2,6-Di-tert-butyl-4-[(1-methyl-1H-benzimidazol-2-yl)imino]cyclo­hexa-2,5-dien-1-one

Borbulevych, O.Ya.

doi:10.1107/S1600536807003315

2,6-Di-tert-butyl-4-[(1-methyl-1H-benzimidazol-2-yl)imino]cyclohexa-2,5-dien-1-one

Except for two pairs of methyl groups, all non-H atoms of the title compound, C₂₂H₂₇N₃O, occupy special positions on a mirror plane. The molecules are packed in a herring-bone manner and form stacks along [010].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807003315/bi2151sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807003315/bi2151Isup2.hkl Contains datablock I

CCDC reference: 636158

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R factor = 0.064
wR factor = 0.214
Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.33 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.66 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      37.00 A   3 

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97.

2,6-Di-tert-butyl-4-[(1-methyl-1H-benzimidazol-2-yl)imino]cyclohexa- 2,5-dien-1-one top

Crystal data top

C₂₂H₂₇N₃O	F(000) = 752
M_r = 349.47	D_x = 1.107 Mg m⁻³
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 24 reflections
a = 18.372 (4) Å	θ = 10–11°
b = 6.7816 (14) Å	µ = 0.07 mm⁻¹
c = 16.833 (3) Å	T = 293 K
V = 2097.3 (7) Å³	Prism, yellow
Z = 4	0.50 × 0.30 × 0.30 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.000
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 1.6°
Graphite monochromator	h = −21→0
θ/2θ scans	k = −8→0
1985 measured reflections	l = 0→20
1985 independent reflections	2 standard reflections every 98 reflections
996 reflections with I > 2σ(I)	intensity decay: 3.7%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.064	H-atom parameters constrained
wR(F²) = 0.214	w = 1/[σ²(F_o²) + (0.1333P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
1985 reflections	Δρ_max = 0.28 e Å⁻³
154 parameters	Δρ_min = −0.23 e Å⁻³
12 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.019 (4)

Special details top

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.2289 (2)	0.2500	0.1741 (2)	0.185 (3)
N1	0.00602 (17)	0.2500	0.37636 (18)	0.0483 (9)
N2	−0.06078 (17)	0.2500	0.49479 (19)	0.0514 (9)
N3	0.06047 (19)	0.2500	0.51014 (19)	0.0555 (10)
C1	0.1793 (2)	0.2500	0.2218 (3)	0.0792 (16)
C2	0.1031 (2)	0.2500	0.1933 (2)	0.0559 (11)
C3	0.0507 (2)	0.2500	0.2479 (2)	0.0505 (10)
H3	0.0026	0.2500	0.2307	0.061*
C4	0.0641 (2)	0.2500	0.3318 (2)	0.0447 (10)
C5	0.1394 (2)	0.2500	0.3583 (2)	0.0520 (11)
H5	0.1492	0.2500	0.4125	0.062*
C6	0.1948 (2)	0.2500	0.3070 (2)	0.0529 (11)
C7	0.0059 (2)	0.2500	0.4586 (2)	0.0474 (10)
C8	−0.0491 (2)	0.2500	0.5748 (2)	0.0549 (11)
C9	−0.0953 (3)	0.2500	0.6401 (3)	0.0700 (14)
H9	−0.1456	0.2500	0.6340	0.084*
C10	−0.0639 (4)	0.2500	0.7137 (3)	0.0808 (16)
H10	−0.0933	0.2500	0.7586	0.097*
C11	0.0122 (4)	0.2500	0.7228 (3)	0.0820 (16)
H11	0.0317	0.2500	0.7738	0.098*
C12	0.0581 (3)	0.2500	0.6597 (3)	0.0745 (14)
H12	0.1083	0.2500	0.6668	0.089*
C13	0.0276 (2)	0.2500	0.5831 (2)	0.0552 (11)
C14	0.0887 (3)	0.2500	0.1037 (3)	0.0743 (15)
C15	0.0081 (3)	0.2500	0.0870 (3)	0.107 (2)
H15A	−0.0005	0.2500	0.0308	0.160*
H15B	−0.0133	0.1344	0.1102	0.160*
C16	0.1209 (3)	0.0659 (9)	0.0663 (2)	0.149 (2)
H16A	0.1003	−0.0489	0.0909	0.223*
H16B	0.1727	0.0656	0.0737	0.223*
H16C	0.1101	0.0645	0.0105	0.223*
C17	0.2743 (2)	0.2500	0.3350 (3)	0.0696 (14)
C18	0.2788 (3)	0.2500	0.4249 (3)	0.109 (2)
H18A	0.3289	0.2500	0.4412	0.164*
H18B	0.2551	0.3656	0.4453	0.164*
C19	0.3131 (2)	0.0645 (7)	0.3042 (3)	0.1257 (19)
H19A	0.3139	0.0663	0.2472	0.189*
H19B	0.2877	−0.0507	0.3223	0.189*
H19C	0.3621	0.0621	0.3240	0.189*
C20	−0.1312 (2)	0.2500	0.4558 (3)	0.0724 (14)
H20A	−0.1690	0.2500	0.4952	0.109*
H20B	−0.1357	0.3656	0.4232	0.109*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.055 (2)	0.430 (11)	0.069 (2)	0.000	0.009 (2)	0.000
N1	0.047 (2)	0.049 (2)	0.049 (2)	0.000	0.0019 (15)	0.000
N2	0.050 (2)	0.047 (2)	0.058 (2)	0.000	0.0091 (17)	0.000
N3	0.062 (2)	0.055 (2)	0.049 (2)	0.000	−0.0029 (18)	0.000
C1	0.043 (3)	0.133 (5)	0.062 (3)	0.000	0.011 (2)	0.000
C2	0.042 (2)	0.075 (3)	0.051 (3)	0.000	0.003 (2)	0.000
C3	0.043 (2)	0.056 (2)	0.052 (3)	0.000	−0.0028 (19)	0.000
C4	0.042 (2)	0.044 (2)	0.048 (2)	0.000	0.0018 (18)	0.000
C5	0.050 (2)	0.052 (2)	0.054 (2)	0.000	−0.007 (2)	0.000
C6	0.040 (2)	0.062 (3)	0.056 (3)	0.000	−0.003 (2)	0.000
C7	0.048 (2)	0.041 (2)	0.053 (2)	0.000	0.000 (2)	0.000
C8	0.077 (3)	0.038 (2)	0.050 (3)	0.000	0.009 (2)	0.000
C9	0.093 (3)	0.052 (3)	0.065 (3)	0.000	0.024 (3)	0.000
C10	0.130 (5)	0.058 (3)	0.055 (3)	0.000	0.025 (3)	0.000
C11	0.123 (5)	0.072 (3)	0.051 (3)	0.000	0.001 (3)	0.000
C12	0.098 (4)	0.067 (3)	0.059 (3)	0.000	−0.004 (3)	0.000
C13	0.072 (3)	0.042 (2)	0.051 (3)	0.000	0.000 (2)	0.000
C14	0.062 (3)	0.112 (4)	0.049 (3)	0.000	0.001 (2)	0.000
C15	0.070 (3)	0.199 (7)	0.051 (3)	0.000	−0.011 (2)	0.000
C16	0.173 (5)	0.196 (5)	0.077 (3)	0.070 (4)	−0.013 (3)	−0.055 (3)
C17	0.041 (2)	0.092 (4)	0.076 (3)	0.000	−0.010 (2)	0.000
C18	0.057 (3)	0.179 (6)	0.092 (4)	0.000	−0.030 (3)	0.000
C19	0.062 (2)	0.136 (4)	0.180 (5)	0.037 (3)	−0.018 (2)	−0.048 (4)
C20	0.051 (3)	0.090 (4)	0.076 (3)	0.000	0.008 (2)	0.000

Geometric parameters (Å, º) top

O1—C1	1.214 (5)	C10—H10	0.930
N1—C4	1.305 (5)	C11—C12	1.358 (7)
N1—C7	1.384 (5)	C11—H11	0.930
N2—C8	1.364 (5)	C12—C13	1.404 (6)
N2—C7	1.368 (5)	C12—H12	0.930
N2—C20	1.452 (5)	C14—C15	1.507 (7)
N3—C7	1.326 (5)	C14—C16	1.519 (5)
N3—C13	1.369 (5)	C14—C16ⁱ	1.519 (5)
C1—C6	1.462 (6)	C15—H15A	0.960
C1—C2	1.480 (6)	C15—H15B	0.960
C2—C3	1.332 (5)	C16—H16A	0.960
C2—C14	1.531 (6)	C16—H16B	0.960
C3—C4	1.433 (6)	C16—H16C	0.960
C3—H3	0.930	C17—C18	1.517 (7)
C4—C5	1.454 (5)	C17—C19ⁱ	1.536 (5)
C5—C6	1.335 (5)	C17—C19	1.536 (5)
C5—H5	0.930	C18—H18A	0.960
C6—C17	1.534 (6)	C18—H18B	0.960
C8—C9	1.388 (6)	C19—H19A	0.960
C8—C13	1.417 (6)	C19—H19B	0.960
C9—C10	1.368 (7)	C19—H19C	0.960
C9—H9	0.930	C20—H20A	0.960
C10—C11	1.405 (8)	C20—H20B	0.960

C4—N1—C7	125.2 (3)	C11—C12—H12	121.0
C8—N2—C7	107.4 (3)	C13—C12—H12	121.0
C8—N2—C20	125.9 (3)	N3—C13—C12	130.4 (4)
C7—N2—C20	126.7 (3)	N3—C13—C8	110.5 (4)
C7—N3—C13	104.7 (3)	C12—C13—C8	119.2 (4)
O1—C1—C6	120.1 (4)	C15—C14—C16	107.8 (3)
O1—C1—C2	119.7 (4)	C15—C14—C16ⁱ	107.8 (3)
C6—C1—C2	120.2 (4)	C16—C14—C16ⁱ	110.6 (5)
C3—C2—C1	117.4 (4)	C15—C14—C2	110.7 (4)
C3—C2—C14	123.8 (4)	C16—C14—C2	110.0 (3)
C1—C2—C14	118.9 (4)	C16ⁱ—C14—C2	110.0 (3)
C2—C3—C4	123.8 (4)	C14—C15—H15A	110.2
C2—C3—H3	118.1	C14—C15—H15B	109.1
C4—C3—H3	118.1	H15A—C15—H15B	109.5
N1—C4—C3	115.2 (3)	C14—C16—H16A	109.5
N1—C4—C5	127.0 (4)	C14—C16—H16B	109.5
C3—C4—C5	117.8 (3)	H16A—C16—H16B	109.5
C6—C5—C4	121.8 (4)	C14—C16—H16C	109.5
C6—C5—H5	119.1	H16A—C16—H16C	109.5
C4—C5—H5	119.1	H16B—C16—H16C	109.5
C5—C6—C1	119.0 (4)	C18—C17—C6	111.0 (4)
C5—C6—C17	121.8 (4)	C18—C17—C19ⁱ	108.1 (3)
C1—C6—C17	119.1 (4)	C6—C17—C19ⁱ	109.8 (2)
N3—C7—N2	112.7 (3)	C18—C17—C19	108.1 (3)
N3—C7—N1	130.8 (4)	C6—C17—C19	109.8 (3)
N2—C7—N1	116.6 (3)	C19ⁱ—C17—C19	109.9 (5)
N2—C8—C9	133.2 (5)	C17—C18—H18A	109.7
N2—C8—C13	104.7 (3)	C17—C18—H18B	109.4
C9—C8—C13	122.0 (4)	H18A—C18—H18B	109.5
C10—C9—C8	117.3 (5)	C17—C19—H19A	109.5
C10—C9—H9	121.4	C17—C19—H19B	109.5
C8—C9—H9	121.4	H19A—C19—H19B	109.5
C9—C10—C11	121.3 (5)	C17—C19—H19C	109.5
C9—C10—H10	119.4	H19A—C19—H19C	109.5
C11—C10—H10	119.4	H19B—C19—H19C	109.5
C12—C11—C10	122.1 (5)	N2—C20—H20A	109.4
C12—C11—H11	118.9	N2—C20—H20B	109.5
C10—C11—H11	118.9	H20A—C20—H20B	109.5
C11—C12—C13	118.1 (5)

O1—C1—C2—C3	180.0	C7—N2—C8—C13	0.0
C6—C1—C2—C3	0.0	C20—N2—C8—C13	180.0
O1—C1—C2—C14	0.0	N2—C8—C9—C10	180.000 (1)
C6—C1—C2—C14	180.0	C13—C8—C9—C10	0.000 (1)
C1—C2—C3—C4	0.0	C8—C9—C10—C11	0.000 (1)
C14—C2—C3—C4	180.0	C9—C10—C11—C12	0.000 (2)
C7—N1—C4—C3	180.0	C10—C11—C12—C13	0.000 (1)
C7—N1—C4—C5	0.0	C7—N3—C13—C12	180.0
C2—C3—C4—N1	180.0	C7—N3—C13—C8	0.0
C2—C3—C4—C5	0.0	C11—C12—C13—N3	180.0
N1—C4—C5—C6	180.0	C11—C12—C13—C8	0.000 (1)
C3—C4—C5—C6	0.0	N2—C8—C13—N3	0.0
C4—C5—C6—C1	0.0	C9—C8—C13—N3	180.0
C4—C5—C6—C17	180.0	N2—C8—C13—C12	180.0
O1—C1—C6—C5	180.0	C9—C8—C13—C12	0.000 (1)
C2—C1—C6—C5	0.0	C3—C2—C14—C15	0.0
O1—C1—C6—C17	0.0	C1—C2—C14—C15	180.0
C2—C1—C6—C17	180.0	C3—C2—C14—C16	−119.0 (3)
C13—N3—C7—N2	0.0	C1—C2—C14—C16	61.0 (3)
C13—N3—C7—N1	180.0	C3—C2—C14—C16ⁱ	119.0 (3)
C8—N2—C7—N3	0.0	C1—C2—C14—C16ⁱ	−61.0 (3)
C20—N2—C7—N3	180.0	C5—C6—C17—C18	0.0
C8—N2—C7—N1	180.0	C1—C6—C17—C18	180.0
C20—N2—C7—N1	0.0	C5—C6—C17—C19ⁱ	−119.5 (3)
C4—N1—C7—N3	0.0	C1—C6—C17—C19ⁱ	60.5 (3)
C4—N1—C7—N2	180.0	C5—C6—C17—C19	119.5 (3)
C7—N2—C8—C9	180.000 (1)	C1—C6—C17—C19	−60.5 (3)
C20—N2—C8—C9	0.000 (1)

Symmetry code: (i) x, −y+1/2, z.

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2,6-Di-tert-butyl-4-[(1-methyl-1H-benzimidazol-2-yl)imino]cyclo­hexa-2,5-dien-1-one

Supporting information

Key indicators

checkCIF/PLATON results

2,6-Di-tert-butyl-4-[(1-methyl-1H-benzimidazol-2-yl)imino]cyclohexa-2,5-dien-1-one