7-(4-Methyl­phen­yl)-5-(methyl­sulfan­yl)-2-phenyl-1,3-benzothia­zole-4-carbonitrile

In the title compound, C₂₂H₁₆N₂S₂, the benzothia­zole and tolyl ring systems are inclined at an angle of 31.23 (8)°, and the dihedral angle between the phenyl and benzothiazole rings is 7.567 (2)°. In the crystal structure, inter­molecular C—H...N hydrogen bonds link the mol­ecules into a two-dimensional sheet and π–π stacking inter­actions [perpendicular distance 3.6170 (4) Å] reinforce the crystal cohesion.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.056
• wR factor = 0.129
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT391_ALERT_3_B Deviating Methyl C12     H-C-H Bond Angle ......      99.00 Deg.
PLAT735_ALERT_1_B D-H     Calc     1.05(4), Rep    1.045(5) ......       8.00 su-Ra
              C14  -H14     1.555   1.555
PLAT736_ALERT_1_B H...A   Calc     2.68(4), Rep    2.685(6) ......       6.67 su-Ra
              H14  -N1      1.555   3.775

Alert level C
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.33 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S2
PLAT245_ALERT_2_C U(iso) H22B    Smaller than U(eq) C22     by ...       0.01 AngSq
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT350_ALERT_3_C Short   C-H Bond (0.96A)   C12    -   H12B   ...       0.82 Ang.
PLAT350_ALERT_3_C Short   C-H Bond (0.96A)   C22    -   H22B   ...       0.83 Ang.
PLAT351_ALERT_3_C Long    C-H Bond (0.96A)   C22    -   H22A   ...       1.16 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C4     -   C21    ...       1.44 Ang.
PLAT390_ALERT_3_C Deviating Methyl C22     X-C-H Bond Angle ......     117.00 Deg.
PLAT390_ALERT_3_C Deviating Methyl C22     X-C-H Bond Angle ......     102.00 Deg.
PLAT391_ALERT_3_C Deviating Methyl C12     H-C-H Bond Angle ......     119.00 Deg.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14    ..  N1      ..       2.68 Ang.

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
   3 ALERT level B = Potentially serious problem
  13 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   9 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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S1. Comment

Benzothiazoles are bicyclic ring systems with multiple applications. They comprise a novel class of therapeutic compounds shown to exert a wide range of biological activities. Substituted derivatives of benzothiazole demonstrate several interesting pharmacological functions due to their potent capacity to interfere with cellular structures. For instance, the phenyl-substituted benzothiazoles show antitumor activity (Bradshaw, Bibby et al., 2002; Bradshaw, Chua et al., 2002; Hutchinson et al., 2002). They also act as antimicrobial (Holbová et al., 1990; Brownlee et al., 1992) and antimycobacterial (Sidóová & Odlerová, 1990) agents. In adition, they are used in the preparation of dyes (Brooker et al., 1940), organic synthesis of thermostable polymers (Corey & Boger, 1978) and as herbicides which inhibit photosynthesis (Králová et al., 1992). In this paper, we report the structure of the title compound, (I), which has been synthesized in our laboratory.

In (I), the benzothiazole and methylphenyl rings are inclined at an angle of 31.23 (8)° to each other (Fig. 1). The 2-subtituted phenyl ring is inclined with respect to benzothiazole ring at an angle of 7.74 (10)°. The methylthio and carbonitrile groups are cis to each other. The molecules of (I) are linked by C—H···N hydrogen bonds into two dimensional sheets via dimers (Table 1, Fig. 2). Their packing motifs correspond to Etter's descriptors, R²₂(14) and R²₂(22) (Bernstein et al., 1995). The molecular packing is further stabilized by π-π stacking interactions between the benzene rings; C13—C13* (* = 2 - x,-0.5 + y,0.5 - z) distance is 3.6170 (4) Å

Related literature

For related literature, see: Bernstein et al. (1995); Bradshaw, Bibby et al. (2002); Bradshaw, Chua et al. (2002); Brooker et al. (1940); Brownlee et al. (1992); Corey & Boger (1978); Hedge et al. (2006); Holbová et al. (1990); Hutchinson et al. (2002); Králová et al. (1992); Sidóová & Odlerová (1990).

S2. Experimental

To a suspension of NaH (60%, 0.88 g, 22 mmol) in dry benzene (20 ml) and dry DMF (20 ml) under stirring, a solution of (2-phenyl-1,3-thiazol-4-yl)- acetonitrile (2 g, 10 mmol) in dry benzene (10 ml) was added at 281 K over a period of 15 min and further stirred at 273–361 K for 15 min. Solution of a-oxoketene dithioacetal (10 mmol) in dry DMF (10 ml) was added slowly over 10 min to this mixture with stirring at 273–361 K. The reaction mixture was stirred at room temperature for 4–5 h. The solution was poured into an aqueous ammonium chloride solution (8%, 200 ml), and extracted with benzene (50 ml × 2). The collective extract was washed with water (100 ml × 3), dried over anhydrous sodium sulfate, passed through a silica bed, and concentrated. After standing for 2 h, the crystallized material was separated by filtration and washed with a mixture of benzene and hexane (1:1) to afford a colorless solid, 5-(4-methylphenyl)-3-(methylthio)-5-oxo- 2-(2-phenyl-1,3-thiazol-4-yl)pent-2-enenitrile.

The solution of 5-(4-Methylphenyl)-3-(methylthio)-5-oxo- 2-(2-phenyl-1,3-thiazol-4-yl)pent-2-enenitrile(2.5 mmol) and p-toluene sulphonic acid (1 g, 5.3 mmol) in benzene was refluxed for 4–6 h. The reaction mixture (monitored by TLC) was concentrated, dissolved in chloroform, and poured into aqueous sodium bicarbonate solution (6%, 150 ml). The organic layer was separated, washed with water (100 ml × 3), and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to yield the greenish yellow oil, which was purified by column chromatography using a benzene-hexane mixture (45:55v/v-80:20v/v) as eluent to furnish a yellow or greenish yellow solid 7-(4-methylphenyl)- 5-(methylthio)-2-phenyl-1,3-benzothiazole-4-carbonitrile (Hedge et al., 2006). Good quality single-crystals of (I) were grown from a chloroform solution by slow evaporation at room temperature.

S3. Refinement

All H atoms were located from Fourier difference maps and refined isotropically.

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids.
	Fig. 2. A view of the unit cell packing of (I).

7-(4-Methylphenyl)-5-(methylsulfanyl)-2-phenyl-1,3-benzothiazole-4-carbonitrile

Crystal data

C22H16N2S2	F(000) = 776
Mr = 372.49	Dx = 1.338 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 500 reflections
a = 11.4142 (11) Å	θ = 1.0–25.0°
b = 7.9101 (8) Å	µ = 0.30 mm^−1
c = 20.553 (2) Å	T = 293 K
β = 94.869 (2)°	Rectangular, yellow
V = 1849.0 (3) Å^3	0.3 × 0.2 × 0.1 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2730 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
Graphite monochromator	θmax = 25.0°, θmin = 1.8°
φ and ω scans	h = −13→13
12852 measured reflections	k = −9→9
3260 independent reflections	l = −24→24

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.129	All H-atom parameters refined
S = 1.15	w = 1/[σ^2(Fo^2) + (0.0511P)^2 + 0.8652P] where P = (Fo^2 + 2Fc^2)/3
3260 reflections	(Δ/σ)max = 0.001
237 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.19 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.

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

	x	y	z	Uiso*/Ueq
C1	0.9027 (2)	0.7127 (4)	−0.02928 (14)	0.0446 (7)
C2	0.8276 (3)	0.6166 (4)	0.05881 (15)	0.0467 (7)
C3	1.0029 (3)	0.7342 (4)	0.01428 (14)	0.0452 (7)
C4	0.9041 (3)	0.7583 (4)	−0.09522 (15)	0.0483 (7)
C5	1.0078 (3)	0.8232 (4)	−0.11692 (15)	0.0531 (8)
C6	1.1065 (3)	0.8403 (4)	−0.07267 (16)	0.0520 (8)
H6	1.175 (3)	0.877 (4)	−0.0863 (17)	0.058 (10)*
C7	1.1080 (3)	0.8004 (4)	−0.00666 (15)	0.0455 (7)
C8	1.2178 (3)	0.8258 (4)	0.03667 (15)	0.0466 (7)
C9	1.2497 (3)	0.7210 (5)	0.08930 (17)	0.0526 (8)
H9	1.205 (3)	0.630 (4)	0.0988 (15)	0.055 (9)*
C10	1.3538 (3)	0.7431 (5)	0.12779 (19)	0.0594 (9)
H10	1.374 (4)	0.662 (5)	0.165 (2)	0.082 (12)*
C11	1.4303 (3)	0.8725 (5)	0.11495 (17)	0.0589 (9)
C12	1.5458 (4)	0.8981 (9)	0.1561 (3)	0.0849 (14)
H12A	1.535 (4)	0.999 (7)	0.185 (3)	0.117 (17)*
H12B	1.598 (5)	0.901 (8)	0.131 (3)	0.13 (2)*
H12C	1.561 (5)	0.810 (7)	0.191 (3)	0.13 (2)*
C13	1.3986 (3)	0.9782 (5)	0.06248 (19)	0.0616 (10)
H13	1.445 (3)	1.068 (5)	0.0526 (17)	0.055 (9)*
C14	1.2947 (3)	0.9560 (4)	0.02381 (18)	0.0547 (8)
H14	1.276 (3)	1.041 (5)	−0.0146 (16)	0.045 (9)*
C15	0.7422 (3)	0.5403 (4)	0.09969 (15)	0.0481 (7)
C16	0.7639 (3)	0.5262 (5)	0.16663 (18)	0.0615 (9)
H16	0.832 (3)	0.560 (4)	0.1869 (17)	0.064 (11)*
C17	0.6819 (4)	0.4536 (6)	0.2037 (2)	0.0732 (12)
H17	0.699 (3)	0.449 (5)	0.248 (2)	0.075 (13)*
C18	0.5773 (4)	0.3960 (6)	0.1740 (2)	0.0717 (11)
H18	0.522 (3)	0.346 (4)	0.1975 (16)	0.065 (10)*
C19	0.5544 (3)	0.4091 (5)	0.1075 (2)	0.0662 (10)
H19	0.479 (3)	0.366 (5)	0.0883 (19)	0.082 (12)*
C20	0.6359 (3)	0.4809 (5)	0.07039 (19)	0.0587 (9)
H20	0.621 (3)	0.491 (4)	0.0263 (18)	0.059 (10)*
C21	0.8001 (3)	0.7345 (5)	−0.13869 (16)	0.0536 (8)
C22	1.1479 (5)	0.9563 (8)	−0.2095 (3)	0.0882 (15)
H22A	1.171 (5)	1.083 (8)	−0.183 (3)	0.15 (2)*
H22B	1.145 (3)	0.976 (5)	−0.249 (2)	0.077 (13)*
H22C	1.204 (5)	0.870 (7)	−0.201 (3)	0.13 (2)*
N1	0.8054 (2)	0.6455 (4)	−0.00331 (13)	0.0476 (6)
N2	0.7190 (3)	0.7147 (5)	−0.17417 (16)	0.0748 (10)
S1	0.96953 (7)	0.67111 (11)	0.09166 (4)	0.0508 (3)
S2	1.00579 (9)	0.87246 (18)	−0.20032 (5)	0.0879 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0435 (16)	0.0431 (17)	0.0476 (18)	0.0030 (13)	0.0067 (14)	0.0010 (13)
C2	0.0461 (17)	0.0455 (18)	0.0485 (18)	0.0039 (14)	0.0035 (14)	−0.0013 (14)
C3	0.0469 (16)	0.0458 (18)	0.0431 (17)	0.0071 (13)	0.0044 (14)	0.0016 (13)
C4	0.0467 (18)	0.0505 (19)	0.0475 (17)	0.0046 (14)	0.0033 (14)	0.0045 (15)
C5	0.0530 (19)	0.059 (2)	0.0469 (18)	0.0035 (15)	0.0044 (15)	0.0078 (15)
C6	0.0445 (18)	0.057 (2)	0.054 (2)	−0.0019 (15)	0.0057 (15)	0.0068 (16)
C7	0.0450 (16)	0.0420 (17)	0.0497 (18)	0.0039 (13)	0.0049 (14)	0.0010 (14)
C8	0.0453 (16)	0.0473 (18)	0.0476 (18)	0.0040 (14)	0.0071 (14)	−0.0036 (14)
C9	0.0471 (18)	0.054 (2)	0.057 (2)	−0.0050 (16)	0.0040 (16)	0.0005 (16)
C10	0.054 (2)	0.067 (2)	0.056 (2)	0.0049 (18)	0.0008 (17)	−0.002 (2)
C11	0.0469 (18)	0.073 (2)	0.057 (2)	0.0010 (17)	0.0042 (16)	−0.0173 (18)
C12	0.057 (3)	0.114 (4)	0.082 (3)	−0.009 (3)	−0.006 (2)	−0.018 (3)
C13	0.054 (2)	0.063 (2)	0.069 (2)	−0.0132 (18)	0.0139 (19)	−0.0110 (19)
C14	0.053 (2)	0.051 (2)	0.061 (2)	0.0006 (16)	0.0084 (16)	−0.0004 (17)
C15	0.0475 (17)	0.0498 (18)	0.0475 (18)	0.0017 (14)	0.0071 (14)	−0.0012 (14)
C16	0.055 (2)	0.077 (3)	0.052 (2)	−0.0065 (19)	0.0001 (17)	0.0034 (18)
C17	0.078 (3)	0.091 (3)	0.053 (2)	−0.008 (2)	0.015 (2)	0.012 (2)
C18	0.066 (2)	0.080 (3)	0.072 (3)	−0.009 (2)	0.024 (2)	0.008 (2)
C19	0.056 (2)	0.074 (3)	0.070 (3)	−0.0126 (19)	0.0108 (19)	−0.004 (2)
C20	0.056 (2)	0.069 (2)	0.051 (2)	−0.0031 (17)	0.0042 (17)	−0.0007 (18)
C21	0.0526 (19)	0.064 (2)	0.0448 (19)	0.0011 (16)	0.0080 (16)	0.0060 (16)
C22	0.077 (3)	0.116 (5)	0.074 (3)	−0.010 (3)	0.022 (3)	0.033 (3)
N1	0.0458 (14)	0.0511 (17)	0.0459 (16)	0.0019 (12)	0.0037 (12)	0.0006 (13)
N2	0.0580 (19)	0.106 (3)	0.058 (2)	−0.0108 (18)	−0.0041 (16)	0.0010 (18)
S1	0.0471 (5)	0.0616 (5)	0.0436 (5)	−0.0010 (4)	0.0030 (3)	0.0013 (4)
S2	0.0671 (6)	0.1441 (12)	0.0514 (6)	−0.0234 (6)	−0.0009 (5)	0.0296 (6)

Geometric parameters (Å, º)

C1—N1	1.379 (4)	C12—H12A	1.01 (6)
C1—C3	1.402 (4)	C12—H12B	0.82 (6)
C1—C4	1.404 (4)	C12—H12C	1.01 (6)
C2—N1	1.301 (4)	C13—C14	1.381 (5)
C2—C15	1.470 (4)	C13—H13	0.92 (4)
C2—S1	1.755 (3)	C14—H14	1.05 (3)
C3—C7	1.409 (4)	C15—C16	1.382 (5)
C3—S1	1.740 (3)	C15—C20	1.389 (5)
C4—C5	1.397 (4)	C16—C17	1.380 (5)
C4—C21	1.436 (5)	C16—H16	0.89 (4)
C5—C6	1.394 (4)	C17—C18	1.372 (6)
C5—S2	1.756 (3)	C17—H17	0.91 (4)
C6—C7	1.392 (4)	C18—C19	1.373 (5)
C6—H6	0.90 (4)	C18—H18	0.92 (4)
C7—C8	1.487 (4)	C19—C20	1.374 (5)
C8—C9	1.387 (4)	C19—H19	0.98 (4)
C8—C14	1.393 (4)	C20—H20	0.91 (3)
C9—C10	1.382 (5)	C21—N2	1.140 (4)
C9—H9	0.91 (3)	C22—S2	1.778 (5)
C10—C11	1.385 (5)	C22—H22A	1.16 (7)
C10—H10	1.01 (4)	C22—H22B	0.83 (4)
C11—C13	1.388 (5)	C22—H22C	0.94 (6)
C11—C12	1.518 (5)
N1—C1—C3	116.1 (3)	H12A—C12—H12C	98 (4)
N1—C1—C4	123.2 (3)	H12B—C12—H12C	112 (5)
C3—C1—C4	120.7 (3)	C14—C13—C11	121.7 (3)
N1—C2—C15	123.3 (3)	C14—C13—H13	117 (2)
N1—C2—S1	115.6 (2)	C11—C13—H13	121 (2)
C15—C2—S1	121.1 (2)	C13—C14—C8	120.6 (4)
C1—C3—C7	121.3 (3)	C13—C14—H14	117.5 (19)
C1—C3—S1	108.6 (2)	C8—C14—H14	121.9 (19)
C7—C3—S1	130.1 (2)	C16—C15—C20	118.7 (3)
C5—C4—C1	118.8 (3)	C16—C15—C2	122.0 (3)
C5—C4—C21	121.8 (3)	C20—C15—C2	119.2 (3)
C1—C4—C21	119.4 (3)	C17—C16—C15	120.7 (4)
C6—C5—C4	119.2 (3)	C17—C16—H16	118 (2)
C6—C5—S2	123.9 (2)	C15—C16—H16	121 (2)
C4—C5—S2	116.9 (2)	C18—C17—C16	119.8 (4)
C7—C6—C5	123.8 (3)	C18—C17—H17	122 (2)
C7—C6—H6	116 (2)	C16—C17—H17	118 (2)
C5—C6—H6	120 (2)	C17—C18—C19	120.2 (4)
C6—C7—C3	116.2 (3)	C17—C18—H18	121 (2)
C6—C7—C8	119.5 (3)	C19—C18—H18	118 (2)
C3—C7—C8	124.2 (3)	C18—C19—C20	120.2 (4)
C9—C8—C14	117.5 (3)	C18—C19—H19	117 (2)
C9—C8—C7	122.6 (3)	C20—C19—H19	122 (2)
C14—C8—C7	119.9 (3)	C19—C20—C15	120.4 (3)
C10—C9—C8	121.8 (3)	C19—C20—H20	121 (2)
C10—C9—H9	116 (2)	C15—C20—H20	119 (2)
C8—C9—H9	122 (2)	N2—C21—C4	178.6 (3)
C9—C10—C11	120.7 (4)	S2—C22—H22A	116 (3)
C9—C10—H10	119 (2)	S2—C22—H22B	102 (3)
C11—C10—H10	120 (2)	H22A—C22—H22B	107 (4)
C10—C11—C13	117.8 (3)	S2—C22—H22C	109 (4)
C10—C11—C12	121.6 (4)	H22A—C22—H22C	114 (5)
C13—C11—C12	120.6 (4)	H22B—C22—H22C	107 (4)
C11—C12—H12A	107 (3)	C2—N1—C1	110.5 (3)
C11—C12—H12B	108 (4)	C3—S1—C2	89.17 (15)
H12A—C12—H12B	118 (5)	C5—S2—C22	104.5 (2)
C11—C12—H12C	113 (3)
N1—C1—C3—C7	179.5 (3)	C6—C7—C8—C14	31.5 (4)
C4—C1—C3—C7	−0.6 (5)	C3—C7—C8—C14	−149.7 (3)
N1—C1—C3—S1	−1.6 (3)	C14—C8—C9—C10	−0.2 (5)
C4—C1—C3—S1	178.3 (2)	C7—C8—C9—C10	177.9 (3)
N1—C1—C4—C5	−179.1 (3)	C7—C8—C14—C13	−178.1 (3)
C3—C1—C4—C5	1.0 (5)	N1—C2—C15—C16	−173.5 (3)
N1—C1—C4—C21	−0.2 (5)	S1—C2—C15—C16	7.7 (4)
C3—C1—C4—C21	179.9 (3)	N1—C2—C15—C20	6.3 (5)
C1—C4—C5—C6	0.2 (5)	S1—C2—C15—C20	−172.5 (3)
C21—C4—C5—C6	−178.7 (3)	C20—C15—C16—C17	0.4 (6)
C1—C4—C5—S2	178.2 (2)	C2—C15—C16—C17	−179.8 (4)
C21—C4—C5—S2	−0.7 (4)	C2—C15—C20—C19	−180.0 (3)
C4—C5—C6—C7	−1.8 (5)	C15—C2—N1—C1	−178.1 (3)
S2—C5—C6—C7	−179.7 (3)	S1—C2—N1—C1	0.7 (4)
C5—C6—C7—C3	2.1 (5)	C3—C1—N1—C2	0.6 (4)
C5—C6—C7—C8	−179.1 (3)	C4—C1—N1—C2	−179.3 (3)
C1—C3—C7—C6	−0.8 (4)	C1—C3—S1—C2	1.6 (2)
S1—C3—C7—C6	−179.5 (2)	C7—C3—S1—C2	−179.6 (3)
C1—C3—C7—C8	−179.6 (3)	N1—C2—S1—C3	−1.4 (3)
S1—C3—C7—C8	1.6 (5)	C15—C2—S1—C3	177.5 (3)
C6—C7—C8—C9	−146.5 (3)	C6—C5—S2—C22	−3.8 (4)
C3—C7—C8—C9	32.3 (5)	C4—C5—S2—C22	178.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···N1^i	1.045 (5)	2.685 (6)	3.367 (5)	123

Symmetry code: (i) −x+2, −y+2, −z.