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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229622002984/dv3017sup1.cif
Contains datablocks Ol-MeOH, Ol-EtOH, Ol-IsoProp, Ol-IsoBut, Ol-Etox, Ol-Chl, Ol-Acn, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229622002984/dv3017Ol-MeOHsup2.hkl
Contains datablock Ol-MeOH

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229622002984/dv3017Ol-EtOHsup3.hkl
Contains datablock Ol-EtOH

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229622002984/dv3017Ol-IsoPropsup4.hkl
Contains datablock Ol-IsoProp

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229622002984/dv3017Ol-IsoButsup5.hkl
Contains datablock Ol-IsoBut

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229622002984/dv3017Ol-Etoxsup6.hkl
Contains datablock Ol-Etox

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229622002984/dv3017Ol-Chlsup7.hkl
Contains datablock Ol-Chl

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229622002984/dv3017Ol-Acnsup8.hkl
Contains datablock Ol-Acn

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229622002984/dv3017sup9.pdf
Additional tables and figures

CCDC references: 2144598; 2144597; 2144596; 2144595; 2144594; 2144593; 2144592

Computing details top

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-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazol-3-ium-5-carboxylate methanol monosolvate (Ol-MeOH) top
Crystal data top
C24H26N6O3·CH4OF(000) = 1016
Mr = 478.55Dx = 1.253 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 9.94703 (14) ÅCell parameters from 12956 reflections
b = 17.8262 (2) Åθ = 5.8–71.5°
c = 14.3100 (2) ŵ = 0.71 mm1
β = 92.0063 (14)°T = 99 K
V = 2535.85 (7) Å3Plate, colourless
Z = 40.1 × 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 Source4601 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.022
Detector resolution: 16.4335 pixels mm-1θmax = 71.7°, θmin = 4.5°
ω scansh = 1212
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
k = 2121
Tmin = 0.762, Tmax = 1.000l = 1217
19216 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.054H 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 reflectionsΔρmax = 0.48 e Å3
326 parametersΔρmin = 0.73 e Å3
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
xyzUiso*/Ueq
O10.08903 (11)0.67348 (7)0.21763 (8)0.0170 (3)
H10.0724450.6976980.1706970.026*
O30.21302 (12)0.77326 (8)0.04154 (8)0.0233 (3)
N60.20984 (13)0.73007 (8)0.35306 (9)0.0143 (3)
H60.1933180.7194720.4101490.017*
N50.31731 (13)0.76119 (7)0.23076 (9)0.0129 (3)
O20.00419 (13)0.75961 (9)0.09008 (9)0.0305 (3)
C150.18216 (15)0.75015 (9)0.20160 (11)0.0133 (3)
C90.70199 (15)0.68372 (9)0.04910 (11)0.0142 (3)
H90.7833580.6955940.0226350.017*
N10.79226 (16)0.53253 (9)0.21501 (11)0.0230 (3)
C130.53036 (17)0.59383 (10)0.08289 (12)0.0179 (4)
H130.4975000.5449990.0806430.021*
C110.50521 (16)0.72291 (9)0.13045 (11)0.0133 (3)
C160.11599 (16)0.72949 (9)0.28017 (11)0.0133 (3)
C120.45616 (16)0.64979 (10)0.12467 (12)0.0168 (3)
H120.3731190.6383730.1489850.020*
C100.62951 (16)0.73920 (9)0.09310 (11)0.0142 (3)
H100.6640850.7875820.0977190.017*
C140.42889 (16)0.78657 (9)0.17393 (11)0.0151 (3)
H14A0.4908150.8159140.2129590.018*
H14B0.3934140.8190650.1245980.018*
C80.65379 (16)0.61027 (9)0.04425 (11)0.0152 (3)
C180.13036 (17)0.76192 (9)0.10288 (11)0.0155 (3)
C170.33015 (16)0.74944 (9)0.32251 (12)0.0147 (3)
C60.73429 (16)0.55068 (10)0.00141 (13)0.0188 (4)
C50.75874 (18)0.55605 (11)0.09646 (14)0.0245 (4)
H50.7259400.5971360.1301900.029*
C220.45465 (17)0.75251 (10)0.38277 (12)0.0189 (4)
H22A0.4302750.7587780.4473430.023*
H22B0.5070940.7959090.3654700.023*
C190.02932 (16)0.70935 (9)0.29785 (12)0.0162 (3)
C230.54184 (18)0.68159 (11)0.37469 (13)0.0242 (4)
H23A0.5725120.6778000.3112550.029*
H23B0.6206240.6865830.4161110.029*
C70.76671 (19)0.48034 (10)0.14915 (14)0.0247 (4)
C20.85541 (19)0.43261 (11)0.00161 (16)0.0296 (4)
H20.8868590.3906800.0342900.035*
C10.78422 (17)0.48850 (10)0.04826 (14)0.0218 (4)
N20.7680 (2)0.50345 (10)0.29921 (13)0.0363 (4)
N30.7294 (3)0.43495 (12)0.28413 (15)0.0505 (6)
C200.10632 (19)0.78073 (12)0.32024 (17)0.0328 (5)
H20A0.1065660.8137670.2672470.049*
H20B0.0636450.8052020.3731660.049*
H20C0.1972240.7681700.3343860.049*
C30.8789 (2)0.43957 (12)0.09229 (17)0.0341 (5)
H30.9270980.4026200.1224890.041*
N40.7270 (2)0.41865 (10)0.19123 (14)0.0421 (5)
C40.8313 (2)0.50110 (12)0.14183 (15)0.0319 (5)
H40.8475730.5057750.2051650.038*
C210.0370 (2)0.65276 (12)0.37716 (13)0.0276 (4)
H21A0.1283790.6364020.3825240.041*
H21B0.0064910.6758010.4347130.041*
H21C0.0189470.6103920.3642690.041*
C240.4685 (2)0.61003 (13)0.39874 (18)0.0396 (5)
H24A0.4340460.6142200.4603680.059*
H24B0.5295500.5684190.3967800.059*
H24C0.3952710.6021260.3543100.059*
O1A0.1684 (3)0.39116 (15)0.3783 (3)0.0921 (9)
H1AA0.1082450.3615000.3900150.138*
C1A0.1490 (6)0.4557 (2)0.4244 (3)0.1074 (17)
H1AB0.1934900.4958260.3931250.161*
H1AC0.1852550.4512230.4871660.161*
H1AD0.0543990.4661100.4257240.161*
H1A0.823 (2)0.5777 (10)0.2142 (18)0.036 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0179 (6)0.0203 (6)0.0127 (6)0.0044 (5)0.0022 (4)0.0004 (5)
O30.0190 (6)0.0392 (8)0.0119 (6)0.0024 (5)0.0013 (5)0.0005 (5)
N60.0146 (6)0.0199 (7)0.0084 (6)0.0003 (5)0.0004 (5)0.0011 (5)
N50.0116 (6)0.0162 (7)0.0110 (6)0.0004 (5)0.0007 (5)0.0020 (5)
O20.0183 (6)0.0509 (9)0.0216 (7)0.0095 (6)0.0071 (5)0.0162 (6)
C150.0110 (7)0.0145 (7)0.0144 (8)0.0011 (6)0.0015 (6)0.0026 (6)
C90.0110 (7)0.0201 (8)0.0116 (7)0.0009 (6)0.0002 (6)0.0007 (6)
N10.0274 (8)0.0172 (7)0.0241 (8)0.0052 (6)0.0029 (6)0.0018 (6)
C130.0162 (8)0.0170 (8)0.0204 (9)0.0030 (6)0.0013 (6)0.0029 (6)
C110.0124 (7)0.0185 (8)0.0090 (7)0.0009 (6)0.0013 (6)0.0006 (6)
C160.0139 (7)0.0138 (7)0.0119 (8)0.0012 (6)0.0005 (6)0.0032 (6)
C120.0130 (7)0.0209 (8)0.0167 (8)0.0028 (6)0.0028 (6)0.0017 (6)
C100.0137 (7)0.0165 (8)0.0121 (8)0.0020 (6)0.0021 (6)0.0014 (6)
C140.0139 (7)0.0171 (8)0.0144 (8)0.0018 (6)0.0028 (6)0.0015 (6)
C80.0130 (7)0.0192 (8)0.0133 (8)0.0007 (6)0.0010 (6)0.0017 (6)
C180.0166 (8)0.0170 (8)0.0128 (8)0.0004 (6)0.0019 (6)0.0004 (6)
C170.0146 (8)0.0170 (8)0.0125 (8)0.0009 (6)0.0001 (6)0.0033 (6)
C60.0123 (7)0.0192 (8)0.0248 (9)0.0041 (6)0.0024 (6)0.0066 (7)
C50.0216 (9)0.0267 (9)0.0257 (10)0.0068 (7)0.0070 (7)0.0067 (8)
C220.0148 (8)0.0287 (9)0.0129 (8)0.0013 (7)0.0026 (6)0.0024 (7)
C190.0136 (8)0.0199 (8)0.0151 (8)0.0030 (6)0.0019 (6)0.0055 (6)
C230.0177 (8)0.0387 (11)0.0160 (8)0.0060 (7)0.0024 (6)0.0028 (8)
C70.0245 (9)0.0160 (8)0.0331 (10)0.0023 (7)0.0051 (8)0.0008 (7)
C20.0190 (9)0.0185 (9)0.0511 (13)0.0011 (7)0.0012 (8)0.0097 (9)
C10.0149 (8)0.0179 (8)0.0324 (10)0.0032 (6)0.0007 (7)0.0070 (7)
N20.0523 (11)0.0282 (9)0.0280 (9)0.0144 (8)0.0031 (8)0.0061 (7)
N30.0831 (16)0.0311 (10)0.0371 (11)0.0249 (10)0.0031 (10)0.0076 (8)
C200.0167 (9)0.0299 (10)0.0522 (13)0.0019 (8)0.0094 (8)0.0180 (9)
C30.0219 (9)0.0293 (10)0.0519 (13)0.0053 (8)0.0121 (9)0.0232 (10)
N40.0661 (14)0.0234 (9)0.0362 (10)0.0167 (9)0.0048 (9)0.0035 (8)
C40.0278 (10)0.0360 (11)0.0327 (11)0.0099 (8)0.0137 (8)0.0166 (9)
C210.0266 (9)0.0414 (11)0.0148 (9)0.0158 (8)0.0001 (7)0.0016 (8)
C240.0406 (12)0.0337 (12)0.0445 (13)0.0107 (9)0.0008 (10)0.0062 (10)
O1A0.0680 (16)0.0613 (15)0.149 (3)0.0112 (12)0.0309 (16)0.0264 (16)
C1A0.190 (5)0.048 (2)0.086 (3)0.011 (3)0.038 (3)0.0010 (19)
Geometric parameters (Å, º) top
O1—H10.8200C5—C41.391 (3)
O1—C191.4254 (19)C22—H22A0.9700
O3—C181.240 (2)C22—H22B0.9700
N6—H60.8600C22—C231.540 (3)
N6—C161.375 (2)C19—C201.525 (2)
N6—C171.334 (2)C19—C211.522 (3)
N5—C151.407 (2)C23—H23A0.9700
N5—C141.470 (2)C23—H23B0.9700
N5—C171.331 (2)C23—C241.515 (3)
O2—C181.263 (2)C7—C11.468 (3)
C15—C161.373 (2)C7—N41.321 (3)
C15—C181.501 (2)C2—H20.9300
C9—H90.9300C2—C11.405 (3)
C9—C101.388 (2)C2—C31.378 (3)
C9—C81.395 (2)N2—N31.296 (3)
N1—C71.342 (2)N3—N41.360 (3)
N1—N21.341 (2)C20—H20A0.9600
N1—H1A0.860 (17)C20—H20B0.9600
C13—H130.9300C20—H20C0.9600
C13—C121.389 (2)C3—H30.9300
C13—C81.395 (2)C3—C41.381 (3)
C11—C121.393 (2)C4—H40.9300
C11—C101.395 (2)C21—H21A0.9600
C11—C141.511 (2)C21—H21B0.9600
C16—C191.519 (2)C21—H21C0.9600
C12—H120.9300C24—H24A0.9600
C10—H100.9300C24—H24B0.9600
C14—H14A0.9700C24—H24C0.9600
C14—H14B0.9700O1A—H1AA0.8200
C8—C61.494 (2)O1A—C1A1.343 (4)
C17—C221.485 (2)C1A—H1AB0.9600
C6—C51.393 (3)C1A—H1AC0.9600
C6—C11.398 (3)C1A—H1AD0.9600
C5—H50.9300
C19—O1—H1109.5C23—C22—H22B109.0
C16—N6—H6124.9O1—C19—C16110.11 (13)
C17—N6—H6124.9O1—C19—C20110.20 (15)
C17—N6—C16110.27 (14)O1—C19—C21105.83 (13)
C15—N5—C14127.65 (13)C16—C19—C20109.00 (14)
C17—N5—C15109.15 (13)C16—C19—C21110.72 (14)
C17—N5—C14123.08 (13)C21—C19—C20110.95 (16)
N5—C15—C18123.52 (14)C22—C23—H23A108.9
C16—C15—N5105.96 (14)C22—C23—H23B108.9
C16—C15—C18130.50 (14)H23A—C23—H23B107.7
C10—C9—H9119.7C24—C23—C22113.39 (16)
C10—C9—C8120.55 (14)C24—C23—H23A108.9
C8—C9—H9119.7C24—C23—H23B108.9
C7—N1—H1A134.3 (17)N1—C7—C1126.58 (17)
N2—N1—C7109.11 (16)N4—C7—N1108.02 (18)
N2—N1—H1A116.6 (17)N4—C7—C1125.36 (18)
C12—C13—H13119.7C1—C2—H2119.8
C12—C13—C8120.54 (15)C3—C2—H2119.8
C8—C13—H13119.7C3—C2—C1120.3 (2)
C12—C11—C10119.03 (15)C6—C1—C7121.76 (16)
C12—C11—C14123.16 (14)C6—C1—C2119.78 (18)
C10—C11—C14117.79 (14)C2—C1—C7118.45 (18)
N6—C16—C19120.00 (14)N3—N2—N1106.03 (17)
C15—C16—N6106.67 (14)N2—N3—N4111.04 (18)
C15—C16—C19133.32 (15)C19—C20—H20A109.5
C13—C12—C11120.49 (15)C19—C20—H20B109.5
C13—C12—H12119.8C19—C20—H20C109.5
C11—C12—H12119.8H20A—C20—H20B109.5
C9—C10—C11120.47 (15)H20A—C20—H20C109.5
C9—C10—H10119.8H20B—C20—H20C109.5
C11—C10—H10119.8C2—C3—H3119.8
N5—C14—C11113.36 (13)C2—C3—C4120.36 (18)
N5—C14—H14A108.9C4—C3—H3119.8
N5—C14—H14B108.9C7—N4—N3105.80 (17)
C11—C14—H14A108.9C5—C4—H4120.2
C11—C14—H14B108.9C3—C4—C5119.6 (2)
H14A—C14—H14B107.7C3—C4—H4120.2
C9—C8—C13118.88 (15)C19—C21—H21A109.5
C9—C8—C6120.02 (14)C19—C21—H21B109.5
C13—C8—C6121.10 (15)C19—C21—H21C109.5
O3—C18—O2125.66 (16)H21A—C21—H21B109.5
O3—C18—C15118.33 (15)H21A—C21—H21C109.5
O2—C18—C15116.01 (15)H21B—C21—H21C109.5
N6—C17—C22123.97 (15)C23—C24—H24A109.5
N5—C17—N6107.92 (14)C23—C24—H24B109.5
N5—C17—C22128.03 (15)C23—C24—H24C109.5
C5—C6—C8119.51 (16)H24A—C24—H24B109.5
C5—C6—C1118.65 (17)H24A—C24—H24C109.5
C1—C6—C8121.83 (16)H24B—C24—H24C109.5
C6—C5—H5119.4C1A—O1A—H1AA109.5
C4—C5—C6121.23 (19)O1A—C1A—H1AB109.5
C4—C5—H5119.4O1A—C1A—H1AC109.5
C17—C22—H22A109.0O1A—C1A—H1AD109.5
C17—C22—H22B109.0H1AB—C1A—H1AC109.5
C17—C22—C23112.74 (14)H1AB—C1A—H1AD109.5
H22A—C22—H22B107.8H1AC—C1A—H1AD109.5
C23—C22—H22A109.0
4-(2-Hydroxypropan-2-yl)-2-propyl-1-({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazol-3-ium-5-carboxylate ethanol monosolvate (Ol-EtOH) top
Crystal data top
C24H26N6O3·C2H6OF(000) = 1048
Mr = 492.57Dx = 1.282 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 9.7816 (3) ÅCell parameters from 8672 reflections
b = 18.3758 (5) Åθ = 3.9–71.5°
c = 14.1998 (4) ŵ = 0.72 mm1
β = 91.029 (3)°T = 100 K
V = 2551.93 (12) Å3Plate, colourless
Z = 40.09 × 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 Source4318 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.026
Detector resolution: 16.4335 pixels mm-1θmax = 71.8°, θmin = 3.9°
ω scansh = 1211
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
k = 2221
Tmin = 0.664, Tmax = 1.000l = 1217
14146 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.058H 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 reflectionsΔρmax = 0.72 e Å3
335 parametersΔρmin = 0.70 e Å3
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
xyzUiso*/Ueq
O20.00151 (14)0.23927 (8)0.39924 (10)0.0212 (3)
O30.20612 (14)0.27871 (9)0.44191 (10)0.0249 (4)
O10.08597 (14)0.15891 (8)0.26463 (9)0.0210 (3)
H10.0727650.1802970.3143270.031*
N60.19828 (16)0.23065 (9)0.12936 (11)0.0170 (4)
H60.1799190.2213520.0715920.020*
N50.30981 (16)0.26154 (9)0.25274 (11)0.0155 (3)
C120.44340 (19)0.15043 (11)0.36141 (13)0.0173 (4)
H120.3571450.1414060.3375090.021*
C90.69796 (18)0.17740 (11)0.43706 (13)0.0152 (4)
H90.7821620.1870920.4637520.018*
C100.62751 (19)0.23272 (10)0.39281 (13)0.0148 (4)
H100.6660580.2788950.3886200.018*
C150.17444 (19)0.24734 (10)0.28287 (13)0.0152 (4)
C170.3204 (2)0.25096 (11)0.16024 (14)0.0173 (4)
N10.7605 (2)0.03376 (10)0.25966 (13)0.0258 (4)
C110.49938 (18)0.21998 (10)0.35445 (13)0.0146 (4)
C130.5151 (2)0.09457 (11)0.40364 (14)0.0188 (4)
H130.4774280.0481480.4065850.023*
C180.12382 (19)0.25595 (10)0.38254 (14)0.0161 (4)
C140.42613 (19)0.28356 (11)0.31049 (13)0.0161 (4)
H14A0.4906550.3106420.2714410.019*
H14B0.3934240.3157690.3600980.019*
C210.0524 (2)0.15682 (12)0.09983 (14)0.0237 (5)
H21A0.1439350.1384480.0954810.035*
H21B0.0308280.1856070.0451410.035*
H21C0.0104650.1168360.1034450.035*
C70.7255 (2)0.01552 (12)0.32536 (16)0.0267 (5)
C160.10595 (19)0.22675 (10)0.20339 (13)0.0149 (4)
C80.64378 (19)0.10740 (11)0.44192 (13)0.0167 (4)
C10.7636 (2)0.01289 (11)0.42512 (16)0.0228 (4)
C190.04113 (19)0.20355 (11)0.18745 (13)0.0172 (4)
C230.5289 (2)0.18372 (13)0.10332 (15)0.0244 (5)
H23A0.5603190.1763840.1670250.029*
H23B0.6089520.1885730.0625000.029*
C220.4461 (2)0.25476 (12)0.09992 (14)0.0207 (4)
H22A0.4207290.2644570.0354030.025*
H22B0.5027300.2947400.1208710.025*
C60.72504 (19)0.04665 (11)0.48199 (14)0.0189 (4)
C50.7640 (2)0.04763 (12)0.57569 (16)0.0246 (5)
H50.7387420.0865340.6141070.030*
N20.7041 (3)0.01500 (12)0.17711 (15)0.0407 (5)
C30.8780 (2)0.06768 (13)0.5558 (2)0.0351 (6)
H30.9295530.1054240.5805160.042*
C20.8388 (2)0.06990 (12)0.46297 (19)0.0305 (5)
H20.8625930.1096140.4255320.037*
C240.4487 (3)0.11728 (14)0.07347 (19)0.0359 (6)
H24A0.4136100.1249510.0115560.054*
H24B0.5076560.0754990.0728230.054*
H24C0.3741450.1093100.1171150.054*
C200.1303 (2)0.27169 (12)0.18099 (17)0.0254 (5)
H20A0.1258630.2984670.2389050.038*
H20B0.0978530.3016550.1299350.038*
H20C0.2232770.2576960.1700860.038*
N40.6477 (3)0.06542 (12)0.28500 (16)0.0460 (6)
C40.8405 (2)0.00913 (14)0.61229 (18)0.0336 (6)
H40.8666350.0078580.6749100.040*
N30.6346 (3)0.04411 (13)0.19327 (17)0.0560 (8)
O1A0.3183 (3)0.41712 (15)0.3267 (2)0.0702 (7)
H1AA0.3947590.4354140.3295070.105*
C1A0.0874 (4)0.4319 (2)0.3722 (3)0.0716 (10)
H1AB0.0623600.4355030.3067180.107*
H1AC0.0285820.4625420.4083930.107*
H1AD0.0781410.3824020.3926340.107*
C2A0.2303 (4)0.4555 (3)0.3860 (4)0.0842 (13)
H2AA0.2371800.5071760.3729170.101*
H2AB0.2580940.4476300.4510890.101*
H1A0.809 (3)0.0725 (12)0.262 (2)0.034 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0179 (7)0.0296 (8)0.0161 (7)0.0035 (6)0.0035 (5)0.0035 (6)
O30.0185 (7)0.0438 (9)0.0124 (7)0.0027 (6)0.0003 (6)0.0035 (6)
O10.0232 (7)0.0261 (8)0.0137 (7)0.0078 (6)0.0003 (6)0.0011 (6)
N60.0164 (8)0.0237 (9)0.0109 (8)0.0004 (6)0.0002 (6)0.0019 (6)
N50.0130 (7)0.0201 (8)0.0136 (8)0.0004 (6)0.0006 (6)0.0029 (6)
C120.0135 (9)0.0229 (10)0.0154 (9)0.0029 (7)0.0008 (7)0.0001 (7)
C90.0126 (8)0.0218 (10)0.0112 (8)0.0012 (7)0.0015 (7)0.0014 (7)
C100.0149 (9)0.0174 (9)0.0118 (9)0.0027 (7)0.0030 (7)0.0010 (7)
C150.0139 (9)0.0166 (9)0.0151 (10)0.0006 (7)0.0008 (7)0.0019 (7)
C170.0162 (9)0.0221 (10)0.0135 (9)0.0002 (7)0.0003 (7)0.0039 (7)
N10.0337 (10)0.0197 (9)0.0240 (9)0.0048 (8)0.0018 (8)0.0021 (7)
C110.0138 (9)0.0201 (10)0.0097 (9)0.0006 (7)0.0019 (7)0.0002 (7)
C130.0179 (9)0.0197 (10)0.0189 (10)0.0048 (7)0.0009 (7)0.0021 (8)
C180.0165 (9)0.0174 (9)0.0144 (9)0.0023 (7)0.0001 (7)0.0015 (7)
C140.0147 (9)0.0193 (9)0.0145 (9)0.0020 (7)0.0022 (7)0.0012 (7)
C210.0235 (10)0.0317 (12)0.0158 (10)0.0071 (9)0.0013 (8)0.0004 (8)
C70.0335 (12)0.0176 (10)0.0288 (12)0.0019 (9)0.0043 (9)0.0017 (9)
C160.0151 (9)0.0173 (9)0.0122 (9)0.0019 (7)0.0005 (7)0.0026 (7)
C80.0155 (9)0.0206 (10)0.0141 (9)0.0002 (7)0.0016 (7)0.0010 (7)
C10.0197 (10)0.0194 (10)0.0293 (11)0.0038 (8)0.0012 (8)0.0057 (8)
C190.0151 (9)0.0222 (10)0.0142 (9)0.0017 (7)0.0002 (7)0.0028 (7)
C230.0160 (9)0.0401 (13)0.0170 (10)0.0043 (9)0.0014 (8)0.0038 (9)
C220.0158 (9)0.0338 (12)0.0125 (9)0.0012 (8)0.0022 (7)0.0031 (8)
C60.0153 (9)0.0188 (10)0.0229 (10)0.0041 (7)0.0014 (7)0.0056 (8)
C50.0229 (10)0.0257 (11)0.0253 (11)0.0063 (8)0.0050 (8)0.0056 (9)
N20.0658 (15)0.0313 (11)0.0251 (10)0.0156 (10)0.0028 (10)0.0039 (9)
C30.0230 (11)0.0268 (12)0.0557 (16)0.0025 (9)0.0081 (10)0.0202 (11)
C20.0253 (11)0.0192 (11)0.0471 (15)0.0006 (9)0.0028 (10)0.0083 (10)
C240.0336 (13)0.0365 (14)0.0378 (14)0.0068 (10)0.0043 (10)0.0041 (11)
C200.0167 (10)0.0281 (11)0.0316 (12)0.0020 (8)0.0061 (8)0.0022 (9)
N40.0754 (17)0.0280 (11)0.0347 (12)0.0199 (11)0.0085 (11)0.0004 (9)
C40.0280 (11)0.0381 (13)0.0351 (13)0.0102 (10)0.0130 (10)0.0172 (11)
N30.100 (2)0.0355 (13)0.0330 (12)0.0290 (13)0.0143 (13)0.0002 (10)
O1A0.0647 (16)0.0664 (16)0.0800 (18)0.0069 (13)0.0138 (14)0.0104 (13)
C1A0.076 (3)0.068 (2)0.072 (2)0.002 (2)0.016 (2)0.008 (2)
C2A0.079 (3)0.076 (3)0.099 (3)0.019 (2)0.019 (2)0.035 (2)
Geometric parameters (Å, º) top
O2—C181.253 (2)C13—C81.400 (3)
O3—C181.248 (2)C21—C191.517 (3)
O1—C191.431 (2)C7—C11.472 (3)
N6—C171.333 (3)C7—N41.329 (3)
N6—C161.375 (3)C16—C191.521 (3)
N5—C151.409 (2)C8—C61.489 (3)
N5—C171.330 (3)C1—C61.407 (3)
N5—C141.471 (2)C1—C21.393 (3)
C12—C111.393 (3)C19—C201.530 (3)
C12—C131.386 (3)C23—C221.537 (3)
C9—C101.385 (3)C23—C241.516 (3)
C9—C81.393 (3)C6—C51.391 (3)
C10—C111.395 (3)C5—C41.390 (3)
C15—C181.499 (3)N2—N31.299 (3)
C15—C161.376 (3)C3—C21.380 (4)
C17—C221.487 (3)C3—C41.387 (4)
N1—C71.340 (3)N4—N31.368 (3)
N1—N21.349 (3)O1A—C2A1.405 (5)
C11—C141.511 (3)C1A—C2A1.473 (6)
C17—N6—C16110.07 (16)C15—C16—C19132.44 (17)
C15—N5—C14127.87 (16)C9—C8—C13118.71 (18)
C17—N5—C15109.22 (16)C9—C8—C6120.40 (17)
C17—N5—C14122.91 (16)C13—C8—C6120.79 (18)
C13—C12—C11120.58 (17)C6—C1—C7120.51 (19)
C10—C9—C8120.56 (17)C2—C1—C7119.4 (2)
C9—C10—C11120.77 (18)C2—C1—C6120.1 (2)
N5—C15—C18124.05 (17)O1—C19—C21106.12 (16)
C16—C15—N5105.70 (16)O1—C19—C16108.92 (15)
C16—C15—C18130.23 (17)O1—C19—C20110.34 (16)
N6—C17—C22124.06 (18)C21—C19—C16111.30 (16)
N5—C17—N6108.14 (17)C21—C19—C20111.35 (17)
N5—C17—C22127.65 (17)C16—C19—C20108.76 (16)
C7—N1—N2109.22 (19)C24—C23—C22113.56 (17)
C12—C11—C10118.74 (17)C17—C22—C23111.87 (17)
C12—C11—C14123.36 (16)C1—C6—C8120.20 (18)
C10—C11—C14117.86 (17)C5—C6—C8120.87 (19)
C12—C13—C8120.60 (18)C5—C6—C1118.93 (19)
O2—C18—C15116.79 (17)C4—C5—C6120.4 (2)
O3—C18—O2125.39 (18)N3—N2—N1106.3 (2)
O3—C18—C15117.82 (17)C2—C3—C4120.0 (2)
N5—C14—C11113.26 (16)C3—C2—C1120.3 (2)
N1—C7—C1125.6 (2)C7—N4—N3106.1 (2)
N4—C7—N1107.9 (2)C3—C4—C5120.3 (2)
N4—C7—C1126.5 (2)N2—N3—N4110.5 (2)
N6—C16—C15106.85 (16)O1A—C2A—C1A111.3 (3)
N6—C16—C19120.71 (17)
4-(2-Hydroxypropan-2-yl)-2-propyl-1-({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazol-3-ium-5-carboxylate isopropanol monosolvate (Ol-IsoProp) top
Crystal data top
C24H26N6O3·C3H8OF(000) = 1080
Mr = 506.60Dx = 1.292 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 9.76826 (15) ÅCell parameters from 9444 reflections
b = 18.4810 (3) Åθ = 4.5–71.6°
c = 14.42279 (19) ŵ = 0.72 mm1
β = 90.7205 (13)°T = 102 K
V = 2603.49 (6) Å3Needle, colourless
Z = 40.1 × 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 Source4590 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.021
Detector resolution: 16.4335 pixels mm-1θmax = 71.8°, θmin = 3.9°
ω scansh = 1111
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
k = 1922
Tmin = 0.882, Tmax = 1.000l = 1717
17119 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.0598P)2 + 1.5357P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
5025 reflectionsΔρmax = 0.44 e Å3
345 parametersΔρmin = 0.31 e Å3
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
xyzUiso*/Ueq
O30.70456 (10)0.22752 (6)0.04285 (7)0.0217 (2)
O20.49687 (10)0.25938 (6)0.09015 (7)0.0209 (2)
O10.41152 (11)0.33762 (6)0.22560 (7)0.0215 (2)
H10.4280270.3178970.1760580.032*
N60.69619 (12)0.26039 (6)0.35459 (8)0.0158 (2)
H60.6781490.2679070.4119960.019*
N50.80642 (12)0.23239 (6)0.23091 (8)0.0150 (2)
C170.81746 (14)0.23941 (7)0.32274 (9)0.0164 (3)
C160.60387 (14)0.26830 (7)0.28212 (9)0.0152 (3)
C91.19586 (14)0.32133 (8)0.05290 (9)0.0166 (3)
H91.2805640.3125710.0263890.020*
N11.25083 (14)0.46063 (7)0.23430 (9)0.0226 (3)
C150.67193 (14)0.24946 (7)0.20280 (9)0.0153 (3)
C180.62102 (14)0.24489 (7)0.10362 (9)0.0156 (3)
C110.99571 (14)0.27623 (7)0.13092 (9)0.0154 (3)
C190.45808 (14)0.29264 (7)0.30022 (9)0.0173 (3)
C120.93979 (14)0.34562 (8)0.12766 (9)0.0180 (3)
H120.8531090.3538030.1514660.022*
C220.94335 (14)0.23319 (8)0.38130 (10)0.0192 (3)
H22A0.9986810.1932830.3593360.023*
H22B0.9181340.2229980.4448160.023*
C81.14163 (14)0.39113 (8)0.05155 (9)0.0167 (3)
C11.25951 (15)0.51108 (8)0.07383 (10)0.0205 (3)
C101.12470 (14)0.26483 (7)0.09340 (9)0.0162 (3)
H101.1634710.2188930.0955290.019*
C51.26767 (15)0.45415 (8)0.07599 (10)0.0227 (3)
H51.2444670.4163810.1157890.027*
C140.92241 (14)0.21197 (7)0.17226 (9)0.0165 (3)
H14A0.8891710.1811790.1223840.020*
H14B0.9872720.1840760.2090870.020*
C61.22416 (14)0.45280 (8)0.01555 (10)0.0184 (3)
N41.13994 (17)0.56033 (8)0.21235 (10)0.0336 (3)
O1A1.19649 (15)0.08233 (8)0.19033 (11)0.0458 (3)
H1AA1.1184860.0659390.1903040.069*
C231.02750 (15)0.30363 (8)0.37822 (10)0.0219 (3)
H23A1.1068220.2986370.4188580.026*
H23B1.0602210.3108130.3156710.026*
C131.01209 (14)0.40250 (8)0.08931 (10)0.0187 (3)
H130.9742000.4486610.0886530.022*
C21.33652 (16)0.56880 (8)0.04023 (12)0.0258 (3)
H21.3585010.6074030.0790110.031*
C71.21801 (16)0.51144 (8)0.17169 (10)0.0221 (3)
C31.38009 (16)0.56871 (9)0.05035 (12)0.0286 (4)
H31.4324670.6068780.0724260.034*
C210.45069 (16)0.33925 (9)0.38706 (10)0.0242 (3)
H21A0.5151250.3782850.3826970.036*
H21B0.4723620.3103000.4405300.036*
H21C0.3599330.3585420.3927110.036*
N31.12500 (18)0.53700 (8)0.30149 (10)0.0390 (4)
C41.34568 (16)0.51169 (9)0.10832 (11)0.0284 (4)
H41.3749380.5118110.1694350.034*
C240.94659 (18)0.36985 (9)0.40724 (12)0.0306 (4)
H24A0.8763170.3796000.3618090.046*
H24B1.0068550.4107540.4119680.046*
H24C0.9054380.3610680.4662760.046*
N21.19240 (16)0.47718 (8)0.31519 (10)0.0324 (3)
C200.36737 (16)0.22560 (9)0.30834 (13)0.0284 (4)
H20A0.2753140.2401600.3215630.043*
H20B0.4014230.1953180.3575520.043*
H20C0.3683900.1992140.2510210.043*
C2A1.2838 (2)0.03478 (10)0.14016 (12)0.0355 (4)
H2A1.2821950.0130530.1694480.043*
C1A1.4280 (2)0.06532 (11)0.14775 (15)0.0447 (5)
H1AB1.4309440.1117710.1180650.067*
H1AC1.4906950.0330430.1180410.067*
H1AD1.4532770.0704210.2119480.067*
C3A1.2382 (3)0.02746 (13)0.04091 (14)0.0547 (6)
H3AA1.1453470.0104460.0384950.082*
H3AB1.2963100.0064470.0098850.082*
H3AC1.2436920.0736840.0108250.082*
H1A1.3011 (18)0.4223 (9)0.2273 (14)0.030 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0204 (5)0.0317 (6)0.0131 (5)0.0008 (4)0.0016 (4)0.0013 (4)
O20.0193 (5)0.0270 (5)0.0165 (5)0.0031 (4)0.0020 (4)0.0034 (4)
O10.0263 (5)0.0243 (5)0.0138 (5)0.0084 (4)0.0006 (4)0.0008 (4)
N60.0186 (6)0.0185 (6)0.0103 (5)0.0003 (4)0.0009 (4)0.0011 (4)
N50.0168 (6)0.0150 (5)0.0134 (5)0.0001 (4)0.0011 (4)0.0012 (4)
C170.0198 (7)0.0145 (6)0.0149 (6)0.0010 (5)0.0012 (5)0.0021 (5)
C160.0186 (7)0.0135 (6)0.0136 (6)0.0016 (5)0.0002 (5)0.0019 (5)
C90.0158 (6)0.0199 (7)0.0141 (6)0.0017 (5)0.0003 (5)0.0016 (5)
N10.0309 (7)0.0173 (6)0.0198 (6)0.0039 (5)0.0010 (5)0.0015 (5)
C150.0160 (6)0.0137 (6)0.0162 (7)0.0004 (5)0.0006 (5)0.0016 (5)
C180.0197 (7)0.0131 (6)0.0140 (6)0.0024 (5)0.0007 (5)0.0011 (5)
C110.0176 (7)0.0175 (7)0.0111 (6)0.0001 (5)0.0013 (5)0.0005 (5)
C190.0183 (7)0.0183 (7)0.0152 (6)0.0025 (5)0.0014 (5)0.0024 (5)
C120.0168 (6)0.0203 (7)0.0169 (6)0.0028 (5)0.0016 (5)0.0004 (5)
C220.0193 (7)0.0235 (7)0.0148 (6)0.0023 (5)0.0012 (5)0.0021 (5)
C80.0186 (7)0.0184 (7)0.0132 (6)0.0006 (5)0.0012 (5)0.0004 (5)
C10.0209 (7)0.0166 (7)0.0241 (7)0.0033 (5)0.0004 (5)0.0041 (5)
C100.0188 (7)0.0155 (6)0.0142 (6)0.0020 (5)0.0010 (5)0.0011 (5)
C50.0227 (7)0.0230 (7)0.0226 (7)0.0043 (6)0.0021 (6)0.0034 (6)
C140.0171 (6)0.0169 (6)0.0155 (6)0.0024 (5)0.0025 (5)0.0003 (5)
C60.0163 (7)0.0180 (7)0.0209 (7)0.0038 (5)0.0005 (5)0.0042 (5)
N40.0497 (9)0.0225 (7)0.0288 (7)0.0080 (6)0.0075 (6)0.0000 (6)
O1A0.0444 (8)0.0383 (7)0.0548 (9)0.0066 (6)0.0089 (7)0.0052 (6)
C230.0189 (7)0.0297 (8)0.0170 (7)0.0027 (6)0.0013 (5)0.0025 (6)
C130.0202 (7)0.0162 (7)0.0196 (7)0.0034 (5)0.0003 (5)0.0011 (5)
C20.0249 (8)0.0167 (7)0.0356 (9)0.0005 (6)0.0015 (6)0.0039 (6)
C70.0278 (8)0.0143 (7)0.0241 (7)0.0005 (6)0.0006 (6)0.0009 (5)
C30.0236 (8)0.0220 (8)0.0403 (9)0.0006 (6)0.0050 (6)0.0134 (7)
C210.0275 (8)0.0279 (8)0.0173 (7)0.0094 (6)0.0006 (6)0.0015 (6)
N30.0610 (10)0.0271 (8)0.0292 (8)0.0120 (7)0.0114 (7)0.0007 (6)
C40.0265 (8)0.0326 (9)0.0263 (8)0.0071 (7)0.0083 (6)0.0119 (7)
C240.0321 (9)0.0256 (8)0.0340 (9)0.0057 (7)0.0044 (7)0.0030 (7)
N20.0488 (9)0.0247 (7)0.0236 (7)0.0074 (6)0.0061 (6)0.0019 (5)
C200.0200 (7)0.0248 (8)0.0408 (9)0.0017 (6)0.0085 (7)0.0020 (7)
C2A0.0477 (11)0.0271 (8)0.0319 (9)0.0045 (7)0.0029 (8)0.0037 (7)
C1A0.0505 (12)0.0346 (10)0.0492 (12)0.0037 (9)0.0069 (9)0.0020 (8)
C3A0.0776 (16)0.0524 (13)0.0341 (11)0.0189 (12)0.0009 (10)0.0070 (9)
Geometric parameters (Å, º) top
O3—C181.2471 (17)C5—C61.392 (2)
O2—C181.2546 (17)C5—C41.392 (2)
O1—H10.8200C14—H14A0.9700
O1—C191.4296 (16)C14—H14B0.9700
N6—H60.8600N4—C71.324 (2)
N6—C171.3335 (18)N4—N31.366 (2)
N6—C161.3796 (18)O1A—H1AA0.8200
N5—C171.3338 (18)O1A—C2A1.428 (2)
N5—C151.4059 (17)C23—H23A0.9700
N5—C141.4716 (17)C23—H23B0.9700
C17—C221.4875 (19)C23—C241.519 (2)
C16—C151.3752 (19)C13—H130.9300
C16—C191.5192 (19)C2—H20.9300
C9—H90.9300C2—C31.379 (2)
C9—C81.395 (2)C3—H30.9300
C9—C101.3874 (19)C3—C41.384 (3)
N1—C71.339 (2)C21—H21A0.9600
N1—N21.3407 (18)C21—H21B0.9600
N1—H1A0.868 (15)C21—H21C0.9600
C15—C181.5109 (18)N3—N21.300 (2)
C11—C121.3946 (19)C4—H40.9300
C11—C101.3935 (19)C24—H24A0.9600
C11—C141.5130 (18)C24—H24B0.9600
C19—C211.5226 (19)C24—H24C0.9600
C19—C201.529 (2)C20—H20A0.9600
C12—H120.9300C20—H20B0.9600
C12—C131.385 (2)C20—H20C0.9600
C22—H22A0.9700C2A—H2A0.9800
C22—H22B0.9700C2A—C1A1.520 (3)
C22—C231.541 (2)C2A—C3A1.500 (3)
C8—C61.4930 (19)C1A—H1AB0.9600
C8—C131.3997 (19)C1A—H1AC0.9600
C1—C61.407 (2)C1A—H1AD0.9600
C1—C21.396 (2)C3A—H3AA0.9600
C1—C71.473 (2)C3A—H3AB0.9600
C10—H100.9300C3A—H3AC0.9600
C5—H50.9300
C19—O1—H1109.5C5—C6—C1118.51 (13)
C17—N6—H6124.9C7—N4—N3105.69 (13)
C17—N6—C16110.18 (11)C2A—O1A—H1AA109.5
C16—N6—H6124.9C22—C23—H23A108.9
C17—N5—C15109.15 (11)C22—C23—H23B108.9
C17—N5—C14122.86 (11)H23A—C23—H23B107.8
C15—N5—C14127.96 (11)C24—C23—C22113.16 (12)
N6—C17—N5108.02 (12)C24—C23—H23A108.9
N6—C17—C22123.95 (12)C24—C23—H23B108.9
N5—C17—C22127.75 (12)C12—C13—C8120.62 (13)
N6—C16—C19120.43 (12)C12—C13—H13119.7
C15—C16—N6106.57 (12)C8—C13—H13119.7
C15—C16—C19133.00 (13)C1—C2—H2119.9
C8—C9—H9119.7C3—C2—C1120.14 (15)
C10—C9—H9119.7C3—C2—H2119.9
C10—C9—C8120.65 (12)N1—C7—C1125.20 (13)
C7—N1—N2109.02 (13)N4—C7—N1108.31 (13)
C7—N1—H1A128.7 (13)N4—C7—C1126.47 (14)
N2—N1—H1A122.3 (13)C2—C3—H3120.1
N5—C15—C18123.77 (12)C2—C3—C4119.85 (14)
C16—C15—N5106.06 (12)C4—C3—H3120.1
C16—C15—C18130.16 (13)C19—C21—H21A109.5
O3—C18—O2125.87 (12)C19—C21—H21B109.5
O3—C18—C15117.98 (12)C19—C21—H21C109.5
O2—C18—C15116.15 (12)H21A—C21—H21B109.5
C12—C11—C14123.22 (12)H21A—C21—H21C109.5
C10—C11—C12118.79 (12)H21B—C21—H21C109.5
C10—C11—C14117.98 (12)N2—N3—N4110.58 (13)
O1—C19—C16109.44 (11)C5—C4—H4119.7
O1—C19—C21105.81 (11)C3—C4—C5120.60 (15)
O1—C19—C20110.48 (12)C3—C4—H4119.7
C16—C19—C21111.29 (12)C23—C24—H24A109.5
C16—C19—C20108.59 (11)C23—C24—H24B109.5
C21—C19—C20111.22 (12)C23—C24—H24C109.5
C11—C12—H12119.7H24A—C24—H24B109.5
C13—C12—C11120.64 (13)H24A—C24—H24C109.5
C13—C12—H12119.7H24B—C24—H24C109.5
C17—C22—H22A109.5N3—N2—N1106.38 (13)
C17—C22—H22B109.5C19—C20—H20A109.5
C17—C22—C23110.86 (11)C19—C20—H20B109.5
H22A—C22—H22B108.1C19—C20—H20C109.5
C23—C22—H22A109.5H20A—C20—H20B109.5
C23—C22—H22B109.5H20A—C20—H20C109.5
C9—C8—C6120.28 (12)H20B—C20—H20C109.5
C9—C8—C13118.59 (13)O1A—C2A—H2A108.9
C13—C8—C6121.04 (12)O1A—C2A—C1A107.08 (15)
C6—C1—C7120.50 (13)O1A—C2A—C3A111.53 (18)
C2—C1—C6120.47 (14)C1A—C2A—H2A108.9
C2—C1—C7119.02 (14)C3A—C2A—H2A108.9
C9—C10—C11120.66 (12)C3A—C2A—C1A111.48 (17)
C9—C10—H10119.7C2A—C1A—H1AB109.5
C11—C10—H10119.7C2A—C1A—H1AC109.5
C6—C5—H5119.8C2A—C1A—H1AD109.5
C4—C5—H5119.8H1AB—C1A—H1AC109.5
C4—C5—C6120.42 (15)H1AB—C1A—H1AD109.5
N5—C14—C11113.39 (11)H1AC—C1A—H1AD109.5
N5—C14—H14A108.9C2A—C3A—H3AA109.5
N5—C14—H14B108.9C2A—C3A—H3AB109.5
C11—C14—H14A108.9C2A—C3A—H3AC109.5
C11—C14—H14B108.9H3AA—C3A—H3AB109.5
H14A—C14—H14B107.7H3AA—C3A—H3AC109.5
C1—C6—C8120.41 (12)H3AB—C3A—H3AC109.5
C5—C6—C8121.08 (13)
4-(2-Hydroxypropan-2-yl)-2-propyl-1-({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazol-3-ium-5-carboxylate isobutanol monosolvate (Ol-IsoBut) top
Crystal data top
C24H26N6O3·C4H10OF(000) = 1112
Mr = 520.63Dx = 1.276 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 9.77352 (14) ÅCell parameters from 15971 reflections
b = 19.3316 (3) Åθ = 3.8–71.4°
c = 14.34250 (17) ŵ = 0.71 mm1
β = 90.3045 (11)°T = 101 K
V = 2709.81 (7) Å3Needle, colourless
Z = 40.1 × 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 Source4555 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.038
Detector resolution: 16.4335 pixels mm-1θmax = 71.8°, θmin = 3.8°
ω scansh = 1112
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
k = 2320
Tmin = 0.867, Tmax = 1.000l = 1717
39211 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.040H 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 reflectionsΔρmax = 0.28 e Å3
354 parametersΔρmin = 0.25 e Å3
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
xyzUiso*/Ueq
O30.21070 (10)0.23719 (6)0.93756 (6)0.0236 (2)
O20.00955 (10)0.27749 (5)0.88809 (6)0.0223 (2)
O10.08312 (10)0.33774 (5)0.74124 (6)0.0224 (2)
H10.0643030.3244150.7940550.034*
N60.20129 (11)0.25845 (6)0.62321 (7)0.0169 (2)
H60.1823990.2626720.5648580.020*
N50.31406 (11)0.23926 (6)0.75053 (7)0.0166 (2)
N10.77103 (12)0.45658 (7)0.70946 (8)0.0229 (3)
C120.44547 (14)0.35633 (8)0.83769 (9)0.0216 (3)
H120.3577700.3612030.8130820.026*
C170.32356 (13)0.24110 (7)0.65766 (9)0.0174 (3)
C160.10964 (13)0.26863 (7)0.69448 (9)0.0164 (3)
C90.70260 (13)0.34260 (7)0.91725 (9)0.0200 (3)
H90.7874410.3374030.9460790.024*
N30.66416 (15)0.52609 (8)0.62152 (10)0.0351 (3)
N20.72761 (13)0.46750 (7)0.62113 (9)0.0291 (3)
C110.50239 (13)0.29079 (7)0.84586 (8)0.0171 (3)
C100.63168 (13)0.28462 (7)0.88656 (9)0.0187 (3)
H100.6709440.2410630.8932320.022*
C190.03892 (13)0.28727 (7)0.67487 (9)0.0177 (3)
C180.12949 (14)0.25697 (7)0.87526 (9)0.0172 (3)
C80.64774 (14)0.40840 (7)0.90522 (9)0.0203 (3)
C210.05546 (14)0.32068 (8)0.57947 (9)0.0219 (3)
H21A0.1477220.3368910.5720660.033*
H21B0.0357060.2872740.5318730.033*
H21C0.0066130.3589510.5742380.033*
C70.73265 (14)0.50958 (8)0.76250 (10)0.0238 (3)
C220.44824 (14)0.23095 (8)0.60020 (9)0.0227 (3)
H22A0.4213480.2180590.5373660.027*
H22B0.5020360.1933750.6261730.027*
C130.51754 (14)0.41471 (8)0.86573 (10)0.0235 (3)
H130.4787770.4582920.8581390.028*
C140.43178 (13)0.22566 (7)0.81218 (9)0.0178 (3)
H14A0.4974740.1973560.7790260.021*
H14B0.4008700.1995090.8658050.021*
N40.66531 (14)0.55403 (7)0.70898 (10)0.0326 (3)
C60.72930 (14)0.47110 (8)0.93046 (10)0.0231 (3)
C50.77063 (15)0.48287 (8)1.02236 (11)0.0283 (3)
H50.7484380.4509901.0684250.034*
C10.76574 (14)0.51968 (8)0.86232 (10)0.0238 (3)
C200.12547 (15)0.22172 (8)0.68302 (11)0.0263 (3)
H20A0.1140770.2022570.7441480.040*
H20B0.0966240.1887540.6370930.040*
H20C0.2200610.2329870.6729420.040*
C230.53665 (14)0.29692 (9)0.59652 (10)0.0276 (3)
H23A0.5739410.3058060.6581750.033*
H23B0.6128660.2890130.5548060.033*
C240.45874 (17)0.36044 (9)0.56391 (11)0.0336 (4)
H24A0.4109950.3500150.5069550.050*
H24B0.5218150.3976610.5534040.050*
H24C0.3941120.3738150.6107470.050*
C20.83879 (15)0.57911 (8)0.88668 (11)0.0290 (3)
H20.8612780.6113530.8411430.035*
C150.17941 (13)0.25597 (7)0.77622 (9)0.0164 (3)
C30.87781 (16)0.59020 (9)0.97824 (12)0.0333 (4)
H30.9260430.6299280.9944330.040*
C40.84478 (16)0.54192 (9)1.04571 (11)0.0333 (4)
H40.8723440.5489791.1071360.040*
O1A0.61938 (12)0.08041 (7)0.73781 (9)0.0419 (3)
H1AA0.5385380.0763800.7518220.063*
C2A0.83577 (16)0.04822 (8)0.80825 (11)0.0288 (3)
H2A0.8736320.0619200.7478650.035*
C3A0.70055 (17)0.08513 (9)0.82076 (12)0.0349 (4)
H3AA0.6513620.0645790.8723840.042*
H3AB0.7171360.1333830.8354990.042*
C1A0.93650 (18)0.06988 (10)0.88409 (12)0.0399 (4)
H1AB0.9500190.1190290.8815140.060*
H1AC1.0223080.0468330.8746140.060*
H1AD0.9006970.0574410.9439970.060*
C4A0.8156 (2)0.02944 (9)0.80751 (14)0.0424 (4)
H4AA0.7917870.0448480.8689570.064*
H4AB0.8987600.0515790.7884050.064*
H4AC0.7433610.0411390.7646990.064*
H1A0.8176 (18)0.4202 (8)0.7227 (13)0.035 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0232 (5)0.0380 (6)0.0096 (4)0.0028 (4)0.0012 (4)0.0013 (4)
O20.0230 (5)0.0321 (6)0.0119 (4)0.0061 (4)0.0024 (4)0.0024 (4)
O10.0288 (5)0.0274 (5)0.0110 (4)0.0088 (4)0.0006 (4)0.0001 (4)
N60.0194 (5)0.0241 (6)0.0073 (5)0.0007 (4)0.0010 (4)0.0001 (4)
N50.0174 (5)0.0223 (6)0.0100 (5)0.0008 (4)0.0012 (4)0.0012 (4)
N10.0251 (6)0.0230 (6)0.0205 (6)0.0024 (5)0.0027 (5)0.0016 (5)
C120.0190 (6)0.0260 (7)0.0198 (7)0.0029 (5)0.0032 (5)0.0006 (5)
C170.0200 (6)0.0205 (7)0.0117 (6)0.0006 (5)0.0006 (5)0.0016 (5)
C160.0201 (6)0.0182 (7)0.0110 (6)0.0008 (5)0.0003 (5)0.0010 (5)
C90.0174 (6)0.0291 (8)0.0134 (6)0.0018 (5)0.0000 (5)0.0008 (5)
N30.0383 (8)0.0355 (8)0.0313 (7)0.0061 (6)0.0073 (6)0.0061 (6)
N20.0310 (7)0.0331 (7)0.0233 (6)0.0010 (5)0.0053 (5)0.0050 (5)
C110.0193 (6)0.0235 (7)0.0084 (6)0.0003 (5)0.0007 (5)0.0000 (5)
C100.0194 (6)0.0236 (7)0.0132 (6)0.0039 (5)0.0009 (5)0.0010 (5)
C190.0185 (6)0.0225 (7)0.0123 (6)0.0023 (5)0.0004 (5)0.0013 (5)
C180.0222 (6)0.0186 (7)0.0109 (6)0.0014 (5)0.0008 (5)0.0009 (5)
C80.0201 (6)0.0259 (7)0.0150 (6)0.0000 (5)0.0024 (5)0.0017 (5)
C210.0235 (7)0.0293 (8)0.0128 (6)0.0051 (6)0.0017 (5)0.0002 (5)
C70.0212 (7)0.0219 (7)0.0283 (8)0.0004 (5)0.0005 (5)0.0019 (6)
C220.0202 (7)0.0350 (8)0.0129 (6)0.0041 (6)0.0010 (5)0.0021 (5)
C130.0227 (7)0.0229 (7)0.0249 (7)0.0031 (5)0.0018 (5)0.0000 (6)
C140.0189 (6)0.0221 (7)0.0122 (6)0.0031 (5)0.0024 (5)0.0004 (5)
N40.0335 (7)0.0281 (7)0.0362 (7)0.0059 (6)0.0036 (6)0.0040 (6)
C60.0183 (6)0.0265 (8)0.0245 (7)0.0024 (5)0.0004 (5)0.0061 (6)
C50.0259 (7)0.0343 (9)0.0247 (7)0.0000 (6)0.0011 (6)0.0053 (6)
C10.0210 (7)0.0224 (7)0.0279 (8)0.0031 (5)0.0007 (5)0.0043 (6)
C200.0208 (7)0.0283 (8)0.0300 (8)0.0016 (6)0.0024 (6)0.0026 (6)
C230.0200 (7)0.0483 (10)0.0145 (6)0.0051 (6)0.0011 (5)0.0048 (6)
C240.0379 (9)0.0382 (9)0.0247 (8)0.0123 (7)0.0042 (6)0.0012 (7)
C20.0276 (8)0.0231 (8)0.0363 (8)0.0002 (6)0.0024 (6)0.0059 (6)
C150.0177 (6)0.0194 (7)0.0120 (6)0.0002 (5)0.0001 (5)0.0014 (5)
C30.0292 (8)0.0298 (8)0.0410 (9)0.0025 (6)0.0016 (7)0.0141 (7)
C40.0287 (8)0.0426 (10)0.0287 (8)0.0001 (7)0.0020 (6)0.0167 (7)
O1A0.0313 (6)0.0527 (8)0.0415 (7)0.0034 (6)0.0020 (5)0.0007 (6)
C2A0.0320 (8)0.0297 (8)0.0247 (7)0.0003 (6)0.0023 (6)0.0039 (6)
C3A0.0351 (9)0.0345 (9)0.0353 (9)0.0000 (7)0.0040 (7)0.0055 (7)
C1A0.0402 (10)0.0462 (11)0.0333 (9)0.0004 (8)0.0039 (7)0.0089 (8)
C4A0.0531 (11)0.0310 (9)0.0430 (10)0.0014 (8)0.0058 (8)0.0048 (8)
Geometric parameters (Å, º) top
O3—C181.2518 (16)C22—H22B0.9700
O2—C181.2520 (17)C22—C231.542 (2)
O1—H10.8200C13—H130.9300
O1—C191.4313 (16)C14—H14A0.9700
N6—H60.8600C14—H14B0.9700
N6—C171.3336 (17)C6—C51.395 (2)
N6—C161.3769 (16)C6—C11.403 (2)
N5—C171.3362 (16)C5—H50.9300
N5—C141.4710 (16)C5—C41.392 (2)
N5—C151.4061 (16)C1—C21.396 (2)
N1—N21.3505 (17)C20—H20A0.9600
N1—C71.3313 (19)C20—H20B0.9600
N1—H1A0.858 (14)C20—H20C0.9600
C12—H120.9300C23—H23A0.9700
C12—C111.3884 (19)C23—H23B0.9700
C12—C131.389 (2)C23—C241.517 (2)
C17—C221.4876 (18)C24—H24A0.9600
C16—C191.5208 (18)C24—H24B0.9600
C16—C151.3750 (18)C24—H24C0.9600
C9—H90.9300C2—H20.9300
C9—C101.388 (2)C2—C31.382 (2)
C9—C81.391 (2)C3—H30.9300
N3—N21.2913 (19)C3—C41.384 (3)
N3—N41.366 (2)C4—H40.9300
C11—C101.3941 (18)O1A—H1AA0.8200
C11—C141.5137 (18)O1A—C3A1.429 (2)
C10—H100.9300C2A—H2A0.9800
C19—C211.5209 (18)C2A—C3A1.513 (2)
C19—C201.528 (2)C2A—C1A1.522 (2)
C18—C151.5045 (17)C2A—C4A1.514 (2)
C8—C131.3954 (19)C3A—H3AA0.9700
C8—C61.494 (2)C3A—H3AB0.9700
C21—H21A0.9600C1A—H1AB0.9600
C21—H21B0.9600C1A—H1AC0.9600
C21—H21C0.9600C1A—H1AD0.9600
C7—N41.3249 (19)C4A—H4AA0.9600
C7—C11.479 (2)C4A—H4AB0.9600
C22—H22A0.9700C4A—H4AC0.9600
C19—O1—H1109.5C7—N4—N3106.10 (13)
C17—N6—H6124.9C5—C6—C8120.83 (13)
C17—N6—C16110.25 (11)C5—C6—C1118.41 (14)
C16—N6—H6124.9C1—C6—C8120.76 (13)
C17—N5—C14123.07 (11)C6—C5—H5119.7
C17—N5—C15108.98 (11)C4—C5—C6120.58 (15)
C15—N5—C14127.86 (10)C4—C5—H5119.7
N2—N1—H1A119.9 (13)C6—C1—C7122.08 (13)
C7—N1—N2109.13 (12)C2—C1—C7117.37 (14)
C7—N1—H1A130.9 (13)C2—C1—C6120.53 (14)
C11—C12—H12119.5C19—C20—H20A109.5
C11—C12—C13120.98 (13)C19—C20—H20B109.5
C13—C12—H12119.5C19—C20—H20C109.5
N6—C17—N5108.00 (11)H20A—C20—H20B109.5
N6—C17—C22124.26 (12)H20A—C20—H20C109.5
N5—C17—C22127.61 (12)H20B—C20—H20C109.5
N6—C16—C19121.39 (11)C22—C23—H23A108.9
C15—C16—N6106.61 (11)C22—C23—H23B108.9
C15—C16—C19131.96 (12)H23A—C23—H23B107.7
C10—C9—H9119.7C24—C23—C22113.55 (12)
C10—C9—C8120.50 (12)C24—C23—H23A108.9
C8—C9—H9119.7C24—C23—H23B108.9
N2—N3—N4110.45 (12)C23—C24—H24A109.5
N3—N2—N1106.35 (12)C23—C24—H24B109.5
C12—C11—C10118.38 (13)C23—C24—H24C109.5
C12—C11—C14123.38 (12)H24A—C24—H24B109.5
C10—C11—C14118.23 (12)H24A—C24—H24C109.5
C9—C10—C11120.90 (13)H24B—C24—H24C109.5
C9—C10—H10119.6C1—C2—H2119.9
C11—C10—H10119.6C3—C2—C1120.23 (15)
O1—C19—C16109.25 (10)C3—C2—H2119.9
O1—C19—C21106.14 (11)N5—C15—C18123.98 (11)
O1—C19—C20110.19 (11)C16—C15—N5106.15 (11)
C16—C19—C20108.51 (11)C16—C15—C18129.85 (12)
C21—C19—C16111.34 (11)C2—C3—H3120.1
C21—C19—C20111.39 (11)C2—C3—C4119.71 (15)
O3—C18—O2125.62 (12)C4—C3—H3120.1
O3—C18—C15117.54 (12)C5—C4—H4119.7
O2—C18—C15116.83 (11)C3—C4—C5120.53 (15)
C9—C8—C13118.71 (13)C3—C4—H4119.7
C9—C8—C6120.47 (12)C3A—O1A—H1AA109.5
C13—C8—C6120.78 (13)C3A—C2A—H2A108.1
C19—C21—H21A109.5C3A—C2A—C1A110.34 (13)
C19—C21—H21B109.5C3A—C2A—C4A110.75 (14)
C19—C21—H21C109.5C1A—C2A—H2A108.1
H21A—C21—H21B109.5C4A—C2A—H2A108.1
H21A—C21—H21C109.5C4A—C2A—C1A111.19 (15)
H21B—C21—H21C109.5O1A—C3A—C2A110.64 (13)
N1—C7—C1126.43 (13)O1A—C3A—H3AA109.5
N4—C7—N1107.98 (13)O1A—C3A—H3AB109.5
N4—C7—C1125.50 (14)C2A—C3A—H3AA109.5
C17—C22—H22A109.3C2A—C3A—H3AB109.5
C17—C22—H22B109.3H3AA—C3A—H3AB108.1
C17—C22—C23111.77 (12)C2A—C1A—H1AB109.5
H22A—C22—H22B107.9C2A—C1A—H1AC109.5
C23—C22—H22A109.3C2A—C1A—H1AD109.5
C23—C22—H22B109.3H1AB—C1A—H1AC109.5
C12—C13—C8120.44 (13)H1AB—C1A—H1AD109.5
C12—C13—H13119.8H1AC—C1A—H1AD109.5
C8—C13—H13119.8C2A—C4A—H4AA109.5
N5—C14—C11113.39 (11)C2A—C4A—H4AB109.5
N5—C14—H14A108.9C2A—C4A—H4AC109.5
N5—C14—H14B108.9H4AA—C4A—H4AB109.5
C11—C14—H14A108.9H4AA—C4A—H4AC109.5
C11—C14—H14B108.9H4AB—C4A—H4AC109.5
H14A—C14—H14B107.7
4-(2-Hydroxypropan-2-yl)-2-propyl-1-({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazol-3-ium-5-carboxylate 2-ethoxyethanol monosolvate (Ol-Etox) top
Crystal data top
C24H26N6O3·C4H10O2F(000) = 1144
Mr = 536.63Dx = 1.266 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 10.25267 (10) ÅCell parameters from 23615 reflections
b = 19.21448 (19) Åθ = 3.9–71.6°
c = 14.29015 (17) ŵ = 0.72 mm1
β = 90.1353 (10)°T = 102 K
V = 2815.15 (5) Å3Block, colourless
Z = 40.1 × 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 Source5006 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.035
Detector resolution: 16.4335 pixels mm-1θmax = 71.8°, θmin = 3.9°
ω scansh = 1212
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
k = 2323
Tmin = 0.768, Tmax = 1.000l = 1714
49601 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.045H 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 reflectionsΔρmax = 0.37 e Å3
362 parametersΔρmin = 0.33 e Å3
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
xyzUiso*/Ueq
O10.60362 (11)0.16191 (6)0.81750 (8)0.0245 (3)
H10.5813250.1753420.8695290.037*
O20.50886 (12)0.21671 (7)0.96486 (8)0.0279 (3)
O30.32340 (11)0.26633 (7)1.00938 (8)0.0265 (3)
N50.22819 (13)0.26548 (7)0.82093 (9)0.0183 (3)
O2A0.62705 (12)0.44438 (7)0.89518 (10)0.0335 (3)
N60.33551 (13)0.24406 (7)0.69459 (9)0.0191 (3)
H60.3541430.2397580.6362280.023*
N10.23209 (14)0.05301 (8)0.80254 (10)0.0251 (3)
C160.42076 (15)0.23136 (8)0.76711 (11)0.0186 (3)
N30.11680 (16)0.02456 (9)0.73972 (12)0.0359 (4)
N40.13834 (16)0.04558 (8)0.82944 (12)0.0342 (4)
C120.07940 (15)0.15755 (9)0.91489 (11)0.0211 (3)
H120.1618670.1469550.8919570.025*
C80.12309 (15)0.11947 (9)0.98507 (11)0.0216 (3)
C90.16549 (15)0.18836 (9)0.98551 (11)0.0218 (3)
H90.2471100.1992151.0097350.026*
C110.03662 (15)0.22613 (8)0.91531 (11)0.0192 (3)
C140.11802 (15)0.28640 (8)0.88065 (11)0.0199 (3)
H14A0.0623390.3178510.8455710.024*
H14B0.1517310.3117350.9342080.024*
C150.35415 (15)0.24491 (8)0.84856 (11)0.0186 (3)
C70.21000 (16)0.00399 (9)0.86755 (13)0.0253 (4)
C180.39868 (15)0.24218 (8)0.94884 (11)0.0200 (3)
C190.56205 (16)0.21100 (9)0.74868 (11)0.0214 (3)
C130.00007 (16)0.10471 (9)0.94846 (12)0.0227 (3)
H130.0290250.0588880.9465250.027*
C10.25209 (16)0.00817 (9)0.96594 (13)0.0251 (4)
C220.10109 (16)0.27517 (9)0.66954 (12)0.0230 (3)
H22A0.1264380.2830060.6050410.028*
H22B0.0558630.3164070.6913870.028*
C60.20895 (16)0.06329 (9)1.02246 (12)0.0237 (4)
N20.17305 (15)0.03465 (8)0.72262 (11)0.0310 (3)
C170.22014 (15)0.26394 (8)0.72761 (11)0.0192 (3)
C100.08703 (15)0.24087 (9)0.95014 (11)0.0213 (3)
H100.1173610.2864860.9496800.026*
C50.24548 (18)0.06413 (10)1.11649 (13)0.0303 (4)
H50.2164700.0999491.1550390.036*
C230.00836 (16)0.21235 (10)0.67430 (12)0.0271 (4)
H23A0.0240350.2078350.7377290.033*
H23B0.0658350.2209040.6336550.033*
C210.57619 (19)0.17429 (11)0.65491 (12)0.0336 (4)
H21A0.6639290.1575830.6482640.050*
H21B0.5568680.2063560.6052580.050*
H21C0.5167020.1357610.6520310.050*
O1A0.89444 (15)0.41222 (8)0.85200 (13)0.0499 (4)
H1AA0.9605120.4286260.8284720.075*
C30.36862 (18)0.04103 (10)1.09647 (16)0.0366 (5)
H30.4230430.0751851.1209120.044*
C20.33204 (17)0.04371 (10)1.00334 (15)0.0313 (4)
H20.3607180.0800780.9656020.038*
C240.0726 (2)0.14451 (10)0.64571 (14)0.0358 (4)
H24A0.1114340.1498030.5850700.054*
H24B0.0081720.1082770.6434460.054*
H24C0.1387610.1325070.6905180.054*
C2A0.50476 (19)0.41650 (10)0.92256 (16)0.0368 (5)
H2AA0.4738930.4398420.9784740.044*
H2AB0.5134450.3672620.9361890.044*
C3A0.72463 (19)0.43084 (11)0.96284 (15)0.0363 (4)
H3AA0.7286130.3813050.9756440.044*
H3AB0.7038440.4547561.0206860.044*
C40.32437 (19)0.01235 (11)1.15325 (14)0.0358 (4)
H40.3475520.0134901.2161140.043*
C200.64705 (18)0.27610 (10)0.75316 (17)0.0373 (5)
H20A0.6388310.2972390.8137320.056*
H20B0.6193320.3084560.7059420.056*
H20C0.7364560.2635730.7426260.056*
C1A0.4105 (2)0.42707 (12)0.8444 (2)0.0514 (6)
H1AB0.4403650.4025190.7899530.077*
H1AC0.4040610.4758240.8304030.077*
H1AD0.3264550.4096860.8623050.077*
C4A0.8530 (2)0.45542 (12)0.92695 (17)0.0443 (5)
H4AA0.8452490.5031100.9053970.053*
H4AB0.9171690.4541680.9769140.053*
H1A0.279 (2)0.0909 (9)0.8072 (16)0.038 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0286 (6)0.0293 (6)0.0156 (6)0.0085 (5)0.0003 (5)0.0019 (5)
O20.0266 (6)0.0408 (7)0.0164 (6)0.0088 (5)0.0041 (5)0.0040 (5)
O30.0235 (6)0.0424 (7)0.0135 (6)0.0029 (5)0.0007 (4)0.0021 (5)
N50.0192 (6)0.0202 (6)0.0154 (6)0.0000 (5)0.0002 (5)0.0000 (5)
O2A0.0294 (7)0.0337 (7)0.0372 (8)0.0007 (5)0.0003 (5)0.0076 (6)
N60.0224 (7)0.0236 (7)0.0114 (6)0.0005 (5)0.0002 (5)0.0011 (5)
N10.0245 (7)0.0250 (7)0.0257 (8)0.0024 (6)0.0005 (6)0.0031 (6)
C160.0218 (8)0.0186 (7)0.0153 (7)0.0016 (6)0.0009 (6)0.0005 (6)
N30.0333 (8)0.0369 (9)0.0376 (9)0.0063 (7)0.0016 (7)0.0101 (7)
N40.0324 (8)0.0292 (8)0.0411 (10)0.0062 (6)0.0000 (7)0.0057 (7)
C120.0192 (7)0.0274 (8)0.0167 (8)0.0037 (6)0.0008 (6)0.0002 (6)
C80.0219 (8)0.0254 (8)0.0174 (8)0.0007 (6)0.0016 (6)0.0005 (6)
C90.0185 (7)0.0274 (8)0.0196 (8)0.0024 (6)0.0003 (6)0.0035 (6)
C110.0204 (7)0.0245 (8)0.0126 (7)0.0001 (6)0.0027 (6)0.0010 (6)
C140.0195 (7)0.0225 (8)0.0176 (8)0.0019 (6)0.0014 (6)0.0022 (6)
C150.0186 (7)0.0199 (7)0.0172 (8)0.0005 (6)0.0001 (6)0.0001 (6)
C70.0217 (8)0.0222 (8)0.0320 (9)0.0004 (6)0.0032 (7)0.0011 (7)
C180.0213 (8)0.0229 (8)0.0159 (8)0.0025 (6)0.0004 (6)0.0005 (6)
C190.0227 (8)0.0258 (8)0.0158 (8)0.0034 (6)0.0024 (6)0.0037 (6)
C130.0234 (8)0.0225 (8)0.0222 (8)0.0039 (6)0.0012 (6)0.0015 (6)
C10.0204 (8)0.0236 (8)0.0314 (9)0.0045 (6)0.0008 (7)0.0042 (7)
C220.0242 (8)0.0281 (8)0.0167 (8)0.0023 (7)0.0031 (6)0.0016 (6)
C60.0199 (8)0.0240 (8)0.0273 (9)0.0044 (6)0.0017 (6)0.0038 (7)
N20.0297 (8)0.0356 (8)0.0276 (8)0.0013 (6)0.0019 (6)0.0075 (7)
C170.0222 (8)0.0187 (7)0.0166 (8)0.0020 (6)0.0001 (6)0.0019 (6)
C100.0214 (8)0.0229 (8)0.0195 (8)0.0032 (6)0.0024 (6)0.0022 (6)
C50.0309 (9)0.0304 (9)0.0298 (10)0.0042 (7)0.0065 (7)0.0025 (7)
C230.0238 (8)0.0413 (10)0.0162 (8)0.0058 (7)0.0027 (6)0.0025 (7)
C210.0351 (10)0.0474 (11)0.0182 (9)0.0163 (8)0.0027 (7)0.0002 (8)
O1A0.0364 (8)0.0359 (8)0.0775 (12)0.0009 (6)0.0197 (8)0.0112 (8)
C30.0276 (9)0.0314 (10)0.0509 (13)0.0024 (8)0.0096 (8)0.0155 (9)
C20.0247 (9)0.0248 (9)0.0443 (11)0.0013 (7)0.0013 (8)0.0049 (8)
C240.0465 (11)0.0321 (10)0.0288 (10)0.0121 (8)0.0051 (8)0.0026 (8)
C2A0.0335 (10)0.0282 (9)0.0486 (12)0.0005 (8)0.0074 (9)0.0021 (9)
C3A0.0374 (10)0.0371 (10)0.0342 (11)0.0033 (8)0.0026 (8)0.0035 (8)
C40.0363 (10)0.0376 (10)0.0334 (10)0.0065 (8)0.0129 (8)0.0100 (8)
C200.0228 (9)0.0331 (10)0.0560 (13)0.0002 (8)0.0085 (8)0.0054 (9)
C1A0.0350 (11)0.0387 (12)0.0806 (18)0.0005 (9)0.0087 (11)0.0081 (12)
C4A0.0356 (11)0.0404 (12)0.0568 (14)0.0035 (9)0.0070 (10)0.0069 (10)
Geometric parameters (Å, º) top
O1—H10.8200C22—H22A0.9700
O1—C191.4271 (19)C22—H22B0.9700
O2—C181.252 (2)C22—C171.490 (2)
O3—C181.250 (2)C22—C231.538 (2)
N5—C141.4731 (19)C6—C51.396 (3)
N5—C151.406 (2)C10—H100.9300
N5—C171.336 (2)C5—H50.9300
O2A—C2A1.419 (2)C5—C41.386 (3)
O2A—C3A1.414 (2)C23—H23A0.9700
N6—H60.8600C23—H23B0.9700
N6—C161.376 (2)C23—C241.517 (3)
N6—C171.331 (2)C21—H21A0.9600
N1—C71.342 (2)C21—H21B0.9600
N1—N21.341 (2)C21—H21C0.9600
N1—H1A0.874 (16)O1A—H1AA0.8200
C16—C151.376 (2)O1A—C4A1.421 (3)
C16—C191.524 (2)C3—H30.9300
N3—N41.363 (2)C3—C21.385 (3)
N3—N21.299 (2)C3—C41.384 (3)
N4—C71.321 (2)C2—H20.9300
C12—H120.9300C24—H24A0.9600
C12—C111.389 (2)C24—H24B0.9600
C12—C131.388 (2)C24—H24C0.9600
C8—C91.393 (2)C2A—H2AA0.9700
C8—C131.396 (2)C2A—H2AB0.9700
C8—C61.493 (2)C2A—C1A1.489 (3)
C9—H90.9300C3A—H3AA0.9700
C9—C101.387 (2)C3A—H3AB0.9700
C11—C141.512 (2)C3A—C4A1.490 (3)
C11—C101.392 (2)C4—H40.9300
C14—H14A0.9700C20—H20A0.9600
C14—H14B0.9700C20—H20B0.9600
C15—C181.504 (2)C20—H20C0.9600
C7—C11.474 (3)C1A—H1AB0.9600
C19—C211.522 (2)C1A—H1AC0.9600
C19—C201.526 (2)C1A—H1AD0.9600
C13—H130.9300C4A—H4AA0.9700
C1—C61.403 (3)C4A—H4AB0.9700
C1—C21.398 (2)
C19—O1—H1109.5N6—C17—N5107.90 (14)
C15—N5—C14128.24 (13)N6—C17—C22124.88 (14)
C17—N5—C14122.58 (13)C9—C10—C11120.79 (15)
C17—N5—C15109.18 (13)C9—C10—H10119.6
C3A—O2A—C2A111.48 (15)C11—C10—H10119.6
C16—N6—H6124.8C6—C5—H5119.5
C17—N6—H6124.8C4—C5—C6120.97 (18)
C17—N6—C16110.34 (13)C4—C5—H5119.5
C7—N1—H1A128.6 (15)C22—C23—H23A108.9
N2—N1—C7109.22 (15)C22—C23—H23B108.9
N2—N1—H1A122.2 (15)H23A—C23—H23B107.8
N6—C16—C19121.19 (14)C24—C23—C22113.19 (14)
C15—C16—N6106.73 (14)C24—C23—H23A108.9
C15—C16—C19131.97 (14)C24—C23—H23B108.9
N2—N3—N4111.34 (15)C19—C21—H21A109.5
C7—N4—N3105.41 (15)C19—C21—H21B109.5
C11—C12—H12119.8C19—C21—H21C109.5
C13—C12—H12119.8H21A—C21—H21B109.5
C13—C12—C11120.45 (15)H21A—C21—H21C109.5
C9—C8—C13118.49 (15)H21B—C21—H21C109.5
C9—C8—C6120.08 (14)C4A—O1A—H1AA109.5
C13—C8—C6121.43 (15)C2—C3—H3119.9
C8—C9—H9119.7C4—C3—H3119.9
C10—C9—C8120.55 (15)C4—C3—C2120.13 (18)
C10—C9—H9119.7C1—C2—H2119.9
C12—C11—C14123.43 (14)C3—C2—C1120.10 (18)
C12—C11—C10118.85 (15)C3—C2—H2119.9
C10—C11—C14117.72 (14)C23—C24—H24A109.5
N5—C14—C11113.92 (13)C23—C24—H24B109.5
N5—C14—H14A108.8C23—C24—H24C109.5
N5—C14—H14B108.8H24A—C24—H24B109.5
C11—C14—H14A108.8H24A—C24—H24C109.5
C11—C14—H14B108.8H24B—C24—H24C109.5
H14A—C14—H14B107.7O2A—C2A—H2AA110.0
N5—C15—C18123.64 (14)O2A—C2A—H2AB110.0
C16—C15—N5105.84 (13)O2A—C2A—C1A108.27 (18)
C16—C15—C18130.49 (14)H2AA—C2A—H2AB108.4
N1—C7—C1124.95 (15)C1A—C2A—H2AA110.0
N4—C7—N1108.28 (16)C1A—C2A—H2AB110.0
N4—C7—C1126.65 (16)O2A—C3A—H3AA109.8
O2—C18—C15117.38 (14)O2A—C3A—H3AB109.8
O3—C18—O2125.23 (15)O2A—C3A—C4A109.30 (17)
O3—C18—C15117.38 (14)H3AA—C3A—H3AB108.3
O1—C19—C16109.45 (12)C4A—C3A—H3AA109.8
O1—C19—C21105.75 (13)C4A—C3A—H3AB109.8
O1—C19—C20110.08 (14)C5—C4—H4120.0
C16—C19—C20108.99 (14)C3—C4—C5120.03 (18)
C21—C19—C16111.33 (14)C3—C4—H4120.0
C21—C19—C20111.19 (15)C19—C20—H20A109.5
C12—C13—C8120.84 (15)C19—C20—H20B109.5
C12—C13—H13119.6C19—C20—H20C109.5
C8—C13—H13119.6H20A—C20—H20B109.5
C6—C1—C7119.85 (15)H20A—C20—H20C109.5
C2—C1—C7119.95 (16)H20B—C20—H20C109.5
C2—C1—C6120.18 (17)C2A—C1A—H1AB109.5
H22A—C22—H22B108.0C2A—C1A—H1AC109.5
C17—C22—H22A109.3C2A—C1A—H1AD109.5
C17—C22—H22B109.3H1AB—C1A—H1AC109.5
C17—C22—C23111.55 (14)H1AB—C1A—H1AD109.5
C23—C22—H22A109.3H1AC—C1A—H1AD109.5
C23—C22—H22B109.3O1A—C4A—C3A109.88 (18)
C1—C6—C8121.69 (15)O1A—C4A—H4AA109.7
C5—C6—C8119.73 (16)O1A—C4A—H4AB109.7
C5—C6—C1118.56 (16)C3A—C4A—H4AA109.7
N3—N2—N1105.75 (15)C3A—C4A—H4AB109.7
N5—C17—C22126.95 (14)H4AA—C4A—H4AB108.2
4-(2-Hydroxypropan-2-yl)-2-propyl-1-({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazol-3-ium-5-carboxylate chloroform monosolvate (Ol-Chl) top
Crystal data top
C24H26N6O3·CHCl3F(000) = 1176
Mr = 565.87Dx = 1.415 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 10.0422 (2) ÅCell parameters from 6973 reflections
b = 18.3553 (4) Åθ = 3.9–72.1°
c = 14.4134 (3) ŵ = 3.45 mm1
β = 91.5895 (17)°T = 100 K
V = 2655.76 (10) Å3Block, colourless
Z = 40.1 × 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 Source4777 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.018
Detector resolution: 16.4335 pixels mm-1θmax = 72.6°, θmin = 3.9°
ω scansh = 1212
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
k = 2221
Tmin = 0.500, Tmax = 1.000l = 1710
10501 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.068H 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 reflectionsΔρmax = 0.99 e Å3
342 parametersΔρmin = 1.70 e Å3
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
xyzUiso*/Ueq
Cl1A0.28099 (10)0.06796 (5)0.52320 (7)0.0396 (3)
Cl2A0.10358 (12)0.04080 (5)0.60011 (8)0.0496 (3)
Cl3A0.37726 (19)0.07611 (10)0.56808 (10)0.0915 (7)
O30.29097 (18)0.26688 (11)1.01341 (12)0.0137 (4)
O20.4933 (2)0.23652 (13)1.05854 (14)0.0208 (5)
N50.1938 (2)0.26884 (11)1.20243 (14)0.0073 (4)
N60.3003 (2)0.24327 (12)1.32647 (14)0.0079 (4)
H60.3172110.2362751.3839550.009*
O10.59226 (18)0.17429 (10)1.19849 (12)0.0122 (4)
H10.5692090.1906111.1484710.018*
N10.2844 (2)0.04061 (13)1.21077 (16)0.0148 (5)
C110.0053 (2)0.22717 (14)1.10698 (17)0.0081 (5)
C80.1482 (2)0.11352 (14)1.03501 (17)0.0101 (5)
N20.2555 (3)0.01436 (14)1.29524 (18)0.0226 (6)
C130.0249 (2)0.09943 (15)1.07418 (18)0.0121 (5)
H130.0063480.0518091.0769450.014*
C210.5516 (3)0.17321 (18)1.35963 (19)0.0193 (6)
H21A0.4993610.1295761.3557960.029*
H21B0.5214860.2013381.4122950.029*
H21C0.6436140.1605771.3663400.029*
C150.3250 (2)0.25149 (13)1.17412 (17)0.0075 (5)
N40.2131 (3)0.06922 (15)1.1899 (2)0.0292 (6)
C170.1825 (2)0.26367 (14)1.29467 (17)0.0088 (5)
C120.0511 (2)0.15573 (15)1.10894 (18)0.0115 (5)
H120.1335330.1455921.1338100.014*
C140.0833 (2)0.29108 (14)1.14417 (17)0.0086 (5)
H14A0.1185440.3195041.0923390.010*
H14B0.0233120.3221221.1802660.010*
C90.1938 (2)0.18526 (14)1.03270 (17)0.0097 (5)
H90.2750050.1956551.0062300.012*
C100.1188 (2)0.24140 (14)1.06961 (17)0.0092 (5)
H100.1515470.2887811.0693820.011*
C180.3735 (2)0.25189 (14)1.07371 (17)0.0096 (5)
C160.3912 (2)0.23504 (13)1.25354 (17)0.0076 (5)
C50.2551 (3)0.05657 (16)0.8993 (2)0.0179 (6)
H50.2237030.0955320.8637490.021*
C10.2780 (3)0.00507 (15)1.0463 (2)0.0139 (5)
C60.2289 (2)0.05429 (15)0.99398 (19)0.0127 (5)
C20.3498 (3)0.06026 (16)1.0033 (2)0.0195 (6)
H20.3810500.0997441.0379490.023*
C70.2576 (3)0.01094 (15)1.1470 (2)0.0157 (6)
C220.0603 (2)0.27585 (15)1.35346 (18)0.0128 (5)
H22A0.0227420.3229291.3383060.015*
H22B0.0845690.2770991.4181080.015*
C190.5364 (2)0.21767 (14)1.27189 (18)0.0102 (5)
N30.2131 (3)0.05163 (16)1.2818 (2)0.0331 (7)
C30.3748 (3)0.05656 (17)0.9093 (2)0.0237 (7)
H30.4233750.0932000.8812310.028*
C240.0019 (4)0.14158 (19)1.3650 (2)0.0294 (7)
H24A0.0770640.1290701.3255440.044*
H24B0.0685390.1071521.3560600.044*
H24C0.0276090.1405251.4286300.044*
C230.0459 (3)0.21713 (18)1.34094 (19)0.0193 (6)
H23A0.1232440.2288361.3799190.023*
H23B0.0733680.2174861.2769450.023*
C40.3273 (3)0.00168 (18)0.8573 (2)0.0233 (7)
H40.3437310.0041360.7942220.028*
C200.6108 (3)0.29033 (17)1.2774 (3)0.0263 (7)
H20A0.7033130.2813141.2879690.039*
H20B0.5735070.3188781.3274710.039*
H20C0.6022190.3163511.2200540.039*
C1A0.2421 (5)0.0250 (2)0.5292 (3)0.0424 (10)
H1AA0.2178940.0414640.4663330.051*
H1A0.316 (4)0.085 (2)1.203 (2)0.021 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.0400 (5)0.0276 (5)0.0511 (6)0.0071 (4)0.0002 (4)0.0057 (4)
Cl2A0.0680 (7)0.0283 (5)0.0525 (6)0.0150 (4)0.0035 (5)0.0018 (4)
Cl3A0.1184 (13)0.0935 (11)0.0650 (8)0.0740 (10)0.0454 (9)0.0390 (8)
O30.0108 (9)0.0235 (10)0.0067 (9)0.0006 (7)0.0013 (7)0.0000 (7)
O20.0123 (9)0.0376 (13)0.0122 (9)0.0093 (9)0.0066 (7)0.0090 (9)
N50.0047 (9)0.0101 (10)0.0069 (10)0.0000 (7)0.0017 (7)0.0003 (8)
N60.0065 (9)0.0130 (10)0.0041 (9)0.0011 (8)0.0007 (7)0.0006 (8)
O10.0116 (8)0.0171 (9)0.0077 (8)0.0063 (7)0.0031 (7)0.0000 (7)
N10.0170 (11)0.0114 (12)0.0160 (11)0.0017 (9)0.0028 (9)0.0010 (9)
C110.0059 (11)0.0124 (12)0.0059 (11)0.0000 (9)0.0027 (8)0.0003 (9)
C80.0079 (11)0.0121 (12)0.0101 (12)0.0003 (9)0.0024 (9)0.0004 (9)
N20.0316 (14)0.0185 (13)0.0177 (12)0.0040 (11)0.0017 (10)0.0045 (10)
C130.0097 (12)0.0107 (12)0.0158 (13)0.0030 (10)0.0004 (10)0.0006 (10)
C210.0164 (13)0.0313 (16)0.0100 (12)0.0113 (12)0.0013 (10)0.0001 (12)
C150.0044 (11)0.0091 (11)0.0089 (12)0.0004 (9)0.0032 (9)0.0011 (9)
N40.0448 (17)0.0152 (13)0.0273 (15)0.0097 (12)0.0027 (12)0.0021 (11)
C170.0072 (11)0.0097 (12)0.0094 (12)0.0011 (9)0.0016 (9)0.0018 (9)
C120.0071 (11)0.0157 (13)0.0119 (12)0.0023 (10)0.0009 (9)0.0004 (10)
C140.0064 (11)0.0113 (12)0.0081 (11)0.0017 (9)0.0015 (9)0.0004 (9)
C90.0059 (11)0.0150 (13)0.0080 (11)0.0013 (9)0.0022 (8)0.0013 (9)
C100.0073 (11)0.0108 (12)0.0092 (11)0.0023 (9)0.0030 (9)0.0007 (9)
C180.0106 (12)0.0099 (12)0.0082 (12)0.0010 (9)0.0035 (9)0.0008 (9)
C160.0065 (11)0.0083 (11)0.0078 (11)0.0020 (9)0.0035 (9)0.0013 (9)
C50.0161 (13)0.0175 (14)0.0204 (14)0.0022 (11)0.0036 (11)0.0028 (11)
C10.0095 (12)0.0110 (12)0.0211 (14)0.0029 (10)0.0023 (10)0.0033 (10)
C60.0076 (11)0.0116 (12)0.0188 (13)0.0027 (9)0.0010 (10)0.0030 (10)
C20.0133 (13)0.0121 (13)0.0330 (16)0.0007 (10)0.0020 (11)0.0051 (12)
C70.0149 (13)0.0108 (13)0.0210 (14)0.0007 (10)0.0046 (11)0.0003 (10)
C220.0078 (11)0.0213 (14)0.0089 (12)0.0027 (10)0.0045 (9)0.0019 (10)
C190.0063 (11)0.0129 (12)0.0114 (12)0.0021 (9)0.0005 (9)0.0040 (10)
N30.0536 (19)0.0208 (14)0.0248 (14)0.0119 (13)0.0008 (13)0.0059 (11)
C30.0143 (13)0.0187 (15)0.0384 (18)0.0015 (11)0.0076 (12)0.0133 (13)
C240.0331 (18)0.0299 (18)0.0251 (16)0.0159 (14)0.0023 (13)0.0036 (13)
C230.0084 (12)0.0385 (18)0.0107 (13)0.0072 (12)0.0049 (10)0.0036 (12)
C40.0222 (15)0.0244 (16)0.0239 (15)0.0053 (12)0.0111 (12)0.0092 (12)
C200.0095 (13)0.0173 (15)0.052 (2)0.0023 (11)0.0067 (13)0.0089 (14)
C1A0.073 (3)0.0260 (19)0.0281 (19)0.0014 (19)0.0005 (18)0.0012 (15)
Geometric parameters (Å, º) top
Cl1A—C1A1.753 (4)C17—C221.489 (3)
Cl2A—C1A1.772 (5)C12—H120.9300
Cl3A—C1A1.730 (5)C14—H14A0.9700
O3—C181.248 (3)C14—H14B0.9700
O2—C181.249 (3)C9—H90.9300
N5—C151.405 (3)C9—C101.391 (4)
N5—C171.335 (3)C10—H100.9300
N5—C141.468 (3)C16—C191.524 (3)
N6—H60.8600C5—H50.9300
N6—C171.334 (3)C5—C61.397 (4)
N6—C161.381 (3)C5—C41.389 (4)
O1—H10.8200C1—C61.407 (4)
O1—C191.426 (3)C1—C21.399 (4)
N1—N21.348 (4)C1—C71.474 (4)
N1—C71.342 (4)C2—H20.9300
N1—H1A0.88 (4)C2—C31.386 (5)
C11—C121.390 (4)C22—H22A0.9700
C11—C141.517 (3)C22—H22B0.9700
C11—C101.396 (3)C22—C231.530 (4)
C8—C131.399 (4)C19—C201.532 (4)
C8—C91.395 (4)C3—H30.9300
C8—C61.488 (4)C3—C41.382 (5)
N2—N31.297 (4)C24—H24A0.9600
C13—H130.9300C24—H24B0.9600
C13—C121.387 (4)C24—H24C0.9600
C21—H21A0.9600C24—C231.511 (5)
C21—H21B0.9600C23—H23A0.9700
C21—H21C0.9600C23—H23B0.9700
C21—C191.516 (4)C4—H40.9300
C15—C181.514 (3)C20—H20A0.9600
C15—C161.373 (4)C20—H20B0.9600
N4—C71.320 (4)C20—H20C0.9600
N4—N31.364 (4)C1A—H1AA0.9800
C15—N5—C14127.9 (2)C4—C5—C6121.2 (3)
C17—N5—C15109.1 (2)C6—C1—C7121.9 (2)
C17—N5—C14123.0 (2)C2—C1—C6120.0 (3)
C17—N6—H6125.0C2—C1—C7118.1 (3)
C17—N6—C16110.0 (2)C5—C6—C8119.0 (2)
C16—N6—H6125.0C5—C6—C1118.3 (3)
C19—O1—H1109.5C1—C6—C8122.6 (2)
N2—N1—H1A122 (2)C1—C2—H2119.7
C7—N1—N2108.9 (2)C3—C2—C1120.5 (3)
C7—N1—H1A129 (2)C3—C2—H2119.7
C12—C11—C14123.2 (2)N1—C7—C1126.3 (3)
C12—C11—C10118.9 (2)N4—C7—N1108.3 (3)
C10—C11—C14117.8 (2)N4—C7—C1125.3 (3)
C13—C8—C6121.5 (2)C17—C22—H22A108.9
C9—C8—C13118.6 (2)C17—C22—H22B108.9
C9—C8—C6119.9 (2)C17—C22—C23113.1 (2)
N3—N2—N1106.1 (2)H22A—C22—H22B107.8
C8—C13—H13119.7C23—C22—H22A108.9
C12—C13—C8120.7 (2)C23—C22—H22B108.9
C12—C13—H13119.7O1—C19—C21105.8 (2)
H21A—C21—H21B109.5O1—C19—C16110.3 (2)
H21A—C21—H21C109.5O1—C19—C20110.0 (2)
H21B—C21—H21C109.5C21—C19—C16112.1 (2)
C19—C21—H21A109.5C21—C19—C20111.4 (2)
C19—C21—H21B109.5C16—C19—C20107.3 (2)
C19—C21—H21C109.5N2—N3—N4111.0 (3)
N5—C15—C18123.4 (2)C2—C3—H3120.1
C16—C15—N5106.2 (2)C4—C3—C2119.9 (3)
C16—C15—C18130.4 (2)C4—C3—H3120.1
C7—N4—N3105.8 (3)H24A—C24—H24B109.5
N5—C17—C22127.0 (2)H24A—C24—H24C109.5
N6—C17—N5108.1 (2)H24B—C24—H24C109.5
N6—C17—C22124.9 (2)C23—C24—H24A109.5
C11—C12—H12119.7C23—C24—H24B109.5
C13—C12—C11120.7 (2)C23—C24—H24C109.5
C13—C12—H12119.7C22—C23—H23A109.0
N5—C14—C11113.1 (2)C22—C23—H23B109.0
N5—C14—H14A109.0C24—C23—C22113.1 (2)
N5—C14—H14B109.0C24—C23—H23A109.0
C11—C14—H14A109.0C24—C23—H23B109.0
C11—C14—H14B109.0H23A—C23—H23B107.8
H14A—C14—H14B107.8C5—C4—H4120.0
C8—C9—H9119.7C3—C4—C5120.1 (3)
C10—C9—C8120.6 (2)C3—C4—H4120.0
C10—C9—H9119.7C19—C20—H20A109.5
C11—C10—H10119.7C19—C20—H20B109.5
C9—C10—C11120.5 (2)C19—C20—H20C109.5
C9—C10—H10119.7H20A—C20—H20B109.5
O3—C18—O2125.7 (2)H20A—C20—H20C109.5
O3—C18—C15117.7 (2)H20B—C20—H20C109.5
O2—C18—C15116.7 (2)Cl1A—C1A—Cl2A111.6 (2)
N6—C16—C19120.4 (2)Cl1A—C1A—H1AA107.7
C15—C16—N6106.6 (2)Cl2A—C1A—H1AA107.7
C15—C16—C19132.7 (2)Cl3A—C1A—Cl1A111.7 (3)
C6—C5—H5119.4Cl3A—C1A—Cl2A110.2 (2)
C4—C5—H5119.4Cl3A—C1A—H1AA107.7
4-(2-Hydroxypropan-2-yl)-2-propyl-1-({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazol-3-ium-5-carboxylate acetonitrile monosolvate (Ol-Acn) top
Crystal data top
C24H26N6O3·C2H3NF(000) = 1032
Mr = 487.56Dx = 1.274 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 9.92522 (7) ÅCell parameters from 25587 reflections
b = 17.86566 (12) Åθ = 4.5–71.4°
c = 14.34306 (10) ŵ = 0.71 mm1
β = 91.4370 (6)°T = 110 K
V = 2542.52 (3) Å3Needle, colourless
Z = 40.1 × 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 Source4602 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.038
Detector resolution: 16.4335 pixels mm-1θmax = 71.7°, θmin = 4.5°
ω scansh = 1211
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
k = 2121
Tmin = 0.289, Tmax = 1.000l = 1717
43452 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.050H 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 reflectionsΔρmax = 0.47 e Å3
347 parametersΔρmin = 0.71 e Å3
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
xyzUiso*/UeqOcc. (<1)
O10.90689 (11)0.17622 (6)0.20891 (7)0.0194 (2)
H10.9261660.1980760.1607760.029*
O31.21197 (12)0.27756 (8)0.03063 (8)0.0302 (3)
N61.20504 (12)0.23466 (7)0.34207 (8)0.0170 (3)
H61.1878110.2243910.3991200.020*
N51.31393 (12)0.26543 (7)0.21972 (8)0.0157 (3)
O21.00561 (12)0.25223 (8)0.07649 (8)0.0327 (3)
C91.70037 (14)0.18371 (8)0.04021 (10)0.0164 (3)
H91.7818640.1947920.0127210.020*
C101.62789 (15)0.24025 (8)0.08197 (10)0.0163 (3)
H101.6626430.2885830.0840940.020*
C161.11200 (15)0.23328 (8)0.26916 (10)0.0159 (3)
C111.50347 (14)0.22544 (8)0.12082 (10)0.0153 (3)
C141.42692 (15)0.28981 (8)0.16281 (10)0.0175 (3)
H14A1.4885760.3193510.2013020.021*
H14B1.3925460.3217300.1129520.021*
C121.45439 (15)0.15252 (9)0.11852 (10)0.0190 (3)
H121.3710500.1419540.1436620.023*
C131.52867 (15)0.09537 (9)0.07904 (11)0.0203 (3)
H131.4957110.0466430.0792870.024*
C81.65252 (15)0.11052 (8)0.03896 (10)0.0176 (3)
C151.17969 (15)0.25341 (8)0.19052 (10)0.0160 (3)
C181.12875 (16)0.26239 (9)0.09122 (10)0.0194 (3)
N11.79072 (15)0.03609 (8)0.21193 (10)0.0272 (3)
C190.96525 (15)0.21467 (9)0.28696 (10)0.0186 (3)
C231.53900 (17)0.18804 (11)0.36270 (12)0.0290 (4)
H23A1.5697960.1843670.2992170.035*
H23B1.6178070.1937770.4034480.035*
C51.75653 (17)0.05224 (10)0.09981 (12)0.0279 (4)
H51.7225970.0919190.1351900.033*
C11.78385 (16)0.01091 (9)0.04734 (12)0.0250 (4)
C61.73274 (15)0.04975 (9)0.00460 (11)0.0213 (3)
C221.44986 (16)0.25805 (10)0.37108 (11)0.0223 (3)
H22A1.4247470.2640260.4355740.027*
H22B1.5015310.3017700.3537720.027*
C71.76619 (18)0.01707 (9)0.14821 (13)0.0280 (4)
N21.76726 (19)0.00850 (9)0.29715 (12)0.0406 (4)
N41.7280 (2)0.07822 (9)0.19200 (13)0.0469 (5)
C171.32560 (15)0.25422 (8)0.31130 (10)0.0171 (3)
C210.95370 (18)0.16176 (11)0.36946 (11)0.0288 (4)
H21A0.8614130.1468330.3754840.043*
H21B0.9839730.1867510.4254200.043*
H21C1.0084290.1183180.3595560.043*
C31.87947 (19)0.06329 (11)0.09116 (16)0.0390 (5)
H31.9285130.1006990.1200010.047*
C21.85617 (18)0.06748 (10)0.00284 (15)0.0338 (4)
H21.8886180.1081200.0371300.041*
C41.83000 (19)0.00348 (11)0.14282 (14)0.0370 (5)
H41.8459810.0006130.2063350.044*
N31.7300 (3)0.06029 (10)0.28431 (14)0.0559 (6)
C241.4676 (2)0.11625 (12)0.38747 (16)0.0439 (5)
H24A1.3925450.1085500.3450260.066*
H24B1.4358010.1196100.4499930.066*
H24C1.5291030.0749980.3831110.066*
C200.88951 (17)0.28742 (10)0.30324 (15)0.0332 (4)
H20A0.8958120.3188580.2492420.050*
H20B0.9284460.3127120.3564760.050*
H20C0.7965320.2765790.3142720.050*
N1A1.2974 (7)0.0694 (3)0.3504 (5)0.163 (2)
C2A1.2437 (11)0.0377 (5)0.4077 (6)0.114 (2)0.6
C1AB1.109 (3)0.0504 (16)0.4489 (19)0.272 (14)0.4
H1AA1.0443700.0185940.4173670.408*0.4
H1AB1.1665690.0206220.4887260.408*0.4
H1AC1.0622580.0865210.4857530.408*0.4
H1A1.818 (2)0.0804 (10)0.2057 (16)0.040 (6)*
C2B1.1876 (14)0.0881 (7)0.3820 (9)0.114 (2)0.4
C1AA1.1780 (9)0.0083 (6)0.4845 (6)0.153 (5)0.6
H1AD1.0818460.0033860.4790750.230*0.6
H1AE1.2024740.0599980.4779700.230*0.6
H1AF1.2086710.0096630.5444010.230*0.6
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0206 (5)0.0229 (5)0.0145 (5)0.0039 (4)0.0024 (4)0.0010 (4)
O30.0221 (6)0.0547 (8)0.0139 (5)0.0003 (5)0.0011 (4)0.0018 (5)
N60.0167 (6)0.0230 (6)0.0113 (6)0.0005 (5)0.0002 (5)0.0018 (5)
N50.0142 (6)0.0190 (6)0.0141 (6)0.0012 (5)0.0004 (5)0.0031 (5)
O20.0223 (6)0.0536 (8)0.0219 (6)0.0095 (6)0.0070 (5)0.0134 (5)
C90.0132 (7)0.0220 (7)0.0140 (6)0.0008 (5)0.0003 (5)0.0010 (5)
C100.0161 (7)0.0172 (7)0.0156 (7)0.0017 (5)0.0014 (5)0.0009 (5)
C160.0155 (7)0.0173 (7)0.0148 (7)0.0024 (5)0.0007 (5)0.0032 (5)
C110.0147 (7)0.0199 (7)0.0111 (6)0.0010 (5)0.0017 (5)0.0006 (5)
C140.0157 (7)0.0191 (7)0.0177 (7)0.0016 (6)0.0024 (5)0.0012 (6)
C120.0152 (7)0.0225 (8)0.0194 (7)0.0027 (6)0.0034 (5)0.0017 (6)
C130.0190 (7)0.0184 (7)0.0235 (8)0.0037 (6)0.0022 (6)0.0029 (6)
C80.0157 (7)0.0201 (7)0.0169 (7)0.0007 (6)0.0002 (5)0.0019 (6)
C150.0147 (7)0.0176 (7)0.0156 (7)0.0024 (5)0.0007 (5)0.0025 (5)
C180.0204 (8)0.0228 (8)0.0148 (7)0.0019 (6)0.0019 (6)0.0003 (6)
N10.0328 (8)0.0182 (7)0.0304 (8)0.0041 (6)0.0016 (6)0.0029 (6)
C190.0153 (7)0.0236 (8)0.0168 (7)0.0017 (6)0.0012 (5)0.0055 (6)
C230.0201 (8)0.0466 (10)0.0199 (8)0.0099 (7)0.0039 (6)0.0051 (7)
C50.0255 (8)0.0281 (9)0.0304 (9)0.0068 (7)0.0081 (7)0.0079 (7)
C10.0189 (7)0.0184 (8)0.0378 (9)0.0032 (6)0.0001 (6)0.0073 (7)
C60.0145 (7)0.0206 (7)0.0290 (8)0.0041 (6)0.0036 (6)0.0071 (6)
C220.0177 (7)0.0326 (9)0.0164 (7)0.0010 (6)0.0028 (6)0.0039 (6)
C70.0284 (9)0.0163 (7)0.0391 (10)0.0008 (6)0.0042 (7)0.0010 (7)
N20.0596 (11)0.0288 (8)0.0333 (9)0.0104 (8)0.0021 (8)0.0077 (7)
N40.0722 (13)0.0231 (8)0.0453 (10)0.0127 (8)0.0040 (9)0.0042 (7)
C170.0166 (7)0.0199 (7)0.0149 (7)0.0016 (5)0.0004 (5)0.0036 (5)
C210.0262 (8)0.0428 (10)0.0173 (8)0.0119 (7)0.0002 (6)0.0005 (7)
C30.0255 (9)0.0296 (9)0.0625 (13)0.0046 (7)0.0140 (9)0.0245 (9)
C20.0224 (8)0.0205 (8)0.0583 (12)0.0004 (7)0.0002 (8)0.0119 (8)
C40.0327 (10)0.0391 (10)0.0401 (10)0.0119 (8)0.0165 (8)0.0198 (8)
N30.0928 (16)0.0301 (9)0.0445 (11)0.0189 (10)0.0023 (10)0.0098 (8)
C240.0493 (12)0.0385 (11)0.0438 (11)0.0150 (9)0.0009 (9)0.0041 (9)
C200.0189 (8)0.0294 (9)0.0516 (11)0.0005 (7)0.0077 (7)0.0159 (8)
N1A0.185 (5)0.117 (4)0.185 (5)0.024 (3)0.031 (4)0.030 (3)
C2A0.148 (6)0.100 (5)0.093 (4)0.020 (4)0.016 (4)0.014 (3)
C1AB0.26 (2)0.29 (2)0.27 (2)0.024 (16)0.047 (16)0.029 (16)
C2B0.148 (6)0.100 (5)0.093 (4)0.020 (4)0.016 (4)0.014 (3)
C1AA0.127 (7)0.184 (9)0.147 (8)0.038 (7)0.044 (6)0.129 (8)
Geometric parameters (Å, º) top
O1—C191.4241 (17)N1—N21.344 (2)
O3—C181.244 (2)C19—C211.521 (2)
N6—C161.3778 (19)C19—C201.522 (2)
N6—C171.332 (2)C23—C221.538 (2)
N5—C141.4696 (18)C23—C241.512 (3)
N5—C151.4031 (19)C5—C61.392 (2)
N5—C171.3309 (19)C5—C41.388 (2)
O2—C181.248 (2)C1—C61.403 (2)
C9—C101.385 (2)C1—C71.466 (3)
C9—C81.391 (2)C1—C21.403 (2)
C10—C111.393 (2)C22—C171.486 (2)
C16—C151.375 (2)C7—N41.321 (2)
C16—C191.522 (2)N2—N31.295 (2)
C11—C141.512 (2)N4—N31.362 (3)
C11—C121.391 (2)C3—C21.376 (3)
C12—C131.388 (2)C3—C41.383 (3)
C13—C81.397 (2)N1A—C2A1.141 (8)
C8—C61.493 (2)N1A—C2B1.236 (13)
C15—C181.508 (2)C2A—C1AA1.532 (12)
N1—C71.336 (2)C1AB—C2B1.422 (17)
C17—N6—C16110.11 (12)O1—C19—C20109.86 (13)
C15—N5—C14127.72 (12)C16—C19—C20108.51 (13)
C17—N5—C14122.95 (12)C21—C19—C16110.94 (13)
C17—N5—C15109.27 (12)C21—C19—C20111.35 (14)
C10—C9—C8120.68 (13)C24—C23—C22113.42 (15)
C9—C10—C11120.65 (14)C4—C5—C6121.13 (18)
N6—C16—C19120.18 (13)C6—C1—C7122.11 (15)
C15—C16—N6106.61 (13)C2—C1—C6119.83 (17)
C15—C16—C19133.17 (13)C2—C1—C7118.05 (16)
C10—C11—C14118.32 (13)C5—C6—C8119.51 (15)
C12—C11—C10118.81 (13)C5—C6—C1118.53 (15)
C12—C11—C14122.87 (13)C1—C6—C8121.95 (14)
N5—C14—C11113.21 (12)C17—C22—C23112.84 (13)
C13—C12—C11120.61 (14)N1—C7—C1126.70 (15)
C12—C13—C8120.48 (14)N4—C7—N1108.19 (17)
C9—C8—C13118.73 (13)N4—C7—C1125.06 (16)
C9—C8—C6120.24 (13)N3—N2—N1105.90 (16)
C13—C8—C6121.03 (13)C7—N4—N3105.70 (16)
N5—C15—C18123.98 (13)N6—C17—C22124.08 (13)
C16—C15—N5105.96 (12)N5—C17—N6108.04 (13)
C16—C15—C18130.05 (14)N5—C17—C22127.81 (14)
O3—C18—O2125.30 (14)C2—C3—C4120.06 (16)
O3—C18—C15118.06 (14)C3—C2—C1120.49 (18)
O2—C18—C15116.62 (13)C3—C4—C5119.96 (18)
C7—N1—N2109.20 (15)N2—N3—N4111.01 (16)
O1—C19—C16110.22 (11)N1A—C2A—C1AA176.7 (11)
O1—C19—C21105.95 (12)N1A—C2B—C1AB128.6 (17)
Molecular interaction energies (kJ mol-1) for selected contacts top
CrystalInteraction pairContactEeleEpolEdispErepEtot
Ol-MeOHOlmersartan–methanolO1A—H1AA···O2-38.2-8.4-9.5517.6-38.5
Ol–OlN6—H6···O3-99.2-35.2-45.868.0-112.2
Ol–OlN1—H1A···O1-75.5-19.3-37.142.6-89.2
Ol-EtOHOlmersartan–ethanolO1A—H1AA···N3-10.0-3.0-16.013.3-15.7
Ol–OlN6—H6···O3-107.3-37.4-48.070.4-122.3
Ol–OlN1—H1A···O1-81.0-20.3-39.348.5-92.1
Ol-IsoPropOlmersartan–isopropanolO1A—H1AA···N3-10.4-3.9-21.613.5-22.3
Ol–OlN6—H6···O3-100.5-35.0-53.060.3-128.2
Ol–OlN1—H1A···O1-79.5-19.8-39.046.9-91.4
Ol-IsoButOlmersartan–isobutanolO1A—H1AA···N4-40.1-7.7-33.235.8-45.2
Ol–OlN6—H6···O3-110.5-37.2-42.969.0-121.6
Ol–OlN1—H1A···O1-81.6-20.4-39.248.2-93.0
Ol-EthoxOlmersartan–ethoxyethanolO1A—H1AA···N4-36.7-7.3-14.330.5-27.8
Ol–OlN6—H6···O3-111.3-37.0-46.369.2-127.4
Ol–OlN1—H1A···O1-83.8-22.5-33.048.2-91.1
Ol-ChlOlmersartan–chloroformC20—H20A···Cl1-12.5-3.6-13.98.1-21.9
Ol–OlN6—H6···O3-106.9-35.8-46.965.2-124.4
Ol–OlN1—H1A···O1-68.8-17.7-37.341.2-82.6
Ol-AcnOlmersatan–acetonitrileC1A—H1AB···N2-18.0-2.5-8.510.7-18.3
Ol–OlN6—H6···O3-101.6-35.6-46.062.0-121.2
Ol–OlN1—H1A···O1-77.5-20.0-37.845.4-89.9
Abbreviation: Ol is olmesartan.
Crystal energies (kJ mol-1) top
Ecoul is the Coulombic term, Epol the polarization term, Edisp the dispersion term, Erep the repulsion term and Elatt the total energy term.
StructureEcoulEpolEdispErepElatt
Ol-109.3-48.6-202.2111.0-249.1
Ol-MeOH-63.2-33.0-129.375.3-150.3
Ol-EtOH-61.5-35.5-135.176.4-155.6
Ol-IsoProp-60.1-39.4-140.675.4-164.7
Ol-Ethox-68.3-36.3-148.083.3-169.3
Ol-Chl-55.5-29.4-144.674.0-155.5
Ol-Acn-58.8-32.0-120.760.6-150.8
 

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