A com­parison of three crystalline forms of miconazole: solvent-free, ethanol monosolvate and hemihydrate

The crystal structures of miconazole {MIC, C₁₈H₁₄Cl₄N₂O, systematic name (RS)-1-[2-(2,4-di­chloro­benz­yloxy)-2-(2,4-di­chloro­phen­yl)eth­yl]-1H-imidazole}, its ethanol monosolvate (C₁₈H₁₄Cl₄N₂O·C₂H₅OH) and its hemihydrate (C₁₈H₁₄Cl₄N₂O·0.5H₂O) were com­pared. A detailed com­parison of the mol­ecular conformation of the miconazole mol­ecules showed a structural similarity of the solvate forms, whereas the unsolvated form is related to the gas-phase structure. This suggests that the mol­ecular conformation of miconazole is influenced by solvent mol­ecules. The crystal architectures of the considered solvatomorphs are differentiated by the inter­molecular inter­actions formed by ethanol and water mol­ecules. The structural studies are enriched by Hirshfeld surface and energy framework analysis. The pairwise model energies of the dominant contacts were estimated to be in the range 20–70 kJ mol⁻¹. It is inter­esting that the contribution of dispersive forces predominates over the electrostatic forces.

Computing details

For all structures, data collection: CrysAlis PRO (Rigaku OD, 2021); cell refinement: CrysAlis PRO (Rigaku OD, 2021); data reduction: CrysAlis PRO (Rigaku OD, 2021); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b) and publCIF (Westrip, 2010).

(RS)-1-[2-(2,4-Dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole (MIC)

Crystal data

C18H14Cl4N2O	F(000) = 848
Mr = 416.11	Dx = 1.493 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.1902 (5) Å	Cell parameters from 6096 reflections
b = 18.5341 (8) Å	θ = 2.6–29.6°
c = 14.2507 (7) Å	µ = 0.65 mm^−1
β = 102.814 (6)°	T = 293 K
V = 1851.81 (18) Å^3	Prism, colourless
Z = 4	0.15 × 0.10 × 0.02 mm

Data collection

Rigaku XtaLAB Synergy Dualflex HyPix diffractometer	7789 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Mo) X-ray Source	3850 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	Rint = 0.057
ω scans	θmax = 28.0°, θmin = 2.6°
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2021)	h = −8→9
Tmin = 0.984, Tmax = 0.996	k = −24→24
7789 measured reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.138	w = 1/[σ^2(Fo^2) + (0.0683P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.88	(Δ/σ)max < 0.001
7789 reflections	Δρmax = 0.22 e Å^−3
227 parameters	Δρmin = −0.21 e Å^−3
0 restraints

Special details

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. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.68824 (15)	0.17840 (5)	0.66591 (6)	0.0804 (3)
Cl2	0.68906 (15)	0.46252 (5)	0.59908 (7)	0.0794 (3)
Cl3	0.24762 (17)	0.01407 (5)	0.22361 (8)	0.0892 (3)
Cl4	0.08129 (14)	0.16042 (7)	−0.10809 (7)	0.0957 (4)
O1	0.5211 (3)	0.15622 (11)	0.34559 (14)	0.0559 (5)
N1	0.7834 (4)	0.04527 (14)	0.43453 (19)	0.0580 (6)
N2	0.7429 (4)	−0.07207 (18)	0.4525 (3)	0.0828 (10)
C1	0.6057 (4)	0.15782 (16)	0.4462 (2)	0.0515 (7)
H1	0.527172	0.129766	0.481121	0.062*
C2	0.7990 (4)	0.12183 (17)	0.4569 (2)	0.0596 (8)
H2A	0.868596	0.145360	0.414468	0.072*
H2B	0.871349	0.128103	0.522479	0.072*
C3	0.7542 (5)	−0.0085 (2)	0.4926 (3)	0.0739 (10)
H3	0.742981	−0.001151	0.555641	0.089*
C4	0.7670 (6)	−0.0579 (2)	0.3628 (3)	0.0925 (13)
H4	0.765698	−0.092567	0.315486	0.111*
C5	0.7930 (7)	0.0128 (2)	0.3513 (3)	0.0886 (12)
H5	0.813746	0.035301	0.296112	0.106*
C6	0.6268 (4)	0.23446 (16)	0.4851 (2)	0.0503 (7)
C7	0.6635 (4)	0.24907 (17)	0.5833 (2)	0.0546 (7)
C8	0.6819 (4)	0.31846 (18)	0.6198 (2)	0.0587 (8)
H8	0.705115	0.326855	0.685736	0.070*
C9	0.6646 (4)	0.37477 (17)	0.5553 (2)	0.0579 (8)
C10	0.6300 (5)	0.36308 (18)	0.4577 (2)	0.0602 (8)
H10	0.619176	0.401724	0.415225	0.072*
C11	0.6117 (4)	0.29330 (16)	0.4239 (2)	0.0559 (7)
H11	0.588458	0.285396	0.357855	0.067*
C12	0.3171 (4)	0.16181 (18)	0.3241 (2)	0.0598 (8)
H12A	0.278459	0.206467	0.349735	0.072*
H12B	0.262363	0.121804	0.352604	0.072*
C13	0.2501 (4)	0.16037 (16)	0.2166 (2)	0.0530 (7)
C14	0.2189 (4)	0.09641 (16)	0.1643 (2)	0.0566 (7)
C15	0.1655 (4)	0.0963 (2)	0.0652 (2)	0.0646 (8)
H15	0.143930	0.052975	0.031537	0.078*
C16	0.1448 (4)	0.1607 (2)	0.0169 (2)	0.0643 (9)
C17	0.1735 (5)	0.2258 (2)	0.0659 (3)	0.0667 (9)
H17	0.158809	0.269406	0.032798	0.080*
C18	0.2242 (4)	0.22397 (17)	0.1647 (2)	0.0630 (8)
H18	0.241914	0.267442	0.198140	0.076*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1130 (8)	0.0780 (6)	0.0459 (4)	0.0017 (5)	0.0083 (4)	0.0109 (4)
Cl2	0.1009 (7)	0.0651 (5)	0.0707 (6)	−0.0039 (5)	0.0158 (5)	−0.0137 (4)
Cl3	0.1257 (9)	0.0580 (5)	0.0883 (7)	−0.0008 (5)	0.0333 (6)	0.0073 (5)
Cl4	0.0762 (6)	0.1549 (11)	0.0516 (5)	−0.0220 (6)	0.0047 (4)	0.0061 (6)
O1	0.0508 (12)	0.0680 (13)	0.0459 (11)	0.0033 (9)	0.0044 (9)	−0.0054 (10)
N1	0.0576 (15)	0.0595 (15)	0.0531 (15)	0.0058 (12)	0.0037 (12)	0.0024 (13)
N2	0.078 (2)	0.062 (2)	0.106 (3)	0.0003 (15)	0.0170 (18)	0.006 (2)
C1	0.0499 (17)	0.0593 (17)	0.0428 (15)	−0.0025 (14)	0.0045 (12)	0.0004 (13)
C2	0.0583 (19)	0.0577 (18)	0.0589 (19)	0.0020 (14)	0.0046 (14)	−0.0018 (15)
C3	0.080 (2)	0.070 (2)	0.076 (3)	0.0044 (18)	0.0261 (19)	0.007 (2)
C4	0.112 (3)	0.069 (3)	0.085 (3)	0.011 (2)	−0.001 (2)	−0.015 (2)
C5	0.133 (4)	0.071 (2)	0.057 (2)	0.012 (2)	0.011 (2)	−0.0013 (19)
C6	0.0452 (17)	0.0605 (17)	0.0445 (15)	0.0005 (13)	0.0089 (12)	−0.0008 (13)
C7	0.0515 (18)	0.0645 (19)	0.0460 (15)	0.0009 (14)	0.0072 (13)	0.0034 (14)
C8	0.059 (2)	0.073 (2)	0.0421 (15)	−0.0019 (16)	0.0075 (13)	−0.0065 (15)
C9	0.0544 (19)	0.0610 (19)	0.0581 (18)	−0.0024 (14)	0.0122 (14)	−0.0041 (15)
C10	0.067 (2)	0.0619 (19)	0.0512 (17)	−0.0024 (15)	0.0128 (15)	0.0065 (15)
C11	0.0603 (19)	0.0650 (19)	0.0425 (15)	−0.0017 (15)	0.0118 (13)	−0.0003 (14)
C12	0.0552 (19)	0.070 (2)	0.0529 (17)	0.0025 (15)	0.0089 (14)	−0.0067 (16)
C13	0.0425 (16)	0.0609 (18)	0.0535 (16)	0.0032 (13)	0.0058 (13)	−0.0020 (15)
C14	0.0540 (18)	0.0560 (17)	0.0603 (19)	−0.0029 (14)	0.0139 (15)	0.0013 (15)
C15	0.062 (2)	0.071 (2)	0.062 (2)	−0.0147 (16)	0.0140 (16)	−0.0139 (17)
C16	0.0416 (17)	0.096 (3)	0.0526 (17)	−0.0067 (17)	0.0041 (13)	0.0053 (19)
C17	0.056 (2)	0.071 (2)	0.069 (2)	0.0067 (16)	0.0061 (16)	0.0155 (18)
C18	0.060 (2)	0.0572 (19)	0.067 (2)	0.0040 (15)	0.0029 (16)	−0.0015 (16)

Geometric parameters (Å, º)

Cl1—C7	1.744 (3)	C6—C7	1.391 (4)
Cl2—C9	1.737 (3)	C7—C8	1.383 (4)
Cl3—C14	1.734 (3)	C8—C9	1.379 (4)
Cl4—C16	1.738 (3)	C8—H8	0.9300
O1—C1	1.429 (3)	C9—C10	1.374 (4)
O1—C12	1.434 (3)	C10—C11	1.376 (4)
N1—C3	1.341 (5)	C10—H10	0.9300
N1—C5	1.346 (5)	C11—H11	0.9300
N1—C2	1.453 (4)	C12—C13	1.500 (4)
N2—C3	1.303 (5)	C12—H12A	0.9700
N2—C4	1.354 (6)	C12—H12B	0.9700
C1—C2	1.519 (4)	C13—C18	1.382 (4)
C1—C6	1.520 (4)	C13—C14	1.392 (4)
C1—H1	0.9800	C14—C15	1.380 (4)
C2—H2A	0.9700	C15—C16	1.369 (5)
C2—H2B	0.9700	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.386 (5)
C4—C5	1.339 (6)	C17—C18	1.376 (5)
C4—H4	0.9300	C17—H17	0.9300
C5—H5	0.9300	C18—H18	0.9300
C6—C11	1.386 (4)
C1—O1—C12	113.6 (2)	C7—C8—H8	121.1
C3—N1—C5	104.9 (3)	C10—C9—C8	121.7 (3)
C3—N1—C2	127.2 (3)	C10—C9—Cl2	119.5 (3)
C5—N1—C2	127.8 (3)	C8—C9—Cl2	118.8 (2)
C3—N2—C4	103.3 (3)	C9—C10—C11	119.0 (3)
O1—C1—C2	105.5 (2)	C9—C10—H10	120.5
O1—C1—C6	111.8 (2)	C11—C10—H10	120.5
C2—C1—C6	111.0 (2)	C10—C11—C6	122.1 (3)
O1—C1—H1	109.5	C10—C11—H11	119.0
C2—C1—H1	109.5	C6—C11—H11	119.0
C6—C1—H1	109.5	O1—C12—C13	107.4 (2)
N1—C2—C1	112.5 (3)	O1—C12—H12A	110.2
N1—C2—H2A	109.1	C13—C12—H12A	110.2
C1—C2—H2A	109.1	O1—C12—H12B	110.2
N1—C2—H2B	109.1	C13—C12—H12B	110.2
C1—C2—H2B	109.1	H12A—C12—H12B	108.5
H2A—C2—H2B	107.8	C18—C13—C14	117.0 (3)
N2—C3—N1	113.9 (4)	C18—C13—C12	120.4 (3)
N2—C3—H3	123.1	C14—C13—C12	122.6 (3)
N1—C3—H3	123.1	C15—C14—C13	121.7 (3)
C5—C4—N2	110.9 (4)	C15—C14—Cl3	118.3 (3)
C5—C4—H4	124.6	C13—C14—Cl3	120.1 (2)
N2—C4—H4	124.6	C16—C15—C14	119.2 (3)
C4—C5—N1	107.0 (4)	C16—C15—H15	120.4
C4—C5—H5	126.5	C14—C15—H15	120.4
N1—C5—H5	126.5	C15—C16—C17	121.2 (3)
C11—C6—C7	116.8 (3)	C15—C16—Cl4	119.2 (3)
C11—C6—C1	121.2 (2)	C17—C16—Cl4	119.6 (3)
C7—C6—C1	122.0 (3)	C18—C17—C16	118.1 (3)
C8—C7—C6	122.7 (3)	C18—C17—H17	121.0
C8—C7—Cl1	117.2 (2)	C16—C17—H17	121.0
C6—C7—Cl1	120.1 (2)	C17—C18—C13	122.8 (3)
C9—C8—C7	117.8 (3)	C17—C18—H18	118.6
C9—C8—H8	121.1	C13—C18—H18	118.6
C12—O1—C1—C2	157.6 (2)	C7—C8—C9—C10	0.1 (5)
C12—O1—C1—C6	−81.7 (3)	C7—C8—C9—Cl2	−179.4 (2)
C3—N1—C2—C1	−81.5 (4)	C8—C9—C10—C11	0.2 (5)
C5—N1—C2—C1	97.7 (4)	Cl2—C9—C10—C11	179.7 (3)
O1—C1—C2—N1	−67.7 (3)	C9—C10—C11—C6	0.1 (5)
C6—C1—C2—N1	171.0 (3)	C7—C6—C11—C10	−0.6 (4)
C4—N2—C3—N1	0.1 (4)	C1—C6—C11—C10	179.9 (3)
C5—N1—C3—N2	−0.6 (4)	C1—O1—C12—C13	179.2 (2)
C2—N1—C3—N2	178.8 (3)	O1—C12—C13—C18	−92.5 (3)
C3—N2—C4—C5	0.4 (5)	O1—C12—C13—C14	84.9 (3)
N2—C4—C5—N1	−0.7 (5)	C18—C13—C14—C15	0.3 (5)
C3—N1—C5—C4	0.7 (4)	C12—C13—C14—C15	−177.1 (3)
C2—N1—C5—C4	−178.6 (3)	C18—C13—C14—Cl3	−179.9 (2)
O1—C1—C6—C11	−15.6 (4)	C12—C13—C14—Cl3	2.7 (4)
C2—C1—C6—C11	101.9 (3)	C13—C14—C15—C16	0.7 (5)
O1—C1—C6—C7	164.9 (2)	Cl3—C14—C15—C16	−179.1 (2)
C2—C1—C6—C7	−77.6 (4)	C14—C15—C16—C17	−1.0 (5)
C11—C6—C7—C8	0.9 (4)	C14—C15—C16—Cl4	179.0 (2)
C1—C6—C7—C8	−179.6 (3)	C15—C16—C17—C18	0.2 (5)
C11—C6—C7—Cl1	−179.1 (2)	Cl4—C16—C17—C18	−179.8 (2)
C1—C6—C7—Cl1	0.4 (4)	C16—C17—C18—C13	0.9 (5)
C6—C7—C8—C9	−0.7 (5)	C14—C13—C18—C17	−1.2 (5)
Cl1—C7—C8—C9	179.3 (2)	C12—C13—C18—C17	176.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N2^i	0.98	2.57	3.534 (4)	167
C5—H5···Cl2^ii	0.93	2.75	3.534 (4)	142

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, −y+1/2, z−1/2.

(RS)-1-[2-(2,4-Dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole ethanol monosolvate (MIC_EtOH)

Crystal data

C18H14Cl4N2O·C2H6O	Z = 2
Mr = 462.18	F(000) = 476
Triclinic, P1	Dx = 1.430 Mg m^−3
a = 8.0766 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.5926 (3) Å	Cell parameters from 11675 reflections
c = 13.0383 (4) Å	θ = 2.6–30.6°
α = 115.423 (3)°	µ = 0.57 mm^−1
β = 99.068 (2)°	T = 293 K
γ = 94.776 (2)°	Prism, colourless
V = 1073.06 (6) Å^3	0.15 × 0.10 × 0.04 mm

Data collection

Rigaku XtaLAB Synergy Dualflex HyPix diffractometer	5130 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Mo) X-ray Source	3866 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	Rint = 0.036
ω scans	θmax = 28.0°, θmin = 2.6°
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2021)	h = −10→10
Tmin = 0.749, Tmax = 1.000	k = −15→15
24180 measured reflections	l = −16→17

Refinement

Refinement on F^2	Primary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0433P)^2 + 0.1988P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
5130 reflections	Δρmax = 0.28 e Å^−3
258 parameters	Δρmin = −0.26 e Å^−3
0 restraints

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.14615 (5)	0.08937 (5)	−0.05873 (5)	0.07059 (17)
Cl2	0.70773 (7)	−0.04509 (5)	−0.21679 (5)	0.07166 (17)
Cl3	0.67375 (7)	0.26069 (5)	0.46201 (4)	0.06363 (15)
Cl4	1.03341 (6)	0.73384 (5)	0.74446 (4)	0.06272 (15)
O1	0.48976 (13)	0.43158 (11)	0.23092 (9)	0.0402 (2)
O2	0.7124 (2)	0.74307 (17)	0.25280 (15)	0.0777 (5)
N1	0.21936 (16)	0.52871 (14)	0.13424 (11)	0.0418 (3)
N2	0.0041 (2)	0.62447 (17)	0.19415 (14)	0.0586 (4)
C1	0.37277 (19)	0.34750 (16)	0.12555 (13)	0.0391 (3)
H1	0.275927	0.306907	0.142209	0.047*
C2	0.3125 (2)	0.43001 (18)	0.06778 (14)	0.0466 (4)
H2A	0.410557	0.472184	0.055019	0.056*
H2B	0.239912	0.373782	−0.007706	0.056*
C3	0.0507 (2)	0.51503 (19)	0.12910 (15)	0.0500 (4)
H3	−0.024188	0.437205	0.084697	0.060*
C4	0.1519 (3)	0.7116 (2)	0.24283 (19)	0.0661 (5)
H4	0.159886	0.798734	0.293764	0.079*
C5	0.2853 (3)	0.6544 (2)	0.20713 (18)	0.0614 (5)
H5	0.398861	0.693353	0.228280	0.074*
C6	0.45550 (18)	0.24380 (16)	0.04228 (13)	0.0382 (3)
C7	0.36393 (19)	0.12702 (17)	−0.04457 (14)	0.0440 (4)
C8	0.4390 (2)	0.03650 (17)	−0.12479 (15)	0.0494 (4)
H8	0.375017	−0.041364	−0.182530	0.059*
C9	0.6109 (2)	0.06525 (17)	−0.11646 (15)	0.0475 (4)
C10	0.7070 (2)	0.17954 (18)	−0.03113 (16)	0.0514 (4)
H10	0.823274	0.197012	−0.026139	0.062*
C11	0.6286 (2)	0.26845 (17)	0.04737 (14)	0.0461 (4)
H11	0.693174	0.346293	0.104702	0.055*
C12	0.5327 (2)	0.37092 (16)	0.30356 (13)	0.0396 (3)
H12A	0.579419	0.293805	0.261831	0.048*
H12B	0.431301	0.345013	0.324908	0.048*
C13	0.66083 (18)	0.46299 (15)	0.41111 (12)	0.0368 (3)
C14	0.7314 (2)	0.42108 (16)	0.49085 (13)	0.0402 (3)
C15	0.8474 (2)	0.50206 (17)	0.59270 (13)	0.0451 (4)
H15	0.893305	0.471767	0.644574	0.054*
C16	0.8924 (2)	0.62846 (17)	0.61466 (13)	0.0441 (4)
C17	0.8280 (2)	0.67429 (17)	0.53826 (15)	0.0485 (4)
H17	0.861490	0.760103	0.554361	0.058*
C18	0.7119 (2)	0.59063 (17)	0.43642 (14)	0.0447 (4)
H18	0.667869	0.621257	0.384377	0.054*
C19	0.7899 (4)	0.8659 (3)	0.3475 (3)	0.0888 (8)
H19A	0.834458	0.922848	0.317696	0.107*
H19B	0.884063	0.854632	0.396659	0.107*
C20	0.6654 (5)	0.9243 (3)	0.4158 (3)	0.1124 (10)
H20A	0.575800	0.940105	0.368168	0.169*
H20B	0.720196	1.004767	0.481182	0.169*
H20C	0.618696	0.866454	0.442960	0.169*
H2	0.798 (4)	0.705 (3)	0.228 (3)	0.120 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0309 (2)	0.0699 (3)	0.0767 (3)	−0.0029 (2)	0.0080 (2)	0.0048 (3)
Cl2	0.0562 (3)	0.0592 (3)	0.0752 (3)	0.0155 (2)	0.0253 (2)	0.0031 (2)
Cl3	0.0854 (4)	0.0482 (3)	0.0555 (3)	0.0027 (2)	−0.0015 (2)	0.0287 (2)
Cl4	0.0518 (3)	0.0664 (3)	0.0423 (2)	0.0018 (2)	−0.00336 (18)	0.0051 (2)
O1	0.0401 (6)	0.0408 (6)	0.0352 (5)	0.0072 (5)	0.0002 (4)	0.0156 (5)
O2	0.0623 (9)	0.0746 (11)	0.0882 (11)	0.0216 (8)	0.0226 (8)	0.0254 (9)
N1	0.0385 (7)	0.0498 (8)	0.0385 (7)	0.0138 (6)	0.0052 (5)	0.0209 (6)
N2	0.0541 (9)	0.0702 (11)	0.0603 (9)	0.0278 (8)	0.0176 (8)	0.0327 (9)
C1	0.0312 (7)	0.0471 (9)	0.0345 (7)	0.0078 (6)	0.0034 (6)	0.0151 (7)
C2	0.0460 (9)	0.0588 (11)	0.0389 (8)	0.0210 (8)	0.0114 (7)	0.0227 (8)
C3	0.0397 (8)	0.0585 (11)	0.0518 (10)	0.0124 (8)	0.0076 (7)	0.0249 (9)
C4	0.0735 (14)	0.0523 (12)	0.0653 (12)	0.0199 (10)	0.0153 (10)	0.0180 (10)
C5	0.0525 (11)	0.0540 (12)	0.0649 (12)	0.0032 (9)	0.0058 (9)	0.0184 (9)
C6	0.0312 (7)	0.0443 (9)	0.0354 (7)	0.0074 (6)	0.0035 (6)	0.0155 (7)
C7	0.0293 (7)	0.0496 (10)	0.0454 (9)	0.0051 (7)	0.0038 (6)	0.0158 (7)
C8	0.0405 (9)	0.0426 (9)	0.0485 (9)	0.0028 (7)	0.0030 (7)	0.0082 (7)
C9	0.0402 (8)	0.0465 (10)	0.0476 (9)	0.0119 (7)	0.0110 (7)	0.0123 (8)
C10	0.0302 (8)	0.0561 (11)	0.0556 (10)	0.0058 (7)	0.0087 (7)	0.0144 (8)
C11	0.0328 (8)	0.0473 (10)	0.0439 (9)	0.0021 (7)	0.0038 (6)	0.0096 (7)
C12	0.0397 (8)	0.0416 (9)	0.0367 (8)	0.0083 (7)	0.0043 (6)	0.0180 (7)
C13	0.0346 (7)	0.0408 (8)	0.0327 (7)	0.0104 (6)	0.0084 (6)	0.0134 (6)
C14	0.0424 (8)	0.0415 (9)	0.0361 (8)	0.0097 (7)	0.0087 (6)	0.0164 (7)
C15	0.0447 (9)	0.0545 (10)	0.0343 (8)	0.0140 (8)	0.0058 (7)	0.0182 (7)
C16	0.0365 (8)	0.0502 (10)	0.0337 (8)	0.0079 (7)	0.0053 (6)	0.0086 (7)
C17	0.0513 (10)	0.0386 (9)	0.0471 (9)	0.0047 (7)	0.0058 (7)	0.0135 (7)
C18	0.0457 (9)	0.0450 (9)	0.0415 (8)	0.0091 (7)	0.0033 (7)	0.0194 (7)
C19	0.0898 (18)	0.0771 (17)	0.102 (2)	0.0156 (14)	0.0355 (15)	0.0378 (16)
C20	0.143 (3)	0.078 (2)	0.120 (3)	0.0361 (19)	0.052 (2)	0.0370 (18)

Geometric parameters (Å, º)

Cl1—C7	1.7375 (16)	C8—C9	1.376 (2)
Cl2—C9	1.7355 (16)	C8—H8	0.9300
Cl3—C14	1.7366 (17)	C9—C10	1.374 (2)
Cl4—C16	1.7434 (16)	C10—C11	1.385 (2)
O1—C1	1.4205 (18)	C10—H10	0.9300
O1—C12	1.4215 (18)	C11—H11	0.9300
O2—C19	1.429 (3)	C12—C13	1.500 (2)
O2—H2	0.88 (3)	C12—H12A	0.9700
N1—C3	1.346 (2)	C12—H12B	0.9700
N1—C5	1.354 (2)	C13—C18	1.380 (2)
N1—C2	1.457 (2)	C13—C14	1.391 (2)
N2—C3	1.314 (2)	C14—C15	1.383 (2)
N2—C4	1.363 (3)	C15—C16	1.371 (3)
C1—C2	1.516 (2)	C15—H15	0.9300
C1—C6	1.521 (2)	C16—C17	1.372 (2)
C1—H1	0.9800	C17—C18	1.390 (2)
C2—H2A	0.9700	C17—H17	0.9300
C2—H2B	0.9700	C18—H18	0.9300
C3—H3	0.9300	C19—C20	1.464 (4)
C4—C5	1.353 (3)	C19—H19A	0.9700
C4—H4	0.9300	C19—H19B	0.9700
C5—H5	0.9300	C20—H20A	0.9600
C6—C7	1.384 (2)	C20—H20B	0.9600
C6—C11	1.388 (2)	C20—H20C	0.9600
C7—C8	1.388 (2)
C1—O1—C12	112.51 (12)	C11—C10—H10	120.4
C19—O2—H2	105 (2)	C10—C11—C6	121.39 (15)
C3—N1—C5	106.99 (15)	C10—C11—H11	119.3
C3—N1—C2	126.80 (15)	C6—C11—H11	119.3
C5—N1—C2	126.07 (15)	O1—C12—C13	109.86 (13)
C3—N2—C4	104.28 (16)	O1—C12—H12A	109.7
O1—C1—C2	107.00 (13)	C13—C12—H12A	109.7
O1—C1—C6	112.06 (12)	O1—C12—H12B	109.7
C2—C1—C6	107.83 (12)	C13—C12—H12B	109.7
O1—C1—H1	110.0	H12A—C12—H12B	108.2
C2—C1—H1	110.0	C18—C13—C14	117.38 (14)
C6—C1—H1	110.0	C18—C13—C12	122.69 (14)
N1—C2—C1	114.19 (12)	C14—C13—C12	119.93 (14)
N1—C2—H2A	108.7	C15—C14—C13	122.61 (15)
C1—C2—H2A	108.7	C15—C14—Cl3	118.21 (12)
N1—C2—H2B	108.7	C13—C14—Cl3	119.18 (12)
C1—C2—H2B	108.7	C16—C15—C14	117.80 (15)
H2A—C2—H2B	107.6	C16—C15—H15	121.1
N2—C3—N1	112.10 (17)	C14—C15—H15	121.1
N2—C3—H3	124.0	C15—C16—C17	121.88 (15)
N1—C3—H3	124.0	C15—C16—Cl4	118.75 (13)
C5—C4—N2	110.92 (19)	C17—C16—Cl4	119.36 (14)
C5—C4—H4	124.5	C16—C17—C18	119.06 (16)
N2—C4—H4	124.5	C16—C17—H17	120.5
C4—C5—N1	105.72 (18)	C18—C17—H17	120.5
C4—C5—H5	127.1	C13—C18—C17	121.24 (15)
N1—C5—H5	127.1	C13—C18—H18	119.4
C7—C6—C11	117.46 (14)	C17—C18—H18	119.4
C7—C6—C1	122.84 (13)	O2—C19—C20	110.2 (2)
C11—C6—C1	119.57 (14)	O2—C19—H19A	109.6
C6—C7—C8	122.37 (14)	C20—C19—H19A	109.6
C6—C7—Cl1	120.52 (12)	O2—C19—H19B	109.6
C8—C7—Cl1	117.10 (13)	C20—C19—H19B	109.6
C9—C8—C7	118.11 (16)	H19A—C19—H19B	108.1
C9—C8—H8	120.9	C19—C20—H20A	109.5
C7—C8—H8	120.9	C19—C20—H20B	109.5
C10—C9—C8	121.51 (15)	H20A—C20—H20B	109.5
C10—C9—Cl2	119.35 (13)	C19—C20—H20C	109.5
C8—C9—Cl2	119.15 (13)	H20A—C20—H20C	109.5
C9—C10—C11	119.16 (15)	H20B—C20—H20C	109.5
C9—C10—H10	120.4
C12—O1—C1—C2	169.42 (12)	C7—C8—C9—C10	0.4 (3)
C12—O1—C1—C6	−72.58 (15)	C7—C8—C9—Cl2	−179.12 (14)
C3—N1—C2—C1	−88.93 (19)	C8—C9—C10—C11	−0.8 (3)
C5—N1—C2—C1	95.9 (2)	Cl2—C9—C10—C11	178.75 (14)
O1—C1—C2—N1	−63.34 (17)	C9—C10—C11—C6	0.7 (3)
C6—C1—C2—N1	175.94 (14)	C7—C6—C11—C10	−0.2 (3)
C4—N2—C3—N1	0.0 (2)	C1—C6—C11—C10	−176.29 (16)
C5—N1—C3—N2	0.1 (2)	C1—O1—C12—C13	178.03 (11)
C2—N1—C3—N2	−175.75 (15)	O1—C12—C13—C18	5.8 (2)
C3—N2—C4—C5	−0.1 (2)	O1—C12—C13—C14	−175.05 (12)
N2—C4—C5—N1	0.2 (2)	C18—C13—C14—C15	0.6 (2)
C3—N1—C5—C4	−0.2 (2)	C12—C13—C14—C15	−178.61 (14)
C2—N1—C5—C4	175.75 (16)	C18—C13—C14—Cl3	−179.05 (12)
O1—C1—C6—C7	156.72 (15)	C12—C13—C14—Cl3	1.79 (19)
C2—C1—C6—C7	−85.78 (19)	C13—C14—C15—C16	0.3 (2)
O1—C1—C6—C11	−27.4 (2)	Cl3—C14—C15—C16	179.90 (12)
C2—C1—C6—C11	90.08 (17)	C14—C15—C16—C17	−1.1 (2)
C11—C6—C7—C8	−0.2 (3)	C14—C15—C16—Cl4	178.10 (11)
C1—C6—C7—C8	175.77 (15)	C15—C16—C17—C18	0.9 (2)
C11—C6—C7—Cl1	−178.97 (13)	Cl4—C16—C17—C18	−178.22 (13)
C1—C6—C7—Cl1	−3.0 (2)	C14—C13—C18—C17	−0.7 (2)
C6—C7—C8—C9	0.1 (3)	C12—C13—C18—C17	178.45 (15)
Cl1—C7—C8—C9	178.91 (14)	C16—C17—C18—C13	0.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2^i	0.88 (3)	1.99 (3)	2.869 (2)	172 (3)
C5—H5···O2	0.93	2.49	3.398 (3)	166

Symmetry code: (i) x+1, y, z.

(RS)-1-[2-(2,4-Dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole hemihydrate (MIC_0.5H2O)

Crystal data

2C18H14Cl4N2O·H2O	F(000) = 1736
Mr = 850.24	Dx = 1.439 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.0630 (3) Å	Cell parameters from 11558 reflections
b = 33.2610 (16) Å	θ = 2.6–31.0°
c = 16.5481 (7) Å	µ = 0.62 mm^−1
β = 117.864 (3)°	T = 293 K
V = 3923.4 (3) Å^3	Needle, colourless
Z = 4	0.12 × 0.06 × 0.04 mm

Data collection

Rigaku XtaLAB Synergy Dualflex HyPix diffractometer	9339 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Mo) X-ray Source	6260 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	Rint = 0.048
ω scans	θmax = 28.0°, θmin = 2.5°
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2021)	h = −10→10
Tmin = 0.857, Tmax = 1.000	k = −42→43
45202 measured reflections	l = −20→21

Refinement

Refinement on F^2	Primary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.0381P)^2 + 1.322P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
9339 reflections	Δρmax = 0.40 e Å^−3
468 parameters	Δρmin = −0.28 e Å^−3
2 restraints

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.70158 (7)	0.20292 (2)	0.64935 (4)	0.05809 (16)
Cl2	0.18072 (9)	0.19687 (2)	0.76263 (5)	0.07108 (19)
Cl3	0.24111 (13)	0.02107 (2)	0.41323 (6)	0.0960 (3)
Cl4	−0.32437 (12)	0.02855 (3)	0.07000 (6)	0.1052 (3)
Cl5	0.68527 (7)	0.09835 (2)	−0.28394 (4)	0.05897 (16)
Cl6	1.22207 (9)	0.06365 (2)	−0.37584 (4)	0.07210 (19)
Cl7	1.22930 (12)	−0.00976 (2)	0.13554 (5)	0.0890 (2)
Cl8	1.78209 (11)	0.06398 (3)	0.42507 (5)	0.1083 (3)
O1	0.2630 (2)	0.15330 (4)	0.38629 (9)	0.0559 (4)
O2	1.1467 (2)	0.10884 (4)	0.00241 (9)	0.0508 (4)
O3	0.3841 (3)	0.20511 (8)	0.04599 (18)	0.0917 (6)
N1	0.4930 (3)	0.21547 (6)	0.36275 (12)	0.0548 (5)
N2	0.5342 (5)	0.20483 (7)	0.24160 (18)	0.0865 (7)
N3	0.8862 (3)	0.17374 (6)	−0.04043 (12)	0.0569 (5)
N4	0.6856 (4)	0.18401 (9)	0.01256 (18)	0.0895 (8)
C1	0.3960 (3)	0.17619 (6)	0.46075 (14)	0.0480 (5)
H1	0.519448	0.163330	0.485287	0.058*
C2	0.4030 (3)	0.21731 (6)	0.42105 (15)	0.0541 (5)
H2A	0.276182	0.227428	0.385827	0.065*
H2B	0.471043	0.235987	0.470714	0.065*
C3	0.4140 (4)	0.20459 (8)	0.27436 (17)	0.0702 (7)
H3	0.288298	0.197663	0.240204	0.084*
C4	0.6982 (5)	0.21632 (10)	0.3132 (3)	0.0884 (9)
H4	0.810644	0.219201	0.310936	0.106*
C5	0.6772 (4)	0.22302 (9)	0.3883 (2)	0.0737 (7)
H5	0.769185	0.231124	0.445610	0.088*
C6	0.3409 (3)	0.18091 (6)	0.53656 (13)	0.0430 (4)
C7	0.4697 (3)	0.19338 (6)	0.62376 (13)	0.0419 (4)
C8	0.4231 (3)	0.19842 (6)	0.69335 (14)	0.0452 (5)
H8	0.512332	0.206794	0.751067	0.054*
C9	0.2407 (3)	0.19072 (7)	0.67517 (15)	0.0490 (5)
C10	0.1075 (3)	0.17834 (7)	0.58965 (16)	0.0572 (6)
H10	−0.014826	0.173090	0.578278	0.069*
C11	0.1583 (3)	0.17386 (7)	0.52126 (15)	0.0547 (5)
H11	0.068128	0.165922	0.463381	0.066*
C12	0.2773 (3)	0.11100 (7)	0.40170 (16)	0.0587 (6)
H12A	0.262042	0.104702	0.455093	0.070*
H12B	0.399648	0.101554	0.412365	0.070*
C13	0.1262 (3)	0.09079 (7)	0.31868 (16)	0.0533 (5)
C14	0.0981 (4)	0.04955 (7)	0.31723 (17)	0.0626 (6)
C15	−0.0402 (4)	0.03025 (8)	0.2416 (2)	0.0726 (7)
H15	−0.057407	0.002628	0.242215	0.087*
C16	−0.1511 (4)	0.05258 (9)	0.16603 (19)	0.0697 (7)
C17	−0.1293 (4)	0.09312 (8)	0.16416 (18)	0.0709 (7)
H17	−0.206216	0.107970	0.112438	0.085*
C18	0.0099 (3)	0.11188 (8)	0.24084 (16)	0.0634 (6)
H18	0.025136	0.139557	0.239674	0.076*
C21	1.0023 (3)	0.11427 (6)	−0.08828 (13)	0.0465 (5)
H21	0.889081	0.100122	−0.096147	0.056*
C22	0.9647 (3)	0.15933 (7)	−0.09847 (14)	0.0534 (5)
H22A	1.081152	0.173431	−0.082773	0.064*
H22B	0.878139	0.165363	−0.161759	0.064*
C23	0.7097 (4)	0.16848 (9)	−0.05411 (19)	0.0713 (7)
H23	0.616251	0.155454	−0.104575	0.086*
C24	0.8560 (5)	0.19958 (10)	0.0723 (2)	0.0890 (10)
H24	0.882190	0.212424	0.126934	0.107*
C25	0.9806 (4)	0.19364 (9)	0.04073 (17)	0.0740 (7)
H25	1.105748	0.201500	0.068588	0.089*
C26	1.0567 (3)	0.09968 (6)	−0.15940 (13)	0.0428 (4)
C27	0.9243 (3)	0.09325 (6)	−0.25002 (13)	0.0430 (4)
C28	0.9729 (3)	0.08237 (6)	−0.31672 (14)	0.0468 (5)
H28	0.881519	0.078497	−0.376879	0.056*
C29	1.1606 (3)	0.07737 (7)	−0.29179 (15)	0.0499 (5)
C30	1.2967 (3)	0.08266 (8)	−0.20273 (15)	0.0566 (6)
H30	1.422457	0.078656	−0.186609	0.068*
C31	1.2443 (3)	0.09399 (7)	−0.13746 (15)	0.0526 (5)
H31	1.336487	0.097905	−0.077492	0.063*
C32	1.1574 (3)	0.06946 (6)	0.03767 (14)	0.0492 (5)
H32A	1.182458	0.050138	0.000794	0.059*
H32B	1.039489	0.062406	0.036366	0.059*
C33	1.3141 (3)	0.06876 (6)	0.13486 (14)	0.0473 (5)
C34	1.3572 (3)	0.03368 (7)	0.18546 (15)	0.0549 (5)
C35	1.4993 (4)	0.03144 (9)	0.27474 (17)	0.0697 (7)
H35	1.525958	0.007487	0.307428	0.084*
C36	1.5993 (3)	0.06587 (9)	0.31331 (16)	0.0682 (7)
C37	1.5612 (3)	0.10123 (9)	0.26620 (16)	0.0681 (7)
H37	1.630056	0.124227	0.293744	0.082*
C38	1.4183 (3)	0.10250 (7)	0.17668 (16)	0.0585 (6)
H38	1.392399	0.126545	0.144359	0.070*
H3A	0.434 (7)	0.2015 (16)	0.1051 (14)	0.20 (2)*
H3B	0.468 (5)	0.1927 (12)	0.036 (3)	0.155 (18)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0426 (3)	0.0822 (4)	0.0516 (3)	−0.0098 (3)	0.0238 (2)	−0.0016 (3)
Cl2	0.0688 (4)	0.0923 (5)	0.0716 (4)	−0.0116 (3)	0.0490 (3)	−0.0094 (3)
Cl3	0.1383 (7)	0.0538 (4)	0.0861 (5)	0.0011 (4)	0.0443 (5)	0.0101 (4)
Cl4	0.0897 (5)	0.1140 (7)	0.0997 (6)	−0.0337 (5)	0.0342 (5)	−0.0542 (5)
Cl5	0.0388 (2)	0.0773 (4)	0.0552 (3)	0.0049 (3)	0.0172 (2)	0.0077 (3)
Cl6	0.0669 (4)	0.0976 (5)	0.0588 (4)	0.0161 (3)	0.0353 (3)	−0.0020 (3)
Cl7	0.1287 (6)	0.0476 (4)	0.0800 (5)	−0.0016 (4)	0.0399 (4)	0.0089 (3)
Cl8	0.0867 (5)	0.1646 (9)	0.0442 (4)	0.0311 (5)	0.0060 (3)	0.0108 (4)
O1	0.0747 (10)	0.0437 (8)	0.0423 (8)	−0.0050 (7)	0.0215 (7)	−0.0032 (6)
O2	0.0609 (8)	0.0469 (8)	0.0355 (7)	0.0024 (7)	0.0148 (6)	0.0064 (6)
O3	0.0875 (14)	0.1095 (18)	0.0935 (17)	−0.0056 (13)	0.0550 (14)	0.0016 (14)
N1	0.0713 (12)	0.0514 (11)	0.0442 (10)	−0.0045 (9)	0.0291 (9)	0.0001 (8)
N2	0.139 (2)	0.0707 (16)	0.0802 (17)	0.0027 (15)	0.0764 (18)	0.0039 (13)
N3	0.0641 (12)	0.0620 (12)	0.0441 (10)	0.0197 (9)	0.0249 (9)	0.0087 (9)
N4	0.0946 (18)	0.111 (2)	0.0844 (17)	0.0345 (16)	0.0595 (16)	0.0187 (15)
C1	0.0572 (12)	0.0434 (11)	0.0421 (11)	−0.0024 (9)	0.0221 (9)	−0.0032 (9)
C2	0.0740 (14)	0.0464 (12)	0.0453 (12)	−0.0047 (11)	0.0306 (11)	−0.0029 (9)
C3	0.102 (2)	0.0618 (16)	0.0521 (14)	−0.0123 (14)	0.0403 (14)	−0.0049 (12)
C4	0.102 (2)	0.083 (2)	0.108 (3)	0.0175 (18)	0.072 (2)	0.0267 (19)
C5	0.0710 (16)	0.0785 (19)	0.0689 (17)	0.0005 (14)	0.0303 (14)	0.0160 (14)
C6	0.0469 (10)	0.0394 (11)	0.0412 (11)	0.0004 (9)	0.0193 (9)	0.0023 (8)
C7	0.0383 (9)	0.0447 (11)	0.0424 (11)	−0.0005 (8)	0.0185 (8)	0.0050 (8)
C8	0.0424 (10)	0.0506 (12)	0.0403 (11)	−0.0025 (9)	0.0174 (9)	0.0023 (9)
C9	0.0486 (11)	0.0525 (13)	0.0532 (12)	−0.0005 (10)	0.0299 (10)	0.0017 (10)
C10	0.0406 (11)	0.0656 (15)	0.0654 (15)	−0.0062 (10)	0.0247 (10)	−0.0074 (12)
C11	0.0451 (11)	0.0607 (14)	0.0491 (12)	−0.0039 (10)	0.0143 (10)	−0.0064 (10)
C12	0.0790 (15)	0.0459 (13)	0.0515 (13)	−0.0022 (11)	0.0307 (12)	−0.0016 (10)
C13	0.0678 (13)	0.0488 (13)	0.0533 (13)	−0.0081 (11)	0.0365 (11)	−0.0090 (10)
C14	0.0807 (16)	0.0513 (14)	0.0665 (15)	−0.0061 (12)	0.0433 (13)	−0.0043 (12)
C15	0.0912 (19)	0.0512 (15)	0.089 (2)	−0.0222 (14)	0.0531 (17)	−0.0219 (14)
C16	0.0713 (16)	0.0735 (18)	0.0727 (18)	−0.0189 (14)	0.0407 (14)	−0.0274 (15)
C17	0.0780 (17)	0.0708 (18)	0.0564 (15)	−0.0065 (14)	0.0250 (13)	−0.0078 (13)
C18	0.0774 (16)	0.0520 (14)	0.0559 (14)	−0.0099 (12)	0.0270 (12)	−0.0052 (11)
C21	0.0481 (11)	0.0516 (12)	0.0364 (11)	0.0034 (9)	0.0169 (9)	0.0062 (9)
C22	0.0636 (13)	0.0575 (14)	0.0416 (11)	0.0138 (11)	0.0266 (10)	0.0100 (10)
C23	0.0728 (17)	0.0812 (19)	0.0664 (16)	0.0160 (14)	0.0379 (14)	0.0095 (14)
C24	0.105 (2)	0.107 (2)	0.0584 (17)	0.043 (2)	0.0413 (17)	0.0031 (16)
C25	0.0745 (16)	0.089 (2)	0.0513 (14)	0.0235 (15)	0.0230 (13)	−0.0036 (13)
C26	0.0430 (10)	0.0440 (11)	0.0382 (10)	0.0026 (9)	0.0162 (8)	0.0056 (8)
C27	0.0381 (9)	0.0434 (11)	0.0449 (11)	0.0009 (8)	0.0171 (9)	0.0056 (9)
C28	0.0448 (10)	0.0497 (12)	0.0389 (11)	−0.0005 (9)	0.0138 (9)	−0.0002 (9)
C29	0.0503 (11)	0.0537 (13)	0.0476 (12)	0.0049 (10)	0.0245 (10)	0.0019 (10)
C30	0.0391 (10)	0.0723 (16)	0.0548 (13)	0.0058 (10)	0.0190 (10)	0.0026 (11)
C31	0.0416 (10)	0.0666 (15)	0.0410 (11)	0.0010 (10)	0.0121 (9)	0.0031 (10)
C32	0.0617 (12)	0.0440 (12)	0.0394 (11)	0.0037 (10)	0.0214 (10)	0.0049 (9)
C33	0.0551 (12)	0.0486 (12)	0.0391 (11)	0.0098 (10)	0.0227 (9)	0.0048 (9)
C34	0.0702 (14)	0.0493 (13)	0.0481 (12)	0.0123 (11)	0.0301 (11)	0.0054 (10)
C35	0.0848 (17)	0.0736 (18)	0.0482 (14)	0.0293 (15)	0.0291 (13)	0.0202 (13)
C36	0.0615 (14)	0.096 (2)	0.0384 (12)	0.0246 (14)	0.0161 (11)	0.0085 (13)
C37	0.0634 (14)	0.0772 (18)	0.0508 (14)	0.0014 (13)	0.0158 (12)	−0.0038 (13)
C38	0.0660 (14)	0.0534 (14)	0.0489 (13)	0.0027 (11)	0.0209 (11)	0.0042 (11)

Geometric parameters (Å, º)

Cl1—C7	1.7426 (19)	C12—C13	1.503 (3)
Cl2—C9	1.739 (2)	C12—H12A	0.9700
Cl3—C14	1.743 (3)	C12—H12B	0.9700
Cl4—C16	1.744 (3)	C13—C18	1.379 (3)
Cl5—C27	1.7455 (19)	C13—C14	1.389 (3)
Cl6—C29	1.741 (2)	C14—C15	1.385 (4)
Cl7—C34	1.743 (2)	C15—C16	1.367 (4)
Cl8—C36	1.746 (2)	C15—H15	0.9300
O1—C1	1.419 (2)	C16—C17	1.362 (4)
O1—C12	1.425 (3)	C17—C18	1.388 (3)
O2—C21	1.417 (2)	C17—H17	0.9300
O2—C32	1.420 (2)	C18—H18	0.9300
O3—H3A	0.874 (19)	C21—C26	1.515 (3)
O3—H3B	0.870 (19)	C21—C22	1.523 (3)
N1—C3	1.344 (3)	C21—H21	0.9800
N1—C5	1.364 (3)	C22—H22A	0.9700
N1—C2	1.455 (3)	C22—H22B	0.9700
N2—C3	1.312 (3)	C23—H23	0.9300
N2—C4	1.355 (4)	C24—C25	1.346 (4)
N3—C23	1.344 (3)	C24—H24	0.9300
N3—C25	1.366 (3)	C25—H25	0.9300
N3—C22	1.456 (3)	C26—C27	1.392 (3)
N4—C23	1.312 (3)	C26—C31	1.394 (3)
N4—C24	1.365 (4)	C27—C28	1.381 (3)
C1—C6	1.522 (3)	C28—C29	1.380 (3)
C1—C2	1.529 (3)	C28—H28	0.9300
C1—H1	0.9800	C29—C30	1.377 (3)
C2—H2A	0.9700	C30—C31	1.383 (3)
C2—H2B	0.9700	C30—H30	0.9300
C3—H3	0.9300	C31—H31	0.9300
C4—C5	1.348 (4)	C32—C33	1.511 (3)
C4—H4	0.9300	C32—H32A	0.9700
C5—H5	0.9300	C32—H32B	0.9700
C6—C7	1.390 (3)	C33—C38	1.378 (3)
C6—C11	1.392 (3)	C33—C34	1.383 (3)
C7—C8	1.378 (3)	C34—C35	1.385 (3)
C8—C9	1.381 (3)	C35—C36	1.374 (4)
C8—H8	0.9300	C35—H35	0.9300
C9—C10	1.380 (3)	C36—C37	1.364 (4)
C10—C11	1.380 (3)	C37—C38	1.389 (3)
C10—H10	0.9300	C37—H37	0.9300
C11—H11	0.9300	C38—H38	0.9300
C1—O1—C12	114.17 (16)	C16—C17—H17	120.6
C21—O2—C32	114.50 (15)	C18—C17—H17	120.6
H3A—O3—H3B	98 (4)	C13—C18—C17	122.1 (2)
C3—N1—C5	106.3 (2)	C13—C18—H18	119.0
C3—N1—C2	127.1 (2)	C17—C18—H18	119.0
C5—N1—C2	126.5 (2)	O2—C21—C26	112.89 (16)
C3—N2—C4	104.3 (2)	O2—C21—C22	105.38 (17)
C23—N3—C25	106.7 (2)	C26—C21—C22	110.12 (16)
C23—N3—C22	126.8 (2)	O2—C21—H21	109.5
C25—N3—C22	126.5 (2)	C26—C21—H21	109.5
C23—N4—C24	105.3 (2)	C22—C21—H21	109.5
O1—C1—C6	112.19 (17)	N3—C22—C21	112.10 (18)
O1—C1—C2	105.75 (17)	N3—C22—H22A	109.2
C6—C1—C2	110.18 (17)	C21—C22—H22A	109.2
O1—C1—H1	109.5	N3—C22—H22B	109.2
C6—C1—H1	109.5	C21—C22—H22B	109.2
C2—C1—H1	109.5	H22A—C22—H22B	107.9
N1—C2—C1	112.14 (18)	N4—C23—N3	111.6 (3)
N1—C2—H2A	109.2	N4—C23—H23	124.2
C1—C2—H2A	109.2	N3—C23—H23	124.2
N1—C2—H2B	109.2	C25—C24—N4	110.1 (3)
C1—C2—H2B	109.2	C25—C24—H24	125.0
H2A—C2—H2B	107.9	N4—C24—H24	125.0
N2—C3—N1	112.5 (3)	C24—C25—N3	106.2 (3)
N2—C3—H3	123.8	C24—C25—H25	126.9
N1—C3—H3	123.8	N3—C25—H25	126.9
C5—C4—N2	111.2 (3)	C27—C26—C31	116.89 (18)
C5—C4—H4	124.4	C27—C26—C21	122.09 (17)
N2—C4—H4	124.4	C31—C26—C21	120.94 (18)
C4—C5—N1	105.8 (3)	C28—C27—C26	122.68 (17)
C4—C5—H5	127.1	C28—C27—Cl5	116.84 (15)
N1—C5—H5	127.1	C26—C27—Cl5	120.47 (15)
C7—C6—C11	116.89 (19)	C29—C28—C27	118.29 (19)
C7—C6—C1	121.48 (17)	C29—C28—H28	120.9
C11—C6—C1	121.61 (18)	C27—C28—H28	120.9
C8—C7—C6	122.76 (18)	C30—C29—C28	121.2 (2)
C8—C7—Cl1	117.07 (15)	C30—C29—Cl6	120.45 (16)
C6—C7—Cl1	120.17 (15)	C28—C29—Cl6	118.32 (16)
C7—C8—C9	118.28 (19)	C29—C30—C31	119.31 (19)
C7—C8—H8	120.9	C29—C30—H30	120.3
C9—C8—H8	120.9	C31—C30—H30	120.3
C10—C9—C8	121.2 (2)	C30—C31—C26	121.59 (19)
C10—C9—Cl2	120.16 (16)	C30—C31—H31	119.2
C8—C9—Cl2	118.63 (16)	C26—C31—H31	119.2
C11—C10—C9	119.07 (19)	O2—C32—C33	108.14 (17)
C11—C10—H10	120.5	O2—C32—H32A	110.1
C9—C10—H10	120.5	C33—C32—H32A	110.1
C10—C11—C6	121.8 (2)	O2—C32—H32B	110.1
C10—C11—H11	119.1	C33—C32—H32B	110.1
C6—C11—H11	119.1	H32A—C32—H32B	108.4
O1—C12—C13	108.36 (19)	C38—C33—C34	117.5 (2)
O1—C12—H12A	110.0	C38—C33—C32	122.14 (19)
C13—C12—H12A	110.0	C34—C33—C32	120.4 (2)
O1—C12—H12B	110.0	C33—C34—C35	122.7 (2)
C13—C12—H12B	110.0	C33—C34—Cl7	119.16 (17)
H12A—C12—H12B	108.4	C35—C34—Cl7	118.17 (19)
C18—C13—C14	116.9 (2)	C36—C35—C34	117.6 (2)
C18—C13—C12	122.2 (2)	C36—C35—H35	121.2
C14—C13—C12	120.9 (2)	C34—C35—H35	121.2
C15—C14—C13	122.0 (2)	C37—C36—C35	121.7 (2)
C15—C14—Cl3	118.8 (2)	C37—C36—Cl8	119.3 (2)
C13—C14—Cl3	119.2 (2)	C35—C36—Cl8	118.9 (2)
C16—C15—C14	118.8 (2)	C36—C37—C38	119.3 (3)
C16—C15—H15	120.6	C36—C37—H37	120.4
C14—C15—H15	120.6	C38—C37—H37	120.4
C17—C16—C15	121.5 (2)	C33—C38—C37	121.2 (2)
C17—C16—Cl4	119.3 (2)	C33—C38—H38	119.4
C15—C16—Cl4	119.2 (2)	C37—C38—H38	119.4
C16—C17—C18	118.8 (3)
C12—O1—C1—C6	−78.4 (2)	C32—O2—C21—C26	−81.7 (2)
C12—O1—C1—C2	161.48 (18)	C32—O2—C21—C22	158.12 (17)
C3—N1—C2—C1	82.6 (3)	C23—N3—C22—C21	−74.8 (3)
C5—N1—C2—C1	−94.6 (3)	C25—N3—C22—C21	101.9 (3)
O1—C1—C2—N1	−70.9 (2)	O2—C21—C22—N3	−66.2 (2)
C6—C1—C2—N1	167.66 (17)	C26—C21—C22—N3	171.81 (17)
C4—N2—C3—N1	0.3 (3)	C24—N4—C23—N3	−0.7 (3)
C5—N1—C3—N2	−0.3 (3)	C25—N3—C23—N4	0.5 (3)
C2—N1—C3—N2	−178.0 (2)	C22—N3—C23—N4	177.8 (2)
C3—N2—C4—C5	−0.1 (3)	C23—N4—C24—C25	0.6 (4)
N2—C4—C5—N1	0.0 (3)	N4—C24—C25—N3	−0.3 (3)
C3—N1—C5—C4	0.2 (3)	C23—N3—C25—C24	−0.1 (3)
C2—N1—C5—C4	177.9 (2)	C22—N3—C25—C24	−177.4 (2)
O1—C1—C6—C7	164.04 (18)	O2—C21—C26—C27	164.41 (18)
C2—C1—C6—C7	−78.4 (2)	C22—C21—C26—C27	−78.1 (2)
O1—C1—C6—C11	−17.5 (3)	O2—C21—C26—C31	−18.8 (3)
C2—C1—C6—C11	100.0 (2)	C22—C21—C26—C31	98.6 (2)
C11—C6—C7—C8	0.6 (3)	C31—C26—C27—C28	−1.0 (3)
C1—C6—C7—C8	179.13 (19)	C21—C26—C27—C28	175.89 (19)
C11—C6—C7—Cl1	179.98 (16)	C31—C26—C27—Cl5	178.38 (16)
C1—C6—C7—Cl1	−1.5 (3)	C21—C26—C27—Cl5	−4.7 (3)
C6—C7—C8—C9	0.0 (3)	C26—C27—C28—C29	0.6 (3)
Cl1—C7—C8—C9	−179.43 (16)	Cl5—C27—C28—C29	−178.84 (16)
C7—C8—C9—C10	−0.1 (3)	C27—C28—C29—C30	0.6 (3)
C7—C8—C9—Cl2	179.84 (16)	C27—C28—C29—Cl6	−179.99 (16)
C8—C9—C10—C11	−0.4 (3)	C28—C29—C30—C31	−1.3 (4)
Cl2—C9—C10—C11	179.69 (18)	Cl6—C29—C30—C31	179.30 (18)
C9—C10—C11—C6	1.0 (4)	C29—C30—C31—C26	0.9 (4)
C7—C6—C11—C10	−1.1 (3)	C27—C26—C31—C30	0.3 (3)
C1—C6—C11—C10	−179.6 (2)	C21—C26—C31—C30	−176.7 (2)
C1—O1—C12—C13	178.72 (17)	C21—O2—C32—C33	−178.74 (16)
O1—C12—C13—C18	4.8 (3)	O2—C32—C33—C38	1.2 (3)
O1—C12—C13—C14	−175.3 (2)	O2—C32—C33—C34	−179.16 (19)
C18—C13—C14—C15	−0.2 (4)	C38—C33—C34—C35	−0.3 (3)
C12—C13—C14—C15	179.9 (2)	C32—C33—C34—C35	−180.0 (2)
C18—C13—C14—Cl3	179.69 (18)	C38—C33—C34—Cl7	179.97 (17)
C12—C13—C14—Cl3	−0.2 (3)	C32—C33—C34—Cl7	0.3 (3)
C13—C14—C15—C16	0.5 (4)	C33—C34—C35—C36	0.2 (4)
Cl3—C14—C15—C16	−179.4 (2)	Cl7—C34—C35—C36	179.88 (19)
C14—C15—C16—C17	−0.6 (4)	C34—C35—C36—C37	0.2 (4)
C14—C15—C16—Cl4	179.4 (2)	C34—C35—C36—Cl8	−178.92 (18)
C15—C16—C17—C18	0.4 (4)	C35—C36—C37—C38	−0.4 (4)
Cl4—C16—C17—C18	−179.6 (2)	Cl8—C36—C37—C38	178.69 (19)
C14—C13—C18—C17	0.0 (4)	C34—C33—C38—C37	0.1 (3)
C12—C13—C18—C17	179.8 (2)	C32—C33—C38—C37	179.7 (2)
C16—C17—C18—C13	−0.1 (4)	C36—C37—C38—C33	0.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N2	0.87 (2)	2.02 (2)	2.878 (4)	168 (5)
O3—H3B···N4	0.87 (2)	1.99 (2)	2.823 (3)	160 (4)
C2—H2B···O3^i	0.97	2.59	3.354 (3)	136
C22—H22A···O3^ii	0.97	2.60	3.451 (3)	147
C25—H25···O3^ii	0.93	2.44	3.236 (4)	143

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x+1, y, z.