Red, orange and yellow crystals of 4,5-­bis(4-methoxy­phenyl)-2-(3-nitro­phenyl)-1H-imidazole

Red non-solvate crystals of the title compound from ethanol, C₂₃H₁₉N₃O₄, orange solvate crystals from tert-butanol, C₂₃H₁₉N₃O₄·C₄H₁₀O, yellow solvate crystals from dioxane-water, C₂₃H₁₉N₃O₄·0.5C₄H₈O₂, and intense yellow solvate crystals from benzene-N,N'-dimethylformamide, C₂₃H₁₉N₃O₄·C₆H₆, differ from each other in their molecular conformation and hydrogen-bonding scheme. The bathochromic shifts of the crystal color are explained by the molecular planarity and charge-transfer effect among the imidazole mol­ecules.

S1. Comment

4,5-Bis(4-methoxyphenyl)-2-(3-nitrophenyl)-1H-imidazole crystallizes in different colored states by changing the solvent (Sakaino et al., 1996). Recently, we reported yellow solvate crystals from ethyl acetate. The guest solvent molecules were lost without destruction of the network of host imidazole molecules upon heating at 353 K under 2 Torr (1 Torr = 133.322 Pa) (Inouye et al., 1999). Here, we wish to report four other crystals: red non-solvate crystals from ethanol, (1), orange solvate crystals from t-butanol, (2), yellow solvate crystals from dioxane-water, (3), and intense yellow solvate crystals from benzene-DMF(10:1), (4). \sch

The numbering of the host molecule is the same in all crystals. Fig. 1 represents the molecular structure of (1). Two independent molecules (designated as A and B) were found in (1) and they differ in the conformation of the molecules as shown by the dihedral angle between the imidazole ring (C10 to N14, designated as I) and three benzene rings [C4 to C9 (II), C15 to C20 (III) and C23 to C28 (IV)]. In molecule A, I/II = 3.8 (3), I/III = 4.5 (4), and I/IV = 62.5 (2)°. In molecule B, I/II = 7.5 (4), I/III = 31.7 (5) and 15.0 (8) (1:1), and I/IV = 55.9 (2)°. The host molecules lie as a sheet and are connected through a weak hydrogen bonding between N—H and O of the nitro group (see Table 1). The imizadole ring of molecule A in a sheet faces to the nitrophenyl ring of molecules A and B in the upper and lower sheets, respectively. The short intermolecular distances betweeen the imidazole ring and the nitrophenyl ring are C6A—C12A(1 − x, 1 − y, 1 − z) = 3.515 (8) Å and C4A—C10B(1/2 − x, 1/2 + y, 1 − z) = 3.481 (8) Å, respectively. The molecular planarity and intermolecular charge transfer effect from the imidazole ring to the nitrophenyl ring may cause the bathochromic shift of the color. Two host molecules in (2) are arranged to have a center of symmetry and are connected with each other by two t-butanol molecules. The O31—H31 of t-butanol bonds to N14 of the imidazole while O31 bonds to H11—N11 of the imidazole (see Fig. 2 and Table 2). The dihedral angles between the rings are (I/II) = 10.2 (2), (I/III) = 40.2 (2), and (I/IV) = 29.7 (1)°. The facing of the imidazole ring to the nitrophenyl ring [N11—C6(-x, 1 − y, −z) = 3.554 (4) Å] may cause a slight bathochromic shift of the color. In (III), on the other hand, dioxane connects two host molecules by intermolecular hydrogen bondings between O and H—N to have a center of symmetry at the center of dioxane (see Fig. 3 and Table 3). The dihedral angles between the rings are (I/II) = 7.0 (1), (I/III) = 77.9 (1), and (I/IV)=12.4 (1)°. The packing pattern of (4) is shown in Fig. 4. The dihedral angles between the rings are (I/II) = 14.0 (2), (I/III) = 36.5 (1), and (I/IV) = 42.9 (1)°. The host molecules in (4) are connected directly through intermolecular hydrogen bondings between N11—H11 and N14 of the imidazole ring (see Fig. 4 and Table 4). These arrangements were similar to the ethyl acetate solvate crystals (Inouye et al., 1999). However, (4) is centro-symmetric, while the latter is chiral. The guest benzene molecules in (4) form a column structure in the holes along the [101] axis.

S2. Experimental

Crystals (1) to (4) were obtained from the respective solutions. Compound (1): red thin plates from ethanol; found: C 68.87, H 4.77, N 10.56%; calculated for C₂₃H₁₉N₃O₄: C 68.81, H 4.77, N 10.47%. Compound (2): orange needles from t-butanol saturated at 353 K; found:C 68.15, H 6.12, N 8.79%; calculated for C₂₃H₁₉N₃O₄+C₄H₁₀O: C 68.19, H 6.16, N 8.84%. Compound (3): yellow needles from dioxane-water (3:1); found:C 67.33, H 5.16, N 9.45%; calculated for C₂₃H₁₉N₃O₄+1/2C₄H₈O₂: C 67.40, H 5.20, N 9.43%. Compound (4): golden yellow needles from benzene-DMF (10:1); found:C 72.32, H 5.26, N 8.80%; calculated for C₂₃H₁₉N₃O₄+C₆H₆: C 72.63, H 5.26, N 8.76%.

S3. Refinement

Several disorders are found in (1) and (4). In (1), one of the methoxyphenyl ring (C15B–C22B:C15C–C22C = 0.54:0.46) and O2B and O2C (0.54:0.46) in molecule B were disordered and treated under constraints that corresponding bond lengths in both conformations are similar to each other within 0.01 Å. C15C to C22C were refined isotropically. In (4), the guest benzene molecules (C31A—C36A:C31B—C36B = 0.70:0.30) were disordered and treated as ideal hexagones (C—C = 1.390 and C—H = 0.93 Å with U's of H being set at 1.2 times those of the attached non-H stoms). C31B to C36B were refined isotopically. The positions of aromatic H, NH, and OH were refined in the final calculations. The methyl H were calculated geometrically (C—H = 0.96 Å and U's were set at 1.5 times those of the attached non-H atoms).

Computing details

For all compounds, data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: ORTEPII (Johnson, 1976).

Figures

	Fig. 1. Molecular structure of (1) showing 50% probability displacement ellipsoids (ORTEPII; Johnson, 1976). For clarity, only one of the disordered position of O2B and C15B—C22B, and only the H atom of the N—H group are included. The dotted lines show the hydrogen bonding.
	Fig. 2. Molecular arrangement of (2) showing 50% probability displacement ellipsoids (ORTEPII; Johnson, 1976). For clarity, only the H atom of the N—H group are included, with dotted lines showing the hydrogen bonding.
	Fig. 3. Molecular structure of (3) showing 50% probability displacement ellipsoids (ORTEPII; Johnson, 1976). For clarity, only the H atom of the N—H group are included, with dotted lines showing the hydrogen bonding.
	Fig. 4. Packing pattern of (4) (ORTEPII; Johnson, 1976), with dotted lines showing the hydrogen bonding.

(1) 4,5-Bis(4-methoxyphenyl)-2-(3-nitrophenyl)-1H-imidazole

Crystal data

C23H19N3O4	F(000) = 1680
Mr = 401.41	Dx = 1.360 Mg m^−3 Dm = 1.34 (2) Mg m^−3 Dm measured by flotation
Monoclinic, P21/a	Mo Kα radiation, λ = 0.71073 Å
a = 21.004 (5) Å	Cell parameters from 25 reflections
b = 13.061 (3) Å	θ = 10.0–13.8°
c = 14.441 (4) Å	µ = 0.10 mm^−1
β = 98.266 (11)°	T = 293 K
V = 3920.5 (17) Å^3	Plate, red
Z = 8	0.35 × 0.25 × 0.04 mm

Data collection

Enraf-Nonius CAD4 diffractometer	Rint = 0.093
Radiation source: fine-focus sealed tube	θmax = 30.5°, θmin = 1.4°
Graphite monochromator	h = −29→29
ω–2θ scans	k = 0→18
12374 measured reflections	l = 0→20
11950 independent reflections	3 standard reflections every 120 min
3236 reflections with I > 2σ(I)	intensity decay: 3.7%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.086	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.221	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	Calculated w = 1/[σ^2(Fo^2) + (0.1751P)^2] where P = (Fo^2 + 2Fc^2)/3
11945 reflections	(Δ/σ)max = −0.001
675 parameters	Δρmax = 0.29 e Å^−3
22 restraints	Δρmin = −0.32 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

− 13.506 (0.140) x + 2.576 (0.109) y + 11.910 (0.044) z = 2.426 (0.082)

* 0.000 (0.000) O1A * 0.000 (0.000) O2A * 0.000 (0.000) N3A

Rms deviation of fitted atoms = 0.000

− 12.717 (0.039) x + 2.180 (0.033) y + 12.378 (0.018) z = 2.652 (0.026)

Angle to previous plane (with approximate e.s.d.) = 3.53 (0.72)

* 0.004 (0.004) C4A * 0.004 (0.004) C5A * −0.007 (0.004) C6A * 0.002 (0.005) C7A * 0.005 (0.005) C8A * −0.008 (0.004) C9A

Rms deviation of fitted atoms = 0.005

− 13.227 (0.044) x + 2.870 (0.034) y + 11.955 (0.023) z = 2.505 (0.036)

Angle to previous plane (with approximate e.s.d.) = 3.84 (0.34)

* 0.005 (0.003) C10A * 0.000 (0.003) N11A * −0.005 (0.003) C12A * 0.008 (0.003) C13A * −0.008 (0.003) N14A

Rms deviation of fitted atoms = 0.006

− 12.516 (0.046) x + 2.130 (0.040) y + 12.475 (0.022) z = 2.816 (0.047)

Angle to previous plane (with approximate e.s.d.) = 4.46 (0.37)

* 0.007 (0.005) C15A * 0.008 (0.005) C16A * −0.020 (0.005) C17A * 0.015 (0.005) C18A * 0.000 (0.005) C19A * −0.011 (0.005) C20A

Rms deviation of fitted atoms = 0.012

− 13.227 (0.044) x + 2.870 (0.034) y + 11.955 (0.023) z = 2.505 (0.036)

Angle to previous plane (with approximate e.s.d.) = 4.46 (0.37)

* 0.005 (0.003) C10A * 0.000 (0.003) N11A * −0.005 (0.003) C12A * 0.008 (0.003) C13A * −0.008 (0.003) N14A

Rms deviation of fitted atoms = 0.006

19.209 (0.021) x + 5.264 (0.029) y − 1.402 (0.039) z = 11.014 (0.029)

Angle to previous plane (with approximate e.s.d.) = 62.52 (1/5)

* 0.003 (0.004) C23A * 0.000 (0.005) C24A * −0.004 (0.005) C25A * 0.005 (0.005) C26A * −0.002 (0.004) C27A * −0.002 (0.004) C28A

Rms deviation of fitted atoms = 0.003

− 12.534 (0.375) x − 3.103 (0.148) y + 12.192 (0.123) z = 1.804 (0.266)

Angle to previous plane (with approximate e.s.d.) = 52.06 (1.19)

* 0.000 (0.000) O1B * 0.000 (0.000) O2B * 0.000 (0.000) N3B

Rms deviation of fitted atoms = 0.000

15.349 (0.036) x + 1.522 (0.035) y − 11.129 (0.023) z = 0.342 (0.026)

Angle to previous plane (with approximate e.s.d.) = 11.68 (1.86)

* 0.001 (0.004) C4B * 0.007 (0.004) C5B * −0.009 (0.004) C6B * 0.002 (0.005) C7B * 0.006 (0.005) C8B * −0.008 (0.005) C9B

Rms deviation of fitted atoms = 0.006

19.478 (0.202) x + 0.509 (0.184) y − 7.243 (0.304) z = 4.749 (0.299)

Angle to previous plane (with approximate e.s.d.) = 21.17 (1.77)

* 0.000 (0.000) O1B * 0.000 (0.000) O2C * 0.000 (0.000) N3B

Rms deviation of fitted atoms = 0.000

15.349 (0.036) x + 1.522 (0.035) y − 11.129 (0.023) z = 0.342 (0.026)

Angle to previous plane (with approximate e.s.d.) = 21.17 (1.77)

* 0.001 (0.004) C4B * 0.007 (0.004) C5B * −0.009 (0.004) C6B * 0.002 (0.005) C7B * 0.006 (0.005) C8B * −0.008 (0.005) C9B

Rms deviation of fitted atoms = 0.006

− 13.689 (0.046) x − 2.669 (0.037) y + 11.791 (0.025) z = 0.475 (0.019)

Angle to previous plane (with approximate e.s.d.) = 7.54 (0.36)

* 0.006 (0.003) C10B * −0.005 (0.003) N11B * 0.002 (0.004) C12B * 0.002 (0.004) C13B * −0.005 (0.003) N14B

Rms deviation of fitted atoms = 0.004

13.366 (0.118) x + 8.489 (0.059) y − 7.259 (0.076) z = 0.928 (0.018)

Angle to previous plane (with approximate e.s.d.) = 31.68 (0.54)

* −0.015 (0.013) C15B * −0.008 (0.012) C16B * 0.037 (0.009) C17B * −0.043 (0.010) C18B * 0.019 (0.009) C19B * 0.009 (0.011) C20B

Rms deviation of fitted atoms = 0.026

− 13.689 (0.046) x − 2.669 (0.037) y + 11.791 (0.025) z = 0.475 (0.019)

Angle to previous plane (with approximate e.s.d.) = 31.68 (0.54)

* 0.006 (0.003) C10B * −0.005 (0.003) N11B * 0.002 (0.004) C12B * 0.002 (0.004) C13B * −0.005 (0.003) N14B

Rms deviation of fitted atoms = 0.004

4.819 (0.061) x − 6.646 (0.029) y + 11.381 (0.025) z = 4.805 (0.008)

Angle to previous plane (with approximate e.s.d.) = 55.91 (0.21)

* 0.001 (0.005) C23B * −0.008 (0.005) C24B * 0.005 (0.005) C25B * 0.004 (0.005) C26B * −0.011 (0.005) C27B * 0.009 (0.005) C28B

Rms deviation of fitted atoms = 0.007

− 13.689 (0.046) x − 2.669 (0.037) y + 11.791 (0.025) z = 0.475 (0.019)

Angle to previous plane (with approximate e.s.d.) = 55.91 (0.21)

* 0.006 (0.003) C10B * −0.005 (0.003) N11B * 0.002 (0.004) C12B * 0.002 (0.004) C13B * −0.005 (0.003) N14B

Rms deviation of fitted atoms = 0.004

14.543 (0.139) x + 5.477 (0.092) y − 9.828 (0.090) z = 0.216 (0.030)

Angle to previous plane (with approximate e.s.d.) = 15.03 (0.84)

* −0.021 (0.016) C15C * 0.012 (0.015) C16C * 0.022 (0.012) C17C * −0.047 (0.014) C18C * 0.036 (0.015) C19C * −0.003 (0.015) C20C

Rms deviation of fitted atoms = 0.028

Refinement. Refinement on F² for ALL reflections except for 2 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _refine_ls_R_factor_gt etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1A	0.2439 (2)	0.2953 (3)	0.4164 (3)	0.0667 (13)
O2A	0.1865 (2)	0.4026 (4)	0.3281 (4)	0.0691 (14)
N3A	0.2329 (2)	0.3820 (4)	0.3852 (4)	0.0498 (13)
C4A	0.2787 (3)	0.4634 (4)	0.4193 (4)	0.0407 (14)
C5A	0.3331 (3)	0.4396 (4)	0.4793 (4)	0.0399 (13)
H5A	0.339 (3)	0.378 (4)	0.501 (4)	0.039 (16)*
C6A	0.3768 (3)	0.5178 (4)	0.5096 (4)	0.0380 (13)
C7A	0.3622 (3)	0.6165 (4)	0.4780 (4)	0.050 (2)
H7A	0.390 (2)	0.672 (4)	0.494 (4)	0.034 (14)*
C8A	0.3066 (3)	0.6384 (5)	0.4173 (5)	0.054 (2)
H8A	0.300 (3)	0.705 (5)	0.394 (4)	0.054 (17)*
C9A	0.2645 (3)	0.5622 (5)	0.3864 (4)	0.047 (2)
H9A	0.228 (3)	0.570 (5)	0.341 (5)	0.07 (2)*
C10A	0.4358 (3)	0.4938 (4)	0.5736 (4)	0.0386 (13)
N11A	0.4809 (2)	0.5643 (4)	0.6061 (3)	0.0423 (12)
H11A	0.481 (3)	0.627 (4)	0.586 (4)	0.044 (17)*
C12A	0.5279 (3)	0.5180 (4)	0.6688 (4)	0.0378 (13)
C13A	0.5078 (3)	0.4172 (4)	0.6719 (4)	0.0361 (12)
N14A	0.4509 (2)	0.4030 (3)	0.6110 (3)	0.0420 (11)
C15A	0.5839 (3)	0.5742 (4)	0.7141 (4)	0.0402 (13)
C16A	0.5891 (3)	0.6784 (5)	0.7016 (6)	0.060 (2)
H16A	0.561 (3)	0.712 (5)	0.665 (4)	0.054 (19)*
C17A	0.6408 (3)	0.7348 (5)	0.7417 (6)	0.063 (2)
H17A	0.643 (4)	0.809 (7)	0.731 (6)	0.12 (3)*
C18A	0.6894 (3)	0.6887 (5)	0.8011 (5)	0.052 (2)
C19A	0.6867 (3)	0.5846 (5)	0.8149 (5)	0.063 (2)
H19A	0.718 (3)	0.547 (5)	0.854 (5)	0.06 (2)*
C20A	0.6349 (3)	0.5284 (5)	0.7716 (5)	0.057 (2)
H20A	0.633 (3)	0.461 (5)	0.778 (4)	0.053 (18)*
O21A	0.7385 (2)	0.7504 (3)	0.8403 (4)	0.0753 (15)
C22A	0.7878 (4)	0.7075 (6)	0.9060 (6)	0.088 (3)
H22A	0.8176	0.7601	0.9299	0.133*
H22B	0.8100	0.6555	0.8762	0.133*
H22C	0.7692	0.6777	0.9567	0.133*
C23A	0.5360 (3)	0.3315 (4)	0.7305 (4)	0.0394 (13)
C24A	0.5419 (3)	0.3356 (5)	0.8280 (4)	0.055 (2)
H24A	0.521 (4)	0.395 (6)	0.848 (5)	0.09 (3)*
C25A	0.5675 (3)	0.2557 (5)	0.8829 (5)	0.058 (2)
H25A	0.574 (3)	0.260 (4)	0.948 (4)	0.047 (16)*
C26A	0.5888 (3)	0.1688 (4)	0.8414 (4)	0.0472 (15)
C27A	0.5832 (3)	0.1624 (4)	0.7463 (4)	0.0450 (15)
H27A	0.598 (3)	0.102 (5)	0.716 (4)	0.051 (17)*
C28A	0.5571 (3)	0.2433 (4)	0.6917 (5)	0.0444 (14)
H28A	0.554 (2)	0.231 (4)	0.626 (4)	0.041 (15)*
O29A	0.6143 (2)	0.0936 (3)	0.9027 (3)	0.0650 (13)
C30A	0.6351 (4)	0.0017 (5)	0.8646 (5)	0.079 (2)
H30A	0.6503	−0.0448	0.9144	0.118*
H30B	0.6693	0.0164	0.8292	0.118*
H30C	0.5998	−0.0290	0.8244	0.118*
O1B	0.4617 (2)	−0.2000 (3)	0.5717 (4)	0.078 (2)
O2B	0.5198 (9)	−0.090 (2)	0.6596 (11)	0.067 (6)	0.54
O2C	0.5008 (12)	−0.101 (3)	0.6840 (11)	0.074 (8)	0.46
N3B	0.4712 (3)	−0.1135 (4)	0.6036 (4)	0.060 (2)
C4B	0.4317 (3)	−0.0290 (4)	0.5606 (4)	0.0415 (14)
C5B	0.3832 (3)	−0.0513 (4)	0.4901 (4)	0.0411 (14)
H5B	0.379 (2)	−0.120 (4)	0.475 (3)	0.033 (14)*
C6B	0.3446 (3)	0.0273 (4)	0.4490 (4)	0.0365 (13)
C7B	0.3581 (3)	0.1261 (4)	0.4803 (4)	0.046 (2)
H7B	0.332 (3)	0.181 (4)	0.453 (4)	0.039 (15)*
C8B	0.4078 (3)	0.1476 (5)	0.5514 (5)	0.054 (2)
H8B	0.419 (3)	0.216 (5)	0.570 (5)	0.08 (2)*
C9B	0.4447 (3)	0.0684 (5)	0.5926 (5)	0.050 (2)
H9B	0.474 (3)	0.078 (5)	0.634 (4)	0.051 (19)*
C10B	0.2906 (3)	0.0012 (4)	0.3784 (4)	0.0397 (13)
N11B	0.2444 (2)	0.0667 (4)	0.3387 (4)	0.0444 (12)
H11B	0.248 (3)	0.130 (5)	0.354 (5)	0.07 (2)*
C12B	0.2014 (3)	0.0120 (4)	0.2770 (4)	0.0453 (15)
C13B	0.2243 (3)	−0.0864 (4)	0.2812 (4)	0.0426 (14)
N14B	0.2803 (2)	−0.0929 (3)	0.3442 (3)	0.0457 (12)
C15B	0.1488 (8)	0.0549 (13)	0.2124 (9)	0.050 (5)	0.54
C16B	0.1148 (6)	0.1365 (11)	0.2444 (9)	0.054 (4)	0.54
H16B	0.1281	0.1633	0.3037	0.065*	0.54
C17B	0.0624 (6)	0.1777 (11)	0.1897 (8)	0.056 (3)	0.54
H17B	0.0418	0.2356	0.2085	0.068*	0.54
C18B	0.0411 (4)	0.1297 (11)	0.1054 (7)	0.043 (3)	0.54
C19B	0.0754 (6)	0.0520 (9)	0.0692 (8)	0.055 (3)	0.54
H19B	0.0624	0.0268	0.0092	0.066*	0.54
C20B	0.1288 (6)	0.0132 (9)	0.1236 (8)	0.052 (3)	0.54
H20B	0.1517	−0.0404	0.1017	0.063*	0.54
O21B	−0.0128 (4)	0.1642 (7)	0.0426 (6)	0.068 (2)	0.54
C22B	−0.0498 (9)	0.2458 (13)	0.0708 (14)	0.092 (6)	0.54
H22D	−0.0906	0.2482	0.0312	0.138*	0.54
H22E	−0.0273	0.3092	0.0659	0.138*	0.54
H22F	−0.0565	0.2355	0.1345	0.138*	0.54
C15C	0.1447 (9)	0.0688 (13)	0.2325 (13)	0.033 (4)*	0.46
C16C	0.1273 (7)	0.1677 (11)	0.2586 (12)	0.041 (5)*	0.46
H16C	0.1519	0.1977	0.3102	0.049*	0.46
C17C	0.0767 (7)	0.2227 (12)	0.2132 (11)	0.054 (5)*	0.46
H17C	0.0684	0.2887	0.2325	0.065*	0.46
C18C	0.0378 (7)	0.1780 (11)	0.1378 (10)	0.045 (4)*	0.46
C19C	0.0548 (10)	0.0845 (13)	0.1025 (15)	0.063 (7)*	0.46
H19C	0.0327	0.0584	0.0471	0.075*	0.46
C20C	0.1054 (6)	0.0319 (11)	0.1520 (9)	0.046 (4)*	0.46
H20C	0.1143	−0.0330	0.1307	0.056*	0.46
O21C	−0.0119 (6)	0.2440 (9)	0.0956 (8)	0.072 (4)*	0.46
C22C	−0.0633 (9)	0.1929 (16)	0.0402 (15)	0.081 (7)*	0.46
H22G	−0.0886	0.2417	0.0010	0.122*	0.46
H22H	−0.0898	0.1600	0.0802	0.122*	0.46
H22I	−0.0464	0.1425	0.0020	0.122*	0.46
C23B	0.1989 (3)	−0.1808 (4)	0.2324 (4)	0.0418 (14)
C24B	0.1371 (3)	−0.2149 (5)	0.2380 (5)	0.052 (2)
H24B	0.115 (3)	−0.178 (5)	0.275 (5)	0.07 (2)*
C25B	0.1138 (3)	−0.3057 (5)	0.1960 (5)	0.051 (2)
H25B	0.070 (3)	−0.330 (4)	0.200 (4)	0.042 (15)*
C26B	0.1524 (3)	−0.3622 (5)	0.1465 (4)	0.052 (2)
C27B	0.2136 (3)	−0.3286 (5)	0.1389 (5)	0.063 (2)
H27B	0.243 (3)	−0.365 (5)	0.107 (5)	0.08 (2)*
C28B	0.2371 (4)	−0.2394 (6)	0.1828 (5)	0.062 (2)
H28B	0.277 (4)	−0.217 (6)	0.177 (6)	0.12 (3)*
O29B	0.1346 (2)	−0.4534 (3)	0.1012 (3)	0.0700 (14)
C30B	0.0743 (4)	−0.4946 (6)	0.1109 (6)	0.093 (3)
H30D	0.0694	−0.5601	0.0805	0.140*
H30E	0.0410	−0.4493	0.0828	0.140*
H30F	0.0710	−0.5027	0.1762	0.140*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.066 (3)	0.044 (3)	0.083 (3)	−0.008 (2)	−0.013 (3)	−0.001 (2)
O2A	0.049 (3)	0.067 (3)	0.083 (3)	−0.004 (2)	−0.018 (3)	−0.001 (3)
N3A	0.042 (3)	0.050 (3)	0.054 (3)	−0.003 (2)	−0.001 (3)	−0.002 (3)
C4A	0.049 (4)	0.030 (3)	0.042 (3)	0.001 (3)	0.006 (3)	−0.001 (3)
C5A	0.044 (3)	0.033 (3)	0.043 (3)	0.002 (3)	0.007 (3)	0.003 (3)
C6A	0.042 (3)	0.035 (3)	0.037 (3)	0.004 (2)	0.002 (3)	0.004 (3)
C7A	0.061 (4)	0.032 (3)	0.052 (4)	−0.007 (3)	−0.007 (3)	−0.001 (3)
C8A	0.069 (4)	0.038 (3)	0.052 (4)	0.008 (3)	−0.007 (3)	0.009 (3)
C9A	0.048 (4)	0.045 (4)	0.044 (4)	0.007 (3)	−0.005 (3)	−0.005 (3)
C10A	0.050 (4)	0.034 (3)	0.031 (3)	−0.001 (3)	0.003 (3)	−0.004 (2)
N11A	0.047 (3)	0.027 (2)	0.051 (3)	0.001 (2)	0.003 (2)	0.004 (2)
C12A	0.036 (3)	0.031 (3)	0.046 (3)	0.007 (2)	0.007 (3)	0.002 (3)
C13A	0.036 (3)	0.037 (3)	0.035 (3)	0.001 (2)	0.003 (2)	−0.002 (2)
N14A	0.049 (3)	0.036 (2)	0.040 (3)	0.001 (2)	0.002 (2)	0.004 (2)
C15A	0.038 (3)	0.036 (3)	0.046 (3)	0.002 (3)	0.004 (3)	0.004 (3)
C16A	0.039 (4)	0.048 (4)	0.085 (5)	−0.005 (3)	−0.015 (4)	0.014 (4)
C17A	0.046 (4)	0.046 (4)	0.094 (6)	−0.010 (3)	−0.003 (4)	0.011 (4)
C18A	0.039 (3)	0.049 (4)	0.066 (4)	−0.004 (3)	0.001 (3)	−0.005 (3)
C19A	0.051 (4)	0.051 (4)	0.080 (5)	0.007 (3)	−0.012 (4)	0.009 (4)
C20A	0.052 (4)	0.040 (4)	0.072 (5)	−0.001 (3)	−0.016 (4)	0.009 (3)
O21A	0.058 (3)	0.058 (3)	0.102 (4)	−0.016 (2)	−0.014 (3)	0.002 (3)
C22A	0.065 (5)	0.097 (6)	0.091 (6)	−0.002 (5)	−0.030 (5)	0.000 (5)
C23A	0.038 (3)	0.039 (3)	0.038 (3)	−0.006 (3)	−0.004 (3)	−0.001 (3)
C24A	0.067 (4)	0.058 (4)	0.042 (4)	0.020 (4)	0.012 (3)	0.000 (3)
C25A	0.071 (5)	0.064 (4)	0.036 (4)	0.023 (4)	0.000 (3)	0.007 (3)
C26A	0.047 (3)	0.045 (3)	0.048 (4)	0.004 (3)	−0.001 (3)	0.013 (3)
C27A	0.056 (4)	0.032 (3)	0.044 (4)	0.003 (3)	−0.003 (3)	0.006 (3)
C28A	0.052 (4)	0.043 (3)	0.037 (3)	−0.005 (3)	0.004 (3)	−0.001 (3)
O29A	0.086 (3)	0.061 (3)	0.045 (3)	0.017 (3)	−0.001 (2)	0.017 (2)
C30A	0.104 (6)	0.052 (4)	0.075 (5)	0.022 (4)	−0.005 (5)	0.024 (4)
O1B	0.092 (4)	0.033 (2)	0.094 (4)	0.009 (2)	−0.034 (3)	−0.001 (2)
O2B	0.062 (10)	0.048 (8)	0.078 (10)	0.004 (7)	−0.034 (9)	0.003 (8)
O2C	0.080 (15)	0.068 (11)	0.060 (9)	−0.011 (11)	−0.039 (11)	−0.002 (10)
N3B	0.067 (4)	0.038 (3)	0.068 (4)	0.003 (3)	−0.015 (3)	0.001 (3)
C4B	0.039 (3)	0.035 (3)	0.047 (3)	0.001 (2)	−0.003 (3)	0.002 (3)
C5B	0.051 (4)	0.026 (3)	0.045 (3)	−0.006 (3)	0.001 (3)	−0.006 (3)
C6B	0.034 (3)	0.035 (3)	0.038 (3)	0.006 (2)	−0.001 (2)	−0.001 (2)
C7B	0.051 (4)	0.029 (3)	0.054 (4)	0.003 (3)	−0.008 (3)	−0.002 (3)
C8B	0.064 (4)	0.029 (3)	0.064 (4)	−0.004 (3)	−0.009 (3)	−0.005 (3)
C9B	0.051 (4)	0.039 (3)	0.054 (4)	−0.012 (3)	−0.014 (3)	−0.006 (3)
C10B	0.036 (3)	0.033 (3)	0.048 (3)	−0.004 (3)	0.001 (3)	−0.002 (3)
N11B	0.046 (3)	0.032 (3)	0.051 (3)	−0.001 (2)	−0.007 (2)	0.003 (2)
C12B	0.042 (3)	0.044 (3)	0.044 (3)	−0.014 (3)	−0.011 (3)	0.004 (3)
C13B	0.044 (3)	0.038 (3)	0.044 (3)	−0.006 (3)	−0.002 (3)	−0.005 (3)
N14B	0.043 (3)	0.040 (3)	0.052 (3)	−0.003 (2)	−0.002 (2)	−0.005 (2)
C15B	0.060 (9)	0.056 (9)	0.030 (9)	−0.022 (7)	−0.007 (8)	0.001 (6)
C16B	0.052 (8)	0.064 (9)	0.041 (7)	−0.014 (8)	−0.016 (6)	0.002 (7)
C17B	0.043 (7)	0.063 (9)	0.060 (9)	−0.007 (7)	−0.004 (7)	0.003 (8)
C18B	0.014 (5)	0.076 (11)	0.038 (7)	0.001 (6)	−0.004 (5)	−0.006 (8)
C19B	0.063 (8)	0.056 (8)	0.042 (7)	−0.003 (7)	−0.007 (7)	−0.006 (6)
C20B	0.050 (8)	0.053 (7)	0.052 (8)	0.003 (6)	0.001 (7)	0.002 (6)
O21B	0.049 (5)	0.089 (7)	0.065 (6)	0.014 (5)	0.000 (4)	0.017 (5)
C22B	0.054 (10)	0.129 (18)	0.096 (14)	−0.001 (12)	0.021 (10)	0.046 (14)
C23B	0.047 (3)	0.039 (3)	0.037 (3)	−0.004 (3)	−0.005 (3)	−0.003 (3)
C24B	0.056 (4)	0.048 (4)	0.052 (4)	−0.013 (3)	0.010 (3)	−0.010 (3)
C25B	0.051 (4)	0.043 (3)	0.057 (4)	−0.012 (3)	0.005 (3)	−0.007 (3)
C26B	0.066 (4)	0.045 (4)	0.041 (3)	−0.012 (3)	−0.007 (3)	−0.007 (3)
C27B	0.057 (4)	0.055 (4)	0.077 (5)	−0.001 (4)	0.011 (4)	−0.017 (4)
C28B	0.054 (4)	0.059 (4)	0.073 (5)	−0.008 (4)	0.010 (4)	−0.017 (4)
O29B	0.078 (3)	0.056 (3)	0.074 (3)	−0.016 (3)	0.005 (3)	−0.025 (2)
C30B	0.094 (6)	0.075 (5)	0.107 (7)	−0.036 (5)	0.004 (5)	−0.032 (5)

Geometric parameters (Å, º)

O1A—N3A	1.229 (6)	C6B—C10B	1.453 (7)
O2A—N3A	1.213 (6)	C7B—C8B	1.385 (8)
N3A—C4A	1.469 (7)	C7B—H7B	0.96 (5)
C4A—C5A	1.366 (8)	C8B—C9B	1.374 (9)
C4A—C9A	1.392 (8)	C8B—H8B	0.96 (7)
C5A—C6A	1.400 (8)	C9B—H9B	0.81 (6)
C5A—H5A	0.87 (5)	C10B—N14B	1.330 (7)
C6A—C7A	1.388 (8)	C10B—N11B	1.357 (7)
C6A—C10A	1.471 (7)	N11B—C12B	1.374 (7)
C7A—C8A	1.384 (8)	N11B—H11B	0.85 (6)
C7A—H7A	0.94 (5)	C12B—C13B	1.370 (8)
C8A—C9A	1.363 (9)	C12B—C15B	1.452 (10)
C8A—H8A	0.94 (6)	C12B—C15C	1.470 (10)
C9A—H9A	0.95 (7)	C13B—N14B	1.382 (7)
C10A—N14A	1.322 (7)	C13B—C23B	1.479 (7)
C10A—N11A	1.355 (7)	C15B—C20B	1.400 (9)
N11A—C12A	1.380 (7)	C15B—C16B	1.399 (9)
N11A—H11A	0.87 (6)	C16B—C17B	1.370 (10)
C12A—C13A	1.385 (7)	C16B—H16B	0.93
C12A—C15A	1.460 (7)	C17B—C18B	1.386 (11)
C13A—N14A	1.390 (7)	C17B—H17B	0.93
C13A—C23A	1.475 (7)	C18B—C19B	1.390 (11)
C15A—C16A	1.380 (8)	C18B—O21B	1.418 (11)
C15A—C20A	1.392 (8)	C19B—C20B	1.371 (10)
C16A—C17A	1.371 (9)	C19B—H19B	0.93
C16A—H16A	0.86 (6)	C20B—H20B	0.93
C17A—C18A	1.375 (9)	O21B—C22B	1.413 (13)
C17A—H17A	0.99 (9)	C22B—H22D	0.96
C18A—O21A	1.366 (7)	C22B—H22E	0.96
C18A—C19A	1.376 (9)	C22B—H22F	0.96
C19A—C20A	1.385 (9)	C15C—C16C	1.409 (9)
C19A—H19A	0.94 (6)	C15C—C20C	1.411 (9)
C20A—H20A	0.89 (6)	C16C—C17C	1.370 (10)
O21A—C22A	1.415 (8)	C16C—H16C	0.93
C22A—H22A	0.96	C17C—C18C	1.392 (11)
C22A—H22B	0.96	C17C—H17C	0.93
C22A—H22C	0.96	C18C—C19C	1.390 (11)
C23A—C28A	1.381 (8)	C18C—O21C	1.422 (12)
C23A—C24A	1.397 (8)	C19C—C20C	1.377 (11)
C24A—C25A	1.373 (9)	C19C—H19C	0.93
C24A—H24A	0.95 (7)	C20C—H20C	0.93
C25A—C26A	1.388 (9)	O21C—C22C	1.414 (13)
C25A—H25A	0.94 (6)	C22C—H22G	0.96
C26A—C27A	1.364 (8)	C22C—H22H	0.96
C26A—O29A	1.377 (7)	C22C—H22I	0.96
C27A—C28A	1.383 (8)	C23B—C28B	1.381 (8)
C27A—H27A	0.98 (6)	C23B—C24B	1.386 (8)
C28A—H28A	0.96 (5)	C24B—C25B	1.388 (8)
O29A—C30A	1.416 (8)	C24B—H24B	0.91 (6)
C30A—H30A	0.96	C25B—C26B	1.372 (9)
C30A—H30B	0.96	C25B—H25B	0.99 (5)
C30A—H30C	0.96	C26B—O29B	1.384 (7)
O1B—N3B	1.226 (6)	C26B—C27B	1.378 (9)
O2B—N3B	1.246 (9)	C27B—C28B	1.383 (9)
O2C—N3B	1.247 (10)	C27B—H27B	0.95 (7)
N3B—C4B	1.465 (7)	C28B—H28B	0.91 (8)
C4B—C5B	1.364 (8)	O29B—C30B	1.404 (8)
C4B—C9B	1.368 (8)	C30B—H30D	0.96
C5B—C6B	1.387 (7)	C30B—H30E	0.96
C5B—H5B	0.93 (5)	C30B—H30F	0.96
C6B—C7B	1.382 (7)
O2A—N3A—O1A	122.8 (5)	C6B—C7B—H7B	119 (3)
O2A—N3A—C4A	119.4 (5)	C8B—C7B—H7B	119 (3)
O1A—N3A—C4A	117.7 (5)	C9B—C8B—C7B	119.1 (6)
C5A—C4A—C9A	123.0 (6)	C9B—C8B—H8B	119 (4)
C5A—C4A—N3A	119.7 (5)	C7B—C8B—H8B	122 (4)
C9A—C4A—N3A	117.3 (5)	C4B—C9B—C8B	118.8 (6)
C4A—C5A—C6A	118.9 (5)	C4B—C9B—H9B	119 (4)
C4A—C5A—H5A	120 (4)	C8B—C9B—H9B	122 (4)
C6A—C5A—H5A	121 (4)	N14B—C10B—N11B	110.9 (5)
C7A—C6A—C5A	118.1 (5)	N14B—C10B—C6B	123.1 (5)
C7A—C6A—C10A	122.1 (5)	N11B—C10B—C6B	125.9 (5)
C5A—C6A—C10A	119.8 (5)	C10B—N11B—C12B	108.0 (5)
C8A—C7A—C6A	121.8 (6)	C10B—N11B—H11B	118 (5)
C8A—C7A—H7A	116 (3)	C12B—N11B—H11B	134 (5)
C6A—C7A—H7A	123 (3)	C13B—C12B—N11B	105.4 (5)
C9A—C8A—C7A	120.3 (6)	C13B—C12B—C15B	128.3 (7)
C9A—C8A—H8A	121 (4)	N11B—C12B—C15B	125.8 (8)
C7A—C8A—H8A	119 (4)	C13B—C12B—C15C	138.5 (8)
C8A—C9A—C4A	117.9 (6)	N11B—C12B—C15C	115.9 (7)
C8A—C9A—H9A	126 (4)	C12B—C13B—N14B	110.2 (5)
C4A—C9A—H9A	116 (4)	C12B—C13B—C23B	131.3 (5)
N14A—C10A—N11A	110.7 (5)	N14B—C13B—C23B	118.4 (5)
N14A—C10A—C6A	125.4 (5)	C10B—N14B—C13B	105.4 (5)
N11A—C10A—C6A	123.8 (5)	C20B—C15B—C16B	119.9 (10)
C10A—N11A—C12A	109.1 (5)	C20B—C15B—C12B	122.6 (10)
C10A—N11A—H11A	124 (4)	C16B—C15B—C12B	117.3 (8)
C12A—N11A—H11A	127 (4)	C17B—C16B—C15B	121.0 (12)
N11A—C12A—C13A	104.2 (5)	C17B—C16B—H16B	119.5
N11A—C12A—C15A	121.9 (5)	C15B—C16B—H16B	119.5
C13A—C12A—C15A	133.9 (5)	C16B—C17B—C18B	117.4 (12)
N14A—C13A—C12A	110.2 (5)	C16B—C17B—H17B	121.3
N14A—C13A—C23A	119.9 (5)	C18B—C17B—H17B	121.3
C12A—C13A—C23A	129.8 (5)	C17B—C18B—C19B	122.8 (10)
C10A—N14A—C13A	105.8 (5)	C17B—C18B—O21B	123.0 (10)
C16A—C15A—C20A	115.8 (6)	C19B—C18B—O21B	113.7 (8)
C16A—C15A—C12A	120.7 (5)	C20B—C19B—C18B	118.7 (11)
C20A—C15A—C12A	123.6 (5)	C20B—C19B—H19B	120.7
C17A—C16A—C15A	123.1 (7)	C18B—C19B—H19B	120.7
C17A—C16A—H16A	115 (4)	C19B—C20B—C15B	119.7 (11)
C15A—C16A—H16A	122 (4)	C19B—C20B—H20B	120.2
C18A—C17A—C16A	120.1 (6)	C15B—C20B—H20B	120.2
C18A—C17A—H17A	119 (5)	C22B—O21B—C18B	118.4 (12)
C16A—C17A—H17A	121 (5)	O21B—C22B—H22D	109.5
O21A—C18A—C17A	116.7 (6)	O21B—C22B—H22E	109.5
O21A—C18A—C19A	124.6 (6)	H22D—C22B—H22E	109.5
C17A—C18A—C19A	118.7 (6)	O21B—C22B—H22F	109.5
C18A—C19A—C20A	120.3 (7)	H22D—C22B—H22F	109.5
C18A—C19A—H19A	125 (4)	H22E—C22B—H22F	109.5
C20A—C19A—H19A	115 (4)	C16C—C15C—C20C	113.0 (11)
C15A—C20A—C19A	121.9 (6)	C16C—C15C—C12B	124.8 (10)
C15A—C20A—H20A	117 (4)	C20C—C15C—C12B	121.9 (10)
C19A—C20A—H20A	121 (4)	C17C—C16C—C15C	124.5 (14)
C18A—O21A—C22A	118.7 (5)	C17C—C16C—H16C	117.8
O21A—C22A—H22A	109.5	C15C—C16C—H16C	117.8
O21A—C22A—H22B	109.5	C16C—C17C—C18C	118.9 (14)
H22A—C22A—H22B	109.5	C16C—C17C—H17C	120.6
O21A—C22A—H22C	109.5	C18C—C17C—H17C	120.6
H22A—C22A—H22C	109.5	C19C—C18C—C17C	120.1 (14)
H22B—C22A—H22C	109.5	C19C—C18C—O21C	125.9 (12)
C28A—C23A—C24A	116.9 (6)	C17C—C18C—O21C	113.2 (11)
C28A—C23A—C13A	121.8 (5)	C20C—C19C—C18C	117.9 (17)
C24A—C23A—C13A	121.3 (5)	C20C—C19C—H19C	121.0
C25A—C24A—C23A	121.6 (6)	C18C—C19C—H19C	121.0
C25A—C24A—H24A	127 (5)	C19C—C20C—C15C	125.0 (15)
C23A—C24A—H24A	111 (5)	C19C—C20C—H20C	117.5
C24A—C25A—C26A	119.8 (6)	C15C—C20C—H20C	117.5
C24A—C25A—H25A	122 (4)	C22C—O21C—C18C	114.2 (14)
C26A—C25A—H25A	119 (4)	O21C—C22C—H22G	109.5
C27A—C26A—O29A	125.0 (6)	O21C—C22C—H22H	109.5
C27A—C26A—C25A	119.9 (6)	H22G—C22C—H22H	109.5
O29A—C26A—C25A	115.2 (6)	O21C—C22C—H22I	109.5
C26A—C27A—C28A	119.8 (6)	H22G—C22C—H22I	109.5
C26A—C27A—H27A	121 (3)	H22H—C22C—H22I	109.5
C28A—C27A—H27A	119 (3)	C28B—C23B—C24B	118.0 (6)
C23A—C28A—C27A	122.0 (6)	C28B—C23B—C13B	120.9 (5)
C23A—C28A—H28A	124 (3)	C24B—C23B—C13B	121.1 (5)
C27A—C28A—H28A	114 (3)	C23B—C24B—C25B	121.6 (7)
C26A—O29A—C30A	117.9 (5)	C23B—C24B—H24B	116 (4)
O29A—C30A—H30A	109.5	C25B—C24B—H24B	122 (4)
O29A—C30A—H30B	109.5	C26B—C25B—C24B	119.3 (6)
H30A—C30A—H30B	109.5	C26B—C25B—H25B	119 (3)
O29A—C30A—H30C	109.5	C24B—C25B—H25B	122 (3)
H30A—C30A—H30C	109.5	C25B—C26B—O29B	124.7 (6)
H30B—C30A—H30C	109.5	C25B—C26B—C27B	119.9 (6)
O1B—N3B—O2C	120.3 (18)	O29B—C26B—C27B	115.4 (6)
O1B—N3B—O2B	123.2 (14)	C26B—C27B—C28B	120.5 (7)
O1B—N3B—C4B	118.9 (5)	C26B—C27B—H27B	124 (4)
O2C—N3B—C4B	118.1 (19)	C28B—C27B—H27B	115 (4)
O2B—N3B—C4B	116.7 (14)	C23B—C28B—C27B	120.7 (7)
C5B—C4B—C9B	122.8 (5)	C23B—C28B—H28B	119 (6)
C5B—C4B—N3B	118.2 (5)	C27B—C28B—H28B	120 (6)
C9B—C4B—N3B	118.9 (5)	C26B—O29B—C30B	118.0 (6)
C4B—C5B—C6B	119.3 (5)	O29B—C30B—H30D	109.5
C4B—C5B—H5B	115 (3)	O29B—C30B—H30E	109.5
C6B—C5B—H5B	126 (3)	H30D—C30B—H30E	109.5
C7B—C6B—C5B	118.1 (5)	O29B—C30B—H30F	109.5
C7B—C6B—C10B	123.5 (5)	H30D—C30B—H30F	109.5
C5B—C6B—C10B	118.4 (5)	H30E—C30B—H30F	109.5
C6B—C7B—C8B	122.0 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11A—H11A···O1B^i	0.87 (6)	2.30 (6)	3.135 (6)	161 (5)
N11B—H11B···O1A	0.85 (6)	2.35 (7)	3.190 (7)	170 (6)

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

(2) 4,5-Bis(4-methoxyphenyl)-2-(3-nitrophenyl)-1H-imidazole t-butanol solvate

Crystal data

C23H19N3O4·C4H10O	F(000) = 1008
Mr = 475.53	Dx = 1.277 Mg m^−3 Dm = 1.30 (2) Mg m^−3 Dm measured by flotation
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 15.331 (3) Å	Cell parameters from 25 reflections
b = 18.419 (3) Å	θ = 10.3–13.8°
c = 8.8318 (14) Å	µ = 0.09 mm^−1
β = 97.401 (8)°	T = 293 K
V = 2473.2 (7) Å^3	Needle, orange
Z = 4	0.40 × 0.20 × 0.15 mm

Data collection

Enraf-Nonius CAD4 diffractometer	Rint = 0.030
Radiation source: fine-focus sealed tube	θmax = 30.5°, θmin = 1.7°
Graphite monochromator	h = −21→21
ω–2θ scans	k = 0→26
7957 measured reflections	l = 0→12
7523 independent reflections	3 standard reflections every 120 min
3296 reflections with I > 2σ(I)	intensity decay: 3.5%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.193	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	Calculated w = 1/[σ^2(Fo^2) + (0.1826P)^2 + 0.6023P] where P = (Fo^2 + 2Fc^2)/3
7523 reflections	(Δ/σ)max = −0.001
377 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

5.356 (0.049) x − 3.326 (0.142) y + 7.655 (0.012) z = 0.255 (0.032)

* 0.000 (0.000) O1 * 0.000 (0.000) O2 * 0.000 (0.000) N3

Rms deviation of fitted atoms = 0.000

4.384 (0.026) x − 2.489 (0.031) y + 7.983 (0.007) z = 0.409 (0.012)

Angle to previous plane (with approximate e.s.d.) = 4.78 (0.30)

* −0.009 (0.003) C4 * 0.005 (0.002) C5 * 0.003 (0.003) C6 * −0.007 (0.003) C7 * 0.003 (0.004) C8 * 0.005 (0.003) C9

Rms deviation of fitted atoms = 0.006

− 6.704 (0.021) x − 3.615 (0.028) y + 7.189 (0.008) z = 0.123 (0.015)

Angle to previous plane (with approximate e.s.d.) = 10.21 (0.19)

* −0.010 (0.002) C10 * 0.014 (0.002) N11 * −0.012 (0.002) C12 * 0.006 (0.002) C13 * 0.002 (0.002) N14

Rms deviation of fitted atoms = 0.010

− 13.832 (0.011) x − 4.044 (0.025) y + 2.224 (0.013) z = 1.755 (0.019)

Angle to previous plane (with approximate e.s.d.) = 40.24 (0.15)

* 0.004 (0.002) C15 * −0.004 (0.003) C16 * −0.005 (0.003) C17 * 0.014 (0.002) C18 * −0.014 (0.002) C19 * 0.005 (0.003) C20

Rms deviation of fitted atoms = 0.009

− 6.704 (0.021) x − 3.615 (0.028) y + 7.189 (0.008) z = 0.123 (0.015)

Angle to previous plane (with approximate e.s.d.) = 40.24 (0.15)

* −0.010 (0.002) C10 * 0.014 (0.002) N11 * −0.012 (0.002) C12 * 0.006 (0.002) C13 * 0.002 (0.002) N14

Rms deviation of fitted atoms = 0.010

6.339 (0.021) x + 5.790 (0.027) y + 7.014 (0.008) z = 4.903 (0.016)

Angle to previous plane (with approximate e.s.d.) = 29.65 (0.14)

* −0.002 (0.002) C23 * −0.001 (0.003) C24 * 0.004 (0.003) C25 * −0.003 (0.003) C26 * 0.000 (0.003) C27 * 0.003 (0.002) C28

Rms deviation of fitted atoms = 0.002

Refinement. Refinement on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _refine_ls_R_factor_gt etc. and is not relevant to the choice of reflections for refinement. R- factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O1	0.0177 (3)	0.20786 (14)	0.1112 (4)	0.0791 (9)
O2	0.1349 (3)	0.1779 (2)	0.0162 (5)	0.1067 (13)
N3	0.0881 (3)	0.2230 (2)	0.0685 (4)	0.0666 (9)
C4	0.1182 (3)	0.2984 (2)	0.0782 (4)	0.0502 (8)
C5	0.0631 (2)	0.3505 (2)	0.1265 (4)	0.0424 (7)
H5	0.005 (2)	0.3370 (18)	0.151 (4)	0.045 (9)*
C6	0.0918 (2)	0.4229 (2)	0.1331 (4)	0.0396 (7)
C7	0.1736 (3)	0.4381 (2)	0.0917 (5)	0.0598 (10)
H7	0.193 (3)	0.487 (2)	0.086 (5)	0.071 (12)*
C8	0.2272 (3)	0.3839 (2)	0.0465 (6)	0.0741 (13)
H8	0.286 (3)	0.398 (2)	0.026 (5)	0.078 (13)*
C9	0.2004 (3)	0.3131 (2)	0.0394 (5)	0.0630 (11)
H9	0.240 (3)	0.272 (2)	0.016 (5)	0.072 (12)*
C10	0.0372 (2)	0.47878 (15)	0.1905 (3)	0.0362 (6)
N11	0.0602 (2)	0.54989 (13)	0.2015 (3)	0.0381 (6)
H11	0.103 (3)	0.570 (2)	0.156 (4)	0.058 (11)*
C12	0.0003 (2)	0.5857 (2)	0.2789 (3)	0.0376 (6)
C13	−0.0604 (2)	0.53370 (15)	0.3068 (3)	0.0377 (6)
N14	−0.0364 (2)	0.46743 (13)	0.2517 (3)	0.0392 (6)
C15	0.0140 (2)	0.6622 (2)	0.3259 (3)	0.0373 (6)
C16	0.0449 (2)	0.7136 (2)	0.2308 (4)	0.0449 (8)
H16	0.060 (3)	0.700 (2)	0.130 (5)	0.068 (12)*
C17	0.0584 (3)	0.7850 (2)	0.2774 (4)	0.0507 (9)
H17	0.081 (3)	0.819 (2)	0.222 (5)	0.057 (11)*
C18	0.0402 (2)	0.8063 (2)	0.4206 (4)	0.0435 (7)
C19	0.0116 (2)	0.7555 (2)	0.5182 (4)	0.0453 (8)
H19	−0.001 (2)	0.7675 (19)	0.624 (4)	0.052 (10)*
C20	−0.0026 (2)	0.6844 (2)	0.4691 (4)	0.0449 (7)
H20	−0.023 (3)	0.649 (2)	0.538 (5)	0.059 (11)*
O21	0.0532 (2)	0.87845 (12)	0.4554 (3)	0.0586 (7)
C22	0.0442 (3)	0.9012 (2)	0.6060 (5)	0.0689 (12)
H22A	0.0561	0.9523	0.6158	0.103*
H22B	0.0850	0.8750	0.6775	0.103*
H22C	−0.0147	0.8917	0.6267	0.103*
C23	−0.1407 (2)	0.5397 (2)	0.3804 (3)	0.0377 (6)
C24	−0.1912 (2)	0.6033 (2)	0.3736 (4)	0.0491 (8)
H24	−0.172 (3)	0.645 (2)	0.316 (4)	0.059 (11)*
C25	−0.2673 (2)	0.6072 (2)	0.4399 (5)	0.0548 (9)
H25	−0.308 (3)	0.651 (2)	0.433 (5)	0.065 (11)*
C26	−0.2965 (2)	0.5477 (2)	0.5145 (4)	0.0480 (8)
C27	−0.2485 (2)	0.4841 (2)	0.5239 (4)	0.0464 (8)
H27	−0.271 (2)	0.4405 (19)	0.577 (4)	0.054 (10)*
C28	−0.1711 (2)	0.4809 (2)	0.4571 (4)	0.0411 (7)
H28	−0.138 (2)	0.437 (2)	0.464 (4)	0.057 (11)*
O29	−0.3729 (2)	0.55830 (14)	0.5768 (4)	0.0709 (9)
C30	−0.4066 (3)	0.5004 (2)	0.6562 (6)	0.0789 (14)
H30A	−0.4615	0.5147	0.6887	0.118*
H30B	−0.3655	0.4882	0.7438	0.118*
H30C	−0.4158	0.4590	0.5902	0.118*
O31	0.1605 (2)	0.60988 (14)	−0.0279 (3)	0.0549 (7)
H31	0.134 (3)	0.590 (3)	−0.115 (6)	0.099 (17)*
C32	0.2377 (2)	0.6467 (2)	−0.0661 (4)	0.0516 (9)
C33	0.3040 (3)	0.5907 (3)	−0.1044 (6)	0.0787 (13)
H33A	0.3515	0.6147	−0.1451	0.118*
H33B	0.2759	0.5573	−0.1787	0.118*
H33C	0.3266	0.5647	−0.0135	0.118*
C34	0.2720 (3)	0.6888 (3)	0.0774 (5)	0.0755 (13)
H34A	0.3241	0.7150	0.0607	0.113*
H34B	0.2856	0.6557	0.1609	0.113*
H34C	0.2278	0.7225	0.1010	0.113*
C35	0.2113 (4)	0.6964 (2)	−0.2000 (6)	0.0815 (14)
H35A	0.2615	0.7239	−0.2214	0.122*
H35B	0.1662	0.7290	−0.1758	0.122*
H35C	0.1894	0.6681	−0.2879	0.122*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.122 (3)	0.047 (2)	0.076 (2)	−0.009 (2)	0.043 (2)	−0.0053 (14)
O2	0.141 (3)	0.048 (2)	0.140 (3)	0.028 (2)	0.051 (3)	−0.015 (2)
N3	0.097 (3)	0.044 (2)	0.061 (2)	0.015 (2)	0.021 (2)	0.0017 (15)
C4	0.070 (2)	0.038 (2)	0.044 (2)	0.012 (2)	0.011 (2)	0.0022 (14)
C5	0.050 (2)	0.038 (2)	0.041 (2)	0.0034 (14)	0.0109 (14)	−0.0014 (13)
C6	0.042 (2)	0.0386 (15)	0.039 (2)	0.0024 (12)	0.0095 (13)	−0.0044 (12)
C7	0.054 (2)	0.048 (2)	0.082 (3)	−0.004 (2)	0.025 (2)	−0.008 (2)
C8	0.051 (2)	0.068 (3)	0.109 (4)	0.007 (2)	0.031 (2)	−0.014 (2)
C9	0.062 (2)	0.058 (2)	0.073 (3)	0.019 (2)	0.022 (2)	−0.009 (2)
C10	0.038 (2)	0.0352 (14)	0.0351 (15)	0.0005 (12)	0.0057 (12)	−0.0023 (12)
N11	0.0402 (14)	0.0362 (12)	0.0397 (14)	−0.0008 (11)	0.0116 (11)	−0.0011 (11)
C12	0.041 (2)	0.0358 (14)	0.037 (2)	0.0007 (12)	0.0092 (12)	−0.0025 (12)
C13	0.041 (2)	0.0330 (14)	0.039 (2)	0.0002 (12)	0.0053 (12)	−0.0017 (12)
N14	0.0439 (14)	0.0336 (12)	0.0415 (14)	0.0015 (10)	0.0110 (11)	−0.0022 (10)
C15	0.039 (2)	0.0340 (14)	0.039 (2)	−0.0028 (12)	0.0078 (13)	−0.0048 (12)
C16	0.058 (2)	0.040 (2)	0.039 (2)	−0.0060 (14)	0.0144 (15)	−0.0015 (13)
C17	0.064 (2)	0.041 (2)	0.051 (2)	−0.012 (2)	0.021 (2)	0.0004 (15)
C18	0.041 (2)	0.036 (2)	0.054 (2)	−0.0038 (13)	0.0097 (14)	−0.0062 (13)
C19	0.054 (2)	0.041 (2)	0.043 (2)	−0.0017 (14)	0.015 (2)	−0.0072 (14)
C20	0.055 (2)	0.039 (2)	0.043 (2)	−0.0032 (14)	0.017 (2)	−0.0018 (14)
O21	0.074 (2)	0.0373 (12)	0.069 (2)	−0.0113 (11)	0.0270 (14)	−0.0124 (11)
C22	0.077 (3)	0.054 (2)	0.079 (3)	−0.014 (2)	0.022 (2)	−0.029 (2)
C23	0.040 (2)	0.0345 (14)	0.040 (2)	0.0003 (12)	0.0109 (13)	−0.0021 (12)
C24	0.051 (2)	0.035 (2)	0.064 (2)	0.0028 (14)	0.019 (2)	0.009 (2)
C25	0.052 (2)	0.039 (2)	0.077 (3)	0.0062 (15)	0.024 (2)	0.006 (2)
C26	0.047 (2)	0.043 (2)	0.057 (2)	−0.0004 (14)	0.017 (2)	−0.0021 (15)
C27	0.055 (2)	0.039 (2)	0.048 (2)	−0.0011 (14)	0.018 (2)	0.0046 (14)
C28	0.047 (2)	0.0330 (14)	0.044 (2)	0.0028 (13)	0.0097 (14)	0.0017 (13)
O29	0.063 (2)	0.055 (2)	0.104 (2)	0.0059 (13)	0.048 (2)	0.0074 (15)
C30	0.076 (3)	0.065 (3)	0.106 (4)	−0.001 (2)	0.052 (3)	0.010 (3)
O31	0.0530 (14)	0.0573 (15)	0.056 (2)	−0.0184 (12)	0.0137 (12)	−0.0106 (12)
C32	0.050 (2)	0.058 (2)	0.049 (2)	−0.017 (2)	0.014 (2)	−0.006 (2)
C33	0.054 (2)	0.098 (3)	0.086 (3)	−0.001 (2)	0.013 (2)	−0.020 (3)
C34	0.074 (3)	0.084 (3)	0.068 (3)	−0.027 (2)	0.005 (2)	−0.019 (2)
C35	0.110 (4)	0.063 (3)	0.070 (3)	−0.019 (3)	0.006 (3)	0.011 (2)

Geometric parameters (Å, º)

O1—N3	1.221 (5)	O21—C22	1.419 (5)
O2—N3	1.225 (4)	C22—H22A	0.96
N3—C4	1.463 (5)	C22—H22B	0.96
C4—C9	1.374 (5)	C22—H22C	0.96
C4—C5	1.382 (4)	C23—C28	1.389 (4)
C5—C6	1.403 (4)	C23—C24	1.402 (4)
C5—H5	0.98 (4)	C24—C25	1.373 (5)
C6—C7	1.379 (5)	C24—H24	0.99 (4)
C6—C10	1.458 (4)	C25—C26	1.383 (5)
C7—C8	1.385 (5)	C25—H25	1.03 (4)
C7—H7	0.95 (4)	C26—O29	1.371 (4)
C8—C9	1.365 (6)	C26—C27	1.379 (5)
C8—H8	0.98 (4)	C27—C28	1.394 (4)
C9—H9	1.01 (4)	C27—H27	1.01 (4)
C10—N14	1.329 (4)	C28—H28	0.95 (4)
C10—N11	1.357 (4)	O29—C30	1.410 (5)
N11—C12	1.381 (4)	C30—H30A	0.96
N11—H11	0.90 (4)	C30—H30B	0.96
C12—C13	1.379 (4)	C30—H30C	0.96
C12—C15	1.477 (4)	O31—C32	1.440 (4)
C13—N14	1.381 (4)	O31—H31	0.90 (5)
C13—C23	1.470 (4)	C32—C35	1.510 (6)
C15—C20	1.383 (4)	C32—C33	1.516 (6)
C15—C16	1.389 (4)	C32—C34	1.521 (5)
C16—C17	1.384 (5)	C33—H33A	0.96
C16—H16	0.98 (4)	C33—H33B	0.96
C17—C18	1.387 (5)	C33—H33C	0.96
C17—H17	0.89 (4)	C34—H34A	0.96
C18—O21	1.372 (4)	C34—H34B	0.96
C18—C19	1.381 (4)	C34—H34C	0.96
C19—C20	1.389 (4)	C35—H35A	0.96
C19—H19	1.00 (4)	C35—H35B	0.96
C20—H20	0.97 (4)	C35—H35C	0.96
O1—N3—O2	123.1 (4)	H22A—C22—H22B	109.5
O1—N3—C4	118.9 (3)	O21—C22—H22C	109.5
O2—N3—C4	118.0 (4)	H22A—C22—H22C	109.5
C9—C4—C5	123.8 (3)	H22B—C22—H22C	109.5
C9—C4—N3	117.7 (3)	C28—C23—C24	117.1 (3)
C5—C4—N3	118.5 (3)	C28—C23—C13	120.7 (3)
C4—C5—C6	118.2 (3)	C24—C23—C13	122.2 (3)
C4—C5—H5	120 (2)	C25—C24—C23	121.3 (3)
C6—C5—H5	121.5 (19)	C25—C24—H24	121 (2)
C7—C6—C5	118.2 (3)	C23—C24—H24	118 (2)
C7—C6—C10	122.1 (3)	C26—C25—C24	120.4 (3)
C5—C6—C10	119.6 (3)	C26—C25—H25	115 (2)
C8—C7—C6	121.6 (4)	C24—C25—H25	124 (2)
C8—C7—H7	118 (3)	O29—C26—C27	125.0 (3)
C6—C7—H7	120 (3)	O29—C26—C25	115.0 (3)
C9—C8—C7	121.0 (4)	C27—C26—C25	120.0 (3)
C9—C8—H8	122 (3)	C26—C27—C28	119.1 (3)
C7—C8—H8	117 (3)	C26—C27—H27	120 (2)
C8—C9—C4	117.2 (3)	C28—C27—H27	121 (2)
C8—C9—H9	123 (2)	C23—C28—C27	122.1 (3)
C4—C9—H9	120 (2)	C23—C28—H28	119 (2)
N14—C10—N11	110.4 (2)	C27—C28—H28	119 (2)
N14—C10—C6	125.9 (3)	C26—O29—C30	118.6 (3)
N11—C10—C6	123.4 (3)	O29—C30—H30A	109.5
C10—N11—C12	108.3 (3)	O29—C30—H30B	109.5
C10—N11—H11	125 (2)	H30A—C30—H30B	109.5
C12—N11—H11	127 (2)	O29—C30—H30C	109.5
C13—C12—N11	105.2 (3)	H30A—C30—H30C	109.5
C13—C12—C15	133.5 (3)	H30B—C30—H30C	109.5
N11—C12—C15	121.0 (3)	C32—O31—H31	107 (3)
N14—C13—C12	109.6 (3)	O31—C32—C35	108.9 (3)
N14—C13—C23	119.9 (3)	O31—C32—C33	109.1 (3)
C12—C13—C23	130.5 (3)	C35—C32—C33	111.0 (4)
C10—N14—C13	106.4 (2)	O31—C32—C34	104.5 (3)
C20—C15—C16	118.0 (3)	C35—C32—C34	111.8 (4)
C20—C15—C12	120.1 (3)	C33—C32—C34	111.3 (4)
C16—C15—C12	121.9 (3)	C32—C33—H33A	109.5
C15—C16—C17	121.1 (3)	C32—C33—H33B	109.5
C15—C16—H16	121 (2)	H33A—C33—H33B	109.5
C17—C16—H16	118 (2)	C32—C33—H33C	109.5
C18—C17—C16	120.1 (3)	H33A—C33—H33C	109.5
C18—C17—H17	116 (3)	H33B—C33—H33C	109.5
C16—C17—H17	124 (3)	C32—C34—H34A	109.5
O21—C18—C17	116.0 (3)	C32—C34—H34B	109.5
O21—C18—C19	124.4 (3)	H34A—C34—H34B	109.5
C17—C18—C19	119.6 (3)	C32—C34—H34C	109.5
C18—C19—C20	119.6 (3)	H34A—C34—H34C	109.5
C18—C19—H19	123 (2)	H34B—C34—H34C	109.5
C20—C19—H19	117 (2)	C32—C35—H35A	109.5
C15—C20—C19	121.6 (3)	C32—C35—H35B	109.5
C15—C20—H20	119 (2)	H35A—C35—H35B	109.5
C19—C20—H20	119 (2)	C32—C35—H35C	109.5
C18—O21—C22	117.8 (3)	H35A—C35—H35C	109.5
O21—C22—H22A	109.5	H35B—C35—H35C	109.5
O21—C22—H22B	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O31	0.90 (4)	2.08 (4)	2.915 (4)	155 (3)
O31—H31···N14^i	0.90 (4)	2.09 (6)	2.930 (4)	156 (5)

Symmetry code: (i) −x, −y+1, −z.

(3) 4,5-Bis(4-methoxyphenyl)-2-(3-nitrophenyl)-1H-imidazole 0.5-dioxane solvate

Crystal data

C23H19N3O4·0.5C4H8O2	Z = 2
Mr = 445.46	F(000) = 468
Triclinic, P1	Dx = 1.329 Mg m^−3 Dm = 1.32 (2) Mg m^−3 Dm measured by flotation
a = 9.510 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.236 (4) Å	Cell parameters from 25 reflections
c = 9.168 (2) Å	θ = 11.4–13.8°
α = 104.651 (13)°	µ = 0.09 mm^−1
β = 92.624 (15)°	T = 293 K
γ = 85.83 (2)°	Plate, yellow
V = 1113.1 (5) Å^3	0.40 × 0.40 × 0.10 mm

Data collection

Enraf-Nonius CAD4 diffractometer	Rint = 0.040
Radiation source: fine-focus sealed tube	θmax = 30.5°, θmin = 1.6°
Graphite monochromator	h = −13→13
ω–2θ scans	k = −18→18
7159 measured reflections	l = 0→13
6768 independent reflections	3 standard reflections every 120 min
4190 reflections with I > 2σ(I)	intensity decay: 0.9%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Calculated w = 1/[σ^2(Fo^2) + (0.0793P)^2 + 0.2048P] where P = (Fo^2 + 2Fc^2)/3
6768 reflections	(Δ/σ)max = 0.001>
377 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

4.143 (0.025) x + 5.280 (0.106) y + 6.196 (0.063) z = 0.507 (0.030)

* 0.000 (0.000) O1 * 0.000 (0.000) O2A * 0.000 (0.000) N3

Rms deviation of fitted atoms = 0.000

5.433 (0.008) x − 0.367 (0.012) y + 7.484 (0.006) z = 0.923 (0.005)

Angle to previous plane (with approximate e.s.d.) = 25.44 (0.61)

* 0.005 (0.002) C4 * −0.001 (0.001) C5 * −0.004 (0.001) C6 * 0.004 (0.002) C7 * 0.000 (0.002) C8 * −0.005 (0.002) C9

Rms deviation of fitted atoms = 0.004

− 3.194 (0.042) x − 3.147 (0.108) y + 8.765 (0.014) z = 0.761 (0.030)

Angle to previous plane (with approximate e.s.d.) = 19.66 (1/3)

* 0.000 (0.000) O1 * 0.000 (0.000) O2B * 0.000 (0.000) N3

Rms deviation of fitted atoms = 0.000

5.433 (0.008) x − 0.367 (0.012) y + 7.484 (0.006) z = 0.923 (0.005)

Angle to previous plane (with approximate e.s.d.) = 19.66 (1/3)

* 0.005 (0.002) C4 * −0.001 (0.001) C5 * −0.004 (0.001) C6 * 0.004 (0.002) C7 * 0.000 (0.002) C8 * −0.005 (0.002) C9

Rms deviation of fitted atoms = 0.004

4.646 (0.006) x − 1.255 (0.010) y + 8.060 (0.004) z = 0.703 (0.006)

Angle to previous plane (with approximate e.s.d.) = 6.95 (0.11)

* −0.008 (0.001) C10 * 0.008 (0.001) N11 * −0.006 (0.001) C12 * 0.001 (0.001) C13 * 0.004 (0.001) N14

Rms deviation of fitted atoms = 0.006

7.880 (0.005) x + 7.351 (0.008) y + 0.805 (0.008) z = 7.637 (0.005)

Angle to previous plane (with approximate e.s.d.) = 77.92 (0.06)

* −0.004 (0.001) C15 * −0.004 (0.001) C16 * 0.010 (0.001) C17 * −0.008 (0.001) C18 * 0.001 (0.001) C19 * 0.005 (0.001) C20

Rms deviation of fitted atoms = 0.006

4.646 (0.006) x − 1.255 (0.010) y + 8.060 (0.004) z = 0.703 (0.006)

Angle to previous plane (with approximate e.s.d.) = 77.92 (0.06)

* −0.008 (0.001) C10 * 0.008 (0.001) N11 * −0.006 (0.001) C12 * 0.001 (0.001) C13 * 0.004 (0.001) N14

Rms deviation of fitted atoms = 0.006

5.713 (0.005) x + 0.842 (0.009) y + 7.029 (0.005) z = 0.589 (0.008)

Angle to previous plane (with approximate e.s.d.) = 12.40 (0.09)

* −0.004 (0.001) C23 * 0.003 (0.001) C24 * 0.001 (0.001) C25 * −0.004 (0.001) C26 * 0.003 (0.001) C27 * 0.001 (0.001) C28

Rms deviation of fitted atoms = 0.003

Refinement. Refinement on F² for ALL reflections except for 12 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _refine_ls_R_factor_gt etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.7080 (2)	0.03857 (14)	0.3587 (3)	0.1119 (7)
O2A	0.5404 (15)	−0.0670 (8)	0.3366 (11)	0.116 (3)	0.50
O2B	0.5732 (15)	−0.0837 (8)	0.2657 (11)	0.116 (3)	0.50
N3	0.5937 (2)	0.00989 (14)	0.3067 (3)	0.0902 (6)
C4	0.4992 (2)	0.08102 (13)	0.2424 (2)	0.0604 (5)
C5	0.5297 (2)	0.18459 (13)	0.2704 (2)	0.0510 (4)
H5	0.609 (2)	0.2083 (16)	0.335 (2)	0.065 (6)*
C6	0.4412 (2)	0.25230 (12)	0.2098 (2)	0.0455 (3)
C7	0.3250 (2)	0.2123 (2)	0.1225 (3)	0.0690 (5)
H7	0.262 (2)	0.2562 (18)	0.083 (3)	0.077 (7)*
C8	0.2966 (3)	0.1084 (2)	0.0973 (3)	0.0852 (7)
H8	0.213 (3)	0.0828 (19)	0.036 (3)	0.090 (7)*
C9	0.3838 (2)	0.0413 (2)	0.1580 (3)	0.0769 (6)
H9	0.365 (3)	−0.032 (2)	0.137 (3)	0.094 (8)*
C10	0.4703 (2)	0.36281 (11)	0.2414 (2)	0.0416 (3)
N11	0.38083 (15)	0.43603 (10)	0.19920 (15)	0.0442 (3)
H11	0.291 (2)	0.4287 (16)	0.155 (2)	0.069 (6)*
C12	0.4389 (2)	0.53124 (11)	0.2493 (2)	0.0421 (3)
C13	0.5659 (2)	0.51096 (11)	0.3184 (2)	0.0414 (3)
N14	0.58447 (13)	0.40494 (9)	0.31231 (14)	0.0423 (3)
C15	0.3609 (2)	0.62678 (12)	0.2255 (2)	0.0424 (3)
C16	0.3551 (2)	0.64835 (13)	0.0846 (2)	0.0494 (4)
H16	0.405 (2)	0.6005 (15)	0.002 (2)	0.059 (5)*
C17	0.2781 (2)	0.73542 (14)	0.0611 (2)	0.0553 (4)
H17	0.274 (2)	0.7472 (16)	−0.036 (3)	0.071 (6)*
C18	0.2027 (2)	0.80105 (12)	0.1769 (2)	0.0539 (4)
C19	0.2081 (2)	0.78107 (14)	0.3177 (2)	0.0637 (5)
H19	0.163 (3)	0.8215 (19)	0.400 (3)	0.084 (7)*
C20	0.2873 (2)	0.69429 (14)	0.3411 (2)	0.0582 (4)
H20	0.297 (2)	0.6793 (18)	0.440 (3)	0.083 (7)*
O21	0.1243 (2)	0.88230 (10)	0.1396 (2)	0.0784 (4)
C22	0.0398 (3)	0.9485 (2)	0.2532 (4)	0.1234 (12)
H22A	−0.0121	1.0007	0.2127	0.185*
H22B	0.0991	0.9820	0.3363	0.185*
H22C	−0.0249	0.9077	0.2874	0.185*
C23	0.6719 (2)	0.58377 (11)	0.3930 (2)	0.0414 (3)
C24	0.6705 (2)	0.68699 (13)	0.3784 (2)	0.0501 (4)
H24	0.600 (2)	0.7104 (15)	0.319 (2)	0.062 (5)*
C25	0.7702 (2)	0.75407 (13)	0.4518 (2)	0.0540 (4)
H25	0.766 (2)	0.8269 (16)	0.445 (2)	0.061 (5)*
C26	0.8754 (2)	0.72057 (12)	0.5419 (2)	0.0477 (4)
C27	0.8801 (2)	0.61901 (13)	0.5569 (2)	0.0494 (4)
H27	0.953 (2)	0.5911 (15)	0.617 (2)	0.060 (5)*
C28	0.7787 (2)	0.55205 (12)	0.4828 (2)	0.0457 (3)
H28	0.7852 (17)	0.4802 (13)	0.4924 (18)	0.045 (4)*
O29	0.96917 (14)	0.79261 (10)	0.6114 (2)	0.0637 (3)
C30	1.0656 (2)	0.7656 (2)	0.7200 (3)	0.0707 (6)
H30A	1.1219	0.8237	0.7636	0.106*
H30B	1.1258	0.7062	0.6722	0.106*
H30C	1.0145	0.7487	0.7976	0.106*
O31	0.09737 (14)	0.44547 (11)	0.07708 (14)	0.0645 (4)
C32	0.0583 (3)	0.4035 (2)	−0.0768 (2)	0.0692 (5)
H32A	−0.027 (3)	0.359 (2)	−0.089 (3)	0.118 (10)*
H32B	0.147 (3)	0.362 (2)	−0.126 (3)	0.095 (8)*
C33	−0.0156 (3)	0.5123 (2)	0.1526 (2)	0.0777 (7)
H33A	0.014 (3)	0.543 (2)	0.251 (3)	0.094 (8)*
H33B	−0.112 (4)	0.468 (3)	0.142 (4)	0.129 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0918 (13)	0.0749 (11)	0.172 (2)	0.0032 (10)	−0.0422 (13)	0.0474 (12)
O2A	0.129 (6)	0.067 (5)	0.174 (9)	−0.016 (4)	−0.019 (6)	0.072 (6)
O2B	0.147 (8)	0.050 (3)	0.158 (8)	−0.006 (3)	−0.033 (6)	0.046 (5)
N3	0.0923 (15)	0.0529 (10)	0.132 (2)	0.0000 (10)	−0.0184 (13)	0.0405 (11)
C4	0.0606 (11)	0.0434 (9)	0.0808 (13)	0.0005 (8)	0.0018 (9)	0.0232 (9)
C5	0.0485 (9)	0.0434 (8)	0.0622 (10)	−0.0014 (7)	0.0006 (8)	0.0157 (7)
C6	0.0451 (8)	0.0415 (8)	0.0512 (8)	−0.0007 (6)	0.0052 (7)	0.0138 (6)
C7	0.0637 (12)	0.0529 (10)	0.0889 (15)	−0.0046 (9)	−0.0210 (11)	0.0190 (10)
C8	0.0731 (14)	0.0570 (12)	0.122 (2)	−0.0171 (10)	−0.0316 (14)	0.0178 (12)
C9	0.0726 (14)	0.0447 (10)	0.113 (2)	−0.0144 (9)	−0.0082 (13)	0.0187 (11)
C10	0.0431 (8)	0.0401 (7)	0.0431 (7)	0.0018 (6)	0.0030 (6)	0.0140 (6)
N11	0.0439 (7)	0.0414 (7)	0.0475 (7)	0.0018 (5)	0.0003 (6)	0.0129 (5)
C12	0.0470 (8)	0.0391 (7)	0.0410 (7)	0.0028 (6)	0.0053 (6)	0.0121 (6)
C13	0.0462 (8)	0.0393 (7)	0.0396 (7)	0.0030 (6)	0.0041 (6)	0.0126 (6)
N14	0.0454 (7)	0.0391 (6)	0.0442 (6)	0.0018 (5)	0.0025 (5)	0.0146 (5)
C15	0.0419 (8)	0.0402 (7)	0.0456 (8)	0.0022 (6)	0.0010 (6)	0.0131 (6)
C16	0.0498 (9)	0.0514 (9)	0.0492 (9)	0.0085 (7)	0.0078 (7)	0.0188 (7)
C17	0.0537 (10)	0.0558 (10)	0.0627 (11)	0.0033 (8)	0.0000 (8)	0.0287 (8)
C18	0.0459 (9)	0.0357 (7)	0.0808 (12)	0.0006 (6)	−0.0047 (8)	0.0176 (8)
C19	0.0730 (13)	0.0440 (9)	0.0670 (12)	0.0113 (8)	0.0135 (10)	0.0031 (8)
C20	0.0750 (12)	0.0493 (9)	0.0475 (9)	0.0092 (8)	0.0074 (8)	0.0098 (7)
O21	0.0715 (9)	0.0465 (7)	0.1181 (12)	0.0139 (6)	−0.0048 (8)	0.0286 (7)
C22	0.119 (2)	0.066 (2)	0.177 (3)	0.049 (2)	0.024 (2)	0.028 (2)
C23	0.0441 (8)	0.0397 (7)	0.0413 (7)	0.0020 (6)	0.0050 (6)	0.0124 (6)
C24	0.0520 (9)	0.0458 (8)	0.0565 (9)	−0.0003 (7)	−0.0060 (7)	0.0220 (7)
C25	0.0582 (10)	0.0410 (8)	0.0667 (11)	−0.0029 (7)	−0.0034 (8)	0.0215 (8)
C26	0.0476 (9)	0.0425 (8)	0.0516 (9)	−0.0019 (6)	0.0004 (7)	0.0100 (7)
C27	0.0492 (9)	0.0465 (8)	0.0531 (9)	0.0027 (7)	−0.0049 (7)	0.0162 (7)
C28	0.0508 (9)	0.0381 (7)	0.0496 (8)	0.0021 (6)	−0.0006 (7)	0.0150 (6)
O29	0.0618 (8)	0.0493 (7)	0.0787 (9)	−0.0099 (6)	−0.0152 (6)	0.0150 (6)
C30	0.0588 (11)	0.0610 (11)	0.0866 (14)	−0.0043 (9)	−0.0177 (10)	0.0113 (10)
O31	0.0573 (7)	0.0763 (9)	0.0575 (7)	0.0112 (6)	−0.0096 (6)	0.0184 (6)
C32	0.0685 (13)	0.0705 (13)	0.0622 (12)	0.0113 (11)	−0.0018 (10)	0.0100 (10)
C33	0.086 (2)	0.093 (2)	0.0487 (11)	0.0228 (13)	0.0038 (10)	0.0171 (11)

Geometric parameters (Å, º)

O1—N3	1.213 (3)	C19—C20	1.385 (3)
O2A—N3	1.264 (11)	C19—H19	0.91 (2)
O2B—N3	1.228 (11)	C20—H20	0.97 (2)
N3—C4	1.467 (3)	O21—C22	1.418 (3)
C4—C9	1.371 (3)	C22—H22A	0.96
C4—C5	1.379 (2)	C22—H22B	0.96
C5—C6	1.386 (2)	C22—H22C	0.96
C5—H5	0.96 (2)	C23—C28	1.387 (2)
C6—C7	1.390 (3)	C23—C24	1.405 (2)
C6—C10	1.462 (2)	C24—C25	1.379 (3)
C7—C8	1.380 (3)	C24—H24	0.93 (2)
C7—H7	0.93 (2)	C25—C26	1.387 (2)
C8—C9	1.373 (3)	C25—H25	0.98 (2)
C8—H8	0.98 (3)	C26—O29	1.369 (2)
C9—H9	0.97 (3)	C26—C27	1.383 (2)
C10—N14	1.323 (2)	C27—C28	1.391 (2)
C10—N11	1.361 (2)	C27—H27	0.97 (2)
N11—C12	1.374 (2)	C28—H28	0.97 (2)
N11—H11	0.93 (2)	O29—C30	1.417 (2)
C12—C13	1.379 (2)	C30—H30A	0.96
C12—C15	1.478 (2)	C30—H30B	0.96
C13—N14	1.389 (2)	C30—H30C	0.96
C13—C23	1.469 (2)	O31—C32	1.422 (2)
C15—C20	1.382 (2)	O31—C33	1.427 (3)
C15—C16	1.390 (2)	C32—C33^i	1.480 (3)
C16—C17	1.378 (2)	C32—H32A	1.02 (3)
C16—H16	0.98 (2)	C32—H32B	1.03 (3)
C17—C18	1.381 (3)	C33—C32^i	1.480 (3)
C17—H17	0.94 (2)	C33—H33A	0.93 (3)
C18—O21	1.370 (2)	C33—H33B	1.11 (3)
C18—C19	1.379 (3)
O1—N3—O2B	120.5 (7)	C20—C19—H19	115.5 (15)
O1—N3—O2A	121.8 (7)	C15—C20—C19	121.1 (2)
O1—N3—C4	118.8 (2)	C15—C20—H20	116.9 (14)
O2B—N3—C4	117.0 (7)	C19—C20—H20	121.9 (14)
O2A—N3—C4	117.3 (7)	C18—O21—C22	117.3 (2)
C9—C4—C5	123.1 (2)	O21—C22—H22A	109.5
C9—C4—N3	118.2 (2)	O21—C22—H22B	109.5
C5—C4—N3	118.6 (2)	H22A—C22—H22B	109.5
C4—C5—C6	119.0 (2)	O21—C22—H22C	109.5
C4—C5—H5	119.1 (12)	H22A—C22—H22C	109.5
C6—C5—H5	121.8 (12)	H22B—C22—H22C	109.5
C5—C6—C7	118.2 (2)	C28—C23—C24	117.09 (15)
C5—C6—C10	119.67 (15)	C28—C23—C13	120.21 (13)
C7—C6—C10	122.2 (2)	C24—C23—C13	122.70 (14)
C8—C7—C6	121.5 (2)	C25—C24—C23	121.4 (2)
C8—C7—H7	118.2 (14)	C25—C24—H24	119.8 (12)
C6—C7—H7	120.3 (14)	C23—C24—H24	118.9 (12)
C9—C8—C7	120.4 (2)	C24—C25—C26	120.4 (2)
C9—C8—H8	120.1 (14)	C24—C25—H25	120.9 (12)
C7—C8—H8	119.4 (14)	C26—C25—H25	118.7 (12)
C4—C9—C8	117.8 (2)	O29—C26—C27	124.10 (15)
C4—C9—H9	122.1 (15)	O29—C26—C25	116.42 (14)
C8—C9—H9	120.1 (15)	C27—C26—C25	119.5 (2)
N14—C10—N11	111.26 (13)	C26—C27—C28	119.69 (15)
N14—C10—C6	125.65 (13)	C26—C27—H27	122.9 (12)
N11—C10—C6	123.09 (14)	C28—C27—H27	117.4 (11)
C10—N11—C12	107.83 (13)	C23—C28—C27	121.99 (14)
C10—N11—H11	129.0 (13)	C23—C28—H28	119.4 (10)
C12—N11—H11	122.9 (13)	C27—C28—H28	118.6 (10)
N11—C12—C13	105.52 (13)	C26—O29—C30	117.70 (14)
N11—C12—C15	119.82 (14)	O29—C30—H30A	109.5
C13—C12—C15	134.63 (15)	O29—C30—H30B	109.5
C12—C13—N14	109.75 (13)	H30A—C30—H30B	109.5
C12—C13—C23	129.26 (13)	O29—C30—H30C	109.5
N14—C13—C23	120.98 (13)	H30A—C30—H30C	109.5
C10—N14—C13	105.61 (12)	H30B—C30—H30C	109.5
C20—C15—C16	118.51 (15)	C32—O31—C33	110.0 (2)
C20—C15—C12	120.80 (14)	O31—C32—C33^i	111.2 (2)
C16—C15—C12	120.64 (14)	O31—C32—H32A	112.2 (17)
C17—C16—C15	120.6 (2)	C33^i—C32—H32A	105.2 (16)
C17—C16—H16	120.2 (11)	O31—C32—H32B	105.7 (14)
C15—C16—H16	119.2 (11)	C33^i—C32—H32B	109.8 (14)
C16—C17—C18	120.2 (2)	H32A—C32—H32B	113 (2)
C16—C17—H17	118.9 (13)	O31—C33—C32^i	111.3 (2)
C18—C17—H17	120.8 (13)	O31—C33—H33A	108.9 (16)
O21—C18—C19	124.7 (2)	C32^i—C33—H33A	108.3 (16)
O21—C18—C17	115.5 (2)	O31—C33—H33B	109.8 (17)
C19—C18—C17	119.8 (2)	C32^i—C33—H33B	103.3 (16)
C18—C19—C20	119.7 (2)	H33A—C33—H33B	115 (2)
C18—C19—H19	124.8 (15)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O31	0.93 (2)	1.96 (2)	2.878 (2)	168 (2)

(4) 4,5-Bis(4-methoxyphenyl)-2-(3-nitrophenyl)-1H-imidazole benzene solvate

Crystal data

C23H19N3O4·C6H6	F(000) = 1008
Mr = 479.52	Dx = 1.272 Mg m^−3 Dm = 1.25 (2) Mg m^−3 Dm measured by flotation
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.614 (2) Å	Cell parameters from 25 reflections
b = 29.011 (5) Å	θ = 11.3–13.8°
c = 8.984 (2) Å	µ = 0.09 mm^−1
β = 91.933 (10)°	T = 293 K
V = 2504.3 (9) Å^3	Needle, intense yellow
Z = 4	0.40 × 0.40 × 0.30 mm

Data collection

Enraf-Nonius CAD4 diffractometer	Rint = 0.025
Radiation source: fine-focus sealed tube	θmax = 30.0°, θmin = 1.4°
Graphite monochromator	h = −13→13
ω–2θ scans	k = 0→40
7687 measured reflections	l = 0→12
7270 independent reflections	3 standard reflections every 120 min
3320 reflections with I > 2σ(I)	intensity decay: −0.9%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.191	H atoms treated by a mixture of independent and constrained refinement
S = 0.88	Calculated w = 1/[σ^2(Fo^2) + (0.1839P)^2 + 0.8562P] where P = (Fo^2 + 2Fc^2)/3
7258 reflections	(Δ/σ)max = 0.001
379 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

7.363 (0.048) x − 8.213 (0.081) y − 5.416 (0.059) z = 4.451 (0.087)

* 0.000 (0.000) O1 * 0.000 (0.000) O2 * 0.000 (0.000) N3

Rms deviation of fitted atoms = 0.000

7.231 (0.009) x − 6.966 (0.041) y − 5.738 (0.010) z = 4.617 (0.019)

Angle to previous plane (with approximate e.s.d.) = 3.32 (0.79)

* −0.006 (0.002) C4 * 0.007 (0.002) C5 * −0.001 (0.002) C6 * −0.006 (0.002) C7 * 0.007 (0.003) C8 * −0.001 (0.003) C9

Rms deviation of fitted atoms = 0.006

7.733 (0.008) x − 11.640 (0.040) y − 4.178 (0.011) z = 3.923 (0.015)

Angle to previous plane (with approximate e.s.d.) = 14.01 (0.19)

* 0.005 (0.002) C10 * −0.006 (0.002) N11 * 0.004 (0.002) C12 * −0.001 (0.002) C13 * −0.002 (0.002) N14

Rms deviation of fitted atoms = 0.004

7.400 (0.009) x + 5.817 (0.044) y − 5.675 (0.010) z = 7.363 (0.007)

Angle to previous plane (with approximate e.s.d.) = 36.46 (0.13)

* −0.004 (0.002) C15 * 0.004 (0.002) C16 * 0.001 (0.002) C17 * −0.005 (0.003) C18 * 0.005 (0.003) C19 * 0.000 (0.003) C20

Rms deviation of fitted atoms = 0.004

7.733 (0.008) x − 11.640 (0.040) y − 4.178 (0.011) z = 3.923 (0.015)

Angle to previous plane (with approximate e.s.d.) = 36.46 (0.13)

* 0.005 (0.002) C10 * −0.006 (0.002) N11 * 0.004 (0.002) C12 * −0.001 (0.002) C13 * −0.002 (0.002) N14

Rms deviation of fitted atoms = 0.004

− 2.235 (0.014) x + 11.188 (0.036) y + 8.087 (0.006) z = 0.659 (0.012)

Angle to previous plane (with approximate e.s.d.) = 42.86 (0.14)

* −0.008 (0.002) C23 * 0.007 (0.003) C24 * 0.002 (0.003) C25 * −0.009 (0.002) C26 * 0.008 (0.002) C27 * 0.001 (0.002) C28

Rms deviation of fitted atoms = 0.007

Refinement. Refinement on F² for ALL reflections except for 12 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _refine_ls_R_factor_gt etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	1.2600 (4)	0.29055 (13)	0.4503 (4)	0.1100 (13)
O2	1.3138 (4)	0.36117 (12)	0.4164 (4)	0.1102 (12)
N3	1.2496 (3)	0.32663 (13)	0.3815 (4)	0.0727 (9)
C4	1.1534 (3)	0.32837 (12)	0.2514 (4)	0.0533 (8)
C5	1.0837 (3)	0.28899 (12)	0.2090 (3)	0.0454 (7)
H5	1.102 (4)	0.2602 (11)	0.258 (4)	0.054 (9)*
C6	0.9888 (3)	0.29083 (10)	0.0887 (3)	0.0413 (6)
C7	0.9691 (4)	0.33270 (12)	0.0139 (4)	0.0539 (8)
H7	0.901 (4)	0.3347 (12)	−0.070 (5)	0.069 (11)*
C8	1.0433 (4)	0.37141 (14)	0.0580 (4)	0.0649 (9)
H8	1.027 (4)	0.4000 (14)	0.005 (4)	0.071 (11)*
C9	1.1361 (4)	0.37001 (14)	0.1781 (4)	0.0645 (10)
H9	1.177 (4)	0.3962 (12)	0.209 (4)	0.053 (9)*
C10	0.9088 (3)	0.25018 (10)	0.0449 (3)	0.0403 (6)
N11	0.8322 (2)	0.24673 (9)	−0.0847 (2)	0.0411 (5)
H11	0.844 (4)	0.2666 (12)	−0.164 (4)	0.055 (9)*
C12	0.7682 (3)	0.20464 (10)	−0.0883 (3)	0.0402 (6)
C13	0.8078 (3)	0.18359 (10)	0.0449 (3)	0.0414 (6)
N14	0.8952 (2)	0.21240 (8)	0.1267 (2)	0.0425 (6)
C15	0.6785 (3)	0.19088 (10)	−0.2162 (3)	0.0420 (6)
C16	0.5968 (3)	0.22335 (11)	−0.2910 (3)	0.0483 (7)
H16	0.596 (4)	0.2571 (11)	−0.258 (4)	0.053 (9)*
C17	0.5112 (3)	0.21159 (13)	−0.4142 (3)	0.0538 (8)
H17	0.462 (4)	0.2368 (14)	−0.468 (5)	0.076 (12)*
C18	0.5089 (3)	0.16645 (13)	−0.4624 (3)	0.0567 (8)
C19	0.5909 (4)	0.13363 (14)	−0.3909 (4)	0.0644 (9)
H19	0.588 (4)	0.1021 (15)	−0.426 (5)	0.081 (12)*
C20	0.6745 (4)	0.14554 (12)	−0.2687 (4)	0.0549 (8)
H20	0.734 (4)	0.1217 (12)	−0.219 (4)	0.054 (9)*
O21	0.4266 (3)	0.15068 (10)	−0.5796 (3)	0.0805 (8)
C22	0.3376 (5)	0.1824 (2)	−0.6548 (5)	0.0851 (14)
H22A	0.2713	0.1942	−0.5870	0.128*
H22B	0.2892	0.1671	−0.7360	0.128*
H22C	0.3916	0.2073	−0.6927	0.128*
C23	0.7713 (3)	0.13789 (10)	0.1029 (3)	0.0422 (6)
C24	0.6373 (3)	0.12022 (12)	0.0922 (4)	0.0541 (8)
H24	0.565 (4)	0.1382 (12)	0.044 (4)	0.064 (10)*
C25	0.6075 (4)	0.07666 (14)	0.1436 (4)	0.0613 (9)
H25	0.514 (4)	0.0669 (12)	0.134 (4)	0.064 (10)*
C26	0.7108 (3)	0.04969 (11)	0.2081 (3)	0.0518 (7)
C27	0.8447 (3)	0.06687 (12)	0.2235 (4)	0.0545 (8)
H27	0.918 (3)	0.0473 (11)	0.266 (4)	0.047 (8)*
C28	0.8743 (3)	0.11028 (12)	0.1707 (3)	0.0495 (7)
H28	0.971 (4)	0.1197 (12)	0.181 (4)	0.063 (10)*
O29	0.6941 (3)	0.00510 (9)	0.2561 (3)	0.0725 (8)
C30	0.5607 (5)	−0.0154 (2)	0.2366 (8)	0.113 (2)
H30A	0.5655	−0.0472	0.2658	0.169*
H30B	0.5308	−0.0133	0.1338	0.169*
H30C	0.4956	0.0005	0.2969	0.169*
C31A	0.7978 (6)	0.5126 (3)	0.1027 (3)	0.078 (2)	0.70
H31A	0.7901	0.5106	−0.0006	0.093*	0.70
C32A	0.7641 (5)	0.5535 (2)	0.1737 (9)	0.072 (2)	0.70
H32A	0.7340	0.5788	0.1179	0.086*	0.70
C33A	0.7755 (6)	0.5565 (2)	0.3280 (10)	0.071 (2)	0.70
H33A	0.7530	0.5838	0.3755	0.085*	0.70
C34A	0.8206 (7)	0.5186 (3)	0.4113 (3)	0.077 (2)	0.70
H34A	0.8282	0.5207	0.5146	0.092*	0.70
C35A	0.8543 (6)	0.4778 (2)	0.3403 (10)	0.083 (2)	0.70
H35A	0.8844	0.4524	0.3961	0.100*	0.70
C36A	0.8428 (6)	0.4747 (2)	0.1860 (10)	0.081 (2)	0.70
H36A	0.8654	0.4474	0.1385	0.097*	0.70
C31B	0.7736 (14)	0.5330 (7)	0.1102 (14)	0.073 (5)*	0.30
H31B	0.7484	0.5449	0.0169	0.088*	0.30
C32B	0.7578 (12)	0.5597 (3)	0.237 (3)	0.067 (5)*	0.30
H32B	0.7220	0.5894	0.2286	0.080*	0.30
C33B	0.7954 (14)	0.5420 (6)	0.3764 (16)	0.067 (5)*	0.30
H33B	0.7848	0.5599	0.4612	0.081*	0.30
C34B	0.8489 (13)	0.4976 (7)	0.3889 (12)	0.063 (4)*	0.30
H34B	0.8741	0.4858	0.4821	0.075*	0.30
C35B	0.8648 (13)	0.4709 (3)	0.262 (2)	0.075 (5)*	0.30
H35B	0.9006	0.4412	0.2705	0.090*	0.30
C36B	0.8271 (15)	0.4887 (6)	0.1227 (15)	0.076 (5)*	0.30
H36B	0.8377	0.4708	0.0379	0.092*	0.30

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.127 (3)	0.104 (3)	0.094 (2)	−0.005 (2)	−0.068 (2)	0.004 (2)
O2	0.101 (2)	0.112 (3)	0.114 (3)	−0.029 (2)	−0.051 (2)	−0.025 (2)
N3	0.061 (2)	0.088 (2)	0.067 (2)	−0.004 (2)	−0.023 (2)	−0.017 (2)
C4	0.045 (2)	0.066 (2)	0.048 (2)	−0.0030 (14)	−0.0071 (13)	−0.0109 (15)
C5	0.045 (2)	0.053 (2)	0.0376 (14)	−0.0005 (13)	−0.0066 (11)	−0.0002 (13)
C6	0.0400 (14)	0.052 (2)	0.0321 (12)	−0.0016 (12)	−0.0019 (10)	−0.0025 (11)
C7	0.055 (2)	0.061 (2)	0.044 (2)	−0.002 (2)	−0.0086 (14)	0.0013 (14)
C8	0.070 (2)	0.055 (2)	0.068 (2)	−0.006 (2)	−0.009 (2)	0.003 (2)
C9	0.063 (2)	0.059 (2)	0.071 (2)	−0.012 (2)	−0.008 (2)	−0.009 (2)
C10	0.0412 (14)	0.050 (2)	0.0293 (12)	−0.0004 (12)	−0.0023 (10)	−0.0004 (11)
N11	0.0448 (12)	0.0501 (14)	0.0280 (10)	−0.0022 (11)	−0.0045 (9)	−0.0002 (10)
C12	0.0403 (14)	0.047 (2)	0.0332 (12)	0.0001 (12)	−0.0011 (10)	−0.0023 (11)
C13	0.0387 (13)	0.052 (2)	0.0331 (13)	0.0006 (12)	−0.0035 (10)	−0.0015 (12)
N14	0.0460 (13)	0.0508 (14)	0.0304 (11)	−0.0009 (10)	−0.0052 (9)	−0.0001 (10)
C15	0.0412 (14)	0.054 (2)	0.0302 (12)	−0.0031 (12)	−0.0031 (10)	−0.0013 (12)
C16	0.051 (2)	0.051 (2)	0.0415 (15)	−0.0017 (13)	−0.0104 (12)	−0.0038 (13)
C17	0.052 (2)	0.063 (2)	0.045 (2)	−0.004 (2)	−0.0132 (13)	0.0015 (15)
C18	0.054 (2)	0.074 (2)	0.041 (2)	−0.014 (2)	−0.0119 (13)	−0.0091 (15)
C19	0.074 (2)	0.060 (2)	0.058 (2)	−0.006 (2)	−0.011 (2)	−0.014 (2)
C20	0.061 (2)	0.051 (2)	0.052 (2)	0.001 (2)	−0.0092 (15)	−0.0066 (15)
O21	0.081 (2)	0.094 (2)	0.064 (2)	−0.0130 (15)	−0.0315 (14)	−0.0176 (14)
C22	0.083 (3)	0.106 (3)	0.063 (2)	−0.030 (2)	−0.039 (2)	0.012 (2)
C23	0.0439 (15)	0.049 (2)	0.0330 (13)	0.0003 (12)	−0.0040 (11)	−0.0019 (12)
C24	0.043 (2)	0.062 (2)	0.057 (2)	0.0001 (14)	−0.0039 (14)	0.015 (2)
C25	0.043 (2)	0.074 (2)	0.066 (2)	−0.008 (2)	−0.002 (2)	0.016 (2)
C26	0.057 (2)	0.052 (2)	0.046 (2)	−0.0041 (14)	−0.0023 (13)	0.0083 (13)
C27	0.051 (2)	0.059 (2)	0.052 (2)	0.0038 (15)	−0.0129 (14)	0.006 (2)
C28	0.044 (2)	0.057 (2)	0.046 (2)	−0.0023 (14)	−0.0108 (13)	0.0005 (14)
O29	0.070 (2)	0.065 (2)	0.082 (2)	−0.0119 (13)	−0.0070 (13)	0.0243 (13)
C30	0.083 (3)	0.085 (3)	0.169 (6)	−0.027 (3)	−0.008 (3)	0.050 (3)
C31A	0.082 (4)	0.085 (5)	0.064 (4)	0.012 (4)	−0.008 (3)	−0.006 (3)
C32A	0.081 (4)	0.071 (4)	0.063 (4)	0.008 (3)	0.006 (3)	0.000 (3)
C33A	0.067 (3)	0.074 (4)	0.073 (5)	−0.010 (3)	0.008 (3)	−0.004 (4)
C34A	0.089 (4)	0.075 (5)	0.065 (4)	−0.010 (4)	0.004 (3)	0.001 (3)
C35A	0.103 (5)	0.072 (4)	0.074 (5)	−0.007 (4)	−0.004 (4)	0.014 (4)
C36A	0.095 (5)	0.063 (4)	0.084 (5)	0.004 (3)	−0.009 (4)	−0.003 (4)

Geometric parameters (Å, º)

O1—N3	1.218 (5)	C23—C28	1.397 (4)
O2—N3	1.212 (4)	C24—C25	1.379 (5)
N3—C4	1.467 (4)	C24—H24	0.96 (4)
C4—C5	1.372 (4)	C25—C26	1.377 (5)
C4—C9	1.383 (5)	C25—H25	0.94 (4)
C5—C6	1.392 (4)	C26—O29	1.375 (4)
C5—H5	0.95 (3)	C26—C27	1.383 (5)
C6—C7	1.398 (4)	C27—C28	1.379 (5)
C6—C10	1.455 (4)	C27—H27	0.97 (3)
C7—C8	1.381 (5)	C28—H28	0.97 (4)
C7—H7	0.99 (4)	O29—C30	1.419 (5)
C8—C9	1.378 (5)	C30—H30A	0.96
C8—H8	0.97 (4)	C30—H30B	0.96
C9—H9	0.89 (3)	C30—H30C	0.96
C10—N14	1.328 (4)	C31A—C32A	1.39
C10—N11	1.361 (3)	C31A—C36A	1.39
N11—C12	1.367 (4)	C31A—H31A	0.93
N11—H11	0.92 (4)	C32A—C33A	1.39
C12—C13	1.385 (4)	C32A—H32A	0.93
C12—C15	1.468 (4)	C33A—C34A	1.39
C13—N14	1.380 (4)	C33A—H33A	0.93
C13—C23	1.471 (4)	C34A—C35A	1.39
C15—C16	1.386 (4)	C34A—H34A	0.93
C15—C20	1.397 (4)	C35A—C36A	1.39
C16—C17	1.399 (4)	C35A—H35A	0.93
C16—H16	1.02 (3)	C36A—H36A	0.93
C17—C18	1.379 (5)	C31B—C32B	1.39
C17—H17	0.99 (4)	C31B—C36B	1.39
C18—O21	1.374 (4)	C31B—H31B	0.93
C18—C19	1.381 (5)	C32B—C33B	1.39
C19—C20	1.382 (5)	C32B—H32B	0.93
C19—H19	0.97 (4)	C33B—C34B	1.39
C20—H20	0.99 (3)	C33B—H33B	0.93
O21—C22	1.412 (5)	C34B—C35B	1.39
C22—H22A	0.96	C34B—H34B	0.93
C22—H22B	0.96	C35B—C36B	1.39
C22—H22C	0.96	C35B—H35B	0.93
C23—C24	1.387 (4)	C36B—H36B	0.93
O2—N3—O1	123.2 (3)	C24—C23—C13	122.7 (3)
O2—N3—C4	118.6 (4)	C28—C23—C13	119.8 (3)
O1—N3—C4	118.2 (3)	C23—C24—C25	121.3 (3)
C5—C4—C9	123.1 (3)	C23—C24—H24	119 (2)
C5—C4—N3	118.8 (3)	C25—C24—H24	119 (2)
C9—C4—N3	118.2 (3)	C26—C25—C24	120.4 (3)
C4—C5—C6	119.0 (3)	C26—C25—H25	123 (2)
C4—C5—H5	121 (2)	C24—C25—H25	117 (2)
C6—C5—H5	120 (2)	O29—C26—C25	125.2 (3)
C5—C6—C7	118.8 (3)	O29—C26—C27	115.2 (3)
C5—C6—C10	120.4 (3)	C25—C26—C27	119.6 (3)
C7—C6—C10	120.8 (2)	C26—C27—C28	119.8 (3)
C8—C7—C6	120.6 (3)	C26—C27—H27	119.2 (18)
C8—C7—H7	120 (2)	C28—C27—H27	120.9 (19)
C6—C7—H7	120 (2)	C27—C28—C23	121.5 (3)
C7—C8—C9	121.0 (4)	C27—C28—H28	116 (2)
C7—C8—H8	119 (2)	C23—C28—H28	123 (2)
C9—C8—H8	120 (2)	C26—O29—C30	118.0 (3)
C8—C9—C4	117.6 (3)	O29—C30—H30A	109.5
C8—C9—H9	119 (2)	O29—C30—H30B	109.5
C4—C9—H9	123 (2)	H30A—C30—H30B	109.5
N14—C10—N11	110.6 (2)	O29—C30—H30C	109.5
N14—C10—C6	125.5 (2)	H30A—C30—H30C	109.5
N11—C10—C6	123.9 (2)	H30B—C30—H30C	109.5
C10—N11—C12	108.4 (2)	C32A—C31A—C36A	120.0
C10—N11—H11	123 (2)	C32A—C31A—H31A	120.0
C12—N11—H11	127 (2)	C36A—C31A—H31A	120.0
N11—C12—C13	105.2 (2)	C31A—C32A—C33A	120.0
N11—C12—C15	120.9 (2)	C31A—C32A—H32A	120.0
C13—C12—C15	133.9 (3)	C33A—C32A—H32A	120.0
N14—C13—C12	109.7 (3)	C32A—C33A—C34A	120.0
N14—C13—C23	120.3 (2)	C32A—C33A—H33A	120.0
C12—C13—C23	129.9 (3)	C34A—C33A—H33A	120.0
C10—N14—C13	106.0 (2)	C35A—C34A—C33A	120.0
C16—C15—C20	117.9 (3)	C35A—C34A—H34A	120.0
C16—C15—C12	120.2 (3)	C33A—C34A—H34A	120.0
C20—C15—C12	121.9 (3)	C34A—C35A—C36A	120.0
C15—C16—C17	121.8 (3)	C34A—C35A—H35A	120.0
C15—C16—H16	121.3 (19)	C36A—C35A—H35A	120.0
C17—C16—H16	116.9 (19)	C35A—C36A—C31A	120.0
C18—C17—C16	118.8 (3)	C35A—C36A—H36A	120.0
C18—C17—H17	123 (2)	C31A—C36A—H36A	120.0
C16—C17—H17	118 (2)	C32B—C31B—C36B	120.0
O21—C18—C19	115.6 (3)	C32B—C31B—H31B	120.0
O21—C18—C17	124.0 (3)	C36B—C31B—H31B	120.0
C19—C18—C17	120.4 (3)	C31B—C32B—C33B	120.0
C18—C19—C20	120.3 (3)	C31B—C32B—H32B	120.0
C18—C19—H19	119 (3)	C33B—C32B—H32B	120.0
C20—C19—H19	121 (3)	C34B—C33B—C32B	120.0
C19—C20—C15	120.8 (3)	C34B—C33B—H33B	120.0
C19—C20—H20	119.6 (19)	C32B—C33B—H33B	120.0
C15—C20—H20	119.6 (19)	C33B—C34B—C35B	120.0
C18—O21—C22	118.3 (3)	C33B—C34B—H34B	120.0
O21—C22—H22A	109.5	C35B—C34B—H34B	120.0
O21—C22—H22B	109.5	C34B—C35B—C36B	120.0
H22A—C22—H22B	109.5	C34B—C35B—H35B	120.0
O21—C22—H22C	109.5	C36B—C35B—H35B	120.0
H22A—C22—H22C	109.5	C35B—C36B—C31B	120.0
H22B—C22—H22C	109.5	C35B—C36B—H36B	120.0
C24—C23—C28	117.5 (3)	C31B—C36B—H36B	120.0

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···N14^i	0.92 (4)	2.06 (4)	2.933 (3)	158 (3)

Symmetry code: (i) x, −y+1/2, z−1/2.