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The crystal structure of the cocrystal salt form of the antimalarial drug pyrimethamine with 2,4-dihydroxybenzoic acid in methanol [systematic name: 2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidin-1-ium 2,4-dihydroxybenzoate methanol monosolvate, C12H14ClN4+·C7H5O4−·CH3OH] has been studied using X-ray diffraction data collected at room temperature. The crystal structure was refined using the classical Independent Atom Model (IAM) and the Multipolar Atom Model by transferring electron-density parameters from the ELMAM2 database. The Cl atom was refined anharmonically. The results of both refinement methods have been compared. The intermolecular interactions have been characterized on the basis of Hirshfeld surface analysis and topological analysis using Bader's theory of Atoms in Molecules. The results show that the molecular assembly is built primarily on the basis of charge transfer between 2,4-dihydroxybenzoic acid and pyrimethamine, which results in strong intermolecular hydrogen bonds. This fact is further validated by the calculation of the electrostatic potential based on transferred electron-density parameters.
Supporting information
CCDC reference: 1810824
Data collection: APEX2 (Bruker, 2014); cell refinement: APEX2 (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: MoPro (Jelsch et al., 2005); molecular graphics: Mercury (Macrae et al., 2008) and MoProViewer (Guillot,
2011); software used to prepare material for publication: publCIF (Westrip, 2010).
2,4-Diamino-5-(4-chlorophenyl)-6-ethylpyrimidin-1-ium
2,4-dihydroxybenzoate methanol monosolvate
top
Crystal data top
C12H14ClN4+·C7H5O4−·CH4O | Z = 2 |
Mr = 434.86 | F(000) = 456 |
Triclinic, P1 | Dx = 1.373 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.0137 (4) Å | Cell parameters from 845 reflections |
b = 10.6080 (6) Å | θ = 1.7–28.4° |
c = 11.8132 (6) Å | µ = 0.22 mm−1 |
α = 84.941 (3)° | T = 296 K |
β = 85.798 (2)° | Rod like, colorless |
γ = 69.408 (2)° | 0.42 × 0.32 × 0.28 mm |
V = 1052.18 (9) Å3 | |
Data collection top
Bruker Kappa APEXII CCD detector diffractometer | 5192 independent reflections |
Radiation source: fine-focus sealed tube | 3920 reflections with > 2.0σ(I) |
Graphite monochromator | Rint = 0.026 |
ω and φ scan | θmax = 28.4°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = 0→12 |
Tmin = 0.913, Tmax = 0.941 | k = −12→14 |
18806 measured reflections | l = −15→15 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.061 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.01P)2 + 0.2P] where P = (Fo2 + 2Fc2)/3 |
5182 reflections | (Δ/σ)max = 0.001 |
271 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
Special details top
Refinement. Refinement of F2 against reflections.
The threshold expression of F2 > 2sigma(F2) is
used for calculating R-factors(gt) 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 | x | y | z | Uiso*/Ueq | |
CL1 | 0.33917 (5) | 0.65702 (4) | 0.66837 (3) | 0.06917 (6) | |
N1 | 0.49573 (12) | 0.76445 (10) | −0.01870 (8) | 0.04435 (12) | |
N2 | 0.30231 (11) | 0.97539 (9) | 0.01302 (7) | 0.03601 (11) | |
H2A | 0.23472 | 1.07388 | −0.02262 | 0.05240 | |
N3 | 0.58108 (14) | 0.60521 (11) | 0.12608 (9) | 0.05699 (14) | |
H3A | 0.66202 | 0.54971 | 0.06645 | 0.05975 | |
H3B | 0.58525 | 0.57582 | 0.21289 | 0.05739 | |
N4 | 0.42086 (12) | 0.92775 (10) | −0.16533 (8) | 0.04617 (12) | |
C1 | 0.36847 (13) | 0.77349 (11) | 0.29333 (9) | 0.03487 (12) | |
C2 | 0.41118 (15) | 0.84220 (13) | 0.37355 (10) | 0.04276 (15) | |
H2 | 0.45150 | 0.92513 | 0.34528 | 0.06197 | |
C3 | 0.40338 (15) | 0.80602 (14) | 0.48885 (10) | 0.04662 (16) | |
H3 | 0.43513 | 0.86093 | 0.55043 | 0.07108 | |
C4 | 0.35427 (15) | 0.69867 (13) | 0.52432 (9) | 0.04350 (14) | |
C5 | 0.31429 (16) | 0.62668 (13) | 0.44737 (11) | 0.04883 (16) | |
H5 | 0.27862 | 0.54146 | 0.47659 | 0.06249 | |
C6 | 0.32080 (15) | 0.66498 (13) | 0.33185 (10) | 0.04378 (15) | |
H6 | 0.28857 | 0.60915 | 0.27130 | 0.05634 | |
C7 | 0.37513 (13) | 0.81587 (11) | 0.17042 (9) | 0.03530 (12) | |
C8 | 0.48437 (14) | 0.72848 (12) | 0.09141 (9) | 0.04050 (13) | |
C9 | 0.40732 (13) | 0.88723 (11) | −0.05628 (9) | 0.03643 (12) | |
C10 | 0.28437 (13) | 0.94036 (11) | 0.12575 (9) | 0.03415 (12) | |
C11 | 0.15735 (14) | 1.04593 (12) | 0.18997 (9) | 0.04290 (14) | |
H11A | 0.17458 | 1.14275 | 0.17218 | 0.05727 | |
H11B | 0.16803 | 1.01938 | 0.28119 | 0.05922 | |
C12 | −0.00847 (16) | 1.06057 (16) | 0.15766 (12) | 0.06105 (18) | |
H12A | −0.02503 | 0.96466 | 0.17263 | 0.06199 | |
H12B | −0.02206 | 1.09325 | 0.06888 | 0.06026 | |
H12C | −0.09536 | 1.13435 | 0.20784 | 0.06519 | |
H4A | 0.35680 | 1.02537 | −0.19574 | 0.05493 | |
H4B | 0.50171 | 0.86365 | −0.21649 | 0.05922 | |
O1 | −0.12156 (11) | 0.77498 (9) | 0.06705 (7) | 0.05233 (11) | |
O2 | −0.24389 (10) | 0.80607 (8) | 0.23764 (7) | 0.05055 (10) | |
O3 | 0.13368 (11) | 0.57317 (9) | 0.03745 (7) | 0.06016 (12) | |
H3C | 0.04025 | 0.65741 | 0.02147 | 0.05307 | |
O4 | 0.29860 (10) | 0.23892 (8) | 0.33503 (7) | 0.04685 (10) | |
H4C | 0.26858 | 0.21448 | 0.41339 | 0.06035 | |
C13 | −0.13934 (14) | 0.73606 (12) | 0.17024 (9) | 0.03873 (13) | |
C14 | −0.02874 (13) | 0.60170 (11) | 0.21147 (9) | 0.03473 (12) | |
C15 | 0.10360 (14) | 0.52848 (12) | 0.14411 (9) | 0.03901 (13) | |
C16 | 0.21195 (14) | 0.40712 (12) | 0.18746 (9) | 0.04283 (14) | |
H16 | 0.31466 | 0.35200 | 0.13565 | 0.05911 | |
C17 | 0.18823 (13) | 0.35672 (11) | 0.29675 (9) | 0.03611 (13) | |
C18 | 0.05498 (15) | 0.42560 (12) | 0.36399 (9) | 0.04299 (14) | |
H18 | 0.03474 | 0.38497 | 0.44870 | 0.06575 | |
C19 | −0.05053 (14) | 0.54690 (12) | 0.32008 (9) | 0.04207 (14) | |
H19 | −0.15358 | 0.60014 | 0.37244 | 0.06595 | |
O5 | 0.23042 (12) | 0.14695 (9) | 0.54390 (7) | 0.05488 (12) | |
H5A | 0.23976 | 0.17247 | 0.62158 | 0.06964 | |
C20 | 0.0976 (2) | 0.10696 (18) | 0.54816 (14) | 0.0736 (2) | |
H20A | 0.05890 | 0.11098 | 0.46338 | 0.07710 | |
H20B | 0.00337 | 0.17435 | 0.59849 | 0.08158 | |
H20C | 0.12758 | 0.00543 | 0.58587 | 0.08161 | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
CL1 | 0.0932 (3) | 0.0603 (2) | 0.03487 (16) | −0.0082 (2) | 0.01056 (16) | 0.00861 (14) |
N1 | 0.0481 (6) | 0.0342 (6) | 0.0314 (5) | 0.0075 (4) | 0.0044 (4) | 0.0014 (4) |
N2 | 0.0370 (5) | 0.0307 (5) | 0.0297 (4) | 0.0011 (4) | −0.0014 (4) | −0.0009 (4) |
H2A | 0.05560 | 0.04234 | 0.04176 | 0.00340 | −0.00183 | 0.00241 |
N3 | 0.0660 (7) | 0.0374 (6) | 0.0390 (5) | 0.0139 (5) | 0.0059 (5) | 0.0057 (4) |
H3A | 0.05438 | 0.05253 | 0.04813 | 0.00732 | 0.01229 | 0.00228 |
H3B | 0.05893 | 0.05356 | 0.04018 | 0.00094 | 0.00375 | 0.00771 |
N4 | 0.0491 (6) | 0.0400 (6) | 0.0312 (5) | 0.0044 (5) | 0.0041 (4) | 0.0045 (4) |
C1 | 0.0374 (6) | 0.0333 (6) | 0.0285 (5) | −0.0062 (5) | −0.0013 (4) | 0.0004 (4) |
C2 | 0.0534 (7) | 0.0451 (7) | 0.0324 (6) | −0.0210 (6) | −0.0047 (5) | 0.0027 (5) |
H2 | 0.07840 | 0.05412 | 0.04616 | −0.01536 | −0.00742 | 0.00600 |
C3 | 0.0562 (7) | 0.0504 (8) | 0.0312 (6) | −0.0162 (6) | −0.0061 (5) | 0.0015 (5) |
H3 | 0.10098 | 0.06467 | 0.04151 | −0.02043 | −0.01143 | −0.00017 |
C4 | 0.0465 (7) | 0.0407 (7) | 0.0313 (5) | −0.0028 (5) | 0.0032 (5) | 0.0047 (5) |
C5 | 0.0594 (8) | 0.0401 (7) | 0.0434 (7) | −0.0164 (6) | 0.0085 (6) | 0.0032 (5) |
H5 | 0.07706 | 0.05693 | 0.04358 | −0.01460 | 0.00634 | 0.00439 |
C6 | 0.0539 (7) | 0.0395 (7) | 0.0382 (6) | −0.0172 (6) | 0.0018 (5) | −0.0033 (5) |
H6 | 0.06638 | 0.05229 | 0.04007 | −0.00901 | 0.00375 | −0.00329 |
C7 | 0.0378 (6) | 0.0319 (6) | 0.0269 (5) | −0.0012 (5) | 0.0002 (4) | −0.0008 (4) |
C8 | 0.0443 (6) | 0.0314 (6) | 0.0306 (5) | 0.0042 (5) | 0.0017 (5) | 0.0015 (5) |
C9 | 0.0363 (6) | 0.0332 (6) | 0.0286 (5) | 0.0010 (5) | 0.0018 (4) | −0.0011 (4) |
C10 | 0.0345 (6) | 0.0317 (6) | 0.0294 (5) | −0.0028 (5) | −0.0017 (4) | −0.0031 (4) |
C11 | 0.0450 (7) | 0.0380 (7) | 0.0340 (6) | 0.0014 (5) | −0.0008 (5) | −0.0088 (5) |
H11A | 0.06180 | 0.04469 | 0.05461 | −0.00564 | −0.00190 | −0.00216 |
H11B | 0.06628 | 0.05862 | 0.03619 | −0.00195 | 0.00042 | −0.00199 |
C12 | 0.0416 (7) | 0.0708 (10) | 0.0595 (8) | −0.0063 (7) | 0.0111 (6) | −0.0125 (7) |
H12A | 0.06273 | 0.04421 | 0.06714 | −0.00554 | −0.00015 | 0.00121 |
H12B | 0.06024 | 0.06741 | 0.04171 | −0.00905 | −0.00145 | 0.00011 |
H12C | 0.05873 | 0.05885 | 0.06056 | 0.00319 | 0.00981 | −0.02275 |
H4A | 0.05911 | 0.04529 | 0.04338 | 0.00048 | 0.00000 | 0.00565 |
H4B | 0.06154 | 0.05209 | 0.04283 | 0.00307 | 0.01195 | −0.00021 |
O1 | 0.0615 (6) | 0.0385 (5) | 0.0341 (4) | 0.0076 (4) | 0.0032 (4) | 0.0078 (4) |
O2 | 0.0504 (5) | 0.0400 (5) | 0.0379 (4) | 0.0107 (4) | 0.0045 (4) | 0.0030 (4) |
O3 | 0.0653 (6) | 0.0496 (6) | 0.0363 (4) | 0.0104 (4) | 0.0145 (4) | 0.0085 (4) |
H3C | 0.05585 | 0.03992 | 0.04635 | 0.00279 | 0.00178 | 0.00135 |
O4 | 0.0480 (5) | 0.0365 (5) | 0.0383 (4) | 0.0065 (4) | −0.0024 (4) | 0.0017 (3) |
H4C | 0.06385 | 0.05447 | 0.04625 | −0.00457 | 0.00459 | 0.00971 |
C13 | 0.0413 (6) | 0.0313 (6) | 0.0321 (6) | 0.0005 (5) | −0.0004 (5) | 0.0018 (5) |
C14 | 0.0357 (6) | 0.0289 (6) | 0.0300 (5) | 0.0000 (5) | −0.0004 (4) | 0.0002 (4) |
C15 | 0.0428 (6) | 0.0334 (6) | 0.0286 (5) | 0.0007 (5) | 0.0031 (5) | −0.0007 (4) |
C16 | 0.0431 (6) | 0.0351 (7) | 0.0324 (5) | 0.0065 (5) | 0.0055 (5) | 0.0005 (5) |
H16 | 0.06083 | 0.04742 | 0.04718 | 0.00539 | 0.00998 | −0.00075 |
C17 | 0.0386 (6) | 0.0293 (6) | 0.0304 (5) | 0.0008 (5) | −0.0017 (4) | −0.0024 (4) |
C18 | 0.0478 (7) | 0.0337 (7) | 0.0311 (5) | 0.0035 (5) | 0.0050 (5) | 0.0038 (5) |
H18 | 0.06856 | 0.06220 | 0.04823 | −0.00629 | 0.01085 | 0.01155 |
C19 | 0.0427 (6) | 0.0344 (7) | 0.0330 (6) | 0.0039 (5) | 0.0064 (5) | 0.0024 (5) |
H19 | 0.05816 | 0.05955 | 0.05840 | 0.00109 | 0.01808 | 0.00201 |
O5 | 0.0646 (6) | 0.0529 (6) | 0.0401 (5) | −0.0137 (5) | 0.0020 (4) | 0.0013 (4) |
H5A | 0.07959 | 0.07025 | 0.04809 | −0.01643 | 0.00158 | 0.00955 |
C20 | 0.0670 (10) | 0.0770 (12) | 0.0685 (10) | −0.0169 (9) | 0.0055 (8) | −0.0022 (8) |
H20A | 0.07861 | 0.08248 | 0.06156 | −0.02234 | −0.00910 | 0.02163 |
H20B | 0.07232 | 0.07757 | 0.08007 | −0.01329 | 0.01424 | 0.00383 |
H20C | 0.08235 | 0.07022 | 0.08053 | −0.01971 | −0.00990 | 0.03309 |
Geometric parameters (Å, º) top
CL1—C4 | 1.7278 (11) | C11—H11B | 1.0920 |
N1—C9 | 1.3222 (14) | C11—H11A | 1.0920 |
N1—C8 | 1.3298 (14) | C12—H12A | 1.0770 |
N2—C9 | 1.3563 (13) | C12—H12B | 1.0770 |
N2—C10 | 1.3642 (13) | C12—H12C | 1.0770 |
N2—H2A | 1.0734 (2) | O1—C13 | 1.2693 (13) |
N3—C8 | 1.3393 (14) | O2—C13 | 1.2553 (13) |
N3—H3A | 1.0348 | O3—C15 | 1.3493 (13) |
N3—H3B | 1.0447 | O3—H3C | 1.0037 |
N4—C9 | 1.3324 (13) | O4—C17 | 1.3594 (13) |
N4—H4B | 1.0090 | O4—H4C | 0.9837 |
N4—H4A | 1.0388 | C13—C14 | 1.4872 (15) |
C1—C7 | 1.4849 (14) | C14—C15 | 1.4063 (15) |
C1—C6 | 1.3942 (17) | C14—C19 | 1.3908 (15) |
C1—C2 | 1.3964 (16) | C15—C16 | 1.3950 (15) |
C2—C3 | 1.3858 (16) | C16—C17 | 1.3844 (15) |
C2—H2 | 1.0830 | C16—H16 | 1.0830 |
C3—C4 | 1.3826 (18) | C17—C18 | 1.3974 (15) |
C3—H3 | 1.0830 | C18—C19 | 1.3867 (16) |
C4—C5 | 1.3797 (18) | C18—H18 | 1.0830 |
C5—C6 | 1.3921 (16) | C19—H19 | 1.0830 |
C5—H5 | 1.0830 | O5—C20 | 1.3999 (19) |
C6—H6 | 1.0830 | O5—H5A | 0.9968 |
C7—C8 | 1.4408 (15) | C20—H20A | 1.0770 |
C7—C10 | 1.3682 (15) | C20—H20B | 1.0770 |
C10—C11 | 1.5037 (15) | C20—H20C | 1.0770 |
C11—C12 | 1.5211 (19) | | |
| | | |
C9—N1—C8 | 118.58 (9) | C8—C7—C1 | 121.14 (8) |
C9—N2—C10 | 120.79 (8) | C10—C7—C1 | 122.91 (9) |
C9—N2—H2A | 118.480 | C12—C11—H11B | 109.046 |
C10—N2—H2A | 120.725 | C12—C11—H11A | 109.070 |
C8—N3—H3A | 117.422 | H11B—C11—H11A | 107.966 |
C8—N3—H3B | 119.300 | H12A—C12—H12B | 109.384 |
H3A—N3—H3B | 122.458 | H12A—C12—H12C | 109.809 |
C9—N4—H4B | 118.256 | H12B—C12—H12C | 109.280 |
C9—N4—H4A | 121.090 | C15—O3—H3C | 104.751 |
H4B—N4—H4A | 120.468 | C17—O4—H4C | 109.567 |
C7—C1—C6 | 121.54 (9) | C15—C14—C19 | 117.97 (9) |
C7—C1—C2 | 120.15 (9) | C17—C16—C15 | 120.06 (9) |
C6—C1—C2 | 118.30 (10) | C17—C16—H16 | 119.847 |
C3—C2—H2 | 119.271 | C19—C18—H18 | 120.763 |
C4—C3—C2 | 119.02 (10) | C20—O5—H5A | 107.051 |
C4—C3—H3 | 120.363 | H20A—C20—H20B | 109.262 |
C5—C4—C3 | 121.37 (11) | H20A—C20—H20C | 109.353 |
C6—C5—H5 | 120.580 | H20B—C20—H20C | 109.601 |
C8—C7—C10 | 115.89 (9) | | |
| | | |
CL1—C4—C5—C6 | 177.37 (3) | C6—C1—C7—C10 | 117.9 (2) |
CL1—C4—C5—H5 | −2.77 | H6—C6—C1—C7 | 0.51 |
CL1—C4—C3—C2 | −178.13 (2) | C7—C8—N1—C9 | 2.57 (15) |
CL1—C4—C3—H3 | 1.82 | C7—C10—N2—C9 | 1.22 (15) |
N1—C9—N2—C10 | 0.34 (14) | C7—C10—C11—C12 | −107.1 (2) |
N1—C9—N2—H2A | 179.53 | C7—C10—C11—H11B | 14.09 |
N1—C9—N4—H4B | −1.80 | C7—C10—C11—H11A | 131.94 |
N1—C9—N4—H4A | −176.85 | C8—C7—C10—C11 | 176.97 (16) |
N1—C8—N3—H3A | 3.86 | C9—N2—C10—C11 | −176.82 (13) |
N1—C8—N3—H3B | 173.75 | C10—C11—C12—H12A | 57.40 |
N1—C8—C7—C10 | −1.05 (15) | C10—C11—C12—H12B | −62.36 |
N1—C8—C7—C1 | −178.52 (5) | C10—C11—C12—H12C | 177.90 |
N2—C9—N1—C8 | −2.21 (15) | H11A—C11—C12—H12A | 178.31 |
N2—C9—N4—H4B | 177.80 | H11A—C11—C12—H12B | 58.55 |
N2—C9—N4—H4A | 2.75 | H11A—C11—C12—H12C | −61.18 |
N2—C10—C7—C8 | −0.85 (15) | H11B—C11—C12—H12A | −64.01 |
N2—C10—C7—C1 | 176.57 (11) | H11B—C11—C12—H12B | 176.24 |
N2—C10—C11—C12 | 70.81 (19) | H11B—C11—C12—H12C | 56.50 |
N2—C10—C11—H11B | −167.99 | O1—C13—C14—C15 | 8.49 (15) |
N2—C10—C11—H11A | −50.14 | O1—C13—C14—C19 | −173.81 (15) |
H2A—N2—C9—N4 | −0.07 | O2—C13—C14—C15 | −170.86 (15) |
H2A—N2—C10—C7 | −177.95 | O2—C13—C14—C19 | 6.84 (16) |
H2A—N2—C10—C11 | 4.01 | O3—C15—C14—C13 | −2.75 (14) |
N3—C8—N1—C9 | −177.31 (19) | O3—C15—C14—C19 | 179.50 (16) |
N3—C8—C7—C10 | 178.82 (18) | O3—C15—C16—C17 | 179.43 (16) |
N3—C8—C7—C1 | 1.35 (15) | O3—C15—C16—H16 | −0.71 |
H3A—N3—C8—C7 | −176.02 | H3C—O3—C15—C14 | −4.73 |
H3B—N3—C8—C7 | −6.13 | H3C—O3—C15—C16 | 177.00 |
N4—C9—N2—C10 | −179.25 (16) | O4—C17—C16—C15 | −179.22 (16) |
N4—C9—N1—C8 | 177.4 (2) | O4—C17—C16—H16 | 0.91 |
C1—C7—C10—C11 | −5.62 (14) | O4—C17—C18—C19 | 178.47 (18) |
C1—C6—C5—C4 | 0.67 (17) | O4—C17—C18—H18 | −1.47 |
C1—C6—C5—H5 | −179.20 | H4C—O4—C17—C16 | 179.64 |
C1—C2—C3—C4 | 0.85 (17) | H4C—O4—C17—C18 | −0.45 |
C1—C2—C3—H3 | −179.09 | C13—C14—C15—C16 | 175.47 (14) |
C2—C1—C7—C8 | 114.9 (2) | C13—C14—C19—C18 | −176.24 (13) |
C2—C1—C7—C10 | −62.38 (19) | C13—C14—C19—H19 | 4.06 |
C2—C1—C6—C5 | 0.63 (18) | C14—C15—C16—C17 | 1.13 (16) |
C2—C1—C6—H6 | −179.19 | C14—C15—C16—H16 | −179.01 |
C2—C3—C4—C5 | 0.50 (18) | C14—C19—C18—C17 | 0.40 (16) |
H2—C2—C1—C7 | −1.30 | C14—C19—C18—H18 | −179.65 |
H2—C2—C1—C6 | 178.41 | C15—C14—C19—C18 | 1.53 (16) |
H2—C2—C3—C4 | −178.96 | C15—C14—C19—H19 | −178.17 |
H2—C2—C3—H3 | 1.09 | C15—C16—C17—C18 | 0.87 (16) |
C3—C4—C5—C6 | −1.25 (18) | C16—C17—C18—C19 | −1.62 (16) |
C3—C4—C5—H5 | 178.62 | C16—C17—C18—H18 | 178.43 |
C3—C2—C1—C7 | 178.89 (7) | C16—C15—C14—C19 | −2.29 (16) |
C3—C2—C1—C6 | −1.40 (18) | H16—C16—C17—C18 | −179.00 |
H3—C3—C4—C5 | −179.55 | C17—C18—C19—H19 | −179.90 |
C4—C5—C6—H6 | −179.51 | H18—C18—C19—H19 | 0.05 |
C5—C6—C1—C7 | −179.67 (3) | H5A—O5—C20—H20A | 160.85 |
H5—C5—C6—H6 | 0.62 | H5A—O5—C20—H20B | 41.16 |
C6—C1—C7—C8 | −64.80 (19) | H5A—O5—C20—H20C | −78.99 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3B···C1 | 1.05 (2) | 2.51 (2) | 2.9011 (18) | 101 (1) |
N3—H3B···C6 | 1.05 (2) | 2.59 (2) | 3.193 (2) | 115 (1) |
C11—H11B···C1 | 1.09 (10) | 2.60 (2) | 3.0522 (19) | 104 (2) |
C11—H11B···C2 | 1.09 (10) | 2.57 (4) | 3.321 (2) | 125 (3) |
O3—H3C···O1 | 1.00 (2) | 1.64 (2) | 2.5591 (16) | 149 (2) |
O3—H3C···C13 | 1.00 (2) | 2.30 (2) | 2.9024 (17) | 117 (1) |
O4—H4C···O5 | 0.97 (2) | 1.72 (2) | 2.6820 (16) | 170 (1) |
O4—H4C···C20 | 0.97 (2) | 2.61 (2) | 3.474 (2) | 149 (2) |
O5—H5A···O2i | 1.00 (3) | 1.70 (3) | 2.6904 (16) | 169 (1) |
N2—H2A···O1ii | 1.07 (2) | 1.64 (2) | 2.7046 (15) | 175 (1) |
N2—H2A···C13ii | 1.07 (2) | 2.50 (2) | 3.5152 (17) | 158 (1) |
C12—H12B···O1ii | 1.08 (9) | 2.60 (5) | 3.409 (2) | 131 (4) |
N4—H4A···O2ii | 1.04 (2) | 1.77 (2) | 2.8023 (16) | 176 (3) |
N4—H4A···C13ii | 1.04 (2) | 2.63 (2) | 3.5757 (19) | 152 (9) |
N3—H3A···O3iii | 1.03 (2) | 2.20 (2) | 3.2278 (17) | 170 (3) |
N4—H4B···O4iii | 1.03 (2) | 2.22 (2) | 3.2051 (16) | 167 (6) |
C16—H16···N1iii | 1.08 (5) | 2.20 (6) | 3.2736 (18) | 174 (1) |
N3—H3B···CL1iv | 1.05 (2) | 2.62 (2) | 3.4364 (14) | 133 (1) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y+2, −z; (iii) −x+1, −y+1, −z; (iv) −x+1, −y+1, −z+1. |
Refinement details topRefinement IAM_SHELX | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.125, 1.06 |
No. of reflections | 5182 |
No. of parameters | 282 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å-3) | 0.35, -0.44 |
| |
Refinement IAM_MoPro | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.085, 1.38 |
No. of reflections | 5182 |
No. of parameters | 281 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å-3) | 0.26, -0.25 |
| |
Refinement ELMAM2_MoPro | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.061, 1.02 |
No. of reflections | 5182 |
No. of parameters | 271 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å-3) | 0.18, -0.33 |
Topological properties at the critical points of O···H, C···H and H···H
intermolecular interactions in the crystal packing of compound (2) for the
ELMAM2 model.
d12, d1cp and d2cp are the distances (Å)
between the two atoms, between the first atom and the CP, and between the
CP and the second atom. ρCP is the total electron density (e Å-3) at
the CP and \nabla2ρCP, its Laplacian (e Å-5). λ1, λ2 and
λ3 are the eigenvalues (e Å-5) of the Hessian matrix
∂2ρ/∂xi ∂xj·ε = λ1/λ2 - 1 is the
ellipticity. GCP is the bond kinetic energy and
VCP is the bond potential energy (kJ mol -1 Bohr-1) topInteracting atoms | d12 (Å) | d1CP (Å) | d2CP (Å) | ρCP (e Å-3) | \nabla2ρCP (e Å-5) | λ1 (e Å-5) | λ2 (e Å-5) | λ3 (e Å-5) | ε | GCP | VCP |
Cl1···H3Bi | 2.6225 | 1.6966 | 0.9345 | 0.0665 | 0.7 | -0.23 | -0.18 | 1.11 | 0.2941 | 16.07 | -13.16 |
Cl1···H12Cii | 2.9231 | 1.8176 | 1.1065 | 0.0467 | 0.43 | -0.15 | -0.15 | 0.73 | 0.0243 | 9.66 | -7.67 |
N1···H16iii | 2.1967 | 1.3735 | 0.8233 | 0.1276 | 1.36 | -0.62 | -0.59 | 2.57 | 0.0576 | 34.76 | -32.56 |
H2A···O1iv | 1.6329 | 0.5324 | 1.1006 | 0.3732 | 2.47 | -2.66 | -2.65 | 7.78 | 0.0025 | 105.39 | -143.45 |
H3A···O3iii | 2.2044 | 0.84 | 1.365 | 0.0983 | 0.88 | -0.49 | -0.47 | 1.85 | 0.0413 | 22.54 | -21.09 |
H3···O4i | 2.6735 | 1.1499 | 1.543 | 0.0363 | 0.63 | -0.11 | -0.07 | 0.81 | 0.4732 | 12.63 | -8.18 |
H12B···O1iv | 2.6039 | 1.0954 | 1.5088 | 0.0414 | 0.66 | -0.12 | -0.1 | 0.89 | 0.2247 | 13.58 | -9.11 |
H4A···O2iv | 1.7652 | 0.5941 | 1.171 | 0.256 | 2.22 | -1.62 | -1.61 | 5.44 | 0.006 | 72.53 | -84.68 |
H4B···O4iii | 2.215 | 0.848 | 1.3678 | 0.0968 | 0.9 | -0.47 | -0.46 | 1.83 | 0.018 | 22.65 | -20.91 |
O2···H5Av | 1.7032 | 1.1286 | 0.5758 | 0.327 | 1.23 | -2.3 | -2.27 | 5.81 | 0.0166 | 70.96 | -108.31 |
H3C···O1' | 1.6421 | 0.5356 | 1.1102 | 0.3642 | 2.25 | -2.63 | -2.32 | 7.2 | 0.1337 | 98.96 | -136.64 |
Symmetry codes: (i) -x+1, -y+1, -z+1;
(ii) -x, -y+2, -z+1;
(iii) -x+1, -y+1, -z;
(iv) -x, -y+2, -z;
(v) -x, -y+1, -z+1. |
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