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Iclaprim and mesylate mol­ecules are linked into a hydrogen-bonded mol­ecular tape, the central section of which is composed of fused rings.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989022011689/wm5666sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989022011689/wm5666Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989022011689/wm5666Isup3.cml
Supplementary material

CCDC reference: 2224639

Computing details top

Data collection: APEX3 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: XP in SHELXTL (Sheldrick, 2008), Mercury (Macrae et al., 2020); software used to prepare material for publication: PLATON (Spek, 2020) and publCIF (Westrip, 2010).

2,6-Diamino-5-[(2-cyclopropyl-7,8-dimethoxy-2H-1-benzopyran-5-yl)methyl]pyrimidin-1-ium methanesulfonate top
Crystal data top
C19H23N4O3+·CH3O3SZ = 2
Mr = 450.51F(000) = 476
Triclinic, P1Dx = 1.433 Mg m3
a = 5.4726 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.8450 (4) ÅCell parameters from 9886 reflections
c = 22.1395 (11) Åθ = 2.3–25.3°
α = 98.094 (2)°µ = 0.20 mm1
β = 93.754 (2)°T = 223 K
γ = 98.919 (2)°Prism, colourless
V = 1043.98 (9) Å30.21 × 0.18 × 0.03 mm
Data collection top
Bruker D8 QUEST PHOTON 100
diffractometer
3851 measured reflections
Radiation source: Incoatec Microfocus3851 independent reflections
Multi layered optics monochromator3507 reflections with I > 2σ(I)
Detector resolution: 10.4 pixels mm-1θmax = 25.4°, θmin = 2.4°
φ and ω scansh = 66
Absorption correction: multi-scan
(TWINABS; Bruker, 2013)
k = 1010
Tmin = 0.910, Tmax = 0.971l = 2610
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.104 w = 1/[σ2(Fo2) + (0.0406P)2 + 0.7995P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
3851 reflectionsΔρmax = 0.57 e Å3
320 parametersΔρmin = 0.30 e Å3
10 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.026 (3)
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.3058 (4)0.7951 (2)0.38547 (8)0.0428 (5)
O20.9479 (4)1.1480 (2)0.33158 (8)0.0413 (5)
O30.6716 (4)1.0418 (2)0.41560 (7)0.0418 (5)
N10.0557 (4)0.9523 (2)0.10508 (8)0.0239 (4)
H1N0.015 (5)1.042 (3)0.1116 (12)0.035 (7)*
N20.0189 (3)0.7157 (2)0.03914 (8)0.0240 (4)
N30.2450 (4)0.8895 (2)0.02407 (10)0.0314 (5)
H3A0.292 (5)0.976 (2)0.0359 (11)0.030 (7)*
H3B0.318 (5)0.831 (3)0.0091 (10)0.041 (8)*
N40.2945 (4)0.5524 (2)0.05307 (9)0.0296 (4)
H4A0.215 (5)0.491 (3)0.0214 (10)0.042 (8)*
H4B0.416 (4)0.528 (3)0.0742 (11)0.034 (7)*
C10.2336 (4)0.9125 (2)0.14129 (10)0.0230 (5)
H10.30240.98210.17650.028*
C20.0565 (4)0.8502 (2)0.05556 (9)0.0219 (4)
C30.2094 (4)0.6806 (2)0.07298 (9)0.0216 (4)
C40.3182 (4)0.7772 (2)0.12931 (9)0.0210 (4)
C50.5138 (5)0.7290 (3)0.17050 (10)0.0287 (5)
H5A0.47040.61770.17150.034*
H5B0.67310.74640.15270.034*
C60.5457 (4)0.8135 (3)0.23546 (10)0.0263 (5)
C70.7329 (4)0.9416 (3)0.25216 (10)0.0280 (5)
H70.83590.97480.22260.034*
C80.7705 (4)1.0212 (3)0.31165 (10)0.0291 (5)
C90.6184 (5)0.9716 (3)0.35590 (10)0.0292 (5)
C100.4339 (5)0.8453 (3)0.33923 (10)0.0289 (5)
C110.3909 (5)0.7643 (3)0.27896 (10)0.0297 (5)
C120.1991 (6)0.6280 (3)0.26835 (13)0.0480 (7)
H120.17960.56220.23050.058*
C130.0514 (6)0.5956 (3)0.31140 (14)0.0506 (8)
H130.06840.50520.30380.061*
C140.0691 (5)0.6975 (4)0.37117 (13)0.0477 (7)
H140.05060.76880.36580.057*
C150.0006 (7)0.6284 (4)0.42415 (16)0.0603 (9)
H150.088 (6)0.537 (3)0.4274 (16)0.072*
C160.0784 (9)0.7122 (6)0.47930 (19)0.0775 (11)
H16A0.051 (8)0.687 (5)0.5200 (11)0.093*
H16B0.082 (9)0.821 (3)0.4736 (19)0.093*
C170.2553 (8)0.5873 (6)0.4384 (2)0.0800 (12)
H17A0.310 (8)0.490 (3)0.4518 (19)0.096*
H17B0.369 (7)0.614 (5)0.4075 (15)0.096*
C181.1370 (5)1.1840 (3)0.29246 (12)0.0407 (6)
H18A1.25671.27180.31280.061*
H18B1.06371.20930.25490.061*
H18C1.21991.09530.28300.061*
C190.4888 (7)1.1252 (4)0.44003 (14)0.0568 (8)
H19A0.53891.16680.48270.085*
H19B0.33081.05620.43680.085*
H19C0.47191.20950.41720.085*
S10.73446 (11)0.29318 (6)0.12358 (2)0.02483 (16)
O40.9826 (3)0.26069 (18)0.14030 (8)0.0348 (4)
O50.5834 (3)0.16098 (19)0.08426 (8)0.0381 (4)
O60.7365 (3)0.43739 (19)0.09992 (8)0.0362 (4)
C200.5874 (5)0.3152 (3)0.19206 (11)0.0339 (6)
H20A0.59740.22630.21270.051*
H20B0.41450.32270.18270.051*
H20C0.66940.40860.21850.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0498 (11)0.0446 (10)0.0295 (9)0.0066 (9)0.0072 (8)0.0039 (8)
O20.0414 (11)0.0421 (10)0.0327 (9)0.0078 (8)0.0035 (8)0.0043 (8)
O30.0470 (12)0.0497 (11)0.0230 (8)0.0026 (9)0.0004 (8)0.0070 (7)
N10.0272 (10)0.0169 (9)0.0275 (10)0.0082 (8)0.0012 (8)0.0003 (7)
N20.0252 (10)0.0222 (9)0.0236 (9)0.0068 (8)0.0005 (8)0.0014 (7)
N30.0311 (11)0.0299 (11)0.0323 (11)0.0133 (9)0.0084 (9)0.0021 (9)
N40.0301 (11)0.0273 (10)0.0288 (10)0.0134 (9)0.0077 (9)0.0094 (8)
C10.0248 (11)0.0207 (10)0.0221 (10)0.0037 (9)0.0009 (9)0.0002 (8)
C20.0227 (11)0.0224 (10)0.0214 (10)0.0048 (9)0.0037 (9)0.0041 (8)
C30.0221 (11)0.0206 (10)0.0217 (10)0.0036 (9)0.0026 (9)0.0018 (8)
C40.0222 (11)0.0204 (10)0.0201 (10)0.0041 (9)0.0025 (9)0.0013 (8)
C50.0334 (13)0.0278 (11)0.0256 (11)0.0133 (10)0.0025 (10)0.0002 (9)
C60.0306 (12)0.0270 (11)0.0226 (11)0.0145 (10)0.0033 (9)0.0003 (9)
C70.0283 (12)0.0320 (12)0.0247 (11)0.0085 (10)0.0025 (9)0.0040 (9)
C80.0291 (13)0.0280 (11)0.0288 (12)0.0052 (10)0.0027 (10)0.0017 (9)
C90.0342 (13)0.0318 (12)0.0205 (11)0.0071 (10)0.0019 (9)0.0005 (9)
C100.0348 (13)0.0284 (11)0.0251 (11)0.0090 (10)0.0017 (10)0.0059 (9)
C110.0321 (13)0.0267 (11)0.0291 (11)0.0064 (10)0.0038 (11)0.0020 (9)
C120.0526 (18)0.0426 (15)0.0401 (15)0.0066 (14)0.0002 (14)0.0057 (12)
C130.0493 (18)0.0459 (16)0.0488 (17)0.0112 (14)0.0013 (14)0.0034 (13)
C140.0366 (15)0.0582 (18)0.0450 (16)0.0016 (13)0.0020 (13)0.0079 (13)
C150.061 (2)0.0572 (19)0.062 (2)0.0019 (17)0.0203 (17)0.0109 (16)
C160.072 (3)0.097 (3)0.064 (2)0.002 (3)0.026 (2)0.019 (2)
C170.046 (2)0.112 (3)0.089 (3)0.002 (2)0.014 (2)0.048 (3)
C180.0365 (15)0.0428 (14)0.0404 (14)0.0013 (12)0.0012 (12)0.0081 (12)
C190.069 (2)0.0547 (18)0.0415 (16)0.0133 (17)0.0076 (15)0.0144 (13)
S10.0219 (3)0.0225 (3)0.0302 (3)0.0083 (2)0.0031 (2)0.0019 (2)
O40.0245 (9)0.0312 (8)0.0486 (10)0.0121 (7)0.0063 (8)0.0022 (7)
O50.0330 (9)0.0345 (9)0.0417 (10)0.0086 (8)0.0085 (8)0.0093 (7)
O60.0366 (10)0.0325 (9)0.0468 (10)0.0173 (8)0.0103 (8)0.0150 (7)
C200.0357 (14)0.0319 (12)0.0333 (13)0.0051 (11)0.0015 (11)0.0034 (10)
Geometric parameters (Å, º) top
O1—C101.365 (3)C10—C111.410 (3)
O1—C141.431 (3)C11—C121.451 (4)
O2—C81.364 (3)C12—C131.323 (4)
O2—C181.420 (3)C12—H120.9400
O3—C91.371 (3)C13—C141.481 (4)
O3—C191.423 (4)C13—H130.9400
N1—C11.341 (3)C14—C151.441 (4)
N1—C21.362 (3)C14—H140.9900
N1—H1N0.85 (3)C15—C171.458 (5)
N2—C21.330 (3)C15—C161.463 (5)
N2—C31.345 (3)C15—H151.007 (18)
N3—C21.325 (3)C16—C171.500 (6)
N3—H3A0.857 (17)C16—H16A0.965 (19)
N3—H3B0.869 (17)C16—H16B0.988 (19)
N4—C31.322 (3)C17—H17A0.958 (19)
N4—H4A0.871 (17)C17—H17B0.971 (19)
N4—H4B0.863 (17)C18—H18A0.9700
C1—C41.347 (3)C18—H18B0.9700
C1—H10.9400C18—H18C0.9700
C3—C41.444 (3)C19—H19A0.9700
C4—C51.510 (3)C19—H19B0.9700
C5—C61.510 (3)C19—H19C0.9700
C5—H5A0.9800S1—O61.4442 (16)
C5—H5B0.9800S1—O51.4588 (17)
C6—C71.394 (3)S1—O41.4658 (17)
C6—C111.395 (3)S1—C201.763 (2)
C7—C81.390 (3)C20—H20A0.9700
C7—H70.9400C20—H20B0.9700
C8—C91.400 (3)C20—H20C0.9700
C9—C101.375 (3)
C10—O1—C14119.5 (2)C12—C13—C14122.0 (3)
C8—O2—C18117.48 (19)C12—C13—H13119.0
C9—O3—C19115.4 (2)C14—C13—H13119.0
C1—N1—C2119.79 (18)O1—C14—C15109.1 (2)
C1—N1—H1N121.2 (18)O1—C14—C13112.5 (2)
C2—N1—H1N118.9 (18)C15—C14—C13118.4 (3)
C2—N2—C3118.52 (18)O1—C14—H14105.2
C2—N3—H3A119.3 (18)C15—C14—H14105.2
C2—N3—H3B121.4 (19)C13—C14—H14105.2
H3A—N3—H3B119 (3)C14—C15—C17123.6 (4)
C3—N4—H4A118.4 (19)C14—C15—C16124.3 (3)
C3—N4—H4B119.0 (18)C17—C15—C1661.8 (3)
H4A—N4—H4B122 (3)C14—C15—H15110 (2)
N1—C1—C4122.8 (2)C17—C15—H15108 (2)
N1—C1—H1118.6C16—C15—H15120 (2)
C4—C1—H1118.6C15—C16—C1758.9 (3)
N3—C2—N2120.8 (2)C15—C16—H16A124 (3)
N3—C2—N1117.59 (19)C17—C16—H16A112 (3)
N2—C2—N1121.6 (2)C15—C16—H16B109 (3)
N4—C3—N2117.50 (19)C17—C16—H16B118 (3)
N4—C3—C4120.4 (2)H16A—C16—H16B120 (4)
N2—C3—C4122.07 (19)C15—C17—C1659.3 (3)
C1—C4—C3114.73 (19)C15—C17—H17A120 (3)
C1—C4—C5123.42 (19)C16—C17—H17A120 (3)
C3—C4—C5121.84 (18)C15—C17—H17B110 (3)
C6—C5—C4114.54 (18)C16—C17—H17B120 (3)
C6—C5—H5A108.6H17A—C17—H17B114 (4)
C4—C5—H5A108.6O2—C18—H18A109.5
C6—C5—H5B108.6O2—C18—H18B109.5
C4—C5—H5B108.6H18A—C18—H18B109.5
H5A—C5—H5B107.6O2—C18—H18C109.5
C7—C6—C11119.7 (2)H18A—C18—H18C109.5
C7—C6—C5119.6 (2)H18B—C18—H18C109.5
C11—C6—C5120.8 (2)O3—C19—H19A109.5
C8—C7—C6121.3 (2)O3—C19—H19B109.5
C8—C7—H7119.3H19A—C19—H19B109.5
C6—C7—H7119.3O3—C19—H19C109.5
O2—C8—C7125.0 (2)H19A—C19—H19C109.5
O2—C8—C9115.5 (2)H19B—C19—H19C109.5
C7—C8—C9119.5 (2)O6—S1—O5113.41 (11)
O3—C9—C10121.8 (2)O6—S1—O4113.82 (11)
O3—C9—C8119.0 (2)O5—S1—O4111.29 (10)
C10—C9—C8119.0 (2)O6—S1—C20105.55 (11)
O1—C10—C9116.1 (2)O5—S1—C20105.63 (12)
O1—C10—C11121.4 (2)O4—S1—C20106.36 (11)
C9—C10—C11122.4 (2)S1—C20—H20A109.5
C6—C11—C10118.2 (2)S1—C20—H20B109.5
C6—C11—C12125.0 (2)H20A—C20—H20B109.5
C10—C11—C12116.7 (2)S1—C20—H20C109.5
C13—C12—C11120.6 (3)H20A—C20—H20C109.5
C13—C12—H12119.7H20B—C20—H20C109.5
C11—C12—H12119.7
C2—N1—C1—C43.6 (3)C7—C8—C9—C100.3 (3)
C3—N2—C2—N3179.3 (2)C14—O1—C10—C9161.4 (2)
C3—N2—C2—N10.5 (3)C14—O1—C10—C1123.3 (4)
C1—N1—C2—N3174.6 (2)O3—C9—C10—O10.6 (3)
C1—N1—C2—N25.3 (3)C8—C9—C10—O1174.7 (2)
C2—N2—C3—N4174.6 (2)O3—C9—C10—C11174.6 (2)
C2—N2—C3—C45.9 (3)C8—C9—C10—C110.5 (4)
N1—C1—C4—C32.4 (3)C7—C6—C11—C101.3 (3)
N1—C1—C4—C5178.4 (2)C5—C6—C11—C10178.4 (2)
N4—C3—C4—C1173.2 (2)C7—C6—C11—C12176.3 (2)
N2—C3—C4—C17.3 (3)C5—C6—C11—C123.4 (4)
N4—C3—C4—C56.0 (3)O1—C10—C11—C6173.7 (2)
N2—C3—C4—C5173.5 (2)C9—C10—C11—C61.3 (4)
C1—C4—C5—C620.0 (3)O1—C10—C11—C121.8 (4)
C3—C4—C5—C6160.8 (2)C9—C10—C11—C12176.7 (2)
C4—C5—C6—C796.5 (3)C6—C11—C12—C13176.0 (3)
C4—C5—C6—C1183.8 (3)C10—C11—C12—C138.9 (4)
C11—C6—C7—C80.5 (3)C11—C12—C13—C141.7 (5)
C5—C6—C7—C8179.1 (2)C10—O1—C14—C15165.4 (3)
C18—O2—C8—C712.6 (3)C10—O1—C14—C1331.8 (4)
C18—O2—C8—C9167.6 (2)C12—C13—C14—O121.4 (4)
C6—C7—C8—O2179.5 (2)C12—C13—C14—C15150.4 (3)
C6—C7—C8—C90.3 (3)O1—C14—C15—C17149.3 (4)
C19—O3—C9—C1070.3 (3)C13—C14—C15—C1780.3 (5)
C19—O3—C9—C8115.5 (3)O1—C14—C15—C1672.7 (5)
O2—C8—C9—O36.2 (3)C13—C14—C15—C16156.8 (4)
C7—C8—C9—O3174.0 (2)C14—C15—C16—C17113.3 (4)
O2—C8—C9—C10179.5 (2)C14—C15—C17—C16114.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O4i0.85 (3)1.99 (3)2.827 (2)168 (3)
N3—H3A···O5i0.86 (2)2.06 (2)2.896 (3)166 (2)
N3—H3B···O5ii0.87 (2)2.15 (2)2.871 (3)140 (2)
N4—H4A···N2ii0.87 (2)2.27 (2)3.107 (3)163 (2)
N4—H4B···O60.86 (2)2.11 (2)2.948 (3)163 (2)
Symmetry codes: (i) x1, y+1, z; (ii) x, y+1, z.
 

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