(3Z)-3-Benzyl­idene-1H-benzimidazo[1,2-a]imidazol-2(3H)-one

In the title compound, C₁₆H₁₁N₃O, the mol­ecular conformation is partially determined by an intra­molecular C—H...π(ring) inter­action. In the crystal, pairwise N—H...N hydrogen bonds form dimers, which associate into stacks through a combination of C—H...O, C—H...π(ring) and offset π–π stacking inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.136
• Data-to-parameter ratio = 10.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full value Low .      0.949 Note
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          2 Check

Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.744 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600        110 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Note

Alert level G
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         65 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          3 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   2 ALERT level B = A potentially serious problem, consider carefully
   3 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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   1 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, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(3Z)-3-Benzylidene-1H-benzimidazo[1,2-a]imidazol-2(3H)-one

Crystal data

C16H11N3O	Z = 2
Mr = 261.28	F(000) = 272
Triclinic, P1	Dx = 1.412 Mg m^−3
a = 6.6849 (3) Å	Cu Kα radiation, λ = 1.54178 Å
b = 8.9428 (5) Å	Cell parameters from 3426 reflections
c = 10.7445 (5) Å	θ = 5.2–72.5°
α = 103.935 (3)°	µ = 0.74 mm^−1
β = 95.015 (4)°	T = 150 K
γ = 96.860 (3)°	Plate, colourless
V = 614.44 (5) Å^3	0.21 × 0.15 × 0.02 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2249 independent reflections
Radiation source: INCOATEC IµS micro-focus source	1810 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.032
Detector resolution: 10.4167 pixels mm^-1	θmax = 72.5°, θmin = 5.2°
ω scans	h = −8→7
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −11→9
Tmin = 0.83, Tmax = 0.98	l = −13→13
4587 measured reflections

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)] = 0.047	Hydrogen site location: difference Fourier map
wR(F^2) = 0.136	All H-atom parameters refined
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0532P)^2 + 0.4943P] where P = (Fo^2 + 2Fc^2)/3
2249 reflections	(Δ/σ)max = 0.001
225 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.26 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.

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 > 2sigma(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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.9044 (2)	0.95697 (17)	0.15628 (15)	0.0297 (4)
N1	0.7919 (3)	0.4128 (2)	0.07214 (17)	0.0235 (4)
N2	0.6348 (3)	0.60823 (19)	0.17826 (16)	0.0205 (4)
N3	0.9139 (3)	0.6904 (2)	0.09709 (17)	0.0237 (4)
H3A	1.019 (4)	0.680 (3)	0.047 (3)	0.044 (8)*
C1	0.6146 (3)	0.3508 (2)	0.11504 (19)	0.0215 (4)
C2	0.5370 (3)	0.1964 (2)	0.1005 (2)	0.0245 (5)
H2	0.609 (4)	0.114 (3)	0.058 (3)	0.039 (7)*
C3	0.3508 (3)	0.1635 (2)	0.1428 (2)	0.0262 (5)
H3	0.285 (4)	0.056 (3)	0.127 (3)	0.031 (6)*
C4	0.2429 (3)	0.2818 (3)	0.1978 (2)	0.0267 (5)
H4	0.107 (4)	0.254 (3)	0.222 (2)	0.027 (6)*
C5	0.3203 (3)	0.4385 (2)	0.21698 (19)	0.0223 (4)
H5	0.247 (4)	0.526 (3)	0.260 (3)	0.029 (6)*
C6	0.5095 (3)	0.4707 (2)	0.17753 (19)	0.0212 (4)
C7	0.6545 (3)	0.7717 (2)	0.21504 (19)	0.0219 (4)
C8	0.8346 (3)	0.8244 (2)	0.15278 (19)	0.0232 (5)
C9	0.7924 (3)	0.5630 (2)	0.11100 (19)	0.0216 (4)
C10	0.5593 (3)	0.8678 (2)	0.2973 (2)	0.0234 (5)
H10	0.599 (4)	0.983 (3)	0.307 (2)	0.031 (6)*
C11	0.4150 (3)	0.8193 (2)	0.3810 (2)	0.0232 (5)
C12	0.4692 (4)	0.7249 (3)	0.4607 (2)	0.0273 (5)
H12	0.607 (4)	0.693 (3)	0.460 (3)	0.041 (8)*
C13	0.3346 (4)	0.6764 (3)	0.5388 (2)	0.0333 (5)
H13	0.375 (4)	0.610 (3)	0.596 (3)	0.039 (7)*
C14	0.1420 (4)	0.7199 (3)	0.5370 (2)	0.0373 (6)
H14	0.044 (5)	0.685 (3)	0.592 (3)	0.052 (9)*
C15	0.0887 (4)	0.8166 (3)	0.4608 (3)	0.0365 (6)
H15	−0.049 (5)	0.846 (4)	0.462 (3)	0.057 (9)*
C16	0.2245 (3)	0.8687 (3)	0.3846 (2)	0.0288 (5)
H16	0.189 (4)	0.940 (3)	0.329 (3)	0.039 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0337 (9)	0.0220 (8)	0.0333 (9)	−0.0005 (6)	0.0081 (7)	0.0075 (6)
N1	0.0260 (9)	0.0214 (9)	0.0234 (9)	0.0039 (7)	0.0091 (7)	0.0040 (7)
N2	0.0202 (9)	0.0188 (8)	0.0215 (8)	0.0019 (6)	0.0053 (7)	0.0029 (6)
N3	0.0243 (9)	0.0213 (9)	0.0251 (9)	0.0010 (7)	0.0090 (7)	0.0041 (7)
C1	0.0234 (10)	0.0218 (10)	0.0190 (9)	0.0034 (8)	0.0058 (8)	0.0035 (7)
C2	0.0290 (11)	0.0209 (10)	0.0217 (10)	0.0031 (8)	0.0050 (9)	0.0016 (8)
C3	0.0325 (12)	0.0208 (10)	0.0232 (10)	−0.0019 (9)	0.0064 (9)	0.0033 (8)
C4	0.0272 (12)	0.0281 (11)	0.0241 (11)	−0.0011 (9)	0.0089 (9)	0.0056 (9)
C5	0.0212 (10)	0.0266 (11)	0.0170 (9)	0.0026 (8)	0.0011 (8)	0.0022 (8)
C6	0.0268 (11)	0.0187 (10)	0.0176 (9)	0.0031 (8)	0.0062 (8)	0.0028 (7)
C7	0.0244 (11)	0.0204 (10)	0.0207 (10)	0.0022 (8)	0.0045 (8)	0.0046 (8)
C8	0.0260 (11)	0.0229 (11)	0.0191 (10)	0.0006 (8)	0.0029 (8)	0.0037 (8)
C9	0.0216 (10)	0.0224 (10)	0.0198 (10)	0.0017 (8)	0.0064 (8)	0.0028 (8)
C10	0.0254 (11)	0.0218 (11)	0.0224 (10)	0.0051 (8)	0.0047 (8)	0.0034 (8)
C11	0.0263 (11)	0.0204 (10)	0.0202 (10)	0.0033 (8)	0.0051 (8)	−0.0008 (8)
C12	0.0303 (12)	0.0262 (11)	0.0253 (11)	0.0066 (9)	0.0052 (9)	0.0045 (9)
C13	0.0447 (14)	0.0325 (12)	0.0239 (11)	0.0055 (10)	0.0095 (10)	0.0073 (9)
C14	0.0415 (14)	0.0399 (14)	0.0296 (12)	0.0019 (11)	0.0173 (11)	0.0045 (10)
C15	0.0282 (13)	0.0410 (14)	0.0388 (13)	0.0076 (10)	0.0115 (11)	0.0037 (11)
C16	0.0288 (12)	0.0292 (12)	0.0276 (11)	0.0079 (9)	0.0044 (9)	0.0034 (9)

Geometric parameters (Å, º)

O1—C8	1.212 (3)	C5—C6	1.388 (3)
N1—C9	1.306 (3)	C5—H5	1.01 (3)
N1—C1	1.409 (3)	C7—C10	1.337 (3)
N2—C9	1.375 (3)	C7—C8	1.509 (3)
N2—C6	1.401 (3)	C10—C11	1.472 (3)
N2—C7	1.406 (3)	C10—H10	1.01 (3)
N3—C9	1.365 (3)	C11—C12	1.394 (3)
N3—C8	1.392 (3)	C11—C16	1.397 (3)
N3—H3A	0.93 (3)	C12—C13	1.384 (3)
C1—C2	1.382 (3)	C12—H12	1.00 (3)
C1—C6	1.418 (3)	C13—C14	1.388 (4)
C2—C3	1.386 (3)	C13—H13	1.00 (3)
C2—H2	0.97 (3)	C14—C15	1.382 (4)
C3—C4	1.394 (3)	C14—H14	0.99 (3)
C3—H3	0.98 (3)	C15—C16	1.386 (3)
C4—C5	1.394 (3)	C15—H15	0.98 (3)
C4—H4	0.98 (2)	C16—H16	1.01 (3)
C9—N1—C1	103.06 (16)	O1—C8—N3	126.4 (2)
C9—N2—C6	106.03 (16)	O1—C8—C7	127.33 (19)
C9—N2—C7	109.67 (17)	N3—C8—C7	106.19 (17)
C6—N2—C7	144.18 (18)	N1—C9—N3	134.23 (19)
C9—N3—C8	109.39 (17)	N1—C9—N2	115.54 (18)
C9—N3—H3A	121.3 (18)	N3—C9—N2	110.20 (17)
C8—N3—H3A	128.7 (18)	C7—C10—C11	125.17 (19)
C2—C1—N1	128.60 (19)	C7—C10—H10	116.6 (14)
C2—C1—C6	120.20 (19)	C11—C10—H10	118.1 (14)
N1—C1—C6	111.18 (17)	C12—C11—C16	118.8 (2)
C1—C2—C3	118.06 (19)	C12—C11—C10	119.93 (19)
C1—C2—H2	120.3 (16)	C16—C11—C10	121.3 (2)
C3—C2—H2	121.6 (16)	C13—C12—C11	120.8 (2)
C2—C3—C4	121.4 (2)	C13—C12—H12	120.8 (16)
C2—C3—H3	120.7 (15)	C11—C12—H12	118.5 (16)
C4—C3—H3	117.6 (15)	C12—C13—C14	120.0 (2)
C3—C4—C5	121.7 (2)	C12—C13—H13	120.2 (16)
C3—C4—H4	119.3 (14)	C14—C13—H13	119.7 (16)
C5—C4—H4	119.0 (14)	C15—C14—C13	119.6 (2)
C6—C5—C4	116.56 (19)	C15—C14—H14	119.8 (18)
C6—C5—H5	120.6 (14)	C13—C14—H14	120.6 (18)
C4—C5—H5	122.8 (14)	C14—C15—C16	120.7 (2)
C5—C6—N2	133.96 (19)	C14—C15—H15	117.5 (19)
C5—C6—C1	121.92 (18)	C16—C15—H15	121.8 (19)
N2—C6—C1	104.03 (17)	C15—C16—C11	120.1 (2)
C10—C7—N2	131.17 (19)	C15—C16—H16	121.8 (16)
C10—C7—C8	124.17 (19)	C11—C16—H16	118.1 (16)
N2—C7—C8	104.25 (16)
C9—N1—C1—C2	179.9 (2)	N2—C7—C8—O1	178.3 (2)
C9—N1—C1—C6	1.4 (2)	C10—C7—C8—N3	167.8 (2)
N1—C1—C2—C3	−175.2 (2)	N2—C7—C8—N3	−5.5 (2)
C6—C1—C2—C3	3.1 (3)	C1—N1—C9—N3	−176.5 (2)
C1—C2—C3—C4	0.5 (3)	C1—N1—C9—N2	1.3 (2)
C2—C3—C4—C5	−2.3 (3)	C8—N3—C9—N1	176.2 (2)
C3—C4—C5—C6	0.5 (3)	C8—N3—C9—N2	−1.6 (2)
C4—C5—C6—N2	179.0 (2)	C6—N2—C9—N1	−3.5 (2)
C4—C5—C6—C1	3.1 (3)	C7—N2—C9—N1	179.52 (17)
C9—N2—C6—C5	−172.6 (2)	C6—N2—C9—N3	174.82 (17)
C7—N2—C6—C5	2.6 (5)	C7—N2—C9—N3	−2.2 (2)
C9—N2—C6—C1	3.9 (2)	N2—C7—C10—C11	5.8 (4)
C7—N2—C6—C1	179.1 (3)	C8—C7—C10—C11	−165.6 (2)
C2—C1—C6—C5	−5.0 (3)	C7—C10—C11—C12	51.9 (3)
N1—C1—C6—C5	173.59 (19)	C7—C10—C11—C16	−129.4 (2)
C2—C1—C6—N2	177.99 (19)	C16—C11—C12—C13	2.1 (3)
N1—C1—C6—N2	−3.4 (2)	C10—C11—C12—C13	−179.1 (2)
C9—N2—C7—C10	−168.0 (2)	C11—C12—C13—C14	1.0 (3)
C6—N2—C7—C10	16.9 (5)	C12—C13—C14—C15	−2.6 (4)
C9—N2—C7—C8	4.7 (2)	C13—C14—C15—C16	1.0 (4)
C6—N2—C7—C8	−170.4 (3)	C14—C15—C16—C11	2.2 (4)
C9—N3—C8—O1	−179.3 (2)	C12—C11—C16—C15	−3.7 (3)
C9—N3—C8—C7	4.5 (2)	C10—C11—C16—C15	177.6 (2)
C10—C7—C8—O1	−8.3 (4)

Hydrogen-bond geometry (Å, º)

Cg3 and Cg4 are the centroids of the C1–C6 and C11–C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N1^i	0.93 (3)	1.98 (3)	2.876 (2)	162 (3)
C16—H16···O1^ii	1.01 (3)	2.58 (3)	3.412 (3)	139 (2)
C5—H5···Cg4	1.01 (3)	2.65 (3)	3.512 (2)	143 (3)
C10—H10···Cg4^iii	1.01 (3)	2.88 (2)	3.606 (2)	129.0 (15)
C13—H13···Cg3^iv	1.00 (3)	2.73 (3)	3.474 (2)	132 (2)

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