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Seven solvates of the angiotensin II receptor blocker agent olmesartan (C24H26N6O3), namely, the methanol (C24H26N6O3·CH4O), ethanol (C24H26N6O3·C2H6O), isopropanol (C24H26N6O3·C3H8O), isobutanol (C24H26N6O3·C4H10O), 2-ethoxyethanol (C24H26N6O3·C4H10O2), chloroform (C24H26N6O3·CHCl3) and acetonitrile (C24H26N6O3·C2H3N) solvates, were successfully obtained. The crystal structures were determined using the single-crystal X-ray diffraction technique and the structural features are described, each solvate containing one molecule of olmesartan and one of solvent in the asymmetric unit. The samples were also analyzed by powder X-ray diffraction. Total lattice energies and binding energies between the olmesartan and solvent molecules were evaluated, which can be partitioned into electrostatic, polarization, dispersion and repulsion components. Hirshfeld and fingerprint plot analysis was performed to highlight the intermolecular contacts. Hydrogen bonding and supramolecular arrangements were comparatively studied for the seven solvates.
Supporting information
CCDC references: 2144598; 2144597; 2144596; 2144595; 2144594; 2144593; 2144592
For all structures, data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
4-(2-Hydroxypropan-2-yl)-2-propyl-1-({4-[2-(1
H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1
H-imidazol-3-ium-5-carboxylate
methanol monosolvate (Ol-MeOH)
top
Crystal data top
C24H26N6O3·CH4O | F(000) = 1016 |
Mr = 478.55 | Dx = 1.253 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 9.94703 (14) Å | Cell parameters from 12956 reflections |
b = 17.8262 (2) Å | θ = 5.8–71.5° |
c = 14.3100 (2) Å | µ = 0.71 mm−1 |
β = 92.0063 (14)° | T = 99 K |
V = 2535.85 (7) Å3 | Plate, colourless |
Z = 4 | 0.1 × 0.09 × 0.01 mm |
Data collection top
Agilent SuperNova Dual Source diffractometer with an Eos detector | 4874 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 4601 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.022 |
Detector resolution: 16.4335 pixels mm-1 | θmax = 71.7°, θmin = 4.5° |
ω scans | h = −12→12 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −21→21 |
Tmin = 0.762, Tmax = 1.000 | l = −12→17 |
19216 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.149 | w = 1/[σ2(Fo2) + (0.0791P)2 + 2.3619P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
4874 reflections | Δρmax = 0.48 e Å−3 |
326 parameters | Δρmin = −0.73 e Å−3 |
1 restraint | |
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. |
Refinement. Single crystals of each solvate were selected and analysed using a
SuperNova diffractometer equipped with dual X-ray sources (Cu and Mo), using
Cu radiation and Eos CCD detector. The X-ray tube has been set to operate at
50 kV and 0.8 mA. Diffraction intensities were collected and corrected for
Lorentz, polarization and absorption effects using CrysAlis PRO software
(Agilent, 2012). Because of highly disordered solvent
molecules in crystal
lattices the investigated crystals were kept at low temperatures (100 K)
during data collection. Using Olex2 (Dolomanov et al., 2009), the
structures were solved with the ShelXS (Sheldrick, 2008)
structure solution
program using Direct Methods and refined with the ShelXL (Sheldrick, 2015)
refinement package by Least Squares minimisation. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | −0.08903 (11) | 0.67348 (7) | 0.21763 (8) | 0.0170 (3) | |
H1 | −0.072445 | 0.697698 | 0.170697 | 0.026* | |
O3 | 0.21302 (12) | 0.77326 (8) | 0.04154 (8) | 0.0233 (3) | |
N6 | 0.20984 (13) | 0.73007 (8) | 0.35306 (9) | 0.0143 (3) | |
H6 | 0.193318 | 0.719472 | 0.410149 | 0.017* | |
N5 | 0.31731 (13) | 0.76119 (7) | 0.23076 (9) | 0.0129 (3) | |
O2 | 0.00419 (13) | 0.75961 (9) | 0.09008 (9) | 0.0305 (3) | |
C15 | 0.18216 (15) | 0.75015 (9) | 0.20160 (11) | 0.0133 (3) | |
C9 | 0.70199 (15) | 0.68372 (9) | 0.04910 (11) | 0.0142 (3) | |
H9 | 0.783358 | 0.695594 | 0.022635 | 0.017* | |
N1 | 0.79226 (16) | 0.53253 (9) | 0.21501 (11) | 0.0230 (3) | |
C13 | 0.53036 (17) | 0.59383 (10) | 0.08289 (12) | 0.0179 (4) | |
H13 | 0.497500 | 0.544999 | 0.080643 | 0.021* | |
C11 | 0.50521 (16) | 0.72291 (9) | 0.13045 (11) | 0.0133 (3) | |
C16 | 0.11599 (16) | 0.72949 (9) | 0.28017 (11) | 0.0133 (3) | |
C12 | 0.45616 (16) | 0.64979 (10) | 0.12467 (12) | 0.0168 (3) | |
H12 | 0.373119 | 0.638373 | 0.148985 | 0.020* | |
C10 | 0.62951 (16) | 0.73920 (9) | 0.09310 (11) | 0.0142 (3) | |
H10 | 0.664085 | 0.787582 | 0.097719 | 0.017* | |
C14 | 0.42889 (16) | 0.78657 (9) | 0.17393 (11) | 0.0151 (3) | |
H14A | 0.490815 | 0.815914 | 0.212959 | 0.018* | |
H14B | 0.393414 | 0.819065 | 0.124598 | 0.018* | |
C8 | 0.65379 (16) | 0.61027 (9) | 0.04425 (11) | 0.0152 (3) | |
C18 | 0.13036 (17) | 0.76192 (9) | 0.10288 (11) | 0.0155 (3) | |
C17 | 0.33015 (16) | 0.74944 (9) | 0.32251 (12) | 0.0147 (3) | |
C6 | 0.73429 (16) | 0.55068 (10) | −0.00141 (13) | 0.0188 (4) | |
C5 | 0.75874 (18) | 0.55605 (11) | −0.09646 (14) | 0.0245 (4) | |
H5 | 0.725940 | 0.597136 | −0.130190 | 0.029* | |
C22 | 0.45465 (17) | 0.75251 (10) | 0.38277 (12) | 0.0189 (4) | |
H22A | 0.430275 | 0.758778 | 0.447343 | 0.023* | |
H22B | 0.507094 | 0.795909 | 0.365470 | 0.023* | |
C19 | −0.02932 (16) | 0.70935 (9) | 0.29785 (12) | 0.0162 (3) | |
C23 | 0.54184 (18) | 0.68159 (11) | 0.37469 (13) | 0.0242 (4) | |
H23A | 0.572512 | 0.677800 | 0.311255 | 0.029* | |
H23B | 0.620624 | 0.686583 | 0.416111 | 0.029* | |
C7 | 0.76671 (19) | 0.48034 (10) | 0.14915 (14) | 0.0247 (4) | |
C2 | 0.85541 (19) | 0.43261 (11) | 0.00161 (16) | 0.0296 (4) | |
H2 | 0.886859 | 0.390680 | 0.034290 | 0.035* | |
C1 | 0.78422 (17) | 0.48850 (10) | 0.04826 (14) | 0.0218 (4) | |
N2 | 0.7680 (2) | 0.50345 (10) | 0.29921 (13) | 0.0363 (4) | |
N3 | 0.7294 (3) | 0.43495 (12) | 0.28413 (15) | 0.0505 (6) | |
C20 | −0.10632 (19) | 0.78073 (12) | 0.32024 (17) | 0.0328 (5) | |
H20A | −0.106566 | 0.813767 | 0.267247 | 0.049* | |
H20B | −0.063645 | 0.805202 | 0.373166 | 0.049* | |
H20C | −0.197224 | 0.768170 | 0.334386 | 0.049* | |
C3 | 0.8789 (2) | 0.43957 (12) | −0.09229 (17) | 0.0341 (5) | |
H3 | 0.927098 | 0.402620 | −0.122489 | 0.041* | |
N4 | 0.7270 (2) | 0.41865 (10) | 0.19123 (14) | 0.0421 (5) | |
C4 | 0.8313 (2) | 0.50110 (12) | −0.14183 (15) | 0.0319 (5) | |
H4 | 0.847573 | 0.505775 | −0.205165 | 0.038* | |
C21 | −0.0370 (2) | 0.65276 (12) | 0.37716 (13) | 0.0276 (4) | |
H21A | −0.128379 | 0.636402 | 0.382524 | 0.041* | |
H21B | −0.006491 | 0.675801 | 0.434713 | 0.041* | |
H21C | 0.018947 | 0.610392 | 0.364269 | 0.041* | |
C24 | 0.4685 (2) | 0.61003 (13) | 0.39874 (18) | 0.0396 (5) | |
H24A | 0.434046 | 0.614220 | 0.460368 | 0.059* | |
H24B | 0.529550 | 0.568419 | 0.396780 | 0.059* | |
H24C | 0.395271 | 0.602126 | 0.354310 | 0.059* | |
O1A | 0.1684 (3) | 0.39116 (15) | 0.3783 (3) | 0.0921 (9) | |
H1AA | 0.108245 | 0.361500 | 0.390015 | 0.138* | |
C1A | 0.1490 (6) | 0.4557 (2) | 0.4244 (3) | 0.1074 (17) | |
H1AB | 0.193490 | 0.495826 | 0.393125 | 0.161* | |
H1AC | 0.185255 | 0.451223 | 0.487166 | 0.161* | |
H1AD | 0.054399 | 0.466110 | 0.425724 | 0.161* | |
H1A | 0.823 (2) | 0.5777 (10) | 0.2142 (18) | 0.036 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0179 (6) | 0.0203 (6) | 0.0127 (6) | −0.0044 (5) | −0.0022 (4) | −0.0004 (5) |
O3 | 0.0190 (6) | 0.0392 (8) | 0.0119 (6) | 0.0024 (5) | 0.0013 (5) | 0.0005 (5) |
N6 | 0.0146 (6) | 0.0199 (7) | 0.0084 (6) | −0.0003 (5) | 0.0004 (5) | −0.0011 (5) |
N5 | 0.0116 (6) | 0.0162 (7) | 0.0110 (6) | 0.0004 (5) | 0.0007 (5) | −0.0020 (5) |
O2 | 0.0183 (6) | 0.0509 (9) | 0.0216 (7) | −0.0095 (6) | −0.0071 (5) | 0.0162 (6) |
C15 | 0.0110 (7) | 0.0145 (7) | 0.0144 (8) | 0.0011 (6) | −0.0015 (6) | −0.0026 (6) |
C9 | 0.0110 (7) | 0.0201 (8) | 0.0116 (7) | −0.0009 (6) | 0.0002 (6) | 0.0007 (6) |
N1 | 0.0274 (8) | 0.0172 (7) | 0.0241 (8) | −0.0052 (6) | −0.0029 (6) | 0.0018 (6) |
C13 | 0.0162 (8) | 0.0170 (8) | 0.0204 (9) | −0.0030 (6) | 0.0013 (6) | −0.0029 (6) |
C11 | 0.0124 (7) | 0.0185 (8) | 0.0090 (7) | 0.0009 (6) | −0.0013 (6) | −0.0006 (6) |
C16 | 0.0139 (7) | 0.0138 (7) | 0.0119 (8) | 0.0012 (6) | −0.0005 (6) | −0.0032 (6) |
C12 | 0.0130 (7) | 0.0209 (8) | 0.0167 (8) | −0.0028 (6) | 0.0028 (6) | −0.0017 (6) |
C10 | 0.0137 (7) | 0.0165 (8) | 0.0121 (8) | −0.0020 (6) | −0.0021 (6) | 0.0014 (6) |
C14 | 0.0139 (7) | 0.0171 (8) | 0.0144 (8) | −0.0018 (6) | 0.0028 (6) | −0.0015 (6) |
C8 | 0.0130 (7) | 0.0192 (8) | 0.0133 (8) | 0.0007 (6) | −0.0010 (6) | −0.0017 (6) |
C18 | 0.0166 (8) | 0.0170 (8) | 0.0128 (8) | 0.0004 (6) | −0.0019 (6) | −0.0004 (6) |
C17 | 0.0146 (8) | 0.0170 (8) | 0.0125 (8) | 0.0009 (6) | −0.0001 (6) | −0.0033 (6) |
C6 | 0.0123 (7) | 0.0192 (8) | 0.0248 (9) | −0.0041 (6) | 0.0024 (6) | −0.0066 (7) |
C5 | 0.0216 (9) | 0.0267 (9) | 0.0257 (10) | −0.0068 (7) | 0.0070 (7) | −0.0067 (8) |
C22 | 0.0148 (8) | 0.0287 (9) | 0.0129 (8) | −0.0013 (7) | −0.0026 (6) | −0.0024 (7) |
C19 | 0.0136 (8) | 0.0199 (8) | 0.0151 (8) | −0.0030 (6) | 0.0019 (6) | −0.0055 (6) |
C23 | 0.0177 (8) | 0.0387 (11) | 0.0160 (8) | 0.0060 (7) | −0.0024 (6) | −0.0028 (8) |
C7 | 0.0245 (9) | 0.0160 (8) | 0.0331 (10) | −0.0023 (7) | −0.0051 (8) | −0.0008 (7) |
C2 | 0.0190 (9) | 0.0185 (9) | 0.0511 (13) | −0.0011 (7) | −0.0012 (8) | −0.0097 (9) |
C1 | 0.0149 (8) | 0.0179 (8) | 0.0324 (10) | −0.0032 (6) | −0.0007 (7) | −0.0070 (7) |
N2 | 0.0523 (11) | 0.0282 (9) | 0.0280 (9) | −0.0144 (8) | −0.0031 (8) | 0.0061 (7) |
N3 | 0.0831 (16) | 0.0311 (10) | 0.0371 (11) | −0.0249 (10) | −0.0031 (10) | 0.0076 (8) |
C20 | 0.0167 (9) | 0.0299 (10) | 0.0522 (13) | −0.0019 (8) | 0.0094 (8) | −0.0180 (9) |
C3 | 0.0219 (9) | 0.0293 (10) | 0.0519 (13) | −0.0053 (8) | 0.0121 (9) | −0.0232 (10) |
N4 | 0.0661 (14) | 0.0234 (9) | 0.0362 (10) | −0.0167 (9) | −0.0048 (9) | 0.0035 (8) |
C4 | 0.0278 (10) | 0.0360 (11) | 0.0327 (11) | −0.0099 (8) | 0.0137 (8) | −0.0166 (9) |
C21 | 0.0266 (9) | 0.0414 (11) | 0.0148 (9) | −0.0158 (8) | 0.0001 (7) | 0.0016 (8) |
C24 | 0.0406 (12) | 0.0337 (12) | 0.0445 (13) | 0.0107 (9) | 0.0008 (10) | 0.0062 (10) |
O1A | 0.0680 (16) | 0.0613 (15) | 0.149 (3) | −0.0112 (12) | 0.0309 (16) | −0.0264 (16) |
C1A | 0.190 (5) | 0.048 (2) | 0.086 (3) | −0.011 (3) | 0.038 (3) | 0.0010 (19) |
Geometric parameters (Å, º) top
O1—H1 | 0.8200 | C5—C4 | 1.391 (3) |
O1—C19 | 1.4254 (19) | C22—H22A | 0.9700 |
O3—C18 | 1.240 (2) | C22—H22B | 0.9700 |
N6—H6 | 0.8600 | C22—C23 | 1.540 (3) |
N6—C16 | 1.375 (2) | C19—C20 | 1.525 (2) |
N6—C17 | 1.334 (2) | C19—C21 | 1.522 (3) |
N5—C15 | 1.407 (2) | C23—H23A | 0.9700 |
N5—C14 | 1.470 (2) | C23—H23B | 0.9700 |
N5—C17 | 1.331 (2) | C23—C24 | 1.515 (3) |
O2—C18 | 1.263 (2) | C7—C1 | 1.468 (3) |
C15—C16 | 1.373 (2) | C7—N4 | 1.321 (3) |
C15—C18 | 1.501 (2) | C2—H2 | 0.9300 |
C9—H9 | 0.9300 | C2—C1 | 1.405 (3) |
C9—C10 | 1.388 (2) | C2—C3 | 1.378 (3) |
C9—C8 | 1.395 (2) | N2—N3 | 1.296 (3) |
N1—C7 | 1.342 (2) | N3—N4 | 1.360 (3) |
N1—N2 | 1.341 (2) | C20—H20A | 0.9600 |
N1—H1A | 0.860 (17) | C20—H20B | 0.9600 |
C13—H13 | 0.9300 | C20—H20C | 0.9600 |
C13—C12 | 1.389 (2) | C3—H3 | 0.9300 |
C13—C8 | 1.395 (2) | C3—C4 | 1.381 (3) |
C11—C12 | 1.393 (2) | C4—H4 | 0.9300 |
C11—C10 | 1.395 (2) | C21—H21A | 0.9600 |
C11—C14 | 1.511 (2) | C21—H21B | 0.9600 |
C16—C19 | 1.519 (2) | C21—H21C | 0.9600 |
C12—H12 | 0.9300 | C24—H24A | 0.9600 |
C10—H10 | 0.9300 | C24—H24B | 0.9600 |
C14—H14A | 0.9700 | C24—H24C | 0.9600 |
C14—H14B | 0.9700 | O1A—H1AA | 0.8200 |
C8—C6 | 1.494 (2) | O1A—C1A | 1.343 (4) |
C17—C22 | 1.485 (2) | C1A—H1AB | 0.9600 |
C6—C5 | 1.393 (3) | C1A—H1AC | 0.9600 |
C6—C1 | 1.398 (3) | C1A—H1AD | 0.9600 |
C5—H5 | 0.9300 | | |
| | | |
C19—O1—H1 | 109.5 | C23—C22—H22B | 109.0 |
C16—N6—H6 | 124.9 | O1—C19—C16 | 110.11 (13) |
C17—N6—H6 | 124.9 | O1—C19—C20 | 110.20 (15) |
C17—N6—C16 | 110.27 (14) | O1—C19—C21 | 105.83 (13) |
C15—N5—C14 | 127.65 (13) | C16—C19—C20 | 109.00 (14) |
C17—N5—C15 | 109.15 (13) | C16—C19—C21 | 110.72 (14) |
C17—N5—C14 | 123.08 (13) | C21—C19—C20 | 110.95 (16) |
N5—C15—C18 | 123.52 (14) | C22—C23—H23A | 108.9 |
C16—C15—N5 | 105.96 (14) | C22—C23—H23B | 108.9 |
C16—C15—C18 | 130.50 (14) | H23A—C23—H23B | 107.7 |
C10—C9—H9 | 119.7 | C24—C23—C22 | 113.39 (16) |
C10—C9—C8 | 120.55 (14) | C24—C23—H23A | 108.9 |
C8—C9—H9 | 119.7 | C24—C23—H23B | 108.9 |
C7—N1—H1A | 134.3 (17) | N1—C7—C1 | 126.58 (17) |
N2—N1—C7 | 109.11 (16) | N4—C7—N1 | 108.02 (18) |
N2—N1—H1A | 116.6 (17) | N4—C7—C1 | 125.36 (18) |
C12—C13—H13 | 119.7 | C1—C2—H2 | 119.8 |
C12—C13—C8 | 120.54 (15) | C3—C2—H2 | 119.8 |
C8—C13—H13 | 119.7 | C3—C2—C1 | 120.3 (2) |
C12—C11—C10 | 119.03 (15) | C6—C1—C7 | 121.76 (16) |
C12—C11—C14 | 123.16 (14) | C6—C1—C2 | 119.78 (18) |
C10—C11—C14 | 117.79 (14) | C2—C1—C7 | 118.45 (18) |
N6—C16—C19 | 120.00 (14) | N3—N2—N1 | 106.03 (17) |
C15—C16—N6 | 106.67 (14) | N2—N3—N4 | 111.04 (18) |
C15—C16—C19 | 133.32 (15) | C19—C20—H20A | 109.5 |
C13—C12—C11 | 120.49 (15) | C19—C20—H20B | 109.5 |
C13—C12—H12 | 119.8 | C19—C20—H20C | 109.5 |
C11—C12—H12 | 119.8 | H20A—C20—H20B | 109.5 |
C9—C10—C11 | 120.47 (15) | H20A—C20—H20C | 109.5 |
C9—C10—H10 | 119.8 | H20B—C20—H20C | 109.5 |
C11—C10—H10 | 119.8 | C2—C3—H3 | 119.8 |
N5—C14—C11 | 113.36 (13) | C2—C3—C4 | 120.36 (18) |
N5—C14—H14A | 108.9 | C4—C3—H3 | 119.8 |
N5—C14—H14B | 108.9 | C7—N4—N3 | 105.80 (17) |
C11—C14—H14A | 108.9 | C5—C4—H4 | 120.2 |
C11—C14—H14B | 108.9 | C3—C4—C5 | 119.6 (2) |
H14A—C14—H14B | 107.7 | C3—C4—H4 | 120.2 |
C9—C8—C13 | 118.88 (15) | C19—C21—H21A | 109.5 |
C9—C8—C6 | 120.02 (14) | C19—C21—H21B | 109.5 |
C13—C8—C6 | 121.10 (15) | C19—C21—H21C | 109.5 |
O3—C18—O2 | 125.66 (16) | H21A—C21—H21B | 109.5 |
O3—C18—C15 | 118.33 (15) | H21A—C21—H21C | 109.5 |
O2—C18—C15 | 116.01 (15) | H21B—C21—H21C | 109.5 |
N6—C17—C22 | 123.97 (15) | C23—C24—H24A | 109.5 |
N5—C17—N6 | 107.92 (14) | C23—C24—H24B | 109.5 |
N5—C17—C22 | 128.03 (15) | C23—C24—H24C | 109.5 |
C5—C6—C8 | 119.51 (16) | H24A—C24—H24B | 109.5 |
C5—C6—C1 | 118.65 (17) | H24A—C24—H24C | 109.5 |
C1—C6—C8 | 121.83 (16) | H24B—C24—H24C | 109.5 |
C6—C5—H5 | 119.4 | C1A—O1A—H1AA | 109.5 |
C4—C5—C6 | 121.23 (19) | O1A—C1A—H1AB | 109.5 |
C4—C5—H5 | 119.4 | O1A—C1A—H1AC | 109.5 |
C17—C22—H22A | 109.0 | O1A—C1A—H1AD | 109.5 |
C17—C22—H22B | 109.0 | H1AB—C1A—H1AC | 109.5 |
C17—C22—C23 | 112.74 (14) | H1AB—C1A—H1AD | 109.5 |
H22A—C22—H22B | 107.8 | H1AC—C1A—H1AD | 109.5 |
C23—C22—H22A | 109.0 | | |
4-(2-Hydroxypropan-2-yl)-2-propyl-1-({4-[2-(1
H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1
H-imidazol-3-ium-5-carboxylate
ethanol monosolvate (Ol-EtOH)
top
Crystal data top
C24H26N6O3·C2H6O | F(000) = 1048 |
Mr = 492.57 | Dx = 1.282 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 9.7816 (3) Å | Cell parameters from 8672 reflections |
b = 18.3758 (5) Å | θ = 3.9–71.5° |
c = 14.1998 (4) Å | µ = 0.72 mm−1 |
β = 91.029 (3)° | T = 100 K |
V = 2551.93 (12) Å3 | Plate, colourless |
Z = 4 | 0.09 × 0.09 × 0.01 mm |
Data collection top
Agilent SuperNova Dual Source diffractometer with an Eos detector | 4875 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 4318 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.026 |
Detector resolution: 16.4335 pixels mm-1 | θmax = 71.8°, θmin = 3.9° |
ω scans | h = −12→11 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −22→21 |
Tmin = 0.664, Tmax = 1.000 | l = −12→17 |
14146 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.058 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.164 | w = 1/[σ2(Fo2) + (0.0819P)2 + 2.3824P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
4875 reflections | Δρmax = 0.72 e Å−3 |
335 parameters | Δρmin = −0.70 e Å−3 |
1 restraint | |
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. |
Refinement. Single crystals of each solvate were selected and analysed using a
SuperNova diffractometer equipped with dual X-ray sources (Cu and Mo), using
Cu radiation and Eos CCD detector. The X-ray tube has been set to operate at
50 kV and 0.8 mA. Diffraction intensities were collected and corrected for
Lorentz, polarization and absorption effects using CrysAlis PRO software
(Agilent, 2012). Because of highly disordered solvent
molecules in crystal
lattices the investigated crystals were kept at low temperatures (100 K)
during data collection. Using Olex2 (Dolomanov et al., 2009), the
structures were solved with the ShelXS (Sheldrick, 2008)
structure solution
program using Direct Methods and refined with the ShelXL (Sheldrick, 2015)
refinement package by Least Squares minimisation. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O2 | −0.00151 (14) | 0.23927 (8) | 0.39924 (10) | 0.0212 (3) | |
O3 | −0.20612 (14) | 0.27871 (9) | 0.44191 (10) | 0.0249 (4) | |
O1 | 0.08597 (14) | 0.15891 (8) | 0.26463 (9) | 0.0210 (3) | |
H1 | 0.072765 | 0.180297 | 0.314327 | 0.031* | |
N6 | −0.19828 (16) | 0.23065 (9) | 0.12936 (11) | 0.0170 (4) | |
H6 | −0.179919 | 0.221352 | 0.071592 | 0.020* | |
N5 | −0.30981 (16) | 0.26154 (9) | 0.25274 (11) | 0.0155 (3) | |
C12 | −0.44340 (19) | 0.15043 (11) | 0.36141 (13) | 0.0173 (4) | |
H12 | −0.357145 | 0.141406 | 0.337509 | 0.021* | |
C9 | −0.69796 (18) | 0.17740 (11) | 0.43706 (13) | 0.0152 (4) | |
H9 | −0.782162 | 0.187092 | 0.463752 | 0.018* | |
C10 | −0.62751 (19) | 0.23272 (10) | 0.39281 (13) | 0.0148 (4) | |
H10 | −0.666058 | 0.278895 | 0.388620 | 0.018* | |
C15 | −0.17444 (19) | 0.24734 (10) | 0.28287 (13) | 0.0152 (4) | |
C17 | −0.3204 (2) | 0.25096 (11) | 0.16024 (14) | 0.0173 (4) | |
N1 | −0.7605 (2) | 0.03376 (10) | 0.25966 (13) | 0.0258 (4) | |
C11 | −0.49938 (18) | 0.21998 (10) | 0.35445 (13) | 0.0146 (4) | |
C13 | −0.5151 (2) | 0.09457 (11) | 0.40364 (14) | 0.0188 (4) | |
H13 | −0.477428 | 0.048148 | 0.406585 | 0.023* | |
C18 | −0.12382 (19) | 0.25595 (10) | 0.38254 (14) | 0.0161 (4) | |
C14 | −0.42613 (19) | 0.28356 (11) | 0.31049 (13) | 0.0161 (4) | |
H14A | −0.490655 | 0.310642 | 0.271441 | 0.019* | |
H14B | −0.393424 | 0.315769 | 0.360098 | 0.019* | |
C21 | 0.0524 (2) | 0.15682 (12) | 0.09983 (14) | 0.0237 (5) | |
H21A | 0.143935 | 0.138448 | 0.095481 | 0.035* | |
H21B | 0.030828 | 0.185607 | 0.045141 | 0.035* | |
H21C | −0.010465 | 0.116836 | 0.103445 | 0.035* | |
C7 | −0.7255 (2) | −0.01552 (12) | 0.32536 (16) | 0.0267 (5) | |
C16 | −0.10595 (19) | 0.22675 (10) | 0.20339 (13) | 0.0149 (4) | |
C8 | −0.64378 (19) | 0.10740 (11) | 0.44192 (13) | 0.0167 (4) | |
C1 | −0.7636 (2) | −0.01289 (11) | 0.42512 (16) | 0.0228 (4) | |
C19 | 0.04113 (19) | 0.20355 (11) | 0.18745 (13) | 0.0172 (4) | |
C23 | −0.5289 (2) | 0.18372 (13) | 0.10332 (15) | 0.0244 (5) | |
H23A | −0.560319 | 0.176384 | 0.167025 | 0.029* | |
H23B | −0.608952 | 0.188573 | 0.062500 | 0.029* | |
C22 | −0.4461 (2) | 0.25476 (12) | 0.09992 (14) | 0.0207 (4) | |
H22A | −0.420729 | 0.264457 | 0.035403 | 0.025* | |
H22B | −0.502730 | 0.294740 | 0.120871 | 0.025* | |
C6 | −0.72504 (19) | 0.04665 (11) | 0.48199 (14) | 0.0189 (4) | |
C5 | −0.7640 (2) | 0.04763 (12) | 0.57569 (16) | 0.0246 (5) | |
H5 | −0.738742 | 0.086534 | 0.614107 | 0.030* | |
N2 | −0.7041 (3) | 0.01500 (12) | 0.17711 (15) | 0.0407 (5) | |
C3 | −0.8780 (2) | −0.06768 (13) | 0.5558 (2) | 0.0351 (6) | |
H3 | −0.929553 | −0.105424 | 0.580516 | 0.042* | |
C2 | −0.8388 (2) | −0.06990 (12) | 0.46297 (19) | 0.0305 (5) | |
H2 | −0.862593 | −0.109614 | 0.425532 | 0.037* | |
C24 | −0.4487 (3) | 0.11728 (14) | 0.07347 (19) | 0.0359 (6) | |
H24A | −0.413610 | 0.124951 | 0.011556 | 0.054* | |
H24B | −0.507656 | 0.075499 | 0.072823 | 0.054* | |
H24C | −0.374145 | 0.109310 | 0.117115 | 0.054* | |
C20 | 0.1303 (2) | 0.27169 (12) | 0.18099 (17) | 0.0254 (5) | |
H20A | 0.125863 | 0.298467 | 0.238905 | 0.038* | |
H20B | 0.097853 | 0.301655 | 0.129935 | 0.038* | |
H20C | 0.223277 | 0.257696 | 0.170086 | 0.038* | |
N4 | −0.6477 (3) | −0.06542 (12) | 0.28500 (16) | 0.0460 (6) | |
C4 | −0.8405 (2) | −0.00913 (14) | 0.61229 (18) | 0.0336 (6) | |
H4 | −0.866635 | −0.007858 | 0.674910 | 0.040* | |
N3 | −0.6346 (3) | −0.04411 (13) | 0.19327 (17) | 0.0560 (8) | |
O1A | 0.3183 (3) | 0.41712 (15) | 0.3267 (2) | 0.0702 (7) | |
H1AA | 0.394759 | 0.435414 | 0.329507 | 0.105* | |
C1A | 0.0874 (4) | 0.4319 (2) | 0.3722 (3) | 0.0716 (10) | |
H1AB | 0.062360 | 0.435503 | 0.306718 | 0.107* | |
H1AC | 0.028582 | 0.462542 | 0.408393 | 0.107* | |
H1AD | 0.078141 | 0.382402 | 0.392634 | 0.107* | |
C2A | 0.2303 (4) | 0.4555 (3) | 0.3860 (4) | 0.0842 (13) | |
H2AA | 0.237180 | 0.507176 | 0.372917 | 0.101* | |
H2AB | 0.258094 | 0.447630 | 0.451089 | 0.101* | |
H1A | −0.809 (3) | 0.0725 (12) | 0.262 (2) | 0.034 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O2 | 0.0179 (7) | 0.0296 (8) | 0.0161 (7) | 0.0035 (6) | −0.0035 (5) | −0.0035 (6) |
O3 | 0.0185 (7) | 0.0438 (9) | 0.0124 (7) | 0.0027 (6) | 0.0003 (6) | −0.0035 (6) |
O1 | 0.0232 (7) | 0.0261 (8) | 0.0137 (7) | 0.0078 (6) | −0.0003 (6) | 0.0011 (6) |
N6 | 0.0164 (8) | 0.0237 (9) | 0.0109 (8) | 0.0004 (6) | −0.0002 (6) | 0.0019 (6) |
N5 | 0.0130 (7) | 0.0201 (8) | 0.0136 (8) | −0.0004 (6) | 0.0006 (6) | 0.0029 (6) |
C12 | 0.0135 (9) | 0.0229 (10) | 0.0154 (9) | 0.0029 (7) | 0.0008 (7) | 0.0001 (7) |
C9 | 0.0126 (8) | 0.0218 (10) | 0.0112 (8) | 0.0012 (7) | −0.0015 (7) | −0.0014 (7) |
C10 | 0.0149 (9) | 0.0174 (9) | 0.0118 (9) | 0.0027 (7) | −0.0030 (7) | −0.0010 (7) |
C15 | 0.0139 (9) | 0.0166 (9) | 0.0151 (10) | −0.0006 (7) | −0.0008 (7) | 0.0019 (7) |
C17 | 0.0162 (9) | 0.0221 (10) | 0.0135 (9) | 0.0002 (7) | 0.0003 (7) | 0.0039 (7) |
N1 | 0.0337 (10) | 0.0197 (9) | 0.0240 (9) | 0.0048 (8) | −0.0018 (8) | −0.0021 (7) |
C11 | 0.0138 (9) | 0.0201 (10) | 0.0097 (9) | −0.0006 (7) | −0.0019 (7) | 0.0002 (7) |
C13 | 0.0179 (9) | 0.0197 (10) | 0.0189 (10) | 0.0048 (7) | 0.0009 (7) | 0.0021 (8) |
C18 | 0.0165 (9) | 0.0174 (9) | 0.0144 (9) | −0.0023 (7) | −0.0001 (7) | 0.0015 (7) |
C14 | 0.0147 (9) | 0.0193 (9) | 0.0145 (9) | 0.0020 (7) | 0.0022 (7) | 0.0012 (7) |
C21 | 0.0235 (10) | 0.0317 (12) | 0.0158 (10) | 0.0071 (9) | 0.0013 (8) | −0.0004 (8) |
C7 | 0.0335 (12) | 0.0176 (10) | 0.0288 (12) | 0.0019 (9) | −0.0043 (9) | −0.0017 (9) |
C16 | 0.0151 (9) | 0.0173 (9) | 0.0122 (9) | −0.0019 (7) | −0.0005 (7) | 0.0026 (7) |
C8 | 0.0155 (9) | 0.0206 (10) | 0.0141 (9) | −0.0002 (7) | −0.0016 (7) | 0.0010 (7) |
C1 | 0.0197 (10) | 0.0194 (10) | 0.0293 (11) | 0.0038 (8) | −0.0012 (8) | 0.0057 (8) |
C19 | 0.0151 (9) | 0.0222 (10) | 0.0142 (9) | 0.0017 (7) | 0.0002 (7) | 0.0028 (7) |
C23 | 0.0160 (9) | 0.0401 (13) | 0.0170 (10) | −0.0043 (9) | −0.0014 (8) | 0.0038 (9) |
C22 | 0.0158 (9) | 0.0338 (12) | 0.0125 (9) | 0.0012 (8) | −0.0022 (7) | 0.0031 (8) |
C6 | 0.0153 (9) | 0.0188 (10) | 0.0229 (10) | 0.0041 (7) | 0.0014 (7) | 0.0056 (8) |
C5 | 0.0229 (10) | 0.0257 (11) | 0.0253 (11) | 0.0063 (8) | 0.0050 (8) | 0.0056 (9) |
N2 | 0.0658 (15) | 0.0313 (11) | 0.0251 (10) | 0.0156 (10) | 0.0028 (10) | −0.0039 (9) |
C3 | 0.0230 (11) | 0.0268 (12) | 0.0557 (16) | 0.0025 (9) | 0.0081 (10) | 0.0202 (11) |
C2 | 0.0253 (11) | 0.0192 (11) | 0.0471 (15) | 0.0006 (9) | −0.0028 (10) | 0.0083 (10) |
C24 | 0.0336 (13) | 0.0365 (14) | 0.0378 (14) | −0.0068 (10) | 0.0043 (10) | −0.0041 (11) |
C20 | 0.0167 (10) | 0.0281 (11) | 0.0316 (12) | −0.0020 (8) | 0.0061 (8) | 0.0022 (9) |
N4 | 0.0754 (17) | 0.0280 (11) | 0.0347 (12) | 0.0199 (11) | 0.0085 (11) | −0.0004 (9) |
C4 | 0.0280 (11) | 0.0381 (13) | 0.0351 (13) | 0.0102 (10) | 0.0130 (10) | 0.0172 (11) |
N3 | 0.100 (2) | 0.0355 (13) | 0.0330 (12) | 0.0290 (13) | 0.0143 (13) | 0.0002 (10) |
O1A | 0.0647 (16) | 0.0664 (16) | 0.0800 (18) | −0.0069 (13) | 0.0138 (14) | −0.0104 (13) |
C1A | 0.076 (3) | 0.068 (2) | 0.072 (2) | −0.002 (2) | 0.016 (2) | 0.008 (2) |
C2A | 0.079 (3) | 0.076 (3) | 0.099 (3) | −0.019 (2) | 0.019 (2) | −0.035 (2) |
Geometric parameters (Å, º) top
O2—C18 | 1.253 (2) | C13—C8 | 1.400 (3) |
O3—C18 | 1.248 (2) | C21—C19 | 1.517 (3) |
O1—C19 | 1.431 (2) | C7—C1 | 1.472 (3) |
N6—C17 | 1.333 (3) | C7—N4 | 1.329 (3) |
N6—C16 | 1.375 (3) | C16—C19 | 1.521 (3) |
N5—C15 | 1.409 (2) | C8—C6 | 1.489 (3) |
N5—C17 | 1.330 (3) | C1—C6 | 1.407 (3) |
N5—C14 | 1.471 (2) | C1—C2 | 1.393 (3) |
C12—C11 | 1.393 (3) | C19—C20 | 1.530 (3) |
C12—C13 | 1.386 (3) | C23—C22 | 1.537 (3) |
C9—C10 | 1.385 (3) | C23—C24 | 1.516 (3) |
C9—C8 | 1.393 (3) | C6—C5 | 1.391 (3) |
C10—C11 | 1.395 (3) | C5—C4 | 1.390 (3) |
C15—C18 | 1.499 (3) | N2—N3 | 1.299 (3) |
C15—C16 | 1.376 (3) | C3—C2 | 1.380 (4) |
C17—C22 | 1.487 (3) | C3—C4 | 1.387 (4) |
N1—C7 | 1.340 (3) | N4—N3 | 1.368 (3) |
N1—N2 | 1.349 (3) | O1A—C2A | 1.405 (5) |
C11—C14 | 1.511 (3) | C1A—C2A | 1.473 (6) |
| | | |
C17—N6—C16 | 110.07 (16) | C15—C16—C19 | 132.44 (17) |
C15—N5—C14 | 127.87 (16) | C9—C8—C13 | 118.71 (18) |
C17—N5—C15 | 109.22 (16) | C9—C8—C6 | 120.40 (17) |
C17—N5—C14 | 122.91 (16) | C13—C8—C6 | 120.79 (18) |
C13—C12—C11 | 120.58 (17) | C6—C1—C7 | 120.51 (19) |
C10—C9—C8 | 120.56 (17) | C2—C1—C7 | 119.4 (2) |
C9—C10—C11 | 120.77 (18) | C2—C1—C6 | 120.1 (2) |
N5—C15—C18 | 124.05 (17) | O1—C19—C21 | 106.12 (16) |
C16—C15—N5 | 105.70 (16) | O1—C19—C16 | 108.92 (15) |
C16—C15—C18 | 130.23 (17) | O1—C19—C20 | 110.34 (16) |
N6—C17—C22 | 124.06 (18) | C21—C19—C16 | 111.30 (16) |
N5—C17—N6 | 108.14 (17) | C21—C19—C20 | 111.35 (17) |
N5—C17—C22 | 127.65 (17) | C16—C19—C20 | 108.76 (16) |
C7—N1—N2 | 109.22 (19) | C24—C23—C22 | 113.56 (17) |
C12—C11—C10 | 118.74 (17) | C17—C22—C23 | 111.87 (17) |
C12—C11—C14 | 123.36 (16) | C1—C6—C8 | 120.20 (18) |
C10—C11—C14 | 117.86 (17) | C5—C6—C8 | 120.87 (19) |
C12—C13—C8 | 120.60 (18) | C5—C6—C1 | 118.93 (19) |
O2—C18—C15 | 116.79 (17) | C4—C5—C6 | 120.4 (2) |
O3—C18—O2 | 125.39 (18) | N3—N2—N1 | 106.3 (2) |
O3—C18—C15 | 117.82 (17) | C2—C3—C4 | 120.0 (2) |
N5—C14—C11 | 113.26 (16) | C3—C2—C1 | 120.3 (2) |
N1—C7—C1 | 125.6 (2) | C7—N4—N3 | 106.1 (2) |
N4—C7—N1 | 107.9 (2) | C3—C4—C5 | 120.3 (2) |
N4—C7—C1 | 126.5 (2) | N2—N3—N4 | 110.5 (2) |
N6—C16—C15 | 106.85 (16) | O1A—C2A—C1A | 111.3 (3) |
N6—C16—C19 | 120.71 (17) | | |
4-(2-Hydroxypropan-2-yl)-2-propyl-1-({4-[2-(1
H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1
H-imidazol-3-ium-5-carboxylate
isopropanol monosolvate (Ol-IsoProp)
top
Crystal data top
C24H26N6O3·C3H8O | F(000) = 1080 |
Mr = 506.60 | Dx = 1.292 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 9.76826 (15) Å | Cell parameters from 9444 reflections |
b = 18.4810 (3) Å | θ = 4.5–71.6° |
c = 14.42279 (19) Å | µ = 0.72 mm−1 |
β = 90.7205 (13)° | T = 102 K |
V = 2603.49 (6) Å3 | Needle, colourless |
Z = 4 | 0.1 × 0.01 × 0.01 mm |
Data collection top
Agilent SuperNova Dual Source diffractometer with an Eos detector | 5025 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 4590 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.021 |
Detector resolution: 16.4335 pixels mm-1 | θmax = 71.8°, θmin = 3.9° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −19→22 |
Tmin = 0.882, Tmax = 1.000 | l = −17→17 |
17119 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.0598P)2 + 1.5357P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
5025 reflections | Δρmax = 0.44 e Å−3 |
345 parameters | Δρmin = −0.31 e Å−3 |
1 restraint | |
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. |
Refinement. Single crystals of each solvate were selected and analysed using a
SuperNova diffractometer equipped with dual X-ray sources (Cu and Mo), using
Cu radiation and Eos CCD detector. The X-ray tube has been set to operate at
50 kV and 0.8 mA. Diffraction intensities were collected and corrected for
Lorentz, polarization and absorption effects using CrysAlis PRO software
(Agilent, 2012). Because of highly disordered solvent
molecules in crystal
lattices the investigated crystals were kept at low temperatures (100 K)
during data collection. Using Olex2 (Dolomanov et al., 2009), the
structures were solved with the ShelXS (Sheldrick, 2008)
structure solution
program using Direct Methods and refined with the ShelXL (Sheldrick, 2015)
refinement package by Least Squares minimisation. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O3 | 0.70456 (10) | 0.22752 (6) | 0.04285 (7) | 0.0217 (2) | |
O2 | 0.49687 (10) | 0.25938 (6) | 0.09015 (7) | 0.0209 (2) | |
O1 | 0.41152 (11) | 0.33762 (6) | 0.22560 (7) | 0.0215 (2) | |
H1 | 0.428027 | 0.317897 | 0.176058 | 0.032* | |
N6 | 0.69619 (12) | 0.26039 (6) | 0.35459 (8) | 0.0158 (2) | |
H6 | 0.678149 | 0.267907 | 0.411996 | 0.019* | |
N5 | 0.80642 (12) | 0.23239 (6) | 0.23091 (8) | 0.0150 (2) | |
C17 | 0.81746 (14) | 0.23941 (7) | 0.32274 (9) | 0.0164 (3) | |
C16 | 0.60387 (14) | 0.26830 (7) | 0.28212 (9) | 0.0152 (3) | |
C9 | 1.19586 (14) | 0.32133 (8) | 0.05290 (9) | 0.0166 (3) | |
H9 | 1.280564 | 0.312571 | 0.026389 | 0.020* | |
N1 | 1.25083 (14) | 0.46063 (7) | 0.23430 (9) | 0.0226 (3) | |
C15 | 0.67193 (14) | 0.24946 (7) | 0.20280 (9) | 0.0153 (3) | |
C18 | 0.62102 (14) | 0.24489 (7) | 0.10362 (9) | 0.0156 (3) | |
C11 | 0.99571 (14) | 0.27623 (7) | 0.13092 (9) | 0.0154 (3) | |
C19 | 0.45808 (14) | 0.29264 (7) | 0.30022 (9) | 0.0173 (3) | |
C12 | 0.93979 (14) | 0.34562 (8) | 0.12766 (9) | 0.0180 (3) | |
H12 | 0.853109 | 0.353803 | 0.151466 | 0.022* | |
C22 | 0.94335 (14) | 0.23319 (8) | 0.38130 (10) | 0.0192 (3) | |
H22A | 0.998681 | 0.193283 | 0.359336 | 0.023* | |
H22B | 0.918134 | 0.222998 | 0.444816 | 0.023* | |
C8 | 1.14163 (14) | 0.39113 (8) | 0.05155 (9) | 0.0167 (3) | |
C1 | 1.25951 (15) | 0.51108 (8) | 0.07383 (10) | 0.0205 (3) | |
C10 | 1.12470 (14) | 0.26483 (7) | 0.09340 (9) | 0.0162 (3) | |
H10 | 1.163471 | 0.218893 | 0.095529 | 0.019* | |
C5 | 1.26767 (15) | 0.45415 (8) | −0.07599 (10) | 0.0227 (3) | |
H5 | 1.244467 | 0.416381 | −0.115789 | 0.027* | |
C14 | 0.92241 (14) | 0.21197 (7) | 0.17226 (9) | 0.0165 (3) | |
H14A | 0.889171 | 0.181179 | 0.122384 | 0.020* | |
H14B | 0.987272 | 0.184076 | 0.209087 | 0.020* | |
C6 | 1.22416 (14) | 0.45280 (8) | 0.01555 (10) | 0.0184 (3) | |
N4 | 1.13994 (17) | 0.56033 (8) | 0.21235 (10) | 0.0336 (3) | |
O1A | 1.19649 (15) | 0.08233 (8) | 0.19033 (11) | 0.0458 (3) | |
H1AA | 1.118486 | 0.065939 | 0.190304 | 0.069* | |
C23 | 1.02750 (15) | 0.30363 (8) | 0.37822 (10) | 0.0219 (3) | |
H23A | 1.106822 | 0.298637 | 0.418858 | 0.026* | |
H23B | 1.060221 | 0.310813 | 0.315671 | 0.026* | |
C13 | 1.01209 (14) | 0.40250 (8) | 0.08931 (10) | 0.0187 (3) | |
H13 | 0.974200 | 0.448661 | 0.088653 | 0.022* | |
C2 | 1.33652 (16) | 0.56880 (8) | 0.04023 (12) | 0.0258 (3) | |
H2 | 1.358501 | 0.607403 | 0.079011 | 0.031* | |
C7 | 1.21801 (16) | 0.51144 (8) | 0.17169 (10) | 0.0221 (3) | |
C3 | 1.38009 (16) | 0.56871 (9) | −0.05035 (12) | 0.0286 (4) | |
H3 | 1.432467 | 0.606878 | −0.072426 | 0.034* | |
C21 | 0.45069 (16) | 0.33925 (9) | 0.38706 (10) | 0.0242 (3) | |
H21A | 0.515125 | 0.378285 | 0.382697 | 0.036* | |
H21B | 0.472362 | 0.310300 | 0.440530 | 0.036* | |
H21C | 0.359933 | 0.358542 | 0.392711 | 0.036* | |
N3 | 1.12500 (18) | 0.53700 (8) | 0.30149 (10) | 0.0390 (4) | |
C4 | 1.34568 (16) | 0.51169 (9) | −0.10832 (11) | 0.0284 (4) | |
H4 | 1.374938 | 0.511811 | −0.169435 | 0.034* | |
C24 | 0.94659 (18) | 0.36985 (9) | 0.40724 (12) | 0.0306 (4) | |
H24A | 0.876317 | 0.379600 | 0.361809 | 0.046* | |
H24B | 1.006855 | 0.410754 | 0.411968 | 0.046* | |
H24C | 0.905438 | 0.361068 | 0.466276 | 0.046* | |
N2 | 1.19240 (16) | 0.47718 (8) | 0.31519 (10) | 0.0324 (3) | |
C20 | 0.36737 (16) | 0.22560 (9) | 0.30834 (13) | 0.0284 (4) | |
H20A | 0.275314 | 0.240160 | 0.321563 | 0.043* | |
H20B | 0.401423 | 0.195318 | 0.357552 | 0.043* | |
H20C | 0.368390 | 0.199214 | 0.251021 | 0.043* | |
C2A | 1.2838 (2) | 0.03478 (10) | 0.14016 (12) | 0.0355 (4) | |
H2A | 1.282195 | −0.013053 | 0.169448 | 0.043* | |
C1A | 1.4280 (2) | 0.06532 (11) | 0.14775 (15) | 0.0447 (5) | |
H1AB | 1.430944 | 0.111771 | 0.118065 | 0.067* | |
H1AC | 1.490695 | 0.033043 | 0.118041 | 0.067* | |
H1AD | 1.453277 | 0.070421 | 0.211948 | 0.067* | |
C3A | 1.2382 (3) | 0.02746 (13) | 0.04091 (14) | 0.0547 (6) | |
H3AA | 1.145347 | 0.010446 | 0.038495 | 0.082* | |
H3AB | 1.296310 | −0.006447 | 0.009885 | 0.082* | |
H3AC | 1.243692 | 0.073684 | 0.010825 | 0.082* | |
H1A | 1.3011 (18) | 0.4223 (9) | 0.2273 (14) | 0.030 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O3 | 0.0204 (5) | 0.0317 (6) | 0.0131 (5) | 0.0008 (4) | 0.0016 (4) | −0.0013 (4) |
O2 | 0.0193 (5) | 0.0270 (5) | 0.0165 (5) | 0.0031 (4) | −0.0020 (4) | −0.0034 (4) |
O1 | 0.0263 (5) | 0.0243 (5) | 0.0138 (5) | 0.0084 (4) | −0.0006 (4) | 0.0008 (4) |
N6 | 0.0186 (6) | 0.0185 (6) | 0.0103 (5) | −0.0003 (4) | 0.0009 (4) | 0.0011 (4) |
N5 | 0.0168 (6) | 0.0150 (5) | 0.0134 (5) | −0.0001 (4) | 0.0011 (4) | 0.0012 (4) |
C17 | 0.0198 (7) | 0.0145 (6) | 0.0149 (6) | −0.0010 (5) | 0.0012 (5) | 0.0021 (5) |
C16 | 0.0186 (7) | 0.0135 (6) | 0.0136 (6) | −0.0016 (5) | 0.0002 (5) | 0.0019 (5) |
C9 | 0.0158 (6) | 0.0199 (7) | 0.0141 (6) | 0.0017 (5) | −0.0003 (5) | −0.0016 (5) |
N1 | 0.0309 (7) | 0.0173 (6) | 0.0198 (6) | 0.0039 (5) | 0.0010 (5) | −0.0015 (5) |
C15 | 0.0160 (6) | 0.0137 (6) | 0.0162 (7) | −0.0004 (5) | 0.0006 (5) | 0.0016 (5) |
C18 | 0.0197 (7) | 0.0131 (6) | 0.0140 (6) | −0.0024 (5) | 0.0007 (5) | 0.0011 (5) |
C11 | 0.0176 (7) | 0.0175 (7) | 0.0111 (6) | 0.0001 (5) | −0.0013 (5) | −0.0005 (5) |
C19 | 0.0183 (7) | 0.0183 (7) | 0.0152 (6) | 0.0025 (5) | 0.0014 (5) | 0.0024 (5) |
C12 | 0.0168 (6) | 0.0203 (7) | 0.0169 (6) | 0.0028 (5) | 0.0016 (5) | −0.0004 (5) |
C22 | 0.0193 (7) | 0.0235 (7) | 0.0148 (6) | 0.0023 (5) | −0.0012 (5) | 0.0021 (5) |
C8 | 0.0186 (7) | 0.0184 (7) | 0.0132 (6) | −0.0006 (5) | −0.0012 (5) | 0.0004 (5) |
C1 | 0.0209 (7) | 0.0166 (7) | 0.0241 (7) | 0.0033 (5) | −0.0004 (5) | 0.0041 (5) |
C10 | 0.0188 (7) | 0.0155 (6) | 0.0142 (6) | 0.0020 (5) | −0.0010 (5) | −0.0011 (5) |
C5 | 0.0227 (7) | 0.0230 (7) | 0.0226 (7) | 0.0043 (6) | 0.0021 (6) | 0.0034 (6) |
C14 | 0.0171 (6) | 0.0169 (6) | 0.0155 (6) | 0.0024 (5) | 0.0025 (5) | −0.0003 (5) |
C6 | 0.0163 (7) | 0.0180 (7) | 0.0209 (7) | 0.0038 (5) | 0.0005 (5) | 0.0042 (5) |
N4 | 0.0497 (9) | 0.0225 (7) | 0.0288 (7) | 0.0080 (6) | 0.0075 (6) | 0.0000 (6) |
O1A | 0.0444 (8) | 0.0383 (7) | 0.0548 (9) | −0.0066 (6) | 0.0089 (7) | −0.0052 (6) |
C23 | 0.0189 (7) | 0.0297 (8) | 0.0170 (7) | −0.0027 (6) | −0.0013 (5) | 0.0025 (6) |
C13 | 0.0202 (7) | 0.0162 (7) | 0.0196 (7) | 0.0034 (5) | 0.0003 (5) | 0.0011 (5) |
C2 | 0.0249 (8) | 0.0167 (7) | 0.0356 (9) | 0.0005 (6) | −0.0015 (6) | 0.0039 (6) |
C7 | 0.0278 (8) | 0.0143 (7) | 0.0241 (7) | 0.0005 (6) | −0.0006 (6) | −0.0009 (5) |
C3 | 0.0236 (8) | 0.0220 (8) | 0.0403 (9) | 0.0006 (6) | 0.0050 (6) | 0.0134 (7) |
C21 | 0.0275 (8) | 0.0279 (8) | 0.0173 (7) | 0.0094 (6) | 0.0006 (6) | −0.0015 (6) |
N3 | 0.0610 (10) | 0.0271 (8) | 0.0292 (8) | 0.0120 (7) | 0.0114 (7) | −0.0007 (6) |
C4 | 0.0265 (8) | 0.0326 (9) | 0.0263 (8) | 0.0071 (7) | 0.0083 (6) | 0.0119 (7) |
C24 | 0.0321 (9) | 0.0256 (8) | 0.0340 (9) | −0.0057 (7) | 0.0044 (7) | −0.0030 (7) |
N2 | 0.0488 (9) | 0.0247 (7) | 0.0236 (7) | 0.0074 (6) | 0.0061 (6) | −0.0019 (5) |
C20 | 0.0200 (7) | 0.0248 (8) | 0.0408 (9) | −0.0017 (6) | 0.0085 (7) | 0.0020 (7) |
C2A | 0.0477 (11) | 0.0271 (8) | 0.0319 (9) | −0.0045 (7) | 0.0029 (8) | 0.0037 (7) |
C1A | 0.0505 (12) | 0.0346 (10) | 0.0492 (12) | −0.0037 (9) | 0.0069 (9) | −0.0020 (8) |
C3A | 0.0776 (16) | 0.0524 (13) | 0.0341 (11) | −0.0189 (12) | −0.0009 (10) | 0.0070 (9) |
Geometric parameters (Å, º) top
O3—C18 | 1.2471 (17) | C5—C6 | 1.392 (2) |
O2—C18 | 1.2546 (17) | C5—C4 | 1.392 (2) |
O1—H1 | 0.8200 | C14—H14A | 0.9700 |
O1—C19 | 1.4296 (16) | C14—H14B | 0.9700 |
N6—H6 | 0.8600 | N4—C7 | 1.324 (2) |
N6—C17 | 1.3335 (18) | N4—N3 | 1.366 (2) |
N6—C16 | 1.3796 (18) | O1A—H1AA | 0.8200 |
N5—C17 | 1.3338 (18) | O1A—C2A | 1.428 (2) |
N5—C15 | 1.4059 (17) | C23—H23A | 0.9700 |
N5—C14 | 1.4716 (17) | C23—H23B | 0.9700 |
C17—C22 | 1.4875 (19) | C23—C24 | 1.519 (2) |
C16—C15 | 1.3752 (19) | C13—H13 | 0.9300 |
C16—C19 | 1.5192 (19) | C2—H2 | 0.9300 |
C9—H9 | 0.9300 | C2—C3 | 1.379 (2) |
C9—C8 | 1.395 (2) | C3—H3 | 0.9300 |
C9—C10 | 1.3874 (19) | C3—C4 | 1.384 (3) |
N1—C7 | 1.339 (2) | C21—H21A | 0.9600 |
N1—N2 | 1.3407 (18) | C21—H21B | 0.9600 |
N1—H1A | 0.868 (15) | C21—H21C | 0.9600 |
C15—C18 | 1.5109 (18) | N3—N2 | 1.300 (2) |
C11—C12 | 1.3946 (19) | C4—H4 | 0.9300 |
C11—C10 | 1.3935 (19) | C24—H24A | 0.9600 |
C11—C14 | 1.5130 (18) | C24—H24B | 0.9600 |
C19—C21 | 1.5226 (19) | C24—H24C | 0.9600 |
C19—C20 | 1.529 (2) | C20—H20A | 0.9600 |
C12—H12 | 0.9300 | C20—H20B | 0.9600 |
C12—C13 | 1.385 (2) | C20—H20C | 0.9600 |
C22—H22A | 0.9700 | C2A—H2A | 0.9800 |
C22—H22B | 0.9700 | C2A—C1A | 1.520 (3) |
C22—C23 | 1.541 (2) | C2A—C3A | 1.500 (3) |
C8—C6 | 1.4930 (19) | C1A—H1AB | 0.9600 |
C8—C13 | 1.3997 (19) | C1A—H1AC | 0.9600 |
C1—C6 | 1.407 (2) | C1A—H1AD | 0.9600 |
C1—C2 | 1.396 (2) | C3A—H3AA | 0.9600 |
C1—C7 | 1.473 (2) | C3A—H3AB | 0.9600 |
C10—H10 | 0.9300 | C3A—H3AC | 0.9600 |
C5—H5 | 0.9300 | | |
| | | |
C19—O1—H1 | 109.5 | C5—C6—C1 | 118.51 (13) |
C17—N6—H6 | 124.9 | C7—N4—N3 | 105.69 (13) |
C17—N6—C16 | 110.18 (11) | C2A—O1A—H1AA | 109.5 |
C16—N6—H6 | 124.9 | C22—C23—H23A | 108.9 |
C17—N5—C15 | 109.15 (11) | C22—C23—H23B | 108.9 |
C17—N5—C14 | 122.86 (11) | H23A—C23—H23B | 107.8 |
C15—N5—C14 | 127.96 (11) | C24—C23—C22 | 113.16 (12) |
N6—C17—N5 | 108.02 (12) | C24—C23—H23A | 108.9 |
N6—C17—C22 | 123.95 (12) | C24—C23—H23B | 108.9 |
N5—C17—C22 | 127.75 (12) | C12—C13—C8 | 120.62 (13) |
N6—C16—C19 | 120.43 (12) | C12—C13—H13 | 119.7 |
C15—C16—N6 | 106.57 (12) | C8—C13—H13 | 119.7 |
C15—C16—C19 | 133.00 (13) | C1—C2—H2 | 119.9 |
C8—C9—H9 | 119.7 | C3—C2—C1 | 120.14 (15) |
C10—C9—H9 | 119.7 | C3—C2—H2 | 119.9 |
C10—C9—C8 | 120.65 (12) | N1—C7—C1 | 125.20 (13) |
C7—N1—N2 | 109.02 (13) | N4—C7—N1 | 108.31 (13) |
C7—N1—H1A | 128.7 (13) | N4—C7—C1 | 126.47 (14) |
N2—N1—H1A | 122.3 (13) | C2—C3—H3 | 120.1 |
N5—C15—C18 | 123.77 (12) | C2—C3—C4 | 119.85 (14) |
C16—C15—N5 | 106.06 (12) | C4—C3—H3 | 120.1 |
C16—C15—C18 | 130.16 (13) | C19—C21—H21A | 109.5 |
O3—C18—O2 | 125.87 (12) | C19—C21—H21B | 109.5 |
O3—C18—C15 | 117.98 (12) | C19—C21—H21C | 109.5 |
O2—C18—C15 | 116.15 (12) | H21A—C21—H21B | 109.5 |
C12—C11—C14 | 123.22 (12) | H21A—C21—H21C | 109.5 |
C10—C11—C12 | 118.79 (12) | H21B—C21—H21C | 109.5 |
C10—C11—C14 | 117.98 (12) | N2—N3—N4 | 110.58 (13) |
O1—C19—C16 | 109.44 (11) | C5—C4—H4 | 119.7 |
O1—C19—C21 | 105.81 (11) | C3—C4—C5 | 120.60 (15) |
O1—C19—C20 | 110.48 (12) | C3—C4—H4 | 119.7 |
C16—C19—C21 | 111.29 (12) | C23—C24—H24A | 109.5 |
C16—C19—C20 | 108.59 (11) | C23—C24—H24B | 109.5 |
C21—C19—C20 | 111.22 (12) | C23—C24—H24C | 109.5 |
C11—C12—H12 | 119.7 | H24A—C24—H24B | 109.5 |
C13—C12—C11 | 120.64 (13) | H24A—C24—H24C | 109.5 |
C13—C12—H12 | 119.7 | H24B—C24—H24C | 109.5 |
C17—C22—H22A | 109.5 | N3—N2—N1 | 106.38 (13) |
C17—C22—H22B | 109.5 | C19—C20—H20A | 109.5 |
C17—C22—C23 | 110.86 (11) | C19—C20—H20B | 109.5 |
H22A—C22—H22B | 108.1 | C19—C20—H20C | 109.5 |
C23—C22—H22A | 109.5 | H20A—C20—H20B | 109.5 |
C23—C22—H22B | 109.5 | H20A—C20—H20C | 109.5 |
C9—C8—C6 | 120.28 (12) | H20B—C20—H20C | 109.5 |
C9—C8—C13 | 118.59 (13) | O1A—C2A—H2A | 108.9 |
C13—C8—C6 | 121.04 (12) | O1A—C2A—C1A | 107.08 (15) |
C6—C1—C7 | 120.50 (13) | O1A—C2A—C3A | 111.53 (18) |
C2—C1—C6 | 120.47 (14) | C1A—C2A—H2A | 108.9 |
C2—C1—C7 | 119.02 (14) | C3A—C2A—H2A | 108.9 |
C9—C10—C11 | 120.66 (12) | C3A—C2A—C1A | 111.48 (17) |
C9—C10—H10 | 119.7 | C2A—C1A—H1AB | 109.5 |
C11—C10—H10 | 119.7 | C2A—C1A—H1AC | 109.5 |
C6—C5—H5 | 119.8 | C2A—C1A—H1AD | 109.5 |
C4—C5—H5 | 119.8 | H1AB—C1A—H1AC | 109.5 |
C4—C5—C6 | 120.42 (15) | H1AB—C1A—H1AD | 109.5 |
N5—C14—C11 | 113.39 (11) | H1AC—C1A—H1AD | 109.5 |
N5—C14—H14A | 108.9 | C2A—C3A—H3AA | 109.5 |
N5—C14—H14B | 108.9 | C2A—C3A—H3AB | 109.5 |
C11—C14—H14A | 108.9 | C2A—C3A—H3AC | 109.5 |
C11—C14—H14B | 108.9 | H3AA—C3A—H3AB | 109.5 |
H14A—C14—H14B | 107.7 | H3AA—C3A—H3AC | 109.5 |
C1—C6—C8 | 120.41 (12) | H3AB—C3A—H3AC | 109.5 |
C5—C6—C8 | 121.08 (13) | | |
4-(2-Hydroxypropan-2-yl)-2-propyl-1-({4-[2-(1
H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1
H-imidazol-3-ium-5-carboxylate
isobutanol monosolvate (Ol-IsoBut)
top
Crystal data top
C24H26N6O3·C4H10O | F(000) = 1112 |
Mr = 520.63 | Dx = 1.276 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 9.77352 (14) Å | Cell parameters from 15971 reflections |
b = 19.3316 (3) Å | θ = 3.8–71.4° |
c = 14.34250 (17) Å | µ = 0.71 mm−1 |
β = 90.3045 (11)° | T = 101 K |
V = 2709.81 (7) Å3 | Needle, colourless |
Z = 4 | 0.1 × 0.01 × 0.01 mm |
Data collection top
Agilent SuperNova Dual Source diffractometer with an Eos detector | 5270 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 4555 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.038 |
Detector resolution: 16.4335 pixels mm-1 | θmax = 71.8°, θmin = 3.8° |
ω scans | h = −11→12 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −23→20 |
Tmin = 0.867, Tmax = 1.000 | l = −17→17 |
39211 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.108 | w = 1/[σ2(Fo2) + (0.0527P)2 + 1.2805P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
5270 reflections | Δρmax = 0.28 e Å−3 |
354 parameters | Δρmin = −0.25 e Å−3 |
1 restraint | |
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. |
Refinement. Single crystals of each solvate were selected and analysed using a
SuperNova diffractometer equipped with dual X-ray sources (Cu and Mo), using
Cu radiation and Eos CCD detector. The X-ray tube has been set to operate at
50 kV and 0.8 mA. Diffraction intensities were collected and corrected for
Lorentz, polarization and absorption effects using CrysAlis PRO software
(Agilent, 2012). Because of highly disordered solvent
molecules in crystal
lattices the investigated crystals were kept at low temperatures (100 K)
during data collection. Using Olex2 (Dolomanov et al., 2009), the
structures were solved with the ShelXS (Sheldrick, 2008)
structure solution
program using Direct Methods and refined with the ShelXL (Sheldrick, 2015)
refinement package by Least Squares minimisation. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O3 | 0.21070 (10) | 0.23719 (6) | 0.93756 (6) | 0.0236 (2) | |
O2 | 0.00955 (10) | 0.27749 (5) | 0.88809 (6) | 0.0223 (2) | |
O1 | −0.08312 (10) | 0.33774 (5) | 0.74124 (6) | 0.0224 (2) | |
H1 | −0.064303 | 0.324415 | 0.794055 | 0.034* | |
N6 | 0.20129 (11) | 0.25845 (6) | 0.62321 (7) | 0.0169 (2) | |
H6 | 0.182399 | 0.262672 | 0.564858 | 0.020* | |
N5 | 0.31406 (11) | 0.23926 (6) | 0.75053 (7) | 0.0166 (2) | |
N1 | 0.77103 (12) | 0.45658 (7) | 0.70946 (8) | 0.0229 (3) | |
C12 | 0.44547 (14) | 0.35633 (8) | 0.83769 (9) | 0.0216 (3) | |
H12 | 0.357770 | 0.361203 | 0.813082 | 0.026* | |
C17 | 0.32356 (13) | 0.24110 (7) | 0.65766 (9) | 0.0174 (3) | |
C16 | 0.10964 (13) | 0.26863 (7) | 0.69448 (9) | 0.0164 (3) | |
C9 | 0.70260 (13) | 0.34260 (7) | 0.91725 (9) | 0.0200 (3) | |
H9 | 0.787441 | 0.337403 | 0.946079 | 0.024* | |
N3 | 0.66416 (15) | 0.52609 (8) | 0.62152 (10) | 0.0351 (3) | |
N2 | 0.72761 (13) | 0.46750 (7) | 0.62113 (9) | 0.0291 (3) | |
C11 | 0.50239 (13) | 0.29079 (7) | 0.84586 (8) | 0.0171 (3) | |
C10 | 0.63168 (13) | 0.28462 (7) | 0.88656 (9) | 0.0187 (3) | |
H10 | 0.670944 | 0.241063 | 0.893232 | 0.022* | |
C19 | −0.03892 (13) | 0.28727 (7) | 0.67487 (9) | 0.0177 (3) | |
C18 | 0.12949 (14) | 0.25697 (7) | 0.87526 (9) | 0.0172 (3) | |
C8 | 0.64774 (14) | 0.40840 (7) | 0.90522 (9) | 0.0203 (3) | |
C21 | −0.05546 (14) | 0.32068 (8) | 0.57947 (9) | 0.0219 (3) | |
H21A | −0.147722 | 0.336891 | 0.572066 | 0.033* | |
H21B | −0.035706 | 0.287274 | 0.531873 | 0.033* | |
H21C | 0.006613 | 0.358951 | 0.574238 | 0.033* | |
C7 | 0.73265 (14) | 0.50958 (8) | 0.76250 (10) | 0.0238 (3) | |
C22 | 0.44824 (14) | 0.23095 (8) | 0.60020 (9) | 0.0227 (3) | |
H22A | 0.421348 | 0.218059 | 0.537366 | 0.027* | |
H22B | 0.502036 | 0.193375 | 0.626173 | 0.027* | |
C13 | 0.51754 (14) | 0.41471 (8) | 0.86573 (10) | 0.0235 (3) | |
H13 | 0.478777 | 0.458292 | 0.858139 | 0.028* | |
C14 | 0.43178 (13) | 0.22566 (7) | 0.81218 (9) | 0.0178 (3) | |
H14A | 0.497474 | 0.197356 | 0.779026 | 0.021* | |
H14B | 0.400870 | 0.199509 | 0.865805 | 0.021* | |
N4 | 0.66531 (14) | 0.55403 (7) | 0.70898 (10) | 0.0326 (3) | |
C6 | 0.72930 (14) | 0.47110 (8) | 0.93046 (10) | 0.0231 (3) | |
C5 | 0.77063 (15) | 0.48287 (8) | 1.02236 (11) | 0.0283 (3) | |
H5 | 0.748438 | 0.450990 | 1.068425 | 0.034* | |
C1 | 0.76574 (14) | 0.51968 (8) | 0.86232 (10) | 0.0238 (3) | |
C20 | −0.12547 (15) | 0.22172 (8) | 0.68302 (11) | 0.0263 (3) | |
H20A | −0.114077 | 0.202257 | 0.744148 | 0.040* | |
H20B | −0.096624 | 0.188754 | 0.637093 | 0.040* | |
H20C | −0.220061 | 0.232987 | 0.672942 | 0.040* | |
C23 | 0.53665 (14) | 0.29692 (9) | 0.59652 (10) | 0.0276 (3) | |
H23A | 0.573941 | 0.305806 | 0.658175 | 0.033* | |
H23B | 0.612866 | 0.289013 | 0.554806 | 0.033* | |
C24 | 0.45874 (17) | 0.36044 (9) | 0.56391 (11) | 0.0336 (4) | |
H24A | 0.410995 | 0.350015 | 0.506955 | 0.050* | |
H24B | 0.521815 | 0.397661 | 0.553404 | 0.050* | |
H24C | 0.394112 | 0.373815 | 0.610747 | 0.050* | |
C2 | 0.83879 (15) | 0.57911 (8) | 0.88668 (11) | 0.0290 (3) | |
H2 | 0.861278 | 0.611353 | 0.841143 | 0.035* | |
C15 | 0.17941 (13) | 0.25597 (7) | 0.77622 (9) | 0.0164 (3) | |
C3 | 0.87781 (16) | 0.59020 (9) | 0.97824 (12) | 0.0333 (4) | |
H3 | 0.926043 | 0.629928 | 0.994433 | 0.040* | |
C4 | 0.84478 (16) | 0.54192 (9) | 1.04571 (11) | 0.0333 (4) | |
H4 | 0.872344 | 0.548979 | 1.107136 | 0.040* | |
O1A | 0.61938 (12) | 0.08041 (7) | 0.73781 (9) | 0.0419 (3) | |
H1AA | 0.538538 | 0.076380 | 0.751822 | 0.063* | |
C2A | 0.83577 (16) | 0.04822 (8) | 0.80825 (11) | 0.0288 (3) | |
H2A | 0.873632 | 0.061920 | 0.747865 | 0.035* | |
C3A | 0.70055 (17) | 0.08513 (9) | 0.82076 (12) | 0.0349 (4) | |
H3AA | 0.651362 | 0.064579 | 0.872384 | 0.042* | |
H3AB | 0.717136 | 0.133383 | 0.835499 | 0.042* | |
C1A | 0.93650 (18) | 0.06988 (10) | 0.88409 (12) | 0.0399 (4) | |
H1AB | 0.950019 | 0.119029 | 0.881514 | 0.060* | |
H1AC | 1.022308 | 0.046833 | 0.874614 | 0.060* | |
H1AD | 0.900697 | 0.057441 | 0.943997 | 0.060* | |
C4A | 0.8156 (2) | −0.02944 (9) | 0.80751 (14) | 0.0424 (4) | |
H4AA | 0.791787 | −0.044848 | 0.868957 | 0.064* | |
H4AB | 0.898760 | −0.051579 | 0.788405 | 0.064* | |
H4AC | 0.743361 | −0.041139 | 0.764699 | 0.064* | |
H1A | 0.8176 (18) | 0.4202 (8) | 0.7227 (13) | 0.035 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O3 | 0.0232 (5) | 0.0380 (6) | 0.0096 (4) | 0.0028 (4) | −0.0012 (4) | 0.0013 (4) |
O2 | 0.0230 (5) | 0.0321 (6) | 0.0119 (4) | 0.0061 (4) | 0.0024 (4) | 0.0024 (4) |
O1 | 0.0288 (5) | 0.0274 (5) | 0.0110 (4) | 0.0088 (4) | 0.0006 (4) | −0.0001 (4) |
N6 | 0.0194 (5) | 0.0241 (6) | 0.0073 (5) | 0.0007 (4) | −0.0010 (4) | −0.0001 (4) |
N5 | 0.0174 (5) | 0.0223 (6) | 0.0100 (5) | 0.0008 (4) | −0.0012 (4) | −0.0012 (4) |
N1 | 0.0251 (6) | 0.0230 (6) | 0.0205 (6) | 0.0024 (5) | −0.0027 (5) | 0.0016 (5) |
C12 | 0.0190 (6) | 0.0260 (7) | 0.0198 (7) | 0.0029 (5) | −0.0032 (5) | 0.0006 (5) |
C17 | 0.0200 (6) | 0.0205 (7) | 0.0117 (6) | −0.0006 (5) | −0.0006 (5) | −0.0016 (5) |
C16 | 0.0201 (6) | 0.0182 (7) | 0.0110 (6) | −0.0008 (5) | 0.0003 (5) | −0.0010 (5) |
C9 | 0.0174 (6) | 0.0291 (8) | 0.0134 (6) | 0.0018 (5) | 0.0000 (5) | −0.0008 (5) |
N3 | 0.0383 (8) | 0.0355 (8) | 0.0313 (7) | 0.0061 (6) | −0.0073 (6) | 0.0061 (6) |
N2 | 0.0310 (7) | 0.0331 (7) | 0.0233 (6) | 0.0010 (5) | −0.0053 (5) | 0.0050 (5) |
C11 | 0.0193 (6) | 0.0235 (7) | 0.0084 (6) | 0.0003 (5) | 0.0007 (5) | 0.0000 (5) |
C10 | 0.0194 (6) | 0.0236 (7) | 0.0132 (6) | 0.0039 (5) | 0.0009 (5) | 0.0010 (5) |
C19 | 0.0185 (6) | 0.0225 (7) | 0.0123 (6) | 0.0023 (5) | −0.0004 (5) | −0.0013 (5) |
C18 | 0.0222 (6) | 0.0186 (7) | 0.0109 (6) | −0.0014 (5) | 0.0008 (5) | −0.0009 (5) |
C8 | 0.0201 (6) | 0.0259 (7) | 0.0150 (6) | 0.0000 (5) | 0.0024 (5) | −0.0017 (5) |
C21 | 0.0235 (7) | 0.0293 (8) | 0.0128 (6) | 0.0051 (6) | −0.0017 (5) | 0.0002 (5) |
C7 | 0.0212 (7) | 0.0219 (7) | 0.0283 (8) | −0.0004 (5) | −0.0005 (5) | 0.0019 (6) |
C22 | 0.0202 (7) | 0.0350 (8) | 0.0129 (6) | 0.0041 (6) | 0.0010 (5) | −0.0021 (5) |
C13 | 0.0227 (7) | 0.0229 (7) | 0.0249 (7) | 0.0031 (5) | −0.0018 (5) | 0.0000 (6) |
C14 | 0.0189 (6) | 0.0221 (7) | 0.0122 (6) | 0.0031 (5) | −0.0024 (5) | −0.0004 (5) |
N4 | 0.0335 (7) | 0.0281 (7) | 0.0362 (7) | 0.0059 (6) | −0.0036 (6) | 0.0040 (6) |
C6 | 0.0183 (6) | 0.0265 (8) | 0.0245 (7) | 0.0024 (5) | 0.0004 (5) | −0.0061 (6) |
C5 | 0.0259 (7) | 0.0343 (9) | 0.0247 (7) | 0.0000 (6) | 0.0011 (6) | −0.0053 (6) |
C1 | 0.0210 (7) | 0.0224 (7) | 0.0279 (8) | 0.0031 (5) | 0.0007 (5) | −0.0043 (6) |
C20 | 0.0208 (7) | 0.0283 (8) | 0.0300 (8) | −0.0016 (6) | −0.0024 (6) | 0.0026 (6) |
C23 | 0.0200 (7) | 0.0483 (10) | 0.0145 (6) | −0.0051 (6) | 0.0011 (5) | −0.0048 (6) |
C24 | 0.0379 (9) | 0.0382 (9) | 0.0247 (8) | −0.0123 (7) | −0.0042 (6) | 0.0012 (7) |
C2 | 0.0276 (8) | 0.0231 (8) | 0.0363 (8) | −0.0002 (6) | 0.0024 (6) | −0.0059 (6) |
C15 | 0.0177 (6) | 0.0194 (7) | 0.0120 (6) | 0.0002 (5) | 0.0001 (5) | −0.0014 (5) |
C3 | 0.0292 (8) | 0.0298 (8) | 0.0410 (9) | −0.0025 (6) | 0.0016 (7) | −0.0141 (7) |
C4 | 0.0287 (8) | 0.0426 (10) | 0.0287 (8) | −0.0001 (7) | −0.0020 (6) | −0.0167 (7) |
O1A | 0.0313 (6) | 0.0527 (8) | 0.0415 (7) | 0.0034 (6) | −0.0020 (5) | −0.0007 (6) |
C2A | 0.0320 (8) | 0.0297 (8) | 0.0247 (7) | −0.0003 (6) | 0.0023 (6) | −0.0039 (6) |
C3A | 0.0351 (9) | 0.0345 (9) | 0.0353 (9) | 0.0000 (7) | 0.0040 (7) | −0.0055 (7) |
C1A | 0.0402 (10) | 0.0462 (11) | 0.0333 (9) | −0.0004 (8) | −0.0039 (7) | −0.0089 (8) |
C4A | 0.0531 (11) | 0.0310 (9) | 0.0430 (10) | 0.0014 (8) | −0.0058 (8) | −0.0048 (8) |
Geometric parameters (Å, º) top
O3—C18 | 1.2518 (16) | C22—H22B | 0.9700 |
O2—C18 | 1.2520 (17) | C22—C23 | 1.542 (2) |
O1—H1 | 0.8200 | C13—H13 | 0.9300 |
O1—C19 | 1.4313 (16) | C14—H14A | 0.9700 |
N6—H6 | 0.8600 | C14—H14B | 0.9700 |
N6—C17 | 1.3336 (17) | C6—C5 | 1.395 (2) |
N6—C16 | 1.3769 (16) | C6—C1 | 1.403 (2) |
N5—C17 | 1.3362 (16) | C5—H5 | 0.9300 |
N5—C14 | 1.4710 (16) | C5—C4 | 1.392 (2) |
N5—C15 | 1.4061 (16) | C1—C2 | 1.396 (2) |
N1—N2 | 1.3505 (17) | C20—H20A | 0.9600 |
N1—C7 | 1.3313 (19) | C20—H20B | 0.9600 |
N1—H1A | 0.858 (14) | C20—H20C | 0.9600 |
C12—H12 | 0.9300 | C23—H23A | 0.9700 |
C12—C11 | 1.3884 (19) | C23—H23B | 0.9700 |
C12—C13 | 1.389 (2) | C23—C24 | 1.517 (2) |
C17—C22 | 1.4876 (18) | C24—H24A | 0.9600 |
C16—C19 | 1.5208 (18) | C24—H24B | 0.9600 |
C16—C15 | 1.3750 (18) | C24—H24C | 0.9600 |
C9—H9 | 0.9300 | C2—H2 | 0.9300 |
C9—C10 | 1.388 (2) | C2—C3 | 1.382 (2) |
C9—C8 | 1.391 (2) | C3—H3 | 0.9300 |
N3—N2 | 1.2913 (19) | C3—C4 | 1.384 (3) |
N3—N4 | 1.366 (2) | C4—H4 | 0.9300 |
C11—C10 | 1.3941 (18) | O1A—H1AA | 0.8200 |
C11—C14 | 1.5137 (18) | O1A—C3A | 1.429 (2) |
C10—H10 | 0.9300 | C2A—H2A | 0.9800 |
C19—C21 | 1.5209 (18) | C2A—C3A | 1.513 (2) |
C19—C20 | 1.528 (2) | C2A—C1A | 1.522 (2) |
C18—C15 | 1.5045 (17) | C2A—C4A | 1.514 (2) |
C8—C13 | 1.3954 (19) | C3A—H3AA | 0.9700 |
C8—C6 | 1.494 (2) | C3A—H3AB | 0.9700 |
C21—H21A | 0.9600 | C1A—H1AB | 0.9600 |
C21—H21B | 0.9600 | C1A—H1AC | 0.9600 |
C21—H21C | 0.9600 | C1A—H1AD | 0.9600 |
C7—N4 | 1.3249 (19) | C4A—H4AA | 0.9600 |
C7—C1 | 1.479 (2) | C4A—H4AB | 0.9600 |
C22—H22A | 0.9700 | C4A—H4AC | 0.9600 |
| | | |
C19—O1—H1 | 109.5 | C7—N4—N3 | 106.10 (13) |
C17—N6—H6 | 124.9 | C5—C6—C8 | 120.83 (13) |
C17—N6—C16 | 110.25 (11) | C5—C6—C1 | 118.41 (14) |
C16—N6—H6 | 124.9 | C1—C6—C8 | 120.76 (13) |
C17—N5—C14 | 123.07 (11) | C6—C5—H5 | 119.7 |
C17—N5—C15 | 108.98 (11) | C4—C5—C6 | 120.58 (15) |
C15—N5—C14 | 127.86 (10) | C4—C5—H5 | 119.7 |
N2—N1—H1A | 119.9 (13) | C6—C1—C7 | 122.08 (13) |
C7—N1—N2 | 109.13 (12) | C2—C1—C7 | 117.37 (14) |
C7—N1—H1A | 130.9 (13) | C2—C1—C6 | 120.53 (14) |
C11—C12—H12 | 119.5 | C19—C20—H20A | 109.5 |
C11—C12—C13 | 120.98 (13) | C19—C20—H20B | 109.5 |
C13—C12—H12 | 119.5 | C19—C20—H20C | 109.5 |
N6—C17—N5 | 108.00 (11) | H20A—C20—H20B | 109.5 |
N6—C17—C22 | 124.26 (12) | H20A—C20—H20C | 109.5 |
N5—C17—C22 | 127.61 (12) | H20B—C20—H20C | 109.5 |
N6—C16—C19 | 121.39 (11) | C22—C23—H23A | 108.9 |
C15—C16—N6 | 106.61 (11) | C22—C23—H23B | 108.9 |
C15—C16—C19 | 131.96 (12) | H23A—C23—H23B | 107.7 |
C10—C9—H9 | 119.7 | C24—C23—C22 | 113.55 (12) |
C10—C9—C8 | 120.50 (12) | C24—C23—H23A | 108.9 |
C8—C9—H9 | 119.7 | C24—C23—H23B | 108.9 |
N2—N3—N4 | 110.45 (12) | C23—C24—H24A | 109.5 |
N3—N2—N1 | 106.35 (12) | C23—C24—H24B | 109.5 |
C12—C11—C10 | 118.38 (13) | C23—C24—H24C | 109.5 |
C12—C11—C14 | 123.38 (12) | H24A—C24—H24B | 109.5 |
C10—C11—C14 | 118.23 (12) | H24A—C24—H24C | 109.5 |
C9—C10—C11 | 120.90 (13) | H24B—C24—H24C | 109.5 |
C9—C10—H10 | 119.6 | C1—C2—H2 | 119.9 |
C11—C10—H10 | 119.6 | C3—C2—C1 | 120.23 (15) |
O1—C19—C16 | 109.25 (10) | C3—C2—H2 | 119.9 |
O1—C19—C21 | 106.14 (11) | N5—C15—C18 | 123.98 (11) |
O1—C19—C20 | 110.19 (11) | C16—C15—N5 | 106.15 (11) |
C16—C19—C20 | 108.51 (11) | C16—C15—C18 | 129.85 (12) |
C21—C19—C16 | 111.34 (11) | C2—C3—H3 | 120.1 |
C21—C19—C20 | 111.39 (11) | C2—C3—C4 | 119.71 (15) |
O3—C18—O2 | 125.62 (12) | C4—C3—H3 | 120.1 |
O3—C18—C15 | 117.54 (12) | C5—C4—H4 | 119.7 |
O2—C18—C15 | 116.83 (11) | C3—C4—C5 | 120.53 (15) |
C9—C8—C13 | 118.71 (13) | C3—C4—H4 | 119.7 |
C9—C8—C6 | 120.47 (12) | C3A—O1A—H1AA | 109.5 |
C13—C8—C6 | 120.78 (13) | C3A—C2A—H2A | 108.1 |
C19—C21—H21A | 109.5 | C3A—C2A—C1A | 110.34 (13) |
C19—C21—H21B | 109.5 | C3A—C2A—C4A | 110.75 (14) |
C19—C21—H21C | 109.5 | C1A—C2A—H2A | 108.1 |
H21A—C21—H21B | 109.5 | C4A—C2A—H2A | 108.1 |
H21A—C21—H21C | 109.5 | C4A—C2A—C1A | 111.19 (15) |
H21B—C21—H21C | 109.5 | O1A—C3A—C2A | 110.64 (13) |
N1—C7—C1 | 126.43 (13) | O1A—C3A—H3AA | 109.5 |
N4—C7—N1 | 107.98 (13) | O1A—C3A—H3AB | 109.5 |
N4—C7—C1 | 125.50 (14) | C2A—C3A—H3AA | 109.5 |
C17—C22—H22A | 109.3 | C2A—C3A—H3AB | 109.5 |
C17—C22—H22B | 109.3 | H3AA—C3A—H3AB | 108.1 |
C17—C22—C23 | 111.77 (12) | C2A—C1A—H1AB | 109.5 |
H22A—C22—H22B | 107.9 | C2A—C1A—H1AC | 109.5 |
C23—C22—H22A | 109.3 | C2A—C1A—H1AD | 109.5 |
C23—C22—H22B | 109.3 | H1AB—C1A—H1AC | 109.5 |
C12—C13—C8 | 120.44 (13) | H1AB—C1A—H1AD | 109.5 |
C12—C13—H13 | 119.8 | H1AC—C1A—H1AD | 109.5 |
C8—C13—H13 | 119.8 | C2A—C4A—H4AA | 109.5 |
N5—C14—C11 | 113.39 (11) | C2A—C4A—H4AB | 109.5 |
N5—C14—H14A | 108.9 | C2A—C4A—H4AC | 109.5 |
N5—C14—H14B | 108.9 | H4AA—C4A—H4AB | 109.5 |
C11—C14—H14A | 108.9 | H4AA—C4A—H4AC | 109.5 |
C11—C14—H14B | 108.9 | H4AB—C4A—H4AC | 109.5 |
H14A—C14—H14B | 107.7 | | |
4-(2-Hydroxypropan-2-yl)-2-propyl-1-({4-[2-(1
H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1
H-imidazol-3-ium-5-carboxylate
2-ethoxyethanol monosolvate (Ol-Etox)
top
Crystal data top
C24H26N6O3·C4H10O2 | F(000) = 1144 |
Mr = 536.63 | Dx = 1.266 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 10.25267 (10) Å | Cell parameters from 23615 reflections |
b = 19.21448 (19) Å | θ = 3.9–71.6° |
c = 14.29015 (17) Å | µ = 0.72 mm−1 |
β = 90.1353 (10)° | T = 102 K |
V = 2815.15 (5) Å3 | Block, colourless |
Z = 4 | 0.1 × 0.09 × 0.05 mm |
Data collection top
Agilent SuperNova Dual Source diffractometer with an Eos detector | 5469 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 5006 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.035 |
Detector resolution: 16.4335 pixels mm-1 | θmax = 71.8°, θmin = 3.9° |
ω scans | h = −12→12 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −23→23 |
Tmin = 0.768, Tmax = 1.000 | l = −17→14 |
49601 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.125 | w = 1/[σ2(Fo2) + (0.0513P)2 + 2.2675P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
5469 reflections | Δρmax = 0.37 e Å−3 |
362 parameters | Δρmin = −0.33 e Å−3 |
1 restraint | |
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. |
Refinement. Single crystals of each solvate were selected and analysed using a
SuperNova diffractometer equipped with dual X-ray sources (Cu and Mo), using
Cu radiation and Eos CCD detector. The X-ray tube has been set to operate at
50 kV and 0.8 mA. Diffraction intensities were collected and corrected for
Lorentz, polarization and absorption effects using CrysAlis PRO software
(Agilent, 2012). Because of highly disordered solvent
molecules in crystal
lattices the investigated crystals were kept at low temperatures (100 K)
during data collection. Using Olex2 (Dolomanov et al., 2009), the
structures were solved with the ShelXS (Sheldrick, 2008)
structure solution
program using Direct Methods and refined with the ShelXL (Sheldrick, 2015)
refinement package by Least Squares minimisation. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.60362 (11) | 0.16191 (6) | 0.81750 (8) | 0.0245 (3) | |
H1 | 0.581325 | 0.175342 | 0.869529 | 0.037* | |
O2 | 0.50886 (12) | 0.21671 (7) | 0.96486 (8) | 0.0279 (3) | |
O3 | 0.32340 (11) | 0.26633 (7) | 1.00938 (8) | 0.0265 (3) | |
N5 | 0.22819 (13) | 0.26548 (7) | 0.82093 (9) | 0.0183 (3) | |
O2A | 0.62705 (12) | 0.44438 (7) | 0.89518 (10) | 0.0335 (3) | |
N6 | 0.33551 (13) | 0.24406 (7) | 0.69459 (9) | 0.0191 (3) | |
H6 | 0.354143 | 0.239758 | 0.636228 | 0.023* | |
N1 | −0.23209 (14) | 0.05301 (8) | 0.80254 (10) | 0.0251 (3) | |
C16 | 0.42076 (15) | 0.23136 (8) | 0.76711 (11) | 0.0186 (3) | |
N3 | −0.11680 (16) | −0.02456 (9) | 0.73972 (12) | 0.0359 (4) | |
N4 | −0.13834 (16) | −0.04558 (8) | 0.82944 (12) | 0.0342 (4) | |
C12 | 0.07940 (15) | 0.15755 (9) | 0.91489 (11) | 0.0211 (3) | |
H12 | 0.161867 | 0.146955 | 0.891957 | 0.025* | |
C8 | −0.12309 (15) | 0.11947 (9) | 0.98507 (11) | 0.0216 (3) | |
C9 | −0.16549 (15) | 0.18836 (9) | 0.98551 (11) | 0.0218 (3) | |
H9 | −0.247110 | 0.199215 | 1.009735 | 0.026* | |
C11 | 0.03662 (15) | 0.22613 (8) | 0.91531 (11) | 0.0192 (3) | |
C14 | 0.11802 (15) | 0.28640 (8) | 0.88065 (11) | 0.0199 (3) | |
H14A | 0.062339 | 0.317851 | 0.845571 | 0.024* | |
H14B | 0.151731 | 0.311735 | 0.934208 | 0.024* | |
C15 | 0.35415 (15) | 0.24491 (8) | 0.84856 (11) | 0.0186 (3) | |
C7 | −0.21000 (16) | 0.00399 (9) | 0.86755 (13) | 0.0253 (4) | |
C18 | 0.39868 (15) | 0.24218 (8) | 0.94884 (11) | 0.0200 (3) | |
C19 | 0.56205 (16) | 0.21100 (9) | 0.74868 (11) | 0.0214 (3) | |
C13 | −0.00007 (16) | 0.10471 (9) | 0.94846 (12) | 0.0227 (3) | |
H13 | 0.029025 | 0.058888 | 0.946525 | 0.027* | |
C1 | −0.25209 (16) | 0.00817 (9) | 0.96594 (13) | 0.0251 (4) | |
C22 | 0.10109 (16) | 0.27517 (9) | 0.66954 (12) | 0.0230 (3) | |
H22A | 0.126438 | 0.283006 | 0.605041 | 0.028* | |
H22B | 0.055863 | 0.316407 | 0.691387 | 0.028* | |
C6 | −0.20895 (16) | 0.06329 (9) | 1.02246 (12) | 0.0237 (4) | |
N2 | −0.17305 (15) | 0.03465 (8) | 0.72262 (11) | 0.0310 (3) | |
C17 | 0.22014 (15) | 0.26394 (8) | 0.72761 (11) | 0.0192 (3) | |
C10 | −0.08703 (15) | 0.24087 (9) | 0.95014 (11) | 0.0213 (3) | |
H10 | −0.117361 | 0.286486 | 0.949680 | 0.026* | |
C5 | −0.24548 (18) | 0.06413 (10) | 1.11649 (13) | 0.0303 (4) | |
H5 | −0.216470 | 0.099949 | 1.155039 | 0.036* | |
C23 | 0.00836 (16) | 0.21235 (10) | 0.67430 (12) | 0.0271 (4) | |
H23A | −0.024035 | 0.207835 | 0.737729 | 0.033* | |
H23B | −0.065835 | 0.220904 | 0.633655 | 0.033* | |
C21 | 0.57619 (19) | 0.17429 (11) | 0.65491 (12) | 0.0336 (4) | |
H21A | 0.663929 | 0.157583 | 0.648264 | 0.050* | |
H21B | 0.556868 | 0.206356 | 0.605258 | 0.050* | |
H21C | 0.516702 | 0.135761 | 0.652031 | 0.050* | |
O1A | 0.89444 (15) | 0.41222 (8) | 0.85200 (13) | 0.0499 (4) | |
H1AA | 0.960512 | 0.428626 | 0.828472 | 0.075* | |
C3 | −0.36862 (18) | −0.04103 (10) | 1.09647 (16) | 0.0366 (5) | |
H3 | −0.423043 | −0.075185 | 1.120912 | 0.044* | |
C2 | −0.33204 (17) | −0.04371 (10) | 1.00334 (15) | 0.0313 (4) | |
H2 | −0.360718 | −0.080078 | 0.965602 | 0.038* | |
C24 | 0.0726 (2) | 0.14451 (10) | 0.64571 (14) | 0.0358 (4) | |
H24A | 0.111434 | 0.149803 | 0.585070 | 0.054* | |
H24B | 0.008172 | 0.108277 | 0.643446 | 0.054* | |
H24C | 0.138761 | 0.132507 | 0.690518 | 0.054* | |
C2A | 0.50476 (19) | 0.41650 (10) | 0.92256 (16) | 0.0368 (5) | |
H2AA | 0.473893 | 0.439842 | 0.978474 | 0.044* | |
H2AB | 0.513445 | 0.367262 | 0.936189 | 0.044* | |
C3A | 0.72463 (19) | 0.43084 (11) | 0.96284 (15) | 0.0363 (4) | |
H3AA | 0.728613 | 0.381305 | 0.975644 | 0.044* | |
H3AB | 0.703844 | 0.454756 | 1.020686 | 0.044* | |
C4 | −0.32437 (19) | 0.01235 (11) | 1.15325 (14) | 0.0358 (4) | |
H4 | −0.347552 | 0.013490 | 1.216114 | 0.043* | |
C20 | 0.64705 (18) | 0.27610 (10) | 0.75316 (17) | 0.0373 (5) | |
H20A | 0.638831 | 0.297239 | 0.813732 | 0.056* | |
H20B | 0.619332 | 0.308456 | 0.705942 | 0.056* | |
H20C | 0.736456 | 0.263573 | 0.742626 | 0.056* | |
C1A | 0.4105 (2) | 0.42707 (12) | 0.8444 (2) | 0.0514 (6) | |
H1AB | 0.440365 | 0.402519 | 0.789953 | 0.077* | |
H1AC | 0.404061 | 0.475824 | 0.830403 | 0.077* | |
H1AD | 0.326455 | 0.409686 | 0.862305 | 0.077* | |
C4A | 0.8530 (2) | 0.45542 (12) | 0.92695 (17) | 0.0443 (5) | |
H4AA | 0.845249 | 0.503110 | 0.905397 | 0.053* | |
H4AB | 0.917169 | 0.454168 | 0.976914 | 0.053* | |
H1A | −0.279 (2) | 0.0909 (9) | 0.8072 (16) | 0.038 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0286 (6) | 0.0293 (6) | 0.0156 (6) | 0.0085 (5) | 0.0003 (5) | 0.0019 (5) |
O2 | 0.0266 (6) | 0.0408 (7) | 0.0164 (6) | 0.0088 (5) | −0.0041 (5) | −0.0040 (5) |
O3 | 0.0235 (6) | 0.0424 (7) | 0.0135 (6) | 0.0029 (5) | 0.0007 (4) | −0.0021 (5) |
N5 | 0.0192 (6) | 0.0202 (6) | 0.0154 (6) | 0.0000 (5) | −0.0002 (5) | 0.0000 (5) |
O2A | 0.0294 (7) | 0.0337 (7) | 0.0372 (8) | 0.0007 (5) | 0.0003 (5) | 0.0076 (6) |
N6 | 0.0224 (7) | 0.0236 (7) | 0.0114 (6) | −0.0005 (5) | 0.0002 (5) | 0.0011 (5) |
N1 | 0.0245 (7) | 0.0250 (7) | 0.0257 (8) | 0.0024 (6) | 0.0005 (6) | −0.0031 (6) |
C16 | 0.0218 (8) | 0.0186 (7) | 0.0153 (7) | −0.0016 (6) | −0.0009 (6) | 0.0005 (6) |
N3 | 0.0333 (8) | 0.0369 (9) | 0.0376 (9) | 0.0063 (7) | 0.0016 (7) | −0.0101 (7) |
N4 | 0.0324 (8) | 0.0292 (8) | 0.0411 (10) | 0.0062 (6) | 0.0000 (7) | −0.0057 (7) |
C12 | 0.0192 (7) | 0.0274 (8) | 0.0167 (8) | 0.0037 (6) | 0.0008 (6) | −0.0002 (6) |
C8 | 0.0219 (8) | 0.0254 (8) | 0.0174 (8) | 0.0007 (6) | −0.0016 (6) | 0.0005 (6) |
C9 | 0.0185 (7) | 0.0274 (8) | 0.0196 (8) | 0.0024 (6) | 0.0003 (6) | −0.0035 (6) |
C11 | 0.0204 (7) | 0.0245 (8) | 0.0126 (7) | 0.0001 (6) | −0.0027 (6) | −0.0010 (6) |
C14 | 0.0195 (7) | 0.0225 (8) | 0.0176 (8) | 0.0019 (6) | 0.0014 (6) | −0.0022 (6) |
C15 | 0.0186 (7) | 0.0199 (7) | 0.0172 (8) | −0.0005 (6) | −0.0001 (6) | 0.0001 (6) |
C7 | 0.0217 (8) | 0.0222 (8) | 0.0320 (9) | 0.0004 (6) | −0.0032 (7) | −0.0011 (7) |
C18 | 0.0213 (8) | 0.0229 (8) | 0.0159 (8) | −0.0025 (6) | −0.0004 (6) | −0.0005 (6) |
C19 | 0.0227 (8) | 0.0258 (8) | 0.0158 (8) | 0.0034 (6) | 0.0024 (6) | 0.0037 (6) |
C13 | 0.0234 (8) | 0.0225 (8) | 0.0222 (8) | 0.0039 (6) | −0.0012 (6) | 0.0015 (6) |
C1 | 0.0204 (8) | 0.0236 (8) | 0.0314 (9) | 0.0045 (6) | −0.0008 (7) | 0.0042 (7) |
C22 | 0.0242 (8) | 0.0281 (8) | 0.0167 (8) | 0.0023 (7) | −0.0031 (6) | 0.0016 (6) |
C6 | 0.0199 (8) | 0.0240 (8) | 0.0273 (9) | 0.0044 (6) | 0.0017 (6) | 0.0038 (7) |
N2 | 0.0297 (8) | 0.0356 (8) | 0.0276 (8) | 0.0013 (6) | 0.0019 (6) | −0.0075 (7) |
C17 | 0.0222 (8) | 0.0187 (7) | 0.0166 (8) | −0.0020 (6) | 0.0001 (6) | 0.0019 (6) |
C10 | 0.0214 (8) | 0.0229 (8) | 0.0195 (8) | 0.0032 (6) | −0.0024 (6) | −0.0022 (6) |
C5 | 0.0309 (9) | 0.0304 (9) | 0.0298 (10) | 0.0042 (7) | 0.0065 (7) | 0.0025 (7) |
C23 | 0.0238 (8) | 0.0413 (10) | 0.0162 (8) | −0.0058 (7) | −0.0027 (6) | 0.0025 (7) |
C21 | 0.0351 (10) | 0.0474 (11) | 0.0182 (9) | 0.0163 (8) | 0.0027 (7) | −0.0002 (8) |
O1A | 0.0364 (8) | 0.0359 (8) | 0.0775 (12) | 0.0009 (6) | 0.0197 (8) | 0.0112 (8) |
C3 | 0.0276 (9) | 0.0314 (10) | 0.0509 (13) | 0.0024 (8) | 0.0096 (8) | 0.0155 (9) |
C2 | 0.0247 (9) | 0.0248 (9) | 0.0443 (11) | 0.0013 (7) | −0.0013 (8) | 0.0049 (8) |
C24 | 0.0465 (11) | 0.0321 (10) | 0.0288 (10) | −0.0121 (8) | 0.0051 (8) | −0.0026 (8) |
C2A | 0.0335 (10) | 0.0282 (9) | 0.0486 (12) | 0.0005 (8) | 0.0074 (9) | 0.0021 (9) |
C3A | 0.0374 (10) | 0.0371 (10) | 0.0342 (11) | 0.0033 (8) | −0.0026 (8) | 0.0035 (8) |
C4 | 0.0363 (10) | 0.0376 (10) | 0.0334 (10) | 0.0065 (8) | 0.0129 (8) | 0.0100 (8) |
C20 | 0.0228 (9) | 0.0331 (10) | 0.0560 (13) | −0.0002 (8) | 0.0085 (8) | 0.0054 (9) |
C1A | 0.0350 (11) | 0.0387 (12) | 0.0806 (18) | 0.0005 (9) | −0.0087 (11) | 0.0081 (12) |
C4A | 0.0356 (11) | 0.0404 (12) | 0.0568 (14) | −0.0035 (9) | −0.0070 (10) | 0.0069 (10) |
Geometric parameters (Å, º) top
O1—H1 | 0.8200 | C22—H22A | 0.9700 |
O1—C19 | 1.4271 (19) | C22—H22B | 0.9700 |
O2—C18 | 1.252 (2) | C22—C17 | 1.490 (2) |
O3—C18 | 1.250 (2) | C22—C23 | 1.538 (2) |
N5—C14 | 1.4731 (19) | C6—C5 | 1.396 (3) |
N5—C15 | 1.406 (2) | C10—H10 | 0.9300 |
N5—C17 | 1.336 (2) | C5—H5 | 0.9300 |
O2A—C2A | 1.419 (2) | C5—C4 | 1.386 (3) |
O2A—C3A | 1.414 (2) | C23—H23A | 0.9700 |
N6—H6 | 0.8600 | C23—H23B | 0.9700 |
N6—C16 | 1.376 (2) | C23—C24 | 1.517 (3) |
N6—C17 | 1.331 (2) | C21—H21A | 0.9600 |
N1—C7 | 1.342 (2) | C21—H21B | 0.9600 |
N1—N2 | 1.341 (2) | C21—H21C | 0.9600 |
N1—H1A | 0.874 (16) | O1A—H1AA | 0.8200 |
C16—C15 | 1.376 (2) | O1A—C4A | 1.421 (3) |
C16—C19 | 1.524 (2) | C3—H3 | 0.9300 |
N3—N4 | 1.363 (2) | C3—C2 | 1.385 (3) |
N3—N2 | 1.299 (2) | C3—C4 | 1.384 (3) |
N4—C7 | 1.321 (2) | C2—H2 | 0.9300 |
C12—H12 | 0.9300 | C24—H24A | 0.9600 |
C12—C11 | 1.389 (2) | C24—H24B | 0.9600 |
C12—C13 | 1.388 (2) | C24—H24C | 0.9600 |
C8—C9 | 1.393 (2) | C2A—H2AA | 0.9700 |
C8—C13 | 1.396 (2) | C2A—H2AB | 0.9700 |
C8—C6 | 1.493 (2) | C2A—C1A | 1.489 (3) |
C9—H9 | 0.9300 | C3A—H3AA | 0.9700 |
C9—C10 | 1.387 (2) | C3A—H3AB | 0.9700 |
C11—C14 | 1.512 (2) | C3A—C4A | 1.490 (3) |
C11—C10 | 1.392 (2) | C4—H4 | 0.9300 |
C14—H14A | 0.9700 | C20—H20A | 0.9600 |
C14—H14B | 0.9700 | C20—H20B | 0.9600 |
C15—C18 | 1.504 (2) | C20—H20C | 0.9600 |
C7—C1 | 1.474 (3) | C1A—H1AB | 0.9600 |
C19—C21 | 1.522 (2) | C1A—H1AC | 0.9600 |
C19—C20 | 1.526 (2) | C1A—H1AD | 0.9600 |
C13—H13 | 0.9300 | C4A—H4AA | 0.9700 |
C1—C6 | 1.403 (3) | C4A—H4AB | 0.9700 |
C1—C2 | 1.398 (2) | | |
| | | |
C19—O1—H1 | 109.5 | N6—C17—N5 | 107.90 (14) |
C15—N5—C14 | 128.24 (13) | N6—C17—C22 | 124.88 (14) |
C17—N5—C14 | 122.58 (13) | C9—C10—C11 | 120.79 (15) |
C17—N5—C15 | 109.18 (13) | C9—C10—H10 | 119.6 |
C3A—O2A—C2A | 111.48 (15) | C11—C10—H10 | 119.6 |
C16—N6—H6 | 124.8 | C6—C5—H5 | 119.5 |
C17—N6—H6 | 124.8 | C4—C5—C6 | 120.97 (18) |
C17—N6—C16 | 110.34 (13) | C4—C5—H5 | 119.5 |
C7—N1—H1A | 128.6 (15) | C22—C23—H23A | 108.9 |
N2—N1—C7 | 109.22 (15) | C22—C23—H23B | 108.9 |
N2—N1—H1A | 122.2 (15) | H23A—C23—H23B | 107.8 |
N6—C16—C19 | 121.19 (14) | C24—C23—C22 | 113.19 (14) |
C15—C16—N6 | 106.73 (14) | C24—C23—H23A | 108.9 |
C15—C16—C19 | 131.97 (14) | C24—C23—H23B | 108.9 |
N2—N3—N4 | 111.34 (15) | C19—C21—H21A | 109.5 |
C7—N4—N3 | 105.41 (15) | C19—C21—H21B | 109.5 |
C11—C12—H12 | 119.8 | C19—C21—H21C | 109.5 |
C13—C12—H12 | 119.8 | H21A—C21—H21B | 109.5 |
C13—C12—C11 | 120.45 (15) | H21A—C21—H21C | 109.5 |
C9—C8—C13 | 118.49 (15) | H21B—C21—H21C | 109.5 |
C9—C8—C6 | 120.08 (14) | C4A—O1A—H1AA | 109.5 |
C13—C8—C6 | 121.43 (15) | C2—C3—H3 | 119.9 |
C8—C9—H9 | 119.7 | C4—C3—H3 | 119.9 |
C10—C9—C8 | 120.55 (15) | C4—C3—C2 | 120.13 (18) |
C10—C9—H9 | 119.7 | C1—C2—H2 | 119.9 |
C12—C11—C14 | 123.43 (14) | C3—C2—C1 | 120.10 (18) |
C12—C11—C10 | 118.85 (15) | C3—C2—H2 | 119.9 |
C10—C11—C14 | 117.72 (14) | C23—C24—H24A | 109.5 |
N5—C14—C11 | 113.92 (13) | C23—C24—H24B | 109.5 |
N5—C14—H14A | 108.8 | C23—C24—H24C | 109.5 |
N5—C14—H14B | 108.8 | H24A—C24—H24B | 109.5 |
C11—C14—H14A | 108.8 | H24A—C24—H24C | 109.5 |
C11—C14—H14B | 108.8 | H24B—C24—H24C | 109.5 |
H14A—C14—H14B | 107.7 | O2A—C2A—H2AA | 110.0 |
N5—C15—C18 | 123.64 (14) | O2A—C2A—H2AB | 110.0 |
C16—C15—N5 | 105.84 (13) | O2A—C2A—C1A | 108.27 (18) |
C16—C15—C18 | 130.49 (14) | H2AA—C2A—H2AB | 108.4 |
N1—C7—C1 | 124.95 (15) | C1A—C2A—H2AA | 110.0 |
N4—C7—N1 | 108.28 (16) | C1A—C2A—H2AB | 110.0 |
N4—C7—C1 | 126.65 (16) | O2A—C3A—H3AA | 109.8 |
O2—C18—C15 | 117.38 (14) | O2A—C3A—H3AB | 109.8 |
O3—C18—O2 | 125.23 (15) | O2A—C3A—C4A | 109.30 (17) |
O3—C18—C15 | 117.38 (14) | H3AA—C3A—H3AB | 108.3 |
O1—C19—C16 | 109.45 (12) | C4A—C3A—H3AA | 109.8 |
O1—C19—C21 | 105.75 (13) | C4A—C3A—H3AB | 109.8 |
O1—C19—C20 | 110.08 (14) | C5—C4—H4 | 120.0 |
C16—C19—C20 | 108.99 (14) | C3—C4—C5 | 120.03 (18) |
C21—C19—C16 | 111.33 (14) | C3—C4—H4 | 120.0 |
C21—C19—C20 | 111.19 (15) | C19—C20—H20A | 109.5 |
C12—C13—C8 | 120.84 (15) | C19—C20—H20B | 109.5 |
C12—C13—H13 | 119.6 | C19—C20—H20C | 109.5 |
C8—C13—H13 | 119.6 | H20A—C20—H20B | 109.5 |
C6—C1—C7 | 119.85 (15) | H20A—C20—H20C | 109.5 |
C2—C1—C7 | 119.95 (16) | H20B—C20—H20C | 109.5 |
C2—C1—C6 | 120.18 (17) | C2A—C1A—H1AB | 109.5 |
H22A—C22—H22B | 108.0 | C2A—C1A—H1AC | 109.5 |
C17—C22—H22A | 109.3 | C2A—C1A—H1AD | 109.5 |
C17—C22—H22B | 109.3 | H1AB—C1A—H1AC | 109.5 |
C17—C22—C23 | 111.55 (14) | H1AB—C1A—H1AD | 109.5 |
C23—C22—H22A | 109.3 | H1AC—C1A—H1AD | 109.5 |
C23—C22—H22B | 109.3 | O1A—C4A—C3A | 109.88 (18) |
C1—C6—C8 | 121.69 (15) | O1A—C4A—H4AA | 109.7 |
C5—C6—C8 | 119.73 (16) | O1A—C4A—H4AB | 109.7 |
C5—C6—C1 | 118.56 (16) | C3A—C4A—H4AA | 109.7 |
N3—N2—N1 | 105.75 (15) | C3A—C4A—H4AB | 109.7 |
N5—C17—C22 | 126.95 (14) | H4AA—C4A—H4AB | 108.2 |
4-(2-Hydroxypropan-2-yl)-2-propyl-1-({4-[2-(1
H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1
H-imidazol-3-ium-5-carboxylate
chloroform monosolvate (Ol-Chl)
top
Crystal data top
C24H26N6O3·CHCl3 | F(000) = 1176 |
Mr = 565.87 | Dx = 1.415 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 10.0422 (2) Å | Cell parameters from 6973 reflections |
b = 18.3553 (4) Å | θ = 3.9–72.1° |
c = 14.4134 (3) Å | µ = 3.45 mm−1 |
β = 91.5895 (17)° | T = 100 K |
V = 2655.76 (10) Å3 | Block, colourless |
Z = 4 | 0.1 × 0.05 × 0.05 mm |
Data collection top
Agilent SuperNova Dual Source diffractometer with an Eos detector | 5115 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 4777 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.018 |
Detector resolution: 16.4335 pixels mm-1 | θmax = 72.6°, θmin = 3.9° |
ω scans | h = −12→12 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −22→21 |
Tmin = 0.500, Tmax = 1.000 | l = −17→10 |
10501 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.068 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.187 | w = 1/[σ2(Fo2) + (0.0977P)2 + 6.8312P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.002 |
5115 reflections | Δρmax = 0.99 e Å−3 |
342 parameters | Δρmin = −1.70 e Å−3 |
0 restraints | |
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. |
Refinement. Single crystals of each solvate were selected and analysed using a
SuperNova diffractometer equipped with dual X-ray sources (Cu and Mo), using
Cu radiation and Eos CCD detector. The X-ray tube has been set to operate at
50 kV and 0.8 mA. Diffraction intensities were collected and corrected for
Lorentz, polarization and absorption effects using CrysAlis PRO software
(Agilent, 2012). Because of highly disordered solvent
molecules in crystal
lattices the investigated crystals were kept at low temperatures (100 K)
during data collection. Using Olex2 (Dolomanov et al., 2009), the
structures were solved with the ShelXS (Sheldrick, 2008)
structure solution
program using Direct Methods and refined with the ShelXL (Sheldrick, 2015)
refinement package by Least Squares minimisation. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1A | 0.28099 (10) | 0.06796 (5) | 0.52320 (7) | 0.0396 (3) | |
Cl2A | 0.10358 (12) | −0.04080 (5) | 0.60011 (8) | 0.0496 (3) | |
Cl3A | 0.37726 (19) | −0.07611 (10) | 0.56808 (10) | 0.0915 (7) | |
O3 | −0.29097 (18) | −0.26688 (11) | 1.01341 (12) | 0.0137 (4) | |
O2 | −0.4933 (2) | −0.23652 (13) | 1.05854 (14) | 0.0208 (5) | |
N5 | −0.1938 (2) | −0.26884 (11) | 1.20243 (14) | 0.0073 (4) | |
N6 | −0.3003 (2) | −0.24327 (12) | 1.32647 (14) | 0.0079 (4) | |
H6 | −0.317211 | −0.236275 | 1.383955 | 0.009* | |
O1 | −0.59226 (18) | −0.17429 (10) | 1.19849 (12) | 0.0122 (4) | |
H1 | −0.569209 | −0.190611 | 1.148471 | 0.018* | |
N1 | 0.2844 (2) | −0.04061 (13) | 1.21077 (16) | 0.0148 (5) | |
C11 | −0.0053 (2) | −0.22717 (14) | 1.10698 (17) | 0.0081 (5) | |
C8 | 0.1482 (2) | −0.11352 (14) | 1.03501 (17) | 0.0101 (5) | |
N2 | 0.2555 (3) | −0.01436 (14) | 1.29524 (18) | 0.0226 (6) | |
C13 | 0.0249 (2) | −0.09943 (15) | 1.07418 (18) | 0.0121 (5) | |
H13 | −0.006348 | −0.051809 | 1.076945 | 0.014* | |
C21 | −0.5516 (3) | −0.17321 (18) | 1.35963 (19) | 0.0193 (6) | |
H21A | −0.499361 | −0.129576 | 1.355796 | 0.029* | |
H21B | −0.521486 | −0.201338 | 1.412295 | 0.029* | |
H21C | −0.643614 | −0.160577 | 1.366340 | 0.029* | |
C15 | −0.3250 (2) | −0.25149 (13) | 1.17412 (17) | 0.0075 (5) | |
N4 | 0.2131 (3) | 0.06922 (15) | 1.1899 (2) | 0.0292 (6) | |
C17 | −0.1825 (2) | −0.26367 (14) | 1.29467 (17) | 0.0088 (5) | |
C12 | −0.0511 (2) | −0.15573 (15) | 1.10894 (18) | 0.0115 (5) | |
H12 | −0.133533 | −0.145592 | 1.133810 | 0.014* | |
C14 | −0.0833 (2) | −0.29108 (14) | 1.14417 (17) | 0.0086 (5) | |
H14A | −0.118544 | −0.319504 | 1.092339 | 0.010* | |
H14B | −0.023312 | −0.322122 | 1.180266 | 0.010* | |
C9 | 0.1938 (2) | −0.18526 (14) | 1.03270 (17) | 0.0097 (5) | |
H9 | 0.275005 | −0.195655 | 1.006230 | 0.012* | |
C10 | 0.1188 (2) | −0.24140 (14) | 1.06961 (17) | 0.0092 (5) | |
H10 | 0.151547 | −0.288781 | 1.069382 | 0.011* | |
C18 | −0.3735 (2) | −0.25189 (14) | 1.07371 (17) | 0.0096 (5) | |
C16 | −0.3912 (2) | −0.23504 (13) | 1.25354 (17) | 0.0076 (5) | |
C5 | 0.2551 (3) | −0.05657 (16) | 0.8993 (2) | 0.0179 (6) | |
H5 | 0.223703 | −0.095532 | 0.863749 | 0.021* | |
C1 | 0.2780 (3) | 0.00507 (15) | 1.0463 (2) | 0.0139 (5) | |
C6 | 0.2289 (2) | −0.05429 (15) | 0.99398 (19) | 0.0127 (5) | |
C2 | 0.3498 (3) | 0.06026 (16) | 1.0033 (2) | 0.0195 (6) | |
H2 | 0.381050 | 0.099744 | 1.037949 | 0.023* | |
C7 | 0.2576 (3) | 0.01094 (15) | 1.1470 (2) | 0.0157 (6) | |
C22 | −0.0603 (2) | −0.27585 (15) | 1.35346 (18) | 0.0128 (5) | |
H22A | −0.022742 | −0.322929 | 1.338306 | 0.015* | |
H22B | −0.084569 | −0.277099 | 1.418108 | 0.015* | |
C19 | −0.5364 (2) | −0.21767 (14) | 1.27189 (18) | 0.0102 (5) | |
N3 | 0.2131 (3) | 0.05163 (16) | 1.2818 (2) | 0.0331 (7) | |
C3 | 0.3748 (3) | 0.05656 (17) | 0.9093 (2) | 0.0237 (7) | |
H3 | 0.423375 | 0.093200 | 0.881231 | 0.028* | |
C24 | −0.0019 (4) | −0.14158 (19) | 1.3650 (2) | 0.0294 (7) | |
H24A | −0.077064 | −0.129070 | 1.325544 | 0.044* | |
H24B | 0.068539 | −0.107152 | 1.356060 | 0.044* | |
H24C | −0.027609 | −0.140525 | 1.428630 | 0.044* | |
C23 | 0.0459 (3) | −0.21713 (18) | 1.34094 (19) | 0.0193 (6) | |
H23A | 0.123244 | −0.228836 | 1.379919 | 0.023* | |
H23B | 0.073368 | −0.217486 | 1.276945 | 0.023* | |
C4 | 0.3273 (3) | −0.00168 (18) | 0.8573 (2) | 0.0233 (7) | |
H4 | 0.343731 | −0.004136 | 0.794222 | 0.028* | |
C20 | −0.6108 (3) | −0.29033 (17) | 1.2774 (3) | 0.0263 (7) | |
H20A | −0.703313 | −0.281314 | 1.287969 | 0.039* | |
H20B | −0.573507 | −0.318878 | 1.327471 | 0.039* | |
H20C | −0.602219 | −0.316351 | 1.220054 | 0.039* | |
C1A | 0.2421 (5) | −0.0250 (2) | 0.5292 (3) | 0.0424 (10) | |
H1AA | 0.217894 | −0.041464 | 0.466333 | 0.051* | |
H1A | 0.316 (4) | −0.085 (2) | 1.203 (2) | 0.021 (9)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1A | 0.0400 (5) | 0.0276 (5) | 0.0511 (6) | −0.0071 (4) | 0.0002 (4) | −0.0057 (4) |
Cl2A | 0.0680 (7) | 0.0283 (5) | 0.0525 (6) | −0.0150 (4) | 0.0035 (5) | 0.0018 (4) |
Cl3A | 0.1184 (13) | 0.0935 (11) | 0.0650 (8) | 0.0740 (10) | 0.0454 (9) | 0.0390 (8) |
O3 | 0.0108 (9) | 0.0235 (10) | 0.0067 (9) | −0.0006 (7) | −0.0013 (7) | 0.0000 (7) |
O2 | 0.0123 (9) | 0.0376 (13) | 0.0122 (9) | 0.0093 (9) | −0.0066 (7) | −0.0090 (9) |
N5 | 0.0047 (9) | 0.0101 (10) | 0.0069 (10) | 0.0000 (7) | −0.0017 (7) | 0.0003 (8) |
N6 | 0.0065 (9) | 0.0130 (10) | 0.0041 (9) | 0.0011 (8) | −0.0007 (7) | 0.0006 (8) |
O1 | 0.0116 (8) | 0.0171 (9) | 0.0077 (8) | 0.0063 (7) | −0.0031 (7) | 0.0000 (7) |
N1 | 0.0170 (11) | 0.0114 (12) | 0.0160 (11) | 0.0017 (9) | −0.0028 (9) | −0.0010 (9) |
C11 | 0.0059 (11) | 0.0124 (12) | 0.0059 (11) | 0.0000 (9) | −0.0027 (8) | −0.0003 (9) |
C8 | 0.0079 (11) | 0.0121 (12) | 0.0101 (12) | −0.0003 (9) | −0.0024 (9) | 0.0004 (9) |
N2 | 0.0316 (14) | 0.0185 (13) | 0.0177 (12) | 0.0040 (11) | −0.0017 (10) | −0.0045 (10) |
C13 | 0.0097 (12) | 0.0107 (12) | 0.0158 (13) | 0.0030 (10) | −0.0004 (10) | 0.0006 (10) |
C21 | 0.0164 (13) | 0.0313 (16) | 0.0100 (12) | 0.0113 (12) | −0.0013 (10) | 0.0001 (12) |
C15 | 0.0044 (11) | 0.0091 (11) | 0.0089 (12) | −0.0004 (9) | −0.0032 (9) | 0.0011 (9) |
N4 | 0.0448 (17) | 0.0152 (13) | 0.0273 (15) | 0.0097 (12) | −0.0027 (12) | −0.0021 (11) |
C17 | 0.0072 (11) | 0.0097 (12) | 0.0094 (12) | −0.0011 (9) | −0.0016 (9) | 0.0018 (9) |
C12 | 0.0071 (11) | 0.0157 (13) | 0.0119 (12) | 0.0023 (10) | 0.0009 (9) | −0.0004 (10) |
C14 | 0.0064 (11) | 0.0113 (12) | 0.0081 (11) | 0.0017 (9) | 0.0015 (9) | −0.0004 (9) |
C9 | 0.0059 (11) | 0.0150 (13) | 0.0080 (11) | 0.0013 (9) | −0.0022 (8) | −0.0013 (9) |
C10 | 0.0073 (11) | 0.0108 (12) | 0.0092 (11) | 0.0023 (9) | −0.0030 (9) | −0.0007 (9) |
C18 | 0.0106 (12) | 0.0099 (12) | 0.0082 (12) | −0.0010 (9) | −0.0035 (9) | −0.0008 (9) |
C16 | 0.0065 (11) | 0.0083 (11) | 0.0078 (11) | −0.0020 (9) | −0.0035 (9) | 0.0013 (9) |
C5 | 0.0161 (13) | 0.0175 (14) | 0.0204 (14) | 0.0022 (11) | 0.0036 (11) | 0.0028 (11) |
C1 | 0.0095 (12) | 0.0110 (12) | 0.0211 (14) | 0.0029 (10) | −0.0023 (10) | 0.0033 (10) |
C6 | 0.0076 (11) | 0.0116 (12) | 0.0188 (13) | 0.0027 (9) | 0.0010 (10) | 0.0030 (10) |
C2 | 0.0133 (13) | 0.0121 (13) | 0.0330 (16) | 0.0007 (10) | −0.0020 (11) | 0.0051 (12) |
C7 | 0.0149 (13) | 0.0108 (13) | 0.0210 (14) | −0.0007 (10) | −0.0046 (11) | −0.0003 (10) |
C22 | 0.0078 (11) | 0.0213 (14) | 0.0089 (12) | 0.0027 (10) | −0.0045 (9) | 0.0019 (10) |
C19 | 0.0063 (11) | 0.0129 (12) | 0.0114 (12) | 0.0021 (9) | −0.0005 (9) | 0.0040 (10) |
N3 | 0.0536 (19) | 0.0208 (14) | 0.0248 (14) | 0.0119 (13) | −0.0008 (13) | −0.0059 (11) |
C3 | 0.0143 (13) | 0.0187 (15) | 0.0384 (18) | 0.0015 (11) | 0.0076 (12) | 0.0133 (13) |
C24 | 0.0331 (18) | 0.0299 (18) | 0.0251 (16) | −0.0159 (14) | −0.0023 (13) | −0.0036 (13) |
C23 | 0.0084 (12) | 0.0385 (18) | 0.0107 (13) | −0.0072 (12) | −0.0049 (10) | 0.0036 (12) |
C4 | 0.0222 (15) | 0.0244 (16) | 0.0239 (15) | 0.0053 (12) | 0.0111 (12) | 0.0092 (12) |
C20 | 0.0095 (13) | 0.0173 (15) | 0.052 (2) | −0.0023 (11) | 0.0067 (13) | 0.0089 (14) |
C1A | 0.073 (3) | 0.0260 (19) | 0.0281 (19) | −0.0014 (19) | −0.0005 (18) | −0.0012 (15) |
Geometric parameters (Å, º) top
Cl1A—C1A | 1.753 (4) | C17—C22 | 1.489 (3) |
Cl2A—C1A | 1.772 (5) | C12—H12 | 0.9300 |
Cl3A—C1A | 1.730 (5) | C14—H14A | 0.9700 |
O3—C18 | 1.248 (3) | C14—H14B | 0.9700 |
O2—C18 | 1.249 (3) | C9—H9 | 0.9300 |
N5—C15 | 1.405 (3) | C9—C10 | 1.391 (4) |
N5—C17 | 1.335 (3) | C10—H10 | 0.9300 |
N5—C14 | 1.468 (3) | C16—C19 | 1.524 (3) |
N6—H6 | 0.8600 | C5—H5 | 0.9300 |
N6—C17 | 1.334 (3) | C5—C6 | 1.397 (4) |
N6—C16 | 1.381 (3) | C5—C4 | 1.389 (4) |
O1—H1 | 0.8200 | C1—C6 | 1.407 (4) |
O1—C19 | 1.426 (3) | C1—C2 | 1.399 (4) |
N1—N2 | 1.348 (4) | C1—C7 | 1.474 (4) |
N1—C7 | 1.342 (4) | C2—H2 | 0.9300 |
N1—H1A | 0.88 (4) | C2—C3 | 1.386 (5) |
C11—C12 | 1.390 (4) | C22—H22A | 0.9700 |
C11—C14 | 1.517 (3) | C22—H22B | 0.9700 |
C11—C10 | 1.396 (3) | C22—C23 | 1.530 (4) |
C8—C13 | 1.399 (4) | C19—C20 | 1.532 (4) |
C8—C9 | 1.395 (4) | C3—H3 | 0.9300 |
C8—C6 | 1.488 (4) | C3—C4 | 1.382 (5) |
N2—N3 | 1.297 (4) | C24—H24A | 0.9600 |
C13—H13 | 0.9300 | C24—H24B | 0.9600 |
C13—C12 | 1.387 (4) | C24—H24C | 0.9600 |
C21—H21A | 0.9600 | C24—C23 | 1.511 (5) |
C21—H21B | 0.9600 | C23—H23A | 0.9700 |
C21—H21C | 0.9600 | C23—H23B | 0.9700 |
C21—C19 | 1.516 (4) | C4—H4 | 0.9300 |
C15—C18 | 1.514 (3) | C20—H20A | 0.9600 |
C15—C16 | 1.373 (4) | C20—H20B | 0.9600 |
N4—C7 | 1.320 (4) | C20—H20C | 0.9600 |
N4—N3 | 1.364 (4) | C1A—H1AA | 0.9800 |
| | | |
C15—N5—C14 | 127.9 (2) | C4—C5—C6 | 121.2 (3) |
C17—N5—C15 | 109.1 (2) | C6—C1—C7 | 121.9 (2) |
C17—N5—C14 | 123.0 (2) | C2—C1—C6 | 120.0 (3) |
C17—N6—H6 | 125.0 | C2—C1—C7 | 118.1 (3) |
C17—N6—C16 | 110.0 (2) | C5—C6—C8 | 119.0 (2) |
C16—N6—H6 | 125.0 | C5—C6—C1 | 118.3 (3) |
C19—O1—H1 | 109.5 | C1—C6—C8 | 122.6 (2) |
N2—N1—H1A | 122 (2) | C1—C2—H2 | 119.7 |
C7—N1—N2 | 108.9 (2) | C3—C2—C1 | 120.5 (3) |
C7—N1—H1A | 129 (2) | C3—C2—H2 | 119.7 |
C12—C11—C14 | 123.2 (2) | N1—C7—C1 | 126.3 (3) |
C12—C11—C10 | 118.9 (2) | N4—C7—N1 | 108.3 (3) |
C10—C11—C14 | 117.8 (2) | N4—C7—C1 | 125.3 (3) |
C13—C8—C6 | 121.5 (2) | C17—C22—H22A | 108.9 |
C9—C8—C13 | 118.6 (2) | C17—C22—H22B | 108.9 |
C9—C8—C6 | 119.9 (2) | C17—C22—C23 | 113.1 (2) |
N3—N2—N1 | 106.1 (2) | H22A—C22—H22B | 107.8 |
C8—C13—H13 | 119.7 | C23—C22—H22A | 108.9 |
C12—C13—C8 | 120.7 (2) | C23—C22—H22B | 108.9 |
C12—C13—H13 | 119.7 | O1—C19—C21 | 105.8 (2) |
H21A—C21—H21B | 109.5 | O1—C19—C16 | 110.3 (2) |
H21A—C21—H21C | 109.5 | O1—C19—C20 | 110.0 (2) |
H21B—C21—H21C | 109.5 | C21—C19—C16 | 112.1 (2) |
C19—C21—H21A | 109.5 | C21—C19—C20 | 111.4 (2) |
C19—C21—H21B | 109.5 | C16—C19—C20 | 107.3 (2) |
C19—C21—H21C | 109.5 | N2—N3—N4 | 111.0 (3) |
N5—C15—C18 | 123.4 (2) | C2—C3—H3 | 120.1 |
C16—C15—N5 | 106.2 (2) | C4—C3—C2 | 119.9 (3) |
C16—C15—C18 | 130.4 (2) | C4—C3—H3 | 120.1 |
C7—N4—N3 | 105.8 (3) | H24A—C24—H24B | 109.5 |
N5—C17—C22 | 127.0 (2) | H24A—C24—H24C | 109.5 |
N6—C17—N5 | 108.1 (2) | H24B—C24—H24C | 109.5 |
N6—C17—C22 | 124.9 (2) | C23—C24—H24A | 109.5 |
C11—C12—H12 | 119.7 | C23—C24—H24B | 109.5 |
C13—C12—C11 | 120.7 (2) | C23—C24—H24C | 109.5 |
C13—C12—H12 | 119.7 | C22—C23—H23A | 109.0 |
N5—C14—C11 | 113.1 (2) | C22—C23—H23B | 109.0 |
N5—C14—H14A | 109.0 | C24—C23—C22 | 113.1 (2) |
N5—C14—H14B | 109.0 | C24—C23—H23A | 109.0 |
C11—C14—H14A | 109.0 | C24—C23—H23B | 109.0 |
C11—C14—H14B | 109.0 | H23A—C23—H23B | 107.8 |
H14A—C14—H14B | 107.8 | C5—C4—H4 | 120.0 |
C8—C9—H9 | 119.7 | C3—C4—C5 | 120.1 (3) |
C10—C9—C8 | 120.6 (2) | C3—C4—H4 | 120.0 |
C10—C9—H9 | 119.7 | C19—C20—H20A | 109.5 |
C11—C10—H10 | 119.7 | C19—C20—H20B | 109.5 |
C9—C10—C11 | 120.5 (2) | C19—C20—H20C | 109.5 |
C9—C10—H10 | 119.7 | H20A—C20—H20B | 109.5 |
O3—C18—O2 | 125.7 (2) | H20A—C20—H20C | 109.5 |
O3—C18—C15 | 117.7 (2) | H20B—C20—H20C | 109.5 |
O2—C18—C15 | 116.7 (2) | Cl1A—C1A—Cl2A | 111.6 (2) |
N6—C16—C19 | 120.4 (2) | Cl1A—C1A—H1AA | 107.7 |
C15—C16—N6 | 106.6 (2) | Cl2A—C1A—H1AA | 107.7 |
C15—C16—C19 | 132.7 (2) | Cl3A—C1A—Cl1A | 111.7 (3) |
C6—C5—H5 | 119.4 | Cl3A—C1A—Cl2A | 110.2 (2) |
C4—C5—H5 | 119.4 | Cl3A—C1A—H1AA | 107.7 |
4-(2-Hydroxypropan-2-yl)-2-propyl-1-({4-[2-(1
H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1
H-imidazol-3-ium-5-carboxylate
acetonitrile monosolvate (Ol-Acn)
top
Crystal data top
C24H26N6O3·C2H3N | F(000) = 1032 |
Mr = 487.56 | Dx = 1.274 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 9.92522 (7) Å | Cell parameters from 25587 reflections |
b = 17.86566 (12) Å | θ = 4.5–71.4° |
c = 14.34306 (10) Å | µ = 0.71 mm−1 |
β = 91.4370 (6)° | T = 110 K |
V = 2542.52 (3) Å3 | Needle, colourless |
Z = 4 | 0.1 × 0.02 × 0.01 mm |
Data collection top
Agilent SuperNova Dual Source diffractometer with an Eos detector | 4937 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 4602 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.038 |
Detector resolution: 16.4335 pixels mm-1 | θmax = 71.7°, θmin = 4.5° |
ω scans | h = −12→11 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −21→21 |
Tmin = 0.289, Tmax = 1.000 | l = −17→17 |
43452 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.050 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.133 | w = 1/[σ2(Fo2) + (0.0664P)2 + 1.6749P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
4937 reflections | Δρmax = 0.47 e Å−3 |
347 parameters | Δρmin = −0.71 e Å−3 |
29 restraints | |
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. |
Refinement. Single crystals of each solvate were selected and analysed using a
SuperNova diffractometer equipped with dual X-ray sources (Cu and Mo), using
Cu radiation and Eos CCD detector. The X-ray tube has been set to operate at
50 kV and 0.8 mA. Diffraction intensities were collected and corrected for
Lorentz, polarization and absorption effects using CrysAlis PRO software
(Agilent, 2012). Because of highly disordered solvent
molecules in crystal
lattices the investigated crystals were kept at low temperatures (100 K)
during data collection. Using Olex2 (Dolomanov et al., 2009), the
structures were solved with the ShelXS (Sheldrick, 2008)
structure solution
program using Direct Methods and refined with the ShelXL (Sheldrick, 2015)
refinement package by Least Squares minimisation. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.90689 (11) | 0.17622 (6) | 0.20891 (7) | 0.0194 (2) | |
H1 | 0.926166 | 0.198076 | 0.160776 | 0.029* | |
O3 | 1.21197 (12) | 0.27756 (8) | 0.03063 (8) | 0.0302 (3) | |
N6 | 1.20504 (12) | 0.23466 (7) | 0.34207 (8) | 0.0170 (3) | |
H6 | 1.187811 | 0.224391 | 0.399120 | 0.020* | |
N5 | 1.31393 (12) | 0.26543 (7) | 0.21972 (8) | 0.0157 (3) | |
O2 | 1.00561 (12) | 0.25223 (8) | 0.07649 (8) | 0.0327 (3) | |
C9 | 1.70037 (14) | 0.18371 (8) | 0.04021 (10) | 0.0164 (3) | |
H9 | 1.781864 | 0.194792 | 0.012721 | 0.020* | |
C10 | 1.62789 (15) | 0.24025 (8) | 0.08197 (10) | 0.0163 (3) | |
H10 | 1.662643 | 0.288583 | 0.084094 | 0.020* | |
C16 | 1.11200 (15) | 0.23328 (8) | 0.26916 (10) | 0.0159 (3) | |
C11 | 1.50347 (14) | 0.22544 (8) | 0.12082 (10) | 0.0153 (3) | |
C14 | 1.42692 (15) | 0.28981 (8) | 0.16281 (10) | 0.0175 (3) | |
H14A | 1.488576 | 0.319351 | 0.201302 | 0.021* | |
H14B | 1.392546 | 0.321730 | 0.112952 | 0.021* | |
C12 | 1.45439 (15) | 0.15252 (9) | 0.11852 (10) | 0.0190 (3) | |
H12 | 1.371050 | 0.141954 | 0.143662 | 0.023* | |
C13 | 1.52867 (15) | 0.09537 (9) | 0.07904 (11) | 0.0203 (3) | |
H13 | 1.495711 | 0.046643 | 0.079287 | 0.024* | |
C8 | 1.65252 (15) | 0.11052 (8) | 0.03896 (10) | 0.0176 (3) | |
C15 | 1.17969 (15) | 0.25341 (8) | 0.19052 (10) | 0.0160 (3) | |
C18 | 1.12875 (16) | 0.26239 (9) | 0.09122 (10) | 0.0194 (3) | |
N1 | 1.79072 (15) | 0.03609 (8) | 0.21193 (10) | 0.0272 (3) | |
C19 | 0.96525 (15) | 0.21467 (9) | 0.28696 (10) | 0.0186 (3) | |
C23 | 1.53900 (17) | 0.18804 (11) | 0.36270 (12) | 0.0290 (4) | |
H23A | 1.569796 | 0.184367 | 0.299217 | 0.035* | |
H23B | 1.617807 | 0.193777 | 0.403448 | 0.035* | |
C5 | 1.75653 (17) | 0.05224 (10) | −0.09981 (12) | 0.0279 (4) | |
H5 | 1.722597 | 0.091919 | −0.135190 | 0.033* | |
C1 | 1.78385 (16) | −0.01091 (9) | 0.04734 (12) | 0.0250 (4) | |
C6 | 1.73274 (15) | 0.04975 (9) | −0.00460 (11) | 0.0213 (3) | |
C22 | 1.44986 (16) | 0.25805 (10) | 0.37108 (11) | 0.0223 (3) | |
H22A | 1.424747 | 0.264026 | 0.435574 | 0.027* | |
H22B | 1.501531 | 0.301770 | 0.353772 | 0.027* | |
C7 | 1.76619 (18) | −0.01707 (9) | 0.14821 (13) | 0.0280 (4) | |
N2 | 1.76726 (19) | 0.00850 (9) | 0.29715 (12) | 0.0406 (4) | |
N4 | 1.7280 (2) | −0.07822 (9) | 0.19200 (13) | 0.0469 (5) | |
C17 | 1.32560 (15) | 0.25422 (8) | 0.31130 (10) | 0.0171 (3) | |
C21 | 0.95370 (18) | 0.16176 (11) | 0.36946 (11) | 0.0288 (4) | |
H21A | 0.861413 | 0.146833 | 0.375484 | 0.043* | |
H21B | 0.983973 | 0.186751 | 0.425420 | 0.043* | |
H21C | 1.008429 | 0.118318 | 0.359556 | 0.043* | |
C3 | 1.87947 (19) | −0.06329 (11) | −0.09116 (16) | 0.0390 (5) | |
H3 | 1.928513 | −0.100699 | −0.120001 | 0.047* | |
C2 | 1.85617 (18) | −0.06748 (10) | 0.00284 (15) | 0.0338 (4) | |
H2 | 1.888618 | −0.108120 | 0.037130 | 0.041* | |
C4 | 1.83000 (19) | −0.00348 (11) | −0.14282 (14) | 0.0370 (5) | |
H4 | 1.845981 | −0.000613 | −0.206335 | 0.044* | |
N3 | 1.7300 (3) | −0.06029 (10) | 0.28431 (14) | 0.0559 (6) | |
C24 | 1.4676 (2) | 0.11625 (12) | 0.38747 (16) | 0.0439 (5) | |
H24A | 1.392545 | 0.108550 | 0.345026 | 0.066* | |
H24B | 1.435801 | 0.119610 | 0.449993 | 0.066* | |
H24C | 1.529103 | 0.074998 | 0.383111 | 0.066* | |
C20 | 0.88951 (17) | 0.28742 (10) | 0.30324 (15) | 0.0332 (4) | |
H20A | 0.895812 | 0.318858 | 0.249242 | 0.050* | |
H20B | 0.928446 | 0.312712 | 0.356476 | 0.050* | |
H20C | 0.796532 | 0.276579 | 0.314272 | 0.050* | |
N1A | 1.2974 (7) | −0.0694 (3) | 0.3504 (5) | 0.163 (2) | |
C2A | 1.2437 (11) | −0.0377 (5) | 0.4077 (6) | 0.114 (2) | 0.6 |
C1AB | 1.109 (3) | −0.0504 (16) | 0.4489 (19) | 0.272 (14) | 0.4 |
H1AA | 1.044370 | −0.018594 | 0.417367 | 0.408* | 0.4 |
H1AB | 1.166569 | −0.020622 | 0.488726 | 0.408* | 0.4 |
H1AC | 1.062258 | −0.086521 | 0.485753 | 0.408* | 0.4 |
H1A | 1.818 (2) | 0.0804 (10) | 0.2057 (16) | 0.040 (6)* | |
C2B | 1.1876 (14) | −0.0881 (7) | 0.3820 (9) | 0.114 (2) | 0.4 |
C1AA | 1.1780 (9) | 0.0083 (6) | 0.4845 (6) | 0.153 (5) | 0.6 |
H1AD | 1.081846 | 0.003386 | 0.479075 | 0.230* | 0.6 |
H1AE | 1.202474 | 0.059998 | 0.477970 | 0.230* | 0.6 |
H1AF | 1.208671 | −0.009663 | 0.544401 | 0.230* | 0.6 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0206 (5) | 0.0229 (5) | 0.0145 (5) | −0.0039 (4) | −0.0024 (4) | −0.0010 (4) |
O3 | 0.0221 (6) | 0.0547 (8) | 0.0139 (5) | 0.0003 (5) | 0.0011 (4) | 0.0018 (5) |
N6 | 0.0167 (6) | 0.0230 (6) | 0.0113 (6) | 0.0005 (5) | 0.0002 (5) | −0.0018 (5) |
N5 | 0.0142 (6) | 0.0190 (6) | 0.0141 (6) | 0.0012 (5) | 0.0004 (5) | −0.0031 (5) |
O2 | 0.0223 (6) | 0.0536 (8) | 0.0219 (6) | −0.0095 (6) | −0.0070 (5) | 0.0134 (5) |
C9 | 0.0132 (7) | 0.0220 (7) | 0.0140 (6) | −0.0008 (5) | −0.0003 (5) | 0.0010 (5) |
C10 | 0.0161 (7) | 0.0172 (7) | 0.0156 (7) | −0.0017 (5) | −0.0014 (5) | 0.0009 (5) |
C16 | 0.0155 (7) | 0.0173 (7) | 0.0148 (7) | 0.0024 (5) | −0.0007 (5) | −0.0032 (5) |
C11 | 0.0147 (7) | 0.0199 (7) | 0.0111 (6) | 0.0010 (5) | −0.0017 (5) | −0.0006 (5) |
C14 | 0.0157 (7) | 0.0191 (7) | 0.0177 (7) | −0.0016 (6) | 0.0024 (5) | −0.0012 (6) |
C12 | 0.0152 (7) | 0.0225 (8) | 0.0194 (7) | −0.0027 (6) | 0.0034 (5) | −0.0017 (6) |
C13 | 0.0190 (7) | 0.0184 (7) | 0.0235 (8) | −0.0037 (6) | 0.0022 (6) | −0.0029 (6) |
C8 | 0.0157 (7) | 0.0201 (7) | 0.0169 (7) | 0.0007 (6) | −0.0002 (5) | −0.0019 (6) |
C15 | 0.0147 (7) | 0.0176 (7) | 0.0156 (7) | 0.0024 (5) | −0.0007 (5) | −0.0025 (5) |
C18 | 0.0204 (8) | 0.0228 (8) | 0.0148 (7) | 0.0019 (6) | −0.0019 (6) | −0.0003 (6) |
N1 | 0.0328 (8) | 0.0182 (7) | 0.0304 (8) | −0.0041 (6) | −0.0016 (6) | 0.0029 (6) |
C19 | 0.0153 (7) | 0.0236 (8) | 0.0168 (7) | −0.0017 (6) | 0.0012 (5) | −0.0055 (6) |
C23 | 0.0201 (8) | 0.0466 (10) | 0.0199 (8) | 0.0099 (7) | −0.0039 (6) | −0.0051 (7) |
C5 | 0.0255 (8) | 0.0281 (9) | 0.0304 (9) | −0.0068 (7) | 0.0081 (7) | −0.0079 (7) |
C1 | 0.0189 (7) | 0.0184 (8) | 0.0378 (9) | −0.0032 (6) | −0.0001 (6) | −0.0073 (7) |
C6 | 0.0145 (7) | 0.0206 (7) | 0.0290 (8) | −0.0041 (6) | 0.0036 (6) | −0.0071 (6) |
C22 | 0.0177 (7) | 0.0326 (9) | 0.0164 (7) | −0.0010 (6) | −0.0028 (6) | −0.0039 (6) |
C7 | 0.0284 (9) | 0.0163 (7) | 0.0391 (10) | −0.0008 (6) | −0.0042 (7) | −0.0010 (7) |
N2 | 0.0596 (11) | 0.0288 (8) | 0.0333 (9) | −0.0104 (8) | −0.0021 (8) | 0.0077 (7) |
N4 | 0.0722 (13) | 0.0231 (8) | 0.0453 (10) | −0.0127 (8) | −0.0040 (9) | 0.0042 (7) |
C17 | 0.0166 (7) | 0.0199 (7) | 0.0149 (7) | 0.0016 (5) | −0.0004 (5) | −0.0036 (5) |
C21 | 0.0262 (8) | 0.0428 (10) | 0.0173 (8) | −0.0119 (7) | 0.0002 (6) | 0.0005 (7) |
C3 | 0.0255 (9) | 0.0296 (9) | 0.0625 (13) | −0.0046 (7) | 0.0140 (9) | −0.0245 (9) |
C2 | 0.0224 (8) | 0.0205 (8) | 0.0583 (12) | −0.0004 (7) | −0.0002 (8) | −0.0119 (8) |
C4 | 0.0327 (10) | 0.0391 (10) | 0.0401 (10) | −0.0119 (8) | 0.0165 (8) | −0.0198 (8) |
N3 | 0.0928 (16) | 0.0301 (9) | 0.0445 (11) | −0.0189 (10) | −0.0023 (10) | 0.0098 (8) |
C24 | 0.0493 (12) | 0.0385 (11) | 0.0438 (11) | 0.0150 (9) | −0.0009 (9) | 0.0041 (9) |
C20 | 0.0189 (8) | 0.0294 (9) | 0.0516 (11) | 0.0005 (7) | 0.0077 (7) | −0.0159 (8) |
N1A | 0.185 (5) | 0.117 (4) | 0.185 (5) | −0.024 (3) | −0.031 (4) | 0.030 (3) |
C2A | 0.148 (6) | 0.100 (5) | 0.093 (4) | 0.020 (4) | 0.016 (4) | −0.014 (3) |
C1AB | 0.26 (2) | 0.29 (2) | 0.27 (2) | −0.024 (16) | 0.047 (16) | 0.029 (16) |
C2B | 0.148 (6) | 0.100 (5) | 0.093 (4) | 0.020 (4) | 0.016 (4) | −0.014 (3) |
C1AA | 0.127 (7) | 0.184 (9) | 0.147 (8) | −0.038 (7) | −0.044 (6) | 0.129 (8) |
Geometric parameters (Å, º) top
O1—C19 | 1.4241 (17) | N1—N2 | 1.344 (2) |
O3—C18 | 1.244 (2) | C19—C21 | 1.521 (2) |
N6—C16 | 1.3778 (19) | C19—C20 | 1.522 (2) |
N6—C17 | 1.332 (2) | C23—C22 | 1.538 (2) |
N5—C14 | 1.4696 (18) | C23—C24 | 1.512 (3) |
N5—C15 | 1.4031 (19) | C5—C6 | 1.392 (2) |
N5—C17 | 1.3309 (19) | C5—C4 | 1.388 (2) |
O2—C18 | 1.248 (2) | C1—C6 | 1.403 (2) |
C9—C10 | 1.385 (2) | C1—C7 | 1.466 (3) |
C9—C8 | 1.391 (2) | C1—C2 | 1.403 (2) |
C10—C11 | 1.393 (2) | C22—C17 | 1.486 (2) |
C16—C15 | 1.375 (2) | C7—N4 | 1.321 (2) |
C16—C19 | 1.522 (2) | N2—N3 | 1.295 (2) |
C11—C14 | 1.512 (2) | N4—N3 | 1.362 (3) |
C11—C12 | 1.391 (2) | C3—C2 | 1.376 (3) |
C12—C13 | 1.388 (2) | C3—C4 | 1.383 (3) |
C13—C8 | 1.397 (2) | N1A—C2A | 1.141 (8) |
C8—C6 | 1.493 (2) | N1A—C2B | 1.236 (13) |
C15—C18 | 1.508 (2) | C2A—C1AA | 1.532 (12) |
N1—C7 | 1.336 (2) | C1AB—C2B | 1.422 (17) |
| | | |
C17—N6—C16 | 110.11 (12) | O1—C19—C20 | 109.86 (13) |
C15—N5—C14 | 127.72 (12) | C16—C19—C20 | 108.51 (13) |
C17—N5—C14 | 122.95 (12) | C21—C19—C16 | 110.94 (13) |
C17—N5—C15 | 109.27 (12) | C21—C19—C20 | 111.35 (14) |
C10—C9—C8 | 120.68 (13) | C24—C23—C22 | 113.42 (15) |
C9—C10—C11 | 120.65 (14) | C4—C5—C6 | 121.13 (18) |
N6—C16—C19 | 120.18 (13) | C6—C1—C7 | 122.11 (15) |
C15—C16—N6 | 106.61 (13) | C2—C1—C6 | 119.83 (17) |
C15—C16—C19 | 133.17 (13) | C2—C1—C7 | 118.05 (16) |
C10—C11—C14 | 118.32 (13) | C5—C6—C8 | 119.51 (15) |
C12—C11—C10 | 118.81 (13) | C5—C6—C1 | 118.53 (15) |
C12—C11—C14 | 122.87 (13) | C1—C6—C8 | 121.95 (14) |
N5—C14—C11 | 113.21 (12) | C17—C22—C23 | 112.84 (13) |
C13—C12—C11 | 120.61 (14) | N1—C7—C1 | 126.70 (15) |
C12—C13—C8 | 120.48 (14) | N4—C7—N1 | 108.19 (17) |
C9—C8—C13 | 118.73 (13) | N4—C7—C1 | 125.06 (16) |
C9—C8—C6 | 120.24 (13) | N3—N2—N1 | 105.90 (16) |
C13—C8—C6 | 121.03 (13) | C7—N4—N3 | 105.70 (16) |
N5—C15—C18 | 123.98 (13) | N6—C17—C22 | 124.08 (13) |
C16—C15—N5 | 105.96 (12) | N5—C17—N6 | 108.04 (13) |
C16—C15—C18 | 130.05 (14) | N5—C17—C22 | 127.81 (14) |
O3—C18—O2 | 125.30 (14) | C2—C3—C4 | 120.06 (16) |
O3—C18—C15 | 118.06 (14) | C3—C2—C1 | 120.49 (18) |
O2—C18—C15 | 116.62 (13) | C3—C4—C5 | 119.96 (18) |
C7—N1—N2 | 109.20 (15) | N2—N3—N4 | 111.01 (16) |
O1—C19—C16 | 110.22 (11) | N1A—C2A—C1AA | 176.7 (11) |
O1—C19—C21 | 105.95 (12) | N1A—C2B—C1AB | 128.6 (17) |
Molecular interaction energies (kJ mol-1) for selected contacts topCrystal | Interaction pair | Contact | Eele | Epol | Edisp | Erep | Etot |
Ol-MeOH | Olmersartan–methanol | O1A—H1AA···O2 | -38.2 | -8.4 | -9.55 | 17.6 | -38.5 |
| Ol–Ol | N6—H6···O3 | -99.2 | -35.2 | -45.8 | 68.0 | -112.2 |
| Ol–Ol | N1—H1A···O1 | -75.5 | -19.3 | -37.1 | 42.6 | -89.2 |
Ol-EtOH | Olmersartan–ethanol | O1A—H1AA···N3 | -10.0 | -3.0 | -16.0 | 13.3 | -15.7 |
| Ol–Ol | N6—H6···O3 | -107.3 | -37.4 | -48.0 | 70.4 | -122.3 |
| Ol–Ol | N1—H1A···O1 | -81.0 | -20.3 | -39.3 | 48.5 | -92.1 |
Ol-IsoProp | Olmersartan–isopropanol | O1A—H1AA···N3 | -10.4 | -3.9 | -21.6 | 13.5 | -22.3 |
| Ol–Ol | N6—H6···O3 | -100.5 | -35.0 | -53.0 | 60.3 | -128.2 |
| Ol–Ol | N1—H1A···O1 | -79.5 | -19.8 | -39.0 | 46.9 | -91.4 |
Ol-IsoBut | Olmersartan–isobutanol | O1A—H1AA···N4 | -40.1 | -7.7 | -33.2 | 35.8 | -45.2 |
| Ol–Ol | N6—H6···O3 | -110.5 | -37.2 | -42.9 | 69.0 | -121.6 |
| Ol–Ol | N1—H1A···O1 | -81.6 | -20.4 | -39.2 | 48.2 | -93.0 |
Ol-Ethox | Olmersartan–ethoxyethanol | O1A—H1AA···N4 | -36.7 | -7.3 | -14.3 | 30.5 | -27.8 |
| Ol–Ol | N6—H6···O3 | -111.3 | -37.0 | -46.3 | 69.2 | -127.4 |
| Ol–Ol | N1—H1A···O1 | -83.8 | -22.5 | -33.0 | 48.2 | -91.1 |
Ol-Chl | Olmersartan–chloroform | C20—H20A···Cl1 | -12.5 | -3.6 | -13.9 | 8.1 | -21.9 |
| Ol–Ol | N6—H6···O3 | -106.9 | -35.8 | -46.9 | 65.2 | -124.4 |
| Ol–Ol | N1—H1A···O1 | -68.8 | -17.7 | -37.3 | 41.2 | -82.6 |
Ol-Acn | Olmersatan–acetonitrile | C1A—H1AB···N2 | -18.0 | -2.5 | -8.5 | 10.7 | -18.3 |
| Ol–Ol | N6—H6···O3 | -101.6 | -35.6 | -46.0 | 62.0 | -121.2 |
| Ol–Ol | N1—H1A···O1 | -77.5 | -20.0 | -37.8 | 45.4 | -89.9 |
Abbreviation: Ol is olmesartan. |
Crystal energies (kJ mol-1) topEcoul is the Coulombic term,
Epol the polarization term,
Edisp the dispersion term,
Erep the repulsion term and
Elatt the total energy term. |
Structure | Ecoul | Epol | Edisp | Erep | Elatt |
Ol | -109.3 | -48.6 | -202.2 | 111.0 | -249.1 |
Ol-MeOH | -63.2 | -33.0 | -129.3 | 75.3 | -150.3 |
Ol-EtOH | -61.5 | -35.5 | -135.1 | 76.4 | -155.6 |
Ol-IsoProp | -60.1 | -39.4 | -140.6 | 75.4 | -164.7 |
Ol-Ethox | -68.3 | -36.3 | -148.0 | 83.3 | -169.3 |
Ol-Chl | -55.5 | -29.4 | -144.6 | 74.0 | -155.5 |
Ol-Acn | -58.8 | -32.0 | -120.7 | 60.6 | -150.8 |
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