Structural studies of various olmesartan solvates

Grosu, I.G.; Martin, F.; Turza, A.; Miclaus, M.; Kacso, I.; Borodi, G.

doi:10.1107/S2053229622002984

Structural studies of various olmesartan solvates

I. G. Grosu, F. Martin, A. Turza, M. Miclaus, I. Kacso and G. Borodi

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.

Keywords: olmesartan; isostructural; solid form; crystal structure; angiotensin II receptor blocker agent.

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Supporting information

	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
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229622002984/dv3017Ol-MeOHsup2.hkl Contains datablock Ol-MeOH
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229622002984/dv3017Ol-EtOHsup3.hkl Contains datablock Ol-EtOH
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229622002984/dv3017Ol-IsoPropsup4.hkl Contains datablock Ol-IsoProp
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229622002984/dv3017Ol-IsoButsup5.hkl Contains datablock Ol-IsoBut
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229622002984/dv3017Ol-Etoxsup6.hkl Contains datablock Ol-Etox
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229622002984/dv3017Ol-Chlsup7.hkl Contains datablock Ol-Chl
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229622002984/dv3017Ol-Acnsup8.hkl Contains datablock Ol-Acn
	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·CH₄O	F(000) = 1016
M_r = 478.55	D_x = 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	R_int = 0.022
Detector resolution: 16.4335 pixels mm^-1	θ_max = 71.7°, θ_min = 4.5°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −21→21
T_min = 0.762, T_max = 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(F_o²) + (0.0791P)² + 2.3619P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
4874 reflections	Δρ_max = 0.48 e Å⁻³
326 parameters	Δρ_min = −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	U_iso*/U_eq
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-(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·C₂H₆O	F(000) = 1048
M_r = 492.57	D_x = 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	R_int = 0.026
Detector resolution: 16.4335 pixels mm^-1	θ_max = 71.8°, θ_min = 3.9°
ω scans	h = −12→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −22→21
T_min = 0.664, T_max = 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(F_o²) + (0.0819P)² + 2.3824P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
4875 reflections	Δρ_max = 0.72 e Å⁻³
335 parameters	Δρ_min = −0.70 e Å⁻³
1 restraint

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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-(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·C₃H₈O	F(000) = 1080
M_r = 506.60	D_x = 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	R_int = 0.021
Detector resolution: 16.4335 pixels mm^-1	θ_max = 71.8°, θ_min = 3.9°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −19→22
T_min = 0.882, T_max = 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(F_o²) + (0.0598P)² + 1.5357P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
5025 reflections	Δρ_max = 0.44 e Å⁻³
345 parameters	Δρ_min = −0.31 e Å⁻³
1 restraint

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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-(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·C₄H₁₀O	F(000) = 1112
M_r = 520.63	D_x = 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	R_int = 0.038
Detector resolution: 16.4335 pixels mm^-1	θ_max = 71.8°, θ_min = 3.8°
ω scans	h = −11→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −23→20
T_min = 0.867, T_max = 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(F_o²) + (0.0527P)² + 1.2805P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
5270 reflections	Δρ_max = 0.28 e Å⁻³
354 parameters	Δρ_min = −0.25 e Å⁻³
1 restraint

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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-(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·C₄H₁₀O₂	F(000) = 1144
M_r = 536.63	D_x = 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	R_int = 0.035
Detector resolution: 16.4335 pixels mm^-1	θ_max = 71.8°, θ_min = 3.9°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −23→23
T_min = 0.768, T_max = 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(F_o²) + (0.0513P)² + 2.2675P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
5469 reflections	Δρ_max = 0.37 e Å⁻³
362 parameters	Δρ_min = −0.33 e Å⁻³
1 restraint

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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-(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·CHCl₃	F(000) = 1176
M_r = 565.87	D_x = 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	R_int = 0.018
Detector resolution: 16.4335 pixels mm^-1	θ_max = 72.6°, θ_min = 3.9°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −22→21
T_min = 0.500, T_max = 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(F_o²) + (0.0977P)² + 6.8312P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.002
5115 reflections	Δρ_max = 0.99 e Å⁻³
342 parameters	Δρ_min = −1.70 e Å⁻³
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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-(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·C₂H₃N	F(000) = 1032
M_r = 487.56	D_x = 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	R_int = 0.038
Detector resolution: 16.4335 pixels mm^-1	θ_max = 71.7°, θ_min = 4.5°
ω scans	h = −12→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −21→21
T_min = 0.289, T_max = 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(F_o²) + (0.0664P)² + 1.6749P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
4937 reflections	Δρ_max = 0.47 e Å⁻³
347 parameters	Δρ_min = −0.71 e Å⁻³
29 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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 top

Crystal	Interaction pair	Contact	E_ele	E_pol	E_disp	E_rep	E_tot
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) top

E_coul is the Coulombic term, E_pol the polarization term, E_disp the dispersion term, E_rep the repulsion term and E_latt the total energy term.

Structure	E_coul	E_pol	E_disp	E_rep	E_latt
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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