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At 106 (2) K, the title mol­ecule has monoclinic P21/c symmetry with four mol­ecules in the unit cell. The imidazole ring is rotated 80.7 (1)° relative to the phenyl ring. Inter­molecular stabilization primarily results from close contacts between the N-atom at the 3-position on the imidazole ring and the C—H bond at the 4-position on the neighboring DippIm.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989023009179/oi2001sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989023009179/oi2001Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989023009179/oi2001Isup3.cml
Supplementary material

CCDC reference: 2302037

Computing details top

Data collection: APEX3 (Bruker, 2018); cell refinement: SAINT V8.40A (Bruker, 2018); data reduction: SAINT V8.40A (Bruker, 2018); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2019/3/1 (Sheldrick, 2015b) and OLEX2 (Dolomanov et al., 2009); molecular graphics: Mercury (Macrae et al., 2020).

1-(2,6-Diisopropylphenyl)-1H-imidazole top
Crystal data top
C15H20N2F(000) = 496
Mr = 228.33Dx = 1.125 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 5.6642 (13) ÅCell parameters from 9863 reflections
b = 16.519 (6) Åθ = 2.8–47.3°
c = 14.414 (6) ŵ = 0.07 mm1
β = 90.73 (2)°T = 106 K
V = 1348.6 (8) Å3Prism, colorless
Z = 40.20 × 0.15 × 0.10 mm
Data collection top
Bruker D8 Venture Kappa
diffractometer
2750 reflections with I > 2σ(I)
Radiation source: microfocus sealed tubeRint = 0.030
φ and ω scansθmax = 27.1°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
h = 77
k = 2121
22918 measured reflectionsl = 1818
2975 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040All H-atom parameters refined
wR(F2) = 0.099 w = 1/[σ2(Fo2) + (0.0376P)2 + 0.5846P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
2975 reflectionsΔρmax = 0.26 e Å3
234 parametersΔρmin = 0.23 e Å3
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.44635 (15)0.73907 (5)0.71450 (6)0.0157 (2)
H10.113 (3)0.7150 (9)0.6734 (10)0.023 (3)*
C10.2081 (2)0.73808 (7)0.72124 (8)0.0215 (2)
N20.13631 (17)0.77200 (6)0.79847 (7)0.0245 (2)
H20.337 (3)0.8212 (9)0.9035 (11)0.028 (4)*
C20.3404 (2)0.79580 (7)0.84352 (8)0.0218 (2)
C30.5334 (2)0.77620 (7)0.79331 (7)0.0189 (2)
H30.701 (3)0.7824 (9)0.8042 (10)0.024 (3)*
C40.58676 (18)0.70733 (6)0.64044 (7)0.0155 (2)
H40.518 (3)0.8608 (9)0.6295 (10)0.028 (4)*
C50.67446 (19)0.76113 (6)0.57433 (7)0.0173 (2)
H50.881 (3)0.7657 (9)0.4575 (10)0.026 (4)*
C70.8606 (2)0.64725 (7)0.49976 (7)0.0204 (2)
H70.806 (3)0.5371 (9)0.5612 (10)0.028 (4)*
C80.77076 (19)0.59529 (7)0.56604 (8)0.0200 (2)
H80.455 (3)0.5972 (9)0.7572 (10)0.026 (4)*
C90.63395 (18)0.62423 (6)0.63861 (7)0.0171 (2)
H90.928 (4)0.8858 (12)0.6469 (14)0.059 (6)*
H120.429 (3)0.9356 (11)0.4939 (12)0.043 (4)*
C120.8378 (3)0.90170 (9)0.59054 (13)0.0409 (4)
H110.794 (3)0.9602 (11)0.5977 (12)0.045 (5)*
C110.4803 (3)0.87601 (8)0.48960 (11)0.0388 (3)
C100.6171 (2)0.85084 (7)0.57667 (8)0.0222 (2)
H100.933 (3)0.8961 (11)0.5377 (13)0.042 (5)*
C150.3703 (2)0.50568 (8)0.66749 (10)0.0305 (3)
H160.457 (3)0.4716 (11)0.6197 (13)0.049 (5)*
H170.311 (3)0.4685 (10)0.7143 (11)0.037 (4)*
H180.829 (3)0.4848 (10)0.7182 (12)0.042 (4)*
H190.680 (3)0.4898 (10)0.8134 (12)0.040 (4)*
H200.856 (3)0.5610 (10)0.7892 (11)0.036 (4)*
H150.237 (3)0.5350 (10)0.6368 (11)0.040 (4)*
C140.7432 (2)0.52320 (9)0.76253 (10)0.0314 (3)
H140.337 (4)0.8422 (13)0.4783 (14)0.061 (6)*
C130.5411 (2)0.56655 (7)0.71156 (8)0.0209 (2)
H130.588 (3)0.8716 (11)0.4351 (14)0.051 (5)*
C60.81454 (19)0.72946 (7)0.50430 (7)0.0196 (2)
H60.954 (2)0.6261 (8)0.4495 (9)0.020 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0140 (4)0.0180 (4)0.0150 (4)0.0011 (3)0.0003 (3)0.0003 (3)
C10.0145 (5)0.0295 (6)0.0205 (5)0.0011 (4)0.0007 (4)0.0026 (4)
N20.0167 (5)0.0336 (6)0.0232 (5)0.0032 (4)0.0024 (4)0.0032 (4)
C20.0204 (5)0.0268 (6)0.0181 (5)0.0024 (4)0.0020 (4)0.0036 (4)
C30.0173 (5)0.0224 (5)0.0170 (5)0.0004 (4)0.0004 (4)0.0029 (4)
C40.0127 (5)0.0195 (5)0.0144 (5)0.0011 (4)0.0003 (4)0.0015 (4)
C50.0171 (5)0.0191 (5)0.0158 (5)0.0003 (4)0.0022 (4)0.0000 (4)
C70.0181 (5)0.0272 (6)0.0162 (5)0.0017 (4)0.0027 (4)0.0041 (4)
C80.0196 (5)0.0191 (5)0.0214 (5)0.0023 (4)0.0004 (4)0.0030 (4)
C90.0151 (5)0.0193 (5)0.0169 (5)0.0001 (4)0.0009 (4)0.0001 (4)
C120.0394 (8)0.0226 (6)0.0603 (10)0.0047 (6)0.0099 (7)0.0053 (6)
C110.0495 (9)0.0227 (6)0.0437 (8)0.0063 (6)0.0175 (7)0.0030 (6)
C100.0284 (6)0.0177 (5)0.0205 (5)0.0011 (4)0.0023 (4)0.0019 (4)
C150.0263 (6)0.0265 (6)0.0387 (7)0.0063 (5)0.0001 (5)0.0054 (5)
C140.0278 (6)0.0359 (7)0.0303 (6)0.0002 (5)0.0021 (5)0.0130 (6)
C130.0212 (5)0.0194 (5)0.0222 (5)0.0012 (4)0.0040 (4)0.0026 (4)
C60.0185 (5)0.0252 (6)0.0151 (5)0.0027 (4)0.0009 (4)0.0015 (4)
Geometric parameters (Å, º) top
N1—C11.3544 (14)C12—H90.99 (2)
N1—C31.3769 (14)C12—H111.004 (18)
N1—C41.4382 (14)C12—C101.5173 (19)
C1—H10.950 (15)C12—H100.945 (18)
C1—N21.3153 (16)C11—H121.028 (18)
N2—C21.3759 (16)C11—C101.5245 (18)
C2—H20.961 (15)C11—H141.00 (2)
C2—C31.3578 (16)C11—H131.00 (2)
C3—H30.965 (15)C10—H40.967 (15)
C4—C51.3988 (15)C15—H161.019 (19)
C4—C91.3988 (15)C15—H170.975 (17)
C5—C101.5176 (16)C15—H150.998 (18)
C5—C61.3937 (16)C15—C131.5280 (17)
C7—C81.3860 (16)C14—H181.027 (18)
C7—C61.3845 (17)C14—H190.988 (17)
C7—H60.969 (14)C14—H200.968 (17)
C8—H70.984 (15)C14—C131.5300 (17)
C8—C91.3941 (15)C13—H80.968 (15)
C9—C131.5180 (15)C6—H50.981 (15)
C1—N1—C3107.02 (9)H12—C11—H14108.4 (15)
C1—N1—C4127.58 (9)H12—C11—H13107.0 (14)
C3—N1—C4125.40 (9)C10—C11—H12110.7 (10)
N1—C1—H1120.6 (9)C10—C11—H14112.7 (12)
N2—C1—N1112.01 (10)C10—C11—H13108.5 (11)
N2—C1—H1127.4 (9)H14—C11—H13109.4 (16)
C1—N2—C2104.73 (10)C5—C10—H4108.1 (9)
N2—C2—H2121.7 (9)C5—C10—C11110.78 (10)
C3—C2—N2110.95 (10)C12—C10—H4106.8 (9)
C3—C2—H2127.4 (9)C12—C10—C5111.56 (11)
N1—C3—H3121.5 (8)C12—C10—C11111.51 (12)
C2—C3—N1105.30 (10)C11—C10—H4107.8 (9)
C2—C3—H3133.2 (8)H16—C15—H17106.9 (14)
C5—C4—N1118.59 (9)H16—C15—H15109.6 (14)
C9—C4—N1118.64 (9)H17—C15—H15110.4 (14)
C9—C4—C5122.75 (10)C13—C15—H16109.8 (11)
C4—C5—C10121.82 (10)C13—C15—H17110.3 (10)
C6—C5—C4117.73 (10)C13—C15—H15109.8 (10)
C6—C5—C10120.44 (10)H18—C14—H19107.2 (13)
C8—C7—H6120.1 (8)H18—C14—H20109.4 (13)
C6—C7—C8120.25 (10)H19—C14—H20107.9 (13)
C6—C7—H6119.6 (8)C13—C14—H18110.3 (9)
C7—C8—H7118.6 (9)C13—C14—H19110.0 (10)
C7—C8—C9121.15 (10)C13—C14—H20111.9 (10)
C9—C8—H7120.3 (9)C9—C13—H8109.0 (8)
C4—C9—C13122.34 (10)C9—C13—C15110.37 (10)
C8—C9—C4117.31 (10)C9—C13—C14111.28 (10)
C8—C9—C13120.34 (10)C15—C13—H8107.8 (9)
H9—C12—H11107.3 (15)C15—C13—C14110.94 (11)
H9—C12—H10109.9 (16)C14—C13—H8107.4 (9)
H11—C12—H10108.8 (15)C5—C6—H5119.8 (8)
C10—C12—H9112.2 (12)C7—C6—C5120.78 (10)
C10—C12—H11109.9 (10)C7—C6—H5119.4 (8)
C10—C12—H10108.6 (11)
N1—C1—N2—C20.11 (13)C4—C5—C6—C71.25 (16)
N1—C4—C5—C102.52 (15)C4—C9—C13—C15116.01 (12)
N1—C4—C5—C6178.59 (9)C4—C9—C13—C14120.37 (12)
N1—C4—C9—C8179.92 (9)C5—C4—C9—C81.27 (15)
N1—C4—C9—C130.36 (15)C5—C4—C9—C13179.01 (10)
C1—N1—C3—C20.09 (12)C7—C8—C9—C41.46 (16)
C1—N1—C4—C5100.55 (13)C7—C8—C9—C13178.81 (10)
C1—N1—C4—C980.74 (14)C8—C7—C6—C51.08 (17)
C1—N2—C2—C30.05 (14)C8—C9—C13—C1563.71 (14)
N2—C2—C3—N10.03 (13)C8—C9—C13—C1459.92 (14)
C3—N1—C1—N20.13 (13)C9—C4—C5—C10178.83 (10)
C3—N1—C4—C579.97 (13)C9—C4—C5—C60.06 (16)
C3—N1—C4—C998.74 (13)C10—C5—C6—C7177.65 (10)
C4—N1—C1—N2179.68 (10)C6—C5—C10—C1263.43 (15)
C4—N1—C3—C2179.66 (10)C6—C5—C10—C1161.42 (15)
C4—C5—C10—C12117.71 (13)C6—C7—C8—C90.33 (17)
C4—C5—C10—C11117.43 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···N2i0.966 (17)2.474 (17)3.416 (2)164.9 (12)
Symmetry code: (i) x+1, y, z.
 

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