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We present here a new structure of a 1:1 salt of trimethoprim with hemifumarate, highlighted by single-crystal X-ray diffraction and computational conformational studies. This salt was formed during cocrystallization assays conducted to combine trimethoprim and other APIs whose combination exhibits interesting properties. Theoretical in vacuo investigations have been performed on the organic salt through a DFT two-dimensional conformational scan of torsion angles between the two aromatic moieties of trimethoprim. The evaluation of relative energies for hydrogen-bond interactions in the structure has also been performed. Comparison with conformational data from structures implying trimethoprim retrieved from the Cambridge Structural Database (CSD) shows good agreement with theoretical results, proving the validity of vacuum ab initio calculations in describing the energetic landscape of the molecule and thereby gain initial insight into the prediction process for possible new conformations and therefore potential new polymorphs.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520615008422/dk5035sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520615008422/dk5035Isup2.hkl
Contains datablock I

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520615008422/dk5035sup3.pdf
Extra tables and figures

CCDC reference: 1062325

Computing details top

Data collection: CrysAlis PRO, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01); cell refinement: CrysAlis PRO, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01); data reduction: CrysAlis PRO, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
[Figure 11]
(I) top
Crystal data top
C14H19N4O3·C4H3O4Z = 4
Mr = 406.40F(000) = 856
Triclinic, P1Dx = 1.409 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.4700 (5) ÅCell parameters from 6640 reflections
b = 14.6637 (10) Åθ = 3.0–28.8°
c = 15.0285 (10) ŵ = 0.11 mm1
α = 61.535 (7)°T = 293 K
β = 83.550 (5)°Prism, colourless
γ = 71.020 (5)°0.4 × 0.3 × 0.15 mm
V = 1915.6 (2) Å3
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
6752 independent reflections
Radiation source: fine-focus sealed tube5223 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 5.1856 pixels mm-1θmax = 25.0°, θmin = 2.7°
ω scansh = 1212
Absorption correction: multi-scan
CrysAlis PRO, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
k = 1717
Tmin = 0.978, Tmax = 1.000l = 1717
16621 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0561P)2 + 0.1954P]
where P = (Fo2 + 2Fc2)/3
6752 reflections(Δ/σ)max = 0.001
593 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C14H19N4O3·C4H3O4γ = 71.020 (5)°
Mr = 406.40V = 1915.6 (2) Å3
Triclinic, P1Z = 4
a = 10.4700 (5) ÅMo Kα radiation
b = 14.6637 (10) ŵ = 0.11 mm1
c = 15.0285 (10) ÅT = 293 K
α = 61.535 (7)°0.4 × 0.3 × 0.15 mm
β = 83.550 (5)°
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
6752 independent reflections
Absorption correction: multi-scan
CrysAlis PRO, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
5223 reflections with I > 2σ(I)
Tmin = 0.978, Tmax = 1.000Rint = 0.028
16621 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.19 e Å3
6752 reflectionsΔρmin = 0.22 e Å3
593 parameters
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.61271 (15)0.38736 (12)0.11002 (12)0.0283 (4)
C20.72682 (16)0.29744 (13)0.10319 (13)0.0320 (4)
C30.85082 (16)0.29909 (13)0.08334 (13)0.0324 (4)
C40.96309 (16)0.20984 (13)0.07619 (13)0.0307 (4)
C50.11865 (16)0.88629 (12)0.11644 (13)0.0320 (4)
C60.23237 (17)0.79751 (13)0.10839 (14)0.0369 (4)
C70.35606 (16)0.79909 (13)0.08889 (13)0.0323 (4)
C80.46522 (16)0.71149 (13)0.07756 (13)0.0325 (4)
C90.15899 (16)0.40975 (13)0.11932 (12)0.0325 (4)
C110.03401 (16)0.49566 (13)0.17210 (12)0.0309 (4)
C120.03922 (16)0.53913 (12)0.20899 (12)0.0313 (4)
C130.17243 (17)0.51564 (13)0.19324 (13)0.0337 (4)
H130.22470.54290.21450.040*
C140.03083 (18)0.61316 (14)0.25435 (13)0.0394 (4)
H14A0.09140.67900.20220.047*
H14B0.03710.63420.27240.047*
C150.11169 (18)0.56891 (14)0.34698 (13)0.0370 (4)
C160.23083 (19)0.63986 (14)0.35654 (14)0.0428 (5)
H160.26470.70990.30320.051*
C170.30025 (19)0.60721 (15)0.44525 (15)0.0433 (5)
C180.25000 (19)0.50329 (15)0.52489 (14)0.0426 (5)
C190.13568 (19)0.42945 (14)0.51280 (14)0.0422 (4)
C200.06590 (19)0.46258 (14)0.42431 (13)0.0408 (4)
H200.01150.41340.41700.049*
C210.4828 (2)0.77353 (16)0.37748 (18)0.0679 (7)
H21A0.42620.81960.35660.102*
H21B0.56800.80810.39650.102*
H21C0.49770.76170.32250.102*
C220.4062 (3)0.4224 (2)0.63259 (19)0.0896 (9)
H22A0.48290.47170.58620.134*
H22B0.43460.39920.70090.134*
H22C0.36730.36000.62140.134*
C230.0037 (3)0.24246 (17)0.58657 (18)0.0744 (7)
H23A0.01530.23610.52910.112*
H23B0.01060.17510.64720.112*
H23C0.08760.25840.57850.112*
C310.66032 (16)0.92351 (12)0.10837 (12)0.0311 (4)
C330.47925 (16)1.00526 (12)0.17511 (12)0.0303 (4)
C340.56370 (16)1.03973 (12)0.21362 (12)0.0298 (4)
C350.69486 (16)1.01285 (12)0.19287 (13)0.0338 (4)
H350.75401.03360.21570.041*
C360.51024 (17)1.10216 (14)0.27322 (13)0.0374 (4)
H36A0.49321.17940.22740.045*
H36B0.42441.09160.29960.045*
C370.60313 (17)1.06979 (14)0.36048 (13)0.0359 (4)
C380.64078 (18)1.14762 (15)0.36848 (14)0.0399 (4)
H380.61681.21900.31630.048*
C390.71441 (19)1.11987 (17)0.45407 (15)0.0478 (5)
C400.75048 (19)1.01289 (19)0.53234 (14)0.0529 (5)
C410.7164 (2)0.93428 (16)0.52149 (15)0.0515 (5)
C420.64308 (19)0.96303 (14)0.43668 (14)0.0457 (5)
H420.62010.91010.43050.055*
C430.7160 (3)1.3025 (2)0.3906 (2)0.1008 (10)
H43A0.75821.30590.32940.151*
H43B0.74491.34590.41100.151*
H43C0.61951.33010.37870.151*
C440.9517 (3)0.9365 (4)0.6369 (2)0.1404 (17)
H44A0.97410.86900.63420.211*
H44B0.98070.92210.70200.211*
H44C0.99630.98370.58480.211*
C450.7174 (3)0.74947 (19)0.5971 (2)0.0951 (10)
H45A0.62050.76930.59540.143*
H45B0.75450.68080.65590.143*
H45C0.74970.74330.53720.143*
N10.74417 (14)0.95647 (11)0.13979 (11)0.0347 (3)
N20.23291 (15)0.45310 (11)0.14707 (11)0.0346 (3)
N30.22090 (18)0.34339 (14)0.08010 (13)0.0473 (4)
N40.16757 (15)0.51959 (15)0.17719 (13)0.0459 (4)
N50.71163 (17)0.86200 (13)0.06254 (12)0.0424 (4)
N60.34737 (15)1.02638 (14)0.18853 (13)0.0448 (4)
N70.52898 (13)0.94731 (11)0.12455 (11)0.0341 (3)
N80.02669 (13)0.42998 (11)0.13116 (11)0.0356 (3)
O10.63853 (11)0.47112 (9)0.09711 (10)0.0414 (3)
O20.50113 (11)0.37246 (9)0.12951 (10)0.0465 (3)
O30.94075 (11)0.11664 (9)0.11219 (10)0.0419 (3)
O41.06846 (12)0.22568 (10)0.03920 (11)0.0496 (4)
O50.00559 (12)0.87427 (10)0.12681 (12)0.0551 (4)
O60.14465 (11)0.96717 (9)0.11117 (10)0.0454 (3)
O70.57081 (13)0.72676 (11)0.04089 (12)0.0598 (4)
O90.44029 (11)0.61980 (9)0.10893 (9)0.0405 (3)
O110.41846 (14)0.67168 (11)0.46167 (11)0.0604 (4)
O120.30967 (15)0.47548 (12)0.61707 (10)0.0572 (4)
O130.10111 (15)0.32714 (11)0.59374 (10)0.0610 (4)
O160.75361 (16)1.19234 (15)0.46839 (12)0.0706 (5)
O170.80959 (15)0.98777 (15)0.62184 (11)0.0792 (5)
O180.75826 (17)0.83128 (13)0.60107 (11)0.0785 (5)
H20.7037 (17)0.2371 (14)0.1155 (13)0.037 (5)*
H30.8806 (19)0.3583 (15)0.0733 (14)0.050 (5)*
H3M0.166 (2)0.3156 (17)0.0599 (16)0.061 (6)*
H3N0.302 (3)0.3385 (17)0.0622 (17)0.066 (7)*
H4M0.211 (2)0.5663 (17)0.2015 (15)0.059 (6)*
H4N0.212 (2)0.4963 (16)0.1498 (15)0.053 (6)*
H5M0.653 (2)0.8363 (17)0.0426 (16)0.060 (6)*
H5N0.793 (2)0.8538 (16)0.0422 (15)0.055 (6)*
H60.2051 (19)0.7381 (15)0.1163 (14)0.049 (5)*
H6M0.312 (2)1.0579 (17)0.2223 (16)0.057 (6)*
H6N0.297 (2)1.0006 (16)0.1595 (16)0.059 (6)*
H70.3852 (18)0.8579 (14)0.0794 (14)0.045 (5)*
H1N0.838 (2)0.9362 (16)0.1299 (15)0.063 (6)*
H2N0.322 (2)0.4371 (16)0.1377 (15)0.059 (6)*
H90.521 (2)0.5624 (17)0.1033 (16)0.071 (6)*
H41.023 (2)0.0568 (18)0.1101 (17)0.078 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0219 (9)0.0276 (8)0.0337 (9)0.0027 (7)0.0002 (7)0.0160 (7)
C20.0269 (9)0.0252 (8)0.0452 (11)0.0058 (7)0.0038 (8)0.0194 (8)
C30.0262 (9)0.0292 (9)0.0452 (11)0.0050 (7)0.0035 (8)0.0226 (8)
C40.0229 (9)0.0330 (9)0.0407 (10)0.0047 (7)0.0026 (8)0.0234 (8)
C50.0221 (9)0.0285 (8)0.0427 (10)0.0023 (7)0.0028 (7)0.0185 (8)
C60.0279 (9)0.0283 (9)0.0571 (12)0.0076 (7)0.0072 (8)0.0237 (9)
C70.0266 (9)0.0265 (8)0.0444 (11)0.0058 (7)0.0047 (8)0.0191 (8)
C80.0240 (9)0.0323 (9)0.0446 (10)0.0056 (7)0.0045 (8)0.0231 (8)
C90.0265 (9)0.0347 (9)0.0327 (9)0.0075 (7)0.0044 (7)0.0150 (8)
C110.0241 (9)0.0374 (9)0.0301 (9)0.0081 (7)0.0041 (7)0.0164 (8)
C120.0295 (9)0.0312 (8)0.0310 (9)0.0084 (7)0.0014 (7)0.0136 (7)
C130.0308 (9)0.0327 (9)0.0364 (10)0.0127 (7)0.0002 (8)0.0132 (8)
C140.0428 (11)0.0383 (9)0.0440 (11)0.0165 (8)0.0100 (9)0.0237 (9)
C150.0426 (10)0.0421 (10)0.0390 (10)0.0188 (8)0.0066 (8)0.0262 (9)
C160.0499 (12)0.0386 (10)0.0423 (11)0.0159 (9)0.0111 (9)0.0211 (9)
C170.0470 (11)0.0459 (11)0.0505 (12)0.0207 (9)0.0154 (9)0.0316 (10)
C180.0502 (12)0.0553 (11)0.0358 (11)0.0284 (10)0.0087 (9)0.0255 (9)
C190.0510 (12)0.0434 (10)0.0375 (11)0.0195 (9)0.0035 (9)0.0186 (9)
C200.0440 (11)0.0425 (10)0.0430 (11)0.0141 (8)0.0019 (9)0.0251 (9)
C210.0707 (16)0.0455 (12)0.0753 (16)0.0101 (11)0.0225 (13)0.0278 (12)
C220.092 (2)0.126 (2)0.0558 (16)0.0756 (19)0.0142 (14)0.0225 (16)
C230.0841 (18)0.0502 (13)0.0650 (16)0.0059 (12)0.0069 (13)0.0160 (12)
C310.0240 (9)0.0303 (8)0.0342 (10)0.0056 (7)0.0047 (7)0.0139 (8)
C330.0233 (8)0.0335 (8)0.0326 (9)0.0066 (7)0.0027 (7)0.0160 (8)
C340.0252 (9)0.0282 (8)0.0330 (9)0.0061 (7)0.0012 (7)0.0136 (7)
C350.0275 (9)0.0329 (9)0.0419 (10)0.0101 (7)0.0006 (8)0.0174 (8)
C360.0316 (9)0.0381 (9)0.0458 (11)0.0058 (8)0.0011 (8)0.0249 (9)
C370.0308 (9)0.0420 (10)0.0362 (10)0.0082 (8)0.0045 (8)0.0218 (8)
C380.0382 (10)0.0468 (10)0.0383 (11)0.0140 (8)0.0051 (8)0.0228 (9)
C390.0360 (11)0.0769 (14)0.0465 (12)0.0219 (10)0.0090 (9)0.0397 (12)
C400.0325 (11)0.0889 (16)0.0326 (11)0.0085 (10)0.0018 (9)0.0315 (12)
C410.0394 (11)0.0547 (12)0.0361 (12)0.0015 (9)0.0054 (9)0.0136 (10)
C420.0445 (11)0.0411 (10)0.0450 (12)0.0062 (8)0.0021 (9)0.0197 (9)
C430.133 (3)0.095 (2)0.115 (3)0.065 (2)0.005 (2)0.059 (2)
C440.0425 (16)0.276 (5)0.071 (2)0.012 (2)0.0121 (14)0.078 (3)
C450.100 (2)0.0458 (14)0.0776 (19)0.0059 (14)0.0209 (16)0.0027 (13)
N10.0198 (7)0.0394 (8)0.0453 (9)0.0084 (6)0.0066 (7)0.0216 (7)
N20.0212 (8)0.0363 (8)0.0441 (9)0.0082 (6)0.0037 (7)0.0179 (7)
N30.0314 (9)0.0586 (10)0.0648 (12)0.0128 (8)0.0172 (9)0.0426 (10)
N40.0233 (8)0.0692 (11)0.0641 (11)0.0107 (8)0.0064 (8)0.0490 (10)
N50.0267 (9)0.0518 (9)0.0551 (10)0.0073 (7)0.0120 (8)0.0352 (9)
N60.0221 (8)0.0691 (11)0.0639 (11)0.0116 (7)0.0101 (8)0.0503 (10)
N70.0224 (7)0.0437 (8)0.0440 (9)0.0092 (6)0.0068 (6)0.0282 (7)
N80.0250 (8)0.0471 (8)0.0424 (9)0.0108 (6)0.0062 (6)0.0281 (7)
O10.0246 (6)0.0341 (6)0.0737 (9)0.0040 (5)0.0035 (6)0.0351 (6)
O20.0221 (6)0.0393 (7)0.0789 (10)0.0073 (5)0.0109 (6)0.0314 (7)
O30.0269 (7)0.0308 (6)0.0692 (9)0.0046 (5)0.0102 (6)0.0288 (6)
O40.0303 (7)0.0490 (7)0.0849 (10)0.0152 (6)0.0240 (7)0.0457 (7)
O50.0224 (7)0.0459 (7)0.1039 (12)0.0090 (6)0.0158 (7)0.0439 (8)
O60.0264 (7)0.0348 (6)0.0831 (10)0.0036 (5)0.0047 (6)0.0380 (7)
O70.0356 (8)0.0551 (8)0.1103 (12)0.0194 (6)0.0326 (8)0.0581 (9)
O90.0280 (7)0.0311 (6)0.0629 (9)0.0035 (5)0.0092 (6)0.0275 (6)
O110.0619 (9)0.0524 (8)0.0597 (9)0.0146 (7)0.0259 (8)0.0276 (7)
O120.0638 (9)0.0793 (10)0.0397 (8)0.0374 (8)0.0137 (7)0.0293 (7)
O130.0706 (10)0.0530 (8)0.0427 (8)0.0150 (7)0.0017 (7)0.0113 (7)
O160.0699 (11)0.1080 (13)0.0700 (11)0.0428 (10)0.0050 (8)0.0602 (11)
O170.0464 (9)0.1414 (15)0.0431 (9)0.0118 (9)0.0031 (7)0.0480 (10)
O180.0759 (12)0.0664 (10)0.0440 (9)0.0056 (9)0.0003 (8)0.0050 (8)
Geometric parameters (Å, º) top
C1—O21.2356 (19)C23—H23A0.9600
C1—O11.2634 (18)C23—H23B0.9600
C1—C21.501 (2)C23—H23C0.9600
C2—C31.304 (2)C31—N71.3288 (19)
C2—H20.921 (17)C31—N51.331 (2)
C3—C41.487 (2)C31—N11.347 (2)
C3—H30.956 (19)C33—N61.327 (2)
C4—O41.2190 (19)C33—N71.3450 (19)
C4—O31.2999 (19)C33—C341.434 (2)
C5—O51.2348 (19)C34—C351.344 (2)
C5—O61.2658 (19)C34—C361.513 (2)
C5—C61.496 (2)C35—N11.358 (2)
C6—C71.300 (2)C35—H350.9300
C6—H60.954 (19)C36—C371.511 (2)
C7—C81.482 (2)C36—H36A0.9700
C7—H70.949 (18)C36—H36B0.9700
C8—O71.2176 (19)C37—C381.381 (2)
C8—O91.3016 (19)C37—C421.382 (2)
C9—N31.329 (2)C38—C391.391 (3)
C9—N81.329 (2)C38—H380.9300
C9—N21.350 (2)C39—O161.366 (2)
C11—N41.329 (2)C39—C401.394 (3)
C11—N81.3377 (19)C40—O171.376 (2)
C11—C121.432 (2)C40—C411.394 (3)
C12—C131.346 (2)C41—O181.367 (2)
C12—C141.502 (2)C41—C421.374 (3)
C13—N21.361 (2)C42—H420.9300
C13—H130.9300C43—O161.422 (3)
C14—C151.519 (2)C43—H43A0.9600
C14—H14A0.9700C43—H43B0.9600
C14—H14B0.9700C43—H43C0.9600
C15—C161.385 (2)C44—O171.420 (3)
C15—C201.387 (2)C44—H44A0.9600
C16—C171.391 (2)C44—H44B0.9600
C16—H160.9300C44—H44C0.9600
C17—O111.371 (2)C45—O181.426 (3)
C17—C181.383 (3)C45—H45A0.9600
C18—O121.381 (2)C45—H45B0.9600
C18—C191.391 (3)C45—H45C0.9600
C19—O131.367 (2)N1—H1N0.95 (2)
C19—C201.391 (2)N2—H2N0.90 (2)
C20—H200.9300N3—H3M0.94 (2)
C21—O111.422 (2)N3—H3N0.85 (2)
C21—H21A0.9600N4—H4M0.90 (2)
C21—H21B0.9600N4—H4N0.88 (2)
C21—H21C0.9600N5—H5M0.95 (2)
C22—O121.403 (3)N5—H5N0.86 (2)
C22—H22A0.9600N6—H6M0.82 (2)
C22—H22B0.9600N6—H6N0.97 (2)
C22—H22C0.9600O3—H41.02 (2)
C23—O131.405 (2)O9—H91.01 (2)
O2—C1—O1125.25 (13)N5—C31—N1118.82 (15)
O2—C1—C2117.01 (14)N6—C33—N7115.39 (15)
O1—C1—C2117.73 (14)N6—C33—C34122.44 (14)
C3—C2—C1125.38 (15)N7—C33—C34122.15 (14)
C3—C2—H2120.2 (10)C35—C34—C33115.22 (14)
C1—C2—H2114.4 (10)C35—C34—C36121.89 (15)
C2—C3—C4125.01 (15)C33—C34—C36122.89 (14)
C2—C3—H3123.2 (11)C34—C35—N1122.45 (16)
C4—C3—H3111.8 (11)C34—C35—H35118.8
O4—C4—O3123.77 (13)N1—C35—H35118.8
O4—C4—C3120.49 (14)C37—C36—C34114.73 (13)
O3—C4—C3115.74 (14)C37—C36—H36A108.6
O5—C5—O6125.42 (13)C34—C36—H36A108.6
O5—C5—C6116.20 (14)C37—C36—H36B108.6
O6—C5—C6118.38 (14)C34—C36—H36B108.6
C7—C6—C5125.57 (16)H36A—C36—H36B107.6
C7—C6—H6121.3 (11)C38—C37—C42119.51 (17)
C5—C6—H6113.1 (11)C38—C37—C36120.43 (15)
C6—C7—C8124.19 (16)C42—C37—C36119.90 (16)
C6—C7—H7122.8 (11)C37—C38—C39120.40 (17)
C8—C7—H7113.0 (11)C37—C38—H38119.8
O7—C8—O9123.46 (14)C39—C38—H38119.8
O7—C8—C7120.60 (15)O16—C39—C38123.94 (19)
O9—C8—C7115.94 (14)O16—C39—C40116.18 (19)
N3—C9—N8118.84 (16)C38—C39—C40119.88 (18)
N3—C9—N2118.89 (16)O17—C40—C41120.7 (2)
N8—C9—N2122.26 (14)O17—C40—C39120.0 (2)
N4—C11—N8116.70 (16)C41—C40—C39119.08 (18)
N4—C11—C12120.75 (15)O18—C41—C42124.7 (2)
N8—C11—C12122.56 (14)O18—C41—C40115.0 (2)
C13—C12—C11115.36 (14)C42—C41—C40120.33 (18)
C13—C12—C14122.68 (15)C41—C42—C37120.72 (18)
C11—C12—C14121.78 (14)C41—C42—H42119.6
C12—C13—N2121.90 (16)C37—C42—H42119.6
C12—C13—H13119.0O16—C43—H43A109.5
N2—C13—H13119.0O16—C43—H43B109.5
C12—C14—C15117.43 (13)H43A—C43—H43B109.5
C12—C14—H14A107.9O16—C43—H43C109.5
C15—C14—H14A107.9H43A—C43—H43C109.5
C12—C14—H14B107.9H43B—C43—H43C109.5
C15—C14—H14B107.9O17—C44—H44A109.5
H14A—C14—H14B107.2O17—C44—H44B109.5
C16—C15—C20119.45 (16)H44A—C44—H44B109.5
C16—C15—C14118.23 (15)O17—C44—H44C109.5
C20—C15—C14122.20 (15)H44A—C44—H44C109.5
C15—C16—C17120.52 (17)H44B—C44—H44C109.5
C15—C16—H16119.7O18—C45—H45A109.5
C17—C16—H16119.7O18—C45—H45B109.5
O11—C17—C18115.39 (15)H45A—C45—H45B109.5
O11—C17—C16124.65 (17)O18—C45—H45C109.5
C18—C17—C16119.96 (16)H45A—C45—H45C109.5
O12—C18—C17119.81 (16)H45B—C45—H45C109.5
O12—C18—C19120.58 (17)C31—N1—C35119.43 (14)
C17—C18—C19119.54 (16)C31—N1—H1N120.9 (12)
O13—C19—C18114.35 (16)C35—N1—H1N119.5 (13)
O13—C19—C20125.47 (17)C9—N2—C13119.51 (14)
C18—C19—C20120.18 (17)C9—N2—H2N119.2 (13)
C15—C20—C19120.06 (16)C13—N2—H2N121.2 (13)
C15—C20—H20120.0C9—N3—H3M117.1 (12)
C19—C20—H20120.0C9—N3—H3N119.9 (15)
O11—C21—H21A109.5H3M—N3—H3N121.5 (19)
O11—C21—H21B109.5C11—N4—H4M118.4 (13)
H21A—C21—H21B109.5C11—N4—H4N119.5 (13)
O11—C21—H21C109.5H4M—N4—H4N121.6 (19)
H21A—C21—H21C109.5C31—N5—H5M119.0 (12)
H21B—C21—H21C109.5C31—N5—H5N121.2 (13)
O12—C22—H22A109.5H5M—N5—H5N119.0 (18)
O12—C22—H22B109.5C33—N6—H6M120.1 (15)
H22A—C22—H22B109.5C33—N6—H6N117.4 (12)
O12—C22—H22C109.5H6M—N6—H6N122.5 (19)
H22A—C22—H22C109.5C31—N7—C33118.45 (14)
H22B—C22—H22C109.5C9—N8—C11118.21 (14)
O13—C23—H23A109.5C4—O3—H4112.6 (12)
O13—C23—H23B109.5C8—O9—H9111.9 (12)
H23A—C23—H23B109.5C17—O11—C21117.11 (14)
O13—C23—H23C109.5C18—O12—C22115.41 (16)
H23A—C23—H23C109.5C19—O13—C23119.67 (15)
H23B—C23—H23C109.5C39—O16—C43117.38 (18)
N7—C31—N5118.91 (16)C40—O17—C44117.14 (17)
N7—C31—N1122.24 (14)C41—O18—C45117.2 (2)
O2—C1—C2—C3179.96 (17)C34—C36—C37—C38126.38 (16)
O1—C1—C2—C31.2 (3)C34—C36—C37—C4258.2 (2)
C1—C2—C3—C4179.66 (16)C42—C37—C38—C392.2 (2)
C2—C3—C4—O4166.26 (18)C36—C37—C38—C39173.20 (15)
C2—C3—C4—O314.3 (3)C37—C38—C39—O16178.95 (16)
O5—C5—C6—C7173.97 (19)C37—C38—C39—C400.0 (2)
O6—C5—C6—C75.3 (3)O16—C39—C40—O176.5 (2)
C5—C6—C7—C8177.56 (16)C38—C39—C40—O17172.56 (15)
C6—C7—C8—O7166.05 (19)O16—C39—C40—C41178.47 (16)
C6—C7—C8—O914.0 (3)C38—C39—C40—C412.5 (3)
N4—C11—C12—C13175.43 (16)O17—C40—C41—O186.2 (2)
N8—C11—C12—C134.5 (2)C39—C40—C41—O18178.72 (16)
N4—C11—C12—C140.2 (3)O17—C40—C41—C42172.20 (16)
N8—C11—C12—C14179.74 (15)C39—C40—C41—C422.8 (3)
C11—C12—C13—N21.2 (2)O18—C41—C42—C37178.93 (16)
C14—C12—C13—N2176.41 (15)C40—C41—C42—C370.7 (3)
C13—C12—C14—C15125.77 (18)C38—C37—C42—C411.9 (3)
C11—C12—C14—C1559.3 (2)C36—C37—C42—C41173.54 (15)
C12—C14—C15—C16143.39 (17)N7—C31—N1—C352.3 (2)
C12—C14—C15—C2040.7 (2)N5—C31—N1—C35175.45 (15)
C20—C15—C16—C173.8 (3)C34—C35—N1—C311.6 (2)
C14—C15—C16—C17172.26 (16)N3—C9—N2—C13175.86 (15)
C15—C16—C17—O11179.86 (17)N8—C9—N2—C133.2 (2)
C15—C16—C17—C180.3 (3)C12—C13—N2—C92.4 (2)
O11—C17—C18—O127.5 (3)N5—C31—N7—C33176.95 (15)
C16—C17—C18—O12172.09 (16)N1—C31—N7—C330.8 (2)
O11—C17—C18—C19175.59 (16)N6—C33—N7—C31179.88 (15)
C16—C17—C18—C194.8 (3)C34—C33—N7—C311.4 (2)
O12—C18—C19—O137.7 (2)N3—C9—N8—C11179.04 (16)
C17—C18—C19—O13175.49 (16)N2—C9—N8—C110.0 (2)
O12—C18—C19—C20171.56 (16)N4—C11—N8—C9176.00 (16)
C17—C18—C19—C205.3 (3)C12—C11—N8—C93.9 (2)
C16—C15—C20—C193.3 (3)C18—C17—O11—C21171.92 (18)
C14—C15—C20—C19172.61 (16)C16—C17—O11—C218.5 (3)
O13—C19—C20—C15179.61 (17)C17—C18—O12—C2295.7 (2)
C18—C19—C20—C151.3 (3)C19—C18—O12—C2287.4 (2)
N6—C33—C34—C35179.42 (16)C18—C19—O13—C23173.33 (18)
N7—C33—C34—C351.9 (2)C20—C19—O13—C237.5 (3)
N6—C33—C34—C360.4 (3)C38—C39—O16—C430.1 (3)
N7—C33—C34—C36178.21 (15)C40—C39—O16—C43178.9 (2)
C33—C34—C35—N10.4 (2)C41—C40—O17—C4482.9 (3)
C36—C34—C35—N1179.74 (15)C39—C40—O17—C44102.1 (3)
C35—C34—C36—C3738.9 (2)C42—C41—O18—C452.9 (3)
C33—C34—C36—C37141.21 (16)C40—C41—O18—C45175.50 (18)

Experimental details

Crystal data
Chemical formulaC14H19N4O3·C4H3O4
Mr406.40
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)10.4700 (5), 14.6637 (10), 15.0285 (10)
α, β, γ (°)61.535 (7), 83.550 (5), 71.020 (5)
V3)1915.6 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.4 × 0.3 × 0.15
Data collection
DiffractometerXcalibur, Ruby, Gemini ultra
diffractometer
Absorption correctionMulti-scan
CrysAlis PRO, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
Tmin, Tmax0.978, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
16621, 6752, 5223
Rint0.028
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.120, 1.04
No. of reflections6752
No. of parameters593
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.19, 0.22

Computer programs: CrysAlis PRO, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01), SHELXL97 (Sheldrick, 1997).

 

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