560 (7)
H130.42241.03420.17370.067*
C140.4000 (3)0.8395 (3)0.0182 (3)0.0504 (6)
H140.47910.79010.04000.060*
S10.12948 (9)0.16484 (12)0.44482 (10)0.0755 (3)
Cl20.09672 (10)0.13237 (10)0.24752 (10)0.0799 (3)
Cl30.00862 (15)0.45308 (11)0.63792 (11)0.1030 (4)
O10.2246 (2)0.1452 (2)0.2355 (2)0.0627 (6)
O20.3728 (2)0.0447 (2)0.3554 (2)0.0553 (5)
C150.0179 (3)0.0300 (3)0.3540 (3)0.0536 (7)
C160.1232 (3)0.0732 (3)0.3801 (3)0.0448 (6)
C170.1415 (3)0.2201 (3)0.4775 (3)0.0525 (6)
H170.23050.26830.50820.063*
C180.0167 (4)0.2808 (4)0.5196 (3)0.0645 (8)
C190.2496 (3)0.0166 (3)0.3186 (3)0.0470 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1212 (8)0.0349 (4)0.0871 (7)0.0069 (4)0.0239 (6)0.0089 (4)
N10.0672 (14)0.0323 (10)0.0461 (12)0.0060 (9)0.0185 (10)0.0144 (9)
N20.0623 (13)0.0336 (10)0.0549 (14)0.0009 (9)0.0219 (11)0.0144 (10)
N30.0498 (11)0.0363 (10)0.0412 (11)0.0040 (8)0.0121 (9)0.0147 (9)
N40.0691 (14)0.0376 (11)0.0491 (13)0.0017 (10)0.0213 (11)0.0185 (10)
C20.0453 (12)0.0339 (11)0.0421 (13)0.0053 (9)0.0070 (10)0.0129 (10)
C40.0452 (12)0.0348 (11)0.0382 (13)0.0079 (9)0.0051 (10)0.0124 (10)
C50.0539 (14)0.0329 (11)0.0373 (13)0.0061 (10)0.0088 (10)0.0107 (10)
C60.0708 (17)0.0355 (12)0.0412 (14)0.0061 (12)0.0154 (12)0.0113 (11)
C70.112 (3)0.0410 (15)0.0560 (19)0.0004 (16)0.0343 (18)0.0144 (14)
C80.104 (3)0.107 (3)0.091 (3)0.014 (3)0.025 (2)0.054 (3)
C90.0559 (14)0.0335 (12)0.0380 (13)0.0042 (10)0.0123 (11)0.0139 (10)
C100.0652 (17)0.0480 (15)0.0401 (14)0.0023 (12)0.0054 (12)0.0158 (12)
C110.0667 (17)0.0515 (15)0.0514 (17)0.0107 (13)0.0152 (14)0.0250 (14)
C120.0734 (18)0.0335 (12)0.0527 (17)0.0025 (12)0.0218 (14)0.0152 (12)
C130.0667 (17)0.0377 (13)0.0533 (17)0.0134 (12)0.0012 (13)0.0084 (12)
C140.0559 (15)0.0387 (13)0.0517 (16)0.0026 (11)0.0039 (12)0.0151 (12)
S10.0624 (5)0.0995 (7)0.0784 (6)0.0239 (5)0.0116 (4)0.0496 (6)
Cl20.0761 (6)0.0808 (6)0.0842 (6)0.0264 (4)0.0292 (5)0.0403 (5)
Cl30.1455 (10)0.0716 (6)0.0807 (7)0.0497 (6)0.0346 (7)0.0203 (5)
O10.0803 (13)0.0369 (10)0.0644 (13)0.0122 (9)0.0298 (11)0.0097 (9)
O20.0557 (11)0.0482 (10)0.0553 (12)0.0064 (8)0.0137 (9)0.0139 (9)
C150.0612 (16)0.0568 (16)0.0516 (16)0.0012 (13)0.0065 (13)0.0316 (14)
C160.0566 (14)0.0395 (12)0.0427 (14)0.0061 (11)0.0065 (11)0.0207 (11)
C170.0665 (17)0.0426 (14)0.0475 (16)0.0095 (12)0.0007 (13)0.0178 (12)
C180.083 (2)0.0579 (17)0.0558 (18)0.0221 (15)0.0138 (16)0.0271 (15)
C190.0624 (16)0.0365 (12)0.0440 (14)0.0065 (11)0.0159 (12)0.0161 (11)
Geometric parameters (Å, º) top
Cl1—C121.740 (3)C9—C101.384 (4)
N1—C21.354 (3)C9—C141.390 (4)
N1—C61.365 (3)C10—C111.381 (4)
N1—H10.8600C10—H100.9300
N2—C21.323 (3)C11—C121.377 (4)
N2—H2B0.8600C11—H110.9300
N2—H2A0.8600C12—C131.365 (4)
N3—C21.327 (3)C13—C141.386 (4)
N3—C41.345 (3)C13—H130.9300
N4—C41.324 (3)C14—H140.9300
N4—H4A0.8600S1—C181.718 (4)
N4—H4B0.8600S1—C151.719 (3)
C4—C51.433 (3)Cl2—C151.701 (3)
C5—C61.357 (3)Cl3—C181.716 (3)
C5—C91.494 (3)O1—C191.251 (3)
C6—C71.522 (4)O2—C191.259 (3)
C7—C81.456 (6)C15—C161.358 (4)
C7—H7B0.9700C16—C171.429 (4)
C7—H7A0.9700C16—C191.506 (4)
C8—H8C0.9600C17—C181.335 (4)
C8—H8A0.9600C17—H170.9300
C8—H8B0.9600
C2—N1—C6121.2 (2)C10—C9—C14118.9 (2)
C2—N1—H1119.4C10—C9—C5120.5 (2)
C6—N1—H1119.4C14—C9—C5120.6 (2)
C2—N2—H2B120.0C11—C10—C9120.6 (3)
C2—N2—H2A120.0C11—C10—H10119.7
H2B—N2—H2A120.0C9—C10—H10119.7
C2—N3—C4117.9 (2)C12—C11—C10119.1 (3)
C4—N4—H4A120.0C12—C11—H11120.4
C4—N4—H4B120.0C10—C11—H11120.4
H4A—N4—H4B120.0C13—C12—C11121.7 (2)
N2—C2—N3120.6 (2)C13—C12—Cl1119.6 (2)
N2—C2—N1117.4 (2)C11—C12—Cl1118.6 (2)
N3—C2—N1122.0 (2)C12—C13—C14118.9 (3)
N4—C4—N3117.1 (2)C12—C13—H13120.6
N4—C4—C5120.6 (2)C14—C13—H13120.6
N3—C4—C5122.3 (2)C13—C14—C9120.8 (3)
C6—C5—C4116.6 (2)C13—C14—H14119.6
C6—C5—C9122.7 (2)C9—C14—H14119.6
C4—C5—C9120.6 (2)C18—S1—C1590.36 (15)
C5—C6—N1119.3 (2)C16—C15—Cl2130.2 (2)
C5—C6—C7124.9 (2)C16—C15—S1112.6 (2)
N1—C6—C7115.7 (2)Cl2—C15—S1117.20 (17)
C8—C7—C6112.5 (3)C15—C16—C17111.4 (3)
C8—C7—H7B109.1C15—C16—C19126.8 (2)
C6—C7—H7B109.1C17—C16—C19121.8 (2)
C8—C7—H7A109.1C18—C17—C16112.6 (3)
C6—C7—H7A109.1C18—C17—H17123.7
H7B—C7—H7A107.8C16—C17—H17123.7
C7—C8—H8C109.5C17—C18—Cl3127.2 (3)
C7—C8—H8A109.5C17—C18—S1113.0 (3)
H8C—C8—H8A109.5Cl3—C18—S1119.8 (2)
C7—C8—H8B109.5O1—C19—O2125.1 (3)
H8C—C8—H8B109.5O1—C19—C16118.0 (2)
H8A—C8—H8B109.5O2—C19—C16116.9 (2)
C4—N3—C2—N2176.6 (2)C9—C10—C11—C121.1 (4)
C4—N3—C2—N14.4 (4)C10—C11—C12—C130.2 (4)
C6—N1—C2—N2175.3 (3)C10—C11—C12—Cl1179.7 (2)
C6—N1—C2—N35.7 (4)C11—C12—C13—C141.1 (4)
C2—N3—C4—N4176.2 (2)Cl1—C12—C13—C14179.0 (2)
C2—N3—C4—C52.7 (4)C12—C13—C14—C91.4 (4)
N4—C4—C5—C6170.4 (3)C10—C9—C14—C130.5 (4)
N3—C4—C5—C68.5 (4)C5—C9—C14—C13179.7 (2)
N4—C4—C5—C96.8 (4)C18—S1—C15—C160.3 (2)
N3—C4—C5—C9174.4 (2)C18—S1—C15—Cl2179.96 (18)
C4—C5—C6—N17.2 (4)Cl2—C15—C16—C17180.0 (2)
C9—C5—C6—N1175.8 (3)S1—C15—C16—C170.4 (3)
C4—C5—C6—C7169.6 (3)Cl2—C15—C16—C190.3 (4)
C9—C5—C6—C77.4 (5)S1—C15—C16—C19179.9 (2)
C2—N1—C6—C50.6 (4)C15—C16—C17—C180.3 (3)
C2—N1—C6—C7176.5 (3)C19—C16—C17—C18180.0 (2)
C5—C6—C7—C897.2 (4)C16—C17—C18—Cl3178.4 (2)
N1—C6—C7—C885.9 (4)C16—C17—C18—S10.1 (3)
C6—C5—C9—C1098.4 (3)C15—S1—C18—C170.1 (3)
C4—C5—C9—C1078.5 (3)C15—S1—C18—Cl3178.4 (2)
C6—C5—C9—C1482.4 (4)C15—C16—C19—O10.8 (4)
C4—C5—C9—C14100.7 (3)C17—C16—C19—O1178.9 (2)
C14—C9—C10—C110.8 (4)C15—C16—C19—O2179.2 (3)
C5—C9—C10—C11178.4 (2)C17—C16—C19—O21.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.861.822.627 (3)155
N2—H2A···O20.862.132.969 (3)165
N2—H2B···O2i0.862.022.855 (3)163
N4—H4A···N3ii0.862.283.107 (3)160
N4—H4B···O2iii0.862.463.113 (3)133
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y+1, z+1; (iii) x, y+1, z.
2,4-Diamino-5-(4-chlorophenyl)-6-ethylpyrimidin-1-ium 5-bromothiophene-2-carboxylate (VII) top
Crystal data top
C12H14ClN4+·C5H2BrO2SF(000) = 1840
Mr = 455.76Dx = 1.513 Mg m3
Monoclinic, C2/cCu Kα radiation, λ = 1.54184 Å
a = 17.0836 (6) ÅCell parameters from 3232 reflections
b = 15.8893 (3) Åθ = 4.0–74.6°
c = 16.4764 (5) ŵ = 5.17 mm1
β = 116.538 (4)°T = 293 K
V = 4001.2 (2) Å3Prism, colorless
Z = 80.25 × 0.15 × 0.10 mm
Data collection top
Agilent SuperNova Dual Source
diffractometer with an Atlas detector
3801 independent reflections
Radiation source: SuperNova (Cu) X-ray Source3191 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.024
Detector resolution: 10.4933 pixels mm-1θmax = 70.1°, θmin = 4.0°
ω scansh = 2015
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
k = 1913
Tmin = 0.623, Tmax = 1.000l = 2018
7903 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.053 w = 1/[σ2(Fo2) + (0.0842P)2 + 5.1068P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.160(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.97 e Å3
3801 reflectionsΔρmin = 0.84 e Å3
283 parametersExtinction correction: SHELXT (Sheldrick, 2015a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
67 restraintsExtinction coefficient: 0.00072 (9)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.69998 (9)0.89606 (7)0.96608 (6)0.0831 (4)
N10.51122 (15)0.65646 (16)0.47653 (15)0.0445 (5)
H10.46330.62930.44660.053*
N20.54779 (19)0.62888 (19)0.36144 (17)0.0600 (7)
H2B0.58240.63290.33650.072*
H2A0.49900.60240.33420.072*
N30.64467 (15)0.70435 (15)0.48450 (14)0.0415 (5)
N40.73645 (16)0.78250 (17)0.60459 (16)0.0510 (6)
H4A0.77070.78560.57920.061*
H4B0.75060.80670.65590.061*
C20.56975 (19)0.66358 (18)0.44217 (17)0.0430 (6)
C40.66219 (17)0.74053 (16)0.56478 (17)0.0389 (5)
C50.60292 (17)0.73491 (17)0.60479 (17)0.0395 (6)
C60.52743 (17)0.69182 (18)0.55770 (17)0.0410 (6)
C70.45797 (19)0.6771 (2)0.5887 (2)0.0523 (7)
H7A0.46750.71530.63820.063*
H7B0.40110.68980.53920.063*
C80.4578 (4)0.5881 (3)0.6198 (4)0.0910 (14)
H8A0.44330.55040.56960.136*
H8B0.41530.58280.64270.136*
H8C0.51470.57440.66690.136*
C90.62628 (17)0.77495 (17)0.69469 (17)0.0398 (6)
C100.58558 (19)0.84802 (19)0.70127 (19)0.0461 (6)
H100.54260.87250.64910.055*
C110.6085 (2)0.88521 (19)0.7854 (2)0.0511 (7)
H110.58070.93420.78970.061*
C120.6720 (2)0.8491 (2)0.86128 (19)0.0524 (7)
C130.7135 (3)0.7772 (2)0.8570 (2)0.0619 (8)
H130.75680.75370.90950.074*
C140.6905 (2)0.7398 (2)0.7737 (2)0.0541 (7)
H140.71830.69050.77040.065*
S1A0.19412 (17)0.48790 (18)0.15394 (12)0.0550 (6)0.7687 (16)
C17A0.1247 (5)0.4217 (4)0.1722 (5)0.0629 (18)0.7687 (16)
C18A0.1514 (5)0.4039 (4)0.2609 (5)0.0631 (16)0.7687 (16)
H18A0.12050.36980.28240.076*0.7687 (16)
C19A0.2320 (10)0.4435 (10)0.3173 (10)0.058 (6)0.7687 (16)
H19A0.26170.43680.37990.070*0.7687 (16)
Br1A0.02332 (5)0.38313 (6)0.07422 (6)0.1213 (4)0.7687 (16)
S1B0.2280 (8)0.4399 (8)0.3148 (7)0.045 (3)0.2313 (16)
C18B0.1424 (15)0.4009 (14)0.2184 (12)0.059 (5)0.2313 (16)
C17B0.1400 (12)0.4402 (14)0.1451 (12)0.055 (5)0.2313 (16)
H17B0.09410.43480.08720.066*0.2313 (16)
C19B0.215 (2)0.491 (3)0.1652 (14)0.051 (7)0.2313 (16)
H19B0.23090.51570.12390.062*0.2313 (16)
C160.26188 (19)0.49522 (18)0.2650 (2)0.0476 (7)
Br1B0.06494 (14)0.32211 (14)0.2266 (2)0.1011 (10)0.2313 (16)
O10.38002 (16)0.55285 (17)0.38749 (15)0.0665 (7)
O20.35672 (16)0.59419 (17)0.24860 (16)0.0639 (6)
C150.33930 (19)0.55171 (19)0.30269 (19)0.0476 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1160 (9)0.0919 (7)0.0491 (5)0.0155 (6)0.0438 (5)0.0245 (4)
N10.0357 (11)0.0603 (14)0.0370 (11)0.0122 (10)0.0158 (9)0.0077 (10)
N20.0549 (15)0.0908 (19)0.0403 (13)0.0296 (14)0.0266 (12)0.0245 (13)
N30.0381 (11)0.0558 (13)0.0330 (10)0.0090 (10)0.0179 (9)0.0074 (9)
N40.0434 (13)0.0735 (16)0.0418 (12)0.0200 (12)0.0241 (11)0.0201 (11)
C20.0429 (14)0.0545 (15)0.0329 (12)0.0075 (12)0.0180 (11)0.0053 (11)
C40.0363 (13)0.0477 (13)0.0337 (12)0.0022 (10)0.0165 (10)0.0019 (10)
C50.0360 (13)0.0495 (14)0.0353 (12)0.0006 (11)0.0179 (11)0.0034 (10)
C60.0352 (13)0.0521 (14)0.0384 (13)0.0014 (11)0.0188 (11)0.0018 (11)
C70.0371 (14)0.0728 (19)0.0515 (16)0.0087 (13)0.0238 (13)0.0104 (14)
C80.102 (3)0.102 (3)0.096 (3)0.003 (3)0.068 (3)0.024 (3)
C90.0360 (13)0.0509 (14)0.0362 (12)0.0060 (11)0.0194 (10)0.0053 (10)
C100.0413 (14)0.0542 (15)0.0430 (14)0.0012 (12)0.0191 (12)0.0030 (11)
C110.0518 (17)0.0519 (15)0.0582 (18)0.0092 (13)0.0322 (15)0.0145 (13)
C120.0619 (19)0.0637 (18)0.0403 (14)0.0152 (15)0.0306 (14)0.0106 (13)
C130.071 (2)0.074 (2)0.0357 (15)0.0057 (17)0.0185 (15)0.0004 (14)
C140.0579 (18)0.0607 (17)0.0416 (15)0.0101 (14)0.0203 (14)0.0039 (13)
S1A0.0517 (13)0.0643 (10)0.0391 (6)0.0057 (9)0.0114 (6)0.0156 (5)
C17A0.050 (3)0.055 (4)0.075 (5)0.016 (3)0.020 (3)0.015 (3)
C18A0.059 (3)0.050 (3)0.086 (4)0.010 (2)0.037 (4)0.007 (3)
C19A0.040 (7)0.057 (9)0.071 (9)0.005 (6)0.020 (6)0.007 (6)
Br1A0.0880 (5)0.1293 (7)0.1002 (6)0.0533 (5)0.0004 (4)0.0370 (4)
S1B0.051 (6)0.047 (5)0.042 (4)0.008 (4)0.025 (4)0.000 (3)
C18B0.056 (11)0.046 (9)0.088 (16)0.019 (8)0.043 (13)0.015 (12)
C17B0.031 (7)0.064 (11)0.060 (10)0.017 (7)0.011 (6)0.024 (8)
C19B0.036 (12)0.068 (12)0.045 (8)0.028 (9)0.014 (8)0.002 (9)
C160.0388 (14)0.0487 (14)0.0502 (16)0.0009 (12)0.0154 (13)0.0105 (12)
Br1B0.0666 (13)0.0859 (14)0.149 (2)0.0304 (10)0.0466 (13)0.0133 (13)
O10.0555 (13)0.0873 (17)0.0455 (12)0.0266 (12)0.0124 (10)0.0044 (11)
O20.0578 (14)0.0851 (16)0.0518 (12)0.0132 (12)0.0270 (11)0.0004 (11)
C150.0373 (14)0.0580 (16)0.0442 (15)0.0027 (12)0.0153 (12)0.0057 (12)
Geometric parameters (Å, º) top
Cl1—C121.741 (3)C11—C121.363 (5)
N1—C21.356 (3)C11—H110.9300
N1—C61.360 (3)C12—C131.362 (5)
N1—H10.8600C13—C141.383 (4)
N2—C21.330 (3)C13—H130.9300
N2—H2B0.8600C14—H140.9300
N2—H2A0.8600S1A—C161.676 (3)
N3—C21.322 (4)S1A—C17A1.709 (7)
N3—C41.347 (3)C17A—C18A1.352 (9)
N4—C41.319 (3)C17A—Br1A1.867 (7)
N4—H4A0.8600C18A—C19A1.418 (16)
N4—H4B0.8600C18A—H18A0.9300
C4—C51.437 (4)C19A—C161.439 (13)
C5—C61.356 (4)C19A—H19A0.9300
C5—C91.493 (3)S1B—C161.486 (9)
C6—C71.505 (4)S1B—C18B1.723 (17)
C7—C81.504 (6)C18B—C17B1.344 (18)
C7—H7A0.9700C18B—Br1B1.870 (19)
C7—H7B0.9700C17B—C19B1.42 (2)
C8—H8A0.9600C17B—H17B0.9300
C8—H8B0.9600C19B—C161.47 (2)
C8—H8C0.9600C19B—H19B0.9300
C9—C101.382 (4)C16—C151.485 (4)
C9—C141.391 (4)Br1B—Br1Bi2.655 (5)
C10—C111.392 (4)O1—C151.252 (4)
C10—H100.9300O2—C151.255 (4)
C2—N1—C6120.8 (2)C12—C11—H11120.4
C2—N1—H1119.6C10—C11—H11120.4
C6—N1—H1119.6C13—C12—C11121.7 (3)
C2—N2—H2B120.0C13—C12—Cl1119.5 (3)
C2—N2—H2A120.0C11—C12—Cl1118.9 (2)
H2B—N2—H2A120.0C12—C13—C14119.3 (3)
C2—N3—C4117.7 (2)C12—C13—H13120.4
C4—N4—H4A120.0C14—C13—H13120.4
C4—N4—H4B120.0C13—C14—C9120.7 (3)
H4A—N4—H4B120.0C13—C14—H14119.6
N3—C2—N2120.3 (2)C9—C14—H14119.6
N3—C2—N1122.8 (2)C16—S1A—C17A92.6 (3)
N2—C2—N1116.9 (2)C18A—C17A—S1A113.2 (5)
N4—C4—N3116.5 (2)C18A—C17A—Br1A126.9 (6)
N4—C4—C5121.4 (2)S1A—C17A—Br1A119.9 (4)
N3—C4—C5122.1 (2)C17A—C18A—C19A112.0 (8)
C6—C5—C4117.0 (2)C17A—C18A—H18A124.0
C6—C5—C9123.2 (2)C19A—C18A—H18A124.0
C4—C5—C9119.9 (2)C18A—C19A—C16111.2 (10)
C5—C6—N1119.7 (2)C18A—C19A—H19A124.4
C5—C6—C7125.2 (2)C16—C19A—H19A124.4
N1—C6—C7115.1 (2)C16—S1B—C18B94.8 (8)
C8—C7—C6112.5 (3)C17B—C18B—S1B109.5 (13)
C8—C7—H7A109.1C17B—C18B—Br1B129.6 (14)
C6—C7—H7A109.1S1B—C18B—Br1B120.7 (11)
C8—C7—H7B109.1C18B—C17B—C19B113.0 (16)
C6—C7—H7B109.1C18B—C17B—H17B123.5
H7A—C7—H7B107.8C19B—C17B—H17B123.5
C7—C8—H8A109.5C17B—C19B—C16105.9 (17)
C7—C8—H8B109.5C17B—C19B—H19B127.0
H8A—C8—H8B109.5C16—C19B—H19B127.0
C7—C8—H8C109.5C19A—C16—C15125.7 (7)
H8A—C8—H8C109.5C19B—C16—C15115.9 (11)
H8B—C8—H8C109.5C19B—C16—S1B115.7 (10)
C10—C9—C14118.6 (2)C15—C16—S1B128.4 (5)
C10—C9—C5121.0 (2)C19A—C16—S1A110.9 (6)
C14—C9—C5120.4 (2)C15—C16—S1A123.3 (3)
C9—C10—C11120.5 (3)C18B—Br1B—Br1Bi137.0 (8)
C9—C10—H10119.8O1—C15—O2126.5 (3)
C11—C10—H10119.8O1—C15—C16115.0 (3)
C12—C11—C10119.3 (3)O2—C15—C16118.5 (3)
C4—N3—C2—N2177.9 (3)C10—C9—C14—C130.3 (5)
C4—N3—C2—N10.5 (4)C5—C9—C14—C13178.9 (3)
C6—N1—C2—N30.1 (4)C16—S1A—C17A—C18A0.4 (6)
C6—N1—C2—N2178.4 (3)C16—S1A—C17A—Br1A178.8 (4)
C2—N3—C4—N4178.5 (3)S1A—C17A—C18A—C19A1.2 (11)
C2—N3—C4—C50.8 (4)Br1A—C17A—C18A—C19A179.6 (8)
N4—C4—C5—C6178.7 (3)C17A—C18A—C19A—C162.6 (14)
N3—C4—C5—C60.5 (4)C16—S1B—C18B—C17B4 (2)
N4—C4—C5—C91.9 (4)C16—S1B—C18B—Br1B179.9 (15)
N3—C4—C5—C9179.0 (2)S1B—C18B—C17B—C19B10 (3)
C4—C5—C6—N10.0 (4)Br1B—C18B—C17B—C19B175 (3)
C9—C5—C6—N1179.4 (3)C18B—C17B—C19B—C1611 (4)
C4—C5—C6—C7178.6 (3)C18A—C19A—C16—C15174.0 (6)
C9—C5—C6—C70.9 (5)C18A—C19A—C16—S1A2.9 (12)
C2—N1—C6—C50.2 (4)C17B—C19B—C16—C15174.7 (18)
C2—N1—C6—C7178.5 (3)C17B—C19B—C16—S1B8 (3)
C5—C6—C7—C8105.8 (4)C18B—S1B—C16—C19B2 (2)
N1—C6—C7—C872.8 (4)C18B—S1B—C16—C15179.3 (10)
C6—C5—C9—C1074.2 (4)C17A—S1A—C16—C19A1.9 (7)
C4—C5—C9—C10106.4 (3)C17A—S1A—C16—C15175.1 (4)
C6—C5—C9—C14106.6 (3)C17B—C18B—Br1B—Br1Bi101 (3)
C4—C5—C9—C1472.8 (4)S1B—C18B—Br1B—Br1Bi74 (2)
C14—C9—C10—C110.2 (4)C19A—C16—C15—O10.3 (9)
C5—C9—C10—C11179.4 (3)C19B—C16—C15—O1178 (2)
C9—C10—C11—C120.5 (4)S1B—C16—C15—O10.9 (8)
C10—C11—C12—C130.2 (5)S1A—C16—C15—O1176.2 (3)
C10—C11—C12—Cl1179.9 (2)C19A—C16—C15—O2178.9 (8)
C11—C12—C13—C140.2 (5)C19B—C16—C15—O24 (2)
Cl1—C12—C13—C14179.5 (3)S1B—C16—C15—O2179.5 (7)
C12—C13—C14—C90.5 (5)S1A—C16—C15—O22.4 (4)
Symmetry code: (i) x, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.861.792.636 (4)167
N2—H2A···O20.862.202.999 (4)154
N2—H2B···O2ii0.862.172.983 (4)156
N4—H4A···N3iii0.862.142.998 (4)179
N4—H4B···O2iv0.862.373.055 (4)137
Symmetry codes: (ii) x+1, y, z+1/2; (iii) x+3/2, y+3/2, z+1; (iv) x+1/2, y+3/2, z+1/2.
2,4-Diamino-5-(4-chlorophenyl)-6-ethylpyrimidin-1-ium anthracene-9-carboxylate methanol monosolvate monohydrate (VIII) top
Crystal data top
C12H14ClN4+·C15H9O2·C2H6O·H2OF(000) = 1128
Mr = 535.03Dx = 1.257 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 9.5195 (5) ÅCell parameters from 3464 reflections
b = 15.7842 (11) Åθ = 3.5–26.3°
c = 18.8336 (8) ŵ = 0.17 mm1
β = 92.293 (4)°T = 293 K
V = 2827.6 (3) Å3Prism, colorless
Z = 40.40 × 0.20 × 0.10 mm
Data collection top
Agilent SuperNova Dual Source
diffractometer with an Atlas detector
6466 independent reflections
Radiation source: SuperNova (Mo) X-ray Source3240 reflections with I > 2σ(I)
Detector resolution: 10.4933 pixels mm-1Rint = 0.036
ω scansθmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
h = 1212
Tmin = 0.521, Tmax = 1.000k = 2016
15577 measured reflectionsl = 2324
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.058 w = 1/[σ2(Fo2) + (0.0651P)2 + 0.1856P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.173(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.22 e Å3
6466 reflectionsΔρmin = 0.25 e Å3
364 parametersExtinction correction: SHELXL2014 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
9 restraintsExtinction coefficient: 0.0039 (9)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.13326 (11)0.14732 (7)0.10217 (5)0.1146 (4)
N10.20914 (19)0.50959 (13)0.16314 (8)0.0525 (5)
H10.18290.52800.20350.063*
N20.3892 (2)0.60564 (15)0.16893 (10)0.0695 (7)
H2B0.46190.62890.15140.083*
H2A0.35930.62290.20890.083*
N30.37026 (19)0.51682 (13)0.07231 (9)0.0540 (5)
N40.3470 (2)0.42930 (13)0.02286 (9)0.0607 (6)
H4A0.42120.45240.03880.073*
H4B0.30470.38970.04670.073*
C20.3238 (2)0.54371 (16)0.13453 (11)0.0518 (6)
C40.2979 (2)0.45465 (16)0.03846 (10)0.0492 (6)
C50.1740 (2)0.41696 (15)0.06574 (10)0.0464 (5)
C60.1338 (2)0.44692 (16)0.12996 (10)0.0497 (6)
C70.0096 (3)0.41584 (18)0.16882 (12)0.0640 (7)
H7A0.04730.37990.13740.077*
H7B0.04750.46400.18160.077*
C80.0508 (4)0.3667 (2)0.23539 (14)0.0986 (11)
H8A0.09980.40340.26860.148*
H8B0.11090.32040.22340.148*
H8C0.03220.34500.25640.148*
C90.0966 (2)0.35019 (16)0.02515 (10)0.0486 (6)
C100.0247 (3)0.36899 (18)0.03779 (13)0.0705 (8)
H100.02390.42450.05440.085*
C110.0467 (3)0.3069 (2)0.07691 (14)0.0793 (8)
H110.09540.32080.11910.095*
C120.0450 (3)0.2255 (2)0.05325 (14)0.0697 (8)
C130.0274 (3)0.2048 (2)0.00861 (15)0.0818 (9)
H130.02960.14890.02430.098*
C140.0969 (3)0.26707 (19)0.04751 (13)0.0685 (7)
H140.14490.25260.08970.082*
O10.09127 (19)0.59001 (14)0.27045 (9)0.0815 (6)
O20.2907 (2)0.65119 (15)0.30345 (10)0.0927 (7)
C150.1657 (3)0.63709 (18)0.31033 (12)0.0624 (7)
C160.0911 (3)0.68011 (18)0.37016 (11)0.0588 (7)
C170.0955 (3)0.64225 (18)0.43788 (12)0.0627 (7)
C180.1728 (3)0.5680 (2)0.45422 (14)0.0835 (9)
H180.22130.54120.41870.100*
C190.1778 (4)0.5350 (2)0.52095 (17)0.1066 (12)
H190.22990.48620.53060.128*
C200.1050 (5)0.5740 (3)0.57517 (18)0.1129 (13)
H200.11010.55120.62070.136*
C210.0288 (4)0.6432 (2)0.56222 (14)0.0899 (10)
H210.02040.66720.59890.108*
C220.0201 (3)0.6818 (2)0.49335 (12)0.0689 (8)
C230.0566 (3)0.7541 (2)0.47885 (13)0.0709 (8)
H230.10830.77790.51470.085*
C240.0595 (3)0.79269 (18)0.41272 (13)0.0634 (7)
C250.1360 (3)0.8682 (2)0.39747 (17)0.0798 (9)
H250.18930.89230.43260.096*
C260.1333 (3)0.9056 (2)0.33346 (19)0.0889 (9)
H260.18280.95560.32510.107*
C270.0553 (3)0.8693 (2)0.27877 (18)0.0897 (9)
H270.05360.89550.23460.108*
C280.0165 (3)0.7966 (2)0.29046 (14)0.0762 (8)
H280.06630.77340.25370.091*
C290.0184 (3)0.75462 (18)0.35686 (12)0.0594 (7)
O1W0.3231 (3)0.68555 (17)0.14092 (12)0.0941 (7)
H1W0.276 (4)0.666 (3)0.1754 (15)0.141*
H2W0.290 (4)0.7337 (12)0.140 (2)0.141*
O30.1936 (2)0.6008 (2)0.25040 (12)0.1119 (8)
H30.10880.59540.25860.168*
C300.2627 (5)0.6093 (4)0.31547 (17)0.160 (2)
H30A0.19490.59240.35260.192*0.443 (10)
H30B0.27860.66940.32190.192*0.443 (10)
H30C0.31490.55740.32290.192*0.557 (10)
H30D0.19090.61280.35340.192*0.557 (10)
C31A0.3908 (7)0.5686 (7)0.3311 (5)0.127 (5)0.443 (10)
H31A0.44910.60710.35620.191*0.443 (10)
H31B0.37120.51960.36020.191*0.443 (10)
H31C0.43870.55140.28770.191*0.443 (10)
C31B0.3465 (10)0.6708 (8)0.3229 (5)0.180 (6)0.557 (10)
H31D0.37230.67410.37160.270*0.557 (10)
H31E0.42920.66230.29290.270*0.557 (10)
H31F0.30130.72250.30980.270*0.557 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1323 (8)0.1142 (8)0.0979 (6)0.0528 (6)0.0100 (5)0.0311 (5)
N10.0507 (11)0.0695 (14)0.0382 (8)0.0002 (10)0.0144 (8)0.0086 (9)
N20.0630 (13)0.0932 (18)0.0536 (11)0.0182 (12)0.0182 (10)0.0250 (11)
N30.0537 (11)0.0672 (14)0.0420 (9)0.0026 (10)0.0135 (8)0.0073 (9)
N40.0675 (13)0.0715 (15)0.0446 (9)0.0133 (11)0.0207 (9)0.0107 (10)
C20.0489 (13)0.0648 (17)0.0421 (10)0.0034 (12)0.0081 (9)0.0042 (11)
C40.0519 (13)0.0592 (16)0.0371 (10)0.0055 (12)0.0095 (9)0.0013 (10)
C50.0484 (12)0.0537 (14)0.0373 (10)0.0048 (11)0.0059 (9)0.0040 (10)
C60.0497 (13)0.0600 (16)0.0400 (10)0.0059 (12)0.0080 (9)0.0028 (11)
C70.0623 (15)0.0766 (19)0.0549 (13)0.0059 (14)0.0238 (11)0.0100 (13)
C80.123 (3)0.112 (3)0.0623 (16)0.022 (2)0.0307 (17)0.0156 (17)
C90.0514 (13)0.0533 (16)0.0417 (11)0.0045 (11)0.0096 (9)0.0038 (11)
C100.094 (2)0.0572 (18)0.0593 (15)0.0020 (15)0.0141 (13)0.0041 (13)
C110.092 (2)0.084 (2)0.0606 (15)0.0015 (18)0.0209 (14)0.0046 (16)
C120.0746 (18)0.073 (2)0.0627 (15)0.0137 (15)0.0120 (13)0.0077 (14)
C130.111 (2)0.059 (2)0.0761 (18)0.0147 (18)0.0071 (17)0.0090 (16)
C140.0836 (19)0.068 (2)0.0538 (13)0.0003 (15)0.0003 (12)0.0092 (14)
O10.0658 (12)0.1105 (17)0.0692 (11)0.0030 (11)0.0159 (9)0.0410 (11)
O20.0651 (12)0.137 (2)0.0774 (12)0.0075 (12)0.0225 (10)0.0464 (12)
C150.0573 (16)0.080 (2)0.0501 (13)0.0047 (14)0.0100 (11)0.0135 (13)
C160.0559 (14)0.0694 (18)0.0519 (12)0.0022 (13)0.0134 (10)0.0165 (12)
C170.0690 (16)0.0671 (19)0.0529 (13)0.0061 (14)0.0135 (11)0.0135 (13)
C180.094 (2)0.090 (2)0.0673 (17)0.0136 (19)0.0186 (15)0.0008 (16)
C190.134 (3)0.107 (3)0.080 (2)0.023 (2)0.018 (2)0.010 (2)
C200.148 (3)0.122 (3)0.0705 (19)0.012 (3)0.025 (2)0.014 (2)
C210.109 (3)0.108 (3)0.0553 (16)0.002 (2)0.0266 (16)0.0072 (17)
C220.0773 (18)0.076 (2)0.0545 (14)0.0079 (16)0.0194 (12)0.0163 (14)
C230.0728 (17)0.082 (2)0.0594 (15)0.0074 (16)0.0246 (13)0.0239 (15)
C240.0574 (15)0.0628 (18)0.0706 (15)0.0043 (14)0.0117 (12)0.0208 (14)
C250.0693 (18)0.073 (2)0.098 (2)0.0008 (16)0.0175 (15)0.0196 (17)
C260.075 (2)0.073 (2)0.118 (2)0.0093 (17)0.0090 (18)0.003 (2)
C270.090 (2)0.088 (2)0.091 (2)0.007 (2)0.0105 (17)0.0118 (19)
C280.0755 (19)0.091 (2)0.0635 (15)0.0072 (17)0.0147 (13)0.0042 (16)
C290.0556 (14)0.0690 (18)0.0543 (13)0.0059 (13)0.0108 (11)0.0135 (13)
O1W0.0987 (17)0.1035 (19)0.0807 (13)0.0149 (14)0.0115 (11)0.0223 (14)
O30.0762 (14)0.157 (2)0.1023 (15)0.0081 (16)0.0031 (12)0.0314 (16)
C300.104 (4)0.224 (6)0.153 (4)0.001 (4)0.019 (3)0.065 (4)
C31A0.093 (7)0.161 (12)0.126 (7)0.003 (6)0.010 (5)0.009 (7)
C31B0.106 (7)0.292 (17)0.141 (7)0.016 (8)0.000 (5)0.094 (9)
Geometric parameters (Å, º) top
Cl1—C121.737 (3)C17—C221.434 (3)
N1—C21.349 (3)C18—C191.360 (4)
N1—C61.359 (3)C18—H180.9300
N1—H10.8600C19—C201.399 (5)
N2—C21.315 (3)C19—H190.9300
N2—H2B0.8600C20—C211.329 (5)
N2—H2A0.8600C20—H200.9300
N3—C21.338 (2)C21—C221.432 (4)
N3—C41.345 (3)C21—H210.9300
N4—C41.325 (2)C22—C231.377 (4)
N4—H4A0.8600C23—C241.386 (4)
N4—H4B0.8600C23—H230.9300
C4—C51.434 (3)C24—C251.420 (4)
C5—C61.367 (3)C24—C291.442 (3)
C5—C91.481 (3)C25—C261.344 (4)
C6—C71.498 (3)C25—H250.9300
C7—C81.513 (4)C26—C271.415 (4)
C7—H7A0.9700C26—H260.9300
C7—H7B0.9700C27—C281.348 (4)
C8—H8A0.9600C27—H270.9300
C8—H8B0.9600C28—C291.415 (4)
C8—H8C0.9600C28—H280.9300
C9—C101.378 (3)O1W—H1W0.832 (10)
C9—C141.378 (3)O1W—H2W0.824 (10)
C10—C111.388 (4)O3—C301.4205 (10)
C10—H100.9300O3—H30.8200
C11—C121.359 (4)C30—C31B1.268 (9)
C11—H110.9300C30—C31A1.4195 (10)
C12—C131.369 (4)C30—H30A0.9700
C13—C141.379 (4)C30—H30B0.9700
C13—H130.9300C30—H30C0.9700
C14—H140.9300C30—H30D0.9700
O1—C151.255 (3)C31A—H31A0.9600
O2—C151.222 (3)C31A—H31B0.9600
C15—C161.516 (3)C31A—H31C0.9600
C16—C291.382 (4)C31B—H31D0.9600
C16—C171.408 (3)C31B—H31E0.9600
C17—C181.411 (4)C31B—H31F0.9600
C2—N1—C6121.84 (17)C19—C18—H18119.4
C2—N1—H1119.1C17—C18—H18119.4
C6—N1—H1119.1C18—C19—C20120.4 (3)
C2—N2—H2B120.0C18—C19—H19119.8
C2—N2—H2A120.0C20—C19—H19119.8
H2B—N2—H2A120.0C21—C20—C19120.7 (3)
C2—N3—C4117.76 (18)C21—C20—H20119.7
C4—N4—H4A120.0C19—C20—H20119.7
C4—N4—H4B120.0C20—C21—C22121.8 (3)
H4A—N4—H4B120.0C20—C21—H21119.1
N2—C2—N3120.1 (2)C22—C21—H21119.1
N2—C2—N1118.34 (18)C23—C22—C21122.9 (2)
N3—C2—N1121.6 (2)C23—C22—C17119.6 (2)
N4—C4—N3116.21 (19)C21—C22—C17117.5 (3)
N4—C4—C5120.7 (2)C22—C23—C24122.3 (2)
N3—C4—C5123.08 (17)C22—C23—H23118.9
C6—C5—C4115.9 (2)C24—C23—H23118.9
C6—C5—C9123.49 (19)C23—C24—C25122.8 (2)
C4—C5—C9120.63 (17)C23—C24—C29118.7 (3)
N1—C6—C5119.82 (19)C25—C24—C29118.5 (3)
N1—C6—C7115.21 (17)C26—C25—C24121.5 (3)
C5—C6—C7125.0 (2)C26—C25—H25119.3
C6—C7—C8112.9 (2)C24—C25—H25119.3
C6—C7—H7A109.0C25—C26—C27120.3 (3)
C8—C7—H7A109.0C25—C26—H26119.8
C6—C7—H7B109.0C27—C26—H26119.8
C8—C7—H7B109.0C28—C27—C26120.2 (3)
H7A—C7—H7B107.8C28—C27—H27119.9
C7—C8—H8A109.5C26—C27—H27119.9
C7—C8—H8B109.5C27—C28—C29122.1 (3)
H8A—C8—H8B109.5C27—C28—H28118.9
C7—C8—H8C109.5C29—C28—H28118.9
H8A—C8—H8C109.5C16—C29—C28123.2 (2)
H8B—C8—H8C109.5C16—C29—C24119.4 (2)
C10—C9—C14117.6 (3)C28—C29—C24117.4 (3)
C10—C9—C5120.7 (2)H1W—O1W—H2W99 (4)
C14—C9—C5121.7 (2)C30—O3—H3109.5
C9—C10—C11121.4 (3)C31B—C30—O3118.8 (7)
C9—C10—H10119.3C31A—C30—O3124.7 (6)
C11—C10—H10119.3C31A—C30—H30A106.2
C12—C11—C10119.6 (3)O3—C30—H30A106.2
C12—C11—H11120.2C31A—C30—H30B106.2
C10—C11—H11120.2O3—C30—H30B106.2
C11—C12—C13120.3 (3)H30A—C30—H30B106.4
C11—C12—Cl1119.9 (2)C31B—C30—H30C107.6
C13—C12—Cl1119.8 (3)O3—C30—H30C107.6
C12—C13—C14119.7 (3)C31B—C30—H30D107.6
C12—C13—H13120.1O3—C30—H30D107.6
C14—C13—H13120.1H30C—C30—H30D107.0
C9—C14—C13121.4 (2)C30—C31A—H31A109.5
C9—C14—H14119.3C30—C31A—H31B109.5
C13—C14—H14119.3H31A—C31A—H31B109.5
O2—C15—O1124.9 (2)C30—C31A—H31C109.5
O2—C15—C16118.9 (2)H31A—C31A—H31C109.5
O1—C15—C16116.1 (2)H31B—C31A—H31C109.5
C29—C16—C17121.5 (2)C30—C31B—H31D109.5
C29—C16—C15119.5 (2)C30—C31B—H31E109.5
C17—C16—C15119.0 (2)H31D—C31B—H31E109.5
C16—C17—C18123.1 (2)C30—C31B—H31F109.5
C16—C17—C22118.5 (3)H31D—C31B—H31F109.5
C18—C17—C22118.3 (2)H31E—C31B—H31F109.5
C19—C18—C17121.2 (3)
C4—N3—C2—N2178.5 (2)O1—C15—C16—C1795.3 (3)
C4—N3—C2—N10.6 (3)C29—C16—C17—C18177.5 (3)
C6—N1—C2—N2178.3 (2)C15—C16—C17—C183.6 (4)
C6—N1—C2—N30.8 (4)C29—C16—C17—C221.2 (4)
C2—N3—C4—N4179.7 (2)C15—C16—C17—C22177.7 (2)
C2—N3—C4—C50.5 (3)C16—C17—C18—C19177.9 (3)
N4—C4—C5—C6179.0 (2)C22—C17—C18—C190.8 (5)
N3—C4—C5—C61.2 (3)C17—C18—C19—C200.4 (6)
N4—C4—C5—C91.3 (3)C18—C19—C20—C210.8 (6)
N3—C4—C5—C9178.4 (2)C19—C20—C21—C221.4 (6)
C2—N1—C6—C50.0 (3)C20—C21—C22—C23179.1 (3)
C2—N1—C6—C7179.9 (2)C20—C21—C22—C170.9 (5)
C4—C5—C6—N11.0 (3)C16—C17—C22—C231.4 (4)
C9—C5—C6—N1178.7 (2)C18—C17—C22—C23179.8 (3)
C4—C5—C6—C7178.9 (2)C16—C17—C22—C21178.6 (3)
C9—C5—C6—C71.4 (4)C18—C17—C22—C210.2 (4)
N1—C6—C7—C869.8 (3)C21—C22—C23—C24177.3 (3)
C5—C6—C7—C8110.1 (3)C17—C22—C23—C242.7 (4)
C6—C5—C9—C10111.1 (3)C22—C23—C24—C25178.8 (3)
C4—C5—C9—C1068.6 (3)C22—C23—C24—C291.3 (4)
C6—C5—C9—C1470.8 (3)C23—C24—C25—C26177.9 (3)
C4—C5—C9—C14109.6 (3)C29—C24—C25—C262.2 (4)
C14—C9—C10—C110.9 (4)C24—C25—C26—C271.3 (5)
C5—C9—C10—C11179.1 (2)C25—C26—C27—C280.2 (5)
C9—C10—C11—C120.6 (4)C26—C27—C28—C290.7 (5)
C10—C11—C12—C130.3 (4)C17—C16—C29—C28177.2 (2)
C10—C11—C12—Cl1179.6 (2)C15—C16—C29—C284.0 (4)
C11—C12—C13—C141.0 (4)C17—C16—C29—C242.6 (4)
Cl1—C12—C13—C14179.7 (2)C15—C16—C29—C24176.3 (2)
C10—C9—C14—C130.2 (4)C27—C28—C29—C16180.0 (3)
C5—C9—C14—C13178.4 (2)C27—C28—C29—C240.3 (4)
C12—C13—C14—C90.7 (4)C23—C24—C29—C161.3 (4)
O2—C15—C16—C2995.3 (3)C25—C24—C29—C16178.6 (2)
O1—C15—C16—C2983.6 (3)C23—C24—C29—C28178.4 (2)
O2—C15—C16—C1785.9 (3)C25—C24—C29—C281.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.861.842.671 (3)161
O1W—H1W···O30.83 (3)1.89 (4)2.712 (3)168 (5)
N2—H2A···O20.861.972.829 (3)175
N2—H2B···O1Wi0.862.253.080 (3)162
O3—H3···O10.821.912.728 (3)175
N4—H4A···N3ii0.862.163.006 (3)167
N4—H4B···O1Wiii0.862.152.871 (3)141
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z; (iii) x, y+1, z.
Bis[2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidin-1-ium] naphthalene-1,5-disulfonate (IX) top
Crystal data top
2C12H14ClN4+·C10H6O6S22Z = 3
Mr = 785.71F(000) = 1224
Triclinic, P1Dx = 1.419 Mg m3
a = 10.7421 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.7053 (4) ÅCell parameters from 8734 reflections
c = 24.5947 (8) Åθ = 3.3–29.5°
α = 85.450 (3)°µ = 0.35 mm1
β = 87.699 (3)°T = 293 K
γ = 63.459 (3)°Prism, colorless
V = 2757.86 (16) Å30.60 × 0.40 × 0.15 mm
Data collection top
Agilent SuperNova Dual Source
diffractometer with an Atlas detector
12628 independent reflections
Radiation source: SuperNova (Mo) X-ray Source9180 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.025
Detector resolution: 10.4933 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = 1313
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
k = 1512
Tmin = 0.784, Tmax = 1.000l = 3130
25967 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.126 w = 1/[σ2(Fo2) + (0.0484P)2 + 1.0461P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.002
12628 reflectionsΔρmax = 0.45 e Å3
706 parametersΔρmin = 0.55 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S1A0.62574 (6)0.52251 (5)0.68473 (2)0.04102 (14)
S2A0.34145 (6)1.16218 (5)0.59755 (2)0.04086 (14)
S3B0.10394 (6)0.17877 (6)1.03066 (2)0.04328 (14)
Cl1B0.84874 (9)0.15386 (8)0.51678 (3)0.0740 (2)
Cl1A0.46575 (14)0.24419 (11)1.12142 (3)0.1209 (4)
Cl1C0.19389 (10)0.63173 (10)0.82549 (3)0.1029 (3)
O1A0.65040 (17)0.47013 (16)0.74113 (6)0.0504 (4)
O2A0.53248 (18)0.48564 (16)0.65817 (7)0.0522 (4)
O3A0.75295 (18)0.49597 (17)0.65505 (7)0.0578 (5)
O4A0.29612 (18)1.21432 (16)0.54254 (6)0.0516 (4)
O5A0.2269 (2)1.21172 (17)0.63613 (7)0.0664 (5)
O6A0.4612 (2)1.17545 (17)0.61325 (8)0.0643 (5)
O1B0.20227 (18)0.13773 (15)0.98567 (6)0.0512 (4)
O2B0.02714 (18)0.17879 (17)1.01878 (7)0.0564 (4)
O3B0.16230 (18)0.10850 (16)1.08227 (6)0.0512 (4)
N1B0.98632 (18)0.02742 (17)0.84240 (7)0.0389 (4)
H1B0.95640.07090.86430.047*
N2B1.0944 (2)0.0013 (2)0.91490 (7)0.0542 (6)
H2B11.14380.03290.92860.065*
H2B21.06400.04380.93540.065*
N3B1.11250 (19)0.09212 (18)0.83038 (7)0.0399 (4)
N4B1.1261 (2)0.18385 (19)0.74694 (7)0.0472 (5)
H4B11.17490.21470.76160.057*
H4B21.10760.19950.71270.057*
N1A0.49816 (18)0.35564 (17)0.79213 (7)0.0375 (4)
H1A0.53940.39310.77270.045*
N2A0.4269 (2)0.31398 (19)0.71286 (7)0.0471 (5)
H2A10.38310.28250.69540.057*
H2A20.47140.35090.69530.057*
N3A0.35752 (19)0.24875 (17)0.79456 (7)0.0381 (4)
N4A0.2965 (2)0.1852 (2)0.87733 (7)0.0500 (5)
H4A10.25020.15530.86040.060*
H4A20.29860.17870.91240.060*
N1C0.04610 (19)0.66654 (18)0.51177 (7)0.0420 (4)
H1C0.12760.70420.49750.050*
N2C0.0435 (2)0.60835 (19)0.42648 (8)0.0492 (5)
H2C10.11240.56950.40500.059*
H2C20.03940.64900.41360.059*
N3C0.1933 (2)0.54250 (18)0.49900 (8)0.0476 (5)
N4C0.3411 (2)0.4906 (2)0.57002 (9)0.0667 (6)
H4C10.40830.45270.54770.080*
H4C20.35820.49130.60380.080*
C2B1.0656 (2)0.0221 (2)0.86256 (8)0.0380 (5)
C4B1.0792 (2)0.1120 (2)0.77731 (8)0.0366 (5)
C5B0.9970 (2)0.0601 (2)0.75389 (8)0.0363 (4)
C6B0.9522 (2)0.0108 (2)0.78864 (8)0.0367 (5)
C7B0.8644 (2)0.0725 (2)0.77332 (9)0.0466 (6)
H7B10.90150.15860.79050.056*
H7B20.86930.07880.73410.056*
C8B0.7134 (3)0.0013 (3)0.79027 (13)0.0716 (8)
H8B10.70830.01170.82870.107*
H8B20.66270.04510.78200.107*
H8B30.67360.08390.77070.107*
C2A0.4261 (2)0.3057 (2)0.76685 (8)0.0349 (4)
C4A0.3644 (2)0.2411 (2)0.84953 (8)0.0357 (4)
C5A0.4415 (2)0.2904 (2)0.87810 (8)0.0347 (4)
C6A0.5075 (2)0.3484 (2)0.84749 (8)0.0357 (4)
C7A0.5999 (3)0.3981 (2)0.86949 (9)0.0494 (6)
H7A10.57120.42250.90640.059*
H7A20.59080.47380.84740.059*
C8A0.7498 (3)0.2987 (4)0.86955 (16)0.0926 (11)
H8A10.75960.22510.89260.139*
H8A20.80720.33370.88300.139*
H8A30.77800.27400.83310.139*
C2C0.0650 (2)0.6055 (2)0.47943 (9)0.0418 (5)
C4C0.2102 (2)0.5484 (2)0.55220 (10)0.0463 (5)
C5C0.0965 (2)0.6136 (2)0.58855 (9)0.0430 (5)
C6C0.0332 (2)0.6705 (2)0.56644 (9)0.0427 (5)
C7C0.1664 (2)0.7429 (2)0.59613 (10)0.0513 (6)
H7C10.16230.70010.63190.062*
H7C20.24240.74220.57640.062*
C8C0.1955 (3)0.8794 (3)0.60258 (14)0.0772 (9)
H8C10.12330.88070.62390.116*
H8C20.28350.92270.62070.116*
H8C30.19830.92180.56730.116*
C9B0.9608 (2)0.0855 (2)0.69486 (8)0.0386 (5)
C10B1.0616 (2)0.0317 (3)0.65523 (9)0.0478 (6)
H10B1.15330.01980.66560.057*
C11B1.0279 (3)0.0535 (3)0.60055 (9)0.0536 (6)
H11B1.09620.01740.57420.064*
C12B0.8927 (3)0.1288 (2)0.58561 (9)0.0487 (6)
C13B0.7909 (3)0.1844 (3)0.62333 (11)0.0595 (7)
H13B0.69950.23590.61250.071*
C14B0.8260 (3)0.1631 (2)0.67780 (10)0.0545 (6)
H14B0.75730.20190.70370.065*
C9A0.4470 (2)0.2781 (2)0.93868 (8)0.0364 (5)
C10A0.3705 (3)0.3831 (2)0.96847 (9)0.0466 (5)
H10A0.31390.46140.95040.056*
C11A0.3773 (3)0.3730 (3)1.02453 (10)0.0598 (7)
H11A0.32710.44421.04430.072*
C12A0.4585 (3)0.2576 (3)1.05061 (9)0.0619 (7)
C13A0.5331 (3)0.1512 (3)1.02239 (10)0.0613 (7)
H13A0.58650.07271.04090.074*
C14A0.5281 (3)0.1619 (2)0.96625 (9)0.0497 (6)
H14A0.57970.09050.94680.060*
C9C0.1210 (2)0.6166 (2)0.64731 (9)0.0479 (5)
C10C0.0767 (3)0.5517 (3)0.68785 (11)0.0655 (7)
H10C0.03180.50460.67790.079*
C11C0.0987 (4)0.5569 (3)0.74220 (12)0.0741 (9)
H11C0.06820.51400.76880.089*
C12C0.1655 (3)0.6251 (3)0.75684 (11)0.0660 (8)
C13C0.2107 (3)0.6894 (3)0.71842 (11)0.0663 (8)
H13C0.25610.73560.72890.080*
C14C0.1880 (3)0.6849 (3)0.66358 (10)0.0568 (6)
H14C0.21850.72870.63740.068*
C15A0.5414 (2)0.6924 (2)0.68794 (8)0.0369 (5)
C16A0.5287 (3)0.7405 (2)0.73792 (8)0.0457 (5)
H16A0.55710.68530.76920.055*
C17A0.4728 (3)0.8732 (2)0.74188 (9)0.0485 (6)
H17A0.46250.90540.77600.058*
C18A0.4336 (2)0.9551 (2)0.69691 (8)0.0424 (5)
H18A0.40071.04230.70040.051*
C19A0.4420 (2)0.9097 (2)0.64440 (8)0.0336 (4)
C20A0.3976 (2)0.9939 (2)0.59607 (8)0.0362 (5)
C21A0.4050 (2)0.9452 (2)0.54677 (8)0.0427 (5)
H21A0.37451.00050.51560.051*
C22A0.4584 (2)0.8124 (2)0.54241 (8)0.0439 (5)
H22A0.46340.78100.50840.053*
C23A0.5025 (2)0.7301 (2)0.58710 (8)0.0403 (5)
H23A0.53780.64260.58340.048*
C24A0.4957 (2)0.7754 (2)0.63970 (8)0.0335 (4)
C16B0.0849 (3)0.3710 (2)1.08970 (9)0.0515 (6)
H16B0.11760.30791.11810.062*
C15B0.0656 (2)0.3407 (2)1.03946 (9)0.0408 (5)
C24B0.0140 (2)0.4360 (2)0.99514 (8)0.0391 (5)
C23B0.0079 (3)0.4088 (2)0.94230 (9)0.0468 (5)
H23B0.01040.32570.93550.056*
C22B0.0553 (3)0.5026 (3)0.90141 (9)0.0562 (7)
H22B0.06850.48260.86690.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0451 (3)0.0384 (3)0.0428 (3)0.0227 (3)0.0064 (2)0.0014 (2)
S2A0.0492 (3)0.0400 (3)0.0328 (3)0.0201 (3)0.0035 (2)0.0039 (2)
S3B0.0577 (4)0.0406 (3)0.0401 (3)0.0307 (3)0.0072 (2)0.0010 (2)
Cl1B0.1186 (6)0.0787 (5)0.0427 (3)0.0599 (5)0.0259 (4)0.0078 (3)
Cl1A0.1973 (12)0.1175 (8)0.0310 (4)0.0546 (8)0.0176 (5)0.0010 (4)
Cl1C0.0920 (6)0.1121 (7)0.0491 (4)0.0068 (5)0.0111 (4)0.0167 (4)
O1A0.0604 (10)0.0493 (10)0.0467 (9)0.0311 (9)0.0001 (8)0.0092 (7)
O2A0.0646 (11)0.0481 (10)0.0538 (10)0.0341 (9)0.0032 (8)0.0009 (8)
O3A0.0507 (10)0.0515 (10)0.0671 (11)0.0211 (9)0.0202 (8)0.0021 (8)
O4A0.0602 (10)0.0518 (10)0.0386 (8)0.0226 (9)0.0084 (7)0.0088 (7)
O5A0.0811 (13)0.0469 (11)0.0497 (10)0.0123 (10)0.0238 (9)0.0023 (8)
O6A0.0700 (12)0.0516 (11)0.0795 (13)0.0336 (10)0.0282 (10)0.0040 (9)
O1B0.0681 (11)0.0470 (10)0.0440 (9)0.0318 (9)0.0153 (8)0.0037 (7)
O2B0.0652 (11)0.0581 (11)0.0624 (11)0.0434 (10)0.0008 (9)0.0038 (8)
O3B0.0663 (11)0.0469 (10)0.0444 (9)0.0310 (9)0.0059 (8)0.0065 (7)
N1B0.0482 (11)0.0438 (11)0.0361 (9)0.0315 (9)0.0020 (8)0.0012 (8)
N2B0.0796 (15)0.0766 (15)0.0342 (10)0.0610 (14)0.0052 (9)0.0065 (9)
N3B0.0484 (11)0.0515 (11)0.0329 (9)0.0345 (10)0.0012 (8)0.0006 (8)
N4B0.0661 (13)0.0639 (13)0.0323 (9)0.0482 (12)0.0010 (9)0.0017 (9)
N1A0.0457 (10)0.0407 (10)0.0348 (9)0.0279 (9)0.0045 (8)0.0000 (7)
N2A0.0654 (13)0.0574 (13)0.0314 (9)0.0393 (11)0.0014 (9)0.0006 (8)
N3A0.0468 (10)0.0444 (11)0.0317 (9)0.0284 (9)0.0013 (7)0.0008 (7)
N4A0.0679 (13)0.0750 (15)0.0331 (9)0.0559 (12)0.0002 (9)0.0015 (9)
N1C0.0420 (10)0.0403 (11)0.0460 (10)0.0207 (9)0.0041 (8)0.0013 (8)
N2C0.0500 (12)0.0487 (12)0.0457 (11)0.0188 (10)0.0016 (9)0.0042 (9)
N3C0.0492 (12)0.0404 (11)0.0482 (11)0.0152 (9)0.0035 (9)0.0039 (9)
N4C0.0504 (13)0.0689 (16)0.0605 (14)0.0065 (12)0.0116 (11)0.0107 (11)
C2B0.0439 (12)0.0423 (12)0.0355 (11)0.0265 (10)0.0019 (9)0.0014 (9)
C4B0.0403 (11)0.0410 (12)0.0332 (10)0.0228 (10)0.0056 (9)0.0032 (9)
C5B0.0384 (11)0.0414 (12)0.0343 (10)0.0223 (10)0.0026 (8)0.0043 (9)
C6B0.0369 (11)0.0390 (12)0.0387 (11)0.0207 (10)0.0017 (9)0.0055 (9)
C7B0.0560 (14)0.0512 (14)0.0467 (13)0.0363 (12)0.0041 (11)0.0024 (11)
C8B0.0514 (16)0.084 (2)0.090 (2)0.0393 (16)0.0081 (15)0.0035 (17)
C2A0.0406 (11)0.0345 (11)0.0321 (10)0.0193 (10)0.0013 (8)0.0006 (8)
C4A0.0398 (11)0.0404 (12)0.0319 (10)0.0227 (10)0.0000 (8)0.0001 (9)
C5A0.0398 (11)0.0370 (12)0.0316 (10)0.0208 (10)0.0005 (8)0.0023 (8)
C6A0.0394 (11)0.0361 (12)0.0355 (10)0.0203 (10)0.0007 (9)0.0030 (9)
C7A0.0647 (16)0.0599 (16)0.0448 (13)0.0464 (14)0.0009 (11)0.0064 (11)
C8A0.0581 (19)0.103 (3)0.132 (3)0.047 (2)0.0207 (19)0.017 (2)
C2C0.0499 (13)0.0327 (12)0.0451 (12)0.0206 (10)0.0014 (10)0.0017 (9)
C4C0.0489 (13)0.0352 (12)0.0510 (13)0.0154 (11)0.0048 (11)0.0001 (10)
C5C0.0493 (13)0.0385 (12)0.0441 (12)0.0226 (11)0.0030 (10)0.0013 (10)
C6C0.0503 (13)0.0399 (13)0.0465 (12)0.0286 (11)0.0009 (10)0.0007 (10)
C7C0.0460 (13)0.0599 (16)0.0544 (14)0.0301 (13)0.0025 (11)0.0004 (12)
C8C0.0612 (18)0.0614 (19)0.108 (3)0.0249 (16)0.0143 (17)0.0243 (17)
C9B0.0470 (12)0.0420 (12)0.0350 (10)0.0272 (11)0.0002 (9)0.0033 (9)
C10B0.0437 (13)0.0672 (17)0.0405 (12)0.0309 (13)0.0008 (10)0.0094 (11)
C11B0.0602 (16)0.0772 (19)0.0382 (12)0.0426 (15)0.0048 (11)0.0139 (12)
C12B0.0746 (17)0.0484 (14)0.0376 (12)0.0403 (14)0.0095 (12)0.0015 (10)
C13B0.0596 (16)0.0515 (16)0.0555 (15)0.0137 (13)0.0145 (13)0.0010 (12)
C14B0.0540 (15)0.0517 (15)0.0454 (13)0.0121 (12)0.0007 (11)0.0058 (11)
C9A0.0415 (11)0.0443 (13)0.0310 (10)0.0261 (10)0.0013 (9)0.0016 (9)
C10A0.0522 (14)0.0451 (14)0.0399 (12)0.0195 (11)0.0017 (10)0.0009 (10)
C11A0.0814 (19)0.0571 (17)0.0391 (13)0.0282 (15)0.0045 (13)0.0120 (12)
C12A0.085 (2)0.0704 (19)0.0306 (11)0.0353 (17)0.0076 (12)0.0010 (12)
C13A0.0787 (19)0.0542 (17)0.0433 (13)0.0233 (15)0.0153 (13)0.0078 (12)
C14A0.0590 (15)0.0418 (14)0.0422 (12)0.0169 (12)0.0033 (11)0.0032 (10)
C9C0.0484 (13)0.0460 (14)0.0455 (13)0.0179 (11)0.0029 (10)0.0001 (10)
C10C0.085 (2)0.0578 (17)0.0554 (16)0.0349 (16)0.0005 (14)0.0062 (13)
C11C0.089 (2)0.0633 (19)0.0528 (16)0.0211 (18)0.0058 (15)0.0084 (14)
C12C0.0522 (16)0.0669 (19)0.0463 (14)0.0033 (14)0.0039 (12)0.0066 (13)
C13C0.0468 (15)0.089 (2)0.0589 (17)0.0234 (15)0.0018 (13)0.0218 (15)
C14C0.0484 (14)0.0738 (19)0.0512 (14)0.0295 (14)0.0022 (11)0.0075 (13)
C15A0.0420 (11)0.0407 (12)0.0339 (10)0.0241 (10)0.0023 (9)0.0003 (9)
C16A0.0635 (15)0.0489 (14)0.0302 (10)0.0308 (12)0.0026 (10)0.0035 (9)
C17A0.0715 (16)0.0520 (15)0.0277 (10)0.0319 (13)0.0018 (10)0.0056 (10)
C18A0.0558 (14)0.0394 (13)0.0346 (11)0.0231 (11)0.0006 (10)0.0047 (9)
C19A0.0339 (10)0.0414 (12)0.0294 (10)0.0205 (9)0.0014 (8)0.0013 (8)
C20A0.0377 (11)0.0432 (12)0.0310 (10)0.0211 (10)0.0004 (8)0.0009 (9)
C21A0.0498 (13)0.0527 (14)0.0294 (10)0.0265 (12)0.0040 (9)0.0012 (9)
C22A0.0548 (14)0.0575 (15)0.0273 (10)0.0312 (12)0.0019 (9)0.0090 (10)
C23A0.0456 (12)0.0456 (13)0.0360 (11)0.0256 (11)0.0056 (9)0.0068 (9)
C24A0.0329 (10)0.0419 (12)0.0311 (10)0.0220 (9)0.0022 (8)0.0010 (8)
C16B0.0754 (17)0.0503 (15)0.0355 (11)0.0348 (14)0.0032 (11)0.0041 (10)
C15B0.0503 (13)0.0403 (12)0.0387 (11)0.0271 (11)0.0046 (9)0.0002 (9)
C24B0.0469 (12)0.0416 (12)0.0365 (11)0.0269 (10)0.0036 (9)0.0019 (9)
C23B0.0620 (15)0.0434 (13)0.0425 (12)0.0300 (12)0.0021 (11)0.0038 (10)
C22B0.088 (2)0.0547 (16)0.0349 (12)0.0396 (15)0.0046 (12)0.0042 (11)
Geometric parameters (Å, º) top
S1A—O3A1.4399 (16)C4C—C5C1.435 (3)
S1A—O2A1.4492 (17)C5C—C6C1.362 (3)
S1A—O1A1.4560 (15)C5C—C9C1.485 (3)
S1A—C15A1.786 (2)C6C—C7C1.493 (3)
S2A—O6A1.4339 (17)C7C—C8C1.505 (4)
S2A—O4A1.4479 (15)C7C—H7C10.9700
S2A—O5A1.4511 (18)C7C—H7C20.9700
S2A—C20A1.787 (2)C8C—H8C10.9600
S3B—O2B1.4494 (17)C8C—H8C20.9600
S3B—O1B1.4518 (16)C8C—H8C30.9600
S3B—O3B1.4554 (16)C9B—C14B1.382 (3)
S3B—C15B1.780 (2)C9B—C10B1.386 (3)
Cl1B—C12B1.743 (2)C10B—C11B1.381 (3)
Cl1A—C12A1.738 (2)C10B—H10B0.9300
Cl1C—C12C1.741 (3)C11B—C12B1.367 (4)
N1B—C2B1.352 (3)C11B—H11B0.9300
N1B—C6B1.362 (3)C12B—C13B1.363 (4)
N1B—H1B0.8600C13B—C14B1.379 (3)
N2B—C2B1.314 (3)C13B—H13B0.9300
N2B—H2B10.8600C14B—H14B0.9300
N2B—H2B20.8600C9A—C14A1.382 (3)
N3B—C2B1.336 (2)C9A—C10A1.384 (3)
N3B—C4B1.342 (2)C10A—C11A1.377 (3)
N4B—C4B1.330 (2)C10A—H10A0.9300
N4B—H4B10.8600C11A—C12A1.361 (4)
N4B—H4B20.8600C11A—H11A0.9300
N1A—C2A1.352 (3)C12A—C13A1.369 (4)
N1A—C6A1.362 (2)C13A—C14A1.378 (3)
N1A—H1A0.8600C13A—H13A0.9300
N2A—C2A1.324 (2)C14A—H14A0.9300
N2A—H2A10.8600C9C—C14C1.380 (3)
N2A—H2A20.8600C9C—C10C1.401 (3)
N3A—C2A1.333 (2)C10C—C11C1.378 (4)
N3A—C4A1.351 (2)C10C—H10C0.9300
N4A—C4A1.321 (2)C11C—C12C1.364 (4)
N4A—H4A10.8600C11C—H11C0.9300
N4A—H4A20.8600C12C—C13C1.368 (4)
N1C—C2C1.349 (3)C13C—C14C1.389 (3)
N1C—C6C1.364 (3)C13C—H13C0.9300
N1C—H1C0.8600C14C—H14C0.9300
N2C—C2C1.327 (3)C15A—C16A1.369 (3)
N2C—H2C10.8600C15A—C24A1.425 (3)
N2C—H2C20.8600C16A—C17A1.403 (3)
N3C—C2C1.328 (3)C16A—H16A0.9300
N3C—C4C1.339 (3)C17A—C18A1.352 (3)
N4C—C4C1.334 (3)C17A—H17A0.9300
N4C—H4C10.8600C18A—C19A1.419 (3)
N4C—H4C20.8600C18A—H18A0.9300
C4B—C5B1.433 (3)C19A—C24A1.425 (3)
C5B—C6B1.365 (3)C19A—C20A1.432 (3)
C5B—C9B1.490 (3)C20A—C21A1.364 (3)
C6B—C7B1.495 (3)C21A—C22A1.408 (3)
C7B—C8B1.517 (4)C21A—H21A0.9300
C7B—H7B10.9700C22A—C23A1.352 (3)
C7B—H7B20.9700C22A—H22A0.9300
C8B—H8B10.9600C23A—C24A1.424 (3)
C8B—H8B20.9600C23A—H23A0.9300
C8B—H8B30.9600C16B—C15B1.361 (3)
C4A—C5A1.431 (3)C16B—C22Bi1.401 (3)
C5A—C6A1.356 (3)C16B—H16B0.9300
C5A—C9A1.486 (3)C15B—C24B1.429 (3)
C6A—C7A1.492 (3)C24B—C23B1.415 (3)
C7A—C8A1.507 (4)C24B—C24Bi1.430 (4)
C7A—H7A10.9700C23B—C22B1.358 (3)
C7A—H7A20.9700C23B—H23B0.9300
C8A—H8A10.9600C22B—C16Bi1.401 (3)
C8A—H8A20.9600C22B—H22B0.9300
C8A—H8A30.9600
O3A—S1A—O2A113.98 (11)C8C—C7C—H7C1109.1
O3A—S1A—O1A112.48 (11)C6C—C7C—H7C2109.1
O2A—S1A—O1A111.17 (9)C8C—C7C—H7C2109.1
O3A—S1A—C15A104.88 (10)H7C1—C7C—H7C2107.8
O2A—S1A—C15A108.05 (10)C7C—C8C—H8C1109.5
O1A—S1A—C15A105.63 (10)C7C—C8C—H8C2109.5
O6A—S2A—O4A113.05 (10)H8C1—C8C—H8C2109.5
O6A—S2A—O5A113.16 (12)C7C—C8C—H8C3109.5
O4A—S2A—O5A111.22 (11)H8C1—C8C—H8C3109.5
O6A—S2A—C20A105.59 (10)H8C2—C8C—H8C3109.5
O4A—S2A—C20A105.14 (10)C14B—C9B—C10B117.8 (2)
O5A—S2A—C20A108.07 (10)C14B—C9B—C5B121.2 (2)
O2B—S3B—O1B112.36 (10)C10B—C9B—C5B120.9 (2)
O2B—S3B—O3B112.17 (9)C11B—C10B—C9B121.0 (2)
O1B—S3B—O3B112.84 (11)C11B—C10B—H10B119.5
O2B—S3B—C15B106.37 (11)C9B—C10B—H10B119.5
O1B—S3B—C15B106.85 (9)C12B—C11B—C10B119.1 (2)
O3B—S3B—C15B105.64 (10)C12B—C11B—H11B120.4
C2B—N1B—C6B122.19 (16)C10B—C11B—H11B120.4
C2B—N1B—H1B118.9C13B—C12B—C11B121.6 (2)
C6B—N1B—H1B118.9C13B—C12B—Cl1B119.1 (2)
C2B—N2B—H2B1120.0C11B—C12B—Cl1B119.4 (2)
C2B—N2B—H2B2120.0C12B—C13B—C14B118.8 (2)
H2B1—N2B—H2B2120.0C12B—C13B—H13B120.6
C2B—N3B—C4B118.29 (17)C14B—C13B—H13B120.6
C4B—N4B—H4B1120.0C13B—C14B—C9B121.6 (2)
C4B—N4B—H4B2120.0C13B—C14B—H14B119.2
H4B1—N4B—H4B2120.0C9B—C14B—H14B119.2
C2A—N1A—C6A121.98 (16)C14A—C9A—C10A118.8 (2)
C2A—N1A—H1A119.0C14A—C9A—C5A120.8 (2)
C6A—N1A—H1A119.0C10A—C9A—C5A120.38 (19)
C2A—N2A—H2A1120.0C11A—C10A—C9A120.7 (2)
C2A—N2A—H2A2120.0C11A—C10A—H10A119.7
H2A1—N2A—H2A2120.0C9A—C10A—H10A119.7
C2A—N3A—C4A117.05 (17)C12A—C11A—C10A119.2 (3)
C4A—N4A—H4A1120.0C12A—C11A—H11A120.4
C4A—N4A—H4A2120.0C10A—C11A—H11A120.4
H4A1—N4A—H4A2120.0C11A—C12A—C13A121.5 (2)
C2C—N1C—C6C122.05 (19)C11A—C12A—Cl1A119.3 (2)
C2C—N1C—H1C119.0C13A—C12A—Cl1A119.2 (2)
C6C—N1C—H1C119.0C12A—C13A—C14A119.2 (2)
C2C—N2C—H2C1120.0C12A—C13A—H13A120.4
C2C—N2C—H2C2120.0C14A—C13A—H13A120.4
H2C1—N2C—H2C2120.0C13A—C14A—C9A120.5 (2)
C2C—N3C—C4C117.2 (2)C13A—C14A—H14A119.7
C4C—N4C—H4C1120.0C9A—C14A—H14A119.7
C4C—N4C—H4C2120.0C14C—C9C—C10C117.9 (2)
H4C1—N4C—H4C2120.0C14C—C9C—C5C120.5 (2)
N2B—C2B—N3B120.38 (18)C10C—C9C—C5C121.6 (2)
N2B—C2B—N1B118.53 (17)C11C—C10C—C9C120.8 (3)
N3B—C2B—N1B121.08 (18)C11C—C10C—H10C119.6
N4B—C4B—N3B116.32 (18)C9C—C10C—H10C119.6
N4B—C4B—C5B120.97 (18)C12C—C11C—C10C119.7 (3)
N3B—C4B—C5B122.70 (17)C12C—C11C—H11C120.1
C6B—C5B—C4B116.46 (18)C10C—C11C—H11C120.1
C6B—C5B—C9B122.39 (18)C11C—C12C—C13C121.1 (3)
C4B—C5B—C9B121.14 (17)C11C—C12C—Cl1C119.9 (2)
N1B—C6B—C5B119.25 (18)C13C—C12C—Cl1C118.9 (3)
N1B—C6B—C7B115.14 (17)C12C—C13C—C14C119.3 (3)
C5B—C6B—C7B125.60 (19)C12C—C13C—H13C120.4
C6B—C7B—C8B112.5 (2)C14C—C13C—H13C120.4
C6B—C7B—H7B1109.1C9C—C14C—C13C121.1 (3)
C8B—C7B—H7B1109.1C9C—C14C—H14C119.4
C6B—C7B—H7B2109.1C13C—C14C—H14C119.4
C8B—C7B—H7B2109.1C16A—C15A—C24A120.9 (2)
H7B1—C7B—H7B2107.8C16A—C15A—S1A117.87 (16)
C7B—C8B—H8B1109.5C24A—C15A—S1A121.11 (16)
C7B—C8B—H8B2109.5C15A—C16A—C17A119.8 (2)
H8B1—C8B—H8B2109.5C15A—C16A—H16A120.1
C7B—C8B—H8B3109.5C17A—C16A—H16A120.1
H8B1—C8B—H8B3109.5C18A—C17A—C16A121.1 (2)
H8B2—C8B—H8B3109.5C18A—C17A—H17A119.4
N2A—C2A—N3A120.50 (18)C16A—C17A—H17A119.4
N2A—C2A—N1A117.41 (17)C17A—C18A—C19A120.9 (2)
N3A—C2A—N1A122.09 (18)C17A—C18A—H18A119.5
N4A—C4A—N3A117.50 (18)C19A—C18A—H18A119.5
N4A—C4A—C5A119.60 (18)C18A—C19A—C24A118.70 (18)
N3A—C4A—C5A122.90 (17)C18A—C19A—C20A122.5 (2)
C6A—C5A—C4A117.04 (18)C24A—C19A—C20A118.79 (18)
C6A—C5A—C9A122.25 (18)C21A—C20A—C19A120.0 (2)
C4A—C5A—C9A120.71 (16)C21A—C20A—S2A118.20 (16)
C5A—C6A—N1A118.92 (18)C19A—C20A—S2A121.68 (16)
C5A—C6A—C7A124.91 (19)C20A—C21A—C22A120.9 (2)
N1A—C6A—C7A116.01 (17)C20A—C21A—H21A119.6
C6A—C7A—C8A111.1 (2)C22A—C21A—H21A119.6
C6A—C7A—H7A1109.4C23A—C22A—C21A120.7 (2)
C8A—C7A—H7A1109.4C23A—C22A—H22A119.6
C6A—C7A—H7A2109.4C21A—C22A—H22A119.6
C8A—C7A—H7A2109.4C22A—C23A—C24A120.9 (2)
H7A1—C7A—H7A2108.0C22A—C23A—H23A119.6
C7A—C8A—H8A1109.5C24A—C23A—H23A119.6
C7A—C8A—H8A2109.5C23A—C24A—C19A118.70 (18)
H8A1—C8A—H8A2109.5C23A—C24A—C15A122.9 (2)
C7A—C8A—H8A3109.5C19A—C24A—C15A118.37 (18)
H8A1—C8A—H8A3109.5C15B—C16B—C22Bi120.0 (2)
H8A2—C8A—H8A3109.5C15B—C16B—H16B120.0
N2C—C2C—N3C119.7 (2)C22Bi—C16B—H16B120.0
N2C—C2C—N1C118.2 (2)C16B—C15B—C24B121.2 (2)
N3C—C2C—N1C122.2 (2)C16B—C15B—S3B118.05 (17)
N4C—C4C—N3C115.9 (2)C24B—C15B—S3B120.72 (17)
N4C—C4C—C5C121.0 (2)C23B—C24B—C15B123.1 (2)
N3C—C4C—C5C123.2 (2)C23B—C24B—C24Bi118.9 (2)
C6C—C5C—C4C116.6 (2)C15B—C24B—C24Bi117.9 (2)
C6C—C5C—C9C122.4 (2)C22B—C23B—C24B120.8 (2)
C4C—C5C—C9C121.0 (2)C22B—C23B—H23B119.6
C5C—C6C—N1C118.6 (2)C24B—C23B—H23B119.6
C5C—C6C—C7C126.2 (2)C23B—C22B—C16Bi121.1 (2)
N1C—C6C—C7C115.2 (2)C23B—C22B—H22B119.4
C6C—C7C—C8C112.5 (2)C16Bi—C22B—H22B119.4
C6C—C7C—H7C1109.1
C4B—N3B—C2B—N2B179.3 (2)C9A—C10A—C11A—C12A1.2 (4)
C4B—N3B—C2B—N1B0.1 (3)C10A—C11A—C12A—C13A0.2 (4)
C6B—N1B—C2B—N2B179.7 (2)C10A—C11A—C12A—Cl1A179.3 (2)
C6B—N1B—C2B—N3B1.1 (3)C11A—C12A—C13A—C14A1.4 (4)
C2B—N3B—C4B—N4B178.9 (2)Cl1A—C12A—C13A—C14A179.6 (2)
C2B—N3B—C4B—C5B0.7 (3)C12A—C13A—C14A—C9A1.1 (4)
N4B—C4B—C5B—C6B179.1 (2)C10A—C9A—C14A—C13A0.3 (3)
N3B—C4B—C5B—C6B0.6 (3)C5A—C9A—C14A—C13A179.8 (2)
N4B—C4B—C5B—C9B0.3 (3)C6C—C5C—C9C—C14C112.0 (3)
N3B—C4B—C5B—C9B179.3 (2)C4C—C5C—C9C—C14C68.8 (3)
C2B—N1B—C6B—C5B1.2 (3)C6C—C5C—C9C—C10C67.5 (3)
C2B—N1B—C6B—C7B179.8 (2)C4C—C5C—C9C—C10C111.7 (3)
C4B—C5B—C6B—N1B0.4 (3)C14C—C9C—C10C—C11C0.4 (4)
C9B—C5B—C6B—N1B178.3 (2)C5C—C9C—C10C—C11C179.2 (3)
C4B—C5B—C6B—C7B179.3 (2)C9C—C10C—C11C—C12C0.5 (5)
C9B—C5B—C6B—C7B0.5 (4)C10C—C11C—C12C—C13C0.3 (5)
N1B—C6B—C7B—C8B76.2 (3)C10C—C11C—C12C—Cl1C179.9 (2)
C5B—C6B—C7B—C8B102.7 (3)C11C—C12C—C13C—C14C0.0 (4)
C4A—N3A—C2A—N2A178.3 (2)Cl1C—C12C—C13C—C14C179.8 (2)
C4A—N3A—C2A—N1A0.9 (3)C10C—C9C—C14C—C13C0.1 (4)
C6A—N1A—C2A—N2A177.9 (2)C5C—C9C—C14C—C13C179.5 (2)
C6A—N1A—C2A—N3A1.4 (3)C12C—C13C—C14C—C9C0.1 (4)
C2A—N3A—C4A—N4A179.8 (2)O3A—S1A—C15A—C16A112.70 (18)
C2A—N3A—C4A—C5A0.3 (3)O2A—S1A—C15A—C16A125.37 (18)
N4A—C4A—C5A—C6A179.1 (2)O1A—S1A—C15A—C16A6.3 (2)
N3A—C4A—C5A—C6A1.1 (3)O3A—S1A—C15A—C24A63.79 (18)
N4A—C4A—C5A—C9A0.6 (3)O2A—S1A—C15A—C24A58.14 (18)
N3A—C4A—C5A—C9A179.2 (2)O1A—S1A—C15A—C24A177.19 (15)
C4A—C5A—C6A—N1A0.6 (3)C24A—C15A—C16A—C17A1.3 (3)
C9A—C5A—C6A—N1A179.72 (19)S1A—C15A—C16A—C17A175.16 (18)
C4A—C5A—C6A—C7A175.9 (2)C15A—C16A—C17A—C18A1.5 (4)
C9A—C5A—C6A—C7A4.4 (4)C16A—C17A—C18A—C19A2.9 (4)
C2A—N1A—C6A—C5A0.6 (3)C17A—C18A—C19A—C24A1.4 (3)
C2A—N1A—C6A—C7A175.2 (2)C17A—C18A—C19A—C20A178.1 (2)
C5A—C6A—C7A—C8A92.5 (3)C18A—C19A—C20A—C21A178.5 (2)
N1A—C6A—C7A—C8A82.9 (3)C24A—C19A—C20A—C21A1.0 (3)
C4C—N3C—C2C—N2C176.48 (19)C18A—C19A—C20A—S2A5.4 (3)
C4C—N3C—C2C—N1C4.2 (3)C24A—C19A—C20A—S2A175.14 (14)
C6C—N1C—C2C—N2C178.75 (18)O6A—S2A—C20A—C21A111.94 (18)
C6C—N1C—C2C—N3C1.9 (3)O4A—S2A—C20A—C21A7.8 (2)
C2C—N3C—C4C—N4C176.2 (2)O5A—S2A—C20A—C21A126.69 (18)
C2C—N3C—C4C—C5C3.1 (3)O6A—S2A—C20A—C19A64.27 (19)
N4C—C4C—C5C—C6C179.5 (2)O4A—S2A—C20A—C19A175.96 (16)
N3C—C4C—C5C—C6C0.3 (3)O5A—S2A—C20A—C19A57.10 (19)
N4C—C4C—C5C—C9C1.2 (3)C19A—C20A—C21A—C22A1.1 (3)
N3C—C4C—C5C—C9C179.6 (2)S2A—C20A—C21A—C22A175.14 (17)
C4C—C5C—C6C—N1C2.7 (3)C20A—C21A—C22A—C23A0.5 (3)
C9C—C5C—C6C—N1C178.06 (19)C21A—C22A—C23A—C24A0.2 (3)
C4C—C5C—C6C—C7C179.7 (2)C22A—C23A—C24A—C19A0.3 (3)
C9C—C5C—C6C—C7C0.5 (3)C22A—C23A—C24A—C15A179.78 (19)
C2C—N1C—C6C—C5C1.7 (3)C18A—C19A—C24A—C23A179.25 (18)
C2C—N1C—C6C—C7C179.58 (19)C20A—C19A—C24A—C23A0.3 (3)
C5C—C6C—C7C—C8C82.4 (3)C18A—C19A—C24A—C15A1.3 (3)
N1C—C6C—C7C—C8C95.2 (3)C20A—C19A—C24A—C15A179.20 (17)
C6B—C5B—C9B—C14B68.6 (3)C16A—C15A—C24A—C23A177.9 (2)
C4B—C5B—C9B—C14B110.1 (3)S1A—C15A—C24A—C23A5.7 (3)
C6B—C5B—C9B—C10B111.3 (2)C16A—C15A—C24A—C19A2.7 (3)
C4B—C5B—C9B—C10B70.0 (3)S1A—C15A—C24A—C19A173.71 (14)
C14B—C9B—C10B—C11B0.9 (3)C22Bi—C16B—C15B—C24B0.7 (4)
C5B—C9B—C10B—C11B179.0 (2)C22Bi—C16B—C15B—S3B179.7 (2)
C9B—C10B—C11B—C12B0.3 (4)O2B—S3B—C15B—C16B114.6 (2)
C10B—C11B—C12B—C13B1.0 (4)O1B—S3B—C15B—C16B125.21 (19)
C10B—C11B—C12B—Cl1B178.60 (18)O3B—S3B—C15B—C16B4.8 (2)
C11B—C12B—C13B—C14B0.3 (4)O2B—S3B—C15B—C24B64.4 (2)
Cl1B—C12B—C13B—C14B179.3 (2)O1B—S3B—C15B—C24B55.8 (2)
C12B—C13B—C14B—C9B1.0 (4)O3B—S3B—C15B—C24B176.22 (17)
C10B—C9B—C14B—C13B1.6 (4)C16B—C15B—C24B—C23B179.8 (2)
C5B—C9B—C14B—C13B178.3 (2)S3B—C15B—C24B—C23B0.9 (3)
C6A—C5A—C9A—C14A105.4 (3)C16B—C15B—C24B—C24Bi1.4 (4)
C4A—C5A—C9A—C14A75.0 (3)S3B—C15B—C24B—C24Bi179.7 (2)
C6A—C5A—C9A—C10A74.8 (3)C15B—C24B—C23B—C22B179.1 (2)
C4A—C5A—C9A—C10A104.9 (2)C24Bi—C24B—C23B—C22B0.3 (4)
C14A—C9A—C10A—C11A1.5 (3)C24B—C23B—C22B—C16Bi0.4 (4)
C5A—C9A—C10A—C11A178.7 (2)
Symmetry code: (i) x, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2B—H2B1···O1Bii0.862.213.030 (3)158
N1A—H1A···O1A0.861.902.752 (3)170
N1B—H1B···O3Biii0.861.952.778 (3)160
N1C—H1C···O4Aiv0.861.902.755 (3)173
N2B—H2B2···O2Biii0.862.042.889 (3)169
N4B—H4B1···N3Aii0.862.353.192 (3)165
N4B—H4B2···O5Av0.862.272.940 (2)135
N2A—H2A1···O6Avi0.862.382.965 (3)125
N2A—H2A2···O2A0.862.102.936 (3)164
N4A—H4A1···N3Bvii0.862.112.955 (3)170
N4A—H4A2···O1B0.862.172.913 (2)145
N2C—H2C1···O3Aviii0.861.972.818 (3)169
N2C—H2C2···O5Aiv0.862.273.102 (3)162
N4C—H4C2···O2A0.862.323.027 (3)140
C8B—H8B1···O3Biii0.962.593.380 (4)140
Symmetry codes: (ii) x+1, y, z; (iii) x+1, y, z+2; (iv) x, y+2, z+1; (v) x+1, y1, z; (vi) x, y1, z; (vii) x1, y, z; (viii) x+1, y+1, z+1.
Internal angles at atom N1 (C2—N1—C6) in (I)–(XI) compared with neutral TMP and PMN top
CompoundAngle
Neutral TMPa115.5 (5)
(I)119.5 (2)
(II)120.3 (2)
(III)120.23 (19)
((IV)119.92 (14)
(V), Molecule A120.09 (19)
(V), Molecule B120.31 (19)
Neutral PMNb, Molecule A116.25 (18)
Neutral PMNb, Molecule A116.09 (18)
(VI)121.2 (2)
((VII))120.8 (3)
(VIII)121.5 (2)
(IX), Molecule A121.97 (19)
(IX), Molecule B122.21 (19)
(IX), Molecule C122.0 (2)
Reference: (a) Koetzle & Williams (1976); (b) Sethuraman & Muthiah (2002).
Torsion and dihedral angles (°) between the pyrimidine and benzene ring planes of TMP salts top
CompoundTorsion angleDihedral angle pyrimidine/phenyl ring
τ1(C4—C5—C7—C8)τ2(C5—C7—C8—C9)
Neutral TMPa-89.4 (1)153.3 (1)71.33 (2)
(I)-75.0 (3)-22.3 (3)86.00 (10)
(II)-56.5 (4)-37.0 (4)77.01 (12)
(III))-56.6 (3)-37.0 (3)77.26 (10)
(IV))74.8 (2)23.7 (2)88.16 (7)
(V), Molecule A-177.2 (2)-175. 37 (19)83.77 (11)
(V), Molecule B83.5 (3)86.5 (3)89.10 (11)
Reference: (a) Koetzle & Williams (1976).
Torsion and dihedral angles (°) between the pyrimidine and benzene ring plane of the PMN salts top
CompoundTorsion angle C5—C6—C7—C8Dihedral angle pyrimidine/phenyl
Neutral PMNa, Molecule A89.5 (2)74.4 (1)
Neutral PMNa, Molecule B97.8 (1)82.4 (1)
(VI)97.2 (4)80.42 (13)
(VII)-105.7 (4)73.24 (15)
(VIII)110.0 (4)69.56 (17)
(IX), Molecule A92.6 (3)74.50 (13)
(IX), Molecule B-102.7 (3)68.86 (12)
(IX), Molecule C82.4 (3)68.69 (13)
Reference: (a) Sethuraman & Muthiah (2002).
 

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