Crystal structure of 1-(2,6-diiso­propyl­phen­yl)-1H-imidazole

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.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 106 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.099
• Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.124 Check

Author Response: This large K variance results from weak reflections with Fc/Fc(max) = 0.000.

PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          3 Report

Author Response: Reflections missing due to interference by beamstop.

Alert level G
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         12 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

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

Crystal data

C15H20N2	F(000) = 496
Mr = 228.33	Dx = 1.125 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.6642 (13) Å	Cell parameters from 9863 reflections
b = 16.519 (6) Å	θ = 2.8–47.3°
c = 14.414 (6) Å	µ = 0.07 mm^−1
β = 90.73 (2)°	T = 106 K
V = 1348.6 (8) Å^3	Prism, colorless
Z = 4	0.20 × 0.15 × 0.10 mm

Data collection

Bruker D8 Venture Kappa diffractometer	2750 reflections with I > 2σ(I)
Radiation source: microfocus sealed tube	Rint = 0.030
φ and ω scans	θmax = 27.1°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −7→7
	k = −21→21
22918 measured reflections	l = −18→18
2975 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	All H-atom parameters refined
wR(F^2) = 0.099	w = 1/[σ^2(Fo^2) + (0.0376P)^2 + 0.5846P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
2975 reflections	Δρmax = 0.26 e Å^−3
234 parameters	Δρmin = −0.23 e Å^−3

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
N1	0.44635 (15)	0.73907 (5)	0.71450 (6)	0.0157 (2)
H1	0.113 (3)	0.7150 (9)	0.6734 (10)	0.023 (3)*
C1	0.2081 (2)	0.73808 (7)	0.72124 (8)	0.0215 (2)
N2	0.13631 (17)	0.77200 (6)	0.79847 (7)	0.0245 (2)
H2	0.337 (3)	0.8212 (9)	0.9035 (11)	0.028 (4)*
C2	0.3404 (2)	0.79580 (7)	0.84352 (8)	0.0218 (2)
C3	0.5334 (2)	0.77620 (7)	0.79331 (7)	0.0189 (2)
H3	0.701 (3)	0.7824 (9)	0.8042 (10)	0.024 (3)*
C4	0.58676 (18)	0.70733 (6)	0.64044 (7)	0.0155 (2)
H4	0.518 (3)	0.8608 (9)	0.6295 (10)	0.028 (4)*
C5	0.67446 (19)	0.76113 (6)	0.57433 (7)	0.0173 (2)
H5	0.881 (3)	0.7657 (9)	0.4575 (10)	0.026 (4)*
C7	0.8606 (2)	0.64725 (7)	0.49976 (7)	0.0204 (2)
H7	0.806 (3)	0.5371 (9)	0.5612 (10)	0.028 (4)*
C8	0.77076 (19)	0.59529 (7)	0.56604 (8)	0.0200 (2)
H8	0.455 (3)	0.5972 (9)	0.7572 (10)	0.026 (4)*
C9	0.63395 (18)	0.62423 (6)	0.63861 (7)	0.0171 (2)
H9	0.928 (4)	0.8858 (12)	0.6469 (14)	0.059 (6)*
H12	0.429 (3)	0.9356 (11)	0.4939 (12)	0.043 (4)*
C12	0.8378 (3)	0.90170 (9)	0.59054 (13)	0.0409 (4)
H11	0.794 (3)	0.9602 (11)	0.5977 (12)	0.045 (5)*
C11	0.4803 (3)	0.87601 (8)	0.48960 (11)	0.0388 (3)
C10	0.6171 (2)	0.85084 (7)	0.57667 (8)	0.0222 (2)
H10	0.933 (3)	0.8961 (11)	0.5377 (13)	0.042 (5)*
C15	0.3703 (2)	0.50568 (8)	0.66749 (10)	0.0305 (3)
H16	0.457 (3)	0.4716 (11)	0.6197 (13)	0.049 (5)*
H17	0.311 (3)	0.4685 (10)	0.7143 (11)	0.037 (4)*
H18	0.829 (3)	0.4848 (10)	0.7182 (12)	0.042 (4)*
H19	0.680 (3)	0.4898 (10)	0.8134 (12)	0.040 (4)*
H20	0.856 (3)	0.5610 (10)	0.7892 (11)	0.036 (4)*
H15	0.237 (3)	0.5350 (10)	0.6368 (11)	0.040 (4)*
C14	0.7432 (2)	0.52320 (9)	0.76253 (10)	0.0314 (3)
H14	0.337 (4)	0.8422 (13)	0.4783 (14)	0.061 (6)*
C13	0.5411 (2)	0.56655 (7)	0.71156 (8)	0.0209 (2)
H13	0.588 (3)	0.8716 (11)	0.4351 (14)	0.051 (5)*
C6	0.81454 (19)	0.72946 (7)	0.50430 (7)	0.0196 (2)
H6	0.954 (2)	0.6261 (8)	0.4495 (9)	0.020 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0140 (4)	0.0180 (4)	0.0150 (4)	0.0011 (3)	0.0003 (3)	−0.0003 (3)
C1	0.0145 (5)	0.0295 (6)	0.0205 (5)	0.0011 (4)	−0.0007 (4)	−0.0026 (4)
N2	0.0167 (5)	0.0336 (6)	0.0232 (5)	0.0032 (4)	0.0024 (4)	−0.0032 (4)
C2	0.0204 (5)	0.0268 (6)	0.0181 (5)	0.0024 (4)	0.0020 (4)	−0.0036 (4)
C3	0.0173 (5)	0.0224 (5)	0.0170 (5)	0.0004 (4)	−0.0004 (4)	−0.0029 (4)
C4	0.0127 (5)	0.0195 (5)	0.0144 (5)	0.0011 (4)	−0.0003 (4)	−0.0015 (4)
C5	0.0171 (5)	0.0191 (5)	0.0158 (5)	−0.0003 (4)	−0.0022 (4)	0.0000 (4)
C7	0.0181 (5)	0.0272 (6)	0.0162 (5)	0.0017 (4)	0.0027 (4)	−0.0041 (4)
C8	0.0196 (5)	0.0191 (5)	0.0214 (5)	0.0023 (4)	0.0004 (4)	−0.0030 (4)
C9	0.0151 (5)	0.0193 (5)	0.0169 (5)	−0.0001 (4)	−0.0009 (4)	0.0001 (4)
C12	0.0394 (8)	0.0226 (6)	0.0603 (10)	−0.0047 (6)	−0.0099 (7)	−0.0053 (6)
C11	0.0495 (9)	0.0227 (6)	0.0437 (8)	0.0063 (6)	−0.0175 (7)	0.0030 (6)
C10	0.0284 (6)	0.0177 (5)	0.0205 (5)	0.0011 (4)	0.0023 (4)	0.0019 (4)
C15	0.0263 (6)	0.0265 (6)	0.0387 (7)	−0.0063 (5)	−0.0001 (5)	0.0054 (5)
C14	0.0278 (6)	0.0359 (7)	0.0303 (6)	0.0002 (5)	−0.0021 (5)	0.0130 (6)
C13	0.0212 (5)	0.0194 (5)	0.0222 (5)	0.0012 (4)	0.0040 (4)	0.0026 (4)
C6	0.0185 (5)	0.0252 (6)	0.0151 (5)	−0.0027 (4)	0.0009 (4)	0.0015 (4)

Geometric parameters (Å, º)

N1—C1	1.3544 (14)	C12—H9	0.99 (2)
N1—C3	1.3769 (14)	C12—H11	1.004 (18)
N1—C4	1.4382 (14)	C12—C10	1.5173 (19)
C1—H1	0.950 (15)	C12—H10	0.945 (18)
C1—N2	1.3153 (16)	C11—H12	1.028 (18)
N2—C2	1.3759 (16)	C11—C10	1.5245 (18)
C2—H2	0.961 (15)	C11—H14	1.00 (2)
C2—C3	1.3578 (16)	C11—H13	1.00 (2)
C3—H3	0.965 (15)	C10—H4	0.967 (15)
C4—C5	1.3988 (15)	C15—H16	1.019 (19)
C4—C9	1.3988 (15)	C15—H17	0.975 (17)
C5—C10	1.5176 (16)	C15—H15	0.998 (18)
C5—C6	1.3937 (16)	C15—C13	1.5280 (17)
C7—C8	1.3860 (16)	C14—H18	1.027 (18)
C7—C6	1.3845 (17)	C14—H19	0.988 (17)
C7—H6	0.969 (14)	C14—H20	0.968 (17)
C8—H7	0.984 (15)	C14—C13	1.5300 (17)
C8—C9	1.3941 (15)	C13—H8	0.968 (15)
C9—C13	1.5180 (15)	C6—H5	0.981 (15)
C1—N1—C3	107.02 (9)	H12—C11—H14	108.4 (15)
C1—N1—C4	127.58 (9)	H12—C11—H13	107.0 (14)
C3—N1—C4	125.40 (9)	C10—C11—H12	110.7 (10)
N1—C1—H1	120.6 (9)	C10—C11—H14	112.7 (12)
N2—C1—N1	112.01 (10)	C10—C11—H13	108.5 (11)
N2—C1—H1	127.4 (9)	H14—C11—H13	109.4 (16)
C1—N2—C2	104.73 (10)	C5—C10—H4	108.1 (9)
N2—C2—H2	121.7 (9)	C5—C10—C11	110.78 (10)
C3—C2—N2	110.95 (10)	C12—C10—H4	106.8 (9)
C3—C2—H2	127.4 (9)	C12—C10—C5	111.56 (11)
N1—C3—H3	121.5 (8)	C12—C10—C11	111.51 (12)
C2—C3—N1	105.30 (10)	C11—C10—H4	107.8 (9)
C2—C3—H3	133.2 (8)	H16—C15—H17	106.9 (14)
C5—C4—N1	118.59 (9)	H16—C15—H15	109.6 (14)
C9—C4—N1	118.64 (9)	H17—C15—H15	110.4 (14)
C9—C4—C5	122.75 (10)	C13—C15—H16	109.8 (11)
C4—C5—C10	121.82 (10)	C13—C15—H17	110.3 (10)
C6—C5—C4	117.73 (10)	C13—C15—H15	109.8 (10)
C6—C5—C10	120.44 (10)	H18—C14—H19	107.2 (13)
C8—C7—H6	120.1 (8)	H18—C14—H20	109.4 (13)
C6—C7—C8	120.25 (10)	H19—C14—H20	107.9 (13)
C6—C7—H6	119.6 (8)	C13—C14—H18	110.3 (9)
C7—C8—H7	118.6 (9)	C13—C14—H19	110.0 (10)
C7—C8—C9	121.15 (10)	C13—C14—H20	111.9 (10)
C9—C8—H7	120.3 (9)	C9—C13—H8	109.0 (8)
C4—C9—C13	122.34 (10)	C9—C13—C15	110.37 (10)
C8—C9—C4	117.31 (10)	C9—C13—C14	111.28 (10)
C8—C9—C13	120.34 (10)	C15—C13—H8	107.8 (9)
H9—C12—H11	107.3 (15)	C15—C13—C14	110.94 (11)
H9—C12—H10	109.9 (16)	C14—C13—H8	107.4 (9)
H11—C12—H10	108.8 (15)	C5—C6—H5	119.8 (8)
C10—C12—H9	112.2 (12)	C7—C6—C5	120.78 (10)
C10—C12—H11	109.9 (10)	C7—C6—H5	119.4 (8)
C10—C12—H10	108.6 (11)
N1—C1—N2—C2	−0.11 (13)	C4—C5—C6—C7	1.25 (16)
N1—C4—C5—C10	−2.52 (15)	C4—C9—C13—C15	116.01 (12)
N1—C4—C5—C6	178.59 (9)	C4—C9—C13—C14	−120.37 (12)
N1—C4—C9—C8	−179.92 (9)	C5—C4—C9—C8	−1.27 (15)
N1—C4—C9—C13	0.36 (15)	C5—C4—C9—C13	179.01 (10)
C1—N1—C3—C2	−0.09 (12)	C7—C8—C9—C4	1.46 (16)
C1—N1—C4—C5	100.55 (13)	C7—C8—C9—C13	−178.81 (10)
C1—N1—C4—C9	−80.74 (14)	C8—C7—C6—C5	−1.08 (17)
C1—N2—C2—C3	0.05 (14)	C8—C9—C13—C15	−63.71 (14)
N2—C2—C3—N1	0.03 (13)	C8—C9—C13—C14	59.92 (14)
C3—N1—C1—N2	0.13 (13)	C9—C4—C5—C10	178.83 (10)
C3—N1—C4—C5	−79.97 (13)	C9—C4—C5—C6	−0.06 (16)
C3—N1—C4—C9	98.74 (13)	C10—C5—C6—C7	−177.65 (10)
C4—N1—C1—N2	179.68 (10)	C6—C5—C10—C12	−63.43 (15)
C4—N1—C3—C2	−179.66 (10)	C6—C5—C10—C11	61.42 (15)
C4—C5—C10—C12	117.71 (13)	C6—C7—C8—C9	−0.33 (17)
C4—C5—C10—C11	−117.43 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N2^i	0.966 (17)	2.474 (17)	3.416 (2)	164.9 (12)

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